The Unofficial Biography Of Kimmay

Prequel: The Nature Of Love

by G L Hudson

 

Chapter 3

Excerpts from Cynthia L. May's diary

In late summer I had comfortably adjusted to my new profession. I started using my spare time to look around for a boyfriend. I spent several hours each week around the Notre Dame campus. In the middle of August not much was happening. Summer school was over, and the kids hadn't started returning for the fall semester. So, I used the time to familiarize myself with the area.

The first week in September I was walking around the student union area when I spotted a couple of boys walking towards the union. One of them was on the short side, thin and from a distance looked to be rather young. I decided to follow him. They headed towards the snack shop, bought some food and sat down at a table. I walked over to another table and sat down facing the younger boy. He was very young looking. He had almost no facial hair, and his complexion was very smooth for a boy. His nose was larger than a girl's, but on the small side for a boy. His facial features were also on the small side, as were his hands. He had medium brown hair, not very long, but then again not cut in a buzz that was popular with many of the boys. He didn't have an earring or any visible tattoos. He looked like an old-fashioned, 'clean-cut' American boy.

The two of them stood to walk away, and it was easy to see that he was a small boy. He was probably no taller than me and not much heavier. I decided that the boy had potential, so I followed him out of the union. He and his buddy walked over to a grassy area and sat down. They both opened their books, but it was obvious that they were interested in something other than books. I studied him for a few more minutes and then decided that I should try him out.

I walked over to him and asked if I could join him. I started some small talk and found him to be very shy. He barely talked. Getting information out of him was like pulling teeth. I finally found out that he was a freshman and a music major. Both good items I decided. After a bit more small talk, I decided that I liked his looks and wanted to make a move on him. I asked if he would show me around the campus, and we were able to break away from his roommate. When I had him alone I began stroking his ego, building him up and probing him for more information about himself.

We spent most of the day together and I liked what I saw. His physical size and appearance were not masculine, but neither was he as feminine as I would have liked. His physical appearance would be relatively easy to alter. He didn't have strong family ties, and he didn't know many people at school yet, so it would be rather easy to isolate him. He was very naïve about girls, and had little experience with them, so he would have few references with which to compare our relationship and how I treated him. And he didn't appear to be strong willed or know what it was he wanted out of life, so again it would be easy to control and manipulate him.

I took him to dinner at a German restaurant and began the introduction to his most important fall course, 'Girls-R-Us 101'. His introduction began with his new lifestyle, especially his diet. I introduced him to the Atkin's diet, and started encouraging him to eliminate french fries and carbohydrates from his diet. I wanted to encourage him to keep healthy, and to look after his appearance. I told him that his hair was pretty, and that he would look much sexier with longer hair.

I changed the conversation to talk about women; what they were wearing, and how he felt about different clothing fashions and hairstyles. Every time a girl would walk by, I would ask him a specific question about her. Was she pretty? What was pretty about her? Do you like her hair? Should she change her hair color? Was her hair too curly or too straight? Were her shoes appropriate for her dress, or skirt or jeans? How could we dress or change that girl to make her more attractive? I made him think constantly about feminine topics. I constantly praised women showing off smooth legs. I repeatedly asked him questions to keep him thinking about women and clothing and makeup and hair styling. I criticized men, and especially women, who were dressed too casual. Men and women wearing shorts were pointed out and I tried to always find negative things to say. I gushed over women wearing nice dresses or wearing more than the minimal amount of makeup. I found something negative to say about every man that walked by us. I especially criticized men with facial, chest or leg hair.

At one point during the dinner I talked him into trading drivers licenses so that I could get his vital statistics. I pointed out his picture, and again mentioned how much nicer he would look with longer hair. I memorized his height (one inch shorter than me), his weight (fifteen pounds more than me), his birth date and social security number. I excused my self and went to the bathroom where I wrote down the data on a note pad so that I wouldn't forget any of the information.

After we finished eating, we sat at the table and continued to talk. I was getting a sore throat doing all of the talking. At one point I took out a compact mirror and my lipstick, and made a big production out of refreshing my lipstick. When I saw him watching me intently, I asked him to lean towards me and pucker his lips. He resisted, but I insisted. "It is a very light shade, no one will notice. You will love the taste. It's full of moisturizers and emollients, and it is really good for your lips." I kept up the persuasion and finally he relented. I smoothed the lipstick over his lips and then made him smack his lips to even it out. You could barely see the lipstick on him, but it had been an important step.

It was starting to get late, so we walked out to the car. I put my arm through his as we walked to the car. I didn't use my electronic key to unlock the door. Instead I walked to the passenger side of the car, unlocked the door, then opened it and held it for him while he got in. Before I had left the house that morning, I had engaged the childproof locks. It forced the passenger to wait for me to walk around and open the door from the outside. I told him I had done this because I drove into all types of neighborhoods on my sales rounds, and I felt safer this way. When we used my car, I wanted him to get used to being treated like a girl on a date. I closed the door and went to my side and got in. On the way to his dorm he still had not asked for my telephone number. I decided that I didn't want to lose him over his trivial shyness, so I brought up the subject myself and gave him my number.

When we came to a stop I gave him an encouraging kiss, then walked around the car to let him out. I drove one block down the street and parked the car. I opened the trunk and took out a dozen flyers from the local Reproductive Fertility Center. I walked back to the dorm and put two into his mailbox, and then one into the mailboxes of the surrounding rooms. If the topic came up, I wanted him to think that there had been a mass mailing to the dorm. Later I would leave one with the mail at my house, so I could bring up the topic with him then.

It had been a good day. The process had started. The next Monday I began to make arrangements. I called the beauty salon and made an 11:00A.M. appointment for a wash and set in two weeks. I went shopping and bought satin sheets and pillowcases. I went to Victoria's Secret and bought 2 negligees and 2 robes for Matt. They were all made of satin. One was lavender, ankle length and had double spaghetti straps that crossed in the back. The bodice was low cut and would show plenty of cleavage, once it started to grow. It came with matching tap pants. The second was red, with spaghetti straps and a scalloped, lace lined bodice. The hem would barely cover the bottom of his cheeks. It was very sexy. It came with matching bikini style panties. With the combination of satin sheets and these satin negligees, he was probably going to slide out of bed once or twice a night. I also bought him a couple of white, satin camisoles in different styles. Two had adjustable spaghetti straps, two were sleeveless with wide straps, and two had short cap sleeves. All of them had adorable lace trim around the bodice. He was going to be inundated in soft fabrics and sexy, feminine attire.

The following Friday, I picked up Matt as we had arranged. We went out to catch a burger, and I complained that I was feeling a little tired. Instead of catching a movie at the theater, I suggested that we pick up a movie at Blockbuster and watch it at my house. He agreed. But once we were back at my house, I started working on getting him to model for me. I wanted to practice my photography skills, and I wanted to get some "before" pictures. It didn't take much convincing and I soon had him modeling for me.

After a few pictures I talked him into taking off his shirt. I was happy to see how little hair he had. But I played it up like he was covered with hair. I pointed out that professional male models shaved their chest hair and I suggested that he do the same. Once I offered to shave his chest for him, he quickly agreed. I took him to the bathroom and prepped him for shaving. Then, to make it more sexual for him, I took off my top, using the premise that I didn't want to get water on my tee shirt. He of course, bought the story. Once I had his chest shaved, I immediately started to shave his armpits. This caught him by surprise, as I intended, and I had to use a bit more persuasion to get him to allow me to continue. Actually, he was rather easy to manipulate. I soon had his chest and armpits totally shaved and we headed back to the studio to continue the shoot.

After we finished taking pictures. I downloaded them onto the computer and we started looking at them. I was happy to see that he was more than a little interested in the pictures. I used the opportunity to ask his opinion and get him as involved as possible. I knew that this would help in the future when I wanted to work on more 'artistic' pictures. We actually had a couple of decent pictures, and I moved these into another file for future printing at a professional shop.

By the time that we had finished with the pictures it was late and time to take Matt back to the dorms. To his credit, he asked if he could see me the next day. He volunteered to mow the lawn, and I accepted his offer. I took him out to the car and again opened his door for him, took him to the dorm and gave him a long kiss, then walked around the car to open his door and let him out. It was another successful day, but Saturday turned out even better.

He rode his bike to my house the next day. I puttered around the house in my negligee for a couple of hours waiting for him to arrive. I met him at the door, while wearing just my negligee. He wanted to get started immediately with the mowing but I managed to stall him for at least thirty minutes, so that he could see me walking around in my negligee. Finally, I could stall him no longer and I showed him where the gas and mower were located. But before he started I made him come into my bedroom and sit at my vanity while he applied suntan lotion. I made him apply lipstick to protect his lips. There was nothing special about the lipstick, but I convinced him that it would be good sun protection.

He went outside and proceeded with his chores, while I changed into a pretty sundress. When he finished mowing he was drenched in sweat. What an opportunity I thought. I told him he needed to take a shower and clean up. I led him to the bathroom where I introduced him to parts of his future beauty regimen. First I gave him some alpha-hydroxy facial cleanser and told him how to use it. Then I showed him the routine for using shampoo and a cream rinse. I went under the sink and pulled out a baby powder scented anti-perspirant. While he was cleaning up I went through my dresser and found some cotton panties with a wide elastic waist. I was tempted to give him some bikini panties, but I wanted him to be comfortable in his first pair of women's panties.

When I heard him finish drying, I knocked on the door and told him to reach out and I would hand him some clean underwear. He took the underwear and closed the door, then I heard a yell as he complained that I had given him some women's panties. "It's all I have," I told him. "They'll have to do." He threatened to put on his own underwear and I insisted that he couldn't. As long as I gave him the excuse that I was the one insisting on the panties, I knew he would quickly agree. And he did. When he came out of the bathroom I was standing in the hall to catch him by surprise. I knew right away that he liked them. He had an erection. I joked with him a bit and complimented him on his nice smell. I tousled his semi-wet hair and said, "You really have to think about letting this grow longer. You look cute now, but longer hair would make you irresistible to all the girls."

I insisted on having a light lunch, and then headed to the mall for an afternoon of shopping. I took him through every woman's store that I could find. I tried on numerous dresses, suits, skirts and tops. I made him come back to the dressing area and inspect every outfit that I tried. I always explained what the garment was called, what fabric it was made with, how it should be worn, what should be worn with it, the accessories that could be used to compliment the outfit, and on and on. I continuously asked his opinion about the clothes. I held the clothes up to him to see how they might fit him. (I told him that I was doing it to help visualize how the clothes would fit on me.)

Along with the specific clothes shopping, I commented on all of the women that we encountered. I talked about their choices in clothes, hairstyles and makeup. I pointed out the good, the bad and the ugly. I asked for his comments and opinions. I pushed him to become very critical of other people's dress and behavior. How they walked, talked and acted. I always found something negative to say about men. I especially criticized body hair and short hairstyles. Once in a while we would spot a man with longer hair, and I pointed out how nice it looked, but how much nicer it could look if it had a better color or better upkeep. His 'Girls-R-Us 101' class continued all afternoon.

By the end of a long day of shopping, all that I had bought was a pair of black heels in extra wide. I thought Matt would be able to use them with his Halloween costume. On the way back to the car I took him through the cosmetics department of one of the larger stores. Acting like it was a spur of the moment thought, I sat him down in a chair at the cosmetics counter and went to find a salesgirl. I explained to her that my boyfriend liked lipstick and I wanted to buy him an especially creamy variety. I told her to make it a nude or very light color, and that we were going to tell him that it was to protect his lips from the sun.

When we walked back to the counter, I watched closely as she told him what she was going to do. I loved watching him squirm just a bit, but quickly give in. I knew that these little feminine touches were titillating and keeping him excited and interested. They were working exactly as I hoped. The saleslady searched through a drawer full of lipsticks until she found one marked nude. She opened the tube of lipstick and applied it to Matt's lips. She instructed him to look in the mirror.

"I guess you can't really notice it," he said. I smiled.

I recommended Chinese carry out and that we take it to my house and watch the movie we had picked up the previous night. During the movie I made it a point of cuddling with him and keeping him excited. At the end of the night I told him it was time to go. He was ready to walk out the door while still wearing his panties. I had to remind him that he was still wearing my panties. I wasn't sure if he really forgot, or if he wanted to keep them. I thought asking him such a question could potentially push him into a defensive position, so I kept it to myself. After he changed, we loaded his bicycle in the trunk of my car and I again opened his door and seated him. I gave him a long kiss at the dormitory and then let him out.

The next day was Sunday. I called Valerie and spent over two hours talking with her. I told her all the details on how we had met and what we had done. She insisted that I e-mail her some of the pictures that I had taken. I did that while we were talking, and when she saw the pictures she congratulated me on my find. "He is going to make a pretty bride. Remember, I want to be one of your bridesmaids," she said.

"Not a bridesmaid," I replied, "I want you to be my maid-of-honor. And I want Sam to be one of my bridesmaids. Do you think he will do it?"

"That's hard to say. Normally, I think he would do anything you asked, but he is no longer the little boy that you and I used to dress up and put lipstick on. It will probably depend on who else is there that knows him. But by all means, ask him. I would love to dress him up one more time."

After two hours on the phone with Valerie, I spent another two hours talking with mom. She also wanted to see the pictures. "You have a pretty boy friend. I think he will be something very special." I wasn't sure if mom was playing with me or acknowledging what I had said I wanted many years ago. Mom could be cryptic at times.

Finally, the following weekend arrived. This was going to be an important weekend, and I was very nervous about it. There was a band playing at the student union, so that was our first stop. We watched and danced a bit and then headed over to a local burger joint. The band had been very loud, so we hadn't had much opportunity to talk. We both ordered burgers and salads with no fries. I insisted that we toss at least half of the buns. They were just too rich in carbohydrates and unhealthy. Matt agreed. After eating I went into my purse and pulled out my lipstick and a small mirror. I had deliberately brought a darker shade of lipstick than I had used the previous weekend. Again, I made a big production of refreshing my lipstick. I offered the mirror to Matt and asked if he had brought his lipstick with him. He had not. I gave him the lecture on taking take of his complexion and keeping his lips well moisturized. I then offered him my lipstick. "I can't put that on," he said. "It's too red. People will notice."

"Then lean over, and I'll put it on for you. If you haven't noticed it's getting dark out. People will not notice. People aren't expecting men to wear lipstick. If they notice anything, and I doubt that they will, they'll notice that you have rosy red lips. They won't for a second think it is lipstick. And finally, it's not that noticeable at all." I gave him a stern look with my eyes, but a slight grin with my lips. He thought about it for about ten seconds while I continued to hold the lipstick in my hand. He finally leaned forward without saying a word and let me apply the lipstick. "Smack your lips together." He did. "Now lean over here and give me a kiss." I gave him a gentle kiss so that we would not smear our lipstick. "You have to admit, not only does it feel good, but it tastes good too." I smiled, trying to encourage him into a brighter mood. He finally relented.

He gave me a smile and in a quiet voice said, "Yeah I guess your right. Your lipstick isn't that noticeable, and I do like the taste of it. Can I have another taste?"

"You devil! Of course you can have another kiss. You can have all the kisses that you want." I gave him his kiss and gave myself a sigh of relief. For a minute there, I had thought he was going to refuse. We were back on course.

We decided to go to a coffeehouse. I spent the evening lecturing on Girls-R-Us 101. I had decided to tone it down a bit from our previous dates. I had sensed earlier that he was showing a bit of resistance. I kept the lecture on a positive tone. We only discussed the good fashion styles we saw. And I spent more time asking about school and his classes and how he was acclimating himself to college life. The coffeehouse might not have been the best idea. At one point he took a sip from his glass and then set it down in front of himself. I could see that he was looking at the mark his lipstick had left on the glass. I reached over and wiped it off with my napkin. "Sweety, I promise you, no one can notice." He still didn't look too happy. "Would you like to go over to my house and watch some television on the couch?"

That seemed to work. "Yeah, I think that would be better."

It was about a fifteen minute walk to the car and the entire way he never said a word. I took his arm in mine and walked along next to him. I knew that sooner or later we would have our "Come to Jesus" meeting and I was afraid this might be the time. It was happening earlier in our relationship than I thought it would. I knew it would come one day, and I tried to rehearse it in my mind one more time, but I just couldn't concentrate. How was I going to answer him when he asked, "Why are you feminizing me?" I had the basic answers thought out, but it was going to be tricky. And then what should I do? I had this weekend planned out. I had made appointments with the beauty salon. Should I continue with the plan, modify it or scrap it and try to save the relationship? Just as we arrived at the car I decided that we would go forward with the planned weekend. If I was going to lose him, I might as well do it early so I could start looking for someone else as soon as possible.

I opened the car door and he silently climbed in. I thought I would try one more time to open him up. "Sweety, you're very quiet tonight. Is something wrong? Did I do something to upset you?"

It worked. "Oh no, it's not anything you did. I just didn't have a very good day … or week … or month for that matter."

"Let's talk about it. Can I help?"

"I thought going away to college was going to change everything. I had no friends at home and I have none here. I just don't belong here. This college thing doesn't seem to be working. It's no fun. I'm thinking about dropping out."

Oh my, oh my, oh my! What a relief. He was homesick, that was all. My plan to isolate him from other friends and boys was working better than I had thought. He obviously wasn't around on weekends to go out with the other kids in his dorm and bond, and now he was feeling alone. This was exactly what I had wanted to accomplish. It happened faster than I expected. But now I had to be careful. I didn't want him to drop out. Not yet. Eventually I needed him to leave school and move in with me, but not yet. He wasn't ready.

"How about me?" I asked. "Don't I count as a friend?" Laying a little guilt on him would help my position.

"Cynthia, you are the only good thing that has happened to me here. In fact, you're the best thing that has ever happened to me. I don't want to lose you. I'm just feeling down right now. Things just aren't going the way that I had hoped." He was very somber.

"Don't worry, you're going to make friends," I lied. "Some people just take longer than others. And usually, when you do make those friends, that friendship is much stronger and lasts much longer. Hang in there, it's going to get better." And much sooner than he thought. I was going to slip him half a Valium when we got back to my place.

We reached my house and I opened his door and let him out of the car. I walked him into the house and sat him down on the couch. "Do you like wine?"

"I've only had it once or twice, it's ok," he said. I left him on the couch and headed to the kitchen where I dropped half a Valium into his red wine. I had deliberately left him sitting on the couch. I had left the mail sitting there, and on top of the mail I had left a flyer from the Reproductive Fertility Center.

When I returned I gave him the wine and with a 'Cheers' I took a sip and sat down next to him. I picked up the flyer and said, "I guess they didn't know who was living here," and I handed it to him.

"I've seen this before. They sent them to the dorm."

"What do you think of it?" I probed.

"I don't know. It doesn't seem to apply to me. Who would ever want to use my sperm?" he said disconsolately.

"I might," I said. "But I think there are good reasons to consider it. It's kind of an insurance package. What would you do if you had an accident and couldn't have kids? I know that a lot of professional athletes store their sperm in case of an accident. Rodeo and football players do it. Some servicemen do it if they are heading to hazardous duty. You really should think about. I think it is a good idea. Just as insurance." And the seed was planted. Something for him to think about. I would continue bringing it up in the future until I had him convinced to store his sperm. It was an important part of my plan.

I turned on the television and we cuddled on the couch and made small talk for a while. It was starting to get late and it was time for his next step. "Instead of me giving you a ride back to your room, would you mind spending the night with me?" I asked. A cautionary smile crept over his lips. "Now don't get me wrong. This is not an invitation for sex. I need to know someone a lot longer before I take that step. You can sleep under the sheet and I'll sleep over the sheet. That way there is no temptation to step over the bounds." I paused for a just a second and then with my best seductive smile I added, "I would like you to stay."

He wasn't quite sure what to stay, but I knew he wanted to sleep over. "I suppose that would work. We'll be on opposite sides of the sheets, so I guess that's ok."

"Great! This will be fun," I said enthusiastically. "Let's get cleaned up then. Come on, I'll show you." And I led him to the bathroom. "Here is some Noxema, it's a makeup remover and moisturizer. You can clean your face with it. Would you please do me a favor though?" I asked.

"Ok," was his entire answer. He wasn't much of a talker.

"Would you please shave for me? I don't like beards or hairy men." The last thing he needed to do was shave. He barely had any peach fuzz on his upper lip. But this served to set the stage for later things, and it did stroke his ego.

Again, he shook his head yes and said, "Ok."

"When you're done shaving, here is a new toothbrush for you to use. And after you wash your pits, please use this deodorant, it's the same one you used last weekend. In the meantime I'll find you something to wear," and I headed out the door before he could say anything.

I went into my bedroom, turned down the bed, then picked up the long, lavender nightgown and the matching pair of tap pants. This was going to be fun I thought to myself. I stood outside the door until I thought he might be about finished. I knocked on the door and announced that I had his nightclothes. He opened the door and peaked out at me. I offered him the clothes. "You want me to wear these?" he asked incredulously.

"Yep. It's all I have. I think you will like the way they feel," I said. I gave him a big smile.

The Valium must have been working. He returned my smile and said, "Somehow this doesn't surprise me."

I went back into the bedroom and sat on the bed waiting for him. After a few minutes he came out. He had the straps crossed and he was looking very sheepish. I could tell that he had an erection. Bingo! Things were going as planned. "Come here, you have the straps crossed. Let me help you." I pulled the gown up high enough to get his arms out, corrected the direction of the straps and slid it back over his head. "There you go. You can have this side of the bed. I'll get cleaned up and be right back." I wanted him to have a few minutes to slide around in all that satin and enjoy it by himself.

I cleaned up and put on a pair of tap pants and a long black negligee that featured plenty of lace. "Are you all settled in?" I asked.

"I think so, I believe I'm under the sheets and I have laid out the top sheet on your side of the bed so you will be on top of it."

"Great, then out go the lights." I hit the light switch and made my way around to the other side of the bed. I climbed in, organized the blankets and sheets, and then slid over next to him. "Are you comfy?"

"Yeah. I just hope I don't slide out of the bed. These sheets and nightgown are really slippery."

"They're supposed to be," I told him. "It's one of the benefits of the softer side. And we call it a negligee, not nightgown," I corrected. I reached over and slid down his sheet. I gently rubbed his arm. "Does everything fit?"

"I think so. Every time I roll over this nightgown … I mean negligee, wraps its self around my legs and hips."

"You'll get used to it. It will become second nature to reach down and slide it around you back to the straight position." I then reached my hand over to his chest and gently massaged his chest. There was just the faintest bit of stubble where he had shaved his chest the previous weekend. "Sweety, would you do me a favor tomorrow?"

"Sure, what?"

"When you take your shower tomorrow morning, would you shave your chest and armpits. They're feeling stubbly, and I hate stubble. Would that be ok?" I pleaded.

"I guess I could."

"Thanks, and by the way, you smell wonderful. I leaned over and gave him a long lingering kiss, while I continued to massage his chest. "Sweet dreams."

We woke up the next morning at 8:00. "Good morning," I cooed. I rolled over to face him. "Did you sleep alright?" I leaned over to him and gave him a nice kiss.

He returned my kiss then complained, "I kept getting all tangled up in this negligee. It was frustrating,"

"What did you think of the satin sheets?"

"They felt nice, really smooth and silky. I could get used to this," he joked.

"I hope so," I answered. "Time to get up and get something to eat. I have a robe and slippers you can wear. Wait right here." I put on my robe and slippers and brought him his robe with the same fuzzy slippers that I was wearing.

We wandered down to the kitchen and had a leisure breakfast. I slipped him the other half of the Valium. I thought it would help lift his spirits. We had a long leisure breakfast. He helped me cook some eggs and nuke some bacon. We talked about school a little and I steered the discussion to friends. I tried to convince him that the quality of your friends is more important than the quantity. And I opened up my house to him a bit more. Up until now I had kept our relationship a weekend relationship. But now I told him that if he needed someone to talk to he could come over and visit me. I warned him that I did do some over night traveling, so he would have to call in advance.

After breakfast I offered to let him clean up first. I showed him the alpha-hydroxy facial cleanser, reminded him about the shampoo and crème rinse and made sure his toothbrush and deodorant were out and available. Then I gave him a kiss and reminded him to shave his chest and armpits. "While you're showering, I'll get you some clean underwear. Did you wear an undershirt?" The answer was affirmative. While he was finishing up, I pulled out some high cut cotton panties and the camisole with the cap sleeves. I added some thin, nylon socks to the pile and handed them to him when he was finished.

"More girly underwear?" he yelled through the door.

"It's all I have," I retorted.

"Do you want me to wear this undershirt also?"

"It is a camisole, and yes, put it on. You will like how it feels on your smooth chest. It's satin."

When he came out of the bathroom I asked him how he liked the feel of the camisole. "I have to admit, it does feel smooth. Is everything you own made out of satin?"

"Not everything, but I do like the finer things in life. I love softer, feminine clothes. It is one of the benefits of living on the softer side of life." I was trying to use the term 'softer side' as often as possible. I wanted Matt to associate this euphemism for feminine without having to say the word feminine. I thought it would make it easier for him to later accept some of his feminization, without the negative connotation associated with giving up his masculinity.

I took over the bathroom and completed my morning regimen. I asked him to return to my bedroom where I had him sit at my vanity. I had him apply the facial moisture that I handed him. I wanted him to get used to using this moisturizer each and every morning. Later it would contain his hormones. Then I took out my nude lipstick and gave it to him to apply to his lips. "Hopefully you will start remembering the lipstick that I bought for you. It is much better for moisturizing and protecting from UV rays than this brand. It is much higher quality." I was hoping that I could make him feel a little guilty about me spending that much money on him.

We walked out to the car and headed towards the beauty salon. "Where are we going?" he wanted to know.

"Well, first we're going to the beauty salon. I'm going to get a wash and set. Then I need to buy a new bra and some other under things. After that we can catch a bite to eat and maybe an afternoon matinee. Does that sound ok?"

"Do I need to go to the beauty salon with you? I could just wander around the mall while waiting for you," he suggested.

"The beauty salon isn't at the mall. It is off by itself. It won't take long," I lied. I was going to make sure that it took well over an hour. This was going to be his introduction to beauty salons. I wanted him to spend as much time as possible in the salon. I wanted him to smell the fragrances, the odors associated with permanent hair-set solutions, and the nail polish. I wanted him to sit there and see the women getting their hair washed and curled, their nails manicured and all of the comings and goings. I wanted him to leaf through Cosmopolitan and Glamour and hairstyle books. I wanted his senses totally inundated with the aura of a beauty salon.

When we arrived at the salon, I seated him as close as possible to the action and I made sure that he could see me. I handed him a couple of women's magazines before I walked off with Pamela. I gave Pamela my instructions and then walked over to the sink to have my hair washed and rinsed. I waved at Matt on the way over and the way back. Pamela took me to her station and began to comb out my hair and roll it. I was looking towards the mirror, but I could see Matt in the reflection. He was looking through his magazine, but I noticed him looking over in my direction several times. During the set I told Pamela that my boyfriend was thinking about growing his hair long. "When we finish, would you mind walking over and taking a quick look at his hair. Just let me know if there are any special hair care products that you would recommend, and if and when you might need to style it a little so that it could grow out without looking messy and out of control." Pamela agreed.

Pamela finished rolling up my hair and escorted me over to the hair dryer. I again smiled and waved at Matt. I spent about thirty minutes under the dryer before Pamela retrieved me. She removed the rollers and brushed out my style. It had taken a total of one hour and fifteen minutes. I was satisfied with the time. Pamela and I walked over to see Matt.

"Matt, this is Pamela. Pamela this is Matt." They shook hands. I looked at Matt, "I mentioned to Pamela that you might consider letting your hair grow out, and I asked her to take a quick look and see what she might recommend."

Before Matt could respond, Pamela asked him to turn around. Matt complied quietly. She looked through his locks and then turned him back around, facing towards her. "You have really nice hair, Matt. I don't see any split ends. It is in good condition. I think you would look really good with longer hair and the right style. I would suggest just letting it grow for now. Maybe in four to six weeks you could come back in and we could tidy it up a bit as it grows out. I would recommend buying a good quality rinse to make sure that you don't get split ends."

We said thanks, I paid the bill and gave Pamela a nice tip. Out to the car and off to the mall. On the way Matt commented on Pamela's inspection. "So, you think I should let my hair grow longer, do you?"

"I've said that before," I replied. "You have pretty hair and in a longer style I think you would look very attractive. At least think about it won't you? Please?" I gave him one of my cute smiles.

"Well, we will see. I have been thinking about it. How would I style it though? I don't know how to do that or what would look good."

"That's easy," I told him. "Just let Pamela handle everything. She is a professional and she can make the best decision." Left unsaid was the fact that she would be taking instructions from me. The beauty salon trip had gone very well I thought. Now it was time to introduce him to lingerie.

When we reached the mall I parked the car, opened his door and we walked arm in arm to Victoria's Secret. A saleslady stopped us and asked if she could be of help. I said I wanted to look into a different style of brassiere and said that I wanted to start from scratch. We walked to the back and she showed me through the different styles of bras she had. I made a point of asking Matt as many questions as I could. I wanted his opinion on everything. We checked out everything from under-wires to water bras. I chose a rear hook under wire and a front closure push-up bra for starters. The woman took me to the fitting room and I removed my sweater and bra. She measured me, then went back to the front of the shop to pick up the correct sizes. When she returned I started trying on the different styles. I kept Matt close by so that he could hear our conversation. A couple of times I called him into the fitting room to look at the bra and ask for his "professional" opinion.

I stalled the shopping session as long as I could. After picking out the right style and size, I led Matt around the store to look at panties and stockings. We left the store an hour later. Matt had been totally immersed in lingerie and feminine conversation.

We caught a bite to eat in the food court and then headed to the theater for the afternoon matinee. It was another chick movie. We had the theater almost to ourselves, so I whispered throughout the movie, commenting on hairstyles and fashions. Another 'Girls-R-Us 101' lecture. I don't know if he was getting totally sick of hearing all this fashion talk or if he was starting to succumb, but I kept pushing it on him.

After the movie we went to the local botanical garden and strolled around. We returned to my house at about 6:30. We were both a little tired from the walking so we decided to turn on the TV and spend the night in. We settled on popcorn and diet colas for dinner.

There wasn't much on the television, and I asked Matt if he would model for me. I wanted to try out some new poses and techniques that I had read about. He agreed and we headed towards the studio. I set up everything and took three or four shots. Then I went into the next stage of my weekend plan. "Matt, can I ask another favor? I know I impose on you a lot but I would really appreciate it." With that lead in, he was obligated to assure me that I did not impose too much upon him and to go ahead and ask whatever I would like. He was getting easier and easier to manipulate.

"Matt, you were so cute in your negligee last night, would you model it for me?" His face almost registered shock. I was definitely imposing now. I gave him my most pleading look.

"I don't know. I feel kind of funny about posing in women's clothes."

Now I was going to have to work with him. "No one will ever see the pictures except you and me. And I did like seeing you dressed in it. And when we finish with the pictures, you will already be dressed for bed. Would you stay the night with me again?" There, I had invited him to spend the night if he would dress for me. I thought that would be enough convincing and of course I was right.

"As long as we keep the pictures to ourselves, I guess it would be ok."

"Of course," I lied. If the pictures were any good, I would be sharing them with Valerie the next day. "Great, let's get you cleaned up and changed." I led him into the bathroom and told him to prepare like he was going to bed. Cleanse and moisturize his face, shave (for his ego again), brush his teeth and apply his anti-perspirant. I went and retrieved his tap pants, negligee and robe.

I didn't realize until later that the main reason he hesitated was because he knew he was going to have an erection, and it was going to stick out plain as day. He solved the problem for the most part, by leaving on his panties. Before we started the shoot I gave him a kiss in appreciation. We started with his robe on and we took a few pictures of him standing and sitting on the stool. After a few pictures I stopped and said that the pictures just didn't look right with him in his bare feet. "Wait here, I'll be right back." I went to my closet and took out the three-inch black heels I had bought last weekend. "Sit on the stool and I'll put these on you. When I bought these last weekend I didn't think you would be the first one to wear them." I had lied again. It was starting to become a habit, and I giggled to myself.

I deleted the pictures that I had taken already and began over. He looked much better wearing the heels. He had to hold on to the stool at first, while he acclimated himself to the heels, but since they were only three-inch heels it didn't take him long. He would have looked even better with a wig and makeup, but that would have to wait a couple more weeks. After a few pictures with him wearing his robe, I then asked him to drop the robe around his shoulders and give us a tease. A few more pictures and I had him drop the bottom of the robe to the floor and hold it by the collar behind him. We put him through a few more poses then removed the robe all together. With his freshly shaved chest and armpits, he had a smooth, girlish look. We took negligee pictures sitting and standing and a couple of pictures squatting on the floor. His figure was of course flat and about ten pounds too heavy, but I did see potential. I was looking forward to his development.

We finished with his modeling and then I went and changed into my negligee and robe. We put on our fuzzy slippers and sat down in front of the computer to look through the results. I was impressed with Matt's enthusiasm. He took the attitude of trying to compose the best possible picture and look his best. He was starting to think about his image and was slowly attempting to present a lithe and pretty form to his modeling, although I think it was only subconsciously. In one picture it was evident that he had an erection under his negligee. "You look a little pudgy in this picture," I said.

"Where, what do you mean?"

"Right here," and I pointed to his apparent erection.

"Well that is hardly my fault," he told me. "You put me in these sexy, slippery clothes, and then you prance around here looking as beautiful as an angel. What did you expect?"

"Touché!" I had to give him credit, he was starting to pick up on what I was doing to him. And he was climbing out of his shell. He deserved encouragement. "And right you are. I wanted you to enjoy these clothes, and I guess you are. I revel in the softer side of life and I was hoping you would too. But sweety, I am sorry but I have to put you off for a little while. I'm not ready to get too intimate yet. Can you wait?"

"Sure. I wasn't trying to push you into something you didn't want to do." He sounded apologetic, like it was all his fault. Things were going better and better I decided.

I took him to bed with the same rules as Friday night. We lay in bed and talked for a while. Then I gave him a final kiss and he rolled over, facing away from me. "There is something wrong about this," he said in a quiet but very serious tone.

"What do you mean?" I asked. I also tried to use a quiet, but serious tone to my voice.

"Me… lying here wearing a purple negligee."

I tried to use an upbeat tone, "It's lavender, actually. And you're wearing it because that is all I had to give you. You couldn't wear just your birthday suit."

"And posing for you while wearing women's clothing," he said. He still didn't roll over to face me.

"You were just doing me a favor. I asked for your help and you were generous enough to help me."

"And I helped you go through the pictures and pick out the sexiest ones."

"We weren't trying to pick out the sexiest pictures, we were trying to pick out the best. The best in composition and the best in lighting. I noticed the artist in you while we were doing it. You were just as interested as I was in trying to improve the quality of the photos. Picking out the sexiest was not the intention of either one of us."

"But guys just don't dress up in women's clothing. And the scariest part is that I like it. I like the soft, cool feeling of this negligee and these satin sheets. I shaved my chest hair and armpits. You don't see me trying to run away from you, do you? I really like being here, this way with you."

"Matt, you are simply enjoying the softer side of life. Unfortunately, society seems to have decided that the softer things in life should belong only to women, and these things should be labeled feminine. That's just not right. I love being a woman and some of the things that I enjoy the most are the soft things, the aromas and perfumes, the soft curly hair falling against my face, having soft skin and feeling soft fabrics as they brush and rub against that skin. There is no reason in the world that men shouldn't be able to enjoy the sensual and soft side of life. Society shouldn't force you to have to forgo the luxuries of life. It isn't fair.

"And the reason that you shaved your chest and armpit hair is because I asked you. You did that for me because you are unselfish. The reason that I asked you to do it is because I am selfish. Like I said, I truly love the softer side of life. I don't care for hairy men with scratchy beards, or more hair on their body than a gorilla. I don't want to cuddle with a man with hard, coarse skin that is full of calluses. I want to share the softer side of life with my man, and I want him to be able to enjoy and appreciate it also. I want you to enjoy the luxuries of life. That is why I asked you to do it for me. I hope you can understand that," I pleaded.

He rolled over to face me. "I think I do. I do feel better now. Thanks." He leaned over to me and gave me a kiss.

I rolled onto my back and stared at the ceiling. I think we just had our Come-To-Jesus talk, I thought. And I think I am starting to like this man, more and more.

"Sweety, one more thing. I'm not ready to get intimate yet. Not yet, but I think that day will come. And if we do get intimate, we owe each other something. I trust you and I hope that you trust me, but in this age of AIDS we should prove our own trust by getting check-ups and sharing those results. Nothing hidden. The entire report and results. It usually takes a couple of weeks to schedule check-ups and get the results. If we did this now, when we are ready for taking our relationship to the next level we won't have to wait. Would you be willing to get a blood test to check for AIDS, and the other things?"

He didn't hesitate for a moment. "Yes," came immediately from the other side of the bed. I fell asleep with a smile in my heart.

 

Chapter 4

Transcripts from conversations with Melissa Ann May

I had had one of the worst weeks of my life. I was miserable. I had come to the conclusion that after 4 weeks at this place, I had no friends. I was studying by myself and I was eating by myself. The guys on the floor rarely asked me to join them for a game of baskets or to walk together over to the cafeteria for dinner. I was starting to think that this whole college thing was a mistake. Life was no different than before, just the location had changed.

Then the weekend came. I met up with Cynthia and had probably the best weekend of my life. It was weird though. I wasn't sure what was really going on between us. When she asked me to sleep over I couldn't believe it. It was great! I had to wear a negligee, which worried me at first. But I ended up enjoying the comfort and feel. Saturday morning was spent at the beauty parlor and shopping for a bra. Some of it was sexy and fun, but mostly I was bored. Saturday night I stayed with Cynthia again, and again I wore her negligee. I was starting to get used to having it wrap around me during the night. I stayed for breakfast Sunday morning, then Cynthia gave me a ride back to the dorm for the rest of Sunday. I cleaned up my remaining homework and watched a bit of TV on Jeff's set.

The rest of the week was about the same as the previous week, but it didn't bother me as much. I called Cynthia in the evenings and we talked for a bit. It was good just to hear her voice. We made arrangements for me to ride my bike over to her house Friday night and meet up for a 6:00 dinner. She called out for chicken and we made a salad to go along with the chicken. I cleaned the dishes and she went in to the living room to wait for me.

When I had finished in the kitchen, I joined Cynthia on the couch. She immediately handed me a new flyer from the Reproductive Fertility Center and asked if I had given it any more thought. I hadn't, it still didn't seem to make much sense to me. "I really think you should consider this," she told me. "In fact, I am so convinced that I will pay the first year's bill. I'll write a check tonight if you will agree to go over there this week and make a deposit."

"But I still don't see why," I said. "I'm no athlete. And I'm not heading off to war."

"But accidents do happen; auto accidents, bike accidents. The world will surprise you and this is just cheap insurance. Please?" She gave me those big sad eyes and I couldn't resist. Plus, it was only going to cost me some time, nothing else.

"I give in, I'll do it."

"Good. Now there is one tiny catch." I rolled my eyes in a mocking manner. "When you fill out the paperwork, I want you to list me as a recipient." She looked very serious.

"I can do that?"

"Yes, it's easy. And you can use my address here if you want. It would probably be easier than using a dorm room as your address."

I agreed to everything. She left the room and went to her office. She brought back a check attached to a registration form. I took the form and commented, "You really planned this out, didn't you?"

"Sweety, the more I thought about it, the more sense it made to me. I do like to plan for the future. I tend to be pretty conservative in my finances and insurance ideas. Now that that is settled, I thought I would open up to you and show you a little bit of my childhood." She reached over to the table and pulled a large scrapbook onto her lap. We squeezed together and she started a narrative of 'Cynthia – The Early Years'.

We spent almost an hour and a half going through her scrapbook, looking at photos and bits of souvenirs from school plays and activities. It was rather interesting and we had a few good laughs over some of the pictures. We especially laughed and joked about her Halloween costumes.

When we finished she put the book down and got us both a small glass of red wine. I had never really drunk alcohol before last weekend, and I still didn't care very much for it. I sipped the wine, and just a small amount warmed me up.

"Do you know what the date is today?" she asked.

"Ah, September 28, I believe."

"Right. And do you know what the next month coming up is?"

"October …?" I said, feeling I was being baited along for some purpose.

"And do you know what happens in October?"

"Let me just take a wild guess; Halloween?"

"Bingo," she yelled. "Give the man a cigar. And guess what is my favorite holiday of the whole, wide year," she challenged.

"Well, that would have to be another Halloween, I do believe."

"Bingo again! I love Halloween. Could you tell by my scrapbook?" I nodded my head and took a sip of wine. I wasn't sure where this was going, but Cynthia was enthused about it. "This is going to be my first Halloween since moving away from home and college. I really love dressing up for it, and it is so much better if you have someone dressing up with you. Someone you can share it all with. Do you think you might know someone who would enjoy sharing Halloween with me?" She leaned over close to me and batted her eyelashes as she looked me in the eyes and asked her question.

I was going to play along. "I'm not sure," I answered. "I could look around and see if I could find someone. What is it worth to you?""

"Oh, I don't know," and she tried to give me a far away, thinking look. "Let's see, I would supply the costumes and makeup. There would be no, well almost no, out of pocket expenses for this favor. And there might be a special reward for the right person. Something that would definitely bring a smile to someone's face."

"Well, in that case, I might consider offering my services."

"Would you? Thanks, thanks, thanks. This really does mean a lot to me. I've even started looking ahead at calendars to see where there are going to be costume parties. I love to get all dolled up for Halloween. But be forewarned, I do take this serious. I go all out for Halloween. Some of our costumes may be rather elaborate."

"Such as …?" I asked.

"I'm not sure yet. Sometimes I wander through consignment shops and second hand stores looking for cheap clothes and ideas. We would have to do some shopping, which as you know is one of my other favorite past times. But we'll do a couple of costumes. There will be parties, probably three or four or, if we are lucky, maybe five nights, and we will do different costumes for each night."

"You do get a little elaborate, don't you? Do you have any ideas or thoughts what we might go as?"

"Well, there are the old standbys such as a witch, or French maid, or princess or queen. We could go as cowgirls, or cheerleaders. It's really easy to go to a costume store and pick up something, but that is kind of cheating. I like to try and do it all by myself. One year Valerie and I went as Bavarian beer hall girls. That was an easy costume. Or we could try going as a celebrity like Marilyn Monroe or Madonna or Cher, even." She just started gushing with enthusiasm as she started talking about costumes.

"And what about me?" I asked. "Any ideas for me?"

"What do you mean, any ideas for you? These are ideas for both of us. We would go together with the same costumes. It makes it twice the fun."

My mouth fell open and I just looked at her. "You want me to dress up in female costumes?" I asked.

"Yes. Please don't change your mind, it will be tons of fun. I promise. I guarantee you will like it. Have I steered you wrong yet?" She was pumped so full of energy that there was no way she would take no for an answer.

"But I'll look like a fool. Someone I know might see me." I was trying to think of rational excuses, but I knew I was going to lose.

"No one, and I me no one, will recognize you. And you will not look foolish. When I'm done with you, you will look fantastic. I seriously doubt that anyone will be able to tell you are even a guy. I've been thinking about this, and I'm sure I can make you look perfect."

"You've been thinking about this? How long?" I wanted to know.

"Well, you know how much I like Halloween. I've been working on ideas since last Sunday."

"And what kind of ideas have you come up with?"

"I just told you some of the ideas for costumes. For you though, we will have to do some extra work with foundation undergarments and wigs. Makeup will also be a problem because of your beard, but I've got an idea there also. For your beard we will go to one of those theater shops and pick up what they call beard cover. It is heavy makeup designed to be used on stage under the glare of bright lights. So, I think it will work fine in a dimly lit club or street. For undergarments we will buy you a corset to shrink your waist. They have padded underpants that can give you a fatter butt and hips. And of course we will have to get you a bra. You can try them on and we will see what works and what doesn't. I'm sure that by the time we get you dressed, you will be very convincing."

"I'm doomed," I laughed.

"No you're not! You'll love it, I promise." Cynthia gave me a huge hug and a long kiss. "Thanks," she whispered in my ear. "Now, would you like to get ready for bed? Same rules as last week."

"That sounds like a good idea." I headed off to the bathroom, where once again Cynthia showed me where the moisturizer, razor, toothbrush and anti-perspirant were located. She had set aside a permanent location in the medicine cabinet for my things. I started to clean up and she went to get me my negligee. I shaved my chest and armpits for her, along with my face. A few minutes later she knocked on the door. I opened the door a crack, reached out and she put the negligee in my hand. I pulled the clothes into the bathroom, closed the door and let out a yell. "What is this?" The negligee and bikini panties were bright red and half the size of last week's negligee.

"I'm sorry," she yelled back through the door. "I didn't have time to wash your lavender set. Besides, you said that you were getting all wrapped up in the lavender outfit. You shouldn't have that problem with this negligee."

"You can say that again," I replied. I finished dressing and walked out into the hall. She was standing there looking at me and smiling.

"Wow, you are hot," she cooed. "And it looks like your getting a little pudgy, too."

"I can't help it," I complained. "I'm not exactly proud of my self control."

She walked over to me and gave me a tight hug, grinding her hips against my bulge. "I'm honored that you think enough of me to get excited. And don't be sorry. It's part of life. In fact it's one of the better parts of life. Climb into bed and I'll join you as soon as I clean up and change."

I had a difficult time sleeping that night. The satin sheets, the bikini panties and negligee just felt too wonderful. I spent the night trying to hide my erection from Cynthia.

The next morning we awoke and cuddled in bed for a while. "Wait here and I'll get your robe," she said as she hopped out of bed and headed towards her closet. She brought out a red, knee length robe that matched my negligee. Needless to say, it also was satin.

We had a leisurely breakfast and I cleaned up when we were done. While I was clearing the table, Cynthia went to the bathroom and completed her morning toiletry. I followed after she was finished. After cleaning up, Cynthia handed me clean panties, camisole and socks. She asked me if I had my lipstick. "I have a confession to make," I said. "I couldn't take a chance on my roommate finding it, so I hid it in the glove compartment of your car."

"I understand," she replied. "Here, put on this moisturizer, and when we get in the car you can use the vanity mirror to apply your lipstick. In the future I'll carry it in my purse for you and you can wear it on the weekends. The car isn't a good place to leave it, because on a warm day it may melt."

We finished up and headed to the car. She was carrying a small bag with looped handles, along with her purse. "What are we doing today?" I asked.

"I have an appointment at the beauty salon to get my legs waxed. Would you like to join me?" She was smiling, but I don't think she was joking.

"If I walked into the shower back in the dorm with my legs shaved, I'd be killed. I would never live down the humiliation. It's tough enough hiding my bare armpits. I have to walk around like a mummy with my arms planted against my sides."

"Not surprising," she said just as we reached the car. She unlocked the passenger door and I sat down. After she climbed behind the wheel and started the car, she continued, "Don't forget your lipstick. After the beauty salon, we're going shopping to get a bra for you."

"What?" I screeched. "You can't be serious!"

She started laughing and told me, "Relax. It's for your Halloween costumes, and we're not going to Victoria's Secret. I called a small shop that specializes in women's undergarments and made an appointment for today. The owner will close the shop, and we will be the only ones there."

"When did you make an appointment?" I wanted to know.

"Monday."

"Monday? We didn't even discuss this until last night."

She smiled and glanced over at me, "I know."

"You sure take me for granted," and I gave her my best pout.

"Oh no, dear. Trust me, I never take you for granted."

We reached the beauty salon and she dropped me off in the waiting area. The smells were wonderful. I especially liked the smell of the solutions used for hair permanents. I flipped through women's magazines for almost an hour before she returned. She paid her bill, made her next appointment and we left.

It was getting close to noon when we parked at Sofia's House of Glamour. Cynthia picked up her purse and small bag, then walked around the car and opened my door. I walked up to the shop with a lot of apprehension. We walked in the door and headed towards the sales counter located near the back.

A woman of about 40 greeted us. "Hi, I'm Sophia. Might you be Cynthia and Matt?"

"Yes we are," said Cynthia, and the three of us shook hands.

"Well let's get started, shall we?" Sophia walked to the front of the store, closed and locked the front door. She turned around the closed/open sign and pulled down a curtain over the window in the door. She walked back to us and looked at Cynthia, "Did you bring your items?"

"Right here," announced Cynthia as she held up the bag.

"Good, why don't you two go back to the fitting room and get ready. I'll wait here and finish up the morning's paper work."

Cynthia and I found our way back to the fitting room and entered. It had a small bench, a few hooks to hang clothes and a large floor length mirror. Cynthia pulled the contents from the bag. They looked like a thong and pantyhose. "Strip down and put on this gaff," which she was holding up for me to see. "I bought it at a dance studio. It holds your penis back between your legs and gives you a smooth looking crotch and frontal view. To fully protect your testicles, you push them up into your body before pulling up the gaff. Then put your panties back on and I'll come show you how to put on your hose."

In the loudest whisper I could muster, I yelled, "I do what to my testicles?"

"He said it would be a bit funny feeling at first, but you get used to it quickly. There is no pain involved."

"That's what he told you. You don't have to do it!" I was starting to panic.

"Here is what he said; you lay your scrotum and penis in the palm of your hand, then slowly close your hand, fist-like, from the end of your penis towards your body. You slowly push the testicles along as you close your hand, and they slide up into the body. You will feel only a momentary fullness, then it is gone. That's what he said."

"Easy for you to say. You wouldn't mind performing the operation would you?"

I actually got a laugh out of her. "I might hurt you, I don't know my own strength."

She left and I followed her instructions. I had to try it several times, but I finally did it. The guy at the dance studio was right, it didn't hurt and once the gaff was holding them in place I felt almost nothing. I guess you learn something everyday – even if it is totally weird.

I called her back when I was ready. I was standing in the fitting room with just the gaff, panties and my camisole on. "How did it go?" she asked. "Is everything ok?"

"Actually, yes. It went ok after I figured out how to do it. It feels a bit weird, but actually I don't notice it much at all."

"That's a relief. I was concerned when he told me about it. Ok, sit down on the bench." I did as I was told. "These are dancing tights. They are just like panty hose, but they are not as sheer. They will hide your leg hair. You hold the panty end and using both hands you pull the leg into a bunch like this." I watched as she rolled up the leg in her two hands. Next, you insert your foot, go ahead, and you pull up the leg to about your calf. That's right. Now, roll up the other leg and insert your foot in that leg." Again I did as I was told. "Now take turns from leg to leg and work the panties up both legs. Stand. Pull them up tight over you waist. Excellent. You can take off the camisole, you won't need it right now," and she then led me from the fitting room. She called out to Sophia, "We're all set, now."

Sophia came out from behind the counter and stopped to look at me. "Turn around please," and she used a rotation of her hand to show me what she wanted. "You have a lot of potential. Mind you, it wouldn't hurt to drop 5 or 10 pounds around your waist, but your size and stature will be very conducive to the look we will be trying to achieve. I think your upper body will be fine as is. If you will follow me, we will start over here with a corset."

We followed her over into one corner of the store. The area was filled with what looked like biking shorts, girdles and some tight fitting garments. She pointed to a group and looked over towards Cynthia, "These are our corsets. The first step to a flattering figure is a small waist. It adds dimension to the feminine curves that we want to achieve, and it will make the bust and hips look more pronounced. Now, do you want a corset with garters?"

"I think so," said Cynthia. "In your opinion, can we pull black stockings over these dancing tights?" Sophia answered yes. "Ok then we want garters, but can they be detachable for when we don't use them?"

"Absolutely," said Sophia. "I would recommend one of these sturdier corsets, here. They have front hooks, back lacing and are very durable. The goal is to take three to five inches off the waist. Six inches will be very tight, so it depends on the person wearing it. Let's get your waist size Matt, and then try one of these on."

Sophia pulled a fabric ruler from her pocket, wrapped it around my waist and announced that I was 29 and one-half inch. She opened a cupboard under the displays and after a bit of searching pulled out a box and opened it.

"Let's try this one. Our goal should be to get you down to 24 or 26 inches. I think that will fit nicely with your stature and body size. Let me show you how to use this. The back is already laced up, so all you have to do is open the laces as wide as they will go, and wrap it around your waist with the hooks in front." She wrapped it around me while I held my arms up out of the way. "You want it to be close, but not tight, when the laces are open as they are now. This looks fine. Here Matt, you start at the top and hook all of the clasps."

A small ball on one side fit into a hole in the clasp in the other side, then pulled into a narrowing of the hole that held the ball tight. I hooked the clasps from top to bottom.

Sophia took the corset and slid it up on me. "For a woman you want the corset lower, to pull in the waist right over the hips. But on a man, you have the problem with the ribs coming down lower, so we pull the corset up onto the bottom of the ribs to hold them and give a smoother contour into the waist. Ok?" Cynthia and I both shook our heads yes. "Good. Now Matt, turn around and face the other way. Cynthia, you have to grab the laces in the middle of the corset, here and here." I could feel Cynthia grab them. "Now pull tight. Matt, exhale and suck in your stomach. Cynthia, pull." I could feel the corset pull in tight around my waist. " Ok, that's a start, but you are going to want to cinch it tighter than that. Matt, ready? Exhale. Cynthia, pull again."

This time the corset pulled very tight. It was very constricting. "I can barely breathe," I whispered.

"Don't worry," Sophia assured me. "It will take some time to get used to this but you will. Take short, shallow breaths, and don't try anything too exerting. I strongly suggest you wear this corset around the house, and under your clothing when you go out. It will take some time to get used to it, and the more practice you have the better off you will be when you go out to your parties." She turned her attention to Cynthia. Now take the loops that you have in each hand and tie them together in a knot. Don't worry about getting them untied later. The larger diameter cord that we use will easily untie." I could feel Cynthia tying off the cords. "Ok, Matt how does that feel? Walk around a bit."

I tried to walk. It was difficult. I could barley breath, and the constricting fit made it difficult to bend over. In fact I couldn't bend over at all. Sophia must have noticed.

"If you are alone, you will probably want to put your shoes on before your corset. You will find it very difficult to bend over if you pull the corset properly tight. But you will also notice the excellent posture it gives you. You will stand and sit much more straight. Now then, let's re-measure you and see what we have." This time my waist was 26 inches. "You can probably get it down a little smaller, but after looking at you I think 26 inches will look nice. You will have a pretty figure."

Sophia took Cynthia by the arm and pulled her about ten feet away from me. "Matt, would you turn around where you are standing, please?" I did as I was told. Sophia started talking to Cynthia, while they both looked at me. "Look at Matt's waist and hips." Matt, please turn sideways to us. "We're looking at the relationship between his waist, hips and butt. Frankly, I think he looks thin, like a young teenager. He certainly does not look full hipped like a woman in her mid twenties. The look is up to you, what ever you prefer. We do have girdles with hip padding, and hip and butt padding together, and we have panties with hip padding. The girdles will provide the most padding. It comes down to what age you would like Matt to look. If you want to give him a young, teenage look, I would stay right where you are."

Cynthia looked over at me. "What age do you want to be? Teen or twenty?"

"I don't know," I said. "I would think that staying closer to my real age makes things easier."

"Can't argue with that," Sophia said. "And I do think he will look better with a slim, and younger looking figure. I think it will look sexy."

"I agree," said Cynthia. "Ok, what's next?"

Sophia looked at me, waved her hand to follow and said, "We can skip the hip padding then. Matt, you need a bra and some boobs."

That got a chuckle out of me. "Boobs are good, I like boobs."

We walked over to another corner of the store. Sophia started to point out different style bras. Underwire, push-up, running, padded, water bras, long-lines, front closure, rear closure, nursing (I don't think you will need one of those she quipped) and the list went on. In one ear and out the other. Cynthia started asking if I had any preferences. I was too ignorant to offer any. I thought front closure would be easier than back, but she told me that I could hook them both in front, then spin the back closure around and slide the straps over my arms. In the end, nothing mattered to me. So in the end we tried on, what seemed to me, all of them.

First, Sophia measured me at several locations around the chest and pronounced me a 34, AAA. "Triple A, I guess I'll have to start doing my exercises," I laughed. As strange as all of this was, I felt comfortable with these two women and I had decided to go along with everything in the spirit of Halloween and fun.

"Don't worry about that," Sophia said with a large smile. "We can make you any size that you want." We started trying on bras. Bra after bra after bra. After trying on about two dozen bras, the two of them seemed somewhat satisfied. Sophia turned to Cynthia, "B ok or do you want something bigger?"

"Since we decided to keep Matt's figure teen size, I think a smaller bust size would be better. But it's really up to Matt. He should get what he wants. Matt, do you want to be small, medium or large?"

"Speaking as a guy, bigger is better," and I tried to give them a lecherous look. "But, it should probably be correct with age. Proportionate would be more realistic, wouldn't it?"

"I agree," said Sophia. "Everybody agree with B?" Everyone agreed. "Ok, you have a B on, so walk this way." We stopped at a glass-topped counter full of silicone boobs. "We have a wide array of silicone breasts," she said. "Do either of you have any preferences?" Neither of us said a word. "First, since this is only for a costume, I wouldn't recommend anything too expensive."

Cynthia interrupted her, "I don't want to pay a fortune, but please make sure that we have a realistic look and feel. I don't want him to look fake."

"Understood. Then let's start with a full form. It will fill the bra from under the arm to the front. That is what we recommend for our full mastectomy patients. It gives the fullest and most realistic profile."

Sophia walked behind the counter and searched underneath for a minute. She brought the boxes around to the front and opened them. "Now these come with an attachable nipple. You use a bit of natural latex to attach them. Some women never use them, and some like to use them with certain bras in special circumstances." She pulled open the top of my left bra cup and slid the breast form in. It felt cold. She pushed it around for a couple of seconds to put it into the correct position. Then she did the same with the right form. "They feel cool now, but in about ten minutes they will warm up to your body temperature. How do they feel?"

"Kind of big," I said. I shook them sideways and up and down to get the feel for them. "They don't jiggle as much as I thought they would."

"That's because your brassier is holding them in place. With a properly fitted bra, your boobs shouldn't jiggle all over. But if you want them to jiggle, these breast forms are made to be glued to your skin. The glue is very strong and will hold for a week or more, depending on how much you sweat. They can even be worn in a shower. When glued to your skin, you don't have to wear a bra, although it is still recommended. You don't want one to come un-glued at the wrong time. But when applied with glue and without a bra, they will jiggle to your little heart's content."

"Matt, there is a full length mirror over there, why don't you take a look and see what you think. Cynthia, let's you and me step back and get an overall view of Matt's figure."

I looked in the mirror. All I could see was me standing there wearing a bra, corset and pantyhose. I certainly didn't think I had a girlish figure. Granted, my waist was much smaller but it just didn't look like anything else. I mentioned this to Cynthia.

"Don't worry, with the right clothes your figure will be stunning. Speaking of which," and she turned to Sophia, "we will need a couple of slips. A medium length one about knee-length, and a longer one mid-calf. White for the longer slip, black for the shorter one."

Sophia led us over to another area and took out a long, white slip and held it up in front of me. "Try this on honey," she said. Now I was a honey. She slipped it over my head and pulled it into place. She adjusted my shoulder straps then stepped back to admire her work. "Look in the mirror Matt, and see if that makes your figure look better."

I looked and I had to admit that my figure did look smoother and a little curvy.

"You will look even better with a dress having a fitted waist. That will show off your tiny waist and give your hips and top much more shape. I think that one will fit. Let's take it off and try on the black one."

We finished with the slips and Sophia asked Cynthia if there was anything else we needed. "Stockings, tan and black with a back seam." Sophia went to a rack and pulled out two packages of each and carried them and the slips over to the counter.

"Anything else?"

"We will need a black bra, same style and size, and panties." We walked over to the racks holding panties.

"What style?" Sophia asked Cynthia.

"White, cotton, high hip cut, and also some bikini." That raised my eyebrows. I cleared my throat and looked at Cynthia. "Don't worry, after you get used to them you will love them. Wait till we get to thong underwear," and she grinned. Turning back to Sophia, "Size five please. I think six of each will work." Sophia picked out the right panties and carried them over to the counter.

"Will that be all?"

"I think so. That should break the bank."

"Great, I guess we're done. Matt I guess you can go change now, but I recommend that you spend as much time as possible getting used to your new foundations. It will be difficult at first to keep from pulling and tugging and squirming. You don't want to do that when you go out in public, so the more accustomed you get before hand the better off you will be."

I started walking back to the fitting room, but Cynthia grabbed my arm and walked with me. "Matt, if you would please, would you leave the panty hose, bra and corset on? I agree with Sophia, it is going to take time to become acclimated to these garments, especially getting into and out of cars and sitting. Is that ok with you?" I agreed. "If you would then, hand me your breast forms and I'll put them back in their boxes. When you're not wearing them, they should stay in their special boxes to help them retain their shape." I pulled out the breast forms and handed them to her. "Thanks, I'll go pay the bill and come back to get you."

I went into the dressing room, and tried to put on my socks. Bending over while wearing the corset was almost impossible, but I eventually managed. Then I put on my pants, but they were way too big around the waist. The corset had shrunk my waist below the capability of my belt. There were not enough holes in my belt to be able to hold up my pants. I put on my shirt and shoes. When I looked in the mirror I could see the outlines of my bra, especially the straps. I stepped into my shoes and put on my jacket and walked out to the front counter.

As I walked up to the counter, the girls saw me and started laughing. "I guess those pants are a little too big for you now," Cynthia snorted and kept laughing.

"Just a bit," I said.

"Don't worry, we will stop at the mall and get you some new ones," she said.

I walked over to the counter just as I saw her hand Sophia a check. It was for $450. I couldn't believe my eyes. Cynthia finished up and picked up our packages. I took the packages from her and she walked me to the car. After I got in I looked at Cynthia and asked her how much she had paid for everything. "Not much," she replied.

"I saw your check," I said. "It was for over $400 dollars. You can't spend that much on a costume for me. I'll pay you back." I didn't know how I was going to pay her back. That was just an obscene amount of money for a Halloween costume.

She glanced over at me as she continued driving, "No you won't. I'm the one who asked you to dress up with me, I'm the one who picked out, excuse me, I should say helped pick out the clothes and I am the one who will pay for it. Don't worry about it. You weren't supposed to see the prices."

"But I did. You shouldn't spend that much of your hard earned money on me."

"Well, you just hit the nail on the head. It is my money and I can spend it as I see fit. And I would like nothing more than to spend that money on my boyfriend." And her tone of voice indicated that the conversation was finished. I remained silent.

"Let's stop by the mall and I'll get you a new pair of pants."

"I think I need more than that," I added. "You can see my bra outline and especially the straps."

"No problem, we will look for a large oversize sweater to help cover you."

"And one other thing. I insist on buying these," I said. "Please."

She looked over at me and smiled. "That would be fine."

We walked into J. C. Penny and she led me over to the misses department. "We're in the girls department, shouldn't we be in the men's area?" I asked.

"Nope. With those under garments, you now have a girl's figure. So we are right where we belong." It made sense to me. Cynthia went poking through the department and I followed around. We stopped once or twice for her to hold some jeans up to my waist. She asked what my inseam was and I said, "26 inches. It depends on the jeans also." She picked up three pairs of jeans and gave them to me to carry.

I then followed her over to the sweaters. She looked through the sweaters and must have held ten different types and colors up to me. She picked out three sweaters and carried them while I followed her to the fitting room.

"Empty your pockets, I'll put everything in my purse." After following her instructions, she gave me back the three pairs of jeans and sent me into the fitting room. "I want you to come out and show me each pair." Again, I did as I was told. The jeans were two-pocket style. No pockets in the back, which meant no place for my wallet. "You won't need a pocket for your wallet. It ruins the look and curves. Most of the time when you are wearing these jeans you will be carrying a purse." Each time I stepped out, she tugged at the waist, checked to see how tight they were, told me to twirl around a couple of times and then passed judgement. "This pair is the best. Put them back on, and we'll see how the sweaters go with them."

We went through the same routine with the sweaters. The sweaters she checked not only for fit, but also for bra coverage. She pronounced her favorite and asked for mine. I told her that I trusted her opinion implicitly. "You can leave them on. We'll have the clerk cut the tags off at the register."

At the register I paid $45.00. I was worried the sales clerk might say something about me wearing girl's clothes, but she never did. She placed my old clothes in the bag and we left.

It was pushing 4:00 in the afternoon and I was starting to get hungry. We hadn't had any lunch. Cynthia suggested salads in the food court.

"Do you mind salad? I think Sophia was right. You would look much better if you dropped five or ten pounds.

"A salad is alright," I said, "but I have already lost five pounds since we started dating. I don't eat bread or fries anymore and I am probably now at the lowest I've been in over two years."

"That's great, Sweetie. But it doesn't hurt to always watch your weight. Losing a couple more pounds really would make you look better."

We had our salads and then decided to do some more shopping. "You're going to need some shoes," Cynthia started. "Since we don't know for sure what our costumes will be, let's just get you generic loafers today."

We headed to Shoemart and began looking around. I tried on a couple different pairs, and we settled on some black loafers with one and ½ inch heels. Cynthia also asked me to try on different styles of shoes with higher heels. She asked me to walk in them to see if I felt comfortable. She said she was trying to get an idea about what I could wear, so she could take it into account when we went costume shopping. I felt like a fool. There was one female clerk in the store and I know she kept watching me. I felt very uncomfortable. I was glad to pay and leave.

It was pushing 6:00 and we decided to pick up a movie and head home. We chose Lord of the Rings, Fellowship of the Ring.

When we returned to Cynthia's, she wasn't ready to watch the movie immediately. She went into the kitchen and brought out half a glass of red wine for me and a full glass for herself. "Matt, thank you so much for going along with me today. I know you felt awkward at times, and I know it wasn't always fun. So, I just want you to know how much I appreciate you agreeing to Halloween with me. Now I know you are probably getting tired of wearing that corset, so before we watch the movie I would suggest that we change into our negligees and robes to get a bit more comfortable. How does that sound to you?"

"Music to my ears. Almost as good as Beethoven," I answered.

'Great," she said, and led me to the bedroom. "I've cleared a drawer in my dresser for your things. We can put your camisole, panties and everything in here. I've also cleared a small portion of my closet for your sweater, robes and negligees. Do you need a hand taking off your corset?"

"Please," I begged. I stripped down to my pantyhose. Cynthia handed me my satin panties, negligee and robe and sent me off to the bathroom. When I returned, she had all of my new clothes folded and placed into the drawer. She handed me my fuzzy slippers and headed off to the bathroom.

When she came out we hugged and kissed for a bit, and then she asked for one more favor before the movie. "Would you take my picture?"

"Why?" I wanted to know.

"Because I think you have the eye and talent for composition. I would like to see what hidden talents you might have. Secondly, if you can come up with some better angles and shots, I can steal them from you. Pretty selfish, huh?"

"Normally I would agree with you, but I saw you spend a lot of unselfish money today. And you know, I have kind of wanted to be the one behind the camera. Let's give it a try."

Cynthia gave me a quick review of how to handle the camera. I had watched her use it for several weeks now, so it really wasn't a challenge. I posed her for almost an hour before I realized how much time had passed.

"Before we check these out, do you mind if I take a few of you really quick?" she asked. So I ended up posing in my red outfit for another half-hour. When she finished she gave me an option; we could either proof our pictures or watch the movie. I opted for the movie, knowing that it was a long movie and it was going to be late when we finished. We went to bed after midnight.

Sunday morning after breakfast, I cleaned up and prepared to head back to the books. "Before you leave, there is something I would like to show you," she announced. She led me to the bathroom and explained that it was time to learn how to wash my own dainties. We filled up the bathroom sink with lukewarm water and a mild detergent. Cynthia started with the pantyhose and whites, camisole and panties. I was shown how to gently scrub them, rinse them several times, and then hang them over a line in the bathtub. Then I rinsed out the sink and started over with the lavender negligee and tap pants from the previous week. After hanging those on the line, I was finally instructed to wash the red negligee and panties that I had worn the previous two nights. I hung those on the line and rinsed out the sink.

I'll put them away for you when they dry," Cynthia said. "And before you go, there is one last thing that we need to do." She led me to her vanity and had me sit down. "Place your hands on the vanity, palm down. You will need to let your nails grow longer for Halloween. Men's nails aren't very strong, so I'm going to give them a coat of nail hardener."

I pulled my hands away. "I can't go around with nail polish on," I said.

"Put your hands back," and she actually picked up one of my hands and placed it back on her vanity. "I'm not coloring your nails, I'm applying a clear hardener to prevent them from splitting and chipping. The hardener is clear and no one will notice."

"But people will notice my long fingernails," I protested.

"Maybe, but I doubt it. I don't think we have enough time for your nails to grow to a noticeable length. We only have a couple of weeks. At best, when we apply polish at Halloween, they will look to be a short to medium length for a woman." And that is how I started growing my nails long.

 

Chapter 5

Excerpts from Cynthia L. May's Diary

On Sunday the 21^st, after Matt had left, I called Valerie. We spent hours on the phone. She wanted to see the latest pictures of Matt in his lavender negligee. I e-mailed her all of the pictures, and together we picked out the six best that I put in my special folder for printing later. I invited Valerie to come visit and meet Matt. We decided on three weeks later, the weekend of Saturday, October 12.

"Would you please bring your birth certificate with you?" I asked.

"Why? What do you have in mind?"

"I need an ID for Matt, so that he can get into the bars at Halloween. He isn't twenty-one yet."

Valerie's voice went up an octave and she squealed, "Have you already talked him into cross-dressing?"

"Not yet, but next weekend I will. It will take about two weeks to get him ready. By then I'll know what kind of wig, color and styling he will be wearing. I'd like you to wear his wig and get a legal photo ID so he can use it for getting into the bars. No one else will ever have to know. Will you do it?"

Valerie agreed to help, but it wasn't quite that easy. I had to make a few more concessions to her. It was all in good fun.

On Monday I made a few calls to set up a shopping trip for Matt. We would begin his transformation next weekend.

The following weekend he was in much better spirits. On Friday I introduced him to his red negligee. He looked very cute in it. He had nice legs, but I was going to have to get that leg hair off as soon as possible. On Saturday I took him to Sophia's to buy his foundation garments. He was in a quiet mood. He hardly said anything the entire time. He was reserved in his cooperation. It was like pulling teeth to get him to do anything. I was actually getting worried that I was pushing him too fast. I didn't want to loose him, but I had to get him ready and in the mood for Halloween. Everything was going to depend on a successful Halloween.

Sophia on the other hand, was great. She played the part just as I asked her. She mentioned Matt's weight and waist size and suggested that he loose weight. A couple of times she told him to wear the corset and bra as often as possible to get used to them. She did a really nice job. The final cost was less than I planned, but still very high for my financial condition. We were going to have to be successful in our consignment shop searches.

That night I was able to convince him to pose for pictures in his red bedtime outfit. His training was starting to pay off. He was now shaving his chest and armpits without being asked. We didn't get a chance to proof our pictures, so I did it the next day when I was online with Valerie. I had to take a few jokes from her when she saw my pictures, but to be fair I thought Matt did a very credible job as a photographer. I think eight of the red outfit pictures were moved into the printing file. At the end of the conversation, Valerie confirmed that she would visit in two weeks and she would bring her birth certificate.

The following Friday was boy's night. We started early and caught a matinee action movie. We ate at the Ponderosa and stayed away from the fries and bread. Matt said that he had lost two or three pounds that week … maybe. Weights go up and down whenever they like. During dinner I asked Matt if he had went to the Reproductive Fertility Clinic. He had.

"I went on Tuesday and made my donation. They said I needed to come back two more times. So I returned on Thursday," he explained. "I'll go back next week and finalize everything. Happy?"

I assured him that I was happy. After dinner I freshened my lipstick and handed his lipstick to him. He took my mirror and quickly applied it. I gave him an appreciative kiss. We then went out to a teen dance hall. Matt was, as expected, a poor dancer but I worked with him and he improved throughout the night. Line dancing was going to be his strength. It turned out to be a good place to watch the fashions and talk about them. Now that Matt had a better understanding of women's lingerie and under garments he was starting to become a bit more talkative and opinionated. By the end of the night I had a sore throat, but this time it was from yelling over the music, not because I had to do all of the talking. 'Girls-R-Us 101' was progressing very nicely, and in two weeks he would ready for 'We-B-Grls'.

I took Matt home and told him to pick out his bedtime outfit by himself. He chose the lavender negligee with the matching tap pants. It had been a long day and we were both glad to climb into bed.

The next morning we had breakfast and cleaned up. I told Matt to shave absolutely as close as possible. After he finished cleaning up, I told him that we would be shopping for a wig, and I asked him to wear his new undergarments for the day. He put on his gaffe, picked out some panties, put on his dancer's tights and brassiere. Then he asked me for help with his corset. I pulled it as tight as I could. He put on his jeans, camisole, and sweater and announced that he was ready. I handed him his lipstick and then put it back in my purse when he was finished.

I put his breast forms in a small tote bag, along with a sleeveless, tank top. I explained my plan to him, and he helped me put my camera equipment in the trunk of the car.

We drove off to my beauty salon and started what was to be a fun day. I had decided to have my hair trimmed and tinted. I wanted to give Matt plenty of time to enjoy the sights and smells and sounds of the salon. I wanted him to feel very comfortable there. After all, I was hoping that he would be spending his career in a salon as a hairdresser, manager and owner. Pamela needed almost two hours to finish. When she finished I asked her to take a look at Matt's hair. She said it was still too short to need trimming, but the back of his neck was starting to get shaggy. She suggested that he come in sometime and she would clean him up. Pamela also told him that his hair was long enough to start using a good conditioner on a regular basis. Matt bought the recommended conditioner and I made an appointment for the both of us in two weeks.

From the salon we went to a Merle Norman salon. This was one of their stand-alone salons away from the mall. Rhonda met us at the front counter and escorted us to a private room in the back.

Rhonda sat Matt in a chair, put a plastic cape around his neck, and then sat in another chair where she could face the two of us. "Now, tell me what you are looking for," she said.

I took over. "We're a couple of Halloween freaks. We are going to dress up in a couple of different costumes. Matt and I are going to wear the same costumes each time, and each time we will be dressed in some female role. We take our costumes serious and we want Matt to be convincing when he is dressed as a woman. Very convincing. We will be going over to a wig shop after our appointment here to pick out just the right wig for Matt. But to help make sure that we get the right hair color, I think Matt needs to be wearing the same shades and colors of makeup that he will be wearing on Halloween. Matt is here to have his color determined, to see how to apply makeup and to purchase the correct items for him to wear. In other words, make him beautiful, but make him believable. We are not trying to achieve a drag queen look. We want this to be as real as it would be for any other female customer." What a mouthful, but I meant every bit of it and I was going to make sure that Matt walked out of there looking beautiful.

"Sounds like fun," Rhonda responded. "Color matching will be no problem, and of course we sell only the finest cosmetics. What kind of look are you trying to achieve. Day time or night time, business, casual, or sultry?"

I took over again, "We will be going to night time parties, but I would also like your opinion on a professional day-time look. Matt will be aiming for a late teens appearance. Like a nineteen or twenty year old. We would like something to go with that look; innocent but a bit on the sexy side. Nothing too overwhelming, but then again, not the girl next-door look. Eye makeup, mascara and liner, but not too heavy. Some blush and a vibrant lip color. I can't tell you hair color, because we want that to go along with your colors here. Is it possible?"

"We will see," she answered. "First let's work on your coloring; winter spring, summer or fall. Matt, you are very fair complected. What we would refer to as winter. We will start with a lighter base and foundation and then move on from there."

After choosing the foundation and applying it, she looked at me and asked for my approval. "That looks nice. Good start."

Rhonda then went to the blush. She showed Matt how to circle the apple of his cheek and sweep it up towards his temple. Next she brought a slightly darker blush along the bottom edge of the brighter blush. "Always take a sponge and blend these two together. You want the shading to look smooth and natural. It will help give the appearance of higher cheekbones and fuller cheeks. Over these two dust on a translucent powder. It tames the color and gives your cheeks a more natural appearance."

She looked at me for approval. I nodded my head and she continued. "Next, your nose is a little large for a woman. So we will apply a slightly darker shade of powder along the sides of the nose. We are not going to hi-light the top of the nose. That will make you look like a drag queen."

I interrupted her. "As you go along and choose the different colors you are going to use, would you please write them down so that we can purchase the correct items later?"

"I would be happy to do that," and she began a list. "Next the lips. We will outline your lips because we want to make them a bit fuller than they are now. We have, in my opinion, two choices on how to go with the lip color. During the day I would suggest a rather saturated pink. Pink is your color, and if you want a sexier look, the more saturated pink is better. However, for evening I never recommend pink. We should lean towards a redder look. How would you like to proceed now?"

"We will be out mostly at night, so let's go for the night time look. However, write down the pink lip liner and lipstick that you would recommend for day time."

"Very good," and she wrote down the names on her list. "Ok, we apply the lip liner and we are going to follow the outside line of your lips. This will make your lips a bit larger, but not drag queen large. Next the lipstick." She applied the lipstick and continued. "And after the lipstick we will apply this lighter color to the center part of your lips. After we blend it in, it gives a slightly lighter color to this area of the lips, and this will make your lips look fuller and poutier. And finally, we will brush on a very light coat of translucent powder to help stay the color."

"Ok Matt, take a look in the mirror and see what we have done. Does this look ok?"

Matt, as usual, muttered something that was probably an affirmative.

"Ok then. Did you watch how I applied everything? Do you know how to apply your lipstick?"

"I think so," he answered. "I know I can't apply it with as much skill as you have, but I think I know the order and where to put everything."

I smiled at him. He was trying more than I had thought. Maybe this was going better than I had been thinking.

Rhonda continued with her lesson. "Next we have the eyes. We will be going for the doe in the headlights look. By that, I mean innocent and bright. With your fair complexion I am going to use a light shadow under and over your eye, to give you a more youthful innocence." She applied the shadow, then changed her attention slightly. "Before we give you that dramatic-eye look, we need to address your eyebrows. They are too bushy for your look."

I interrupted, "We will tweeze and shape his eyebrows later. Can you try and work around them for now? Maybe apply a concealer over the more bushy part?"

"Sure. What I'll do is apply a rather heavy concealer, about the same shade as your highlighter shadow."

She applied a heavy cover with a wand and blended it in with a small sponge. "That's about as good as I can cover the eye brows. Now, I'll apply a medium shade of brown with this brow pencil and I'll shape a thin brow, or at least as well as I can today. Next a bit of light pink shadow over the brow." Rhonda swept it on with two different brushes, contouring it to his eye. "Now we will apply just a smidgen of gray to the crease to add to the definition. Matt, I think the first couple of times you do your makeup, you may want a bit of help from Cynthia."

Matt chuckled out loud. "I think it will be more than a 'bit'."

"That's probably true," Rhonda smiled. "Moving along, I'm going to use a pencil and apply a light gray eyeliner on the top and bottom lashes. We will outline the entire eye. After applying it, we will take a small swab and smear the liner ever so slightly to give it a softer look. Like this." She was doing a very good job describing and showing Matt what she was doing. "And now, I am going to curl your lashes and apply mascara. Look straight ahead and try not to blink." She took her lash curler and pressed the upper lashes on both eyes several times. "Finally, a brown mascara. If you want more dramatic eyes use black mascara, but I warn you, a little black goes a long way. You should always apply at least two coats of mascara. When the mascara is dried, take a small comb like this one and brush them out to eliminate any clumping."

And Rhonda was finished. The lesson had taken a bit over one hour. "What do you think?" she asked both of us.

"I think you did a fine job, but mine is not the most important opinion. Matt, what do you think?"

Matt looked in the mirror for a couple of seconds, turned his head side-to-side and looked up and down. "Cynthia, I have to admit it looks pretty decent. I doubt that I could ever apply it and make me look this good."

"Thanks Rhonda. Let's go down your list and decide what we need to purchase today," I said.

We ended up buying 90% of the items on her list for a whopping $175. Again, my poor finances took a heavy hit. But on the other hand, I felt that Merle Norman cosmetics were of high quality and we shouldn't have to purchase more cosmetics for Matt for a long time. We picked up our packages and headed for the next stop.

Matt did his best to hide his face as we drove to Wigs and Hair. I handed the tote bag to Matt, and I got my camera and strobe from the trunk. We walked into the store, and there were two women customers talking to the saleslady. The saleslady excused herself and came over to us. "Can I help you?"

"I'm Cynthia and this is Matt, I called you for an appointment today."

"Yes, I remember. I'm Mandy. Welcome, and come this way." She led us to a small room towards the back of the store. "If you will wait here, I'll finish with my other customers and be right back." There was one chair in front of a well-lit mirror. I told Matt to go ahead and change. He pulled off his sweater and took the breast forms out of the tote bag and inserted them in his bra. Then he pulled on the white, sleeveless tank top. It was ribbed and had a surplice neckline and empire seaming. It was a tight fit and helped show off his narrow waist. Again, I explained that we wanted to show more skin around the face and neck area to get a better fit for the wig color.

It took Mandy almost 15 minutes to get back with us, and I was becoming a little impatient. She finally returned and apologized, "Sorry for the delay. Now, how may I help you?"

I gave her the standard Halloween story while Matt sat there. I said that I wanted to make sure Matt was as convincing as possible in his costumes, and that we needed a good quality wig. I didn't want a $60 wig that looked like it was a $60 wig. I then explained that we wanted to try on a series of wigs to find the perfect style for Matt. We wanted to start with a short, pageboy style and look at as many colors as she had. Then we wanted to pick the best color and look at a wide range of lengths and styles. Then, when we had picked out the best style, we wanted to take another look at colors. And finally, I said that I wanted to take a picture of Matt with each wig so that I could use it later to buy a second wig if necessary. I said it depended on what costumes we picked out.

The real reason for the pictures was to help me pick the best style and color when we started styling Matt's real hair. As his hair grew out, I wanted to style it in a continuing range of nice feminine styles that matched up with his hair length at that time. These pictures would help tremendously.

Mandy began bringing in wigs. She would show Matt how to put it on, then brush and fluff it out and give it a bit more style. Matt would stand up and I would take a picture, and then we would discuss the merits of the wig, and how it fit Matt's face shape and color. We looked at about ten colors and styles of short pageboy styles and decided that we all liked the darker chestnut brown for color. Then we started with longer wigs and looked through about another twelve or fifteen wigs. Each time I took another picture. This was a tougher decision, and we ended up going with Matt's preference. It was a pretty, shoulder-length wig cut in layers and curled in soft, medium sized curls. It had short, thin bangs. They could be brushed down in straight bangs, or swirled up and to the sides to expose more of his forehead. He looked very nice in the wig. And finally, we looked at another five or six colors. I loved the same style in a lighter red and a darker auburn. But Matt wanted to stay with the more conservative chestnut. I would have put him in either red wig. He would have driven the boys crazy. But I knew he wasn't ready for that type of attention yet. Chestnut it was.

I paid for the wig. We had picked out an expensive one, $185. Like everything else, it was more expensive than I expected but it was the last expensive piece of the new Matt. And it made him look real. He would have no problem passing as a real woman.

It was getting late in the afternoon, but I had one more stop planned. This one I hadn't told Matt about. We left the wig shop with Matt totally en-femme. He left on the white tank, his breast forms and his light windbreaker. With his new wig and makeup he looked very pretty and passable. A close look showed that his nose was bigger than I would have liked, and his cheeks were not as full as a real girl's. He was pretty, but not beautiful. That would have to come later. But for now I was very happy with his progress. We still needed to shape his eyebrows and add some accessories. But we were making nice progress.

As we were riding in the car I made my announcement to Matt. "I'd like to stop at the mall and do one more thing. Is that ok with you?"

"Dressed like this?" He looked very apprehensive.

"Matt, you look very good. Much better than you think. Unless someone really studies you, they won't be able to tell you're not just another pretty girl. And sooner or later you will have to get used to going out in public. This will be a short trip to allow you more experience."

"What do you want to do at the mall?"

I swallowed and said, "I want to get your ears pierced."

He just looked at me. "I think I can handle that. Most guys now-a-days have pierced ears. Does it hurt?"

"There is a momentary sting. And it will throb later tonight and tomorrow. But it isn't a sharp, lasting pain."

"What kind of earrings am I getting?"

"They will put in studs to hold the hole open while your ears heal. You will have to leave the studs in for several days. Then you can take them out for short periods of time, a couple of hours now and then. But if you leave them out too long, the holes will heal shut. So it is best to always wear earrings. The shop is offering two free pairs of earrings if you have your ears pierced and buy one pair of earrings. We will buy you some standard hoops, and then look at whatever else they have. Ok?"

"Don't you think she will be able to tell I'm a guy when she starts talking to me?"

"Don't say a word. I'll do all of the talking. When I ask you a question, just shake your head yes or no. And I bet you she doesn't figure out you're a guy. Trust me, you look really good. Really, really good." I gave him the most reassuring smile in my inventory.

We reached the mall and I parked the car. I walked around to the other side of the car and let Matt out. "Here," and I handed him my purse. "You will look better carrying a purse. Put the strap over your left shoulder and hold the strap here, in front of your shoulder. When it is time to pay, take out my wallet and make the purchase. Take small steps, don't try and hurry anywhere. Ready?"

"Which way to the firing squad?" he asked.

"No firing squad, but you are going to be looked at by guys. Look straight ahead and keep walking. Trust me, you are very pretty and you are going to turn a few heads. Ignore everyone. If someone says something nice to you, give him a little smile. If they say something stupid, keep walking or turn away. If a situation comes up that you are not sure about, look at me and I will intervene. I will run interference for you. Just remember, you are pretty. Enjoy the situation. And also remember, I love you." I gave him a quick peck on the cheek. "Let's go gorgeous."

We walked into the mall. I tried to keep the pace constant and slow. I didn't want him to get hyper and freak out on me. I noticed a few guys glance at us as we walked down the main concourse. About half way towards the center of the mall was a small earring kiosk. We stopped and I got the girl's attention. "My friend would like to have her ears pierced."

The girl welcomed us and told Matt to sit down on a stool next to her work area. She proceeded to explain the process and read all of the usual warnings. Matt shook his head yes or no and I translated, explaining she had just had her tonsils out, and it was painful to talk. The girl explained their special and asked us to pick out the earrings we wanted. We chose the hoops and told her that Matt would wear those rings when we were finished. We would carryout the studs and the other two sets that we were picking out. Both sets were single stones, one a rhinestone and the other a small ruby type stone.

The girl swabbed Matt's ear lobes and punched them with her tool. They bled a little and she staunched the bleeding, then inserted the hoops. She rang up the bill and presented Matt with the bill. He set my purse on the counter, took out my billfold and paid her. We collected the receipt and extra earrings and left.

After we had walked away I asked Matt if it had hurt. "Actually, it wasn't as bad as I thought it might be. And I like they way they hang and sway from my earlobe. It's a neat feeling."

"Well I am glad to hear that. I was probably more nervous than you. And by the way, do you think she picked up that you are a guy?"

"I don't know," he said. "Do you think so?"

"Not a chance. Not a chance. You were great. Girl you go! How are you feeling? Are you ok? Shall we get a bite to eat?" I tried to act as excited and as enthusiastic as possible.

"Yeah, I think I'll be ok. I am hungry. Let's go for it," and he said it with conviction.

"Would you like to stop at the girl's room first?" He said no, so I walked us down to the food court. "What do you want, I'll order for both of us." He wanted a hamburger and salad. I placed the order and since Matt had my purse, he paid.

We found a table out of the way where we could watch the foot traffic through the mall. "Here, give me your purse. I normally set it on my lap where no one can see it. Or you can hook the strap around a chair back and set the purse on the chair where it is out of sight." We began to unwrap our meals. "Take small bites. Large bites smear you lipstick. Kind of curl your lips a little rather than use them to grab the food."

He took a bite and I complemented him on his technique.

We sat there eating, and I pointed out other girls and critiqued their looks. I voiced some negative comments about a few guys, especially those with facial hair or greasy hair. I pointed out how girls walked together and how they actually walked, how they took steps. I pointed out a few tables that had both boys and girls. I talked about how the girls were tossing their hair, leaning forward towards their guys as they talked and other techniques they were using to flirt.

Lunch was going nicely when two boys carrying their lunch trays walked over to our table. They were in their early twenties. The taller one spoke to Matt. "We saw the two of you sitting here and thought we would ask if we could join you. May we?"

I took over immediately. "That's sweet guys, and normally we might ask you to sit, but we are just finishing up and we're already late meeting our boyfriends down at the arcade. Maybe next time," and I gave them a sweet smile. They took the hint and went over to another table and sat down by themselves.

I grinned at Matt and he grinned at me. "Is there any doubt in your mind any more?" I asked. "The front boy wasn't talking to me, he was talking to you."

"He wasn't my type," Matt smirked. "Oh wow. I have to hand it to you, you were right. And you are smooth. You handled them easily."

"It's just experience. As a girl, you learn early how to handle guys when they hit on you. Never insult them, just let them know there is someone else and he is close by. Start taking notes girl, you are going to break some hearts."

"God, I was scared when they first came over. But now I have to admit, and if you ever tell anyone else I'll choke you, I have to admit that it was kind of a rush. An ego boost. Boy, you did a fantastic job with some limited material." He was starting to get a little giddy.

"Never underestimate your own native talent. You can't make a silk purse out of a sow's ear. Or was that a cow's snout?" I started laughing. I was getting giddy too. This encounter couldn't have been better if it was planned. Those two boys pushed our schedule ahead by a couple of weeks. Matt was quickly picking up confidence. "Shall we get going before someone else comes along?"

I handed my purse to Matt, and we walked out. "What would you like to do now?" I asked. "Shopping? Movie? Dancing?"

"I'm not sure," he said. "Not dancing, I'm not ready for that. My corset is starting to cut me in half, and I would love to take it off. But I wouldn't mind walking around a little more also."

"Let's just walk through a couple of shops and see what they have. We can't buy anything though, I think I've spent enough money for one day. How does that sound?"

He agreed and we walked through the mall, stopping at a couple of women's shops. I did all of the talking when the sales clerks approached us. We finally worked our way back down the mall and out to the car. I opened Matt's door and let him in. I got in behind the wheel and looked at him. I beamed my largest smile at him and he smiled back at me. We sat there for a minute talking with our eyes and smiles. "Quite a day wasn't it?" I said.

"Yeah it was. It certainly wasn't what I had expected. I have to admit again, that was a fantastic adrenaline rush in the food court Do girls get a rush when a boy comes over to talk to them. I mean, I don't have any interest at all in boys," and he gave me a flirty smile, "but just the fact that they came over to talk with us makes me feel kind of special. Maybe it is making me arrogant, but it says that you must be pretty and attractive. Doesn't it?"

"It is a reaffirmation of your looks. It says that you are attractive to the opposite sex. It is an ego boost. Some girls get hooked on it. First they dress sexy, then trashy. They flirt and tease with boys to continuously boost their own ego. It can be addictive. It is a great feeling, but be careful. Don't let it hook you. Keep your perspective." He leaned back in his seat, and took a deep breath. "Shall we go home?"

We were half way home when I remembered. "I forgot to tell you two things for next week. First I made appointments with a local doctor to get blood tests next Saturday. Is that ok?"

"Yep."

"And second, my best friend is coming from Milwaukee to visit. She is coming on Friday and leaving on Sunday. I would love to have you meet her. And nothing has to change between us. We can keep our routine. Valerie, can use the pullout bed in the living room couch."

"Well, one thing has to change," Matt said. "I can't wear you negligee."

"Yes you can. Valerie is my best friend, she already knows all about us. Trust me it is not a problem. We can even go out together as girlfriends, now that you getting the hang of this."

"Who else have you told?" he demanded in a raised voice. He obviously wasn't happy that Valerie knew about him cross-dressing.

"Matt, don't worry. Valerie and I have been best friends since kindergarten. Nothing between us goes any farther. She has seen your pictures and she thinks you are adorable. She has said numerous times that she envies me. Valerie also thinks that men should be able to enjoy the softer side of life. She thinks exactly as you and I do. She is truly a soul mate and would never do or say anything to hurt either one of us. She really, really likes you already. Please, don't worry. You will see. She really wants to meet you."

"I'm just surprised, is all. I never thought that any one else would ever know about this. I have to admit, it leaves me feeling vulnerable. I feel like this is out of my control."

It is out of your control, I thought. It was always out of your control. "Matt, nothing has changed, it's exactly the same as it was." That much was true. "Please keep an open mind. You will enjoy Valerie. She is a lot of fun to be around. And she is very protective. She already likes you and will do anything to protect you." I decided that even though it had been a great day, a half of Valium in a glass of red wine was going to be needed tonight. I didn't want him to linger on this. It was going to be bad enough next Saturday when we went to the doctor. I didn't need to make it any worse now.

We reached home and I immediately went into the kitchen and poured our wine. I gave Matt his wine and Valium, and then decided to try another ploy to get his mind off Valerie. "You know Matt, a girl as attractive as you can't be called 'you' and 'her' all the time. You really should think of a female name to use. Something that fits your persona. Have you thought about it at all?"

His answer surprised me, "Yes I did think about it today. Especially while we were shopping at the end of the day."

"That's great," I gushed. "Any ideas?"

"I thought it might be good to stay with the same initials. I was trying to think of a first name that started with M. Something like Mary or Margaret or Michelle."

"Or Melissa, Megan or Marsha," I added.

"There is also Mimi, Minerva, Maude," and he started laughing with Maude. I thought he was going to spill his wine.

"And let's not forget Mabel," I laughed. "I like Melissa, Michelle and Megan. What do you like?"

"I like those too. Megan is ok, but maybe a bit yuppie. I think I prefer Melissa."

"Then Melissa it is," I pronounced. I raised my wine glass and made a salute, "To Melissa, my beautiful boyfriend."

"To Melissa." And we drank. The Valium was fast acting, and he became noticeably more relaxed. "Cynthia, what do you want to do now?"

"Let's go get my camera and all of your things out of the car. I'll clean out a drawer in my vanity for your cosmetics. And then let's look at your pictures from last week. We never looked at them, you know." Melissa finished her wine and we went and collected her new things. We took her makeup into the bedroom and filled my vanity. I suggested that we both freshen our lipstick.

We sat down in front of the computer and did a quick look through at our pictures from the previous weekend. We each pointed out a couple of improvements that we had made, and we thought of a couple other items that we could try. "Would you be willing to try some new ideas?" I asked.

"If I can also take a few of you. But we need to get moving, this corset has almost cut me in half."

We quickly set up, and I asked Melissa for one favor. "Would you put on my black heels?" She agreed and I ran and got them. I slipped them on her feet and began my turn behind the camera. This was Melissa's first photo shoot, and I had all kinds of angles and looks that I wanted to try. I shot almost thirty pictures.

Then it was Melissa's turn to take the shots. She put me through my usual poses, and then startled me. "Can I shoot you in the nude?" she asked.

The wine and Valium must have really been doing their work. I wasn't sure what to say at first. Then I decided that eventually I was going to want to shoot her in the nude, so now was as good as anytime to start. After a bit of hesitation I said, "Yes. I've never been asked to pose in the nude before and I can't think of a better photographer to start with. But first, my photographer has to give me a kiss of encouragement." I got my kiss. "Ok, no porno!" I laughed. "What would you like me to do?"

Melissa posed me in several positions, but made more lighting changes than we had ever tried. "We need to have another light mounted on the ceiling for over head lighting. And it would be nice to have another strictly for backlighting. Maybe something a little softer than the others," she said.

"Well, we have a little problem. It's called cash flow. I've been running over my limit lately, and to be honest, there are some other things I'd like to buy for you before we begin thinking about new camera equipment dear," I told her.

"I'm sorry," and her voice was indeed very apologetic. "I guess I'm getting a little carried away. I'm starting to like the creative element of this. It never occurred to me that money was tight. I hadn't given it a thought. I suppose I thought that you were making almost fifty thousand a year, and I thought that was a very good salary."

I sometimes forgot how young and naïve Melissa was. "You don't need to be apologetic. But fifty thousand isn't nearly as much as you might think. For instance, I get paid about $4000 per month. Of that, the government takes 30% or $1200. That means I only see $2800 per month. I pay $800 per month for this house. That leaves $2000. Then, electric and gas take about $250. I don't have cable, and the company pays for all Internet and telecommunications, including my cell phone. Fortunately, the company also supplies a car, gas and insurance. As long as I keep my personal use of the car to a very low level, I don't need to worry about transportation expenses. So where were we? Oh, about $1750 per month." I was on a roll. I had gone over this in my mind hundreds of times.

"The company provides no pension, but they do have a 401k. That 401k will have to take care of me in my old age, so I put in the maximum that I'm allowed. That comes to 15% or $600 per month. Now I'm down to $1150 per month. I allocate $600 per month for me. That takes care of weekly visits to the beauty salon and for clothes. I admit that sounds like a lot of self-indulgence. But first, as I have said over and over, I truly enjoy being a woman and I love living on the softer-side of life. I make no apologies for it. Secondly, I make my living selling. And as much as we would like to think that selling is based on ability and not appearance, it simply isn't true. If I want to be successful I have to keep my looks up. So now I'm down to $550 per month." I had to stop to take a breath. Melissa was just standing in the middle of the room holding the camera and listening intently.

"$550 and I haven't spent any money on food yet. Fortunately, my sales job helps on that. I eat a very small breakfast; partly to save money but also to maintain my figure. I can usually find someone to take to lunch. So I have a large lunch and charge it to the company. In the evening, I again try to eat small. But food still takes about $100 per week. That leaves $150 for entertainment and the other fun things in my life," and I gave her a nice, big smile. "You for instance."

I think Melissa was a bit stunned. She didn't say anything for a minute. "You've spent a fortune on me recently. I didn't realize the situation. I should do more. I'm sorry, I guess ..."and her voice trailed off.

I stood up and walked over to Melissa and gave her a tight hug. There we stood; me nude and Melissa dressed as a woman for the first time in her life. Melissa was unsure of herself. Thrilled at being hit on by a boy earlier today, but now feeling awkward and guilty. And a cold camera poking me in the back.

"Melissa, don't feel sorry. Don't feel guilty. I love having you here. I love sharing with you. I love posing nude for you," as I tried to add a little levity to the situation. "Sweetie, I have money in savings and as I said before, I reserve the right to spend it on my friends."

Actually, I had a lot of money in savings. Like Matt, I went to school on scholarship. It certainly paid to graduate from high school a semester early as valedictorian. When I was a little girl, dad started saving for my college years. We were not rich, but we were frugal. Dad had set aside almost $50,000 for me. In the fall of 2000, the bursar's office reorganized and lost track of my scholarship. It looked like I was going to have to pay my own way. We couldn't have gotten any luckier. Dad pulled the money out just as the Bush stock market crash began. Dad sold almost at the peak. Buy low, sell high. For once it worked for someone other than just the inside traders.

Dad split the money into three parts; a three-month, six-month and a twelve-month CD. When the three-month and six month CDs came due, dad put them into twelve-month CDs. The following fall, for graduation mom and dad started gifting it to me at $20,000 per year. In December 2001 I received $20,000, and in January 2002 I received another $20,000 tax-free. At this time I had $40,000 in my savings. Not bad. In January 2003 I would get another $20,000 and knowing my dad I would probably receive $20 grand in 2004 also. But Melissa didn't need to know all of that yet.

"Don't worry," I told her. "I'm doing alright. Especially when I have you to hold."

We stood there for another minute, and then I tried to break the mood. "You're probably getting tired of that corset, I bet. Are we done taking pictures?" She shook her head yes. "Good, I was starting to get a little cold. Before we go change, let me look at your makeup," and I pushed her back to arms length. "Boys have much more oily skin than girls, and it makes your makeup look shiny or even worse. But your makeup and skin look good, after how long? You've been wearing it for over eight hours. And it still looks good. You look great! Come on, let's change clothes," and I led her to the bathroom.

When we reached the bathroom, I helped her get out her toiletries. "You might have to wash your skin twice with the Noxema. You have a lot of makeup on. Make sure to gently work it around your lashes and brows. Don't forget to shave, brush your teeth and apply your anti-perspirant. I'll take your wig and place it on the stand." She handed me the wig. "I'll bring you your negligee, which one would you like?" I asked.

She asked for the lavender negligee. "Me thinks you prefer the longer gown," I said. Her answer was yes.

We both cleaned up and went to bed. We hugged for a while and I really enjoyed the smell of his soft skin and the silky smoothness of his gown. I fell asleep very happy.

Sunday morning we ate breakfast, read the paper and looked at last night's pictures. I had several nice pictures of Melissa to send Valerie. And I was also toying with the idea of sending some to mom. Melissa's pictures of me were surprising. The different lighting schemes were very good. Some of the pictures had a very artistic look to them. I complimented Matt, and told him that he had some hidden talent for photography. He seemed pleased with the pictures also.

I sent Matt off to wash his dainties and clean himself up. When he was done I sat him at the vanity and gave him the special facial moisturizer that he always used. I had him put on his lipstick and then I applied another coat of hardener to his nails. I drove him back to the dorm and gave him a big kiss to send him off to his studies.

Back at the house I collated the weekend pictures and sent the best ones to mom and Valerie. I talked with Valerie for my usual two hours as we set up her visit for the next weekend. My conversation with mom was cooler than normal. She had received the pictures. She complimented Melissa on her appearance. But she asked me several different times, in several different ways, if I was sure of the direction I was gong with my relationship. She was not judgmental, but pushing to see if this was what I really wanted. Had I given any thoughts to my long-term relationship with Matt? I assured her that I was very happy with the way things were going, that I had given everything a great deal of thought, and most importantly, Matt was happy. That seemed to satisfy mom, and the last half hour was the usual up-beat tone for us.

(continued)

  

  

  

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