Jasmine Cally Vail – The Awakening

by

G. L. Hudson

 

CHAPTER FOUR

Monday morning, I arrived a bit after 7:00 and Jason came in about 7:30. I heard him out in the bullpen area, shuffling around and turning on additional lights. About 5 minutes later he came into my office and placed a small vase with two roses on my desk. He stood back and smiled.

"What's this all about?" I asked.

"It's just a little thank you for helping out this weekend. It meant a lot to me."

I smiled. I felt proud of myself. Amazing considering how much time we girls would spend tearing him apart behind his back. That thought made me feel a bit of shame. "Jason, I'm glad I could help." He walked out of my office about six inches taller than when he came in.

Sure enough, at lunch Jasmine brought up my weekend and asked how my Saturday with Jason had gone. She was particularly mean. "Did he have a lot of dolls to move? Do his Barbie dolls have a large wardrobe? Does he have the Malibu Barbie beach house? Does he sleep with his teddy bear? Did you see his jammies? Do they have feet in them?"

That last question got a pretty good laugh from all of the girls, even me. It was mean, I know it, but I was back with the girls. I was reverting back into their mentality. I wasn't proud of myself, but I laughed. They were the only social group I had any contact with. I felt that I needed them, so I succumbed to my baser emotions.

Monday afternoon was a first. Mikey came to my office and asked me out Wednesday night. I thought that maybe he was getting serious. But his timing was bad. This was the week for my board exams. I was going to take an extra day of vacation for studying and then two days to take the boards and decompress. I made a counter offer for Saturday. He accepted.

Saturday came and he picked me up at 7:00 P.M. He took me to a very upscale restaurant and we had a scrumptious meal. They had a piano bar and we decided to stay there and have a cocktail after dinner. Mikey was very charming and humorous. He told me a bit about his childhood and some stories from his latest international business trips. I was favorably impressed with him. And I was horny.

I decided that I would take him home and sleep with him. When he took me home, I asked him to come up to my apartment. When we arrived, I put on some soft music and offered him a bit of wine. We sat on the sofa and immediately began kissing. Kissing soon turned into pawing and petting, followed by the slow removal of various bits and pieces of clothing. I was getting turned on and so was he. I suggested that we adjourn to the bedroom where it would be a bit more comfortable.

We helped each other finish stripping and I was impressed with his size. He was the biggest man that I had ever had. We slipped into my bed, and he immediately rolled on top of me and slipped his penis inside me. I was hoping for more foreplay and attention, but I was just as excited as he was. He was big, but I was so wet he had no trouble entering me. I loved the feeling of his large penis inside me. He literally filled me up and it felt great. It took him less than 2 or 3 minutes to orgasm. After he reached orgasm he stopped his thrusting. I wasn't finished, and I was forced to start pushing harder, which was a bit difficult under his weight. But eventually I was able to bring myself to orgasm.

After finishing, he kissed me, pulled his penis out, rolled over and immediately fell to sleep. That was it! That was the end of the evening. I was left lying there, facing the ceiling wondering what had just happened. I got out of bed and went to the bathroom. I cleaned up, put on a negligee then went to the kitchen to get a bit of juice. When I came back to bed he was snoring, oblivious to the rest of the world. 'Just like a man', I thought. I eventually fell asleep next to him.

The next morning he really pissed me off. I woke up at 7:00 and he was getting dressed. He leaned over and kissed me, "Gotta go, I have a tee time of 8:00. I have to hurry. I'll call you, bye." And out the door he went. Slam, bam, thank you ma'am. I had been used and thrown away. At least that's the way it felt. I was hot! If I had had a knife I think I would have cut off his manhood! The nerve of that son-of –a-bitch! Use 'em and throw 'em away! I lay in bed seething for about another half hour. I couldn't get back to sleep. I was too angry.

I headed to the bathroom to take a nice long bath. When I reached the bathroom, things got worse. The floor was covered with water. I looked around and saw water running from the ceiling and down the wall. "God damn it!" I swore. I walked out to the living room and called the super and reported it. I changed into some old clothes, then went back to the bathroom and started mopping up the mess.

About 45 minutes later the super knocked on the front door. "Sorry for the trouble. Your upstairs neighbor put some stockings in the sink and left the water running. The stockings got caught in the over-flow drain and the sink ran over. She went to church and forgot all about the water running. Can I see the damage?"

I unlatched the door and let him in. He took a quick look at the bathroom and announced that he would have someone fix the plaster on the ceiling later in the week. "It will need to dry out before we can do anything. It ran down the wall?" he asked.

"Yea."

"And then across the floor." I shook my head yes. "Maybe we better check the adjacent room." He led me into the spare bedroom. The water had leaked under the wall and had soaked the bottom of two boxes. He helped unstack the boxes and move the two wet ones to a dry spot. He took the mop and soaked up the remaining water.

"I'd check out those boxes and make sure nothing was ruined. If it was you'll have to check with your renter's insurance to take care of it," he told me.

"You don't cover damage to personal items?" I asked.

"Nope. We only insure the building and fixtures. Personal property has to be covered by your own insurance." He walked to the front door. "Again, I'm sorry for the inconvenience. We'll probably come back on Wednesday or Thursday to fix the damage to the ceiling. I'll let you know before we start. Have a nice day," and out the door he went.

'Have a nice day!' What a nice day it was shaping up to be. My boyfriend was a prick, a big prick, but a prick none-the-less. And now this. I didn't have any renter's insurance. I had forgotten all about it. I hoped there wasn't anything expensive in the wet boxes.

I went to the kitchen and pulled out a steak knife and returned to the bedroom. Jason must have used half a roll of duct tape on each box. I cut through the tape on the first box, tossed the knife aside and opened the flaps. I was confused by what I saw. There was a woman's brassiere sitting on top. That didn't seem right at all. I lifted out the brassiere and picked up the next garment. It was a white half-slip. I took out the next garment, a full-length slip. Then a couple more half-slips, followed by some very nice camisoles. As I reached the bottom I found a dozen or more women's panties. The panties were soaking wet. I took them into the bathroom and laid them across the shower rod and the knobs of the bathtub faucet.

This was rather interesting I thought. I wondered if they belonged to Jason's mother and he had them by mistake. I was quickly cured of that fantasy when I opened the second box. It had a shoebox on top. I opened it and found a couple of computer disks and some pictures. They were pictures of a nice looking girl in her late teens. It looked like she was modeling clothes. In a few of the pictures she had short blonde hair, in some she had straight black hair and in others she had curly red hair. She looked a bit familiar.

I set the shoebox aside and noticed a couple of magazines. There were two magazines titled 'Forced Womanhood' and about 6 'Transformation' magazines. A quick look showed that they were all about transvestites and crossdressing. In the bottom of the box I found a leather corset, a couple of girdles, 3 or 4 panties with built in fanny pads, 4 garter belts and two all-in-one panty-girdle-bra foundations. All of the clothes were wet, so I took them to the kitchen and hung them up.

Then I returned to the bedroom. Jason was a TV! How interesting I thought. And how appropriate. It was beginning to make sense now. I thought he was a little effeminate, but I had never pictured him as being gay. Very interesting indeed. And how intriguing! I decided to open the rest of his boxes and see what else he had.

I spent the next 3 hours snooping through all of his belongings. As I pulled sweaters and skirts and dresses and all types of female clothing out of the boxes, I noticed that I was running out of room on the bed and dresser. I decided that I had better hang up the clothes and I began placing the other items in his dresser. I didn't want to take a chance on any more accidents.

I couldn't believe the extensive wardrobe he had. Besides all the clothes that a girl could possibly want, he had 4 different wigs, each with its own Styrofoam head. I placed them on the upper shelf in the closet. He had over a dozen pairs of shoes; everything from sandals to knee high boots with stiletto heels. There was jewelry, purses, scarves and a nice leather winter coat. There was enough makeup for a lifetime. He had perfume, nail polish, and plenty of nail buffers and files. There were more than 30 pairs of nylons, many still in their original bags. He had thigh highs, knee highs, stockings for use with garters and many different styles and colors of pantyhose and tights. It was amazing.

In addition he had satin sheets, pillow cases and a frilly pink down comforter. It was obvious where all of his money was going. After putting his other things away, I made the bed using his sheets and comforter. They were better than anything that I had, and they did belong to his bed.

I picked up the shoebox of CDs and carried his magazines into the kitchen. I was starting to get hungry, so I made myself a sandwich and took out a beer (I had earned it) and I began flipping through his magazines. They were very amusing and often hilarious. I loved the pictures in the 'Forced Womanhood' magazine. In the 'Transformation ' magazine, I had to admit that I was impressed by some of the girls. They looked very nice and made convincing girls. At least in the pictures.

After flipping through the magazines, I washed my dishes and went back to the living room. I took out my laptop and booted up. When it was ready, I slid in one of the CDs and pulled up the index. It was full of pictures and jpegs, text articles and many html files. I copied them over to the C drive and then slid in the next CD. He had about 15 CDs, so there were a ton of files. I sorted by file type and brought up a thumbnail screen on the pictures. I glanced at them quickly, and saw that they were like the pictures that he had printed.

When I first saw his prints it hadn't dawned on me who was in the pictures. It never entered my mind. I didn't see Jason in those pictures. But now that I knew, I did indeed see his features and body language. He was very good though. He looked very convincing, very feminine, very pretty. In some he tried to look too sexy, and he didn't quite pull it off. Maybe it was a lack of experience or confidence, or maybe it was just too over the top. But there was potential in those pictures. With coaching and practice, I was confident that he could be the sex-kitten he was attempting to emulate.

I flipped through a hundred or more jpegs and then took a look at the text files. They were split about fifty- fifty between technical computer articles and fictional stories about transvestites and crossdressers. There were too many to skim through, so I just read the titles and figured out the idea behind most of them. Then I took a look at the html files. They were from his web site 'Jasmine's World'. Jasmine, I thought. I wondered if he had named himself (herself) after Jasmine at work. I looked at just enough files to pick up the address of his web site.

I plugged my laptop into my data line and dialed up his webpage. It was about his feminine side and was full of pictures, stories and links. It also had a biography page. That was the most interesting part. It was rather long and tended to ramble. I read it twice. It explained a lot. His brother's job and travel gave Jasmine all the time she needed to pursue her hobby. He had been dressing since he was 6 years old. His mother had caught him when he was seven and told his father. His father ridiculed and teased him constantly about it. That explained a few things for me. No wonder his dad was such a jerk.

He only dressed at home and had never been out in public. He was very active in chat rooms and liked to hear about other girl's episodes out in the real world. Someday he hoped to feel pretty and confident enough to venture out. Maybe someday he could make it to one of the conventions that crossdressers held across the country.

Then he mentioned his friend. Me! He even used my real name, although he spelled it incorrectly; Karin. Karin worked with him and was a real nice girl. She was beautiful (blush, blush), very feminine and best of all, very nice to him. He wished he could share his secret with her and have her accept him as he was. (Well now he had.) It was his fantasy. It might become his worst nightmare I thought. I was mad that he had used my real name. What if someone from work stumbled on this site, saw Jasmine and figured out it was really Jason and then figured out that Karin was really Karen. Not likely, but I was not in a good mood and that thought stuck in my mind.

I looked through some more of his web site and decided to take a look at his message book. There were many complimentary letters about his appearance and his site. And there were a couple of vulgar comments as well. I noticed that the vulgar messages were from the last two days only. Then it dawned on me that he probably deleted those messages when he reviewed his webpage. I looked at his links page and saw tons of links to other CD personal pages, on-line shopping sites, advocacy sites and a couple of local CD clubs.

I checked the clock on top of the TV and it said 8:00 P.M. I had spent all day going through Jason's clothes and effects and looking at his webpage. I realized I was hungry and went to the kitchen to make some pasta.

I sat at the table and leafed through one of his magazines. I couldn't believe that the day had disappeared on me. Then I realized that I wasn't as angry as I had been. In spite of the water leak, and that stupid Mikey, I wasn't feeling as ornery. I was still a bit angry, and I didn't like having my name on Jason's webpage, but I was feeling a bit better. Then I started thinking about Jason. I liked him a little bit, but he wasn't a man. At best, he was a little kid. At worst he was an effeminate sissy who wanted to be treated like a girl. I felt that he was nice enough person, but of little interest to me in terms of male-female relationships.

To this day, I can't figure out how I came to my next decision. I think it was a combination of being mad at Mikey in particular and men in general. It probably had a little to do with Jason using my name, and it probably had a lot to do with how I felt about Jason as a person and how I saw him in relation to me. Especially in his social relationship to me; I saw him as nice but inferior. I was older, had more education and a better job, better social skills and more friends, although neither one of us had that many friends. And I also felt a little sorry for him. His parents had totally destroyed his confidence and self-esteem.

I had decided to toy and tease Jason. I would give him some of what he wanted, in that I would help him enjoy his feminine wishes. But I was going to be a bit cruel about it. I was going to control him and make him do what I wanted. I was going to humiliate him a bit and titillate him a bit. I wasn't sure how it would play out, but I knew how it was going to start. I went into my closet and found a small shopping bag from Victoria's Secret. It had a square bottom and two looped handles on top. I went into Jason's room and pulled open his panty drawer. I found a nice pair of high-cut, cotton panties and dropped them in the bag. I wrote a little note and dropped it in the bag, and then set the bag next to my briefcase, so that I wouldn't forget it Monday morning.

 

Monday morning I arrived at the office earlier than normal. I went to Jason's desk and put the bag in his lower desk drawer. Then I took a sticky note and wrote, 'There is a little gift for you in your bottom desk drawer.' I left the note on top of his desk. I went to my desk and began preparing for the day, but I was listening for Jason. He was usually the second person to arrive each morning.

About ten minutes later I heard Jason arrive and go to his desk. He saw the note on his desk and he opened his bottom desk drawer and took out the Victoria's Secret bag and read the note. The note was written on my best stationary and said:

A pair of pretty panties for a pretty Jasmine.

Put the panties on and put your old panties in the bag.

Then come to my office and model them for me.

I would have loved to have seen his face when he read the note. I leaned back in my chair and waited to see what happened. It was about 5 minutes later that he came to my office. I heard a little tap on the door and looked up. His face was pure white. Every bit of blood had drained out and he looked like a ghost. "Hi Jason. How ya' doing today?"

"Ok," he answered quietly. "I … ahh … found these in my desk. I think you meant to put them in Jasmine's desk."

"Oh no," I said with a big smile. "I put them in the correct Jasmine's desk. Did you read the note?"

"Ahhh … yea."

"Well then you know what to do. I'll wait here for you to return. Go." He hesitated and I repeated, "Go, before the others begin to arrive." He slowly turned and walked away. As soon as he was out of earshot I began giggling. This was fun.

He returned about 5 minutes later and he was holding the bag. "Bring the bag over here," I instructed. He brought the bag and handed it to me. I set it on my desk and looked in the bag. I saw his under shorts in the bag. "Good job," I complimented him. I took the shorts out and held them up for us both to look at. "Boxers. I would have taken you for a briefs man, Jason. Oh well. Go close the door, would you please?" I asked sweetly. Jason did as he was told. "Just a sec," and I took the bag with his shorts and put them in my bottom desk drawer. "Ok, show me your panties. I want to see how they look on you."

"What?" he asked incredulously.

"You heard me honey. Drop your trousers and show me your panties," I repeated with more authority.

"But … but this isn't right," he protested.

"I don't care if you think its right or not sweetie, do it!" He slowly unbuckled his pants , unzipped them and then unfastened the button. He stood there holding his pants up with his hands. "Go ahead," I urged. "Let's see."

He let his trousers slide down to his knees. I could see that he was trembling and his knees were shaking ever so perceptibly. His shirttail was rather long and was covering his panties. "Hold up your shirt so I can see your panties," I said. He lifted his shirt. I could see the panties fit nicely. I half expected to see an erection, but instead I saw nothing. He had tucked his penis between his legs.

I gave Jason a big smile. "They look very nice on you. And you look so smooth, with no unsightly bulges. Thanks for modeling them for me. You can pull your pants back up now."

He pulled his pants back up, fastened them and tucked his shirt tail back in. "Why don't you open the door before anyone notices that we have it closed," I told him. He opened the door and took a quick look outside. "Anybody else here yet?"

"No."

"Good, then I have one more favor to ask you. Can you show me how to take this picture and make it background?" I pointed to my computer.

Without saying a word, he dutifully walked over to my side of the desk, looked at my computer screen and gasped. "Where did you get this?"

"Oh, I think you know," I teased. "Now I know I can make this into my background, but I don't remember exactly how. I think I need to do a right hand click or something?"

"You can't put this picture on your screen," he whined. "Somebody might see it."

"Jason, nobody will see it. The only other person besides me that ever sees this computer is you. And even if someone did accidentally see it, they wouldn't know who it is. They would just think it was another pretty girl. Now, what do I do?"

He bent over my keyboard and started making the proper adjustments. I reached behind him and ran my hand over his bottom. I could feel the elastic in the panties as I ran my hand over them. "They fit you so well, Jason. Better than I imagined."

He quickly finished his adjustments, then stood up and stepped away from me. "There, it's now your background. Is there anything else you need?" he asked coldly.

"No, I think that will be fine for now. Thanks Jason, you can go." As he walked out the door I watched his rear end to see if there was any swish. When he left I broke into the biggest grin and I had to fight myself to keep from laughing out loud. That had been more fun than I thought it would be. I enjoyed being in that position of power. I wished I could have done something like that to Mikey, but since I couldn't, Jason was going to have to be his surrogate.

I smiled through the entire morning as I was working. At lunch, the real Jasmine poked her head in my office and announced the time. The usual 4 of us walked down to the cafeteria and picked up our food. We sat down and shared some small talk about the weekend, and then Jasmine hit me with the bombshell, "How was your date with Mikey?"

I wasn't aware that she knew about the date, but I said, "It went ok. We had a nice dinner."

"Did you have a nice time afterwards?"

I was puzzled as to just exactly what she meant. "We had a nice time in the lounge."

"I mean later than that."

"What exactly do you mean?" I asked. I was becoming nervous as to where she thought she was going with this conversation. It was none of her business.

"According to Mikey, he spent the evening and the two of got to know each other much more intimately."

My heart skipped a beat and I could feel my face flush and turn warm. I immediately went on the defensive. "Who told you that?" I demanded.

"It seems that Mikey told several people that. I heard it from Janice in sales."

"Well I'm different than Mikey. I don't talk about my personal life or spread stupid gossip." I was pissed off and ready to kill. I was mad at Mikey for being such an ass-hole, and I was even madder at Jasmine for throwing my indiscretion in my face. I finished my meal and excused myself. The other three girls gave me a smirk as I left the table.

I stomped back to my office and slammed the door shut. I threw myself into my chair and started to cry. I couldn't believe it. I hadn't been at this stupid company for more than a couple of weeks and my reputation was destroyed. I would have killed that Mikey right then and there. In fact, I had a couple of fantasies on how I might kill the son-of-a bitch.

It took almost 15 minutes before I could pull myself back together. I dried my tears and gathered my composure. I opened my office door and returned to my desk. I stared at the girl on my computer screen. Oh how I wished that that picture was Mikey and not Jason. Jason was going to suffer because of my anger at Mikey. I knew it wasn't right and I couldn't help myself. The only thing that saved Jason was the fact that he was such a nice kid. A wimp, but a nice kid. In the end, he did temper my anger but I was still going to go ahead with some of my thoughts and emotions.

Jason usually picked me up around 2:30 to go get a soft drink. But 2:30 came and went, and Jason was nowhere in sight. So I went and got him. I walked over to Jason's desk and said, "Jason, let's go get a drink."

"No, I'm not thirsty."

"Sure you are, come on and take a break."

"No really, I don't think so."

"Yes I insist," I said in a low forceful voice. Then I changed to a louder and more cheerful tone, "I'm buying. Let's go."

He reluctantly stood up and followed me out the door. When we were alone in the hall he turned to me said, "How could you? I trusted you."

"You can trust me," I replied.

"How can I do that? You obviously went through my things," he accused.

"Jason dear, I had no choice. There was a little accident."

"What do you mean an accident? What happened?"

"The people in the apartment upstairs let their sink overflow. The water ran through the ceiling and into my apartment. It got some of your boxes wet. I was worried that the water was going to damage something, so I had to open the boxes. I mean, I had no idea what was in the boxes and you never told me not to open them. But don't worry, there was no permanent damage to anything. I had to dry out some of you panties and things, but they'll be fine."

"How many boxes?"

"A few."

"Did you go through all of them?"

"Well that's a funny thing," I smiled. "Once I started going through the damaged boxes, I figured that I might as well hang up and put away some of the clothes that I found. And since I had already started, I decided that I might as well put everything away. It's much better for your clothes if they're properly folded and hung up."

"So you went through all of my personal items?" Again he was very upset.

I decided to change the subject a bit. "Did you know that we wear the same size?" I asked. "You have some really pretty clothes, you know. Do you mind if I borrow some now and then?"

He squeezed his lips tightly together and said nothing. We had reached the vending machines and I dropped a few quarters in the pop machine, "Help your self," I said. He pushed the diet coke button. I slid in another couple of coins and retrieved a coke for myself.

'So why are you doing this to me?"

"Doing what?" I asked innocently.

"You know damn well what," he said through clenched teeth.

"Because I can," I answered.

"So what else are you going to do?"

"I'm not sure yet," I answered honestly.

"Are you going to tell other people?"

"No." And then I thought for a couple of moments. "I don't think so. At least not now. I guess it depends."

His eyes were wide open and showing panic. "Depends on what?"

"On you, dear."

"Me?"

"Yea. It depends on whether or not you want me to tell someone."

"No! I don't want you to totally ruin my life. Is that clear enough?"

He had said that too forcefully for my current attitude and anger level. Not anger at Jason, but anger at the world. "And it depends on how well you behave and listen to me."

He just looked at me and then turned away. I gave him a couple of seconds to collect his thoughts, then I walked around in front of him. I softened my voice. "Jason, don't worry. You may actually enjoy some of this." I gave him a little smile. He did not return the smile. "Shall we return to work?"

The rest of the day was difficult. I tried to work, but my mind kept drifting over to murder and torture. I wished there was some way that I could hurt Mikey as much as he had hurt me. I knew that my thinking was wrong. But I felt so stupid and vulnerable. I finished up early, about 6:00, and I packed up my briefcase, took the Victoria's Secret bag from my desk and went to my car.

I drove home and pulled into the underground parking garage. I walked over to the elevator and pushed the button. While waiting for the elevator, I noticed that there was a trashcan sitting beside the elevator. I reached into my bag, took out Jason's underwear and dropped them in the can.

 

CHAPTER FIVE

On Tuesday morning I put the Victoria's Secret bag back in Jason's desk drawer. I left a note on his desk instructing him to follow yesterday's procedure. I heard him arrive around 7:15 and he came into my office about 10 minutes later. He was holding the bag in his hand.

"Close the door and bring me the bag," I instructed. He handed me the bag and I looked inside. "Very good. Now show me your new panties." He dropped his trousers and they slid down to his knees. "Lift up your shirt tail. Now turn around for me, honey." He struggled to turn around with his pants arranged around his ankles. "Those look really pretty on you. You have a gorgeous tush honey. What do you think? Do you like these better than the ones you wore yesterday?"

He shrugged his shoulders. I raised my voice a bit, "Oh come on Jason. This is fun. Enjoy it. I'm not hurting you. I'm sure that you have an opinion. Which ones do you like the best?"

"These are fine," he grudgingly said.

"Good. I'm glad you like them. Now pull up your pants and come over here. I want to show you today's background picture." He pulled his pants up and walked over. "What do you think?" I had displayed a nice picture of him wearing a cashmere sweater with a short skirt. He had on his blonde wig. "It's a nice ensemble and you make it look very good, Jasmine. But just a bit of advice; the color of that sweater is a bit bold so your lipstick should be less bold. They end up fighting against each other for attention. You see what I mean?"

"I guess."

"Good, and I would recommend suntan hose rather than the dark blue tights that you're wearing. Don't try to throw too much color together. I really like that sweater though. Do you like it?"

A shoulder shrug from Jason.

"Its cashmere and I love cashmere. Its so soft and sensuous, isn't it." Jason didn't answer. "Jasmine honey, I'm only trying to help you here. Do you like the cashmere sweater or don't you?"

"Yes."

"Good. Well that's all. You can return to your desk."

"What are you going to do with the picture that you had on yesterday?"

"Nothing. I plan on putting up a new picture each day. Why?"

"Would you please delete the old picture then? I really don't want someone else to stumble upon it in the future."

I thought about it for a second. "Sure, dear. That's a very reasonable request. How do I do it?"

Jason bent over my computer and showed me how. I patted him on his tush and said, "Thanks. You can go now." After Jason left, I reloaded the picture and opened a new directory called Govt. I put the picture in that directory.

Jasmine stopped by to pick me up for lunch but I was in no mood to be ridiculed. Or at least I didn't want to take a chance of being put in that position again today. I told her that I had to finish a report for my boss, and I was going to work through lunch. I told her, "Don't forget me tomorrow though. Ok?"

At 2:30 I knew that Jason wasn't going to come get me for our break, so I went and picked him up. "I'm buying I announced." He dutifully stood up and followed me down the hall. "So where did Jasmine come from?" I asked. "Did you name your self after our other Jasmine?"

"No. I named my alter ego Jasmine many years ago. Working with another Jasmine is just a coincidence."

"I like the name," I said with sincerity. "Its pretty and feminine. Actually, I prefer multi-syllabic names. Do you have a middle name also?"

"James."

"That's not what I meant. And what do you use for a last name?"

"I've never used either a middle or last name. I always wanted to be known by a single name."

"Like Cher?"

"Maybe."

We reached the vending machines and I bought him his diet coke. "So when did you start dressing?"

"Did you go to my web site? Its in my biography."

"I read your biography. You mentioned the first time that you got caught, but you didn't say when you really got into it. And oh, by the way, I read the part about your dad. Do you remember when I helped you move your stuff to my house? When we were driving back to my apartment after lunch?"

"Yea."

"I said you dad was an ass-hole. In retrospect … I really meant it." I gave him a little smile. He returned the smile. At least a little smile. The corners of his mouth gave him away just the slightest. "So when did you get serious?"

"I was always serious. I knew when I was really young that I wanted to wear girl's clothes and play with the girls. But I didn't really get the chance until mom and dad moved up north and left my brother and me on our own. That is when I started actually buying clothes and things."

"And when your brother was off traveling, you had the opportunity to dress up?"

"Yea, but that was after he graduated and got a job. Before that when he was still in school, it was a little more difficult. I had to be careful that he didn't come home unexpectedly and catch me."

"Did you have many opportunities back then?"

"Actually I did. After mom and dad were out of the way, he pretty much did what he wanted. He stayed over at a friend's about half the time. So I took advantage of those opportunities."

"So why do you do it?"

"I don't really know. I just know that I have wanted to do it ever since I can remember. It's not something you just decide to do one day. You're born with it. It's hard-wired into you. I just know I really like it, and I would be horrified if anyone else found out." He looked at me, almost pleading with his eyes.

"Well, let's hope there is no reason for that to happen," I told him. We had reached the security door into the law department. "Jason, I have one more question that I would like to ask you. Are you gay?"

"No!" he said adamantly. "I'm 100% heterosexual."

'Except that you just don't get many chances to practice it,' I thought to myself.

We returned to the office and our work. That night I threw his second pair of underwear away.

On Wednesday I put a pair of pink bikini panties with a little bow in front, in the bag and put it in his desk. I didn't leave a note on his desk though. I heard him come into the office and I waited for about ten minutes, but he didn't show up. So I called his extension, "Jason, where are you?" I asked.

"I'm sitting right here at my desk."

"You didn't put your panties on and come show them to me."

"What panties?"

"Jason sweetie, I'm not going to play this game with you. I didn't leave a note on your desk because I thought you were bright enough to understand the routine. You know there is a pretty bag waiting for you in your lower desk drawer. There will be a pretty bag waiting for you everyday from now on. So quit stalling and come model them for me, and I'll show you today's picture. Chop, chop, sweetie," and I hung up.

Five minutes later Jason showed up with his little bag. I didn't have to say a word when he arrived. He closed the door behind him and then handed me the bag. I didn't even look in it. I quickly placed it in my desk drawer and waited for him to drop his trousers. Again he had tucked in his penis and the front of his crotch was very smooth. I complimented him on his look. "I really like the way you present yourself, honey. You look so smooth and sleek in front. Now spin around and let me see your cute tush." He spun around and then returned to face me. "You have just a darling rear end. I could bite it," I said with a clear grin.

"So which is your favorite so far? The high cut hip style or the bikini style?"

"They're both about the same."

"No they're not. Every girl has a preference. What's yours?"

"The high cut style, I guess."

"I like you in the bikini cut, myself. We'll let you wear both styles. That way we both are happy. So come see what I've posted today."

He walked over and stood behind my chair while I showed him the computer screen. I had posted a picture of Jasmine in a short dress with a low cut bodice. It was a pretty floral print. She was wearing stockings and 3-inch heels. Today she was a red-head.

"Do you like this picture?"

"Not particularly."

"Why not?"

"I don't know. I don't think I look enough like a girl."

"Oh sure you do. Your figure is especially nice. What are you wearing underneath?"

"I wore a corset laced really tight."

"It did a good job. It pulled your waist in and made your hips more prominent. And what did you do for boobs. They look very real."

"I have a pair of breast forms. Size 34B."

"They look good. Your figure is really nice in this picture. But can I make a couple of suggestions?" I looked at him, but he said nothing. "I'll take that as a yes. The skirt on your dress is clinging to your stockings. Either wear a short slip underneath, or get yourself a can of anti-static spray. Either will allow the dress lo lay smoother. Second, if you're going to show that much cleavage, wear a necklace that drapes a little low. Some girls take a pendant necklace and lay it just above or just in the cleavage. As it is, you have too much skin without something to pull the eye away. Understand?"

Jason shook his head yes.

"I didn't hear you. Do you understand what I'm saying?"

"Yes."

"Good. And finally, never use blue eyeshadow. Unless you're trying to be campy or look like a drag queen, blue almost never works. Stay with earth tones, smoky gray for evenings and if you really want some more color, go with lavender or even pink. Ok?"

"Yes."

"Good. Is there anything else?"

"Did you erase yesterday's picture."

"I sure did sweetie. Ok?"

"Yea."

"Well then, back to work." I watched him walk out and again I didn't notice any swish. Jasmine was obviously making that up. But a thought ran through my mind – he might look nice with a swish. I chuckled and went to work.

I worked through the morning and had lunch with the girls. I think they got my message from yesterday, because no one brought up Mikey. At one point Jason walked by the table and never said a word. Terri noticed the lack of civility. "No hello from Jason? He must be getting stuck up."

"Maybe that's his problem," Jasmine said. "Maybe he got something stuck up his ass last night." The other girls started laughing.

"He did look like he was walking a little lopsided today." They never passed up an opportunity to poke fun at him.

At 2:30 I went over to Jason's desk and asked him to go to the vending machines. "You know Jason, you used to come to my office and pick me up for our afternoon break. Why don't you come get me anymore?" I was teasing him and he didn't like it.

"I'm very busy."

"Well starting tomorrow, I want you to start picking me up again. No more sulking. I know you're mad at me, but you'll get over it. And the sooner the better. We're still friends, right?"

He didn't say anything.

"Jason, honey. Neither one of us has any friends at this place. We're all we each have. We have to stick together."

"Except for the girls that you eat lunch with and Mikey."

I tried to ignore the Mikey reference. "That's a bit different, Jason. Girl's usually have lunch together, and the two of us can't eat together."

"And why not?"

"Because of office politics and gossip. The first thing you know, people will see us together and think something is going on. It's inevitable. Then after the rumors fly all over the company, HR will step in and move one or the other of us to a different department, because they can't have us working together. That's the way it is in big companies. You know that."

"And what about Mikey?"

I stiffened at that name. "What about Mikey?"

"Aren't you and Mikey an item?"

"Not anymore. You don't have to worry about Mikey. He never was and never will be my friend. And that assumes that I don't murder him!"

"Then the stories are true, aren't they?"

"I don't know what stories you're referring to and I don't care to know. Subject closed."

We reached the vending machines and he stepped in front of me. "Let me buy you a coke today. I think you need it more than I do." He grinned ever so slightly. I was pleased. The rest of the afternoon passed in typical routine.

That night after I reached my apartment, I threw away Jason's third pair of underpants.

On Thursday I gave Jason a plain white pair of high-cut panties. He didn't have any other colors in that style. On Friday we tried something different. I gave Jason a pair of his padded panties. They had extra padding on the derriere and gave the wearer a plumper, more feminine look. Jason came into my office and handed me the little bag with his male underpants in it. As usual, I had him drop his trousers so I could see that he was wearing his panties du jour. They did plump up his tush. "Pull your pants up, sweetie. I want to see what you look like from behind."

He pulled up his dockers and fastened his belt. His dockers were a bit larger and more baggy than I had been expecting. When he turned around I could barely notice that he was wearing any padding. I was disappointed. I had him come over to my desk and I showed him the daily picture. Jasmine was wearing a pantsuit with piping around the cuffs and neck. It wasn't very becoming and I pointed out why. Jasmine was a bit disappointed but understood my critique. She was a very attentive learner. When I was finished, Jason again asked if I had deleted yesterday's picture. "No, why don't you handle that from now on, ok?"

Jason leaned over the keypad and began looking for the picture. When he bent forward the rear of his trousers pulled tight, and I could see the extra padding from his new panties. They gave him a much fuller, and feminine buttom. I was pleased. When he left I reloaded the picture.

For some reason Jasmine never stopped by to ask me out Friday night. Lunch was typical. We insulted Linda behind her back. We ripped apart two other secretaries who had obviously dressed for Friday night hunting, and of course we threw a few comments in Jason's direction. No one noticed Jason's enhanced derriere and I was a little disappointed. Maybe next time, I thought.

At 2:30 Jason came to my office and asked me to join him for a walk down to the vending machines. "Thank you Jason, I would be happy to join you." When we reached the hall I took a quick look around to make no one was watching, then I reached down and grabbed Jason's ass. He jumped and quickly stepped away from me.

"Don't do that," he hissed at me.

"Why not, my cute sweetie? You have a great ass."

"Because some one might see, that's why."

"So?"

"So I'd have to charge you with sexual harassment." He gave me an ever so slight grin. I grinned also.

"I have a new word for you today. Callipygian. Have you ever heard it?"

"No."

"To be blunt, it means cute ass. And that's what you have and what you are. Callipygian. I think that would be a good middle name for you. Cally. What do you think?"

"I think you made it up."

"Not a chance," I said. "I'll bet you its real."

"Ok, you're on. There is no way in the world it's real. What's the bet for?"

"Winner decides?"

That stopped him for a moment. That was a real bet and he knew it. And I knew, or I was pretty sure, what his choice would be. I knew it was churning through his mind. "Ok, but it has to be in the dictionary."

I held out my hand. "Then it's a bet. Now all I have to do is decide what I want. Hmmm … " I knew it was real word and I had already decided what my claim would be. And we would have done it no matter what.

We returned to the office and went to his desk. He took out a dictionary and opened it to the Cs. "How do you spell it?"

I smiled. I knew he would never find it in an abridged dictionary. I spelled it out. "Ah ha! It's not here. I win," he gloated.

"Not so fast Kreskin. Let's go look at a real dictionary." The office had an unabridged dictionary back in the documents area. I led him back to the documents area and looked around to see if any one else was there. The place was empty. I opened the dictionary and quickly found callipygian. The smile on his face dropped to his shoes. "Well there you have it sweetie." I reached down and squeezed his ass. "Dinner. Tomorrow tonight. My apartment at 6:30. Don't be late." I pursed my lips and blew him a kiss. Damn I was good!

 

I spent the day cleaning the apartment and shopping. I wanted to put on a nice dinner for Jason. This was going to be an awesome evening. I was thrilled with my devious thinking. Not only did I know that I was going to enjoy this, but I was pretty sure Jason was going to be ecstatic. Only, he would never admit it.

At 6:39 the doorbell rang. I strolled over in my designer jeans and cashmere sweater and opened the door. "Hello Jason," I said seductively. "Welcome to my web." I gave him a bewitching smile.

"Ahhh … hi." I already had him back on his heels. I pulled him into the room and gave him a quick kiss on the cheek.

"What have you brought me?"

"Ahhh … wine," he said in a rather stunned voice.

"Wonderful. Red. Are you a wine connoisseur?"

"No."

"Neither am I. Red is supposed to be served at room temperature, but I prefer my wine cold. Do you mind if I put it in the freezer?"

"Ok." Jason was so assertive and decisive … not. I smiled at that thought. I led him into the kitchen.

"Would you mind giving me a hand? Do you like pasta?" I didn't give him a chance to answer. "Here put this on," and I held out an apron for him. He put his arms through the straps and I walked behind him and tied the straps. It was frilly pink apron and looked very feminine. I grabbed another apron, yellow, and put it on. "Would you mind straining the pasta please, I want to work on the sauce a bit longer."

"What do I do?"

"Take the pot over to the sink and pour it into the strainer. That will eliminate the water. Then take the pasta out of the strainer and put it back in the pot and place it on the stove." He followed my instructions. "Now come over here and stir this sauce. I have some garlic bread in the oven and I want to check on it." Again he did as he was told.

I continued to give him his instructions and he followed them as much as he could. Finally I told him, "Go to the freezer and get out your wine. There are two chilled wine glasses in there also. I told you I like my wine chilled. There is a corkscrew on the counter over there. Fill the glasses and bring them to the table."

"How did you know that I was going to bring wine?"

"Because I own you, Jason. Simple as that. Now shall we eat?"

We both sat down and I filled his plate with pasta then handed him the garlic bread. "Do you like pasta?"

"No."

"Good, enjoy. How about wine? Do you like wine?"

"No."

"Good. Prost!" and I made him clink glasses. We ate in silence for a few minutes. "So Jason, how was your week?" I asked innocently. He stared at me. "I'm making conversation. You have to talk Jason. Otherwise your food fills up your belly and causes you to barf it out later."

"Good. That should be fun to watch."

I laughed. "You do know how to charm a girl." He actually smiled a bit also. "How was your week? Be honest now."

He was silent. I could tell he was thinking of an answer and I allowed him some time. "I was scared."

"That's nice. What else?"

"I lost my trust in someone that I liked."

"That's nice. What else?"

"I felt belittled and trashed like never before."

"That part's a lie. No one has ever treated you as badly as your father. And truth be known, you liked parts of what you did this week. Admit it."

"No I didn't. I've never felt so trapped, so scared and so intimidated in my life."

"Most of that is true. But it doesn't alter the fact that you liked it. Somewhere deep inside your gut, you liked it. Admit it."

"I did not and no matter how much you try and salve your conscience, it isn't true. You treated me like a piece of chattel and you're the one that liked it. Not me."

"You know sweetie, you might be right." I took another bite of pasta and smile at him. "Do you really hate pasta?"

"To be honest …"

"We can be honest," I said.

"No, pasta is not one of my favorites."

"That's nice. Have some more," and I threw another large scoop on his plate.

He looked me in the eye. "What is it with you? Why are you doing this? What do you want from me? Are you trying to crush me? Destroy me? Why?"

I could see a tear in the corner of his eye. I had a momentary pang of guilt, but it quickly passed. I knew he liked this and wanted this, whether he knew it or not, and whether he would admit it or not. "Why? I told you why Jason. Because I can." I gave him a sinister smile. I could see him cringe ever so slightly.

"Finish your pasta. We have sherbet for dessert."

The rest of the meal's conversation was confined to meaningless etiquette. As the meal came to an end I asked, "How was it?"

"I've had worse."

"Well thank you. I will take that as a compliment. Would you like anything else?'

"Maybe just a wee bit of wine."

"Oh, I'm sorry Jason. No more alcohol now. We have a big night ahead of us, and I don't want you getting tired too early."

His head jerked up, he looked me in the eye and his head listed ever so slightly to his right. "What do you mean a big night?" he asked suspiciously.

"Were going out to a club, Jasmine."

I could see the breath rush out of his lungs. "What do you mean we're going to a club?"

"Well," I began with a big breath, "as I understand it, Jasmine has never gone out in public. Am I right?"

"No. I'm not going out."

"Sure you are Jasmine. We're going out to a great club called Glitter. I used to go there all the time with my old roommate. It's a gay bar." His eyebrows popped up. "She was a lesbian and loved the place. And on Saturday nights they have a drag show at midnight. Has Jasmine ever seen a drag show?" No answer. "Jasmine? Have you ever seen a drag show?"

"No."

"Trust me. This will be the most memorable night of your young life. In a way, this is a birth. A re-birth. It will be the first night out ever for Jasmine. And she will love it. Now, we have to start getting ready. How long will it take you to get made up?"

"I'm not going out in public."

I stood up, put my hands on the table and leaned across towards Jason. I used a very steady, very deliberate and very forceful voice, "Yes you will dress up and yes you will go out with me. You have no choice in this matter. It is what I want, and it is what you want. Now quit being a pain in the ass and answer me, how long will it take you to get ready?"

"Probably an hour or two. I have to shave, put on my makeup … probably an hour for all of that, then dressing ..."

"Ok, then let's get started. We can forget about the dishes tonight. I'll stack them in the sink and you go clean up." He looked at me. "Go! Now!"

"I don't have anything," he said exasperated.

"Calm down. Everything that you need is in the spare bedroom. I put away all of your things. Take a look around and you will find everything that you need. Now, take a deep breath, relax and go. Trust me, you will have a wonderful time. Its what you've always wanted. Stop denying it, grasp the opportunity, thank me and go!"

He went, but he didn't thank me. He would. I was pretty sure of that. Maybe not tonight, but someday. I could wait. And in the meantime, I was going to enjoy the opportunity that had dropped into my lap.

I stacked the dishes in the sink, then went and got ready. I brushed my hair and gave it a quick spritz of hair spray. I sat down in front of my vanity and applied a light coat of foundation, and brushed on some blush to hi-lite my cheekbones. I brushed out my eyebrows with a light brown color, applied eye shadow and fluffed my eyelashes with a dark brown mascara. I outlined my lips and then filled them in with a cranberry colored lipstick. I switched from studs to drop earrings, put on a gold necklace and some dangling bracelets. A nice fashionable, but casual look. I was ready. I went to check on Jason.

He was still in the bathroom. I knocked on the door, "How you doing in there?"

"Fine."

"You presentable?"

"No.

"Good, I'm coming in." I gave him just a moment to shout no, and he didn't say a word, so I walked in. He was sitting on the toilet, naked except for his padded panties. His face was covered with 5 or 6 blood stained bits of toilet paper. He looked hilarious. I couldn't help my self and I started laughing. I started laughing hilariously. I fell backwards against the wall and slowly slid to the floor, laughing at the top of my lungs. He stared at me, his eyes glistening from tears. "Are you the same Jason as the one in Friday the Thirteenth?"

That broke him loose. I've never seen anyone laugh and cry at the same time. He grabbed another handful of toilet paper and wiped his eyes. "I can't do anything right," he sobbed. "I wanted to shave extra close, and look what I did." He started sobbing again. "I can't even be a failure without failing."

That got my attention. I quit laughing and stood up. "Come here," I said. "Pull that toilet paper off your face." I turned on the cold water and let it run until it was good and cold. I filled up the sink and handed Jason a washcloth. "Come over here and soak your face with cold water. That will stop the bleeding and prevent any scabs from forming. Get to it," I instructed him. I stepped back and continued to encourage him. It took a full fifteen minutes before the bleeding was fully stopped.

"See? The cold water even reduces the localized swelling from the cuts. Now, what do you need to do next?"

"Brush my teeth and apply some anti-perspirant."

"Ok, get to it."

He started to loose his composure again, "I don't have any."

"Yes you do," I quickly said. "Come on," and I led him into the spare bedroom. "All of your stuff is here," and I gave him a quick tour as to where I had put everything. "Here's your toiletries. Go brush your teeth and then come back here."

He returned in a few minutes. "Ok, now what do you do?" I asked.

"Usually I put on my under garments," he sniffed.

"Fine, then let's do that. I'll help. What do you want first?"

"My corset."

I knew exactly where it was. I went to his dresser and took it out. "How do you put it on?"

He put it around his waist and hooked the eyelets in the front. "Can you pull it tight in the back?"

"How? Where?" I asked.

"Grab the laces in the middle and pull them as tight as you can." I did as I was told. "Tighter," he said. I pulled as tight as I could. "Tie it in a knot, otherwise it might come loose."

I tied a knot. "Ok, now what?"

"My bra and breast forms." I showed him the correct drawer for his bras. I had left his breast forms in their molded boxes and had placed them up in the closet. I took them from the shelf and set them on his dresser. He picked out a white, underwire bra and expertly slipped it on and fastened it behind his back. He took the breast forms and squeezed them into his bra. He pushed them around for a minute until he was satisfied with their placement.

"Looking nice," I told him. "Now what?"

"Nylons."

I showed him the correct drawer. He had tons of nylons. He took out some knee highs and sat down on the bed. "Wait," I interrupted. "You can't wear those. I want you to wear a skirt."

"I can't," he protested, "I have hairy legs. And besides, you're wearing jeans."

Yes, his legs were hairy. "Well, what did you do in your pictures?"

"I wore dancer's tights."

"Ok, wear dancer tights."

"That won't work. They look ok in pictures, but in the real world they look fake and hokey. It won't work," Jason complained.

I had a flash of inspiration, but it would have to wait until another time. "Ok, maybe jeans would be better for your first night out. They do eliminate a lot of problems." Jason had to really struggle to get the stockings on. The corset made it extremely difficult for him to bend over and reach his feet.

"Now I need a camisole." I picked out a very attractive, pink camisole that was covered with lace and handed it to him.

"Next?"

"Make-up."

"Ok, everything is over here. Wait," and I went and picked up a shoebox. "Pick out what you want and place it in here." He went through the thousands of bottles and tubes and cosmetics that he owned and picked out the necessary ones. He placed them in the box. "Ok, follow me. We can use the vanity in my room."

I led him into my bedroom and sat him in front of the vanity mirror. "Let me help," I offered. "Where do you usually start?"

He handed me a small container labeled 'beard-cover'. "The first thing I do is take a sponge and use this to cover my beard"

"Ok, let me do it." I used the sponge to wipe the heavy goo over his beard. "It would be better if you got electrolysis and got rid of this beard," I joked. Another inspirational idea popped into my head. I filed it for future use. "Now what?"

"I use translucent powder, just a bit to set the beard cover."

"No problem," and I took a brush and applied a light coat of powder. "Next?"

"Now I usually apply regular foundation over my entire face and neck."

Man, we were starting to apply a lot of makeup. There has to be a better way I thought. I took a fresh sponge and applied the foundation over his face and down over his neck. "How's that look?" I asked.

"That's nice. Next, another light dusting of powder to set it." That took me just a minute or two. "Now I usually apply some blush."

"Ok, were going to change the routine a bit. The blush you use is way too dark. It might work on a model with high cheekbones, but it isn't for you. You need something lighter. Give me a sec. and I'll be right back." I went back to his room and searched through his collection of cosmetics. I found a lighter, pinker color and returned to Jason. I brushed it lightly over his cheeks and blended it up towards his hairline. "Watch what I'm doing here. I think this will work better for you and your complexion."

"I think that looks better than what you usually do," I said. "What do you think? Is it ok?"

"Yea, I guess its ok."

"Good. Now what?"

"Next, I do my eye brows."

"Your eyes. Great. First things first. Wait here just a minute." I went to the bathroom and located my tweezers. I sat sown in front of Jason and told him, "I'm going to clean up your brows."

"No," he yelled. "You can't pluck my eye brows."

"Yes I can, and yes I will. Quit panicking every time I do something. I'm going to clean them up, pluck a few stragglers and even them out. It won't kill you, so sit there and be quiet."

"But …"

"But nothing," I said. "I'm not going to going to arch them and make them look real femmy." And then my third inspiration of the night hit. I'd have his eyebrows waxed at a salon later. I was a genius!

After plucking his brows, I took his brow pencil and colored in a nice clean line. Then I took his eyelid sealer and applied a first coat over his eyelids. After it set for a moment I brushed on a light pink shadow, spreading it up high under his brows. I wanted to give him a bright-eyed innocent look. I put a light lavender over his lower lids, and then used a tiny bit of gray through the crease.

Next I found a light brown eyeliner and outlined his eyes. I didn't take it all the way to the inside corner of his eyes. I wanted to try and pull the look to his outer eye. I smudged the eyeliner with a brush and gave his eyes a nice soft look. I handed him his lash curler and told him that he had to curl his own lashes. When he finished, I applied two coats of dark brown mascara for him. I finished by taking a lash brush and combing out the lumps and blobs. His eyes looked nice, not perfect, but passable for his first night out.

"Ok, lips. Right?"

"Yes," he said.

"Before I show you how to apply lipstick, what are you going to wear?"

"I don't know. Can you help me decide?"

"Sure, let's take a look at that extensive wardrobe of yours." First I helped him pick out a tight pair of stone washed jeans. "Let's give you a top that hangs out and is nice and long. You don't want something so short that when you bend over it pulls up and exposes your cami." I found a nice silk blouse with cap sleeves and a square neckline. It was a soft powder blue color.

"Shoes," I said. "How good are you with heels?"

"Decent I think."

"Do you want to try heels?"

"I think I can."

"They will make you a lot more dressy." I found him a pair of 3-inch straps and helped him put them on. That corset really did make it tough for him to bend over. "You look good in heels," I told him. "Let's go finish your makeup." I looked through his cosmetics until I found a lipstick color that I thought would match his top. Then I searched for a slightly darker lip liner. I found a great, although not perfect, match. It was amazing how many cosmetics he had.

I sat him on the bed and applied first the lip liner, giving him slightly larger and more pouty lips, and then the lipstick. "Here, take this Kleenex and blot your lips." I pressed a bit of powder on his lips, and then re-applied just a bit of lipstick. "There, that should last for a while. You see how I did that right?"

"Yep."

"Good. I do like that color on you. What do you have for jewelry?"

That brought my fourth inspiration for the night. He needed to have his ears pierced. I found some clip on earrings that I liked. I gave him a slim silver necklace, bracelets and some rings. He must have spent a fortune on his hobby. I couldn't believe all of the jewelry we had to choose from. All that was left were his wigs.

One by one we tried on his wigs. First we put on his short blonde wig. It looked cute. Next we tried his long black wig. It was ok, but I wasn't sure that black was his color. Next was his curly red wig. I liked the color, but the long collection of curls was a bit over the top, at least for tonight. Last he put on his long, straight brunette wig. I decided that it had the best chance. To be honest, none of them were quite right for him. I straightened the wig and combed down his bangs. Then I brushed out the wig and tried to get it to lay flat. It wasn't a very expensive wig and it showed. Jason's hair was going to be the weak part of his look. But it was the best we had.

"We're finished sweetie. Pick out a nice perfume and spray it on your neck and wrists." He – she- did as I instructed. "Do you have a purse? I put them here in the closet." We searched through a dozen purses and picked out a nice brown purse with a long a strap. "Ok, come out into the living room and let's take a look at the new Jasmine."

I stood off to the side of the room and watched Jasmine walk out. My first impression was very positive. She was rather small and had a nice figure with lots of curves. I thought her chest and hips were well proportioned and fit her stature well. Her hair was off just a bit, but I knew that already. I wasn't sure if it was the color or the style, but I certainly wasn't satisfied with the look.

Her best feature was her face. Unlike most men, she did not have an oval face. It was wider, (dare I say round?) like a good model's face. She had a small, upturned nose that was very feminine when surrounded with made up eyes and red lips. Her cheekbones were flat, but the blush helped. The makeup gave her a very pretty face. Her face was definitely her best feature.

She claimed that she was ok in heels, but she walked like a cow. She was going to need a lot of work on walking, moving her arms and hands and reducing the amount of sway in her hips. She didn't hold her head right either. She tended to slump her shoulders and hold her chin down. I was going to have to train the girl and make her work at it.

And then there was her voice. That would take a long time, I knew.

But for her first night out, she would be fine. We were going to a gay bar and transvestites were always accepted there, so there wouldn't be any problem with passing. If she did fool a few people, that would be frosting on the cake.

"We're going to walk down to the car," I told her. "But first walk across the room." She was trying to place one foot in front of the other. "Stop placing one foot in front of the other, like your trying to walk a tightrope."

"But that's how models walk," she explained.

"Exactly. That is how models walk when they're modeling, but that is not how normal women walk. Besides, it's forcing your hips to sway too much. You look like you're working the street with those hips. Now try it again. More natural."

She walked across the room a couple of times. "Better, now take shorter steps. You're a beautiful girl basking in the attention of all the men as you walk across the room. Slow down and enjoy it." She crossed the room again, and looked a bit better. "Now hold your elbows closer to your side. Move your lower arms more and your shoulders less. Better, better. This time, look where you're going. Hold your head up higher. You want to look those men in the eye as you glide past them. Don't look at the floor so much."

She tried, but kept glancing at the floor. "I'm not sure that I can keep from looking at the floor. I'm not that sure of myself in these heels, and I'm afraid of stepping on something or tripping over something."

"Ok, that will take practice and confidence. Keep your purse strap over your shoulder and hold the strap with one hand. Elbows in," I reminded her. "Less hips. Small steps. Chin up."

"Blah, blah, blah," she screamed. "I can't do all of that at once."

"You had better learn, or everyone in the world will know that you're a man in heels! And you will NOT walk that way when you are in my company, or I will leave you behind. Try it again." I made her cross the room a couple more times, then gave up. "I guess I'll have to take you as you are. What do you have in your purse?"

"Nothing."

"That's not going to work is it? Let's get you the things you'll need. Go find your lipstick and lip liner, your facial powder and a brush, and your mascara. Do you have a small hairbrush? Put a bottle of clear nail polish in too. You'll need your wallet, some Kleenex and a tampon."

"A tampon? What am I supposed to do with that?"

"Use your imagination," I teased. "Every girl in the world carries an emergency tampon in her purse. You will too. I'll get one for you."

After filling her purse I asked, "Are you ready to meet the world?"

"I don't know," she sighed.

"Well it doesn't matter, does it? What I say goes, and I say let's go." I led her out the door and down the hall towards the elevator. "Chin up," I reminded her. We stepped into the elevator and she slumped one hip and stood like a man. "Stand up! You stand like a man in drag. You're a young lady, act like a lady!"

"Yes ma'am!"

"And I like that respect. You shall show me more of it."

The elevator reached the garage and I led her to the passenger side of the car. "Do you know how to sit down like a lady?"

"Yes." She turned sideways to the seat and sat down with her feet together on the pavement. Then she swung both feet together into the car. She looked up at me asked, "How did I do ma'am?"

"Not bad. But when you're in pants, you can step into the car." I smiled at her and shut her door.

I sat down behind the wheel and placed my purse on the floor behind me. "Put your purse on the floor between your legs," I instructed. I started the car and we drove to Glitter.

Glitter Night Club is located in the gay district. On Saturday nights the entire area is a hot bed of activity. People come from all over greater Chicago to dance and be seen in the various clubs. And all of those people meant lots of cars with only a limited amount of parking spaces. We had to park 5 blocks away. Which was ok with me, because it gave Jasmine more opportunity to work on her walk.

"Chin up, shoulders back," I reminded her over and over.

We had to stop at a corner for the streetlight to turn. Jasmine turned to me and said, "I'm getting sick of all the instructions. I'm trying! You're starting to sound like a bitch."

I gave her my most devious smile, "If you want me to be a bitch, you haven't seen anything yet. I'll treat you like a piece of shit. Is that the way you want it?"

She dropped her eyes and looked at her heels. "No, I'm sorry."

"You certainly are sorry, and your only chance of ever passing as anything other than a man in drag is by listening to me and doing what I tell you. Is that asking too much?"

"No."

"Good. Elbows in." As we walked the rest of the way to Glitter, I realized I was starting to like this situation. I was totally in charge. Even though I liked him, and even felt sorry for him, I had no trouble reverting to an authoritarian mode. I felt no guilt or shame at all. I was learning something about myself that I had never realized. I didn't think that I was hurting him, and I knew that he did indeed like crossdressing. And I suspected that being forced into this position, allowed him to rationalize his doubts about wanting to look and act like a girl. The situation was cathartic for both of us.

We reached Glitter and walked in the front door. There were people all over. The bouncer stopped us as we came in. "Hi girls. Can I see some ID?" I handed him my ID, he glanced at it and gave it back. Jasmine gave him hers and he took a few extra seconds to look at. "Thanks girls. Have a great time," and he waved us in.

I didn't have to worry about Jasmine's walk anymore. The place was so busy that we were bounced around like balls in a pinball machine. We struggled to a stand-up table near the dance floor. We set our purses on the table and laid claim. The music was being pumped out at ear splitting level. The floor was packed and the crowd was bouncing up and down to the music. There was no way to tell who was dancing with whom.

Jasmine and I didn't even try to talk, it would have been futile. One dance morphed into another as the DJ kept the music pounding out a rhythm. People came and people left the floor and the overall mob kept bouncing and bopping. A waitress finally came to our table and I yelled in her ear. She eventually found her way back with 4 cokes. I was thirsty, and I knew we wouldn't see her for another half hour or more. I pushed 2 cokes over to Jasmine. She chugged her first coke like a guy. I shook my head in disgust and pulled a mirror from my purse and handed it to her. I pointed to the corners of her mouth. She had smeared her lipstick because she wasn't careful. I handed her other coke to her and motioned for her to follow me.

We carried our drinks into the restroom and waited for a place at the vanity. The room was packed and each girl was checking her makeup and touching up imperfections. We made our way to the counter and I set down my purse and reached into hers. I took out her lip liner and a Kleenex. I carefully touched up the corners of her mouth and then re-applied her lipstick. Not another girl gave us a second look.

"Act like a lady," I told her. "Think before you act. You're a dainty feminine flower. Be one."

A girl standing nearby said, "That's right girl. Wow 'em with your charms. You got 'em."

We both laughed and gave her a thumbs up. We carried our drinks back into the noise and mayhem. We found a place by the bar and a single stool opened up. I motioned for Jasmine to sit down. I figured her heels were probably starting to tire her feet. I motioned for her to cross her legs. She didn't look right so I took my hands and pushed her legs into their proper position.

When I used to frequent the Glitter, there was one transvestite that I thought looked reasonable, and I enjoyed talking with her. Her name was Tara. She was at the club and spotted me. "Hi, Karen," she yelled. "I haven't seen you in awhile."

"I got a knew job and I moved across town. How have you been?"

"Great. Whose your friend?"

"Jasmine." I yelled. I introduced the two of them. They began talking and ended up talking for the rest of the night. They bought each other drinks and had an animated conversation. I couldn't hear what they were saying, but several times I saw Jasmine point at me. Sometimes they laughed and sometimes Tara gave me a disgusted shake of her head. I had an idea what they might be talking about and I smiled back.

I was watching the action around the club when I saw Gloria. I motioned to Jasmine to stay where she was and I bumped my way over to Gloria. We hugged and then I asked her to come outside with me. We got our hands stamped and went outside where it was cooler and quieter.

"Gloria, how have you been?"

"Wonderful. How's the new job?"

"It sucks. I'm working in a pig pen. Its full of pigs."

"Welcome to the real world sister."

"Thanks. Can I ask a favor?"

"Why not?"

"I'm serious about the job. It pretty much sucks as far social life goes. All of the other lawyers are men, and not a single one will give me the time of day. There are a couple of secretaries and paralegals that eat lunch with me, and that is about the extent of my human contact. The problem is, one of the girls is hot for me. She knows I'm hetero, but she won't give up. I'm real short on friends and I don't want to get too blunt and chase her away."

"I get the picture. You are sexy, Karen. How can I help?"

"If I bring her here, maybe we could 'accidentally' meet up with you. And maybe when I'm off buying drinks or sitting in the girl's room, you could kind of set her straight?"

"Is she cute?"

"Yea, she is very pretty."

"How old is she?"

"I think 27."

"Yea, I'll help you out. When?"

"How 'bout I give you call? Maybe next Friday? I'm not sure."

"I'd be glad to help out an old roomie. Especially if she brings me a live hotty. So is that what brings you back to your old roots?"

"That, and I brought a TV down here."

"Karen, you doing charity work?"

"Not quite. It's a rather interesting situation. He's a TV but really shy. I've kind of taken over and I'm forcing him along. It's fun. He has to do what I tell him to do."

"What, are you blackmailing him?"

"In a way. I have never even thought of doing something like this, but I'm having a fun time. It's my way to get back at all of the ass-hole men I've ever known."

Gloria laughed. "Sounds like fun. Can I help? Just kidding. Is he inside?"

"Yea."

"Show him to me, will ya?"

I led Gloria back inside and took her over to Jasmine. I introduced her to both Jasmine and Tara. "Hi girls," was the first and only thing I heard Gloria say. They talked for a long time and I saw them laugh several times. At one point I saw Gloria reach out and squeeze Jasmine's boobs. Then she reached over to Tara and squeezed her boobs. A little while later she took both by the hand and led them onto the dance floor. I caught glimpses of them on and off, but they were swallowed by the pulsating crowd. I took control of the bar stool, sat down and kept an eye on purses and drinks.

I glanced at my watch and noticed that it was after midnight. Finally, I thought. That meant that we were getting close to the drag show, and the super loud music would soon come to an end. Thankfully, it only took another five minutes to finish the dancing. The girls came back, panting and sweating. Jasmines face was shining, and it looked like her triangle was getting glossy. "Tara are you going to stay for the show?"

"Absolutely!"

"Would you watch our drinks? Jasmine needs to fix her face."

"Go," she said. "I'll be here."

I handed Jasmine her purse, took her by the arm and led her to the girls room. The crowd was starting to thin out and it was easier to get in. "Go take a pee, then I'll fix your face. You were sweating on the dance floor and it's blemishing your makeup."

Either she really had to pee, or she was having trouble with her zipper. It took a long time for her to resurface. The room was still crowded as I started instructing her on her makeup. I turned her towards the mirror and pointed out the spots where her sweat was thinning her makeup. I dabbed a bit of foundation on the spots and smoothed it out. Then I gave her the brush and powder and told her to brush on a thin layer of the powder. A couple of the other girls glanced over at us, but no one said a word or raised an eyebrow. As long as she was wearing lipstick she was welcome in the girl's room. Only in a gay bar do you see what tolerance is really about, I thought.

We went back to the bar and met Tara. I ordered a beer for both of us, since it would probably be the one and only alcoholic drink for either of us. When the beer arrived I said, "Be a flower. Don't guzzle it." Both she and Tara gave me dirty look.

The house lights dimmed and the stage lights came on. The little disco ball above the stage started rotating and jewels of light spread across the room. The hostess came out on the stage to a rousing applause. She welcomed the crowd, told a few ribald jokes, and traded a couple of insults with two guys who laughed hilariously. Then she introduced their first entertainer, a buxom beauty from Texas.

Annie Oakley came on stage wearing a frilly skirt and western shirt, boots and spurs. She began lip syncing a song that I don't recall. It was a rompous cowboy song, and the crowd hooted and hollered and clapped along. Tara took a dollar bill from her purse and walked up and handed it to Annie. She blew Tara a kiss and kept 'singing'. A few others took up money and each received an air kiss or a wink. Jasmine was watching with rapt attention.

Annie finished to a nice applause and ran back stage. The hostess returned and started trading ribald insults with the two guys again. Then she introduced the second entertainer. She was a tall, gorgeous beauty who could dance like a Rockette. She performed a high powered number with plenty of dancing and lip synching. She twirled, pirouetted and did the splits. She had the folks lined up around the stage waiting for her to finish so they could hand her their dollar bills.

Jasmine watched the show and was transfixed by the girls. She laughed too long and too loud. She traded whispers and laughs with Tara. She tapped her toe and clapped along with the music. But mostly, she watched with her mouth open. At one point, I reached over and tapped her under her chin to close her mouth. She gave me a quick grin and then turned back to the show.

The show lasted a little over an hour. It was late and time to go. I told her we needed to leave. She and Tara traded phone numbers and email addresses and we finally headed home. As we stepped outside, the cool air blew over us and it felt great. It was so much quieter my ears felt like there was a pressure on them, like walking into an anechoic chamber. I put my arm through Jasmine's and we quietly walked side by side. We listened to the sounds of the city, the chatter in the distance, the sirens, the laughing outside the bars as we passed by them.

"How was your evening?" I asked.

"Ok." It was if she was shrugging off a boring time. I knew better.

"What did you give Tara?"

"My email address."

"Is that all?"

"We traded telephone numbers also."

"She was attractive," I said. Jasmine gave me a nasty look. I smiled and said, "You did seem interested in her."

"Get real."

We reached the car, and we both climbed in. I began navigating the night-time streets back to my apartment. "So did you have a nice time?"

"I guess." She was non-committal.

"Would you like to do it again?"

She shrugged her shoulders.

"Well if your not that interested, I'll throw out all of your clothes tomorrow. I thought you wanted to do this, but maybe I was wrong." She looked at me. "Silly me, I thought I was doing you a favor, something that you wanted."

"Ok, you win. I loved it. It's hard admitting that to you. I don't … I didn't … You are just so …" It was obvious she was having a difficult time admitting her true feelings.

"What's the matter? Cat got your tongue?"

"Frustrating, intolerable, exasperating, …"

"Thank you. You're welcome. So admit it, you love putting on that bra and feeling the way it tightly hugs you. You love the taste of the lipstick, the smell of your perfume, the jiggle of the bracelets around your wrists, the sound of your heels clicking on the pavement and the feel of your long hair against your cheek. They really turn you on don't they."

"Yes. They do. They always have and you know it. You have me and there is nothing I can do about it."

"Your both right and wrong. I do have you, but there is something you can do." I waited for her 'What?' "You can enjoy it. You can embrace it with your heart and soul. You can live. You can do what I tell you to do."

She didn't answer. She leaned back and quietly enjoyed the ride back to my apartment. She basked in the after-glow, the adrenaline let-down of her best night ever. Back at my apartment I helped her take off her heels, and I released her from the corset. I made sure that she had a good cold cream to clean off her makeup

After she finished in the bathroom, I washed my face and prepared for bed. When I came out, she was standing in the doorway to her bedroom. She was wearing a knee length negligee with spaghetti straps and a plunging neckline. "You have a pretty negligee. Goodnight," and I gave her a quick kiss on the cheek as I headed to my room.

 

I woke up at about 10:30. I rubbed the sleep from my eyes and climbed out of my bed. I put on my robe and strolled out into the kitchen. The table had been cleared from last night, the dishes rinsed and placed in the dishwasher, and the stove was in the middle of making breakfast. Toast and bacon were already lying on a plate. The frying pan was sitting on the stove and the carton of eggs was sitting next to the stove.

I heard the front door close, and Jason walked in with the Sunday paper. "Mornin' sleepy head. How do you like your eggs?"

"Sunny side over. What are you doing?"

"Making breakfast silly."

"No, I mean what are you doing dressed? Don't you know that on Sunday mornings girls sit around in their robes, sip coffee and eat cinnamon rolls while they do the Sunday crossword puzzle?" That threw her off balance. She thought she was going to get an atta-girl and I tripped her up. Damn, I was good.

 

(continued)

  

  

  

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