Jasmine Cally Vail – The Awakening

by

G. L. Hudson

 

CHAPTER SIX

On Monday morning I put a pair of bikini panties and a camisole in the Victoria's Secret bag. Shortly after arriving, Jason came to my office with the Victoria's Secret bag and another a paper bag. He set both on my desk and then closed the door. "Good morning," he said. "I don't want to keep my panties at my current apartment, I'm afraid someone will see them. Can you take them to your apartment and put them away for me?"

"Have they been washed?" I asked.

"Huh?"

"Did you wash them?"

"No."

"Then the answer is no, I will not take them home with me."

"But how am I going to wash them?" he whined.

"How do wash your boy's underwear?"

"I take them to the laundromat, but I can't do that with these."

"Why can't you?" I wanted to know.

"Because someone might see them."

"Well boo hoo. Just tell them you only wear them at work. Or you could say they belong to your girl friend."

"I guess so."

"That's what you could do, but I recommend washing them in your bathroom sink with a mild detergent and hanging them over the bathtub to dry. It's much gentler and the panties will last longer. That's how you should wash all of your dainties. Here," and I handed him the bag. "Don't bring them back until they've been washed." He reluctantly took the bag.

"Take your shirt off, I want to see how your camisole fits." He removed his shirt. I could see chest hair above the bodice. I smiled knowing I would handle that problem this Saturday. "And drop the trousers. I want to see how they go together." He dropped the trousers and showed me his bikini panties. He had his penis tucked between his legs, and he had a nice smooth presentation in front, although he was too flat above. "You look good in women's lingerie. Ok, you can put your clothes back on."

He put his clothes back on and I told him to come look at my computer screen. I showed him another picture of Jasmine and explained how plaids don't go with stripes. As he bent over to delete my last background picture, I could make out the outline of his camisole straps under his shirt. I wondered if anyone else would notice. It wasn't until Wednesday that one of the girls brought it up at lunch.

Jasmine watched him walk by at lunch and then whispered in a conspiratorial voice, "Did you look at Jason when he walked by?" Everyone shrugged. "Look at his shoulders and upper back. I think the swish is wearing a camisole under his shirt."

"No!"

"You're kidding. I didn't see."

"Well look when he goes by next time."

"I'm going to make it a point to stop by his desk this afternoon and get a closer look."

"Wait a minute," I counseled. "If he is wearing a cami underneath, don't say anything."

"Why not."

"Because you don't want to spook him. Let's see if he wears it again. Or if he wears something even more interesting," I giggled.

"Great idea. Let's see how far he will go if he doesn't think anyone notices."

"Exactly," I said, and laughed with the girls.

Early in the week I called and made a salon appointment for the two of us. I set up a hair appointment for me at 10:00 on Saturday morning, and a waxing appointment for Jason at 10:30. I wanted him to sit in the salon for 30 minutes and relax, before I sprung the surprise on him. I told the girl that I wanted his legs, chest and underarms waxed.

On Friday afternoon as we were walking to the vending machines I told Jason, "I want you to come to my apartment tomorrow morning. Be there by 9:30, no later."

"Why?"

"Because I have a hair appointment at 10:00 and I don't want to be late. It's difficult enough getting these appointments and I don't want to make my stylist mad."

"And you want me to come with you?"

"Yes."

"Why?"

"Because we have some shopping to do afterwards."

"What if I stay over tonight?"

"Nope. I already have a date tonight." The bounce went out of his step when he heard that. My date was with the real Jasmine. She had asked me to go out with her after work, I had immediately called Gloria and asked if she could meet us at Glitter. After work on Friday, I drove the two of us to Glitter and was able to get a nearby parking space. We walked to the club and both of us were carded.

"Do you come here often?" she asked me.

"I used to. I lived across the street when I was going to school. It was very convenient, and they have great food if you get here early enough."

We found a table and the waitress brought us a couple of drinks and gave us a food menu. We weren't there more than 15 minutes when Gloria showed up. "Karen," she exclaimed. "What are you doing here?"

"I just thought I'd stop by after work and get a bite to eat and a sandwich. Gloria, this is a friend from work, Jasmine. Jasmine, Gloria used to be my roommate." They shook hands. "Gloria will you join us? We were just about to order."

Gloria sat down and we started chatting away. The waitress came back and we placed our orders. I allowed Gloria and Jasmine to talk as much as possible, and I tried to stay out of the conversation. They were making good headway when the food arrived. Gloria was explaining the area to Jasmine, telling her about the other clubs and the nightlife. I finished eating and excused myself, so the two of them could talk in private. I was hoping Gloria could explain my sexual preferences to Jasmine.

As I was returning to the table, Gloria came walking by on her way to the restroom. "Any luck?" I asked.

"No problem," she said. "Jasmine is a real looker, and we have a lot in common. I think I took care of your problem too."

"Thanks," and I went back to the table.

"So Jasmine, what do you think of Glitter?"

"Nice place. I had a nice talk with Gloria, She's pretty neat."

"Yea, she was a good roommate."

"She asked me to join her club hopping tonight. Do you mind?"

"Not at all. Enjoy yourself. I was feeling tired and was hoping to call it an early evening."

So Gloria had done her job, and there were no hard feelings. Everything worked out for the best.

 

Saturday morning Jason arrived punctually at 9:30. "Let's go," I said as I hurried him out the door. He had brought his clean panties and camisoles with him, and I just tossed the bag on the sofa as we left. It took almost 25 minutes to drive to the salon and get a parking space. I made it just in time. I don't think Jason suspected anything, at least he didn't show any signs. I left him sitting in the waiting area with a couple of fashion magazines to read.

I was having my hair trimmed when I saw the girl walk up to Jason. He sat in the chair and looked surprised as the girl talked to him. He stood up reluctantly and followed her, giving me a quizzical look as he walked by. I smiled at him and gave him a wink. My stylist finished up about a half hour later and I took a seat in the waiting area. I waited another 40 minutes before Jason came out of the waxing room. He walked over to me and gave me a pained grin. "Don't forget to tip her," I said. I motioned towards the desk where he was to pay. He walked over and spent at least ten minutes talking to the receptionist. He turned and slowly walked over to me. He was looking at his feet and he wasn't smiling.

"What's the matter?"

"I have a little money problem," he said very quietly.

"You didn't bring enough money, did you?"

He shook his head no.

"Just use your credit card. They'll take plastic."

"That's another problem. I tried, but the credit card company said I was at my maximum. They won't pay." He refused to look up at me.

"For crying out loud," I said. "You maxed your card? How much is the max?"

"$8000."

"I don't believe it. Have you no common sense?"

He continued to look at he floor and make little wimpering sounds. "Can you help me out, please? I'll pay you back."

"How?" I snarled. I went over to the receptionist and paid his $75 bill. I gave the girl who served him a ten spot.

I stomped out of the salon and Jason shuffled after me. We went back to the car and got in without saying a word. I sat behind the wheel for a minute, collecting my thoughts. "Jason, eight thousand dollars?" He said nothing. "How many other cards do you have?"

"Just that one."

"What did you spend the money on?"

"Computers and clothes."

"Girl's clothes?"

"Yea."

"You've got to do something about that. How much do you pay back each month?"

"Whatever the minimum is."

"Jason!" I yelled. "They're charging you 18%. You'll be in debt for the rest of your life!"

"I know, I know. But no matter how hard I try, I just can't seem to make things even out."

"That's because you're not even trying. That's $85 that you owe me, and I will keep track!"

I wasn't sure if I wanted to continue the shopping day. I had some things I wanted him to get, but he didn't have any money. I sat there and glared at him for a couple seconds before I decided to go ahead and at least get his ears pierced. I'd add it to his bill. I drove us to a local jewelry store and walked him inside.

"Can I help you?" the saleslady asked.

"Yes, my friend here wants to get his ears pierced. I see you have a nice sale in progress."

"Yes we do. With each ear piercing we have a buy one get one free sale."

"Good. He wants two earrings on each ear. One in the lobe and one a bit higher on the outer edge."

"What?" Jason asked.

"Just as you wanted," I said. I stared at him and made it clear that that was what he really wanted. "Right?"

"Yea," he whispered quietly.

"If you'll follow me over here we can get started," the girl said. Jason sat down and the girl pierced first his right and then his left ear lobe. She gave him some gauze to hold over each lobe to catch the blood. When it had essentially stopped bleeding, she put a small post in each lobe. Then she repeated the procedure slightly above each lobe, and again inserted a post.

"Shall we look at earrings?" she asked. She led us to a display of men's rings, and I had Jason pick out a small stud for each lobe, and a small ring for above. "If you purchase those rings, you can pick out two of equal or lesser price."

"Let's look over here," I suggested, and led him to the girl's counter.

"These are for girls," the saleslady said helpfully.

"We know," I answered. "This is what he is looking for. He wants a couple of drop earrings that he can wear to the clubs." The girl looked surprised, then gave Jason a little smirk. Jason smiled back.

We picked out two sets of drop earrings, one rhinestone and one with a purple stone, and I paid for everything. Jason owed me another $80. I put the receipt in a small pocket of my purse. I would keep track of his debts. When we returned to my apartment I wrote the specifics on the back of each receipt and put them in my jewelry box.

I called Jason and we walked into his room. "I want you to wear nail polish tonight. Let's pick out a color you like then I'll help you get ready." He picked out a dark pink with glitter in it. I took him into the living room and sat him down on the floor. I pulled a low coffee table over in front of him and I sat down on the other side. "I was going to have you get a manicure today, but your money situation stopped that. Honestly Jason, we will have to do something about your financial situation."

I picked up a file and began filing his nails. "Your nails are too short to do much with them. All I am going to do is file them round and clean them up. Then we can let them grow. You'll be able to keep them manicured and shaped with regular attention. You will have to wear nail hardener from now on. All of the time. Is that understood?"

"Yes."

"After I'm done filing them, I will apply one coat of color. After they dry I will apply a second coat. That will be all we'll do for this weekend. On Sunday, you will remove the color and apply the hardener. But you will leave the polish on your toenails."

"You said 'this weekend'. Does that mean we'll continue to do this every weekend?"

"That depends entirely on you."

"You mean I get a choice in this?"

"Heavens no, silly girl. What I decide depends on how you react. You might want to think about your attitude. I might decide to totally humiliate you in front of your family and friends, I might decide to help you achieve your greatest fantasy, or I might do something totally irrational and unheard of." His enthusiastic smile slipped off his face.

"Now watch closely as I apply this polish. You will do the same for me, only I'm going to pick a color that isn't such a fashion disaster." I smiled as he glanced at the polish and furrowed his brows. I applied his first coat. "Lean back against the couch and stretch your legs out in front of you." I took his shoes and socks off. "Stay there, I'll be right back. I forgot the cotton balls."

I returned and stuffed a cotton ball between each toe and then I applied the polish to his toenails. "Sit there and relax and don't touch your nails. It's tempting to touch them to see if they're dry. Don't do it. You'll regret it. I'll be back in a few minutes." I went into the kitchen, poured us each a coke and added a couple of ice cubes. I took them back out and handed one to Jason.

"So tell me, how in the hell did you spend $8000?"

"Well I didn't mean to. It just happened." I snorted. "It just crept up on me. I bought a new computer so that I could load up the latest software for web page publishing. That was $2500. That was probably the single biggest buy. I bought most of my clothes on-line. The problem is you can't check the size. So I bought several items that I couldn't even use. I found several good sites for transvestites, and I always found something new that I liked. I ended up with 6 or 7 wigs. I tossed a couple when I moved here because they were so bad. In fact, I purged a lot of items when I packed for here."

"When I first started dressing, I was pretty pathetic. I kept going to personal web pages of the better looking girls and I would study what they were doing, and I would try to emulate that. I bought a lot of styles and colors and things that just didn't work for me." He sighed. "But I was becoming obsessed. So I kept working at it, and I gradually got better. When I got to the point of respectability, I had to buy a good digital camera with a strobe so that I could take pictures for my own web page. I had to buy odds and ends like a tripod, a trip wire, soft focus lens, software for touch-up work, and pretty soon that all added up to real money." He shrugged his shoulders in an act of confession, "I just didn't realize what I was doing. I was lost in my fantasy world."

"Did you ever see Tara on line?"

"Yea, I did. She has a beautiful page. Not only is she a great looking girl, but she is willing to push the envelope a little. She gets a bit kinky."

"Is that what you were talking about the other night?"

"Yea."

"What do you know about her?"

"Not much. She's from Chicago and a lawyer like you."

"Really? That might be useful. Is she straight?"

Jason cringed. "She's bi."

"Do you like her?"

Again he cringed. "I like her as a crossdresser. I like her feminine persona. She is beautiful, sexy and ultra-passable. I'm in love with that female persona. But knowing what is underneath, I would never go there. I am 100% hetero."

"100%?" I asked with upraised eyebrows.

"99%."

I interrupted the conversation and handed her my nail polish. "Your nails should be dry enough. I want you to do my toes first, than we'll slide over to the table and I want you to do my fingernails." Jason started stuffing cotton between my toes.

"So you're 99%?"

"That didn't come out right. I guess I mean I'm curious. Not for myself. I mean not that I would want to do anything with a man, but I guess I'd like to see a pretty TV with another TV or maybe a real girl."

"What do you think of me?"

He turned red and blushed. I was afraid he was going to spread that polish all over my toes.

"I'm a girl, aren't I?"

"Oh yes," he sighed.

"Am I pretty?"

"You're the most beautiful woman that I have ever known. I really mean that."

"Do you like me?"

"Yes."

"Is that why you do what I tell you to do?"

He started becoming defensive. I was pushing into a psychological area that he was unsure of. "Maybe. Mostly because you threatened to expose me."

"I did?"

"Yea. I don't think I could handle that."

"I never threatened to expose you. Not verbally at least", and I smiled. "You might be surprised what you can handle. You just need some more self-confidence." I thought for a minute and then decided to take Jason to the next level. "Jason, lean over here and kiss me."

"Wh … what?"

"You heard exactly what I said. Don't ever question me again. Now do as I told you." He got up on his knees and leaned over and gave me a kiss on the lips. I made it a quick kiss. "Did you like that?"

"Yes," he said quietly.

"Good. Now finish my nails." As he returned to my nails, I hit him with the punch line, "Jason, if I ever tell you to kiss Tara, I expect you to do it."

He stopped with my nails and just looked at me. "Ok." I could barley hear him, but I knew I had him scared. We said very little as we finished applying polish to each other's nails. We each received two coats before I told Jason to go take a nap. "Last weekend was tough on me," I confessed. "I must be getting old. If I want to keep up with you tonight, I need a nap too." I gave him a gentle smile and went to my room.

I woke an hour later and knocked on Jason's door. "Get up sleepy head." When he answered the door he was still rubbing the sleep from his eyes. "Jason, it's time for you to learn to cook. But first, let's put your breasts on. You have glue for your breast forms right?"

"Yea. I have a couple of bottles in fact."

"Good. Strip, put on your panties with the padded ass, a bra and slip in your breast forms. Bring the glue and boxes for your breast forms."

It's amazing what you can learn on-line. I was about to put my surfing to practice. He came back out prepared as I had instructed. I took a pen , pulled down his bra so I could see the breast forms. I made a couple of marks on his skin to show where the breast forms sat against his chest. "Ok, take off the forms and bra." I took the glue and painted his skin inside the pen marks. While that dried I laid his breast forms upside down in their holders, and covered their entire underside with the glue. It took about ten minutes for them to dry.

I picked up the breast forms and stuck them against his skin. "Hold that one while I press on the second one. Now let me hold them both and I want you to put on your bra." I didn't want them to slip before he could get the bra on. I thought they would stay in place already, but I wanted the bra to hold them in place until they were firmly adhered. Once he had the bra in place I said, "Go put your robe on, and then I will give you your first cooking lesson."

When he came to the kitchen I told him, "I'm going to show you how to cook pasta."

"But I don't like pasta."

"I know. Now let's get started."

He was attentive enough and I think he learned a little. At the end of dinner I said, "Stack the dishes in the sink. You can clean up tomorrow morning. And remember to stay in your negligee and robe tomorrow morning."

"Ok."

"You should say 'yes ma'am' when I give you instructions."

"Yes ma'am."

"That's better. Now go shave, and shave close!"

He returned from the bathroom about twenty minutes later. "Were you bleeding?"

"Yea."

Is that what took so long?"

Yes."

"You're going to have to get better at that. Now, take off your robe and bra."

He did as I told him. I gripped his breast forms and jiggled them. They held tight in place. "Jump," I told Jason. I watched his breasts bounce up and down, lagging behind just a bit. They flopped up and down and looked very real. "That's great. They really look good. I'm impressed. Let's get you into your corset." Before Jason could put on his corset I gave him a pair of panty hose. "First things first I said."

I tied him into his corset, then gave him a camisole and he slid it over his faux tits. Without help from any other clothes, he had a nice figure. I was impressed.

"Do you want to wear a skirt or dress tonight?"

"Dress."

"Wrong. You're not ready. Let's look at your skirts. What do you have that is about knee length?" He had 8 or 9 choices. I couldn't believe how many clothes he had. We picked out a tight, silk floral print that hung nice and flowed with his movements. "I want a sleeveless top that can show off your freshly waxed pits. Something tight that will emphasize your boobs and narrow waist." We found a pretty white top with a deep V-neck and a bit longer than his waistline. We tried it tucked and out and decided it should be left out.

"You handled 3 inch heels last weekend, so let's do it again." I helped him into the heels and then found a nice necklace and bracelet. "I'd love to give you those nice drop earrings, but you need some healing time first. Bring your makeup into my room. You can use my vanity. I'm not going to help you tonight, I want you to apply your own makeup. I'll supervise and tell you what to do."

I learned a lesson that night. Don't dress Jasmine before she puts on her makeup. She had powder all over her top and we had to switch to a different top after her makeup was finished. We tried on a couple of her wigs and even though it wasn't the best match, I had her wear the long red wig. It made her feel more feminine because she could swing her hair around. I spritzed her with perfume and then told her to go fill her purse while I started getting ready.

When we were ready to go, I asked to see her purse. "Do you have Kleenex?"

"Yes."

Do you have a tampon?"

"No."

"What did I tell you last week?"

"All girls always carry a tampon in their purse in case of emergency." I went into the bathroom and retrieved one for her.

As I handed her the tampon I said, "Don't ever forget again. There will be a penalty next time. Understand?"

"Yes ma'am."

"Good answer, Jasmine. Let's go party."

I took her to another gay nightclub. Like Glitter, this one also catered to both men and women. I didn't think she was ready for an all female club. My plan was to take her to mixed clubs, then male then all female and finally out into the hetero world. It wasn't as noisy as Glitter and I was able to talk with her throughout the evening. I pointed out the way the girls dressed, and walked and how they held their hands and arms and gave her instructions on girl body language.

We danced several times and I allowed her to have two drinks. I took her to the girl's room a couple of times to freshen her makeup and become more comfortable in the girl's environment. There were a couple of crossdressers there and Jasmine talked with each of them. None of them was that convincing, but that didn't stop her from collecting more e-mail addresses.

We left the club around 2:00 A.M. and I took her to an all night coffee house. We sipped coffee and continued our girl talk. It was pleasant evening and we enjoyed the walk back to the car. Several times during the night I had to remind her how she should walk and comport herself. She seemed to be either slow at learning it, or sloppy in remembering it.

When we reached my apartment I helped her out of her heels and corset, and I watched over her to make sure that she was thorough in removing her makeup and applying her cold cream. I sent her to her bedroom to change into her negligee. She was still wearing her wig when she came out for her goodnight kiss. I preferred her with the wig, and in conjunction with the breast forms that she was still wearing I thought she looked nice. Before I sent her to bed I complimented her hair and general appearance. "I don't want you to get your hair cut anymore. You're going to let it grow out, understand?"

"Yes ma'am."

"Did you have a good time tonight?"

"Yes ma'am."

"Sleep well," and I gave her a quick peck on the cheek.

Sunday morning Jasmine remembered what she had been told. She put a robe over her negligee and wore her wig. She had the kitchen cleaned up before I came out of my bedroom. I sent her down to get the paper while I headed to the bathroom. "I can't go down to the lobby like this," she complained. "I don't have any makeup on and I look ridiculous."

"That's too bad," I sad with mock concern. "Do it anyway. If you see anyone, smile and say 'good morning' ".

When she returned I asked if she ran into anyone. "No."

"See, you get worried over the most inconsequential things. Now go make us some breakfast, I'm hungry."

 

On Monday morning I slipped a pair of thigh-highs along with panties and a camisole into her bag. When she came into my office she handed me the bag and I glanced in. "What are these?" I asked as I took out a pair of panties.

"I ran out of my men's underwear. Can you bring some back to me tomorrow?"

"Sorry sweetie, no can do."

"Why not?"

"Because I threw them all away. You don't have any."

"How could you do that?" he demanded.

"Easy. You know that trash container by the elevator in my garage? I just throw them in there when I go home every night."

"But now I don't have any."

"You don't need any. From now on you will wear nothing but women's panties. And don't whine about it, you prefer them and we both know it. And the same goes with camisoles. I don't want you to wear your men's undershirts anymore. You will wear nothing but camisoles. Lord knows you have enough. Now quickly before anyone gets here, show me what you have on."

Jason dropped his trousers and showed me his panties and nylons. Then he took off his shirt and showed me his camisole. "You look pretty in girl's clothes Jason. You were born to wear them. And you have very nice legs. You need to show them off more. Ok. Put everything back on, and let's take a look at today's picture of Jasmine."

Jason and I looked at Jasmine's picture and talked about her choice of accessories with the dress that she wore. Her pierced ears were going to make things easier for her in that area. She deleted the picture and left for her desk. As usual, I reloaded the picture and put it in my Govt directory.

At lunch, the topic du jour was Jason's earrings.

"How utterly girly. Two rings in each ear. There is no doubt anymore."

"You're right. He's not only gay, but I think he's a transvestite."

"No. Yea that would make sense."

"Is he wearing a camisole today?"

"I'm pretty sure he is. What a swish."

"He is just too hilarious."

"You meant just too sad."

"I've got to tell Sue in administration. She'll love this."

And so the character assassination proceeded. Poor Jason.

Jason came to my office and asked me to join him for a soda. "I never asked you Jason. How did you like your waxing?"

"For my legs it wasn't as bad as I thought it would be. But waxing my chest did hurt."

"Do you like the smooth, clean feel? Can you notice it under your clothes."

"Yes and yes. Especially when I'm in my negligee. The fabric feels so smooth and cool against my skin. I love it," he smiled.

"How about your thigh-highs? How do they feel?"

"I like 'em, but as the day goes on the elastic is cutting into my thighs more and more. I keep catching myself reaching down to tug on them."

"You'll get used to them and they'll feel just like second nature to you. Isn't it fun dressing in girl's clothes?"

A huge smile spread across his face, "Yea, it is. Thanks."

"Don't thank me yet," I warned. "You might want to change your mind later."

"I doubt it."

 

Tuesday did not start out as a good day for Jason. He came into my office with his little bag and he set in on my desk. He closed the door and dropped his pants without saying a word. He pulled off his shirt and showed me his dainty underwear. "Every time you show me your undies, I am amazed at how pretty you are in lingerie. You truly were born to be a sissy."

He didn't respond to my baiting, so I asked, "Jason, you're not talking much this morning. What's wrong?"

"I have to move."

"Move out of your loft?"

"Yea. The lady's father passed away last night. The funeral is later this week. She said that her mother couldn't continue living alone and would need to move in with her. She needs my room back."

"That's too bad," I said. "Do you know what you're going to do?"

"I'm not sure. I don't have my parent's money yet, so I still don't have any money for a security deposit. There is only one thing that I can think of."

"What's that?"

"Can I move in with you? Can I live in your second bedroom? I'll pay rent."

For once he caught me off guard. I fell back into my chair. He stood there with his big puppy dog eyes pleading and begging. I knew I would have to say yes. But not right away. I wanted to think things over first. I'd tell him later. "That's a big request Jason. Let me think about it, ok?"

"Ok. Do you want to show me today's picture?"

"Let's skip it for today. Why don't you go back to your desk and get to work."

I spent the morning thinking about Jason and how to handle his request. I wasn't going to turn him down, I just wanted to think about the best way to handle it. I reached into my desk and pulled out a disk with standard law forms on it. I slipped it into the computerand pulled up the form for power of attorney and put his and my names in the proper places. I modified it slightly and when I was satisfied I printed it out.

I called Jason and asked him to come to my office. He knocked on the door and announced his presence. "You call?"

"Yes Jason. Come in and close the door." He closed the door. "Sit down." He sat. "I've been thinking over your request and I have decided to let you move in with me."

A huge exhale of relief come from Jason. "Thank you, thank …" I cut him off.

"Just a minute, its not that easy. There are going to be some rules."

"Ok,"

"First, I'm not letting Jason move in, I'm letting Jasmine move in." His eyebrows shot up and he gave me a quizzical look, but he said nothing. "The only time I want to see Jason is when he goes to and returns from work. The rest of the time I expect to see Jasmine properly dressed. Is that acceptable?"

"I can do that," he replied. I could see that he was apprehensive, and he should have been.

"Jason will be expected to continue our dress-up game at work, or a variation thereof. Can you do that?"

"I guess."

"No guessing. Yes or no? You will be expected to sign this contract."

Gulp. "Yes."

"Next, I expect Jasmine to help around the house; cooking, cleaning, laundry and the sort. Will you help?"

"Absolutely." That was an easy agreement for Jason. "What about rent?"

"I'm getting to that. It is going to be very expensive." He swallowed. "I have here a form for power of attorney. You will give me complete control over your finances. You will be given $50 a week for your own expenses. You can spend that on anything you want. I will set aside $100 per week for Jasmine to use at the beauty salon, shopping or other female necessities. She can spend that money only with my approval. The rest of your money will be split in half. One half will go towards paying off your credit card and the other half will be put in escrow for you. It will be your savings. In exchange for this, you will have no rent and no expenses – other than your food. Do you agree?"

"I think so."

"Here, take this contract back to your desk and read it thoroughly. If you agree, sign it and bring it back to me." He took the contract and left. I knew he would be back with the signed agreement. I'd have it by the end of the day. When our afternoon break rolled around he came to my office and gave me the signed forms.

Out in the hallway I said to him, "I'll ask you one last time Jason, are you comfortable with the contract? Can you live up to it?"

"I'll be honest, I'm a little nervous. No, I'm scared. I don't know how far to trust you, but I am going to trust you. I just hope you will treat me right."

"Jason, that's a stupid wish. Don't ever wish for people to treat you right. Always put yourself in a position so you don't have to trust. Take some control of your life."

"I'll try." he said. I started laughing. "What's so funny?"

"You'll try. Jason, you just did the opposite. Are you sure that you want to do this? I don't want you to whine and force me to kick you out later. There is no turning back. You will live by my rules."

"I don't think I have a choice. I put myself in this position with my stupid spending habits."

"Ok, I hope you don't live to regret this. How much stuff do you have to move?"

"Not much."

"Can it fit in my car?"

"Yea, I'm pretty sure."

"Then we'll move you tonight. Just so you know, I'm leaving as soon as we are done here, and I will go to your bank and present this power of attorney form and take control of your account. I'll be back by 5:00 to pick you up."

I did exactly what I said. At 5:00 I returned to the office and collected the things from my office, shut down my computer and picked up Jason. As we walked to the elevator I handed him a money envelope.

"What's this," he asked.

"This week's $50. You are going to have to learn how to be frugal from now on. I want you to start brown bagging lunch tomorrow. The cafeteria is too expensive for you."

"You're serious aren't you?"

"Absolutely, sweetie."

We spent the evening moving him into his new home.

The next morning I reminded him to pack his lunch. "Also, before you get fully dressed, I want you to come show me what you are wearing for lingerie. I want to see panties, a camisole and stockings to begin with."

"What do you mean to begin with?"

"Eventually, we are going to expand your wardrobe, sweetie. Now go do as I say."

"But, I'm not sure …"

"Jason!" I raised my voice. "It's getting late and I will not debate this with you. You signed the agreement now get over it!"

We were the first to arrive at work and we both went to our desks and began our day. I put a new background on my computer, but didn't bother showing it to Jason. It wasn't necessary anymore. About 9:00 I called Jasmine and asked her to come to my office.

"Karen, how's it going?"

"Good. Look, I have a favor to ask you. You and the rest of the girls."

"What is it?"

"As you know, I take a soda break every afternoon with Jason. He told me yesterday that he has money problems and can't afford to eat at the cafeteria anymore. He is going to brown bag his lunch. Well, I thought it would be nice to invite him to bring his lunch and sit with us in the cafeteria. What do you think?"

"With the little fruit? Why would I want to do that?"

"Well first, if we don't he won't be walking through the cafeteria showing us what he is wearing for the day. Second, it let's us get a closer look at what he's wearing. Third, it might be fun to surround him with girl talk. It might be interesting to see what comes out. I just think it would be nice to him, and advantageous for us."

"But we only have a table for four."

"We could move to one of the round tables. Ask the other girls and see if they will agree. Ok? As a favor? And if they agree, we still don't say anything to him about his clothes or earrings, right?"

"I'll check and see."

"Thanks."

Jasmine returned about an hour later. "Ok, we've agreed that we will try it for a week and see if it works out."

"Great, thanks. Tell everyone thanks. Do you want to go invite him?"

"Me? Why me?"

"It would be a nice gesture is all. Please?"

She shook her head as she walked out the door.

About half an hour later Jason walked in. "Karen, Jasmine asked me to join you for lunch. She insisted. I don't know if I can."

"What did you tell her?"

"I said I wasn't sure."

"Go right back to her and say thank you, it is most gracious of you to invite me and I accept."

"But I'm nervous about saying something that I shouldn't. You know, about you letting me stay with you."

"Act shy and say little for the first several days until you become more accustomed to the situation. You can do it, sweetie. Now go."

Lunch actually went quite well. Jason said little, was polite and listened to the girls rip everyone else apart. It was a real awakening for her. "Is that what real girls talk about?" she asked me that night. "Was that a typical conversation?"

"It sure was sweetie. It's something you need to learn about if your going to be a passable girl."

 

CHAPTER SEVEN

Jason, Jasmine and I soon fell into a comfortable routine. Each morning I told Jason what to wear, and he would model it for me. I had him switch between different styles of panties, camisoles, and stockings. When we returned home each night, Jasmine changed clothes, put on makeup and a wig. Jasmine dressed a bit more dressy than you would expect at home, but we used each and every night to practice her fashion sense as well her deportment and voice. On weekends we began dressing Jasmine to the nines and taking her to different clubs. All gay clubs.

Jasmine was getting better with her walk and talk and deportment. Her hair was growing longer, and we began experimenting with styling it. I felt it might be long enough to style and wear in public. We began with curlers, hot iron curlers or a blow dryer. I wasn't very good at hair styling, but we continued to try and try. I finally gave up.

I had decided that Jasmine was ready to step into the real world, and I knew she couldn't do it with the wigs that she had. I asked Jasmine for help. She spent a lot of time on the Internet and I thought that maybe we could find some help there. I told her that I wanted to take her out into the real public; the world of heterosexual night clubs. And I emphasized that we needed to have her appearance as perfect as possible. We needed hair help. Her job was to check the Internet and find a local business or woman who could help.

Jasmine came through. She gave me the name of a local salon that serviced the transvestite and crossdressing community. I called and explained the situation. The problem was Jasmine's hair wasn't quite long enough for a real cut and style, so I wanted a best attempt for one night. The stylist suggested something a bit more permanent than a one night style.

"What about hair extensions?" she asked.

"Tell me about it," I responded.

"We use 100% real human hair. It is virtually undetectable from your own. We can attach hair shafts of any length . They are semi-permanently attached to the existing hair with a keratin adhesive. Chemically it is very similar to the hair itself, so it bonds very tightly and withstands the normal care and abuse that hair goes through. The extensions can then be cut, colored or styled to match the existing hair. It can last up to 6 or 8 weeks with proper care. After that time, you need to stop in and we will fill in missing or damaged strands. The attachments are close to the scalp and difficult to notice. Pulling the hair tight, as in a pony tail makes the attachments slightly more visible, but from a distance it is still very difficult to notice."

"How much does it cost?"

"That depends on many factors."

"Just give me a range."

"$200 to $400."

"Ouch. How long does it take?"

"Probably 3 to 5 hours, depending on coloring, cutting and styling."

"Do you have to color? Can you match the existing hair color?"

"Usually we can come very close. But for best results, we advise coloring."

"I'm sure you do," I laughed. "Seriously, we're a little short on change right now. Can you match the color and save us a few bucks?"

"Probably, ma'am. We really won't know until we have a chance to sit down for a consultation. Can we make an appointment?"

"Is this weekend open?"

"I'm sorry, but our stylist trained for this operation only works weekdays. Are you available this Friday?"

Big sigh, "Sure. Mark us down for the morning."

"Is ten ok?"

"Sure. Make the appointment for Jasmine. I'll give you my telephone number."

I informed Jason that he would have to take a vacation day on Friday.

"Why."

"Because you're going to get hair extensions."

"Aren't they very expensive?"

"Yes they are. This is going to shoot your beauty salon budget for a long time. No more leg waxing for a while."

"That's too bad," and he smiled.

"Yes it is," I responded. "Your hair grows in much slower and much softer when you wax."

"Is it really worth the cost? I mean couldn't I just buy a really nice wig?"

"Maybe. But we can get your money's worth with the weave."

"How?' Jason asked.

"The stylist said they can last up to 8 weeks. By then your own hair will be long enough and we can have it styled then."

"Wait a minute. You expect me to wear this weave for 8 weeks? I thought this was just for the weekend. I can't do that."

"Why not?"

"What will I do for work?"

"We'll tie it back it in a pony tail."

"I mean what will I tell everyone?" He sounded desperate.

"No problem, I've got you covered there. You just tell everyone that you are joining a local community play and you need long hair for your character. Simple, no?"

"And what character and what play would that be?"

"Hair."

"Hair?"

"Hair."

Jason started laughing. "You can't possibly be serious."

"Serious as a heart attack," I smiled.

"No … you can't," he began to whimper.

"Of course I can, and I will. Have you ever seen Hair?"

"I've never heard of it."

"My, my. You are an under-educated youth aren't you? Go to the library this week and rent the video. I suggest that the rest of this week you watch it several times and memorize it. When you tell people that you are in the play, they are going to ask lots of questions and you better know the answers."

"Is it playing somewhere?"

"How would I know?"

"But you said that I should say that I am in the play. If it isn't playing anywhere, everyone will know that I'm lying." He was getting hyper over this little detail. I really didn't care.

"Figure it out, Jason. Lie. Make something up. Say its just starting at such a little community playhouse that no one outside of your neighborhood has ever heard of it. Tell them you are a transvestite and you are practicing your hobby. I don't care, sweetie. My God! I'm bending over backwards to help you out, to help you enjoy what you love, and all I get is bitching and whining! If it's too fucking much for you, get the fuck out!" I had gotten loud and abrupt. I was getting fed up with his constant bitching.

"I'm sorry," he whimpered. "I do appreciate what you are doing for me."

"Like no friggin' rent for instance?"

"Yes." He was very contrite. "I'll think of something. I'll handle it. Please, I really appreciate everything that you have done for me. Really. I'm sorry. I'll do whatever you say."

"Damn," I said and I left the room shaking my head. I congratulated myself all the way to my room. I hadn't planned that, but I had just taken total control of his life. Wow!

Just for the fun of it, the next morning I made him wear a pair of one-inch hoop earrings in his lobes. The girls complimented him at lunch.

"They're very sexy, Jason."

"I love the way they compliment your eyes," snicker, snicker.

"You look so sweet, darling."

They looked so nice that I made them a permanent addition to his panties, stockings and camisole. I was looking forward to expanding the wardrobe.

Friday eventually rolled around. After his shower, I had Jason glue on his breast forms and put on a bra. I made him wear a panty girdle with a padded rear end. I told him to put on a garter belt and stockings and 3-inch heels. I helped him into his corset and we pulled it as tight as we could. We picked out a short skirt and a sleeveless Tee for him to wear. "No makeup, except for a light lipstick," I said. "We'll do your nails this afternoon."

"What about a wig to wear on the way there?"

"It'll just get in the way. Let's just go as you are."

"I look like a freak."

"You'll look fine when we leave the salon. Get your purse and let's go. And make sure that you have your tampon."

We drove to the salon and walked in. The receptionist was expecting us, but I think she was still a bit shocked by Jasmine's appearance. She wasn't totally ugly, but without appropriate hair she was obviously a he.

"Gina will be your stylist today, Jasmine. Can I get you a coffee or soft drink?"

"Thanks, a diet coke would be nice."

"And you miss?" she looked at me.

"Coffee, cream and sugar, thanks."

Gina showed up immediately. She took us to her station, which was very secluded. She immediately tried to calm Jasmine's nerves and set the mood. "Jasmine, you like very nice and I promise you that when you leave you will not believe how beautiful you are. You have a tremendous number of colors, lengths, and styles to choose from. We'll try and work together to give you a look that is uniquely yours. Something that will enhance your individual beauty and make you feel as feminine as a goddess. There are many questions that I need to ask and the first one is, what do you want to accomplish? What is your goal?"

And thus began Jasmine's transformation into a truly beautiful girl. As I have said before, she already had a nice figure and her face, when made-up, was very feminine and pretty. Her hair and nails had been her weak points, and Gina eliminated one of those weak points. I stayed with Jasmine the entire time (I even took some pictures) except for the bathroom breaks. Gina was amazing. She was a talented artist and a fantastic psychologist. She made Jasmine feel so comfortable and feminine that I had to compliment her.

"How did you learn your 'bedside manner'?" I asked. "Have you been handling TVs a long time?"

"Jasmine is only my second customer. But I did practice on my little brothers when I was younger. And Karen, this isn't difficult. She wants to be treated like every other girl. You just have to remember that this is all new, and you have to explain a bit more than normal. I love doing this. I would much rather turn an ugly duckling boy into a pretty girl than deal with a snobby, rich, sorority girl. And just between you and me, she's a cutey. I envy you." She gave me a smug smile and returned to Jasmine.

After interviewing Jasmine, Gina set to work. She had some hair that perfectly matched Jasmine's color and she told us flat out that it was sheer luck. One in a thousand. Jasmine had looked through several hairstyle books, and she and Gina decided on shoulder length hair. Gina pointed out many different styles that would be available with the extensions that Gina would give her. Gina explained several times the limitations, instructions on care, no-nos and general maintenance. Brushing and combing would have to be very delicate and careful and done with a soft-paddle brush. Jasmine would have to tie her hair back in a braid or ponytail for sleeping. She would have to make sure the hair and especially the roots were dry after washing. Her hair would tend to dry out if she washed it more than every other day. She would have to carefully separate the strands every morning and there were a few other items to remember.

Gina said that she would set Jasmine's hair in a curly style for the weekend. But she also handed Jasmine a couple of small pamphlets on hair care, extension care and some styles that would go with the style that she was getting. "Do you have much experience with setting and styling your own hair?" Gina asked.

"None at all."

Gina looked at me, "That will be your job then. Study that styling pamphlet. There are some really cute and easy styles for Jasmine's hair. Help her out, she has a lot to learn." Then she returned to Jasmine, "And Jasmine, if you would like, you can come back anytime and I'll give you a nice wash and set and I'll explain everything I do as I style your hair. The first appointment will be half price."

Jasmine was sincerely appreciative. "Thanks Gina. You're really kind. Money is tight, but one way or another, I'll be back." Then for the first time that I could remember, Jasmine said something truly funny and forward, "Gina, will you marry me?" We all laughed and Gina flashed her wedding ring in Jasmine's face.

Gina spent a long time with Jasmine. She sectioned Jasmine's hair, pinned each section out of the way, and took a small strand of Jasmine's hair and fastened an extension to it. The extensions were attached with a proprietary adhesive which was activated with a tweezer like heat unit. The attachments were about 2 centimeters from the scalp and very tiny. After attaching a row of extensions, Gina released the next section of hair and attached the next group. It took almost two hours to slowly work her way around Jasmine's scalp. When all of the hair was attached, she led Jasmine to the sink. "I'm going to wash and shampoo your hair so it will be wet. That makes it lie flat and makes it much easier to cut the hair. Almost all haircuts are done with the hair wet. I'm going to trim the extensions to an even length. All strands will be allowed to hang to the bottom of your style. I'm not going to layer your hair. This will make it easier for you to pull it behind for a ponytail. It will look much better that way, and when you want, it can look like a boy's ponytail."

Jasmine looked at me and grinned. She had the look of a woman who couldn't believe how wonderful her life had become.

"This style still leaves you many options for styling and curling. I'm sure you are going to want it nice and curly when you go out clubbing. Am I right?"

"Girl, you are so right. I love long, curly hair. You can't make it curly enough," and Jasmine beamed a huge smile. She was loving the attention and the possibilities.

"And you will find this styling easy. You can use wet sets, hot curlers or even a hot curling iron. Now let me warn you, curling irons are the most difficult to master and can be the most damaging. Be very careful with the hot iron, don't let it touch the adhesive and attachment area. I'd leave them alone until you have plenty of experience with curlers. Hair curlers are messy, but they're sexy, feminine and fun."

"Ok," she sighed. Jasmine was having the time of her life.

"So just relax, while I turn you into Chicago's newest diva. Don't forget me when you become rich and famous."

Gina, shampooed Jasmine's hair, wrapped a towel around her head and led her to a styling station. She quickly combed out the extensions and hair and trimmed them to a uniform length just above the shoulders. Next, Gina pulled over a cart loaded with curlers and accessories. She parted Jasmines hair down the center and then began sectioning the rest of her hair. Gina then used small curlers to roll up her hair. After pinning the last curler, Gina took Jasmine's hand and led her to the dryers. After checking the air temperature and getting Jasmine a Cosmpolitan, I pulled Gina aside.

"Gina, you have been an absolute darling today. Jasmine will never forget this day."

"I hope not, Gina agreed. "This is an important moment for all girls; their first salon visit!"

"Can I ask you to do one more thing?"

"Sure."

"Would you wax her eyebrows?"

"Sorry, I don't do that, but we have someone who can. Will that be alright?"

"Sure."

"What do you want? Thin a little or thin a lot? Lot's of arch?"

"Thin them down to an average level. Give them a bit of arch. I want her to look feminine, but not like some drag star who paints them on."

"I think I know what you are looking for. I'll have a Janice handle everything."

She left Jasmine under the dryer for about 40 minutes. Then she led her over to Janice's station. "Janice is going to clean up your brows. Don't worry, I've told her not to go to extremes. But with this do that I'm giving you, you have to have nice eyes. And your brows are critical to the right look. Jasmine, when were done with you Chicago will worship at your feet."

Janice introduced herself, then took a small stick and spread a small amount of warm wax under Jasmine's brow. She pressed a cloth against the wax, pressed it down, then ripped it off. Jasmine didn't complain at all. Janice then took her tweezers and began cleaning up the brows and around them. She repeated her efforts on the other eyebrow, then pronounced Jasmine beautiful. She walked Jasmine back to Gina's station.

"Jasmine, your brows look perfect. You are going to love your total look. Let's unroll these curlers and see what we have. Gina unrolled the first curler, and Jasmine's hair popped back into its curled position. Jasmine was watching in the mirror and she marveled at that single, perfect curl lying on the side of her head. It was beautiful. Gorgeous. The epitome of what she had always dreamed about. Jasmine was becoming a beautiful woman. Nothing in the entire world could be better.

Gina carefully unrolled each curler and placed it and it's pin in their proper bucket. After all of the curlers had been removed she stood behind Jasmine and they both looked in the mirror. "What do you think Jasmine, should we leave them right where they are?"

"Gina, you have no idea how thrilled I am. I love the curls. Yes, can we leave them right where they are?"

Gina laughed, "We could, Jasmine. I love the look of those little curls as much as you do. But trust me, they will look more 'finished' and pretty after I brush them out. With this much hair, you are going to love the volume and flow of your style. I'm going to frame your face, because you have such a great facial shape. I wouldn't do this with the normal oval face shape. But you face is rounder, and I'm going to make you beautiful. Prepare to break hearts, girl."

Gina was right. Not only was she a wonderful stylist, but she was also a phenomenal psychologist. Jasmine was finally finished. She was beautiful inside and out. Her style was perfect for her facial structure and she had never 'felt' prettier in her life. For Jasmine, the price was worth every penny. For me, the banker, I was wondering how I had come to the point where I was subsidizing Jasmine's metamorphosis. But she did look good. Mmmmmm.

We thanked Gina and returned home. We had a late lunch and then I gave Jasmine a home-made manicure. Her nails had been growing for a couple of weeks and they were getting longer, but still had a ways to go. I removed the hardener from her nails, then took a file and shaped them the best that I could. I applied two coats of her glittery pink polish.

We went through her wardrobe and picked out her clothes and jewelry for the evening. She chose a black dress with a dramatic asymmetrical hemline. The hem started at her right knee and ended at her left calf. It had long sleeves with a deep surplice neckline and ruched sides to accent her thin waist. For hose she chose black stockings with a back seam. They would go nicely with her open toed 3-inch black velvet heels. Jasmine decided to go with silver jewelry including a silver pendant with a large faux-ruby and three smaller ones. It would sit over her cleavage and look very smart. She chose large 3-inch drop earrings and finished it with silver bangle bracelets and a couple of silver rings.

I helped Jasmine tuck her new hair into a shower cap and then sent her to the bathroom for a long, fragrant bubble bath. I told her to make sure she shaved her legs and armpits. After her bath she dusted herself with perfumed powder, shaved ultra close, brushed her teeth and returned to her room. I had dressed while she was in the bathroom, so I was available to help her dress. After pulling up her padded panties, I joined her in her room and assisted with her corset. She put a black brassiere over her breast forms and had a great start to a beautiful, thin figure. I had to help her slide on her stockings and attach them to her garters. I instructed Jasmine to wear a black, thigh high slip.

Next, I led her to my vanity and sat her down in front of the mirror. I supervised her make-up application, but only had to make one or two very minor comments. Jasmine was progressing very nicely in her make-up application technique and choice of proper cosmetics. She finished with her lip liner and lipstick, and then I presented her with gloss to put over the lipstick. It made her lips shine.

We both returned to her room where she put on her dress and heels. She looked very pretty. I mean VERY pretty. She added her jewelry and we were almost ready. I took her back to my vanity, seated her and fluffed out her hair, brushing it back into place and spraying it with a strong hair spray.

"Stand up," I ordered. "Turn around. Now twirl around." She twirled and the hem of her dress flew up, but didn't expose her slip. "My gosh but you make one beautiful woman. What do you think?"

Jasmine had been bubbling ever since we returned from the stylist, but she was reaching a crescendo. "I just love how I look. I feel so pretty and feminine. I've been waiting my entire life for this, and now its here," she gushed. "I couldn't be any happier than I am right now. Thank you for everything you have done, Karen. I love you."

"Careful," I said through a grin. "Don't go all mushy on me. Do you have your purse?"

"No let me go prepare it." She had chosen a small black clutch purse, so she had to choose carefully what she was going to take. She returned to the living room and held up a tampon. "Look what I remembered." She smiled and dropped it into her purse. "Jasmine ready and reporting for her date, Ms. Karen," she announced.

"Let's do it then. Head up, elbows tight, walk like the beautiful, confident woman you are Jasmine." I took her to my car and opened her door. She sat down and very properly swung both her feet into the car. She straightened her dress and then announced that she was ready. I closed her door and entered the driver's side. "You know Jasmine, we are way too beautiful for this ole rust bucket. I have to get me some new wheels one of these days."

We went to a nice downtown restaurant. It was a dressier establishment, but the prices weren't astronomical. Money was a bit tight for the two of us. The maitre'd escorted us to our seats and we received a few polite looks as we walked by. We sat opposite each other at a small, intimate table. The room was on the dark side and there was a small candle on our table. The flickering flame caused the light to dance off Jasmine's jewelry and lips. The lip gloss she was wearing really made her lips look luscious. Almost kissable I thought. She was very attractive and I was beginning to become more attracted than I had anticipated.

The busboy came back and filled our water glasses. The waiter arrived and handed us a wine list. "It is my honor to serve two beautiful ladies this evening," he said as he gave us both a large and friendly smile. Would the ladies like a drink?"

"I think we will both have a glass of wine. Let me check the wine list first."

"Certainly," he said. "I am sorry but it is mandatory, may I see some ID?"

He looked at my driver's license and handed it back with a smile. Jasmine handed him her license and the smile disappeared from his face. A rather gruff, "Oh, one of those," slipped out of his mouth. He dropped the license next to her plate and turned back to me, "I'll return when you have read the menu."

The rest of the night he was cold and at times surly towards the two of us. He rarely talked to Jasmine, preferring to talk to her through me. We also seemed to get a lot of walk-bys and side looks from the rest of the staff. Half way through the meal I asked, "How is Jasmine enjoying her first evening out?"

She gave a little grimace and said, "I'm feeling awkward. Everyone seems to be interested in walking by and looking at me. I don't really like it."

"Unfortunately, our waiter has a problem with your real sex. If it wasn't for checking your ID no one would have known. But I think in a way it is very positive."

"How do you see that?"

"I think you are so beautiful that no one can believe you aren't anything other than a beautiful woman. They're walking by to see how passable and beautiful you are. In a way, I think you pass with flying colors!" That made her feel better.

"As soon as were done with the entrée, we'll get out of here. We'll check out some of the clubs and once were in, no one will think you're anything but one hot chick. It'll get better, I promise." And it did. We went to two upper-end clubs and after the bouncers checked IDs, there was not a single negative incident the rest of the night. But there were several fun incidents. The boys loved Jasmine, and Jasmine loved the accomplishment of fooling the boys.

Jasmine was indeed one hot chick and she got plenty of attention from the bachelors and bachelor wannabes. I had dressed much more conservative than Jasmine, and I had done that on purpose. I wanted her to get the attention when we reached the clubs, and my plan worked perfectly. Several times we were approached by a pair of guys, and the best looking one, the alpha-male, always went for Jasmine. A couple other times, a single guy came over and hit on Jasmine. She deserved the attention and her mood improved perceptibly as the night went on.

Twice we agreed to dance when asked, and we also danced a couple of dances together. Jasmine wasn't very good at small talk, and I usually kept the conversation flowing. She was surprised at how fast the men moved towards physical contact. It startled her the first time a guy put his arm around her waist and led her towards the dance floor. After that, someone was always touching her arm or hand or even pushing her hair off her face. That actually made her the happiest. It was obvious that her extensions were passing the test.

As the night moved along, someone else was becoming more interested in Jasmine. That someone was me. I was starting to get turned-on and I wasn't sure why. I knew that she was a he underneath, but on the surface she was a beautiful woman. She was really hot, but I had never been drawn towards a woman before. I couldn't decide which side of her was pulling me towards her. I thought it was her physical male side, but I continuously thought about her female attractiveness. I liked the idea that men found her attractive and the women saw her as pretty. I found her hair sexy, her lips inviting, her figure shapely and her personality demure. I was confused as to why I was becoming excited when I saw her walk, or cross her legs, or flip her hair. But I too started to touch her more. I couldn't resist. She was small in most features and looked very feminine. Why did I find that so attractive? I rubbed her arm when we talked. I touched her hair several times as I complimented her on her looks. I even reached down and squeezed her ass and called her Cally. I was subconsciously trying to seduce her. Maybe it wasn't even subconscious. As the evening wore on I wanted her more and more. I couldn't keep my hands off her.

I don't know if Jasmine Cally realized what I was doing or not. Maybe she did, maybe her senses were satiated on everything going on; the men, the dancing, the soft clothes, the aroma of perfume and sweat, or the tickle of new curly hair brushing against the soft skin on her face and neck. Maybe it was just my imagination, but I thought she was responding to my attention. She smiled continuously, and her hand movements became more expansive as the evening wore on.

But the night eventually began winding down. The boys were asking for telephone numbers and offering rides or late night coffee stops. Boys and girls were starting to couple up, and the clubs were starting to thin out. It was time for us to go. Jasmine was so hyped on adrenaline that she wasn't ready to leave yet. She was totally immersed in her role and she was loving every minute of the show. I decided to switch my role a little. "Jasmine, have you had a nice evening?"

"It's been great. Other than the dinner problem, I have never had a better time," she effused.

"Well, I was wondering … would you be interested in a ride home or maybe … a late night coffee?"

"A coffee would be nice. I'm flying so high I don't think I could land if I wanted to."

"May I walk you to my automobile then?"

"Certainly," and she offered me her arm. I wrapped my arm through hers and we leaned and bumped against each other as we walked to the car. When we reached the car we stopped in front of the passenger's door. Before opening the door, I wrapped my arms around her waist and pulled her tight against me. I slowly leaned forward and planted a gentle kiss on her lips. I pressed my breasts against her breasts, my hips against her hips. When I opened my eyes, she was staring into them. I leaned back and a smile started to creep across her lips. "Maybe I don't need a coffee," she said. Jasmine wrapped her arms around my neck and kissed me. She pressed her lips tighter against mine.

I broke our kiss and slid my hand down to her ass. I gave her a squeeze and murmured, "Maybe we should go home … to bed. It is getting late you know."

"Hmmmmm …" she agreed.

I opened her door and let her get situated before I closed it. I entered my side of the car and started it up. Jasmine said, "Just a second," and leaned over for a kiss. A gentle, sweet kiss on her beautiful soft lips. I could taste her lipstick and wondered why it tasted so sweet. I gave her knee a little squeeze and drove us home. We kissed all the way up in the elevator.

We held hands as we walked into her bedroom. I sat her down on the bed, and then crouched on the floor to remove her heels. I slid my hands up her right leg, feeling the smoothness of her stocking. She moaned ever so imperceptibly as I reached under the hem of her dress and found her garters. I snapped them open and gathered the top of them in my hands. I slowly pulled them down her leg as she shifted her weight onto her opposite hip, making it easier to slide down her stocking. I looked up and she smiled at me. I repeated the process with her other stocking.

I stood and offered her my hands. She took hold and I pulled her to her feet. I again wrapped my arms around her waist and pulled her lips to mine. This time we kissed passionately, smearing our lipstick over each other. I broke our buss and saw the mess that I had made. I laughed softly and said, "Sweetie, you have to do a better job of putting on your lipstick."

Jasmine returned my smile and said, "I see you also have a problem. You must be lipstick challenged."

"Let me help you out of your dress, then you can use the bathroom first." I helped with her dress then sent her off on her way. I hung up her dress and put her shoes away. I returned to my room and stripped down. I put on a teal colored baby doll covered with lace appliqués. I was in a fog as I returned to Jasmine's room and fell down on her bed. I had my eyes closed and was gently rubbing my stomach when I heard her return. I smiled and looked up, "You look awful tall from here. Have you grown?"

She tittered and mused, "I think I grew a lot tonight. Your turn." This time she offered me her hands and pulled me up to my feet.

I walked to the bathroom and washed my face. I opened my cold cream jar and scooped a glop into my fingers. I squished it between my fingers and then massaged into over my face. I was moving in slow motion, enjoying and concentrating on the soft and slick sensations. I felt as feminine as I had ever felt in my entire life. I was planning on making love to a beautiful woman and I still didn't fully understand my emotions and feelings. I was confused, but I didn't care. I was concentrating on my femininity and on Jasmine's. I slowly scrubbed the cosmetics from my face, and then took a warm washcloth and wiped the residue from my tingling skin. I finished my routine and returned to Jasmine.

She was wearing a short, bright red negligee that barely covered her crotch. She was prone on her bed trying to look provocative. It wasn't necessary and I told her so. "Jasmine, I have never wanted anyone as much as I want you right now. I would love to crawl on top of you and make love until you begged for mercy. But we have to do something first."

She gave me a puzzled look and said, "Oh my! I never thought about that. I don't have any."

I smirked and said, "Don't worry about that, sweetie. I have you covered ... literally. What I meant was I need to braid your hair so that we can pin it up. We spent too much money on your new hair, to take a chance of pulling it out when I make mad and passionate love to you."

"You're too practical," and she laughed softly. She sat up on the edge of the bed and said, "On the other hand, I can't think of anything more exciting than you running your hands through my new hair and braiding it. I've never had my hair braided, and I would love to enjoy one more exciting, new sensation."

I sat behind her on the bed and curled my legs under me. I removed two bands from my wrist and handed them to her. "Hand these back when I'm done." I gently pulled her hair behind her and carefully split it into three unruly strands. I then began weaving her hair into a loose braid. I thought I was back in grade school as I braided my best girl friend's hair. "This is like a sleep over," I told her. "Like two grade school girls as they play hair styling on their sleepover."

"That's neat," Jasmine answered. "I hope this ends up a bit more adult, though." We both giggled softly.

"Give me those bands," and I wrapped them around the end of her newly braided hair. "Get up," I said. I pulled the comforter down on her bed, and laid back her satin sheets. I held up the sheet and said, " Slip in here my little sweetie. I'll tuck you in." She crawled into the bed and I pulled the sheet up to her chin. I gave her a kiss and said, " Sweet dreams my little sweetie."

"You're not joining me?" she said disconsolately.

"Oh yes, you sexy thing. Oh yes. But let me get the light first. We're going to practice anatomy by Braille. Do you see that condom package on your night stand? Unwrap it and leave it where you can reach it." She did as she was told. I flipped the light switch and carefully made my way to her bed. I slipped under the sheets and slid against her.

I gently kissed her and slid one hand across her negligee. I reached her breast and massaged and kneaded it. It felt almost real. I even used my finger to circle and caress her nipple. I slipped my tongue into her mouth and played with her tongue, as my hand continued down her stomach and reached her penis. It was fully erect and very sensitive. As soon as I touched it she reflexively pulled away. Then she relaxed and allowed me to gently rake my fingernails down its shaft. I could feel her penis jerk several times as the stimulation from my nails turned her into jelly.

"Hand me that condom, sweetie," and I unrolled it over her penis. I had never felt so sexy and horny and wet in my life. I slid my leg over her and shifted my weight on top. I pushed my wet crotch against her penis and positioned the shaft against my clit. I rubbed until my clit couldn't handle the stimulation any longer. I lifted up on her, and let her penis slip into my wet pussy. She slipped in easily and felt so nice. Jasmine was not well endowed, and would never be mistaken for a Mikey. But by being on top, I was able to control her position and pressure and was able to satisfy my desires. I rocked back and forth, in and out and Jasmine quickly came. At least she lasted longer than Mikey. I continued pushing and thrusting harder and harder until I reached my orgasm.

I fell on top of her, exhausted and sweaty, and kissed her on her lips. I gave her one soft kiss after another, as I kept her penis trapped inside me. I kissed her lips and her cheeks, her forehead and her eyelids, her chin and nose.

I eventually rolled off Jasmine and landed on my back. Jasmine used her elbow to push herself up and lean over me. She continued to kiss me. "I loved that," she said. "I never dreamed I could enjoy something so much. I love you." And she continued to kiss me.

'Oh, oh,' I thought. 'This will take some damage control. But tomorrow is soon enough.' I let her continue to kiss me, and slowly start examining my body. Her hand slid over my negligee and reached my breast. It was her turn to caress my nipples. Eventually her hand reached down to my hem and slid underneath and up towards my breast. "Just a minute sweetie," and I pulled my negligee off. "That should make it easier, sexy."

Jasmine continued her anatomy lesson. I let her explore my entire body. I had to give her a bit of encouragement at times. "Don't be afraid to use your lips and tongue sweetie. Kiss my nipple. Lick it." I eventually encouraged her to move down between my legs. She buried her nose in my crotch as I helped her explore my vagina with her tongue. I pressed my clitoris against her tongue when she finally found it. It felt wonderful. "Is your condom still on?" I whispered.

"Yes," she answered.

"Great, come up here." Jasmine gave me one more lick, then slid her self up and began pushing her penis against my pussy. Her aim was poor, and I reached between us and helped her enter me. Before she began thrusting, she kissed me. I could taste my fluids and smell my aroma on her lips. It caught me a bit by surprise. I had never tasted or smelled myself before. At first I didn't like it. But as Jasmine began slowly, almost effeminately, pumping and thrusting into my pussy I began to become more aroused and started to respond to the taste and smell. I began to associate them with the pleasure I was beginning to feel. I decided I liked the smell. I liked the taste. I wanted them as Jasmine continued to thrust and pound against my pussy.

I had my arms wrapped around her back and I pulled her tight and rocked my hips in rhythm with her. She was being too gentle and I wanted more power. I wanted her to get rougher and stronger with me. I began pushing even harder and squeezing tighter. Jasmine received the message and began returning the pressure and force. She was lasting much longer than the first time and she was bringing me closer and closer to orgasm. I shuddered and clutched her as tight as I could. I clenched my teeth as I pulled her into me as the intensity rolled through me. I held my breath as my orgasm flowed through me, then exhaled in a loud gasp as I tried to catch my breath.

I had forgotten about Jasmine, but she must have cum at about the same time. She was breathing and panting just as hard as I was. We slowly caught our breath as Jasmine remained inside me. I squeezed my muscles and gave her penis a tug.

"I can feel that," she said.

"Do you like it?"

"Oh, yea," she whispered. "I can feel it and it is wonderful. You are wonderful. You're fantastic in fact. Thank you for the best night of my life."

I kissed her on her soft lips. "Jasmine, would you do me a favor?"

"Anything."

"Would you get off me? I can't breathe." She laughed and rolled off me. "Jasmine?"

"Yea?"

"I have a confession to make."

"What?"

"I had a wonderful time also. Now, let's lie here and just enjoy our closeness. I am so totally exhausted and I think I could fall asleep in a blink." I whispered. I quickly drifted off to sleep.

 

Jasmine was missing when I awoke. It took me a second or two to recall where I was, then I relaxed and smiled. I snuggled into the satin sheets and enjoyed their softness caressing my skin. It was only a few minutes later and I could smell bacon. I crawled out of bed and slipped into my baby-doll. I found Jasmine in her robe, hovering around the stove.

"Hi sleepy," she called over her shoulder. "Breakfast is almost ready. Take a seat." I sat at the table and watched her move around the kitchen.

"You'll make someone a fine wife one day, Jasmine."

"I'm practicing my audition," she told me. She brought a plate of eggs, bacon and toast and set it in front of me. She leaned over and kissed me as she set the plate down. She brought her own plate to the table and sat opposite. "I had a wonderful time last night. Thank you so much."

I smiled and continued with my meal. "What would you like to do today?"

"I don't know. Anything as long as I get to wear the right clothes," she smiled. The right clothes meant women's clothes.

"Why don't we go down to the lake edge? We can enjoy the sun, maybe stop by the aquarium and perhaps get in a little shopping."

"That sounds nice."

"We'll go casual and you can get used to being in public. Work on your voice, and walk and stuff, ya'know."

"Great. I'd love that."

After breakfast I had her clean up and shave very close. As I was supervising her makeup application I said, "Ya know Jasmine, you might want to consider doing something about your beard."

"Like what?"

"Electrolysis. It's not easy, but it would allow you to reduce the amount of foundation that you have to wear. For a casual day, you are going to look heavily made-up. You would be much more natural without all this makeup."

"But its expensive and takes a long time. I've read that some girls have two or three appointments a week and it still takes months to finish. And the money!"

"I know. You'll have to wait until you are in a better financial position. Whatever happened to that $10,000 that your parents were going to give you?"

"The last I heard, they were still promising to send me the money, but that was a couple of weeks ago."

"Well, that would make it easy, wouldn't it?"

"Yea. I hope it's not just a dream."

After putting Jasmine into her normal foundation garments, I picked out a pair of white Capri pants for her. She chose a beige sweater with three quarter length sleeves. She wore knee high nylons and sandals. I had her let down her hair and brush it out. Her hair still had a little curl and body from yesterday's styling.

We spent the rest of the morning walking along Lake Michigan. We walked through the Shedd Aquarium and then drove up to the Naval Pier for a light lunch and some additional strolling. After the Naval Pier we walked over to the downtown area and did a bit of window shopping. I let her try on a couple of darling dresses, but no money was spent. She couldn't afford anything, and I was not keen on enlarging her wardrobe. My own wardrobe needed some business suits.

We returned to the apartment around 5:00. I suggested that we eat in and then go catch a movie. I had a couple of coupons from work that would save us a few bucks on the movies. After the movie, we walked over to a neighborhood bar. It was populated by twenty-somethings. It was primarily a sports bar that had a good singles atmosphere. There was no dancing. We talked with a couple of girls, and had a few boys try out their lines on us. We allowed two guys to sit with us and buy us a drink. While the guys were probably very serious, Jasmine and I were relaxed and open to flirting. We had no intention of doing anything with the guys, but the sexually charged banter was fun. We probably led them on more than we should have. It was a nice bar and I thought we would return in the future, so there was no reason to earn a reputation as a tease.

When we returned home we were both relaxed, and a bit tired. We had been on the go all day. We both completed our nightly cleansing routine and we both ended up wearing our sexiest negligees. We sat on the couch while I helped Jasmine practice braiding her own hair. She wasn't very good and we giggled over the results. After getting a reasonable braid, we fell into each other's arms and started kissing and making out. She had a raging erection and her negligee just couldn't keep it covered. Her hem was so short, that no matter how many times she pulled it down, a bit of kissing and squirming and she popped right back out. She was small for guy, but being small was more of a turn-on for me than a large penis. It looked more appropriate and feminine when it kept peeking out from under her pink satin. It wasn't long before she was on her back, lying on the couch while I licked and stroked her little cock. I soon brought her to climax, and I allowed her to spurt her semen over her bare stomach. She held her negligee up, while I got some Kleenex and I cleaned her up.

Afterwards I made her lie on the couch so I could watch her penis shrink after orgasm. It was an interesting sight and I was turned on by the process. As her penis shrunk, it kept oozing small amounts of semen and I would wipe the tip and keep it clean. It was rather interesting, and I was surprised by how small her flaccid penis was. It almost looked like a button on a fur coat. When it was small enough, and I was horny enough, I stroked her until she was again hard and ready for more. I unrolled a condom over her, then mounted her. I was extremely wet, and with her being so small, she had no problem slipping into me. I took my time bringing both of us to orgasm.

It was my first time for making love on a couch, and it was rather crowded and uncomfortable. I loved it. I was already thinking of new locations where I could take Jasmine. She was very good at being submissive, and I knew I would have no problem taking her whenever and wherever I wanted. It might even become a fun game, I thought. How risque could I get?

We spent the evening in her bed, with her tightly cuddled against my back and her arm over my waist. I enjoyed being held, even if it was by a girlie-boy.

Sunday was the end of her first weekend with hair extensions. We didn't get dressed until almost noon. We spent the day much as we had Saturday. Jasmine dressed in a broom skirt and frilly blouse. We walked around the downtown area, window shopping and trying on a few dresses. I let her buy another set of pierced earrings, but held the line on all other spending.

Sunday night we did not make love. I sent her to her own bed and I slept in mine. I didn't want her to think we were too much of a couple. Sleeping together every night would allow her to become too comfortable with the idea of 'us'. I had decided that I was only going to sleep with her once or twice a week. I still wanted her thinking of us separately: me as in Jasmine (not Jason), and you as in Karen.

 

(continued)

  

  

  

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