Internal Affairs By Anna V. Hedge Copyright 2002 Anna V. Hedge avhedge@yahoo.com
Chapter I
My name is John Smith. I am, just like my name, a just another person in this world. I am 5'10" with dark hair and glasses. The glasses I inherited from my mom's side of the family. I've been wearing glasses forever, well since third grade. I have an average body. I am 28 years old. I am a salesman at a computer company where the pay is good enough to allow me to enjoy certain luxuries. I also like cross-dressing. My desire for women's clothing started from an early age. By the time I was 12 I already had a nice stash that included several outfits, bras, panties, and nylons, all, of course, courtesy of my mom, step-mom, and sisters. While I enjoy women's clothing, I have never managed to tell anyone about my hobby. Yes, my hobby. I consider it a hobby because it soothes my mind and body. Being a woman for a weekend at home, or even for just an evening has always allowed me to relax and to enter the world of Jessica Smith. I had been dressing secretly until I turned 26, when I unexpectedly fell in love with a lawyer, Katie McWilliams.
Katie and I dated for about a year before we decided to move in together. Since our relationship started, I avoided dressing up for fear that she might find out and that I would lose her. That, however, did not keep me from wondering how would her outfits look on me. I also found myself at times thinking as a woman when we were having sex. Yes, I would fantasize about her being in me instead of the other way around. Oddly enough, those were the best orgasms. About 3 months ago I decided to propose to her. She accepted, and we have been planning the wedding for a year from next month.
A couple of weeks ago I decided to come clean to hear about my cross-dressing past. I told her that I had been doing for a very long time. That it was something that just seemed to be in my mind no matter how hard I tried to fight it out. But most importantly, that I had not dressed up since I met her. Surprisingly, she asked me whether I had thought about dressing since I met her. I told her that it was hard to keep the thoughts off my mind, but that even though I had thought about it every now and again, I had fought off the desire to put on feminine attire. She smiled, kissed me deeply, and thanked me for trusting her with this.
About a week later, Katie came home and asked me if I wanted to spend Thanksgiving at her parent's cabin. Her parents had died several years ago, and Katie being the sole child, inherited the property. We usually drove there to spend long weekends since it was only a 3-hour drive from the city. I agreed that it would be a good idea, and that this way we could have a nice romantic Thanksgiving weekend.
On Wednesday night before Thanksgiving I started loading our stuff into our car's trunk. I noticed that Katie had packed 3 large suitcases for the trip, as well as her makeup bag. I made nothing of it, and we set out. The drive to the cabin was fairly uneventful except that Katie seemed somewhat anxious to get there. She also managed to tell me that she was sure that this was going to be one of the best weekends of my life.
We got to the cabin around eleven thirty at night. As soon as we walked in, Katie took my hand and took me to the sofa. As we both sat down, she looked straight to my eyes and told me:
"John," her eyes looked filled with joy, "I understand how hard it's been for you to hold off your desires to be a woman while we have been going out."
My mind started racing. Where was she going with this? Was she about to break up with me?
"So, I decided to give you a whole weekend to be a girl." She said with a large smile.
"What are you talking about?"
"I spent the last week buying clothes for you so that we can have a girl's weekend. Just your girl self and me."
I couldn't believe my ears.
"But before we start, and I can tell by that look of yours that you're intrigued, I need to know what is your...your girl name?"
"My girl name?" I asked while my mind remained puzzled by Katie's proposal.
"Jessica." I said while managing to say it in as girly a way as possible.
"Well, Jessica. I think this is going to be lots of fun."
Katie grabbed my hand and headed to our bedroom. There she opened one of the suitcases and pulled out a little box that contained hair-removal strips. As she opened the box, I started to think about what was about to happen to me.
"Don't just stand there, take off your clothes" she said while looking straight at me.
I did as told. She then reached towards the suitcase and pulled out a silk fuchsia robe which she tossed my way and asked me to put it on. Once I had the robe on, Katie sat me on the bed and started removing all my body hair. She started with my legs and once she was finished she gave me a bikini line. Then she proceeded to take off the few hairs that were in my belly and breast region, and proceeded to my armpits and forearms. Finally, she moved to my face. Up to now, I had not protested, but when she headed towards my eyebrows I objected.
"Don't worry, we'll take them all off on Sunday and you will just tell people that you had a small accident with the fireplace" she stated as if she had expected my objection.
I shrugged and Katie proceeded to give me the most wonderful, and beautifully arched eyebrows. Once the hair-removal procedure was done, she instructed me to take a hot bubble bath. She prepared the bath for me by adding several soaps and other items to the water. When I was finished with the bath, I found myself marveling at the smoothness of my skin, and upon looking at the mirror I loved the appearance of my eyebrows.
As I finished drying myself up, I put on the fuchsia robe, and walked into our bedroom. What I saw gave me an instant erection. On the bed there was a light pink satin baby doll and its matching panties. I looked up and Katie was looking right at me.
"I take it by your unwomanly reaction that you like the baby doll" she had a wide smile. "Well what are you waiting for, try it on. But before you do so, I also got you these."
She was holding a light pink satin bra, which matched the baby doll and panties, on one hand, and a box holding a pair of breast forms on the other. I was astonished.
"I figured if you were to be a girl for the weekend, you might as well go all the way" she said.
She approached me, gave me a light kiss on the lips, tossed the bra and breast-forms on the bed, and proceeded to move down on my now extremely evident hard-on. She licked my penis while massaging my balls. I was so aroused that I came in seconds. She cleaned my dick when I finished. She then gave me a kiss which included the last part of my cum which I sloshed around my mouth and swallowed.
"Well," she said, "it looks like Jessica has just being baptized."
I looked at her, still not believing what had just happened. I slowly started to grasp what had happened and came to realize that I had greatly enjoyed it. Even the taste of my own cum! She must have seen my look of happiness because she gave me a light kiss and then handed me my bra.
I put on my bra, with the skill of someone who had done this before. She then handed me the breast forms which game a nice bust line. Before I put on the panties she handed me a roll of surgical tape and added that it so that I could "tighten" my "equipment." I then pushed my nuts up and taped them out of the way, and sent my penis back between my legs. As I finished putting on my panties, what remained behind was a nice flat surface instead of my so-called equipment. The baby doll slipped right on, and with my new bust line, it looked great. I felt a new hard on starting to build, but just as I was about to head to the bathroom to relieve myself, Katie sat me down at the vanity and started to work on my toe nails.
Once she was finished painting my toenails dark red, she moved on to placing extensions on my nails. She worked swiftly and when she asked me what color I wanted them, I asked for a French Tip.
"Then we'll have to go into town tomorrow to get your nails done," she said while looking at me like a child who just met her hero.
Before I could object she stated applying the same color nail polish on my nails as she had done on my toenails. As I waited for my nails to dry, Katie started getting ready for bed. She emerged from the bathroom wearing her flannel pajamas. She looked at me, and using her index finger asked me to come to her. I stood up and as I approached her she told me to stop.
"C'mon Jessica. You have to walk like a girl if you want to be a girl."
The next hour Katie showed me how to walk like a girl without overdoing it. After that she had me walk on different size heels until we were both exhausted and decided it was time to head for bed. She had me remove my wig before going to bed. As we fell asleep, I cuddled against Katie and felt her breathing as I fell asleep.
Chapter II
As the bright ray of light hit my face, I glanced up to see a slight figure holding standing by the curtain. Katie was looking fabulous. She was wearing a pair of tight shorts and a sports bra. Her hair was in a ponytail. Her tennis shoes told me that she was getting ready for her morning workout.
"Good morning sunshine."
"Hmm. Good morning," I replied as I looked for my glasses on the table.
"Well, it's time for our morning workout."
"Our morning workout?"
Before I could finish my question I figured out what she meant when she tossed me a pair of black shorts similar to hers, a sports bra, a black leotard, and pointed to the corner of the room where a pair of socks with pink trim and tennis shoes were waiting for me.
As soon as I finished putting on my shoes I joined Katie on the adjacent room where she had the TV waiting with an aerobics tape. What followed was one of the most grueling workouts of my life. I had never imagined that aerobics could be so demanding. I had seen Katie workout for quite some time but I had never imagine how hard this things could be. On top of that, the breast forms provided a bounce to my chest area that took me a while to get used to. At the end of the workout I was exhausted.
Katie went to the kitchen while I went ahead to take a shower. The hot water felt like heaven. As I stepped out of the shower Katie handed me one of her health drinks. I looked puzzled as I never got used to the taste of the drink, but when she said, "a girl needs to eat healthier," I just took the drink. As I stepped into the bedroom my clothes for the day were waiting for me on the bed.
"You can get dressed by yourself while I take a bath?" Katie asked me as she was removing her clothing and walking into the bathroom.
"No problem," I replied as I headed towards my attire.
The first thing at hand was to tape my nuts out of the way. Once that was taken care of I put on my silky black panties. An equally black bustier was then waiting for me. Luckily I had done the hook-and-eye closure before and it was on me in no time. The bustier made it somewhat hard to breathe, and once the breast forms were in place, the whole thing was a tight fit. The garter belt came on next and the light brown colored stockings finished the work. I started to look at myself on the mirror by turning one way and another.
"You look fantastic," Katie said with a smile. "Let me put something on quick so that we can do your makeup.
She put on her red velvet bra and red velvet panties and told me to sit at the vanity. She started applying foundation. She moved efficiently as she added the eye shadow, mascara, and eyeliner in a jiffy. Next she worked on my lips using lip liner followed by the lipstick, which was of dark red. She finished off with the blush, and finished her work by putting my wig on.
"All right Jessie. Now finish dressing yourself up while I get ready. We have an appointment at the nail salon in an hour and a half and it is an hour drive."
I nodded and started towards the bed. I picked up the satin silver blouse and buttoned it carefully with my manicured nails. The black skirt came on next. It went down to about a couple of inches above my knees. The outfit was finalized with a pair of 2-inch heels, a lady's watch, and a gold chain with a small pendant.
"Ready to go," said a now fully dressed Katie.
She looked better with every day. She was wearing a black skirt, black nylons, black pumps, and a button down pink shirt. Her face was lightly made up. She looked perfect.
"Katie, since when do salons open on Thanksgiving?"
"Don't be silly Jessie. We're going to Mel's salon. I called her last night and asked if we could come in for a quick manicure."
"You told your cousin Melanie about me?"
"Don't worry. She said she wouldn't tell anyone. Besides, she told me she couldn't wait to see what you looked like."
"But..."
"No buts miss. After all, wasn't it you that wanted a French Tip?"
With that the discussion was over. She handed me my purse, and we headed out towards the car.
The drive to the salon was nerve wrecking. I kept on looking at myself on the mirror and Katie kept telling me that I looked great. At one point, I decided to see what Katie had packed in my purse, and to my surprise I found a napkin. I picked it up and Katie looked at me and smiled.
"You're enjoying this more than me aren't you?" I asked and then we both started laughing.
We finally arrived, and to my chagrin, Mel didn't seem to be around. Katie said that we should knock to see if she was in there. As I stepped out of the car, another car pulled right next to us. I straightened my skirt walked towards the salon ignoring the car. Just as I was about to knock I heard a voice calling me.
"Oh my God! John, is that you?"
I turned around to find Mel with a look of great surprise.
"Hi Mel. Nice seeing you again," I replied with as feminine a voice as I could muster.
"Wow. You look fantastic. Katie you did a hell of a job, or did you do it yourself?" she asked while winking at me.
She moved slowly towards the door and opened the salon holding the door open for Katie and me to go in. She then closed the door and relocked it.
"I just can't believe it's you," Mel said while looking at me.
"She looks gorgeous doesn't she?" Katie asked.
"Yes she does. If I didn't know him...I mean her, I would've thought she was one of us."
Both girls were now checking me out.
"So, John..." Mel started.
"Jessica, or Jessie." Katie corrected.
"What can I do for you today?"
"She was thinking about a manicure. French Tip, and I was thinking about fixing up that hair underneath the wig a little to make it more feminine."
I started to object, but Melanie grabbed my hand and sat me down at one of the stations and started talking with Katie about my hair. Before I could utter a word she had taken my wig off and started working on my hair. After about an hour and a half, she had my hair looking totally different, and she then started to work on my nails. In another half hour she was done with my nails and I felt wonderful.
"Well gorgeous, you are all set," Mel was staring at me.
"What is it?" I asked her.
"You looked so amazing. I just can't get over the fact that underneath this girl is my cousin's fiancee."
"Well, get used to it girl," I replied jokingly.
"Are you planning on staying this way long?" Mel asked.
"Nope, just until the end of the weekend."
"Well, let's just see what happens with the weekend," Katie intervened.
Mel and I looked at Katie. What did she mean by "let see what happens?"
To be continued...