Crystal's StorySite


My First Time

Sally Ann


I've always wanted to chronicle my story. I don't consider myself a writer but I'll give it my best shot. To begin with I'm sitting here, it's early in the A.M. I'm wearing a pink bathrobe over a red baby doll set. I threw on a wig for effect. My face is a sight with makeup leftover from last night. I went out with a couple of TG friends to a TG friendly bar and had a great time. Enough of that.

I started my dressing as many other cross dressers by playing dress up with my cousin. It was all quite innocent. It wasn't a very elaborate dress up session at first just a dress. Neither my mother or my aunt gave it much thought, just kids playing and staying out of trouble. I think I was around 7 the first time. It got to be that every time I went over to Haley's house I'd end up in a dress, I wasn't coerced, it didn't take much for me to be convinced to play Haley's favorite game. I had an androgynous name Jamie so it fit either way I was dressed. Neither of us knew what sex was so it didn't have a sexual aspect. I do remember the funny tingling feeling I would get when I slipped into a dress, a feeling I still get and long for to this day.

At about 10 years old the game took a more serious turn. When I arrived at my cousins to stay the weekend I found that Haley had a friend over. Julie was about a year older then Haley and I and was considerably bigger then we were. Right off the bat she made it clear that she didn't have any room for me. I didn't know why. I just met her. Well anyway Haley, as always, decides I was to be one of the girls. Some how I thought that Julie might like me more that way, maybe she just didn't like boys.

So, as I had done dozens of times before, pulled off my tee shirt and accepted a dress from Haley a dress I had worn before. Nothing fancy just a cotton print with puffed sleeves a lace bodice that tied in the back. I was still wearing my shorts that disappeared under the skirt.

I remember feeling especially self conscience with the new person there but it was just something Haley and I always did. Julie just smirked at me. She told me in no uncertain terms that I was just a boy in a dress. I was also a big chicken and that to prove I wasn't that I should let them dress me up as a REAL girl. I honestly didn't know what she met by REAL. I suppose she could see the dumbfounded look on my face. So she went to Haley's dresser and fished out a pair of panties and a training bra. She hung them over her arm as she opened up another drawer and took out a pair of tights. From another drawer she selected a nylon slip. Watching her shop I was starting to get the picture. She taunted me with the garments and to my surprise Haley sided with her. I wasn't going to be called chicken so I told them I'd do it. Little did I know that I was about to make a major turning point in my life. I was told to drop my shorts and underpants. I did so being kind of embarrassed about my underpants but did none the less. Julie handed me the nylon panties and rather sternly told me to put them on. I accepted the panties from her. The silky feeling on my hands gave me an advanced warning of what they would feel like on my young bottom. I felt silly standing there without any underwear on but you couldn't see anything with the dress covering up my bare butt. I got a dirty look from Julie and giggles from Haley. I fiddled with the garment trying to get it in the right position. I remember that I couldn't figure out which hole was which. Julie snatched the garment form me, lined it up properly and gave it back and told me to get on with it. With red face I stepped one foot and then the other into the leg holes and drew the panties up, I'll never forget the feeling. One girl smirking and the other one laughing as a tiny piece of nylon emasculated me. I was made to sit on the bed as Julie rolled up the tights and applied them to my legs. The white garment caressed me and sent even more new feelings through my body. It was over now I was no more then a toy to the two girls. Julie untied the bow on my dress unbuttoned it and pulled it over my head. I was told to hold out my arms and the bra slid over my outstretched arms and onto my chest. Haley, who had taken up position behind me, giggled as she fastened the bra and cooed as she adjusted the straps. Haley giggled and Julie smirked with a evil grin as that surveyed me for what seemed like forever. I turned, and for the first time caught a glimpse of my self in the mirror on Haley's closet door. I could make out the dark blue panties through the tights. The pressure of the tights combined with the silkiness of the panties and the new feeling of the bra is burnt into my brain. I was embarrassed standing there in girls underwear almost hoping that they would get on with it. At least I'd be covered up even if it was a dress. Julie mater-of- factly rolled up the slip, had me put my arms straight up and pulled the nylon garment down over my head and adjusted it. Each new garment seemed to have its own magic. I was now encased in nylon. The dress followed quickly. The dress took on new meaning now that it was fully complimented with girls underwear. Julie made the most evil giggling as she buttoned the back of the dress and tightly tied the bow. The two were so happy with themselves. Julie was especially proud of her accomplishment having emasculated a boy. And I figured that it was all over. Wrong again. From nowhere came a tube of lipstick, my head was forced back, and my lips were painted. I accepted it with no resistance I realized at this point that I was really enjoying my transformation I couldn't explain the wonderful feelings I was experiencing but I know that I liked it, I loved it. They finished up with some blush and some eye makeup. My hair which was long enough to pass as a girls was styled with a couple of barrettes and it was finished. Julie parked me in front of the mirror so that I could admire myself. I couldn't believe what was looking back at me. If I had my way I would have stayed there in front of that mirror forever. I didn't care anymore what they did to me I was in love with the reflection in the mirror. I didn't care if they laughed or giggled. I was in my own little feminine world and didn't give a damn what was around me.

The two dragged me sheepishly down to the kitchen to show my mother and aunt there new creation. The two ladies were pleasantly shocked when they figured out who the new little girl was. They had a good laugh and I got a few remarks about being the girl my mother always wanted. But other then that they didn't make much of a deal about it. Its funny cause now Julie was being nice to me its as though I was a girl now and so was accepted. I stayed a girl the rest of the day. The only really embarrassing moments were when Haley's older brother came home and later when my uncle came home from work. But even they just made a couple of smart as remarks and went about their business. Jamie, the girl Jamie was born that day and has so far lived happily ever after. I think I would get carpel tunnel trying to type all the feminine adventures I had in the years between then and now. But there is something really special about the first time that you are completely dressed. My TG friends express the same sentiments. I was just fortunate to have it when I was young and could pass so well.




2004 by Sally Ann. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.