This is a work of fiction. Any similarity to real persons, places or events is strictly incidental.
When I was 16 I lived in a small mid-western town with my mom. My father had died when I was 5 and my mom had never remarried or had any other kids. I kept myself busy with a paper route, the Internet and computer games. Mom worked two jobs and I spent a lot of the time on my own.
One day the elderly couple next door moved out and put their house up for sale. It wasn't long before it sold though. The new owner was a single guy about 26 yrs old named Gary, and he worked from home developing web sites. Because I was home alone often, I soon met my neighbor and we became computer geek buddies. He showed me lots of cool things on the computer and I learned a lot. I tried to find out more about his web sites, but he kept changing the subject. I figured it had to be some kind of secret business deal that no one was supposed to know about or a trade secret or something and let it go at that. I did notice, however, that he never seemed to go out on dates. I asked him about this and he said that he had recently gotten divorced and wasn't ready for that yet.
One weekend my mom got a phone call from my uncle in NY. My mother's aunt had passed away and she had to go to the funeral. She said she'd be gone a week and had to find a sitter for me. I was really upset about that. I mean, I'm 16 and spend most of my time alone anyway, why did I need a sitter? She was adamant though. That's when I got the idea that I could stay with Gary for the week. My mom liked the idea and called Gary to see if it would be OK. Gary agreed and we were all set. I was to spend the evening at Gary's house after school, but would clean up in our house. Not too bad. Almost like not having a sitter at all! The next night after school I stopped by Gary's house, he gave me a key and he showed me my room. That night was pretty uneventful. I played some computer games on my laptop and went to bed. I got back after school the next afternoon and Gary had left a note on the refrigerator saying he was out for a few hours and would be home at 7pm or so. I decided this was a perfect time to explore the house. Snoop to be exact. I soon found a closet that I didn't expect. It was in a back bedroom and contained women's clothing! I checked the dresser and I found women's underwear. What I found next really shocked me. I saw a picture of Gary in a dress and a wig. Further investigation uncovered the makeup and wig. I also found... vibrators, dildos and all sorts of other sex toys. As I stood there looking at the secrets I had found, a wild thought entered my head. What would I look like as a woman? I had to find out. I figured I had a couple hours until Gary got home, so why not?
I quickly stripped and pulled a bra and panties out of the dresser. I slid the panties up my legs and loved the way they caressed my cock and ass. It took a little while to figure out how to put on a bra, but I managed. I stuffed a couple of panties in each cup to fill them out and decided to try on some stockings and a garter. I was really careful putting them on, as I didn't want to rip them. I'd seen my mom put hers on once and tried to copy her. The silky feel made my cock harder than it had ever been. I looked thought the closet and chose a pretty blue dress and slipped it on. I did my best to zip it up but couldn't quite get it all the way. I found a pair of black high heels and tried them on. Not a bad fit, only a size too big. I walked down to my room to look in the mirror on the back of my door. As I twirled and posed in front of the mirror I couldn't believe how feminine I looked. I knew right then that I would do this as much as possible. I opened the door to go take the dress and underwear off and bumped right into Gary!
"I see you found a way to stay occupied." Gary said. I didn't know what to do. I tried to stammer an excuse, but all he said was, "It's OK. I don't mind. Lets go back to my dressing room and chat, OK?" I followed him down the hall, back to the room with all the dresses. He sat me down and said, "For starters, let's get that dress zipped up, OK?'" He zipped me up and started explaining about his "other" life as "Gina" the web mistress of an online porn site and web cam for transvestites. He asked me what I thought about that and I said, "It kinda explains why you got divorced, doesn't it?" "Yeah, it kinda does, doesn't it." he laughed. "You know, you look pretty good in that dress. Want to try getting dressed all the way?" "Sure, why not?" He told me to sit at the makeup table and relax while he did my makeup. It took him a while. Then he chose a blonde wig that was almost the same color as my own hair. He then told me to close my eyes and led me back to his room. He has large mirrored closet doors and told me to take a look. "I look like a real woman!" I gasped. "You do indeed. A very beautiful one at that." I bushed and said, "Thank you, Gary."
He told me to wait downstairs for him and that he'd be down in a bit. He came downstairs, or should I say "she" came downstairs about 45 minutes later. Gina was a vision of loveliness, with a sexy edge to her. She wore a rather conservative blouse and skirt, but with 4" heels and seamed stockings. I noticed her breasts shook as she walked. Apparently she had breast forms that I hadn't discovered. She then handed me a purse and took me by the arm. She led me to the garage and her car. I asked where we were going and all she said was "Dinner... out." I tried to object, but Gina wouldn't relent. "Just follow my lead and all will be well."
We drove a couple hours away and went to a nice restaurant for dinner. I followed her advice and let the waiter pull out my chair and acted the part of a young lady out with her older cousin. My fears soon dissipated and I felt completely at ease. As we walked back to the car, I noticed a few young men giving us the eye and I winked at one. I loved this! I was going to do this all week if I could. On the ride home I couldn't help but rub my legs together and feel the silky pantyhose rub against itself. I was having a "hard" time and Gina noticed I'm sure.
Once back at Gina's she lit some candles and put on some soft music. We danced with each other and Gina kept rubbing my ass and pulling me close. I looked up at her and was surprised to see the lust in her eyes. Surprised because it echoed my feelings. She bent low to kiss me and I closed my eyes. The kiss was warm and tender, her hand softly caressed my face. I kissed her with a passion I had never known in my young life. "I want you to make me a woman." I whispered softly in her ear. She kissed my lips and pulled me by the hand to her bedroom. I didn't resist as she took off my dress and pulled off my panties, refastening my garters to my stockings as she did. My young cock sprang free and was already dripping pre-come. She knelt and licked the tip to get a big drop on her tongue. My cock responded with a big twitch as a moan escaped my lips. She stood up and removed her skirt and blouse and pulled off her panties. She had hers over her garter straps. I'd remember that for next time. She laid me down on the bed and we kissed for a while. Finally she reached into the nightstand and produced some lube. A generous coating on my "pussy" and she slipped a finger in. I gasped at the intrusion but was eagerly anticipating something... bigger. As soon as I started squirming on her finger she decided I was ready. Lifting my legs and placing a pillow under my as she kissed me and said, "Tonight you will be a woman. My woman." I felt her cock at my ass and I grunted as the head was pushed into my cherry "pussy". She went slow and was soon deep in my ass. She rested there so I could get used to her, then she started thrusting slowly. She kissed me and told me I was beautiful. An angel. I kissed her back and said, "I love your cock in my pussy. I love you!" Soon she was thrusting into me faster and faster. My cock was twitching and my balls were tight, I was going to come and neither of us had touched my cock! Just as I started to come, Gina gave a shudder and came in my ass. I went limp and savored the feeling of her come in my ass. She was beautiful and I loved her. We laid there in each other arms until her cock went soft and slipped out of my tender ass. Later that night we did many more things. I sucked my first cock and got to fuck her "pussy". We spent every night in bed and I learned how to dress myself and apply my own makeup.
After my mom came home I still spent a lot of time at Gary's on the weekends and after school. I even bought some of my own clothes, which I kept at Gary's, of course. When I turned 18 and graduated, I moved away to go to college and now spend my life as a woman. I started hormones in my junior year at college and am now more feminine than ever. Gary came to visit me recently and we relived some old times. I now work as an IT Manager and have several boyfriends. Someday, I hope to get married. All thanks to Gary and "Gina".