Where it happened: Her apartment
Langauge: English
Sex: Male
Rating: 10
Category: Straight
Hi, I’m glad I found this site because I’ve been looking for a place to tell someone my story.
I’m going to put this here first so there are no misunderstandings. I am a cross dresser, I don’t dress everyday but I do enjoy wearing ladies clothing from time to time and I guess I do do it more often after my experience.
When I was 20 and still a virgin, I had a habit of going out wearing ladies underthings under my guy clothes just because I liked the way they felt(I still do for that matter), anyways I was sitting at a fast food place eating a burger and fries when this very beautiful older lady(about 25 to 30) walked up and asked if she could sit with me. I told her sure, they started going on about how busy the place was and what not. Then she asked me if I minded her making a personal comment. I told her that would be fine, then she told me that she could see my bra through my tee shirt and my pantyhose were sticking out of the top of my jeans. I started to freak but she but she told me not to worry, in fact that’s why she sat down with me in the first place. I was kind of in shock for a while after that but she did her best to keep me calmed down.(You see, I’ve never talked to anyone about my cross dressing before this.) Anyway, she told me she had a thing for cross dressers and wanted to make a deal with me. She told me that she would let me do anything I like with her if I would let her turn me into a girl and be her girlfriend for a week or maybe longer if I liked. I told her that I would love to go for something like that(I was unemployed at the time so I didn’t need to be seen by anyone). So after we both finished our meals, I followed her to her apartment.
When we got to her place she said that she wanted to wax my legs and face and then give me a pedicure/manicure. When she was done with that she handed me a pair of black sandals with about 3″heels and asked me to try them on. I thought they were rather tight but they did fit. She told me that I could wear those until she could get me my own pair. Then she got me a dark red skirt that came down in between my hips and my knees and a black top. she gave me some stuffing for my bra and instructed me not to wear the pantyhose as she wanted me to show off the red nail polish on my toe nails. After I got all dressed up she said that there was a problem and asked me to pull my skirt and panties down. She said that she could see my hard on through the dress and had to find a way to hide it. She decided to give me a quick hand job so that it wouldn’t get hard again for a while then she tucked it in between my legs and pulled my panties up tight and had me put my skirt back on. She then brushed out my hair and put it in a ponytail and helped me with my make up and we left to go shopping
I have to say I was really scared to go out in public dressed this way but she assured me that no body would know the difference but I still felt very vulnerable being dressed up out in the public. The feeling was sort of erotic for me. As we were walking to her car she asked me to make sure that I keep my knees together so I didn’t look like a slut. When we got to the car, she showed me how a lady gets in and out of the car by sitting in the seat and then move my legs in while keeping them together. After all, I wouldn’t want any guys trying to sneak a peak of my panties. When we got to the mall, she told me that she was going to get me 2 outfits and was going to get me something sexy. We first went to a department store and we got almost everything there but she wanted to stop by an accessories shop to get me ears pierced and what ever else we might find. As I was trying on the clothes she asked the sales girl if it was okay if I could wear my purchases out of the store, she said that as long as they were paid for so I ended up wearing a purple dress with a ruffled short skirt and a pair of matching open toed pumps with about 3 1/2 heels. We went to get my ears pierced and got some nice gold hoops to wear. After we were done shopping I had 2 complete outfits and she told me that I wouldn’t be wearing any guy clothes while I was with her. I told her that I didn’t really want to anyways and she said that she was hoping I felt that way. When we were done shopping she took me out to dinner at a nice restaurant. While we were there, we started playing footsie under the table and she put her foot right on my crotch and promised a wild time tonight. then she asked what she should call me as Kevin just wouldn’t do, I told her that I kind of liked Kalista or Kali for short. She said that sounded great. When we were done with dinner we went straight back to her place. She gave me a short night gown and put one one herself. I stripped to just my panties and put the night gown on. When I was done she was sitting on the sofa. I sat next to her and we started kissing and both of our hands were all over each others bodies. I started licking her boobs and worked my way down to her well trimmed mound. I was rather apprehensive as I’ve never had real sex before much less given oral sex but she assured me that it would be fine so I just dove in. she guided me as to where she wanted me to lick her the she grabbed my hand a guided my fingers in to her wanting pussy. I was licking her and fingering her until she had a few orgasms and the she moved to the floor and said that she was ready for me to enter her. She reached into my panties and pulled out my 5″ wonder and got it nice and hard, then guided me into her waiting hole. I started thrusting in and out until we both came together in a wonderful explosion of emotions and feeling.
I stayed with her for almost a month after that never even having to think about wearing pants. That was the best time of my life. We still see each other from time to time bit nothing will ever beat that first night
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