I found out I had a liking for crossdressers when I was 19 yrs old. I was going out with Kelli, who was 17 at the time. I met her younger brother Eric, briefly when I went to pick her up to go to the movies or just hang out. He was 16 then.
He was thin and had longish hair and looked a lot like his sister. I mean I could see the family resemblance.
One night after dropping her off from our date and having been making out for what seemed like an eternity with me only getting hard from having my tongue in her mouth and my hand up her shirt I was walking back to my car which I had to park down the street when I saw a nice looking girl walking towards me. She had on a skirt and a t shirt and tennis shoes. As she passed I smiled and she said "hi". I said hello and kept walking but much slower. I turned around because she looked familiar and got a nice look at her from behind. I still had a hard on from my gf not relieving me and seeing this girl just made me hornier.
I got to my car and turned as I got in seeing the girl still walking down the street.
I started my car and drove slowly with my windows down because back then my car didn't have air conditioning. I slowed even more when I got to the girl walking and asked her if she needed a ride. She smiled and said she was just out walking and lived just around the block. I really wanted to get to know this girl so I asked her if she just wanted to go riding around with me.
She smiled again and after a moment said ok. She got in the car and we drove a little ways. I asked her her name and she told me it was Tonya. I told her mine and said something like" you look nice in that skirt". She seemed to like that and said thank you. I kept feeling like we had met before and was staring at her chest a bit because it looked like she was developing nicely and I was wanting to get my hands on her breasts if things would go that way.
I asked her if there was any place she'd like to go and she said "I don't know maybe someplace quiet".
I drove about a mile to place on the edge of town where we could be alone and see some city lights and maybe car headlights coming our way if we got enchanted with each other and didn't want to get caught undressed. She looked a little young but at 19 I was horny and thought maybe this was the girl for me.
I parked the car, turned off the lights and said you can move closer to me if you want. She said ok. Then I asked her if we had met before. She said yes but didn't say where and I was thinking maybe she was maybe someone from school or a friend of a friend. We started kissing and her mouth was soft and her tongue was eager in my mouth and I went to run my hand over her t shirt to get a feel of her **** when she stopped stopped me by lightly pushing my hand away. We continued kissing and I had my hand on her leg and was inching it slowly up under her skirt. She didn't seem to mind. I was so wanting to finger her and was getting so aroused when she stopped me just short of touching her panties.
Then she stopped kissing me and said maybe I should take her back and that maybe this wasn't a good idea. I apologized for trying to go too far but that I really liked her and was getting really turned on. Her hand slowly went to my crotch and she felt the bulge in my pants.
She said, "Wow, you are turned on". and then, " maybe I can do something about that".
I kissed her and she started undoing my belt. I reached down and helped her. I undid my pants button and pulled my zipper down thinking maybe she was going to give me a ******* or better yet a blow job. Her hand went over the bulge in my underwear and rubbed a bit and then I felt her fingers sliding into my shorts and tug my **** out with just the head sticking out of the top of my underwear. Her fingers circled around the head and and she asked me if I liked that. Did I ever. I said yes of course and then her hand was stroking me while we kissed and she felt the precum on the tip of my **** and stopped. She put her hand to her mouth and tasted the wetness and then her head went down towards my lap and it was so amazing feeling her lips just on the tip of my **** head and her tongue swirling around. The feeling of her light sucking and then more of my **** in her mouth.
I rested my hand on the back of her head while she sucked my ****. I layed back and would look down every once in awhile not believing I had just met this girl and twenty minutes later she's sucking my ****. I was in heaven.
She looked up at me with her hand around the shaft of my **** and asked me if I liked it. I said, "yes, it feels so good".
We kissed and then she went back to sucking my **** with more enthusiasm. A few minutes later I started to *** and told her I was ready thinking she would pull her mouth away just as I orgasmed. At least that's what I was used to from other girls. She didn't. She kept sucking and I spasmed and my **** throbbed and squirted hot *** into Tonya's warm mouth. She swallowed and kept sucking. It felt so good finally ******* and being swallowed. What a turn on.
Finally I made her stop sucking because it felt so good it was painful and I really had to pee.
We kissed afterwards and her mouth tasted different but nice and I didn't care as I realized I was tasting not only my **** but also the remnants of my *** in her mouth. I was in love...
I got out of the car and went pee. She did too but went behind a tree for modesty. We got back in the car and we kissed a little more and hugged and finally she said, "You better take me back. It's getting late and I don't want to get in trouble."
We drove back with my arm around her shoulders. I dropped her off where I met her and asked her for her number because I wanted to see her again. She wouldn't give it to me but said, "Don't worry, we'll see each other again. After all you know the neighborhood where I live and she walked away.
A couple of nights later I went to pick up Kelli for our movie night but really thinking about Tonya. I sat on her couch for about twenty minutes when she finally came down the hall. I said we had to hurry or we'll be late for the movie. We got in the car and as we drove away from her house she said she was sorry for taking so long but she had to help her brother a little before she left and she had to wait til her parents had left for the evening before she could help him. I asked her why, of course and she said, " well..." I said, "yeah, and...?". She said she was taking some of her clothes into him so he could try them on and she was doing his make up when I rang the doorbell....
Damn, was I surprised when I realized that Tonya was actually Eric. I was so confused by my sexuality at that point but knew I liked what had happened and at times was really wanting it to happen again. I couldn't believe I was so turned on when everything I was brought up to believe was somehow skewed.
I didn't tell Kelli what had happened but she did notice I was somewhat distant with her for awhile. I did see tonya again after I dropped Kelli off from our date.
While making out with Tonya I told her I knew who she, or he, or she, was. I was still confused and didn't want anyone to know. Eventually Tonya and my sexual relationship went further as I ended up stroking her **** as we kissed and she stroked mine before she gave me head. We eventually had intercourse if that's what you call it and after asking her what it was like to suck **** she said, "Why not try it. I'm not going to tell anyone."

OmniFix69 OmniFix69
51-55, M
6 Responses Aug 15, 2014

A great experience.

A walk on the wildside

a good story and for once one that sounds as if it could be true
thank you for telling it 10/10%

Great story. Well said. Nice for you to go with the flow and enjoy all life has to offer.

Sexy story

A wonderful story, Tonya must be very passable to make it through the first session without you knowing who she really was. Thanks for sharing.

Deep down I think I knew she was a guy but I wanted to be intimate and alone with her. Something taboo that no one would know about. A one time thing that was addicting. I also thought Eric was attractive and that set me off balance feeling that away about a guy a couple of years younger than I was.

Yes, that could and would set you off balance. But you went with your intuition and enjoyed the experience. I never would have. Your Rock!