My First Time

I was in 10th grade I had been cross dressing for a few years, burrowing clothes from my mom when I was home alone. Mom worked so I had several hours after school to have fun. We our neighbors next door had a wonderful train set up in the basement and I would sometimes go over and get to play with it. Their son was a senior and he and his dad had spent many years building the set. So I was really impressed by it.

Well one day I was over and running the trains Paul said he has t make a phone call and left me alone. well as I was looking around I found a few adult women magazines and a few gay men magazines. I was looking at them when Paul came back and caught me. I was embarrassed but he said it was okay and that he loved looking at them too. We both were a little aroused looking at them together and I remember that he lifted up my tee shirt and just stated lightly brushing my nipples and asked if I like that. Well I couldn't hide the fact that I did love his touch and he liked doing it.

He then kissed me and led me over to an old sofa, he sat me down and then unzipped his pants and showed me his erect ****. Now I had often touched mine and made me feel so good and I have seen many pictures of them but here was one right in front of me. He pushed between my legs and his **** touched my lips. I knew then just what I wanted to do, kissing his **** head and tasting his pre-***, I was hooked. I started giving him a blow job, my first and not my last. I was in heaven and so was he for it didn't take long he was squirting *** into my mouth. I loved it and still do.

We had fun the rest of the year and when his mom was home he would come over to my house and I would dress up for him. He got me to try make up and he even brought me an old wig of his mom's that she didn't use. it was then I knew I was going to let my hair grow long and since all the kids were with a little pleading I was allowed to do also.

Sad to say after he graduated Paul went off to college. I saw him a few times on his breaks but so missed our daily play. Loved how he made me feel like a girl and I did love his ****, miss it even today.
Terriwish Terriwish
36-40, T
3 Responses Dec 14, 2012

wonderful, thanks for sharing :)

A tender lover is the best kind!

A beautiful story of your sexual awakening to new possibilities. Would like to learn more about you, and will check more on your profile, like: are you married, or gay (or both). Happy to know you. Love, Marcy.