Written by Jeff

13 Mar 2012

I had been dressing up in womens clothes since my early teens, when I was 18 I had my first experience of giving a blowjob and taking anal,but didn't dress for that.

The time had come for me to experience more and not only that but to dress up as well. After taking my boyfriend bareback for a few weeks I arranged for him to come and see me at my house, when I was alone for the whole day, and Mum had gone to work.

From my Mums wardrobe I dressed in black lycra panties, basque, blonde wig and black stockings with the suspenders coming from the basque, this was my first proper dressing and I was so nervous.

I waited for my boyfriend to arrive. Soon he came in through the back door of the house, and I called him to come upstairs. Without a word he put his hand down to feel the stockings against my leg. It made my cock spring up to attention.

In my wig I looked the sexy girl I wanted to be and was ready. He pulled down his jeans and told me to suck his cock to which I eagerly did. I was excited but nervous, like I hadn't ever had anal sex. I had found and used a smallish vibrator that was in Mums stuff. I switched it on and stroked my stocking tops with it. My boyfriends cock was huge, about twice the size of mine and he started to grow hard. I reached for the lube and appied a generous amount to the monster shaft that was about to assault me.

I could tell it wouldn't be long before he wanted it inside of me. I started to suck again, only this time faster. He pulled it out of my hungry mouth and spun me over onto my front, he lubed his cock head up and tried to push it inside of me.

I could feel it going in but it hurt so much, we must have tried about 20 times but it wouldn't go. I must have been tight due to my nervousness, I was cleching my ass.

Eventually he lay on his back and told me to ride him. I got on top and started to straddle him lowering myself onto his ever growing cock. Finally I managed to ease it inside, for the first 5 mins I pretended that I loved it even though it hurt, and all I wanted to do was tell him I couldn't take it, but I didn't and I'm glad, as it started to feel really nice and I started to push down hard to meet his thrusts.

After riding him like this for about 10 minutes,and listening to his dirty talking, it wasn't long before he shot his hot load deep inside my ass, thrusting again and again and again.....about ten giant pushes. Telling me how he had just taken my new virginity as a CD, he said how good a fit I was, and how tight and warm my pussy was... even better than straight bareback we had done before. He loved my ass being tied and packaged in the suspenders, as he watched me fuck his dick. We have met quite a few times since then and experimented in lots of new ways..........