My girlfriend and I have always been a little kinky. We liked to tie each other up every now and then. We both enjoyed it every time we did it. I didn’t realize that it was only the start of something that would land me in the position I am in now, on my knees dressed in a slutty skirt and panties with makeup and a wig, taking her friend’s dick in my ass while I ate another guy’s cum out of her freshly fucked pussy.

I guess it all started a few months back on my birthday. I had wanted to fuck my girlfriend Jennifer’s ass for a while but hadn’t wanted to bring the subject up for fear that she would be pissed off at me. It was my birthday, however, and I felt that maybe she would be up for giving me a little extra this one day.

We were making out in my bed when I decided to bring the subject up.

“Babe, since it’s my birthday and all, I was wondering if we could, you know, try some anal,” I said and added, “just this once,” when I saw the look she started to make. She was quiet for a second, I started to worry that I had made a mistake but then she batted her eyes at me and smiled.

“Sure Timmy (that’s me), we can try some, but if you expect me to do it then I expect you to also,” I smiled and laughed when she said this, thinking there was no way I would let anything like that happen because I was straight and besides, after I did her I could always say no to whatever she wanted, right?

She got up off the bed and began seductively pulling off her shirt and bra. I sat transfixed as she exposed her soft, delicate skin to my eyes. Her long dark brown hair cascaded down over her shoulders. She cupped her breasts and squeezed them together, teasing the nipples to hardness with her fingers. I sat up and whipped off my shirt and shucked my jeans. My dick was already rock hard and jutting out the flap of my boxers. Jennifer giggled as she watched my dick bounce around as I grabbed the lube off the dresser.

A little pressure, lots of lube, and about two minutes later I collapsed on her, panting, as my cock squirted cum into her tight asshole. She smiled up at me, brushing her hand along my cheek and asked if I had enjoyed it.

“That was one of the most intense orgasms I’ve ever had,” I admitted to her. She smiled and said she hoped it was because she planned on trying it again. I smiled to myself and began kissing her, telling her how much I loved her, completely forgetting about the stipulation I had agreed to.

School ended for the year soon after and since I spent so much time studying for the end of the year tests, I didn’t get to see her as much as I wanted. It wasn’t until a week after school ended, on her birthday, that we got to spend some time alone together. Her parents had left her home alone that night so we could have a few friends over and throw a nice party for her. It was late when we finally kicked everyone out of the house so we could have some privacy. Her parents wouldn’t be back for a few more hours but we wasted no time running to her room and jumping into bed together.