Chapter 1

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.

I lay on my back with Jennifer straddling my waist when she said, "Hey, for my birthday, I want to tie you up and have my way with you!" I laughed, thinking that this would be almost as enjoyable for me as it would be for her, so why not?

"Sure," I said and quickly got undressed. Jennifer went over to the closet and came back with a few of her thongs. She had me lie back on the bed and tied my hands to the headboard. Then she put a pillow under my hips, lifting them off the bed a few extra inches. She grabbed each of my legs in turn and tied them to the posts at the foot of the bed. It was a little different than what we usually did, my legs were spread wider than normal, but with my dick rock hard and my mind on what I thought was coming, I really wasn't in a position to question it.

When she had me all secured she pulled off her top and bra and leaned over me. She left her hard nipples drag across my chest and up to my face. I sucked on one nipple and then the other for a few minutes before leaning down to whisper in my ear.

"Remember a few weeks back on your birthday when you fucked my ass? I said you could only do it if you let me fuck yours. Well it's time to pay up mister and I don't want to hear any of your complaining, so why don't you suck on these for a while," she said and stuffed her used panties in my mouth. I could taste the sweet juice of her pussy; she must have been wet for a while, I thought. The look of fear and apprehension must have been apparent on my face for she giggled at me.

"Don't worry, if I can take your dick you can sure take mine," and she held up a realistic looking dildo. "I know it's a little bigger than yours but I'm sure it will fit," she said with an evil smile. "Don't even try to tell me you don't want this, your dick is rock hard. Now be a good little slut and relax for me will you?"

Relax? How was I supposed to do that when I was about to get my ass stuffed like a cheap little slut? But I realized she was right, my dick was rock hard, and while I thought about that a wave of euphoria washed over me as she slid her slick, lubed hand up and down my hardon. I gasped into the panties in my mouth, my eyes unfocused and all thoughts of resisting fled from my mind. At first I didn't even notice the lubed finger that wormed its way into my asshole. She slid it slowly in and out, moving it side to side to loosen me up before adding a second. With two fingers in me she slowly massaged my prostate, an organ I didn't even know I had or that gave me so much pleasure until a moment ago. I started moaning while she was fingering me, humping my dick up, trying desperately to get some more fiction on it. But if anything, she loosened her grip and gave me only the barest of touches.

"Hmm, does my naughty little slut like having her little asspussy touched?" Jennifer moaned in my ear. I didn't even know where she was coming up with these things she was saying but for some reason it was driving me crazy and I moaned out in agreement. "That's right, little sluts love having their pussies touched, don't they?" She giggled as she gently stroked the sensitive tip of my penis. "They love having their little clitties rubbed too, don't they?" I whimpered a little at her intense assault on that sensitive place but she let up before it could become unbearable.