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Group sex story - Jenny and I had been dating for about three years. It was fairly serious, but never in a way that we figured would ever lead to marriage. We were both just too independent for that. What held us together was the sex, in a lot of ways. And the sex we did in a lot of ways. She was more experienced than I was when we met, when she was on the rebound from dating a friend I knew casually.
After three years, though, we were pretty much at the same level experience wise... and the same level was becoming a little too routine.
Jenny was always open to suggestions and ideas with it came to sex play. Once, I'd suggested a threesome, her and another woman and I. She went for it right away. She brought home a woman-friend from work one evening, a lady named Lisa. Lisa wasn't as attractive as Jenny, but good-looking enough for our purposes.
Jenny took her out to a bar that night together, and by the time they got back they were both pretty tipsy. It didn't take much work to get Lisa into bed with the two of us.
I started in on Jenny first so Lisa could watch us. I played with Jenny's tit and watched Lisa watching us as she got hotter and hotter. It was only a few minutes before I was able to slip into Jenny's cunt. I was surprised when Lisa crawled up and straddled Jenny's face, grinding against Jenny's tongue. Just when I thought I would come. I slipped out of Jenny and pushed Lisa down onto the mattress and entered her. Lisa rolled slightly over and went to work on licking Jenny while I continued to fuck her. The sight of the two women was too much for me and I exploded in Lisa.
The best part, though, was watching Jenny and Lisa afterward, first sixty-nining each other, then working at each other with their fingers. Then Jenny pulled out of Lisa and to my surprise, she pulled a strap-on dildo from her dresser drawer. It was about ten inches long, thick, and black. Although it was clearly hard, it had a lot of give, like a real cock. She buckled one strap around her hips, and laced another through her legs, so it was on tight, the butt of the dildo positioned to slip into her hole and grind against her clit.
Once it was securely in place, she lay on top of Lisa, who spread her legs and wrapped them around Jenny's waist. It took Jenny a moment to position herself, but then she found the entrance to Lisa's pussy, and slid it slowly in to the hilt. By now, Lisa's eyes were glazed, her head thrown back as Jenny began to slide in and out of her pussy. Soon Jenny was bucking and thrusting like a man would, Lisa rising to meet her every thrust. She grabbed Lisa's hands and pinned them to the bed, arching her back and flicking her hips in rapid thrusts.
By this time I was hard again (and then some), and Jenny saw the look in my eye. Without a word, she rolled over so that Lisa was now on top, straddling the dildo. I moved around back and lubricated my already-slick cock with the juices from their cunts. Positioning myself behind Lisa, I slid easily up her ass.
In a moment, we were both in place, Jenny and her dildo in Lisa's pussy, me and my dick in Lisa's ass. We quickly found a rhythm. Every time Lisa bucked back off the dildo, she'd push me deeper into her, and vice-versa. Best of all, I could feel the dildo sliding in and out against the thin tissue between us, and the thought of it excited me even more. I thought about what it must be like for Lisa, how this double-filling must feel like, and with that thought -- I exploded inside her, just as both of them came in a long groaning orgasm as well.
The memory of that evening stayed with me for a long time, especially the part about feeling the dildo inside Lisa, and watching her being fucked by Jenny. I began to wonder more and more what it must feel like to be fucked. The more I wondered about it, the more obsessed I became with the idea. Finally, one night, after a long night of lovemaking, I confided my thoughts to Jenny.
She said that she had a solution, and pulled out the strap-on dildo again. She put it in my hands, let me feel it, and said that since it was late, and we were too tired to really enjoy it this time, she'd do it to me next weekend... and she promised that it would be something special in every sense.
I spent the next week thinking about it and anticipating it. When the night finally came, I showed up at her house hot and ready to go. Our foreplay was even more frantic than usual, and I could see that she was as turned on by what was to come as I.
Finally, she said that if she was going to do the fucking, she was going to call the shots, and do it her way. Knowing the many things she was into, I was more than willing to accommodate. The main thing was a blindfold; she wanted me to be able to imagine being truly fucked. I accepted this without question and put it on.
I could feel her long, manicured fingernails probing at and into my ass, slender and delicate. She had me get up on all fours to give her better access. First one, then two, then three fingers. She leaned over me, and I could feel her breasts on my back as she continued her probing. After a moment, when I was nice and relaxed back there, she told me she was going to put on the dildo. I waited in breathless anticipation, unable to see what she was doing, but remembering every detail from when she'd worn it last.
At last, she said she was ready, and told me to grab the headboard with both hands, to steady myself. I did. After a moment, I felt a rubbery hardness poking at my ass. It felt big, impossibly big. But I was determined to take it all. I moved my legs further apart to accommodate it. Inch by inch, it slid in, the sensation was incredible, stretching and a little painful at first, but that part quickly passed.
Finally, I could feel all of it inside me. All of my sensations were focused entirely on my filled ass. I didn't move for a long moment, letting myself get used to the feelings. Then, slowly, I began to move back and forth, and it began to slide in and out of me, slowly at first, then faster. I began bucking harder now, driving back to meet each thrust.
It was after only a few minutes of this that I noticed something was wrong. The dildo seemed actually bigger than it had moments before. It seemed to flex more than I'd remembered. And I could feel hairs that shouldn't be there brushing against my ass and legs.
I whipped off the blindfold and turned to see not Jenny, but Mark (my casual friend, and her old lover) behind me. Jenny stood behind him, watching. She smiled as she saw that I knew. "Surprise," she said. "After all, what's good for the goose..." Even from here I could see the base of the rubber on his cock, which had added to the illusion.
Mark slowed his thrusting, met my eyes. "If you want me to stop, I will," he said. I hesitated only a moment before shaking my head, no. He smiled and started thrusting into me again, harder now, no longer making any pretense at gentleness. I gasped and fell forward onto the pillow as he slammed into my ass, again and again, grabbing my hips and pulling me back onto him.
After a moment, Jenny slid beneath me on the bed, and raised her legs to give me access to her ass. I slid in on the first try, and now it truly was just like Lisa, right there in the middle of the sandwich, him thrusting into me from behind, her taking me in her own ass at the same time.
Mark continued to get bigger in me, until suddenly he tensed and I could feel the heat of his cum filling the condom inside my ass. Instantly, I came as well, filling Jenny, who held me tight to her as an orgasm rippled through her body as well. It went on for what seemed an eternity until we all finally collapsed onto one another, sweating and gasping.
Over the course of the long night, we reversed many times, once with Mark sandwiched between Jenny, and me and then with Jenny between the two of us. But nothing ever quite equaled that first time, and one of the best surprises I'd ever received.
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