Becoming Kari [transformation]

Kari and I have known each other for a few years now. We initially met when she was taking a class at a community college with my ex. We did a double date a couple times, my ex and I with Kari and her boyfriend. It was always a bit awkward as neither couple seemed to be matched up properly. Kari and I had more in common with each other than either of us did with our partners. It showed, as both of us broke up with our respective significant others.

Kari eventually changed schools and moved to the same town I was in, even renting an apartment a few blocks away from mine. Unfortunately, things never progressed between us. Friend-zone as it may be. We ended up being pretty close friends. We would party and hang out. Occasionally the games would turn to sexual topics. Again nothing came of it, but I learned a lot about Kari.

Kari eventually started dating a new guy, Matt. Typical frat dude. Liked to party, being a student clearly came second. He treated her well enough and she still spent some time with me. She shared some of their exploits and some of their fantasies.

Fulfilling a Fantasy [Gay] [MM]

Sex with a man. It’s a fantasy some straight guys have but few act on it. For quite a while I have thought about going through with it. I didn’t really have a fantasy guy picked out, except for one aspect… his cock. My fantasy guy had a big cock. I figured if I was going to go through with the fantasy I would go big or go home. I would talk to guys online and it would get me hot, but as soon as I blew my load that desire to try it out for real slipped away. Heather and I had talked about these fantasies at length; the idea of me hooking up with another guy was as big of a turn-on to her as her being with another woman was for me. Sometimes we would bring ass play into the bedroom and I went as far as buying a strapon for her to wear. Still, nothing happened beyond talking. I had pretty much concluded that it was always going to remain a fantasy, one not to be acted upon.

Late Night Reunion [MF]

It had been a few weeks since Heather and I had broken up. Heather and I were an average couple. She had a good body, a great smile, 34B tits, and nice tight ass. She kept her pussy smooth all the time and it would drip with the slightest attention. We had dated for about 6 months but it was clear our lives were going in two different directions. It was the goal of both of us to remain friends, a daunting task for any couple that splits up. That brings us to this story…

For the last few days Heather and I have been talking more than we had since we broke up. And just as when we were dating the topic often turned to sex. We had a healthy sex life, despite the fact that we both lived with our parents. When we were in the bedroom there was one thing that was true, we always were trying new things, whether it’s a different position, a different hole, or just something totally kinky.

Late Night Reunion [mf]

It had been a few weeks since Heather and I had broken up. Heather and I were an average couple. She had a good body, a great smile, 34B tits, and nice tight ass. She kept her pussy smooth all the time and it would drip with the slightest attention. We had dated for about 6 months but it was clear our lives were going in two different directions. It was the goal of both of us to remain friends, a daunting task for any couple that splits up. That brings us to this story…

For the last few days Heather and I have been talking more than we had since we broke up. And just as when we were dating the topic often turned to sex. We had a healthy sex life, despite the fact that we both lived with our parents. When we were in the bedroom there was one thing that was true, we always were trying new things, whether it’s a different position, a different hole, or just something totally kinky.

Fulfilling a Fantasy [MM] [First time] [anal]

Sex with a man. It’s a fantasy some straight guys have but few act on it. For quite a while I have thought about going through with it. I didn’t really have a fantasy guy picked out, except for one aspect… his cock. My fantasy guy had a big cock. I figured if I was going to go through with the fantasy I would go big or go home. I would talk to guys online and it would get me hot, but as soon as I blew my load that desire to try it out for real slipped away. Heather and I had talked about these fantasies at length; the idea of me hooking up with another guy was as big of a turn-on to her as her being with another woman was for me. Sometimes we would bring ass play into the bedroom and I went as far as buying a strapon for her to wear. Still, nothing happened beyond talking. I had pretty much concluded that it was always going to remain a fantasy, one not to be acted upon.