My friend Steph has been my number one support during the separation from my spouse and the only person I know in real life who is aware of my new slutty streak. Steph is deep in the local kink scene and she has offered to bring me along to sex parties but so far I’ve declined. Recently though she offered to set me up with a younger guy who she told me is very mature, knows how to handle himself, is into no strings attached situations, and takes good care of the people he doms.

So I started messaging with Connor (M25) over the weekend and he gave me a whole laundry list of kinks that he is into: ropes, impact, degradation, and the like. Most of them were a hard pass for me. Not to kink shame anyone, I just happen to be pretty vanilla outside of my newfound love of exhibitionism. He did offer nipple play, which I am very into and asked if I would be into anal, which I decided could be fun. I’ve only had anal sex once before when I was in high school. It was with a guy I had a huge crush on and wanted to impress, but he had a really small dick and I barely felt anything. The whole thing was kind of disappointing and we never spoke again. But that was a long time ago and I figured I would give it another try.

Connor came over last night and we didn’t waste any time on chit chat. We went straight to my bedroom and he told me to take my clothes off and lie on the bed. I had told him that I wanted to be a pillow princess and just have him act on my body while I took it easy and he was happy to oblige. He took his shirt off but left his pants on to start and took out these small magnetic balls. After teasing my nipples enough to get them erect, he used the balls on me like clamps, putting one on either side of a nipple so that they’d squeeze together, pinching my nipples hard. With my nipples clamped like that he brushed them very gently with the tips of his fingers and kissed them lightly. I was getting insanely wet and asked him if it was okay to use a toy on myself. He told me to go right ahead and even got me my little pink vibrator out of the nightstand.

He slowly ramped up the intensity of the nipple play until he was pinching, pulling, sucking, and biting on them, mixing in some very soft petting and kisses all up and down my body and face. I have no idea how many times I came but eventually he asked me if I wanted him to fuck me. I said yes. He asked me if I wanted him to put in my butt and I said yes, please. He finally took off his pants and he was rock hard. His cock was pretty big, not porn star big, but big enough to make me wonder for a moment if it was a good idea to try to fit in my ass. He must have seen the concern on my face and assured me he’d go very slow. He told me to lie on my side and get comfortable with pillows however I wanted, which I did.

And he did go very slow. He used my favorite lube and, kneeling behind me, started with his finger to get me used to the penetration. When he positioned his cock on my hole, he took probably a whole two minutes of teasing and careful progress just to get the tip in. He stayed there, making very shallow thrusts for a long while. The sensation was unlike anything I’ve felt before. I had to turn the vibe off so that I could just be there with the feeling of having my asshole and insides stretched. He asked if I wanted him to go deeper and I could just barely nod and say “uh-huh.” He took his time, making sure that I got used to each new centimeter that he penetrated me before moving forward to the next. It was hard to breathe and I was cumming in new ways that I had never even imagined, orgasms from deep deep inside of me that seemed to last forever. He was very attentive to my needs the whole time, stroking my body gently and telling me how beautiful I was, how much he loved being inside of me, what a good job I was doing taking his big cock in my ass, all of which made me cum even harder.

When he was all the way in, his hips pressed against my butt cheeks, he began to rock back and forth and a whole new wave of sensations came on. I turned to jelly, completely surrendered to him. He picked up the pace so gradually I didn’t notice it at first until my whole body was shaking. He kept my body steady by cupping me around the shoulders, breasts, and hips and kept his dick buried deep inside of me. Then he slowed down again and asked if he could move my body, gently rolled me onto my stomach, climbed on top, and penetrated me again. His thrusts were still slow and steady, but now his stroke drew his cock all the way back out to the opening of my ass before sliding all the way back in each time. Orgasm is the wrong word for what I was experiencing at that point, it was more of an all-encompassing wave of mental and physical power and powerlessness wrapped into one.

When he finally finished deep inside of me he stayed lying on top of me for a long minute, then slowly pulled his still hard cock out of me, giving me one last rush of pleasure. He took good care of me afterwards, holding me, petting and kissing my hair, and asking me how I felt, if there were any parts that I liked the most or that I wished had been different, and so on. I told him it was perfect, exactly what I wanted and that I would let him know if I wanted to do something like this again. I might, but my asshole is still throbbing and my morning poop was also a new experience, so we’ll see.