3rd time receiving anal, an MFM suddenly turns MMF
I was in my early 20s and had made friends with a couple that was close to my own age, slightly older. We had partied a few times and I really found her attractive and it seemed mutual. Eventually I got a call from the guy and was invited over to join them in a sex 3 way that Saturday. I arrived and the guy, Sam was the only one there. His girlfriend was at work but would arrive in a couple of hours and join us and we’d get it on. So we got stoned together and talked about sex, and he showed me a box of rubbers and a tube of KY jelly he had, to keep things clean and slick of course, and I agreed it was a good idea. So he set both of these items on the coffee table and we worked on the bong and some drinks. I really didn’t think anything was going on other than getting ready to eat and fuck his girlfriend Jana, but after awhile and after I got very high I kind of thought he was eyeing my butt which was in some tight shorts, and he brushed up against me a few times. I could also see his hard on prominently in his shorts and I had one also as I anticipated Jana’s arrival. She arrived and got down to the bong smoking, and after a few minutes Sam left and allowed me and Jana to be alone together for awhile. Our clothes came off quickly and she sucked me off, I returned the favor and ate her out good (skinny sexy gothic blonde) and we fucked. After catching our breathes she started asking me if I’d ever tried sex with a man before, suddenly the KY jelly and rubbers made sense. I confided in her it had been many years ago but I had received anal twice as a teen and it was OK the first time but too painful the next time. She asked about cock sucking and I told her no, I had no interest in sucking or having a guy do that to me. She then confided in me that Sam was bisexual and would really enjoy fucking me and she would enjoy watching but Sam would only fuck me, no sucking.
I was surprised, however I’d done it before, and She also said Sam was not real big and it probably wouldn’t hurt much if at all and he’d use plenty of KY jelly and a rubber. “Pretty please? For me?” How could I say no, so although I was still apprehensive, I agreed. We went back out to the living room and Sam arrived back home (he brought snacks for later). Jana took him aside and discussed the results of our conversation, then I watched him take off his pants and his erect cock sprang out, my first look at it. She was right it wasn’t too big maybe 5 inches so average, but what I noticed was the head was really pronounced. The head was sort of bullet shaped and wider than the shaft, circumcised, nice tight balls (he was also blonde to the core). I reached out and touched it and his balls, I guess I wanted to touch what was going into my butt. Then Jana told me to bend over the coffee table and I nervously assumed the position. I watched over my shoulder as she put the rubber on Sam and squeezed a generous glob of lube on the head and a line down the shaft, she then spread my tight butt cheeks open and rubbed some in my ass crack, then inserted her finger slowly, lubed me up inside, and withdrew. Soon I felt his greased cock head against my butthole and he pushed forward. About half the head was in and he held it there for me to adjust to it. My butt had not been penetrated by a cock in years, but I gradually relaxed and pushed back on him. He then pushed the head all the way in and slowly pushed it deeper. Soon most of the shaft was in and he began diligently fucking my ass while she cheered him on. I was really tight and it hurt more than I thought it would but I wanted him to nut inside me so I persevered, but the big cock head was challenging especially when he pulled it out. She
ran two fingers in me to re lube and put another gob on him with a fresh rubber. He shoved it back in but I was grateful for the re lubrication. He went for a long time and finally he sped way up and I felt his cock swell up and spasm and knew that finally he had cum. He pulled out and the cool air felt really strange on my open butthole, and I was sore as hell, but I didn’t regret doing it and allowed him to do it again several times after that.
I was surprised, however I’d done it before, and She also said Sam was not real big and it probably wouldn’t hurt much if at all and he’d use plenty of KY jelly and a rubber. “Pretty please? For me?” How could I say no, so although I was still apprehensive, I agreed. We went back out to the living room and Sam arrived back home (he brought snacks for later). Jana took him aside and discussed the results of our conversation, then I watched him take off his pants and his erect cock sprang out, my first look at it. She was right it wasn’t too big maybe 5 inches so average, but what I noticed was the head was really pronounced. The head was sort of bullet shaped and wider than the shaft, circumcised, nice tight balls (he was also blonde to the core). I reached out and touched it and his balls, I guess I wanted to touch what was going into my butt. Then Jana told me to bend over the coffee table and I nervously assumed the position. I watched over my shoulder as she put the rubber on Sam and squeezed a generous glob of lube on the head and a line down the shaft, she then spread my tight butt cheeks open and rubbed some in my ass crack, then inserted her finger slowly, lubed me up inside, and withdrew. Soon I felt his greased cock head against my butthole and he pushed forward. About half the head was in and he held it there for me to adjust to it. My butt had not been penetrated by a cock in years, but I gradually relaxed and pushed back on him. He then pushed the head all the way in and slowly pushed it deeper. Soon most of the shaft was in and he began diligently fucking my ass while she cheered him on. I was really tight and it hurt more than I thought it would but I wanted him to nut inside me so I persevered, but the big cock head was challenging especially when he pulled it out. She
ran two fingers in me to re lube and put another gob on him with a fresh rubber. He shoved it back in but I was grateful for the re lubrication. He went for a long time and finally he sped way up and I felt his cock swell up and spasm and knew that finally he had cum. He pulled out and the cool air felt really strange on my open butthole, and I was sore as hell, but I didn’t regret doing it and allowed him to do it again several times after that.
61-69, M
