I’ve known Caleb for a quite a few years, originally friends with my bf and then became mine when we got together. He’s such a generous and lovely guy! My bf considers him one of his closest friends and the same goes for him. Never saw him take a girl home when we went clubbing nor did he ever seem to have a girlfriend. My bf told me he’s still a virgin and gets nervous around girls when it progress past friendship. I felt pretty sorry for him but he said not to say anything about it. One night, on a drunken night out, he confessed to me when we were alone that he was indeed a virgin and wish he could fuck someone like me. That last sentence must have sobered him up cause he immediately apologised repeatedly and asked not to tell my bf.
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We weren’t very far into our hotwifing situation and had only seen one other person join our bedroom. I brought up Caleb as potential but he wasn’t sure about letting friends know about our situation as we didn’t want to get judged but as Caleb is such a close friend, he was open to it. Over the next year, we started to role play the idea of me taking Caleb’s virginity. It was incredibly hot and got us both going. About Caleb, he is tall and quite gamer nerdy (he is my bf gamer friend after all). He goes to the gym with my bf but he is still a bit chubby. Whenever I hug him, my head is always on his chest cause he’s that much taller.
Over a year later, Caleb was talking to my bf and saying that he might hire an escort to just lose his virginity as he was already 26 at this stage. This was the perfect setup. My bf said not to do that and instead suggested fucking me. He said that was a great offer but no cause he didn’t want to ruin his friendship with me or my bf. It wasn’t until we were having a board game night where it was me, my bf and Caleb playing. My bf brought up that he had offered me to take his virginity. Caleb turned super red apologetically reassuring that he said no and my bf was being weird. I chimed in saying I would be happy to take his virginity! He looked at me shocked and ask really? I said of course I would because I love him so dearly as a friend. Only if he was comfortable for his first time to be with me though. The choice was his, no pressure. He sat there thinking in silence for a bit and he finally said he would be down.
I pushed him down onto the couch and got on top of him. Put his hand on my tit and started to kiss him. I could feel him immediately go hard. I worked my way down and pulled his pants off and asked if he was ready. He said yes and I put it in my mouth. My bf was on the other couch, hand in pants grinning. He was surprising a good size and I couldn’t go all the way down. As I was sucking, my bf came round and started to take off my skirt for me. Then my undies and slowly started to finger me. It felt so good and I was getting so wet. I asked Caleb if he wanted to put it in and he said yes. My bf grabbed him a condom and I put it on for him. I laid on my back and he slowly put his cock in my wet pussy. It was such a rush watching him in so much pleasure. He must have been nervous though, as he went soft after a little bit. I told him not to worry and jerked him off to get him hard. Got him a new condom and slid his cock back inside me. He had a good technique and I was feeling good. After a couple of minutes, he came. He said that felt incredible and I told him to go to the bathroom to clean up. My bf took this chance to give me a real good fucking. I came twice from him. Caleb had come out cleaned and dress and I motioned him over. I gave him a kiss and told him to play with my nipples as my bf was pounding me. My bf finished by cumming inside me and we went to get ourselves clean.
Afterward, Caleb told me that was amazing and thanked us. He couldn’t be happier to have lost his virginity to me and I was honestly so proud to have been the one to take it. I told him to come back next Saturday and I’ll give him another round. He excited said yes. we started playing board games again and of course, that second round came earlier as we fucked again that night.