I have a tiny penis and had never given my gf an orgasm when fucking her ( only through oral or digital play) We had ventured into more expansive sex life which included cuckold sex play. One of our hook ups was inspired by my gf wanting to be fucked by a virgin ( actually hard to come by) However a guy I had befriended in my workplace was a self confessed virgin - never even had a girlfriend before. I talked him into a threesome featuring my gf. He was very nervous about it at first but when he met my gf it inspired him to chance embarrassing failure. It also settled his nerves a bit when I told him I have a small penis and had never made her cum with it. As for himself he was definitely well endowed. Right at the start of our engagement she boosted his ego by being very impressed with his manhood. He was still a bit nervy and worried about his stamina - very fearful he would cum too quick or even prematurely. He need not have fretted though because although he probably didn't last for even a minute when he fucked her she was so excited by the breaking his cherry thing she came very quickly herself. He recovered and fucked her a second time - he definitely was far less inhibited and much more confident and lasted long enough to give her multiple screaming orgasms. I had never seen her so enraptured. She was crying out and moaning while practically screaming for him to fuck her harder. She loudly announced it when she started cumming and was actually crying.
How are the two of you handling the situation? Is she expecting more action with him and him with her? Are you still having sex with her?
Past tense. She has moved to North America because of her career. Still have contact and she may be coming to Britain this summer but she is in a exclusive relationship now and I don't think her s/o has any interest in anything outside of monogamy.
He fucked her a couple more times that I know about but I wasn't involved except she told me about it and gave me some details. He actually became very emboldened by the whole experience and lost his shyness with women. The fact that he so easily made my gf cum gave him the confidence to chat up women and the only reason he didn't fuck my gf again was he actually got himself a gf of his own. My gf told me that not only did he have good stamina he also had quick recovery. The last time he fucked her he managed to do it three times and might have done her again but she was totally sated and drifted off to sleep while playing with his cock to make him hard again. They didn't fuck again but she sucked his cock in the morning