I'm not sure if this is the right place to post but here it goes...I have a straight friend who knows I have sex with other men and was nervously asked me to experiment having sex with him. So we discussed it beforehand and decided I'd top for the first time and he'd bottom (his first m2m experience). We decided to skip the foreplay and get down to business and if he was too uncomfortable to just say "Stop". For him, he strongly hinted at being at the very least, uncomfortable, maybe having pain. His face was wincing all the time, so I took it slower but that didn't seem to change anything. He encouraged me to continue. I decided to finish up in doggy and just get it done with. Post coital we cuddled and he thanked me and we kissed (which I would call the best part of the experience) So my questions are: If someone is clearly not 100% enjoying sex, as a top, does it ruin it for you? (Smiling bottom talking here) He said he enjoyed the experience despite the pain. Do you think he'll handle it better next time if we were to try?
I don't really know what else you could have done. He was a willing participant, you communicated before and during to check he was okay with everything and he encouraged you to continue and even said he enjoyed it afterwards. In fairness, people pull different facial expressions when they are bottoming, so what you may have thought was a wince might not have been. If he asks to do it again, it's likely he enjoyed it more than you imagined. I guess my best advice would be to use plenty of lube beforehand and re-apply during sex to avoid pain. Bottoming can be intense, but it shouldn't be painful. In most cases, when it's painful for the bottom, it's due to insufficient lube.
Yes, that would make it difficult, if not ruin it, for me. I don't want my partner to be in pain, so it does lessen my enjoyment of the experience if my partner is in pain. It can take a lot of work, patience, and practice (and lube) for him to learn to relax and get used to the feeling.
jumping right into the action is something I wouldnt recommend.. however I am a woman so its different. I think a slower pace is better for me. some times what goes on in the movies dont really work for real life. i have had sex with men and a few just want to bend me over like i am Jenna Jameson and go to town and that doesnt work for me
@Jared J To answer your questions: 1. For me, it does ruin the experience if my partner is not totally into it. There are lots of other ways, as I'm sure you are aware, to have intimacy without pain...so you can stop the intercourse and do that for awhile. 2. Will he handle it better the next time? Possibly. I'm not an expert on being a top...by any means. But, I do know that everyone is built a bit differently and sometimes a different position is better. So, you might try that. Also, foreplay can be really helpful to reduce the stress and help to relax and that can make all the difference. That foreplay could include massage and "toys".
Well we did try again, this time he didn't bottom but we did other fun things and he did climb on top of me. He did admit that he was a in a bit of pain and didn't feel great afterwards from the first time. The funny part is: I feel like I am in this with him. I am 31 years old and this is the first time I've been with someone not much older than me (he's 30) and I like him beyond sex which is the first time I've felt this way with a guy.
Yet, you consider him straight? His sexuality is his to define of course. So, maybe it can’t go any further. FWIW, I’m married, and in love with, a woman, and I also have a FWB who I feel I do love in a different way and our intimacy is incredible. I also had a straight friend, who recently passed away, of 40 years and I loved him dearly...and sorta platonically romantically. Love can take many forms and I’m finding some of us can express that love in different ways. So, even if this doesn’t go anywhere beyond what you have, it sounds special! The trick is to manage your expectations about what he can offer you in return.
In an age of texting we called and talked on the phone a bit this week whicy was nice. He is confiding in me that he has really enjoyed being with me and exploring at least having sex with men. We aren't going to say we are in a relationship or anything as we are decent friends to begin with but that might change in time, we've both left that as a possibility. We did hook up a few more times and he actually spent the night with me on Saturday night which was great. What can I say? I really like him and I find his innocence and discovery to be charming.