How do I (30F) make first-time sex more comfortable for my inexperienced partner (30M)? How should I initiate?

Hi /r/datingoverthirty,

For those of you (particularly men) who lost your virginity at a later-than-average age, what did your partner do/what could they have to make the experience more comfortable for you, both initiating/discussing sex and during the act itself?

I (30F) have been seeing a guy (30M) that I really like for about a month and it’s been great: he’s smart, funny, considerate, and interested in getting to know me as a person and is very open to sharing personal things about himself with me. That said, we haven’t progressed too far physically yet, as in, we haven’t done anything beyond kissing yet. In fact, we didn’t have our first kiss until our fourth date (I initiated and he was very receptive and has since initiated kissing himself) and he’s hinted around at the fact that he doesn’t have very much romantic or sexual experience which I suspected from the jump and am very much okay with. That said, it’s been a month and I’m pretty damn hot for this man. We see each about every other day and my desire to drag him into bed has grown steadily. Generally speaking, I know how to get things started, but given his stated inexperience, I’m trying to keep a little bit of a lid on my libido until he’s ready for more.

Based on how the early stages of being physical (breaking touch barrier, kissing, making out, etc.) have gone, I’m definitely going to have to be the one to move things forward sexually, which is fine. My conundrum is finding the best way to do this. I really like this guy, enough that I’d honestly be happy to DTR and move forward with calling ourselves a couple at this point which is something I’m normally terrified of doing (I’m usually an open multi-dater, this is the first time I’ve dated one guy without wanting to date anyone else in about five years). I’m not sure if he’s actually a virgin, but I suspect he is so I want to give him his own space and time to be ready to have sex, but I also don’t want to sort of leave him hanging on figuring out how to get there on his own.

I guess my question is, for those of you who have been in a similar situation what would you have wanted your partner to do? Directly start a conversation about where you are as far as being ready to move things forward physically and whether you’d be more comfortable doing that after explicitly declaring exclusivity? Just sort of nudging things toward sex by getting increasingly physical? Something else? Honestly, I’d really like to have a conversation about it (without mentioning that I think he’s a virgin/asking him to admit that, obviously), but I’m not sure if that’s something that’d be awkward/embarrassing?

Also, as far as having sex with him for the first time goes, any tips for helping an inexperienced partner feel comfortable in the bedroom the first few times/taking some of the pressure off the situation?

I’m sure I’m overthinking this like I did with being the one to kiss him first so I appreciate any help you can give me! I just really like this guy and don’t want to screw things up, haha.

Submitted May 22, 2019 at 01:10AM

Hi /r/datingoverthirty,For those of you (particularly men) who lost your virginity at a later-than-average age, what did your partner do/what could they have to make the experience more comfortable for you, both initiating/discussing sex and during the act itself?I (30F) have been seeing a guy (30M) that I really like for about a month and it’s been great: he’s smart, funny, considerate, and interested in getting to know me as a person and is very open to sharing personal things about himself with me. That said, we haven’t progressed too far physically yet, as in, we haven’t done anything beyond kissing yet. In fact, we didn’t have our first kiss until our fourth date (I initiated and he was very receptive and has since initiated kissing himself) and he’s hinted around at the fact that he doesn’t have very much romantic or sexual experience which I suspected from the jump and am very much okay with. That said, it’s been a month and I’m pretty damn hot for this man. We see each about every other day and my desire to drag him into bed has grown steadily. Generally speaking, I know how to get things started, but given his stated inexperience, I’m trying to keep a little bit of a lid on my libido until he’s ready for more.Based on how the early stages of being physical (breaking touch barrier, kissing, making out, etc.) have gone, I’m definitely going to have to be the one to move things forward sexually, which is fine. My conundrum is finding the best way to do this. I really like this guy, enough that I’d honestly be happy to DTR and move forward with calling ourselves a couple at this point which is something I’m normally terrified of doing (I’m usually an open multi-dater, this is the first time I’ve dated one guy without wanting to date anyone else in about five years). I’m not sure if he’s actually a virgin, but I suspect he is so I want to give him his own space and time to be ready to have sex, but I also don’t want to sort of leave him hanging on figuring out how to get there on his own.I guess my question is, for those of you who have been in a similar situation what would you have wanted your partner to do? Directly start a conversation about where you are as far as being ready to move things forward physically and whether you’d be more comfortable doing that after explicitly declaring exclusivity? Just sort of nudging things toward sex by getting increasingly physical? Something else? Honestly, I’d really like to have a conversation about it (without mentioning that I think he’s a virgin/asking him to admit that, obviously), but I’m not sure if that’s something that’d be awkward/embarrassing?Also, as far as having sex with him for the first time goes, any tips for helping an inexperienced partner feel comfortable in the bedroom the first few times/taking some of the pressure off the situation?I’m sure I’m overthinking this like I did with being the one to kiss him first so I appreciate any help you can give me! I just really like this guy and don’t want to screw things up, haha.