Sex with great woman who has never had an orgasm with another person

Puffdaddy316

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Met this fine woman a few weeks ago and have started dating.

We slept together several times and before the first time she told me she didn't have a lot of experience with guys and has never had an orgasm with one.

Manually, we got her about 90% of the way there tonight and overall, the sex has really been great from my end. She enjoys it, initiates it often and has said things like "I think I'm getting closer to being able to cum."

I kind of don't want to mess with progress but at the same time I'd like to see how she makes herself come via masturbation so I can learn.

At what point should I ask for this? I'd obviously preface it by saying I'd only want that if she was comfortable with it.

Or do I give her a few more weeks? It's early, but I'm serious about this girl. She's terrific. I just want the bedroom experience to be as awesome for her as it is for me.
 

Cowboy_Doc

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The only advice I could give is to focus on helping her enjoy the experience. Try not to frame things in typical male goal-oriented fashion. I.e., "Show me what feels good to you?" or "I want to give you pleasure" rather than "I want to see what makes you cum". It sounds like you're doing a great job of making her feel good. Keep focusing on that (even if/when you ask her to show you how she masterbates) instead of how to make her orgasm, and the orgasm will more than likely follow as a result. You have undertaken a noble quest.... I hope you are both adequately rewarded. :biggrin1:
 

HiddenLacey

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Even if she would pleasure herself in front of you, it doesn't mean she would really be comfortable/ relaxed enough to get into it the way she would alone.

I'm not her, but I can give you advise based on what works for me. About 80% of my ability to get off with a man is in my mind. If I don't stop thinking it will never happen. Either I have to be very comfortable and relaxed with him or he has to completely overwhelm me.

For myself, the ability to be really comfortable and relaxed comes with time and his actions towards me. Laying back and masturbating for a man isn't the most comfortable thing in the beginning. Best thing that ever happened for me was a partner that said, "rub your clit for me" while I was on top. Immediately I felt shy and didn't want to but in the moment while he kept talking to me and I was extremely aroused and I could watch him watching me... well it worked for me. It seemed as though everything I did ramped up his desire. Of course such a thing may not work for her at all, but it's an idea.

I wouldn't ask her to masturbate while having a sex conversation. I wouldn't respond well, meaning it would make me tense and nervous to feel like I had to put on a show. However, during the moment when I was with someone and naked and aroused, it might have a good effect. Especially if he pulled away and told me while touching himself. I think it would be easier to just go with it. I think that if I watched him and he was focusing on what I was doing instead of watching my face it would probably help as well. I would stop thinking and just watch how he touched himself.

Being shy about sex sucks, but once past that point, it's great.

Please note that this is my opinion. The above works for me. Women are all different of course and if any other's read this or respond they may completely disagree with me. You know her, you can decide what approach may work the best for her. Luck!
 

AlteredEgo

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The OP sounds really considerate, and nice.

I don't really like to be watched masturbating, but it can be fun for me if we both masturbate together. If there is something for me to watch other than him, that can help me, because I am less aware of being observed. I happen to like porn though, so for me, thats an option.
 

Puffdaddy316

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Update: she's been terrific. The whole relationship has.

Havent need to ask her to do anything on her own but have rather asked her to put her hand on fine when I'm fingering her, put her hands on my head when I go down on her and whisper to me while we're fucking.

She's said this is the best she's had and is totally convinced it'll happen soon.

Seems like she's getting closer and closer and even said "this is the closest I've EVER gotten, feels great and I'm not worried at all.

Honestly, I think she's terrific in many ways beyond the bedroom and that she'll have her day.

Rightfully, she's not remotely self-conscious and in fact we both view this as a fun "challenge."

What was a concern, with communication, now seems like something that has enhanced the relationship.

"there's no rush," she says, "plenty of time."

That's taken the pressure that I'd been feeling off me in a big way. That communication is the big lesson here, I think.
 

Puffdaddy316

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Update: she's been terrific. The whole relationship has.

Havent need to ask her to do anything on her own but have rather asked her to put her hand on fine when I'm fingering her, put her hands on my head when I go down on her and whisper to me while we're fucking.

She's said this is the best she's had and is totally convinced it'll happen soon.

Seems like she's getting closer and closer and even said "this is the closest I've EVER gotten, feels great and I'm not worried at all.

Honestly, I think she's terrific in many ways beyond the bedroom and that she'll have her day.

Rightfully, she's not remotely self-conscious and in fact we both view this as a fun "challenge."

What was a concern, with communication, now seems like something that has enhanced the relationship.

"there's no rush," she says, "plenty of time."

That's taken the pressure that I'd been feeling off me in a big way. That communication is the big lesson here, I think.