dating a man who only dated women before

[pbr92]

Hi all,

For the past couple of months I've been dating someone who previously only had relationships with women (although he's had gay encounters before). I love this person, and I want this relationship to work out but I'm dealing with sexual insecurities that I've never had to deal with before: i.e. does he miss pussy, do I pleasure him better/the same way as a women, is the sex as good etc.

For the record, the last time I was with a woman I was 16, and I'm now 26 - only been with men since then.

Any ideas on how I can overcome these insecurities? Honestly any relevant advice would be greatly appreciated. The insecurities actually make me not want to have sex with him or shy me away from having sex with him at times.

 

[Croft85]

The best way to overcome your insecurities is by have an open and honest conversation with him. But remember out of all the girls out there he chose you not them.

 

[KaraBulut]

I love this person, and I want this relationship to work...

If this is true...

... have an open and honest conversation with him.

...then this is your best advice.

One suggestion: talk about how you feel, not about his history or the women he's been with. This is about your insecurity... it's not going to go away if the pussy were to go away; and you're going to feel insecure when the issue of his attraction to other men comes up in future.

Your insecurity is what is straining your relationship and it's something you have to work on together.

 

[Just Do It]

Consider this first from a different angle, that of his possible insecurities, not yours.

I would just say exercise caution before you invest too much time. My first two ‘love interests’ were guys who had been partnered only to women. They had had experiences with guys but always on the DL so they were able to maintain their standing with family, friends, community members, co-workers, etc. Then after a few whiffs of trouble—i.e., facing discrimination as men involved with a man—they immediately went back to women, where they knew they were ‘safe.’ One of them was actually pretty condescending about it—‘You know, I don’t have to live this way like you do. What were you going to do, follow me around the rest of my life?’

Is this guy out or does he expect you to slither around in the dark while he continues to interact with others close to him? How does he react if you hold his hand or kiss him in públic? Does he plan on making you a full part of his life? Or has he just watched the struggles men partnered with men face, fearing it may crash down on him too later in life?

I’d say make sure this particular aspect is in order, then proceed to the other questions, e.g., if you expect to have a monogamous relationship, will you be able to satisfy his erotic needs? I am married to a man who didn’t even have girlfriends in high school as I did. At the beginning he asked me a few questions about those relationships and came away satisfied and secure that I could be fully happy with a man. There would be no ‘female’ complications, which I’m sure you realize could be pretty heavy indeed.

 

[pbr92]

Consider this first from a different angle, that of his possible insecurities, not yours.

I would just say exercise caution before you invest too much time. My first two ‘love interests’ were guys who had been partnered only to women. They had had experiences with guys but always on the DL so they were able to maintain their standing with family, friends, community members, co-workers, etc. Then after a few whiffs of trouble—i.e., facing discrimination as men involved with a man—they immediately went back to women, where they knew they were ‘safe.’ One of them was actually pretty condescending about it—‘You know, I don’t have to live this way like you do. What were you going to do, follow me around the rest of my life?’

Is this guy out or does he expect you to slither around in the dark while he continues to interact with others close to him? How does he react if you hold his hand or kiss him in públic? Does he plan on making you a full part of his life? Or has he just watched the struggles men partnered with men face, fearing it may crash down on him too later in life?

I’d say make sure this particular aspect is in order, then proceed to the other questions, e.g., if you expect to have a monogamous relationship, will you be able to satisfy his erotic needs? I am married to a man who didn’t even have girlfriends in high school as I did. At the beginning he asked me a few questions about those relationships and came away satisfied and secure that I could be fully happy with a man. There would be no ‘female’ complications, which I’m sure you realize could be pretty heavy indeed.

I don't really think that's a problem for him. He acknowledges he loves me and that he doesn't want to hide me to his family, so he knows that taking that step (if he wants to be with me the way he says he does) is going to come at some point or another. I'm very patient about this because I had to go through it too, so it's not a big deal to me at the moment. After all, I'm dating him, not his family. However, that is a red line I've spoken to him about, that I can be patient, but I won't wait forever either. And no, he's not scared to hold my hand, kiss me in public etc.

And now that I really think about it, I'm secure that emotionally I can fulfill him it's just sexually that I'm a little bit scared. I dated girls and had sex with them as well, but not for as long as he did. Eventually I went on to develop a gay personality, and I don't really miss having sex with women or anything like that. I think I forget that sometimes...

 

[Just Do It]

Then it seems the higher of the two hurdles will be cleared (little to no fear of social disapproval). Fortunately this is more common nowadays than in ‘my time,’ when discrimination was much worse.

As for the insecurity, I agree this is where the conversation comes in. It is clear you are a thoughtful, kind, considerate and respectful guy so I’m sure he’ll be happy when the discussions take on those characteristics.

YOLO and mutually falling in love with a man is as you know an amazing thing that not all gay guys get to experience! Both men should take care not to allow for too much interference...especially from beautiful women!

 

[sixthson]

If your bf misses pussy when he's with you, then he will miss dick when he's with a woman. I don't know if he self identifies as bisexual, but lots of people are suspicious of bisexuals because they don't believe they will be content with one person or even capable of it. Just because someone is attracted to someone else doesn't mean they will act on it. As others have said, you need to have some heart to heart talks with him and guard your own heart before giving it away. I would say from your description he is giving all the right signs.

 

[pbr92]

If your bf misses pussy when he's with you, then he will miss dick when he's with a woman.

You got me there. This is something I had completely dismissed.

 

[GayCuriousSub]

that's sort of the way it goes sometimes. you could ask your friend with his woman, himself and YOU

see what happens!!!

 

[DavidBurch]

Hi all,

For the past couple of months I've been dating someone who previously only had relationships with women (although he's had gay encounters before). I love this person, and I want this relationship to work out but I'm dealing with sexual insecurities that I've never had to deal with before: i.e. does he miss pussy, do I pleasure him better/the same way as a women, is the sex as good etc.

For the record, the last time I was with a woman I was 16, and I'm now 26 - only been with men since then.

Any ideas on how I can overcome these insecurities? Honestly any relevant advice would be greatly appreciated. The insecurities actually make me not want to have sex with him or shy me away from having sex with him at times.

I have a very similar story...

 

[Rocky]

I mean, so what if he misses pussy?

Worst case scenario, he cheats on you with a woman. Maybe he needed it. He still might come back to you, though. Build a solid relationship. Get him to love you for you.

But I can understand how nightmarish it is. If he did cheat on you with a woman, what if she got pregnant? Would he marry her and never speak to you again? I have a "straight" / bisexual friend who did that to me before, he blocked me on Facebook after he got married and had a kid with a woman. I'm still upset.

I've thought about being with a woman myself... but I would miss guys. I know I would. So there's that. The problem is, it sounds like he only used to see guys before on the down low. What are his feelings about himself? Does he want to live as a gay man? If he really doesn't.... there's a problem.

 

[KaraBulut]

I have a very similar story...

Which is....?

 

[USEDCAR]

I wonder what the outcome of this was?

I dealt with 2 guys that only dated females. I had bad experiences with both I would never again.

Similar situation, I invested way too much time on a guy who only dated girls but messed with men on the DL. I thought we had a good relationship/Friendship the sex was amazing and we clicked well. We was planning to get a place together too. The Gut never lies he ended up acting weird wasn't hanging out as much. He wanted me to meet his older lady "Friend" and involve her with out hanging out. I seen the flirting and staring and knew something was happening. She made a comment about him having his own nightstand I confronted him and her at different times they lied. Her daughter told me they was messing and gave me a heads up. They both got mad at me for asking the daughter about their relationship. He was seeing her behind my back. His dream was to date her and wanted us to fuck. I told him I wasn't sharing you with a old lady. We tried to talk and things wasn't the same. They are still together today and we stopped talking years ago.

 

[BiGuy1970]

Hi all,

For the past couple of months I've been dating someone who previously only had relationships with women (although he's had gay encounters before). I love this person, and I want this relationship to work out but I'm dealing with sexual insecurities that I've never had to deal with before: i.e. does he miss pussy, do I pleasure him better/the same way as a women, is the sex as good etc.

For the record, the last time I was with a woman I was 16, and I'm now 26 - only been with men since then.

Any ideas on how I can overcome these insecurities? Honestly any relevant advice would be greatly appreciated. The insecurities actually make me not want to have sex with him or shy me away from having sex with him at times.

Does he talk to you about future plans? Does he compliment you about your sex life?

I'm sort of in the same situation as your BF. I'm leaving dating women all together. In fact, I've never had a gay date. So when I do, I'm not going to have a clue as to how to act. My sexual encounters have all be quickies. Sitting and talking to a gay man about live and things has only happened once. And that was someone that was just a friend. We never dated or even seen each other naked.
He might be as lost as I'm about to be. Not knowing what to say. Knowing the conversations should be different, but not knowing the difference. He may have had women like me, who will use your words against you later on.

I think you might trying putting out of your mind (a little harder) and see if anything changes when he gets more used to you, and more comfortable with actually being with another man.