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Been with women a long time, now dating men

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Hi,

Mainly asking other bisexual dudes but willing to hear any thoughts and advice.

My situation: I'm 31 and 2 years (almost) out of a divorce from my ex-wife. We were together since I was 18 so 99% of my sexual experience is with women. It's taken me a long time to recover and feel comfortable dating, but here I am and my online dating filters are geared to men and women. Turns out, guys love me lol. Probably not an unusual experience but I match with men far more frequently and have gotten a few dates like this.

My problem: though my browser history clearly shows that I'm into guys when it comes down to the prospect of having sex with men, I'm very uncomfortable in my skin and I think it's leading me down a path of coming-off as not genuine or maybe prudish around the men I'm dating and texting. I'm not a first-timer when it comes to men and sex, but the last time I had sex with a man was nearly 10 years ago (and it was very awkward), and it comes through when the talk gets sexual. There's a lot of apprehension that I deal with when the prospect of a hookup comes up that I've never dealt with--the guy's basically a stranger, what about STIs, what if he straight up rapes me (a thought that never comes across my mind with women), etc.

So the question: how do I get across to guys that I'm interested in sex but want to get to know you first and get comfortable and we'll all have to wait to whip our dicks out if this is to continue--without totally turning the guy off or falling into a friendzone type of situation? If you're bisexual and like me got into dating men later, how did you get comfortable around men romantically and sexually?

Thanks
 
There’s nothing wrong with telling guys you want to take it slow. It sounds like you may just need time, for a number of reasons.

Yes, some guys may just want a hookup (especially if you’re looking on Grindr or whatever) and they may get turned off. But others will be cool with it. It’s perfectly normal to have awkward moments in any relationship, so don’t worry about that part. Just take it one step at a time, and do what you’re comfortable with, and everything else will follow.

I speak from experience in that it worked for me......|
 
Hi,

Mainly asking other bisexual dudes but willing to hear any thoughts and advice.

My situation: I'm 31 and 2 years (almost) out of a divorce from my ex-wife. We were together since I was 18 so 99% of my sexual experience is with women. It's taken me a long time to recover and feel comfortable dating, but here I am and my online dating filters are geared to men and women. Turns out, guys love me lol. Probably not an unusual experience but I match with men far more frequently and have gotten a few dates like this.

My problem: though my browser history clearly shows that I'm into guys when it comes down to the prospect of having sex with men, I'm very uncomfortable in my skin and I think it's leading me down a path of coming-off as not genuine or maybe prudish around the men I'm dating and texting. I'm not a first-timer when it comes to men and sex, but the last time I had sex with a man was nearly 10 years ago (and it was very awkward), and it comes through when the talk gets sexual. There's a lot of apprehension that I deal with when the prospect of a hookup comes up that I've never dealt with--the guy's basically a stranger, what about STIs, what if he straight up rapes me (a thought that never comes across my mind with women), etc.

So the question: how do I get across to guys that I'm interested in sex but want to get to know you first and get comfortable and we'll all have to wait to whip our dicks out if this is to continue--without totally turning the guy off or falling into a friendzone type of situation? If you're bisexual and like me got into dating men later, how did you get comfortable around men romantically and sexually?

Thanks

You will get more comfortable as time goes on. It took me a long time because of my own internalized homophobia. Do you have any gay or bi friends? I would say start there
 
... I'm very uncomfortable in my skin and I think it's leading me down a path of coming-off as not genuine or maybe prudish around the men I'm dating and texting. I'm not a first-timer when it comes to men and sex, but the last time I had sex with a man was nearly 10 years ago (and it was very awkward), and it comes through when the talk gets sexual. There's a lot of apprehension that I deal with when the prospect of a hookup comes up that I've never dealt with--the guy's basically a stranger, what about STIs, what if he straight up rapes me (a thought that never comes across my mind with women), etc.
If you were prudish, there's nothing wrong with it. Not everyone wants the same thing.

Whether you're inexperienced or you're a total slut, it's better to be who you are and not apologize for it. Any person you date for a long time will figure out the truth.

Regarding your fears about STIs and assault: the whole point of dating and getting to know someone is so that you don't end up in situations with strangers that get out of hand.

...So the question: how do I get across to guys that I'm interested in sex but want to get to know you first and get comfortable and we'll all have to wait to whip our dicks out if this is to continue--without totally turning the guy off or falling into a friendzone type of situation? If you're bisexual and like me got into dating men later, how did you get comfortable around men romantically and sexually?
The answer to your question is that you just say it like that.

To put it bluntly, there's two types of guys: those who are looking for drive-through fast food and those who are looking for a sit-down dining experience. There's nothing wrong with either, as long as everyone is honest about it.

Any guy who doesn't want the same thing that you want isn't your type, is he?

If you are interested in dating and you don't want to jump into bed on the first date- state that up front. Either say it in person or put it on your online profile. You'll save everyone a lot of time by putting it out there and being honest about it.


But let's be real about something: there's a reason that you're 31 and just now going through things that most guys go through in their teens. It has to do with fear and dealing with uncertainty. Dating is a process and you're going to have to take risks to date. That means that you're going to be disappointed and you're going to be hurt. You're never going to have complete control of the situation. But if you want to get something, you have to risk something. Be yourself. Put yourself out there. Don't try to be anything other than who you are.
 
You've been given some stellar responses that address your main concern directly. There's not much more I could add on that front but what I can do is give you something more indirect.

Similar to you, I began dating men only recently, though to be transparent I haven't dated women, and I'm in my late 20s. I had great success with the app OkCupid and I really do think it's a great platform for meeting people. So I highly recommend using it to find people more open to moving a bit slow.

What I think made OkCupid work so well for me is that I always left a message for people that caught my eye--which makes the algorithm prioritize you--and I answered as many 'questions' as I could so the app could select people more likely to be a good fit. One of the questions IS about how soon you think you want to become sexual and what you're more looking from dating, romance or sex?

I also made an effort to find the people who were also putting in the effort. I looked at the questions they answered, read their profile, and if there wasn't anything I moved on. People that are serious about finding someone tend to be patient and committed to trying. If you can, give it a try and hopefully you'll get the results you want.
The person I'm dating has been -so- understanding and helpful. They're okay with things being a bit awkward because it's a learning process. Hopefully there's someone down the road who'll give you that same space to figure things out together!
 
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