Dating someone who might be gay

My high school boyfriend and I were each other's first, both late bloomers and neglected kids. He had sexual encounters as a youth with a boy neighbor. His 19 year marriage to an older frigid woman ended in divorce after we reunited. It's been 5 years and he is very attracted to men who look like him and wants to be with a man. We have sex on overdrive and attend swingers events and parties as exhibitionist. He wants to have sex with every woman there and now men, but hasn't yet. Last night he commented that he would like to be with a man when I next leave for a weekend.

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I'm thinking he is bi but not sure. Do not date this man again. Jesus, this guy did all of this to you--even gave you a disease--and you're still just concerned about the fact that he might be gay? Since I don't know him personally, there's no way to know if he's really gay. From what you describe, I personally would assume he's neither gay nor straight--plenty of people are somewhere in between.

However, as I said, there's no way you or I can know for sure. Only he knows that. The fact that he was increasingly impotent probably has nothing to do with his sexuality, though. He's an older guy, which means his testosterone levels might have taken a dive.


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This hormone is essential for his performance. Supplements don't really help this much; only direct administration of testosterone will raise his levels significantly. Also, he takes nervous system depressants like alcohol on a regular basis. This combo of age and drug abuse will almost certainly make any guy have performance issues. You deserve more than the way that he treated you. If he's addicted to drugs, the drugs will always come first for him. It sounds like he doesn't have every high standards for his life, so why would he have high standards for your relationship?

Having unprotected sex with him especially in the back entrance, which is more dangerous is a bad idea as well, especially if you suspect that he's been fooling around. Extra especially if you suspect that he has been fooling around with other men with no protection. Just don't do it. There are nice men out there who would be happy to be in a committed relationship with you and wouldn't run around doing drugs or two-timing you. The first issue I see here is that if he made those appointments during your relationship not before you got together , then he cheated. That's a bigger problem than his being with a trans lady.


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  • Unless you have an open relationship or something. To answer your question, though, lots of guys find trans women to be taboo and exciting. Believe it or not, most of those guys are straight. The vast majority, in my experience. I've known many, many trans women, and most of their boyfriends are straight. I've also known a few trans ladies who were working girls, such as the kind your boyfriend might have visited, and most of their customers are straight men.

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    If you think about it, it kind of makes sense: Gay guys are interested in men, not women. It's uncommon, in my experience, for a gay guy to be attracted to any kind of woman, transsexual or otherwise. Though it does occasionally happen. So most guys who are into trans women are straight, and some might be bi.

    Like you said, it is sometimes true that a closeted gay guy might try to experiment at first with a trans woman if he's in denial. However, if he really is gay and only interested in men, he probably wouldn't do this multiple times. Being with a trans woman is a very different experience from being with a man, and most gay men would not find it too exciting. But i guess got scared of reality and we ended up together almost 5 years. The reason we aren't together is he had numerous affairs and my gut says that they all weren't just with women.

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    But he still days hes straight. Hes 40 years old 3 kids 3 different mommas and never bern married. I was to blind to see all his red flags. I have been with my man for almost 3 years. The first time we decided to have sex he apologized to me due to his inability to get and maintain an erection. I just figured first time performance issues. We moved in together soon after and not only did this issue continue but the frequency of attempts at having sex diminished greatly. He continued to have erection problems all the time.

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    He was affectionate at times. He was getting high and we figured his impotence was due to that. Then the drinking became prevalent and the impotency became a huge problem. It was very frustrating in the bedroom trying over and over with no results. He was at least providing oral sex to me until he matter of factly stated one night while in bed as he was performing oral sex on me that he didn't like it at all.

    Up until this point I just chalked it up to the drinking and drugs. He had also gone to the doctor to get help. He received a prescription for Cialis which I was more than happy to purchase.

    He also tried using some testosterone supplements to help. He said he would try it but when I would suggest that we finally try it out, he would drink to, I believe to prevent its effectiveness. I have to backtrack a bit, in the beginning he was not at all embarrassed by showing off his body in all its glory to me.

    We are both in our 50's. He is very fit and I had just lost 70 lbs but still insecure about my body and being my first relationship in over 10 years, it was reasonable. Well, as I said he loved prancing around showing off. However I started to become concerned when as he was showing off he would be admiring himself in the mirror and then turn his back to the mirror, spread open his butt cheeks and say so proudly what a gorgeous asshole he had. He did this almost daily.

    I became concerned and thoughts started to swirl around in my head with ideas that I didn't want to believe. Not too long after that he told me about sexual encounters that he had had with a gay male neighbor when he was about My boyfriend stated that he partook in this activity quite a few times.

    He said that it was strictly for the money. At this point we had been together for about a year and I loved him so much that I really was mixed up about what to think but I wasn't willing to let our relationship fail because of something that happened so long ago, but his behavior was very disconcerting to me.

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    He also told me that whenever he had had a relationship with a woman, that the woman would support him exclusively. He didn't work. So now the word gigolo came to mind. I started to think about everything he had said, his previous experiences, his unusual admiration for his asshole, his inability to get an erection, living off of women and his yearly HIV testing and wondered if my partner was gay or bisexual. He has a daughter that is gay and when she told him he became very aggressive and enraged that he cut off all contact. It has been over 15 years since he saw or spoke to her.

    As time went on this situation of no intimacy led to many fights and my feelings became much stronger towards what I believed his sexual preferences were. I am still very much in love with him. I don't know what to think. I can't broach the subject with him for fear of aggression towards me. He tells me that he loves me then the next he hates me. He says I am the reason his life is screwed up, that is the addict talking. Unfortunately at a point when things were extremely bad between us just about three months ago we had a very bad fight and he went on a binge.

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    I wouldn't allow him back in our home unless he got treatment. He choose to go to the city and get high but this time on heroin. He ended up at some unknown females apartment. He told me that he was so high that he collapsed in her shower and that she assisted him in getting out. He stayed with her for days unbeknownst to me. I asked if had sex with her and he said no.

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