Boyfriend with Gay Past

Dear Bill
I'm a woman. My 33 year old boyfriend of 6 months recently admitted to me that when he was a preteen, him and 2 of his best friends would masturbate together, rub on each other, and give each other oral. This happened for over a year. He also just admitted that 2 years ago him and one of his friends went to a hotel, got drunk and blew each other. He claims his friend didn't *** in his mouth, i think he did. He also said his friend licked his but, but he didn't have any anal sex. He said he didn't like it and did it only cuz he was curious about trying it as an adult and it made him know for sure he is not gay. But is this true? Especially considering he was in homosexual relations for over a year as a kid?

We have good sex and He loves kissing me and going down on me and all. He does want anal but i said not until we're married. but he's super clingy, emotional, and insecure about our relationship and my faithfulness. But he's also super macho guy and kind of homophobic so this info caught me by surprise.

I'm trying to be supportive and believe him since he told me something he hadn't told anyone else. But should I worry? Him and his 2 childhood friends are still buddies. he said they don't ever talk about it but he thinks his friends do think about it sometimes. but he said his hotel friend stopped contacting him after a while. Seems like he still wanted contact. These are all men in straight relations now. 2 are married. I'm just worried he's still curious but would not admit it but might do something about it behind my back. What should I do and how can I know he's for sure straight? 

Well, to be blunt this guy doesn't sound totally straight. Some kids may "experiment" in a homoerotic fashion, but it's usually maybe one or two incidents, not over and over and over again. And his recently going to a hotel room with a guy for sex -- never mind how drunk he was -- is another red flag. His homophobia is an even bigger red flag.

To be honest, he sounds like a guy who definitely has homosexual leanings but is fighting them because he's ashamed, or because he thinks only stereotypically "swishy" guys can really be gay [not true; most gay men don't fit the stereotypes]. There are many homosexual men who are basically living straight lives with girlfriends, wives and children and who seek sex with men even as they try to deny their true nature to themselves and everyone else. He is at the very least bisexual, but the thing is that bisexual men are often bi in their activities [they have sex or relationships with both men and women] but in their heart of hearts their preference is often men. The trouble is that most of these guys just can't admit it to themselves.

Men like this are often clinging and possessive and insecure with the women in their lives, because they need these women to prove to themselves and others that they are essentially heterosexual. Sadly, this is generally not the case.

I would suggest a long, non-judgmental talk with your boyfriend, as I suspect there's a lot more going on [in his mind, if nowhere else] than he's telling you. He might need counseling or therapy from a gay or gay-friendly therapist.