Q: I’ve been wondering: Since there are lesbians out there who occasionally crave cock, does the reverse also happen? Are there gay men who occasionally crave pussy? — This Possible?
There are gay men who watch football — hell, I have it on good authority that some gay men play football, TP. So anything is possible. (Also, there are lots of lesbian-identified bisexual women out there, a smaller number of gay-identified bisexual men, and a tiny handful of bisexual-identified football fans.)
Q: I’m a 26-year-old woman. I started dating a fantastic guy a month ago, blah blah blah, we’ve already talked about marriage. The problem is that his dick isn’t up to par size-wise or staying-hard-wise. He was aware of this before I came along, and it made him an enthusiastic and skilled oral performer to make up for it. So for now everything’s great, plenty of orgasms, and we’re lovey-dovey. But eventually I’ll need that filled-up feeling and I’ll have to ask for some dildo/extender/strap-on action. The question is when to ask. He’s a secure guy, and we’ve both been honest about our flaws. If I wait too long to ask, it might make him think I’ve been faking the whole time. And if I ask too soon, I could scare him off or make his performance anxiety worse! How do I know when the right time is? — Half Full
If you were talking about marriage after a month, HF, odds are good this relationship is doomed anyway. So go ahead and ask for dildo/extender/strap-on action now. Don’t say, “Circling back to your subpar dick, darling, I’m gonna need some compensatory dildo action soon.” Instead say, “I’m into penetration toys, and I’m looking forward to getting into them with you — getting them into me, getting them into you. Anything you want to put on the menu, darling?”
Two friends can hook up with a girl or two girls from a bar and have a threesome or a foursome. But can two brothers — with opposite sexual preferences — hook up with a girl and a guy from a bar? Would this be considered wrong? No touching between siblings would occur. — Basic Bros
It would be considered wrong by some — but those people aren’t you, your brother, or the girl and guy you hope to pick up together. Personally, BB, I can barely get an erection if one of my siblings is in the same zip code; I can’t imagine getting one with a sibling in the same room. But if you’re comfortable doing opposite-sexual-preferencey things in close proximity to your brother, go for it.
I am a bisexual man and recently divorced my wife of 30 years. I am currently seeing a very beautiful lady. I satisfy my bisexual desires by going to sex clubs and I always practice safe. I don’t have an issue, I just wanted to tell you I remember one time when you had a column about two guys performing fellatio on another man at the same time. I found it to be such a turn-on and even fantasized I was doing it to you. Hope that doesn’t offend you. — Loving Life
Um, thanks for sharing?
What’s the best dating site for a slightly cynical, tattooed, fortysomething woman looking for a guy? — Tattooed Lady
It depends on the kind of guy you want. Closet case? ChristianMingle. Fuck boy? Tinder. Trump voter? Farmers Only. Compulsive masturbator? Craigslist. Unfuckable loser who is now and will always be a socially maladapted virgin? Return of Kings.