• Ask GayDemon: Daddy Lessons

    Ask GayDemon: Daddy Lessons

    I'm a 55-year-old gay man in good shape, and I have salt 'n pepper hair, and a big grey mustache. I guess I fit the daddy look because I'm constantly being hit on by younger men, even 40-year-olds, who want to call me daddy and be dominated while I'm topping them. I prefer to top, but I've never thought of myself as a daddy and don't really know how to play this role, nor do I want to all the time. Is there an online daddy school where I can learn the ropes? What is this daddy stuff all about?

    -New Daddy

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  • Ask GayDemon: Sprayed by Gender Fluid

    Ask GayDemon: Sprayed by Gender Fluid

    My boyfriend of two years has suddenly decided that he's gender fluid and is demanding that I refer to him as them. He says that some days he feels like a boy and sometimes a girl. He assures me that he wants to keep his penis, but feels that sometimes he might feel like wearing a skirt. But he's not into wigs and make-up. I didn't sign on for this, I'm so confused. He's got a cock. He's a boy. I love him but feel like this is a deal breaker. What do I do?

    -Gender Shook

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  • Ask GayDemon: Under What?

    Ask GayDemon: Under What?

    I have just discovered something a little weird about my boyfriend of six months. Well, maybe it's not so weird. Maybe I'm the weird one. We don't live together yet, and one night at my boyfriend's condo as we got ready for bed, he took off his underwear and put them in a baggy. I asked about it and my boyfriend tells me that he has guys who have standing orders to purchase his well-worn underwear. He's connected with the men on Craigslist, but has never met them in person and has no desire to. They send him money and he sends them another pair of his underwear. Weird, right?

    -Puzzled Witness

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  • Ask GayDemon: To Spank or Not To Spank

    Ask GayDemon: To Spank or Not To Spank

    My boyfriend and I have an open relationship. After one of his recent outings, my boyfriend told me that he got spanked, as in over the guy's knee, then the guy used a belt on him. He really liked it and told me he wants to explore spanking in our relationship. We've always been pretty vanilla, but I have to admit that spanking intrigues me, but it also sounds weird. I guess I should just get over it. Any thoughts or suggestions?

    -Spanking Virgin

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  • Ask GayDemon: Ex Sex Drama

    Ask GayDemon: Ex Sex Drama

    I've been with my boyfriend for four years. We live together and have two cats and we're talking about buying a house, so we're pretty settled. A couple of months ago, I ran into an ex (he was my first big love) and we ended up having sex. I didn't tell my partner and we're not in an open relationship. The ex and I have had two other encounters, and they've been some of the best sex I've ever had, and now I'm wondering if there's still a spark. I don't know what to do.

    -Cat and Ex Lover


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  • Ask GayDemon: It Takes Two to Bareback

    Ask GayDemon: It Takes Two to Bareback

    I've been going out with this guy for six months and everything's going great. He turns me on and our sex life is fun and satisfying except for one thing. I want to stop using condoms. I've tried fucking him a couple of times without a condom and he stops me. I've tried talking about it, but he just says that he's not ready to take that step but won't tell me why. I end up feeling like I can't be trusted. I don't know what to  do.

    -Rubber Hater

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  • Ask GayDemon: Faster than a Speeding Cumshot

    Ask GayDemon: Faster than a Speeding Cumshot

    I cum too quickly and it's ruining my sex life. Heard of a two-minute wonder? I wish I could last two minutes. It doesn't matter if it's a handy, a blowjob, or fucking. I cum in under a minute. What can I do?

    -Quickie Hater

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  • Ask GayDemon: Totally Not Fat

    Ask GayDemon: Totally Not Fat

    I've  got a couple of friends who constantly call themselves fat and are obsessed with the imaginary belly they think they have. They're constantly going on about not being able to get rid of it, but honestly they look fine and there's nothing really to get rid of. I'm concerned their endless body shaming and discussion about diets and workout routines is leading these guys to an eating disorder, if they don't already have one. Anything I can do to help?

    -Ears Are Burning

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  • Ask GayDemon: Bisexual Boyfriend

    Ask GayDemon: Bisexual Boyfriend

    I wasn't completely honest with my boyfriend. I'm not completely gay, I'm actually bi. I've been dating him for about nine months now and I'm missing guy-on-girl action. We're monogamous at the moment. I love this  guy and I'm happy with him, but every once in a while I'd like to jump the fence for an encounter. How do I tackle this one?

    -Baffled Bisexual

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  • Ask GayDemon: Fill Me Up

    Ask GayDemon: Fill Me Up

    I've been dating a guy for about six months and I think I want to settle down with him. The problem is that he's not very well hung. He's good in bed and I mostly enjoy our sex life. But I do enjoy getting fucked. While he's enthusiastic about it, he's just not cutting it in that  feeling full department. I think it's time to introduce a third into our relationship – a giant dildo – how do I broach the subject?

    -That Empty Feeling

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  • Ask GayDemon: Quiet as a Gay Mouse

    Ask GayDemon: Quiet as a Gay Mouse

    My boyfriend wants me to talk more during sex. I'm not a shy person, but dirty talk, or much talk at all in bed, has never been my thing. What the hell am I supposed to say? How can I get comfortable expressing myself in the sack?

    -Loss for Words

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  • Ask GayDemon: What Comes After Two?

    Ask GayDemon: What Comes After Two?

    My partner and I have been together for four years and we've been talking about having a threesome. We've been monogamous until now. How do we find someone to play with?

    -Two Thirds Complete

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  • Ask GayDemon: A Spanking Good Time

    Ask GayDemon: A Spanking Good Time

    I recently discovered that I'm turned on by bondage and spanking. How did I discover that? I picked up a traveling executive and let him tie me up and spank me in his hotel room. I  realized afterwards that I foolishly put a lot of trust in a complete stranger and it could have  gone terribly wrong. But still, I have this burning desire to explore this side of myself. Where do I find like-minded people? How can I do it safely?

    -Eager for More

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  • Ask GayDemon: Friends Without Boundaries

    Ask GayDemon: Friends Without Boundaries

    I'm single but date quite regularly. My problem is that my friends don't have a hands-off policy and constantly come on to my dates. And I'm not talking about secretly slipping a phone number into his hand. WTF? Do I need new friends?

    -Third Wheel

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  • Ask GayDemon: Macho vs. Feminine

    Ask GayDemon: Macho vs. Feminine

    I'm attracted to guys who are on the feminine side, for the lack of a better word, although I really don't like labeling people. However, most of my friends are macho sports jocks (there's that label again) and they give me a hard time about the guys I date. They tease me and make disparaging comments. Is it time to find new friends?

    -Frisky for Femmes

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