Ask GayDemon Blog

My boyfriend doesn’t seem interested in sex anymore. We’ve been having threesomes and we check out other guys all the time, using apps or even out and about. He tells me how hot a guy is and what he’d like to have done to him, but when it comes to our own sex, there’s nothing lately. Has he gone off me?
-One + One = Zero

If you had a boyfriend with a foot kink and suddenly you wore shoes to bed (and not sexy shoes, but something hideous like Kanye West designs) and he lost interest in you because your feet were inaccessible, would you be asking the same question?

He's into threesomes but not twosomes. But you're within the three and you're the constant in the three. So there's your sexual connection.

I’m about to go on our first holiday with my boyfriend. We have been together for about 9 months, so we’ve never really spent quite so much time together and I’m not sure how we will cope. Maybe I’m worrying over nothing, but do you have any tips to avoid this being a disaster in the making?
-Vexed Vacationer

Break up with him just before the vacation and go out on a single date with a new guy and invite him on vacation for your second date. He'll probably be creeped out that you're moving so fast, but if you pay for everything, he's likely to just fake it and go along with you for the vacation experience itself. Not your company.

So you can promise separate beds but then tell the hotel to make sure they actually only have a single bed in the room so then you can fuck the new guy in the middle of the night and if his self-esteem is low enough, he might just not say no.

I am somewhat more wealthy than my boyfriend of a year, but he has a good job and earns well too. We are about to buy a place together, and I’m struggling to decide how we should fund it fairly. It’s not that I don’t want to pay the majority of our mortgage or deposit, but I don’t want him to feel it’s not ours. What should I do?
-Future Homo Owner

You're going to buy a place with your boyfriend of one year? Put a halt to that one right off. And if you do proceed anyhow, make sure you both have legal protections in the event of a separation, fire, if ether or both of you lose your job, etc. 

Addressing those potential issues would actually make the whole thing feel like it's both of yours. As you're both addressing those issues. The "ours" aspect is not just about the physical property, but the whole process.

I've been single for a couple of years. Because as Margaret Cho says: "It seems I lack the low self-esteem to make the necessary compromises." Or I'm just an ugly loser!? But, even if I'm that, I'm an ugly loser with a high sex drive (plus a kinky streak). And I just haven't been very social lately. I kind of keep to myself. Majorly. And I'm about to burst. Is hiring an escort a good idea?
-Hooker Help Wanted

Hiring an escort is a terrible idea. You'd have to pay the guy. That's a terrible idea! For $150 you could get 40 loaves of brear. And eat them all! Plus he'd just blow all the money on jeans and baseball caps and lottery tickets and really loud sneakers.

Which is really great for the Jeans & Caps & Lottery Tix & Sneaks Emporium, but not great for you.

I’ve been reading some BDSM stories and finding myself curious to try submitting to a Master. I’m pretty nervous about stepping into the zone though. How should I take the plunge and where can I find someone to trust?
-Alphabet Soup

Stop reading. It brings nothing but heartache, filling your head with ideas, hopes, dreams, all ultimately leading to disappointment and pain. Oh, whoops, I left something out. I meant to specify "Stop reading Food Network Magazine." Because you'll never make that tuna casserole you've always dreamt of. Never!

But do keep on reading BDSM stories. And know that being nervous is natural. Of course you'd be nervous when you're about to meet a stranger online (who most matches with fiction) and immediately submit to being tied up, used, controlled and anally plunged (I'm thinking that's what you meant by "take the plunge" because there was a Falcon video a long time ago called Plunge or something like that).

I am trying to organise something special for my boyfriend’s birthday, but we have such different interests and I can’t even begin to think what he would enjoy. So instead I thought he’d appreciate something that brings us together more. What would you suggest?
-Empty Handed

I bet you think I'm going to say "double-headed dildo" but you're so wrong. Rather go for the triple-headed dildo. That way it's both a sex toy and a passive aggressive way to tell your boyfriend you want to have a three-way. Or that you want him to stick all three heads into your three assholes.

Just because cleaning a three-headed dildo can be a pain, here are some other options.

I’m just about to propose to my boyfriend somewhere that doesn’t allow gay marriage. I'm worried he’ll say no because of that alone, but I want him to know I want him to be my husband, when and if that ever happens. What would you do?
-Groom Without a Groom

What I would do is realize I'm not attracted to him in the long run and break up with him, because I'd made the wrong choice of guy in the first place and should have focused on being friends with him instead of pursuing anything romantic. Then I'd wallow in self-pity for five minutes, hours or years (depending), followed by brief forays into the dating scene and quick retreats into addictive behaviors like YouTube and pancakes.

I met a new buddy online and we are hanging out a lot, just doing stuff friends do. Things like going for coffee and maybe a few drinks, and going out for lunch together. Then when he’s not around he texts me really flirtatious messages. I think he’s cute, but if I took that as a green light to fool around with him, won’t that make being friends awkward?
-Friend Without Benefits

Him flirting with you is him flirting with you. It's not a green light to fool around with him in the future. It's not like he sends some texts and you have free rein to cum on his face. There are some steps in between.

So I hate to break it to you but you two are dating. And just because you haven't had sex yet doesn't mean it's purely platonic. I don't know what site or app you met on, but it almost doesn't matter. People can meet on Scruff and end up workout partners or going to the movies together or whatever. Like married.

I’m looking for somebody with a specific fetish. I’m really into smoking and wanking, I don’t necessarily want any physical sex, just go get off with a guy who likes smoking too. Where can I find a jerk-off smoking buddy or am I wasting my time?
-Cock Smoker

Wow, this is really going to test the limits of this being a judgment-free zone. Except if you look back at some of my other columns, you'll find I'm judgmental as hell. With love. Well, here goes.

Smoking is toxic, dangerous and expensive and can potentially shorten your time on earth meaning less masturbation time. Plus less money for important things like lube and porn.

I’m a gay guy with a bi boyfriend and he doesn’t always seem keen on sex with guys. When he does it has to be as if it’s “wrong” and “degrading”, but I love him and want to be with him. How can that fit in with my life and what I want or am I kidding myself?
-Gay Meets Bi

I thought it's bisexual folks to who get pinne with the "confused" stereotype. Seems like you're doing your best to counter that because you're the one who's confused.

He totally knows what he wants: sex play with an air of the forbidden. If he actually thought it was wrong, he'd be checking into some ex-gay conversion program (which totally wouldn't work of course). He'd actually be trying to beat the gay out of himself, going to some toupee convention at a Ramada Inn or wherever ex-gays hang out.

I’m in a relationship with a guy who loves to play on cam. It’s not exactly cheating, since he’s not doing anything physical, but I do get jealous. Am I being ridiculous or is this something I should be trying to put a stop to?
-Out of the Spotlight

If by put a stop to, you mean realize it’s futile and ridiculous to try to change someone so you mean break up with him, then go for it. Because the guy you’re in a relationship with is into this, and is into telling you he’s into this. Sounds like he didn’t check out how you’d feel about it though. It’s just part of the package you get with him.

And by the way he is doing something physical. He’s physically touching himself, getting naked, talking or text chatting, and jacking off and/or ejaculating and/or inserting stuff in his stuff. That’s physical.

I think I’m addicted to chem sex. I don’t seem to be able to get fucked or fuck unless I’m high. I’ve tried a few times with different guys and it just isn’t the same. I need to stop for health reasons but just can’t. The only thing I can see working is not having sex, but that’s going to be almost impossible. How can I win?
-Chemical Impulses

I think it's totally fine to have sex while in a lab coat. I know my chemistry teacher looked hot in his. Plus with his dress pants underneath, it was a whole situation of exciting hormonal business stirring afoot. Or those are the metaphors of my dreams. Actually I only took chemistry in high school and my teacher was a never-married Italian dykish lady. Just like I'll be someday! Minus the Italian part.

Oh, I just read the rest of your question. Sounds like you're addicted to tina. And I don't mean F-list actress Tina Yothers of Family Tiesfame and nothing else. I mean meth or whatever it's called. I don't take any nor am I a detox professional so asking me this question is officially your addiction talking because you know I can't help you.

I’m really into watching my boyfriend get fucked by other guys, but he doesn’t know I’m watching. That’s part of the fun for me, but I have a sense of guilt afterwards as I feel I am lying to him. I catch him out at home setting up hookups when he thinks I’m at work and I found a great spot to watch from. What should I do?
-The Ethical Peeper

Since he hasn't flat out asked you, "oh by the way, instead of being at work in the entire expected time frame, were you secretly still lurking at home in some hideway within our place, listening and watching me arrange surreptitious hookups with strangers in our bed then watching us fuck while you jacked off?" then you're not a liar, because you never answered that question with a no.

I'm a 31 year old guy and I'm having trouble talking to my friends about my life. They're mainly all straight and they know I'm gay. I'm out of the closet. But every time they ask me about my private life, even so much as to see if I am dating someone, I get uncomfortable and change the subject. Why might I be struggling so much with talking to my friends about my life?
-Silent Treatment

31? And still using the phrase "out of the closet"? How retro gay chic. How 18th century. Anyhow, it's probably a combination of the following reasons:

I’m going to be alone this Christmas and New Year. I never have been before so not sure what I should do! Normally I’d have my apron on cooking for friends or family but that’s not possible this year. Suggest to me something I can do that isn’t sad or moronic.
-So So Solo

Well this won't reach you in time for Christmas, but let's assume you'll be alone next Christmas too. Hope for the best but plan for the worst, right? Or maybe it's whore for the best but plan for divorce? I really can't remember because I'm in the midst of a holiday party as I right this. I'm definitely not doing something sad or moronic.

The best advice is to volunteer at a shelter. Cook for people in need so you can still wear your Tom of Finland apron you love so much. I'm assuming that's your style but it's even money on that.