1. My partner wants me to give him a ruined orgasm. Where do I go to learn that?
Right here. Ruined orgasms are pretty easy — they’re so simple, in fact, that people sometimes give them to (or inflict them on) their male partners by accident. Here’s how you do it: bring your partner to the point of orgasmic inevitability — get him to that point where there’s no stopping his orgasm; even if Marjorie Taylor Greene were to burst into the room, he’s going to come — and then cease all stimulation. Take your hand off his dick, take his dick out of your mouth, lift your pussy or ass off his dick — whatever you were doing to get him close, stop. He’ll come, but it won’t be anywhere near as pleasurable or intense as his usual orgasms, i.e., the orgasms he has when his cock is stimulated to...
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... the orgasms he has when his cock is stimulated to and through the point of orgasm.
2. How can I be more fuckable? I put myself out there, but no one bites. I’m done being a 31-year-old gay virgin. I am a clean person, shower every day, wear clean clothes, and was voted “most likely to brighten up a day” in school.
Maybe you’re doing something wrong — but I couldn’t tell you what that might be without meeting you, getting to know you, and making polite inquiries about your voting history. But I can tell you what I would do if I were in your shoes: I would hire a brutally honest “life coach,” a personal trainer, and a hooker, but in reverse order.
3. What’s your #1 tip for someone who has never been to a sex party before? It includes a wide range of ages, genders, orientations & proclivities, and many nervous newbies on the invite list.
4. Can a person who has always had open sexual relationships become monogamous?
5. I never visualize having sex with my husband anymore. In my mind, it’s always someone else. Is that bad?
6. Why is anonymous sex — in places like bathhouses and gloryholes — so enticing to queer people like me?
Lesbians aren’t exactly crowding into bathhouses or around glory holes — nor are asexuals (no interest), demisexuals (not enough time to catch feelings), sapiosexuals (can’t demand SAT scores), etc., etc., etc. So, I’m gonna assume you’re a gay man. Before I write another word: not all gay men find anonymous sex and/or public sex environments enticing. But the ones who do… they’re not doing it because they’re gay. They’re doing it because they’re men. I mean, if you told straight men there were places where walls had holes in them and women were kneeling on the other side of those walls waiting to suck them off, straight men would go to those places. (Not all, but lots.) There’s nothing gay men do that straight men wouldn’t if straight men could but straight men can’t because women won’t. As for why women won’t… the answer is equal parts disinterest (on the part of most women) and an entirely reasonable fear of male sexual violence (on the part of all women). (Update: Being called out for bi erasure in this response — which is fair. I’m usually careful to say “gay and bi men” when discussing, well, questions, issues, and concerns that involve men who have sex with men; please see everything I wrote during the monkeypox outbreak. Still, I shouldn’t have left bi men out of this response. Bisexual guys: You’re at the bathhouses too, you’re kneeling on the other side of those glory holes, I see you, and you’re valid.)
7. What do you do when you’re bored with the sexual smorgasbord and just want a few quiet nights in?
You spit the dick out and go home.
8. Quick etiquette question: Can I use my fucking machine in a hotel room?
You’re allowed to fuck in hotel rooms. But fucking machines — at least the ones I’ve been in the same room with — are pretty fucking loud. They start loud, they stay loud. People fucking, on the other hand, typically get loud toward the end of the fucking; so, once the people in the room next to yours can hear you fucking, they know it’s almost over. So, while I think we all have to put up with a little noisy fucking in the next room from time to time, I don’t think it’s reasonable to expect the guests in the next room to put up with the noise of a fucking machine.
9. I’m in love with my roommate. I think he likes me too. I just fear losing his friendship if I tell him. Any thoughts on how I should handle this?
If you don’t open your mouth… your roommate can’t stick his dick in there, right? Just don’t open your mouth and say, “I’m in love with you,” as that will instantly dial the emotional stakes up to 11. Instead, tell your roommate you’re attracted to him and reassure him — before he can even respond — that you will get over the awkwardness (and him) if he doesn’t feel the same way about you.
10. How can I help a quick shooter have a slower draw? This D isn’t lasting long enough for me!
Some medications seem to help premature ejaculators — excuse me: some medications seem to help persons experiencing premature ejaculation (PEPE). Additionally, some PEPEs can train themselves to last longer by jacking off a few hours before sex with a partner, strengthening their pelvic floor muscles, and edging themselves endlessly. But if nothing helps — and sometimes nothing does — and delaying penetration until after you’re satisfied doesn’t work (because only a good, long, hard fuck can satisfy you), get a strap-on dildo. He fucks you with his dick until he’s done, then uses the strap-on until you’re done — or vice-versa. Strap-ons are great, and they’re suddenly everywhere in gay porn… and we all know what that means. (It means straight people will be giving each other strap-on dildos as wedding presents by next summer.)
11. Who has your favorite celebrity armpits?
The very first pair of celebrity armpits I noticed belonged to Robbie Benson. (I hadn’t hit puberty yet, so I didn’t understand why I wanted so badly to be that surfboard.) I don’t currently have a favorite celebrity pair of armpits but I’m open to suggestions — drop your recs in the comments.
12. Top tips for being a good/smart third when playing with a couple?
Be clear about your expectations — what you’re into, what you’re not, what you’re comfortable with, what you aren’t — and politely decline if they aren’t clear about their expectations.
13. I’m a young college professor in New York City and an active Grindr user. Is there a way to block an age range?
In these morally panicked times, it’s probably better to err on the side of not fucking guys young enough to be your students — to say nothing of guys who are your students or who go to your university and might become your students. Unfortunately, there’s no way to block guys by age range on Grindr. So, you’ll have to block them as they come.
14. Why do people say “ethical non-monogamy” when they just mean “dating”?
Because they mean different things. While some ENM people do date, many people in ENM relationships aren’t interested in dating (or aren’t allowed to date) outside sex partners; these people don’t describe themselves as “dating” because 1. they aren’t dating and 2. they don’t want to (or shouldn’t want to) mislead potential new sex partners. And while people who ultimately want a committed ENM relationship can and do date, lots of people who date — lots of people out there fucking around with multiple partners and not lying to anyone about it (and thus non-monogamous and ethical about it) — ultimately want a committed monogamous relationship and identifying as ENM would be misleading.
15. I love sex but I don’t enjoy getting off or seeing cum. Is that weird?
16. If my bisexual husband is fucking men in the ass with a condom but not using a condom with me — his cis wife — am I at risk?
You’re at a slightly higher risk for certain sexually-transmitted infections — primarily HPV and HSV. But since your husband doesn’t look at you and see the reason why he can’t fuck other men, I’d say you’re at a slightly lower risk of divorce. (If your parents were so negligent that they didn’t get you vaccinated against HPV, go get vaccinated now.)
17. Any queer-cuck related porn that you’d recommend?
Jack Hornwood’s erotic novellas — jackhornwood.com — come highly recommended.
18. Would you consider a 67-year-old man who’s had NUMEROUS affairs while in what were supposed to be monogamous relationships and more than a few “friends” who turned out to be more than just friends to have a “propensity” for extra-marital relationships, secrets, and duplicity? Asking for a friend.
Honoring a monogamous commitment is going to be a struggle for this guy — assuming he has any interest in honoring a monogamous commitment — and being with him will be torture for your “friend” whether or not he ever gets around to cheating on her… which he most likely will.
19. I’ve always had to beg my partners to hurt me. Now I finally meet a guy who is legit sadistic, and I’m completely freaked out. He’s very sexy and everything is consensual, and he hasn’t violated any of my limits. But unlike my two previous boyfriends — very sweet guys — this gentleman doesn’t feel the least bit conflicted about hurting me. What should I do?
Send him my way.
20. My husband and I have been together for 15 years now. He’s never been with anyone else and has recently opened up about wanting to explore outside. I do not have this desire. I love him and ultimately want him to be happy, but I also don’t want to make myself unhappy in the process! Can you recommend how to find a sex positive therapist for us to help us navigate through this new path?
Check out AASECT.org.
21. I’m a pretty jacked college student and I get a lot of attention from gay dudes. And that would be great if I was gay but I’m not. Girls expect guys like me to make the first move, but I worry about coming across like an asshole or a harasser. I’m also very submissive but women take one look at me and expect me to be aggressive when what I really want is to be dominated and degraded. I don’t even know how to have that conversation with a girl. Any advice?
Gay guys make great wingmen — so, the next time a gay dude hits on you, tell him you’re flattered but straight and blah blah blah. Then ask him if he knows any hot dominant girls. If he does, ask him to hook a jacked sub up. If he doesn’t, I promise he won’t rest until he finds a hot dominant girl he can introduce you to — particularly if she’s allowed to share all the details with him. And whether he already knows a hot dominant girl or has to go find one, your new gay best friend will be only too happy to have that conversation (at least the first one) for you.
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