{"id":782383,"date":"2026-07-05T19:40:10","date_gmt":"2026-07-05T19:40:10","guid":{"rendered":"https:\/\/www.newsbeep.com\/ca\/782383\/"},"modified":"2026-07-05T19:40:10","modified_gmt":"2026-07-05T19:40:10","slug":"male-anal-sex-advice-men-always-act-so-weird-about-my-favorite-bedroom-activity-im-sick-of-it","status":"publish","type":"post","link":"https:\/\/www.newsbeep.com\/ca\/782383\/","title":{"rendered":"Male anal sex advice: Men always act so weird about my favorite bedroom activity. I’m sick of it!"},"content":{"rendered":"

Sign up for the Slatest<\/a> to get the most insightful analysis, criticism, and advice out there, delivered to your inbox daily.<\/p>\n

How to Do It is Slate\u2019s sex advice column.\u00a0Have a question?\u00a0Send it to Jessica and Rich here.<\/a>\u00a0It\u2019s anonymous!<\/p>\n

Dear How to Do It,<\/p>\n

I have been seeing a new guy for about three months now. We\u2019re having pretty good sex and he\u2019s fairly adventurous from what I can tell. There is something I enjoy doing in bed that hasn\u2019t naturally come up and I\u2019m not really sure how to pose it to him. I\u2019d like to peg him if he\u2019s into it. It\u2019s something I tried out in my last relationship and we both had a lot of fun with it. It ended up being a real high point for the both of us. But I\u2019ve never done it with anyone else, hence the nervousness about figuring out a way to bring this up. What\u2019s a way to tactfully mention it without getting his defenses up? I feel like most men won\u2019t take it well because of the obvious societal reasons and I don\u2019t want to screw up the good thing we have going.<\/p>\n

\u2014It Could Be Fun<\/p>\n

Dear It Could Be Fun,<\/p>\n

I agree with you\u2014this is potentially perilous territory. The straight(\/-ish) guy psyche is such a delicate thing that such a proposition could trigger a crisis as easily as it could trigger a boner. I think the main thing to do here is not to indicate or imply that there is something that you saw or felt in him that led you to this interest. So instead of proposing it by saying, \u201cDo you want to get your butt played with?,\u201d you might lead with yourself: \u201cI love to play with guys\u2019 butts. Is that something you\u2019d be interested in?\u201d As you may know as an experienced butt-player, it\u2019s best to ease into a guy\u2019s hole. I wouldn\u2019t jump to pegging right away, as that could also scare him off. If he says he is interested after you ask, you can then probe exactly what he\u2019s down for. Fingering, rimming, playing with toys, and, yes, pegging can all be floated as options. Let him guide your pace. Maybe you start with fingering and he likes it so much that he wants more.<\/p>\n

I think if he\u2019s down, and you start moving slowly but he\u2019s obviously loving it but things aren\u2019t quite progressing, then you can bring up your pegging past and how much you loved it in your last relationship. That may help him along. Remember to approach him as you would his butt: with lots of patience and lube.<\/p>\n

\n Please keep questions short (<150 words), and don\u2018t submit the same question to multiple columns. We are unable to edit or remove questions after publication. Use pseudonyms to maintain anonymity. Your submission may be used in other Slate advice columns and may be edited for publication.\n <\/p>\n

Dear How to Do It,<\/p>\n

I\u2019m a 31-year-old bisexual trans man. My transition began at age 15 and I am now stealth, live as and am seen as a man in every way. I have been saving up for phalloplasty but it will still be many years before that will be a reality. I absolutely do not want anyone outside of my immediate family and an extremely close handful of friends to ever find out that I have \u201cfemale anatomy.\u201d It doesn\u2019t matter how accepting they are or if they\u2019re trans as well, other people knowing about it at all gives me horrible dysphoria.<\/p>\n

The only sex I\u2019ve had was as a teenager, when I was unable to be stealth and allowed boyfriends to do things that I really hated because of my dysphoria, I was afraid of disappointing them by setting boundaries. I have tried dating asexual people, but found that dating at all just makes me more aware of what I can\u2019t have.<\/p>\n

Lately I\u2019ve been more and more tempted by the idea of trying to find casual sex partners, be that a fuckbuddy or hookups, who would be interested in me getting them off with my hands and\/or mouth but wouldn\u2019t mind me keeping all my clothes on. Someone sitting on my face or fucking my mouth seems like pretty much the only sex that I could actually have without outing myself and being miserable. Lesbians seem to have it pretty easy with this situation where being \u201cstone\u201d is a normal thing for someone to be, but for a man it seems to be pretty much unheard of.<\/p>\n

Even if I present myself as exclusively orally fixated, will potential partners suspect something if I don\u2019t get a noticeable erection from giving head? Would you be suspicious, in a potential receiving partner\u2019s shoes? I have a normal packer, but should I try and find one that gives the impression of a semi, maybe? I know that using a glory hole would solve this problem but that\u2019s a lot less sexy to me. Do you have any advice on how I can have any kind of sex life without feeling like I have a giant blinking neon EUNUCH sign over my head?<\/p>\n

(Please don\u2019t suggest therapy to \u201caccept\u201d more people knowing that I\u2019m trans. I spent plenty of time being out and everyone, even other trans men, still seems to think having a vagina is in some way a reflection on who you are, casually expects you to enjoy or not mind talking about it or even using it, or they act like we\u2019re some kind of \u201cmen lite.\u201d I suspect that once I\u2019ve had bottom surgery, I won\u2019t mind more people knowing that I was assigned female at birth, but right now all that does is remind me how much I hate my body.)<\/p>\n

\u2014Frustrated and Emasculated<\/p>\n

Dear Frustrated and Emasculated,<\/p>\n

In my subjective experience\/understanding, if I brokered no-recip oral sex that was going to be performed on me, I wouldn\u2019t be particularly moved if that which is in my partner\u2019s pants remained immobile. In this kind of sex scenario, my pleasure is his. It\u2019s not about his dick, it\u2019s about mine. That\u2019s the understanding. I would not bat an eye, because I know there are plenty of guys out there who identify as cocksuckers and that their dick is off the table entirely. I don\u2019t know how you\u2019d fare with a woman. I\u2019m sure you could find some that are understanding but vaginal penetration is so common that the lack of an erection could arouse suspicions that it wouldn\u2019t in a seasoned queer guy. I think nonetheless if you state upfront that your mouth is going to be used and your dick will not be involved, most who take you up on this offer will continue accepting that. They may ask why you don\u2019t want reciprocation or why your dick won\u2019t be involved, but as long as you have an explanation for them (\u201cNot my thing,\u201d is something vague but true that could be your go-to), many will accept this if they\u2019re into what you\u2019re offering. There are a lot of people out there who love receiving oral sex, so I don\u2019t think you\u2019d be particularly hard up, especially if you advertise your services on a kink-friendly app like Feeld or FetLife.<\/p>\n

I think this would be a good path for you. It is very common these days to state your interests upfront and to be openly particular. Again, this often comes via stated kinks but having certain limits baked into the experience is something with which most people who hook up are familiar. Minds are more open than ever. People know that you like what you like. Contentious lovers will not challenge this, though horniness does drive people to test certain limits at times. That\u2019s to say that there is no way to absolutely ensure that you won\u2019t be clocked or questioned. It\u2019s a risk that you will be taking every time you hook up. You have gone without for so long in order to protect yourself. Branching out does seem like the right move, but if the potential questioning is too excruciating to make experimenting worth it, waiting until your phalloplasty is probably the safest bet.<\/p>\n

Share Your Story With How to Do It!<\/p>\n

Readers often have great suggestions for our letter writers, occasionally disagree with a point our How to Do It writers make, or simply want to provide some additional advice. Each month, Jessica and Rich will be replying to some of these comments and suggestions from readers.\u00a0Write to us!<\/a><\/p>\n

Dear How to Do It,<\/p>\n

My girlfriend and I have been talking more seriously recently about finally making a threesome happen. We\u2019ve talked about it for years but usually as a shared fantasy that we weren\u2019t going to make happen. But we\u2019ve started talking about it more and have thought about whether we should just do it. How do we figure out which fantasies are better left between us and which to make happen? Complicating this I think is that there will be another person involved and we\u2019re both wanting to respect this other person\u2019s feelings and experience too. Is there a way to test run it before doing the full thing? We really don\u2019t want to get caught in drama of our own making just because we were a little bored and unprepared. But we could also seriously be overthinking as we both tend to do.<\/p>\n

\u2014Discovery Phase<\/p>\n

Dear Discovery Phase,<\/p>\n

Opening up, even in a limited, we-only-play-together capacity, requires consideration and communication. \u201cOverthinking\u201d here, then, would amount to talking yourselves out of a good time or a threeway all together. Up until that point, no amount of thinking is too much thinking.<\/p>\n

You\u2019ll probably have to experience this stuff via trial and error. You won\u2019t know you\u2019ve gone too far until you\u2019re there, but the good news is that it\u2019s generally easy enough to scale back at any time. It helps to think of yourselves as a team\u2014if one feels scared or just bad about stuff, the other should be able to course correct, soothe, and reassure. If one wants to shut down the threesome, the other should be amenable, no matter how much fun they are having.<\/p>\n


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Ahead of time, discuss your fantasies. Write them down in a list and then review it. What seems doable\/not overly intimidating from this vantage point? Start there. Maybe you keep things really light\u2014kissing, manual, oral at most. Maybe that wouldn\u2019t quite satisfy you so you consider vaginal\/anal penetration. In any case, don\u2019t expect things to go too close to plan\u2014there are three people involved here, so things may go off script in a way you didn\u2019t expect, which is OK. Be flexible, expect the unexpected, and don\u2019t get too caught up in how things \u201cshould\u201d go.<\/p>\n

To help orient you, it may be useful to discuss with your potential third what they\u2019re into\/interested in doing with you both. This would be your test run: Meeting up before sex to check the vibe and see how much chemistry exists between the three of you before your clothes come off. It should be a low-pressure hang that is designated as such. No promises that it leads to anything else, but if it goes well, it just might end with the three of you in bed. Definitely do not bring any drama in front of your potential third. There\u2019s no better way to kill the chances of a good time or a threesome happening at all, for that matter.<\/p>\n

\u2014Rich<\/p>\n

More Advice From Slate<\/p>\n

Slate Video Content<\/p>\n

Last night, I went on a date last night with a great, interesting, funny guy that I got along very well with. After dinner, he told me that he has a medical condition that causes incredibly painful erections and, because of this, has had difficulty with intercourse (and subsequently, online dating). Later on, when his pants came off, I found that his penis was bent upwards in a U shape with his head pointing back towards his stomach. Am I a total dick if this is a deal-breaker for me?<\/a><\/p>\n

Get the latest from Prudie and our columnists in your inbox each weekday, plus special bonus letters on Saturdays.\n <\/p>\n","protected":false},"excerpt":{"rendered":"Sign up for the Slatest to get the most insightful analysis, criticism, and advice out there, delivered to…\n","protected":false},"author":2,"featured_media":782384,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[8],"tags":[1129,49,48,75,9748],"class_list":["post-782383","post","type-post","status-publish","format-standard","has-post-thumbnail","category-entertainment","tag-advice","tag-ca","tag-canada","tag-entertainment","tag-sex"],"_links":{"self":[{"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/posts\/782383","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/comments?post=782383"}],"version-history":[{"count":0,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/posts\/782383\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/media\/782384"}],"wp:attachment":[{"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/media?parent=782383"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/categories?post=782383"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.newsbeep.com\/ca\/wp-json\/wp\/v2\/tags?post=782383"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}