My(35M) first gay sexual experience is coming up. What should I know?
February 5, 2020 11:10 PM   Subscribe

I am a 35 year old cis man, and I have been only with women my whole life. Suddenly I find myself being attracted to men, and my first gay sexual experience is coming up! I feel like a teenager again :) How should I prep for this?

Hello. I am a 35 year old cis man, and I've been only with women up to now. I've always considered myself enthusiastically hetero.

A year or so ago, I first experienced the pleasure of anal sex (i.e. having my butt being played with, penetrated with a finger etc) with my female partners.

Since then, I have been fantasising strongly about being penetrated by a real penis. I've begun experiencing some attraction towards men, and (for the first time) been aroused by gay porn. I really want to be fucked by a guy!

So long story short, I've met a kind, gentle gay man who knows about this history of mine and is interested in being my partner in this adventure. The big day is coming up soon. I'm really excited but really nervous! I know I should try to be spontaneous but I have so many questions! What are things I should be keeping in mind? As a man with only heterosexual experience before this, how do I prepare physically? What will help in making the experience as fun as possible?

Thanks for your help and suggestions!
posted by anonymous to Human Relations (9 answers total) 6 users marked this as a favorite

 
Lube. A lot of it. Lube lube lube.

Also have a good poop before your date. A buttplug up there for a while is a good way to make that happen. Laxative might work too, I've never used it. Possibly an enema if you want to deal with getting the equipment for that and learning to use it, do that in the bathroom because messes can happen. Any of these things can result in surprisingly large poops, have the plunger handy just in case.

A plug will also help you get used to "putting things in your butt and leaving it there for a while" as well as help you get in touch with your butt muscles on a much deeper level than you're used to; there's a thing you can learn that is sort of like pushing out a large poop but also has its own special... inner opening sensation, it's hard to describe. Once you learn it it's also useful for smoother excretion, too. You don't need a huge plug, something about the size of a couple of fingers should be sufficient.

Other toys can help too, do not ever put anything up your ass that doesn't have a flare at the bottom unless you are down with appearing on the annual "Things America Got Stuck Up Its Ass" lists, or until you are a Very Advanced Butt-Haver who can casually sit down on a toy with a knot the size of your fist without much warmup. I have been a VABH in the past and it is a lot of fun but it comes after many months of regular practice.

Lube the heck out of anything that goes up your butt. It does not have any natural lubrication. Make sure anything you put up there is clean, you don't want grit getting pushed around those sensitive places.

Go slow, if it hurts then stop and check for blood, if you are bleeding then you are done for now, no matter how badly you really want to go on.

Condoms too of course. Unless you have both been tested for STDs recently and trust each other to tell the truth about that.

Did I mention lube? Hopefully your friend will have some. There's extra-gooey stuff designed for butt stuff, if you're gonna play with toys beforehand then get that, not the slicker stuff for vaginal use.
posted by egypturnash at 12:18 AM on February 6 [5 favorites]


Condom. Lube. Partner who is prepared to go super slow.

Not physical preparation, but be prepared for it to be awkward. Not so much interpersonally, but it might take a bit of maneuvering or a few tries to find a position that's comfortable and will actually work. That's probably true of any penetration with something that's attached to someone, but remember that you're not uniquely bad at anal sex or anything. Even if you have to pause to giggle.
posted by hoyland at 3:32 AM on February 6 [2 favorites]


More lube than you think you need. No, more than that.
posted by PMdixon at 6:10 AM on February 6 [2 favorites]


Even if you fantasize about getting roughly railed, ask your partner to go slooooow, and let any roughness be dirty talk only.

Breeeeeaaaaathe. Everybody talks about lube, but breath is your best friend in butt sex.
posted by ottereroticist at 8:09 AM on February 6 [4 favorites]


Really the important thing is to remember to breathe. But in the interest of education, here’s How to Clean Your Ass Before Anal Sex, an illustrated guide. (Cartoon illustrations, probably nsfw, not for the squeamish.) A master class in technique. You may not ever need to do any of this, but it’s useful to know.
posted by roger ackroyd at 8:15 AM on February 6 [9 favorites]


Beyond what's already been said, even if you think you've completely cleaned yourself out, there might be poop. Better to be okay with that ahead of time. Keep some easy cleanup close and accessible.
posted by miratime at 9:24 AM on February 6 [2 favorites]


Congratulations on discovering and exploring a new side of your sexuality! There's some great advice in this thread.

I'd add that you undoubtedly have a lot of anticipation around this. Be aware that it may not live up the exciting event you may be imagining it to be. Sometimes chemistry is off, sometimes nerves get in the way -- all the things that can make a first time encounter with any partner a little awkward or unfulfilling. I've read of guys experimenting with guys once and deciding it just wasn't for them based on a disappointing first experience -- that may be true for some but I suspect others are closing off future possibilities for themselves.

In terms of broader resources, there's a pretty friendly, supportive, and well-moderated subreddit for bi men: r/bisexualmen -- you might get some additional responses there (though 90% of them would probably be "LUBE!"). You might also find some good reading material in the Sex Ed for Bi Guys series (written by one of the founders and moderators of that subreddit).

As for lube, I find that silicone lubes are the most comfortable -- but that stuff does get everywhere. There are some decent water based ones as well (e.g., I'm pretty fond of Swiss Navy) but I'd avoid the standard drugstore stuff like KY unless they're your only options. I find these tend to dry out quickly and get really gummy/sticky.

Good luck! I hope it's a lovely and exciting experience!
posted by treepour at 10:52 AM on February 6 [2 favorites]


Eating a fair amount of fiber (soluble and insoluble) in the days before can help a lot. Also make sure you're drinking enough water. You'll have more complete BMs and things will be more internally scrubbed. There are even somewhat designery fiber supplements that are formulated with anal sex in mind.

A gentle enema and some toy training also can help things feel great.

Then, start very slow, use lots of lube, and have fun.
posted by quince at 12:01 PM on February 6 [1 favorite]


Laxative might work too, I've never used it.

I would not suggest using a laxative as they can be unpredictable as to when they actually start working. You don't want diarrhea on the big day!

Possibly an enema if you want to deal with getting the equipment for that and learning to use it, do that in the bathroom because messes can happen.

Definitely do it in the bathroom, but just know that taking an enema is really not a big deal. You can get a disposable Fleet enema at the drugstore for a couple of bucks. You stick the plastic nozzle up your bum and squeeze the bottle so the water goes up. Then you will most likely poop out the water along with whatever stool was residing in your lower colon within a few minutes. Taken a few hours before the festivities, this is generally sufficient to be internally clean enough for comfort and confidence.

I would not go crazy on the fiber in the days leading up to your date unless you are very sure you know how it will affect you. Nothing makes me feel less like having any kind of sex than having a gassy, bloated bellyache, never mind getting poked directly up the butt.

I totally agree on the lube, lube, lube, and going slow. If you feel a twinge of pain during insertion, ask your partner to stop immediately. Your ass will involuntarily clench itself shut upon feeling the pain, and continuing to insert will cause further pain and damage. Take a moment to breathe and relax, let your butt completely unclench and relax itself. Add more lube if needed and try again.
posted by Serene Empress Dork at 4:39 PM on February 6 [3 favorites]


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