Hello, wanted to add some perspective from someone who’s done anal for years as a gay male (it being expected in that sphere). But not really started enjoying it until my 30s. This reply got a little away from me in length but still hope its useful.
Some background for context.
I came out at 19 and started sleeping with guys around then. I did some self experimentation and butt stuff wasn’t terrible so I identified as verse but anal was always just… nice enough… not amazing but not awful. Its only recently I took some time to really explore things, changed a few things in my life and properly tried to understand my body that it clicked and I started to really like it, but only with a partner that will listen to my needs.
I find that a lot of men like myself equate being gay with anal. You are exposed to many men online and offline parroting rhetoric that anal is amazing, and mind blowing and will change your life. This combined with the stereo types (I’m a slim hairless man, I’m often expected to bottom even before its discussed and have had people arrange an encounter and show up without prep, or lube and just assume I have all that covered.) So all that led to me bottoming a lot in my early 20s, without really getting the hype. I figured I was missing something, or broken, or just had to try harder.
I’ll try and outline what changed to hopefully help some more people understand themselves a little better through my experience and if that helps them make a decision or find pleasure there then that’s excellent.
Summary of what I changed for tldr:
Became medicated for adhd, which allows me to actually concentrate on sex
Dropped the antidepressant medication because the adhd meds solved a lot of stuff
Found if I invited people to my place, somewhere I had control, felt safe and relaxed, that I was able to prep at my leisure, and could control the temperature! I had a lot more fun.
Found that I liked taking charge as a bottom and could force a slower, more sensual rhythm that way, being pounded is fun for the top and I like it for that, but it doesn’t do a huge amount for me, just goes a bit numb.
What does Anal Sex feel like for you? / When you first started exploring with Anal Sex, what were your experiences?
As I said, I’ve had two types of experiences with this, they’re both very different.
Before: I was 19-31, verse, on antidepressants and with unmedicated adhd and doing anal with people because that’s what sex was for me, I described myself as verse and had the most fun when we flipped but I was adorable and cute when I was younger so bottomed a lot due to pure stereotyping. I enjoyed the intimacy and how much my partner was into it but if I finished bottoming it was because I took matters into my own hand… so to speak. At that time I’d describe the sensation of a slow warmth. More mental than physical, but it never went beyond that.
I took some time post getting medicated for adhd, dropping the anti depressants and finally deciding to find what I liked in the bedroom and see if I can get one of those HFOs the cool guys were talking about. I started the usual suspects. Pounding away with a dildo was ok, Vibrators were nice but didn’t really go anywhere and making them more powerful just numbed me, I tried bigger dildos but they just kinda hurt in places and I actually caused some damage I had to let heal. The issue was the sensations were ok, but without it going anywhere It’d go a bit numb eventually and I’ll lose interest and thus arousal, without which I find the sensation changed from pleasurable to ok… or even not fun.
The breakthrough for me was a quiet sunday. I decided I’d try again… but half ass it.
I had the space heater on because it was cold, rates be damned, I’d had a lovely time with friends the day before, so I was super chill. I’d freshly shaved below and cleaned so I was feeling nice and I even put on some sexy clothes for myself which helped me feel lovely.
I didn’t go for the porn videos this time, just put on a music playlist and grabbed a simple stainless steel wand. Some lube and lying on the bed later I found not searching for “the video”, being warm, relaxed and feeling confident, and the hard toy meant I could really explore and focus on the sensations. Unlike before, I didn’t focus on the goal of cumming. I just pressed what felt nice. Rather than pounding or vibration or anything, steady increasing pressure does it for me. Things built and built and eventually I, to my great surprise, came hands free. It was a warm and slow orgasm, not as sharp as penile but longer and more drawn out.
Best part? No refractory period, just warmth, squirming with pleasure, cum, go again, don’t even start from 0, I’d guess start from around 70%.
This went on for a couple hours, in which time I revisited some of the other toys. Dildos are lovely with different sensations now I know what to look for, less precise than the wand but more a whole sensation than a focused pressure. The vibes are still a bit numbing but you can clench to make them hit where you need too and if I turn them off and only have them on in short bursts they work for me.
Checklist for fun but stuff imo:
- Feel sexy
- Be relaxed
- Be focused on the sex not the porn or the laundry
- Be aroused, if I’m not its kind numb
- Be warm (temperature wise)
- Enjoy the sensations, don’t focus on the end goal, if you’re not, change what your doing.
How would you say Anal Sex and Play has impacted your sex life?
A week or so later and armed with my new sense of butt awareness I asked a friend with benefits if he’d mind being my guinea pig. I’d implemented what I’d learned, I’d tried to take the anxiety out of the equation. Heating was on, I was prepped and dressed up, (cloths over the top) and I knew this person well, we’d been friends before benefits and i trust them. We shared a glass of wine and I took things slow and sensual, not rushing towards endgame. We made out of the sofa, heavy petting and just taking it easy, jokes and laughs and keeping things fun and relaxed.
When we moved to the bedroom I eased into things without going straight for penetration (before, I often enjoyed forplay more than the main event and this time I kept that vibe going). Only once we were both pushed to the edge multiple times and I was as hard as I have every been in my life did I invite him in. I pushed him down gently and got on top, able to control the pace and angle as I now was I trusted that what felt good for me felt good for him too without a need to “FINISH HIM!”.
I tried a number of positions and angles with breaks for making out some more and eventually found myself the little spoon sideways with an upwards angle, moving my hips to the music I’d had on in the background and listening to him breathing get faster and faster. We didn’t finish at the same time, and I didn’t hfo but I only needed the slightest push after he squeezed me close and rode his out. The buildup and journey made it finally one of those mind blowing orgasms to the point where I thought to myself “Good lord! I’ve been doing sex wrong!” Some cuddles, some aftercare and discussion over what worked and what didn’t and we ended up very pleasurable evening. Even letting my man take charge worked for me this time because I’d taught him what worked for me.
Since then I’ve not bottomed (or really slept with) strange any more, I’ve learned it makes me nervous and its not what I’m really into. My friend and I have been seeing each other more often and I hope that in the new year I might move a little closer to him. I’ve also been trying a few new and old things. Estim is pretty fun! Would recommend! Though I feel like I’ve had to take a small course in electrical engineering because i started modifying some stainless steel toys to be electrodes rather than buying them all.
I’d suggest to those that read this whole thing, If anal for you is ok at best. You might be mentally not quite into it, you might be putting up barriers to your own enjoyment, losing interest because of nerves, adhd or distractions (if like me, you were hoping he’d hurry up so you can go back to fun stuff while he’s pounding away check this one) or you might not be with the right person. You might also simply not into it, and that’s fine too. However take the time to understand yourself and decide for yourself rather than going with the flow and hoping for the best. Don’t take 10 years to figure it out.