By: Laura C. Anderson

Six guys confess their best and worst experiences having anal sex.

Warning: some of these testimonials get a bit messy. 

“It was her time of the month” 

“My girlfriend and I were together a few months before we tried anal. It was actually her idea. It was her time of the month so she was on her period and I guess when girls are on their period they get super horny for some reason – I don’t know – but because we couldn’t have sex the normal way she asked if I would try anal as an alternative. I’m a guy so obviously I accepted the challenge and stuck it in. With a little bit of lube it was actually enjoyable for her.”

“I waited to get yelled at”

“This girl who I wasn’t even dating liked kinky sex and so she was always bending over everything. Naturally, I loved it, but this one time while she was bent over her living room sofa, I went to put it in and I got the wrong hole by mistake. Of course, after realizing something was off because that hole was much tighter, I waited to get yelled at. But instead of asking me to pull out she told me she liked it and we kept going.”

“She’s never had a better orgasm before in her life.”

“For five years I’ve done all I could in the sack to try and get my wife to have a mind-blowing orgasm but for some reason I just couldn’t get her there, not without toys and all that. It ate away at my confidence until one day while my wife was actually four months pregnant with our son. We were lying on our sides spooning and I got hard. My wife reached behind her and directed my dick so it was pointing directly at her butthole. Then she started to grind against it. Before I knew it we were having anal sex and after we both finished she told me she’s never had a better orgasm before in her life. Yep, I’m awesome. Manhood in the clear.” 

“I thought it was chocolate.” 

This girl and I were having pretty consistent sex and one day we decided to try anal. A little while after when we’d had our fill, I changed condoms and we went back to missionary sex. I think I must have loosened her up down there because while she was climaxing she started to shit her bed. Not going to lie, when I first looked down I thought it was chocolate or something but then the smell hit me and I realized what happened. Luckily I was on top.” 

“She claims she is still a virgin.”

“I was once with a girl who was a virgin and in order to maintain her virginity she suggested we have anal. Because apparently a dick in your asshole doesn’t count as sex? I later came to find out that was the first time she had any kind of sex whatsoever. Yes, those girls exist. I don’t know why you’d choose anal as your first sexual experience but to this day she claims she is still a virgin.” 

“I had to take her to the school nurse.”

“When I was in high school my girlfriend and I would have sex under the bleachers while everyone else was eating lunch. It was the only time of the day no one had gym or was using the football field. It was too hard to have standard sex so instead she’d bend over and I’d stick it up her ass. It was pretty much our daily routine until the day I pulled out and realized the condom was no longer on my dick. That left two options: either it evaporated or it was stuck inside her butt. Let me tell you, there’s no easy way to break that kind of news to your girlfriend. We were young and we weren’t sure if it could give her an infection or something crazy like that so I had to take her to the school nurse. That was the last time we had anal sex.”

So there you have it, folks. Some of those experiences are so mortifying my only response in the moment would have been to crawl into a very dark hole – and not the same kind of dark hole his dick just came out of. Then again, some of those experiences give a lot of us hope. I guess when it comes time to do the dirty; all I can advise is that you’re prepared for any outcome, whether it’s good, bad, or downright shitty.  

Laura C. Anderson | @s0mebl0nde



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