Stories

Stories from Straight Men who Learned to Love Anal

Shirtless Man in Jeans

One of men’s top sexual fantasies is anal. I’m talking about you being the bottom, not the top!

In recent years, straight men getting topped by a woman with a strap-on has been given a name: pegging.

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Strap-on dildo and harness sets have been selling like hotcakes to heterosexual couples, not just lesbians. And women have been buying butt plugs and dildos for their men.

Submissive guys are often familiar with receiving anal penetration, but every man should experience the mind-blowing physical and psychological sensations that come from getting fucked up the ass.

Stories from Men who Lost their Anal Virginity

“I fantasized a lot about my wife kneeling behind me doggie style and giving my ass a pounding I’d never forget. I brought home this huge strap-on, and she just laughed and pulled out this little flared butt plug not much bigger than her finger. She said I needed to try a plug before the strap-on, and she was right.

When we used the strap-on for the first time, I howled like a banshee. Once she was inside, this strange calm flooded me and I opened to the feeling—sharp and local, but also soft and spread out. I asked permission to rub my hard cock while she thrust into me and all the pain then exploded into my hand in a staggering orgasm.” – Jack, 30

“I had a girlfriend not long ago who would wet a finger in her pussy and then gently roll it around my asshole while she sucked me off. It was amazing. After that, I saw this hot older domme and begged her to punish me with a dildo when I was a bad boy. I’ve had to be punished twice in a row with that dildo, because I wasn’t allowed to come and I did.” – Ali, 26

“My girlfriend loves receiving anal and I thought it would be fun to switch roles one day. I had never had so much as a finger up there. I’ve always been more interested in sticking my cock in a woman’s ass than what happens to mine, I guess! I was up for it but found it hard to relax. She did get a finger in eventually and then a very small toy.

Later I realized we probably should have used some good lube, not just spit. Spitting on your hand only works in porn or for those who have done it a million times and are used to it!”- Pete, 32

“I’m on a medication that makes it difficult to get a hard erection. My girlfriend has a nasty streak, and once when I couldn’t satisfy her she yelled at me. She said that since I couldn’t fuck her properly that maybe she should be the one fucking me. It was a tense moment, but we eventually wondered if there wasn’t an unexpected solution there.

Now she takes out her frustrations on top—with a strap-on. It was weird at first, but honestly, we’ve never been this sexually happy. Through the beast of necessity, we discovered something about ourselves in older age: she likes to take control, and I like to get pegged. It’s win-win.” – Roberto, 58

Tell us what you think!

Tell us what you think!

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