Man Shares How He Learned To Love Being Penetrated By His Girlfriend

March 25, 2016  |  

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It’s Friday, so what the heck: let’s talk about pegging dudes.

More specifically, this article in Esquire magazine entitled, How My Girlfriend Helped Me Fall in Love with Getting Pegged.

And as the title suggests, it’s a heartwarming tale about the time Zachary Zane, a bisexual man who is in a loving and committed relationship with a woman, learned how to love getting a finger – and other things – in the butt.

But of course, it was a process.

Although Zane is bisexual, he writes that he initially wasn’t too keen on the idea, citing a bad singular experience as bottom during a night of rough, drunken and painful anal sex.


“…when my girlfriend told me how arousing she found topping, I promised I’d give it another shot. Not just for her, but for me. I figured I must have been missing something. Queer men had sworn by bottoming since the dawn of man. My gay friends told me there’s nothing more pleasurable than proper prostate stimulation. Millions of men can’t be wrong, can they? I needed to find out.”

Zane writes that learning to love anal stimulation came with plenty of trial and error. The first time he tried it was with his girlfriend, she couldn’t get it in there, telling him, “You’re too tight because you keep clenching.”

Feeling that the problem was mental, his girlfriend suggested that he try stimulating his prostate alone in the shower. That time, the finger went in, but as Zane writes, he still wasn’t quite comfortable.

The next time I tried was with my girlfriend. After multiple attempts in different positions, I finally managed to relax enough for her to get her middle finger inside me. I laid with my back on the bed, legs bent, and it started to feel … nice. Like a massage, except on the inside of my body. I relaxed enough for her to slip her index finger in there too, and that’s when it started to feel really good. We kept it slow and shallow the first few times. After that, we started experimenting with toys and figured out what felt best for me. Thin, long, medium-speed, and vibrating — in case you were wondering. I would orgasm almost instantaneously when she entered me. I began to have orgasms that spread through my entire body like a pulsing electric shock, instead of simple orgasms localized to my junk.

I finally understood what all the fuss was about. I fully believed the hype.”

As Zane writes, the addition of butt-play into their sex life helped their sex life “take on a new and very pleasurable shape.”

He also added:

Although that relationship didn’t last (for other reasons), my love of bottoming did. In the year since my now-ex-girlfriend helped me discover anal delights, I’ve bottomed with many men and a couple of women. Bottoming with a woman, I’ve discovered, is not at all like bottoming with a man. When women play with my anus, it’s a big deal. It’s a thing. It’s kinky. But it doesn’t have to be. Nothing is inherently kinky about anal play. When I’m having anal sex with a man, it’s just sex. That’s what sex is for us. In today’s heteronormative society, where if a man likes anal play he must be gay (nope), many straight women have been afraid to ask me to bottom, afraid to offend me or make a presumption about my sexuality. The thing is, I am bisexual, but enjoying anal penetration has nothing to do with that. I fell in love with bottoming during sex with a woman, and I’m sure plenty of straight men like it too. Can’t hurt to ask, right?

Bottoming, now, has become something that is not only important to my sex life, but important to my well-being. It’s made me a better lover and a better boyfriend to women. Not only am I more aware of physical mechanics (I guarantee that your boyfriend will never power drill you again after you’ve penetrated him), but I feel more connected to the women I’m intimate with.

And sometimes, after I’ve had a rough day at work, I just want to get plowed by a hot woman. What can I say? A man’s got his needs.

I’ll be honest: I have always been curious about butt-play. However I have never had a partner willing to try, which is ironic because they have no qualms about wanting to stick themselves in just about any opening on my body they can find.

I understand though. Folks of all races, religions, genders and class seem to take issue with male penetration. It’s one of the reasons why folks got much more angry over Amber Rose mentioning alleged butt-play with Kanye West than they did over him calling her a “ho” – on multiple occasions.

Still, it’s also kind of messed up that millions – if not billions – of men deny themselves – and truthfully us too – a full sexual experience all because of a fear of “the gay.”

And according to Go Alice!, Columbia University’s health education site:

While anal play may be considered kinky and somewhat taboo, it’s a sexual practice that more than a few men and women, regardless of sexual orientation, enjoy. In men, this potent pleasure point is the prostate, which is found inside their anal canal. The prostate’s primary function, however, is to aid in reproduction. It does this by secreting a fluid into semen before ejaculation occurs, helping with sperm mobility and prolonging the life of the sperm once it leaves the penis.”

See, even nature understands the value in butt-play.


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