https://preview.redd.it/51a8f1qeagrd1.jpg?width=500&format=pjpg&auto=webp&s=61884a648c7c1243096edce65dd2ba7059eb2f79

I've been watching the posts on this subreddit for a while now, and I think it's a good time to share my experience and advice with all of you looking to get pegged.

Let's face reality. You'll never find a woman to peg you if your only strategy entails putting up a post that says, "33M looking for someone to peg me." I'm pretty damn sure there will never be a woman just sitting around with a strap-on waiting for that post to appear in her feed. I'm also pretty damn sure there are no women following this subreddit, but SOMEONE PLEASE PROVE ME WRONG!

There are two guaranteed ways to get pegged:

1. Pay for it.
2. Find a partner who is willing to do it.

Both of these options come with risks.

I think everyone knows the risks associated with prostitution, so I'm not going to cover that.

I can talk about finding a willing partner because I've found three in my lifetime. And each time, it was a little scary being open and honest about my desire for them to fuck me in the ass. On the opposite end of the spectrum, I have been shot down by other partners and potential partners, sometimes in humiliating fashion.

Here's a short rundown of some of my experiences:

1. THE FIRST WIFE: I never brought it up to her. While she enjoyed sex, she was not adventurous at all. She would often chastise me for masturbating or for looking at porn. I did not feel comfortable talking about any of my fantasies with her. It was one of the downfalls of our marriage.
2. THE FIRST PEGGER: We dated a bit before my first marriage. Sex with her was great at the time, but we were young and not very honest with each other. It wasn't until we reconnected years later that we became completely open with each other. She had never pegged anyone before, but once we started she took to it like a fish to water. We used to share our sexual exploits on Tumblr. She would always get off while fucking me in the ass and would often buy new dildos to try on me. She almost broke me with one of them. We shared a story about that night on our Tumblr. This picture above is of us during one of our sessions.
3. THE HUMILIATING SHOOT DOWN: An old high school friend and I flirted repeatedly through the years. Once, I brought up the subject of pegging, and right away, she let me know, "Any guy who likes that is gay." I never mentioned it again, and it turned me off to the point that our flirtation died out soon after.
4. THE SECOND PEGGER: Undeterred by the shootdown, I remained open and honest about my love of getting pegged whenever I talked about sex with a potential partner. At first, this one was unsure about it. However, she didn't say no. After we got comfortable with each other sexually, she would often bring it up on her own. She even bought a pegging starter kit. The dildo was disappointingly small, but she more than made up for it the first time she fucked my ass. It was like some pent-up need unleashed in her. The longer she fucked me, the more passionate she became. After that, pegging was something she initiated on a routine basis. A good time was had by all.
5. THE SECOND WIFE: Much like the first wife, she was pretty much meat and potatoes sexually. I decided to hold back on pegging until I could help her lose some of her inhibitions. That plan backfired extraordinarily. We were watching a sex doc one night, and one of the segments was about pegging. I thought it was the perfect time to talk about it, but while watching the segment, she nearly shouted, "Gross! You wouldn't want to do that, WOULD you?!" It was many years later, when we were having a frank discussion about my dissatisfaction with the declining state of our sex life that I finally brought up pegging. I spoke about how I've always been interested in pegging but stifled that need because of her previous reaction. She didn't remember that had happened and immediately apologized. We've tried pegging since then with varying degrees of success. Honestly, she's not very good at it, especially compared to my past partners. But at least I could finally be honest with her, and she accepted me.

I'm sharing all of this hoping that someone will find it helpful in finding a pegging partner of their own. There are women out there who already enjoy it. There are women out there who haven't done it yet, but could be open to it. It's a scary subject, but if you have a solid relationship with your partner, the worst you'll deal with is her saying no and a potential period of awkwardness. And just because it's a no the first time doesn't mean it won't ever turn into a yes somewhere down the road.

If anyone has any questions, I'll happily answer them to the best of my ability.