The most epic pegging fail… Shit happens [FM]

I’m always fascinated at how y’all respond when I write about pegging because they tend to be popular stories. My theory is that A LOT of y’all have pegging fantasies you’re reluctant to voice, so let me start by saying that pegging (any ass play generally) is fucking awesome. If you’re curious and with a consenting partner, try it. I truly feel bad at how many men are afraid to voice this because I think it’s wrapped up in unhealthy stigmas that shouldn’t exist.

I’ve been so reluctant to write this story out of fear it might dissuade some curious readers, but I also like to take moments to use this account to discuss some of the more “real” intimate parts of sex. It’s not always seamless.

Plus… This story is pretty fucking funny.

I’ve been lucky with ass play generally because I first experimented with a bisexual man. He was very into prep, communication, and general tenderness. The first time I pegged him I immediately understood the appeal. He came so hard his body started convulsing.

It prolongs ejaculation and stimulates a lot of nerve endings. It was super fun to give someone pleasure that way.

Anyway, once when I was in the early stages of a relationship, we exchanged sex stories and pegging came up. This guy was very, VERY eager to try it, and I was down to be his first.

I LOVE unlocking kinks and fetishes with new partners.

So the problem was, I was young. Later in life I would insist partners do research and fully prep, but I didn’t quite know how to insert myself into someone’s anal education before inserting myself into other intimate places. I knew we should have that conversation, but I didn’t know what to say. Instead, I came up with a brilliant solution: I just let him fuck me in the ass first.

So anal sex is an art for me. I have it down to a very specific system I’ve never quite laid out on this account… But fuck it.

First off, I plan the act in advance and go a little too hard in preparation. Much like going into surgery, I don’t eat 12 hours before and I always do some kind of douche or enema before. Then I get lube specifically designed for that part of the body (don’t get fancy- the wrong kind can burn), and start with a butt plug before I actually take a dick. I actually usually give head with a butt plug in because (1) I’ve found the movement is right and (2) men come really fast when they’re doing anal for the first time. It’s usually better to get them off first and go two rounds. Finally, use double the amount of lube you think is necessary and keep the bottle nearby. And of course… shower after.

*Alright… That’s a level of detail about my ass I never thought I’d write, but here we are.*

So I let this dude fuck my ass. It goes pretty seamless with virtually no discomfort or anything… unexpected. I explained my general process and thought he’d naturally pick up on the insinuation that he should do the same.

He did not.

So one night we get home and he is a little tipsy (don’t have anal when you’re tipsy, kids… Trust me). We start off with our usual sex routine. He threw me on the bed and I wrapped my legs around him when he climbed on top of me. He stuck his tongue deep in my mouth and bit my lip slightly before pulling me up so I could straddle him. He pulled my hair and I started begging him to fuck me.

“I want you to feel good,” I moaned into his mouth.

“Really?” He asked as he started kissing my neck.

“Fuck yes. Let me suck you off.”

“I have a better idea,” he whispered as he gently pulled me off of him. He went to my sex drawer and pulled out my favorite butt plug (it vibrated and was a pretty blue color).

So let me explain the scope of my hesitations here. First off, on principle I don’t generally think ass toys are transferable. They’re fine to clean so it’s just a mental hang up, but I feel this is a fair personal boundary. I’m fine with recycling most sex toys and lingerie, but if I was going to stick this thing up this dude’s ass, it was certainly not going back into mine.

Second, we had just eaten, he was tipsy, and had certainly not prepped. Logistically speaking, I’m not sure he was physically ready.

Finally… Getting fucked in the ass is emotional. I don’t know how to explain it, but like 80% of men I’ve pegged have cried after. Fuck, I get emotional after anal sex and I’ve done a lot of ass play (you know… like a slut). It’s a very compromising position that requires a level of trust. I was not totally sure this dude had processed that.

When I voiced these concerns to him, he was pretty fucking insistent that everything would fine. I got the feeling he believed I was overreacting.

So instead of going full strap on, we did compromise that we’d just use the butt plug for stimulation while I sucked him off. This seemed like a fair introduction. However, I did agree to push it in and out so he’d get the sensation.

So yeah, this dude VERY enthusiastically pulled his pants down, bent over, and asked me to go for it. Like a true champ, I fingered him for quite a while to loosen him up with plenty of lube… Hindsight being 20/20, he was perhaps a little TOO loose and relaxed. The plug really slipped RIGHT in, and when it started vibrating, he fucking loved it. He went off about how good it felt.

I got on my knees and took him in my mouth. I went slow at first because I wanted to ease him into it, but when he grabbed my hair and slammed me down I stopped holding back.

I went deep and looked him in the eye as he hit the back of my throat. He started shaking as he gasped. He threw his head back and pulled me so deep I almost gagged. I started fingering his ass, pushing the plug in and out and felt him start to lose control.

He didn’t last long.

So I do not have a dick, but I am fairly certain the sensation of coming when your prostate is being stimulated is… Different. I’ve swallowed a lot of cum, and it feels different coming out… I’ve also never seen men moan the way they do when they come from this method.

This dude SCREAMED my name and I swear almost passed out as he come.

Then he quickly collapsed face down on the bed and I accepted the final piece of this act. I didn’t really think much when I turned the vibrations off and started working the plug out of him. I had grown a little too comfortable with anal apparently and just did it quickly.

That was a mistake.

For those of you who were loved as a child and never had anything pulled out of your ass (*all jokes btw, kinks are normal*), the sensation is odd.

So yes… This dude straight up shit in my hand and didn’t initially realize it.

I was in such shock I wasn’t sure how to respond and I think the words, “Oh, wow… Not the color I expected,” slipped out of my mouth.

Then the smell hit.

He turned around and didn’t initially get what had just occurred. “Huh?” He asked.

“You um… I think you just shit in my hand.”

Then he looked HORRIFIED. I’ve never seen eyes filled with such terror and I went to a law school that employed the Socratic method. His jaw dropped and he looked like he was about to cry, which made it hard for me to process my next move.

After a couple of seconds of calm, I flipped out. I ran to the bathroom, emptied the contents of my hand in the toilet and then tried to wash my hands. However, shit got everywhere and the smell was too strong so I immediately threw up.

He came in to apologize and he started gagging.

“It’s ok!” I helplessly tried to assure him as I heaved the contents of my stomach into the toilet.

*We had had a very nice dinner and this experience REALLY let me examine it from a lot of angles.*

He ran and got cleaning supplies as I finally started washing my hands and managed to get out of my dress (which had certainly been *compromised*). We threw EVERYTHING in the wash, including my clothes and his sheets and then wiped down his bedroom and bathroom.

At some point I looked over and saw tears in his eyes.

“You want to know something?” I asked.

“What?” He answered miserably.

“I once didn’t realize I had gotten my period. A guy went down on me without realizing it and he looked like Count Dracula when he came up for air. He thought I just tasted like pennies.”

He looked at me for a moment, and then we burst out laughing.

“This isn’t going to ruin your attraction to me forever?”

I shrugged. “I still haven’t gotten off and was honestly hoping we could still go again… Maybe after a shower.”

He grinned as I led him back to his newly cleaned bathroom and undressed him. He ended up bending me over after we got clean.

I think the moral of this story is that experimenting is not always super easy and can be a tad embarrassing… But pursue those kinks and unlock that fetish you’re curious about. If you’re with the right person, they won’t give a damn if things get messy.

Source: reddit.com/r/gonewildstories/comments/11c2goc/the_most_epic_pegging_fail_shit_happens_fm