Men are so fucking weird.
I’ve had exactly one dude openly ask me to peg him without any awkwardness. Meanwhile, 4 men I dated have indeed wanted to be pegged.
I actually don’t blame men for this. I think there’s an unjustified stigma I will not be unpacking at this time. Anyway, it makes men feel weird about asking.
Anyway, onetime I was dating a dude who was a bit fascinated by my sexual history. He wasn’t even particularly jealous or weird about it, he just want to hear my stories.
Onetime we were sitting on the couch and in some show we were watching someone mentioned using a butt plug on her boyfriend.
“Oh my god, can you imagine doing that?”
I didn’t even bother looking up from my phone. “What? A butt plug?”
“Yeah! What does that even do?”
I shrugged. “It makes you feel good.”
“You’ve done it?”
“Yeah.”
“Like you’ve had a butt plug in or you’ve put one in a guy.”
I finally put my phone down and stared at him. “Someone has used one on me. I used on one a girl and a boy. I have also full-on gone up a dude’s ass with a strap on.”
“What the fuck? A guy let you?”
“He begged for it.”
“Seriously? Why?”
“It… It feels good. What do you want me to say?”
“Isn’t it disgusting?”
“It doesn’t have to be.”
“Doesn’t it hurt?”
“If it hurts you’re doing it wrong.”
“So what about if you’re doing it right?”
“It feels really good. Dude, a guy once fucked me with a vibrating butt plug in me, and it was heavenly.”
“Really?”
“Yeah.” I went back to playing on my phone.
“Wouldn’t it be so funny if you pegged me?”
I glanced at him sideways. “Do you want to be pegged?”
“No! It’d just be so funny.”
“Mmmmhmmmm.” I went back to my phone.
“Do you like doing it?”
“Pegging dudes? It’s not really an act I seek out, but I enjoy it if they do. It’s kind of like taking anal. It’s a fun detour.”
“Anal is fun for you?”
I smiled at him. “Babe, why are you asking? Are you curious?”
“No! I would never want to do that… to you.”
“Do you want to be pegged, bro?”
“That’d be so funny.”
“Ok.” I went back to my phone again.
*What exactly is my role here? This is a very, very sensitive act that really has to be someone’s own idea. I’m not about to talk this dude into getting pegged.*
“So like, this vibrating butt plug. What did it feel like?”
“Awesome.”
“That’s not something you could recycle on someone else right?”
“Huh? No. You’d have to get your own… Do you want a butt plug?”
“No! It’d just be funny.”
“Ok dude. You seem a little too curious about this.”
“I… I don’t know. Maybe I’m a LITTLE interested.”
“Ok, why don’t you consider it, do some research, and then we can discuss trying it.”
“Convince me.”
“No.”
“Why?”
“I am here for any questions but I will not be convincing you. Go research and do some soul searching. I’ll send you some articles.”
*I feel like this is just as important part about anal sex as the actual act btw.*
A week later I’m reading in bed and he throws me a damn vibrating butt plug.
“If this is for me, I have to prep. You know that right?”
“I do. I have prepped. That’s why my shower was long.”
“We need lube.”
He throws me a bottle. “I’m telling you I did my research.”
“You sure about this?”
He nodded.
But yeah, we didn’t go straight to it. In fact, we talked for close to thirty minutes and I asked him A LOT about boundaries, safe words, and aftercare.
*I do not mean to stereotype, but I’m my experience men get REALLY weird when they’re on the receiving end of butt stuff. I don’t know how to describe this phenomenon, but multiple dudes have cried to me after. It’s hella vulnerable.*
“This is like a really, really big butt plug, dude. Are you sure you want to be this ambitious?”
He shrugged. “If we’re doing this, we’re doing this.”
*I’ve kind of skipped over this in my past posts about pegging, but it takes a VERY long time to insert a foreign object into that area. No matter how much lube you THINK you need, double it. No matter how slow you think you’re going, slow down further. Ask where they’re at every step, and- as odd as this sounds- tell them to relax and “push” out. It’s an art*
I was kind of worried about this dude. I was going very slow but there were a lot of groans.
However, as he was bent over my bed with his asscheeks spread open, he was also super hard. Like hot damn. This dude REALLY was enjoying this. By the time it was all the way in, he was begging me to fuck him.
“Do you want me to turn it on?” I asked.
“Absolutely.”
“Are you sure? It’s going to be really stimulating.”
“Do it.”
So I clicked it on.
“Holy shit!” He yelled as he fell forward and did a weird wiggle. “Fuck, that’s so weird.”
“I can turn it off!”
“No! No! It… Feels good.” He was breathing heavy then and his hands were shaking. “Can I fuck you?”
“I kind of want to suck you off,” I laughed.
“Really?”
“I think you’ve earned it. Can you stand up.”
He could. Barely. He bent over with his hands against the wall as I got on my knees. He had tears in his eyes when I took him in my mouth and started moving my head back and forth. I stopped for a moment when he winced slightly.
“Honey are you ok?”
“It feels so good. I’m just overwhelmed. Please don’t stop.”
So I kept going. I took him deeper and went harder. He stroked my hair gently and whispered something about how good my mouth felt.
When I sped my pace up, he moaned and started hitting the wall with his fists. “It feels so good,” he cried. Literally cried. I’m
mot kidding. The man started crying.
“Babe?”
“Please keep going.”
I dove back in. I took him all the way in my mouth and slammed my head down so he could slide down my throat.
“I’m…” He couldn’t even say it. He came.
Men come slowly when they’re being stimulated in this way. I don’t know how to explain it. It’s a slower trickle that comes in waves.
*Sex is fascinating y’all.*
It took a very, very long time for him to fully come… which honestly made swallowing pretty easy. When he pulled out he immediately ran to the bathroom though.
I heard a whimper and was concerned. “Honey, do you need help getting it out?” I asked.
*Oh the joys of butt stuff you don’t see in porn.*
“I got it out.”
“Are you… ok?” I finally opened the door and saw him on the ground. Crying.
“Oh babe!” I threw myself beside him and hugged him for a long time. “Are you ok?”
“It felt really good. I don’t know why I’m crying. I’ve never come that hard.”
“It’s very confusing. I cried the first time I had anal.”
“Really?”
“Yeah. You just need some aftercare. It’s ok.”
We took a shower together after that and I held him for a very, very long time as we fell asleep.
Why did I write this? I don’t know. I think because it’s ok to ask for things, it’s ok to enjoy it, and then it’s also ok to be confused about some of the emotions it unearths.
Also, for the record, we did it again later and no tears were shed.
Source: reddit.com/r/gonewildstories/comments/x3i3qd/wouldnt_it_be_hilarious_if_you_pegged_me_mf
I’m really glad you wrote this and I hope it gets popular. **so much** discussion of consent and the messy negotiations involved with trying out a new kink. It’s great.
Thanks for sharing and being awesome.
Dang you’re on a roll today with all these amazing stories!
A and I have been exploring pegging after reading one of your other pegging stories. It’s been an interesting experience. As a service sub I love giving my partner pleasure so it was interesting “topping a man” lots of good boys and telling him how proud I was of him. It was a great experience for everyone, thankfully no tears and lots of after care
Damn do I want you! What a lucky guy, he knows this right!🤯😘😘
The prostate is a Pandora’s box of incredible feelings. I wish butt play for men didn’t get the bad rap it gets from porn (seriously… being into butt play and prostate stimulation shouldn’t be associated with being dominated or “a sissy”).
I’ve never done penetration, but there’s plenty to enjoy with external butt stimulation or stimulating the prostate from the outside with vibrators to the perineum.
I am guy and my wife fingers me and I think she loves doing that and i on the receiving end feels good specially how much she turned on its just wow.
As a man who has always been “strictly no butt stuff” I’m now feeling curious. I want to cum so hard I cry. Sounds fucking awesome.
This is so cute
UpdateMe!
I love this. I hope there’s at least a few guys out there reading this to then stop and think.
It’s alright to be curious! Why are yall so afraid.
This is such a great story. I’ve started to warm to the idea of exploring this type of play and this story was an amazing read. Thank you.
As someone who has experimented on myself, but never with a partner, thank you for being so awesome to this other person during their vulnerability.
This is very, very close to home for me, wow. Not sure this is exactly the right forum to elaborate too much, let’s just say I understand fairly well how the scenario explained here played out.
Once again, thank you so much my efriend.
What a great story. Well written.
Love your stories. Can’t wait for the whole book.
You deserve a Pulitzer. This is something I’m very passionate about for several reasons, but pegging should be normalized and performed often
It’s stories like this that leads me to believe the song “You Belong With Me” by Taylor Swift is about pegging or at least anal.
The song starts with lines about the girlfriend being upset because of something that the dude said. It’s quite possible that it’s about pegging. He played it off as a joke, be she just doesn’t get his humour. A clear representation of the stigma sorounding the said act.
The next few lines talks about Taylor doing different stuff on a typical Tuesday night. And how she knows his story. Understanding your partner is a very important aspect of anal.
Now in the prechorus is mostly about roles and stereotypes, where the girlfriend is a cheerleader and Taylor is on the bleachers. Just because you’re a man doesn’t mean you aren’t allowed pleasure derived from the back.
The chorus is mostly about finding the one that understands you and the one has been here all along, you just can’t see it. The right person, along with clear communication will lead you to fulfilling your fantasy
This theme repeats all throughout the whole song. With the bridge emphasizing that the you who makes you laugh when you’re about to cry, the one that knows your favourite songs and dreams. It takes a lot of trust and understanding to allow yourself to be vulnerable.
But line that really drives it home would be “standing by and waiting at your backdoor.” You really can’t get any clearer than that right?
TLDR; it’s ok to want to get pegged gents, go for it if you really want to, Tay-tay has your back!
Also you calling him “honey” makes this story wholesome in a way.
I have no idea how I thought of this, but yeah lol
You really are the Patron Saint of Orgasms, nothing but philanthropy! Keep being you and cheers Ms. V!
Damn… wouldn’t it be so funny if you pegged me 😅🥸
Absolutely beautiful story! Thank you for sharing such an intimate encounter – you are a gifted writer!
Did you progress to pegging? Or he stuck with the plugs?
Experience. There’s no substitute. Like the Cole Porter song, you think a bit of the end of it. (No pun intended.)
I’m too old and in a very vanilla marriage, but I seriously would love for this. I’m honestly scared to ask my wife because of stigma associated with it, even though I don’t *think* it would bother me in particular. I’m actually more worried about what my wife would think of me.
Really positive post here mate. You love to see it.
As a man who actively wants this sort of thing, and has flat out said as much to my wife, it’s a little frustrating that she is way less interested. Not sure if I’ll ever get the chance, but it’s not for lack of openness about it.
Oh my god this is one of the best story i read in here. Not transforming the reality too much, such an amazing way to encourage people to try this, and with very good advice.
You made me want to go back to trying this with my wife, maybe that elusive prostate orgasm will finally be reached !