I took a deep breath, then knocked on the apartment door. This apartment complex wasn’t run down, but it wasn’t fancy either. It was meant to blend in with the rest of the street, which was a good thing. It was the perfect place to do things undisturbed. Which was definitely the case here.
The door opened and Kara, a pretty girl of what appeared to be of mixed Asian and white ethnicity stepped out. She was about early twenties, so about my age, and was dressed casually – just a Nirvana shirt and some jeans with those stylish holes in them. Not that she’d need them in a few minutes. “Welcome! I’m glad you made it. Wow, you’re really cute in person.”
“Um, thanks,” I replied, a little bit nervously. “You’re pretty cute too.”
She smiled and let me indoors. The living room of the apartment had a few couches, which she led me to and sat down with me. The centerpiece of the room was a large table, big and sturdy enough for someone to comfortably get on top of. There were some pillows at the corners, and a hole in the center with a detachable bucket below it.
“So,” I gotta ask,” she spoke with a grin on her face, but it was a very playful grin. “This is your first time visiting me. Why are you looking to get pegged?”
There it was. The million dollar question. The reason for all the secrecy.
“I’m curious, mostly,” I replied with honesty. “It seems like fun, and I want to explore it in a way that doesn’t have me feeling judged or…”
“Degraded?” Kara finished, giggling. “Well, you’ve come to the right place! There’s no judging here, no humiliation of any kind, just fun for everyone involved! Pegging can be quite a fun activity if you have an open mind and the right person. Want to get started?”
“Sure thing, yeah.”
“Let’s start with getting rid of those clothes.” Kara stood up and undressed, first her shirt, then her jeans, and then her bra and panties… until she was completely nude, her dark wide eyes and hair contrasting well with pale, almost alabaster skin. She had a few tattoos, all dark black and also contrasting nicely with her skin.
I wanted nothing more than to ravish her and take her then and there. But I already knew what I’d signed up for. Another time, I told myself as I stripped down as well. I was no athlete but I did what I could to stay in shape. She seemed to like what she saw though, and walked up to me and said “Kiss me” before tickling my stubble and leaning in to lock our lips.
For a few second we made out, and I was more than happy to let my tongue explore the confines of her wet mouth. But then she broke the kiss and told me, “Now get up on that table. Hands and knees on the pillows at the corners.”
I did as she insisted, a little hesitantly, and climbed up the table. Getting into a doggystyle position with my legs spread, I couldn’t help but feel a little awkward in it. But I told myself that I’d already committed to this, and that this was something that was needing to be explored one way or another. Best to do it with an understanding person like Kara. I also noticed that the hole and bucket were position to be aligned with a person’s groin.
“Good! Now hold still while I tie your arms and legs into place.”
“Tie them?”
“To keep you from squirming about, of course. Not to mention that prostate orgasm can be achieved completely hands free. Although I’ll be using mine as needed to enhance the experience.” Kara got a few ropes that looked to be made of a synthetic material and tied my wrists and ankles to the table legs. They were comfortable, and I had enough freedom to move a little bit, but not completely leave the table if I wanted to.
*You signed up for this. Just take it in and relax.*
“We’ll start with fingers.” I looked back to see Kara applying some lube on the pointer and middle fingers on her right hand. “Think of it as a warm up, a tasting of what you’ll be experiencing today. It won’t hurt that much, I promise.”
With my bare ass facing her, I couldn’t just accept what she said at face value. But I kept looking at her to see what she was doing. She set the lube aside-
-and pressed her fingers into my asshole.
There was a bit of discomfort at first, as I’d never had anything up my butt before. I said a silent thanks to myself for following her instructions to try to clean myself down there before coming to the apartment. But after a few seconds, I felt the familiar clench of my hips when I thrust my cock in a cunt. I had never really thought about it, but I realized that when my cock felt it and jolted to full length, it was often accompanied by my asshole tightening.
It was the same effect here. And it felt surprisingly good. It was like there were buttons inside me that controlled if and how I got hard, and Kara’s pressing did the trick to get blood flowing and the heartrate up.
Kara had just unlocked something inside of me, and I was more curious than ever to keep going.
“How does that feel?” Her fingers slipped out to where only the fingertips were still inside.
“That- that was really good, actually.” No lies there.
“How about this?” She pushed the fingers back in, and then began sliding them along the walls of my ass back and forth.
“Oh fuck, that’s good too.”
“I thought so,” she replied. “Many are surprised at how good it can feel to have their ass played with. That goes for girls as well as guys.” After a few fingerings, she reached in again and pushed around, as if this was something she’d done before a lot.
Almost immediately my cock stiffened and straightened out again, but this time the effect was stronger, like electricity going from my groin and all around. Especially at my cock. It almost felt kind of strange and warm, but she kept going there for a moment, tapping that area like I might tap a girl’s clit or nipple.
“You feel that? That’s the feeling of having your prostate massaged. I’m sure you already know, but that’s where your body produces sperm. Working on it can create an orgasm all by itself, and a pretty strong one a well.”
“It does feel great,” I admitted to her. Normally I’d be embarrassed to tell someone that I felt good with things up my butt, but she was trustworthy and didn’t seem like the time to immediately switch to a giant dildo as soon as I felt comfortable.
“Wonderful! Now wait right there for a moment. I need to go get the strapon.” And she left to another room in the apartment, probably a bedroom, to go get what she needed. For a moment, I remained there, hands gripping the edge of the table, ass out in the air for someone to take.
She arrived a moment later with her strapon already around her waist, the dildo in question being a green and blue colored shaft that was shaped like it belonged to the tail of a dragon or some other mythical creature. It wasn’t big, but it was definitely larger than just her fingers. “I try not to use dildos shaped like human dicks because I know some straight guys might not like that,” she told me while lubing the toy.
“Thanks, I think.” I supposed it didn’t really matter any which way, but it was nice that she had me in mind. And the dildo in question looked like it was curved in the tail, as if the person using it was specifically looking to have their G-spot or prostate scratched. Probably made by Bad Dragon.
“Just hold tight, like you did with my fingers,” Kara said as she began to slowly insert the toy into my ass. Like with the fingers, there was an initial sensation of pain and pleasure mixed in all at once, and my face winced as she got the first couple of inches inside of me. But then the whole thing went in, and now it was feeling a lot better.
Because it happened to have part of the toy’s shaft right over my prostate when she paused.
My penis stiffened again.
“That feels good too, right?” she asked, and got another turn of the head and nod from me. My hands and feet couldn’t do anything if they wanted to, but they didn’t need too. Being kept in place was part of the appeal. I could just stay in this position and let Kara make me feel good for as long as I wanted to.
And she proceeded to do just that. Slowly, she moved the dildo in and out of my, gauging my reactions and moans to make sure that it was a good experience for me and that I was getting the pleasure I wanted out of it. My mind briefly wondered if she got any fun outside of being able to penetrate me with a dildo. Some dommes got off to humiliating men like this, but Kara wasn’t that type. Her focus was making sure I was having fun and getting a surreal experience.
“Tell me how good it is,” Kara said, in a voice that was both firm and gentle at the same time. As if she wanted an answer, but decided to dip her words in honey instead of snake venom.
“Fucking… it’s good,” I replied, almost losing my words again as my brain began focusing on the amazing sensation that my ass was giving my cock. She was right. More guys would enjoy it if they had the right person and mindset going in. “Keep rubbing it against my prostate, it feels fucking incredible.”
“That’s more like it.” She started thrusting more regularly, her hand going to my cock to start milking it. The added sensation of her fingers stimulating my foreskin, over the head of my shaft and back, was becoming very overpowering. She also tried to push a little deeper, but not so much that it would hurt like a bitch. The ribbed edges of the dragon tail dildo were doing a fantastic job of massaging my prostate, keeping me hard.
“How much longer now…” I drifted off, too caught up in the sheer pleasure and anticipated bliss of orgasm, just over the upcoming edge.
“We can go for as long or as little as you like,” was Kara’s reply, as she continued to thrust back and forth inside of me. “Do you want to cum sooner or later?”
“Umm…” I wasn’t sure exactly. This was nice as it is, but it almost felt like teasing. I wanted to know what was it that made getting pegged so fun for some guys, and it was building up fast.
“Sounds like a ‘sooner’ to me.” She increased her thrusts, with that plastic dragon tail going in and out of me faster. The part of it that was supposed to hit the g-spot or prostate was working it’s magic. “Tell me how much you’d like to cum, please. It won’t kill you, I promise.”
So I did.
“Ah fuck, fuck, I want to cum so fucking bad from you pegging me, please, please make me cum!” I wasn’t sure why I was like that, like the last girl I’d slept with, but it was something about Kara that made me more comfortable doing so. Maybe it was the pretty face, or how gentle she was with the experience, or just how *fucking good* it all felt. Probably a combination of all three.
Kara giggled and nodded her head. “Alright, hold tight again. This is the best part!” She began thrusting into me with eagerness and intensity, holding my thigh with her free hand while the other jerked me off until the very last second, slowly letting it go to show me what a hands-free orgasm could really feel like.
I felt close, getting closer, getting closer…
And then it happened.
I moaned as the first rope of cum was released, shooting downwards into the bucket and hitting the hard plastic with a sticky splatter. It was soon followed by another, and then another, and then another. As my orgasm was underway, my mind went off and my mouth became slack-jawed, still in awe of what Kara could do to me. For her part she continued to push her Bad Dragon toy inside of me until I seemed completely spent, my prostate having released all it had to offer.
While my head was in a complete doozy, I looked down at the mess I’d made. My cock was still hard, the head glazed with some sort of precum material. All of my ejaculate had fallen neatly into the bucket. My arms and legs were steadily shaking, still in thrall of what a hard plastic shaft inside my ass could do to me. It was so, so blissful.
“The bucket’s for an easier time cleaning up the mess,” she mentioned in passing, as if answering my unspoken question about it. But most of my brain was taking in the newfound sensations of pleasure radiating from my ass.
“Wow,” was all I could say. It had felt fucking incredible to have been pegged.
“I knew you’d like it!” Kara was proud of herself. She deserved to; she’d introduced me to the wonders of assplay in a very affectionate manner. “Wanna do it again?”
“Again?”
“Yes, silly. The fun thing about prostate orgasms is that you can readily repeat them faster than jerking off with just your hands.” The toy remained inside, barely moving along the lining of my asshole.
I thought about it, but only for a minute.
“Do it.”
—
In the end, I would have two more orgasms from Kara’s pegging. Both of them were just as intense as the first one, and left me drooling and my brain in some sort of weird sexual high. By this point, I had my head down to the pillows and my ass up in the air even further, as if begging Kara to do it even more with me. I barely even noticed when she pulled out and released my restraints.
“Take your time,” she told me as she got a small snack out for me, namely some Oreos and a can of Sprite. “Your body is going to feel wobbly for some time. I recommend sitting on the couch. Or maybe lie down.” She giggled again. “I’ll even join you and give you a massage if you like.”
“I’d like that very much.” Slowly, with a lot of shaking, I got up, off the table, and walked over to the couch, knees incredibly weak. I did manage to get my little snack and start consuming it, all while Kara hugged me from behind, kissing my neck and massaging my abs and biceps.
I even managed to bring up the courage to ask her out for coffee next week. It was just as nervewracking as being pegged, but to my delight she said yes and kissed into my shoulder again.
Life was good.
—
*Hey all, first time writing something more submissive. I had a great RP recently where my partner was a dragon girl, and suggested using her tail in my ass… and one thing led to another. Hence the shape of Kara’s toy.*
*One thing that I’ve noticed about pegging communities on reddit and elsewhere, which I don’t really like, is that they make out the guy to be a total sub. Maybe he’ll be sissified, maybe he’ll be cucked in addition to pegged, etc. I personally think you don’t need to be totally submissive to enjoy pegging – it’s just having your prostate scratched pleasurably, and I hoped to capture that kind of feeling in this short story.*
*Kara’s appearance was loosely based on Jade-Anh Ngo, but any attractive pale Eurasian girl will work for her I suppose. I also left her specific relationship to myself vague and open to interpretation. Sex worker, close friend, something in between those two – whatever you imagine really.*
*Hope you enjoy! Please let me know if you liked it! Next up in my mind for a short sexy story is a retelling of the Rape of Persephone by Hades from Greek mythology.*
Source: reddit.com/r/sexystories/comments/htmlvc/my_wholesome_introduction_to_pegging_mf_gentle
Great story. Well written. Now all I need to do is find a woman to peg me with the same care and gentleness.