My First Experience Pegging [F/M]

Background: We were both eighteen at the time. Me a high school junior (adopted and changed schools during the middle of the year) and him a high school senior. I'm Asian, 5'2, long black hair, green eyes, athletic toned petite body, thick ass, 34a tits, and a shaved pussy. He's white, about 6'2, shorter brown hair, blue eyes, muscley toned body, 7 inch uncut cock, shaved.

At the beginning of the school year in one of my classes I ended up meeting this guy who seemed pretty cool. We sat next to eachother and ended up talking quite a bit and got eachothers number. We started exchanging texts and became more flirtatious. I hadn't known him before that year so I started talking to my friends about him. Most of them were jealous because he was pretty attractive and also just a very nice guy. I took this as a sign to go ahead and try to start something more with him. We went on a few dates which were fun and usually ended with some making out which didn't bother me but after a while of this happening I really just wanted to fuck him.

So on our next date I made sure to shave the day of, make my makeup look very nice, and put on some sexy matching panties and something nice on top. It was a dinner date at his house and his parents were gone for the night so I was pretty hopeful I would get some. He made some pasta which was surprisingly good but the whole time I couldn't stop thinking about what I wanted to happen that night. It didn't really help that he was complimenting me the whole night which really made me want to go at it even more.

Flash forward to after dinner, we put the dishes in the sink and head to te TV room and lay down on the couch. We make out a little bit and occasionally look at the whatever we were watching on TV. Eventually he asks if I want to go to his room and, thinking I knew what was up, immediately said yes. So we head upstairs and lay on his bed for a bit kissing until slowly we start stripping eachother, first his shirt, then his pants, then his underwear. It was a little odd to me because usually I was nude before the guy but I figured it was whatever. So I stripped down just to my panties which he immediately pulled off. He started making his way down my body kissing my neck, then my tits, stopping to suck my nipples, continuing down until he got to my pussy. He skipped over my pussy and started to kiss the inside of my thigh which drove me wild.

Then he started to really eat me out. He focused a lot on my clit, sucking and kissing it while he slowly snuck a finger in. He started to finger as he ate me out and within about two minutes I was on the edge of cumming. He didn't stop and continued through my orgasm even with me squirting into his mouth and on his face. My face turned red and I apologized but he said it was hot and that I tasted amazing. Hearing this got me more excited so I got up and kissed, him tasting myself on his tongue.

I made my way down to his cock to return the favor but right before I did he stopped me. He then said he had a question for me so I told him to go ahead. He asked if he I had ever been more dominant with a guy which I honestly hadn't but I said I wanted to try it. He seemed really excited and then asked if I'd like to try it now but a bit more hardcore. I wasn't sure what he meant but I said sure interested in what he meant. He then stood up and went into his closet returning with a seven inch strap on dildo. I was honestly not expecting it at all and was a bit hesitant at first. He then said how he knew it was a strange kink but how he was genuinely into it and that it would mean a lot for me to just try it with him.

Seeing as he seemed to really be into it and that I had never done anything like it I figured why the hell not. So I took it from him and after a minute or two of fumbling around, managed to put it on. I got used to the idea of having a cock for a second and it was honestly pretty hot. I looked at him and saw the huge grin on his face and decided to take charge.

On my knees on his bed, I shuffled over to his face, grabbed the back of his head, and forced him onto my cock. He moaned as his saliva coated the dildo and I pulled out a little bit. I began to slowly fuck his face and more saliva began to accumulate, gradually speeding up until drool was dripping from his mouth and he seemed ready. I put him into his hands and knees and looked at his ass. I had never done anything with a guys ass but he was shaved and it actually looked pretty nice. I buried my face in between his cheeks and began to run my tongue all over his ass as he moaned. After a little bit of this, I worked in a finger and started to slowly pump with that too to get him a little warmed up for my new cock. I started to get really into it and as I picked him, I began to jerk off my dick like it was real. After a while and another finger he seemed ready so I pulled back. My cock was a little dry so I got him to lube it up again and got ready to enter him.

I got up, pressed the tip to his ass, and with him on his hands and knees, slowly pushed in. I heard him moan as I sunk deeper into him until I was practically at the base. He didn't seem like he was ready to take the whole thing quite yet so I just started slow and shallow and gradually made my way deeper and started to speed up a little. I heard him moaning and started to get even more into it, giving his ass a firm slap.

After a little more fucking I pulled out and flipped him onto his back spreading his legs in missionary. I again slowly entered him and this time saw the hot look on his face as he took my cock. I locked eyes as began to speed up a little bit and then noticed his cock. I looked down, and drooled down onto his cock and balls. I spread it around with my hand so he was fully coated and then began to slowly jerk him as I ducked. I'll admit it was actually fairly difficult to multi task like tha let but I managed still and sped up. At this point I was practically pounding his ass and I could see the look of ecstasy on his face.

I spat again onto his cock as I pounded and continued spread it around jerking him more. He moaned and said he was about to cum so I sped up both fucking him and jerking him until he started to shoot cum onto his stomach and chest. He sprayed a good 5-6 ropes of thick cum and payed back with a smile. I continued fucking him for a second and paused inside him once he had finished. I slowly pulled out and took the dildo off before laying down on top of him.

He kissed for a bit before I got up sucked his cock clean and squeezed the last couple of drops onto my tongue before swallowing. Then I wiped the cum off my stomach and did the same before licking up the length of his stomach and chest. I swallowed and layed down next to him to cuddle for a bit. After a little I joked that next time it needed to be him inside my ass which he agreed to before falling asleep.

Hopefully you guys enjoyed the story and I'd love to hear any feedback in the comments. I know it isn't everyone's biggest kink but I figured the population of guys into it would enjoy it.

Source: reddit.com/r/gonewildstories/comments/3ysk33/my_first_experience_pegging_fm

20 comments

  1. it’s refreshing to see a totally different type of story on here for a change. I secretly would want to try this once to see what it’s like the other way around but that’s not gonna happen. Lol Thanks for sharing.

  2. I very much want to do this!! I am actually super submissive, but this is my #1 fantasy. I just can’t find a partner to fulfill it with me!!

  3. I was already planning to peg my boyfriend for the first time during a stay action we have planned for the next few days, and reading your story just made it extra super exciting. The thought of entering him and spitting down onto his cock then jerking and fucking him to completion is so hot, and I didn’t have that visual to aim for until I read this story. Thank you.

  4. Not something I want to do myself but I completely loved this story. Did he ever return the favor ;) ;)

  5. Fantastic story. Well done, very hot. Definitely something I’ve always been curious about.

  6. that was super hot. I remember the first time I got pegged. so much fun, but reading this reminds me that it’s been way too long

  7. No problem. Sadly he went on vacation before we could do it again and when he came back he had to go straight to college orientation so sadly we never got to do it again.

  8. Thanks. I’ll definitely try to get more stories out, I’m just not sure what everyone wants to hear.

  9. With how good the last one was to read you can only get better.. Bounce some ideas around and see what people like. Me personally… I’m down for whatever

  10. Thanks! From what I’ve heard from guys, even smaller anal penetration feels pretty nice.

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