I [m27] was pegged for the first time last weekend by an old college friend [f29] and it ended up being the most fun and positive sexual experience of my life

So a few months ago, I moved to a new city. I barely knew anyone in this foreign place and, of those few who I did know, I definitely wasn’t close enough to any of them to reach out to grab a drink or something. So the only real option was to download Tinder and settle into a quiet routine.

Fast forward to just a couple weeks ago, I was watching TV and swiping away and I came across a familiar face. She was some friend of a friend of a friend I recognized from college but never really ever talked to. Let’s call her Sarah. We weren’t even facebook friends, so bypassing Tinder, I sent her a friend request and reached out on facebook. As luck would have it, she had also recently moved to the area and was in the same boat me, eager to have a friend! We agreed to meet up for a drink after work one day and quickly became friends!

After that, Sarah and I started to hang out after work more often. She’s cute, with strong eastern european features and a big, bright smile. She spends a lot of time at the gym so her obvious muscles, added to her tall frame and sizeable chest, made her stand out. But the most unforgettable piece of all was her wild, bright, fire-orange hair, always tied neatly in a tight pony tail over her usual business casual button down and skirt. Even without makeup, she was cute!

Up until this point, Sarah and I had only really spent short amounts of time together after work at a quiet bar that was in a convenient location. This past week, however, we were at our usual spot, having a few beers and chatting about the weekend, and she asked if I wanted to go out to a few clubs with her and a friend. This was exactly what I had been missing both with moving to the new city and the pandemic so of course I agreed: Friday night, meet at her place to pregame.

The rest of the week dragged on until finally it was Friday night, she texted me her address and I Ubered over to her apartment. To be honest, I was a little nervous. This was the first time I was going to see her not in a sterile business casual setting, plus drinking with someone I had never even met. But as I walked up to her door and knocked, nothing could have prepared me for what waited on the other side.

To preface this, I need to make something clear. Living by myself and working from home without a ton of distractions, I had started watching a lot of porn. Like… a LOT of porn. I’m talking jerking off three… four… sometimes five times a day, and my preferences had gone from cute, little, doe-eyed princesses to dark, dominating, alt-punk girls.

So when the door swung open and there there stood Sarah in high heels, ripped fish nets, a tight black denim skirt, and a black button down tied tightly in front exposing her massive cleavage, barely held together by a thin lace bra, my heart nearly stopped. She just stood there, staring at me with her big brown eyes, just caked in black liner and green eye shadow that matched her exposed, neon green belly button ring. I looked her up and down, taking in everything from her half sleeves of brightly colored tattoos on each arm all the way to her fire red hair, pulled tightly into two top buns. She was such a sight to behold!

I must have been a little too taken aback because she giggled through her bright red lips and said “a little different from work clothes huh?” to which I could only reply, “yeah, I definitely wasn’t expecting that.”

The night got kicked off without a hitch! Her friend was already there, dressed only slightly more conservatively, so we got right to the shots and pregaming! After a short while, we called an Uber and headed downtown to the club area. The plan was to start at one end of the street and just work our way down. We drank and took shots and danced the night away! The more we drank, the more we danced and soon, the girls were taking turns grinding on me. It was all fun and games but I think Sarah knew she had me wrapped around her finger. She would rub her ass against my crotch and even kissed me on the cheek a few times.

Around midnight, the friend (whose name I think was Val?) announced that she was exhausted and wanted to call it a night but said that we should continue to stay out and party! She said goodnight and left so it was just down to me and Sarah. We made it to one or two more places before settling down a bar.

“So what did you think of Val?” Sarah asked once we were sitting down. “I think she had a little crush on you.”

“She’s not really my type,” I said. “I prefer a girl who takes charge and knows what she wants. Someone who can dominate me a little and…” pausing to take an overdramatic look at her long crossed legs, ” someone who can pull off fishnets.”

She laughed and shifted closer to me. “What are you suggesting?” she asked, looking straight at me with her big brown eyes, as if she was reading me.

“I’m just saying, after a long day, I really like a girl who can, I don’t know, put me in my place.”

She took a long, dramatic pause and shifted even closer so our faces were almost touching and whispered, “I’ll put you in your place. I’ll make you gag and choke, I’ll tie you up, and if I want to, I’ll even fuck that tight little ass hole. Starting right now, you’re mine.” I felt her run her hand up my leg to my crotch and grab my throbbing hard cock through my jeans. “Yeah I thought you’d like that.”

At the speed of light, we called an uber and closed our tab and made our way back toward her apartment. For the entire ride, our faces were not more than an inch apart. I tried to kiss her so many times but she just kept her hand firmly on my neck, teasing me with her bright red lips. She even flicked her tongue up and down my lips a few times which drove me crazy.

We finally got dropped off and made our way up the stairs to her apartment door. As she fished out her key, I took advantage of the moment and wrapped my arms around her, one hand on her bare flat belly, the other straight to her massive tits. She gasped loudly and dropped her key and pushed back into me. My hand moved from her stomach to her fire red hair as I pulled it back and finally planted a firm wet kiss on her big red lips. She turned to face me and kissed me one more time before forcibly separating and said “youre going to pay for that. Pick up the key.”

I complied and in a flash, we were inside the apartment, lips locked as we made our way to the bedroom, clothes flying all over the couch and the kitchen as we went. By the time we made it to the bed, all I had left were my jeans which were around my ankles and boxer briefs which were strained to their limit trying to hold back my rock hard cock. She pushed me onto the bed and I was able to get a good look at what she still had on. She had somehow pulled her skirt off over her heals and had lost her shirt so she just stood there in fishnets and a matching lace bra and panties.

Sarah climbed on top of me, pushing me all the way back and straddled my face, shoving my nose into her lacy panties. I could barely breathe as she rode my face. I managed to pull her panties aside and stuck out my tongue so I could taste her shaved, pink cunt. I was so hard it was starting to hurt so I pulled out my cock and started to stroke it as she rode my face.

“Did I say you could jerk off to me?” she scolded as she jumped off my face and gave me a few light slaps. She leaned in for what I thought was going to be a kiss but instead she said, “open your mouth” and spat a massive load right in. Fuck that was hot.

“Take off your pants” she said. I quickly complied, now completely naked as she pulled off her panties. She climbed back on my face, her pussy soaking wet by this point, and leaned down to suck my cock at the same time. We 69’d for just a minute before she started to moan louder and louder. She sat up, shaking just as she came all over my face. I could feel her grool running down my cheek and I damn near came as well.

She rolled over and licked her cum off my face. Without her having to even say it, I opened my mouth and she spat it straight in. She kissed me one more time, then looked me straight in the eyes and said, “you’re going to fuck me, then I’m going to fuck you.” This was going to be a brand new experience for me, but I was beaming.

She rolled off of me and stuck her ass straight in the air. Wasting no time, I knelt behind her and in one swift move, thrust my 7 inch cock all the way inside of her. She squealed and let of a loud “FUCK” before moaning at full volume, total screamer.

As I fucked her from behind, my hands moved between her neck and her ass. She had the most amazing round ass that was clapping loudly with sweat as I thrust my entire shaft in and out. After a minute, she spun around and threw me back down on my back and mounted my cock, still screaming loudly.

She kept riding at full speed for a long time, skillfully bringing me all the way to the edge and back down. After a while, she slowed and leaned in. Kissing me, she said “dont move.”

I instantly got nervous, not really knowing what was coming next. She hopped off the bed and made her way over to her chest of drawers and pulled out a black leather strap on and a long pink dildo. “I told you if I decided I wanted to fuck that tight little butt of yours, I was going to,” she said firmly as she stepped into the harness.

In that moment, I was so terrified and so excited, I was almost shaking. I think she noticed because she softened slightly and asked “Is this the first time you’ve ever done anything like this?”

“Is it that obvious?” I joked.

“You’re actually the first guy I’ve ever used this on so this is new for both of us!” she said with a wink. She grabbed a towel from another drawer and laid it out on the bed and climbed over me to grab the bottle of lube from the night stand. “I promise I’ll be gentle.”

I laid back and took a breath, hoping I was drunk enough that it wouldn’t actually hurt. That was not a small dildo and I am not exactly what you would call experienced in the backdoor department. She positioned in between my legs and began rubbing her lubed rubber cock along my tight virgin asshole. With one hand, she guided the head in and I felt it pop into place. Slowly, she leaned down on top of me and ran her hand through my hair and kissed me gently.

“How does that feel?”

I forced out a “good baby” as she slowly added a little more length, then a little more, adding a small slow pump each time. Our lips stayed locked in a slow kiss and soon she had most of the length of that dildo, buried in my ass. As she fucked me slowly, she sat us and ran her hand along my body and to my cock.

I was so turned on, watching this sexy, dominatrix fuck my ass hole! My cock was standing at full mast as she grasped it firmly and started jerking it off as she thrusted.

In almost no time, I realized it couldn’t control myself anymore. “I’m cumming baby, fuck” I managed to get out in between the moans. With some practiced skill, she swiftly pulled her cock out of my ass and stepped down to the ground and straight to her knees.

I sat up just in time to rocket a huge, heavy rope of thick spunk right on her face and into her waiting mouth. She gasped at the size of the load and stuck out her tongue to catch some of it. In that moment, my entire body just melted amidst the strongest orgasm I’d had in, well, as long as I could remember! After what seemed like a dozen thick ropes, I squeezed the last few drops into her mouth and watched her swallow it.

I collapsed back down on the bed, almost in shock, and damn near passed out. I was in such euphoria I felt like I was floating.

A few moments later, Sarah walked back in the room. At some point, she had removed her big pink strap on and just stood there, stark naked and beautiful. Her make up was smeared as I’m sure she was trying to wipe off the mountains of cum I shot all over her.

She smiled and, without saying a word, climbed into bed and curled up with me. We cuddled quietly, breathing heavily as our sweaty, naked bodies stayed pressed firmly against each other. As I started to come down from my post orgasm high, I could feel my ass hole winking. What a god damn experience!

We kissed slowly for what seemed like hours and eventually just fell asleep in each other’s arms. It wasn’t until we felt the light of the early morning sun start to peak through the windows that we started to stretch and move around. Neither of us had moved a muscle and we were still completely naked, tangled up in each other.

I think we were still both a little drunk in the morning because neither of us had what should have been the hangover of a lifetime. We drank some coffee, hopped in the shower together, and had sex again in bed (this time without the giant pink dildo) until we fell asleep for a nice mid-morning nap.

I didn’t leave until late afternoon. I kissed her deeply before I left and told her I couldn’t wait to see her again. No idea if this is the start of a new relationship or FWB situation or what but it was by far the most fun and comfortable sexual experience of my life. I’m very excited to share it with you all and I will be sure to update you if anything happens in the future!

If you’re still here with me, you’re a champ. Thanks for reading!

Source: reddit.com/r/sexystories/comments/nxsqhw/i_m27_was_pegged_for_the_first_time_last_weekend