So this is actually about the second time we hooked up, but I’ve been thinking about this night a lot lately, especially with bars being closed.
A little about me: I’m 25 now, 5’8″, and about 115 lbs. Everyone likes to describe themselves as athletic but maybe it’d be best to say I was ex-athletic. I ran track and played volleyball in high school but I went to a school more known for academics than sports. Still, even though I wasn’t competing anymore, I genuinely liked fitness. I think like most girls, I’ve had a mixed bag in online dating. Some guys are fun to hang out with, some are really terrible, some just want to have sex but want to lead you on, some are just boring.
This had happened just about a year ago and I was kind of going through a phase where I was more fed up with dating apps than not. I was looking for something more serious but I also wasn’t above swiping right on someone whose primary quality was that they were hot. That’s how I matched with James. He was my age, 6’2″, and while his profile was interesting and it was cool that he was in grad school, honestly what got my attention were his abs. He wasn’t bulky strong, he was actually really lean, but he had a well defined stomach and must have worked out.
Our first date was really flirty, but I really try to not hook up with someone on the first night, so I ended our date before things could progress to a place I’d regret. Our second date, I was absolutely ready and I actually wound sleeping over at his place. Surprisingly, we had great physical chemistry as well. If it wasn’t for corona, I think we’d have seriously dated.
Anyway, James wanted to hang out again over the weekend and recommended a fancy rooftop bar. I was down since I like to dress up and it’s nice to wear heels with someone who will still be taller than me. I won’t mention what city we live in but it gets cold, so I had on a classy little dress but also a big coat since I was taking the train. I didn’t know it at the time but James drove over. We were going to meet downstairs at the main entrance when I saw him pull up and let the valet take his car. It sounds dumb but I was so attracted just watching him get out of his car. I was also seriously cold and he must have realized since he apologized for not offering to pick me up on the way.
Without boring you all with the details, we had a great time at the bar, spent a lot of time talking and getting to know each other, and developing our relationship. That said, by the third round, we also spent a lot of time staring at each other and being a little more flirtatious. When we were walking back to a corner from getting drinks, James let his hand slide down past the small of my back until his fingers were gliding right along the top of my butt. I barely tensed up and he leaned down to tell me about how much he liked how my ass felt. Being a little drunk at this point and bolder than normal, I put my arms around him and whispered in his ear that he could stare at my ass all night.
We spent the next fifteen minutes or so sitting in a corner in that uncomfortable middle ground where the room is full with tension and you’re both waiting for someone to make the next move. His hands were on my hips and I could feel his fingers pressing into my skin. For my part, my hands were in his lap feeling his thighs along his pants. I was extremely turned on and each time I’d shift how I was sitting or recross my legs, I could feel myself getting more and more worked up. Eventually, James stood up, grabbed my wrist, and I followed him. We left the bar but didn’t turn to the elevators. Instead, he went the other way to a stairwell and I followed. I asked him what we were doing since I wasn’t trying to walk down 20+ floors, but we only got down two before he pushed me up hard against a wall and started making out with me.
I was just about ready to melt after like two hours of heavy flirting, so I was very receptive to this. I knew I was moaning a little bit as his hands went down my the front of my dress, along my stomach, until he was cupping me between my legs. I was a little bit shocked but when I opened my eyes a little more to begin to say something, James held me against the wall by my throat and started to rub my pussy so, so slowly.
“Oh, fuck.”
I could feel myself pressing back against the wall while James slid his fingers down the top of my underwear until he was touching my clit. Every part of my body was on fire while this man was just teasing me in this space. Normally, I’d have been a little worried about being caught, but all I could think to do was to take James’ thumb into my mouth and swirl my tongue around it. I could feel him react, and then I felt him slide a finger into my pussy effortlessly. I could hear how wet I was already.
“Fuck, James.”
I opened my legs a little wider as he worked a second finger inside of me. I couldn’t believe how turned on I was. He whispered in my ear that I was dripping wet, and before I knew it, I was tasting my pussy on his fingers. I made sure to stare at him in his eyes while I took his fingers in my mouth, grabbing his wrist and making sure to taste all of me.
He pushed me back up against the wall and was rubbing my clit faster now. I must have been panting because he put his hand over my mouth. I tried to say I was going to cum but it was muffled. He must have felt my legs and stomach tensing up though because he pressed his lips right against my ear.
“Good girl, do it. Fucking do it.”
And with that, ladies and gentlemen, I had my first orgasm ever in a stairwell.
When I was recovering, I was trying to grab onto James to keep balance. But I was also trying to fumble with his pants, to unbutton them, to rub my hand along the outline of cock. James didn’t give me a chance to recover, he pressed me down by my shoulders until I was on my knees and my face with level with his zipper.
I was eager for the chance to get his cock in my mouth. I realize I didn’t say anything before but James had a really nice dick. It was thick, but not painfully so, and long. We had only had sex that one night but every time he thrust inside me, it felt like he was giving me a spinal tap. I’ve had a decent amount of sex in my life but he was the first guy where we had to go slow until I could take all of him. I know that “girl inches” are a thing but he was probably around 8″.
So I was confronting the fact that as I unzipped his pants, this beautiful cock was straining against his underwear. I could see just a little bit of precum poking through and I looked up at him as I rubbed the head of cock. Slowly, I pulled the waistband of his underwear down until his dick was out and I could hold it in both my hands. I licked from the bottom of his cock to the top, moved my tongue around the head, and took a little bit in my mouth before pulling it out.
“Your cock is so big.”
I tried to take more. I had one hand holding him at the bottom of his dick while I tried to move my mouth and lips further down, but it was a struggle with how thick he was. I started moving my lips up and down his cock, letting my spit go down the length of his dick while my hand started working him too. I could hear him moaning, and then I felt his hand between my shoulder blades pulling up the back of my dress exposing my ass in my underwear.
I had never done anything this slutty before, but I knew I wasn’t going to stop. His cock squeezed for a second in my mouth and I thought I was about to make him cum, but he made me stand up and caressed my cheek before kissing me. He told me how great I looked with my lips wrapped around his dick and I told him it was seriously the biggest cock I’ve had but that I loved giving him head.
And then I heard him moan and pull my underwear down my thighs and lift my dress up until it was along my rib cage. I wasn’t sure if he was going to try to fuck me right there against the wall, and honestly even though we didn’t have a condom I probably would have left him, but instead he pressed his cock along my pussy and against my stomach, told me what a perfect slut I was, and came like that along my skin. I could feel him burst along my the underside of my breasts, dripping down the sides of my stomach, and his cock drag down a trail of cum from my bellybutton to my clit.
We caught out breaths, I pulled my underwear up and dress back down, and we made a beeline for the elevator and his car. His cum was still wet along my skin and I was so incredibly turned on. I wound up forgetting my coat at coat check and our cards at the bar, but I didn’t realize until the next morning. The drive back to my place was quick but honestly so tense. He made me push the passenger seat back and play with my pussy while he half watched as he drove through downtown.
We hooked up a few more times and it was no lie probably the best sex of my life, but he had to move back home due to corona so our fun ended in March after a couple of months of intense bursts sex.
Anyway, I hope people enjoyed. I’ve been thinking a lot about some of my experiences with James as I’ve been cooped up during quar so it just came to mind this morning.
Source: reddit.com/r/gonewildstories/comments/l7rfyr/the_first_and_only_time_i_hooked_up_in_a