Cumming inside her on the first date [MF]

One of my biggest fantasies is cumming inside someone on the first date. I’ve certainly had sex on the first date — probably ten times or so in my life — and I’ve had first dates where the first time we had sex, we had brief moments of doing it raw, or I pulled out. But in all my dates I think I’ve only had one date where I actually met someone that night and came inside them later. This is that story.

I met Kaitlyn on tinder, which is rare for me, because I don’t particularly like the site. It tilts towards the shallow, and I’ve always felt I am at my best when people can engage with me for conversation. I work in media and am active in political organizing, and I prefer to have more engaging conversations and get to know people, as I feel more attracted to personalities than looks generally. Obviously, that’s not what Tinder is for.

Fortunately, Kaitlyn was one of the few who was on the same page as me. She was a brunette who’d streaked her shoulder-length hair with blonde. In her photos she had a gummy smile, bright white teeth, a fit but curvy figure, and well-plucked eyebrows. But what entranced me most was her politics — she identified as a socialist. That was what I wanted to talk about, and what I am into, more than looks.

And to set the scene — I’m 5’8”, and have a cyclist’s body — toned legs and a pretty average, slim-ish upper body. We were both 32. I have brown hair going prematurely gray, brown eyes, a young-looking face and a close-cropped beard just beyond a hint of 5 o’clock shadow.

In texts, we built up a rapport about politics, work and music. She worked in media, too, so it seemed already that we had a bit in common. I asked her out on a Friday date and she seemed amenable. We switched to texting and proposed to go out downtown.

We met up at a beer bar that turned out to be absolutely swarmed, standing room only, so we went down the street to smaller, two-story casual bar. We ordered a couple beers and chatted. The conversation was easy and fun with Kaitlyn — I was leading the way, I felt, but she was open to talking about anything. She seemed very eager. I noticed when I hugged her at the beginning of the date that she was an inch or two taller than me, which concerned me — generally I assume taller women are disinterested. But Kaitlyn seemed amenable and very interested for the whole date. She was wearing a skintight pair of denim jeans that hugged her round, protruding ass, a t-shirt that showed a hint of cleavage, and a professional-looking jacket. She looked as though she cared about fashion just as much as me, which is to say, enough to pay attention but not enough to obsess.

In person, Kaitlyn looked slightly different than in her photos — whereas in her photos she was very smily, in real life she had a slight melancholic tinge to her. I could tell that she was not completely happy with her life, and she expressed dismay at her job; she was embarrassed about having a business degree. She was more overtly political in real life, and a musician, too, and I think missed that side of herself. I got the sense that she had compromised in her life a bit.

If I am being honest I feel attracted to the melancholic side of people; I think anyone who is completely satisfied is deluding themselves. I liked that she seemed slightly sad, deep down, and I liked that when she was with me she seemed happy — or rather, we seemed to delight in each other’s company. She was very game to drink with me, and after a few beers we proposed getting “real” food. We walked to a busy order-at-the-counter, fast-casual Indian place. After ordering and sitting down with our food, the date seemed to be going well enough that I thought it would be okay to check with my insecurities. “I noticed you wrote your height in your profile,” I said. (She was 5’10”). “I find that sometimes people do that because they don’t want to date people shorter than them, and sometimes they do it because they just want people to know in case they’re insecure about it. So I wanted to check which it was with you, because I am shorter than you,” I said.

She laughed. “Oh, it’s the latter,” she said. “I have no problem dating people shorter than me,” she added, flashing a smile.

I squeezed her hand. “Okay, good,” I said, “Well, I don’t mind dating people taller than me, either.”

We looked at each other’s eyes. I had a feeling we were going to go home together.

From the indian place we went to a big outdoors bar, where the conversation turned to music. By the end of the night, we were comparing notes on favorite albums, and talking about why the 1990s music we grew up with was so bad in retrospect. I drank way more than I usually drink — about six drinks by the end of the night, maybe more — and wasn’t feeling great. When the bar closed, we walked to the subway together. On the platform, we started making out. There were only a few trains left, and it was that quiet time of night where the platform is sparse.

“So,” I said, holding her hand, “Which way are you headed?”

“I’m taking this train north,” she said. It was the opposite of the direction I’d go to go home. “Are you coming?”

“Sure,” I said. We must have looked disgusting; we were just making out on the platform for about ten minutes before the train arrived. Kaitlyn had soft lips and a gentle touch, and moaned slightly when I would run my hands through her hair or tuck her hair behind her ear, or gently move my fingers down her earlobe to the nape of her neck. On the train to her place, I ran my hand on the seam of her jeans. We were drunk enough at this point that we didn’t completely need to talk.

When we got to her apartment, she showed me around. She had an upright piano and a stack of Jacobins on the dining room table. We talked about the most recent issue, and I fiddled on the piano for a few minutes before she joined me on the seat and we started kissing again. She pulled her shirt off quickly. She seemed to be letting me take the lead, but everything I proposed she was enthusiastic about. “Should we go to your room?” I asked.

“Yes, let’s,” she said. In her room, we made out and removed our clothes until we were laying there, naked, rolling around. She had soft skin and I could feel her goosebumps on her body. I really enjoy eating pussy — it’s an intimate and fun way to get to know someone — so I went down on her and gently licked her. She had a small labia, a very wet and neutral-tasting pussy that was shaved bare save a triangle on her pubes. As she got more into my motions, I put a finger inside her pussy as I licked her clit, which sent her up a bit. She writhed and wiggled and gasped. I actually couldn’t tell if she had come, so I asked, and she affirmed that she had, then pulled me up. Now, I was on top of her, making out, and my cock was perched just outside of her pussy lips, rubbing gently on them. I was going to ask, “do you have a condom?” But I wanted to wait — just to see what would happen.

Before I could do anything else, Kaitlyn just grabbed my cock and rubbed it on her entrance, then slid it in. I couldn’t believe it — here I was fucking her raw, when I’d only met her five hours earlier. There was something so thrilling about this. She lifted her legs way up over my head, and in the dark I had a beautiful view of her wet open pussy, her thick thighs raised at her side. She made guttural squeals and screeches now, sudden gasps of sounds as if she were surprised — “ah!” — “oh—OH!” — as though her pleasure came in short, eruptive bursts. She screamed as she came, and a few seconds later I couldn’t hold it, either. But since I hadn’t discussed it before, I pulled out at the last second and came all over her stomach.

She went to the bathroom to clean up, and came back. There was something sort of hot about how Kaitlyn talked around sex — like it was taboo. I’d just been tested, and I was guessing she had too, but she didn’t bring it up. (Later, after a few more dates, she confirmed that she had).

We cuddled for a bit, and I was so turned on I got hard again. This time, she rolled on top of me, and then started riding me. She had sizable breasts, perhaps D or E cups, and wider aereolas that rose and knotted when her nipples got hard. I squeezed and played with her tits as she ride me, enjoying hearing her whimpering — she was remarkably wet, and I could feel her pussy juice dripping down my shaft and all over my balls, which became cool from the evaporation. I put two hands on her tits and cupped them; it was all too much, her whimpering, the hotness of fucking her raw again; i moved my hands to her hipbones, so I could guide her ass and torso back and forth. “I’m going to cum, oh fuck, oh fuck,” I yelled, so that she would have time to jump off.

I assumed she would hop off, but she didn’t — in fact, she pushed down deeper, and started grinding. I was in disbelief as I started to cum, shooting shot after shot deep in this stranger’s pussy. As I came, I took my hands off her — to let her lead, to see what she would do — and her answer was to grind harder, to massage my cock with her kegels, to encourage me to cum deep inside her.

I kept seeing Kaitlyn for a few more months after that, but in the end, I moved away and it just didn’t work out. But, to this day, she marks the shortest amount of time that I have gone from meeting someone to cumming inside of them.

And yes, a few weeks later, we did have the conversation about sexual health, and she was on birth control and had gotten tested recently, too :) (PSA: Kids, don’t do what I did! Have the conversation about BC and STIs before you have sex.)

Source: reddit.com/r/gonewildstories/comments/jzsmmq/cumming_inside_her_on_the_first_date_mf