[F]rom Germany to [M]anhattan | 2016

This is about a rather brief fling from a few years back. Sorry for my rather dull writing style, I am not a native English speaker, and mostly write technical documentation.

I've lived in Germany at that time, and a friend of mine, Steffen, had friends of his over from the US. We met for brunch on a Sunday, and he hadn't even told me that his friends would join in as well. One of the people joining was Jane. She was here to meet her German boyfriend Jonas at that time. I hadn't met her before, but I knew of her, as she used to be a part of the local hacker scene when she shared a flat with Steffen for a year.

After the okay-ish and rather uneventful brunch, she and some of her friends decided to go to this open-air club next to the river which was open from Friday evening to Monday morning every weekend. If you wanted to get some drinks and listen to minimal techno or whatever was the en vogue style of electronic music at the time on a Sunday at 1pm, this was the place to go. Jane asked me whether I wanted to join, which was kinda unexpected, but since I didn't have any plans for the day, I happily went along. Jonas joined in as well, and even paid for the taxi there. Getting a taxi there, so unusual, the local people all walk. But who am I to complain?

We ordered bottles of Vodka Mate, which is this not very sweet and rather smoky and earthy tasting lemonade, mixed with a shot of vodka. Quite refreshing, doesn't get you too hammered, and it will keep you awake due to an abundance in caffeine. We sat down and chatted, and after about an hour, her boyfriend and the other guy in the group decided to leave and have a nap at home. So it was just me, Jane, and another girl. When the guys had left, they suddenly started opening up more, and we had a great time. We chatted away for hours and hours, until it was almost dark. What I didn't know until then was that the two had taken LSD in the morning, so I, without knowledge, had become their tripsitter for the day.

We eventually decided to move on to a karaoke bar, as Jane was a karaoke afficionado. We got some drinks, and with enough courage, selected some songs to sing and went on the stage. It was quite hilarious, as I had never been doing karaoke before. We eventually sat down to listen to others, when Jane very suddenly started attacking my face with her tongue. Not trying to kiss me, but pretty much trying to shove her tongue down my throat. That was unexpected, but I happily joined in, and a wild make-out session began. We eventually broke, when she got a call from Jonas asking where she was as he wanted to join in. That left me confused, and I was about to leave, but she gave me to understand that he knew that she was going to have fun today, but only he could fuck her tonight. We made out some more, until we met up with her boyfriend and his friends. I had to go home, as it was 1 in the morning, and I had to go to work the next day.

About a month later, I met Jane again at a hacker camp. She was there with Jonas, and nothing happened as I was with another woman at that time (that's a story for another time). I did talk to Jane, though, and I mentioned to her that I was going to visit a schoolfriend of mine in New York after the camp. I had totally forgotten that she was living in New York, as well, so she suggested to meet up one night.

In New York, after I had recovered a bit from the long flight, I texted her, and she suggested to go for karaoke. Of course. Geraldo, my friend with whom I stayed, was cool with it, and so we decided to meet at this karaoke bar in Manhattan. Jane brought a friend, a rather scruffy-looking man, probably 20 years older than either of us. She introduced him as a successful owner of a comic book store. We got this private booth, ordered some drinks package, and started singing away. Rather unexpectedly, my friend Geraldo told me that another schoolfriend of us, who worked in Ohio at that time, had actually driven all the way to New York to surprise us. He eventually joined us, and it was a fun reunion, but soon, the alcohol took over, and I showed more interest in Jane. She smiled at me, took my hand, and we started to make out. What I hadn't told you yet: she was not a traditionally attractive woman. She was not overweight in any sense, but had a bit of a weird build, and a face with some unusual features. But what she lacked in looks, she more than made up for with her wits, her cleverness and the sexual energy that she was spreading.

We eventually lost interest in the karaoke, and she invited me to stay at her place. We parted ways with my friends, who teased me for going with her, and took a cab to her place. There, we immediately went to her bedroom. We just wanted each other, and I wanted to go down on her. But she refused, saying she wanted to get fingered. Hard. I happily obliged. With my index finger, I explored her pussy lips. She was absolutely soaking. I pushed it in, which was met with an audible gasp, and went on to find her g-spot. It didn't take me long to find it, and it felt very distinct, so I started working it. Jane immediately starting moaning and shivering all over her body, so I decided to put in a second finger, which made her moaning louder. After I don't know how long, she asked me to stop. I asked whether I had done something wrong, but she said no, she was just exhausted and couldn't remember how often she had cum.

It was now my turn. Jane started to take my fully erect dick in her mouth. The drinks from earlier inhibited things a bit, so even though I was super horny, I had no fear I'd blow too early. After a few minutes, Jane suddenly gets up, and pulls me sideways on her bed. I wonder what she was up to, when I suddenly felt one of her fingers up my ass. It was just amazing. I had always had a bit of a kink for assplay on me, but it's the kind of thing barely any woman is willing to do, and Jane initiated it without me even saying anything. She touched my prostate, and I felt like I was in heaven. Until she started rimming my asshole and licking my perineum. Absolute bliss. She then started to stroke my dick, while putting even more pressure on my prostate. It didn't take me long to cum, with probably the most intense orgasm in my life. I must have been shaking for a minute or two, and I only regained full consciousness when Jane had already cleaned up all the cum I had shot all over her and me.

We very quickly fell asleep, and the next morning, I woke up with a proper hangover, the one where your head feels like it's going to burst, and where you're completely unable to think straight. Luckily, I had some water next to the bed, and rehydrated. Normally, in such a state, I'd twist one out to feel better, but since I wasn't alone, and Jane had already woken up and had started kissing me, we had a quicky, missionary, standard penis in vagina fucking that wasn't noteworthy but definitely took off the edge. Jane and I then went for breakfast, and parted ways, with plans to meet up another day.

A few days later, she texted me whether we wanted to go for drinks. Her, my friend Geraldo, me, and a friend of Jane's went to a speak-easy bar hidden on the second floor of a Japanese restaurant in the East Village. The cocktails were great, but the conversation was boring, and it didn't get better in the Sake bar we went to afterwards. So Jane and I took a cab back to her place. Less inebriated than last time, we were more coherent in what we did to each other. Since she liked getting fingered last time, I decided to make her cum over and over again. I slowly started with one finger, then with two, then got faster and faster while I added a third and fourth finger. Her moaning became louder and louder, her hips pushed against my fingers, until she started screaming. And she screamed properly. With her prepared, I took the chance and added my thumb so that my whole hand would penetrate her pussy. It didn't take long until her whole body began to shake. I continued fisting her for some time, until her whole-body orgasm subsided and she smiled at me. I pulled out my hand, put on a condom, and immediately pulled her to the edge of the bed. I pushed my hard dick into her, and she moaned, I pulled out again, and pushed it back in, she moaned again, and I continued that a few times until I took her legs, put them over my shoulders, and fucked her as hard and deep as I could. Her moaning got louder and louder, and she asked me to slap her tits and pinch her nipples, which brought her closer to orgasm. It seemed like we were climbing up to an orgasm together, so when we came together, I pulled her towards me as hard as I could, pushing my dick as deep as possible into her. She told me she loved how deep it all felt.

We fell asleep totally exhausted. The next morning, Jane woke me up early because she had to go to work and was horny. She got me hard with just a few strokes, then put on a condom on my dick, straddled me, put me inside her, and kept grinding herself to orgasm. I was too tired to mount her, so I asked her for a handjob. Even though she was in a bit of a rush because of work, she didn't just jerk me off, but took her time. She positioned herself between my legs, spread them, and used a good amount of massage oil to massage my dick, my balls, and my asshole. She then slid a finger up my ass, and started working my dick vigorously with her other hand, all the while she applied pressure on my prostate. I didn't last longer than maybe a minute or two, but it was exactly the right treatment to get started for the day. Jane then cleaned me up, we had a quick shower where I fingered her a bit, but then we really had to go. She got me a coffee from Starbucks, and passionately kissed me good-bye. She had to run for her subway, and I went back home to my friend Geraldo's home.

I never saw her or talked to her again.