Two Girls (24 & 25), Basically One Phone [MFF]

This is not a story where anything absolutely crazy takes place. It is more of a life-anecdote that I still find somehow amusing (and sexy) to think about.

I was a twenty-six year old living in New York. I had a girl I was dating (24) who lived in the East Village, plus a girl on the side (25) for the first half of our relationship. I did break things off with the latter girl once the relationship with my girl I was dating got a little more serious. Then she abruptly broke things off with me (wa-wa-waaaa). But that’s a different, more rom-com-ish story than this one.This is a memory of a particular 18 or so hours during the time when I was seeing them both.

I was at Jenny (girlfriend’s) apartment that day. We’re having sex. Her roommate, who had complained about the noise we made, was out, so it was back to loud sex. We were sideways on her bed. I was on top. I don’t know about you, but I can sometimes get a little tired of looking in my partner’s face the entire time. Jenny was closing her eyes at this point.

I [29m] Juggle Two Women [27,39] in Two Weekends [MFF]

This will be kind of long, but worth it, I think. I’ll still try to keep it sexy W

hen I was 29 and in grad school, I was starting to act like a big manwhore. At one point in the spring of my second year I was sleeping with two women concurrently. One I met online. We’ll call her L (27). We had a phone conversation before our first date where she asked me what I was looking for. Because I was not above telling women what they wanted to hear to get in their pants, I said a relationship.

We went on a lunch date. She asked me if I wanted to come hang out at her apartment at the end of lunch. I pretended to demur, said it felt a little soon – though in reality, I had a condom in my pocket. She apologized and said she understood. I “reconsidered” and said I guess I had some time. So we walked back to her studio apartment in a nice section of the city. She was always home, worked as a marketing associate for a bra retailer – I swear I’m not making that detail up.

Two Girlfriends in Two Weekends – LAUREN [MFF]

I was in my late 20s when this happened, and lived (still live) in Chicago. I was in grad school for filmmaking. I should note that I was a rather arrogant and self-centered person at this time, and I engineered these qualities in a way that I felt attracted women. To a degree, I was correct. I did get laid often enough. But I was also quite lonely. Also drank too much. So yeah, there I was.

The first woman was Lauren. She was a 27 year-old African-American woman who had just moved to Chicago and worked from home as a marketing associate for a bra retailer. I swear I am NOT making that detail up. She and I met on OkCupid, exchanged a handful of messages, and talked by phone soon after. She asked me what I was looking for and I sensed she wanted to hear that I wanted a relationship, so that’s what I said.

Three Journal Entries from my Sex Life [MFF]

*Below I am including three entries from the journals I’ve kept over the years. In these journals I’ve been pretty uninhibited about my sexual conquests. Names, however, have been changed.*

*In this first entry I’m 20 years old, working at a summer camp for families, and have recently fallen into a relationship with one of the girls who works there. I’m also, apparently, reminiscing about my college ex-girlfriend:*

July 21st, 2007

Of the two girls I’ve slept with, it’s different.

Katie was more of an aggressive nymphomaniac with a mostly shaved pussy, who liked to fuck sometimes at night, sometimes in the morning. She liked to be on top, as if she had a sort of domain over me, bobbing up and down at a furious pace at times, or, if I was on top, letting me go hard and fast, and if I slowed up, she urged me to hurry up by putting her hands on my ass and driving me back and forth. We never kissed while doing it, and she always moaned loudly or let out this high-pitched, fluttering coo, making me think she was cumming over and over (that only actually happened once). I never used a condom because she took birth control. My most vivid memory is of me being on top, staring down at her head cocked to the side, as she smiled while half-cooing, half-hyperventilating, her arm sprawled to the side.

I (28m) bang a nurse (35f) on my buddy’s couch, heal her leg [MF]

*Long post – only read if you have time for the whole thing.*

In the summer of 2015, I was 28 years old and halfway through grad school. The summer had been dull and mostly lonely. I wanted something exciting to happen, and with a friend. I hadn’t seen my friend Ben in almost two years. We’d gone to college together and lived in New York for a bit. Now I lived in Chicago and he was in San Francisco. I made a trip out there at the end of the summer, a final hurrah.

Ben, I soon found, still acted like a manchild. He ditched me on that first night to go to a work event that I couldn’t come to because they only had so many tickets, came home very late and completely trashed – with a random hammer in his pocket. I went to sleep on his couch. I slept through him going to the E.R the next morning because he’d hurt his leg.I gave him a very hard time about this first night. And I thought to myself, jeez, he’s going to be like this the whole visit isn’t he? I also thought to myself – So then, we’re in shitshow shenanigans mode again? No problem, I’ll come up with something!

One Night stand with a Nurse (35) on my (28m) Buddy’s couch [MF]

This happened five years ago. I (28m) was visiting one of my best friends in San Francisco late in the summer, before grad school started back up for me. It was a lot of fun and a beautiful city, but as I remember, my friend was kind of a shitshow at the time. He got very drunk the first night at an after-work thing and didn’t get home until very late, somehow with a hammer in his pocket. I gave him a REALLY hard time for that. He also boasted about all the girls he had met via various dating apps (Tinder, CoffeeMeetBagel, etc) and how many he was fucking.

I myself was sort of at the beginning of my manwhore phase right around that time, and so when we were at a bar one night and I noticed this one woman glancing at me multiple times, with some encouragement from my friend, I went up and talked to her. She was short, with curly black hair, a sort of disfigured nose (this I remember–it wasn’t totally repulsive or scary, just maybe a birth defect or something) and an otherwise sweet face/demeanor. Her name was Rachel. She was talking with another girl, whom I also spoke to a bit, but one of my jokes offended her and so it was Rachel who I decided to keep pursuing. She was a nurse from Wisconsin, had lived in San Fran for a few years, had recently broken her leg in a skiing accident and I could see that it was in a cast (this last bit of info is important by the way).

Confessions of a promiscuous College Freshman (str8) (MF)

I’ve gone through promiscuous phases throughout my life. Sometimes it’s made me wonder if I’m a binge-sexer, in the same way some alcoholics are binge-drinkers. Anyway, during my first promiscuous period, I didn’t have the capacity to consider that my behavior was risky and even borderline predatory. I was just into photography, music, pot and getting as much sex as humanly possible. And I had a certain fearlessness that made that end up being quite a lot of sex.

This is about how I broke up with my 22 year-old girlfriend, Kat, in the spring of that year. Kat and I had been dating since shortly before winter break. She seemed out of my league at first but it turned out she wasn’t. I lied to her about my age and we hooked up the first night we met. We made out and I fingered her in her car. Later she found out I was just a freshman and decided to stay with me. She was a sort of former goth chick, dyed black hair, pale skin, tall, wore a lot of dark clothes. She was a criminal justice major. Would late be diagnosed as bi-polar.