Author: henrymillers

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. Read more »

[F]ucking [M]y housemate after years of living together

This happened a few years ago (obviously pre-covid), between me (M31) and my roommate (F31). At the time, I lived in a big house with lots of people — the city I lived in is expensive, so it’s not unusual to live together with many housemates, even in your thirties and forties. In this particular house, many roommates had come and gone over the years but Georgia and I had been housemates for a solid 2 years or so. Our shared house was in an urban area of an east coast city with fairly high crime, and inconvenient to public transit — but the rent was cheap, and Georgia and I were both from working-class families and couldn’t afford better. At the time I worked an office job, and she was a teacher.

First, about Georgia. She was someone that I’d always thought was relatively cute, but didn’t really know that much about her and what she would be like romantically. And, as a housemate, she was of course off-limits. Anyway, she was short, only 5’0”, and extremely petite — in the 100-pound range or so. She was half-Asian and half-white, and had a complexion befitting that combination. I’m 5’9”, 150 lbs, white, broad shoulders, brown hair that is wavy and usually messy, a cyclist physique (toned lower half, average upper half), big lips, faintly jewish features, dark eyebrows, bright blue eyes, 5-o-clock shadow. Read more »