1

"My boss’s daughter (boss was a pub manager) My boss used to give me cash on a Friday night to ‘look after her’ so she could have a couple of drinks and a dance and be safe… He never knew he was paying me to take her knickers off in a nightclub toilet."

2

"Professor at my college and his wife."

3

"I have 3…they were all sisters. And they knew I fucked each one of them. They didn’t care."

4

"A woman who was married to a former Special Forces member of the SWAT team."

5

"A girl from a very conservative family. She had ultra strict parents and it seemed like it was impossible for us to hook up. She had all the features of a girl I would kill for, skinny silky body, long hair and an extremely feminine and delicate energy.

It took me about a year of trying until I finally took her back to my apartment and fucked her her brains out. I felt like an absolute dirty animal afterwards…but it was was really good sex."

6

"Married ex girlfriend. She cheated on me and left me for her current husband. Fucked her a year ago as lockdowns were lifting. 10/10 best revenge fuck."

7

"I had a high school friend who I had a crush on but never acted on it. About 14 years later we saw each other at a mutual friend’s wedding and had sex in the parking lot. If our conservative, old school, friend ever found out, she would never talk to either of us again."

8

"Secretary’s aunt. Total nymphomaniac!"

9

"Best friend’s sister."

10

"I was sleeping with a married woman for like 6 months when I was 20. However, she told me they were separated. I thought she called me at odd hours because of her kids, turns out her man was a truck driver and kept super odd hours. I can’t tell you how many times i fucked that poor man’s wife in their bed."

11

"A girl that I was into when I was in high school. Met her later in life. She was unhappily married and I was in a shitty relationship. It wasn’t right but it felt good at the time."

12

"Two different married women. The first was the same age as me (22-23 at the time) and the second was twice my age. First one I didn’t even know was married and we met several times during one winter.

The second one invited me to a threesome with her and her husband but in the last minute he cancelled but he said it was ok that she and I met alone. I never bothered checking if he actually agreed to it, I don’t even know if he actually agreed to a threesome in the first place. I don’t even know if I ever spoke to him at all, all communication was through text before I met her."

13

"Mom’s married friend, who was also the mother of one of my brother’s good friends. I didn’t have sex with her though, she gave me head."

14

"Former high school crush whose S/O was in jail at the time. She was fun."

15

"An old high school crush. She was in a relationship at the time and we had hooked up before, but one night she and I finally did the deed.

Another time, a college ex and I “reconciled” the semester before she went to study abroad. She was about to be engaged after graduation. Seven years later, she’s getting a divorce and I’m in a relationship."

16

"I had sex with 3 generations of the same family. Not at the same time obviously but spread out over several years. I’ve worked at the same employer since I was a teenager. My boss was the owner’s wife. We had a few weeks long fling that was absolute heaven and sadly short lived. That was grandma.

Her daughter, who was my age, was next. We dated for like 3 years. That was mother.

And later on, her daughter who was 19ish managed to seduce me. That was daughter.

Daughter has since moved away. Mother still works there and we’re friendly and our past is forgotten. Grandma comes in maybe twice a year and always gives me a wink. It’s weird getting this feeling from a woman in her 70’s but it still gives me tingles."

17

"A lady that was getting married in a couple weeks. I didn’t know she was engaged until after."

18

"Guy from work who had a girlfriend at the time. Crashed at his place after a work night out, both drunk. I couldn’t sleep on his couch so we shared his bed…and fucked. Their relationship ended soon after but it was on the rocks to begin with.

Fun Fact: They had a hamster together and they were both so attached to this hamster that they shared custody after they split up – one would drive the whole cage down to the other one’s house every other week. Can’t help but respect that."