“Stephanie” and I have been FWB for about a year. She’d told me before about fucking her neighbor’s dad when she was in high school, but I never got the full down-and-dirty story until the other night, and holy shit was it hot.
First – everything that happened was consensual. She was very clear about that, and she sorta needed to be, for reasons that will become clear.
Stephanie turned 18 a few weeks into her senior year of HS. She was a dyed-blonde varsity cheerleader then. Really pretty. Had given a couple of blowjobs but that was about it. Wanted to get more experience but hadn’t found the right guy, that sort of thing. “Greg” was their family’s neighbor. He was divorced and split custody of a young kid, who Stephanie would occasionally babysit. He’d known her parents for years.
So one night, she was babysitting and had put his kid down for the night. She was watching TV when he got home from a work thing late that evening. When he did, he got a beer and, for the first time, offered her one. She said… sure. He sat next to her and they chatted and watched TV. She says the beer got her a little tipsy. Then, his arm is around her. They keep kinda chatting, watching TV, and at some point, he slips his hand into her top, over her breast. He starts to feel her breast and stroking her nipple. She says it felt really good, and she didn’t know how to tell him to stop. She says she didn’t know if she really wanted him to stop or not. Then, he kisses her and his other hand is on her crotch, over her shorts. She says she sorta spread her legs, mostly out of shock and surprise (again, she was sorta tipsy), not out of telling him to keep doing it… but he took it as a sign to keep going. Pretty soon, his hand is inside her shorts and rubbing her clit. She says it felt better than anything any guy at school had ever done, and she came really soon.
Then, he just sent her home.
The next night, she was scheduled to watch his kid again. But when she gets there, the kid is gone and it’s just Greg. He sorta pins her against the counter and asks if she liked what he did the night before. She was scared, but also… she did, and she sorta nods. He asks if she’d like to do it again, and she said yeah. So he led her upstairs, took off her clothes, and she let him take her virginity on the bed he used to share with his wife.
After that, she started “babysitting” once or twice a week, and each evening, he would fuck her. After a few weeks, he got her to begin stopping by his house on her way to school in the morning (her parents didn’t realize it, since she usually walked to school). She would usually give him a “blowjob,” though the way she describes it, it sounds more like he just liked to fuck her mouth. She would kneel in the foyer and he’d hold her head and thrust into her mouth and throat until he came. She’d have to reapply her makeup for school after sometimes. Or he would fuck her quickly over the sofa. She said she often had to clean herself in the bathroom when she got to school, because cum would start to drip out of her by the time she got there.
Greg pressured her to go on the pill, and she got her mom to let her, saying it was to even out her cycle. After that, he came inside her almost all the time.
He began fucking her in the ass when she was on her period, and that’s how she started to really love anal. She still does, to this day.
And the thing was, she came almost every single time. She says to this day that he knew exactly how to make her cum, really intensely, and that part of it was that she knew how dirty and taboo it all was. She knew he was a dirty old man and sort of a predator, but she fucking loved it, and he never hurt her or anything. Still, today, she masturbates thinking about that dirty old much older man fucking her when she was still in high school.
Post-script: she went to college and that basically cooled things off. When she was home for holidays, occasionally she’d go and “babysit” for old time’s sake.
Source: reddit.com/r/gonewildstories/comments/hk9os9/my_fuck_buddy_26f_lost_her_virginity_at_18_to_her
That is super hot. I had a very similar experience. I wonder how common it actually is?
That’s not hot, this neighbour is an abusive asshole who assaulted her on multiple occassions, and she only managed to deal with it mentally by turning it into a sexual fetish. I’m on this forum a lot because I’m a horny mofo, but I absolutely draw the line at misunderstanding abuse -and what your fuckbuddy experienced was abuse. She developed kinks because of traumatic experiences, I have done the same thing. To develop a kink for a non-consensual experience that felt like assault is a defence mechanism. You need to be more understanding of this for her, because it doesn’t sound like she is. You might find her sexual openness to be lots of fun, but there is a sinister reason why.
My wife’s best friend ended up in a relationship very similar to that, but he was gentle and loving. Even though she was my wife’s best friend since they were 10, she didn’t tell my wife about it until they were in their 30’s, talking about their 1st time. My wife was shocked that it was Mr Jones that she babysat for.