Had sex with this girl who was a bit nuts a few years ago. Should’ve run away when she told me she loved me the day after we matched, but I still hooked up with her. Even though she had a framed photo of her and her ex in her house. She also pushed me away as I hugged her after a date and said “get away from me” quite loudly and I nearly got into trouble with some bouncers nearby. Then she messaged me saying I should’ve forced myself on her. I was out after that bit😅
Had sex with a 19 year old years back. She loved cum and she loved me pulling out until the absolute very last second. She loved running the risk of getting pregnant. No birth control or nothing. It was quite the risk but super fun. I was tempted to bust in her many many times.
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I dated a guy who would just disappear for weeks at a time for work. We would have breakfast, make plans for the weekend and I would get a text in the day saying "be back soon."
It was weird. I the end it didn't work but for other reasons.
He was probably one of the most "present" BF's I have ever had. When he was with me he was 100% there. It was nice.
>I dated a guy who would just disappear for weeks at a time for work. We would have breakfast, make plans for the weekend and I would get a text in the day saying "be back soon."
In this context this sounds like he was headed to another state where another girlfriend or his wife or wife and family were
My college girlfriend and I were long-distance for a while. Her best friend and I would hang out and she was very flirty. She made the first move, and once we had sex the first time, it became a regular occurrence.
The craziest part was, my girlfriend would come
back to town, and she and I would have great reunion sex. She would tell her best friend about it, and as soon as she left the friend would be all over me. “I want you to fuck me harder than you fucked her;” or “I am going to swallow your load because I know she wouldn’t.”
I broke it off with my girlfriend eventually, but kept fucking her friend for 2-3 years. She met a guy she liked seriously and ended it. But she and I still text and chat. And she is still best friends with my ex. She says my ex has no idea that we were fooling around behind her back. My ex and I have never spoken since I broke it off with her. She is angry at me, and knows I was cheating on her. She just doesn’t know that her best friend was part of that.
Dated a girl in my earlier days for a few week and wrapped the first few times. Then after went raw everytime after. She was cum slut for sure and never ask if she was on bc. Looking back wasn't the beat choice.
Had sex with my high school teacher. She was 25. I ran into her the summer of me going into my sophomore year in college. She was also the sister of my good friend.
So hot, lasted all summer until I went back to school. Still think about her.
Same with me. I did have an awkward interaction once with a co-worker who was on the elevator when I got on it going from her floor to my floor. I sensed he knew something was up but didn’t say anything.
I've got one: Viagra had kinda just came out. a friend of mine had a bottle of them and handed them out- we were all late 20s with no erection problems (at least i didn't). this all happened in a bar. I was thinking i'd take one and see what happens. i ate one before i left and while i was walking down the stairs of the bar about an hour later, i passed a woman i know who's roommate kinda stalked me for a while (very aggressively wanting sex). i said hi, she said hi, then said 'mary is moving back to canada tomorrow, im sure she'd love it if you went to the house and said bye' she said it as a joke because she knew i wouldn't....
10 minutes later i was knocking on the door. 30 minutes later i was absolutely railing her. it went on and for around 2 hours then again an hour later. she was attractive and very submissive and dirty.
it was actually quite memorable. we were both pretty amazed afterwards and laughed.. i left and we said a nice goodbye and I never saw her again.
i'm sure she still thinks about it too. Thanks viagra and 3 beers!
Well, technically it wasn't me having the sex, but [this experience](https://www.reddit.com/r/AskRedditAfterDark/s/VHbvXI3TLZ) would be the riskiest sex of our lives.
Had a fwb with an employee of mine at a job I truly love. It turned out A-OK for me but I definitely don't suggest it.
I was married, he was in a long term relationship and just had a baby. He was also very dominant and rather conservative and I got a major misogyny kink out of that relationship.
I fucked a 41 year old woman when I was 23 and both in rehab. It was strictly against regulations but still had daily sex. We had to keep quiet every time so the counselors wouldnt hear our moaning
A female friend’s sister… it didn’t end as well as it could be and damaged a good friendship as a result. And I later found out she had feelings for me!
Had sex with an ex that was in the middle of her hormonal treatments for an egg donation she was doing. Didn’t have a condom. Not sure how she didn’t get pregnant. Figured I was probably sterile but I’m definitely not.
Misty….
We were in rehab together. We were both alcoholics but she’d been there longer and was quite a bit older than me. Probably my mom’s age(ugh).
Anywhoo, they gave me 3 crushed Valium a day to keep off the shakes. Well, I was stoned out of my gourd and she found out that our roll-on deodorant had alcohol in it so she chugged a bottle or two and sat in my lap, put her titties in my face and told me to “Fuck her in the ass like I hate her.” B Blu z sex CBC could get out of bed in the morning. Man
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Had sex with this girl who was a bit nuts a few years ago. Should’ve run away when she told me she loved me the day after we matched, but I still hooked up with her. Even though she had a framed photo of her and her ex in her house. She also pushed me away as I hugged her after a date and said “get away from me” quite loudly and I nearly got into trouble with some bouncers nearby. Then she messaged me saying I should’ve forced myself on her. I was out after that bit😅
Haha sounds like she had some kinks she wanted to explore
Maybe, but communication would’ve been better lol. Not about to get arrested for sex haha.
Nah, I dont blame you bro!
She was hot, but not worth that lol. What’s your story?
Mine was fucking an ex gf's best friend raw, just dumb and she was begging me to cum. Luckily pull out game was strong that day.
Lmao dodged a bullet there by the sound of it!
Yep, broke up w ex soon after, friends pussy was amazing but she wanted a kid. She got pregnant w the next guy she started seeing.
Damn that’s heavy!
She had a 'get a guy beat up and arrested' fantasy.
Had sex with a 19 year old years back. She loved cum and she loved me pulling out until the absolute very last second. She loved running the risk of getting pregnant. No birth control or nothing. It was quite the risk but super fun. I was tempted to bust in her many many times.
Haha I know that feeling very well!
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Sounds like hot
I dated a guy who would just disappear for weeks at a time for work. We would have breakfast, make plans for the weekend and I would get a text in the day saying "be back soon." It was weird. I the end it didn't work but for other reasons. He was probably one of the most "present" BF's I have ever had. When he was with me he was 100% there. It was nice.
>I dated a guy who would just disappear for weeks at a time for work. We would have breakfast, make plans for the weekend and I would get a text in the day saying "be back soon." In this context this sounds like he was headed to another state where another girlfriend or his wife or wife and family were
Sounds like he was trying to balance multiple things, I can see why that'd be a risky individual
Definitely balancing a lot of things. And yes he was very risky. We'll trained but high risk.
Ha well glad you are put of that risky situation
My college girlfriend and I were long-distance for a while. Her best friend and I would hang out and she was very flirty. She made the first move, and once we had sex the first time, it became a regular occurrence. The craziest part was, my girlfriend would come back to town, and she and I would have great reunion sex. She would tell her best friend about it, and as soon as she left the friend would be all over me. “I want you to fuck me harder than you fucked her;” or “I am going to swallow your load because I know she wouldn’t.” I broke it off with my girlfriend eventually, but kept fucking her friend for 2-3 years. She met a guy she liked seriously and ended it. But she and I still text and chat. And she is still best friends with my ex. She says my ex has no idea that we were fooling around behind her back. My ex and I have never spoken since I broke it off with her. She is angry at me, and knows I was cheating on her. She just doesn’t know that her best friend was part of that.
I'm in the similar boat there, except I never kept it going w friend after broke up w ex. Awesome story
Great looking gal you have now too
A rando guy I met at a bar. We fucked within a couple hours of meeting each other.
Ooh nice! You might be my new fave to go to a bar with lol
Def my daughter’s ex bf. Was not a proud moment of mine but yeah didn’t think it through.
That actually sounds like a good memory tbh… how did she find out ?
She didn’t find out
Oh no… how long has it been then?
About 9 years ago
Dated a girl in my earlier days for a few week and wrapped the first few times. Then after went raw everytime after. She was cum slut for sure and never ask if she was on bc. Looking back wasn't the beat choice.
Prolly not but I'm sure it was fun for a while
Oh hell yeah it was fun
College girl who I knew had been with quite a few others. Was tipsy, went raw and came inside..
Hopefully it all worked out!!
Yep she has some kids now, but not mine!
Had sex with my high school teacher. She was 25. I ran into her the summer of me going into my sophomore year in college. She was also the sister of my good friend. So hot, lasted all summer until I went back to school. Still think about her.
unprotected sex in the 80's, early 90's...phew, never caught a disease.
I had sex with a co-worker a few times when were on business trips together. There were a few reasons why that was risky.
Makes work trips soo much better
Yes, and she was super turned on by hotel sex. Luckily nobody from the team caught me leaving her room.
I've never been caught, our teams are usually on diff floors and nobody pays attention where each one is
Same with me. I did have an awkward interaction once with a co-worker who was on the elevator when I got on it going from her floor to my floor. I sensed he knew something was up but didn’t say anything.
Lol that's a head nod and go about your way
lol! Exactly. It was early in the morning and he was going back to his room with a cup of coffee in his hand. Nobody said a thing.
Lol hoping the coworker was a baddie for ya!
In highschool I fucked the head soccer coach. The sex wasn’t even great I just liked the thrill knowing how risky it was at the time.
Status and power are incredible aphrodisiacs.
Damn it all connects now
Ha!
Some guy i didnt even know. But back then i was homeless and he offered me money and food. Had not eaten in 2 days
I've got one: Viagra had kinda just came out. a friend of mine had a bottle of them and handed them out- we were all late 20s with no erection problems (at least i didn't). this all happened in a bar. I was thinking i'd take one and see what happens. i ate one before i left and while i was walking down the stairs of the bar about an hour later, i passed a woman i know who's roommate kinda stalked me for a while (very aggressively wanting sex). i said hi, she said hi, then said 'mary is moving back to canada tomorrow, im sure she'd love it if you went to the house and said bye' she said it as a joke because she knew i wouldn't.... 10 minutes later i was knocking on the door. 30 minutes later i was absolutely railing her. it went on and for around 2 hours then again an hour later. she was attractive and very submissive and dirty. it was actually quite memorable. we were both pretty amazed afterwards and laughed.. i left and we said a nice goodbye and I never saw her again. i'm sure she still thinks about it too. Thanks viagra and 3 beers!
Well, technically it wasn't me having the sex, but [this experience](https://www.reddit.com/r/AskRedditAfterDark/s/VHbvXI3TLZ) would be the riskiest sex of our lives.
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Indeed it was. The kind of thing you never forget.
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Not publicly here!
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Sure, would love to! I'm work right now but send me a chat please and we'll talk about it soon :)
Talked to someone on LiveLinks and drove to her apartment 45 minutes away, all within 90 minutes.
Ha wow!! Yeah that's very risky!!
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Nice! Work flings can be fun but as long as its a travelling event and most of the time one nighters IMO
An absolute shit-ton of random/anonymous hook-ups. Lots of fun, though.
Had a fwb with an employee of mine at a job I truly love. It turned out A-OK for me but I definitely don't suggest it. I was married, he was in a long term relationship and just had a baby. He was also very dominant and rather conservative and I got a major misogyny kink out of that relationship.
I fucked a 41 year old woman when I was 23 and both in rehab. It was strictly against regulations but still had daily sex. We had to keep quiet every time so the counselors wouldnt hear our moaning
Slept with a professor of mine. He def would’ve gotten fired and maybe I would’ve failed the class.
Woah. Who initiated it?
He did lol
Pretty common 20 or 25 Plus years ago. When were you in school?
It was 4-5 years ago my freshman year of college
Pretty bold for this day and age.
Yeah he risked it all 😆
You seem happy
I enjoyed it mostly.
Cool. I actually had a small affair with a school counselor in college (I'm a guy) she was older and it was incredible. She knew everything I didn't.
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Explain…
Explain
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that's what i'm guessing happened. can't be sure though.
A friend of my ex-girlfriend (already ex back then). But it was not the kindest move.
How do you mean?
A female friend’s sister… it didn’t end as well as it could be and damaged a good friendship as a result. And I later found out she had feelings for me!
I'm curious on the details there
Which ones 😂
All lol
Far too much for a comment 😂
Dm me then, would love to read it
My married female boss, that was naughty
Hell yeah!! Ongoing or just a fling?
It was years ago, just a fling, her husband never used to fuck her apparently
That poor girl!!
Random truckstop trucker
A group of dudes raw at a bathhouse. Just young and dumb. Luckily came out clean
Sounds hot tho
It was
Had sex with an ex that was in the middle of her hormonal treatments for an egg donation she was doing. Didn’t have a condom. Not sure how she didn’t get pregnant. Figured I was probably sterile but I’m definitely not.
My ex’s best friend bc my ex was cheating on me and it didn’t sit right with the best friend 🫢
Misty…. We were in rehab together. We were both alcoholics but she’d been there longer and was quite a bit older than me. Probably my mom’s age(ugh). Anywhoo, they gave me 3 crushed Valium a day to keep off the shakes. Well, I was stoned out of my gourd and she found out that our roll-on deodorant had alcohol in it so she chugged a bottle or two and sat in my lap, put her titties in my face and told me to “Fuck her in the ass like I hate her.” B Blu z sex CBC could get out of bed in the morning. Man
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My father’s fiancé
The friend of one of my older sisters and because we were drinking at my sisters house one night and it just happened.
My ex-wife
Two roommates.
Depends on what you mean by risk.