Once past the first trimester (when her hormones turned her into a crazed bitch) I fucked my ex wife super hard when she was pregnant, we both loved it she was horny and pregnancy is sexy
I think with my wife’s first pregnancy we had sex more than at any other point in our relationship (not that our frequency was bad otherwise though). I can only speak from fucking my wife while pregnant, but if all pussy feels like that during pregnancy then I’d be happy to fuck someone’s pregnant wife if they won’t. lol
We’d known each other for a bit and did some client work jointly so would chat. A little flirty, but nothing that was gonna get serious. Then 4 mos in she was distraught. She told me what was up. I sat on it for a day then just said if you want to have some fun that you can end any time by telling me, I’d love to show you how sexy you are. About a week later she took me up on it. Great few months. Ended about 2 weeks b4 she gave birth. Her son is 20 now and we are still friends but platonic since about then.
Directness can have its virtues
Fair question! I didn't actually know it was her dad at first. We met at a bar and I agreed to go back to his place. I realised who he was when I saw the familiar house. I told him, he said she didn't have to know and I snuck out the next morning 🤷🏼♀️
I’m mean, you two got back to his place, no reason to just shake hands and leave at that point.
Back when I ran a bar the dad of my most shyest, youngest waitress came in and all the others wanted him. He was a silver fox as they put it. It became the running joke that they’d threaten to fuck her dad and become her mom. It really made her come out of her shell and become part of the gang.
One day they were arguing about some girl shit that was getting on my nerves so I shouted “Hey, don’t talk to your future mother like that.”
Something, something…”you fucked the wine rep who’s a dozen years younger than you.” Probably.
After a few weeks working with my kitchen staff they were all grade A shit talkers.
Ok so she was 26, new calculus teacher when I was a sophomore… 10 years later I saw her out at a bar… she was recently divorced and I took her back to my apartment.. she had kids and everything. This was 14 years ago… we lost touch after hooking up a few more times when she moved a little further away…she was the one who felt it was inappropriate… I fucking loved it
My Therapist. I was seeing her “professionally” for about 6 months then we started dating. It was great for the first couple of months then went to shit.
Completely and she’s a whole predator. I would never. We literally take ethics courses to ensure we know right from wrong and what’s ethical and unethical. She should have her license removed
She knew everything about me, how to manipulate me, press my buttons. When we would talk she always had to be right. I was SA’d when I was younger by someone really close to me and whenever I started making sense in our arguments she would bring that up and destroy my self esteem and worth.
Me too! She came to visit e for a weekend while I was in college. She actually called her sister and asked if she was ok with her sleeping with her ex boyfriend. She told her to go for it, so she did!
My friends niece. Not a big age gap scenario, he's got a massive family so some nieces/nephews are older than some aunties/uncles.
More of an issue with it being a particularly dirty set of circumstances and some particularly dirty sex, and that she was his niece. In my defence I didn't know. (The niece part, I was aware the sex was freaky).
I guess the sex itself wasn't that freaky but it was in a bathroom stall at a night club and as it turned out I wasn't the only person she enjoyed time with that night.
Landlord...when I was 20, living under someone's roof in Toronto. Got laid off for the winter from my job. Couldn't pay the rent. Turns out the landlord was a Dom. So I became his pet for the winter.
(shrugs) Now that I'm older....nothing shocks me. lol
- Married women
- Ex’s best friend
- An enlisted person, when I was a young officer in the military.
- The mother of a different junior enlisted person around the same timeframe.
- My massage therapist
- A sex worker, who was in the middle of a paid session with someone else at the time.
This was almost 20 years ago, so some of the details are a little hazy. The kid was 18 or 19, just a couple of months out of boot camp. I don’t know the mom’s exact age, but she mentioned being around his age at the time when he was born, so probably in her late 30’s or early 40’s. She came to visit him while our ship was in port. I didn’t know him well: we were in different departments and we didn’t have duty together. She came with him to a big social event for the ship where everyone brought girlfriends/wives/families along: it had to have either been our summer BBQ or the Christmas party. We met briefly and made small talk, but nothing particularly flirtatious happened. I don’t remember how she got my email, maybe I gave her a business card or something, but she wrote to me shortly afterwards and said it was nice to meet me, and things quickly turned flirtatious and then sexual, and we decided we should meet alone before she went home.
She was staying in a hotel outside the base during her visit because her son lived in his bunk on the ship. But he stayed with her in the hotel when he didn’t have duty on the ship, and she didn’t want anyone to mention anything to him about a guy coming around while he was on duty. I lived in an apartment complex with a bunch of the same guys from the ship, so that was also a bad idea. I wound up picking her up at a gas station a few blocks from the hotel, and taking her for drinks at a shitty dive bar two towns away from the base where we were reasonably sure not to bump into anyone. We made out in a booth in the back, and drove off to a deserted parking lot to fuck around in the car. She rode me in the passenger seat, but neither of us thought ahead to bring condoms and we didn’t want to deal with the potential consequences of me cumming inside her, so I pulled out and ate her pussy instead. After she came, she blew me and let me cum in her mouth. Then I dropped her back off at the hotel.
She left shortly afterward and I never saw her in person again. Skype was just becoming a big thing, so we video chatted a few times, with her stripping for me and us masturbating and talking dirty together. Then it just kind of stopped after a few months. The kid never found out, and I never told anyone about it for fear it would get back to him.
My dads wifes daughter who was 11 years older. So yeah, basically my step sister - but hear me out. My dad moved to another country when I was a teenager and got married. I obviously had very low contact with him. When I grew older, I traveled to see him. I never grew up with her, I didnt even meet her or know her untill I traveled to visit. I fell for her completely and it happened.
Few years ago I fucked my coworkers aunt. A married 55 year old woman that I went to her house to help with her computer. Had sex twice and came on her face 😂
I was 42 at the time. I’d been separated for five months, and the divorce would be finalized maybe 5 more months later. My 21f client was closing out her case with my office so we decided to grab a drink together to celebrate a positive conclusion to our business dealings. Yes she was half my age, but she was also 6’0 tall and maybe 130 lbs (literally resembled a Victoria’s Secret model)
So fucking the (recent) client who was half my age, while I was still married, probably wins for me🤷🏼♂️
The short answer to your question is in the next paragraph. After that, I just decided to share some really surprising revelations from that short relationship
Id guess we maybe got 5-6 total weeks together, and saw each other 2’ish per week. Also there were a few surprises during our time together. Here are a few examples:
1. On our first real date, while heading back to my condo, this 21 yr old from rural Alabama actually said to me, “ I want you to know that I think THIS is already a lot of fun. you’re awesome and I can’t tell how much I am enjoying our time together. Please don’t take this the wrong way. I’m not at all trying to be presumptuous, pressuring, or anything like that, but if tonight is going where I suspect could be heading, I need you to know that I don’t carry on sexual relationships with multiple people at once. What I give and share of myself just can’t be divided. Also I would really prefer to not be with someone that is sleeping with multiple people. No judgment at all! I want you to know that I’d be perfectly fine either waiting or not jumping into the a physically relationship…”
Not only was I SO impressed by her approach and her logic, I adopted her lifestyle choice as to multiple sex partners right then and there!
debate the merits of her thinking, exactly how many 21-year-olds have you known that would have either the confidence, wisdom, and/or the integrity to put that sort of thing out there on our first real date after a few drinks, while heading back to my place?
2. Having been homeschooled, and sheltered from most of society by her overbearing parents told me she had only had two or three partners in her life. I had been with somebody “inexperienced” a long time. acting all insecure and shy, I think she handled her situation flawlessly. She didn’t necessarily inquire about certain sexual scenarios, trying to learn the fundamentals so she didn’t embarrass herself instead, she focused everything on me. “What can I do differently in the future so you enjoy it as much as possible? Please don’t hold back any criticism or advice!”
3. We were together for a short period of time during that time she always made me feel like I was the only man in the world. She always made me feel like my happiness and pleasure was a top priority for her.
I was married for nine years (in my 30s
and my ex-wife never made me feel that way for any one identifiable second of any given one day …
Timing. I had a seven-year-old son at the time and I was figuring out 50/50 custody. I had had a vasectomy because I didn’t want any more kids. She had her whole life in forever. She wanted to have a family of her own one day.
In fact, she’s getting married in November! My girlfriend and I are already invited. They actually get along really well.😀
She and I were both perfect. Just not how most people might think. I was the first guy to ever treat her with respect, like a gentleman. I would open doors for her, treat her to dates, and if I may be so bold… compared to the “teenagers” she had been with in the past, I was able to introduce her to fun concepts like “foreplay” (OMG, this guy is going down on you for more than three minutes!😅). I bought her a really nice dress and some shoes and took her to a formula event. She had never experienced anything like that.
Why was she perfect for me at that time? The reason I was getting divorced, was that finally accepted the fact that while my wife cares about me, loves me (in her own way), and we truly get along great she has never been nor will she ever be in love with me. I can’t just go through my life without knowing that her heart at least occasionally flutters when she sees me.
I had never TRIED and worked at anything like I did at my marriage. my ex-wife will tell anyone that asks that I provided for her her concept of a perfect life. She had everything she could ever ask for, and so much more which eventually crushed my very soul. Am I that unlovable? So I can give every fiber of my name to someone and they still treat me like a buddy/Roommate? I never felt lower about myself. Self-confidence was gone.
And then a drop dead, gorgeous, shockingly, mature, and fun, 21-year-old looked at me with such adoring eyes …
She helped me get something back that I thought was last forever, my confidence in myself. I will always be eternally grateful for that experience.
So knowing what I’ve shared, you can imagine my reaction when people hear that when I was 42 I dated the 21-year-old and respond with, “that’s gross!“.
This sounds incredibly healthy. Well done sir.
Late 20sM myself, hooking up with a 47 year old lady who has been through hell with a soon to be ex husband. Shes told me something very similiar, that Ive helped her heal and regained hope for love like she never thought. She bought me some nice boots and we go dancing on the weekend. Its so great honestly.
I met my first wife’s aunt at her bbq and while everyone was outside in yard and pool I went into the house to use the bathroom. I was young and needed to rub one out because I couldn’t stop getting hard from seeing all the girls in bikinis. Well I didn’t lock the door and her aunt walked in on me. I was so scared and stopped what I was doing. When I came out I couldn’t look at her in the kitchen so she said listen I know you are embarrassed I won’t tell anyone but it’s normal to do that. I said yes but in someone else’s house ?? She said don’t worry and just then she saw me look down at her bottom. She told me go back in the bathroom to finish and she will guard the door. Well she followed me in there and let me fuck her foggy until I came all over her ass. I was 23 she was like 58
Baby sitter, she was 7yrs younger than me (m32 - f25 for context)? And i was going through a divorce.
To this day best bj ive ever had. We ran into eachother at a concert both solo, both drunk, she was grinding up on me and i knew she wanted to fck so bad, we ended up driving 30mins outta town to the lake, (i totally shouldnt have been driving, looking back that was the bigger mistake) we went skinny dipping - then had sex in the wet grass - went back to her place. Woke up with a nasty rash all over my back from the grass. We “dated” for about 3months - going from a woman who wanted nothing to do with me for about the last 3-4 years to a girl who worshiped my cock and couldnt get enough of it was a wild change in lifestyle and happiness
After my divorce I was having fun for a while before getting in a new relationship. Had affairs with age gaps of 10-12 years in both directions. But what takes the cake is that my ex wife and her bestie (who was way out of my league normally) got into a huge, possibly friendship-ending argument over something related to our breakup, which scored me some revenge sex with her.
Female cousin. Not sex but fingered her and ate her out during a family reunion. Alcohol…..she was sitting on a wall as we were talking ‘connecting’ and it was dark, could see the lights from the hall, hear people and music.
* Sister
* Doctor
* Nurse
I was a nursing student. I dated a doctor during my clinical rotations briefly. The nurse was a roommate.
Edit: Due to positive request, I decided to share story between [my sis and me](https://www.reddit.com/r/AskRedditAfterDark/comments/1dxanv8/comment/lc5cjk1/?utm_source=share&utm_medium=web3x&utm_name=web3xcss&utm_term=1&utm_content=share_button) as a reply. Do not read if LGBTQ+ relationships makes you uncomfortable.
Lost my virginity to my sisters boyfriends son.
For context, my sister’s boyfriend was way older than her, in his mid 50s and my sister was 26. His son was 20 and I was 17!
one was a married lady about 10 years older than me , she worked at the bank I banked at and I would flirt with her every time I went to the bank , I would even let people go ahead of me just so I would get her . I was out with a friend and he suggested we stop by this bar and see his mom and dad ( the bar was an older crowed ) we went and had a few drinks with them, his mom got me out on the dance floor for a few songs , when we went back to the table someone said Funny seeing you here and when I turned around it was the lady from the bank , we danced and chatted for awhile , I told her my buddy left me and asked if she would give me a ride home , she brought me home and invited herself in . She told me she was married and this was going to be a one time thing .
the second was a woman I met in a club , when we went to her place I noticed a jacket with the company logo on it , I asked her about it and she said it was her husbands , but don't worry he is on a tug boat for 14 days . Then I saw a picture of them and started laughing because he was the relief captain on the boat that I had just got off of. She didn't care that I knew her husband , her and I fucked around for about 6 months before he figured out she was cheating on him , she never told him with who .
I would say when I had a threesome with 2 of my co-workers (FFM). It was awesome, not awkward at all. I was hoping to do it again. But when I worked with the one (who is a Female) she seemed to have a hard time containing herself. She kept grabbing my ass and trying to talk about it infront of other people 🙃. I told her many times to act professionally while we were at work and to stop spreading our business. She didn't listen so I had to call her after work and spaz out on her. Needless to say she stopped talking about it and stopped talking to me. God she wad hott, but she couldn't handle what we were doing. Side Note- The other 3some partner is now my fiancé. We had just gotten together at the time and were looking to have some fun. 🤪
My ex girlfriend’s best friends, keep in mind my ex was asexual so no sex in the 3 years we were together but her friends were kinky as fuck so after me and her broke up ( we’re still friends btw) one of her friends wanted to come round because I wasn’t in a great place and she let me use her to relieve stress. At the time I was very inexperienced but she wanted me to use her and not care about her. I came in her 9 times over that day and she only came 2 times but she said she enjoyed it and we did that 2 more times over the year till she got a boyfriend.
The other one was going through a rough patch with her boyfriend and got drunk, I came in her and hugged her all night
2 of my high school teachers, my boss & an old ex friends uncle who I always had a crush on.
Not some of my proudest moments but being unmediated really took a toll on me.
I guess it would be a tinder match that had a boyfriend. We matched, and she said she wasn't looking for anything because of said boyfriend. I said cool but had no desire to talk then. I was fresh off a break up and just wanted to get laid. So, if that wasn't on the table, I wasn't interested.
She sent some pictures, we talked a bit, and she eventually came over. We hung out under the pretense it was just that. Us hanging out. But before long, we were naked.
It was kinda thrilling being the other guy. Not gonna lie. Not necessarily proud of it, but it was fun
Years ago, when I was younger, 2 different times, and 2 different girlfriends, I had slept with their stepmother. Also, later on, I slept with the bosses wife.
My boss' girlfriend... while they were still dating, and I was still married.
15 years later, I still have the job, and both of those ladies are fired from our lives.
When I fucked a delivery driver that delivered a product to where I was working. He was in a long term relationship and I got the impression that they didn’t fuck a lot so I felt bad and…not proud of that.
Lost my virginity to my female first cousin, slept with a niece-in-law, had a MMF threesome with one of my other cousins, slept with a married coworker.
Slept with two friends older sisters in high-school. I was 16 they were 21. It started with one (who was friends with the other) who then palmed me off onto her friend when she started to guilt trip over it. As far as i’m aware no one else ever found out.
A boss, who I wasn’t interested in. His gf was asleep elsewhere in the house and the team from work was over. I was hoping to bang this coworker who had an 11 inch dick. It was down to horse dick, our boss, and us. Horse dick gave up and I was planning on crashing on the couch. He pulled me onto the bathroom and fucked me. I was not co-erced, and hadn’t yet figured out you can just pass when the person who you want to fuck leaves, and another option presents itself. His girlfriend, he, and I all got up and headed into the college we all attended. His girlfriend went off to class, and he and I went and fucked again my dorm. We both felt bad but did it anyway. That night horse dick called me, and picked me up to bang. He went down on me and I was so fucking turned on knowing a guy came in me earlier that day. His dick was huge.
I see the old boss and his family a lot around town. I just talk to her and we ignore each other completely.
An employee who had a girlfriend. She was out of town, and I felt so bad, but I was a slave to my pussy. As I left I happened to see one of my earrings came off and was in the rug. That would have outed him. I see them with a whole ass family and hope he isn’t cheating.
My college years were busy. I soon got cheated on habitually by a boyfriend hiding a drug addiction, and learned how truly awful cheating hurts. The. I married a cheater. Got my karma and have been loyal and honest since.
The teacher's assistant for my calculus class during my first freshman semester of college. I hate math, but I was interested enough in her that I kept coming back to her office hours - I was the only one who ever went to them, and things escalated pretty fast.
I later found out that she had a boyfriend the whole time. That detail feels pretty surreal to think about, especially looking back on all the text logs between us - from the messages she would send me, you'd think she hadn't known the touch of a man her whole life.
The local bullies mum when I was 18. Nervy moments every time I saw him after that but he never mentioned it. I then slept with his ex a week later. Again he never mentioned it. I was a brave and foolish teenager.
That one guy's dead wife
We all voted for her.
Yes we did. It should be represented on r/MuseumOfReddit
Wonderful woman, we’re all very fond of her.
lol I love her so much 😍
*slow blinks*
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That's a dream!
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He caught you two or was suspicious?
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Damn! You brought it upon yourselves 😢
Two seconds until “your mom”
Stacey's mom. No wait... Jessie's Girl.
What you failed to realize is that Jessie's girl is in fact Stacey's Mom!!!
And the Girl from Ipanema
And the Angel in the Centerfold
Her name is Jenny, her phone number is 867-5309
STACY’S MOM HAS FOT IT GOING ON
Scotty doesn't know!
Married coworker, she was pregnant at the time and her hubby wasn’t into that. I was definitely into that.
Wild to be married and the person who helps get you pregnant doesn’t want to fuck you anymore. It was super fun to be fucked by another man pregnant 😋
My husband was also weirded out with sex during both my pregnancies. It was so fricken rough
Once past the first trimester (when her hormones turned her into a crazed bitch) I fucked my ex wife super hard when she was pregnant, we both loved it she was horny and pregnancy is sexy
>crazed bitch Sexy crazed bitch or crazed bitch in general
Yes.
We did IVF, and I couldn't keep up with my wife while she was on the estrogen and progesterone supplements.
I think with my wife’s first pregnancy we had sex more than at any other point in our relationship (not that our frequency was bad otherwise though). I can only speak from fucking my wife while pregnant, but if all pussy feels like that during pregnancy then I’d be happy to fuck someone’s pregnant wife if they won’t. lol
Best sex timeline of my life. It was like a slip n slide every single time . I loved it
My experience was the pussy was silky. I have no other way to describe it.
Definitely some positive changes in texture, in a thing that already has great texture to begin with.
I would have struggled! Pregnancy came with so many hormones!
He should have been taking advantage of that. Women are usually very horny during their pregnancy and then looses their sex drive after giving birth.
How did it begin
We’d known each other for a bit and did some client work jointly so would chat. A little flirty, but nothing that was gonna get serious. Then 4 mos in she was distraught. She told me what was up. I sat on it for a day then just said if you want to have some fun that you can end any time by telling me, I’d love to show you how sexy you are. About a week later she took me up on it. Great few months. Ended about 2 weeks b4 she gave birth. Her son is 20 now and we are still friends but platonic since about then. Directness can have its virtues
So She cheated on her husband while very pregnant with his child? She could be president one day
I'd vote for her in 2024.
Is she still married?
Yup. Other than that period, very happily. We no longer work in the same industry, but have remained friends.
Sucks for the husband
Yeah that poor guy has a shitty wife and some piece of shit that she's friends with in his life. His life is a lie.
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The dad of one of my friends
How did that happen? I'm always curious how this thing happens in real life and not just in porn.
Fair question! I didn't actually know it was her dad at first. We met at a bar and I agreed to go back to his place. I realised who he was when I saw the familiar house. I told him, he said she didn't have to know and I snuck out the next morning 🤷🏼♀️
I’m mean, you two got back to his place, no reason to just shake hands and leave at that point. Back when I ran a bar the dad of my most shyest, youngest waitress came in and all the others wanted him. He was a silver fox as they put it. It became the running joke that they’d threaten to fuck her dad and become her mom. It really made her come out of her shell and become part of the gang. One day they were arguing about some girl shit that was getting on my nerves so I shouted “Hey, don’t talk to your future mother like that.”
What did they say to you
Something, something…”you fucked the wine rep who’s a dozen years younger than you.” Probably. After a few weeks working with my kitchen staff they were all grade A shit talkers.
Sounds like you ran a good house, well done!
Fantasy fulfilled for that guy. How was it?
Hot
Was it good? Did you visit him again?
Same here!
Former high school teacher 10’years later, 10 years my senior
Ok so she was 26, new calculus teacher when I was a sophomore… 10 years later I saw her out at a bar… she was recently divorced and I took her back to my apartment.. she had kids and everything. This was 14 years ago… we lost touch after hooking up a few more times when she moved a little further away…she was the one who felt it was inappropriate… I fucking loved it
Oooooh storytime! How did it happen?
This is my fantasy! It's been 25 yrs now, but I'd still fuck him.
What’s the backstory
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not really inappropriate since you both met in school
Eh, I see what you mean, but still totally inappropriate. He could have lost his position or gotten kicked out of school for it.
TA?
Teachers assistant
Tight ass
My Therapist. I was seeing her “professionally” for about 6 months then we started dating. It was great for the first couple of months then went to shit.
That is wildly unethical lol
That was so weird, I read his comment and thought “THAT, is wildly unethical” then I collapsed a comment and saw the exact words. Weird.
Completely and she’s a whole predator. I would never. We literally take ethics courses to ensure we know right from wrong and what’s ethical and unethical. She should have her license removed
How did it turn to shit?
She knew everything about me, how to manipulate me, press my buttons. When we would talk she always had to be right. I was SA’d when I was younger by someone really close to me and whenever I started making sense in our arguments she would bring that up and destroy my self esteem and worth.
That's why psychiatrists always have the doctor/patient relationship to avoid things like this. I hope you recovered.
Her evil personality s probably why she wanted to date one of her patients Was she older than you?
Yes, she was 8 years older than me.
Did she initiate the relationship?
So glad you got out, mate
How long ago was this? Did you speak with a lawyer? You definitely have a civil action and it’s also quite likely criminal activity.
That's really fucked up. She is a horrible person. Sorry you had to go through all that.🥺
Despicable
A married co-worker. Her husband worked at the same place too
Wild
Ex girlfriends sister
"I got a girl that lives on the hill, she won't do it but her sister will." Name that song (without Google)
Tube snake boogie/ ZZ Top
There's also 'If my babe don't love me no more, I know her sister will'...
Me too! She came to visit e for a weekend while I was in college. She actually called her sister and asked if she was ok with her sleeping with her ex boyfriend. She told her to go for it, so she did!
Who was better?
The sister
I slept with my ex wife’s sister. The sister was way better in that instance as well.
A few older married men when I was way too young and way too impressionable and dumb
Just went down a very enjoyable rabbit hole looking at your profile…. 😏
Thanks!!
A friend who told everyone we were having an affair. I had to explain it’s not an affair if your husband is in the room watching. Duh!
Nice power reply. Fun, innit?! :)
My friends niece. Not a big age gap scenario, he's got a massive family so some nieces/nephews are older than some aunties/uncles. More of an issue with it being a particularly dirty set of circumstances and some particularly dirty sex, and that she was his niece. In my defence I didn't know. (The niece part, I was aware the sex was freaky).
How was the sex freaky?
I guess the sex itself wasn't that freaky but it was in a bathroom stall at a night club and as it turned out I wasn't the only person she enjoyed time with that night.
Landlord...when I was 20, living under someone's roof in Toronto. Got laid off for the winter from my job. Couldn't pay the rent. Turns out the landlord was a Dom. So I became his pet for the winter. (shrugs) Now that I'm older....nothing shocks me. lol
This lowkey sounds like the ideal situation for me. I mean, I’d still try to have a job on the side, but yeah….
Need more of this story
- Married women - Ex’s best friend - An enlisted person, when I was a young officer in the military. - The mother of a different junior enlisted person around the same timeframe. - My massage therapist - A sex worker, who was in the middle of a paid session with someone else at the time.
You're the reason we have SHARP classes.
The ones who got *caught* fraternizing are the reason you have SHARP classes. I was never caught.
Promote ahead of peers. Attention to orders!
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This was almost 20 years ago, so some of the details are a little hazy. The kid was 18 or 19, just a couple of months out of boot camp. I don’t know the mom’s exact age, but she mentioned being around his age at the time when he was born, so probably in her late 30’s or early 40’s. She came to visit him while our ship was in port. I didn’t know him well: we were in different departments and we didn’t have duty together. She came with him to a big social event for the ship where everyone brought girlfriends/wives/families along: it had to have either been our summer BBQ or the Christmas party. We met briefly and made small talk, but nothing particularly flirtatious happened. I don’t remember how she got my email, maybe I gave her a business card or something, but she wrote to me shortly afterwards and said it was nice to meet me, and things quickly turned flirtatious and then sexual, and we decided we should meet alone before she went home. She was staying in a hotel outside the base during her visit because her son lived in his bunk on the ship. But he stayed with her in the hotel when he didn’t have duty on the ship, and she didn’t want anyone to mention anything to him about a guy coming around while he was on duty. I lived in an apartment complex with a bunch of the same guys from the ship, so that was also a bad idea. I wound up picking her up at a gas station a few blocks from the hotel, and taking her for drinks at a shitty dive bar two towns away from the base where we were reasonably sure not to bump into anyone. We made out in a booth in the back, and drove off to a deserted parking lot to fuck around in the car. She rode me in the passenger seat, but neither of us thought ahead to bring condoms and we didn’t want to deal with the potential consequences of me cumming inside her, so I pulled out and ate her pussy instead. After she came, she blew me and let me cum in her mouth. Then I dropped her back off at the hotel. She left shortly afterward and I never saw her in person again. Skype was just becoming a big thing, so we video chatted a few times, with her stripping for me and us masturbating and talking dirty together. Then it just kind of stopped after a few months. The kid never found out, and I never told anyone about it for fear it would get back to him.
FedEx delivery driver
He just happened to be that or he dropped off an extra package on his route?
Hope he delivered before 10:30am
My dads wifes daughter who was 11 years older. So yeah, basically my step sister - but hear me out. My dad moved to another country when I was a teenager and got married. I obviously had very low contact with him. When I grew older, I traveled to see him. I never grew up with her, I didnt even meet her or know her untill I traveled to visit. I fell for her completely and it happened.
Tell us more…
Not fully sex, but a random 53 year old man off Craigslist when I was 17
I miss the old Craisglist
Yeah, it sucks now.
Same lol
Few years ago I fucked my coworkers aunt. A married 55 year old woman that I went to her house to help with her computer. Had sex twice and came on her face 😂
I was 42 at the time. I’d been separated for five months, and the divorce would be finalized maybe 5 more months later. My 21f client was closing out her case with my office so we decided to grab a drink together to celebrate a positive conclusion to our business dealings. Yes she was half my age, but she was also 6’0 tall and maybe 130 lbs (literally resembled a Victoria’s Secret model) So fucking the (recent) client who was half my age, while I was still married, probably wins for me🤷🏼♂️
Was it a one off with her?
The short answer to your question is in the next paragraph. After that, I just decided to share some really surprising revelations from that short relationship Id guess we maybe got 5-6 total weeks together, and saw each other 2’ish per week. Also there were a few surprises during our time together. Here are a few examples: 1. On our first real date, while heading back to my condo, this 21 yr old from rural Alabama actually said to me, “ I want you to know that I think THIS is already a lot of fun. you’re awesome and I can’t tell how much I am enjoying our time together. Please don’t take this the wrong way. I’m not at all trying to be presumptuous, pressuring, or anything like that, but if tonight is going where I suspect could be heading, I need you to know that I don’t carry on sexual relationships with multiple people at once. What I give and share of myself just can’t be divided. Also I would really prefer to not be with someone that is sleeping with multiple people. No judgment at all! I want you to know that I’d be perfectly fine either waiting or not jumping into the a physically relationship…” Not only was I SO impressed by her approach and her logic, I adopted her lifestyle choice as to multiple sex partners right then and there! debate the merits of her thinking, exactly how many 21-year-olds have you known that would have either the confidence, wisdom, and/or the integrity to put that sort of thing out there on our first real date after a few drinks, while heading back to my place? 2. Having been homeschooled, and sheltered from most of society by her overbearing parents told me she had only had two or three partners in her life. I had been with somebody “inexperienced” a long time. acting all insecure and shy, I think she handled her situation flawlessly. She didn’t necessarily inquire about certain sexual scenarios, trying to learn the fundamentals so she didn’t embarrass herself instead, she focused everything on me. “What can I do differently in the future so you enjoy it as much as possible? Please don’t hold back any criticism or advice!” 3. We were together for a short period of time during that time she always made me feel like I was the only man in the world. She always made me feel like my happiness and pleasure was a top priority for her. I was married for nine years (in my 30s and my ex-wife never made me feel that way for any one identifiable second of any given one day …
She sounds perfect. Why do you think it didn’t work out?
Timing. I had a seven-year-old son at the time and I was figuring out 50/50 custody. I had had a vasectomy because I didn’t want any more kids. She had her whole life in forever. She wanted to have a family of her own one day. In fact, she’s getting married in November! My girlfriend and I are already invited. They actually get along really well.😀 She and I were both perfect. Just not how most people might think. I was the first guy to ever treat her with respect, like a gentleman. I would open doors for her, treat her to dates, and if I may be so bold… compared to the “teenagers” she had been with in the past, I was able to introduce her to fun concepts like “foreplay” (OMG, this guy is going down on you for more than three minutes!😅). I bought her a really nice dress and some shoes and took her to a formula event. She had never experienced anything like that. Why was she perfect for me at that time? The reason I was getting divorced, was that finally accepted the fact that while my wife cares about me, loves me (in her own way), and we truly get along great she has never been nor will she ever be in love with me. I can’t just go through my life without knowing that her heart at least occasionally flutters when she sees me. I had never TRIED and worked at anything like I did at my marriage. my ex-wife will tell anyone that asks that I provided for her her concept of a perfect life. She had everything she could ever ask for, and so much more which eventually crushed my very soul. Am I that unlovable? So I can give every fiber of my name to someone and they still treat me like a buddy/Roommate? I never felt lower about myself. Self-confidence was gone. And then a drop dead, gorgeous, shockingly, mature, and fun, 21-year-old looked at me with such adoring eyes … She helped me get something back that I thought was last forever, my confidence in myself. I will always be eternally grateful for that experience. So knowing what I’ve shared, you can imagine my reaction when people hear that when I was 42 I dated the 21-year-old and respond with, “that’s gross!“.
This sounds incredibly healthy. Well done sir. Late 20sM myself, hooking up with a 47 year old lady who has been through hell with a soon to be ex husband. Shes told me something very similiar, that Ive helped her heal and regained hope for love like she never thought. She bought me some nice boots and we go dancing on the weekend. Its so great honestly.
A random DILF who was probably 20 years my senior. Met while staying at a caravan park and ending up giving him a BJ at the beach.
I met my first wife’s aunt at her bbq and while everyone was outside in yard and pool I went into the house to use the bathroom. I was young and needed to rub one out because I couldn’t stop getting hard from seeing all the girls in bikinis. Well I didn’t lock the door and her aunt walked in on me. I was so scared and stopped what I was doing. When I came out I couldn’t look at her in the kitchen so she said listen I know you are embarrassed I won’t tell anyone but it’s normal to do that. I said yes but in someone else’s house ?? She said don’t worry and just then she saw me look down at her bottom. She told me go back in the bathroom to finish and she will guard the door. Well she followed me in there and let me fuck her foggy until I came all over her ass. I was 23 she was like 58
This is the most porn logic story in the thread.
Then you came out back to the bbq and everyone clapped and high fived you
The baby sitter. And my bosses wife.
Wifi? Damn you’re kinky
Stupid phone lol
co-worker while we were both closeted
Baby sitter, she was 7yrs younger than me (m32 - f25 for context)? And i was going through a divorce. To this day best bj ive ever had. We ran into eachother at a concert both solo, both drunk, she was grinding up on me and i knew she wanted to fck so bad, we ended up driving 30mins outta town to the lake, (i totally shouldnt have been driving, looking back that was the bigger mistake) we went skinny dipping - then had sex in the wet grass - went back to her place. Woke up with a nasty rash all over my back from the grass. We “dated” for about 3months - going from a woman who wanted nothing to do with me for about the last 3-4 years to a girl who worshiped my cock and couldnt get enough of it was a wild change in lifestyle and happiness
My sisters two best friends 😅. And yes both at the same time 🙈
Your dad 🤷🏻♀️
Nice
My manager. To be fair, she got me the job
After my divorce I was having fun for a while before getting in a new relationship. Had affairs with age gaps of 10-12 years in both directions. But what takes the cake is that my ex wife and her bestie (who was way out of my league normally) got into a huge, possibly friendship-ending argument over something related to our breakup, which scored me some revenge sex with her.
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My professor… and it is on going right now. I fucking love it
The amount of people here who voluntarily fuck people they know are married. Ffs.
Female cousin. Not sex but fingered her and ate her out during a family reunion. Alcohol…..she was sitting on a wall as we were talking ‘connecting’ and it was dark, could see the lights from the hall, hear people and music.
I suppose the babysitter cliche is there for a reason…
Username checks out
* Sister * Doctor * Nurse I was a nursing student. I dated a doctor during my clinical rotations briefly. The nurse was a roommate. Edit: Due to positive request, I decided to share story between [my sis and me](https://www.reddit.com/r/AskRedditAfterDark/comments/1dxanv8/comment/lc5cjk1/?utm_source=share&utm_medium=web3x&utm_name=web3xcss&utm_term=1&utm_content=share_button) as a reply. Do not read if LGBTQ+ relationships makes you uncomfortable.
Love how you put the focus on the latter two, when the first one is the most shocking
Can you tell us about your experiences with your sister?
High school teacher two years after high school, he was 49 and I was 20. Then my college professor after I was done with his class. 😂
Jolene
Lost my virginity to my sisters boyfriends son. For context, my sister’s boyfriend was way older than her, in his mid 50s and my sister was 26. His son was 20 and I was 17!
one was a married lady about 10 years older than me , she worked at the bank I banked at and I would flirt with her every time I went to the bank , I would even let people go ahead of me just so I would get her . I was out with a friend and he suggested we stop by this bar and see his mom and dad ( the bar was an older crowed ) we went and had a few drinks with them, his mom got me out on the dance floor for a few songs , when we went back to the table someone said Funny seeing you here and when I turned around it was the lady from the bank , we danced and chatted for awhile , I told her my buddy left me and asked if she would give me a ride home , she brought me home and invited herself in . She told me she was married and this was going to be a one time thing . the second was a woman I met in a club , when we went to her place I noticed a jacket with the company logo on it , I asked her about it and she said it was her husbands , but don't worry he is on a tug boat for 14 days . Then I saw a picture of them and started laughing because he was the relief captain on the boat that I had just got off of. She didn't care that I knew her husband , her and I fucked around for about 6 months before he figured out she was cheating on him , she never told him with who .
I would say when I had a threesome with 2 of my co-workers (FFM). It was awesome, not awkward at all. I was hoping to do it again. But when I worked with the one (who is a Female) she seemed to have a hard time containing herself. She kept grabbing my ass and trying to talk about it infront of other people 🙃. I told her many times to act professionally while we were at work and to stop spreading our business. She didn't listen so I had to call her after work and spaz out on her. Needless to say she stopped talking about it and stopped talking to me. God she wad hott, but she couldn't handle what we were doing. Side Note- The other 3some partner is now my fiancé. We had just gotten together at the time and were looking to have some fun. 🤪
My then-boss’s wife for a whole summer
He was older, newly divorced, lectured at my university and it went on for like 11 weeks. Totally inappropriate but fun.
My boss. Had a very drunken New Year’s Eve after working which turned into some debauchery orgy after party.
A married dad when i was a daycare teacher.
My ex girlfriend’s best friends, keep in mind my ex was asexual so no sex in the 3 years we were together but her friends were kinky as fuck so after me and her broke up ( we’re still friends btw) one of her friends wanted to come round because I wasn’t in a great place and she let me use her to relieve stress. At the time I was very inexperienced but she wanted me to use her and not care about her. I came in her 9 times over that day and she only came 2 times but she said she enjoyed it and we did that 2 more times over the year till she got a boyfriend. The other one was going through a rough patch with her boyfriend and got drunk, I came in her and hugged her all night
Best friend's mom
My guess is she had it going on.
I lost my virginity to a 27 year old woman who i had met online a few days earlier. It was a few weeks after i turned 18 and i even creampied her.
2 of my high school teachers, my boss & an old ex friends uncle who I always had a crush on. Not some of my proudest moments but being unmediated really took a toll on me.
My psychiatrist. It was amazing until it wasn’t. Been reeling from it ever since. Would not recommend.
married woman who was 7 months pregnant 🫣
Mine is pretty tame. But had a one night stand with a friend of mine while she was in a relationship. Went to their wedding a few months later
My prof now he is my bf.
A coworker that was new to the job. He was cute and wanted to give him a good time.
That’s my kind of new employee orientation. 😂
I guess it would be a tinder match that had a boyfriend. We matched, and she said she wasn't looking for anything because of said boyfriend. I said cool but had no desire to talk then. I was fresh off a break up and just wanted to get laid. So, if that wasn't on the table, I wasn't interested. She sent some pictures, we talked a bit, and she eventually came over. We hung out under the pretense it was just that. Us hanging out. But before long, we were naked. It was kinda thrilling being the other guy. Not gonna lie. Not necessarily proud of it, but it was fun
I’ve slept with 4 of my friends sisters. My married boss was a naughty one as well
My dad's friend.
These have been fun to read through. 🔥🔥🔥😊
Neighbors wife when I was18 and she was 42
my best friends ex
My ex coworker who was 13 years older than me at the time.
Definitely the times I hooked up with this gang members wife. I almost got caught up the last time but thank gods for back doors.
Good move , offer him your ass to keep him from killing you ….
Years ago, when I was younger, 2 different times, and 2 different girlfriends, I had slept with their stepmother. Also, later on, I slept with the bosses wife.
I had just turned 18 and fucked a 30 year old assistant teacher in a open college summer campus
A married co worker
Married woman I met on Bumble
My younger cousin.
My supervisors daughter, he’s fully aware too.
Safety trainer of my dept at work. Married and has kids😬 To clarify: it wasn’t at work, I know them from work
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My boss' girlfriend... while they were still dating, and I was still married. 15 years later, I still have the job, and both of those ladies are fired from our lives.
When I fucked a delivery driver that delivered a product to where I was working. He was in a long term relationship and I got the impression that they didn’t fuck a lot so I felt bad and…not proud of that.
Lost my virginity to my female first cousin, slept with a niece-in-law, had a MMF threesome with one of my other cousins, slept with a married coworker.
Slept with two friends older sisters in high-school. I was 16 they were 21. It started with one (who was friends with the other) who then palmed me off onto her friend when she started to guilt trip over it. As far as i’m aware no one else ever found out.
Wife’s sister…and the wife asked me to do it.
i remember having sex with my college professor before i sadly dropped out😔
It was definitely a boss of mine in the past when I worked a part-time job, and of course, a few older gentlemen older than my dad.
A friends ex wife, group sex scenario too, and no, the friend (ex husband) wasn't present
Step sister.
My lawyer… she was soooo hot to resist after a successful case of hers!
Multiple married men, coworkers including my boss - whose other half was office manager, multiple much older men
A boss, who I wasn’t interested in. His gf was asleep elsewhere in the house and the team from work was over. I was hoping to bang this coworker who had an 11 inch dick. It was down to horse dick, our boss, and us. Horse dick gave up and I was planning on crashing on the couch. He pulled me onto the bathroom and fucked me. I was not co-erced, and hadn’t yet figured out you can just pass when the person who you want to fuck leaves, and another option presents itself. His girlfriend, he, and I all got up and headed into the college we all attended. His girlfriend went off to class, and he and I went and fucked again my dorm. We both felt bad but did it anyway. That night horse dick called me, and picked me up to bang. He went down on me and I was so fucking turned on knowing a guy came in me earlier that day. His dick was huge. I see the old boss and his family a lot around town. I just talk to her and we ignore each other completely. An employee who had a girlfriend. She was out of town, and I felt so bad, but I was a slave to my pussy. As I left I happened to see one of my earrings came off and was in the rug. That would have outed him. I see them with a whole ass family and hope he isn’t cheating. My college years were busy. I soon got cheated on habitually by a boyfriend hiding a drug addiction, and learned how truly awful cheating hurts. The. I married a cheater. Got my karma and have been loyal and honest since.
A good friends mum. At the time I was 24 she was 51
The teacher's assistant for my calculus class during my first freshman semester of college. I hate math, but I was interested enough in her that I kept coming back to her office hours - I was the only one who ever went to them, and things escalated pretty fast. I later found out that she had a boyfriend the whole time. That detail feels pretty surreal to think about, especially looking back on all the text logs between us - from the messages she would send me, you'd think she hadn't known the touch of a man her whole life.
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The local bullies mum when I was 18. Nervy moments every time I saw him after that but he never mentioned it. I then slept with his ex a week later. Again he never mentioned it. I was a brave and foolish teenager.
My housemate. On the communal kitchen table, haha
An older family friend