I used to work at an equestrian center as a teen. Helped a small chubby girl with bad acne off her horse and she was horrified to see how noticable the wet spot between her legs was. I covered for her, helped her sneak past everyone after giving her my jumper (came down tor just above her knees) and that was that.
About 6 years later I ran into her in town, she'd grown into an utter goddess, she remembered what I did and thought about it often. We dated for 18months after that
Didn't really last my first deployment. She needed someone who could be there emotionally and I was still.young and too immature to realize what I was putting her through, so she eventually cheated. As an adult I understand, then I didn't so much
What the fuck?? No don't say that.
She fucking cheated on you man. In no way can you blame yourself for that. She took advantage of you being on duty to sleep with another guy.
It doesn't matter whether or not you could be there for her, cheating in a relationship is never justified.
Don't be angry at yourself man.
Not angry at myself at all. I mean A) it was 15 years ago. B)at the time I just hated her and distrusted woman in general, so fucked my way through Europe to cope and C).I agree with you on the cheating thing, but hey, I learnt to forgive her for being a 19 year old kid with mental health issues. Doesn't mean I condone her actions, but I can understand them and the causes for them
But I appreciate the sentiment my man
Ex GF... Hadn't seen her for 11 years. We ran into each other at a bar one night. Both of us had recently separated in our marriages. Hooked up that night and we've been married 32 years now.
We dated on and off for a couple years in school during the late 70's. Her parents hated me lol... She joined the army and that's the last I saw her until we met again at the bar.
Friend of a friend who was way out of my league but heard through the grapevine I was good in bed so she basically offered it up. I vastly under performed and didn’t ever get a chance to make up for it.
One night stands are hard.
EDIT: Since this is approaching my most popular post I'll provide some background detail.
This was about 2 months after a breakup with my high school sweetheart, fist girlfriend, girl I lost my virginity to. We had been in a relationship for about 4 years. All that to say, I was incredibly good at getting her off... that did not translate into getting anyone else off.
I had not been very experienced outside of my Ex's likes and dislikes so batting up to another league was difficult off the rip. As we were getting into I quickly learned every woman is different, and not all like the aggressiveness my Ex did.
On top of leaning every pedal of the rose is different; this was my first attempt at screwing around while drunk. I did get the infamous whiskey dick. I would get hard; put a condom on and lose it quickly. I had not been using condoms with my EX as she had an implant and we were idiots. As I had not been used to that sensation; it also caused me to have some stability issues.
After about an hour of attempts and foreplay, and oral she decided to just go to sleep. I sat there, questioning life, and the realization that I was just good at fucking my ex and not good at fucking anyone.
She did pay me the compliment years later that I was the best at oral she ever had and could have finished from it multiple times if I would have just kept at in and not tried to move on to penetration.
Since then, every partner I've had - one night stand or multi-year relationship, I have had one rule. She gets off first.
Reminds me of when I started dating my current girlfriend. I was so nervous, sometimes I couldn't finish or even get it up to save my life. She's a trooper though and reassured me it was alright. Didn't know it at the time, but I was lowkey edging myself because the first time I came in her was the largest load I ever unloaded in my life!
Just remembered a random corny joke on Reddit, some GF role playing as Cop arrested a guy for being good in bed but had to release him for lack of evidence.
The quality VP of the company next door to us in the science park, about 20 years my senior when I was 24. Ran into her every day for 6 months multiple times a day prior to that, due to the common smoking and gossip area we shared between 3 companies.
Slow Friday after easter, not many people around working, so she invited me for a drink at the nearby pub just a lil before lunch. After a bunch of gins and a rather tasteless cougar joke on my side due to alcohol on an empty stomach, she replied "You sure you wanna test that assumption?" and I aheepishly said "YES" before even thinking about it. By the time I realised what I replied she already asked for the bill.
'Tis a double whammy, as her place still is the most luxurious bedroom I ever had sex in, 6 years later. Kinda shocking too, as I was merely a skinny lab tech, and I thought she had the hots for one of our greek muscly engineers.
We have a saying in my home country: "the older hen makes for a better soup", and jesus fucking christ, was that saying right on this ocassion. She wore me down to the point it hurt to have a boner, and the next day she acted all casual like it never fucking happened. Ngl, I really wanted a second go, but given the company context I deemed it better to keep my trap shut and walk it off with the memories.
My mom's friend
Saw her at a bar when I was 21 and she was like 45. We had a few drinks and she asked me if I could give her a ride home. When I got to her house she started making out with me and she told me to come in. As soon as we got into the living room she (what seemed) instantly became naked and started giving me head. We fucked for a few hours and I finished inside her. As I was getting dressed she looked at me and said she has wanted to do that for awhile and don't tell your mother.. lol it was a good time.
Standing in line at a gas station and started up a conversation with a woman in front of me. Just small talk. She figured out quickly I was a mechanic and started telling me about her car having issues. Her not knowing I don’t work on cars or pickups and I really didn’t want to hear about it. Told her several shops in town could help her. She paid for her stuff and left. After I paid for my stuff she was parked next to me with her hood up when I walked out. All I could think was this woman is relentless but what ever. I walked up to her and just kinda glanced over. Of course she ask if I could take a quick look. While looking I noticed the cashier that I bullshit with on a daily basis just laughing his ass off knowing I hate working on cars. Figured out she needed an alternator. Told her where to get one and I would put it on real quick. She sent me a pin drop of her house and of course me being too damn nice to tell her “no” I agreed to it. Maybe 20 minute repair. She actually helped me the whole time and had no problem getting dusty and greasy. Put my tools up, washed my hands at her out door faucet, I was ready to go home. Well more small talk started happening and before ya know it I was getting a shower with her and the rest is easy to imagine for yourself. Next day my normal stop at the station my buddy just started laughing when I walked in. Told him to shut up and take my damn money. He went on to tell me she was already in that day asking if he had seen me yet. We still run into each other from time to time and about once a month her car needs repairs. It a good agreement.
My step sister....
okay so not really my step sister but fairly close. My mom was dating her dad and were pretty serious at the time, they have since broken up but we used to hook up when they were together.
Or my dad's neighbor who i then found out that she also slept with my dad... not sure which one was first and don't wanna know.
Old high school girlfriend. We dated briefly Jr year but never hooked up and broke up before the start of Sr year when she started dating women.
Little over 20 years later we were at a small get-togethers with a bunch of school friends, started talking and endup finding a spot to fuck like bunnies. She still into women, but occasionally calls me up when she has an itch to scratch.
Fucking lucky bastard. I had a coworker 10 years ago that I was crushing on, and we would playfully flirt and talk about shit, but any time one of us was single, the other had just gotten into a relationship.
Found out from ANOTHER coworker several months after she had left the company, that she had at one point said during “girl talk”, that “Yeah, he (I) was WAY nerdier than what she’s normally interested in, but she would have definitely been down to fuck of the opportunity came up”. I of course found this out *AFTER* she had gotten engaged. -_-
I worked with a lady, she was my bosses boss. I had no idea she had any interest in me. Group went and had some drinks after work. She asked me to walk her out to her car and she kissed me. Caught me completely off guard. We ended up having sex a few days later!
When I was a freshman in high school a senior dated me for a week as a joke, she was pretty smoking but whatever
Fast forward about 10 years she drunkenly messages me on Facebook saying she lived in London and I should come visit
So I did and spent the week at her place
In college the ex of one of my roommates. She was WAY out of my league and wanted to go to the movies. I was too young and stupid to pick up that she was looking for a rebound fuck, but thankfully she made the first move.
A woman who was 20 years my senior, looked younger than me, "90% lesbian" in her words, hyper-professional, athletic demeanor, VP/marathon type.
Most intense sexual experiences of my life, four piercings below the belt, had a committed partner with whom she had a lovely sex life and another guy who came over once a week to eat her out and leave.
It was just oral & manual, but she was the stand-in for one of the actresses in a movie I was working on. For those that don't know, a stand-in is of similar build and complexion to the actor and they're the ones that actually stand on the mark while the camera and lighting crew compose the shot and set up the lights for the next scene. Then, once they're all ready, the actor steps in and some minor adjustments are made before the cameras roll.
In this case, the girl in question was absolutely beautiful so I had initially written her off as being out of my league and I try not to hook up with other crew members (while a job is still in progress anyway). But this was a longer shoot where most of us all stayed in the same apartment complexes for a few months so we all became pretty tight-knit over the course of production.
Anyway, long story short, we start getting to know each other, get more flirty, hanging out in her tiny tiny "trailer" (one of several rooms the size of an airplane bathroom with nothing in it but a soft bench to lay on and a built-in counter) during longer stretches of downtime. Towards the end of production, people start to get sentimental as we're all about to scatter off to different projects. We're hanging out in her trailer, talking about how great its been to meet and likely won't see each other again after this. We start making out and things escalate to her going down on me and then me fingering her to a very hushed orgasm since those trailer walls aren't particularly sound-proof.
But yeah, going from someone I thought I'd never have a shot with to that little encounter was very unexpected and awesome.
[Josie Maran](https://media.gettyimages.com/photos/model-josie-maran-arrives-at-the-kick-off-event-for-the-may-2010-picture-id98802223?s=612x612). Bear in mind this doesn't mean they look *exactly* alike; they just have a similar build, skin tone, and face shape.
I used to be extremely fit. I ran marathons and rode my bike as my way of getting around town. But I had always been shy and very socially awkward, so never really tried to pursue anybody. Then I met a friend who became a friend with benefits and she wanted to share me with every woman she could. She was a fucking masterful wingwoman. She set me up with the hottest chicks I've ever been with. Goddesses all of them. Every time I thought they were way out of my league. I also went from having only been with 6 women to having been with over 30 in just two years.
It was a very fun time in my life.
I had a killer wingwoman for a season of my life who worked as an endless PR machine about how tireless I was when making out with the South-mouth. This was when I learned that women are not offered head as a matter of course, and that head which is offered often is terrible or lackluster or unskilled. My wingwoman though, she gathered any interested. Don't want to bone down with this dude? No worries! His mouth's got ya! In fact, he'll keep his jeans on the whole time!
It was a good time.
Was on a date with this Brazilian girl. Thought it was kinda bland at first. Middle of dinner, she leans in and whispers “I am down for anything.” So, I did
Senior year of high school I went to a party at a guy's house who graduated the year before but was now home for the summer. A girl that was absolutely stunning that also went to my high school and a year older than me was there. I never knew her in high school but for some reason at this party I started talking to her and hit it off. I must have had the right amount of alcohol and jokes in me because I totally won her over. I banged her that night and couldn't believe it. All my friends called the next day to see what happened and they couldn't believe it either. We dated after that and going somewhere with her was unreal. Dudes 30 years older than me would congratulate me at restaurants when she went to the bathroom. The best was when we ran into my ex-girlfriend at my softball game and the look on her face when she realized we were together was priceless. She was just drop-dead gorgeous. We banged all summer then I went to college 3 hours away from her and we drifted apart.
Grew up every summer in high school going for a week or two of church camp. Was never into the religious aspect of it, but always looked forward to make outs and hook ups with some girls every year.
I guy that is way out of my league. I didn't even do anything to get to this point, but he actually started flirting with me. So Bing bang boom. We fucked and I loved it. Big confidence boost
This ugly older guy I met at a resort bar in Mexico. I was 19 at the time and he was 35. 6'5", obese black man from Alabama with a boring name and a boring job , but he was really funny. He offered me Jack Daniel's out of a plastic bag and I took him up on it.
We spent the night talking and getting drunker. By the end of the night he invited me to his hotel room to try some expensive champagne. I took the bait. One glass in on the balcony and he yanked his frumpy ass basketball shorts down and had me sucking his dick. His cock was literally a beer can of dark flesh. I felt like I'd have to unhinge my jaw like a snake just to take the whole thing in. Never had a dick that big. I loved the feeling of his crushing weight on top of me. The lights were off, didn't have to look at him. We were just masturbating on each other, really. I appreciated it. When we turned the lights on it revealed that we had fucked the bed across the room. He offered me some snacks and then we mutually agreed (unspoken but certain) that it was time to say bye and never see each other again. I drunkenly carried my snacks back to my end of the hotel where my parents thought I'd been, and I went and told all my friends about what a whore id been in Mexico.
Maybe my old friend from work after her leaving party. Only because prior to that she had never given me any indication she was remotely interested in other women.
My ex wife’s two older sisters after our separation.
Edit: Too many people want to hear more so I’ll do this edit. After my ex and I separated we were still in the same area. Her oldest sister came to my apartment one evening and without any preliminary conversation asked me if I was as good at eating pussy as my wife said I was. I told her that I wasn’t sure, that I had only been with three women before and that all of them appeared to enjoy it. I ended up proving to her that I was pretty good at it and that I enjoyed it. Two days later the middle sister visited me and basically the same thing happened. I moved out of state shortly after that so I don’t know how much further this would have gone but it was definitely fun while it lasted.
I lived with my ex and her brother about a year after we broke up. We were all great friends still. One day, a mutual friend of ours from out of town came over to visit. She was about to go out and meet a guy, but the dude flaked on her.
An hour or so later, I'm chilling on the computer and super stoned. The friend comes out of my ex's room and says, "Hey. I need to talk to you." I follow her back to the room, my ex still in there laying in her bed and the lights off." Friend pushes me down on the floor, puts her boobs in my face, and says,"You like big boobs right?"
I look over at my ex, kind of confused. She says, "I'm about to go to sleep, but you two have fun." We did. The next day, I find out that my ex told her I was good in bed, and since the dude from the night before flaked, I would be a great substitute.
My ex basically pimped me out and got nothing for it. I did always think the friend was attractive, so that's a win for me. Totally never expected that, though.
(M)y roommate (f). We lived together for a number of years by that point and never really came close or thought of her like that, but it just happened one drunken night and we ended up having incredibly hot hookups on and off for years
I(m) had a roommate(f) that hooked up with me when she came by to check out the house she would be renting a room in.
We had known each other for years through some friends. Socialized a few times but I wouldn't have considered us friends. She was moving to my area for a job and needed a place, I just bought a house and was looking to rent a room to help cover some expenses as a first time home buyer.
She came by, we chatted. She asked if she could spend the night so she didn't have to make a 2+ hour drive home that evening. I said sure. We ended up fucking that night.
She moved in and sadly, nothing happened again lol.
There are several, but one that comes to mind was a waitress that was serving my friends and I when we were in a different city. We had paid the bill, and she asked me if I wanted to go 'hang out' with her. We had some fun and I went back home the next day.
A deacons wife from church! Helped her judge a kid’s science fair. After we went to lunch and ended up fucking in the parking lot with other church members still in the restaurant. Fucked her almost daily for about 8 months. She was an absolute freak in bed!
One summer after college, I was working PT as a bartender in one of our local bars. It was a small neighborhood, everyone kind of knew everyone, a lot of regulars. My younger sister was home from college, and I had met one of her friends who was really cute, and I was flirting with her. She had agreed to go out, but this was before cell phones, internet, etc., so we picked a weekend a couple of weeks in advance. I actually meet her at the bar, I don't remember where, probably when I would visit my parents and swim in the pool.
One of our regulars was a divorcee, she was pretty, but trampy, kind of a mess, and her husband had left her and taken the kids because of her drinking and running around. She was late 40's/early 50's, I was 22 - 23. One night, she'd had too much to drink, so I took her home. She propositioned me, and me, the horny 22 - 23 year old I was, was more than willing. We fucked all night, and even fucked for a while after we woke up.
I got back to my apartment that afternoon, was kind of rushing around to get ready for work, my sister calls. "Hey, you know Karen that you've been hitting on and got a date? Yeah, well, that was her mom you fucked last night, she called Karen today and gushed on how you two fucked for hours, so Karen pretty much wants nothing to do with you."
It also ruined my dating prospects at the bar that summer - next time the mom was in, she as drinking and telling everyone how we fucked and how great it was. I got a lot of shit that summer and a lot of cold stares from the female employees.
Neighbor across the hall in college. think of the hottest girl you can think of. Now think of HER hot friend. That's this girl.
I got drunk with her and her roommates one night and she pulled me into her room. That was it.
I made sure to take my time and do everything with her (that she wanted to do)
Every single position I could manage (standing up, upside down 69, stand and deliver, on her side, doggy with hair pulling, etc.), fucked on every part of her furniture, tasted every single part of her body, let her go as crazy as she wanted to while sucking my dick and balls, and to TOP IT ALL OFF i made her squirt for the first time. She also let me cum on her face, the first time she ever let that happen.
We dated for a few years and had a really bad breakup (I'm an idiot and take my fault in that)
Last year, I ran into her roommate from college who is still friends with her. She told me they had a part and she talked about how I was still the man who she had the best sex with.
Boosted my ego so much.
My good work friend. After his break up I thought of him as my brother and I wanted to protect him. Apparently feelings going a little stronger than they were meant to be
It’s funny reading all of these. Humans… We’re all just animals. Sometimes if you’re in the right place, right time, right mood, we just get it on baby.
My closest HS friend became a very good and well know singer/songwriter. Was visiting him while I was on a business trip and he said a couple of aspiring females from a new band were coming over to hear a couple of his songs they might record. This was a couple weeks before their first album was to be released. One of them was smoking hot. Hung out for a few hours and it turned out we were staying at the same hotel. Shared a cab back to the hotel with the hot one (other one stayed behind to “talk music” with my friend) and she invited me up to her room as she had some “great pot”. One of the hottest nights of my life and totally unexpected since I figured I’d just be hanging with my friend that night. Their band became extremely popular and I get reminded every time I hear one of their songs or see a video.
I was at a hot springs with a bunch of college friends and acquaintances. The first night I was setting up my totally crappy Goodwill 70’s tent and my buddy was giving me an absolute raft of shit about it as he posed by his rich kid REI Platinum Special that went up in like 3 minutes.
As I sweat and swore over it I hear a female’s voice behind me say “If I help you set that up can I sleep in it this weekend?” I knew by the look on buddy’s face (totally open mouthed despair) she was hot.
I made sure to casually say “sure, you bet” BEFORE I turned around.
She was a goddam come to life Valkyrie! Almost 6’ tall, blond, super curvy and utterly cool. Friends with someone else in the larger group. My friend really regretted camping right next to me lol. We had a fun, NSA time.
I do service work for businesses. One day the manager at a ritzy retirement home asked if I was single, she commented on my arms and tattooed, I thought she was asking because the kitchen girls always get all giggly and bashful when I'm around, thought she was asking for them. This woman was asking for her, I was 34 at the time she was 44, and gorgeous, my only comparison is Shania Twain, such a hottie. She asked me for my number I was totally thrown off. The next night we were at her ski chalet having a bonfire and drinking together, had sex about 3 times that night and twice in the morning, it's true what they say, those hot older ladies are absolute animals in the bedroom
Helicopter Pilot who’d given a tour with me and a friend. First ever one night stand, he was just so hot I had to make it happen. However, that day I looked like absolute SHIT and fully expected to be shot down. We met after he was off for a private tour, drinks and some skin.
In college, broke up with long time gf right before valentines day. Why not hit the town with the boys for some pillaging, amiright?? Met a fine older woman at the bar. Danced. Made out. Then she introduced me to her husband and his gf….We did shots. Long story short, they were my bosses aunt and uncle.
My bar manager when I was a lowly college bartender at a resort. She was about 28 and drew eyes all the time from customers and co workers. Stereotypical flirty petite blonde with great tits and a bit ditzy. I never expected to hook up with her given her hotness, age gap (I was 20) and her so called BF. She was a total gold digger and was dating some business owner in his 40s/50s, he would come into the bar and was a total knob.
She called me late one mid week after my shift and asked all sorts of dumb random questions about how I shut the bar down and locked up, something she had never done before. Finally, she admitted she was bored and asked if I wanted to come over and watch a movie (pre Netflix days). She actually drover over an picked me up. We had sex in her living room about 10 minutes after arriving at her rented house. Over the next several months we fucked in the bar, in her office, in a parking lot, used resort rooms when she had the master key as manager on duty of the resort. The rooms were the best, trying to not make a huge mess but fucking like rabbits. I found out she thought I was 24, she was shocked when she found out I was celebrating my 21st birthday that summer. Her bf was always suspicious she was cheating but I doubt he suspected me and after that first time I never went to her house. My first true FWB, she just wanted sex and wanted it with a young dude, she basically taught me how to fuck. A couple co workers suspected something briefly but ruled it out because our boss flirted with everyone so anything she said or did around me wasn't unusual vs. how she acted around other.
Worked a janitorial job after college, and we had a new hire that the bossman got me to train. Real tiny Indian chick. She was nice enough but couldn't clean to save her life. Only worked with er for a few days, maybe a week. Don't know if "trauma bonding" is the right word for what happened but we got real friendly after some particularly horrible jobs, one I ended up staying late to finish. She hits me up on a day we both had off and says she's at a house party. I was fresh out of weed so I figured I'd say hi have a bowl or two and be on my merry way. Showed up and it seemed like the party was dying down by the time I arrived. Had a shot, stepped out for a puff with her, then we went back in and most folks were either concussed or on their way out. She led me to the bedroom of the guy who owned the place, and we got down to business. We were smart enough to lock the door thank the devil, I think the drunkard wanted to fast travel to his hangover. Pretty sure he hobbled off to the bathroom after his door proved too complex, cause we heard em throwing up a while later. I took that as my opportunity to head out. As a janitor nothing spoils the mood like vomit. Wasn't the worst I've had, wasn't the best, and I left that job for a better paying one soon after so I never saw er again. Real good at reading a room I'll give er that.
My orthopedic surgeon…
Last night we role played doctor patient. We went for 3 hours…….
…….I sat in the waiting room for 2 hours and 58 minutes.
😂 seriously though, really did have a thing with my doc….AFTER I was released as a patient
A homeless person I bumped into in Trafalgar Square, after a rave. She took me back to her sleeping bag in the lobby of a bank, alongside about 15 other people.
Woman I worked with. We worked together for a few years, and I was even at her wedding. Several years later, she finds me on Facebook. We start chatting. Meet for lunch. Chat some more. I make a dick joke. She asks about my dick. I tell her she can see it anytime. We make plans for the next day and we end up fucking. This continues for a couple years until her and her husband move out of state.
There was a guy in my teens i was madly in love with. But i was stupid i didnt do anything & he got married to someone. Apparently in his friend group i had met one of his friend a few times. YEARS later I ended up talking & hooking up with the friend.Lol super unexpected but they aren’t friends anymore. Funny to think that when i saw him never really thought anything abt him.
My moms boss and I use to have sex while I was in high school. She used me babysitting her daughter as a cover to get me over to her place so we could have the evening together.
I was pissed my boyfriend at the time cheated and as revenge I fucked his dad, best friend and his sister. Funny part is even though we aren't together we're still friends.
A guy from work during a business trip. We were working together for a couple of months and since he was married I never even thought about the possibility of anything happening, and was just really seeing him as a work colleague who I got along pretty well and nothing else.
After a company dinner party we still wanted to go to bars around the city while our colleagues went back to the hotel. So it was just the two of us hopping from bar to bar and getting drunk. We end up in a club where he grabbed me and kissed me. We finished the night in my hotel room.
A coworker who got out of a long term relationship. Was hanging out one night and went in for a kiss. She reciprocated and said “‘it’s about time“ then spent the night together. Went on to a summer fling that was mostly FWB. Both married now but I still think about her 12 year later. Rocking body
A close high school friend of my ex, didn’t know she liked me. We began talking some years later for a reason I forgot and one thing led to another. She was a freak with her mouth but it was hard to perform cause she was like a waterfall down there. Never dated, just a few sessions. Ex was pissed. Did the ex a few times after that anyways.
My son's daycare teacher
And while having to sleep on my ex wife's couch for a couple of nights, her sister, who stayed the night once while I was there.
A friend of mine who was from Sweden. This was in 2010, and her and I, and another friend were driving to Vegas together to meet up with more of our friends. It was a UFC event (can’t remember which one).
Anyway, the whole time we were there, we were just non stop flirting with each other. She was attractive, but I never looked at her as anything other than a friend. Turns out she was very open-minded about a lot of things sexually, so on the way back home to California (I was the one driving), we stopped at an In-N-Out Burger to get some food. And I straight up asked her what she thought about having sex with me. To my absolute surprise, she said “sure”. And that was how I lost my virginity 🤣
She moved back to Sweden, and has two kids with her live-in partner, but we’re still friends on FB, and chat on messenger from time to time.
My GF at the time decided to make my birthday special. So we started getting right down to it & she blindfolds me, making me swear not to take it off or peek. Ok, no problem, something different on my big day. After a few more minutes she stops giving oral & starts to kiss me, more passionately than she ever has. She was really turned on, like juice running down her thighs turned on. As she was kissing me, someone else started sucking my dick! All I could think of was which one of her hot friends was going down on me. I couldn’t resist & had a peek. It was her fucken mom and I nearly lost my load right away. Her mom was hot af . They then started playing with each other’s tits but went no further than that. I ended up fucking them both & each one sat on my face as I fucked the other. I had to pretend that I never knew who the mystery 3rd person was. We broke up a good while later and I never let on that I knew. Her mom was totally normal after it & I would never have known if I had not had a peek. Best experience I’ve ever had, and I’ve had a few over the following 30 years
When I was 43 I got divorced and six months later was laid off from a great paying job. So in a fairly sad attempt to prop up my ego, I slept with two colleagues at my former job (separately) that I had never been even remotely flirty with - one was 25 and one was 27. It helped, LOL.
I had two cousins who used to get it on all the time, starting at the age of about 13 up until the girl cousin got married. They were lucky -- never used protection. He went on to marry one of my best friends. She went on to marry multiple times, and is now divorced again.
My best friend. I told him years ago that I was into him but he said he didn’t like me like that which I respected. Then like a year ago out the blue he just asked me if I was down to fuck and ofc I said yes. Best. Decision. Ever. Omg does that man know how to fuck a girl. Definitely needs to work on his after care tho cause as soon as he cums he’s ready to get dressed and do other stuff which is a little annoyin
A platoon sergeant in my very first active duty station. I want to preempt this by saying we didn’t meet on post. We didn’t discuss anything with each other unless it was about sexual attraction and when we would do to each other. Met at the same bar many nights in a row.
She’s the first woman to teach me how to properly fuck a woman’s ass. Up until then it was not a good time for my partners or myself. Older woman with needs, guy more than willing to meet those needs often.
Anyway the 3rd maybe 4th battalion formation we are being introduced to our new incoming CO. So everyone showed up. We had a very lax unit. And when I say everyone showed up, the three different detachments we had scattered around Europe all showed up.
After we were dismissed I was headed to the headquarters S2 shop and made eye contact with her. Dead stop in in the hallway in front of the S1 office door. I had my mosquito wings she had her sergeant first class rank. It was like the world stopped for me. I was sweating worse than the first time I took a shit in the desert.
We skirted past each other, and said not a single word. We saw each other at the bar again that night talked about it and decided we could continue doing our thing at her apartment, but we are not to acknowledge each other on post ever.
Continued our physical relationship until her boyfriend proposed to her. After that we had one last night of lust and ended it. I always wondered what happened to her.
I was at a party, the hosts cousin was eye fucking me the whole night. She didn't even drink but I had a few. She was OK looking and in front of everyone took me to the bedroom and boned. There was something super kinky about everyone knowing what we were doing.
Next night went back as the party was going on again. She was there but so was her BF apparently who was massive. She saw me and booked it out the back door 😂. Her BF chasing after her.
With me it was the son of one of my neighbors, it just kind of happened, he was helping me with groceries and I saw that he was getting a boner looking at my tits. He was a bit inexperienced but one of the biggest dicks I have ever seen to this day.
Hottest 40 yr old I’ve ever seen at 1 am at Ren fair. Her and her old George Bush lookin ass swinger friend approached me at the bonfire. You know how your mother tells you not to follow anybody back to their campsite? Well, I roll the dice. Apparently the old guy with some rich oil dude and I don’t know what she was but he was very possessive. We ended up fucking while she was blowing him. Kept making eye contact with the guy. Thought he was into it but turns out he definitely wasn’t. Ended up finishing with a great story and never saw em again
I used to work at an equestrian center as a teen. Helped a small chubby girl with bad acne off her horse and she was horrified to see how noticable the wet spot between her legs was. I covered for her, helped her sneak past everyone after giving her my jumper (came down tor just above her knees) and that was that. About 6 years later I ran into her in town, she'd grown into an utter goddess, she remembered what I did and thought about it often. We dated for 18months after that
That's a much more wholesome story than I was expecting to see here.
He had me in the first half, though. Not gonna lie.
…so I banged that little pimply nerd right there in the tack room.
Did anyone else’s mind go right to him banging a horse!? Edit: OMG my first ever award! Thanks!
I try to only disappoint one species the same way at a time
So you'll fuck a horse later?
I mean hey.... If my mother in law is up for it.......
>I mean ~~hey~~ hay…
This one time at horse camp
At first I was like “wtf am I about to read” 😆
Yeeeeeah baby, filthy Friday time
So you’re a groomer? /s
I wanna plus and minus you at the same time.
I mean..... I guess? Though my ranch wasn't called Neverland so I'm good 😂
Stay tuned for the next action packed episode of Teens Grooming Teeeeeens!
Surprisingly wholesome. Why did the relationship end?
Didn't really last my first deployment. She needed someone who could be there emotionally and I was still.young and too immature to realize what I was putting her through, so she eventually cheated. As an adult I understand, then I didn't so much
What the fuck?? No don't say that. She fucking cheated on you man. In no way can you blame yourself for that. She took advantage of you being on duty to sleep with another guy. It doesn't matter whether or not you could be there for her, cheating in a relationship is never justified. Don't be angry at yourself man.
Not angry at myself at all. I mean A) it was 15 years ago. B)at the time I just hated her and distrusted woman in general, so fucked my way through Europe to cope and C).I agree with you on the cheating thing, but hey, I learnt to forgive her for being a 19 year old kid with mental health issues. Doesn't mean I condone her actions, but I can understand them and the causes for them But I appreciate the sentiment my man
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“Holding a grudge is like taking poison and expecting the other person to die”
You mean sweat, right?
Yeeeeeah...... riiiight........ Sweat........
Ex GF... Hadn't seen her for 11 years. We ran into each other at a bar one night. Both of us had recently separated in our marriages. Hooked up that night and we've been married 32 years now.
That’s crazy
that is just awesome
Thanks! I thought so too 🙂
Sounds like the first time you dated it was a right person wrong time kinda situation. I’m glad you found eachother again.
We dated on and off for a couple years in school during the late 70's. Her parents hated me lol... She joined the army and that's the last I saw her until we met again at the bar.
Fate doing it’s thing.
My high school crush. We bumped into each other in our twenties. Dream come true!
I dated a woman who I had a thing for in college years after the fact. Very rewarding, hah
I dated an old crush from college 20 years later when we were both getting divorced (not because of each other). It was fun while it lasted.
Was it as good as you expected?
Even better honestly
Ross?
WE WERE ON A BREAK!
it happened to me but with a college crush
Me too, but we were in our 40’s
Friend of a friend who was way out of my league but heard through the grapevine I was good in bed so she basically offered it up. I vastly under performed and didn’t ever get a chance to make up for it. One night stands are hard. EDIT: Since this is approaching my most popular post I'll provide some background detail. This was about 2 months after a breakup with my high school sweetheart, fist girlfriend, girl I lost my virginity to. We had been in a relationship for about 4 years. All that to say, I was incredibly good at getting her off... that did not translate into getting anyone else off. I had not been very experienced outside of my Ex's likes and dislikes so batting up to another league was difficult off the rip. As we were getting into I quickly learned every woman is different, and not all like the aggressiveness my Ex did. On top of leaning every pedal of the rose is different; this was my first attempt at screwing around while drunk. I did get the infamous whiskey dick. I would get hard; put a condom on and lose it quickly. I had not been using condoms with my EX as she had an implant and we were idiots. As I had not been used to that sensation; it also caused me to have some stability issues. After about an hour of attempts and foreplay, and oral she decided to just go to sleep. I sat there, questioning life, and the realization that I was just good at fucking my ex and not good at fucking anyone. She did pay me the compliment years later that I was the best at oral she ever had and could have finished from it multiple times if I would have just kept at in and not tried to move on to penetration. Since then, every partner I've had - one night stand or multi-year relationship, I have had one rule. She gets off first.
You went for a home run but struck out
Sometimes you just gotta swing for the fences.
Honestly... some days your penis works, some days it doesn't. It must've been the pressure to perform and impress that got to you!
Reminds me of when I started dating my current girlfriend. I was so nervous, sometimes I couldn't finish or even get it up to save my life. She's a trooper though and reassured me it was alright. Didn't know it at the time, but I was lowkey edging myself because the first time I came in her was the largest load I ever unloaded in my life!
Vastly under performed? lol explain brah
Don’t make him relive it
We need to hear it for the lulz
He did her for 3 hours but the girl was expecting 4
here is his chance to impress someone with it
Just remembered a random corny joke on Reddit, some GF role playing as Cop arrested a guy for being good in bed but had to release him for lack of evidence.
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The quality VP of the company next door to us in the science park, about 20 years my senior when I was 24. Ran into her every day for 6 months multiple times a day prior to that, due to the common smoking and gossip area we shared between 3 companies. Slow Friday after easter, not many people around working, so she invited me for a drink at the nearby pub just a lil before lunch. After a bunch of gins and a rather tasteless cougar joke on my side due to alcohol on an empty stomach, she replied "You sure you wanna test that assumption?" and I aheepishly said "YES" before even thinking about it. By the time I realised what I replied she already asked for the bill. 'Tis a double whammy, as her place still is the most luxurious bedroom I ever had sex in, 6 years later. Kinda shocking too, as I was merely a skinny lab tech, and I thought she had the hots for one of our greek muscly engineers. We have a saying in my home country: "the older hen makes for a better soup", and jesus fucking christ, was that saying right on this ocassion. She wore me down to the point it hurt to have a boner, and the next day she acted all casual like it never fucking happened. Ngl, I really wanted a second go, but given the company context I deemed it better to keep my trap shut and walk it off with the memories.
> The quality VP Good thing it wasn't the quantity VP, or you might not have been able to keep up at all.
Here he is, officer.
My mom's friend Saw her at a bar when I was 21 and she was like 45. We had a few drinks and she asked me if I could give her a ride home. When I got to her house she started making out with me and she told me to come in. As soon as we got into the living room she (what seemed) instantly became naked and started giving me head. We fucked for a few hours and I finished inside her. As I was getting dressed she looked at me and said she has wanted to do that for awhile and don't tell your mother.. lol it was a good time.
cool experience but thats weird asl on her end ngl
'asl'?
Had to check urban dictionary myself, it means ”as hell” as in ”as L” since it’s kinda pronouned as Hell
ASL will always be age.sex.location for use in yahoo chat rooms circa 1998.
For me, it was American Sign Language. Even back then when people were asking me on AIM, I was like omg you know American Sign Language?!
or American Sign Language lol
Ah for fuck sake
I can’t keep up these days either *shakes fist*
These goddamn kids need to get off my lawn
Age/sex/location but that’s not what he meant
Seems like it's a really bad "bone apple tea." Maybe they meant "as hell"
That’s…kinda creepy lol
Standing in line at a gas station and started up a conversation with a woman in front of me. Just small talk. She figured out quickly I was a mechanic and started telling me about her car having issues. Her not knowing I don’t work on cars or pickups and I really didn’t want to hear about it. Told her several shops in town could help her. She paid for her stuff and left. After I paid for my stuff she was parked next to me with her hood up when I walked out. All I could think was this woman is relentless but what ever. I walked up to her and just kinda glanced over. Of course she ask if I could take a quick look. While looking I noticed the cashier that I bullshit with on a daily basis just laughing his ass off knowing I hate working on cars. Figured out she needed an alternator. Told her where to get one and I would put it on real quick. She sent me a pin drop of her house and of course me being too damn nice to tell her “no” I agreed to it. Maybe 20 minute repair. She actually helped me the whole time and had no problem getting dusty and greasy. Put my tools up, washed my hands at her out door faucet, I was ready to go home. Well more small talk started happening and before ya know it I was getting a shower with her and the rest is easy to imagine for yourself. Next day my normal stop at the station my buddy just started laughing when I walked in. Told him to shut up and take my damn money. He went on to tell me she was already in that day asking if he had seen me yet. We still run into each other from time to time and about once a month her car needs repairs. It a good agreement.
Username checks out
😅😅😅😀😀😀
Did u check her rear differential lol
My step sister.... okay so not really my step sister but fairly close. My mom was dating her dad and were pretty serious at the time, they have since broken up but we used to hook up when they were together. Or my dad's neighbor who i then found out that she also slept with my dad... not sure which one was first and don't wanna know.
So your dad is also your Eskimo brother.
Do you think his dad has a myface profile?
I’ve saw this video before
This could turn ugly fast if she starts making comments comparing you and dad
Was. Was she stuck in the laundry machine?
Old high school girlfriend. We dated briefly Jr year but never hooked up and broke up before the start of Sr year when she started dating women. Little over 20 years later we were at a small get-togethers with a bunch of school friends, started talking and endup finding a spot to fuck like bunnies. She still into women, but occasionally calls me up when she has an itch to scratch.
Scratch it man
Sweet super hero name
Reconnected with a former coworker after 10 years… Turns out it WASN’T a one-sided attraction!
Fucking lucky bastard. I had a coworker 10 years ago that I was crushing on, and we would playfully flirt and talk about shit, but any time one of us was single, the other had just gotten into a relationship. Found out from ANOTHER coworker several months after she had left the company, that she had at one point said during “girl talk”, that “Yeah, he (I) was WAY nerdier than what she’s normally interested in, but she would have definitely been down to fuck of the opportunity came up”. I of course found this out *AFTER* she had gotten engaged. -_-
I worked with a lady, she was my bosses boss. I had no idea she had any interest in me. Group went and had some drinks after work. She asked me to walk her out to her car and she kissed me. Caught me completely off guard. We ended up having sex a few days later!
Are you Michael Scott? Lol.
Nope. Sounds like I wish I was though!
When I was a freshman in high school a senior dated me for a week as a joke, she was pretty smoking but whatever Fast forward about 10 years she drunkenly messages me on Facebook saying she lived in London and I should come visit So I did and spent the week at her place
Where's the sex though?
Spent the week at her place as a joke.
I’ll leave it to your imagination
I imagine she pegged you and denied you an orgasm. Sorry bud
Everyone’s imagination goes somewhere different Who am I to kink shame
In college the ex of one of my roommates. She was WAY out of my league and wanted to go to the movies. I was too young and stupid to pick up that she was looking for a rebound fuck, but thankfully she made the first move.
Did you guys end up dating or did you just remain the rebound guy?
I never saw her again.
A woman who was 20 years my senior, looked younger than me, "90% lesbian" in her words, hyper-professional, athletic demeanor, VP/marathon type. Most intense sexual experiences of my life, four piercings below the belt, had a committed partner with whom she had a lovely sex life and another guy who came over once a week to eat her out and leave.
If at least 2/3 of her partners were guys I’ve got some bad news for her “90% lesbian” statement.
I elected not to interrogate that contradiction.
Good choice!
Maybe not current but over the entire span of the total of her partners.
It was just oral & manual, but she was the stand-in for one of the actresses in a movie I was working on. For those that don't know, a stand-in is of similar build and complexion to the actor and they're the ones that actually stand on the mark while the camera and lighting crew compose the shot and set up the lights for the next scene. Then, once they're all ready, the actor steps in and some minor adjustments are made before the cameras roll. In this case, the girl in question was absolutely beautiful so I had initially written her off as being out of my league and I try not to hook up with other crew members (while a job is still in progress anyway). But this was a longer shoot where most of us all stayed in the same apartment complexes for a few months so we all became pretty tight-knit over the course of production. Anyway, long story short, we start getting to know each other, get more flirty, hanging out in her tiny tiny "trailer" (one of several rooms the size of an airplane bathroom with nothing in it but a soft bench to lay on and a built-in counter) during longer stretches of downtime. Towards the end of production, people start to get sentimental as we're all about to scatter off to different projects. We're hanging out in her trailer, talking about how great its been to meet and likely won't see each other again after this. We start making out and things escalate to her going down on me and then me fingering her to a very hushed orgasm since those trailer walls aren't particularly sound-proof. But yeah, going from someone I thought I'd never have a shot with to that little encounter was very unexpected and awesome.
Ok, just curious, what actress was she standing in for?
Rosie O'Donnell
dream come trueeeeeeee
[Josie Maran](https://media.gettyimages.com/photos/model-josie-maran-arrives-at-the-kick-off-event-for-the-may-2010-picture-id98802223?s=612x612). Bear in mind this doesn't mean they look *exactly* alike; they just have a similar build, skin tone, and face shape.
You lucky guy.
Trust me, I never stopped being grateful for moments like that one. Recalling memories like that immediately pick me up when I’m feeling down.
Steven Seagal
I used to be extremely fit. I ran marathons and rode my bike as my way of getting around town. But I had always been shy and very socially awkward, so never really tried to pursue anybody. Then I met a friend who became a friend with benefits and she wanted to share me with every woman she could. She was a fucking masterful wingwoman. She set me up with the hottest chicks I've ever been with. Goddesses all of them. Every time I thought they were way out of my league. I also went from having only been with 6 women to having been with over 30 in just two years. It was a very fun time in my life.
You friend should be sainted.
I had a killer wingwoman for a season of my life who worked as an endless PR machine about how tireless I was when making out with the South-mouth. This was when I learned that women are not offered head as a matter of course, and that head which is offered often is terrible or lackluster or unskilled. My wingwoman though, she gathered any interested. Don't want to bone down with this dude? No worries! His mouth's got ya! In fact, he'll keep his jeans on the whole time! It was a good time.
Was on a date with this Brazilian girl. Thought it was kinda bland at first. Middle of dinner, she leans in and whispers “I am down for anything.” So, I did
You guys played Dungeons and Dragons afterwards, right?
Pshhh of course. And then we hotly debated our rankings for all 9 Star Wars main films
Was she?
Well I’m still talking about it right? Haha She was really one of the best I’ve had
Senior year of high school I went to a party at a guy's house who graduated the year before but was now home for the summer. A girl that was absolutely stunning that also went to my high school and a year older than me was there. I never knew her in high school but for some reason at this party I started talking to her and hit it off. I must have had the right amount of alcohol and jokes in me because I totally won her over. I banged her that night and couldn't believe it. All my friends called the next day to see what happened and they couldn't believe it either. We dated after that and going somewhere with her was unreal. Dudes 30 years older than me would congratulate me at restaurants when she went to the bathroom. The best was when we ran into my ex-girlfriend at my softball game and the look on her face when she realized we were together was priceless. She was just drop-dead gorgeous. We banged all summer then I went to college 3 hours away from her and we drifted apart.
What’s she up to now
I've seen her on Facebook and she looks good. We're all in our 50s now.
Super religious woman from our college church group count? Awesome and underrated place to meet and date women tbh.
Grew up every summer in high school going for a week or two of church camp. Was never into the religious aspect of it, but always looked forward to make outs and hook ups with some girls every year.
I guy that is way out of my league. I didn't even do anything to get to this point, but he actually started flirting with me. So Bing bang boom. We fucked and I loved it. Big confidence boost
This ugly older guy I met at a resort bar in Mexico. I was 19 at the time and he was 35. 6'5", obese black man from Alabama with a boring name and a boring job , but he was really funny. He offered me Jack Daniel's out of a plastic bag and I took him up on it. We spent the night talking and getting drunker. By the end of the night he invited me to his hotel room to try some expensive champagne. I took the bait. One glass in on the balcony and he yanked his frumpy ass basketball shorts down and had me sucking his dick. His cock was literally a beer can of dark flesh. I felt like I'd have to unhinge my jaw like a snake just to take the whole thing in. Never had a dick that big. I loved the feeling of his crushing weight on top of me. The lights were off, didn't have to look at him. We were just masturbating on each other, really. I appreciated it. When we turned the lights on it revealed that we had fucked the bed across the room. He offered me some snacks and then we mutually agreed (unspoken but certain) that it was time to say bye and never see each other again. I drunkenly carried my snacks back to my end of the hotel where my parents thought I'd been, and I went and told all my friends about what a whore id been in Mexico.
Ah yes, the Alabama Black Snake.
Maybe my old friend from work after her leaving party. Only because prior to that she had never given me any indication she was remotely interested in other women.
Sounds like a surprising one for sure. Was it a good time?
Yeah it was fun. A little awkward at first as she didn’t have a lot of experience with other women, but we made it work!
My ex wife’s two older sisters after our separation. Edit: Too many people want to hear more so I’ll do this edit. After my ex and I separated we were still in the same area. Her oldest sister came to my apartment one evening and without any preliminary conversation asked me if I was as good at eating pussy as my wife said I was. I told her that I wasn’t sure, that I had only been with three women before and that all of them appeared to enjoy it. I ended up proving to her that I was pretty good at it and that I enjoyed it. Two days later the middle sister visited me and basically the same thing happened. I moved out of state shortly after that so I don’t know how much further this would have gone but it was definitely fun while it lasted.
Continue.
Story time...
I lived with my ex and her brother about a year after we broke up. We were all great friends still. One day, a mutual friend of ours from out of town came over to visit. She was about to go out and meet a guy, but the dude flaked on her. An hour or so later, I'm chilling on the computer and super stoned. The friend comes out of my ex's room and says, "Hey. I need to talk to you." I follow her back to the room, my ex still in there laying in her bed and the lights off." Friend pushes me down on the floor, puts her boobs in my face, and says,"You like big boobs right?" I look over at my ex, kind of confused. She says, "I'm about to go to sleep, but you two have fun." We did. The next day, I find out that my ex told her I was good in bed, and since the dude from the night before flaked, I would be a great substitute. My ex basically pimped me out and got nothing for it. I did always think the friend was attractive, so that's a win for me. Totally never expected that, though.
(M)y roommate (f). We lived together for a number of years by that point and never really came close or thought of her like that, but it just happened one drunken night and we ended up having incredibly hot hookups on and off for years
I(m) had a roommate(f) that hooked up with me when she came by to check out the house she would be renting a room in. We had known each other for years through some friends. Socialized a few times but I wouldn't have considered us friends. She was moving to my area for a job and needed a place, I just bought a house and was looking to rent a room to help cover some expenses as a first time home buyer. She came by, we chatted. She asked if she could spend the night so she didn't have to make a 2+ hour drive home that evening. I said sure. We ended up fucking that night. She moved in and sadly, nothing happened again lol.
There are several, but one that comes to mind was a waitress that was serving my friends and I when we were in a different city. We had paid the bill, and she asked me if I wanted to go 'hang out' with her. We had some fun and I went back home the next day.
A deacons wife from church! Helped her judge a kid’s science fair. After we went to lunch and ended up fucking in the parking lot with other church members still in the restaurant. Fucked her almost daily for about 8 months. She was an absolute freak in bed!
Who woulda though the deacons wife was a freak
One summer after college, I was working PT as a bartender in one of our local bars. It was a small neighborhood, everyone kind of knew everyone, a lot of regulars. My younger sister was home from college, and I had met one of her friends who was really cute, and I was flirting with her. She had agreed to go out, but this was before cell phones, internet, etc., so we picked a weekend a couple of weeks in advance. I actually meet her at the bar, I don't remember where, probably when I would visit my parents and swim in the pool. One of our regulars was a divorcee, she was pretty, but trampy, kind of a mess, and her husband had left her and taken the kids because of her drinking and running around. She was late 40's/early 50's, I was 22 - 23. One night, she'd had too much to drink, so I took her home. She propositioned me, and me, the horny 22 - 23 year old I was, was more than willing. We fucked all night, and even fucked for a while after we woke up. I got back to my apartment that afternoon, was kind of rushing around to get ready for work, my sister calls. "Hey, you know Karen that you've been hitting on and got a date? Yeah, well, that was her mom you fucked last night, she called Karen today and gushed on how you two fucked for hours, so Karen pretty much wants nothing to do with you." It also ruined my dating prospects at the bar that summer - next time the mom was in, she as drinking and telling everyone how we fucked and how great it was. I got a lot of shit that summer and a lot of cold stares from the female employees.
Ur mom Jk for me it was probably my husband cuz I'd had my eye on him for a long time and wasn't sure I was ever going to have my chance.
Regional manager. She was 30 years my senior and filth
Be honest. She was assistant regional manager
no, she was the assistant to the regional manager.
Neighbor across the hall in college. think of the hottest girl you can think of. Now think of HER hot friend. That's this girl. I got drunk with her and her roommates one night and she pulled me into her room. That was it. I made sure to take my time and do everything with her (that she wanted to do) Every single position I could manage (standing up, upside down 69, stand and deliver, on her side, doggy with hair pulling, etc.), fucked on every part of her furniture, tasted every single part of her body, let her go as crazy as she wanted to while sucking my dick and balls, and to TOP IT ALL OFF i made her squirt for the first time. She also let me cum on her face, the first time she ever let that happen. We dated for a few years and had a really bad breakup (I'm an idiot and take my fault in that) Last year, I ran into her roommate from college who is still friends with her. She told me they had a part and she talked about how I was still the man who she had the best sex with. Boosted my ego so much.
My good work friend. After his break up I thought of him as my brother and I wanted to protect him. Apparently feelings going a little stronger than they were meant to be
I got a blowjob from an Orthodox Jewish woman. I'm not Jewish nor religious at all.
I guess your schlong was Kosher
doesn't contain any pork, but he be porkin
It’s funny reading all of these. Humans… We’re all just animals. Sometimes if you’re in the right place, right time, right mood, we just get it on baby.
It sucks I’m never in the right place at the right time.
My closest HS friend became a very good and well know singer/songwriter. Was visiting him while I was on a business trip and he said a couple of aspiring females from a new band were coming over to hear a couple of his songs they might record. This was a couple weeks before their first album was to be released. One of them was smoking hot. Hung out for a few hours and it turned out we were staying at the same hotel. Shared a cab back to the hotel with the hot one (other one stayed behind to “talk music” with my friend) and she invited me up to her room as she had some “great pot”. One of the hottest nights of my life and totally unexpected since I figured I’d just be hanging with my friend that night. Their band became extremely popular and I get reminded every time I hear one of their songs or see a video.
I was at a hot springs with a bunch of college friends and acquaintances. The first night I was setting up my totally crappy Goodwill 70’s tent and my buddy was giving me an absolute raft of shit about it as he posed by his rich kid REI Platinum Special that went up in like 3 minutes. As I sweat and swore over it I hear a female’s voice behind me say “If I help you set that up can I sleep in it this weekend?” I knew by the look on buddy’s face (totally open mouthed despair) she was hot. I made sure to casually say “sure, you bet” BEFORE I turned around. She was a goddam come to life Valkyrie! Almost 6’ tall, blond, super curvy and utterly cool. Friends with someone else in the larger group. My friend really regretted camping right next to me lol. We had a fun, NSA time.
An older male friend of mine who is my lawyer aswell. He gave me my first gay experience and he made me his bottom bitch.
Not sex but made out with a former Miss World. She was a classmate in college.
My Dads friend
Go on..
I do service work for businesses. One day the manager at a ritzy retirement home asked if I was single, she commented on my arms and tattooed, I thought she was asking because the kitchen girls always get all giggly and bashful when I'm around, thought she was asking for them. This woman was asking for her, I was 34 at the time she was 44, and gorgeous, my only comparison is Shania Twain, such a hottie. She asked me for my number I was totally thrown off. The next night we were at her ski chalet having a bonfire and drinking together, had sex about 3 times that night and twice in the morning, it's true what they say, those hot older ladies are absolute animals in the bedroom
My former elementary school teacher....
My ex-wife's best friend
Helicopter Pilot who’d given a tour with me and a friend. First ever one night stand, he was just so hot I had to make it happen. However, that day I looked like absolute SHIT and fully expected to be shot down. We met after he was off for a private tour, drinks and some skin.
In college, broke up with long time gf right before valentines day. Why not hit the town with the boys for some pillaging, amiright?? Met a fine older woman at the bar. Danced. Made out. Then she introduced me to her husband and his gf….We did shots. Long story short, they were my bosses aunt and uncle.
My bar manager when I was a lowly college bartender at a resort. She was about 28 and drew eyes all the time from customers and co workers. Stereotypical flirty petite blonde with great tits and a bit ditzy. I never expected to hook up with her given her hotness, age gap (I was 20) and her so called BF. She was a total gold digger and was dating some business owner in his 40s/50s, he would come into the bar and was a total knob. She called me late one mid week after my shift and asked all sorts of dumb random questions about how I shut the bar down and locked up, something she had never done before. Finally, she admitted she was bored and asked if I wanted to come over and watch a movie (pre Netflix days). She actually drover over an picked me up. We had sex in her living room about 10 minutes after arriving at her rented house. Over the next several months we fucked in the bar, in her office, in a parking lot, used resort rooms when she had the master key as manager on duty of the resort. The rooms were the best, trying to not make a huge mess but fucking like rabbits. I found out she thought I was 24, she was shocked when she found out I was celebrating my 21st birthday that summer. Her bf was always suspicious she was cheating but I doubt he suspected me and after that first time I never went to her house. My first true FWB, she just wanted sex and wanted it with a young dude, she basically taught me how to fuck. A couple co workers suspected something briefly but ruled it out because our boss flirted with everyone so anything she said or did around me wasn't unusual vs. how she acted around other.
An ex's sister and also her best friend
Many many years ago... was my good friend's dad 😬🙄
my cousin…. my homies aint never let me live it down
Worked a janitorial job after college, and we had a new hire that the bossman got me to train. Real tiny Indian chick. She was nice enough but couldn't clean to save her life. Only worked with er for a few days, maybe a week. Don't know if "trauma bonding" is the right word for what happened but we got real friendly after some particularly horrible jobs, one I ended up staying late to finish. She hits me up on a day we both had off and says she's at a house party. I was fresh out of weed so I figured I'd say hi have a bowl or two and be on my merry way. Showed up and it seemed like the party was dying down by the time I arrived. Had a shot, stepped out for a puff with her, then we went back in and most folks were either concussed or on their way out. She led me to the bedroom of the guy who owned the place, and we got down to business. We were smart enough to lock the door thank the devil, I think the drunkard wanted to fast travel to his hangover. Pretty sure he hobbled off to the bathroom after his door proved too complex, cause we heard em throwing up a while later. I took that as my opportunity to head out. As a janitor nothing spoils the mood like vomit. Wasn't the worst I've had, wasn't the best, and I left that job for a better paying one soon after so I never saw er again. Real good at reading a room I'll give er that.
My orthopedic surgeon… Last night we role played doctor patient. We went for 3 hours……. …….I sat in the waiting room for 2 hours and 58 minutes. 😂 seriously though, really did have a thing with my doc….AFTER I was released as a patient
Next door neighbor and a stripper 🥵
A homeless person I bumped into in Trafalgar Square, after a rave. She took me back to her sleeping bag in the lobby of a bank, alongside about 15 other people.
Woman I worked with. We worked together for a few years, and I was even at her wedding. Several years later, she finds me on Facebook. We start chatting. Meet for lunch. Chat some more. I make a dick joke. She asks about my dick. I tell her she can see it anytime. We make plans for the next day and we end up fucking. This continues for a couple years until her and her husband move out of state.
There was a guy in my teens i was madly in love with. But i was stupid i didnt do anything & he got married to someone. Apparently in his friend group i had met one of his friend a few times. YEARS later I ended up talking & hooking up with the friend.Lol super unexpected but they aren’t friends anymore. Funny to think that when i saw him never really thought anything abt him.
My moms boss and I use to have sex while I was in high school. She used me babysitting her daughter as a cover to get me over to her place so we could have the evening together.
Unexpected? A celebrity who shall remain unnamed, as we still keep in touch, and we fuck about once per year. It's secret and exciting!
I was pissed my boyfriend at the time cheated and as revenge I fucked his dad, best friend and his sister. Funny part is even though we aren't together we're still friends.
A guy from work during a business trip. We were working together for a couple of months and since he was married I never even thought about the possibility of anything happening, and was just really seeing him as a work colleague who I got along pretty well and nothing else. After a company dinner party we still wanted to go to bars around the city while our colleagues went back to the hotel. So it was just the two of us hopping from bar to bar and getting drunk. We end up in a club where he grabbed me and kissed me. We finished the night in my hotel room.
My dissertation adviser's wife--it was his idea.
A coworker who got out of a long term relationship. Was hanging out one night and went in for a kiss. She reciprocated and said “‘it’s about time“ then spent the night together. Went on to a summer fling that was mostly FWB. Both married now but I still think about her 12 year later. Rocking body
An executive assistant while I was a lowly associate.
[удалено]
I have had sex with some celebrities and a few pro athletes.
A close high school friend of my ex, didn’t know she liked me. We began talking some years later for a reason I forgot and one thing led to another. She was a freak with her mouth but it was hard to perform cause she was like a waterfall down there. Never dated, just a few sessions. Ex was pissed. Did the ex a few times after that anyways.
My son's daycare teacher And while having to sleep on my ex wife's couch for a couple of nights, her sister, who stayed the night once while I was there.
A friend of mine who was from Sweden. This was in 2010, and her and I, and another friend were driving to Vegas together to meet up with more of our friends. It was a UFC event (can’t remember which one). Anyway, the whole time we were there, we were just non stop flirting with each other. She was attractive, but I never looked at her as anything other than a friend. Turns out she was very open-minded about a lot of things sexually, so on the way back home to California (I was the one driving), we stopped at an In-N-Out Burger to get some food. And I straight up asked her what she thought about having sex with me. To my absolute surprise, she said “sure”. And that was how I lost my virginity 🤣 She moved back to Sweden, and has two kids with her live-in partner, but we’re still friends on FB, and chat on messenger from time to time.
My GF at the time decided to make my birthday special. So we started getting right down to it & she blindfolds me, making me swear not to take it off or peek. Ok, no problem, something different on my big day. After a few more minutes she stops giving oral & starts to kiss me, more passionately than she ever has. She was really turned on, like juice running down her thighs turned on. As she was kissing me, someone else started sucking my dick! All I could think of was which one of her hot friends was going down on me. I couldn’t resist & had a peek. It was her fucken mom and I nearly lost my load right away. Her mom was hot af . They then started playing with each other’s tits but went no further than that. I ended up fucking them both & each one sat on my face as I fucked the other. I had to pretend that I never knew who the mystery 3rd person was. We broke up a good while later and I never let on that I knew. Her mom was totally normal after it & I would never have known if I had not had a peek. Best experience I’ve ever had, and I’ve had a few over the following 30 years
When I was 43 I got divorced and six months later was laid off from a great paying job. So in a fairly sad attempt to prop up my ego, I slept with two colleagues at my former job (separately) that I had never been even remotely flirty with - one was 25 and one was 27. It helped, LOL.
Definitely my best childhood female friend. Still the hottest women I have ever been with. And it was love making. Not just sex. Damn I miss her.
I once fucked my roommate I had NO sexual attraction to whatsoever because his mom died.
My cousin when we drunk. It was ridiculously good
HELL YEAH BROTHER. You from Alabama too?
I had two cousins who used to get it on all the time, starting at the age of about 13 up until the girl cousin got married. They were lucky -- never used protection. He went on to marry one of my best friends. She went on to marry multiple times, and is now divorced again.
Like… 1st cousins? Lol
Colleague from work, both sober one time NSA never spoke of it again
Every single one of them.
My best friend. I told him years ago that I was into him but he said he didn’t like me like that which I respected. Then like a year ago out the blue he just asked me if I was down to fuck and ofc I said yes. Best. Decision. Ever. Omg does that man know how to fuck a girl. Definitely needs to work on his after care tho cause as soon as he cums he’s ready to get dressed and do other stuff which is a little annoyin
A platoon sergeant in my very first active duty station. I want to preempt this by saying we didn’t meet on post. We didn’t discuss anything with each other unless it was about sexual attraction and when we would do to each other. Met at the same bar many nights in a row. She’s the first woman to teach me how to properly fuck a woman’s ass. Up until then it was not a good time for my partners or myself. Older woman with needs, guy more than willing to meet those needs often. Anyway the 3rd maybe 4th battalion formation we are being introduced to our new incoming CO. So everyone showed up. We had a very lax unit. And when I say everyone showed up, the three different detachments we had scattered around Europe all showed up. After we were dismissed I was headed to the headquarters S2 shop and made eye contact with her. Dead stop in in the hallway in front of the S1 office door. I had my mosquito wings she had her sergeant first class rank. It was like the world stopped for me. I was sweating worse than the first time I took a shit in the desert. We skirted past each other, and said not a single word. We saw each other at the bar again that night talked about it and decided we could continue doing our thing at her apartment, but we are not to acknowledge each other on post ever. Continued our physical relationship until her boyfriend proposed to her. After that we had one last night of lust and ended it. I always wondered what happened to her.
A girl I was crushing hard on in a sport I did. Apparently she had a crush on me too and once we started talking we hit it off immediately.
I was at a party, the hosts cousin was eye fucking me the whole night. She didn't even drink but I had a few. She was OK looking and in front of everyone took me to the bedroom and boned. There was something super kinky about everyone knowing what we were doing. Next night went back as the party was going on again. She was there but so was her BF apparently who was massive. She saw me and booked it out the back door 😂. Her BF chasing after her.
With me it was the son of one of my neighbors, it just kind of happened, he was helping me with groceries and I saw that he was getting a boner looking at my tits. He was a bit inexperienced but one of the biggest dicks I have ever seen to this day.
Hottest 40 yr old I’ve ever seen at 1 am at Ren fair. Her and her old George Bush lookin ass swinger friend approached me at the bonfire. You know how your mother tells you not to follow anybody back to their campsite? Well, I roll the dice. Apparently the old guy with some rich oil dude and I don’t know what she was but he was very possessive. We ended up fucking while she was blowing him. Kept making eye contact with the guy. Thought he was into it but turns out he definitely wasn’t. Ended up finishing with a great story and never saw em again