Hookup/Flirtation Stories

I was traveling for work in, of all places, Jackson, Mississippi. I was there for a week, in a beautiful old hotel. Every night I would go sit in the bar, same HOT, young, country bartender. I was about 30, he was probably 25. At most, there would be 3 or 4 other people in the bar area. I'd always be the last to leave, because I was staying in that hotel. Each night when I was the only one remaining he would have a drink with me, and we would talk about whatever dumb topic. On the 3rd or 4th night, when it was time for him to close up, he said "Well, if you're bored, there's a bar that stays open just across the street." We went over, talked some more, things were flirty. We went our separate ways. Next night, no one else in the hotel bar, same scenario, this time I just said, "We could also keep talking in my hotel room, ya know." He shared that it was against hotel policy, he could be fired, etc. Finally, last night, same scenario, only this time about 10 minutes after I get to my room, I get a knock on the door. It was him. We basically ripped each other's clothes off, fucked and sucked for hours. I got his number, we met up a few times again when I was there. He got married, has two kids. I last saw him about 3 years ago.

Wow, love those stories that happen in the most unexpected of places

The best flirtations are the ones where more than one conversation is happening at once

Isn’t this exact same story on another thread from a week or two ago? Wedding flirtation hookup story..I’m pretty sure!

-100/10 OP

made out lovingly

puhlease

I am assuming OP and R1 are the same person with the same atrocious style.

I met "Duane" at the Y. The first time I saw him he was peeling a sweaty Bike jockstrap off his muscular lower body. The next week, I saw him just exiting the shower. He was wrapped in a towel, but I caught a glimpse of an enticing treasure trail snaking its way down his chest. As he passed, I glimpsed his muscular buttocks and thighs straining against the skimpy threadbare towel.

I'll write more later.

A few stories...all having to do with traveling or living abroad.

First was flirting with a woman. It was the first time I was in San Francisco. I was in my early thirties. I went for a drink at the Top of the Mark. I started talking to an attractive woman at the bar. She worked for the Athletic Department at Cal. We just git it off. She was there for some reception, but she suggested that we meet later at an Italian restaurant on Washington Square. We did. From thee she brought to various spots around SF. It was a great night of flirting, but nothing more -- I told her I was gay. The next morning, there was a package for me at the Front Desk of my hotel. It was a Cal sweat shirt as a thank you.

In Warsaw (again in my early thirties) a 20 something, really good-looking guy cruised me in the Old Town. I thought maybe he was a hustler so I played dumb.

In Munich, I flirted with a guy in the bar of the hotel I was staying at. We left together, started making out in the elevator, and ended up in his room. It was great! Turned kinky -- ended by tying him up and having my way with him -- all consensual

I lived in London one year doing research at the British Library. I brought my lunch every day, and ate it at a table outside the Reading Rooms. I bought chocolate cookies every day too from the same restaurant/cafeteria. The guy behind the counter was a bit older (late 40s to my early 40s). Very handsome...I think he was Turkish. He always smiled when he saw me and started giving me extra cookies without charge. Jesus -- we flirted for weeks.

I don't think these stories are worth much unless they end with, at the very least, some nudity or physical contact.

Gym class in high school. Super hot straight /bi guy in my class. We had a stretch where everyone would pair up, he helped stretch my legs and would caress the up and down very discreetly. We could feel the palpable sexual energy between us. We made out and jerked off several times thereafter

An afternoon's very mild flirtation, also at a straight friend's wedding, but with a twist: he had my dick in his hands the next time we met.

About twenty years ago I was a guest at a wedding on Long Island seated next to a good-looking, very engaging young Indian-American guy in med school at Cornell. He was a classmate of the bride as an undergrad and I'd known both her and the groom since then, but had never met him. We hit it off and had a great time, but I had a bf and was "married" before I was married, so it was nothing more serious than a lot of double entendres and some mutual flirtation. I did think, "Nice guy, great personality, great future." but never gave it or him much thought after that day.

Until the following winter when we met again. I recognized him right away but given the circumstances said nothing at first because of both how I felt and where we were: the ER at the Beth Israel in Boston. He was by then a resident and I was a patient with kidney stones who couldn't pee. He looked at my chart, shook his head, looked at me, and then looked at the chart again but said nothing - all very professional. Until he started to insert the catheter into my penis and said, "I'll be very careful and this will only take a minute."

The morphine had kicked in, my inhibitions had vanished, and I said, "Pity." He looked up, shocked, until I said "John and Katie's wedding, Glen Cove, last June" and he started laughing. He was great (I'd had plenty of other ER trips by then for comparison before they finally blasted 'em out with a laser) and very attentive for the rest of the night. He said I looked so familiar but couldn't place me, maybe because I was clean-shaven at the wedding and had my annual winter beard the second time we met.

I was a little miffed he didn't recognize me right away, but the care I got that night made up for it.

About twenty years ago, when I was in med school, I met this creepy guy at a wedding who kept hitting on me. I tried to be polite, but this guy couldn't take no for an answer.

Flash forward to the following winter, when I was doing my residency at Beth Israel in Boston. There this guy was. I didn't recognize him right away. He was faking kidney stones!

Was he stalking me? He was exhibiting classic drug-seeking behavior. I jammed the catheter into his penis as hard as I could. Hope I was able to discourage him.

[quote]I met "Duane" at the Y. The first time I saw him he was peeling a sweaty Bike jockstrap off his muscular lower body. The next week, I saw him just exiting the shower. He was wrapped in a towel, but I caught a glimpse of an enticing treasure trail snaking its way down his chest. As he passed, I glimpsed his muscular buttocks and thighs straining against the skimpy threadbare towel.

The next time I saw Duane, I knew I had to make a move. I followed him into the shower and slowly lathered his back, my hands trailing down to his firm buttocks. He turned to face me, we kissed deeply under the warm shower and then suddenly a marine burst in and fucked both of us.

[quote] He was by then a resident and I was a patient with kidney stones who couldn't pee.

LOL

I guess flirtation is a lost art. Let's all get back to what we're good at: hooking.

[quote] In Munich, I flirted with a guy in the bar of the hotel I was staying at. We left together, started making out in the elevator, and ended up in his room. It was great! Turned kinky -- ended by tying him up and having my way with him -- all consensual

Turning kinky in Germany - ach, wo sonst?

R13: Were you ever a student at a large midwestern university?

I have to say that, being gay and after 7+ hours of surgery, I "woke up" from my anesthesia to a hot nurse. It was late at night--my surgery hadn't even started until 1:30 pm--and I got my flirt on with no inhibitions because I was basically naked and still drugged. Obviously, nothing happened, but I enjoyed seeing a cutie after my long ordeal.

Ooh fun! I love geriatric porn.

[quote] Wow, love those stories that happen in the most unexpected of places

Yeah, who ever heard of a hookup in a hotel bar.

Charlie/r8, how did the cookie man story end?

R8 Bonnie dear, stories like these are why no college kids take your class seriously ever.

[quote] ... a patient with kidney stones who couldn't pee ...

I hate it when my kidney stones can't pee.

R21, I flirted with the man...that's all.

R22, some students don't take courses seriously. It has nothing to do with me.

Charleston, WV, Holiday Inn .... I came in near midnight, quiet lobby, asked at front desk if I had a package delivered. One guy was Cute, the other ok. Went up to my room. Rather quickly the phone rang once. Later I hearc a hall door open I looke out saw nothing but left my door ajar. Within minutes the un-cute but ok guy came in. I threw him on the bed. He blew me daily for the next three days of my stay.

I walked up to a man at lunch hour at the West Side Club in NYC and asked him if he would fuck me in the ass. He did. Does that count?

I was twenty years old at the time and had just been dumped by my “first love”. Right before the break up I’d met a not-so good looking biracial (black-white) man (early 30s) at a party a friend of mine took me to. I ended up talking with him a lot that night. He started contacting me at work (a bowling alley) about once a week for a month after that. I was annoyed a bit but didn’t have the heart to tell him to stop. I was still reeling from the break up experience and no way did I think this man could help me get over my ex. Then he showed up one Saturday morning. As he was walking towards me I could see his his dick swinging in his cotton shorts. We talked for a bit and then he left. I called him up a few days later and agreed to come over that following Saturday afternoon to his place. He greeted me wearing a t-shirt and cotton shorts. Once again his dick clearly visible. Sitting on his couch, after a little drinking, talking, flirtation I started rubbing his thigh. His shorts were tenting and his dick peaked out of the leg of his shorts. I told him I that I wanted to suck his cock. It was huge and thick (putting him at over ten inches, tip of my thumb to tip of pinky of outstretched hand is over nine inches). I sucked and slobbered over his dick for almost an hour. I experienced no gag reflex. After a break, he fucked me bareback in basically every position we could think of. My body had never been so flexible. I couldn’t touch my dick because he had me on the brink of cumming the whole time. After over an hour of this he told me I had him close. We were in missionary position. He picked up his thrusting and I matched his pace. We were both very vocal throughout our fucking. Finally he came and I jacked myself and cane also. We were both all, “oh baby, oh baby.”at the end. He pulled out gently and we both lay their, satiated.

I got picked up by an NFL quarterback at my divinity school!

Too bad, Kevin, I have a real story: I was working for an urban university and this ex-Dolphin was getting a tax degree on top of his accounting bachelor's. He was gorgeous. I was nice to him, obviously, but he was just another student to me. The guys in the program would mob him, though, and seemed to be thrilled to be with somebody who'd even played pro sports. I actually looked up his file and noticed he was a year or so older than me and a Capricorn. So one day he calls about some financial thing and suddenly starts flirting, like "how'd you like to meet up sometime?" and I was so shocked I just laughed like he was joking and then we both laughed for awhile, and he rung off by saying, "you don't know what you're missing." Long story short, he made a "counseling" appt. and shows up in a muscle shirt, so then I knew he wasn't kidding. Apparently he got my number from a co-worker and called me one of the evenings he was in town the week before Christmas. Gentle readers, he got to my place in a long underwear under jeans and a jacket. He didn't try to hide what he wanted and we had sex. Problem was, I had a crush on someone else at the time and so it was difficult to switch gears, so to speak. Plus, he was kind of not too sophisticated or even intelligent. Still it was one of the most exciting hook-ups of my life. He had a fantastic body and sure didn't mind standing around naked so you could take it in. Nice guy, too. When we realized it wasn't going anywhere, he was still nice to me at work.

One time I was going from New Orleans to Jax Fl on a Trailways bus (remember those? ) and I had missed the earlier bus so the next one wasnt until 2 am. There were very few people in the bus station and I was trying to catch a few winks when in walks this ripped,hot to death ,deeply tanned guy wearing skin tight jeans and t shirt. He had shaggy brown hair streaked with blonde and a deeply southern accent ( I heard him asking what time the next bus was) .

Needless to say I was enchante ,so I perked up and started heavily eye fucking him. I was wearing a tank top,cut off denim shorts and flip flops,and had a bunch of Mardi Gras beads around my neck. He notices me eye fucking him and sits across from me and starts making conversation. Come to find out he was an oil rig worker just in from a 2 month stint going back home to Lake City Fl.

He pulls out a bottle of bourbon and asks me if Id like some,so we sit there smoking cigs and nipping out of his bottle and Im flirting so outrageously it should have been illegal. I can tell he was new to the gay thing as he blushed a couple of times when I was particularly suggestive. BUT,I also noticed the growing mound in his jeans .

Right about then the bus pulls in and Im thinking "fuck!" ,when to my delight that was his bus too. We get on and theres maybe 6 people and they were all asleep . He and I go all the way to the back by the bathroom and sit on the long seat and continue our drinking and smoking ,and my flirting . As we are traveling along,I tell a particularly raunchy story and look over and he is fully erect and was like "goddamn, what am I gonna do now?" I said "oh honey,let me take care of that for you!" reach over,unzip him,and out pops this steel hard 7 inch fat uncut beauty .

I lean over and start lovingly sucking it ,and he responds quite enthusiastically ,then I shit you not,I feel his hand sliding down the back of my shorts and heading for my hole. Im no prude,but even I doubt we could get away with fucking right there when he whispers "what about the bathroom ?" Next thing you know,Im propped up on the sink,my legs on his shoulders,and hes giving me the slow fuck of my life . He doesnt last long considering ,but it was deeply satisfying for both of us.To this day I dont know how in the world we both fit in there,but we did. I was covered in bruises the next day. When I got off the bus the next morning the driver shot me a look of pure disgust and shakes his head.

r29, cool story. How long ago was this?

R31 1978 darling. Note I mentioned smoking in the bus station and on the bus .

Been a while since a good story here

I like the stories that do not end in sex.

Let me tell you about my Josh Hawley story...

Josh Hawley makes all his hookups pose with rubber babies, it's downright creepy.

Very hot, OP.

One day I was at Trader Joe's and this good looking cashier that I had been attracted to for months ( and assumed was straight) - when I got to the head of his line and he said- You've been coming here for a while I should introduce myself. What's your name?- he put out his hand for me to shake then said - Do you live downtown?

I got really uptight but I still thought he was JUST being friendly. One week later I was in the store looking at some items on the shelf and the same guy comes up behind me and says Hi James! as if he knew me. I finally realize he was probably flirting with me but I never did anything about it and I still think about him almost every day since 2015.

Oh well.

My work in the 90s in my late 20s involved a lot of working directly with clients on projects and spending quite a bit of time together. Nearing the end of one major job, with a week's worth of meetings scheduled, the client has a heart attack and is out for the duration, but sent one of his reports to complete the work. My assistant let me know he had arrived and was in the conference room, and I should prepare myself. It didn't dawn on me what she was trying to say (loved her and worked with her for a decade), so when I walked into the room I just about passed out. We'd spoken on the phone numerous times, but this was pre-social media and I had no idea this man was so handsome, built, and just sparkled.

We worked through the project. As the day wore on and we got more comfortable, he'd touch my arm or stand a little closer than you'd expect, but maintained enough professional decorum that I wasn't quite sure. We interacted with a bunch of my team and he charmed them all. Suddenly it was 6:30, everyone had gone home except the two of us. He loosened his tie and undid the top button, revealing a tuft of hair that caught my eye, which he noticed. I just smiled and tried to make small talk when he reached out and pulled me closer and asked if I was comfortable. All I could mumble was "yes" and he leaned in for one of the most passionate kisses I've ever received.

We had our hands all over each other, pulling clothes off. His chest was exactly the type I can't resist, nicely developed but not too big, covered in dark hair in a great pattern, with a lovely treasure trail from his pecs to his belly button, and disappearing into his pants. I traced it down with my tongue, dropping to my knees, feeling his solid 8 inch and thick cock and just as I was unbuckling his belt and getting ready to go down on him, the cleaning lady made noise and flashed the lights outside the conference room. I suggested we go to my place and he agreed, much to my pleasure.

I drove, but had one hand in his lap the whole 15 minute ride. He used both hands, and started talking dirty about what he wanted to do to me. By the time we got to my place, we were both so hot that we didn't make it out of the car before he unzipped my pants, pulled out my cock and swallowed it. He was a pro. It was like being in high school with the windows steaming and all of the discomfort of being in a car, but ending with us both cumming all over each other and making a mess. When we finally got inside, I poured us both a drink, and began again. We fucked all night. Work the next day was rough, but couldn't wait for it to be over because I'd asked him over again before I drove him to his hotel to change. The work day just flew and we managed to be discrete, but couldn't wait to get naked and fuck and flip and fuck all night, both finally falling asleep about 3 am for a couple hours before heading back to the office.

It was the last day we'd planned this project, and we'd wrapped it up in the early afternoon. It was Friday, and in a moment of impulse, I asked him if he wanted to change his return flight plans and stay for the weekend, to which he flashed his gorgeous smile and said "I thought you'd never ask." I lost count of the number of times we both came that weekend. We didn't leave my place except to go to pick up some takeout, and both didn't want the weekend to end. We'd obviously talked a great deal and gotten to know each other, but I was unprepared for it when he said he had to get home and help take care of his father-in-law... my client who'd had the heart attack. I was shocked and pissed and didn't know what to say.

"Well," he said, "at least you know I'm not going to run around the office blabbing about my wild weekend."

R39 Hot until he put your dick in his mouth. Yuck.

Bump

Nice r39, thank you for sharing

Thread deserves a bump!

[quote]and made out lovingly

Seriously? That's it?

Are we in grade school? Your big hookup story is that you "made out lovingly?"

WTF is this place anymore?

My father was in the hospital recovering from major surgery and I was cruised by someone who worked there. I visited dad every night at the same time and every night this guy (very hot btw) would pass by his open door and smile and wave. One night he motioned for me to come out into the hallway, handed me a note with his phone number and walked away. Of course I called him as soon as visiting hours were over and we hooked up that night. He had an amazing ass that I fucked for hours. Oh, dad recovered btw.

Haha, nothing wrong with making out, that’s sometimes the hottest thing of all

Hot one r45, and with a happy ending too!

OP that never happened, but it was hot and I enjoyed reading it all the same. Thanks.

R1 I think you meant to say he fucked you and you sucked him. Thanks.

I enjoyed reading it as well. So much so that I became wet all of a sudden

I’m actually thinking r1 happened

R11 Why do half the recollections I read on DL involve kidney stones?

Hot story though r11

What is it about weddings? Like several posters here, I’ve had some fun times at weddings.

In my late 20s, I was at a wedding of a college friend. I’d never met her younger brother, but had heard about him from her and their other sister. They were always worried about the girls he dated. He was a cute short guy. The reception went late until the night, lots of drinking. At one point he leans into me and tells me that he is “straight” but that I’m a handsome guy and he used to mess around with his high school friend, and then asked me to please not tell anyone. He then sort of led me into some trees on the edge of the reception hall grounds and we made out big time. Hands did get into pants, but no orgasms. It probably only lasted 10 minutes, but it was really hot.

I’ve only seen him once since then, at their mother’s funeral. He was with his wife (who yes, the sisters hate) and a kid. We spoke briefly and he acted very pleased to see me. I’ve never told anyone, because those sisters would freak out.

R54 I think it’s like the one non-business place as an adult that you meet new interesting people in a semi-formal setting where you are both likely drunk? It’s inherently hot.

Yea, plus men dressed up nicely with sharp ties on, gets the pheromones going

R39, you talked a big deal for a whole weekend and he never mentioned he was married? what were you talking about?

Mmmmm nicely dressed men at weddings

I worked at the ad agency Ogilvy about 15 years ago as a copywriter here in NYC. The place is massive of course, and executives from Ogilvy offices around the world would visit for various reasons. Sometimes a new business pitch. Anyway, one morning I rounded the corner to where I sat and noticed a very handsome guy sitting in the seat next to me - it was an open office plan and everyone sat at these long ass tables. When I sat down he immediately flashed a beautiful smile and quipped in an impeccable British accent "Careful! Not too close. I was out last night and I reek like a mojito."

So...there is a type of English guy that just melts my knee caps. I call them the thoroughbreds. As in flawless breeding. These are the guys who went to Eaton or St Paul's, play rugby, drink the bar dry, have thick, muscular haunches and chests that always seem to be bursting out of their tailored shirts. That was this guy. He was a strategist working on a big project for a few weeks. I was immediately tongue tied but he really was friendly so I loosened up pretty quickly.

We got chummy. Took lunch together. Which led to drinks a couple times a week. He was married with two small kids and didnt seem the least bit put off that I talked openly about the guys I hooked up with. In fact, he was curious and would ask for more details. Ha. Anyway, the last day he was there I took him out for drinks and we got fucking annihilated. We started at a pub around the corner, got dinner at Raoul's down in Soho then ended up at a dive bar on the lower east side.

That last bar we were at just pushed us over the edge. At one point, I got up to take a piss and about 30 seconds later he came in and stood next to me at the urinal. He unfurled this massive cock, smiling sheepishly. I cant even tell you how it happened, but the next thing I know, we are in a toilet stall and I was sloppily sucking his dick. He pulled me up at one point and started making making out with me, then said "I taste pretty good don't I?" (thank god the bar was dead...the toilet stall door was flimsy). I don't remember getting home that night.

I called out sick the next day and then he was gone. I got an email from him a week later saying we'd keep in touch. Whatever. The coda to this story: he found me on Facebook a few years after that. And started sending me videos of himself jerking off. HA. So so fucking wild. He only sent 3 or so before he disappeared off social media altogether but I still have them. And I rub it out to him every so often.

I have a few stories. I’ll go with one of my oldest. I introduced myself to the gay scene where I lived when I was twenty. I’m an American born and raised in a foreign country where there was a sizable American/military presence. Anyway, I’d just been dumped by an older American military guy. He was my first love and I was heartbroken. Right before the break up I met an unattractive black guy, about the same age as the soon-to-be ex-boyfriend. We’d struck up a conversation at a party and he tracked my down to where I work (a bowling alley). He called me a few times at work, then one late Saturday morning, he showed up in person. Fortunately, no customers had come in yet. He showed up wearing grey cotton shorts - commando. I could tell, because as he was walking towards the counter his dick was visible and swinging. The next phone call with him was initiated by me and it was for me to come over to his place. I got to his place, he offered me a beer. He was wearing some cotton shorts again, and visibly commando. We talked for a while and I started rubbing his leg. He got hard pretty fast. I asked him if I could see it. I ended up sucking his 10+ inch cock for almost an hour. We took a break, drank a beer, smoked a cigarette and headed to his room. He penetrated me with me lying face down and he’d been grinding against me for a few minutes. It basically slid in. Didn’t need a whole lot of lube. My ex had a beautiful face with a below-average dick, penetration was difficult the first few times. With this guy I just remember pleasure. We fucked in that position for w while, then doggie-style, side-saddle, standing up, missionary. At one point he pulled out, he said, “Wow, you’re gaping.”. We went on for a long while and I didn’t want it to end. Big dicks clip your prostate easily and keep you on the edge of cumming. We got back to original position He told me he was close, so I started pushing back/up as best I could in that position. Then he asked/said, “Can I cum inside you?” Followed almost immediately by “I’m cumming inslde you, I’m cumming inside you!! “. When he was done we both laid there loudly catching our breath. He said, “Thank you.” He also said he hadn’t meant to cum inside me without getting my permission first, but that it just hit him suddenly. We ended up hooking up several times after that, before I moved away and he introduced me to other gay black men and experiences.

I have a few stories. I’ll go with one of my oldest. I introduced myself to the gay scene where I lived when I was twenty. I’m an American born and raised in a foreign country where there was a sizable American/military presence. Anyway, I’d just been dumped by an older American military guy. He was my first love and I was heartbroken. Right before the break up I met an unattractive black guy, about the same age as the soon-to-be ex-boyfriend. We’d struck up a conversation at a party and he tracked my down to where I work (a bowling alley). He called me a few times at work, then one late Saturday morning, he showed up in person. Fortunately, no customers had come in yet. He showed up wearing grey cotton shorts - commando. I could tell, because as he was walking towards the counter his dick was visible and swinging. The next phone call with him was initiated by me and it was for me to come over to his place. I got to his place, he offered me a beer. He was wearing some cotton shorts again, and visibly commando. We talked for a while and I started rubbing his leg. He got hard pretty fast. I asked him if I could see it. I ended up sucking his 10+ inch cock for almost an hour. We took a break, drank a beer, smoked a cigarette and headed to his room. He penetrated me with me lying face down and he’d been grinding against me for a few minutes. It basically slid in. Didn’t need a whole lot of lube. My ex had a beautiful face with a below-average dick, penetration was difficult the first few times. With this guy I just remember pleasure. We fucked in that position for w while, then doggie-style, side-saddle, standing up, missionary. At one point he pulled out, he said, “Wow, you’re gaping.”. We went on for a long while and I didn’t want it to end. Big dicks clip your prostate easily and keep you on the edge of cumming. We got back to original position He told me he was close, so I started pushing back/up as best I could in that position. Then he asked/said, “Can I cum inside you?” Followed almost immediately by “I’m cumming inslde you, I’m cumming inside you!! “. When he was done we both laid there loudly catching our breath. He said, “Thank you.” He also said he hadn’t meant to cum inside me without getting my permission first, but that it just hit him suddenly. We ended up hooking up several times after that, before I moved away and he introduced me to other gay black men and experiences.

Nice story r61!

In the 90’s : I was in a porn shop buying a movie. It was on the bottom shelf. I bent over to pick it up & as i did this a man who was also in the aisle stepped behind me & pushed his crotch into my ass. Nothing came of it but i wasn’t offended. It was strangely erotic.

Adult sex toy shop, similar experience with a guy checking out dildos next to me

R62 Thanks. R63 That was simple and erotic

These stories are stirring me all over

Lol same

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R63 nice

R59, wow that’s hot

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Ha love a good flirty story. Sat next to a hot guy on a flight once and our knees were having a separate conversation. It was so hot

That is hot, r72.

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Nice Physique

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