People Shared Stories Of The Boldest Sexual Advances They’ve Made And I’m SHOCKED That Some Of These Worked

“You miss 100% of the shots you don’t take” — Michael Scott, Wayne Gretzky

That quote doesn’t only apply to sports, it’s a reminder that in life you only get a few truly great opportunities, and if you don’t pounce on those chances you’ll end up at home on some website with ‘tube’ or ‘hub’ in the URL, if you get my drift. Below, a bunch of people shared stories of the boldest sexual advances they’ve ever made, for better or worse, and I hope these will inspire some carpe diem in you bros (via AskReddit):

Was at a party and I was talking to this one girl and then a friend came up and was chatting with us, at one point my drunk ass asked if this is how the threesome starts. Turns out, that is how the threesome started.

I had to get leg surgery, while I was out getting cut up a girl who was kind of on the periphery of our friends also broke her leg. So I’m walking around on crutches… she’s walking around on crutches. Our eyes meet, and I said something like “wanna find out if two people with two legs can fuck?”. She said yes, and the answer is… no unless you have something to hold one of you up.

Back in college I was at a Halloween party. There was a girl dressed up like a condom or sex protection or something, I can’t remember. Anyways, she had like a sash/huge string of packaged condoms around her.
In my drunken confidence, I walked up to her and asked, ‘Can I borrow one of those?’ She replied ‘Sure for who?’ and I quipped back ‘To have sex with you.’ and she just said ‘ok’
Had sex, didn’t know her name and never saw her again. 7/10 but missing the rice.

weird jackie chan condom bow down bowing

My boss was a really good looking woman. A milf describes her quite well. Her personality was relatively flirty so we kind of traded pick up lines here and there, but playfully. We get sent to an event in Vegas, all expenses paid with a few other employees. As it came closer people were in an accident or quit so it ended up just being me and her. Day 1 in Vegas we get Hammered and we’re dancing kind of hanging on each other all playfully though because that’s what I thought it was. We somehow managed to find our way back to the hotel and she said “I hope you have a good night.” I responded with a great drunk idea of saying “I think it will be, I’m going to finish myself off thinking of you.” I was about to slap myself but she responded with a mischievous smile and said I outta come inside so she can show me around. We did horrible things to each other in that room, my love for eating ass was also born that night as well. It could have went pretty bad but the stars lined up for me in that moment. Please don’t try to hit on your boss though there’s a very good chance it won’t go well
TL;DR: Hit on my boss, she gave me a full tour of her birthing caverns instead

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I was at a party and a girl said to me “can you hold my beer?” I didn’t know her or had talked to her before, but I said “ok” and she gave me her beer to hold.
She then took off her jacket and I handed her beer back to her like a normal person would do. She said “thanks.”
I then said to her “can I hold your beer again?”
“Why?” she asked.
“Because every time I hold your beer, you take something off.” I said
“Follow me.” She said. And I followed her upstairs and we had sex.
I love holding other peoples’ beers.

I asked a girl if she’d be my fitness motivation, and asked if I could go down on her, if I reached my weight loss goal. …She replied by saying “Why wait?”

I asked a girl in a club if she wanted to fuck. She said she’d like me to fuck off. Could have gone worse but was unlikely to go better.

TorchIt: We grew up together. I’ve known him since we were about 8. We both crushed on the other a bit throughout high school, but the timing never worked out. When one of us was single, the other was taken. We graduated, lost touch…you know how it goes.
I married a guy. Eventually it came out that he was having an affair, so I packed my stuff, left, and changed my relationship status to single before hitting the road to meet a friend for a much needed drink.
As I’m nursing my stupid cocktail in abject misery, my phone rings. It’s…Mike? Really? Haven’t-seen-except-in-passing-for-ten-years Mike? THAT Mike? I answer it, and he asks where I’m at. I relay my location, to which he replies that my taste in bars is terrible but he’ll be there in fifteen minutes. Click.
Exactly fifteen minutes later, he walks in the door and spots me at the bar. He walks over and I go to give him the long lost friend hug along with a “Wow, how are you?!” Instead, he grabs me by the ponytail, pulls my head back, and kisses me passionately until I can’t breathe. When he finally lets me go, he says “Order me a Blue Moon, dear. Two oranges,” slaps me on the ass, and goes to the bathroom.

That was five years ago. We’ve been together ever since, and our first child is due in May.


Me: “Wanna fuck?”
Her: “Nope”
Me: “Okay cool”

Airplane. The one and only time I’ve ever sat next to a hot chick. I had 2 screwtop (decent Penfolds) bottles of wine I had bought at duty free. As soon as we took off, I said, “wanna get fucked up?” Four hours later and 45 minutes after landing, we were bumping nasties at the Four Seasons in Hong Kong.

A girl from school messaged me on Facebook and asked me to hangout. We met at a bar and she was definitely flirting with me. She was talking about porn and asked if I ever watched it with a girl and I said no to which she replied that I should. I leaned in and whispered in her ear “Let’s go to your place and watch some porn and see where the night goes?” and when I leaned back she smiled at me and said okay. Got to her place and she was a bad kisser and was just all over the place. It was impossible to find any rhythm with her and it was a huge turn off. I didn’t stay long and we never talked again.

This one’s from a lady…That is an important distinction in the context of this story.

I am pretty fond of performing blowjobs. And I’m very curious to what they feel like to recieve. So, in college last year I asked one of my older classmates, who was flirting with me all semester, what a blowjob felt like.
He gave me some bland ass answer. So I took a deep breath and said “if I sucked you off after class, would you give me an answer?”
Blew a load in my mouth and almost gave me a speech about it.

talking speech nigel thornberry the wild thornberrys

This sounds like something a child would write.

A girl asked how my first kiss was like.
I told her my story, before the “What about yours?”
“Oh, that’s great! Mine on the other hand, was awkward…[shares stupid first kiss story]”
“Wow, that kiss sucked. Would you like a better one?”

I’m not very outgoing. Anyone I have been with I usually have known for longer than a night. This was one of the very few instances where me getting out of my comfort zone paid off.
Went to New Orleans for H4H for a week with other college students. We were being housed in a parish that was about 3 blocks away from a downtown area, so after we were done building on houses, we would go out and get fucked up. One day during the week, we all got to go to the French Quarter for the day to do whatever. Me and some friends went to a bar and grill to grab some food to help soak up all the alcohol that would be entering our system that day. The bartender that sat us was incredibly gorgeous. About 5’3″, hundred pounds soaking wet, and perky both in personality and chest. We flirted a little bit throughout the meal and when I went to get everyone drinks. As we paid and we headed out on the town, I thought, “What the hell, I’m only here for the week,” and so I went up to her, and asked her
“When do you get done tonight?”
“8:30, if no one calls in.”
“I’m only in town for the night, and I’d love to see you after work. I’d especially love to fuck you.”
At this point, I’m sweating bullets, and not just because it’s New Orleans at 95 degrees. I thought for sure I’d either get laughed at or smacked in the mouth. Bless her soul, she didn’t skip a beat.
“Definitely! Come by and walk me home.”
To say she was a freak in the sheets would be an appropriate description. By far the ballsiest I’ve ever been in picking someone up, and definitely the only time it’s ever worked out so well.

sexy girl sex fuck bed

Told my best friend I wanted to fuck. He agreed. We did. End case.

Everything about this one is insane.

In high school I fucked off and took a lot of drugs and wound up having to take a math class in summer school to even keep me on track to graduate. It was me and a bunch of other lowlifes schlepping our asses to school during the motherfucking summer to do math.
One day after class a girl I had never spoken to in all my years in middle and high school asked if I could give her a ride home. I thought I was a real bad motherfucker so I said “sure, then we can smoke a bowl and fuck.” Without even missing a beat she said “okay.”
It was at this point I realized I was a big fat pussy, because my heart starting beating out of my chest and my palms got sweaty, just at the prospect that she might be serious and I was about to get laid.
I drove her home and when we walked in her goddamn parents were on the couch and the whole house reeked of cat piss and weed. We went to her garage and sat on a couch (yeah, it was couch in the garage level of white trash). She said she didn’t have any weed (the primary bread winners of the household sitting in the living room watching Rugrats must have smoked it all) but that her older brother had a bottle of GHB in his room.
We drank a couple caps of GHB and started making out until I got hit with a wave of nausea like those old videos of the devastating effects of a nuclear bomb and started emphatically vomiting in her driveway. Her father came out and said “if he dies, he ain’t dying here.” I called my mom to come pick me up and told her that I ate bad chicken from Wendy’s and was too sick to drive home, then went home and went into a G-hole and slept for 22 hours.
I never did fuck that girl but she did pull her tits out and give me a handjob on a lifeguard stand down at the beach. A year later, we both graduated on time.

Looked a girl in the eyes without blinking, “I want to do a sex on you.”
Man did her husband kick the shit out of me.

Went on a first date with a girl from Tinder, just kinda walking around and getting to know each other. It’s getting dark and we’re sitting on a park bench talking. Forget what I said but she responds “well that’s surprising”.
“I’m full of surprises”
“Like what?”
kisses girl
Make out ensued and 15 mins later I’m fingering her on this bench and she asks “Am I going to get to fuck you?”
Didn’t really think of it as bold at the time buy looking back I’d say it’s my top moment.

Sleeping in the same bed with a girl at a buddies cabin (weekend trip with a bunch of us). We had never flirted or anything. Anywho. We’re both in bed, about to go to sleep, I ask if I can go down on her, because i had never done that before. She was shocked, but she said maybe later if she couldnt fall asleep. 5 minutes later I was eating her out. Good times.

He shoots, he scores.

Being 18 and a student, had a gf whose friend from back home came to stay, as my gf was having a night out for her 19th birthday. Inmediately clicked with this girl, knew she liked me – she was the petite brunette Yin to my buxom blonde gf’s Yang.
Night out ended with the two of them doing drunken jokey lipstick lesbian stuff on the dancefloor. Sensing an opportunity, I put my arms around them both, pull them close and give it “How about we go back to yours and do this properly?” in the most serious tone I could manage. Somehow the answer was positive from both. Fucking jackpot.
Come to think of it, the second boldest was the same night… Because of some possessive streak, my gf had insisted that I cum in her mouth at the end of the 3 way. I went and grabbed a shower and a sandwich afterwards and came back in to find my gf snoring but her friend awake. “I wasn’t finished with you” was all it took to get her to ride me on the floor next to the bed.

Last but not least, sometimes all you have to do is ask.

Oh yup, got a short but sweet one. Walked into my flatmates bedroom and asked her if she wanted to fuck. Payed off

parody flirting flirt the little mermaid fucking


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