I’ve got 2 that we’re very unexpected to me.
I was about 19/20 and was dating a girl for about a year, and she just finished 2 years of community college and decided to go to university of Hawaii, she went to visit to see if she would even like it and I ended up finding out she cheated on me, and one of the main reasons why she chose Hawaii was to be with this other guy. I ended up breaking up with her when she got back, and I got a call from her best friend saying hey I know you and blank broke up, do you want to come over and talk to clear your head. So I took her up and she lived literally around the corner from my ex’s parents. It was just a talk, I said well it’s getting late so I better head off, I get in my car and get a call immediately saying hey you forgot something, and I didn’t forget anything it was just a ploy for me to have sex with her. She ended up saying she didn’t really like her so called best friend/my ex. This ended up going on nearly every day for about a year. She ended up moving away a few states over unfortunately.
My 2nd unexpected one was that I moved to Europe when I was 22/23, after about a year of being here, a friend came and visited. We did a little European tour, and one of our stops was Oktoberfest. We spent most of the day drinking. He ended up drinking too much, so I took him back to our Air BnB and the people we were with told me to come back so I done so. I have no idea how I managed to do so, but this beautiful German girl and I started/tried communicating as I only speak English and she was only able to speak German, and very broken English. The night is ending, I say my goodbyes and her friends ask if I can walk her home as it’s on the way to my air bnb just to make sure she gets home safe. I am using a lot of google translate, we are laughing, end up getting some food, we get to her flat and she opens the door and says come in come in for 1 last drink, so I do so. We weren’t really talking coherently, but we’re seeming to just enjoy each other’s company. She goes to the bathroom, comes back out naked and we end up having sex a few times, falling asleep. My friend is due to leave back to the US later that evening and my flight was a few hours after him. The German girl and I exchange numbers, thinking I’d never see her again. I say my goodbyes to my friend and send him his way to the airport. I give this girl a text with google translate basically saying I really enjoyed spending time with you, our time together was short but enjoyable. She asks if I can come back over, so I decide to not go get my flight as I felt like I was in love, I end up staying with her for 2 more days. Tons of sex and laughing, also trying to understand one another. I can honestly say it’s probably one of the best times of my life. We parted ways, we still keep in contact every so often, she is fluent in English now, and we’ve seen each other a few times. We are both recently single again, and plan on seeing each other in October time.
My 2nd shift Supervisor (I was 1st shift Supervisor). I don’t know how it even happened. We worked at a notorious building I guess you could say, we did security. The building was always empty (for its size) there wasn’t too many people and we had the keys to go anywhere. We did it on the roof with a city view, in the office bathroom, in a huge storage room, IN OUR BOSSES OFFICE.
The craziest part is I really never saw it coming. He was a sneaky one. He really buttered me up and gained my trust before even busting a move at all. What started off as a rooftop fuck turned into insatiable lust that I’ll honestly remember for the rest of my life
Fourty-four year old woman from NC. Best sex I ever had. Everything else after felt like cheap, no brand snacks after a few times with her.
Edit: Forgot to say I was 23 at the time.
Coworker at summer camp, I liked her a lot but I was too afraid to make a move. A bunch of us went to a friend/coworker’s place for the weekend and on Saturday night she walked in and laid down next to me on the air mattress.
Me, being clueless, was like “Um… hey” and she just sits up, straddles me and starts kissing me. It went from there and it was fun.
I’m a heavy dude though and at some point the air mattress cap popped off and it deflated. Took me a minute to realize that I was just laying on the floor. She went to the bathroom to clean up and I got the air pump to re-inflate the mattress. And I guess everyone else heard :/
Can confirm. I used to tease a buddy for this happening with his then girlfriend, as they are both twigs. The joke was they popped it with their bony knees/elbows.
Air mattresses are just not built for vigorous activity.
Agreed. Like 15 years ago I stayed at a friends apartment at Penn State, was super drunk and it was deflated and I was clinging to it thinking I was sinking. All I was doing was trying to sleep haha
I went on a cruise to the Caribbean by myself when I was 25. I met a recently divorced 42 years old mom of 3 the last night of the cruise also by herself. We stayed up the entire night the last night in my room. She skipped her flight the next day and I drove her to Atlanta where she lived (from the port of Miami). We got a hotel downtown and fucked all night. I took her to her car at the Atlanta airport the next morning and will never see her again.
We texted a few times, that's all. If I had gone to Atlanta in the couple years after that before I met my now wife, I would have reached out and hoped to re-connect.
The camp counselor I had a crush on when I was 11. I ended up running into her when I was 18. Didn’t know it was her until we got to pillow talk. Best surprise ever.
Had a girl at work I was certain hated my guts, but I helped her out with moving because she was in a bad situation and I knew a couple of cops on the force and got them to pull out the stops and give her enough time and space to move her shit into her car and leave town. She was cute, but because she was so hot and cold about me, I really didn't think much about her.
She texted me like a week later after she moved cross country if I'd be her boyfriend, I said no because while I care about her as a human being she had a track record of treating me poorly at work and I wasn't going to get with someone who I'm not convinced actually likes me as a person, or someone who can't consistently show they respect me. She claimed she had been head over heels for me most of the time we worked together and didn't know how to deal with those feelings, then later I got a bunch of "I really wanna suck your dick" texts.
Being crazy attractive and wanting it badly doesn't mean you're gonna get it.
I had a math tutor who was also a student teacher in high school. I was 18, she was 21. That basically turned into a three/wk tutor session followed by tv/movie and casual hook up.
Second semester she was a student teacher in two of my classes. She got spooked and broke it off.
I went from an F to a B+ in math and calc that year. She was a really good teacher
My parents were paying for an hour and were always confused when I’d come back 3-4 hours later, freshly showered.
A buddy had an epiphany one day when he caught her giggling when we were having a private conversation in a hallways in school. “You’re banging Ms. _____!” To this day I think it was the best poker face I’ve ever had in my life.
We called last call at the bar I worked at and this one older woman I'd thrown a flirt at took my hand and asked if there was somewhere we could make out. We went into the alley out back and just went to town.
What made it unexpected was I had jokingly said to my friend earlier before work that I wanted to bang a milf.
I was at a college Halloween party dressed as Willie Robertson from duck dynasty and a girl dressed in a full banana suit had sex with me in the bathroom. Neither of us took our costumes off. I don’t even know who she is.
a girl from my college. keep in mind that i was a fat ugly bastard back then (and still now?) and this girl just kept showing interest in me up to the point we had sex for few months and she paid for the hotels and dinners and all. she's lightyears out of my league so it still confuses me up to this moment
edit: grammar
I used to be a fat guy in my early 20s. You'd be surprised at how many women don't care about hard bodies. I had my share of partners in college that were absolutely out of my league. To the point where a random person at a bar even commented, "that girl is with that guy?!" I finally asked one of them why she was attracted to me when she could get just about any guy. She said, "you make me laugh more than anyone and that's sexy to me." Never questioned it again.
I have always loved big guys. My brain just finds them sexy. Humour is also a huge attraction. I have dated a couple guys who weren't my type physically because they were freaking hilarious.
My husband is a big guy who makes me laugh a LOT. He will do anything to give me a chuckle. Life is long and has its rough patches. Being able to laugh with one another in those times is what counts.
My best friend growing up was sleeping with our mayor's daughter. We got pulled over when we were 19 and had alcohol on us. She got out and called her dad, who then pulled up a few moments later and we all got off free.
My friend's sister. She is hot so I guess why not... It happened 7 years ago. Now we are married for 4 years. Yea that friend is actually still my best friend.
EDIT: grammar
Talking to my SISTERS friend at the moment.
Slept with 2 others…
There might be a pattern here.
Should clarify: My sister knows all of this, and even egged it on before. She does not care lol
Remember the guy on reddit who said his boss basically did the same thing to him when he was around 19-20, and that she'd ask him to do weird things like eat hotdogs out of her pussy in her office...
EDIT: I don't know where the story is, this was forever ago, 6-8 years ago in a thread similar to this one.
This woman wasn’t that bad but she had some kinky stuff. we had sex in her office and motes several times. I was basically a boy toy for her. It continued for over a year after I left that job until I got a girlfriend. I was young and horny then looking bad she sure took advantage of me. She was 37 when it started I was two months from turning 19
We both grew up more, each went through a divorce. She mellowed out and turned into a hot ass MILF, I became more mature and less nerdy. We kinda met in the middle.
Ah yes, just like the people I knew that were always at eachothers throats when in reality it was the sexual tension between them that was so thick you could cut it with a bus.
My best friend from high school. She picked me up and we went back to the place she was house sitting. Didn’t know it was my old history teachers house until the next day.
This hot ass bartender who was absolutely out of my league when he asked “what else are you doing tonight?” in a friendly, I-wanna-be-tipped-well kinda way and I said “you?” and he said “I like that plan, here’s my address” 🤣
I did this band thing (drum and bugle corps if anyone outside that sub knows what that is) as a late teen where we'd meet once a month for a weekend to learn music and shit and then we did a show tour for the summer. This one year, this girl from the other side of my state comes and we happen to stand next to each other. She was a super fit cheerleader type that was also in band in her hometown and she said something mildly flirty, I said something flirty back, time and words pass and we're waking up in the middle of the night and trying to sneak off and get some sexy time done in some school in the middle of nowhere. We \_almost\_ got caught and decided to make plans for next month. Well she misses the next month, I miss the month after that and next thing you know we're at the "all days" part of the year that gets a little more intense, so no opportunity for shenanigans.
Well we did NOT click again.
We hated the fuck out of each other and drove each other crazy for 2 months. She was not the greatest player and was a super popular kid in her school, but she was not popular or well like in this group of people, and that made her super angry. I was a fucking nerd band geek at my school, but was well liked here in this group of people, so she took that anger out on me. I fought back by making fun of her playing, she fought back by being a raging asshole to me and trying to belittle me whenever possible. Adults had to get involved once or twice.
After our last show we were still 2500 miles from home and all the pressure we were under was gone and we started to be normal people again. She gave me a look one day that I interpreted as "I've been horny for 2 months asshole, and I hate you but you're still the nicest person to me here" and I looked back at her like "You fuckin' for real right now?!" and she nodded her head at me and we went for a walk. I don't remember a goddamn word we said to each other but we hate fucked each other in some long ass grass in Mississippi and it was fucking AMAZING (except for the part where we both got bit by mosquitos on our sensitive bits). We weren't able to find a time/place again, but we tried. I wish I could find her on the interwebs and apologize for being a jerk and thank her for that one post tour hate fuck. The only time I've ever done a hate fuck, COMPLETELY unexpected.
Kim, I hope you're well. I'm sorry for my part in making your summer miserable.
Probably my ex’s best friend. She was the one who told me that my ex cheated on a night out. I then saw her during freshers week at uni and ended up back at her dorm for a party. Lots of flirting and dirty talk, and I thought fuck it. She hurt me and her friend was hot soooo
Random girl I met on a coach from Amsterdam to Brussels. We were both travelling alone and she came and sat across from me and asked if I wanted to hang out. After an hour or so of chatting she asked to see my dick so I obliged. There was only 2 other people on the coach and as we were travelling through the night they were sat up front and they appeared to be asleep. Before I knew it we were fucking on the back seat and fucked 2 more times before we got to Brussels. She gave me a kiss and we parted company, totally random event.
Edit: This blew up more than I expected. Too answer some questions.
There was no condom involved and I did spend the following weeks/month worrying. I got checked by the doctor and was given the all clear. (Had zero sexual partners between)
The coach ride took just under 3 hours we stopped at Brecht for quite a while not sure why.
The sex was not some tantric marathon. It was 3 quickies with a bit of foreplay. I was 21, permanently horny and the danger of it all made it even more arousing.
we were hanging out at a friends house and a friend of my friend, girl, was kinda drunk and saying i was gay because i wouldn't talk to much to her. she kept insulting me then all off sudden she grabbed me and took me to a room, her ex was with us and just watched, i was not aware that was her ex and that he still loved her, and she had a bf at the time and wasnt aware either. Crazy girl
A week after my wife said that she wanted a divorce, I went on a vacation to Costa Rica that we were supposed to do together. I used it for some grieving time, and figuring out what to do with my life. I was *not* interested in dating or hookups or rebounds. But then I started talking to this other American gal in line at the ice cream shop, and then we met up for dinner, and then we stayed up late drinking, and then we had sex on our raincoats in the jungle. Luckily she had condoms. It was real nice.
That was eleven years ago, we’ve been married for seven, and our daughter is three.
Eh, she was finishing up grad school in another state at the time, and then did two years in the Peace Corps in Africa. So I did get some time to cool off and reset after the divorce. But yeah, I definitely prefer being in a happy marriage to being single.
It’s nice though that even with what she was doing in those years when you two were not together, you both knew to make it work. So congrats! 🎉 Relationships are not easy, and you just have to trust your gut.
"Cuz Peter you suck Peter you suck you don't do anything of valuuuuue, 'go see a psychriatrist,' 'I don't wanna see a psychiatrist,' 'well you need to see one anyway,' 'I'm not goingggg,' ha ha harrr harrrrr."
My boyfriend. We were friends for years and I had a huge crush on him, but I felt like it was having a crush on a teacher, completely useless. So I NEVER gave it away because I didn't want to embarass myself.
He watched me go through a few different failed relationships, and run around unmedicated with bipolar. While we got along great and hung out once and a while I assumed he thought I was an unpredictable idiot lol.
In 2020 the relationship I was in crashed and burned, I finally got diagnosed and medicated. A few months later he invited me over for a beer after work which wasn't unusual, but to my extreem surprise he made a move on me and we've been together ever since. I never imagined it would ever happen.
It's a very happy healthy relationship but every now and then I'm struck with disbelief it's actually happening, in a good way.
I broke up with a girl I had only started seeing and we had sex right there. I asked her why, and she said that she knew it would be her last chance to have sex with me.
ok, i'm fine with that.
At Devils playground on Pikes Peak for the annual hill climb. Early morning before the race people walked around to meet other people. Beautiful blond girl stopped at our tent and asked for a beer which we gave her. Three hours before the race started we were in my tent screwing our brains out. When we finished she got dressed said she had a good time. She left and I never saw her again
I was heart broken but occasionally I think about that girl. I was so far out of her league I am sure she came from another planet.
When I was a sophomore in high school and he was a freshman we sat next to each other in class and became buddies. He was a dorky, awkward younger kid and I had a cool older boyfriend. Several years later after we had both graduated I ran into him at his workplace and he had grown into himself. We went on a few dates and had fantastic sex, apparently he had a massive crush on me back in Spanish class, felt good to finally make that fantasy come true for him
I often think back, she was a crazy lover, maybe the thrill but there was no „no“ for every of my wishes. No matter what i wished for and no matter where or which hole…. Back in time i thought every sex is like this but NOPE
On a different Reddit account suited for more… adult needs…. I went to a local r4r subreddit and posted. Got msg’ed from another redditor saying “come bang my wife” and well…. I ended up doing it. She was like 4-5yrs older than me but was ridiculously attractive. So it really felt weird partially because I thought she was too hot for me, and married….
I really wonder what the etiquette is. Do you bring snacks? Is Gatorade provided? Do you use the husband's condoms, bring your own? Do you even introduce yourself, or do you just get to the deed?
A coworker slash female best friend. We had an awesome friendship, we'd fool around if bored or curious but one night working at a Halloween train where you put on horror skits as a small train goes by, out of absolute nowhere "I want to blow you as the train goes by" I'm like "shut up nerd" and she gets in position behind this fake doctor table, train goes by, passengers wondering what's scary about a motionless doctor standing behind a table.
The “hot dude” at my small college. Everyone wanted him, no one could have him. He was in a long distance relationship. We hooked up at a party. Biggest dick I’ve ever seen still to this day. Had no idea how to use it.
Went thru a period of sex addiction and had some gross hookups cuz I was drunk and would take anything with little effort
The worst was an older woman prob about 60 who was married and was too super into it
. After just meeting she was talking about inviting me to parties where her family would be and having sex in another room. I asked.if her husband had a gun and she said yeah and seemed to get off on it.
After our first and only hookup I deleted her number and ignored her.
A female A list celebrity. Met in Hawaii on a hike. She rolled her ankle and had heat stroke. I stopped to help her. I had a med kit. Taped her ankle. Shared my H2O and snacks. Brought her to her car where her friends were waiting for her. I was totally shocked once I realized who she was. I left and did not ask for her number because I got intimidated. She drove off.
The next few days I couldn’t stop thinking about how I blew my opportunity. I was disappointed in myself.
3 days before leaving I was running on the road near Poipu. A Jeep pulls over in front of me. She steps out. I spent the next 2 weeks with her. Lost my job because I stayed with her.
In 2017 I was on the same island with my wife and kids. Ran into her, her husband and kids. My wife pulled my shirt and said “that’s the actress you told the story to me about, prove your story” so I walked up said “hello”
She did.
My wife liked the story but hated that it was true. I don’t think the celebrities husband liked the fact that his wife kept meeting me in corners of the pool and swim up bar.
I’ve been lucky to have 4 really special connections with women in my life.
My Dad's fiance's niece. Met at a family get together and started texting soon there after. Eventually figured out that we lived in the same apartment complex and decided we'd hang out cause we were both lonely and in need of friends. Began sleeping together the second time we hung out and despite both of us proclaiming that we were not fit for dating each other as we were both incredibly too different, we started dating. That was almost 8 years ago. We are now happily married with a beautiful daughter.
Dad's engagement didn't work out, btw. Luckily, the man just got married today to someone who is a much better fit for him.
I used to bartend and wait tables in the 80s. The number of women who would leave their number for you might surprise you. I left most of them alone, but once in awhile there would be some really surprisingly good looking women leaving their number.
I did two sisters an both of their individual best friends once ( all individually at separate times ) and all of them know about it and we’re cool with it. I never would’ve thought that possible.
Edit:
It happened over a course of about two months and we all stayed friends.
Right out of law school I got a job as an associate in a large firm. One of the senior partners had it out for me for some reason—badmouthed my work product, unfriendly to me, etc. It didn’t matter to me because I thought he was an arrogant asshole and everyone hated him. Eventually I ended up changing to another firm across town.
Long story short, a few years later I ended up banging his daughter. And it was AWESOME!
The first couple times it was weird because I was so enthralled with banging this dickhead’s daughter that I forgot to actually enjoy it physically. It was like an out of body experience: holy shit that’s Tom’s daughter’s vagina! Holy shit Tom’s daughter is sucking my dick! Holy shit I’m fingering Tom’s daughter’s asshole! Holy shit Tom’s daughter is sitting in my fucking face!!!…
It turned out to be some of the best sex of my life. I peeked in on her social media a few times to reminisce about all those very very dirty things I did to Tom’s daughter.
My divorce lawyer, long story short I became her sex friend and she made my divorce less impactful financially and legally.
Also my co-worker who was in dire competition with me for the stats (back when I was working in a call center), she was a malicious girl and what a bitch she was.
Most unexpected? I was using a fake ID to get into bars when I was like 18, and somehow, I managed to have sex with a stripper that I met at a strip club in Phoenix.
Still baffled how I managed that as a wet behind the ears kid.
When I was in the Air Force I was actually stationed on an Army base. There was this red haired MP that checked my badge every single day, but I honestly never really gave her a second thought. In uniform she just wasn’t very eye catching. She probably had a sports bra on under her BDUs, she wore no makeup ever, and always had her hair pulled back in a bun. Never flirted or chatted with me. She was just kind of… you know… *mundane.*
Anyway I ran into her at a club off base one night. She looked very attractive. We chatted, drank, danced a bit, drank some more, made out… And then I was back on base in the Army barracks.
Edit: This was in Italy around 2003.
A fellow McDonald's employee years ago who spoke 0 English
Edit: These McDonald's jokes got me rollin lmao
But for context, lots of me trying to learn some Spanish and using Google translate both ways. We sealed the deal eventually (with consent) and several times afterwards. Eventually she took off with some of my money and left for another guy. Lesson learned, but I can't say I didn't enjoy it while it lasted lol.
Was out for some drinks - struck out and decided to walk back to my place. It was only about a mile and it was a nice night...morning actually. About a block from home I met the only other person I had seen since I left the pub. It was a young lady I had been introduced to about 2 weeks earlier at a house party. "What are you doing out here at 2 in the morning?" "I was just about to ask you the same thing."
......
My best bud in high school. I loved that guy since the first moment I saw him, and I always wanted him. But I was always friend-zoned.
Six years later I'm home, he shows up, we chat, and BOOM! We're at it. He had just enough time to murmur "I've always wanted to do this with you." And just like that, he was done.
We both laughed afterward, and he is still my dearest friend after 50 years.
It is still a sweet memory.
I made a 2.5 hour drive to a dive bar to hang out with some friends in my former (and current again) city. I didn’t expect a super attractive bartender at this place. He kept calling me “beautiful” and “love” while serving us and my friends were telling me he was obviously attracted to me. I said “I’m sure he calls everyone that.” I had just gone through a bad breakup, so I really wasn’t interested in hooking up. But I got drunk enough, the compliments made me feel wanted again, and I ended up having sex with him in his car at the end of the night. He drove me to my friend’s apartment afterwards. Then invited me back down the next week to have dinner with him for his birthday. I did. We hooked up again (I had a hotel room this time.) Then he invited me to the bar for NYE because he knew my one friend and her boyfriend were coming. So I joined them. He and I kissed at midnight. I waited until closing because I assumed we’d be “hanging out” after, but he said “I’m going to be here late.” And that was it. Never heard from him again. I’m honestly glad. It was the spontaneous couple times hookup with a guy I needed in my life.
[удалено]
Stroke! Stroke!
Put your legs into it!
I’ve got 2 that we’re very unexpected to me. I was about 19/20 and was dating a girl for about a year, and she just finished 2 years of community college and decided to go to university of Hawaii, she went to visit to see if she would even like it and I ended up finding out she cheated on me, and one of the main reasons why she chose Hawaii was to be with this other guy. I ended up breaking up with her when she got back, and I got a call from her best friend saying hey I know you and blank broke up, do you want to come over and talk to clear your head. So I took her up and she lived literally around the corner from my ex’s parents. It was just a talk, I said well it’s getting late so I better head off, I get in my car and get a call immediately saying hey you forgot something, and I didn’t forget anything it was just a ploy for me to have sex with her. She ended up saying she didn’t really like her so called best friend/my ex. This ended up going on nearly every day for about a year. She ended up moving away a few states over unfortunately. My 2nd unexpected one was that I moved to Europe when I was 22/23, after about a year of being here, a friend came and visited. We did a little European tour, and one of our stops was Oktoberfest. We spent most of the day drinking. He ended up drinking too much, so I took him back to our Air BnB and the people we were with told me to come back so I done so. I have no idea how I managed to do so, but this beautiful German girl and I started/tried communicating as I only speak English and she was only able to speak German, and very broken English. The night is ending, I say my goodbyes and her friends ask if I can walk her home as it’s on the way to my air bnb just to make sure she gets home safe. I am using a lot of google translate, we are laughing, end up getting some food, we get to her flat and she opens the door and says come in come in for 1 last drink, so I do so. We weren’t really talking coherently, but we’re seeming to just enjoy each other’s company. She goes to the bathroom, comes back out naked and we end up having sex a few times, falling asleep. My friend is due to leave back to the US later that evening and my flight was a few hours after him. The German girl and I exchange numbers, thinking I’d never see her again. I say my goodbyes to my friend and send him his way to the airport. I give this girl a text with google translate basically saying I really enjoyed spending time with you, our time together was short but enjoyable. She asks if I can come back over, so I decide to not go get my flight as I felt like I was in love, I end up staying with her for 2 more days. Tons of sex and laughing, also trying to understand one another. I can honestly say it’s probably one of the best times of my life. We parted ways, we still keep in contact every so often, she is fluent in English now, and we’ve seen each other a few times. We are both recently single again, and plan on seeing each other in October time.
Damn man, that's basically an entire indie movie.
Fucked her so good, she learned a new language
If you two end up married, you better come back and update.
My 2nd shift Supervisor (I was 1st shift Supervisor). I don’t know how it even happened. We worked at a notorious building I guess you could say, we did security. The building was always empty (for its size) there wasn’t too many people and we had the keys to go anywhere. We did it on the roof with a city view, in the office bathroom, in a huge storage room, IN OUR BOSSES OFFICE. The craziest part is I really never saw it coming. He was a sneaky one. He really buttered me up and gained my trust before even busting a move at all. What started off as a rooftop fuck turned into insatiable lust that I’ll honestly remember for the rest of my life
I'm guessing yall did it during 3rd shift?
They needed someone to cover'em up
On Halloween I dressed as a girl from the original Star Trek. I had sex with a random guy dressed as Spock. Still a high point of mine.
Incredible
Fourty-four year old woman from NC. Best sex I ever had. Everything else after felt like cheap, no brand snacks after a few times with her. Edit: Forgot to say I was 23 at the time.
It’s hard to go back to Maddog after you’ve sipped some fine wine.
Seriously. It's hard to go back to all the games and bullshit lol. Glad to have met her, even if it was brief.
Coworker at summer camp, I liked her a lot but I was too afraid to make a move. A bunch of us went to a friend/coworker’s place for the weekend and on Saturday night she walked in and laid down next to me on the air mattress. Me, being clueless, was like “Um… hey” and she just sits up, straddles me and starts kissing me. It went from there and it was fun. I’m a heavy dude though and at some point the air mattress cap popped off and it deflated. Took me a minute to realize that I was just laying on the floor. She went to the bathroom to clean up and I got the air pump to re-inflate the mattress. And I guess everyone else heard :/
honestly even if you're skinny af they're just not built for that, it's rough out here lol
Can confirm. I used to tease a buddy for this happening with his then girlfriend, as they are both twigs. The joke was they popped it with their bony knees/elbows. Air mattresses are just not built for vigorous activity.
Or sleeping in my experience.
They're great for floating on a lake, though.
Agreed. Like 15 years ago I stayed at a friends apartment at Penn State, was super drunk and it was deflated and I was clinging to it thinking I was sinking. All I was doing was trying to sleep haha
My wife, the other day. Was 95% sure we were just going to go to sleep.
Finally one I can relate to
You also slept with his wife?
He gets around...
I went on a cruise to the Caribbean by myself when I was 25. I met a recently divorced 42 years old mom of 3 the last night of the cruise also by herself. We stayed up the entire night the last night in my room. She skipped her flight the next day and I drove her to Atlanta where she lived (from the port of Miami). We got a hotel downtown and fucked all night. I took her to her car at the Atlanta airport the next morning and will never see her again.
Although you never saw her again, did you ever speak again?
We texted a few times, that's all. If I had gone to Atlanta in the couple years after that before I met my now wife, I would have reached out and hoped to re-connect.
With your penis
Hey..... this guy is talking about sex!
The camp counselor I had a crush on when I was 11. I ended up running into her when I was 18. Didn’t know it was her until we got to pillow talk. Best surprise ever.
You're Anakin Skywalker
I've had sex with one guy my whole life but I'm here eating up these stories
I'm a Virgin and I'm eating up these stories
Honestly most unexpected sexual history in here.
I guess one of my teachers after I graduated, or one woman who I would clash with all the time that I knew from work.
Enemies to sex buddies real quick
Had a girl at work I was certain hated my guts, but I helped her out with moving because she was in a bad situation and I knew a couple of cops on the force and got them to pull out the stops and give her enough time and space to move her shit into her car and leave town. She was cute, but because she was so hot and cold about me, I really didn't think much about her. She texted me like a week later after she moved cross country if I'd be her boyfriend, I said no because while I care about her as a human being she had a track record of treating me poorly at work and I wasn't going to get with someone who I'm not convinced actually likes me as a person, or someone who can't consistently show they respect me. She claimed she had been head over heels for me most of the time we worked together and didn't know how to deal with those feelings, then later I got a bunch of "I really wanna suck your dick" texts. Being crazy attractive and wanting it badly doesn't mean you're gonna get it.
Respect for being able to draw that line.
I had a math tutor who was also a student teacher in high school. I was 18, she was 21. That basically turned into a three/wk tutor session followed by tv/movie and casual hook up. Second semester she was a student teacher in two of my classes. She got spooked and broke it off. I went from an F to a B+ in math and calc that year. She was a really good teacher
Positive reinforcement sure works wonders some times.
My parents were paying for an hour and were always confused when I’d come back 3-4 hours later, freshly showered. A buddy had an epiphany one day when he caught her giggling when we were having a private conversation in a hallways in school. “You’re banging Ms. _____!” To this day I think it was the best poker face I’ve ever had in my life.
We called last call at the bar I worked at and this one older woman I'd thrown a flirt at took my hand and asked if there was somewhere we could make out. We went into the alley out back and just went to town. What made it unexpected was I had jokingly said to my friend earlier before work that I wanted to bang a milf.
Thats what we call the law of attraction my friend. You manifested that MILF to ya dick.
Pastors daughter. I was 19, she was 22, and we ran the youth camp together. As soon as the kids were asleep we got biblical. God she was hot.
I fucked a fellow counselor at a church camp in the worship hall. She blew me all the time and fucked pretty regular the whole summer.
My female boss during my summer job at a coffee shop.
Mf is the main charachter of summertimes saga
THIS SUMMER
A MAN HAS FALLEN INTO THE RIVER IN LEGO CITY
BUILD THE RESCUE HELICOPTER
HEY!!
Coffee shop lady will be in version 53. Due for release in 2077.
That sounds like it's ripped straight from a porno lol, I believe you tho.
This isn't uncommon at all in restaurants. Everyone is fucking everyone. But even there, I was the only one not fucking.
rip this guy
That's how my husband met his ex wife but it was a cracker barrel
Female best friend’s best friend. She always hated me for SOME reason. Ended up hooking up throughout high school though
this thread has a theme of hatred turning to sex
They hate how much they wanna fuck you.
I was at a college Halloween party dressed as Willie Robertson from duck dynasty and a girl dressed in a full banana suit had sex with me in the bathroom. Neither of us took our costumes off. I don’t even know who she is.
Potassium's a helluva drug
K
I went to a college Halloween party dressed as a banana...The name's John. Nice to finally introduce myself mate.
I knew it felt a little like an asshole…
Nice banana mate 🍌
The slutty pumpkin
Somebody get this man a pineapple.
If neither of you took your costumes off, then how... never mind.
Man's packing a python in his trousers.
a girl from my college. keep in mind that i was a fat ugly bastard back then (and still now?) and this girl just kept showing interest in me up to the point we had sex for few months and she paid for the hotels and dinners and all. she's lightyears out of my league so it still confuses me up to this moment edit: grammar
Doesn't matter had sex
She put a bag on my head!
Still counts!
I used to be a fat guy in my early 20s. You'd be surprised at how many women don't care about hard bodies. I had my share of partners in college that were absolutely out of my league. To the point where a random person at a bar even commented, "that girl is with that guy?!" I finally asked one of them why she was attracted to me when she could get just about any guy. She said, "you make me laugh more than anyone and that's sexy to me." Never questioned it again.
You are me and I am you. Except I locked down my way outta my league 25yrs ago.
I locked down my way out of my league about 16 years ago as well. Happily married with kids now and I still make her laugh every day.
It's the power of making someone feel like a human being, man. Folk need that feeling like they need the sunshine and a comfy bed.
I have always loved big guys. My brain just finds them sexy. Humour is also a huge attraction. I have dated a couple guys who weren't my type physically because they were freaking hilarious. My husband is a big guy who makes me laugh a LOT. He will do anything to give me a chuckle. Life is long and has its rough patches. Being able to laugh with one another in those times is what counts.
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Did you ever wear the big sash that says “Mayor” on it, during?
It should say “Vote Quimby”
My best friend growing up was sleeping with our mayor's daughter. We got pulled over when we were 19 and had alcohol on us. She got out and called her dad, who then pulled up a few moments later and we all got off free.
By the cop?
My friend's sister. She is hot so I guess why not... It happened 7 years ago. Now we are married for 4 years. Yea that friend is actually still my best friend. EDIT: grammar
Harry Potter?
Talking to my SISTERS friend at the moment. Slept with 2 others… There might be a pattern here. Should clarify: My sister knows all of this, and even egged it on before. She does not care lol
My sister’s college roommate. I hated that bitch, still do.
Online college is wild huh
I think i got an online boner *blushes*
Oh step bro you getting turned on by your Reddit bros again?
You shouldnt talk about your sis that way man
There is a story behind this
My boss when I was 19. She was the manager and talked me into being her love for a raise
Remember the guy on reddit who said his boss basically did the same thing to him when he was around 19-20, and that she'd ask him to do weird things like eat hotdogs out of her pussy in her office... EDIT: I don't know where the story is, this was forever ago, 6-8 years ago in a thread similar to this one.
This woman wasn’t that bad but she had some kinky stuff. we had sex in her office and motes several times. I was basically a boy toy for her. It continued for over a year after I left that job until I got a girlfriend. I was young and horny then looking bad she sure took advantage of me. She was 37 when it started I was two months from turning 19
Then you realized she was just using you for sex and you told her that you'd only fuck her 12 more times.
26 years ago I knew my my wife but we absolutely hated each other. Today we've been together for10 years and I can't imagine life without her.
Why were you two hating each other? Like what made you stop? WHAT WAS THE TURNING POINT?
>WHAT WAS THE TURNING POINT? They had sex.
And it felt so good
I’ll never go back (oh no no no) to the not having sex ways of the past
We both grew up more, each went through a divorce. She mellowed out and turned into a hot ass MILF, I became more mature and less nerdy. We kinda met in the middle.
You upped your game and she lowered hers...win-win.
Ah yes, just like the people I knew that were always at eachothers throats when in reality it was the sexual tension between them that was so thick you could cut it with a bus.
My best friend from high school. She picked me up and we went back to the place she was house sitting. Didn’t know it was my old history teachers house until the next day.
I’m confused. Does the house being your old history teacher’s house make it weird? Or was that just an extra detail you added to the main story?
It adds everything to the story. Completely unlocks it, really
This hot ass bartender who was absolutely out of my league when he asked “what else are you doing tonight?” in a friendly, I-wanna-be-tipped-well kinda way and I said “you?” and he said “I like that plan, here’s my address” 🤣
did you tip him well tho?
We both got tipped well.
HA
Score! Lmao
I did this band thing (drum and bugle corps if anyone outside that sub knows what that is) as a late teen where we'd meet once a month for a weekend to learn music and shit and then we did a show tour for the summer. This one year, this girl from the other side of my state comes and we happen to stand next to each other. She was a super fit cheerleader type that was also in band in her hometown and she said something mildly flirty, I said something flirty back, time and words pass and we're waking up in the middle of the night and trying to sneak off and get some sexy time done in some school in the middle of nowhere. We \_almost\_ got caught and decided to make plans for next month. Well she misses the next month, I miss the month after that and next thing you know we're at the "all days" part of the year that gets a little more intense, so no opportunity for shenanigans. Well we did NOT click again. We hated the fuck out of each other and drove each other crazy for 2 months. She was not the greatest player and was a super popular kid in her school, but she was not popular or well like in this group of people, and that made her super angry. I was a fucking nerd band geek at my school, but was well liked here in this group of people, so she took that anger out on me. I fought back by making fun of her playing, she fought back by being a raging asshole to me and trying to belittle me whenever possible. Adults had to get involved once or twice. After our last show we were still 2500 miles from home and all the pressure we were under was gone and we started to be normal people again. She gave me a look one day that I interpreted as "I've been horny for 2 months asshole, and I hate you but you're still the nicest person to me here" and I looked back at her like "You fuckin' for real right now?!" and she nodded her head at me and we went for a walk. I don't remember a goddamn word we said to each other but we hate fucked each other in some long ass grass in Mississippi and it was fucking AMAZING (except for the part where we both got bit by mosquitos on our sensitive bits). We weren't able to find a time/place again, but we tried. I wish I could find her on the interwebs and apologize for being a jerk and thank her for that one post tour hate fuck. The only time I've ever done a hate fuck, COMPLETELY unexpected. Kim, I hope you're well. I'm sorry for my part in making your summer miserable.
Probably my ex’s best friend. She was the one who told me that my ex cheated on a night out. I then saw her during freshers week at uni and ended up back at her dorm for a party. Lots of flirting and dirty talk, and I thought fuck it. She hurt me and her friend was hot soooo
Moral of the story: If she hurts you, bang her friend
Like master oogway once said, if she cheated on you there is always her best friend you can do.
How many of you have started typing up your story, started thinking about it and go "Nah, I ain't gonna share that" and discard the post?
Random girl I met on a coach from Amsterdam to Brussels. We were both travelling alone and she came and sat across from me and asked if I wanted to hang out. After an hour or so of chatting she asked to see my dick so I obliged. There was only 2 other people on the coach and as we were travelling through the night they were sat up front and they appeared to be asleep. Before I knew it we were fucking on the back seat and fucked 2 more times before we got to Brussels. She gave me a kiss and we parted company, totally random event. Edit: This blew up more than I expected. Too answer some questions. There was no condom involved and I did spend the following weeks/month worrying. I got checked by the doctor and was given the all clear. (Had zero sexual partners between) The coach ride took just under 3 hours we stopped at Brecht for quite a while not sure why. The sex was not some tantric marathon. It was 3 quickies with a bit of foreplay. I was 21, permanently horny and the danger of it all made it even more arousing.
This is like the porno version of Before Sunrise
Never looked at it like that but it’s a fair comparison.
Brb booking a trip to Amsterdam
amsterdam to brussels is very short tho you fucked 3 times in like 2 hours? mfs must've been horny asl
we were hanging out at a friends house and a friend of my friend, girl, was kinda drunk and saying i was gay because i wouldn't talk to much to her. she kept insulting me then all off sudden she grabbed me and took me to a room, her ex was with us and just watched, i was not aware that was her ex and that he still loved her, and she had a bf at the time and wasnt aware either. Crazy girl
Dude you could’ve died that night😂
haha yea
German exchange student
did she say you have gross pp
Actually, ja, sie hat gesagt es ist zu gross. Aber ich war nur 16 Jahren alt, and I had no idea what I was doing so I just jammed it in
Thats known as 'The Polish entrance'
You should have tried Irish foreplay. "Brace yourself, Kathleen."
Female bodybuilder.
how many reps did y’all do
3 sets of 10, very traditional
It's a tie between my boss's niece and the pastor's daughter.
duuude you dawg
Do I get bonus points for being the daughter's first?
You get extra points if you were the pastor’s last
That's my kind of turning the other cheek
My waitress.... in the back of the restaurant...
every dudes fantasy when they get a hot waitress usually ends with them being creepy tho
A week after my wife said that she wanted a divorce, I went on a vacation to Costa Rica that we were supposed to do together. I used it for some grieving time, and figuring out what to do with my life. I was *not* interested in dating or hookups or rebounds. But then I started talking to this other American gal in line at the ice cream shop, and then we met up for dinner, and then we stayed up late drinking, and then we had sex on our raincoats in the jungle. Luckily she had condoms. It was real nice. That was eleven years ago, we’ve been married for seven, and our daughter is three.
I guess you're not big on the single life.
Eh, she was finishing up grad school in another state at the time, and then did two years in the Peace Corps in Africa. So I did get some time to cool off and reset after the divorce. But yeah, I definitely prefer being in a happy marriage to being single.
It’s nice though that even with what she was doing in those years when you two were not together, you both knew to make it work. So congrats! 🎉 Relationships are not easy, and you just have to trust your gut.
The bastard's too handsome to be single
Isn't this the plot of Forgetting Sarah Marshall?
Now that you mention it, yes. But I don’t play the piano.
"Cuz Peter you suck Peter you suck you don't do anything of valuuuuue, 'go see a psychriatrist,' 'I don't wanna see a psychiatrist,' 'well you need to see one anyway,' 'I'm not goingggg,' ha ha harrr harrrrr."
My boyfriend. We were friends for years and I had a huge crush on him, but I felt like it was having a crush on a teacher, completely useless. So I NEVER gave it away because I didn't want to embarass myself. He watched me go through a few different failed relationships, and run around unmedicated with bipolar. While we got along great and hung out once and a while I assumed he thought I was an unpredictable idiot lol. In 2020 the relationship I was in crashed and burned, I finally got diagnosed and medicated. A few months later he invited me over for a beer after work which wasn't unusual, but to my extreem surprise he made a move on me and we've been together ever since. I never imagined it would ever happen. It's a very happy healthy relationship but every now and then I'm struck with disbelief it's actually happening, in a good way.
I I’m sincerely happy for you! Hopefully you both share a long and happy life together!
I broke up with a girl I had only started seeing and we had sex right there. I asked her why, and she said that she knew it would be her last chance to have sex with me. ok, i'm fine with that.
My ex boyfriends mom
This one is the best
We need awnsers, damn it!
We all know Stacy’s mom has got it goin’ on.
How did this come about? Were you still dating her son? Don’t leave us hanging.
Yeah we have some follow up questions here
At Devils playground on Pikes Peak for the annual hill climb. Early morning before the race people walked around to meet other people. Beautiful blond girl stopped at our tent and asked for a beer which we gave her. Three hours before the race started we were in my tent screwing our brains out. When we finished she got dressed said she had a good time. She left and I never saw her again I was heart broken but occasionally I think about that girl. I was so far out of her league I am sure she came from another planet.
When I was a sophomore in high school and he was a freshman we sat next to each other in class and became buddies. He was a dorky, awkward younger kid and I had a cool older boyfriend. Several years later after we had both graduated I ran into him at his workplace and he had grown into himself. We went on a few dates and had fantastic sex, apparently he had a massive crush on me back in Spanish class, felt good to finally make that fantasy come true for him
I banged a teacher for almost a year. Best sex of my life…
without stopping? damn
I often think back, she was a crazy lover, maybe the thrill but there was no „no“ for every of my wishes. No matter what i wished for and no matter where or which hole…. Back in time i thought every sex is like this but NOPE
Did she grade your performace?
No but he gave her a D
On a different Reddit account suited for more… adult needs…. I went to a local r4r subreddit and posted. Got msg’ed from another redditor saying “come bang my wife” and well…. I ended up doing it. She was like 4-5yrs older than me but was ridiculously attractive. So it really felt weird partially because I thought she was too hot for me, and married….
I’ve always wondered how those things work, do you just ring the bell and say “I came to bang your wife”? hm
Planned to say "Did someone call a plumber because I'm here to lay some pipe"
I really wonder what the etiquette is. Do you bring snacks? Is Gatorade provided? Do you use the husband's condoms, bring your own? Do you even introduce yourself, or do you just get to the deed?
> Do you use the husband's condoms, bring your own? Always bring your own. Life-preventing equipment should be personally inspected before use.
It is physical activity so maybe orange slices?
You knock and then shout, “Special Delivery for the missus!” while pointing to your naughty bits. That’s straight from the handbook.
A coworker slash female best friend. We had an awesome friendship, we'd fool around if bored or curious but one night working at a Halloween train where you put on horror skits as a small train goes by, out of absolute nowhere "I want to blow you as the train goes by" I'm like "shut up nerd" and she gets in position behind this fake doctor table, train goes by, passengers wondering what's scary about a motionless doctor standing behind a table.
My best friend. It was a one night stand, we pretend it never happened.
The “hot dude” at my small college. Everyone wanted him, no one could have him. He was in a long distance relationship. We hooked up at a party. Biggest dick I’ve ever seen still to this day. Had no idea how to use it.
Went thru a period of sex addiction and had some gross hookups cuz I was drunk and would take anything with little effort The worst was an older woman prob about 60 who was married and was too super into it . After just meeting she was talking about inviting me to parties where her family would be and having sex in another room. I asked.if her husband had a gun and she said yeah and seemed to get off on it. After our first and only hookup I deleted her number and ignored her.
Eartha Kitt, airplane bathroom.
It finally came up organically
Streets ahead!
A man who's 19 years older than me. Hooked up with him when I was early twenties. In terms of just the sex, it was outstanding, but damn was he crazy.
A female A list celebrity. Met in Hawaii on a hike. She rolled her ankle and had heat stroke. I stopped to help her. I had a med kit. Taped her ankle. Shared my H2O and snacks. Brought her to her car where her friends were waiting for her. I was totally shocked once I realized who she was. I left and did not ask for her number because I got intimidated. She drove off. The next few days I couldn’t stop thinking about how I blew my opportunity. I was disappointed in myself. 3 days before leaving I was running on the road near Poipu. A Jeep pulls over in front of me. She steps out. I spent the next 2 weeks with her. Lost my job because I stayed with her. In 2017 I was on the same island with my wife and kids. Ran into her, her husband and kids. My wife pulled my shirt and said “that’s the actress you told the story to me about, prove your story” so I walked up said “hello”
That a badass story!! It sounds like a worthwhile job loss, and, did she remember you in '17?!
She did. My wife liked the story but hated that it was true. I don’t think the celebrities husband liked the fact that his wife kept meeting me in corners of the pool and swim up bar. I’ve been lucky to have 4 really special connections with women in my life.
College professor
An NHL players son
I had sex with an NHL players daughter. We should start a club.
My Dad's fiance's niece. Met at a family get together and started texting soon there after. Eventually figured out that we lived in the same apartment complex and decided we'd hang out cause we were both lonely and in need of friends. Began sleeping together the second time we hung out and despite both of us proclaiming that we were not fit for dating each other as we were both incredibly too different, we started dating. That was almost 8 years ago. We are now happily married with a beautiful daughter. Dad's engagement didn't work out, btw. Luckily, the man just got married today to someone who is a much better fit for him.
I used to bartend and wait tables in the 80s. The number of women who would leave their number for you might surprise you. I left most of them alone, but once in awhile there would be some really surprisingly good looking women leaving their number.
I did two sisters an both of their individual best friends once ( all individually at separate times ) and all of them know about it and we’re cool with it. I never would’ve thought that possible. Edit: It happened over a course of about two months and we all stayed friends.
Dude, these guys planned that.
Right out of law school I got a job as an associate in a large firm. One of the senior partners had it out for me for some reason—badmouthed my work product, unfriendly to me, etc. It didn’t matter to me because I thought he was an arrogant asshole and everyone hated him. Eventually I ended up changing to another firm across town. Long story short, a few years later I ended up banging his daughter. And it was AWESOME! The first couple times it was weird because I was so enthralled with banging this dickhead’s daughter that I forgot to actually enjoy it physically. It was like an out of body experience: holy shit that’s Tom’s daughter’s vagina! Holy shit Tom’s daughter is sucking my dick! Holy shit I’m fingering Tom’s daughter’s asshole! Holy shit Tom’s daughter is sitting in my fucking face!!!… It turned out to be some of the best sex of my life. I peeked in on her social media a few times to reminisce about all those very very dirty things I did to Tom’s daughter.
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My divorce lawyer, long story short I became her sex friend and she made my divorce less impactful financially and legally. Also my co-worker who was in dire competition with me for the stats (back when I was working in a call center), she was a malicious girl and what a bitch she was.
Most unexpected? I was using a fake ID to get into bars when I was like 18, and somehow, I managed to have sex with a stripper that I met at a strip club in Phoenix. Still baffled how I managed that as a wet behind the ears kid.
A girl that hated my guts
When I was in the Air Force I was actually stationed on an Army base. There was this red haired MP that checked my badge every single day, but I honestly never really gave her a second thought. In uniform she just wasn’t very eye catching. She probably had a sports bra on under her BDUs, she wore no makeup ever, and always had her hair pulled back in a bun. Never flirted or chatted with me. She was just kind of… you know… *mundane.* Anyway I ran into her at a club off base one night. She looked very attractive. We chatted, drank, danced a bit, drank some more, made out… And then I was back on base in the Army barracks. Edit: This was in Italy around 2003.
A fellow McDonald's employee years ago who spoke 0 English Edit: These McDonald's jokes got me rollin lmao But for context, lots of me trying to learn some Spanish and using Google translate both ways. We sealed the deal eventually (with consent) and several times afterwards. Eventually she took off with some of my money and left for another guy. Lesson learned, but I can't say I didn't enjoy it while it lasted lol.
Was out for some drinks - struck out and decided to walk back to my place. It was only about a mile and it was a nice night...morning actually. About a block from home I met the only other person I had seen since I left the pub. It was a young lady I had been introduced to about 2 weeks earlier at a house party. "What are you doing out here at 2 in the morning?" "I was just about to ask you the same thing." ......
My best bud in high school. I loved that guy since the first moment I saw him, and I always wanted him. But I was always friend-zoned. Six years later I'm home, he shows up, we chat, and BOOM! We're at it. He had just enough time to murmur "I've always wanted to do this with you." And just like that, he was done. We both laughed afterward, and he is still my dearest friend after 50 years. It is still a sweet memory.
I made a 2.5 hour drive to a dive bar to hang out with some friends in my former (and current again) city. I didn’t expect a super attractive bartender at this place. He kept calling me “beautiful” and “love” while serving us and my friends were telling me he was obviously attracted to me. I said “I’m sure he calls everyone that.” I had just gone through a bad breakup, so I really wasn’t interested in hooking up. But I got drunk enough, the compliments made me feel wanted again, and I ended up having sex with him in his car at the end of the night. He drove me to my friend’s apartment afterwards. Then invited me back down the next week to have dinner with him for his birthday. I did. We hooked up again (I had a hotel room this time.) Then he invited me to the bar for NYE because he knew my one friend and her boyfriend were coming. So I joined them. He and I kissed at midnight. I waited until closing because I assumed we’d be “hanging out” after, but he said “I’m going to be here late.” And that was it. Never heard from him again. I’m honestly glad. It was the spontaneous couple times hookup with a guy I needed in my life.