You Are Dating Him? He Could Be Your Father!

people who have hooked up others with a massive age gap between you how did that happen best friend's mom in high school was going through a divorce known her since i was in third grade one night i go over there to hang with friend she answers the door all disheveled looking seems she'd been crying friends not home are you okay miss friendsman ugg i let myself in and we talk and drink some wine she's all sad no self-confidence i am never going to find another man mister booty tell her she's crazy you're beautiful hard working loving amazing mom you'll get scooped up real quick she laughs i say i'm serious she has nothing to worry about mr friendster is just a dong he will never be happy with anyone if he couldn't see what he had before him cue silence and flirty look we hook up next morning she thanked me for everything and i left she got married like three years later and has seemed super happy ever since did your boy find out i delivered her newspaper and went to collect for the money and she apparently didn't have any instead invited me in and gave 22 year old me the hour of a lifetime margaret was 58. ah so that's what margaret thatcher did on weekends old rich jewish lady hit on me as i was bringing groceries to my car guess she likes young black men she helped pay off my student loans get a sugar mama how old i sort of fooled around with a professor once i'm a male she's female it was a practical class that she taught and we had a lot of one-on-one time with her i was having a lot of problems with a single aspect my work but she said it was otherwise some of the top stuff in her class we got along really well joking and playful teasing she was 40 45 i was 20 she kept office hours on fridays from 3 5 p.m i had to talk to her about an assignment that i did really poorly on i went to see her in discussing it she said okay let's sit down and rework some parts here so sitting side by side we worked on it each doing a piece and leaning over each other there was a strange moment where we made eye contact and she leaned in we kissed and started making out pretty passionately she started feeling me up and i did the same she put her hand on my junk through my jeans and pulled back she said something like oh no we can't do this oh god i'm sorry i said sorry she said no no it's my fault we just kind of sat there for a while in awkward silence i broke the silence and said look i can see how this might be a bad situation for you i just want to you know i won't tell anyone okay we'll just pretend this didn't happen i don't want to freak over your career which i didn't she was a great professor she said thanks i left we didn't work as closely anymore but she still marked me fairly we didn't talk about it again this reminds me of shameless except you didn't continue on with the act just got laid off from my job freshly split with my wife super heartbroken and unsure about my future and my life went to the golf course to watch some play-off hockey with my dad and brother there was this gorgeous sexy milf that served there and since basically everyone in my town was out of work the place was packed i was super attracted to her but because she was being hit in by nearly 50 other men i didn't even bother to because i could tell she was done with being hit on at that point i had talked to her before and we got along quite well so we did kinda know each other anyways turned out to be a great night had fun with my family and some friends the hockey team we were cheering for won their playoff game and we ended up staying until closing almost everyone left including my dad and brother i hadn't drank that much so i was sober but there were about six people lingering around with obvious intentions to try to go home with her i paid my bill and said goodbye when she asked if i'd stay until she closed up to walk her to her car i told her i'd be happy too so i helped her clean a few tables while she was cashing out and kicking out the last six or so patrons over laying it on thick trying to convince her to come home with them they all eventually left she asked for a ride home we got in my truck she asked if i wanted to hang out a bit we went back to my house and for the next couple months we hooked up as much as physically possible it was the best couple months i had had in years we got along laughed cuddled and just enjoyed each other for a few months before we both moved away from town he was mutual and fantastic 10 stroke 10. she had a crush on me i thought she was very hot but holy crap she was at least a decade older than me how intimidating i asked her to join me at a bar for karaoke night we just talked that night the next week she invited me over to her place to watch the first gop nomination debate for the then upcoming 2016 election somehow romance still bloomed she hit on me some more but holy crap she's at least a decade older than me eventually we kept glancing at each other until she leaned over and kissed me i kissed back and she crawled on my lap and took her shirt off and it went from there almost three years later we're getting married this april found the president of france guys hooked up with a single mum at a small town music festival when i was 17 i think she thought i was older than i was even as a 20 year old guy people look pretty much the same in the 17 20 something age range in college i went to a bar that attracted an older crowd to watch a friend's band play there i was 21 at the time most people there were late 30s early 40s was wandering around casually taking to people talked to her 40 something for a while to my surprise she invited me back to her place drunk me said yes she still had it for 40 plus i stayed over that night the next morning as i was leaving i crossed paths with her son in the kitchen as i was walking out he was about my age he stood there confused for a second i saw it in his face the moment he realized what happened i turned and walked to the front door and he yelled really bro i smirked shrugged then opened the door and left you fricked his mom dude cruise ship i was 16 she was not copious amounts of alcohol poor life choices you know i learned things she was undoubtedly disappointed i repeated that pattern for a while i'm afraid hooked up with a guy who was 24 years older than me i'm in my 20s we worked together and got on together well it started with friendly lunches turned into attraction i didn't find him physically attractive at first he was six inches shorter than me and kind of pudgy his personality more than made up for it and over time it changed his looks in my eyes and i became physically attracted to him he appreciated me he genuinely listened to me made me feel like the most beautiful woman in the world he was fun to talk to always had funny stories the age difference never bothered me i could always feel eyes on us when we went out and showed any pda funny how the men would always be the ones to stir women just looked at me like a good digger in the bedroom he had a small dong but always made sure i was taken care of with oral and his hands when you have only had young guys pound on you like a jackrabbit having someone slow down was a fantastic change he spoiled me from beginning to end we eventually stopped seeing each other because we wanted different things in life he had never been married or had kids and that is something that i wanted in my life the split was harder on me i think but i moved on and have the life i had always wanted i hope he is the same as a guy that's getting older it's nice to hear that pounding like a jack rabbit isn't always required i was 21 and she 37 and a fitness instructor met at a bar yada yada yada she took me home found out throughout the course of smashing three times that night into the early morning that she was going through a divorce because her husband admitted to being gay he left her for his best friend as the saying goes right place right time i learned a lot that night and realized so many years later the reason why she was so against anal that night anal on the first date is a lot to ask of anyone tbh regardless of the circumstances looking back this was probably abuse of some form but it never felt that way i was 17 and she was exactly three times my age 52 years old she was an aerobics instructor at a senior assisted living facility and very attractive because of her job i was working in the kitchen washing dishes because it was my final year of high school and my dad thought i needed to hold down a job and learn some responsibility i learned a lot more than that i double check that math i lost after older men all the time they don't lust for me back very often probably the oldest is about a 25 year age difference i am female and came here to say this sometimes it feels like i'm stuck in a cycle of doomed relationships so i feel your pain colon based on the title i initially thought this thread was about multi-generational drug use i now see i was wrong about that played in a cover band in my twenties the other guys were in their 30s and had a fan base that matched their age not mine one of them asked me out for drinks and we ended up hooking up a few times didn't tell the band or her kids who are closer to my age than hers coma or her kids who are closer to my age than hers i would certainly hope so expat in japan with an international age gap story i was 23 she was 48 we met casually online and decided to hang out i asked to go to lunch she skipped the games and came straight to my place two years later we're still together and i cannot fathom dating someone under 40. fun anecdote at first she sidestepped conversations about age until i busted her thanks to being a huge nerd mentioning the 1977 kulthora film horse who elicited a knee jerk response of oh my god i saw it in the theater and i will forever be jealous that she got to see horsou on the big screen i will forever be jealous that you got to see horsoo on the big screen you still can you just need to be on the lookout for it i saw horsou on the big screen during a film festival i saw flyers for it for a different film festival years later although i did not partake because i was more interested in metropolis with a live band we were co-workers i was 21 in uni and she was 33 a mother of two we hung out a few times and then it just happened went on for six months or so i'm only interested in men much older than me my ex was 37 years older than me and we were together for four years we met at work i was a saleswoman and he was a security guard the man i'm with now is turning 60 this year i'm turning 31 we met at a party not me but one of my close friends 26 m is dating a 44yo woman with four kids and a pending divorce they've been together almost a year seem to have stemmed from the mutual desire for sex lots and lots of it we work together at a cinema he was technical guy and i sold popcorn i was invited to help him with this and one thing led to another we managed to keep that going for about three years he turned 43 i turned 20 and then i left the job no ragrets we managed to keep that going for about three years geez you two are insatiable drunk hookups when i was 27 i first had a fling with a 41 year old bored housewife and then with 18 year old girl first lasted for two weeks the other one for two months my wife of eight years is 16 years younger than i am and honestly it just happened i have friends who are about 10 years younger than i am and she was dating the brother of one of them he dumped her and eight months later we started dating i was kind of hesitant to ask her out but when we spent time together we were able to hold intelligent conversations that were mutually interesting she was cute and liked my looks still does thankfully it just kind of developed into a loving relationship she was 22 when we started dating and is 32 now and is pregnant with our first child she constantly tells me she pisses her co-workers off by bragging about how good i am to her she has co-workers that are older than i am all the way down to sim who are younger than she is so it's not an age thing we're just as much in love today as we were eight years ago and are content to spend the rest of our lives together i was an 18 year old college freshman virgin she was a 26 year old super super super senior met her through mutual friends and she was on me like white on rice from the start ended up in a toxic manipulative relationship for about five months before i realized i was being toyed with by that time i was out a fair bit of money a few friends and my grades were in the [ __ ] from stress later found out she had a thing for virgin guys and had done the same crap to several others but she was the first woman to show any physical interest in me at all so it freaked me out pretty good for a while zero stroke 10 would not recommend still regret losing my v card to her wish i had saved it for the wonderful woman i've spent the last five years with i've been with women in their 30s since i was 19. met most of them through wow one through reddit when you're online age becomes more of a point of intrigue than a deal breaker like it would be iral we met on fetlife at the time she was 22 and i was 40 we talked for a day or so and then we decided to meet up for sex it's now six years later and we got married in september on 16. my ex and i did this met at 19 and 41 we were together for two years we had plans for marriage and kids and family i knew he had a daughter from a previous relationship turns out that previous relationship was not so previous but was rather a dead-bedroom marriage held together by hatred and a dual financial bankruptcy he was 43 and i was 28. we met at a pool tournament through mutual friends i needed a place to crash during the tournament and he had an extra bed in his hotel room we hung out and watched happy feet on his dvd player and gave each other back rubs while we both kept telling ourselves not to kiss the other's neck kept it totally pg with some massive willpower on both sides hung out the next day and he kissed me on the cheek as i left i walked away and then turned around and planted a big kiss on him i stayed at his house the next night and the pg went right the frick out the window not sure if it counts as a hookup though because we haven't left each other's side for more than a few days in 10 years and our six and two year old are now watching happy feet with us i tease him about his age occasionally especially since he's only five years younger than my mom but we have the kind of relationship where we can joke around and say really awful but hilarious crap to each other just to make each other laugh it's been good and the only regret i have about his age is that i won't have him in my life longer me and mine are 15 apart and when it works it so works currently dating somebody 14 years older than me 23 stroke 37 he started working at the church i grew up in when i was in early high school and i always loved him witty wise kind and handsome my whole family loves him never thought he could look at me romantically so i tried thinking of him as a brother was always really frustrated by a church rule that said he couldn't be alone with young women never crossed my mind to try anything just wanted to hang out with my favorite person he stopped working there a couple years ago and i'm not a christian anymore but we kept in touch i left a three-plus-year relationship last july and when i told him about it seemed like a damn just broke inside him turned out he'd been wrestling with feelings for me for several years the age difference guilt over our previous mentor minty dynamic doesn't seem to bother him quite as much anymore and i am having the time of my life loving and being loved by my favorite person i had a roommate whose girlfriend moved in with him he wound up not being able to pay his rent so i evicted him she dumped him but let her stay till she got on her feet she's 13 years younger than me once he left she started feeling her oats married for 16 years now we were co-workers i was eight years younger than him and we actually fell in love and were together for about three years we broke up and i still think he is the love of my life her 39 me 21 not really a massive age gap but it was an incredibly fun fwb situation with no strings attached she's still one of the sexiest women i've ever been with mature intelligent hard-working incredible in bed a bit shy of double your age is a pretty big gap tldr flirted with a customer at my job bangin and playing with fake titties ensued i worked as a salesperson at one of the large phone companies in a retail store i had a woman come in looking to get a new phone very attractive athletic blonde i was 24 at the time and she was 36 anyway we flirted a little bit while she was there but i honestly thought it was just her way of haggling then after she left i noticed she forgot one of her items i had her number since i worked for the phone company and texted her to tell her she left it she mentioned that she lived about an hour away and that it would have to be something she would get later but she kept going with the conversation the text got more and more flirty and eventually i volunteered to bring the item to her place she was in lingerie when i arrived this is one of my favorite stories to tell i play for a rugby club in dallas and we had just had our casino night fundraiser so we were all dressed to the nines i happened to be in highland dress killed plaid whole nine yards and looking fly as heck well night was over and the lads and i decide to hit a dive bar close to the venue here's where it gets interesting i walk in and this girl yells hey vincent what the frick i'm a bit taken aback as my name isn't vincent poor girl is mortified and starts backpedaling as she's just shouted at a six feet two inches rugger in a kilt i was far more amused than anything i smirk and just tell her darling you're pretty enough you can accost me anytime she grins i've got mine then it got weird one of the players on the women's team bounces over 52 year old rugby player who also does highland games beautiful farm-built body strong and graceful in all the best ways she's just tipsy enough to be mouthy and saunters between us is just belts out hey if you too frick tonight can i watch i cringe so hard i think i popped a disc in my back girl one kinda looks me up and down looks at girl two and just smirks yeah sure let's do this i'm not really sure what's happening so i'll let girl one tab out then literally throw her over my shoulder she love it to a chorus of shouting and laughing jackass rugby players my team saw the whole thing and we dart out of the bar to her place lucky i was at that magical place where i could still function but not finish about seven hours later we were all exhausted extremely satisfied and revealing in the mix of triumph and shame it was a good night farm built body i am going to compliment my wife with this one i'll let you know how it goes we met online over shared interests by the time we got around to ages we liked each other enough to give it a try it's been just over two years together now in my early 20s i hooked up with multiple women 15 to 20 years older than me turns out i had a huge kink with age gaps some of them were never married and had a thing for young men some were divorced and lonely ninety percent of the time it happened through online dating services now i'm in a happy long-term relationship with someone my age i was 22 and had a thing for old dude so i went on craigslist and found a bunch of guys that were like 50-ish and went and fricked them i am a little late here but boy the thing that happened to me was the wildest thing of my life so for starters i was 25 and she was 41. she is short and petite woman that was pretty hippie-ish me and her we'll call her emily worked at a bar restaurant for a while together and were always flirty but i figured just as a we both work here so it's just work flirt thing i was real wrong about that so anyway me and a couple of my friends went to a party that was at a work buddies house we were just chilling outside and casually talking then the guy's roommate and friends showed up and they are just weird like try to intimidate you and mess with you awkwardly weird at that point me and my friends just looked at each other with the we gotta get out of here look and she's drinking at this point i walked inside to gather out things and try to excuse our way out of there but emily was there and she was just not happy about that i made the excuse of this being my fourth night of drinking in a row and i need to just relax she mocked me and taunted me for a little bit but i was just taking it then it happened me and my buddy were leaned up against the wall and emily walked by she stopped looked at me and deep throated the hinakin bottle she was drinking out of then proceeded to wink and keep walking it's the only time a girl ever made me drop my jaw i immediately turned to my buddy and told him i'm going to get another beer now from there she basically used her witchcraft to get me to her place give me a very seductive tour of her apartment with little breaks of making out all of this culminating up to her room as the last stop in need i say more she blew my mind that night every time i see her she i freaks me and my chest pounds that woman has some type of spell on me and i'm not even mad at it i was 18 working at subway she was a magazine editor she would come in late like seven i would always joke with her tell her shoulder boyfriend pick up some food for you she told me if a guy dropped off food for me i would get on my knees found out where she worked and took her food she was 39 i was 18 we were fbs for a couple of years until she found a guy her closer to her age met her on tinder she's 21 i'm 38 she had bdsm in her profile and i super liked a bee we met for one drink went to her park and she gave me an amazing blowy on the park bench went back to my place and fricked for five hours we see each other weekly it's been going on since october i was 21 or 22 and he was 42 we met while day drinking in the summer took a walk to go get cigarettes and hit it off we dated for almost a year and it was honestly one of the best and most stable relationships i've ever had it sizzled mostly because i was nowhere near ready to settle down he was divorced and wanted kids eventually i did not theatre i was in community college there was a 14-year age gap between me and the guy who i played opposite it's hard to both be single and do really romantic scenes and make out with someone on stage several times a day practice and not have something happen but i have thought gray hair is sexy since early high school at around 20 years old i met a 65 year old online just to satisfy my curiosity since then i have not been with anyone under 50 totally recommend trying sex with an older man usually very relaxed and mellow without the pressure that comes with trying to get a female to orgasm hi goldilocks i was with a woman 10 years older than me for a long time it evolved into a sexless friendship too soft i needed more when we split up i reversed course and started dating a 23 year old she was too much i had forgotten what life was like when you get off of your restaurant job at 1am and head straight to the bar too hard i could not keep up finally i met my wife in addition to being everything i could ever want in a human she's only got three months on me she's just right if you are new to the channel you can subscribe i publish new videos every day until then check another video [Music] bye for now

Channel: UE Stories

Views: 31,409

Keywords: dating age, dating age gaps, dating age difference, dating age range, age gap, dating, #updootst, updoot, reddit, r/askreddit, askreddit, ask reddit, r/, \r, r\, best of reddit, reddit stories, reddit story, top posts, funniest posts, funny, funny posts, funny reddit stories, funny askreddit, reddit funny, askreddit funny, askreddit stories, reddit stories 2021, people of reddit, sub, reddit cringe, memes, toadfilms, updoot everything, updoot reddit, story, stories, rslash, comedy, fresh

Id: Ray6j5VicdU

Length: 26min 14sec (1574 seconds)

Published: Tue Apr 27 2021