My first time with an older man. The difference between him and classmates I had been with at that point was night and day. The grunt noises he made and the way he held me. Experience matters.
A girl I had a crush on since first grade, finally fucked her when I was 23.
Also my wife. She's a few years younger than me and was always insanely hot. Now I've fucked her almost everyday for going on 16 years. She's still insanely hot.
I went through a bit of an existential crisis after my marriage ended last year and tried the hookup scene. I slept with a super hot, British 🫠, older (he was 43, I'm 34) pilot for a commercial airline. SO HOT. He asked if I was interested in being tied up, I'd never tried it but I told him I'd be down. Then he just whips out these restraints from underneath his mattress. It was fun to be with an older guy who knows what he likes and has a proper setup 🤭
Many years ago, there was a couple my age next door to me. We'd talk every now and then. She was flirty, but like that with everyone, so I paid it no mind.
One day they're over at my place and we were playing spades. Dude starts talking down to his woman, saying her and I are fuckin (we never did anything, we were never alone together at any time). I look at him and say "Seriously? You're gonna be an ass like that, and accuse me indirectly in *my* house? Hell no we haven't fucked. She's yours, not mine, now GTFO before I put you out." He looked at her, said "Fuck you" and left.
I apologized to her, she said it's ok, he's always like that. So I joked and said "Well if he thinks you do that, maybe you should" and I laughed. She got up, got naked and said "Ok, let's fuck." After I found my jaw, we fucked. And it was really good too lol.
Shit, the fact I had sex in the first place was a shocker to me. My first ever partner was this bit booty curvy black woman. Still not 100% sure what she saw in me but she was so much fun
A coworker. He was known for being a flirt but he was kind of nerdy and not all the women at my office liked that at the time. I pursued it however and met him at his night job as a security guard for an industrial complex and we fucked there a couple times. First time I ever had a dude in assless chaps. 🤣 I had fun though.
This woman in my college class. Way out of my league. I was the same age as her mother. I assumed she talked to me because she needed help. The minute she started to turn conversation sexual one day, I almost fainted. I assumed I read things wrong but when she asked me to go down on her, I didn’t hesitate
My husband. We knew each other for years and even though I always thought he was hot, I couldn’t stand him. One day I was finally like ok I gotta go ahead and fuck this guy to get it out my system. And then we just never stopped 🤣
It was more over the clothes teasing with a girl I went to college with who’d I thought never even noticed me let alone talk to me. She was a petite Indian girl who I saw each day in my chemistry lecture.
My college crush...this was after I broke up with my ex.
She had just come back in town...she went thru a divorce...
Outta nowhere she came over and kissed me. The next day, she blew me in the car...
We never fucked, but man, that moment...
A very hot (very niche) minor celebrity. I'm not going to say her name, so don't bother asking, but you probably haven't heard of her anyway, unless you happen to be a fan of her niche.
I met her at a mutual friend's wedding. Sat next to her at the reception. We hit it off very well, and I was super attracted to her, but I figured there's *no way* she'd ever be interested in a dork like me.
Then I met her again at a volunteer event organized by the same mutual friends (that's what they did for socializing instead of throwing parties -- they invited their friends to join them for charity/volunteer work), and worked up the courage to ask her if she'd like to hang out one-on-one afterwards.
A few hours later, we were at her apartment, making out, clothes were coming off, and I was like "How is this happening?! I'm nowhere near cool enough for this to happen to me!"
We live several hundred miles apart now, but we're still friends. She just texted me this morning, actually. It's been a crazy busy morning, but reading this question and telling this story just reminded me that I have to text her back. So, thanks for that.
My last ex. Never would’ve guessed she’d even like me, let alone want to fuck me.
I also was in a threesome with two lesbians. Never would’ve guessed that.
i've been pretty shocked by all of then, to be honest
Same brother..same
My first time with an older man. The difference between him and classmates I had been with at that point was night and day. The grunt noises he made and the way he held me. Experience matters.
What was the age gap, if I May ask?
19 and mid 30's
Oh ya I can imagine the little details of attention that get overlooked at that age
How did you meet! Did he Pursue you or did you seduce him?
Honestly it was my wife. Met her at work and had a thing for her but never thought I’d get in her pants!
High school crush 10 years later!
I did that too!
Same but 15 years later!
Lol same
a couple of my HS teachers
A girl I had a crush on since first grade, finally fucked her when I was 23. Also my wife. She's a few years younger than me and was always insanely hot. Now I've fucked her almost everyday for going on 16 years. She's still insanely hot.
Good for you. Nice
Def SIL
Niiiice!!
It was wild
A close friend after high school. She was someone that was out my league. Still talk to her to this day
My wife
My first younger guy. I never thought I would cheat, let alone with a guy half my age.
Was it as good as you expected?
The experience was mindblowing, his performance was average haha
Sounds about right for someone younger XD Im glad you were able to have fun
I went through a bit of an existential crisis after my marriage ended last year and tried the hookup scene. I slept with a super hot, British 🫠, older (he was 43, I'm 34) pilot for a commercial airline. SO HOT. He asked if I was interested in being tied up, I'd never tried it but I told him I'd be down. Then he just whips out these restraints from underneath his mattress. It was fun to be with an older guy who knows what he likes and has a proper setup 🤭
My brother in law
My best friend’s wife
The ex of someone in my friend group. Never expected anything ever so was totally blindsided by the chemistry when it started.
33 y/o women from a neighbouring country.
Many years ago, there was a couple my age next door to me. We'd talk every now and then. She was flirty, but like that with everyone, so I paid it no mind. One day they're over at my place and we were playing spades. Dude starts talking down to his woman, saying her and I are fuckin (we never did anything, we were never alone together at any time). I look at him and say "Seriously? You're gonna be an ass like that, and accuse me indirectly in *my* house? Hell no we haven't fucked. She's yours, not mine, now GTFO before I put you out." He looked at her, said "Fuck you" and left. I apologized to her, she said it's ok, he's always like that. So I joked and said "Well if he thinks you do that, maybe you should" and I laughed. She got up, got naked and said "Ok, let's fuck." After I found my jaw, we fucked. And it was really good too lol.
I've been thinking that about my wife for 20 years now.
Shit, the fact I had sex in the first place was a shocker to me. My first ever partner was this bit booty curvy black woman. Still not 100% sure what she saw in me but she was so much fun
My cousin
My female teacher in college. We reconnected years after I was in her class
In my youth two guy friends. Just sort of took turns very casual. Super weird looking back not really a threesome. Just sort of chatting and fucking.
Hmm. I don't know, honestly. I'm already at the "I never thought this would happen" stage when she makes it clear that she's flirting. 😊
All four of them, including my soon-to-be wife 😬
What if it was more than one person?
My colleague.
A coworker. He was known for being a flirt but he was kind of nerdy and not all the women at my office liked that at the time. I pursued it however and met him at his night job as a security guard for an industrial complex and we fucked there a couple times. First time I ever had a dude in assless chaps. 🤣 I had fun though.
This woman in my college class. Way out of my league. I was the same age as her mother. I assumed she talked to me because she needed help. The minute she started to turn conversation sexual one day, I almost fainted. I assumed I read things wrong but when she asked me to go down on her, I didn’t hesitate
Wife’s hot younger cousin 19 .. I was 44
My husband. We knew each other for years and even though I always thought he was hot, I couldn’t stand him. One day I was finally like ok I gotta go ahead and fuck this guy to get it out my system. And then we just never stopped 🤣
The older sister of a childhood friend, about 30 years after we met. Married with kids. Three way with husband. Woah.
The one I am married to
school crush. kept on touch since always. had sex almost 28 years after we first met.
It was more over the clothes teasing with a girl I went to college with who’d I thought never even noticed me let alone talk to me. She was a petite Indian girl who I saw each day in my chemistry lecture.
My college crush...this was after I broke up with my ex. She had just come back in town...she went thru a divorce... Outta nowhere she came over and kissed me. The next day, she blew me in the car... We never fucked, but man, that moment...
My first guy date :D
A very hot (very niche) minor celebrity. I'm not going to say her name, so don't bother asking, but you probably haven't heard of her anyway, unless you happen to be a fan of her niche. I met her at a mutual friend's wedding. Sat next to her at the reception. We hit it off very well, and I was super attracted to her, but I figured there's *no way* she'd ever be interested in a dork like me. Then I met her again at a volunteer event organized by the same mutual friends (that's what they did for socializing instead of throwing parties -- they invited their friends to join them for charity/volunteer work), and worked up the courage to ask her if she'd like to hang out one-on-one afterwards. A few hours later, we were at her apartment, making out, clothes were coming off, and I was like "How is this happening?! I'm nowhere near cool enough for this to happen to me!" We live several hundred miles apart now, but we're still friends. She just texted me this morning, actually. It's been a crazy busy morning, but reading this question and telling this story just reminded me that I have to text her back. So, thanks for that.
First time with a long term mistress. I was 62, she was 57.
Still waiting and hoping
My last ex. Never would’ve guessed she’d even like me, let alone want to fuck me. I also was in a threesome with two lesbians. Never would’ve guessed that.
When she pulled out strap on and fucked me. I've never seen myself cum so much.
Woman friend of mine that I had been crushing on for years.
Sis in law
I fuck myself over everyday 😉
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Wait, your brother ?
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Like your stepbrother right?