My classmates dad. Well i went jogging through a newer development. Saw a guy working on al old ford galaxy. I was stopped and was like "whoa love the car" we chatted for a bit, he caught me staring at his bulge, he grabs his bulge and the head of his dick peeked out. He led me in. Told his kids to go play down stairs. He f'# me in the bedroom. A couple of weeks later i dropped my classmate off at his house, same house and said, "is Dave your dad." He goes "yeah, you know my dad?" I said, "yeah your dad has a nice car."
My best friend, we'd known each other from childhood and when we were 18 he revealed he had feeling for me and it grew from there. We took each other's virginity and he became my first boyfriend.
To random stranger at an adult bookstore while I was drunk. He was surprisingly gentle. It felt great. The next weekend, I went back again and got fucked by 3 more strangers.
Mine was with a gay neighbor friend I'd known for years, and we had a kind of running joke/teasing that if I ever went gay, I should call him first. As things turned out, we both had relationships that imploded around the same time, so I asked if the offer still stood now that we were both single. We barely made it past the front door at his place before I had his cock in my mouth.
It was very exciting and we had a great time fucking for several hours, but I was a little embarrassed when I had to admit that the reason I could take his big dick so easily was because I'd been practicing with a dildo for months leading up to popping the question !
He's also the first guy who ever called me a slut !
Neighbor guy, down the street. I was 16 at the time and had my sexual feelings awakened by him. He never really groomed me or anything, he was just kind and had an inkling about who I was. My parents were always gone for work so I had a lot of free time and... one thing lead to another and he popped my cherry!
A hookup, older guy in his late 30s, I was 23 at the time - I sucked his dick then he fucked me missionary on his bed….
It was good, but the 19 year old who fucked me bareback about a month later was a proper awakening 🤣
I was 20 and found a guy in his 50's on craiglist who wanted to fuck me. I'd posted about wanting to lose my virginity to a mature top and he responded with pictures. He had his own house in a quiet suburb and seemed like a really genuine guy over email. When we met in person, he talked me through everything as we kissed, I sucked his dick, and he ate my ass then fucked me. He knew I needed someone who would be gentle and he was exactly that. I remember it being uncomfortable at first but never painful although I don't remember where he finished. Probably in the condom that he insisted on using which I am grateful for.
Society makes it hard to have fun. I would have loved to learn about sex from someone I could trust. Especially while I was young.
I started exploring my sexuality after I was 30 and did not feel comfortable until in my 40s.
That's a pretty hot story though, for your sexual submissiveness to be awakened by the same man as your mother. And discovering kinks from finding parents' photos is a time-honoured tradition😛
I started getting my cock sucked by boys at age 14… I was also 14 it wasn’t a sex crime lol. I fucked a woman at age 17 because I thought I should try to be “normal” (straight lol). At age 20 I fucked a boy in the ass for the first time.
Guy who sucked me at 14 was a friend, girl at age 17 was a friend, bottom who gave me my first ass at age 20 was a hookup.
Well I was 17 he was 26 BBC I kinda knew through friends around town his cousin was my age. We exchanged numbers for some weed. Well I went to his house he was freeballing and hung as fuck! I couldn't control my eyes at all. And come to find out he had a girl cancel on him and he took a dick pill. He finally said you like what you see? I bit my lip and he says oh you wanna taste? That's when the Nike shorts drops and he was pretty much hard and thick and a solid 8inches was a beautiful dick. I didn't hesitate I drop down and went to town. At the time it was only the 3rd cock I ever sucked. He stood me up and got me undress. Had me bend over on the couch that's when he check to see if I was clean lol and he ate my ass. Well he was licking my hole he was asking me if I want him to fuck me? I couldn't help but say yes daddy. He ran to the room came out condom and lube.. he fingered me with lube good. He definitely knew what he was doing relaxed me calm me went extra slow let my ass adjust to his size when he went balls deep in my ass and held it my whole body it was insane and I fell In love with being bottom bcuz I got lucky and had a top that knew how to use his big oh dick...
My neighbor in his late thirties. My parents were gone on vacation and a pipe broke down in our basement. They called him to fix it, at least temporarily, but a good guy that he was, he set himself a goal to fix it for real.
As a horny teenager that I was, I kept complimenting him the entire time (somewhat innocently, like "whoa, nice guns, Mr. X. I wish to be as ripped as you are!"). It was late evening, he was already weary after like five hours of work and let's not forget that I kept pouring beer into him the entire time.
I kind of grabbed his bulge when he was resting and he looked at me, shocked, but didn't really stop me. And we went further from there.
The next day was kind of awkward because he had to come back two times more to actually call it done. He was very quiet and unresponsive. Finally I approached him and told him that it was fun but we should probably never mention this again. He agreed and from there we proceeded as if nothing ever happened. I could tell he was relieved, probably expected me to ruin his marriage with some "young and stupid jealous boy" bullshit.
No, frotting, then anal, both ways. As a curious teenager, I owned lube by then, but only a water-based one. To this day, I suspect it might be why I don't like receiving anal – just because of this one experience.
I enjoyed fucking him using that lube, though, so I'm not entirely sure.
Art of seduction is the embodiment of his style. He was only 5 inches long but made the right moves to show me the ways of sex and introduced me to bottomhood!
First blowjob from a girl 11 daughter of my next-door neighbor.
First time I ate a girl out 11 daughter of the next-door neighbor
First time fucking Vag 13 Christian summer camp
First time blowjob from a guy 16 in the shower after football practice
First time fucking a guy 18 my college roommate
First time with a couple 19.
Best mate ... He decided he was Bi ... Ended up with his Girlfriend watching a few weeks later cause she wanted to see! He was a lazy fucker and made me do all the work but fuck he felt good inside me!
Looking back on it now it’s disgusting but I was 15 and he was a 30 year old guy in the military. We only had sex 3 times but up until I was like 22 he would randomly send me money (200-500 every few weeks ) because he said he felt like he had to take care of me. He really was a weirdo and I was young and dumb. No regrets though, the sex was good.
We lived very near the school, as did he. Because I was brought up by my mum alone she was always keen for me to have male role models. So when he made friends with us and over to take me under his wing, mum was very keen. He used to get me to help him with jobs around the school in the evenings, weekends etc so we're were alone a lot. Some might say he groomed.me but when he first told me to suck his dick I was immediately up for it. We went on from there.
A gay couple who I met on Craigslist.
In hindsight, I think I was pretty lucky. I had hooked up with one or two guys before, but I had never been fucked. I didn't really think of myself as a bottom, but I knew I was in some kind of heat. I needed to get fucked.
I rode my bike across the city to their apartment in the middle of the night. They were wonderful hosts; hugged me at the door and made sure I was comfortable. They let me have a shower and then gave me a drink. (It was a sealed can of beer) They let me just talk and go at my own pace. They knew I was practically a virgin, but that I knew what I wanted.
I was barely 18 and they were both in their late 30s. The bottom was a small, dark skinned Asian guy with long hair and a cute little cock and balls--the whole of which I could fit in my mouth soft. He was very attentive to me and taught me a lot about being a bottom over the couple of visits with them. The top was a taller, more slender effeminate man, but he had a HUGE dick. Like, still the biggest I've ever held. It was a fucking white mamba. As I struggled to fit my mouth around him, his tip was cool to the touch, but firm. I could feel the weight of his shaft sagging. I was way out of my league, but his partner coached me and I offered him my ass. With a little poppers, he was able to get it in. I don't think he was really able to thrust that much--it kind of felt like I was sitting on a telephone pole. At least I was able to give him the satisfaction of deflowering a teen with a big ass and a perfect hole.
I was still young and unsure of myself, so the last time I was there, I made up some dumb excuse about my brother needing me and saw myself out. I still think about them and wonder what would have happened if I had the courage to go back. I think I still remember their number, but it's been more than 10 years, so I don't think they'd recognize a message from me. I've always regretted that I never successfully sucked a load from the 'ovaries' of that truly monolithic penis. Now that I'm more in touch with my bottom side, the things I wish I could do and let him do to me.....J & K, if you ever read this and remember me, I want to make it up to you.
To a girl, first girlfriend, summer after high school.
To a guy(s), a couple I met off of Craigslist or grinder (can’t remember) while working in NYC.
They were super sweet, even when I came early and only one of them got to fuck me haha.
They really were genuine guys, had hot cocks, and helped me really explore my sexuality! They did say I had an amazingly tight ass, and both of them did get to finish on my face, so that was fun!
Lost my virginity with a girl I date for a year. But my first time fucking a guy was an older dude living in the gentrified and expensive area of my city who hit me up when I had just moved in. We chatted for a bit and shared some pics. I wanted to get head really badly since I hadn’t had luck in a couple of months, but the problem was that I had just moved into the city and didn’t even have a car. Well, I biked over to his house, he got me in the shower since he liked really clean dicks (I think it was a fetish of his) and then started sucking my cock. I had only fooled a couple of times with other guys prior to that, but this time I was ready to drunk some ass. I asked him if he had a condom an less than 2min later I was pushing in, no lube, no spit. Just raw force on his ass until it pushed in. He freaking loved it. So much so that he was clamping my dick with his hole to the point were he was stretching the condom and pulling it out of my cock. I fucked him for a solid 5min before I unloaded inside the condom and pulled out. The dude couldn’t even move for a solid 5min. It was super intense. I think he hadn’t been fucked in a while and was a good sport for taking dick raw, which is exactly what he wanted. I asked for lube a few times and he kept pushing me inside.
Not my first time doing anal, but it was my first time fucking a man. Funny thing is that he was probably close to my dads age
School mate. I came out to him, he came out to me. One thing led to another and I fucked in after a study session. Then we played video game. We were 16.
At 15 with my 14 year old neighbor. We were horny and taking turn grinding on each other in a shed. Shorts came off and more grinding. Underwear’s came off and more grinding. He was behind me grinding on me and I was hard as a rock. I feel him separating and I thought we were switching again, but he stops and spits on his dick a couple of times and begins to rub it on my ass again…I froze for a minute and then accepted it was going to happen to me first…he kept rubbing and spitting and pushing slowly until the head went in and he came inside a lot a few seconds after that…after a brief pause he was hard again and asked to go again and I said yes. This time was a lot smoother since my ass was all lubed with saliva and cum…he lasted much longer…I had an anal orgasm.
After that day, we kept meeting up almost daily (it was summer break) and I would bottom for him. Even though I was a year older he was physically bigger. We would go in the shed and strip naked and he would bend me over and fucked me until he came 2-3 times. It wasn’t until almost half a year later when I sucked his dick for the first time while playing video games one late night with parents homes.
A guy I met on Craigslist. I was 18 and he was 19. Curious me posted an ad. I was pretty nervous and inexperienced so it took a while to get going but had a good time.
A friend when I was 14. We did everything including an attempt at penetration but we didn’t know what we were doing.
Being that it was the 90s and bisexuality wasn’t a thing, I tell people I lost my virginity with a girl when I was 17.
Wasn’t until many years later I revised that to be the night my friend and I had some good and meaningful sex, even if we didn’t want to admit that’s what it was.
It started slow, he masturbated me a few times, then gave me oral as I lay in bed, I would reach up and grab his much bigger cock and stroke it. Eventually we had anal.
My “step brother”
Long story. Short. My mom has 5 kids. The first three (sector A) have the same dad. Then I (Sector B) have a different one and then my youngest sibling (Sector C) has a different one. My mom and sector A’s dad were together a while but eventually broke up. The dad meets a new lady who has kids (Sector D). I call the dad my dad still so we all hung a lot and we saw each other alot.
Just by chance me and the middle child from sector D, were up late one night and fooled around. Gave him head, he fucked me in the back room lol. Lead to secret encounters for two years
I was 15, he was 45 a guy I met on craigslist because I seriously thought I *had* to lose my virginity but didn't want anyone to know I was gay yet and also figure an older guy would know what he was doing and all. Was it worth it? Probably not. Can't say I regret it but I did end up meeting someone I was I would have lost my virginity to. It wasn't horrible but it's definitely not something I'd be bragging about at any point.
a friend of mine, more wise and more sexually active at my local uni LGBT society, I'd say he did me a small favour, we only did it twice and never had feelings for each other, eventually we parted ways at the end of uni
my very good Discord friend. We talked about it long time and my BF who is really far away and... there seems to be no way he can get here to me, very sadly... :(
We all agreed to this. So when it was all agreed and time was right, i sat on a train, went to my friend and had some raw fun... a threesome actually
- Woman: Blowjob and sex lifeguard at my local pool. I was 19
- Man, Blowjob, mid 50s white guy. Swallowed his load while he watched olympics. I was 30.
- Man, Anal (condom): psychologist or psychiatrist in SF. I was 32.
- Man, Anal (breeding): same guy I blew earlier. I was 34.
I was raped by my high school English teacher. He had this event at his house for the highest performing students and somehow I was the last person to leave. I was 17 and he was in his late 40’s. He started to run some bath water and I was getting ready to go but I had to run to the bathroom first. He then trapped me in the bathroom and proceeded to rape me.
I thought I wanted it for the longest time (like i gave something off” but I didn’t.
I was 57 at Steamworks in Chicago 20 years ago and I was sucking cocks in the maze they had then. A young guy about 25 asked me if we could go to my room. We did and cuddled and blew each other and licked nipples and then he asked if he could fuck me. I said if you use a condom. He said no problem and while putting the condom on asked “Do you want it from the back or the front?” I said, front. He said, good, we can kiss. It was awesome. He pumped and we kissed madly and I reached down to feel his dick in my body. He got breathless and he came I we help each other for awhile. He pulled out took the condom off. We said thanks. He left and I glowed
A 35 year old on Grindr (I’m 19). We’d been talking for a while and he seemed like a pretty good guy so I went for it. I have no regrets. For my first time bottoming and having penetrative sex all together, it was amazing. He was dominant but he was also gentle at first so there wasn’t much discomfort. We got a drink first and he made me try an oyster (which I later found out is an aphrodisiac)
Unfortunately it was a girl and she ended up becoming a lesbian. She was my HS crush and we dated for almost 2yrs before she dumped me and came out as lesbian immediately afterwards
When it comes virginity towards sex (I mean, first sexual exploration), I gave my first blowjob to my cousin. But if you are asking about virginity like penetration, I gave it to a random guy on Grindr.
A military guy I met through Grindr. He was really gentle and knew how to guide me through my first time bottoming. Then went on to invite another guy to fuck me!
Older black guy either in his late 30s or 40s from craigslist and I was 16. He was tall and thin, big low hanging nuts, and a big long veiny cock. Gray pubes. He fucked me slow. I tapped out after 4-5 pumps. Thankfully he was cool and stopped and let me suck him off until nutted down my throat.
Back in the craigslist days (2014?), I met up with a guy in his office. I was 24, he said he was early 40s. Good kisser, nice cock, hairy dad bod. He was a little rough and he was resistant to wearing a condom. I being youngish, naive, and very horny, let him fuck me raw. We started with hand stuff and kissing on a loveseat. Progressed to him bending me over his desk and fucking me (no, I didn't sweep everything off in a fit of passion). Ended up with him pounding me hard on the floor prone until he came on my ass and lower back. I ended up with bruises on my thighs from his desk, and gnarly rug burn on my knees, elbow, and stomach. A few things really linger in my memory: he shared his office space with another guy, who excused himself as I came in. He grinned at me in this way that told me I wasn't the first visitor for this guy. While getting fucked over his desk was awkward and a little painful, him taking me prone on the carpet was so fucking hot. We were pretty loud by the end. I felt so hot having his sweat drip on my back. He gave me some paper towel to clean up and I made a quick exit. He messaged me a few more times to meet up, but he wanted to meet at a bar and I just wasn't feeling it.
It was from a hookup. Not long after turning 18 I had the house to myself for the weekend, I had been curious about having sexy fun with men for a while so I decided to dress up (also been a crossdresser for some time) and smoke up a bit and post an ad on craigslist back when they had a personals section.
Long story short, I sucked one dick, swallowed one load and thought that it wasn't a bad experience. Answered another responder, he had me sucking him sideways so he could reach back and finger fuck my ass, after I swallowed his load he had me sit on his lap and makeout with him as he finger fucked me and stroked my cock until I came all over his chest.
I was in a horny frenzy when he left so I went back to my computer to find another responder, he came over and I couldn't have lead him to my bedroom faster if I tried, I pushed him on the bed and hopped on his lap and started making out with him, letting him feel me up all over before I got down on my knees to take his cock in my mouth. Ended up making him cum in less than five minutes and kept on sucking to the point where he had to gently push me back. Hopped back up on his lap to continue making out with him, he finger fucked my ass even better than the last guy, hit all the right spots and got me so worked up I felt I needed to have more, so I gave him the bottle of lube I keep on my desk, laid back and spread my legs and told him to fuck me.
That first plunge hurt like hell but because I was high as a kite it didn't really bother me as much as it would've otherwise. It felt really damn good when we both got a nice rhythm going and he was hitting just the right spot to drive me fucking wild. He told me that he was about to cum so I wrapped my legs around him and pulled him in for a deep, passionate kiss as I felt his cock start pulsing as he started filling me up.
We fucked another four or five times in different rooms and positions before he had to leave because of how late it was getting, I offered to let him use the shower before he left, hopped in with him and cleaned up his cock so I could suck it again.
A guy I met on SilverDaddies in a Washigton hotel room when I was 52. I had started messing around with guys two years earlier. I am still in occasional touch with him and I can tell you that he LOVES the fact that he popped my cherry.
Told this one before, but the short form is it was a pair of grad students who made me the lunch meat. I fucked and was fucked for the first time within seconds. Fuck, that was hot!
Mine was in high school. We were both on the debate team. All of us flirted with each other. On the drive home from one tournament, while all 15 of us were in the van, he leans over and whispers if I give him a ride home I'll get a big surprise. We drove out in the country and fooled around. Ended up in the backseat on my back and him on to. Spoiled me big time when my first cock was 9".
It was with my highschool boyfriend. We were both 16 and virgins, and I wanted to celebrate Obama’s inauguration by popping my cherry.
We didn’t really know anything when he fucked me the first time, except to use a condom. I knew I needed to relax and thought a few deep breaths would do the trick. I don’t remember if he even tried to finger me.
It was pretty terrible. I cried as discreetly as I could and felt dramatically certain I was pouring blood like the kid in *Kite Runner.* (there was a little blood, but nothing like I was imagining.) Even though the act was a bit of a flop, I was insanely pleased about it and proud of myself.
When I fucked him the first time, I did a lot of research and made sure to take care of him. He loved it and wanted me to top him all the time after that. I’d say “and then we lived happily ever after,” but we broke up in college. We had a few fun years of fucking like rabbits in the meantime, though.
When I was 7 or 8, my bother started to mess around with me and by age 10, I was his toy that did what he said, until maybe around 12 my older sister caught him fucking me and said she would tell unless she got to use me too
My classmates dad. Well i went jogging through a newer development. Saw a guy working on al old ford galaxy. I was stopped and was like "whoa love the car" we chatted for a bit, he caught me staring at his bulge, he grabs his bulge and the head of his dick peeked out. He led me in. Told his kids to go play down stairs. He f'# me in the bedroom. A couple of weeks later i dropped my classmate off at his house, same house and said, "is Dave your dad." He goes "yeah, you know my dad?" I said, "yeah your dad has a nice car."
Damn..... That's crazy
Was he hot?
Lol….. that’s crazy
My boss, in a horse stall! Enough likes and will tell the whole story!
I just added like number 30, how's that?
We’re waiting
60 upvotes. Come on!
My best friend, we'd known each other from childhood and when we were 18 he revealed he had feeling for me and it grew from there. We took each other's virginity and he became my first boyfriend.
That’s lovely.
Sweet
To random stranger at an adult bookstore while I was drunk. He was surprisingly gentle. It felt great. The next weekend, I went back again and got fucked by 3 more strangers.
Hawt !
Mine was with a gay neighbor friend I'd known for years, and we had a kind of running joke/teasing that if I ever went gay, I should call him first. As things turned out, we both had relationships that imploded around the same time, so I asked if the offer still stood now that we were both single. We barely made it past the front door at his place before I had his cock in my mouth. It was very exciting and we had a great time fucking for several hours, but I was a little embarrassed when I had to admit that the reason I could take his big dick so easily was because I'd been practicing with a dildo for months leading up to popping the question ! He's also the first guy who ever called me a slut !
A random BBC in Atlanta back in 2018. It’s been my only time. 🥲
You're welcome
Hell yeah! Nice cock btw!
Congrats on being double caked up
What’s that mean?
You have a nice ass
Thank you. My ass definitely misses it.
Love this level of support and nice dick.
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Pretty amazing!
Just fuck already!!! Sheesh
Neighbor guy, down the street. I was 16 at the time and had my sexual feelings awakened by him. He never really groomed me or anything, he was just kind and had an inkling about who I was. My parents were always gone for work so I had a lot of free time and... one thing lead to another and he popped my cherry!
A hookup, older guy in his late 30s, I was 23 at the time - I sucked his dick then he fucked me missionary on his bed…. It was good, but the 19 year old who fucked me bareback about a month later was a proper awakening 🤣
A deeper awakening one might say?
Exactly!
I was 20 and found a guy in his 50's on craiglist who wanted to fuck me. I'd posted about wanting to lose my virginity to a mature top and he responded with pictures. He had his own house in a quiet suburb and seemed like a really genuine guy over email. When we met in person, he talked me through everything as we kissed, I sucked his dick, and he ate my ass then fucked me. He knew I needed someone who would be gentle and he was exactly that. I remember it being uncomfortable at first but never painful although I don't remember where he finished. Probably in the condom that he insisted on using which I am grateful for.
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I am jealous. Would have loved to have that experience.
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Society makes it hard to have fun. I would have loved to learn about sex from someone I could trust. Especially while I was young. I started exploring my sexuality after I was 30 and did not feel comfortable until in my 40s.
That's a pretty hot story though, for your sexual submissiveness to be awakened by the same man as your mother. And discovering kinks from finding parents' photos is a time-honoured tradition😛
I started getting my cock sucked by boys at age 14… I was also 14 it wasn’t a sex crime lol. I fucked a woman at age 17 because I thought I should try to be “normal” (straight lol). At age 20 I fucked a boy in the ass for the first time. Guy who sucked me at 14 was a friend, girl at age 17 was a friend, bottom who gave me my first ass at age 20 was a hookup.
Well I was 17 he was 26 BBC I kinda knew through friends around town his cousin was my age. We exchanged numbers for some weed. Well I went to his house he was freeballing and hung as fuck! I couldn't control my eyes at all. And come to find out he had a girl cancel on him and he took a dick pill. He finally said you like what you see? I bit my lip and he says oh you wanna taste? That's when the Nike shorts drops and he was pretty much hard and thick and a solid 8inches was a beautiful dick. I didn't hesitate I drop down and went to town. At the time it was only the 3rd cock I ever sucked. He stood me up and got me undress. Had me bend over on the couch that's when he check to see if I was clean lol and he ate my ass. Well he was licking my hole he was asking me if I want him to fuck me? I couldn't help but say yes daddy. He ran to the room came out condom and lube.. he fingered me with lube good. He definitely knew what he was doing relaxed me calm me went extra slow let my ass adjust to his size when he went balls deep in my ass and held it my whole body it was insane and I fell In love with being bottom bcuz I got lucky and had a top that knew how to use his big oh dick...
My neighbor in his late thirties. My parents were gone on vacation and a pipe broke down in our basement. They called him to fix it, at least temporarily, but a good guy that he was, he set himself a goal to fix it for real. As a horny teenager that I was, I kept complimenting him the entire time (somewhat innocently, like "whoa, nice guns, Mr. X. I wish to be as ripped as you are!"). It was late evening, he was already weary after like five hours of work and let's not forget that I kept pouring beer into him the entire time. I kind of grabbed his bulge when he was resting and he looked at me, shocked, but didn't really stop me. And we went further from there. The next day was kind of awkward because he had to come back two times more to actually call it done. He was very quiet and unresponsive. Finally I approached him and told him that it was fun but we should probably never mention this again. He agreed and from there we proceeded as if nothing ever happened. I could tell he was relieved, probably expected me to ruin his marriage with some "young and stupid jealous boy" bullshit.
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No, frotting, then anal, both ways. As a curious teenager, I owned lube by then, but only a water-based one. To this day, I suspect it might be why I don't like receiving anal – just because of this one experience. I enjoyed fucking him using that lube, though, so I'm not entirely sure.
In a forest in france to an asshole that raped me.
I’m so sorry that that happened to you 😢 sending you a hug from afar 🙌🏻
Beautiful start.. ugly ending. Im so ❤️🩹sorry
Thanks❤️ i got over it
Some of my cousins in Calabria mayyy or may not know a guy
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Rape is not very nice. I was 14.
My swimming coach. I was 18 and he was 45
i want to hear more
Art of seduction is the embodiment of his style. He was only 5 inches long but made the right moves to show me the ways of sex and introduced me to bottomhood!
This age gap is so hot!
yes it was ; )
A hookup who I met online
I was 13 with my best friend from my neighborhood we were 14 and both had sex with my brothers girlfriend
First blowjob from a girl 11 daughter of my next-door neighbor. First time I ate a girl out 11 daughter of the next-door neighbor First time fucking Vag 13 Christian summer camp First time blowjob from a guy 16 in the shower after football practice First time fucking a guy 18 my college roommate First time with a couple 19.
Best mate ... He decided he was Bi ... Ended up with his Girlfriend watching a few weeks later cause she wanted to see! He was a lazy fucker and made me do all the work but fuck he felt good inside me!
Looking back on it now it’s disgusting but I was 15 and he was a 30 year old guy in the military. We only had sex 3 times but up until I was like 22 he would randomly send me money (200-500 every few weeks ) because he said he felt like he had to take care of me. He really was a weirdo and I was young and dumb. No regrets though, the sex was good.
School janitor/caretaker when I was 13.
Tell us more
Wow. Yes share
We lived very near the school, as did he. Because I was brought up by my mum alone she was always keen for me to have male role models. So when he made friends with us and over to take me under his wing, mum was very keen. He used to get me to help him with jobs around the school in the evenings, weekends etc so we're were alone a lot. Some might say he groomed.me but when he first told me to suck his dick I was immediately up for it. We went on from there.
A man more than twice my age at a seedy gay bar.
A gay couple who I met on Craigslist. In hindsight, I think I was pretty lucky. I had hooked up with one or two guys before, but I had never been fucked. I didn't really think of myself as a bottom, but I knew I was in some kind of heat. I needed to get fucked. I rode my bike across the city to their apartment in the middle of the night. They were wonderful hosts; hugged me at the door and made sure I was comfortable. They let me have a shower and then gave me a drink. (It was a sealed can of beer) They let me just talk and go at my own pace. They knew I was practically a virgin, but that I knew what I wanted. I was barely 18 and they were both in their late 30s. The bottom was a small, dark skinned Asian guy with long hair and a cute little cock and balls--the whole of which I could fit in my mouth soft. He was very attentive to me and taught me a lot about being a bottom over the couple of visits with them. The top was a taller, more slender effeminate man, but he had a HUGE dick. Like, still the biggest I've ever held. It was a fucking white mamba. As I struggled to fit my mouth around him, his tip was cool to the touch, but firm. I could feel the weight of his shaft sagging. I was way out of my league, but his partner coached me and I offered him my ass. With a little poppers, he was able to get it in. I don't think he was really able to thrust that much--it kind of felt like I was sitting on a telephone pole. At least I was able to give him the satisfaction of deflowering a teen with a big ass and a perfect hole. I was still young and unsure of myself, so the last time I was there, I made up some dumb excuse about my brother needing me and saw myself out. I still think about them and wonder what would have happened if I had the courage to go back. I think I still remember their number, but it's been more than 10 years, so I don't think they'd recognize a message from me. I've always regretted that I never successfully sucked a load from the 'ovaries' of that truly monolithic penis. Now that I'm more in touch with my bottom side, the things I wish I could do and let him do to me.....J & K, if you ever read this and remember me, I want to make it up to you.
To a girl, first girlfriend, summer after high school. To a guy(s), a couple I met off of Craigslist or grinder (can’t remember) while working in NYC. They were super sweet, even when I came early and only one of them got to fuck me haha. They really were genuine guys, had hot cocks, and helped me really explore my sexuality! They did say I had an amazingly tight ass, and both of them did get to finish on my face, so that was fun!
Lost it to a freind at a BBQ Meet up with a bunch of friends from the kink community and a girl took me upstairs to a friends bed and we had sex
Some local dude I met off Reddit :) we talk every day and planning the next meet up
A police officer during the summer before my senior year of high school… god bless America! 🇺🇸
Please share that story. Feel free to DM me
Please tell me!!!
A friend and bunkmate at summer camp in my early teens.
At 16 to a high school girlfriend. 19 was my first experience with a guy, he was 27 seemed extremely old at the time LOL.
Volunteer fireman on Halloween in a glow in the dark room of a haunted house we both were working when I was 16.
Mmmm, a fireman! I still fantasize about them. Nice thought, this.
Lost my virginity with a girl I date for a year. But my first time fucking a guy was an older dude living in the gentrified and expensive area of my city who hit me up when I had just moved in. We chatted for a bit and shared some pics. I wanted to get head really badly since I hadn’t had luck in a couple of months, but the problem was that I had just moved into the city and didn’t even have a car. Well, I biked over to his house, he got me in the shower since he liked really clean dicks (I think it was a fetish of his) and then started sucking my cock. I had only fooled a couple of times with other guys prior to that, but this time I was ready to drunk some ass. I asked him if he had a condom an less than 2min later I was pushing in, no lube, no spit. Just raw force on his ass until it pushed in. He freaking loved it. So much so that he was clamping my dick with his hole to the point were he was stretching the condom and pulling it out of my cock. I fucked him for a solid 5min before I unloaded inside the condom and pulled out. The dude couldn’t even move for a solid 5min. It was super intense. I think he hadn’t been fucked in a while and was a good sport for taking dick raw, which is exactly what he wanted. I asked for lube a few times and he kept pushing me inside. Not my first time doing anal, but it was my first time fucking a man. Funny thing is that he was probably close to my dads age
Guy who invited me to the gay sauna.
My friend, also a classmate :D
an older guy my sophomore year of highschool
a 45yo married man from craigslist staying at a hotel
A nice bi guy from my college when I was 17.
first boyfriend. it was in college.
A furry I met in a Con I was 15, he was 18 and obsessed with my dick
Do you mind sharing if he had sex with you in a fur suit? I’m curious what that would be like
Hot, moisty and uncomftable BUT SO WORTH IT
I got double teamed by my two “straight” friends in high school at a sleepover
School mate. I came out to him, he came out to me. One thing led to another and I fucked in after a study session. Then we played video game. We were 16.
At 15 with my 14 year old neighbor. We were horny and taking turn grinding on each other in a shed. Shorts came off and more grinding. Underwear’s came off and more grinding. He was behind me grinding on me and I was hard as a rock. I feel him separating and I thought we were switching again, but he stops and spits on his dick a couple of times and begins to rub it on my ass again…I froze for a minute and then accepted it was going to happen to me first…he kept rubbing and spitting and pushing slowly until the head went in and he came inside a lot a few seconds after that…after a brief pause he was hard again and asked to go again and I said yes. This time was a lot smoother since my ass was all lubed with saliva and cum…he lasted much longer…I had an anal orgasm. After that day, we kept meeting up almost daily (it was summer break) and I would bottom for him. Even though I was a year older he was physically bigger. We would go in the shed and strip naked and he would bend me over and fucked me until he came 2-3 times. It wasn’t until almost half a year later when I sucked his dick for the first time while playing video games one late night with parents homes.
A stranger at a party lol
Some random guy I found on my college's facebook group. Don't even remember his name.
A guy off Grindr. Met at a local cruising spot park after dark and I got down on all fours with trousers round my ankles and he used me good
A guy I met on Craigslist. I was 18 and he was 19. Curious me posted an ad. I was pretty nervous and inexperienced so it took a while to get going but had a good time.
A friend when I was 14. We did everything including an attempt at penetration but we didn’t know what we were doing. Being that it was the 90s and bisexuality wasn’t a thing, I tell people I lost my virginity with a girl when I was 17. Wasn’t until many years later I revised that to be the night my friend and I had some good and meaningful sex, even if we didn’t want to admit that’s what it was.
My bully, turned friend, during a sleepover at his house lmao. Sleepovers were fun.
Lost my virginity to an older brother of mine. I was 12 and he was 17. Both male.
Wow. How did that make you feel?
It started slow, he masturbated me a few times, then gave me oral as I lay in bed, I would reach up and grab his much bigger cock and stroke it. Eventually we had anal.
Are you okay. That can be traumatic but maybe you enjoyed it.
I have dealt with this in therapy, I know it was not my fault I have no guilt, I was too young and didn't know any better. I'm okay
My dad i was 12
Woah. You ok?
Yeah im ok :)
My “step brother” Long story. Short. My mom has 5 kids. The first three (sector A) have the same dad. Then I (Sector B) have a different one and then my youngest sibling (Sector C) has a different one. My mom and sector A’s dad were together a while but eventually broke up. The dad meets a new lady who has kids (Sector D). I call the dad my dad still so we all hung a lot and we saw each other alot. Just by chance me and the middle child from sector D, were up late one night and fooled around. Gave him head, he fucked me in the back room lol. Lead to secret encounters for two years
Step brother is in quotations cause we have no real relations
I was 15, he was 45 a guy I met on craigslist because I seriously thought I *had* to lose my virginity but didn't want anyone to know I was gay yet and also figure an older guy would know what he was doing and all. Was it worth it? Probably not. Can't say I regret it but I did end up meeting someone I was I would have lost my virginity to. It wasn't horrible but it's definitely not something I'd be bragging about at any point.
Tell us your story?
A closet case
a friend of mine, more wise and more sexually active at my local uni LGBT society, I'd say he did me a small favour, we only did it twice and never had feelings for each other, eventually we parted ways at the end of uni
A random stranger who I never saw again.
my very good Discord friend. We talked about it long time and my BF who is really far away and... there seems to be no way he can get here to me, very sadly... :( We all agreed to this. So when it was all agreed and time was right, i sat on a train, went to my friend and had some raw fun... a threesome actually
- Woman: Blowjob and sex lifeguard at my local pool. I was 19 - Man, Blowjob, mid 50s white guy. Swallowed his load while he watched olympics. I was 30. - Man, Anal (condom): psychologist or psychiatrist in SF. I was 32. - Man, Anal (breeding): same guy I blew earlier. I was 34.
I was raped by my high school English teacher. He had this event at his house for the highest performing students and somehow I was the last person to leave. I was 17 and he was in his late 40’s. He started to run some bath water and I was getting ready to go but I had to run to the bathroom first. He then trapped me in the bathroom and proceeded to rape me. I thought I wanted it for the longest time (like i gave something off” but I didn’t.
So sorry to hear it. Are you doing okay?
Overall yes but I do think that’s why I struggle with men sometimes. It definitely affected me more than I let on. Thank you for asking.
Glad you’re doing okay :) if you ever need someone to talk to, feel free to reach out
I was 57 at Steamworks in Chicago 20 years ago and I was sucking cocks in the maze they had then. A young guy about 25 asked me if we could go to my room. We did and cuddled and blew each other and licked nipples and then he asked if he could fuck me. I said if you use a condom. He said no problem and while putting the condom on asked “Do you want it from the back or the front?” I said, front. He said, good, we can kiss. It was awesome. He pumped and we kissed madly and I reached down to feel his dick in my body. He got breathless and he came I we help each other for awhile. He pulled out took the condom off. We said thanks. He left and I glowed
Wow lovely story :)
A 35 year old on Grindr (I’m 19). We’d been talking for a while and he seemed like a pretty good guy so I went for it. I have no regrets. For my first time bottoming and having penetrative sex all together, it was amazing. He was dominant but he was also gentle at first so there wasn’t much discomfort. We got a drink first and he made me try an oyster (which I later found out is an aphrodisiac)
Did you go bare or safe?
Safe
Unfortunately it was a girl and she ended up becoming a lesbian. She was my HS crush and we dated for almost 2yrs before she dumped me and came out as lesbian immediately afterwards
When it comes virginity towards sex (I mean, first sexual exploration), I gave my first blowjob to my cousin. But if you are asking about virginity like penetration, I gave it to a random guy on Grindr.
An older hookup on grindr I have a thing for older dominant men. And he knew just what to do with me. I get horny thinking about it
It was pretty much a hookup.... tried to stay in contact but it was just weird.
Some Dude on a hookup App.
A military guy I met through Grindr. He was really gentle and knew how to guide me through my first time bottoming. Then went on to invite another guy to fuck me!
Your dad
He was attractive. Dad bod. Its weird when i smell someone/stranger who has that distinct scent of fabric softner it takes me back
Older black guy either in his late 30s or 40s from craigslist and I was 16. He was tall and thin, big low hanging nuts, and a big long veiny cock. Gray pubes. He fucked me slow. I tapped out after 4-5 pumps. Thankfully he was cool and stopped and let me suck him off until nutted down my throat.
Back in the craigslist days (2014?), I met up with a guy in his office. I was 24, he said he was early 40s. Good kisser, nice cock, hairy dad bod. He was a little rough and he was resistant to wearing a condom. I being youngish, naive, and very horny, let him fuck me raw. We started with hand stuff and kissing on a loveseat. Progressed to him bending me over his desk and fucking me (no, I didn't sweep everything off in a fit of passion). Ended up with him pounding me hard on the floor prone until he came on my ass and lower back. I ended up with bruises on my thighs from his desk, and gnarly rug burn on my knees, elbow, and stomach. A few things really linger in my memory: he shared his office space with another guy, who excused himself as I came in. He grinned at me in this way that told me I wasn't the first visitor for this guy. While getting fucked over his desk was awkward and a little painful, him taking me prone on the carpet was so fucking hot. We were pretty loud by the end. I felt so hot having his sweat drip on my back. He gave me some paper towel to clean up and I made a quick exit. He messaged me a few more times to meet up, but he wanted to meet at a bar and I just wasn't feeling it.
It was from a hookup. Not long after turning 18 I had the house to myself for the weekend, I had been curious about having sexy fun with men for a while so I decided to dress up (also been a crossdresser for some time) and smoke up a bit and post an ad on craigslist back when they had a personals section. Long story short, I sucked one dick, swallowed one load and thought that it wasn't a bad experience. Answered another responder, he had me sucking him sideways so he could reach back and finger fuck my ass, after I swallowed his load he had me sit on his lap and makeout with him as he finger fucked me and stroked my cock until I came all over his chest. I was in a horny frenzy when he left so I went back to my computer to find another responder, he came over and I couldn't have lead him to my bedroom faster if I tried, I pushed him on the bed and hopped on his lap and started making out with him, letting him feel me up all over before I got down on my knees to take his cock in my mouth. Ended up making him cum in less than five minutes and kept on sucking to the point where he had to gently push me back. Hopped back up on his lap to continue making out with him, he finger fucked my ass even better than the last guy, hit all the right spots and got me so worked up I felt I needed to have more, so I gave him the bottle of lube I keep on my desk, laid back and spread my legs and told him to fuck me. That first plunge hurt like hell but because I was high as a kite it didn't really bother me as much as it would've otherwise. It felt really damn good when we both got a nice rhythm going and he was hitting just the right spot to drive me fucking wild. He told me that he was about to cum so I wrapped my legs around him and pulled him in for a deep, passionate kiss as I felt his cock start pulsing as he started filling me up. We fucked another four or five times in different rooms and positions before he had to leave because of how late it was getting, I offered to let him use the shower before he left, hopped in with him and cleaned up his cock so I could suck it again.
A friend when we were 14. We had been experimenting with stuff for a while and just decided to try it out one day.
I enjoyed the orgasm and the eroticism of having my penis stroked and sucked. I adjusted and learned to crave his nightly visits to my room.
A guy I met on SilverDaddies in a Washigton hotel room when I was 52. I had started messing around with guys two years earlier. I am still in occasional touch with him and I can tell you that he LOVES the fact that he popped my cherry.
Told this one before, but the short form is it was a pair of grad students who made me the lunch meat. I fucked and was fucked for the first time within seconds. Fuck, that was hot!
Mine was in high school. We were both on the debate team. All of us flirted with each other. On the drive home from one tournament, while all 15 of us were in the van, he leans over and whispers if I give him a ride home I'll get a big surprise. We drove out in the country and fooled around. Ended up in the backseat on my back and him on to. Spoiled me big time when my first cock was 9".
It was with my highschool boyfriend. We were both 16 and virgins, and I wanted to celebrate Obama’s inauguration by popping my cherry. We didn’t really know anything when he fucked me the first time, except to use a condom. I knew I needed to relax and thought a few deep breaths would do the trick. I don’t remember if he even tried to finger me. It was pretty terrible. I cried as discreetly as I could and felt dramatically certain I was pouring blood like the kid in *Kite Runner.* (there was a little blood, but nothing like I was imagining.) Even though the act was a bit of a flop, I was insanely pleased about it and proud of myself. When I fucked him the first time, I did a lot of research and made sure to take care of him. He loved it and wanted me to top him all the time after that. I’d say “and then we lived happily ever after,” but we broke up in college. We had a few fun years of fucking like rabbits in the meantime, though.
rando from craigslist who lied about his age
A coworker and his friends I volunteered was not sure what I was getting into .
My cousin, He was 6 days older than me but was always my boss.
When I was 7 or 8, my bother started to mess around with me and by age 10, I was his toy that did what he said, until maybe around 12 my older sister caught him fucking me and said she would tell unless she got to use me too