>be me 24
>didn't become curious about my sexuality until my late teens
>jerked off to stories over and over again
>finally decided to meet up with someone
>post ad on double list looking for an older man
>get a response from a man in his 50s, clean cut, ddf
>drive over to his house
>undress in his guestroom
>lights dim, I begin to give him head, struggling with my breathing to get it right
>he flips me on my back and I feel his tongue caress the sides of my cheeks before he plays with my hole
>he begins to blow me for a little bit but I'm not that into it
>ask him to fuck me an he obliges
>he slowly slides in and begins to build up speed
>he fucks me raw
>we alternate from missionary to doggy
>really enjoying it at this point
>ask him to finish inside me
>hes more than happy to oblige and finishes deep inside me
>I cant get off so I go home

Mainly into women but I enjoy getting fucked by men. Want to see him again someday as he was able to fuck for longer than the other older men I slept with.

>be me, 19
>friends already lost their v-cards, feel left behind. literally haven't done anything
>this was around 2009 so smart phones weren't really a thing yet
>go on craigslist asking for someone to fuck me
>get all these old men
>some hot guys but im weary that some are pic collectors so I don't go ahead with some of them
>one guy, 30yos, we end up chatting on skype
>meet up a couple of times
>we end up doing it all on our 3rd meet up
>make out, suck each other, he fucks me with lube but im nervous so my hole is tight throughout but he just pounds me like crazy, didnt really enjoy it
>regretted after
>still met up with him a few more times because he had a big dick, but this time he would do more foreplay and eat me out
>my hole relaxes and the sex feels amazing

i ditched him when he tried to come inside me

>be in early 20s
>bifag, mostly want to suck dick
>make Craigslist post
>ignore 90% of them for being too old, ugly dicks, black or fat
>finally have a decent looking guy my age email me
>guy writes half a novel every email, but we agree we should meet up soon
>message him one evening
>he warns me hes kind of drunk but hes down for getting blown
>head over, he let's me in, takes me to his bedroom
>drops his shorts and lies down
>start blowing him, hes still soft
>he only ends up getting half hard
>cums pretty fast
>leave kinda disappointed

>>2691410
I mean, I don’t really get a choice because I was a minor. To tell the first time story at a legal age would be skipping over like 30 encounters. Ironically all of them I wasn’t even 14 yet.

But I digress, I’ll discuss my first time after that.
>26 years old
>online bf is 18
>moves to my country
>suck his cock on my couch, sniffing his unwashed foreskin after the 28 hour travel. Spend the first night sucking each others dicks constantly. Stick it in his ass the next day, blasts cum all over the walls as i unload inside.
>married for 8 years now

Nothing really interesting, I must've been in 5th or 6th grade and was kind of an outcast and befriended another kid who had the same interests. Not sure how but one day we found ourselves at a secluded spot near our school and I don't remember who made the first move but we started making out. We started going to that spot regularly to make out, we would also cuddle, sadly it never led to anything sexual, probably because we were so young, but I guess that was my first, boring, gay experience. He moved schools soon after that and I never saw him again.

I was honest in that other thread.


First time sucking dick I was 21, a senior in college, getting out of a long term relationship. I always thought I might be bi and finally decided if I were going to experiment, that was the right time. I posted on CL personals and eventually agreed to blow a guy in his truck in a dark out of the way parking lot on campus. I was really nervous and he was heavier than I'm really into, but I loved it the second his dick hit my mouth and swallowed without a second thought when he came.
My first time bottoming wasn't very noteworthy. It was a CL ad as well, the guy said he wanted it anonymous as possible. He wanted someone to come over, no names exchanged, he tops with a condom, and then leave. I thought it would be a good, anonymous hookup to try taking dick for the first time. I did show up, he turned out to be a tall skinny Asian guy. We got naked and I laid down on his bed. He sucked my dick for a bit and I came really quickly. Then he put a condom on and we lubes up, and he also came really quickly after entering me. So it wasn't bad or anything, but really quick and kind of awkward.

>>2691511

My first time getting it raw was more exciting. I was back home with my parents for winter break. They've always been the types to go to bed at 8 or 9, so I was often a bored college student with lots of time. I eventually found another CL ad for someone looking for car head and agreed to meet later that night when everyone at my home was asleep. I was super horny in the build up and even toyed my ass in the shower with a round toothbrush holder. When the time came, I snuck out of the house, met him on a street corner, and we went to the dark parking lot behind a nearby strip mall. I remember he had dark hair and glasses. We fooled around a bit and got in the back seat of his car. While I blew him, I let him finger me. Eventually he asked for me to turn around so he could see my ass. He kept spitting on my ass and fingering me, and using his spit to jerk off. Then he asked if he could rub his dick against my crack. I knew where it was going from there but was so crazy horny I didn't care. After a little of the "I just want to poke it a bit," game he eventually shoved all the way into me. Since I was a little prepared from toying myself and the fingering, and he wasn't that big, it didn't hurt too bad. He came after just a few pumps anyway. Didn't warn me at all, he just came. I actually to this day still find that crazy hot, but his energy changed afterwards and he didn't say a thing when he drove me home. I jerked off an enormous load when I got home remembering that I had another man's cum up my ass, then did it again in the morning when I woke up.

My first time was a grindr hookup at age 19. I finally mustered the courage to start looking after years of yearning for men. It helped I wasn't doing much of anything, still lived with my parents and hadn't decided what I wanted to do with my future. Me and this one guy, much older, I assume around 40+, hit it off. He offers to pick me up in his car. I feel my heart pounding in my chest with each passing second until he finally rolls up into my parents garage. I enter and he drives me to a parking lot. We stay pretty silent up until he kisses me. It scared me so bad, feeling his weight on my body and the whole suddenness of it. It was my first kiss, he said I was really good. We drive around some more until we reach a park were he parks the car there. He must've loved the thrill since it was close to a highway, cars speeding past as I unbuckled his belt. I very quickly start sucking him off, his cock was very adorable. I find it funny now, looking back he wasn't my type at all, but his stomach and cock were just too cute. Anyways, he keeps telling me how good I am at this. The words "you'll make a lot of men happy" still echo around my mind, I wish he never said it. Too scared to swallow and ask him if he's fine with finishing via masturbation. He obliges, he was very kind and understanding, and I watch him cum all over himself. He promised me multiple times he would help me release to, but that ended up being false. Frankly it didn't bother me but it did make him a liar, oh well. When he dropped me off I crawled back in bed and checked grindr to see his account had completely disappeared. I never got to learn his name. I regret ever doing this, I think it destroyed my psyche for a year until I was eventually sent to the ER. I also really enjoyed it, every second of it, I still get hard imagining it. Makes me wanna rope. Oh well.

>Be me, 17 years old, left my homophobic country for college, on my own without my parents or anything

> download Grindr
> make a quick profile and start messaging guys
> I’m a black twink BOTTOM and I don’t put my face up so it takes a while for me to get anything
> eventually this one guy he’s 30smth, white Italian, moderately attractive messages me
> he thinks I’m 18, doesn’t know it’s my first time
> we agree to meet him at his hotel room
> when I get there I’m shy as fuck and scared as fuck. He starts touching me and I get an instant boner and try my best to touch back
> he kisses me and that’s my first kiss too. And I’m a surprisingly good kisser according to him even though I’ve never done it before
> he’s a bit rough, grabbing me and carrying me (I’m 5’10 and he’s at least 6 foot) and we get on the bed and he starts to move me to his crotch
> I crack and tell him it’s my first time and then he feels shocked and awful that he wasn’t treating me nicer or slower
> he guides me and I give him head for the first time, he seemed to enjoy it and I’ve practiced a lot on bananas so
> then I tell him I’m not douched so he doesn’t want to try anal
> we eventually jerk off together and he says to message him whenever I’m feeling horny and that he’ll teach me how to have real sex (anal)
> I get so scared and ashamed of myself I block him and delete the app

He was rich too. I shoot my self in the foot thinking about how I probably missed out on a sugar daddy earning big European money. It’s also interesting to think about how confident I’ve become since then. Even though my appearance has barely changed, now I wouldn’t even give someone like him a response.

I'm still a virgin because I passed out when me and my old gf tried to do the deed. MY heart raced so bad holy shit, that wasn't really a first time but we broke up because of that, I was really realyl scared lmao

For me it was when I was 15 in summer camp. Knew I was at least bi even back then. There were 3 of us per cabin and one of the guys got sick and left for home so it was just me and a cute 17yo boy.

Talking about stuff lead to watching porn on his phone led to me ending up on my knees sucking on his uncut cock. He kept making sounds like he liked it, runing hands through my hair and I really liked it.

Came in my mouth I swallowed. After that I sucked his cock like 2 times a day for the next two weeks plus some other stuff before we went hoke and never seen each other again.

>>2691653
Elaborate on the other stuff

>be 18, first year at college
>bisexual, never done anything with a guy but been jacking off to gay porn for a while
>make profile on gay dating site
>it has a list of hookup spots and gloryhole locations
>ride the bus to an adult bookstore
>neighborhood's sketchy but I'm thinking with my dick
>head into booth and put in some cash
>after jacking off for a bit a dick appears from the hole
>medium size uncut, brown skin
>start sucking on it
>feels weird but the guy's moaning so I guess I'm good at this
>he asks to come into my booth
>say yes and unlock it
>a Mexican guy in his 40s comes in, not ugly, not really handsome
>he pulls out his wallet to feed the machine
>catch a look at a picture of him and his wife & daughter
>instant guilt
>make up an excuse and take the bus back into the dorms
I've had better sex since then thankfully, but I still don't fuck with married men unless their partner knows they're sleeping around. Being a homewrecker just doesn't sit right with me.

>>2691410
>me early 30s
>met 40s guy at bath house
>told him he could fuck me and he did
>attraction to men irl joyously confirmed

>>2691410
>bi kid never been with a dude
>the age of craigslist
>finally find a kid around my age and not repulsive and get him to come over
>comes over, smaller dick than he said
>doesn't want to suck me
>fucks me, I barely feel it (smaller than my dildo)
>cums inside me, gets dressed says thanks and leaves
>texts me a couple days later says that was fun, can we do it again
>so he comes over, fucks me for 2 seconds, cums and leaves
>disappointing, but I got some dick, so there's that.

>> In HS straight kinda friend going through some heavy shit
>> It causes him to be isolated from the rest of the friend group
>> Also going through some heavy shit in my life
>> Trauma bonding
>> He's lonely. I'm lonely. Decide to be lonely together. Start hanging out more
>> He's not gay. This is just practice for when I get a BF supposedly
>> Slowly escalates but very one sided
>> I start jerking him off cause that's what a BF would do
>> First time I smell someone elses balls and I love it. Musky. Sweet. Horny
>> It's like I can smell how much he wants to nut
>> At first he's uncomfortable with it but after a few times I guess horny wins out
>> hard to understand what he's thinking but he cums so he's into it?
>> Eventually while jerking him he asks me to "put my mouth on it"
>> I dunno dude that's really really gay
>> He laughs and I keep jerking him but then he ask me again. Just this once. It's just practice.
>> Ok I guess there's no turning back after this.
>> Start sucking. He's had a bj before. Is like coaching me.
>> Cover your teeth. Use your hand. Faster. Slower.
>> I'm gonna cum. Keep your mouth on it.
>> Cums in my mouth. I act like a pussy and don't swallow.
>> Go to bathroom to spit it out
>> Didn't then and still don't like the aftertaste of cum. It stays in your mouth.

That was the first time I sucked him. Will tell the rest later maybe.

>>2691410
Friend discover that's he is gay, hit on me, we fool around, i fuck his ass.

Reposted, true story
>be me
>curious, desperate, and have already fried my brain with yaoi
>have cybersex with guys online
>some want to meet
>flake a lot
First experience
>meet one guy online who wants to use toys on me
>sneak him into my room through the window while I’m supposed to be at school
>jerk together, he uses a plug on me and sucks me at the same time
>lie on the floor so he can ride my dick
>cum instantly and feel gross
>he leaves
>liked how the plug felt
>decide to try more ass play
First time bottoming
>meet college aged dude online
>tell him I want to try bottoming
>late night
>shower and clean ass the best I can
>wait for him in my pajamas under a tree behind my house
>he parks on the street and I sneak out of the shade to his car
>small talk in the back seat
>he pulls his dick out and I just stare at it
>gives me a look that says “it’s not gonna suck itself” but I’m confused
>he pulls my head down and it clicks
>didn’t expect to suck dick since I only wanted to bottom but I have to get him hard somehow
>feeling him get hard in my mouth turns me on. he was about 5”
>put the seats down and lay on my stomach in the trunk space
>he puts on a condom and pulls my pajama pants down
>he sees I went commando for him and calls me a good boy
>works his dick into me and starts to fuck me on my stomach
>feels okay but I’m soft and not very turned on
>car gets hot and the windows steam up
>his shirt and my hoodie come off
>feel his sweat dripping into my back
>cop car drives past and he ducks low to avoid the headlights
>ask what’s wrong but he covers my mouth and holds me still
>adrenaline rush
>feel his bare sweaty chest on my back, his hips on my ass and the pressure of his stiff dick in me
>get hard
>he fucks me for 15 or 20min and finishes in the condom
>pull up my pants, say goodbye
>sneak back inside
>text him I had fun
>jerk off
>decide the idea of being a bottom turns me on and I must explore it more

>>2691829

This would have been the perfect teen relationship for me. I would've sucked his dick whenever he wanted. But it honestly it took him a very long time to initiate anything though. It was always me reaching for his dick. Sometime he even seemed annoyed like ugh now I have to go cum in his mouth again. It made me feel like shit the whole time. I didn't know what they feeling was at the time though so resentment just slowly built up overtime

> hard to remember the first time we fucked
> just like the bj he doesn't initiate the sex but he always escalating it
> more training. stick your tongue all the way out. deeper. good personal cumdump
> he was asking "can I fuck you" after a couple of months
> again he wasn't a virgin and was having sex I assume frequently in his previous relationship
> kinda made me feel like it was something I should be doing for him as his not technically boyfriend
> it's good practice for when you get a bf anon
I know this sounds straight out of a nifty story but I swear it was really like this.
> eventually talks me into it
> terrified I will shit on his dick and he will be disgusted with me
> know nothing about douching, or really how the bowels work. won't learn that stuff for years
> don't remember why I agree to it the day I do
> literally stucking my finger up my butt trying to see if I feel shit and pulling it out
> feel gross af. still terrified there some left
> don't even think we used lube just spit
> his dick is wide and flat like a blunt spear
> hurts. feels like i'm going to take a shit the whole time
> asking him to slow down. asking how much longer.
> is basically ignoring me or tell me he's almost done as he keep fucking away
> it doesn't take a long time but it's so uncomfortable the whole time it feels like it does
> he nuts in me
> tries telling me stuff like that wasn't so bad for me
> feel gross and go take a shower

These are so horrible and tragic that I am sorry I opened the thread, much more read it and considered sharing. Jfc.

>>2691960
that's how gay sex, or I dare say, how gays' get something that shapes them for the rest of their lives. Almost every first time is outside the fairytale romance books people usually fantasize about lol, very fascinating links on rape, molestation, and DL scenes

>>2691960
>>2692136
most of these are grim for sure, but not all of us had shit first times my dudes

>>2691410
nothing special really
>late 2014
>turned 18 that year and I was super horny
>looking at M4M personals on Craigslist
>found a daddy type that I was looking for: dadbod, average sized dick, only in his 40s and uncut
>he was horny and asked me to send him pictures of my ass
>gladly obliged, even sent him a video of me spreading my cheeks wide open for him
>agreed to meet up at a hotel
>opens the door and out loud says "wow"
>we start making out
>I'm hard as diamonds
>He desperately tries to release his raging boner from his pants
>pulls out a perfect cock for me, not too big, not too small, and he pulled back the foreskin to show a gorgeous, smooth pink head
>He pushes my head down, but I'm already on my knees sucking him off
>love the way it feels in my mouth, but somewhat disappointed it didn't have a super distinct taste or smell
>we start undressing completely
>we're completely naked now and he commands me to get on the bed and bend over
>I happily assume the position
>I can feel him poking my ass, slapping his floppy cock against my cheeks, pushing his head against my hole
>eventually he gives up
>I asked him what's up
>he said he recently lost one of his boy toys, because he moved away
>said he didn't expect another boy to want to hook up with him and he was so worried about his performance with me that he couldn't get it up
>ended up talking about his situation and basic getting to know each other type shit
>go home with not a single drop of cum down my throat or in my ass

>be me, closeted hard
>be september this year, out of town for a bachelor party weekend
>last night before driving home 4 hours
>did some performance enhancers, sniff sniff, just a bump tho
>crash a 2 am but can't sleep cause coke
>had my own room at the airbnb so I start jerking my dick and crusing sniffies
>so built up full of cum from a long weekend
>older top says he can host me before I leave town
>get up and pack my stuff at 8am and am the first checked out
>omw to this house, top says it's his own rental and that he's got a friend to double team with me
>awkward energy when I go inside door was cracked open for me to just walk in
>two older daddies sitting on couch
>ask em where they want me and they both stand up and drop pants and i sit on the ottoman
>daddy #1 good size dick 6" cut girthy fills my mouth perfectly
>daddy#2 unfortunately smaller 3" max
>#1 gets hard easily but #2 struggled
>as soon as #2 gets up he nuts and I swallow
>#1 had a 8/10 dick but was more fuzzy then I hope for
>workshop #1 for a while and says he's gonna cum
>pull my own out and jerk myself while he gets himself close
>he comes in my mouth and I swallow him as well
>they both watch and let me milk their flaccid cocks while I finish myself
>eat my own cum and we all walk out together