Tell Us Your 'first Time' Stories

[Guest iJoey]

I was 27 and married just 6 months. I thought I would be able to put my bi past behind me. I met Jesse online and our first meeting had me on my knees sucking his thick 8 inch cock while he fingered my ass. Our next meeting, the next day has me ass up with his cock in my mouth and his dildo in my ass. About two weeks later. I was on my back with his bare cock deep in my ass getting bred. 

 

Thank God my wife was gone all weekend. I was at Jesse's house getting fucked all weekend. I've been a bare back slut ever since. 

 

Jimmy

[00Felix]

First sex with a guy: church camp (!), a counselor who was probably about 20 when I was 15 asked me to help scout a trail for a hike. He took me out in the woods and blew me. He swallowed everything--my dick to the hilt and my cum. He was a really cute Asian dude with a great body.  I kissed him but he didn't want me to do anything else to him. He blew me two more times that week.

 

First time fucking: party for cast members after high school play (I had three lines). Another guy in the cast had a boyfriend who was early 20s and we were all kinda drunk and he took me in the bathroom and dropped his pants and gave me his ass. Big drama afterward when the bf found out. Nobody does drama like a 17 year old betrayed twink, lol.

[RayKindle]

I was 18 and had finally had my fill of dildos. I hopped online and unsuprisingly found a guy willing to fuck my virgin hole. He came over and took things slow, giving me my first kiss, but I had his pants down in no time flat. He fucked me three times that night; refusing to belive that I had never taken a dick, I guess that the dildos gave me plenty of practice. 

 

Thinking back on it, I wouldn't change anything as it set me on my path to be a slut, being used by someone at more or less random. 

[dirtysydguy]

Well my first time getting fucked was when I was 17 and I met a guy who was also 17 online who lived not too far away. We chatted for a few weeks before 1 day his family went out for the day and I was free so I went over. I showered again, mainly just to calm my nerves before heading to his room where I sat with towel wrapped around me and he was dressed in shorts and t-shirt sitting beside me on his bed as we started to watch some online porn videos before starting to grope each other and quickly getting naked as I dropped to my knees to take my first hard cock in my mouth, after a few minutes we moved to the bed where he put me on my back and got between my legs before getting out a pack of doms and getting one out and putting it on, the odd thing was that neither of us had actually fucked a guy before (he had sucked a cock and I had fucked some pussy) so we really had no need for doms but we did, before he pushed my knees to my chest and gave me my first experience of a cock in my ass. I don't remember it lasting too long but we did organise to do it again in2 days time when he would be home alone again and that was the time I first took a raw cock.....and became addicted!!

 

The next time we were getting into it again and this time he rolled me on to my front and got me on my hands and knees at which point he found the thing I love as much as a load of cum being blown on my hole then fucked in my hole and that was the feeling of a wet tongue on my hole, tongue fucking me, devouring my hole, it made me horny like I had never been, the house could have been on fire and I wouldn't have noticed...after 10mins of that (or at least thats what I remember it was but it could have been between 2mins and 30mins in reality) he pushed me hard down so i was laying completely flat face down on the bed my legs spread so he was on his knees between them as he slid his body up the back of mine licking my neck and ears as he rubbed his cock against my wet hole, until then I had never even considered fucking raw but all I could think of was how much I wanted his cock to just slide inside me right then and I may have tried to make that happen as I was grinding my ass back against his cock as it slid up and down between my cheeks teasing my hole then as the grinding got more aggressive as we got hornier we both moved enough to allow the head of his cock to position itself at my hole as he stopped to slide back forward again and i know that I could have moved quickly to prevent it but I willing allowed and probably helped too allow his cock to push inside me raw, as his cock started to push against my hole he pulled back from his hard thrusting movement thankfully, as the head of his cock slid inside me and we both let out a loud audiable groan of pleasure as he stopped, waiting for my reaction which was to push back against him feeling his cock slowly slide balls deep inside me raw, we were both instantly hooked from then as he started to fuck me but didnt last long before advising he was about to cum and I pushed back hard on his cock taking it as deep as I could squeezing my hole hard on it as he unleashed the first ever load of cum to be blown in my ass (the 1st of 5 that day). We would get together at every possible opportunity we could over the next 6 months before I went travelling overseas and just before I got back he went for a 12month overseas university exchange thing. We did happen to find each other again about 5 years later and he invited me over to his apartment and spent the first hour or so trading stories of our various bb experiences before he gave me a load then took 1 from me before sending me off with another load before getting dressed and heading off. Only 1 of the lifts was working at the time and he was on level 15 of his building so I had a bit of a wait before finally getting in the lift which stopped at most floors on the way down and quickly filled up, while I stood in the back corner feeling like a dirty cum slut getting increasingly turned on as his cum started to run down between my cheeks and then the back inside of my legs and as I was wearing a pair of shorts I had a clearly visible wet trail starting to trickle down while no one in the lift had any idea, fucking loved it and have been addicted to that feeling ever since, I LOVE the feel of cum oozing back out of my cum filled hole down my legs after a good fuck session as I make my way home!!  

[cheatingjock]

My first time was Christmas break of my freshman year of college.  I found my high school coach online. I had spent much too much time looking at him shirtless to not recognize him  Spent a weekend at his house. He was the first guy to fuck me, and I took it bare because I trusted him (haha).  Spent the weekend exploring different things, but mostly getting fucked.  He was the only guy to bareback me until my first serious relationship.

[seaguy]

My first time was Christmas break of my freshman year of college.  I found my high school coach online. I had spent much too much time looking at him shirtless to not recognize him  Spent a weekend at his house. He was the first guy to fuck me, and I took it bare because I trusted him (haha).  Spent the weekend exploring different things, but mostly getting fucked.  He was the only guy to bareback me until my first serious relationship.

Coach spent a weekend coaching you on how bareback sex is so much better than condom sex.

[cheatingjock]

Coach spent a weekend coaching you on how bareback sex is so much better than condom sex.

Yes but i didn't learn the lesson for another few years

[cam1972]

Well my first time getting fucked was when I was 17 and I met a guy who was also 17 online who lived not too far away. We chatted for a few weeks before 1 day his family went out for the day and I was free so I went over. I showered again, mainly just to calm my nerves before heading to his room where I sat with towel wrapped around me and he was dressed in shorts and t-shirt sitting beside me on his bed as we started to watch some online porn videos before starting to grope each other and quickly getting naked as I dropped to my knees to take my first hard cock in my mouth, after a few minutes we moved to the bed where he put me on my back and got between my legs before getting out a pack of doms and getting one out and putting it on, the odd thing was that neither of us had actually fucked a guy before (he had sucked a cock and I had fucked some pussy) so we really had no need for doms but we did, before he pushed my knees to my chest and gave me my first experience of a cock in my ass. I don't remember it lasting too long but we did organise to do it again in2 days time when he would be home alone again and that was the time I first took a raw cock.....and became addicted!!

 

The next time we were getting into it again and this time he rolled me on to my front and got me on my hands and knees at which point he found the thing I love as much as a load of cum being blown on my hole then fucked in my hole and that was the feeling of a wet tongue on my hole, tongue fucking me, devouring my hole, it made me horny like I had never been, the house could have been on fire and I wouldn't have noticed...after 10mins of that (or at least thats what I remember it was but it could have been between 2mins and 30mins in reality) he pushed me hard down so i was laying completely flat face down on the bed my legs spread so he was on his knees between them as he slid his body up the back of mine licking my neck and ears as he rubbed his cock against my wet hole, until then I had never even considered fucking raw but all I could think of was how much I wanted his cock to just slide inside me right then and I may have tried to make that happen as I was grinding my ass back against his cock as it slid up and down between my cheeks teasing my hole then as the grinding got more aggressive as we got hornier we both moved enough to allow the head of his cock to position itself at my hole as he stopped to slide back forward again and i know that I could have moved quickly to prevent it but I willing allowed and probably helped too allow his cock to push inside me raw, as his cock started to push against my hole he pulled back from his hard thrusting movement thankfully, as the head of his cock slid inside me and we both let out a loud audiable groan of pleasure as he stopped, waiting for my reaction which was to push back against him feeling his cock slowly slide balls deep inside me raw, we were both instantly hooked from then as he started to fuck me but didnt last long before advising he was about to cum and I pushed back hard on his cock taking it as deep as I could squeezing my hole hard on it as he unleashed the first ever load of cum to be blown in my ass (the 1st of 5 that day). We would get together at every possible opportunity we could over the next 6 months before I went travelling overseas and just before I got back he went for a 12month overseas university exchange thing. We did happen to find each other again about 5 years later and he invited me over to his apartment and spent the first hour or so trading stories of our various bb experiences before he gave me a load then took 1 from me before sending me off with another load before getting dressed and heading off. Only 1 of the lifts was working at the time and he was on level 15 of his building so I had a bit of a wait before finally getting in the lift which stopped at most floors on the way down and quickly filled up, while I stood in the back corner feeling like a dirty cum slut getting increasingly turned on as his cum started to run down between my cheeks and then the back inside of my legs and as I was wearing a pair of shorts I had a clearly visible wet trail starting to trickle down while no one in the lift had any idea, fucking loved it and have been addicted to that feeling ever since, I LOVE the feel of cum oozing back out of my cum filled hole down my legs after a good fuck session as I make my way home!!

Officially boned. Fucking hot story man.

[a6uldeve84u]

The first time I got fucked without a condom was at age 16.  I got my license and 2 days later one of the family cars.  I went to a local YMCA where I had heard rumors of meeting men in the steam room.  Well, I got cruised and did hook up with a guy who was hot.  He was 32, 6'3, 200, hair, and had a cut 9 inch cock.  He convinced me to leave with him and go to his place.

 

When we got there, we got into his bed and began making out including sucking each other.  He began fingering my hole and found it clean.  (I had figured out on my own to use an enema bag just in case.  There wasn't the internet at the time to research.)  Between making out and kissing, he told me he wanted to fuck me.  I told him that would be great but that I had never been fucked.  The way he came to a halt, I thought I was going to be tossed out.  He was just surprised I was a virgin.

 

He had me to suck his dick some more, turned me onto my stomach putting a couple of pillows under my hips, and lubed my ass thoroughly inside.  He then took time to lube his dick as he finger fucked me.  Finally, he took his cum rag and put it in my mouth, gently held my hips, put his dick to my hole, and began pushing with greater pressure.  My sphincter popped open and I saw stars of a million galaxies.  My hands grabbed the sheet, my ass clamped shut, my back strained in an arch, and I screamed wide-eyed into his cum rag.  He was very caring and waited a very long time while my body adjusted to his invasion.

 

He repeatedly asked me if I was okay and shook my head yes.  I was determined to get fucked.  He finally sensed my readiness and began pushing more into me.  My ass burned and hurt but I was not going to stop him.  What seemed like days to get all the way inside me, Glen's pubic hairs finally began tickling and bristling on my ass cheeks.  Once he was finished pushing in, we rested again.  Each of you know what the feeling is like during that first fuck as a bottom.  I was sweating like it was raining and loving all the pain and the now full ass feeling that I felt.

 

Too soon, Glen began pulling his dick out of me.  He fucked me slowly for a very long time and with each piston in and out the pain eased away and euphoric sensation began filling my ass and mind.  He began fucking me faster and as best I could after awhile I began pushing my ass upwards to meet his downward thrust.  He stopped long enough to have me to get up, tossed the pillows to the side, and position me doggy style.  We went back to fucking and by this time he was long dicking me the full length of his cock. 

 

I felt sweat from his body dropping onto me as our tempo increased.  He was now fucking me hard and I was using my hands to brace myself on the bed and pushed backwards onto his cock matching him stroke for stroke.  I was sweating by this time and was in overdrive at lusting for his dick to go in me further.  Within a couple more minutes he asked if I was ready for his load of cum and I told him yes.  Somewhere in the next half dozen or so full length strokes, Glen grabbed my hips hard, slammed his dick as far in my ass as he could, began groaning through his clenched teeth, and for the first time in my life I felt a man's dick swell up even more in my ass and spit out load after load after load of ball juice into me.  My ass instinctively clenched and released his cock milking Glen for all his DNA.  It took a long time for him to finish and when he did he lay down on top of me with his dick still in my ass.  I was now a committed cum-in-my-ass addict.

 

We fucked twice more that night before I went home missing curfew which was well worth it.  Glen and I fucked for the next 6 years every chance I got to get away including when I went away to university.  I would come home and spend the weekend with him claiming to be staying on campus to study.  But, finally on our last weekend after I had graduated, Glen told me he had been transferred and that was the last I saw him.

[Guest ff-whole]

Fuck, I'm 56 now and the first time has been damn far away... 

I really can't remember any more... I do remember I was working as a kid of 15 16 or 17 in a car garage and the mechanic introduced me kinda in man sex... Yes I was under-aged alright... later when I finished technical college and past my 18th and later birthdays we kept meeting a lot... he was into fisting, though his hands were way to big for me, so I had to fist him... Even later when he was married.

The real bare dick unloading inside of me must have been much, much later...

Just the last 7 years, I really started to pig out and take a lot of bare cumshots inside...      

I love it...

[Guest]

I have mentioned this in other threads.  I thought it was unusual, but I guess it's not.  I was 9 when I was raped by a neighbor, which continued for many years.  I really didn't know what sex was, but I was attracted to this guy and he clearly picked up on it.  Seems strange to say, but I figured out very quickly what I was good for, and that has stuck with me my whole life.

[Pozguyinchi]

I have told my story many times on here but I think it can be told again. When I was 9 my step dad and mom broke up. My real father had died and I had become very attached to my step dad. My mom through a course of events gave me the opportunity to move on with my step dad and live. I loved him and jumped at the chance. We moved into a small one bedroom apartment in the city and it was suppose to be a temporary situation but we had to sleep in the same bed. I liked the feeling of having him close to me and snuggled up on me. There was a natural progression of my holding on to his cock throughout the night and feeling it get hard in my hand. It never seemed dirty or wrong. Over time I would snuggle into his furry chest and stroke his cock. He would finger me and we would kiss. This literally went on for years. When I was 13 we had progressed to his big beefy cock rubbing up against my pussy. His precum would make it slick. I had a natural desire to want him inside of me but I let him pick the pace. After a few months of him rubbing his precum cock against my now aching for cock pussy and him cumming on my back when he got off, he started just putting the tip of his big cock in me. He was so gentile and loving. He still would pull out and cum on my back. I don’t know what real sex was but I knew I wanted his cum inside me and not on my back. Over about a three week period he would get his massive cock a little farther in my pussy each night until eventually he was balls deep. He was still always gentle and always asked me if it hurt. It did but my desire to have him in me was so much greater that I didn’t let him know of the pain.  He was still pulling out to cum on my back and I instinctively knew I should be having his cum inside of me. I finally asked him if he would leave it in when he came and he did. I knew at that point that I always wanted to be bred. Over the next 5 years the sex was real and constant. It was a real love story and he taught me what sex between two men should be. 

[Pozlover1]

I spent a lot of time at a friend’s house. Once his dad came home and we had my Chevy completely apart in the garage. To his credit, over the next 3 weeks he showed us how to rebuild an engine. My friend had a brother two years younger, a classic middle child. Several years earlier I had found him when we were both hiding from a seriously dangerous dodgeball game at the Y and I assured him we were right to avoid getting hurt for no reason. But I pretty much found him annoying. 
Once when I spent the night, they sent him to get me up. He did. Later that day and the next weekend we had sex, which I liked way more than I wanted to. This was 1969 and I did not want to be Gay. Plus I could see that we were headed to get caught if we kept it up, all of which is exactly what I told him. I drifted away from that family and they moved away a couple years later. 

Edited December 24, 2019 by Pozlover1

[leatherpunk16]

In the autumn of 1997, I had to move to an apartment with my grandmother. It was a cheap-looking affair: a one-story building with four apartments in it, and we all shared one basement. There were no walls in the basement to signify which corner belonged to which tenant. I wasn't there very long before I noticed that my neighbour had a private room in this basement. His name was Jeff and he was just a couple years younger. I finally met him one night while I was doing laundry downstairs. He and his twerpy little brother marched up to me in that weird way teenagers do when they are on a mission, and started a conversation. I remember very little about it - mostly getting to know one another. This boy was CUTE and his name was Jeff. By this point in my growth, I knew I was gay, but I never had any opportunities to do anything about it. In fact, I wasn't even sure of my inclinations toward men. I hadn't really decided, and it was 'uncool' to be gay at my school, so I kept up appearances when I had to.

Jeff was in fairly good shape, slender and defined, and had sweet eyes and lips. Since I had few friends and he was right next door, Jeff and I hung out quite often. We played video games in his basement, talked about school things and life issues, watched straight porn, and smoked quite an unhealthy number of cigarettes. We would also share a bottle of liquor from time to time. One night in the early spring of 1998, we really pounded the bottle hard, and were drunk as skunks. The room got really quiet, and Jeff was stroking himself a bit and watching me silently. Then he suddenly asked me, "Wanna fuck?" Just bluntly like that. My dick instantly stood up and I said "sure". 

He broke out the lotion, put some on my dick, and bent over for me. I just went with instinct. We agreed on a time limit - just a few seconds to "see what it's like". A few seconds turned into several minutes, and neither one of us wanted to stop. He muffled his moans into a pillow and I just slowly screwed him. Took my sweet time with it, but my inexperience kept telling me to just jackrabbit his hole. Jeff was surprisingly loose for a virgin. I don't remember my thoughts at the time. Eventually I felt that shudder when the climax is about to be reached. I kept it quiet so no one would guess what we were up to, and gave a few hard thrusts, and planted that seed deep. 

Jeff's demeanour suddenly shifted, like he didn't expect me to actually cum inside him. He just lay on the bed, shocked and silent, and I leaned against a wall, totally spent. My mind was blown, and so was my load. I lit a smoke, and just enjoyed the come-down. Jeff quietly withdrew himself, and went out of the room to "spit out a goober", but I think he actually went to the floor drain to squeeze that cum back out. He was gone way too long for just a spit. He came back in, sat down, and joined me in a post-fuck high. He rolled a blunt and smoked it, and just continued to look toward me, but not AT me. Almost no words exchanged. 

Hot story, right? I knew I was gay right then, and I had just bred my friend on a spur of the moment. Evidently, Jeff didn't think it was so hot. A week later, he tried to kill himself. When he came back from the hospital, I offered it to him again, and he absolutely refused. I think he couldn't handle his new-found sexuality, even though he initiated the whole thing. And by the end of the month, he was going to start going to the Catholic school across town, and suddenly moved his home over there. I never saw him again. 

I'm glad I made this discovery with a trusted friend, even if he didn't take it too well. I hope he's okay, and that he accepted his sexuality when he was ready to. I'll probably never know what happened to him.    

[Guest rawbro]

I don't remember much about it anymore because I tried to blank it out of my mind for a few years because I was in denial about liking sex with dudes as well as women but, 10th grade right before school this guy I had been chatting with in an AOL chatroom lived literally down the street from the school, I was worried I would be seen going into his place that morning so I came to school 2 hours earlier. I was super nervous and he was this giant bear of a man, when we got there he told me to get undressed, I did, then he bent me over, ate my ass and introduced me to poppers and something called maximum impact, then he slid into me bareback. It hurt like hell but the last thing I remember was taking a hit of the maximum impact and I'm pretty sure it knocked me out for a bit. He said he stopped fucking me once he saw I was knocked out but the load in my ass said otherwise. I never met him again after this but that was my first time with a guy. I wouldn't hook up with a dude again until I was in my 20s.