First time raw, planned or unplanned?

[Guest BiGuyInWI]

My first ADULT bareback experience: I was in my early 20s, discovering the thrill of anonymous hookups via the internet. I was flirting with an older man who lived in a nearby neighborhood (within bicycling distance) and he convinced me to visit him. I went over nervous as hell but he was sweet and we kissed and petted and he went down on me and rimmed my asshole. He had me on my back on his bed, legs open wide, so ready. His cock wasn't huge but nice and thick, and he mounted me getting balls deep quickly. I loved the feeling of being stuffed by this muscular man. I could tell he was getting close and I hugged him with my arms and legs as he gasped and spurted his load in me. I loved it so much that I held on after he came and he stayed hard, still rocking. After a while he got excited again amd started really fucking my sloppy hole again, gasping 'What are you doing to me?!' He soon shot a second load in me and collapsed. I was so messy and so happy. He said that had never happened to him before.

[hotguy02]

Definitely not planned.  He made a comment that he didn't like using condoms and I took his word that he is neg.  That was like 15 yrs ago to this day he is the only one I let fuck me

[Guest bbbearlover1]

Unplanned. My ex and I always went to bed with me spooning him. As I was waking up, I stretched, and slid right into his pussy.  I did not plan this. I was very much about safe sex and condoms. I pulled out almost as soon as I went in. My ex grabbed my dick, and he put it back in his pussy, telling me it was alright. Once we were clear that we were raw fucking, I fucked the hell out of him. Neither of us had ever raw fucked anyone, and we were amazed and pissed to discover what we'd been missing. That was October 2006, and I haven't worn a condom since (my ex became my ex less than two years after that). I loved pussy, but I was clueless as to how it really felt raw. That was one of the best sexual days of my life (discovering my love of the male ass was first, and the realization of my desire to dominate white males was another).

[hotguy02]

1 minute ago, bbbearlover1 said:

Unplanned. My ex and I always went to bed with me spooning him. As I was waking up, I stretched, and slid right into his pussy.  I did not plan this. I was very much about safe sex and condoms. I pulled out almost as soon as I went in. My ex grabbed my dick, and he put it back in his pussy, telling me it was alright. Once we were clear that we were raw fucking, I fucked the hell out of him. Neither of us had ever raw fucked anyone, and we were amazed and pissed to discover what we'd been missing. That was October 2006, and I haven't worn a condom since (my ex became my ex less than two years after that). I loved pussy, but I was clueless as to how it really felt raw. That was one of the best sexual days of my life (discovering my love of the male ass was first, and the realization of my desire to dominate white males was another).

 

Wow amazing daddy

[Guest]

Totally planned. It was my anal virginity,  too.

I was in my early 30s, and had only  sucked cock a few times since preteen years (my brother got me started). I'd always loved watching gay bareback porn, and always wanted to know what it was like feeling a man pumping his hot cum into me. I told myself that I will fuck women with condoms only when THEY ask, but I'd never ask a man you wear one. I knew that I should take the cum that was offered to me (if it ever was)and never let anything between their cock and my ass. I wanted it, all of it, natural. 

So,  one random Thursday I decided today was the it. No pretense.  I told myself "I'm going to get fucked today, and that's it". I put an ad on  Craigslist Sacramento looking for an older bareback top who could host after I got off work.  I had a couple responses,  but one cock pic from a mid 50s Top did it.  I swear I told myself,  for the first time ever,  "I've got to take have THIS cock.  This delicious - looking,  thick cock must fuck me. I've gotta have it." It was on. Throughout the day i sneaked peeks at that meaty looking dick on my work computer,  always looking over my shoulder to make sure no one could see. 

Nervously I pulled in front of a McMansion in Folsom, Ca. As I applied the parking brake I promised myself I would let this MAN do anything he wanted to me,  and that I would be on my knees sucking this unknown man's cock with 1 minute of stepping inside his house. I wanted to show him,  and myself,  what a fucking slut I want to be. 

I knocked,  he answered,  I stepped inside.  I was greeted by a 5'8 Asian Daddy compared to my 6'1. He was wearing only a leather thong. As he closed the door,  I leaned down to kiss him. He then grabbed me,  kissing me harder, and I melted to my knees to fulfill one of my earlier vows. I now had a total stranger's 8"x5" cock getting hard between my lips in 45 seconds after seeing his face. 

After a few minutes sucking him,  he took me upstairs to his bedroom that had a huge TV playing BB porn. He pushed me to my knees,  and again I worshipped his cock and balls with my tongue for awhile as he glanced between the TV and me. I didn't care of he paid me any attention because I was here to make him pump cum for me.

Without a word,  he guided me to the bed where I got on my hands & knees... telling myself no matter what happens... no matter the pain,  I'm not leaving until I'm bred. I didn't have to wait long at all... because as soon as that thought finished I felt cool lube being wiped on my hole.  Startling,  yes,  but it was soon followed by his cock. I didn't have time to think,  and I liked it that way. 

He wasn't patient,  or gentle.  Of course,  I never asked him to be. He slid inside my virgin hole and just started fucking.  Grabbing my hips,  he just took my easily offered ass and used it. I remember the pain not being as bad as I had feared, but it still hurt.  There wasn't any pleasure at all,  but I didn't care.  I was getting fucked! A real, older man was giving me his bare cock!  I didn't know his real name,  or even his last name... just "Chuck"... and he is going to seed me. I loved it!

About 5 minutes later I felt him slow down his pace into deep thrusts,  and I knew what was cumming. I eagerly awaited the sensation I knew I was about to feel... and THERE it was.  Thick.  Warm.  Creamy.   Perfect.  Only one thing on Earth could feel like that... a man's hot cum inside me. Needless to say,  I was hooked. 

I gave him a deep kiss, then got dressed and left his place, thinking that because I just let a complete stranger buttfuck me that I'm a faggot slut... and faggot sluts take their fucking and leave so as not to be an annoyance or bother to the man who just used them. 

On my way home,  I lit a cigarette and squeezed my sore sphincter, feeling the wetness leaking from me. I told myself i could get used to this as I let out a satisfied exhale. 

Edited December 15, 2017 by ColoradoCub

[rawloadstaken]

I began my voluntary sexual exploration phase just as what became known as the HIV crisis roared into the public eye, and that turned me into a condom advocate. I played around with other guys, but any penetration required a wrapping.

Years later, after my first divorce, I went to a bathhouse and hooked up with a hot cowboy type in the steam room: I was sucking his dick and he just kept rubbing my ass and sliding his fingers in and out of it. We wound up rinsing off and heading to my room, and he started eating me out once we got in there.

I handed him a condom and watched him unwrap it and put it on, then turned around and felt him push into my hole. He’d pull out every now and then to add lube, and I’d occasionally reach behind me to feel the condom. Finally, after about fifteen minutes of driving me into the mattress, he put one hand on the back of my neck and one hand on the small of my back and just plowed the living hell out of me. He stiffened up and started bucking, then slowed down to a couple of long-dickings.

He rested on me for a second, dick still hard in my ass, then reached over and dropped the condom in front of me, pulled out, slapped my ass, and walked out of the room.

I just lay there in shock. Did he just come inside me?

I reached back, and sure enough, my ass was loaded with his cum. I was torn between being horrified and finding it one of the hottest things I’d ever felt. I wound up blowing my own load just by fingering my hole and feeling the cum slosh inside and around my ass.

[Guest FinalDL2021]

My first time was unplanned. I got caught up in the heat of passion, and just rolled with it without mentioning condoms. The guy, I was with, was very hot, and our getting together was unplanned too, which made it more exciting.

 

this was 10 years before I actually made the choice to bareback, and no longer use condoms.

[BottomsUp]

Definitely unplanned. The whole encounter wasn’t planned at all, at least on my part. I was drinking with a guy in my dorm my freshman year of college. The more we drank, the more he would find reasons for touching me. Being the naive 18 year old I was back then, I didn’t know any better and after I was nice and drunk, he began to grope me and tell me how hard I made him. He started to kiss me, almost forcefully before he pulled out a massive 10 inch dick. I struggled to take all of him in my mouth so he pushed me down on his bed and started working fingers into my hole. I was so drunk that I didn’t really know what to think or do and ended up going with it. It wasn’t until he was trying to get his cock inside of me that I realized what was happening and that he wasn’t even wearing a condom. I only used condoms back then and started to panic a bit. It took forever for me to open up enough and I remember feeling like he was spending hours pounding me and splitting me open. When he finally came, I remember how amazing it felt, having him shoot his load inside of me and how he would keep fucking me after he came too. It made me love raw cock and for the next two years we kept this up, always raw and always hot. 

[chargedodger]

Definitely unplanned.Knew NOTHING about sex.A horny older man popped my anal cherry in his camper and came deep inside me with his hand over my mouth.1966.:)

[bareback-flipflop]

Tricky question. Because the very first (with guy) was with my first boyfriend and it was definitely planned.

But if I think about the first with an unknown guy, I must join the lasts. That was Definitely unplanned.  I was 24, I had problems with the guy who was my above-mentioned boyfriend at that time. So I cheated him. I met a guy, after a small talk he offered to take a shower. He had a large shower stall. We took shower together, washed eachother and began to stroke our body and cock. I sucked him and he pushed me to the wall of stall and barebacked me. It was amazing. I didn’t panic, but the top asked me many times, whether I am a regular barebacker. 

[huis_rat]

my 1 time raw was unplanned. he take me hard and pozzed me

[Guest]

I was raped when I was young.  So... unplanned.

[Guest]

Unplanned but not a bad experience. Quite an athletic guy I met and talked to at a gay social event (I think someone's birthday) and he asked for my contact details. I wasn't very confident back then and didn't try and take it further and left the party before most there. An hour later, and after I had gone to bed, this guy appears on my doorstep asking if he could stay with me. I had lube for wanking off with and using my dildo but no condoms and lying in bed he kept trying to push his hard cock into my hole. He was so hot that I soon let him fuck me properly. HIV wasn't widespread in my area back then so I was in fact more concerned about STD's. I would never have let my ex-boyfriend fuck me raw so this was quite a step into the unknown for me. But I woke up with him and he fucked and loaded me again before he left. I got tested not long afterwards and it was in fact a few more years before I had unprotected sex again but this time with a (then) committed new partner. 

[shaved_thong_lover]

Unplanned - Raped by two guys, possibly more.

So I was young, about 18. Started realizing there were gay guys having sex in the dunes at Jones Beach in NY. So went back there a few times and ended up learning how to cruise.  Started off small, sucking cock, then riding guys cocks with condoms and then letting guys fuck me with condoms.  Since I was the youngest most twinkish/jockish guy there and a bit fem wearing a g-string while tanning, I got alot of attention.  So maybe two or three guys would fuck me or make me suck them during a day at the beach. 

I went back one day and two guys wanted to film me, so I let them start camcording me while they were fucking me.  They gave me some shots which I assumed were just some booze and next thing I knew I was in and out of consciousness with guys fucking me and making me suck them all raw.  They had a belt around my neck and were chocking me in and out of consciousness.

I finally woke up in an ambulance, no idea how I got there, oxygen on me, barely could see, totally naked, and bleeding profusely from my hole with intense pain.  Had terrible scars on my neck for months from being choked.  And had to have surgery to remove a corona beer bottle from inside me.

All and all a terrible experience... But since then, I have been a cumdump whore... Not sure if I would have been even if this didnt happen... But that is my first raw experience.

[rawTOP]

Not quite sure how to answer the question… I had my first sexual experience in 1990 at the height of the AIDS crisis. I was pretty adamant about using condoms 'cause getting HIV was a literal death sentence back then. BUT I'd often do 2-3 strokes raw and then put on the condom. But I'm not sure 2-3 strokes counts as bareback sex when you then put on a condom.

In terms of zero condom sex it was definitely unplanned. There was this guy I hooked up with (in either 1990 or 1991) who was a trainer at one of the gyms in Hells Kitchen (so great body). I fucked him with a condom (and probably did the 2-3 strokes of raw), then he fucked me (I was pretty vers back then). He probably started with a few strokes of raw, then he resisted putting on a condom when I asked him to rubber up. I was pretty nervous and kept asking him to put one on. He kept saying he'd pull out before he came. Then he pulled out and came like a 1/2 second later. In hindsight I probably got part of his load in my ass. I was pretty furious with him and left.

In terms of intentionally going bareback I didn't do that until a few years later (1995). I had this rebound relationship right after my lover died of AIDS and the guy was a voracious bottom who talked me into going raw. We both got tested and then after that never used condoms. I loved the sensation of fucking him raw after all those years of condoms and basically dumped as many loads as I could in his ass the months we were together. When we broke up and I started hitting the bathhouses again it was really hard to rubber up since bareback felt so much better and more and more I found myself fucking anonymous cumdumps raw.