First time raw, planned or unplanned?

[ShyBottom]

The raw part was definitely planned, if sorta with apprehension. I'd met this guy on grindr who was incredibly hot, sweet, and totally hung and up till then I'd had barely any experience with other men beyond my ex; even with my ex I'd used condoms.

We were completely into each other and I was excited to have sex again but he mentioned that he basically didn't want to use condoms because he didn't get enough stimulation while wearing them. I started to hesitate because I really wanted to be safe and not start exposing myself to STDs just because I'd left a relationship recently but even while we chatted he kept cool and was incredibly nice and didn't pressure me into changing my mind. Eventually I relented and told him that I really wanted to sleep with him and try going raw but that I wanted it to be special, he was super excited and assured me that it would be.

Meeting him at my place shortly after, I'd never imagined him to be so tall and sexy and things quickly moved to the bedroom. When I saw his dick though I got a little bit scared! It was bigger than anything I'd ever taken, and definitely the thickest, it was maybe around 8 inches but with how strong and tall he was the size got me afraid he would hurt me somehow.  He let me take my time and we began with me sitting on him which god, I can't believe my tiny hole managed to take it in with so little experience. I struggled to bounce myself on him though because of how stretched I felt and after a while he must have got impatient because he put me on the bed and started fucking me from behind. After that he completely went to town pounding into me while I groaned and moaned louder and loader. The bed was literally crashing into the wall and I was completely squashed along the side of the headboard and it got so intense that I had to cry out for him to stop because it was frightening me! He stopped and was so sweet and comforting asking me what's wrong and we just cuddled for a bit and on my request he slipped out his dick which popped out and left me sore and gaping.

Honestly though, although it did overwhelm me at first I started to get so hot from realising how brutally my hole had just been punched open that we started making out again and eventually he put his cock back inside me and it felt incredible. After that he fucked me passionately on my back which was fucking amazing until I realised he was getting close. He was pounding deeper and deeper and I frantically considered asking him to pull out because I wasn't sure! But it was too late and he eventually gasped "I'm gonna cum, I'm cumming in you" and filled me up.

After that first load though I realised how much I loved the feeling of a pulsing cock inside me and after a moment, I let him fuck me and cum inside me again. I spent the rest of the evening and next morning pushing out his semen and feeling it trickle down my thighs. My reluctant first raw experience ended with me being bred twice and loving it!

[Bokkierob]

I guess it was unplanned. He was a lot older than me and I'd been sucking his cock for a month. ||I was a virgin and he was tho first and only man I'd been with. He said it was time I learned to take his cock up my ass. I had no idea what to expect and he took the lead. He eased his bare cock up my ass snd fucked me slow and shot his load in me. He fukkin loved it  It was kinds sore but I was turned on by how much he moaned and enjoyed my virgin asshole

[PozTalkAuthor]

Planned or unplanned, I may say "partially planned"; we planned to have sex but the condom hurt. He then pulled out, aware of my fear for AIDS. He has been very respectful. Other times I've used condoms but raw is better. No, sorry, raw is law. No doubt!

[ijoey]

I had no plan. I had no idea what we were doing. I had sucked his cock just two days before. He used vaseline slid his 7 inccok up and down my crack untill he popped in the head. yeah, it hurt, but he didn't care.

we fucked two more times that night and then every other day for the next two years

[Njn0mc]

Me not planned and the guy took advantage of me when i was passed out drunk and came to when he was pumping hard.

[barebackbro]

My first time was unplanned, though I'd been fantasising about it.

I was fucking a guy with a condom. When I got close, I pulled out and asked where he wanted me to blow. He said 'Wherever you want.' I said 'I want to blow inside you.' I was so turned on that I came as I started pushing my cock back in.

I kept trying that trick for months. This was long before PrEP, so most guys refused and were often angry.

I came to target the guys I knew would take my load. Once I could hold out for longer, I realised how good raw sex felt. Eventually, I basically couldn't get hard if I saw a condom.

 

[barebackbro]

My first time as a bottom - years later - was planned. I was on bbrts for hours every day, but said I would only fuck guys with a condom, then breed them. I didn't bottom much then.

I got to chatting with one very young, very hung guy. For weeks. I made him promise he would fuck for a bit and pull out long before he came. We agreed to meet at a bathhouse and we exchanged maybe 20 messages that night because I was so nervous. When we met, I saw he was at least as hot as his photos.

He said basically nothing in person. He pushed me on my back, spread my legs and fucked me, much harder than I expected. After maybe five minutes, he pulled out and started to go, saying nothing. I felt my ass and thought I was bleeding, until I realised he had blown a massive load in me. I started to say he had promised not to come in me - and he just poked out his tongue and left.

Later, once I'd recovered, I tried to message him to thank him. He had blocked me.

I still love him.

[hotguy02]

When I first met my top daddy I was 19 and he was 30 years older than me.   He was good at getting into my head and seducing my curiosity.  He stated from the very beginning tht he didn't use condoms and I was so entranced in his words that I gave in.   When he first fucked me I felt like I belonged to him since he popped my cherry.   So it came out of my own mouth and told him cum inside me.   I remember going home feeling guilty and dirty and worried about hiv.  But he made me fall in love with him tht weeks later I was back in his bed without him even saying a word 

[Cream4u]

Well my first time RAW... was also my first time having sex with another person. (I mean I only had sex till that time with my left hand a lot).

I remember that ... I was just a young bloke, still wett behind the ears raging with hormons and with no sex experience at all. At the time I was heavy into masturbating and fantasizing about anything that had to do with sex. I was riding a bicycle at the time and lived in Arnhem-Holland where I was going to school close to the city center. After school I sometimes went into the city center and in this case too. I went to V&D a big store to buy something for school. On the other side of the street there was a building with a shop for coffee and snacks. There were bus stops at the front and a public toilet at the back. I put my bicycle there and locked it up.

So far I was still completely ignorant and did not yet realize what for horny stuff would happen to me there that day. I walked into V&D and did my shopping. When I got back to my bike I saw that there was a public toilet there and I needed to pee so I went inside. Immediately upon entering, a heavy piss smell hit my nose. When entering there was a wall to the left where you had to go around it to find 3 urinals and to the right of it were 3 toilet blocks ... with quarter coin machines on the doors for entry.

While I was standing there with my cock out to take a piss, a very slim but older guy, well over his 60 with red hair, entered and came standing next to me at the urinal. He also took out his cock to have a  piss. But after seconds I noticed that he wasn’t pissing so I looked to my right. There I saw with great shock that he was slowly playing with his already half-hard cock showing no shame while he was looking at me and my cock. I was shocked, didn't know what to do. I still didn't realize he was gay and used these toilets as a hunting ground. I saw that his cock was getting hard and his nob looked wet and shiny. He looked straight at me with a horny smile on his lips. I became uncomfortable because my cock started to get hard too. I stuffed my cock back in my pants and with shaking legs I quickly left the toilets, but I did not drive right off but stood next to my bike while I kept an eye on the toilet entrance from a distance. I then noticed that men regularly went in and out, but also a few stayed in much longer than you need the time to do your thing.

It turned out… there was a car park on the opposite of the entrance to the toilets. What I didn't know was that the toilets were a cruising spot, there were lots of gays cruising there and also sitting in their car waiting to see who went into the toilets.

When it calmed down after a while, I went back inside out of curiosity and the horny forbidden feeling I had. I went to the toilet blocks where I saw that something horny had happened here. I watched, mesmerized, that a few heavy fresh loads of cum where lying on the floor and on/in the urinals. I also saw now that there were plenty of traces of yellow thick dried cum. I got so horny about this place that I pulled my rock hard cock out. What I did then was certainly dirty ... but for me so horny ... with my fingers I smeared as much of those thick blobs of smelly cum mixed with piss from the pissoirs on my cock and glans. I pushed as much cum as possible under my foreskin and smeared it into my pubic hair.

I wanted to jerk off with all that horny smelly cum lube over my cock. I was only afraid of being caught, so I quickly went into a still free fixed toilet. I had to put a 25 cents in closed the door and had a safe feeling.

Right there I dropped my pants and started to masturbate with all that cum on and over my boys cock. Such a horny, smooth and smelly lubrication that because of me masturbating quickly started to turn into white cream. I was really shaking on my legs because of the heavy ans horny sensations I was feeling. I think I was  within 2 minutes to ejaculate my cum load.

This was such a horny thing to do .... a horny filthy sex thing. My cock was really hard and I just wanted to cum. While working on my cock I saw a movement from the corner of my left eye. When I looked closely I saw that there was a hole in the thin partition wall to the other toilet and that someone was looking at me and running his fingers through the hole. I was scared lifeless, wanted to stop and leave ..... but the guy put his tongue through the hole and made licking gestures. I don't know where I got the courage but I think my hornyness won over my fear. I then carefully moved my young cock towards the hole and slowly stuck it through. The hole was the right size for my cock and balls. My cock slid straight into a warm and really perfect sucking / licking warm wet mouth. My cock was wrapped up so nice and warm and milked… my legs were shaking. This felt so good!! The warm mouth did not mind that my cock was sticky as hell and fully smeared with cum.

After only a few minutes my cock was bursting to unload my cum. The mouth on the other side apparently figured this out and abruptly stopped letting the pressure of my cock for seconds and then started sucking me again. He did this up to 3 times and stopped just in time.

I went crazy with the horny pleasure he give my cock and I wanted to give him my load. When stopped again, I got frustrated and pulled my cock back. I then heard the person say to me in a whisper “put your cock back through the hole and promise not to pull back off when you feel your  cum come squirting out. Just enjoy the pleasure and joy that I'm going to do to your horny cock.

I quickly put my cock back through the hole again… straight into his horny mouth but only for a short time. Then there was nothing, some low noise, he grabbed my cock again, I briefly felt some counter pressure and again I felt the warmth. A super warmth all over my cock that started to suck / milk me very nice and enjoyable. I didn't have to do anything just to keep my cock fully pressed through the hole.

A few times my cock got free.. then back again completely surrounded by the warm and moist pleasure. I quickly moved towards my orgasm thinking about what he had said. Don't pull back and let my cum spray full. So I did…. I came, my legs where trembling as it fell so good! My cock kept on pumping cum loads of it! A horny heavy odour of musk, piss and smegma cock came up into my nose. When I looked at my cock and was shocked to see that it was full of white foam / slime. And when I pulled my cock back I saw why my orgasm was so intense and horny. My cock had been in his ass.

Yes he had pushed his sloppy and smelly ass over my cock. That was something I had never experienced before. That's why I didn't noticed right away that I had slipped up his ass. This was the first time my virgin cock had really fucked. The voice asked me if I had enjoyed it and I shyly answered with yes.

I then without cleaning my slippery cock quickly went out and as I unlocked my bike the guy whom I just fucked bareback came out. It was the older 60 + slim guy who had been looking at my cock by the urinals before. I knew that he must have had already a few cum loads in his ass from others before my cock slid in his ass.

I can tell you that from that day on I was there almost every day after school and almost always I was lucky to find blobs of sperm for my cock as lube / masturbate and unload my cum ... and very often I had the luck in one of the toilets with gloryhole to shoot my sperm in a sucking mouth or horny sticky-sloppy ass. I really shot loads of cum there. That's where my fetish for gloryhole sex and fucking bareback originated. I'm sure.

All the added pictures are of my cock during Gloryhole action....... My fetisj is clear having anonemous gloryhole sex. 

 

[TightBott7]

First time was unplanned. During my condom days my online profiles always said safe only. But, gradually, I started caving in to alpha tops that insisted on fucking me raw. Somehow, these really knew how to tigger that inner slut in me. And for that I’m grateful.

[Negasswhore]

Definitely Unplanned, I didn´t know what to do except do what I had seen on some Vhs porn films. I was just going to check out a small forest where there was rumour´s that many gay men were having sex had been spreading around town. It was very true though...My true story here   My first time with Men 

[badjujuboy]

Def unplanned… it just happened organically… we were young and thought we were invincible. I ran around with a small circle of guys and we made our way around with each other over time. A few months after taking his raw load, he and his bf at the time got tested due to a scare but tested neg. That made me use condoms until I met my first Daddy after college and it was raw from the get go. So at that point it was planned. He was neg and I wanted his load in my cunt… Now, PrEP allows me to continue enjoying loads. 

Edited February 26, 2023 by badjujuboy

[Guest]

Mine was unplanned but I was hoping he would breed me. We chatted on scruff and I met up at his place after work. He had a beautiful townhouse with a pool. We didn’t even make it inside before he started fingering me and eating me out.  We got into the pool naked and he fucked me half in the water. Clear view of all of his neighbors too. I didn’t care. It was hot. We eventually made it inside and he asked where I wanted his load. I didn’t hesitate - cum in my ass. 

[Jamie85]

Not just planned, but begged for as well.  I had a long time cock feeder that I told I had never been topped and it led to my getting fucked.  With a condom.  I talked, begged hi9m to fuck me bared and it took a couple more fucks before I finally got his cock bare along with his first load of cum in my ass.  It was bare from then on.

[GuelphGuy72]

My first time going bare was planned.