First time raw, planned or unplanned?

[Annapaulamass]

My first time raw was completely unplanned during 80's in a bathroom of a movie theater.

[RaunchFilthPup]

My first time raw WAS my first time.       My track coach.      I just went with what he wanted.     He always was a good teacher  

[lovetobefucked]

First consensual time i was 12. He was a year older. We went skinny dipping while his parents were out. Then we watched a movie while still naked and fell asleep on the couch together. Woke up and he was inside me.  We ended up fucking for hours.

[Shooter_099]

Actually first time raw was planned. Had been with my partner for about two months and always played safe. One night we were fooling around and watched some porn on his laptop in bed. We flicked through a few vids to find one we liked. Didn't realise it was a barebacking vid until the obvious happened.

We didn't say anything for a while, just watched the vid. Turned us both on because we were both rock hard. We then spoke about barebacking and how long we had been together / loved eachother and thought it was about time we fucked raw. We both cum in eachother for the first time and i will always remember it..That was the night that i became a 100% barebacker.

[bareback-flipflop]

Almost twenty years ago, with my first boyfriend. It was totally planned. I couldn’t wait for fucking without condome. 
However, I clearly remember the first unplanned bareback, which happened a year later with a hot guy in his bathroom under the shower. It was better than the planned because it was dirtiest. I cheated my boyfriend and I knew it is something forbidden. 

[Guest Gonegurl]

My first time was definitely unplanned. It was my second date with this hot guy I was seeing a few years ago. He is this tall, slim, hairy, black guy, with a wicked smile. I was totally into him, still am really (even though I dumped him), and should have seen it coming.  We settled on dinner and a movie at his place, and that was it really. 

I got there around seven I think. He opened the door, gave me that smile, and pulled me in by my shirt collar. Strait to a kiss, and then a tour of the apartment. The tour ended in the kitchen, as he was finishing making dinner. It was decent, but word to the wise, always let the chubby one cook. We know what we're doing in there. The conversation never lagged and there were plenty of laughs. Everything seemed to be going well.

Afterward, he ran into his room to change into shorts and a t-shirt, claiming he was warm, and then things shifted to the couch and a movie. Honestly, I have no idea what movie we watched. We were making out two minutes into it, and I wasn't complaining. Things cooled off after a half hour or so, and we settled into watching the movie and cuddling. I am an equal opportunity spoon, but ended up in the little slot.  Lucky for me. He threw a blanket over us, wrapped me in his arms, and I snuggled up to him.

I'll take the blame for starting things. My ass has a mind of it's own, and I don't stop it often. I had settled my ass into his crotch. A few minutes later, I needed to readjust, which may have caused my ass to rub him slightly. He reacted, as any red blooded top does, and pulled me closer. Grinding his crotch into my butt. I didn't fight it, sighed in contentment and pulled his arm around me tighter. I could feel a massive hard on pressing into my ass in retaliation a few moments later. 

This play of bodies and grinding escalated, until he began pulling his shorts and boxers off, and threw them to the floor. I probably could have kept things from getting out of hand. I hadn't planned ahead or prepared for this, but my ass is a whore, and there's no denying it. He kept maneuvering under the blanket, and had my shorts off without protest. My standard jockstrap gave him clear access from there, and he seemed pleased. 

He pulled me back into slot again, spooned up tight, and ground his dick into me. I moved back into him in turn, and realized this dude was hung. If he wasn't close to ten inches, my ass isn't as sensitive as I'd thought. 

We kept it up, for a while. Building up steam. He had me right where he wanted me. He reached down and adjusted his cock to meet my hole. The grinding continued, and he held me tight as the precum started to flow to my ass. That was all it took. I'm tight, but I wanted it. I wiggled my ass, to help his dickhead wet my hole. Then, I don't know who thrust first, but we were both pushing to get his cock in me. Rocking together, he slid in. I'm sure he couldn't have gotten all the way in without lube, but he didn't seem to mind being only halfway. 

We rocked like that. My ass begging for it, and milking him. Him pulling at me and thrusting up into my hole. It couldn't have lasted more than five minutes. His breathing became hard, he wrapped his arms tight, and thrust deep as he could. I think it was also the first night I can say I felt the throbs of his cock as he shot into me. We stayed like that for a minute, him sighing and my hole full. Then he pulled his cock out of me. Clean as far as I could see, thank goodness. He stood up, kissed me, and took me to his shower. I couldn't have asked for a better first breeding. 

 

[Devtylor]

First time was unplanned. Hooked up with a black dude off manhunt years ago. He fucked me with a condom the first time. But after a bit of a rest he wanted to fuck again, this time he just stuck it in me bare. I knew I wanted it and so did he. 

[Fuckhole2bfilled]

First time raw was unplanned with a fuck bud. We had always used a condom anytime he fucked me.  On this day I went over to where he was working, he was the only one there.  He took me upstairs and there I dropped my pants down to my ankles and bent over, he began to rim me. 
Shortly after I felt him pressing his cock as my hungry fuckhole, before I had time to get the condom from the pocket of my pants I was being fucked raw. I enjoyed so much, I guess deep down I always wanted it raw.  He pulled out and came on my back. 
The following week I went to his house where we made out and next thing we were naked and in his bed. Without asking he slid his raw cock deep inside me and proceeded to pound my hole mercilessly for 30 mins. Then as he’s pounding away he looks in my eyes and says “I’m going to cum inside you”, to which I said “breed me” and he let me have it, the feel of his cock throbbing as his warm cum fills my hole made me cum without touching my cock.  
This was 11 years ago, he still fucks me when I’m in town and we haven’t used a condom since then. 

[bivergent]

My first time with a guy was planned but doing it raw with him was unplanned. We had agreed to use condoms but after he had gotten me excited he talked me into letting him enter me without a condom. 

[superstard72]

On 3/29/2020 at 3:16 PM, rawTOP said:

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.

Always fuck raw

[gaypigbb]

It was quite early in my sex experience. After a while of topping i wanted to try bottoming, and had quite a few hookups as a bottom. It felt great! I was strict on always using condoms though. But it was this one time, I remember it well. He had a super hot profile pic on Grindr, and straight to the matter when chatting. I remember his apartment too, and his bedroom with large windows ith view to the street outside his flat. 

I asked him if he had a condom, and he said "sure". We got naked, started kissing, and soon he was on top of me. He was so handsome, and made me really horny. Then he suddenly asked "Sure you need a condom?" I was baffled by the question, since i assumed it was already decided. "Its a thousand times better without it..." Sounded like he gave me a choice - but really, who says no to something thats a thousand times better? So I went with it, and he fucked me hard, lying sideways on the bed. All RAW. Before he shot his load inside me he said "Im cumming soon. Filling you up with my sperm". Then he fucked harder and rougher and came inside my ass. 

Looking back - I was a virgin until that point. Condom sex isnt sex, and have you first tried sweaty, RAW breeding its no way back.
Never touched a condom ever since.

[BB4fking]

My partner always used to fuck me raw so I guess he was the first but that’s not hookup sex which I used condoms for over many years. I lapsed into raw sex a few times in my condom period. The first time I recall was at a sauna while abroad. I had hooked up with a guy in a room at the sauna and I had him put on a condom when he tried to fuck me. However he’d go soft and ask to leave the condom off and I’d let him fuck me raw for a few strokes then put another condom on him and we’d start again. We did that 3 or 4 times but eventually I must have relented because he stuck around and we had some good sex. Good enough that we agreed to leave the sauna and go to my hotel on the explicit understanding that we would fuck raw. He must have been hot because usually I’d have been paranoid about that in the 1990s. He stayed overnight and fucked me several times.

[atlmarketingbiz]

My very first time was bb. Was the day of my HS graduation. Met a guy online. He was straight ish and in town (small town coastal GA) for business. I went to the hotel with intention of just BJ and handjob... he was so turned on that I was a virgin that he asked when I was getting ready to leave if he could pop my Cherry. We didn't have condoms or lube so it was a spit shove and a load. 

[leatherpunk16]

Definitely unplanned for me. I had been seeing a married man on and off for a couple years, and we had been fucking with condoms every time. He was afraid he might give me something that one of his other hos gave to him, so he would always insist on them. I didn't mind. Then on one visit, I was in his studio basement, and we started the usual handjobs and BJs. He turned on bestiality porn, which surprised me because I had never seen or heard of it, and didn't think he'd be into that. We didn't watch it, it was just background noise on a labtop. 

Anycrap, he got me bent over a barstool and proceeded to fuck me. No condom. It felt amazing. We would have finished, too, but we got interrupted by the early arrival of his student. So we threw clothes back on, rushed upstairs, and he shoved me out the backdoor while letting his student in the front. I tiptoed back to my car, and drove home. Never got that load from him. #sadpanda 

[ssoranaid]

Planned. With my ex, I knew he was fucking others and was untested