First time raw, planned or unplanned?

[Pozguyinchi]

My first time was bare. I was 13 and honestly I don’t think I had ever seen a condom. After he came in me something changed and I knew that was the way I wanted it forever. It wasn’t until college that I even thought about any risk involved with getting bred bare. Not that it stopped me. Of course I was poz by age 19

[Tanbbottom]

On 3/31/2020 at 2:59 PM, Guest said:

Unplanned! My first time was around 18. I was of the mindset ‘I’ll only ever use condoms’. Strict, no way around that.

 

While I lived with my parents I’d spend most nights at my buddies place - 40’s hairy bald bear guy. He was my first time topping as I had mostly only done oral and we tried used a condom. Every time I wasn’t able to stay hard, so he’d blow me and we’d cuddle.

 

After this three or so times, we had finished and were all lubed up swinging in a hammock. I was spooning him, hard as diamonds and half asleep. While I don’t remember exactly how, my cock ended up raw inside him and I froze. “I don’t have a condom on”, to which he responded “it’s ok”.

 

Cue the next couple months before heading off to college I’d breed his hole several times a day (luxury of being young and horny).

 

Turns out he was a total raw pig - he had a huge fetish for younger ‘condom to bareback’ that I’m not even sure he knew. Loved being surprised by condom removal and all that.

 

After him I really never went back. Impossible to, in my opinion.

So hot 🔥 

[Tanbbottom]

First time I fucked a guy was bareback. I'd say this was spontaneously and unplanned on my part. He may have been planning it for a while. 

It was early in my coming out. I was married with kids and once a month would explore my gay side spending a weekend with this hot guy. Mostly I spent the days watching gay porn while he was at work. I'd cook him dinner and we spent the evenings having sex. Eventually we got to fucking, he wanted me to do him. This would have been 1989 (fully in the AIDS crisis) Since I had never been with a guy other than blowjobs, and was monogamous in my marriage he had me fuck him bb. It felt amazing to be in his anal cavity. I was afraid I would cum, he assured me he wouldn't mind. I didn't and he had me pee immediately after coming out of him to be sure nothing got lodged in my piss hole. 

I don't recall for sure but am pretty sure the first time I was fucked bb was the first guy I lived with. I talked him into doing me raw. He was very resistant to the idea because he was addicted to sex and very promiscuous. It was only a number of years later that he confessed to me his fear because he let a few guys bb him in the heat of the moment. I was very persuasive and insistent and he finally relented. I loved the feel of his big raw cock in me and that first time he bred me. (Again I insisted!) We were in missionary position. I loved watching his face as he climaxed in me. I loved the feeling of his cum in me. We never used condoms again and bred each other many times. We never got to fucking when we were in threesomes.

So I guess my answer is a combination of unplanned and planned. 

[wbekk85]

i guess it was unplanned. we were in our teens and we didn't think about using rubbers. i actually never used a rubber until i was in my 20s, and by that time i'd fucked and been fucked by several men, and we always shot our loads up each others asses. i'm surprised that i didn't get an std.

[Bottom Jim]

My first time was with a swim team buddy. He came over and we watched some porn  He unzipped me and started to suck me. I returned the favor. All of a sudden  he turned me on my side and went behind me.

before a knew it his dick was in my ass. He fucked me a little before he came in me

it felt great and we thought of condoms Always raw

[hexfet]

Unplanned for sure.  First time having sex and didn’t have anything in the house.  Not sure what I was thinking since it was in the middle of the HIV explosion.  But we were super horny and it happened.  Made condom sex a lot less interesting for sure once I put one on, tried to be a good boy, but well kinda wasn’t that good and or broke a good number just fuckin rough. 

[cannero]

Unplanned: I was in my early twenties and the times I'd been fucked were by similar guys and always rubbered. The fucks were at best uncomfortable and worse painfully unsuccessful, and I assumed I was a crap bottom. One night I was picked up by this older guy from Bristol, and was pleasantly drunk by the time we got into bed. His dick was huge and I had some trepidation, but he lubed well, put the pillow under my arse and just slid in. The fuck was utterly perfect, I had never felt such pleasure, and then he kissed me and said sorry he came, he shouldn't have. It was 1990 and although I periodically fucked covered, I only took cock raw up my arse from then on.

[Oldercumslut]

1st time wasn’t planned or unplanned.  I just wasn’t thinking about it those days.

[Sn00wb00red]

Unplanned. I was in my early 20s and had been out for a few years but never taken it raw beyond the tip a few times. He was a coworker who was always into me, and after a long time flirting he finally convinced me to come to his house at lunchtime.  He was 6’ lean nerdy guy, and was normally a bottom but was very interested in fucking me. Really pretty 8” uncut cock. (I still have a big uncut fetish from this being my first load)
 

He got a little dom with me and was fucking my throat and ordering me around. Eventually I ended up face down on the bed and he asked if he could fuck me raw. I was really into the whole scene so I said yes, but said don’t cum in me. He slid inside me and started fucking me and it felt sooooo much better raw plus that uncut smoothness that only like a minute later I said “I want you to cum inside me” and that really turned him on and he picked up the pace and shot a huge load in my hole ten min later and then laid down on top of me, still inside me, while he got soft. 
 

I drove back to work with the load in my hole, leaking out. Went straight to the bathroom at work and squeezed some out and tasted it and jerked off with it. 
 

Can probably count the number of cocks I took wrapped since then with one hand. I was instantly converted into a pig bottom. He and I played every once in a while for a few years and he even brought a friend once while I was blindfolded, but that’s for another topic. 

[Marlin]

When I met my first bf we played safe for almost a month. In fact the first few nights we didn't even fuck, Passionate kissing and lots of oral, When we did start fucking we always used condoms, no discussion, 

One night we were passionately kissing, making out and sucking each other. I was in love with my bf and really wanted his DNA inside me. After sucking his dick for a while I made sure to get it extra sloppy. I then got up on top of him, sat over his dick and maneuvered it into my ass, slowly letting it sink all the while I was kissing him. He had been inside me before but this felt awesome. I loved the spontaneity and not having to fumble with a condom and psychotically eliminating that latex barrier, I was kissing him deep and started riding him. Within a minute or two he announced he was close to cumming and he wasn't wearing a condom. I told him that I wanted him to cum inside me. It obviously turned him on too as he reached up to kiss me deep just as started feeling his dick spasm inside me knowing I finally had his DNA in me. I rolled off him reached behind and felt his spooge. We cuddled for a while and fell asleep. I kept his load in me all night. The next morning we woke up and I fucked him...no condoms, no discussion. We never wrapped again

[Njn0mc]

3 hours ago, Marlin said:

When I met my first bf we played safe for almost a month. In fact the first few nights we didn't even fuck, Passionate kissing and lots of oral, When we did start fucking we always used condoms, no discussion, 

One night we were passionately kissing, making out and sucking each other. I was in love with my bf and really wanted his DNA inside me. After sucking his dick for a while I made sure to get it extra sloppy. I then got up on top of him, sat over his dick and maneuvered it into my ass, slowly letting it sink all the while I was kissing him. He had been inside me before but this felt awesome. I loved the spontaneity and not having to fumble with a condom and psychotically eliminating that latex barrier, I was kissing him deep and started riding him. Within a minute or two he announced he was close to cumming and he wasn't wearing a condom. I told him that I wanted him to cum inside me. It obviously turned him on too as he reached up to kiss me deep just as started feeling his dick spasm inside me knowing I finally had his DNA in me. I rolled off him reached behind and felt his spooge. We cuddled for a while and fell asleep. I kept his load in me all night. The next morning we woke up and I fucked him...no condoms, no discussion. We never wrapped again

Thats hot!

I love to do sleep overs. Its awesome to wake up naked and next to a naked body.

[atlboy]

It wasn't planned for me lol. He was a lot older than me and we had blown each other but never had anal sex. He was massaging me on a table, like a legit massage. When he got to my legs he would go back and forth between my hole and my inner thigh. I remember laying there thinking how far he was going to take it. Excited and scared at the same time. Then I felt the pressure of his cock against my hole, and he would push it but just a little so it wouldn't go in. I still was thinking he wasn't going to do it all the way since we had never done that (and I was still a virgin). Obviously he pushed inside and fucked me slowly while he was rubbing my shoulders. The moment I got used to him inside me he shot, maybe 30 seconds total. He pulled out and massage was over lol.

[Jimmi]

Unplanned.  The sex was planned.  i was 21 and being a virgin was getting embarrassing.  But i had low self esteem; i didn’t believe anyone would find me sexy.  Met a guy who thought i was hot.  He took me back to his place.  It was the late 1980s and i was a “good boy” so insisted on condoms.  But he talked me out of them.  His cock was huge (i didn’t realise at the time, because he was my first). It hurt so much.  And i loved it. 

[Hottightass4u]

unplanned

[blkboibtm]

Even though I was planning to go raw, the first time was unplanned and prob a rape lol.  Was going back and forth with this top online, he was def into raw told him I hadn't fucked raw but was curious, he kept pushing but I was stead fast, told him we clicked I would consider it.  He picked up on me being naturally sub and that i had zero desire to ever top. He first wasn't going to fuck wit me, but he liked me being sub and he luved blk guys especially btms.  Still in 2010- 2012 it was hard getting over the fact that not every blk guy is a aggressive dom with BBC, though that still is the stereotype def not no where near as bad.  After almost a month of going back and forth we decided to hook up (half the reason it was taking so long was he traveled a lot and I was unsure cuz It was one of the first guys I would meet online for str8 up sex.)  I went over, plug inserted, I get a lil high to had a few drinks to loosen me up.  We were supposed to talk and chill first before doing anything.  He had a apartment, it was dim.  He offered me a drink, he was dressed at this point.  I had turned around to just check out the rest of his apartment, didn't have super bad vibes but was still nervous.  Got scared as fuck when he came up behind me grabbing my ass so hard lol and another around my throat and licking my ear.  I got so turned on I ended up dropping the glass which still had liquor in it, he told me don't worry bout it.  He moved his hand around to my dyck and stroked it for a hot second.  It was getting hard and he wasted no time pulling my sweats off.  I realized at this point he was already naked.  He pulled my shirt off and pushed me towards his couch.  He felt my plug and had me bend forward so he could pull it out.  He started fingering it a bit, talking shit.  Telling me that he knew I came here to be fucked, and made me answer him yes,  This happening so fast I ain't know what the fuck to do, but was still so turned the fuck on.  He put a lil bit on lube on my hole, and fingered still I asked if he had a rubber he showed me a little 3 pack.  It said magnum,  i realized that I hadn't even seen his dyck yet (not in person I did through pics), but before I could get to see it he pushed his hand on my neck so that i was fully face down ass up and he was using a lot of strength, I didn't understand why he was being that hard until I felt him entering me and saying something like I'm giving you what you really want, show you how to be a proper bitch.  He gave me hard first thrust OMG LOL.  He fucked me so good, that shit hurt so good at first.  he realized I wasn't stopping him after bout  5mins cuz I did try to quirm away when he first said something but he had me pinned pretty much.  His rhythm started to change I told him don't cum in me, just as I said that he pushed all his weight on me and started and giving sum hard thrusts I knew he just unloaded in me. He kept stroking me untill he was soft and jsut got up and sat on the couch while I laid there in a heap.  He was asking if iwas okay, and saying wasn't better raw.  I legit ain't know what to say, I was fo real pissed but thaat shit felt good.  He got up threw a towel at me and started walking into the bathroom told me he had things to do so I needed to be gone when he got out! lol  I was a mess for the rest of the day feeling so used, betrayed, violated but I couldn't stop thinking about it.  I ended up masterbating to it later that night using my dildo realizing I still had sum of his babies swimming in me as lube.  I haven't looked back sense.    We linked up couple more times before going off to college, and when I would come home he always wanted it.  He ended up moving and getting marred but we keep in touch and his parents live in the area so we occasionally link up and he sluts me out.  He is a different animal on the phone and when we meet up for sex, after all theses years I nothing but a dump to him.  He still turns me on and he got me to take the leap into whoredom.