First time raw, planned or unplanned?

[CumBustion]

Ummm I’d have to say planned. Then again, I was pretty young and thought condoms were on for heteros to prevent pregnancy. I don’t believe he had any intention of using a jimmy.

[Kimberley]

Both i think, i was still a virgin and always was learned to have safe-sex, my mom even gave me a pack of condoms and told me to use it if i was going to have sex for my own protection. but in my search for my first cock i couldn't ignore it that so much men wanted to bareback me and i got inpired by them. i met a older guy who i sucked his cock once and second date he was going to fuck me. in the heat of the moment i just asked him to fuck me raw and so it was. shooted my virgin ass full with his cum and i was loving it!! 😅

[Guest deepthroatkiss]

unplanned. it just kind of happened and I never went back. bareback is too much fun.

[stupidhOle]

unplanned and at the time it freaked me tf out, but now I jerk off to the memory

[Jimmi]

Completely unplanned.  My first time.  I asked for condom. He talked me out of it. That memory is so hot. 

[InTown]

My first bb was not planned but my first breeding as a bttm was.

[BurnAfterReading17]

Completely not the plan. I was in my "experimenting phase", had jerked off with some of my friends after school a few times but I wanted to try more and I was too shy to tell any of them that. So I did what any horny, curious teen would do and went online. I met a guy a few years older than me, he was 22 but looked 18 at best. After a lot of forth he talked me into meeting up to "just see what happens".

I told my parents I was going to the movies and would be back late. I drove up to his dorm, which was about a half hour away from the small town I lived in. He had a suite with 3 other roommates, everyone had their own small room though. I was so nervous I was literally shaking when we walked into his room and he locked the door. Thankfully he looked exactly how he described, if not better looking. He was so sexy, I didn't know what to do.

He talked to me about anything and everything, just to calm my nerves. Eventually he offered me alcohol, I had never drank before so I accepted and he poured us some shots. After downing two shots and a dozen questions later I was feeling much more comfortable. I think he could tell and that's when he made his move and tried to kiss me. I thought that was pretty gay so I dodged the kiss and told him I wasn't comfortable with that.

"So...what are you comfortable with," he asked.

"I don't know, like...anything else," I laughed.

So he took off his shirt, showing his sexy body. My heart beating so hard and fast I thought it would jump out of my body, he slowly reached over to my shirt and started to lift it up and off. He started to rub my shoulders, then my chest and went lower to unbutton my jeans. He smiled at me, a very sexy smile that must have been from braces in high school, I melted. My pants around my ankles and my very hard dick trying to make it's way out of my gray Old Navy briefs, some precum already forming a wet spot on the pouch.

He stood up in front of me, untying the straps of his gym shorts and pushed them and his boxers to the floor. His dick sprang up and was inches from my face. He was probably a solid 6" cut and a drop of precum was forming at the tip. He just looked at me, I knew what he wanted but I was too nervous to just go for it, so I waited for him to grab my head and pull me in.

I opened my mouth and tasted another guys dick for the first time. I put in my best effort, but it was probably a terrible blow job. I was doing the sucking but for some reason my mouth didn't want to produce any saliva, probably my nerves. After a few minutes he told me to lay back on the bed and I did. He hooked his hands in the waistband of my briefs and pulled them off with little effort. 

He was between my legs and sucking my dick, I was so hard, trying not to moan out of fear he'd think I liked getting a blow job from a guy, but I couldn't help it and the occasional "mmm" or "fuck" escaped my mouth. It only took a couple minutes, less than five, for me to be close to cumming. I warned him I was close and he pulled off. I tried to jerk myself off to finish, but he didn't let me, he told me to "wait, not yet" and continued to slow jerk me with one hand and himself with the other.

He lifted my legs and stuck his tongue in my hole, I let out an audible, "oh shit" and gripped the sheets. That was the most amazing feeling I had ever had. "You like that?" he asked. "Oh man...yeah," was all I could say. "Roll over, I'll do it some more," he suggested. I was happy to, and as promised his tongue quickly was back in my hole while I used his pillow to muffle my moans.

After a few minutes of eating me out I felt something that wasn't his tongue rubbing on my hole. I looked back and he was jerking himself off and rubbing the tip of his dick between my cheeks. I didn't know what to say, my head was spinning from all the pleasure so I just let him continue to jerk off. He spit on my hole, then used the tip of his dick to rub the spit in, it felt so good I let out a soft moan. "You like that?" he asked. Again, I said nothing. He rubbed and then added more spit, then rubbed and added more, it was really feeling good until he tried to push the tip in.

"Oww," I groaned.

"You ok?" he asked.

"That hurt, we can't..." I trailed off.

"If you relax it will feel better, I promise," he said.

"I don't know man...I don't think I'm ready for that," I told him.

He added more saliva and pushed the tip in again. I groaned and winced, "Oh fuck man...I don't think," I started to say.

"Just the tip," he said in a calming voice, "I just want to feel it a little, then I'll pull out and jerk off."

I was naive, horny and overly nervous and just believed him. I just grit my teeth and tried to focus on breathing.

"Just relax," he whispered as he massaged my butt cheeks.

I took an audible deep breath and as I breathed out he pushed in a little more, "Oh fuck dude," I said into the pillow.

"Just relax," he said calmly, as if that was making it better.

"It's too big," I said, teeth clenched.

He slowly kept pushing and I felt him bottom out and lay down on my back, "it's all the way in," he whispered. He just held it there. I didn't know what to say, it didn't feel as good as it looked in the porn I had watched, I thought I was getting ripped open. Then he slowly started to pull out and I felt a hint of relief until he pushed slowly back in.

"Fuuuck, dude," I groaned.

"I knew you could take it," he whispered and kissed my neck.

"Do you have a condom?" I asked.

He pushed in and out a few more times before he answered, "yeah" in a low whisper. Without pulling out he reached into the drawer next to the bed. He thrust a few more times then pulled out and put on the condom. I heard a "click" and felt some cold lube squirt onto my hole. With my face still in the pillow I listened as he added lube to his condom covered dick and it made that distinct squishy sound only condoms make when you jerk off with one. Seconds later he leaned back in and whispered, "just breath" and I felt the head finding my hole again and he pushed in.

"Oh shiiit," I said a little loud.

"Shhh," he let out, "My roommate is home," he half laughed and bottomed out.

I realized this was happening and just grit my teeth and tried to relax as he started to build up a rythm. He moaned into my ear and kissed my neck, "fuck you feel so good," he said several times. After a few minutes it still hurt but there was a new pleasure I had never felt before and I noticed my soft moans turned from pain to pleasurable moans. He pulled out quickly.

"Turn over," he said and I did as I was told as if my body was in autopilot. He put my legs on his shoulders and quickly pushed all the way back in.

"Oh fuck," I said, not muffled by the pillow this time.

"Fuck you're so tight," he said, thrusting harder and deeper as he started to jerk me off.

As he got my dick harder and harder the entire experience started to turn into this amazing feeling running through my body from my head to my toes that curled with every thrust.

"Oh fuck that feels good," I heard myself say.

"Fuck yeah," he said, thrusting even faster.

Very quickly I felt my orgasm building and my toes curled, "Oh shit...dude...I'm gonna cum..." I said.

"fucking cum for me," he whispered and thrust harder which hit my insides just right and my balls tightened and my cum flew out onto my chest and his hand while he kept thrusting in and out.

"Oh fuck," was all I could say as my orgasm subsided and what was the most amazing feeling of him fucking me turned on me and I was no longer enjoying it.

"Fuck you feel so good," he said, smiling at me.

I grit my teeth, "Are you close?"

"Almost," he said, thrusting deep into me.

"Oh fuck," I clenched.

"If I take the condom off, I'll be close faster," he said between thrusts.

"Yeah...ok," I said not really thinking straight, I just wanted him to be done.

He pulled out and pulled off the condom with a snap, tossing it on the bed next to me. He spit on his dick then found my hole and went balls deep again. "Oh fuuuck," he said. I moaned with him, clenching my teeth and breathing hard with every thrust.

"Are you close?" I asked again.

"Getting close," he said, thrusting harder and faster.

"Just don't cum in me," I said, wincing.

"...But I want to..." he started to say and then thrust erratically and I felt him swell and suddenly the thrusting felt so good as I realized his cum was now lubing my hole. "Oh fuck," he said. "Fuuuck..." then he collapsed on me.

"Did...did you..." I tried to form words around all the things I was feeling and thinking.

His head next to mine, my cum squished between us, his cock still in my hole twitching, "yeah..." he kind of laughed, "my bad." He lifted his head and looked me in the eyes, gave me a kiss I couldn't really dodge in this position, then rolled off me, his cock making a "plop" sound and we both just lay there panting. 

[Poz2play]

My first time barebacking was not planned. My friend took me over to his friends house one night after work. I told my wife that I was going to hang out with my friend. She didn’t know that I was cheating on her with him. He was showing me more about the gay lifestyle and sex. He started to flirting with me at work.  So that night we got to his friend’s house. Who was entertaining friends, so we joined in on the fun. From that night on I have not used a condom since. I was the new top in the group. I fucked all 5 of them that night. It was the best sex I’ve ever had to that time. And this was going to be my future. I told my friend that I really liked being gay. 

[tnjon77]

My first time raw was unplanned, but I had wanted to try it ever since the first time I had sex.

Back in college, I had a somewhat regular hookup who was a couple of years older than me.  This was great, because he had his own house, loved to fuck, and I loved getting fucked.  That was it... We were just fuck buddies...  No strings attached.  

Well, a few weeks had gone by and we were both pretty comfortable with the arrangement.  I still really wanted to see what it was like to get fucked raw, but it was [banned word] and I never told him.  Anyway, that night while he was fucking me, the rubber slipped off and he freaked out.  We were deep into the heat of the moment, but he said he needed to find another one.  I told him that I didn't care about the condom, I just wanted his dick back inside me.  At first, he didn't know what to think, but after a couple of seconds, he gave me a crooked smile and fucked me harder than I had ever been fucked before.  I never asked, but I think it was his first time going raw, too.

When he got close, he said he was going to pull out and blow it on my stomach, but I told him no.  I said that since we had gone this far, I wanted his load inside me.  That did it.  He shot instantly.  From then on, he bred me every time.  So did every one else.  My first time fucking raw was the last time I ever had a rubber inside me.

 

[YourNoLimitsBottom]

Unplanned, but we had been together for a while and were comfortable with each other, so I'd also say it was inevitable.

[PendragonSpirit]

Planned. Even before I lost my virginity, when I'd watch porn, I never liked the way condoms looked. So unnatural and just... THERE. I knew from the get-go I'd never do condoms if I could avoid it. To this day, the only time they're involved is if the top insists, and in most cases they've only used a condom the first time. After that, there's just implicit understanding that I want raw cock.

[Barebackbottomno]

Unplanned, raw, lost my virginity to a top.

[Need2submit]

Unplanned.  I had been using condoms when I hooked up, but one night while hooking up with a top from adam4adam the top made a big show about how the rubbers were just too small for him (they weren’t of course) but I decided to say what the fuck—I wanted dick more than an argument.  He proceeded to bone me into paradise and filled my ass with cum.  I’ve never gone near a condom since.  

Edited November 11, 2021 by Need2submit
Needed to add one phrase

[Guest]

He planed it but didn’t tell me till he was ready.

[Medwaym]

Unplanned. I'd arranged just a blow n go meet at mine. When I unzipped the goods and discovered he had 2 cock piercings, my fantasy was about to come true and I knew I needed to feel him go in raw.