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I always say I lost my virginity at 15 with a pretty little brunette. In reality it was a while earlier with my male cousin. 
Kenny was my cousin through my uncle on my father's side. We often got stuck together when I was about ten and it was my weekend to stay with my dad. When we stayed over at each others houses and went to bed we would always end up talking about sex and what we would do if we ever got a girl naked. Kenny had seen his older sister naked once, but I had never seen anything except a picture or two. We got boners and would show each other, but never did anything. We didn’t know how to do anything. This was before the internet, and the closest thing to porn was a Cosmopolitan magazine. 

A few years later, Kenny called and when we were talking he whispered to me that he had finally jerked off and that white stuff shot out of his dick. I was really excited to learn more about it; I had never jerked off. Actually, I didn’t know how to jerk off or have any idea what an orgasm was or what it felt like.

He came over that weekend and stayed the night. Later, after everyone else had gone to bed, I locked my bedroom door and we snuck out the window and smoked a joint that Kenny got from his older brother. We were pretty high when we got back inside. We both got undressed and crawled in bed in our underwear. We were both underdeveloped, but Kenny looked older and had a pretty muscular body for a young boy, at least more than my skinny frame.

I had never smoked pot before and wasn’t prepared for the feelings I started to get. We started talking about sex and very quickly Kenny pulled down his underwear and showed me his boner. Kenny had a bigger dick than I had, and it looked absolutely huge in my state of mind. He had a tuft of pubic hair at the base; more than I had yet grown. I pulled my underwear down and showed him my uncut cock. He stared closely, examining the differences between mine and his. His large cock made me think mine was smaller than average (it wasn’t until many years later that I learned I had a larger than average cock… I’m still not sure if I hadn’t yet filled out, or if Kenny’s dick was just really huge).

I asked him about jerking off and cumming… how he did it and what it felt like. He knelt down on my bed in front of me, grabbed his cock, and started pulling on it. 

“It works better if you get it wet.”

I watched him pull on it for a while, then he stopped and reached out and grabbed mine. I was kinda shocked but very stoned and horny as hell. He seemed surprised as well, feeling the way my foreskin slid forward over the head of my cock and back down the shaft. “Wow… yours is easier to pump. Does that feel good?”

I had to admit it did feel good, and a lot of clear fluid had seeped out the tip, so his hand easily slid up and down my cock. He leaned in so close I thought for a second he was going to put his mouth on it, but then Kenny suddenly dropped on the bed on his side with his back facing me. He spit on his hand and reached back and rubbed it all over the crack of his ass. 

“Here… see if you can put it in my butt.” 

He reached back and spread his ass cheeks apart so I could see his asshole. His hairless ass looked just like a girl’s butt, especially in my stoned state of mind. It wasn’t the pussy I had long imagined, but I suddenly wanted to push my cock into it. I guided the tip against his ass and started pushing. It slipped down and missed a few times before Kenny reached back and grabbed it and guided it against his butthole, then pushed his ass backwards against me.

The feeling of my cock slowly sliding inside his tight asshole was amazing. The heat of his body and the tight ring of his ass expanding as the head popped inside felt amazing… like nothing I had ever felt before. 

Kenny started rocking his ass back and forth on my cock, harder backwards until my whole cock was sliding inside him. “Does that feel good?”

“Umm… yeah… that feels…”

Kenny started bucking his ass faster on my cock.

“Yeah.. wow… that feels really good… keep doing that.”

I hadn’t ever experienced the feelings I was having. My cock was suddenly the center of my world and the heat and the tight ring of Kenny’s asshole was making my head spin. 

“Do you like that?”

“Fuck… um… yeah… that feels good…”

An intense feeling of pleasure and pressure was building in my groin. It grew and grew until it felt like the entire universe was centered on my cock, and I suddenly felt like I needed to pee.

“Keep doing that… Fuck… but it kinda feels like I have to pee.”

Kenny stopped for a moment, “Go ahead… pee in my butt," then humped his ass harder on my cock.

Kenny kept bucking his ass harder and faster on my cock as my head fucking exploded… the pressure building in my groin finally erupted and shot out my cock into Kenny’s ass.


Vivid fireworks flashed through my mind as I experienced my first orgasm. A mind-blowing orgasm. Streams of my cum shot onto Kenny’s ass each time he slammed his ass down on my cock. Again and again he rammed my cock into his asshole until my cock pumped the last of my cum into him and my euphoria slowly began to subside. But Kenny kept bucking his ass on my cock. 

“Okay… oww… slow down… now it kinda hurts”

My mind was spinning around in my post-climax confusion. I didn’t realize what had just happened. My cock was suddenly very sensitive and I was overwhelmed by the paranoid feelings of guilt and vulnerability. I pulled back, my cock popping out of his ass and years of built-up cum spilling out in my bed. 

“You okay? Was that okay?”

I didn’t even know what to say. “That was kinda weird. What happened?” Stupid thing to say, but I was confused… and still very high. I curled up on my side facing away from Kenny. He was still high too, and very horny. “I think you just came. Can I finger-bang you?” 

“Umm.. okay. Just do it slowly”

I expected his fingers, but I could feel him push his hard cock up against me. He tried to push it into my ass, but it hurt when the tip of it popped into my butt. “Ouch! That hurts… your dick is too big.” I pulled back from him and the head of his cock popped out of my ass. 

I was still reeling about what had just happened. I was very high and just wanted to curl up and fall asleep. I could feel Kenny’s dick rubbing against my ass. 

“Can I jack off against your butt?”

“Umm.. okay, just promise you won’t push it inside.”

Kenny jerked his cock faster and faster then pressed the head of his dick against my ass. I could feel him shaking and jerk a few little thrusts against my butthole, then streams of warm cum sprayed against my butt. I could feel some of it shoot inside my ass. It didn’t hurt, but the feeling was weird. Kenny kept shaking and lightly thrusting his cock against me until he was spent. 

He pulled up his underwear, rolled over and was quiet. I pulled up my underwear and slowly drifted off to sleep while my mind spun wildly because of the pot and the feeling of my first climax. 

I had never experienced such an amazing and powerful feeling of pleasure, yet I was embarrassed that it was with my cousin, and with another guy at that!

Kenny and I never discussed what happened after that night. It was my first orgasm, first anal sex, and the only sex I have ever had with a guy. I sometimes wonder if that night started my obsession with anal sex... an obsession that has only increased over the years. 


2023-10-16 22:15:48
mummm nice you should have lubed up and let him fuck you


2023-08-09 16:47:06
Sounds like a fun experience. The first time can be a little hard to wrap our heads around.

Trib FanReport 

2023-06-13 12:04:55
It wasn't my first orgasm but I nutted rubbing my cock in my friend's ass long ago. We didn't penetrate but it still felt as though I was fucking a girl's pussy.
We both enjoyed the experience....No regrets....

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