Let my friend’s brother finish his jerk session with my butthole [FM]

I’ve always loved anal – not just loved it, but CRAVED it, and anyone who has spent enough time around me is well aware of this fact, including my roommate’s brother, Sam.

The three of us (Lisa, her brother Sam, and myself) were living together at the time (I’m 21 now), and there had always been a ton of sexual tension between her brother and myself, but he was the kind of guy who really struggled to make a move on any girl he found attractive, despite the fact I made it painfully obvious that, if he wanted, all he really had to do was ask.

On this particular day, I was lounging around in my underwear and a tank top with no bra, making some food in our kitchen, when I noticed him staring at me from his bedroom doorway. I don’t think he had been there long, and as soon as I glanced in his direction he turned away, closed his door, and started blasting music. I knew him well enough to make the safe assumption that this meant he was going to jerk off, as this seemed to be his go-to routine. Considering this happened at least twice a day, I normally wouldn’t have thought anything of it, but the fact he had been staring at me immediately before deciding to make himself cum had me feeling sexy, and just a little bit naughty :)

He had seen me naked plenty of times, but I had yet to see his dick, and after thinking it over for a minute and allowing my own horniness to build to a boiling point (I wasn’t dating anyone at the time and my sex drive was off the fucking charts), I decided a minor invasion of his privacy at the right moment might just result in something fun! After all, my little whore brain had seen this scenario play out enough times in porn and I figured it wasn’t TOO unrealistic to expect a horny 20-year-old guy to find the courage to make SOME kind of move on a hot girl who clearly intended to catch him wanking.

Not wanting to catch him too late in the act, I quickly bounced over to his door and put my hand on the knob. For a brief moment, I got incredibly nervous and almost decided to turn back and call the whole thing off. My heart was beating fast and a voice in my head was saying, “Come on, Kate, this is ridiculous. You can’t just walk in on someone jerking off and expect anything other than a scene of monumental embarrassment to unfold.”

Fuck it, I thought – who cares if it doesn’t go how I’m hoping? It’ll be a lot of fun if it does, and at least I tried!

Apparently the voice in my head got to me a little though as, instead of bursting in like I had planned, I slowly creaked the door open to get a look inside first and attempt to confirm my suspicions. No surprise, he was definitely jerking off, but it was not quite the scene I expected or, at least, my own reaction wasn’t quite what I thought it would be.

He was sitting at his PC in such an exaggeratedly hunched over and strange position that I momentarily felt a pang of laughter build before I managed to suppress it. I glanced at his monitor to find a wild hentai orgy playing out, and I can’t say I was the least bit surprised. Almost every guy I had dated up until this point seemed absolutely obsessed with jerking off to hentai. I can’t say I fully understand it, but I’d be lying if I said I hadn’t cum to it more than once myself. Sometimes the scenarios are just so hot, and it pushes the right buttons for me.

Anyway, I found myself becoming enthralled with what I was watching – my eyes constantly darting between the screen and his wanking. I couldn’t quite see his dick, as his back was facing me, but I was still enjoying the show, and I was beginning to feel that familiar, cramping emptiness in my holes that signaled I was fully expecting and craving to have something inside of me, and soon. The whore inside me was beginning to take over, and I felt my courage desperation guiding me toward making a move.

I had only been standing there 30 seconds or so, but Sam’s body language was signaling to me that he was building toward cumming, and I definitely didn’t want to miss my opportunity. I opened the door fully, stepped into his room and said, “Hey.” Brilliant and sexy, I know, but the moment had me a bit flustered and I couldn’t think of anything else to say lol. I expected him to turn around in startled bewilderment, but nothing happened…

What the fuck, did he not hear me over the music? “HEY!”, I repeated much louder this time. I must have scared the absolute shit out of him, as his head swung around so fast I practically felt his gaze physically smack me when it found me standing there like an idiot. “Sorry!”, I said, suddenly feeling like I had done something very wrong. Sam seemed momentarily overwhelmed as he clearly tried to figure out what to do first – close the porn, turn down the music, ask me what the fuck I was doing in his room, etc…

I held my ground as he scrambled to hide his dick first, then turned down the music to look up at me and say, “You seriously almost gave me a heart attack.” I was definitely feeling bad now, but I had what felt like a great idea and, perhaps, a way to salvage the trainwreck I was causing. “Sorry, can I make it up to you?”, I said as I made an obvious gesture toward his dick, with my eyebrows raised and a slight smile on my face.

“Are you serious?”, he responded. I was feeling both bold and incredibly eager to escape the awkward part of this experience, so I said plainly, “Do you want to fuck me or not?”

Maybe it was the effortlessness I had gifted him, or the fact that his dick was still hard and his brain set on cumming, but he found the confidence to stand up out of his chair, grab his dick, and motion toward his bed in the corner. Thank fucking God

At this point I was thrilled to find my plan had worked, but even more eager to forget the last 30 seconds and just get to fucking. I closed the door behind me and practically leapt onto his bed in a doggystyle position – pulling my underwear down to my knees and spreading my ass open for him as I craned my head around to watch his reaction. I figured, if I can just keep things moving quickly, then he won’t have time to second guess himself.

His eyes went wide, but he moved toward me and immediately began rubbing the head of his dick against my pussy. Apparently he uses some kind of lube when he jerks off, as his dick was clearly covered in something slippery, and he found no resistance whatsoever has he pushed his larger-than-average cock into my hungry slit without a second thought. I groaned in pleasure and immediately began searching for my first orgasm as he began to pump in and out of me at a pace which suggested he was simply picking back up where he left off before I interrupted him.

I felt as if he was simply using my body to finish his jerk off session, and something about that had me incredibly turned on, and approaching orgasm FAST. Just as I was about to pass the point of no return, he pulled out of me and said, “Fuck!”

Was he about to cum already? I couldn’t blame him, and I expected as much, but I was still hoping I’d get a chance to cum at least.

“I’m not gonna last long. Do you…” He paused for a second and I suddenly felt an overwhelming impatience. If he wasn’t going to cum right that second, then he better get that fucking dick back inside of me immediately.

“What? Spit it out! I was about to cum!”, I almost yelled back at him.

“You like anal, right?”

LMAO. Can’t say I was expecting that, but if that’s what he wanted then I wasn’t about to stop him. As I said, I’m an anal slut, and I knew I’d be cumming within seconds of him fucking my ass.

“Yes, you can fuck my ass if you want, just get it inside of me.”

His dick was already lubed up, but I figured a little extra spit couldn’t hurt, so I quickly spit in my hand and slathered it on my puckered little asshole for him. He didn’t waste any time, and he was lucky I was so experienced with having things shoved in my ass, as he immediately plunged the entirety of his cock, balls deep, into my tight little teenage asshole like I was some kind of fuckdoll for him to use. JACKPOT (I am, and I love being treated like this).

“Oh FUCK!”, I groaned as he continued to use my hole as if it weren’t connected to a living human being. I began furiously rubbing at my clit and, within 15 seconds, I was cumming HARD. I could feel my asshole convulsing on his cock in waves with my orgasm, and he let out a moan of his own as he grabbed my hips hard and began thrusting into my butthole with a clear intent to pump his cum as deep into my guts as he could.

And there it was – one of my favorite feelings in the world – I felt the warm spray of his cum flood my insides as he pounded it into me. It was almost as if he wanted to drive it so far inside me that there wouldn’t be any evidence of him having cum at all, and I was happy to be his receptacle.

He began to slow – breathing hard now and relaxing his grip on my hips as he made one final thrust before slowly pulling out of my now gaping asshole. He put his hands on my butt cheeks and spread me hard, no doubt admiring his work and the filthy view. “Fuck, that’s so hot.”, he said as he moved his face closer to my asshole and seemed to be searching inside of it for any trace of the cum he had just ruthlessly fucked into it. He seemed to be living out a fantasy of some kind, and I was having fun being the one to help him fulfill it.

“Can we do that again sometime?”, he asked as he let go of me and began to clean up.

“You fucking better.”, I responded.

In case you’re wondering, yes, we did fuck again – that day in fact, with his sister in the house and clearly able to hear us lol, but this is already longer than I intended, so maybe I’ll tell that story another time.

Source: reddit.com/r/gonewildstories/comments/wg77k4/let_my_friends_brother_finish_his_jerk_session