Helping My Gay Roommate With His Gag Reflex

Everyone is 18.

He came home exasperated. It was our second night of new student orientation, and he slumped through the door like someone had just told him his favorite pop star was retiring. This was only the second night of college, and both nights in a row my gay roommate, Brandon had come home looking sad and defeated, and I wasn’t about to let it slide again.

We’d been paired as roommates over the summer, randomly through the housing portal. But once I looked him up, his Instagram, his profile pics, it was clear he was gay. Not that it mattered. His bio said something about iced coffee and chaotic good energy, so I figured we’d get along.

We messaged a few times before move-in, mostly about what to bring and who was bringing the mini fridge. It wasn’t long before we were joking around about cleaning schedules and the weirdly shaped floor plan in our suite. He suggested we make it a “fun zone,” and I said only if that meant snacks, zero drama, and at least one weekly dumb game night. We had a vibe, even before we met.

So, safe to say I liked the guy, and considered him a friend from the start. I couldn’t just let him mope like this. I pestered him until he finally let it spill. 

“I got with the hottest guy at the party,” he said, eyes wide, still a little stunned. “But two minutes into things, he left. I think I gagged too hard or something. It’s like, even when I want to be good at it, I mess it up.”

I scoffed. "Who the fuck quits on a BJ just because of a gag reflex? He sounds like a fucking idiot."

I looked at his body. He had a standard male build of a guy who was naturally lean, and played a sport or two, typical college freshman, decent face. I assumed he would be getting with plenty of other gay guys if he was willing.

He piped up. "To be honest, my insecurity about it wasn't helping. I think he sensed it and left."

Ah, the truth of the matter.

He flopped dramatically onto his bed. “My gag reflex is cursed,” he mumbled into a pillow.

I tried not to laugh too hard. “Okay, you know you just need practice, right?” I said it casually, like I was offering to quiz him for a midterm.

He sat up like I’d zapped him. “No shit, but nothing is working.” He looked back down at his phone.

He was quiet for a minute, scrolling on his phone. I decided to offer him some advice.

“So, back in high school, this girl I was hooking up with, Chloe had a similar issue. She wanted to impress this guy she was getting serious with, but she kept panicking and overthinking everything."

His eyes were on me now.

I went on. "She practiced at home, but wasn't getting any better with her gag reflex. So one afternoon, I put her on her back on her bed, and, slowly but surely, I stretched her out. It took the horniness of a male, but the patience of a friend to get it done."

I could see his horny little gay body perking up as I told him the story. I enjoyed the attention. So I went on.

"I probably dumped fifteen loads into her stomach that week, and by the weekend she was fully deep throating her man friend, texting me updates like they were game scores. And he said she crushed it, apparently."

"Well that story is hot as hell, but who's gonna do that for me? My brain freezes up every time I get close to hooking up."

I narrowed my eyes at him. "Maybe you need a straight guy to help you out then... as a friend."

He got quiet, turned red, and I think I saw his ass literally quiver. 

I smirked. "Just hang on a sec." 

I walked out and rummaged through the fridge until I found a cucumber. I didn't know how to pick which one, so I chose the one that matched my own the closest, which happened to be the largest one we had. Not trying to brag, but I have a more than decent sized melon-baller downstairs and it was always a heavy hitter with the ladies. I came back to him holding it like a baton. He looked at it like it had personally offended him.

“That’s what you’re using?” he asked, half-scandalized, half-embarrassed.

I grinned. “What, did you think I was going to use myself? I'm not drunk enough for that shit, gay boy.”

The teasing was clearly torture, but that was half the fun. I grabbed him gently by his curly hair, and he looked me in the eye, his mouth naturally falling open a bit. He really was a horny little guy. I laid him on his back with his head hanging off the edge of the bed. He wordlessly followed my direction, and opened his mouth, sticking his tongue out.

My crotch was right near his face, and I saw him staring at it, drooling. I didn't know why, but I was having a lot of fun with this. He was obviously enjoying himself as well, based on the throbbing bulge in his jeans. He wasn't hiding it.

I held the cucumber in front of my crotch like it was my dick, and I thrust my hips forward, probing his mouth. He closed his lips around it, and started making out with it, his tongue giving it a firm massage.

Nice, I thought, he actually looks good at this.

“Let’s figure this out. I’ll coach. You try not to die.”

I pushed in barely a centimeter, and he gagged, retching roughly against the vegetable. 

I pulled it out. "Alright, we have a baseline."

He sighed, his cheeks red and his eyes filling with some tears from the gagging, and opened his mouth again.

“Okay,” he said. “Just don't make me throw up.”

“Noted,” I said. “And when you're a legend by the weekend, I want you to tell every stud you deep throat that I get the credit for teaching you.”

He smiled. I frowned. "Actually, don't do that." We laughed.

We didn’t know it then, but this ridiculous night, sitting on a twin XL bed with a cucumber and a shared sense of college boredom and curiosity was about the define our dynamic for the entire school year.

I slowly put the cucumber back on his lips. "Ok, relax and we'll try again."

I pushed it gently against his tongue, and I saw him tense up. "Relax, think happy thoughts, it's just a cucumber. There's no one to impress."

I saw his body melt down a little, and I pressed forward again. This time I got halfway into his mouth, and I saw him brace again. Instead of pushing his limits, I pulled it back out to his lips. Then back in and out, in shallow thrusts, massaging his tongue with the cucumber.

"Here's your comfort zone, right here," I said, as I continued gently pressing the large, green vegetable in and out of his mouth. I could tell he was nervous, and his mouth was actually getting a little dry. I pulled out the cucumber. He had learned his place at this point, and stayed put, looking up at me with his mouth open.

I let a large glob of spit drip down from my mouth into his. He accepted it and held it in his mouth, letting out the quietest moan, and involuntarily reaching a hand down, pretending to scratch his balls as he adjusted his raging bulge.

"That's better," I whispered, "nice and wet for me."

I put the cucumber back in, and he started to moan around it. I pressed in a little further this time, watching him accept it in a relaxed state, completely subdued. No nerves, just a role to play in my little game. Without even realizing it, he was getting better at controlling his gag reflex. I took a chance and pressed into his mouth further, making contact with the back of his throat. He gagged again, and I adjusted to pull out the cucumber, but he grabbed my hand, holding me in place, and pulled it back in further. He gagged again, lighter this time, and I pushed past it. 

Quickly, without giving his body a chance to react, I shoved the cucumber down as far as it could go, eight inches into his throat, and momentarily watched his neck bulge out with a thick cylinder stuffed into it before I pulled it all the way out. 

He retched lightly, but didn't gag.

"You're getting better already," I muttered, my tone more serious now, and I pet his hair with my hand.

He smiled. Clearly enjoying this. I started to insert the cucumber again, this time to the top of his throat, and held it again right at my crotch, like I was fucking his throat myself. I grabbed his hand and placed it on my hip. 

"Guide my rhythm."

He gripped my hip firmly, and raised his other hand to it as well, while I held the cucumber in front of me, and continued thrusting into him. Besides a few minor gags, he was taking it "balls deep" in just a few minutes. I was amazed this guy ever even had a gag reflex problem. He started going faster and faster, really tearing himself up, and I watched as a big wet stain on his pants grew wider and darker. He was loving this. 

And just like that, I pulled it out of his mouth, and threw it onto the kitchen counter. 

"Good job tonight." 

His face was pure disappointment, lack of release, tension. He looked almost cute, if you could say that about a guy.  He didn't say anything. I knew he wouldn't. 

I went to bed satisfied, enjoying the power dynamic I was brewing with this gay kid I was paired with. And after all, I was still helping him with his gag reflex problem too. I honestly was looking forward to hearing about him getting better at it. 

We didn't talk about it again that night, and I lay in bed playing on my phone for a few minutes. Then I realized I needed to release my balls, and I pulled up some porn on my phone. I stayed covered with the blanket, but made no attempt to hide what I was doing. I pulled off my underwear, and kept them nearby as I stroked by oversized rod to satisfaction, while he watched out of the corner of my eye. I finished into the underwear, and dropped them on the floor by my bed, and then kept playing on my phone. He rolled over and pretended to sleep, but I could tell he was jerking a well-needed load out of his boy balls. I chuckled, and went to sleep.

—[]—

The next morning, he was gone when I woke up. I had slept naked since my underwear was soaked in jizz. I stood up, stretching my arms over my athletic body, and admired my morning wood in the mirror. I had measured it at just over eight inches, and I didn’t even cheat when I did it. Measuring against my brother over the years proved I was the alpha at home, in both length and thickness, which was nice. 

Just as I was starting a nude flexing routine in the mirror, the door slammed open. Brandon walked in, wearing a towel and holding shower stuff. I didn’t bother to cover up. If we were roommates, he was gonna see some shit. He stopped when he saw me and dropped his shower bag, little bottles rolling everywhere. I just chuckled at first while he fumbled around, and then I bent over to help him pick up his stuff. He was on his knees as well, and when I stood up, my hard-on got within an inch of his face. He stopped and stared, and I even think he took a big whiff through his nose. 

I held out his bottle that I had picked up off the floor, and saw the label said “Astroglide” and “anal lubricant” on it, making me chuckle. I held it out for him, right next to my cock, letting him admire my body up close. I was still hard with my morning wood, and maybe a little extra from the attention I was getting. I saw him swallow hard, reach out and take it from me, his face turning red when he realized what I had seen.

“You must’ve been having fun in there,” I said while I walked over to my closet, flashing him my muscular white ass while I grabbed my bathrobe.

“Have you…” he started, before pausing. I tied my robe in front of me, doing nothing to stop the tent from protruding from my robe.

“Yeah?” I said, grabbing my 3-in-1 bottle and getting ready to head to shower.

“Have you ever… been with a guy?” I chuckled.

“No,” I said, but thought for a second, “well, not sober.”

I saw him wince when I said that. He was such an easy one to mess with. I turned around and headed for the door. I had a nice shower, and rattled my sausage for an easy morning jerk sesh, before heading back. When I opened the door, he was throwing on a pair of pants in a frenzy, facing away from the door. I saw his little ass quivering in fear, so I knew I interrupted something. I guess I came back quicker than he expected. I looked at the paper towels spread on his bed, and I knew he was trying to bust a quick one out while I was in the shower, no doubt spurred on by my teasing that morning. 

I think the torture had hit a breaking point, and I wanted to do something nice for the guy. Besides, why waste the opportunity to let him be a good roommate?

“Hey,” I said, while he was still one leg out of his pants, little ass bouncing around, manically trying to pull them on and hopping on one leg.

He stopped, temporarily giving up on his vain attempts to hide whatever he was trying to hide, and looked over his shoulder at me.

“Lay on the bed, dude,” I said in a friendly tone. He stayed frozen, facing away from me.

“It’s cool, man,” I said quietly.

He started fumbling with his pants again.

“You don’t need those,” I said. And his face turned red.

He didn’t say anything, just kept his head sort of downward, and crawled onto his bed, then lay back in the position of last night. I saw his hard dick for the first time, and I was surprised. It was not small. 

“Damn, dude,” I said, “you’re packing heat down there.” I saw his body tense a bit when I said that. I’m guessing he didn’t expect me to comment on his package.

“Look who’s talking,” he quipped back, looking directly at my own meat pole, which was getting hard again.

“Yeah, but, I think you’re the biggest guy I’ve seen besides myself. You’re gonna do fine with the dudes here.”

“I’m more of a receiver than a giver actually,” he said, “but I appreciate the compliment.”

“Still, dude,” I said.

I walked up to him, my rod and inch from his face, and added one more thing. “You can jerk off if you want.” 

His body melted into the bed when I said that, and he quickly reached for the base of his thick rod, and opened his mouth. He knew what was happening.

I squatted down slowly, and put my hard tip into his mouth. He immediately took to it and started making out with it, a firm grip between his lips and his tongue. I shuttered a bit, not realizing he was going to be this good with his mouth. I was careful not to press forward too quickly, but after the training session from the night before, he was apparently ready. He grabbed my hips and pulled me in. I was stretching his pink lips around my fat girth, since my thickest part is in the middle, and he gagged quickly, but it was only a light one. I let him pull me in further, and he retched once again. It actually felt good when he tensed on my cock, and I couldn’t resist pushing in further. He almost stopped me, but then held my hips tight and braced for my thrusts.

“You’re gonna be a fucking pro,” I muttered between my teeth, as I started entering his throat. He was actually learning much faster than the girl I trained previously. I grabbed the sides of his narrow torso and pulled myself quickly into his poor little throat. I watched his neck bulge out obscenely, while he retched, with a low, struggling sound coming from deep within him. My thick shaft plugged his throat as his body convulsed once, then twice. He slapped my thighs, but I held down firmly, watching his own big, pink dick twitch and start to dribble out pre-cum. It looked even larger because of his small frame. I was so turned on by the fact that my man-handling was having this effect on him, I almost forgot to let him breathe. I pulled out completely, and let him suck in a deep breath, before he coughed and sputtered. He recovered in a few seconds, and muttered only one, rough word out of his battered throat. “More.”

I didn’t hesitate, quickly pushing back in, to the hilt. His body rejected the intrusion, but instead of slapping my thighs this time, he reached for his heavy, red rod. He pushed through the tensing as his throat took a battering from my heavy meat pole, and he stroked himself to the tip, rubbing in his pre-cum and making some vocal sounds through the throat fucking. I started to sweat, and it dripped directly onto his face. I don’t know if he even noticed through the tears and throat juices dribbling out. Somehow, even with his throat completely plugged by my rod and unable to breathe, he groaned from somewhere deep inside.

He released a heavy squirt of thick, white satisfaction that hit me directly in the face. I didn’t even flinch. Something about him getting off to my rough use of his throat made my day, and I quickly released my own throbbing ecstasy directly into his stomach. He continued pumping wet squirts onto his stomach while I gave a couple final thrusts into him, watching the base of my cock pulse between his obscenely stretched lips. He definitely needed to breathe, but he knew it was worth the pain to satisfy me. I pulled out when I felt his body start to go limp, and he sucked in a rapid breath, choking on his own juices and my cum, coughing and sputtering. 

When he recovered, I was sitting on my bed, leaning back on my palms, letting my wet hog rest between my legs. He looked up at me through teary eyes, his wet, red face saying everything. 

When he finally spoke, his voice was harsh and gravely. “Good training sesh.” He cleared his throat again, coughing slightly.

“Yeah,” I said, “guess all you needed was a little push.”

“You know, Cody” he said, his voice clearing up a bit, “you can do that any fucking time you want.”

I laughed. “I know.”