Twenty Strokes or Bust

I stumbled home from the bar around the corner from my apartment, drunk, horny, and also a bit wired from a long week of work. I have been g

I stumbled home from the bar around the corner from my apartment, drunk, horny, and also a bit wired from a long week of work. I have been going there since sophomore year in college when I moved into my studio apartment in 2018. Now I'm 25 and have been a regular here long enough, the bartenders all hook me up with extra drinks. For better or worse, it's a great deal for someone with student loans to pay off.

I kicked off my shoes and pulled out my vape, freshly filled with some THC for extra relaxation. I scrolled Grindr, this one profile looked promising. His name was "LOOKING," he is 27, 6'1", 180lbs, mixed race, his only pic of his headless torso looks like he lives in the gym or at least plays a regular sport. No information of what he's “into” or any tags. I sent a "hey." Then I put on Spotify and jumped in the shower for a 2 am drunk karaoke shower session in case I get lucky.

When I got out, I toweled off, slipped on some faded red Hugo Boss hip briefs that emphasize my Irish skin tone but make my dull red hair pop, and flopped down on my bed to check if I was getting any tonight while T-Swift and I sang about feeling 22.

Amongst other messages, LOOKING messaged me back about twenty minutes ago, "Horny?"

Me: Always!
Me: Not to brag, but I invented it when I was 12.

A few minutes went by, and I tapped a few other guys and started some other potential conversations, but then I got a little red notification, and my dick instantly swelled when I saw it was him again.

LOOKING: LOL, what are you trying to get into?

Me: Vers here, but more often bottom if it gets there. Also cool just jerking off, getting my hole teased, and busting a nut together.

LOOKING: Not looking for penetration? [sent dick pic]

Me: I am, but I'm tight, so you gotta put in the effort before you put your dick in. That dick looks big?

LOOKING: 9" [pic sent two more dick pics]
LOOKING: don’t worry, I’m all about slow and sensual.

Me: Damn, that's big! [unlocked album with all my pics]

LOOKING: Can you handle it?

Me: I don't know, it's been a while since I attempted something that big lol

There was a long pause. I was squeezing my cock in my briefs, shifting my dick around so the leaking precum didn't soak an obvious wet spot. I messaged a few other guys back while waiting to see if this guy ghosted me. After about ten minutes, he hit me back.

LOOKING: Do you do poppers?

Me: I tried them once, but I don't have any.

LOOKING: I have some good ones if you want to let me in that ass. [fire-tapped my ass pic]

LOOKING: Can I fuck you raw?

I looked at his profile again, his status says "negative." I looked at his pics again, he's hot as fuck, and my dick-brain started taking over quickly.

Me: I try to play safe, at least the first time with a guy.

Another long pause.

LOOKING: I get that. I can fuck you with a condom if you want.

Me: safe works for me lol

LOOKING: Can I get a few strokes in bare? If you're as tight as you claim, gonna need to open you up before I put on a condom.

Now I took a while to respond. My head was already spinning from the shots I did with the bartender all night, and my vape was starting to do its job, but looking at his dick pic again, it turned me on so much my dick throbbed and squeezed out another drop of precum into my underwear. I’ve gone bareback before, not with a guy I don’t yet know his name. A few strokes bare would probably be ok if he were gentle, as long as he wasn’t a two-pump chump and burn up on entry.

Me: Do you have control?

Me: Lol, good* control

LOOKING: What do you mean?

Me: of your nuts lol.
Me: If I let you get a few strokes bare, are you going to bust quick or do you have good control?

LOOKING: I have exceptional control 😁

Me: Exceptional? Lol, I didn't know that was a thing.

LOOKING: It's true lol

Me: What makes you exceptional?

I grabbed my dick in my briefs again, giving it a slow stroke and a gentle squeeze. A drop of precum oozed into the fabric stretching over the swollen head.

LOOKING: I can hold my nut until you go insane, or I can bust pretty quick if you prefer.

Me: Sounds like no control with a window like that lol

LOOKING: Let me in that ass and I'll prove it 😜

Me: Like a bet?

LOOKING: if you want it to be, or not lol

This got my heart racing. I love a good challenge. As a kid, I wasn’t allowed to play board games because I would get too competitive, and it would get ugly.

Me: Ok, how does it work?

LOOKING: How many strokes can I get bare?

Me: Lol, how many? I don't know, what's a few? 20? 50? 3?

LOOKING: 50 lol

Me: That seems like full-on fucking 🤔

LOOKING: ok, 20.

I took another hit off my vape.

Me: So you get 20 strokes bare and then wrap up?

LOOKING: No, I get 20 strokes bare, and I have to nut before 20 or I have to wrap up.

Me: Wait, you're gonna cum inside me?

LOOKING: Yeah, that's the bet.

I scrolled up our chat and didn't see anything about that.

Me: Run that by me again? Cuz…it sounds like you’re just going to bareback me and cum in me lol

LOOKING: I'm going to prove you how much control I have. You give me 20 strokes and I'll nut inside you by 20, if not, I'll put a condom on and fuck you all night until you beg me to bust.

Me: How do I know you are in control though?

Me: For all I know you only make it a few thrusts.

LOOKING: You could give me more strokes if you want to be sure. I’ll hold out to 30, 50, whatever you need.

Me: Lol, I need you to wear a condom so I don’t catch anything.

LOOKING: A few gentle strokes is perfectly safe. 😜

Me: Hmmm

LOOKING: What makes it unsafe is the tearing of the skin due to friction. 

LOOKING: When the skin tears you get cum in your bloodstream, that's not safe. Even precum.

LOOKING: If there's no tearing, you can take 100 loads.

LOOKING: lol that's why you can swallow a guy's nut, and it be safe, but if he busts in you after a hard raw fucking you can catch something.

I read and reread his message. I have swallowed guys' loads without hesitation. My dick strained against my underwear, desperate for release. I'm not a science nut, but this kinda made sense. My horniness was taking over, and my competitiveness was rearing its ugly head, giving me an idea.

Me: You don't have anything?

LOOKING: 100% don't have anything and fully vaxed.

I thought about it. Reread all of our messages, my dick is hard as a rock.

Me: So, if you’re so “in control,” how about we make a deal? You get 20 strokes bare. You can only cum in me on the 19th stroke, to prove you’re actually in control. Otherwise, you gotta wrap up.

LOOKING: 20 free strokes, but you gotta give me a window of 5 strokes. I’m good, but I’m not a robot lol.

Me: Gentle strokes.

LOOKING: of course, prefer a slow and sensual fuck anyway.

My heart was pounding, and I took a hit off my vape.

Me: You host or travel?

LOOKING: I host [location sent]

I looked at the map. He was twelve blocks and one avenue away. My heart started beating fast with nerves and excitement, so I took a hit off my vape.

Me: Ok, let me get dressed and I’ll be over in 15.

I quickly dressed in mid-thigh athletic shorts that show off my squat gains and a matching athletic t-shirt that shows off my trim body—then I checked my phone again before heading out.

LOOKING: I prefer you show up naked, but if you gotta get dressed, dress in the bare minimum 😉

Me: Lol, I’m on my way. Wearing gym shorts, briefs, and a t-shirt.

LOOKING: mmm, can’t wait to get my free strokes in you. Coat your guts with my cum.

Trying not to get hard as I walk down the block, I closed my phone. Then, as the blood left my dick, I messaged back.

Me: You only get 20 pumps, then you gotta wrap up. No free strokes.

I adjusted my dick in my underwear.

After another block, I checked again.

LOOKING: If you’re as tight as you say, I’m gonna nut in you on pump 15 lol.

Me: When do we count the first stroke? More than the tip or balls deep?

Another block went by before he responded.

LOOKING: Balls deep.

LOOKING: Is that how u count it?

Me: Makes sense. Once you’re in though…a half pump still counts lol.

Me: But I guess you’re gonna have to tell me when you’re in all the way.

LOOKING: U want me to count as I pump?

Me: Yeah, that would be hot af

My dick started swelling at the idea of him counting out loud. I had to look away from my phone before I was fully hard and became that crazy guy walking through the city with an erection. After a few hits of my vape and I cut across an avenue, my dick had gone fully down I checked my messages.

LOOKING: I will say, “That’s one pump, baby.”

LOOKING: What if I get to 20 and don’t cum, what u want me to do?

Me: Mmmm

I fire-tapped his message.

Me: You’re supposed to pull out and wrap up.

Me: If you get to 20 and can’t cum yet.

LOOKING: Ok, I will pull out and wrap up for u, baby

LOOKING: whatever u want

Me: I thought you had good enough control to nut at whatever pump you want?

I started getting nervous again and took another hit off my vape.

LOOKING: I will cum, depending on when we start counting strokes. Might hit 20 quicker than I want if you can’t handle my big dick.

Me: Do you have a condom?

I walked another block before he responded.

LOOKING: Of course, gonna nut before though 😈

Me: With the condom on, you can fuck me as long as it takes to bust.

I walked three more blocks before checking the address and the messages again.

LOOKING: What if it so good I forget to come out?

Me: What do you mean?

I was getting close to his building and kept it open. My heart is always racing before meeting up with a guy for the first time, but this guy had me leaking precum in my underwear while walking down the street.

LOOKING: What if it gets so good I forget to pull out and put the condom on?

My dick was getting hard as I walked up to his building. I turned towards a trash can on the corner, hoping no one would notice.

Me: Like, you push in and say, “mmm, that’s 20,” and then can’t bring yourself to pull out because my ass is so tight it feels so good, you want more bare strokes?

LOOKING: Yes

I pulled my dick up into the waistband of my briefs and started walking again.

Me: Hmm

Me: I guess it depends

LOOKING: On what?

Me: So you savored your 20 bare strokes?

LOOKING: Yes, I did not pound the hell out of u

LOOKING: Just slowly in and out the whole time

LOOKING: I just wanna make love to you, I don’t want to pound u silly to win the bet lol

Me: And it feels good?

LOOKING: real good, and you took another hit of poppers at stroke 19

Me: Are you close at this point?

My head spun through this conversation, and I was still a block away from making any of it a reality. I knew he was hinting not so subtly for me to give him permission to fuck bare the entire time. But my competitive streak and that last brain cell of self-preservation were not letting that happen.

LOOKING: Yes, I can feel it on the edge. But I need a few more strokes.

I walked up the steps to his building entrance.

Me: How many?

LOOKING: Could be 2, could be 6

Me: Which unit do I buzz?

LOOKING: 2H

I took one last hit off my vape before I hit the buzzer and got in. Entering the lobby and then the steps up to the second floor, I was able to get my erection down enough to take my dick out of the waistband. 

I was at his door in the blink of an eye. He opened it shirtless. His light brown skin was shiny, like he had just put on lotion or did a light workout, and his pecs popped like he was doing pushups. His boxers stuck up slightly over his gym shorts, and an obvious bulge dangled between his legs, definitely a semi from the thickness and the tenting. He had short-cropped hair with a diamond stud in his ear. I couldn’t help but blush when he flashed me a brilliant white smile, then subtly licked his lips as he looked me up and down through glassy eyes.  

He cocked his head for me to come in, and he walked me into his bedroom. I noticed his place smelled like a smoking lounge or Abercrombie and weed…hard to say.

“That’s my roommates' room,” he pointed to a closed door, then we walked to the open door with dim lights and soft music already playing.

His Bluetooth speaker was playing some sex music. His bed had sheets and pillows with no blankets. The nightstand had lube, poppers, but no condoms lay out. He closed the door behind us.

“Is your roommate home?” I asked, turning to get a better look at him.

He shook his head no, then wrapped his arms around my waist, pulling me tight to him. His bulge hit closer to my belly button due to our height difference since I’m 5’6” and he’s over 6’. Then he leaned down and kissed me. It was really sensual, with some light groping of his hands on my ass. I felt my concerns and nerves drifting off as his tongue explored my mouth, and I put my arms around his bare, well-defined shoulders and pivoted my head to the other side to get more of his tongue in me.

He didn’t break our kiss but slowly moved us toward the bed. When the back of my calves felt the baseboards, I felt his hands come up my back, his hands touching my skin, making me inhale deep as he pulled my shirt up and off my torso. Breaking our kiss for a brief moment to pull the shirt over my head and drop it to the floor by my feet, then he was back in my mouth, breathing and quietly moaning as his hands rubbed my back and then dropped down into my underwear to palm my ass cheeks.

“Mmm,” I moaned and inhaled, feeling my cock responding to his touch, straining against the tight material of my briefs, tighter now that his big hands were also inside.

He broke our kiss so he could push my shorts and underwear to the floor, kissing my chest on his way down. My cock sprang free, and his hands came back up the back of my thighs to grab my ass tight, but sensual, lifting me slightly off the ground as he pulled me in for another kiss, letting the index finger of his right hand graze over my hole. 

My hard dick now pressing into his growing bulge as he lay me down on his bed. I fell flat on my back and he stood between my legs, hooking his thumbs on the waistband of his boxers, he quickly shoved them and his shorts down to the floor with a grin. 

I got a quick glance at his thick, growing piece of meat before he climbed on the bed between my legs. His knees pushed my legs apart as he crawled on top of me. My legs straddled his thighs, and he shimmied us further toward the middle of the bed as he pawed at me and kissed me for a few minutes. His massive cock was coming to life like an emergency inflatable raft, warm, soft, and rigid, sliding slowly below my balls and wedging itself between my ass cheeks as his arms wrapped under my armpits and gripped my shoulders from behind, pulling me tighter to him.

“Baby, you’re so hot,” he kissed my neck, then sat up and reached for the lube on his nightstand. He quickly slicked up his dick and then brought his fingers between my legs, swiping across my hole, then added more lube to his fingers, gently massaging it into me. His rigid digits managed to dump a fair amount of lube into me quickly. He stroked the excess onto his cock before dipping it down between my legs, letting the thick head glide over my hole as his hands flanked my shoulders and lowered himself down to kiss me some more. Rocking his hips repeatedly to slick up my crack with his cock, the head crossing over my pucker got a gentle moan from me each time.

He pulled his head back a little, giving me an open-mouthed kiss that was just a tease, as our lips hovered within millimeters of each other, his tongue dropping into my mouth as he hunched his hips. The head of his cock traced the crack of my ass, this time adding pressure that forced a silent moan out of my already open mouth.

His cock found my pucker and pressed a bit harder. “Mmm,” my head tilted back, and he licked my chin, then used his big right hand to gently hold my throat as his next hump got a silent moan out of me. His left hand reached back to the nightstand, grabbing the little brown bottle and shaking it. 

The cap had been replaced with some kind of mechanical top. He put the bottle to my nose, pushed a button, and, in a deep voice, told me to inhale. I took a deep breath, and the poppers hit my lungs instantly. That rush washed over my body, reacting with the booze and my vape to heighten everything and every touch of this moment. 

“Holy shit,” I mumbled. I’ve tried poppers before, but they just gave me an instant headache and a slight lightheadedness. These had my entire body relaxing in waves of pleasure almost instantly.

He released my throat, dropping his right hand down to his dick, wiggling it on my hole as he used his left hand to shake the bottle. Pushing it under my other nostril, he pressed the release button. I inhaled deeply, and he twitched his cock on my hole with even more pressure this time. I relaxed and felt him gently push the head into my ring, just the crown, separating my brown eye just enough that I felt my pucker kiss the tip of his cock, and a rush of electricity shot into my body and came out as another soft moan.

“That’s it, baby, open up for me,” he growled.

My hand dropped down to my dick. I was so hard and horny; the teasing of his fat head on my hole was quickly trying to make me look like the two-pump chump. I don’t care, though. I rocked my hips with his teasing cock as the rush started to subside and enjoyed the pleasure where I’ve usually felt a sting from the breach of my sphincter.

He leaned in and kissed me, his abs stroking my dick as he did. Then he pulled his head back, “I want to get inside this tight ass,” he sat up on his haunches. Using his right hand to slide up and down my crack, then thumping the shaft on my hole. I bit back another gentle moan. He grabbed a pillow with his left hand, then lifted my legs on his shoulders with his right, slipping the pillow under my ass and settling down in a more comfortable position with his cock pointed right at my pucker. He smiled down at me, then pulled the bottle of poppers up to his nose and inhaled on both sides before passing it to me.

He stroked his tool up and down my crack, pausing at my hole to add some gentle pressure. Then he grabbed the bottle of lube and doused his cock head right at my hole, the drips pooling in the crevice, then getting pushed in by the crown of his cock, and my hole started to suck him in.

I groaned and shook the bottle of poppers, quickly figuring out the sport cap. I inhaled deep on both sides and let the rush was over me as my ass slowly opened for his invading cock to sink an inch into me, then popped back out, repeating the motion a few times until he felt like he could push in deeper.

“Mmm…that’s it, baby, open up and let me in,” he hummed.

I took another hit and groaned as his cock started to push gently against the resistance of my tight hole. “Ahhh…fuck you’re big,” I groaned.

“You’re ok, just relax,” he said, leaning over to kiss me, then looking down to watch his cock enter me.

I wrapped my arms around his neck as I pulled him into me. He slowly sank more of his dick into me, and we moaned into each other's mouths. His cock is the biggest I’ve had in a long time, and I was loving the sensation of being stretched out by him, even painfully slow like he was. I let my hands run down the muscles of his back and stretched my legs out wide to let him sink further into me with just his body weight.

“Oh, fuck,” I gasped when I felt his dick poke my inner ring. My toes curled instantly, and my ass muscles flexed.

“That’s it, almost there,” he groaned, pulling his hips back, he thrust gently into me, brushing that inner ring that made my toes curl, and we both groaned.

I took another hit of the poppers and then held the bottle up for him to get a hit. He took a deep breath, holding himself up with his arms, flexing his cock inside me. He hung his head, taking in all the pleasure, then slowly pulled his hips out and sank them deep into my blooming hole.

“Mmmm,” I moaned, feeling that amazing tingle inside me. I gripped my dick and rolled my eyes back into my head. His cock twitched inside me, no doubt adding a drop of precum to the lube, keeping me from being torn open. I slowly stroked my dick between us, biting my lower lip.

He rocked his hips back, almost pulling his cock out of me, then pushed it in slowly, hunching up into me and hitting my inner ring good this time. I groaned, and he leaned over me, wrapping his arms under me again, gripping my shoulders. He pulled me down onto his cock and groaned as he pierced my second ring. “That’s one baby.”

“Ungh,” I groaned from his girth, my eyes popping open, remembering our deal.

He slowly stroked the next full stroke, his cock flexing inside me as he bottomed out and his head pegged my inner ring, almost breaching it but being more gentle this stroke. “Mmm…that’s two.”

I took another hit of the poppers and let him take his time with the next three strokes as my body relaxed and took him deep into me. Sending waves of pleasure through me at an intensity I never felt from hard pounding. I couldn’t even stroke my dick as he held us so tight together, humping gently into me, kissing me passionately, and continued to break the kiss only to count out the next stroke and the next stroke. 

Blowing through five through twelve pretty quickly, not pausing to savor it like he did the first few strokes. I thought I was going to win for sure, and then slowed it up again for thirteen. 

“Ungh,” I groaned as he hunched into me on the fourteenth stroke. “Oh shit,” I felt the pressure as his swollen cock breached my inner ring deep this time. “Fuck,” I inhaled and pulled him tighter to me, digging my heels into his hips.

He held it deep inside me, rolling his hips, his cock getting thicker with each little circle. He licked my lips, panting. “Fuck you’re tight,” he huffed, pulling his hips from my ass, then sank all nine inches into me in a slow but determined thrust. “That’s fifteen, baby,” he flexed his ass muscles, his cock head popping into my inner hole as he threw his head back. “Fuck, I’m close,” he huffed.

“Yeah?” I panted in surprise, my heart pounding.

He grinned, “Oh yeah,” he shook his head, then completed another deep, agonizingly slow stroke, hooking his hips up as he bottomed out. “Ungh…sixteen,” his eyes rolled back into his head as he grinned and flexed his cock inside me.

I was so turned on, my heart was pounding so hard inside me, I felt my ass flexing on his cock, my dick leaking precum between us. Was he cumming? He licked my chin, then kissed me and did it again.

“Mmmm, seventeen baby. You want my nut?” He licked my lips again, teasing my mouth and withholding his kiss.

I grinned at him and shook my head no. Then let my hands drift down his back and cupped his ass as he flexed those sculpted cheeks, and his cock dropped another squirt of precum inside me.

“Too bad, I’m gonna nut in you,” he kissed me and pulled his hips back, his cock only held inside by the tip, and thrust deep into me. “Mmm, eighteen,” he chuckled, then quickly pulled out and thrust harder into me, making my ass clench. “Nineteen,” he huffed, turning his head to stretch his neck as he enjoyed the depths of my body, holding his hips against my ass.

I couldn’t help but watch as all of his muscles flexed as he held himself inside me.

“Take another hit,” he said, rotating his hips gently, pulling my shoulders so he could rock in deeper just a tiny bit.

I nodded, quickly took a hit of his poppers, then offered them to him. He shook his head no, grinning at me, but still circling his hips. The rush washed over my body, I felt my muscles relax. His knees butterflied on the mattress as he held his cock deep inside me, held me tight so our hips didn’t separate. I felt his cock swelling inside me. Then he slowly pulled his cock out, held the tip just inside my outer ring, and kissed me, letting the first inch sink back into me, then the second, then he quickly pushed all of his inches inside me and whispered a choked “twenty,” pulling me tight to him, he rocked his hips halfway out. He groaned louder, pushed in, and moaned into my mouth as I felt his cock twitch inside me. “Mmmm, yeah baby,” he rocked his hips again, his cock punching through my inner ring, the root of his thick meat twitching at the base where my hole clamped tight around it, and I suddenly felt the warm wetness of him unloading inside me. 

“Oh shit,” I huffed as I felt his orgasm making my toes curl as he filled me up.

He hunched into me harder, grunted, twitched a few more times, and then relaxed on top of me, making sure to kiss me and share the air in his lungs along with his orgasm.

After a few more seconds, he broke our kiss and relaxed his grip on me. Pulling his face away from mine, I was able to focus on his grin, beaming with pride in his win.

“Fuck…did you cum in me?” I stretched my legs around his waist, feeling his cock slide easily inside me.

He chuckled, “You know I did,” then sat back on his haunches. “Now it’s your turn,” he started stroking my dick and used his softening dick to slide his cock head over my prostate in tune with his hand stroking my cock. It only took a few synchronized strokes of his fist and dick for him to get me on the edge. I felt my abs and balls tighten, and I curled upward, like a shock forced me into a situp as his cock rocked inside me one more time, and my cum rocketed out of my dick onto my chest. He kept stroking me, tightening his grip and sinking his cock as deep as he could, rubbing my thigh with his free hand and using his thumb to add pressure under my balls. He whispered, “fuck yeah baby,” as the next few shots of cum launched out of my dick, and my shoulders fell back onto the mattress.

“Fuuuuck,” I groaned and twitched under him as he kept stroking me through my orgasm. My cum spewing out over his fist as his tight grip sent me into a frenzy, and I had to pull his hand from my overstimulated cock. “Shit,” I whispered. 

He chuckled, pulling his soft cock slowly from my wet hole. “I told you I had good control,” he grinned down at me.

I shook my head and caught my breath, “I don’t know,” I grumbled. “Some of those strokes really stretched the definition of a single stroke,” I huffed.

He continued to massage my upper thighs and smiled.

“Plus, you took that extra stroke,” I squinted at him, feeling relaxed and fucked out.

He shrugged, “Maybe you win then. We could do a double or nothing later if you want.”

I chuckled, “Nice try.”

He got up a few minutes later and returned with a warm washcloth to clean me up. He cuddled me for a little bit, and I dozed off.

I woke up to the sound of the apartment door opening and closing; the bolt lock echoed through the apartment. It took me a second to realize where I was and whose muscular arms were wrapped around me. Somewhat sober now, I felt guilty for letting this guy bareback me. I slipped out of his bed without waking him and quietly slipped on my clothes. 

I listened at the bedroom door, not hearing anything, I thought I could sneak out, but his roommate was making himself a sandwich in the kitchen. 

“Oh, umm, hi,” I said, slipping my feet into my sneakers.

“What’s up?” he looked me up and down, giving me that knowing look.

I tried to pull the door, then turned both bolt locks, neither of them allowing the door to open. The roommate closed the distance between us, reeking of weed as he reached over me and only turned the top lock, then the knob, and yanked the door open. “It sticks,” he said.

“Thanks,” I flashed him a smile and basically ran out.

I was home in half the time it took me to get there. Showered and in bed before the sun started rising, my brain was swimming in thoughts about what I did tonight. Before I dozed off, I opened Grindr again and looked at his profile. I realized one of his tags was “edging,” and it hit me that’s why he was glistening and his chest was puffed up when I got there. He cheated, he was already on the edge of blowing his load before he even got the tip in me. I shook my head and went to sleep.