I'm a 20 year-old native Midwesterner who hid his gayness until graduating high school. There were a few guys I serviced on the down-low fairly regularly for a few years but for the most part my sexual awakening didn't happen until I got to college. I've never had a shortage of people wanting to fuck meÑand as someone who lost his virginity in elementary school to a blond frosh from the high school who needed to "practice" for her boyfriendÑI've always just fell into sex and never really sought it out. Even when I made a Grindr profile, things were no different.
I'm a bottom and I love to serve. I like being on my knees in front of a hot stud who's horny and just looking to use me so he doesn't have to jerk off. I have fucked women but with men I found I liked the submissive role. It wasn't until just recently that I found out how much fun it can be to be a dominant master of a willing slave.
I commented on a Reddit pic a kid had posted saying he was still a virgin and wanted to lose it. He was super hot and I offered to show him an excellent evening, jokingly, assuming he was too far away to actually meet up. Apparently someone else saw my offer in the days following and asked if I'd take his virginity. He was 29 and struggled with anxiety and depression so I thought I'd be doing a public service. He'd posted in several female forums but found no takers. The pic he sent me wasn't terrible so I said fine, drive up and I'll use my Marriott points to get us a room.
I guess I didn't know what to expect. His pic was uglyÑin real life though, he was much worse. Quite easily the ugliest man I'd ever seen. He had a boil on his forehead that sprouted hair like a fern atop his otherwise bare cranium and his hairline didn't pick up again until the base of his skull. I was starting to realize why he'd never been laid. Fat, bald, and unhygienic. He was also unemployed and not much for conversation.
Before he left he texted me to ask if I was dressing up because the only clothes he has are sweatshirts and jeans. I joked something about being naked when it mattered anyway and he arrived two hours later. I asked if he wanted a drink and he said sure so I called us an uber and we went down to my favorite gay bar.
I order my usual drink, which is top-shelf bourbon, and he offers to pay for both of ours because I got the uber. Ok. As he puts the change back in his wallet he says that $26 in change was the last of his last $40. I just took a drink and tried to smile. We sat and talked a bit but every time I'd ask him things like "what do you like to do?" or "what keeps you busy?" I'd get "not much" as a response. He told me the story of how he lost his last job and it was probably the only time he strung more than five words together.
He worked at CVS as a supervisor and in a "manic episode" stole about $10,000 from the safe. They caught him, of course, and now he was a convicted felon. I had told the bartender as soon as we sat down that it was our first date and after this story I gulped down my drink and slammed the empty glass against the bar, signaling for the hot piece of ass to make his way over here. He brings me another and I hand him my credit card but he refuses, seeing the heap next to me and the look of desperation on my face, a thirst for the fog of booze. He gave me three free double bourbons that night. What an angel. There were so many hotties in the bar that night that I should've asked to sit on my face but I had to suffice with slipping that bartender my number and dealing with this disgrace.
I was pretty sloshed and this guy turns to me and says, "I'm getting pretty tired" (it was 10:30 pm). Ok. Let's go back to the hotel. Whatever. I'm drunk as fuck. I request the uber and we ride back in silence because this mongrel heathen can't converse like an adult. We get upstairs and he opens the wine I told him to bring, because I paid for the hotel. He brings a fucking screw-top `sweet white' out of his bag and pours me a glass and hands it to me. I move over and pat the bed for him to get in. He sets his glass down on the nightstand and says excuse me. Goes to the bathroom and doesn't come out for 15 minutes. When he finally rears his ugly head he is carrying two empty toilet paper rolls and asks me if there is an extra one. Yeah, there were two full ones in the bathroomÉ what could he possibly have done with two rolls of toilet paper?
I was pretty drunk but I look at him now and think he's maybe not so bad. Maybe if I get him out of those unflattering clothes he'll be better looking. Boy was I wrong. I help him get undressed and then I do and we get in bed. He's shaking and can't seem to move his arms. I rub him a bit and try to relax him. I guess he's not completely vile, I think to myself, so I go lower and touch his dick. I stroke him a bit, picking up his limp night crawler from the freshly shaven sack it's retreated into and try to get him hard. Nothing happens. I get the lube and start rubbing him, squeezing his balls and running them between my fingers, rubbing his taint and letting my extended index finger trace his urethra deep into his scrotum, a move that usually leads to a throbbing hard on for most of my dates.
But this guy just can't get hard. Ok. Whatever. We've all been there sometime. I shouldn't judge him for that I think so I go down and think I'm going to lick his balls to see if that gets him hard. I move closer and I'm confronted with the waft of his scent. It's hard to describe. He was showered and not particularly dirty but he also just smelled of grease and grime and there was no way I was getting anywhere near his body now. So I say, "let's go in the shower. That'd be pretty hot, don't you think?"
We get in and I say I have to pee and out of nowhere I ask if he'd let me piss on him. I'm not really into watersports at all but I guess I wanted to degrade him a bit. He says ok and gets on his knees. With my back to the running water, I proceed to empty my bladder on this disgusting man's face and I watch the piss run down his cheeks and matted chest hair. I'm enjoying it pretty well when he decides to open his mouth and take my dick inside. I stopped peeing for a second but it stung so drunk me just let it go again and I filled his mouth with piss and saw him drink it down. That was nice. I kept my dick in his mouth for a bit but I wasn't getting hard looking at his ugly face so I said "let's go back to bed, I want you to say hi to my asshole."
I get on the bed in my sexy pose and raise my ass to him as I sit exposed on all fours. He puts his hand on my back and rubs his fingers down my crack. I ask him if he likes it and he says yeah. I look back and he's still not hard so I say ok, "why don't you try rimming my ass? Lick my hole. Circle your tongue around it and then stick it in and write the alphabet as deep as you can." He does.
I love getting my asshole eaten. It's an incredible feeling and I'll basically do anything I am asked to after a man gets my hole dripping with his saliva. But this time, I was drunk and the person behind me was no man but a beast. I had to fart. I tried to hold it in but when I clenched my hole I pushed his tongue out. So I reached behind me and put my hand on his head, pulling him in closer to me, and I released.
I heard him gag as I let the gas escape me. I felt him try to pull away but I kept my hold on his greasy scalp and let another one rip. He almost passed out, I think, but the tongue-lashing picked up again, stronger than ever. By this time, I was as hard as I'd been in a while. I told him to get on the bed.
I'd never topped a man before and we had agreed that he'd be the top tonight but he wasn't getting hard and I was having too much fun degrading him so I decided I'd fuck him then go back to the bar to find that bartender. He lay down and I threw the blanket over him to cover everything but his ass as he knelt for me on all fours, ready to be penetrated. And with that, I grabbed the lube and put a giant glop on my head. I thought about rubbing it into his hole as I like guys to do to me before they fuck me but I couldn't bring myself to touch him so I said fuck it.
I put my hands on the blanket covering his hips and I lined up my cock to his virgin opening. I could hear his breathing stop as he felt the bluntness against his opening and there was resistance when I tried to push in. I wasn't having it though. I'd just made this mongrel drink my piss and eat one of my farts and now he was going to take a load of my cum whether he wanted it or not. So I pushed in hard. When my head finally broke through his ring I heard him yelp and try to pull away but I grabbed his hair through the blanket and pulled him back against me. I pulled his head up so that his back arched as I pulled out and sunk back in again. The noises he was making were winces of pain but I loved it. I pounded him hard and deep. Rougher than I'd ever been. This was his first time and I wanted him to remember itÑhopefully by having to explain to his mom, with whom he still lived, why his boxers had bloodstained skid-marks four days later.
I pushed his head into the mattress, drunkenly attempting to suffocate him as I pushed him deeper with every smack of my pelvis against his bulbous ass. I fucked him hard and deep for about eight minutes until I felt that familiar tingling at the base of my dick. I pulled out once more and plunged in as deep as I could and I finally burst inside him, filling him with my load. I collapsed on top of the blanket covering his beastly form but even the booze couldn't hide that distinct smell. I quickly got up and sauntered over to the nightstand for my phone. He was still under the blanket and I could hear light crying. I snapped a picture of his hole spread agape and dripping with a pinkish slurry of cum, shit, and blood. I'd made him bleed and there was something so satisfying in that accomplishment.
I pulled the blanket off him and lay down next to him and he turns to me with red eyes and says, "I'm sorry I couldn't get hard. I know how much you wanted me to fuck you." and proceeds to bawl.
Oh my fucking god this piece of filth. I get up and start getting dressed. I say "so I have the room all night but I think I'm going to head home for the night. You're welcome to stay if you don't want to drive back tonight."
"No, I think I'll go. I just need to drive." Speaking between wiping the tears from his face.
"You probably shouldn't drive if you're distraught," I say with whatever concern I can muster for a man I just pissed into, farted into, and came into.
"No, I just hope I don't get pulled over because I'm not allowed to leave the state because I'm a convicted felon."
I stare at him with wide eyes as he's putting his clothes back on and stuffing his shit into his backpack. I say, "ok then, I guess I'm going to go home" and with that, I pick up my bag and walk out the door. It was only about 11 so I lit a cigarette and got in my car.
It was fun I guess. A nice story and I did get my ass eaten and got to cum. The whole ordeal lasted about 90 minutes. I guess I made him rim me longer than I thought I did, haha. There's something about getting your hole licked by someone you don't have to look at that makes time stand still, maybe even more because I could fantasize that the man behind me or under that blanket wasn't the hairy heathen I was fucking but rather some hot Indian twink. I really enjoyed topping him, not so much the actual fucking part, but the fact that I got to abuse him, make him feel like shit to the point of crying, and make him bleed for my pleasure.
That was my first blind date and about a month ago. Just after that I downloaded Grindr but wasn't finding anyone who was worthwhile. I finally said ok, I'll make a second profile that is explicit and anonymous, hoping to find some hotties to fuck. I never spoke to that pound puppy again but I did get some messages from college guys for a quick blowjob or a fuck behind the bookcases in the library during midterms. That is, until I got a message from Chubby 24. This kid was messed up.
He tells me he's into all sorts of stuff and likes to be kinky. I'm intrigued so I ask how he likes to play. He's into punishment. I think he phrased it as, "I know I deserve it sometimes." The picture he sent me wasn't a face but from what I could see he wasn't far behind the other mongrel for ugliest man alive. His cock was not that great, uncircumcised, small, veiny and crooked. He was fatter than me, and itching for someone to punish him. He told me he found a master online who told him to buy a dildo and he did and it arrived earlier this week. He sent me a pic of the giant thing, as thick and longer than the 20oz coke bottle he showed me for scale. It looked terrifying but I wanted to use it on him as soon as I saw it. He said his last master was "evil" and he needed one closer to home. So I obliged. I started by suggesting simple things like nipple clamps and cum deprivation but he liked most when I talked about dripping hot candle wax on him as punishment for not pleasing me well enough. Every new act came with the reply "yes sir" and "as you wish."
I could get used to that, I thought. I told him that I was going to tie my belt around his neck into a choke collar so I could walk him around like the dog he is and when he was being naughty I'd pull it tight around his throat. He said yes sir.
I told him how I wanted to tie the belt to the head of his bed and get on all fours at the foot so that he could eat my hole but I'd be just out of reach. I wanted him to choke himself in order to please me. He said "Yes sir," "I will put my tongue in deep." Ok, now I'm thinking this kid is pretty crazy. I'd never done anything like that to someone but he was chomping at the bit to get me to come over and punish him. I don't even know this kid's name but he wants me to strangle him while he eats my hole.
I take some time off from Grindr to go out with a friend and he messages me asking if there's anything my slave can do for me. I tell him I want him to go into his mother's room and get a pair of her panties and a bra and to put them on and send me a picture. "Ok sir" and fifteen minutes later I have a picture of this pile of filth overfilling his mother's B cups. I commend him for sending me the picture. But I tell him he needs to be punished for going through mommy's drawers. That's not how little boys are supposed to act. His only reply: "yes sir" "how"
So I tell him how I want to brand him before I fuck him so that he knows he's mine and that everyone who fucks him after will know he's my slave. "Yes sir"
I also tell him I want him to be wearing those panties and bra when I come over because he needs to be punished hard for such a transgression. I told him I was going to fuck him with that dildo as his punishment and he replies "but sir it's so big."
"I know. We'll take it slow. I don't want to hurt my slave too much. But once I can get a cucumber up your hole or four fingers, I'm sure we can get the head in."
"Yes sir. I know I deserve it."
Later that night I message him and say, "don't jerk off. If you want to cum you have to ask permission first, from now on."
"Yes sir." I didn't know this kid's name and had only messaged him for 18 hours but he was already willing to let me deprive him of the only fun in his pathetic life: his jerk sessions.
The next day I tell him to give me his phone number and he does. I text him further instructions. It was a Saturday so I told him today, for your punishment, you're not allowed to sit today. "I want you to get a double edge razor blade. Go out and buy one at Walgreens if you don't have one, and put it between your ass cheeks so you can't sit down." "When you want to sit I want you to text me about how much your legs hurt and how you want to sit but will obey"
"Yes sir."
Now it's Sunday so I message him with final instructions.
I ask him for his address and tell him I'll be there soon. I have to go shopping for some toys though. I stop at the grocery store and buy a thick carrot; a zucchini, a cuke, and a butternut squash to fuck him with and stretch his hole for that giant rubber cock his last master made him buy.
When I arrive at his house, I ring the bell and he asks who it is. I realize I don't know this kid's name. Don't know a single thing about his life or have even seen his face, yet I'm here with a duffel bag of rope and toys ready to punish him. He opens the door and, true to instruction, is wearing nothing but his mother's bra and panties.
"Hello master," he mumbles.
"Speak up, slave. If you're going to talk to me do it forcefully. Lord knows I'm going to punish you forcefully." He says yes sir and we walk inside. Takes me to his room and I set down the heavy bag with a thud and watch his eyes fixate on it.
"Lay down on your stomach, little boy. You need to be punished for playing in mommy's drawers."
"Yes sir, I know I deserve it"
I grab the panties and rip them from him, making him yelp as the fabric crushed his balls before my thumb nail pushing into the material caused it to give way. I unhook the bra and he takes it off with no fuss. With his fat ass on display I start the verbal degradation. I smack his ass hard and tell him how fat he is, how ugly he is and I spread his legs and smack his taint, my fingers hitting his balls with each smack. He's enjoying every minute of it so I take off my belt.
By this time his ass is pretty red but the first whack of my thick leather belt against his cheek makes him writhe with pleasure. "You like that, slave, you like it when master punishes you?"
"Yes master, I know I deserve it," he moans.
I whack him again and say he isn't trying hard enough. He has to learn not to be bad. This shouldn't be fun for him. "Yes master."
I reach into my bag and pull out the bottle of isopropyl rubbing alcohol I had with me and wet my hand with it and smack his beet red ass. He screams as the cool liquid touches his skin and stings with the fury of his debauchery. I give him one last smack across his left cheek and put my damp hand against it and he whimpers a haggard breath.
"Alright slave, it's time for you to please me," as I wrap the belt around his neck and pull it tight, lifting him off the mattress.
"Yes sir."
I turn him around and get the rope out of my bag and use it to attach the belt to his headboard. I ask him to pull on it and he strains against the makeshift choke collar as the belt tightens around his neck. Perfect.
I get on all fours and show him my ass, just a few inches from where he could comfortably reach. I look back and see him straining as he pushed his tongue out as far as he can but only lightly grazes me. I certainly didn't shower before coming here. I wanted him to taste me natural, to lick the day-old funk from my dirty hole. I decided to back up into him a bit and boy did he enjoy that little reward. I put my hand on his head behind me and pulled away a bit so the belt would constrict and I held it there for a second while he licked me furiously. I wasn't hearing him breathe after 45 seconds so I backed up and he gasped for air, but I held him close to my hole. I wanted to fart in this kid's mouth too so I pushed out a bit as I backed into his face. I felt I had a fart coming so I grabbed his head and pulled him away from the headboard as I strangled him into my asshole and pushed a small turd from my ass into his hungry mouth. I didn't let up until I was certain he had chewed and swallowed it all. I pushed him back a little so he could breathe and he gasped for air.
I turned around and looked at him and he says, "thank you, master." God this kid is fucked up. I ask him if he's ready for his reward: I was going to fuck him. He responded with his parroted phrase.
So I got up and went to my bag and pulled out my keys and told him to follow me. We walked into his kitchen and I told him to stand here and watch. I took my house key off my key ring and set it on the empty frying pan sitting on the stove. I turned the heat on high and told him to go in my bag and get the coat hanger I brought with.
He looks at me kind of scared and I take the coat hanger and bend it into a branding iron for him. After about 10 minutes on high heat, the pan is smoking and the key is as hot as it needs to be. I pick it up with tongs and put it on the end of the wire hanger.
"Alright, lean over the table. I'm going to brand your ass with my house key so you know I'm always allowed in and so every man who wants to fuck you knows you're mine and that he's just visiting."
"Yes master"
And with that, I spread his legs and pressed the hot key into his left cheek, right next to his hole. The skin there is very sensitive and he screamed as I pressed the hot key against him. Tried to pull away but I pushed harder. After about ten seconds I pulled it away and sure enough I saw the distinctive outline and the mirror of "Schlage" burned into his flesh.
You ready slave? "Yes master" he replies with tears in his eyes. I'm rock hard by now so I just line up and plow into him dry. He's had some of his own toys up there so I know he's not that tight but damn did his ass feel nice. Maybe it was knowing it was mine. I fucked him right into his mother's kitchen table and breed his ass right there. When I pulled out I saw how much cum was dripping from his hole, only inches from the bright red outline of my house key on his cheek.
"Thank you for the present, master."
Oh my god this kid is deranged.
I grab his leash and pull him up. He winces as his ass cheeks touch together and I see him shuffle slowly as he tries to prevent his ass from chafing against the brand but I'm not having it. I pull the belt tight around his neck and guide him quickly into the bedroom and throw him down to the bed.
"You've got cum in your ass, slave. You're all lubed up to get fucked by this giant cock, your punishment for making master wait at the door."
"Yes sir."
"But first, I'm going to stretch you with these vegetables and after, I want you to eat them."
Yes master.
I picked up the carrot. Not huge at the tip but it tapered quickly to about 2.5 inches in diameter. I pushed it into him and pressed it deep, stretching his hole against the cone of the carrot. I spun it around and heard him moan as it graced his prostate. He was feeling pleasure from my punishment so I pushed deeper. By now, the carrot was almost fully inside him and I was holding on only by the leafy tops. I pull it out and the tip is shit covered. I grab his leash and pick up his head and say "here, it's nice and seasoned for you" and I hand him the carrot. He looks at it and grimaces but I pull the leash tighter and he grabs it in his hand and takes a bite of the shitty end.
"Good slave. For your reward, a nice cucumber." And I grab the thick phallic vegetable from my bag and he looks back with a grimace as he sees me eying it up. I press the end at his hole and push into him. It's thick. Huge, really. At least three inches in diameter in the center and I had it an inch deep inside him by the time he really started to whimper. I spun it around slowly in my hand and he moaned so I pushed in deeper. His hole stretched further than any man's should as I watched him writhe into the bed as I pressed it deeper and deeper into him. When it was almost fully inserted, I took it out and spread his ass. His hole was agape from the fucking and the bright red brand inspired me. So I took the butternut squash I had brought with me and broke off the hard brown tip and threw it to the side. I noticed he had finished the carrot so I handed him the warm cucumber that had spent about 10 minutes in his ass and he hungrily took a bite.
Next, I took the squash and squirted some lube on it. My cum was no longer enough lubrication for something as big as a fall squash. I spread him and pressed it against his hole and he stretched even further to accommodate the slippery vegetable. Once I got the tip in, I had to hold it there while he composed himself. His teeth were clenched and his eyes shut as hard as he could to prevent tears. I ran my fingers through his hair and whispered in his ear that he was a good slave and master is sorry that he has to punish him but it is for his own good; he has to learn to behave like a good boy. He opens his eyes and says that dead sexy phrase "yes sir." And I pull the leash tight and slowly press the giant squash up his ass. It was bout 8 inches long before it ended in the testicle-like bulb at the end. I liked that this one had a flared end so I didn't have to worry about losing it inside him so I decided to use it as a butt plug. Once it was in him I grabbed the roll of duct tape and I put a long strip across the squash and onto each cheek so that is was stuck inside him. I say he had eaten half of his shitty cucumber so I picked up the leash and pulled him into the bathroom.
He could barely walk. Between the ass brand and the giant squash in his hole, crawling was near impossible without crying but I loved seeing the tears well up in his eyes so I pulled him tighter and guided him into the tub.
I said to him "master has to pee and you're going to drink it."
"Yes sir"
I grabbed his chin and opened his mouth as I pushed my semi-hard dick between his lips. I let lose a torrent of piss, with one hand behind his head and the other on his leash. He let some leak out at first so I tightened the leash, which made it harder for him to swallow but was good punishment for this disgusting pile of filth kneeling before me.
He finishes drinking my piss but I keep my hold on the back of his head as I slowly start to harden in his mouth. I'm fully hard by this point so I drop the hand behind his head and just guide him down my cock with the belt. I make him deep throat me and I pull his leash tight and I feel it squeeze my cockhead. It was one of the most incredible feelings of my life thus far. I pull out so I don't cum and he spits up a mouthful of piss and vomit into the tub.
"Bad slave. Lick that up." He obliges and I yank him from the floor of the tub when I've tired of watching him do that. I take him to the bed and I throw him to the mattress and he lands ass first so the squash inside him smashes into his insides and his bruised hole stretches even more. "That's for puking on my dick."
I rip the tape off and with it comes the shitty squash. Some of his ass hair was still stuck to the tape but I ripped it off and handed him the squash and said "remember mommy said always eat your vegetables."
"Yes sir" and he took a bite. By this time, his hole was bleeding and agape. I loved it. I picked up the giant rubber cock and showed it to him. I told him I lied when I said it was just going to be the tip. He'd been a bad slave and needed a full punishment. "Yes sir," he said with a mouth full of shit-stained squash.
I put some more lube on the cock and then more in his hole. I put three fingers in his gaped asshole and worked in the fourth. I have big hands. I tried to also get my thumb in but I couldn't get the knuckle in so I could properly first him. I figured he was good and ready to be fucked so I lined up the black dildo and pushed the head in.
He screamed as I pressed the giant head through his ring that was finally stretched to the limit and I just yanked his leash to stop him from waking the neighbors. Unable to breathe, he was also unable to scream and I pressed it into him deeper. This thing was 16 inches long. No way I'd get the whole thing up his poop chute but I was determined to get most of it. I let him down a bit once I was inside about half way and I just held it there until I decided to spin it just to fuck with him. Twisting this giant dick in his hole made him scream and moan into his pillow so I grabbed the leash and picked him up and turned him around and pressed his mouth to my cock. I fucked his throat while I had one hand on his leash and the other driving the giant cock up his ass. When I was about to cum I pulled off of him and told him to sit up. He did.
As he sat on the bed I stood up above him and pushed his head down as I jerked above him. I watched as the rest of the dildo slid into his ass as I pushed him down and I pulled the leash to keep him from keeling over. I was seconds from cumming and I was about to mark my beast again.
"Here it comes slave" and I unleashed four thick ropes of cum across his face. He tried to lick it off but I stopped him. "NO." "Let it dry. I want you to smell me whenever you breathe. And no showering until you ask me."
Yes sir.
"Alright, you've been a good slave. You may cum." He grabs his cock and starts jerking furiously.
"Thank you master, for all you've done for me tonight." And I yank the leash tighter.
"I said you could cum; I didn't say you could talk," so he nods and jerks hard and fast. I told him his cock was pathetic and pulled the belt tighter to stop him from breathing. I see him turning red but I hold it a bit longer. As he's about to cum I see his legs go rigid and he pulls back against the belt so I let go right as he covers himself in cum. One of the biggest loads I've ever seen. I guess that's what happens when master doesn't let you cum for four days.
"Eat it." He brings his hand to his panting mouth as he's trying to catch his breath and licks the sticky white goo from his fingers and goes back for more. He licks it all up like a good little slave.
I take the belt from his neck and walk over to my bag and put my clothes back on. He gets up and pulls the dildo from his ass and I tell him to bed over and show me the gape. It was incredible. Best I've ever seen. His bright red asshole was stretched and ripped near the top and he was dripping blood, cum, and shit down his leg. His cheeks were scarlet from the belting and the alcohol burn and his brand was as vivid as ever.
"Alright, slave, I think it's time for master to go home." He pleads with me not to leave but I packed my things and left him in his parent's house. He was mine and I loved it. I didn't know this kid's name but I had marked him as my slave.
I left and drove back home. We'll see what he says tomorrow.