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”
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.