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[MM] The Humiliation of Jess
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Traditional-Lair is a male/male couple, or multiple men
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Names have been changed to protect the naughty and the guilty. So I am a bisexual dom, I've lived all over the world but currently I'm based in TX. I thought it might be interesting to confess some of my more interesting sins.

It all started like it normally does, a chat request with Hi, always so original. His name was Jess and he wanted a Daddy. Jess was a FTM, 5ft2, 24 years old and eager to please. Yummy. Over the course of a few months, the eager corruption of Jess was fun, he liked to be humiliated, he liked to be denied and he liked to be reminded of his place. All these things I was happy to provide

Jess and I had been playing for a few months at this point, I knew he lived in NY and I was traveling there for work. I asked for a recommendation of a local place to eat while I was there. I didn't expect to meet because truthfully, most of the time, I never meet in person, subs who reach out to me on Reddit. It makes sense Reddit is mostly make believe and there's a world of difference in having a Dom on the internet and one in front of you.

Jess was different, Jess wanted to meet, he wanted to take me to his favorite local bar / diner. With plans set, instructions were laid out, Jess could only edge, no ruined orgasms, not cumming until he saw his Daddy in real life. This was 2 weeks away, to say Jess was needy, would be an understatement, the desperation was ... palpable. Maybe I was being cruel but so is life isn't it?

I arrive at the bar, it's cute, it's trendy in the we're too cool to be obviously trendy way. Everyone in it was so young, it made me feel old. Now here is one of those issues what pops up with playing online, I could recognize Jess from his boy pussy, asshole or tits from 20 feet, but I had never seen his face.

I message him, I tell him to stand up and wave both his hands above his head.

He replies "Really?" probably with the sudden realization that tonight was going to be an experience for him.

My response "Do you really want to get punished before we meet?".

"Sorry Sir", I get a second later.

I stand there, waiting for the show to start, then I see a cute twink (he says he's 5ft2, I think maybe he's 5ft at most) stand up from a table and wave both his hands in the air. Even from the entrance of the bar I can see him starting to blush.

I walk over to him, I am 6ft2, I tower over him, he looks so nervous, like a mouse in front of a bear, I just loom for a few seconds. Jess blush starts to go to a bright red, this was going to be fun.

We sit down and chat, he's telling me about his time in NY. I put my hand on his thigh, I can actually see the goosebumps on his arms. The squirming starts, the pleading eyes look at me, "Please, Daddy, can we just go?",

"Oh no sweetie, I feel like we never talk anymore, let's enjoy your cute bar for a while".

He's trying to talk as my hand is running up and down his thighs, enjoying my time in NY.

Suddenly Jess stops talking, "Oh Christ", there's 3 people walking over to us. "Who are they?" I ask.

"My room mates", Jess's face is so red, it could be used a heating element for a steam turbine.

I look at him, "Oh this is going to be fun", poor Jess looks like he's going to turn into a puddle on the floor.

"Hey Jess!, who's your friend?", I introduce myself, "How'd you guys know each other?", Jess is my bitch boy is what I want to say, but "From the Internet", Jess quickly replies.

My hand is still on his thigh, they notice, the shiver from Jess, I honestly think he may of cum. I smile and ask them about themselves.

The next 20 mins might be the longest of Jess's life. For me, I enjoyed chatting to his room mates. At this point I decide I have enough of the teasing. I settle their tab, thank them for the evening and said I need to get back to my hotel.

I stand up, look at Jess, and say "Come" and tap my leg. We walk out of there with my hand on his lower back. I can feel the heat radiating off him.

The Uber back to the hotel, is uneventful for me. Jess is so turned on that this point, he is trying to air hump without me or the driver noticing.

He fails miserably, I slap his leg and tell him to stop being a needy slut, he groans.

In the elevator up to the room, my hand is down Jess's trousers, I gently probe his ass, my fingers come out of his pants soaking wet. I make him clean my fingers, more groans.

Finally we get into my room, my hand wraps around his throat as I push him to the wall. I whisper in his ear "Are you going to be a good boy for me?" as I kick the door closed. I can see the goose bumps spread as I breathe in his ear.

"Yes Daddy, Please, I'll do anything"

I say "Inspection" .

Jess rips off his clothes and spreads his legs. I honestly wonder if he has wet himself. I roughly probe his cock, boy pussy and ass. His cock is taught and his boy pussy feels like a lake, he starts to groan, I slap his cock and tell him not to be such a desperate slut, he collapses to the ground, groaning. I laugh.

"Look at what a slutty boy you are, get back up whore"

Jess is panting on the floor, "Please Daddy, I need to cum".

"Get back up, now slut"

"Yes Daddy", Jess drags himself back up, wobbling, physically shaking from need. He looks like a strawberry and cream candy, bright red from his head to below his tits, alabaster white legs.

"You're been a needy boy, I thought you want to be a good boy for daddy"

"Yes I want to be a good boy"

"Daddy needs a shower, you will wash me and make sure I am clean"

"Yes Daddy"

I climb into the shower, I tell Jess to get into the shower on his knees. I turn on the shower, Jess yelps from the cold, I tell him stay still, and tell me when the water is hot enough for me. Jess just nods defeated.

He looks pathetic, on his knees, bracing himself against the cold water, goose bumps all over him. So small, so needy. Finally he says the temperature is ready. I climb in, my cock throbbing, Jess's eyes glued to it. Jess starts to wash me, he is so tiny compared to me.

He focuses on my throbbing cock, I squat his hand away, and tell him so stop being such a slut. I make him scrub every part of me, washing the dirt of the city from my body. He is silent as he does it, almost in a trance.

Finally I tell him he's allowed to wash my cock, but only with his mouth. He nods, slowly, reverently he opens his mouth and swallows my cock. I feel his tongue push my foreskin back and him greedily licking my precum.

He's being soft and gentle, loving. I grab the back of his head and thrust my cock down his throat. I hear the gag, I don't care, I see his hands move to his cock and boy pussy. I say "Don't you fucking dare", and proceed to fuck his throat like the hole that he is. His hands are on my buttocks, holding on.

"Do you want Daddy's cum? Have you earned it?", I feel his tiny hands squeeze my buttocks harder.

I tense, "Good Boy", I growl as my cock pumps my seed down his throat.

Jess greedily swallows my seed, like it's a fine wine. I feel his tongue probing my cock, clean all the cum he can find off my cock.

I laugh and call him a greedy slut.

I step out the shower, and tell him to towel me off. I stand there as he is gently dries my body, he's still wet and cold, but I come first. He is belongs to me, my needs come first, always. Finally I allow him to clean himself. He is quiet, he is obviously deep into the subspace at this point. I smile knowingly.

"You've been a slutty boy haven't you?", "Yes Daddy"

"Slutty Boys get punished don't they?", "Yes Daddy"

I sit on the bed.

"Get over my knee Slutty Boy", "Yes Daddy"

"I am going to punish you for being such a Slutty Boy, 10 strikes make sure you thank me after each strike", "Yes Daddy"

The first strike is on the left buttock, gently to start with. "Thank you Daddy"

The second strike is on the right buttock, gently again. "Thank you Daddy"

The third and fourth strikes are harder, his ass starts to go red, each strike solicits a grunt from him through gritted teeth. "Thank You Daddy" x 2

Now the strikes are across both of his buttocks, my hand looks massive compared to his small frame. As each strike lands, harder than before, Jess groans, I can feel the wetness leaking from him. "Thank you Daddy"

I stop and rub his bright red ass, dipping my fingers into his boy pussy, the begging starts "Please Daddy, Please, I need to cum" "ssssh, be a good boy for Daddy" "Yes Daddy I will be good"

The blows and rubbing continue, each time his ass gets redder and his boy pussy opens further, juices running down his legs. He is shaking, one of his legs is twitching. Still no relief.

I look at his ruined boy pussy, so desperate. I tell him to stand up. Even with me sitting down and him standing up, I am almost at eye height he is so small. I notice his tears, he is crying from frustration. "Please Daddy, Please", he is pleading, whining, almost incoherent.

I feel sorry for him, only fleetingly, I sigh.. "OK, You may cum", He groans so deep, I wonder if he has actually cum already.

I tell him I am going to be generous, I am going to put my cock in ass. He can cum with my cock in his ass. But only after I've cum again. He eagerly assumes the position, ass up and arched, legs spread. It's actually hard to find a good angle because he is so small. I push my cock into his boy pussy, coating it as much as I can. His pussy clamps at my cock desperately, he has started to shake again.

"Don't cum" I growl. Finally I think my cock is lubed, I place my head at this ass. I gently push, and tell him to push back. It's slipping and hard, but finally my cock invades his bowels. I grunt, Jess groans, it sounds like his soul is escaping from his mouth. He starts to twitch again. Then I tell him to milk my cock. Jess starts to thrust ass back against my cock, he is like a savage, desperately trying to milk my seed.

Finally, I feel the tell tale sensation from my balls, the stirring of the vinegar strokes. I call him a good boy. I ask him if he wants me to cum in your ass. He begs for my seed. I grab both of ass and shove my cock deep in his ass, pumping my seed into him.

Now I tell him "You may cum", I feel both his hands reach for his cock, he is furiously rubbing his nub, repeating "Thank you Daddy" like it's a religious mantra. It doesn't take long, the force of it ejects my cock from his ass. Wave and Wave of convolutions, tensing and tensing, juices are shooting from his pussy.

Then it stops, he blacks out. I laugh, and wait, after about a minute Jess starts so stir. He looks like a cat the way he thrives on the bed. Rubbing himself over the wet puddle he's left on the bed.

"Thank you Daddy", his eyes are droopy. I will him he's been a good boy. Then I make him sleep on the wet spot. His ass nestled next to my cock as my little spoon.

That's the story of when I met Jess in NY.

Jess, there I told everyone what a wanton slut you are. Be a good boy for Daddy.

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8 months ago