Reluctant Young Men Spanking Clips

Rich uses a wooden spoon on poor Jay's tight, muscular ass to elicit a barrage of pathetic squeals, gasps, and shouts from the frightened young man. Buck naked over Rich's knees, his body trembling, he's hyperventilating, kicking his muscular legs, trying hard not to disgrace himself by crying. "Oh my god" he gasps, then squeals some more in a very undignified, high pitched panting whine.

There is nothing as sexy as a shy, young straight guy about to get a spanking. Jay looks so nervous and scared as Rich takes him OTK and starts to spank. His embarrassed grunts, gasps, pants and whimpers as he bites his lip and thrashes about on Rich's lap, trying desperately to maintain some composure, make him look so vulnerable and immature. Rich turns his sexy, bubble butt bright red, then has him stand, looking bewildered and dazed to face the camera in shame, before being sent to the corner.

Rich always means business when he takes a young man OTK with a bath brush, so Dylan knows he will do his best to make an impression on him. Rich begins a relentless pounding with the brush while scolding the young man while Dylan cries out in a high pitched, pained voice, promising never to try to fool him again and pleading for forgiveness.

With his briefs down around his ankles, his toned, muscular body fully exposed, Dylan is now to endure a harsh beating with a yardstick. He looks and sounds so sad as the beating is about to begin, knowing what's in store, and starts to moan and gasp loudly with every blow. But his moaning turns to a high pitched scream when Rich switches to a cane, and his agonized cries fill the office.

The last time Dylan worked with us he faked crying, thinking he could fool Rich and you. But Rich doesn't like being fooled by young men, and this time Dylan knows that he's really in for it. Rich scolds him for trying to fool his customers as he spanks, but forbids him to shed any fake tears. He intends to make him cry for real. This time it's all natural, all real and very painful, and Dylan is howling and gasping in pain by the time Rich takes the ruler to his muscular butt. But this is only the beginning.

And now the moment we've been waiting for. Rich takes Eco back OTK, and with a mean bath brush begins a relentless spanking that has him kicking his legs, thrashing about on Rich's lap, and eventually crying like a little bitch. Rich scolds him now as he spanks because Eco's mistress advised him it helps to make hem cry.

Now Rich takes a cane to Eco's tender, young ass. He struggles to maintain his composure as Rich whips him, but the cane's stinging bite soon has him crying out in pain. He knows that Rich is in a contest, and won't stop until he makes him cry, like his mistress. The tension and fear only intensify as Rich canes him standing with his hands over his head as he dances, hops and writhes in agony, his only hope is to cry soon to end his agony.

Eco is a 22 year old str8 sub who hates submitting to a man, making this video to please his mistress. Rich does some role playing with him in this video. In Part 1 he takes the young man OTK for a sound spanking, first over his P.J.'s, then on his cute bare butt, before laying him over the bed for a beating with a ruler. He cries out in pain, kicks his legs and struggles as his ass turns bright red but Rich is determined to make him cry, just like his mistress.

Drew looks scared when Rich puts him over a foot stool for a beating with the cane. His body twitches and he gasps in pain with every stroke before he starts to sob, quietly at first, his big cock swinging beneath him as his body spasms with every blow. He's sobbing uncontrollably by the time Rich has him count out the last 25 strokes.

Rich strips Drew naked, removes his belt, and takes him back OTK for a step-daddy style belt spanking that has him crying out in pain. But when Rich switches to a hairbrush, Drew's cries become a pathetic whimpering as he approaches the breaking point, then he starts to sob, quietly at first but eventually becoming louder, until he's broken and crying like a little bitch.

Rich leads young Drew into the room by the ear, takes him over the knee and starts to spank him by hand over his pants until he's grunting and gasping in pain. He lowers his pants and continues over his tight, white briefs, beautifully filled by his tight, muscular, bubble butt. it's clear early on that Rich will eventually break this young man.

Now the ultimate humiliation, an over the knee hairbrush spanking in front of the window, where anyone might see him being punished. The young man soon forgets about this however as he gasps and moans in pain, his breathing is loud and labored as he writhes on Rich's lap and his perfect bubble butt turns an angry shade of red.

Rich lowers the young man's briefs, him to stand exposed, wondering if anyone can see him. But his modesty is soon forgotten, blocked out by the pain Rich inflicts with a rapid hand spanking that has him grunting and gasping in pain, his ass turning bright red as he struggles to maintain his composure. But even that effort is lost when Rich switches to a belt, he kicks his legs, clenches his fists and cries out, no longer concerned about who might see.

Rich takes a muscular, 24 year old straight guy into his office and, in front of the large stroefront windows, with the blinds tilted just enough passing traffic to see if they happen to look the right way, lowers his pants and shorts and delivers an embarrassing and painful spanking with a ruler that has him grunting and gasping in pain.

In Part 3 John is tied to the spanking bench with his ass spread wide and in the air. He's helpless to defend himself as Rich approaches with a cane. His body jerks and he gasps and cries out in pain with every stinging blow. Then Rich switches to a riding crop and John's breathing becomes quick, loud and labored, his cries are a high pitched whimpering as the crop stripes his muscular, vulnerable ass.

With his cock and balls securely locked in the hard, cold steel of the genital stocks and his feet in shackles John is unable to move even slightly without causing himself pain. John struggles to stand completely still as Rich begins a beating with a leather paddle. He cries out in pain but doesn't dare move an inch as Rich punishes his poor ass.

John is back after a three year absence looking more built and sexier than ever

and Rich proves he can still make this straight guy disgrace himself and carry

on like a bitch. In Part 1 Rich takes him OTK and spanks him by hand, with a

belt and a bath brush and once again John can't take the pain as he writhes

and cries in pain as Rich breaks the proud young man.

Theo looks worried as Rich prepares to finish his spanking OTK with a bath brush. The young man tries to take his punishment like a man but soon looses his composure as he breaks down and sobs, crying out loud as his ass turns bright red and bruised.

Bent over a stool with his ass in the air, Theo begins to whimper, whine and cry out in pain, writhing on the stool as Rich whips him with a crop and cane. At times he tries to hide his pain in defiance, not wanting Rich to have the satisfaction of seeing it. But Rich breaks him every time, making him cry out in spite of himself.

Theo is young, cute and very expressive. He's making this video for the money and can't quite believe what he's gotten himself into. Rich takes him OTK for a spanking by hand over his briefs, then lowers them to reveal a very spankable ass and continues with a wooden paddle on his bare butt. Theo moaned and grunted, kicked his legs, and uttered the most pathetic yet sexy "ouch, ouch, ouch" over and over as his ass slowly turned red and bruised.