Charlotte s Punishment Letter
- 1 year ago
- 157
- 0
Find That Guy, Round 3, The Harlot Letter free porn video
Find That Guy: Round 3, The Harlot Letter
Synopsis: In this transgender gameshow, Freddy is made over into a woman,
and he and his girlfriend Sue compete against male contestants in
sexually based challenges, until the only remaining male guess which of
the two is a real woman.
Freddy walked up to stand beside Sue, behind the small podiums provided
for them. It looked like she'd been given at least a little time to clean
up, but she still looked more than a little worn out. They stood there,
side by side and completely nude (So to speak, in Freddy's case) awaiting
the results of round two.
The nude couple had been decimated. They'd lost every point they could
have earned, leaving them with the same seven points they had at the end
of round one.
Miguel had earned 27 points this round. Darren had gained another 30. And
Rick, having faced off against an exhausted and defeated Sue, had
garnered a staggering 39 points. Miguel, who came in third place in the
first round too, was disqualified. The host wished him good luck and said
farewell as he left the stage.
Freddy was actually a little sad to see him go. Draining as it was, the
last round with him had kind of been something special. When he realized
exactly what he was thinking it left him a little shocked. He tried to
pretend to himself that he had never been thinking any such thing. At the
current rate, Freddy was going to end up making denial and selective
memory into art forms.
"Alright, Are you ready for round 3?" the host asked the audience and a
cheer went up in reply. "This round will feature a first for our show..-"
The host paused for dramatic effect. "Audience Participation!!" At that,
the crowd went nuts, cheering and stamping their feet so the whole studio
seemed to shake. The host jumped on quickly into a summation of round
three, which would favor the girls, point wise, like the last round
favored the men.
Freddy and Sue were led off stage. Apparently they would actually be
wearing CLOTHES this time around. Two stage girls helped them into their
costumes. It seemed this game was going to have a Puritan theme, as
Freddy and Sue were dressed like pilgrim women. Sort of.
They were stood in front of mirrors and a team of perky girls commenced
dressing them. Dull grey wool stockings were rolled up their feet. Very
drab, but incredibly form fitting, stopping at mid-thigh. Over those were
pulled billowing long dark skirts covered in pleats. Very conservative,
until you realized they didn't have on any underwear. The skirts just
slipped on, with a couple snaps to hold them in place, but the blouses
were another matter entirely. Colored to match the skirts, a dark drab
bluish grey, they were almost the opposite otherwise. Where the skirts
left everything to the imagination, the blouses left nothing. Long
sleeved, skin tight latex with pure white collars and cuffs, they each
had a large oval cut out of the front, leaving Sue and Freddy's breasts
to hang freely. The flesh exposed like that was more appealing to Freddy
then the complete nudity had been. Looking in the mirror, he could
disregard the fact that it was him, and just appreciate the sight of an
incredibly beautiful woman. His breasts were huge and firm. But they
still moved and bounced freely, the way breasts were meant to. It was an
almost hypnotic sight.
Their outfits were rounded off with dazzlingly white bonnets that let
their hair cascaded down their backs, and a pair of clunky and rather
uncomfortable sandals, adorned with polished brass buckles on the top.
So... Not the most historically accurate costumes, precisely. Then again,
that was probably part of the point.
They were led back on stage, to a cheesy village set. Centered in the set
was a set of wooden stocks. Freddy and Sue walked over to the stocks,
bent over, and put their necks and wrists into the half circle
indentations in the wood. The tops were lowered and locked, securing
their hands and heads in place on one side, while their bodies were bent
over on the other side.
The Guys took their places behind the girls, lifting up the voluminous
skirts and got ready for the game to begin. Here was where the audience
participation came in. In front of the girls a long line of 'Volunteers'
from the audience formed.
The guys would start with 20 points, and lose a point for each minute it
took to make the girls cum. While the girls, on the other hand, would
start with no points, and gain 2 points for each audience member they
brought to orgasm before cumming themselves, with a 3 point bonus if they
could swallow a given load. Though that was mostly up to the man they
were servicing. And as a little twist, Darren and Rick would be limited
to anal penetration to bring the girls off. To affect that, they'd been
given a liberal dash of lubricant before they were dressed.
***
Freddy was feminized, dressed as a promiscuous pilgrim girl, bent over
and bound, with the larges cock he'd ever seen about to take his anal
cherry. It wasn't shaping up to be his best day. The Host said "On your
mark, get set, Go!" and Freddy felt Darren's massive rod impale his ass.
He let out a very high pitched scream, the girly quality of which had
very little to do with how his voice had been changed, and a lot to do
with what felt like about four feet of hard cock sliding up his ass.
Darren reached out and grabbed onto Freddy's hanging tits and used them
as leverage to... my god... to push in MORE of his massive cock. Freddy
couldn't see behind him, but he couldn't imagine there actually being
more to this thing. There were tears running down his cheeks. Thank god
for lube. Without it he was sure he would be dead already.
Darren bottomed out, and Freddy let out an agonized moan. It felt like
his dick was ripping him in half. With his eyes squeezed shut in pain
Freddy didn't see the first guy approaching. The first thing he was aware
of was a salty shaft entering his moaning mouth. He was still too
overwhelmed to manage any kind of technique, luckily the guy eager enough
to make it unnecessary. He just started frantically fucking about six
inches of dick in and out of Freddy's mouth. But Freddy was lucid enough
this time to remember his objective. So when the guy in his mouth started
to tense up Freddy tightened his lips around the shaft and managed to
catch the spray of cum, swallowing it all. The taste was less than
pleasant, but it was still pretty far down Freddy's list of concerns
right now.
Freddy was getting pounded pretty hard from behind at the moment, but the
pain was beginning to fade a little, fading into discomfort. In the
meantime he'd already finished off one guy, the salty jism sliding down
his throat, and the next guy was stepping up. He and Sue were going to
kick ass this round. The next guy stepped up to the plate for his chance
to swing his bat around. About five foot four, maybe two hundred and
fifty pounds of what looked like whale blubber, and three inches of hard
(mostly) dick bobbing in front of him. Freddy smirked at how easy this
would be. A particularly strong thrust from Darren turned it into a grunt
a moment later. Freddy opened his mouth and licked his lips while looking
into the guys eyes, and welcomed Prick Jr. into his waiting mouth.
Tightening his lips around it he gave it a good strong suck like a hard
candy. This elicited a goofy sounding "Wooh" from tubs, so Freddy worked
over the shaft with his tongue while trying to keep the suction up. It
took about fifteen seconds and the heavyset guy was making mewling sounds
and Freddy felt his little cock start to twitch. Just as the first taste
of cum hit Freddy's tongue, the cock popped out of his mouth as the guy
literally fell on his ass. The guy let out a girly squeak, and his one
little shot landed inside Freddy's bonnet, sliding down his forehead and
over one eye.
As tubs embarrassedly and bare assed scrambled away guy number three
stepped up. A twig of a man with a twig of a dick leading the way. Five
ten with about four or five inches pointing at Freddy, this one left
nothing up to chance. Grabbing Freddy by the ears he slid in and stared
humping frantically like he was afraid someone would stop him and tell
him it was all a joke. Judging by the thick as hell glasses and the acne
scars, to his mind that was probably a real danger. Freddy tried to work
on it a little, but the tip kept tickling his tonsils, which few people
ever get to find out, is surprisingly distracting.
With little to do up front, Freddy started noticing the action in back a
bit more. It wasn't exactly easy to ignore, but concentrating on other
things had helped to take his mind off the pounding his formerly virgin
ass was taking. Darren was certainly giving it to him good, or bad
depending on your perspective, but it was going more smoothly now. His
ass had opened up a little, learning how to be a good hostess. A little
stretching and it was still uncomfortable, but the distress was mostly
psychological now. And Freddy had been through too much already to be
phased that badly by a little butt sex with another man, Giant prick
notwithstanding.
Another minute went by and it was finally starting to get to him. He was
so incredibly full, a sensation he'd never experienced before, and then
he was devastatingly empty. Full, and then empty. Full, and then empty.
It was starting to make him light headed. Guy three came in his mouth and
moved on. Still not a pleasant taste, but it was beginning to be old hat
for him. Guy four, average personified stepped up and slid in, moving
back and forth gentle but leaving the rest up to Freddy. He hadn't
exactly been fresh when he'd started, and after being in this position
for so long Freddy's legs and back were working up a real ache. This
reminded him of the sad state Sue had been in and he looked over to check
up on her.
Sue had apparently given up already. Her body hung limp between the
stocks and Rick's rigid dick. It looked uncomfortable as hell, but Freddy
wasn't sure she was even aware enough to notice. He'd got a quick peek
inside her bonnet and her face was completely enveloped in semen,
dripping copiously to the floor. Apparently a helpless, maybe
unconscious, fuckdoll of a woman was a big turn on. The way they were
treating the woman he loved was really starting to piss Freddy off.
The twitch of the cock in his mouth brought his attention back to the
matter at hand. Before he knew what was happening Captain Average had
pulled out, gave his prick a couple jerks, and sprayed his cum all over
Freddy's face. 'Now that's a dick move if ever there was one,' Freddy
thought.
Darren put his hands on Freddy's round ass and started squeezing the
smooth flesh. He kneaded the tender cheeks and messaged them tenderly.
Gentle caressing of just the finger tips across the beautifully rounded
flesh was then punctuated with a resounding smack to each cheek. The
shock of the impact caused Freddy to clamp down hard on Darren's invading
member. This elicited a moan from Freddy as he felt the shaft pulling
against the pressure he'd created. After seeing the response, Darren
began repeating the process, Squeezing and massaging, followed by a
gentle caress and then a sharp smack, sometimes to one cheek, sometimes
to both.
The cock pistoning in and out of his ass, and the clever ministrations
Darren was employing were starting to feel too good. Freddy was feeling
little quivers in his pussy with each thrust, and his ass would clench
each time Darren withdrew, almost like Freddy didn't want to let him go.
Men lined up and made their deposit, either in his mouth or on his face,
but he was no longer focusing on his task. All his attention was now
being focused on the blissful boffing his butt was receiving. Cum slid
down his throat and off his chin in equal measure while he felt the slap
slap slap of Darren's balls against his pussy lips.
The Buzzer sounding broke Freddy from his daze. He looked over at Sue.
She'd come. Now she couldn't earn points anymore, but she'd still be
stuck in that stockade blowing guys until Rick came. Then Freddy saw
Rick's hand, at an angle where the camera couldn't see it. It was in
Sue's pussy. He'd been fingering her to get her off sooner. The Bastard
was cheating. He opened his mouth to protest, and about eight inches of
cock were shoved down his throat. He gagged at the sudden intrusion and
looked up. It was the host!
"Hi, Winnifred. Just thought I'd pay you a quick visit," he said, working
his cock a couple inches further down Freddy's throat. "You know, you
really do make a very beautiful girl. You might consider making it a more
permanent thing," he whispered, while gently, almost lovingly brushing a
strand of cum soaked hair out of Freddy's face.
Freddy tried to tell him about rick cheating, but it just came out as
mumbling and gurgling around his dick. Freddy worked the shaft with his
tongue, sealed his lips, and sucked for all he was worth, trying to get
the host off quickly so he could talk. But it was to no avail. The host
was apparently no light weight like most of the audience members. He had
staying power, and Freddy was nearing his limit. Exhausted and over
stimulated, he was powerless to resist as wave of pleasure came crashing
from his ass, to his pussy. Muscles clenching, tingling all over, Freddy
came like a hurricane. When the spasms of ecstasy waned, Freddy was to
out of it to even notice the streams of cum fire up his ass and down his
throat. Everything faded to a black, dreamless sleep
To Be Continued...
Barbie
- 07.04.2021
- 13
- 0
Charlotte s Mum Actions Mrs Denver s Letter
- 4 years ago
- 51
- 0
Skyrim The Harlot Hero
- 3 years ago
- 36
- 0
