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…

July 2018
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