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There were small round tables, arranged in a semi-circle, each seating people in their finest outfits and jewelry.  Servers were armed with a seemingly endless supply of champagne and wine.  They all faced the stage, wondering what would be presented next. 

This was the Black Gala.  If you knew what it was, you were either in the audience or you were getting sold.

“Sold,” is a misleading word though.  The Black Gala’s wares were willing participants, with contracts stating as such.  

“Ladies and gentleman, we’ve had a pretty good night so far, wouldn’t you say?”  The audience applauded and clinked glasses.  “Our last girl, Irina.  Wow.  Am I right? She was just gorgeous.  Mr. Tallwood, I think you’re going to have a very good year with her.”  There was more applause, and joyous laughter.

“Up next is someone who is...well...let’s just say that we’ve never done anything like this before.”

Backstage, she could hear what the emcee was saying, and she began to sweat again.  How was it possible that this was happening to her?  But she remembered...

Tommy Dodson, the player, the drinker, the party-animal.  Tommy, who managed to somehow drink his way into a private party at the Midnight Wink.  He should’ve been thrown out on his ass, but someone in a suit asked to keep him around - they thought the doofus was entertaining.  They asked if he played poker.  Sure, of course he did.  Damn good at it too.  So they gave him some chips and told him to pull up a chair.

Now, no matter how good you think you are at playing poker, you’re probably not THAT good.  Especially when you’ve been drinking.  Pretty soon, Tommy was out of chips.  “I’ll take some more.”  This was met with understandable skepticism.  “No, it’s cool, I’m good for it.  I’m just getting warmed up anyways.”

Yeah, so they gave him more - and obviously you can tell this was a mistake.  And would you believe this mistake was repeated a few more times?

At the end of the day, Tommy was in the hole.  Let’s not say exactly how much, but we’ll say it was enough.  “Look, fellas, I was obviously a little drunk and I don’t think I knew exactly what I was doing.  No hard feelings, right?”

They had some hard feelings.  Soon, he was getting answers like “Do you know who our boss is?” and “Do you know who runs this game?”  No, he didn’t, but based on those questions, it didn’t sound like he wanted to know.

“You’ve got a week to bring us the money.”

Or else?  Or else what?  Well, a week later, without so much as a phone call from the poker-guys (and just as Tommy is thinking that maybe this was water under the bridge and nobody knew who he was or where he could be found), there was a knock on the door.

“Tommy.  We’re here to collect.  But...we’re guessing that you don’t have our money?”

He got kicked around a little bit.  Slapped around.  Honestly, it could’ve seen worse.  If you’ve watched the movies or seen the TV shows, you were probably expecting something much much worse than that.  But they did drag Tommy to a swank penthouse suite in the city, throwing him on the ground before a big guy in an expensive bathrobe.

“How much does this lowlife owe us?” he asked.  A goon whispered an amount in his ear.  He shrugged and laughed.  “I can tell you right now that this good for nothing moron isn’t any good for it.  Who let him in the game in the first place?  Those are the people I’d like to beat senseless.”

“So what do we do with this guy?”

Bathrobe man looked Tommy over from head to toe.  He stared him in the eyes while he scratched his chin.  He turned away for a moment, staring into space.  Then, he turned back to the goons.  “You know what?  Give him to Sophia.”

“Sophia?”

“Sure.  I bet she can come up with something.”

Flash forward to Tommy finding himself in this posh room in this posh house speaking to a very posh woman while her slightly-less-posh assistant scribbled down notes.

“I’d ask if you knew who I was or what I do,” she said in a voice that dripped with condescension, “but I’m fairly confident I know the answer to that.  So I’m just going to tell you.  Okay?  Okay.  I help girls who have problems.  Money problems.  They come to me, I give them work, and then they’re free to go.  Some stick around...the money is good.  Some go away and I never hear or see from them again.  You’re here because you have money problems.  I’ve been told to help you.  But do you see the problem here?”

Tommy did, as I’m sure that you do too. 

“I’ve thought about it,” she continued, “and this seems like an interesting challenge.  I feel like there’s a market for what I could do with you.  You’re going to be a guinea pig.  How do you feel about that?”

Tommy wasn’t particularly crazy about that.  The alternative was to be beaten into a pile of flesh and bones.

“A one year contract is what I’m proposing.  Whatever you make at auction, you and I will split the difference after your gambling debt and the cost for your...rehabilitation.  It’s not only in your best interest to sign the contract - it’s in your best interest to learn to love your new job.”

He signed it.  The next few days became a confusing whirlwind.  Never before had so many females doted on him at one time.  Except instead of offering the sexual pleasures of his fantasies, he was stripped of his clothes, and shaved and waxed bald.  All of it went.  His leg hair.  His arm hair.  A particularly gruff Swedish woman manhandled his testicles while she shaved his manhood. They even whisked away his luscious blonde hair.  Complaining about it certainly didn’t help, though, and was usually met with a slap to the face or another firm grip on his balls.

“You’re going to learn how to use makeup,” a woman told him.  And everyday for a week straight, he spent hours applying make-up and taking it off, only to re-apply it.

“You’re going to learn how to walk in hi-heels,” another woman told him.  He walked up and down the longest hallway of the house in hi-heels until he felt like his feet were going to fall off.

“You’re getting breast implants.  If you decide you don’t want them when you’re contract is up, talk to Sophie.”  He woke up on a guerny, astonished to tears at the sudden change to the shape of his chest.

“Have you ever taken it in the ass before?” No, he shook his head, his face blushing furiously.  He knew where this conversation was going.  “We should get you used to that.”

They started small, a simple 4 inch black dildo with some lube on it.  He was forced over the side of the bed as two hands pulled open his cheeks while another inserted the object.  It was slow at first.  Just as he began to adapt to the awkward new pleasure being introduced to him as it filled him, it was pulled out again, sending new feelings through his body.  Again, he’d try to adapt, but  just as he began to, it was shoved in again.  The pace changed, and he couldn’t keep up with it.  It was wave after wave of a feeling that his body didn’t know what to do with.  Until finally...

“Catch that in a cup, will you?” the woman with the dildo said to the woman holding his ass.  “This is probably another good lesson.”  He was rolled over, and the contents of the glass were poured into his mouth.  

This was repeated each morning and each night.  Every two days, the size of the dildo was increased.  He was fucked, and then forced to drink his own milk.  At night, he was to practice fellating one of the dildos for an hour.  The size of this dildo, too, expanding over time.

“Is he ready?  The Black Gala is tonight?”

“He’s ready.”

“He can please a man?”

“With a mouth and his ass, yes.”

“And he looks the part?”

“We’ve taken him out in public, yes.  Between his wig, and his chest, nobody knows any better.”

“Excellent.”

And so now, at the Black Gala, she could hear the emcee talking about her on stage.  Without even seeing them, she could sense the crowd - and they were hungry for whatever they were about to see.  Whatever happened tonight, she was going home with someone.  Just a year.  A year of willful servitude.  A year of makeup, fake tits, and swallowing cum...in both her mouth and her ass.

“Ladies and gentlemen...Tammy!”


This story has been re-edited since its original publishing on Tumblr. This version is exclusively for my patrons.

I want to point out, too, that this isn't the type of story I typically write anymore. I decided to include it on Patreon because I did promise to archive all of my previously published pieces. However, my feelings towards "sissies" and "forced feminization" have changed since I originally wrote this piece. While I stand by opportunities to write about silly boys getting humiliated and made to be uncomfortable - using femininity as a "punishment" is, in my opinion, insulting.

I'm sure I'll share more thoughts on this in the future - and I assure you that I'm not shaming anyone or yucking anyone's yum. If you're interested in discussing this subject further, I encourage you to contact me about it.

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