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Transform Me (bodman54xKinkySissy)

Kim, on the other hand, slept wonderfully. She loved knowing that she was training herself a cock sleeve. It may take time, but she figured if she trained him properly, he’d be begging for her cock at any chance he could get it eventually. The thought made her cock tent hard, mixed with her morning wood.

She was stirred awake by the knocking at the door. She sat up, exposing her breasts but concealing the rest under the blanket. “Come in, show me how pretty we are this morning” she called out, eager to see him all dolled up. She didn’t much mind if he butchered the makeup job- she planned to make a mess of his face anyhow. “If you’ve done well maybe I’ll let you taste me” she cooed, a hint that he’d maybe get to lick some pussy this morning.
 
He takes a deep breath and opens the door, walking in and stopping in the doorway. He looks up at her and she can see that his face is a mess.

The eyeliner is not straight, the mascara is smudged and clumped, the foundation is blotchy and the lipstick is all over the place.
 
Kim covered her mouth to avoid laughing directly at him once she saw his mess of a face. “Oh dear. You’ll be spending a lot more time practicing, I can already tell you that. But I’ll help you, don’t worry.”

She smiled as she pointed to the foot of the bed. “Lucky for you, it’s dark under there. Why don’t you crawl in and get some breakfast for yourself? I want to feel that tongue and those lips” she purred, her cock throbbing at it’s full ten inches.
 
He figured pussy would be better, though less filling than one of those shakes. So he crawls under the covers, hampered a bit by the dress and crawls between her legs. It's dark so he can't see anything, but he knows where he is going.

He sticks his tongue out, knowing he's getting close. What he's not expecting is to get a mouthful of warm cock. He lurches back, getting tangled in the covers.
 
Kim could see him getting closer, the anticipation building. She then felt his warm breath, her hands sliding under the covers, ready for what she was sure would be his reaction. Then she felt the contact with her cock and his body pushing back.

She quickly grabbed the sides of his head and pulled him closer, wrapping her strong legs around him to keep him close. She pulled the covers fully away, letting him see her cock in all its glory now. “Yes baby, Mistress Kim has a nice breakfast ready for you” she purred, grinding her hips, smearing his lipstick on her cock head. “Come on now, open wide. I’m so horny you won’t even have to do much this time.”
 
He tries to pull away, his eyes going wide as he sees the absolute monster swaying in front of him. She must have anticipated his response because she grabs him lightning fast, securing him with her powerful legs and holding his head with her hands.

His mouth opens to try to shout but she uses it as an opening to pull him forward, spearing her cock into his mouth. It's so thick that he can barely stretch him mouth wide enough to accommodate it. He starts to gag as she moves his head, fucking his mouth with her cock.
 
Kim moaned as she felt the warmth of his mouth. “That’s it baby. Watch the teeth or lose them” she warned as she pushed a few inches in, knowing she was filling his mouth. God he looked sexy on her cock though, she almost nut just from the view.

“That’s a good girl. Suck it now. Come on, just like the basement. That’s it, mmm you’re gonna make me cum baby. And you’re gonna swallow... it... all” she said as she pumped her cock in and out, careful not to make him gag but still hitting the back of his throat.

She couldn’t help herself, being so horny, her desires took over. She kept her firm grip and ground her dick in his mouth. In no time her cock was swelling and spasming. “Here it comes Lexi. Your first of many!” She said as her cock erupted, shooting thick, heavy streams of her cum. She painted his throat and filled his mouth to the brim, then pulled out and sprayed more across his whorishly made up face. Finally she collapsed back in the bed and giggled at the sight. “Mmm, good god that was hot. Swallow what’s in your mouth, but leave my cum on your face while you go drink your shake and make me breakfast.”
 
He is struggling to resist, trying his best to escape. But she has him locked down tight. He can hear her moans as grunts as she is driving her cock to the back of his throat. He is able to keep his teeth out of the way, knowing there'd be hell to pay if he scrapes her.

He can hear her breath shifting and knows that she is getting close. Her cock swells in his mouth as she cries out, filling his mouth and throat with cum. The amount she lets loose is overwhelming and he gags as she pulls him off, still spraying out of her firehose.

He can feel her coating his face, his eyes closed against the torrent. He swallows as commanded, doing his best not to gag. "Uh. Uh. What would you like," he asks quietly.
 
Kim giggled tiredly now as he tried to process what had happened... and surely what will happen again and again. “Mmm... bacon and some fresh fruit, please. All you have to do is microwave the bacon. Even you can’t fuck that up” she chuckled.

She eventually rolled out of bed and slipped into the shower to clean up. She expertly got ready, dressing in some tight latex red shorts that showed the outline of her cock. There was no sense hiding now. Then she wore a matching red bra and strappy stilettos before putting on her usual make up and straightening out her hair before starting to make her way downstairs.
 
He numbly leaves the room, cum dripping off his face and onto his outfit. He felt so utterly humiliated he thought he was going to die. He doesn't know how he made it to the kitchen without falling but he finds himself mechanically slicing up fruit. He puts the bacon in the microwave, doing something he had done before.

He starts the bacon and grabs the milkshake out of the fridge. Why was he still doing this? Maybe because he would owe a million dollars if he left and he was pretty sure his clothes were gone. He had no escape route.

The microwave beeps and he takes out the bacon, setting it on a plate as his finishes the milkshake.
 
Kim eventually made her way down, seeing Lexi’s cute bum under the skirt. But when he turned, Kim let out a laugh at the sight of her cum still covering his face, a mess of semen and makeup. It was almost adorable and actually quite arousing.

She walked up, now happy she could wear the outfits that showed off her cock as she entered the kitchen. She walked straight to him and freely cupped his ass cheeks, licking along his jawbone and then offering a kiss only to push the cum she’d gathered into his mouth. Another slap to his ass and she sat down, happy to see that he’d finished another shake. At this rate his chest would likely begin to become sore, and when he woke tomorrow he may just have some perky little A cups for her to play with. If she kept him at this pace he could be a C or a D within a week or so. Then she’d just need to decide when to stop. Or maybe she’d let his fans decide.

“Run along now and clean up my room. New sheets on the bed as well. Then meet me in your room so we can go over makeup basics. I can’t have you looking like a clown down on set.”
 
He turns when he hears her coming down the stairs. She is wearing a tight latex skirt which shows off the baseball bat she has between her legs. She walks up to him, her stride confident and in control. She was the mistress of the house and she knew it.

When she reaches him she reaches around, grabbing and fondling his ass cheeks as she bends down, her long tongue dragging across his jaw. She grabs his head, forcing her tongue and her cum into his mouth, forcing him to swallow even more of the thick fluid. He burns with embarrassment, humiliated that this woman was manhandling him so easily.

She tells him to go clean her room and he has no choice but to obey. He troops upstairs, his ankles still buckling in the heels. He enters her room and starts to pick up the clothes on the floor, depositing them in the dirty hamper. he then pokes around, eventually finding the linen closet. He strips the bed, noticing the large stain from her cum in the middle, the sheets joining the clothes. He remakes the bed, finding it difficult to do in the frilly maids dress.

He finishes, looking around and hoping it is acceptable. He turns and leaves her room, walking down the hall and entering his, looking around for her.
 
Kim made her way to Lexi’s room and reorganized the makeup. Once he entered, she took him by the hand and sat him down. “Now sweetie, you have to be gentle with these items, not heavy handed like some silly boy. It’s all about the fine details” she explained. She took a wet wipe and cleaned off his face from the cum and makeup remnants.

What followed was a long, tedious lesson on makeup application. She took out the foundation brush and showed him how to even out blemishes and apply it evenly. Then the blush to accentuate his cheek bones. The eye shadow was of course the hardest, just giving him enough instruction not to look like a clown and give a nice smoke to his lids. Then mascara and eyeliner before reaching his lips. “Now these gorgeous cocksuckers” she teased as she took out a hot pink color, showing him how to apply it. Lastly she took a lip gloss and applied a shine to his lips. “This gloss will have a small skin reaction, so you’ll feel some swelling in your lips. At least until we can get you some injections to plump them up more permanently.”

She spun him around once she was done and showed him the new Lexi. The wig needed some work, but she straightened it out. Besides, he’d grow out his own hair in a matter of weeks with the hair products. “There, now isn’t that better? You look like you’re ready to be absolutely pounded” she said with a giggle, her crotch right near his cheek as she looked in the mirror. “If your lips didn’t look so pretty I might have another go at them. But that can wait.”
 
It was just more piling on of the humiliation. He was sat down and she fussed over him, explaining proper techniques and demonstrating it on him, turning him into a pretty girl in what feels like no time flat. She accentuates his cheekbones, thickened and lengthened his eyelashes, and pretty much doing everything she can to make him look like a woman.

When she was done he looks at the mirror, silently horrified at the sight staring back at him. He looked like a girl, all dolled up and ready to be fucked, just like she said.

She hovered over him, her bulge very obvious in his peripheral vision. he gulps as she jokes about pounding him, but he has a sinking feeling that she isn't joking.
 
Kim let him soak in the sight of himself for a bit before helping him back to his feet. “Right then, time for a bit of training, come along to the basement.” She’d let the setup crew in before she started the lesson on makeup so that they could get the basement ready.

Downstairs in the basement, a treadmill was setup. Just a normal treadmill, but there were some additions. There were some chains with clips hanging from the bar of the treadmill where people usually put their hands. Also a small table setup with a paddle and a flogger.

Kim walked up to the treadmill once they were both down. “Now, a good girl needs to be comfortable in heels. So, let’s get these on you” she said as she showed a different pair. They weren’t awful, nothing like she could have chosen, but they were 4” stilettos, so they would be a challenge. “These clips will have two on your clitty and one on each nipple. So, if you slow down... pain. It’s the best motivator. Now get the heels on and hop up here, put two clips on your clitty foreskin and then two on your nipples, then we’ll start you nice and slow.”
 
He doesn't resist as she pull him to his feet. He follows her downstairs, letting her support him as they negotiated the stairways. They reach that dreaded basement and she unlocks the door, stepping inside and showing him what he was about to endure.

And apparently that was torture. Not only was she going to make him walk on a treadmill in stilts, she was going to make him hurt himself to do it. He hesitates as she thrusts the stilettos to him, taking them but not putting them on.

Looking at her gives him no escape though. He was sure she could force the shoes on his feet if he tried to fight and it would just make everything worse. So he sighs and slips out of his current shoes, wobbling into the higher heels and ever so slowly getting up onto the treadmill. He pauses, just trying to stand upright before a shakey hand reaches out and grabs two of the chains, peeling down the front of the outfit and attaching the two clips to his nipples with a wince. He then takes a deep breath and attaches the remaining clamps to his cock, almost crying out as the teeth dig in. "Please don't do this Mistress Kim," he begs.
 
Kim was barely listening to him as he stepped onto the treadmill and put the clips on. She heard him, of course, pleading with her not to do this. She rolled her eyes as she looked at him. “You know you can leave anytime, sweetie. But if you do, then you forfeit your prize and have to pay back all the money invested in you, which currently is just a shade under $200,000. In a few weeks that will jump up to $500,000 with the hormones and other modifications. So if you’re going to leave, now is the time.”

She reached over and pressed the start button on the treadmill. It would start very slowly, making it easy to keep up. “But if you stay, you’re my bitch, my little sissy bitch. I’ll mold you into my perfect cock sleeve. You’ll crave my dick, and you’ll be well compensated for it. You don’t have anything else to worry about, just keeping me and your fans happy. Your choice.”
 
The treadmill starts to move, slowly as she explains his circumstances. The problem was that he didn't have $200,000 to pay back. Before this he was working paycheck to paycheck at a dead end job. That is why this seemed like such a good opportunity. But now, with every passing detail he was digging himself deeper and deeper.

He's brought back to reality by a searing pain on his left nipple. He had stumbled slightly, pulling that chain taut. He quickly rights himself, with a whimper, holding his arms out to the side and looking down at his feet to balance himself.

He doesn't say anything, knowing that he's damned if he leaves and damned if he doesn't. But if he stays then at least he doesn't have to worry about money anymore. That's something. Right?
 
Kim could see that his lack of a response was basically as good as accepting his new fate. She smiled as he obviously had no idea how far she was allowed to take him. “Good girl” she mused as she sat down and watched for a while.

After a few minutes, when it seemed he was somewhat figuring out the rhythm, she came back and upped the speed just a bit. But then she didn’t sit down. She slid a hand under his skirt and found the plug, pulling it back enough to let it slide out then shoving it back inside him, fucking him with it while he walked. “How’s that, Lexi? Don’t you wish it was a real cock? Tell your fans how much of a sissy you are, how you’re voluntarily training to be my fucking cock slut” she purred as she rhythmically fucked his ass.
 
He is still struggling to walk, his arms out wide as he takes baby steps in the heels. He doesn't even notice her coming over until she has bumped up the speed, causing him to stumble and pull on all the clamps at once.

He let's out a cry, on that gets extended as she begins to fuck his ass with the plug, taunting him as she orders him to verbally humiliate himself in front of who knows how many people.

"Uh. Fuck. I'm such a sissy for you Mistress Kim. I'm here willingly to become your cock sucking sissy slut."
 
Kim giggled as she listened to him quickly talking through the obvious pain. She continued working the plug in and out of him for a few more minutes before pulling it out entirely.

She looked at his new, freshly hairless hole. It looked very inviting now. “I can’t wait until this ass gets nice and plump for me. Maybe I can wait to fuck you until you have that jiggle I like” she said as she went to the table and picked up the next size of plug. She lubed it up and brought it back, teasing his entrance. “I think you’re ready for an upgrade baby. Now don’t slow down” she said as she began to work the thicker plug into him, watching his hole stretch. She knew it would burn and be uncomfortable, but she had to keep progressing him so he could take her cock soon. The audience wouldn’t wait for forever for that moment.
 
He doesn't stop moving, trying not to fall over and rip the clamps off his sensitive areas. He can feel her fucking his ass, pulling the plug almost all the way out before shoving it back in. And suddenly it was gone.

He looks around as she talks about fucking his ass, watching it jiggle as she slams him. He sees her picking up the plug and at the same moment his ankle turns, causing him to stumble and pull on the clamps. He cries out in pain, his foreskin being painfully pulled before he rights himself.

He gets back upright, steadying himself but not even having a second to brace himself as she starts to push the large plug in, stretching him even further as he cries out before the plug settles into his sore ass. He continues to walk, tears starting to form from the pain and humiliation.
 
Kim could see how hard her little Lexi was working, and his ass looked so cute with the plug in. “Alright sweetie, you’ve done well” she said as she reached around and unclipped the clamps from his sore foreskin. She applied a bit of healing lotion to her palm and began to rub it into his cock. At the same time she continued working the thicker plug, twisting it and pushing on it, not wanting to stimulate his cock without also fucking his ass.

“Come on, you know it feels good. Get your clitty hard for Mistress” she purred as she began to slowly stroke his cock. The hormones should have been heightening his sex drive, which she wanted, now she just had to build the connection of getting him turned on by his holes being stimulated.
 
He let's out a little cry as she releases the clamps from his cock. That cry turns into a little moan as she starts to rub lotion on his cock, taking it in her hand and stroking him. He continues to walk, lost in the motions as she both strokes his cock and fucks his ass.

His cock surges to life, growing in her hand and precum beginning to form on the tip, sticking to her as she continues to stroke. He begins to moan, the pleasure coursing through his body causing him to shudder. He closes his eyes, stumbling a bit and tugging on his nipples.
 
Kim was pleased as she felt his cock hardening. “There you go, getting hard while having your pussy played with. In no time that’s all you’ll need to cum, Lexi” she cooed as she rubbed in his precum. She knew she could easily make him cum right there, but she quickly pulled her hand away, not wanting him to get accustomed to just getting to cum whenever he pleased.

“You’ll have to earn future orgasms, darling” she said as she slapped his ass and went to wipe her hands off. She let him continue walking for another ten minutes or so, enough to where he’d likely have some sore calves before she came over and let the machine wind down before helping him to get down.

“Now if you’d really like to cum, I’ll allow it, but only if you rub your clitty while licking and sucking my cock” she said as a proposition. “And if you cum without permission, you’ll be punished. What do you say?”
 
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