Covid 19 - Pete Turned into Charleigh Pt. 03

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Pete's transformation continues, he serves his first man.
7.6k words
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Part 3 of the 5 part series

Updated 06/10/2023
Created 04/22/2020
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His_fag_wife
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"OK off with the wig now and we'll get rid of body hair first and then we can document the necessary changes."

Mistress Red pulled off Charleigh's wig, one of the last vestiges of Charleigh's feminine sissy armor and as Pete looked in the mirror, he wondered if he was doing the right thing. With his bald head, flabby pecs and miniscule caged cock, he certainly didn't feel like a man any more. He thought about his wife Emma, was there even a sliver of hope that she might take him back, should he try? Should he just stop this right now?

Then she removed the ball gag, which had a coating of cum on it still, Mistress Red knelt and unlocked his high heels, slipped them off and then slid the stockings down his hairy legs.

"Just wait until this hair is gone, you'll feel so so sexy, I promise you baby." Red knew Pete was back and very fragile now, if she didn't judge this just right he'd want out, but she knew that she still needed to push him.

"First we'll go for a temporary measure, we can leave talking about making it permanent until later." Although she knew she had to tread carefully she still wanted him to know that this was a process and that there was no going back.

"You've told me so many times that you'd love to shave your legs and armpits like a real gurl, well now you can, how exciting is that?" She picked up the bottle of Nair and told Pete to sit on the stool in front of the mirror. He obeyed automatically, now still thinking about his wife and just what he'd lost, or thrown away.

Red covered both his legs and feet in the cream, massaging it into all the nooks and crannies. She then had him stand and did his entire fat arse, but leaving between the cheeks as he'd already shaved there for her and the Nair would sting too much. "Now stand for me."

Pete stood as the cream began to sting a little. Red had him lift his arms and liberally coated his underarms and then his chest and pecs, making sure his nipples were well covered. Then she moved behind him and repeated the process with his back, shoulders and arms.

"There now how does that feel."

"It's starting to sting Mistress Red."

"Good, that's because it's working it's magic, getting rid of the last bits of manliness, you'll feel so much better once we wash this off and all the hair is gone. In fact I'm thinking it would be best to properly shave your head, after all you can hardly be a sexy girlie with side burns can you baby."

"But it's really stinging Mistress, please can we get it off?"

"OK over to the wet room in the corner and we'll shower it off."

Pete slowly stumbled bow legged across the dungeon to the tiled corner shower area with the drain in the middle of the large shower tray. There were no glass panels around it so that a number of people could have stood in the shower tray area.

Pete stood still, the stinging getting worse with every passing minute, as Red turned on the rainfall shower head and put a wash cloth in Pete's hand.

"Now wipe your body off, I'd start with your nipples as they'll be the most sensitive bits."

Pete did as he was told, washing off the cream and hair with it. In five minutes he was smooth all over.

As Mistress Red handed him a towel she licked her lips without thinking about it, he looked so different with all the hair gone. She had something she really could work with now, she could almost see Charleigh shining through, but not quite yet.

"I don't want you looking in the mirror so let's just put this blindfold on you whilst I get you dressed again."

Pete could not longer see, but his other senses were heightened and he could feel every breath of air on his now hairless body. He felt as though he was as sensitive as a tuning fork. His entire body tingled and he felt somehow lighter, he'd stopped thinking about Emma for the moment.

"OK I've stuck your lovely red plug on the chair over there, I'll guide you to it and then I want you to get it in without touching it. You have to line your boipussy up perfectly and show me you can get it in without any hands, little one, do you think you can do that for me." Smiling at the thought of how hard this would be Red almost giggled as she said this.

"Yes Mistress I'll try my best." Pete had changed back to Charleigh's breathy, slightly lispy girly voice without being told. That was a good sign Red thought.

She guided him over to the chair, got him standing astride it and put his hands on the make up table in front of the chair. "Now bend over for me bitch put your head on the table and pull your cheeks apart for me. As Pete did as he was told she picked up a pot of tiger balm and scooped out a good finger full and smeared it over the tip and top of the plug. This would make things interesting for her little baby gurl.

Pete could smell the unmistakable aroma, he knew what it meant, having been ordered to use it on his cockhead by Mistresses before. But he couldn't be sure where it was, although he thought he knew.

"OK now some lube for my gorgeous girl and then you have to put your hands back flat on the table and start to try and get your pussy filled once more, let's face it, you should be full at all times from now on, OK." With that she dripped a large glob of silicon lube onto Pete's asshole.

"Yes Mistress Red I understand."

Mistress Red used two fingers to rub up and down his ass crack before delving straight into his hole, it embraced the two fingers as though they were nothing.

"Wow, I'm not sure we needed the lube, you are seriously damp down there my girl, you're ready for cock, that's for sure."

Pete wondered if this would be the day that Mistress Red might make him worship a real cock. But he really wasn't sure he was anywhere near ready for that. Not yet, not by a long chalk. "Just rubber cocks Mistress R R R Red?" he stuttered.

"We'll see baby, we'll see, don't worry your pretty little head about that now, just try getting yourself full for me. Show me how good a sissy girl you can be for me." As Pete started to lower his ass towards the head of the plug, his thighs ached, he'd been working them a lot today, what with the heels for such a prolonged period of time. He managed to get the slippery head of the plug butting close to his taint, but as he tried to lower himself it just slipped forward, spreading some tiger balm onto his ball sack. Then he tried again and it slipped backwards smearing the stinging balm through his ass crack.

Red had two phones videoing on the stands next to Pete, the irony was one of the phones was his. She had one set with a view up towards his asshole and the other getting a side on view of the poor sissy desperately trying to get some cock.

While Pete was carrying on with his attempts she moved over to the small drinks fridge in the corner. She took out a milk bottle and picked up 5 shot glasses and moved back to the table.

Pete heard the glasses chinking and realized that a number of items were being put in front of him, then the aroma he knew so well rose up and invaded his nostrils and mixed with the smell of the Tiger balm, it was immediately recognizable as the pungent aroma of cum. But how the fuck could it be, Mistress had fed him every last drop of his recent emission. The thought dawned on him slowly in his heightened and aroused state, shit she must have got some cum from other men. He was immediately repulsed at the thought, there was no way at all that he could eat another mans cum, that was revolting in the extreme, for fucks sake it was downright gay.

"Get it in bitch, you're not concentrating on the job in hand." Red was looking forward to the look on his pretty little face with the next part of her plan.

"Sorry Mistress but I can smell something." He didn't want to say what he thought it was, but wanted to express his trepidation a little.

"That my little girl is both a punishment and also a treat for you, it's a punishment, in that I have 5 shot glasses filled to the brim and if you don't get this plug deep inside you in the next thirty seconds, then I'm going to force you to drink one for me. And if you fail when the minute goes by you'll swig another one down. So don't take over 2 minutes or you'll have to have all 5 of them. But it's also a treat as it will fill you up and satisfy your hunger and of course at the end of this training period you'll grow to love it and crave it. This is simply the start of that process."

As he kept frantically trying to get the butt plug head home and drop onto it, each time it slipped he got more worried.

"But Mistress, you fed me all my cum, this can't be mine." the idea growing in his mind was awful.

"Twenty seconds gone, come on, hurry up. Of course it's not yours silly, but I need you to have a lot of cum, so I've been collecting it for you, from all my clients just in case."

"Thirty seconds, now open wide and carry on."

Pete did as he was told and held his head back and his mouth wide open, his tongue extended like a lap dog, Red was pleased that he was obeying and she simply upended the shot glass of gooey cold cum into his willing mouth, watching it fill up and pool in his mouth, coming up to the top of his teeth.

"Good girl, now swallow." Pete hesitated and Red thought the riding crop might be needed, but then he did as he was told. Cold semen from a fridge, that was some other guys was a whole different challenge than his own warm, fresh cum had been earlier. The concept of drinking another mans cum horrified him, he gagged heavily and very nearly threw up with revulsion.

"Don't do that bitch, if you do, you'll be licking all of the semen vomit off the table, believe me, you don't want that, just take your medicine like a man, well like a dirty little sissy actually, ohh one minute is up, wow time goes fast when you're having fun."

Pete held his mouth clamped shut. He wouldn't do it, so he concentrated on getting the plug in.

"OK slut, just think about this, if you fail to drink when I tell you to, then I'll get a full, cold pint of cum out of the fridge, I'll lock a feeding urinal onto your face and fill it with the pint of slimy cum, then I'll hold your nostrils closed and force feed it to you until your stomach stretches out with it, now open fucking wide for your next shot!"

The thought of a pint was just too much to bear, so he opened once more to accept the full shot glass of cum into his mouth.

"Swallow it all, get ready for the next one, a minute and a half is up. God you're hopeless at this and you with a gaping pussy too, surely you can get it in slut."

Pete was trying but the top of the plug just kept slipping up and down his crack, spreading the tiger balm everywhere. He could smell that and taste the cum, the last shot tasted different to the first one and to his own earlier, it was much more salty. Why on why hadn't he stayed with his wife, what the fuck had he got himself into. He felt as though he'd been in the dungeon for days and it had only been just over two hours. Now she was feeding him other guys cum, what the fuck. This was madness, where would it end? If he had the slightest clue of many of the plans Red had for her new sissy slut he'd be trying to escape right now

Pete swallowed and was told to open wide again for the third shot, he wasn't gagging anymore. Red poured it into his open and apparently willing mouth. "There see baby, that's much better, you almost licked your lips with the last one, really swirl this one around your mouth, I want you to savor it and tell me what it tastes off." The whole situation was getting more wild by the minute and Pete was getting more and more worried, they'd never ever discussed him eating other guys cum, He'd always told her that he hated the taste of his own cum and that he no longer felt submissive as soon as he'd eaten it, on the few occasions he'd been forced to by previous Mistresses. But he'd never have agreed to eating another mans spunk not in a million years, but what choice did he have, the thought of a full pint of cum was horrifying. So he did as he was told and swirled it around his mouth.

"Good girl, now swallow again and describe this cum to me, the texture, taste and which did you like more?"

Pete swallowed again and when he spoke he spoke as Charleigh.

"But Mistress, it's so horrible, it's not mine, I can't do any more, please, please, don't make me, I beg you."

"OK slut your choice, I'll get the full pint and the urinal gag." With that she stood and began walking to the fridge.

"No, no, no, pleaase not that Mistress Red, I can't do that, please nooooo."

"This is your very last fucking chance, tell me how that last shot tasted bitch."

"Yes Mistress, sorry mistress, errr, ummm, it was smoother in texture and more liquid, it tasted a bit metallic." he hoped that would be enough to please her, but in the mood she was in he had no idea if it would.

"Good that's better, now which did you prefer."

"Well I didn't like either ..." She cut across him and shouted, her face close to his, her anger clear on her face.

"Just answer the fucking question you pathetic piggy faggot." Pete was almost crying now, she had nearly broken him. In the past whenever she called him piglet, he'd always felt it was a term of endearment, but with the last outburst it felt like an insult.

"I preferred the second one Mistress, the salty one."

"There, see that's better, I can almost see Charleigh back again, I think once you've relished these last two shots, she'll be fully back with me and ugly pathetic Pete will have gone, let's hope so or we may have to continue the cum training.

Pete knew it was time for Charleigh to appear and to stay. His voice changed back to the breathy, camp and sing song voice from earlier, Pete knew he had to hand over to Charleigh, this was her domain with Mistress Red.

"Ummmmm hellooooo Mistress Red, it;s so good to be back, I'd love to try the last two so I can choose my favorite cum shot for you, ummmm what a lucky little cock slut I am."

Red beamed, "There's my gurl, welcome back Charleigh, now I know you want to look pretty and after you've had your two protein shots, we'll get working on that, here's the first one. Charleigh opened her mouth, licked her lips laciviously and waited for her prize.

"Here it is, looks a little thicker this one, he must have been a mans man."

Charleigh swirled and savored and then held her mouth open until her Mistress gave her permission as she took a close up of Charleighs CUMSLUT collar and the cum in her mouth, with a third phone. "You may swallow bitch."

"Ummmmm ohh that one was thick almost sweet compared to the others, umm that's the winner so far Mistress."

"Good girl, now get that plug in before the last shot, concentrate."

Charleigh pulled her butt cheeks apart and lowered he ass down a little, trying to bear down as though she was trying to take a shit as she had the plug lined up. She got the first inch or so opening her hole up, spreading tiger balm around the rim and then she looked to the side, into the eyes of her superior and pressed down until her butt cheeks were on the cold chair base. She tilted her head back, relishing the fullness and then she leaned back further ensuring that the plug was rammed in as deep as it would go. "Ohhhhhh Goddddd, ohhhhh my, Mistress that sure feels ssoooooooooo bigg" As she said it her asshole and inside of her began to warm up with the Tiger Balm.

"Good Gurl Charleigh, now open wide for me and swallow this last one down for me. Then I want to get you fully made up for the afternoon's fun." Red was loving every minute of this, she had Charleigh fully in her control now.

Charleigh opened her mouth wide and and swallowed as soon as Mistress poured it in as per her demand. Charleigh then went to stand up, but the plug was now suctioned onto the chair and lifted the chair with her. "Good girl, pick up the chair with you and walk over to the dressing table in the corner, this will be where you get made up every morning before you start the day. I'll show you today, but then we'll start you on a range of video tutorials, the last thing I want on you is amateurish makeup.

Charleigh stumbled over the chair pulling the plug out a little and stretching her asshole with each stride, making her moan over and over.

"Your really are a nasty little whore aren't you Charleigh, let's get you looking the part."

Red slid the stockings back up her slut's now hairless legs and then gently slid the high heels on and locked them in place. Then she got Charleigh to stand, "Now I'll get the suction cup to let go and you stand up". Red picked up the D cup sized breast forms and sprayed then each with adhesive and gave them a few minutes to start to get tacky before she carefully arranged them over Charleigh's pecs. She pressed firmly for a few minutes on each one before working with makeup to blend them into Charleigh's skin tone.

"There that's better and I love that the nipples are permanently hard, just as a sluts should be. This Hollister adhesive is meant to be the very best on the market and good for prolonged wear which is what I want. We need you to be wearing these almost twenty four seven, so you get used to the weight of them every day, after all one day you'll need real ones, won't you baby girl."

Charleigh wasn't sure she was ready for that any time soon, but thought it best to agree. "Yes Mistress Red, I will."

Once she'd tested that the breasts weren't moving any time soon, she picked a black leather corset off the rack. She stood behind Charleigh rubbing her breasts against Charleigh's back and then telling her to raise her arms as she held it for Charleigh to connect the clasps in the front which rather than just the usual hooks and eyes. were locking clasps that looked much more substantial. Red then had Charleigh bend forward slightly and began the job of tensioning the corset strings, starting at both the top and bottom to evenly tighten the corset as much as possible. For the final cinch she put her knee into Charleigh's back and pulled with all her might.

"It's hard to breathe Mistress moaned Charleigh."

"Good then it's tight enough for you girl. Now turnaround for me."

"Ohhh my, that does look good, you're starting to look the part. Sit down and we'll work on your makeup and then the wig and then sort your panties out, how's that bombshell plug feeling?"

"I feel so full Mistress Red, it's wonderful and warm thank you."

"Ooooo before you sit down we need these thigh cuffs on to make sure you're comfortable as possible when you're in the box."

Red then went to work, shaping the eyebrows with an eyebrow pencil, then working through her make up skills finishing off with a deep burgundy lipstick with Gloss over the top. It was far from perfect but would do for now, she had some more extreme measures planned once everything else fell into place. After all it was only day One of the likely thirty or so days they would have during lockdown. Good to get off to a strong start though.

As she finished she stood and admired her handiwork. "Now you don't look like a pathetic guy in a dress, you really are starting to look the part of a Sissy slut, but the full transformation will take time."

Red took some more still shots for Charleigh's portfolio and relished how good she was looking. "We are going to need to put you to work to pay for some of these things and your future changes. But after all a good Sissy works for her Mistress and earns the money when she needs to, doesn't she baby."

"Yes Mistress she does."

"And you do want to be the best Sissy you can for me, don't you Charleigh?"

"Yes I do Mistress Red, more than anything else I want to be the best for you, I'll do anything Mistress."

"Indeed you will, indeed you will my little piglet."

"It's time for your first real man, are you OK with that Charleigh, you said you'd do anything to please me."

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