Covid 19 - Pete Turned into Charleigh Pt. 02

She knew Pete wasn't into pain at all, in the initial conversations and texts he had made that very clear, but once she had managed to get him to think of himself as his feminine alter ego, Charleigh, then pain was much more acceptable, Charleigh could take a lot more pain than Pete.

Charleigh longed so much just to please her Mistress and once Pete sunk into subspace and became Charleigh, then pleasing Mistress was an all encompassing urge, she was simply desperate to have her Mistresses approval.

Red knew that to get Charleigh to the party, would mean giving Pete much more pain than he could bear, making him sob and beg through the gag, until he became Charleigh to protect himself from the pain. She had to beat Pete into subspace, to get him to that promised land for subs, where he could wallow in the increased endorphins and adrenaline. Charleigh wasn't just Pete's coping mechanism, becoming her, freed him to be the true submissive slut he longed to be, and much more importantly to become the submissive sissy slut that Red wanted him to be.

Pete was completely focused on his breathing and the images of sluts drinking cum on his screen, with Britney's encouraging remixed sound track. The pain he felt as Red struck his low hanging balls with her riding crop made him scream into the gag. The pain was an eight on the scale of one to ten for him, never easy for a sub to start at that level of pain, but even harder to go up from there.

He focused on dealing with the pain, just as she struck again, his left butt cheek this time, then the right, then his balls, and back to the left cheek. This depraved merry go round continued for a few minutes. In that time, he'd gone through various stages, screaming, begging for mercy into the gag, sobbing and then simply slumped. In just three minutes, she'd hit him over sixty times, his balls were red and his cheeks turning pink. Red breathed in the pain, she loved his fear and the whimpering it was this suffering which turned her on so much.

Pete then felt his Mistress's hand caressing his butt cheeks, sliding between them to graze his freshly shaven ass, skirting around the plug and occasionally pushing on it, eliciting further moans, she grasped his softening cock and stroked it pulling the foreskin back just as he was told to swallow cum on his Sissy hypno. Red purposely held his cock between forefinger and thumb, knowing that later she'd remind Pete of this and make him feel even more inadequate about his cock size, all part of her long term plan.

She cradled his ball sack in her other hand, gently gripping the long silky, smooth sack and two hefty balls. She'd been impressed with the sheer size of his balls compared to his cock, from the very first time he'd knelt naked in front of her in their first session. Maybe it was that which made his cock look even smaller. She stroked his cock a further ten times, quite deliberately making it hard again.

Just as Pete was basking in the soft feel of her hands, she dropped his ball sack and began another three minutes of intensive whipping. The shock took him deeper, just as a defense mechanism, subspace was the only way his brain knew how to deal with this level of pain, the increased endorphins circulating helping him survive the onslaught. He'd long passed the level where he was taking the pain just to please his Mistress. Now he was trying to get through it, plain and simple, this was always a dreadful and yet thrilling point for a sub, not knowing if they could take it, but just enduring it and hoping that it would end some time soon.

After the sixty counted strokes, Red stopped once more and began to massage the ever hotter cheeks, this time she grasped his cock in her hand and then between her forefinger an thumb, and retracted his foreskin with long deliberate strokes of his cock. As she held the foreskin back, the head of his cock swelled an angry purple, naturally holding the foreskin in the retracted position as Red wanted. As she continued to stroke his cock she pulled the butt plug out and slowly forced it back in again, in time with the strokes of his cock, over and over, knowing that Pete was on the very edge of cumming.

As he built to his orgasm and began to shake, she stopped abruptly, leaving him hanging on the edge of orgasm, desperate for release, with none forthcoming.

Red smiled as his entire body shook a little more, but there was no release for her new toy.

She knew that she was going to enjoy teasing him over and over again, making him so desperate to cum, that he'd agree to literally anything she suggested.

This cycle of whipping, caressing, stroking and edging continued for another 3 rounds, until Pete was crying continuously with the pain. His tears dropping on the floor and being recorded doing so, which Red would be able to edit in slow motion for the first transformation film. Her slut had to reach rock bottom, to be able to appreciate the promised land of sissydom.

Red stopped touching him and walked over to the range of dildo's, butt plugs, and strap on's hanging on the wall. The biggest strap on she'd previously used on Pete was 2 1/2 inches in diameter all the way, so although only the same size as the widest point of Pete's butt plug, it was relentless, they was no relaxation for Pete's asshole, it was stretched and stretched further and further.

The last two times she'd used this strap-on, she hadn't warmed Pete's ass up and he'd cried and whimpered at the aggressive invasions, trying in his desperation to move forward, away from her cock, that was how she wanted it again, it simply turned her on in the extreme.

Although she had much bigger strap-ons now, which she'd bought in the last few weeks, today this would do the job, she strapped it on into her new leather harness which was much stronger than any harness she'd had before and would allow her to fuck Pete with absolutely no inhibitions. She wanted the video to record his face as she pounded him into complete submission.

She started again with the crop, just when he thought she'd finished with punishing him. He'd closed down his mind, thinking he'd taken what he needed to, but then she started again, which made him question if it might ever end. She'd never hurt him this much, in previous sessions when his whimpering had got too intense, she'd backed off, but today if anything she was getting more dominant with each cycle. he was beginning to question everything, should he be there with her, what the fuck had he been thinking, was she mad, would this madness ever end. But he couldn't hold a thought for long enough to answer the questions, that was becoming impossible for him as he sank ever deeper into subspace.

As Mistress Red began to caress him, Pete sighed into the ball gag, the punishment temporarily forgotten, Red pulled the butt plug out ever so slowly, getting it to the widest point and moving back and forth a small amount. Holding Pete's asshole at maximum stretch, then as she pulled it out she replaced it with the head of her strap on and slowly pressed forward until the head was lodged firmly in Pete's ass.

She reached forward and removed his headphones.

"Now Charleigh, are you there, my darling?"

"Yesssssssssss Mistress" was just about distinguishable through the gag as Pete nodded.

"Good, that's my girl, now I'm going to remove the gag and I want to only hear Charleigh not Pete, do you understand?" Pete, or should I say Charleigh nodded her head. With that Mistress Red unbuckled the gag.

"Are you here for me Charleigh."

Pete's voice changed completely into that of Charleigh, still deep, but breathy, a dirty slut of a voice. "Yes Mistress Red, I'm here for you."

"Goooood Girllll, that's so much better to have you here with me, we can have so, so, so much fun. But first I'm going to fuck you properly and with the aim of getting you to your first sissygasm, just through being fucked anally, with only the smallest amount of stimulation for that little hard clit of yours, do you understand slut?"

"Yes Mistress Red, please make me cum, God I want to cummmmm, please I'm so desperate, I'll do anything."

"Good girl, that's good that you'll do anything, because guess what I'm going to want you to do once I make you cum."

"Please Mistress Red, please don't make me eat it, I can't do that." Charleigh said this more with defiance than pleading.

"I won't make you eat it."

Charleigh sighed with releif.

"Well not straight away, first just like in Slut Puppy hypno you watched, it will be in you mouth for you to savor."

"No Mistress Red please not that, I can't do it."

"You have no choice you silly girl, you know that's what good sissy sluts do and you want to be the best sissy slut you can be for me don't you Charleigh. Or we can start the beating again, if you prefer."

"Nooooooooo please not that Mistress. I'll do it, I'll do it." Red heard the resignation in Charleighs voice.

"Well it's your choice, a mouthful of cum, or another 3 minutes of beating, which is it to be slut."

"The cum please Mistress, make me eat my cum."

"Beg for it slut and make it good." Red knew this was crucial for Charleigh and the videos.

'Mistress Red, please, please, please make me cum and fill my mouth with my cum, so I can taste it and swish it around my dirty slut mouth to please you, to show you that I want to please you and worship you and make you smile, please I beg you."

"Good gurl, that's so much better, now let the fucking begin."

Charleigh's hole was well worn by now, lubed up both with lube and natural juices. Red was lined up behind her slut and held the strap on head, still at the entrance of Charleigh's hole so that it just held her open a little.

Red took a moment and smiled, counting in her head to ten, building the tension for Charleigh, before she leaned forward with a massive thrust of her hips, clenching her ass as she drove forward and buried the full 10 inches into Charleigh's asspussy in one long stroke. Charleigh's scream was blood curdling, if you'd heard it in isolation, you'd have though someone was being killed. To be filled so much, so hard and so fast. To be taken so roughly was complete, her head spinning.

Red held Charleigh by her hips, holding the cock fully in her, giving no relief for some moments, savoring her ownership of her sissy. She smiled, now she thought it was time to search for that sissygasm that she'd read about. She angled the tip o the dildo straight at the point of the Charleigh's prostrate. And began fucking slowly, using Charleigh's moans to guide her to the perfect spot.

This might take time she thought but it was important. The bowl she'd set on the ledge below Charleigh's cock would catch her Sissy's spurt.

Red focussed on the spot, listening with delight to the strangled moans of Charleigh as she rode on the edge of orgasm for minutes on end. Red was now only rocking back and forth a small amount, once she had the head of her cock on Charleighs prostrate. She worked Charleigh up into an absolute fervor, until she could feel Charleigh literally vibrating beneath her.

Then reaching around Charleighs stomach she held her hard clit just beneath the head, rocking the tight foreskin back and forth with her forefinger and thumb. Red only stroked a few times, before she knew for sure that Charleigh was on the edge of an orgasm. She lifted her hand away from her sissy's clit and kept rubbing her dildo head on the spot.

Charleigh was deep in subspace, but could feel a tingling starting in her toes, going up through her legs and reaching her punished ass and her clit. Her lower body began to shake, her thigh muscles contracting over and over again, her asshole clenching on the dildo deep within her.

Then it happened. The promised land was reached, she had her very first Sissygasm. No one touching her cock, but she spurted and spurted, over and over again, Red massaging her prostrate all the time to milk every last drop of cum from her slut.

Charleigh moaned in her euphoria, "Goddess, i love you Goddess, fuck make me your sisssy, pleasssseee."

"There's my Charleigh, that's right, you do love me and I will make you my Sissy, the best ever sissy, that's what you'll become Charleigh."

"Yes please Mistress Red, ohhhhhhh yes please."

Red finally rested, with her cock deep in Charleighs ass. She was smiling, the first big hurdle was overcome, now to see if Charleigh would be true to her words of a few minutes ago. Submissives always lost so much of their pliability when they came, and she knew from the stories Pete had recounted to her, that he was one of those subs. But Red was not going to accept that. Of that she was sure.

Charleigh always felt guilt racing in once she'd cum, but not this time. She was still high on poppers and breathing in more with each breath. She'd never felt anything like the orgasm she'd just had, her entire body had vibrated. She'd read about Sissygasms and for a long time had believed that they were a fiction.

But now she knew better, it was amazing. She loved it completely, and wanted more, she never wanted the feelings to stop.

Red pulled the dildo out and Charleigh moaned "nooooooo."

"Ahhh does my little slut feel too empty, don't worry I can sort that." With that Red picked up the butt plug and slammed it back in, zipping the body gusset back over but leaving Charleighs tackle hanging out.

"There, there baby, nice and full again, although I think we need to sort that little clit out for now."

"But first, you must be hungry and need something to eat baby, is my little slut hungry?"

"Umm yes Mistress I feel so hungry, please give me something to eat, pleassseee."

"OK hold on, I'll get your protein piglet."

Red picked up the bowl of cum, impressed by the volume, there must be at least a couple of table spoons worth and she knew that was unusual. She reached over for a baby spoon she'd brought into the dungeon and a chair to sit on in front of Charleigh.

She moved her face close to Charleigh's and stroked the side of her face. "Well done baby girl, you did so well, now you deserve your meal."

Red filled the spoon with cum and lifted it to Charleigh's mouth, and held it an inch or so in front of Charleigh.

"I want you to take this in your mouth, but not to swallow it for me. OK?"

Charleigh nodded, she loathed the taste and the humiliation never made up for that, but she had promised and she moved forward enclosing the spoon with her lips and gingerly sucking the cum from the spoon.

"Now hold your mouth open and I'll spoon the rest in, spoon by spoon. But don't swallow any of it, savor and enjoy it, it would be good if you start to get used to it, for the future."

Red filled the spoon and raised it to Charleigh's mouth pouring it forward as you would for a baby, then spoon after spoon until Charleigh's tongue was covered by a deep pool of cum.

"Ohhhh that looks so, so lovely, keep it there while I get a close up photo of you for your profiles. Smile for me my little dirty cumslut ohh and lift your head so they can see your CUM SLUT collar. " Red took the photo's and then replaced the ball gag."

"Now there, that looks so much better and now even if you want to, you won't be able to swallow properly, the ballgag just won't let you. Instead the cum will drip down your throat, drop by horrible drop so you can truly savor and enjoy the taste for the next half hour or so. Now it's time for me to get that ugly little, soft clit of your's under control. Just look at the present I've got you. Have a look at these beauties."

She picked up a tray from across the room with 6 different chastity cages on them, Charleigh recognised one, a two inch long sleeve of metal bars, which Mistress Red had put Charleigh in for the hen do that she'd attended. It had caused much hilarity for the bride and her hens, as Charleighs clit was just too small and too slim for it, the cage swamped her, she barely filled the back of the cage.

Red held this one up to Charleigh's eyes.

"Now we know this one is way too big, remember how those hens laughed and laughed at you, so I'm going to try the next one down and see if that fits, I'll just move the camera and then you can watch the fitting back later. All the footage would be part of the story of Charleigh's transformation. So Red had to play the part a little for the camera.

She fiddled with the next one, a pink plastic cock cage."Jeepers even this one is way too big for your little clit baby, it swamps you. Let's try the next one, after all it's going to be on 24 7, for some time to come."

Charleigh registered that, 24 7, shit she'd never worn chastity for more than a few hours before and then it was homemade chastity, not the real thing.

She picked up the third one, and showed it to Charleigh, "I can't believe that this will fit it's only an inch long, and an inch wide, so it'll be way too small. But let's check it out and see."

"Ohhh my God, even that is too big, it's too wide, you're flopping around in it, fuck it, let's work up from the smallest, maybe the birdcage one will be too small, it's the smallest one I could find on the internet. Just look at it!" She held it close to his face, he couldn't believe how small it was. She held it on her thumb and the end of that filled the cage. It was barely an inch long, only 3/4 of an inch wide had a large urethral plug which looked huge to Charleigh .

"I know, I can't believe how small it is, but look at this lovely plug, I know it will go in deep but you can piss through it and keep the cage on all the time. Although it's so bloody small I can't believe that it will fit anyone.

Red was hitting the small penis humiliation hard for Charleigh, she knew it really pressed Charleighs buttons, she'd seen how humiliated she had been as the Hens laughed at her, but she also knew that Charleigh had been as horny as hell at that point and so perfectly submissive. She reinforced that Pete wasn't a proper man and never could be, his pathetic cock was just too small, so the only option was Charleigh the sissy. The added advantage for Red was that she got off on this and she truly relished humiliating her slut this way, quite simply it made her damp.

Charlie could only wallow in the constant taste of the cum dripping down her throat. She was gagging occasionally. No matter what she'd said to her Mistress, she absolutely hated the taste of cum, even her own, it just made her want to throw up, but the ball gag put paid to that, apart from the occasional gag, which made her swallow a little more each time. There was nothing that could ever change he view of the taste of cum, that bitter, slightly metallic taste was utterly repellent to her and she could never see herself coping let alone relishing eating cum.

Mistress Red had very different ideas to Charleigh on the topic of cum eating. Mistress had a detailed and delicious plan for Charleigh and it involved forcing her to not only face up to her fear and her loathing of cum, but ultimately to learn to love it an crave it. She would simply have no choice whatsoever, Mistress Red would make sure of that, and what's more, she'd enjoy the entire process spoonful by spoonful.

"Ohh my God I need the biggest ring they have to go around your big balls and sack, amazing how you have these huge balls and such a tiny cock, who'd have thought that was even possible." As she was talking she pulled his balls one by one through the ring, then stuffed his cock head through, tugging it with his foreskin. "Well that's pretty snug and shouldn't move too much, but we might swap it out for a smaller ring later, now for the moment of truth."

Charleigh watched his Mistress lube up the hollow urethral tube with a mixture of interest and horror, it was 2 and 1/2 inches long and he knew it would have to go inside his body with the size of the cage she had shown him. Charleigh closed her eyes,she wasn't sure she could watch this at all.