tagTransgender & CrossdressersAliExpress and Sissy Downfall Pt. 04

AliExpress and Sissy Downfall Pt. 04


As Tim added inch after inch, slowly taking his time, stretching his new slut, driving deep into Emma's tight twitching arse, she moaned with the pain like a wounded animal. He loved the supremely tight fit as he slid forward into her, bit by bit. His sweaty ball sack finally rested on Charlies face, each of his big balls settling into Charlies eyes sockets as she continued to lap her Masters cum still dripping from her wifes freshly fucked, sweaty, cum soaked cunt.

Charlie was deep in sub space, no longer thinking about what she was doing, or that it was her wife who had just been fucked and now she was not only cleaning her of another mans cum, but of her Masters cum, whilst he defiled her arse and took her anal virginity right there in front of Charlies eyes.

She was no longer thinking like a man, she was simply a submissive Sissy slut for use and abuse by her Master and new Mistress. What's more, she was loving every moment of it, revelling in the sheer dirty humiliation of the scene.

So many men could never imagine how this could be anything other than complete abject humiliation, but that was just the point, she wasn't a man any longer and she craved the dirtiest humiliation possible, which her betters could subject her to. The more they could make her an absolute cock and cum craving slut, the better and deeper the humiliation, the greater the satisfaction she would find in being a completely controlled sissy slut.

Emma was now draped over Charlies body biting gently on the cage, she was totally turned on and moaning and groaning with each pleasurably painful thrust.

Then Tim withdrew fully and Charlie breathed in the aroma of his wifes ass juices on Tim's cock as he slowly withdrew inch by turgid inch until his glistening lubed cock was fully out of her once more.

"Now lean your head right back Sissy and take my cock and give it a clean so I can fuck her dirty arse once more."

Charlie was on auto pilot, no longer licking her wife, but instantly obeying and leaning her head back over the end of the bed to allow her Master to have a good straight line down her sissy throat. She opened wide to accept his cock."

He slid it in nice and slowly getting to the back of Charlies throat after a few thrusts resulting in deep gagging from Charlie. The feeling of a Sissy gagging hard on his cock was always a turn on for Tim, but he also knew that once he'd trained that response out of them, he really did have a sissy slut for life, on his hands. It took many hours of discomfort, pain, with repeated blackouts for a sissy like Charlie to be able to deepthroat not just his cock, but some of the many bigger ones he might find for his fag wife to worship in the coming years.

He pressed on beyond the back of her mouth into her throat proper, the angle allowing the deepest of intrusions. His pierced cock head lodging at the back of the throat for a second, until with a further thrust and whilst holding his Sissy's head tightly, he drove the cock head to open the back of his sissy sluts throat forcibly.

His pubes rubbing on her face, his big sweaty ball sack hitting the sissies forehead with each thrust. Without the opportunity to breathe she was both gagging violently and her throat was contracting as peoples throats do when then are swimming underwater for some distance.

The milking, clenching feeling on Master Tims cock was heavenly. This was what a fag wife was made for.

Charlie felt as though she were drowning, but couldn't move or do anything to stop the feelings. Just before she blacked out, Tim released her, pulling his cock from her for a moment and then driving straight back into Charlies wifes still gaping asshole, slamming it in hard to get her to grunt loudly for him. She duly did her duty, grunting along with a squeal of pain. When Tim was fucking Emmas ass, Charlie went back to licking her dirty pussy clean.

That was how it went on for a full brutal 15 minutes, hard slams of the magnificent cock into Emma's beautiful big arse, Tim pulling her big cheeks wide apart, stretching her hole and allowing him to get in as deep as humanly possible. Then after a few hard thrusts he'd change and dip into Charlies throat for cleaning, before getting back into fucking Emma in her sumptuous arse.

Emma was on fire, her nerve endings tingling all over, her nipples harder than they had ever been, her clit so, so sensitive. The pain had subsided and now she was consumed by the feelings inside her ass, a sex act which had always disgusted her, in fact appalled her, was not only giving her a huge amount of pleasure, but was also one of the final nails in the coffin of her sissy husbands masculinity.

Tim was enjoying building to the inevitable crescendo as Emmas asshole clenched and milked him and as Charlie managed to lick his balls every few strokes in between worshipping Emmas sloppy pussy. Tim could see that his sissy fag was in absolute sub space now, he was so horny he'd do almost anything Tim suggested.

Now was the time to show Emma that her husband would always be a sissy fag, with a deep rooted need for Gay domination. To show her once and for all, that her macho husband was irretrievably gone, gone forever and a day.

It was time to make Charlie his personal fag slut wife forever, or for as long as it took him to get bored of her and discard her like a dirty, smelly, soiled pair of panties.

Tim held onto Emmas hips and slammed in one final time, erupting inside his new hot wife, breeding , marking her as his property and cuckolding Charlie with another hole, another orifice for the sissies inevitable clean up duties. He held himself in there wallowing in his orgasm as Emma then reached hers, flooding her sissy husbands mouth with a cocktail of her juices mixed with Tims cum.

Charlie was in sissy heaven, lapping, licking and slurping, loving the utter humiliation and not thinking about any of the long term consequences, or even what the rest of the evening would bring. He was gone.

After a few minutes Tim withdrew and just looked down into Charlies eyes, Charlie knew her new duty and opened wide to receive her Masters softening cock covered in cum and Emmas juices, straight down her slutty throat. She sucked and cleaned the cock focussing on the large PA piercing and cleaning it as best she could. The position with her head low down was making her more and more dizzy.

Tim slowly withdrew his freshly cleaned cock from his sluts mouth, smiling down at her and her dishevelled makeup and face, cum in one eye, lipstick smeared and mascara running everywhere.

He wiped a little cum residue from his cock head and lovingly gave his new fag wife another coat of cum lip gloss. He wanted her senses to be filled with the smell of gay sex, to that end he scooped up a large globule of his cum oozing from Emmas asshole and smothered it over Charlies nostrils causing Charlie to breathe in a little and choke but filling her head with the essence of her Masters cum.

Emma was completely spent and her full weight was slumped heavily on Charlie, her head on one side squashing her husbands caged clit and balls.

Tim walked around to her side and whispered that he wanted her to stand when she could and to stay astride her sissy husbands mouth, with her asshole directly over it and to bear down as though she were going to the toilet to feed her husband as much of Master Tims cum as she could.

Her asshole was sore from its first ever ravaging but she complied with her new Masters instructions, standing somewhat gingerly and then squatted slightly, lowering her freshly fucked arsehole to just above her husbands' mouth.

"Pull your ass cheeks apart so your sissy husband can get in there nice and deep to get her sissy treats." Emma was totally shattered but complied, pulling her big ass cheeks as wide apart as she could as she wriggled lower completely smothering her husbands' made up face. She writhed on his tongue then raised up again as she bore down, trying to push all the cum out of her ass into her husbands' willing, open mouth

Tim had picked up his phone and was videoing as each and every drop and globule of sticky cum was being squeezed out of her red raw asshole, direct onto his sissy sluts tongue.

Charlie did not need to be instructed but raised her sissy head and worshipped her wifes ass hole hungrily, gently lapping at the red rim, trying to salve the soreness and work her tongue in as deep as she could to get every sticky drop of sissy goodness out.

As Charlie worshipped, Emma moaned once more revelling in the dirty pleasure of being rimmed. She could only think that she wanted this to be done regularly by her sissy from now on. As regularly as possible. Ummmmm what an amazing fucking feeling she thought, this could be a daily ritual.

When she'd squeezed out as much cum as she could Tim told her to stand and to lie on the bed, whilst he got Charlie in position.

He helped Charlie up onto her heels, she was sweating in her wig and pvc body, the constant throb of her ass pussy as it had been filled for so long was unbearable but also fabulously humiliating and stimulating for a slut like her. But now she was utterly spent. She wanted to lie down next to her wife and be cuddled to sleep. That was not about to happen.

Tim took Charlie to the coffee table and once more stuck the dildo to the centre.

"Godddddd no please Master not that, i can't take any more, i'm fucked."

Tim took the lead this time. "You dirty little whore, talking back to your Master and in front of your Mistress too, now it's time to be punished properly, kneel down bitch." His voice was only slightly raised, but it had menace in it.

Charlie was frightened now, truly frightened, she'd always hated corporal punishment. She did as she was told and gingerly knelt down on the floor.

Tim reached under her, between her legs and opened the crotch zip wide, he grasped hold of the base of the plug with his left hand and first pushed it in as deep as he could, forcing Charlie forward and making her groan. Charlies ass pussy clamped onto the plug even harder, then Tim clamped his right hand over Charlies mouth before pulling the plug straight out in one swift motion with his left hand, not allowing Charlies asspussy the time to adjust. Charlie screamed into his hand.

Tim then slammed the plug back in until her saw her asspussy clench onto it and then he immediately pulled it out again, all the while covering Charlies mouth with his hand to muffle the screams. He carried on this punishment for a few minutes until he'd taken the plug out 50 times. By the end of that Charlie was simply moaning no longer capable of screaming.

Once he stopped she wanted to thank him, but before she could he stood astride her kneeling bent form facing backwards. He bent over and began to smack each butt cheek in turn. The smacking was harder than Charlie had ever taken and she moaned as the blows rained down on both her cheeks and her ass pussy.

Tim knew this was the time to really break her, to make sure she knew without any shadow of a doubt that she had no control anymore and that if she even voiced a little dissent, then there would be serious consequences.

Tim wanted Emma to see this break of her sissy husband, to see the tears, the running mascara, the cum glazed face and cum streaked wig, before finally she would see her husband give up any last vestige of control and see her body slump under the blows.

He continued, smack, smack, smack. Her arse reddening more with each stroke, his hands were now beginning to hurt, but he continued until her butt cheeks were a deep red colour.

She was sobbing now, big heaving sobs, her makeup running and making her look even more dishevelled. But her body was a limp as a rag dolls, her head to the side on the carpet. Tim knew she was spent, but this in his view was not the time to be merciful. It was just the moment to ram in ever harder and deeper to show her the slut she had to become.

He lifted her up and instructed her to kneel on the table in front of the dildo and to bend forward.

Charlie carefully stood up, tears rolling down her face, her ass on fire and her hole still gaping, she looked into her wifes eyes hoping to see pity or compassion, what she saw instead was wanton excitement and a raw sexual energy she'd never witnessed before. She's foolishly thought she'd see a look of horror or at the very least concern, but it was a look of horniness and delight instead.

Charlie knelt on the table and leaned forward, her cum covered face resting on the table.

"Now pull them apart bitch, so your wife can impale you once more." Tim nodded to Emma who got up and walked to her husbands' big sissy butt cheeks.

"You know what she needs now don't you Emma."

"Yes Sir, she needs to be a proper, well behaved Sissy slut, as she watches us."

"That's right and what do Sissy sluts need?"

"They need their pussies to be filled and stretched all the time Sir."

"Good girl, then do it."

Emma got off the bed and stood by her husband, she bent the menacing big lubed up blackdildo towards her sissy husbands slack slut hole, she pushed two fingers in deep, bringing a low moan from her slut. She knew now to open her as wide as possible to accept the big mushroom head of the dildo. Then she lined the head of the black rubber cock up with the now twitching red hole and pushed the head into her husband.

She was genuinely enjoying doing this to her sissy, loving the sheer kinkiness of it, the humiliation of doing this in front of Charlies Master, well in fact just the idea that it was in front of a guy, made it all the more fun. But doing it to her husband, being the one completely in charge was making her wetter and wetter.

Then Emma took Charlie by the shoulders and pulled her up and backwards so the first few inches of the cock were stretching her wide open. She waited for a few seconds and then she pushed with all her might and most of her weight down on her husbands' shoulders forcing each and every veined inch in until her new sissy slut was once again balls deep on the table.

Charlie let out more of a sigh than a moan, she was barely capable of anything else, completely shattered, what little resistance she might have had a little while ago had been fucked out of her.

Tim just waited to see how Emma would progress, would she know what to do next, without being guided? Sure enough she pleased him.

Without any bidding she attached her husbands high heels back to the straps and padlocked them in place. She then took Charlies hands and locked them together behind her back.

Charlie was gently crying, her ass cheeks still burning from the spanking, but the feeling of fullness and stretching as she was impaled was overcoming all other feelings, she felt spent, now she wanted the session to be over, her ass pussy had been full for a few hours now and it was the most sore it had ever been, she longed to go to sleep. But she knew that she could not ask for that or anything else, she just had to take it like the whore she was becoming.

Tim motioned to Emma to come to him and she did, so they were both standing directly in front of Charlies eyes as he pulled her into a deep embrace. This time it was Emma who couldn't help herself, she wanted more, she needed more and sunk to her knees to worship what had just been deep in her ass.

His cock was quite clean thanks to Charlie, but the musky aroma of her own asshole was unmistakable as she slowly ran her tongue around the heavy gauge Prince Albert piercing.

She looked up into her Masters eyes as she bathed the head of his cock in her saliva, "God I love this piercing and how it felt when you fucked my butt hole with it."

"Funny, I thought you were enjoying it, as you might have read in the messages between me and the sissy slut, we talked a lot about me getting her pierced as a mark of her submission to me, we'd even talked about an ass pussy tattoo."

"Ohh fuck really a tattoo, how hot would that be, what kind of piercing had you thought about?

"Let's talk about that over dinner, for now focus on sucking my cock back to life."

"Yes Sir, sorry Sir."

Tim smiled, she really was starting to get the power dynamic between the three of them, she knew her role as a hot wife was to take it in all three holes to keep him satisfied and that she could treat her sissy with as much disdain as she could muster. She was becoming a perfect pet for Tim.

Charlie was slumped forward, shattered, totally tired but deep in sub space, the fullness and stretching she felt although painful, felt somehow right, somehow deserved. She wasn't so much longing for release as becoming reconciled to her lot. She knew from now on her ass pussy was almost never going to be empty.

She watched her wife kneeling before her Master, caressing his pole with one hand whilst cradling his big full balls in her other hand, looking at his magnificent hardening cock as though it were a Gods, which in a way it now was for both of them. Charlie looked back at her own shrivelled, impaled, imprisoned and cum soaked clit and the difference was massive. She was no longer a man.

How could Emma, ever have been satisfied by that pathetic excuse for a cock, by the guy Charlie used to be, the only way she could hope to satisfy her wife now was with her mouth, tongue and her ass pussy, but more importantly with her unquestioning submission. Her completely submissive servitude would satisfy her wife in the future and nothing else. Just to see her smile, even maliciously, would be Charlies' simple reward, was what she now craved. She had to please her wife and her real Master.

As Tim was being sucked, well more worshipped he bent and reached down for the bottle of Pig Sweat poppers and with one hand cupped Charlies chin to raise her head and held the poppers to one of the sissies nostrils closing the other.

Charlie was on complete bottom autopilot, breathing in as much as she could get on board, knowing this would help her deal with the huge rubber cock she was impaled on. Once she had breathed in for the slow count of 15, Tim covered her mouth and pinched her nostrils shut, forcing her to hold in the huge breath she had just taken in. He made her hold it until her Adam's apple started to bob as she longed for breath. Then when Charlie thought she could take no more, Master let her take a breath. The Pig Sweat hit her like a train, taking her to a new height of horniness.

As she wallowed in the pigginess of her position, sitting upright, eyes closed, hands cuffed behind her back, she started to rise up and down off the cock, rotating in position in an attempt to widen herself further and to stimulate her G spot. Tim gazed at her smiling, knowing there was absolutely no going back for this new slut of his. Then as Charlie opened her hazy eyes and saw her wife slurping and sucking Tim's cock as though it were the most delicious lollipop, she was captivated then Charlie looked up into Master Tims eyes to see him smiling, he knew he had won. But there was much further to take these two sluts in front of him.

Tim searched but he could find no signs of revulsion in Charlies eyes, no hint of jealously, just the unmistakable look of a pig faggot who knew its new place in life. Today and the night to come were going to be a lot of fun, although for what he had in mind for his new sissy it would still be a massive stretch for his newest trainee.

He held Emmas head and began to forcibly fuck her face, not going as deep as he did with Charlie but still making her gag hard. As she looked up into his eyes, he could see fear, he felt his balls starting to rise and pulled out of her mouth. "Keep your mouth wide open Emma."

His hips thrust forward one final time into his clenched hand and the first rope of cum shot straight into Emmas' open willing mouth, then the next and the next, a little hitting her upper lip. She stayed kneeling, tits pushed forward, nipples firmly erect as he finished his orgasm and he smiled down at her. He looked across to Charlie who was still fucking herself gently on her table cock. She was looking at her own wife with a mouth full of her Masters seed.

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