tagTransgender & CrossdressersAliExpress and Sissy Downfall Pt. 03

AliExpress and Sissy Downfall Pt. 03


Tim cupped Emma's arse cheek as they went into the hotel room, stroking her, sliding into the cleft of her cheeks, warming her up a little more, not that she needed it.

Charlie didn't notice them come in at all. Not that she could really turn her head with the thick COCKWHORE collar padlocked tightly around her neck. The cords attached to the dildo were also holding her in place. Her eyes were closed as she tried not to feel as though she was being split in half by the monstrous cock which had been buried deep in her for over three hours. She was so exhausted that she simply couldn't lift herself off the dildo at all, it was lodged firmly all the way in her.

Tim sat on the chair directly behind Charlie, completely out of view, he set the bag down on the floor and reached in pulling out the riding crop he'd mentioned earlier and passed it to Emma. She smiled lasciviously.

Emma took in a deep breath and rested her hands on Charlies shoulders, with a little downward pressure to ensure that her sissy husband was fully impaled. Charlie was startled and rose off the cock a couple of inches from shock, before the pressure from Emma's hands forced her back down fully onto it and elicited a long low moan from her Sissy.

Emma leant forward and whispered in her sexiest husky voice into Charlies ear, "How is my little sissy slut of a husband doing, still having fun baby?"

Charlie moaned into the gag, "Noooooo" but all that came out was a long moan.

"Now Charlie I'm going to unlock your gag and then I want you to keep all the cum in your mouth to show me before you swallow like your Sissy hypno videos instruct you too, no spitting it out slut, you understand?"

Charlie said nothing.

The thwack of the leather tip of the riding crop on Charlies right butt cheek shocked Emma with its crack, but the effect on Charlie was much more extreme. As Emma still held her down on the cock she began to whimper from the pain and the intensity it caused deep inside her.

"Now do you understand, bitch?" Emma had raised her voice significantly and also added a harsh edge to it, Tim was sitting, legs crossed, enjoying watching this scene play out.

Charlie weakly nodded her assent.

Emma walked around the front of Charlie and reached over the bed picking up the assorted keys, she then moved behind Charlie and unlocked the gag, as she moved around to the front to remove it, she looked into Charlies eyes, "Remember Sissy, it was you who started this, this is happening as a direct result of your choices. You made your final choice when you spent our family money on the kinky shit you are wearing, or sitting on and those items still on the bed. Nod if you understand Sissy..."

Charlie was tearing up and looked downcast, but nodded.

"Look at me you bitch, I'll tell you when to look down, now I'm your fucking Mistress, that's what you chose when you squatted over that huge cock. The moment you lubed it up and let it stretch your asspussy wide open like a dirty fucking ass whore, the choice was made. As you sank down on it inch by inch, you fucked yourself, literally and metaphorically. You made your final choice. There is no going back, only going deeper now." As she said that she pushed down on his shoulder.

"Now I'm taking the ball gag out, keep your head up and your mouth open and show me your sissy cum puddle in your mouth."

Tim was impressed with Emma, she was taking to this like a duck to water, although he still looked at her as a predator would.

She took the slimy gag out and put it down on the table, Charlie kept her head up and her mouth open showing a large amount of cum and saliva pooling in her mouth.

Emma raised the crop and looked into her eyes once more, "Now swallow your cum bitch, swallow it for me."

Charlie looked into those deep brown eyes and was resigned to her fate, not yet excited about it as she had cum far too recently and too much for that. She closed her mouth and tried to swallow, managing to get half of it down first time.

"All of it bitch."

Charlie swallowed the rest and opened her mouth to show it was gone.

"Good girl, well done, that's going to become a staple of your new high protein diet Charlie, so I hope you like it."

"Yes Mistress thankyou." Charlie really didn't mean it, but figured he had to keep on the right side of his wife at least until he was set free and off this fucking cock.

Emma sat on the coffee table and leaned in close, smelling the cum on her sissy husbands breath and for the first time in her life finding the aroma intoxicating.

'Understand that what you chose, was to put me 100% in charge, that is how it is going to be forever for the two of us. I've read some of your dirty little stories on Literotica, your desperate messages to Masters and Mistresses around the world and your profiles on Fetlife and Collarspace and I finally realise this is a need you simply can't let go of. It's part of you and now it's part of our future relationship, just like you dream about."

She let that sink in for a few moments before continuing.

"We both know these are your deepest, dirtiest fantasies and I'm going to make them happen one by one, taking you further and further into those dirty fantasies, making some things come true that you thought would always have remained only fantasies. But you have to understand that it's far, far, far too late for you to stop this happening. That moment passed, the moment you clicked the lock on these handcuffs. You sealed your fate."

Charlie was desperate now, "But you don't want this Darling, set me free and we can talk about it, I can give this all up, I promise."

"That's your real problem Sissy, now that I'm getting into this, I do want it. I'm actually turned on by the thought of having you as my Sissy slave, at my beck and call. But most of all I want real men who can fuck me properly and have something more in their trousers than this pathetic clit of yours." As she said that she gently cupped his balls and cock cage in her hand.

"Just look at it, it's pathetic, simply could never satisfy a real woman. God just look at you, you've cum again, you dirty little bitch, you've had no one to help you, no stimulation of your clit at all and yet your asspussy still made you spurt."

She held her cum coated fingers up to Charlies mouth. "You know what to do."

"Emma, please don't I beg you, don't make me do that again."

This time the shock of the riding crop directly onto her clit cage made Charlie rise up to stretch the bonds she had, a good 6 inches off the cock base as she started to scream. Emma closed her cum soaked hand over Charlies mouth to stifle the scream.

Then Charlie slammed back down on the cock.

"What the fuck do you not understand about the situation you are in. You are completely and utterly fucked." As she said that she took a pic with her phone of Charlie looking directly into the camera, cum covering her mouth and chin.

"Now should I send this to your Mum and Dad?"

Charlie was in agony and breathless, "pleassseeee nooooo, pleeasseeee don't do that, I beg you, not that."

"Then do as I fucking say, or I will, I'll send it to all your family and friends, see what they think of you then slut."

"When you got all dolled up as a Sissy Slut, when you clasped you collar shut, with its large silver letters Saying COCKWHORE, when you lowered yourself onto this big black dildo, you chose to be a cock slut full stop. Now you are my Sissy slut, do you understand and accept that?" Emma began recording her Sissy husband with her phone.

"Yes Mistress I understand and accept it."

"What do you accept Sissy?" Emma wanted to really pile the humiliation upon her husband now.

"I accept that I am your Sissy slut Mistress."

"That's right and what will you do for me?"

"I'll do anything for you Mistress."

Emma looked intently and asked again "What do you mean by anything, think more of what's in your fantasy stories, as that is what you are going to have to do. Think about being a 2 hole cum whore for me."

"I'll suck any man you command me to, eat as much cum as you desire, dress as you choose and give my ass pussy to anyone you want Mistress."

"Now remember those fucking words, they are all on camera, you're so right, you will do anything and anyone I order you to. Remember you're just a fucking Sissy slut whore now, nothing more, behind closed doors. " Emma slapped Charlies face hard, as she finished speaking.

She gave it a few moments to sink in and then leaned forward close to Charlies face, "Now that I know what you've been up to it's time to make your very darkest Sissy dreams come true. So watch this video and enjoy whilst I get ready for the next stage of your training."

Emma set the Limitless collection of Sissy Hyno videos going on the lap top and plugged in the head phones and placed them over Charlies ears.

She reached over and picked up the bottle of Pig Sweat and opened it, holding it to Charlies left nostril as she closed the right one with her finger and waited for Charlie to inhale, she counted to ten, knowing that Charlie wouldn't be able to hear her perfectly but would see her lips moving, Charlie knew what to do.

Emma carried this out twice loading her Sissy up, then Tim motioned to do two more, so she did just that. Once again Charlie was high and everything felt heightened and more exciting. It knocked the edge off her exhaustion.

"There you go my little Sissy piggy." Charlie could just hear the word piggy.

She reached over for the lip O ring gag and as she raised it to Charlies mouth he simply opened wide to accept the silicon O ring in his mouth and behind his teeth. Now she had bright red plastic lips and a wide 2 ½ inch diameter hole into her throat.

Emma picked up the tea spoon and scooped up 4 spoons of cum from under Charlies cage and fed them into the hole.

As Emma moved around the back of Charlie, Charlie simply focussed on the words coming up and trying to swallow which was hard with the gag in place. Tim smiled at the scene in front of him, he was going to enjoy this.

The messages flashed quickly and repeatedly against a back drop of girls sucking cocks and of sissies dressed up and sucking big mens cocks.

Cock loving Faggot You Love cock You can't stop sucking Worship Cock

Sissy Slave to cock Cum Dumpster Slave to cock Sissy

You love cockWorship cockSissyLimp fairy princess

Give in obeyBeing hypnotisedCock obsessed cum addictedYou're the queen of cock

open those creamy lipsBeg and pleadIt's Sissy spanking time, I'm going to blister you sweet li sissy butt

CraveTrained to give the perfect blow jobSavour the cock suck the cock

You want big black cockCum so warmI love anal

Whore yourself out to buy implantsCum tastes wonderfulFAG


COCKSUCKERLet men fuck youBeg men to fuck you

Swallow huge loadsANAL WHOREIn my ass




Charlie could only think of the words, as a result she was rocking gently on the cock, getting horny once again, just as Tim had thought she would. It didn't take long, Charlie was totally focussed on the images and hypnotic messages working their kinky magic on Charlie.

Emma checked that Charlie was in the zone and just focussing on the music, images and words flashing before her eyes.

She stood in front of Tim, out of sight of her sissy husband and began to undress. She was totally turned on now, loving the sheer sluttiness of stripping in front of a guy she met an hour earlier. She took of her shoes, her trousers and top and stood in her mismatched bra and big pants.

Tim could see just how wet she was, her nude panties showing a big wet patch between her freshly shaven legs.

Despite the frumpiness of her underwear, Emma could see she was having an effect, or at least the entire scene was having an effect on Tim, with his cock straining at the trousers he was wearing.

She took off her bra, freeing her impressive F sized tits, her big nipples erect with obvious excitement. She stripped as seductively as she could, she wanted this man to fuck her brains out right in front of her Sissy husband the thought had her tingling all over.

As she bent forward to remove her moist panties, her tits hung low, Tim was admiring them, looking forward to giving them some pain and attention as he fucked her from behind. She was Rubenesque in shape and all woman in Tim's eyes, although for him it was more about bringing the sub side out in her for him and the Domme side out for her Sissy.

She stood back up, letting him inspect her, her full Brazilian meant the moistness of her pussy was showing clearly. Tim reached forward and she parted her legs for him to allow him easy access. He turned his hand and curled his index finger into her, parting her wet lips and entering her gently. She closed her eyes and let out a little moan.

He raised his wet fingers to her lips and painted her lipstick with her juices. She moaned again, loving every touch.

He reached into her bag and lifted out the corset. "Is this the one?"

"Yes it is." Emma lifted the corset to her and begun to fasten the front from the second clasp down lifting her tits into place, the corset truly making the most of them, she carefully fastened the rest and turned her back to Tim.

"Please can you lace me up?"

"Please can you lace me up, what?" Now was the time to show her, her own place in this pecking order.

"Please can you lace me up, Sir."

"Of course I can slut, no problem at all." Tim smiled happy with how the entire day was working out.

He pulled the strings tighter bit by bit, working the laces from the top and bottom to the middle, enhancing Emma's waist in the process, he'd plainly done this before.

Once he had tightened it enough so that she was slightly breathless, he tied off the laces and picking up the padlock from the ball gag, he locked the laces together with a click.

"See now, your Sissy husband needs you to free him and you need me to free you."

"Yes Sir."

"So now tell him what's about to happen, let him know it's time for the next stage."

As he said this into Emma's ear his hand stroked her butt cheeks, then he cupped the cleft of her buttocks and raised his juice covered index finger between her fleshy arse cheeks and to her the entrance tight ass hole, merely pushing on the pucker, not entering it but applying a little pressure.

"Ummmmm so, so tight for me slut, I'm going to enjoy opening you up in front of him, for your very first time, taking your anal cherry right in front of him will be priceless." As he said that he reached around with his other had and placed his finger on her clit, working it gently. She quivered in his embrace, her cheeks tightening a little. She showed her submissiveness by spreading her legs a little wider apart to give him better access to her holes.

"Ok now go little one and explain what's about to happen to your sissy slut."

Emma walked around Charlie, blocking her view of the laptop and removed the earphones.

"Now are you enjoying yourself Sissy, is this fun for you."

Charlies eyes were on stalks, her wife was naked apart from the corset and looked stunning. Charlie the Sissy suddenly felt like a man again, he loved her complete Brazilian and could see she was totally turned on. Now he just wanted to be set free to fuck her, maybe that's what she'd been planning all along. He was beside himself with lust.

Charlie nodded to his wife to show that he was enjoying his new place.

Emma could almost read his mind, she knew just what her silly sissy was thinking. "Now some of your very dirtiest and very deepest and darkest fantasies are about to come true, it's time for the next stage of your training, are you ready whore."

"Ummm, Umm istress." Charlie tried to talk but just the vaugue sounds of the words came out.

Emma decided she'd better clear things up for her Sissy, "Good little whore, such a good girl. I hope for your sake you're not squatting there hoping that I'll set you free to suck my fabulous pussy, because if you are, you are sadly deluded. You gave up that right when you dressed as a Sissy, you are no longer a man to me. Just my Sissy slut." She let those words sink in.

Charlies frowned, shit this was getting more and more real, for just a few moments she had thought she would get to fuck her wife, but it was the other way around.

"Now don't let me down, live up to your COCKWHORE collar, you hear me. Remember you are the Queen of cock."

Charlie nodded, wondering just what she meant and wondering if someone else was going to be brought into this scene.

Emma put the blind fold on Charlie and then she nodded to Tim.

Tim had stripped whilst Emma was talking to Charlie and was already sporting a semi erect cock. His heavy gauge Prince Albert piercing making him look even more menacing.

Emma leaned in to Charlies ear, "Now it's time for action baby, I need you to get my Bull rock hard, so he can fuck me senseless, right here in front of you. If you were a real man, you'd get up and throw him out on his arse, but because your just a silly Sissy fuck slut, you will worship his cock and get him ready to plough my pussy, for you to watch your manhood being fucked out of you, with each thrust of his Alpha cock in my soping wet pussy."

"After this you will be the proper Sissy cuckold you've always fantasised about being, but never had the balls to actually be one. Now I'm doing it for you, you silly little faggot bitch."

"I'd say open wide, but you are Darling, aren't you." Emma laughed at her own joke as Tim stood with his cock just in front of Charlies red plastic lips.

Charlie could smell cock, he knew that smell, the mix of piss, sweat, pre cum and cock. He was shaking now, high, horny and sore, but excited, his clit trying to harden in its own hell cage.

Emma stood behind Charlie, holding his head completely still, holding it firmly in both hands. Showing her Sissy who was truly in charge. "Here it comes my darling macho husband, unless you don't want to go through with it."

Charlie moaned trying to say no, he was horny, but knew this was a dangerous track to be on.

"That's what I thought, you're desperate to taste my Bull's cock." Emma simply ignored Charlies plea and began to guide the cock into the hole in the lips.

"Now suck for me slut, be the cock whore you were born to be. Worship this cock, try to get it ready for me, I'm desperate for a real cock in me for the first time for years. So you can watch me get fucked properly."

The moment of truth for Charlie, would she simply have the cock in her throat or would she truly worship it.

As Tim's glans entered the hole and then exited the other side inside Charlies mouth her tongue felt the piercing and then she finally knew.

Ohh my Lord, now she was actually sucking Master Tim's cock in from of her wife. Fuck, fuck, fuck. This was way out of control. Her mind spinning she didn't worship the cock in her mouth, she simply allowed it to be there.

Tim nodded to Emma and she hit Charlie hard on the butt, "Make love to it slut, you can't stop sucking, Give in, Obey, Savour your Masters cock." Charlie started to cry.

Tim took hold of the back of Charlies head with one hand and roughly clenched his other hand over Charlies jaw. He leaned in close for the first words Charlie would hear from her Master next to her.

"Now you fucking sissy faggot, I have you. You dirty little whore, not even telling your wife any of this, you are a worthless fucking fag. I am going to share you with Emma, but you will be my fag wife today, when you see me fuck her to heaven and back."

"And now we're going to break the man in you, we're going to make you a complete Sissy fag, no going back. Ever." With that he thrust forward making Charlie gag and holding his cock at the back of her throat. Saying "Bitch", Whore, Slut, Fag with each thrust, reinforcing the hypnotic triggers.

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