AliExpress and Sissy Downfall Pt. 02

Charlie had really done it this time, deciding on his first big self bondage session in his hotel room after picking up all his kinky goodies he bought on AliExpress. Then his wife had surprised him by joining him for the weekend and found him, fully dressed as a Sissy slut, make up, wigs, high heels the lot. Locked in bondage at his own hands. Now she was about to talk to his cyber Master, what more could go wrong?

What on earth was Master Tim going to tell her, shit this was a disaster. Charlies mind was spinning, what the fuck could he do. The very simple answer was absolutely nothing at all.

All he could think of was the taste of cum filling his head, swamping his very thought. He couldn't swallow it, it simply stayed in his mouth as drop by slimy drop it kept his throat coated. All he could smell was his cum that his wife, his own wife had just fed him, fuck this was way, way out of hand.

But then a tiny voice reminded him that he wanted this, that this was his fantasy. Now he wanted to get off the train, but there was simply no choice. Now that he'd cum the black dildo inside him felt too big to handle, he tried to hold himself up off half the cock, but after a few minutes his thighs were burning and he had slump back down and take every last inch of it. Just as he'd planned. Just not that he'd planned it for 3 full hours and that after having a butt plug locked in his poor ass pussy for 90 minutes, by Mistress Tegan.

Emma, Charlies wife, closed the door behind her carrying his laptop and her key card. She was aware that she was getting more and more damp, she really wanted to have some privacy and get herself off, but she didn't have time for that now.

Fuck what should she do now? a quiet place with a drink and some privacy she thought. Maybe that would be easier said than done at the Sky City Grand.

She checked with reception and decided upon Andy's Burgers and Bar, as it had a few booths and she really didn't want anyone looking over her shoulder with what she wanted to be looking at on her husbands laptop.

As it was after the main lunch crowd had departed, she managed to get a perfect booth with a solid wall behind her, so no one could see just what smut she was looking at. She ordered a burger and a Mojito figuring it could go on Charlies work tab and that she really needed a drink or three.

Then as they brought her the drink she took a swig and opened the laptop.

A message was waiting "I'm at the hotel and am happy to chat if you want to?"

Fuck, so Tim really had meant chatting soon. She just wasn't sure if she was ready for this, should she look through the emails, messages, listings, stories and get more of a feel for Charlies depravity and fantasies before she met his so called Master.

She mulled it over for a couple of minutes before thinking, fuck it this guy obviously knows more about my husband and his kinks than I do, so in boots and all.

"I'm at Andy's Burgers and Bar. In the booth, in a black top with a red scarf."

"See you in five." What she didn't know was that Tim had done his research, he knew exactly what she looked like, in fact from chats with Charlie, he knew quite a lot about her which would help him in their discussions.

She opened the messenger stream, from which Charlie had obviously deleted a lot of history, as there wasn't much there for her to see. Not enough for Master Tim to know Charlie as well as he seemed to.

As she looked up from the laptop a smart, 50 year old guy, with salt and pepper hair who obviously worked out a lot, from the look of his honed body, approached her. He set a black leather holdall down by the side of the table.

"Emma I presume."

"Indeed it is, Tim? Or should I say Master Tim?"

She smiled up at him as he shook her hand. He returned her smile.

"Tim will do just fine, I reserve the Master for sluts like your husband."

She recoiled slightly, he'd just met her and straight away this stranger called her husband a slut, then again judging by what she'd just seen and left in their room, he was a complete slut.

"OK where do we start?" she wanted him to take the lead.

It was soon obvious he was more than happy taking the lead.

"Well firstly, let me compliment you on how you dealt with seeing him in all his depraved glory, the feeding and then the ball gag, absolutely priceless. I'm guessing you don't know just how perfect that was?"

"What do you mean perfect?"

"Well for a slut like Charlie, he craves the taste of cum when he's horny, but once he orgasms, he hates it, deplores it and the moment has well and truly passed for him as soon as he cums. But when he had his first anal orgasm and you fed him, he'll have hated it and loved it at the same time. The anal orgasm is a badge of honour for a Sissy."

"That yearning to taste cum passes really quickly for most submissives and he'll have wanted to get the taste out of his mouth, but you did the opposite by making him keep the pool of cum in his mouth then gagging him, that was wonderful." He smiled at her and she was paying total attention to his words, she was engaged already, this was going well he thought.

"Once the ball gag is in place a sub can't really swallow more than a few drops at a time and the gag will make him salivate a lot, by now that saliva will be dripping onto his corset and caged cock. But each time he tries to swallow he'll get a fresh taste of cum, his throat and mouth will be coated with it, it's all he'll be able to smell and taste for the next couple of hours. You nailed it."

"I didn't really know what I was doing, but the videos he was watching suggested that he needed to eat some cum to me. Then I didn't want him calling out for help. He'll be OK though, won't he?"

"He'll be in hell and heaven at the very same time, which is perfect for subs, they shouldn't be allowed to be happy they need to be pushed and stretched. His legs will be really sore now, he won't be able to stay up off the cock for very long and he'll be taking every last inch of that cock, more and more of the time. But he'll be fine." Tim smiled his most reassuring smile, this just kept getting better, but he didn't want to scare her away.

"I presume you know little or nothing about Charlies proclivities, well at least that's what he told me."

"I didn't know about any of this, how long have you known him."

"He first responded to an ad I placed on Collar Space about 3 months ago."

"What was the ad you placed and what's Collar Space?"

"Ok let's start slow, if you put the laptop so we can both see it, but so no one else can."

She turned the laptop so it was in the middle of the table between them with the back of it facing out into the restaurant.

He reached over and used the mousepad to open the tab on Collar Space which Charlie had checked earlier. Pulling up Charlies profile of Subboislutnz.

"This is who your husband really is. A submissive sissy slut looking for domination." He opened the mail tab so Emma could look at some of the message interactions with male and female Dominants, including himself.

She just scrolled through looking at the initial contact between Master Tim and Charlie. She could hear Charlies voice as she read the texts, the excitement in the emails as he saw the picture of the dungeon that Master Tim had sent and especially when he was told about the fucking machine and then she saw the exchange of mobile numbers.

"Did you swap texts with him?"

"Hundreds of them, often whilst the two of you were watching TV together, we spoke on the phone 4 or 5 times, very intense deep conversations."

"What while I was in the room, what did you talk about?"

"No the phone conversations were whilst he was still at work. It started off as it does with most subs, all about his desires, wanting to be tied to my fucking machine, to take the balls on my asshook in his boi pussy."

"Woahh hold on there, a fucking machine and what the fuck is an asshook."

"OK sorry all a little too fast. The fucking machine is just what it sounds like, a dildo on a stand that can be set to any level of depth and intensity. The frame allows a sub to be tied and locked into it. So that they can't move a muscle let alone get away, once they are on it and the machine is on, it simply fucks them as hard as a Master chooses for as long as he chooses."

"And Charlie wanted to be restrained on that machine."

"He virtually came on the spot when I told him about it, it's most sub sissies dream. He couldn't search the internet fast enough for pictures of it to imagine himself on it being fucked into oblivion."

"Seriously he would want to be fucked by a machine and be helpless to stop it????"

"Sure, what a rush for a slut like him. As a submissive it's having the control completely taken away by their Master or Mistress, that's the real excitement. Even if the result is uncomfortable or painful, their response is one of pure excitement."

At that moment the Waitress came across, "Are you joining the lady for lunch Sir."

Tim looked at Emma and she nodded imperceptibly, "I am, in fact I'll have the same as her and if you can get her a top up on the drink too please, I think we might need it."

"I can bring you jug of Mojito if that would suit?"

"Absolutely perfect thanks."

As the waitress left, Emma realised all this talk was definitely turning her on, her pussy was really wet now.

"Is he really a slut or does he just fantasise about it."

"Well let's have a look at his profile on Collar Space and on Fetlife, look at Fetlife here, he has a different nickname on here, he is His_fag_wife, that's the name I gave him."

"Why, because you want him to be your wife, how would that even work."

"I wanted to mark him as mine, so other Doms know not to try with him. He's utterly submissive to me and he likes to cross dress."

"I like to remove every last vestage of manliness from a guy, especially married, outwardly straight ones, to turn them into a complete fag, my fag, that's what I get off on, the sheer humiliation of breaking them. He'd still be your husband, in fact a better version of one, more obedient and doting to you, but to me he'd be a complete fag slut."

"Woah this is too much to take in, what the fuck do I do with all this, it's just too much to take in."

"Like I said we take it slow, let's look at his interests and see how much of a slut you think he is, then you can decide what you want, ohh and also what you're going to do with him later today as he's still impaled on that huge cock for the next hour or so."

"Yes he's got over an hour left on the timer lock, locked onto that giant dildo."

"Just as the slut should be, don't worry, he'll be shit scared about us talking, but his slut fag side will be loving it. If he didn't have that cage on now he'd be rock hard and dripping, that I promise you."

"OK show me the profile Tim. Let's get it over with."

"Look at this one on Fetlife, you can see the pic of him in the corset and this is one of him keeping his cock small with poppers, look at the bottle alongside."

"But why on earth does he want his cock to be small, surely men want to make the most of it."

"But that's just it Emma, he doesn't see himself as a real man, he sees himself as a Sissy sub slut to a real man."

"And what about in relation to me?"

"Well he'd love you to be dominant to him. He would love it if you took control, but I did get him to admit that he really is gay deep down, that he needs to be controlled and fucked by a man."

"Shit so he wants you and not me?" Emma looked really worried now.

"No, no, no, not at all, he wants male domination as well as female domination, he's just never thought it was even possible with you. Didn't the two of you once buy a butt plug in Amsterdam, for you to use on him, but it never happened?"

"My God I'd forgotten about that, I can't even believe that he told you about that. But yes, I guess it just wasn't my thing."

"But it's what he needs, look at what he's searching for on Collar space, Domme Women, Dom Men, and Domme Trans along with you've guessed it Dom/me couples."

"He knows he's completely submissive and a bottom, so that means he wants to be controlled, to be trained as a slut for pussy and cock. But at no time does he think about doing the fucking himself, unless he was ordered to, he thinks about getting fucked now, by women with strap-ons, by Trans Mistresses with She-cocks and by Gay Masters with much bigger cocks that his own."

"Has he just fantasised about this though or actually gone through with some of these things on here?"

"He's definitely gone through with some of them, from what he's said to me, he's not a complete fantasist, although I think that is his main problem, his fantasies are all about him, not about pleasing his Master or Mistress as they should be. He is there to serve their wishes not his. He's had a number of sessions with Pro Mistresses and told me about some TV Mistresses."

"Has he actually sucked a mans cock?" Emma was getting emotional now, it was hard containing her thoughts.

"He has yes, on a few occasions, but he told me always with condoms. But when you read his stories, they are way more fantasy based, so don't worry most of it could never happen."

"Ohhh fuck, what next, what's this about watersports?"

"You know what that is don't you?"

"I think so, he likes to be pissed on?"

"Well a bit more than that, he likes to be forced to drink piss, his and other peoples. If you look at some of his wilder stories on Literotica, you'll see that he's into this a lot."

"Are you into that?" She asked as it sounded as though he was.

"God yes I love having a sub wife who drinks every drop of my piss and swallows my cum, that's what they are there for, to serve my wishes and to worship my body." He was warming to his task of explaining this all now.

"To have a sub, naked, kneeling before me, suckling on my cock and then to hold their head steady between my hands and look down into their eyes and tell them to drink as I let my bladder go is simply delightful."

"Ohh fuck I could never enjoy that."

"Are you sure, it's wonderful, humiliating them in that way."

"Each morning as you shower you could order him to wait kneeling in the shower as you get up for you morning piss and simply stand astride his face and order him to open wide as you let the torrent of fresh strong piss go all over his face and into his waiting mouth. As you pissed on him you'd see him get hard. How does that sound."

"Actually after what he's putting me through it might make me feel better." She smiled at him, a nervous smile, but also a conspiratorial one, she was beginning to get off on their kinky conversation.

"There you go, there are so many little humiliations you can put him through, you get to be the complete boss all the time. You could also try cuckolding him, he seems to be turned on by that too."

"Cuckolding, that's what exactly?"

"Well you keep him in chastity, like the cage he has on now that you saw, although that is an extreme one and probably not good for regular wear. And then you become a hot wife and have sex with whoever you want. His only role would be to be restrained while you fucked in front of him, if that humiliation would get you and your Bull off, or even better the clean-up duties on both of you after you have fucked." He paused, her face was a picture.

"Some hot wives just go out to a club get fucked and then return and have their cuckold clean up after they get home. Others have their Bulls fuck their cuckolds in both holes, it depends entirely on what turns you on, not what turns Charlie on."

"I take it clean up duties mean what I think they mean?"

Tim was enjoying this education process and the occasional smiles from Emma, he'd asked Charlie early on in their conversations if he might be able to involve Emma in their play, but Charlie had been adamant that could never happen. Not that Charlie could influence that now he was still locked riding his big black cock, all alone in his room.

"Indeed it does, eating the cum from your pussy or ass and sucking the Bulls cock clean."

"Jesus this is so wild, I don't know what to say."

Tim reassured her, now he was very keen to have her as well, to help him cement his total control and position with Charlie as his fag slut.

"Take your time, there's no hurry, I can explain bit by bit. Just look at this profile she's a hotwife, getting fucked by the biggest black cocks she can find and then look at this picture, her husband in lingerie and tied up and her squatting over his mouth and squeezing the cum into his open mouth, Charlie liked this photo and he follows them on Fetlife, just as you might on Facebook."

At that moment the waitress came back with their jug of Mojito and the two burgers balanced on her arm, she reached over the laptop setting the jug down, then the plates. As she stood up she saw the screen on Fetlife and Charlie's profile pic.

"Ummm have fun." She said smiling and blushing.

"See it's not that bad, everyone likes a little kink in their life Emma." Tim was keen to just keep upping the ante, stage by kinky stage.

"Maybe they do. Maybe I should." She was really beginning to consider that this might be a lot of fun and if it was what Charlie wanted deep down in his soul.

Tim was taking things slow, just trying to introduce ideas one by one to see if they would fly or not.

They started to eat.

"Good to get our strength up for later." He almost winked at her.

Emma smiled back at him "What do you mean later." She thought she knew the generalities of what he meant but not the specifics and didn't know if she was ready take the leap today as she sipped on her mojito.

"Well, I was thinking we can chat through everything to give you a really good idea of what you're facing and some of the choices you have aside from divorcing him, unless you've crossed the Rubicon on that one."

"No I've not made my mind up yet, but I want to know more about this whole thing.

Tim put his knife and fork down. "Firstly you need to decide if you can cope with sharing him with me or someone like me. The reason I say firstly, is that I'm absolutely convinced that he needs some gay domination in the mix, if he tries to walk away from that, his mind and cock will drag him back, he needs that to be part of the solution."

"OK and then?"

"If you decide you can share, then it's about what really turns you on, and what turns you off. You'd be completely in charge, not him, so it's about what stimulates your mind and body. Then you see if that's enough for him and make your decision. He's really not in a place to object to whatever you suggest, is he?"

"I guess he isn't no, I wonder how he's getting on?"

"Very sore asshole and cock and wishing he'd left some keys close by so he could get out. His legs will be aching so much he'll be fully impaled and his prostate will still be getting stimulated by every movement he makes. He'll be desperate to get the cock out of him, once submissives have had something opening them that wide for so long, that's their only focus, which is why we'll make him do a lot of things before we set him free from the cock he chose to impale his slutty self on."

"This is where we actually teach him, his real, or I should say her real sissy place. To be allowed to get off that cock, is now at your behest and is a gift only you can give. You are now his Goddess, he is simply your sissy slave."

"So you think he'll agree to anything to get off that cock."

"Absolutely anything, she'll beg for it I think, she may even cry in front of you, that is until we get her high and horny again. Her mind will accept a lot today after such a long time in bondage and being fucked for so long, we have to press home these lessons so they are etched in her Sissy slut mind, forever."