AliExpress and Sissy Downfall Pt. 02

Tim couldn't wait to see Charlie in the room and see how desperate she had become over the last few hours. He knew what Emma did not that before the 2 and half hours on the cock she'd already had ninety minutes with the butt plug in, so she really would be well and truly stretched, well beyond her normal limits.

"She might even have cum again. Her head will be spinning. In fact the biggest thing will be what's going on in her brain, she'll be questioning why she's done this, can she stop, she'll be feeling guilty, especially if she comes again without anyone there."

"You think he, sorry she, might have cum with no video to watch, no one there to interact with her, just from that dildo in her asshole."

"Her Ass pussy or Boi cunt, whichever you prefer, it's important we use the female form of words to erase the male left in her. But yes I do think she'll have cum again when we go in, more from the mental side of it, if she has had another anal orgasm then she's in really deep, we need to take her even deeper if that's what we both want, fuck what she wants, it's no longer her choice."

Emma was simply nodding and sipping on her drink.

"But if you go back up there and there is a small pool of cum below her clit cage you'll be able to understand how deeply this all affects her. Then if you want you can feed her again. We both need her to become addicted to cum."

"I really did enjoy feeding him, sorry her, that was fun. I always hated the taste myself and so I'd never swallow, not that I've given her a blow job for years. I suppose that makes me think it must be so much more humiliating for her. I did have her lick me out after she'd cum in me once, but I was a bit pissed at the time. Ohh my God I can't believe I told you that."

Tim ignored the comment "Was she tentative when she cleaned you up or did she appear to love it?" Tim knew the answer as Charlie had told him about the incident previously, but he wasn't going to let onto Emma about that.

"Now that you mention it, she was a little tentative at first, but once she tasted it she really seemed to get off on it."

Tim pressed home his advantage, "Of course she did, she was carrying out your orders, to please you, and cleaning her mess up, she wouldn't have had to fantasise that night, for those few moments you were her Mistress."

"She got rock hard again as soon she licked me." Emma was slowly realising that Tim was right about Charlie.

"So to sum up she's into cross dressing, she loves to be forced to suck cocks, she likes to be pissed on, she's into anything being shoved into her ass pussy, the bigger the better and she loves cum. She wants to be dominated by women, TS's, TV's and Masters and she wants to be trained and forced to be a total slut, does that sum it up for you?" Tim was getting hard now, his PA piercing pressing into his trousers, he needed to get this over the line and soon.

"When you say it like that it sounds almost normal, so you think I can dominate her, I don't have any experience?"

"Yes I'm sure you can, you seem like a natural, the cum, the ball gag, having her clean you out that time, we just need to release your inner Domme. You certainly seem to have dominant tendencies and we just need to cultivate those."

"Easier said than done though, isn't it?"

"Not really no, if that's what you want, then I'm more than happy to help you and train you, so long as I get her as my plaything sometimes too, how does that sound?"

Emma pondered for a few moments again just focussing on her hot, wet pussy, desperate for some attention, surely she wouldn't be this turned on unless she was ready to take a step into the darkness.

Emma was ever so slightly nodding her head, Tim knew he had her close to committing. "I think I'm ready to get to know how to be a Domme. Just the idea is turning me on."

Tim smiled and thought he'd push home his advantage, "Good, how much is it turning you on?"

"Well I'm pretty moist at the moment."

"Perfect, you can have her clean you."

"But I thought you said that should be cleaned of another mans cum?"

"Well that would be the ideal, but I'm presuming you haven't been fucked by anyone else this morning?" he was fishing now, hoping she'd take the bait, she had to think it was her idea.

"Of course I haven't, but that would be the ideal wouldn't it, from what you've said, to really humiliate and emasculate her, especially if it was you who'd fucked me, wouldn't that really mess with her mind after she chose to turn you down as her Dom after all the previous communication to the contrary?" Emma was pushing a few of Tims buttons too now.

Emma was determined to go the whole hog, she thought Tim was hot and his natural Dominance was a huge turn on for her and as the idea crystalised in her mind she was getting hornier and hornier, the mojitos were helping the process as she finished another one. Tim quickly and nonchalantly topped her glass up again, leaving his half full.

"So if she were to see me getting fucked by you, right there in front of her eyes, while she's still being fucked by that cock, restrained and completely helpless to stop it happening, wouldn't that help you break her mentally?" She was almost breathless as she said this, getting more and more turned on, by the second.

"Fuck yes, it would help us break him and create her as a sissy properly, that would completely scramble her mind, especially if you fed her my cock first and had her get me hard, telling her that she's getting me ready to fuck your pussy right there in front of her. That all she will be able to do is to worship my cock to get it as hard as she can.. How does that sound."

"It sounds so beautifully dirty, then you'll cum deep in my pussy and I'll make her lick it clean in front of you?"

"That will really take her a lot further along the track to being a fag and a cuckold, is that what you definitely want. Once we start down this path there is no going back?"

"I want it like I've never wanted anything in my life, the whole idea is such a huge fucking turn on, I could cum right now."

"Emma that would be a real waste, she has to see you cum, loudly right in front of her eyes and I mean really cum hard."

"I'm so turned on right now, I can't see that being a problem, in fact I want you to fuck me soon."

"Hold your horses, this has to be perfect, we want everything to fall into place with her. To dismantle brick by little brick her manliness until all that is left is a wretch of a sissy fag for our amusement."

"Ok so what do we do?" she took a few deep breaths to slow her mind down and then another drink as Tim topped up her Mojito once again.

"Well we both go up and see how she is doing, but I'll stay behind her whilst you talk to her. Use your sexiest voice but any challenges from her or any begging to be set free, and go straight from sexy to angry and totally stern, channel your inner Domme. You are completely in charge of her and any sex she has in the future is totally up to you. Make sure she knows that."

"Remember she no longer has any choices, she made her final choices when she spent your family money on her dirty little hobby and impaled herself on that massive cock and tied herself up. You need to constantly remind her of that, forcefully. This was all her choice, not yours."

Tim rammed home the point "At that point she put you completely in charge of the future for both of you. Remind her, that all her stories, her messages, her profiles make that obvious, that she actually wants this to happen, that her wildest fantasies are coming true and it's far too late to for her to try stop that from happening, her choices today made it inevitable. As soon as she squatted over that enormous cock, she chose her future as a slut."

"She did, didn't she, dirty little sissy slut, I think I'm going to enjoy channelling my inner Domme."

"That's what we need you to do, all those dominant women you've seen in films before, become them. Tell her there is simply no denying that this is what she wants. If she says it was all a fantasy, belittle her, take a photo of her as she is now and hold it up to her face, threaten to show them to her friends, family, colleagues, crush her spirit. Use the words from the Sissy Hypno videos earlier, Cum Whore, sissy slut, bitch, three whole slut, slap her face as you do it. Be the bitch you've always wanted to be, when you've argued in the past, now you can say it all."

"This is now sounding like a lot of fun."

"Once we get in there you can take the gag off and get her, remember to always use female pronouns when you refer to her, get her to show you the pool of cum and spit in her mouth and then have her swallow it for you and show you that it's gone." Emma nodded.

"That will establish that she's now taking orders from you. I think you stripping off to your underwear would be a sexy touch, can I ask are you wearing nice underwear for seeing him or just your normal underwear."

"Just normal big pants, I was thinking I'd be in the room alone before he came back and would change after a bath, my overnight bag is in the room behind him with my corset and stockings in."

"Perfect we'll go in quietly, you can put the lap top down on the bed and let her see the Fetlife page open on her profile that you've been looking at, and the messages from me, and a final window with one of her stories from Literotica, that will freak her out."

"Then what?"

"Then open the loop on the Limitless Sissy Hypno Collection, that's 20 minutes long and is focussed in just the way we want it to be, it'll give us time to get you dressed and help to get her horny again. It focusses on turning straight men into gay sissy faggots, she'll love it."

"As it begins playing look deep into her eyes, and tell her now you understand more of what she's been up to, it's time to make her Sissy dreams come true and then put the headphones back on so she can't hear us, getting ready for the next stage.

"I think for good measure you should also get the bottle of poppers and open them and hold them to each nostril for ten seconds and order her to inhale. That will make her much more pliable and more turned on. Just look into her eyes and say inhale, even though she won't be able to hear properly she'll know what to do."

"So that was the little bottle that was on the table."

"Yes the one that says Pig Sweat, they're used a lot by the gay scene as they relax the anus and get the sub really high, but as a side effect they also shrink a lot of mens cocks, including charlies. Pig sweat is Charlies favourite as it's linked to being a no limits gay pig, with no choice in what you take or are made to drink, including piss and cum." He let that comment lie for only a couple of seconds before moving on, not giving Emma a chance question the statement.

"Then you can change into the corset, I'll help you get dressed and then when she sees you for the first time she'll be beside herself with lust."

"Fuck so I have to strip in front of you?"

"Are you serious? You've just asked me to fuck you, so I don't think that's a major worry, do you?" Tim thought it was time to take it up a notch, yes Emma would be Dominant to Charlie but not to Tim.

"So once you're in just the corset, showing off your pussy, then you'll kneel before her and take the headphones off and ask him if she's having a good time. Remind her that some of her very dirtiest fantasies are about to come true. And then blindfold her, we want her to be wondering if anyone else is in the room."

"I think we also want to remove the element of choice completely, so I saw an O Ring gag with a pair bright red lips on them, fix that tightly to her head and then you can whisper in her ear that you want her, your very own sissy slut to get your Bull hard for you, so he can fuck you senseless, right in front of your manly husband and make her a proper sissy cuckold, just like she's always wanted, OK?"

"Ohhhh God yes, that will be delicious, to see her reaction as you slide the cock in ummmm. Will she suck it happily or try not to?" Emma was genuinely intrigued, she'd never imagined that her darling macho husband would ever suck another mans cock.

"Well as I said she won't have any choice in terms of it being in her mouth and throat with the lip gag on, but in terms of her actually worshipping my cock and doing what she should only time will tell. I think you should have the riding crop that's in my bag here to strike her on her fat ass, if she's not doing what she should. Each time you crack that on her ass cheek she'll move and the cock will fuck her deep. It's perfect bearing in mind how sore she will be by now. Don't worry about tears or whimpering, we need her to be taken deeper than she thought possible OK?"

"So you're sure she'll cry?" Emma sounded unsure if she could go through with that, Tim knew he needed to make sure she was OK with this, it had to be brutal.

"She will and she needs to. She has to cry and beg and then finally accept her fate."

"You'll be the one whispering in her ear, saying open wide darling and worship your Masters cock. Just as you say that she'll might just wonder if it's my cock. The not knowing will be killing the man inside her head."

Tim was over the moon, this was going way better than it had in his plans, this girl was going to be fun, she was getting fully into this, despite what Charlie had said about her being vanilla and frigid. Tim had once told Charlie that he really enjoyed dominating women, but that he loved the brutality of breaking males into fags the most, this time he'd get the best of both worlds.

"So I tell him to get you hard so I can get fucked, is that it?"

"I think we can do better than that, I think tell him that he's now your fluffer, that in future whenever you want to get fucked you'll have him blow the Bull first to prepare him for your pussy or asshole." Tim knew that Emma had never had anal sex, from his chats with Charlie but thought it was worth a push.

"Not my asshole, just my pussy, never my asshole."

"Ohh come on Emma, you're missing out and more importantly it's something you never, ever gave up for Charlie isn't it?" he let the question rest for a few moments.

"He told you that? fuck what a tosser?" Emma was bemused rather than angry.

"He simply answered my questions, I needed to understand his psyche as well as I could and so I asked about sex between the two of you. I know you don't orgasm with him, which is why it's so crucial that he sees you orgasm massively in front of him today."

"Well in the state I'm already in I may cum pretty quickly. I have to warn you."

"Well Emma I have to warn you that I have staying power and we need to show Charlie that she's no longer worthy of you sexually, that I can fuck you for a long time and make you cum, repeatedly, then when I've filled you with my load, you can feed her."

"Ummm I can't believe how much a turn on that statement is." Emma was plainly pretty tipsy now, but getting hornier by the minute.

"I have to say though, if she saw you fucked in both holes that would seriously help the process. The fact you've never allowed Charlie to fuck your arse or even go near it, will make her jealous beyond belief. Now that I think of it, after she's got me hard, you take the blindfold off and, you just suck my cock a couple of times before I slide into your pussy, again something she never gets, that would help too."

Emma looked Tim in the eyes and whispered, so you want all three of my holes is that it Tim?" she smiled as she said it, the Mojito's working their magic.

"That's it exactly, it will crumble the man inside him, piece by little piece."

"Then that's what we should do, but you have to be very gentle with my arse though please, I've never tried that. It's always scared me."

"No need to be frightened, you'll grow to love it, I'll use lots of lube too. I'll be gentle but firm, you'll beg for more and harder, just like she will, I'm sure."

Emma downed the last of her Mojito and immediately Tim topped it up and his own, although that was only his second, Emma had finished the jug almost on her own "One more for the road, for both of us, just to get us in the mood, bottoms up."

Emma snorted a laugh, "Bottoms up, you're a bloody comedian.""

"You won't be saying that when I'm lined up behind you Emma, you'll be begging for me to enter you." Tim knew this would be the case, he'd seen this all before.

They both drained their glasses, Emma signed the bill and put it on Charlies room. Then they stood to go.

Charlie meanwhile was in torment, her pussy stretched for a much longer period that ever before, she was sore now, every time she moved she whimpered and moaned into the ball gag. Taking the entire 10 inches most of the time, every few minutes when it all felt too much she would raise herself on her knees and get as much of the cock out of her asspussy as she could, straining the cords attached to the cuffs on her hands, but now her legs were getting so tired that they started to shake after only 30 seconds of so.

By now she was so exhausted that when she lowered herself back onto the cock, even though she tried not to, she couldn't help fall back onto the cock quite heavily going balls deep, her lube soaked ass cheeks spread wide on the table.

In all her 10 years of experience she'd never had her asspussy held open for this long or this wide for such a length of time.

Her mind was scrambled, the constant flow of the Pig Sweat poppers filling the room and her nostrils. The taste and smell of her cum filling her head combined with the cock deep inside her, meant she could hardly focus on what the hell Emma was doing right now.

Charlie had also cum twice more and was utterly spent, the constant stimulation of her prostrate had pushed her over the edge and milked her balls dry and a puddle of cum was slowly spreading over the table beneath her caged clit, mixing with the saliva that had dripped constantly from her ball gagged mouth. That feeling of total exhaustion after a massive sex session combined with high doses of poppers was washing over her.

As they rode up in the lift, Tim put his hand on Emma's shoulder to both reassure her and to start the process of getting her used to him touching her. She looked up into his eyes and smiled somewhat nervously.

"Don't worry it'll be fun, we just need to get her horny and high again and then the real fun can begin. How excited are you."

"I'm scared, but hot and bothered, I'm soaking down there."

"Let me see." Tim said as he moved closer to her and slid his hand down the front of her trousers, sliding into her panties and cupping her mons. His index finger slid gently into her crack for the briefest moment. She was shaking, not knowing what to do, but telling herself that she'd just asked this man to fuck her, so she could hardly complain at being fingered by him.

"Indeed you are wet little one, quite soaked." He smiled and withdrew his hand raising his finger to his own lips and sucking it clean, and such a lovely flavour too.

That moment where two people just subconsciously know they will kiss for the first time happened as he leaned down and little and she closed the rest of the gap, tasting her own pussy juices on his lips and loving the dirtiness of it.

They lingered over the kiss, Tim drawing her into him so that he could feel her pert nipples through her top brushing his chest and so that she could feel the bulge of his hardening cock. Both of them needed to get to the room soon.

Charlie could only hear her own moans and wasn't aware at all as the door opened.