tagTransgender & CrossdressersAliExpress and Sissy Downfall

AliExpress and Sissy Downfall

byHis_fag_wife©

It all started with a visit to a TV Mistress on a work trip, Charlie had been cross dressing in some way or another since he was a teenager. First just his Mums used panties, then a lodgers underwear and finally he'd started to buy the odd thing himself.

As time went on, BDSM was added into the mix, Charlie realising he was submissive and when he found Sissy Hypno videos and the TS Seduction site he'd found the kinks for him.

Progressing over the years from Female Pro Dommes, to TV and TS Dommes and finally to gay Masters, he knew he just loved to be totally dominated and fucked as a fuckslut and treated as a gay sissy faggot.

But he was married and his vanilla wife had no interest whatsoever in sex, let alone in any form of kink. Their sex life was non-existent and now he found his release from writing stories on Literotica and reading other peoples stories. When he was away on business, he loved nothing more than to be in a hotel room, headphones on, dressed in PVC and stockings watching and listening to sissy hypno videos whilst stuffing his asshole with a good sized dildo.

The visit that changed things was to a Mistress Tegan a TV Mistress and she introduced a couple of extra ideas into Charlies kink vocab, the first being self-bondage and the second that Aliexpress was the source of all sorts of delights, but at a fraction of the cost of buying from his usual sex shops. When Charlie saw her amazing collection of kinky clothes, butt plugs, dildo's and BDSM gear he knew he needed to improve his kink bag for his trips away.

Previously he'd squirreled money away before his trips, but the cost of a corset or a dildo in normal retail was always prohibitive and the fact that guilt so often got the better of him after a trip, that he threw the clothes and gear away, meant it was simply money down the drain.

Now he realised he could kit himself out with much more for a fraction of the cost, a PVC body costing $14 instead of $50, a butt plug for $4 instead of $45, a chastity cage for $14 instead of $150, he was like a kid in a candy shop.

He carefully squirreled some money away until he had $300 and set up an account in his name. That was only part of the conundrum, Mistress Tegan provided the next part, she was happy for him to send items to her house and for him to pick them up from there. As she said when she made the offer, "Just so long as I get to see you wearing the clothes or the other items in use on you, I'm happy." He also asked her to get him a couple of bottles of poppers as she had a very good cheap but quality source.

So he began his shopping list, looking each day and adding, or taking something off or some slight amendment when he found something better or cheaper.

His shopping list was long and included the following

Full make up kit - $10

Large Electro butt plug 2.5in diameter-$5

Black butt plug 2.5 inches diameter - $4

Small chastity cage with urethral insert - $14

PVC body with crotch zip $14

10 inch black dildo 2 inch diameter - $15

13.5 inch black Bam dildo 2.5 inch diameter - $25

Black patent high heels with padlock straps and 5 inch heels -$35

4 pairs of black seamed stockings - $5

Breast forms size C - $26

Water Soluble glue for breasts - $12

3 sets of lingerie - one black, one pink, one red $12

A leather corset - $24

Underbust waist trainer $15

1 black bob wig - $16

10 mini padlocks - $10

Pink silk night gown $4

Short silk dress in gold $14

Large butt plug 2.5 inches in diameter - $4

Enema kit $4

Breast enlarging suction cups $14

Hitachi style wand $14

Timer lock -$6

Full head hood - $12

Ball Gag $3

Open mouth gag with plastic bright red lips. - $2

A wide back leather collar with the words COCKWHORE in silver on the front. $5

Ankle cuffs which could be padlocked shut. $5

All at once he was going to be fully kitted out. It would mean travelling light on his business trips to take the added weight (and then only taking the right things) but his cock was rock hard at the thought. Now he could dress in his favourite pvc slut outfit, or dress for cocktails in his room.

As he pressed order he was intoxicated with the thoughts of what fun he'd have. He had no idea of the Pandoras box he'd just opened.

Hi next trip away necessitated 2 nights in Auckland before he flew onto the US. He'd asked Emma his wife is she'd fancy joining him for the Saturday and through the Sunday evening as he'd be dining out with customers and she could happily join them. A good weekend in a great hotel on the companies dime.

She'd thought about it, but decided against it with the childcare issues just too tricky to sort out. Oh well he thought, it simply meant he could indulge his kinks for more time whilst he was away.

A week later he received a photo from Mistress Tegan showing the full array of his purchases laid out on her bed, with a sheet of A4 paper on which she had written "Come and get it slut!! And bring a big bag."

Now it was real, now he couldn't wait.

He'd booked a great hotel and was flying up early on Saturday morning and then planned to go straight to pick up his purchases before enjoying the afternoon in self-bondage in his hotel room and then a great meal out on the evening. He packed his suitcase with lots of room to spare, he had far fewer clothes than normal to make sure he wasn't over the airline weight limits.

His wife was out with the children in the morning, so they said their goodbyes early. He jumped into the shower, in preparation he shaved his ass crack and his balls. He always left the hair above his cock as it at least made him feel a little bit manly and also his wife wouldn't think anything strange as he occasionally shaved his balls telling her he liked the feeling of it.

She'd made no mention of it until she noticed after one trip that he'd also shaved his chest. His only excuse was close to the truth, saying he'd been drunk and got carried away, as they'd done just that on occasions and he'd shaved her pussy a couple of times in the past.

Once he'd shaved he gave himself had a full enema rinsing 4 times and then waiting to pass as much water into the toilet as possible and then got off to the airport.

He spent the journey detailing the order of play for the day, although he couldn't be sure how long things would take with Miss Tegan as he picked up his gear, she might want to play a little.

Once he'd checked in and dropped off his luggage in his large suite he was desperate to get a cab to Mistress Tegans. He took a bottle of wine with him as a thank you for using her address. He knocked on the door and she was fully dressed as usual and rocking the kinky Domme look that she usually did for sessions.

"Hi Charlie, sorry but we'll have to be quick, I have a client coming in half an hour."

"No problem Mistress Tegan, thanks so much for having the gear delivered here. I can't wait to see it."

"Well come on through then slut and look at your goodies. You are going to have a very kinky time aren't you."

"I certainly hope so Mistress."

As he walked to the bed and surveyed his new collection he was light headed at the possibilities, this afternoon was going to be a lot of fun.

"Here's your Pig Sweat poppers that you like so much. Too strong for me, but I know you love them."

Charlie paid Miss T for the poppers and opened his back pack and began to load his new toys into the bag.

"Hey not so fast slut, I did say I wanted to see some of these on or in use, didn't I?"

"Yes Mistress but I thought you're in a hurry."

"Well I am, but you can hardly go out of here without some discomfort can you. Then you wouldn't be being true to the sissy sub slut you really are."

"So very true." Charlie said as he lowered his eyes. "What would you like to see Mistress?"

"Umm, what indeed, let's have a look. Well if you are going to be decent on the journey to the hotel, then I think we can go with the PVC body and off course your slut hole needs filling and that butt plug looks perfect for that journey."

She paused and surveyed the scene "Then the final point should be the chastity cage I think for some discomfort and to remind you of the slut you are. How does that sound slut? Now get stripped off, I take it you are clean."

"Yes I'm clean and good to go, your choices sound perfect thankyou Mistress." He said as he started to strip off his jeans and polo shirt.

"The high collar of the body will show over your polo shirt, but that's the sort of humiliation you deserve isn't it slut."

"Yes Mistress it is indeed."

"Now sit on the bed so I can fit your chastity cage."

As he took off his socks and was completely naked, his cock was rock hard, now at its full 6 inches.

"Ohh dear we're going to need to do something about that slut aren't we, do you think I should use pain or pleasure to make it go down?"

"Whichever you think I deserve Mistress." He said it hoping for the pleasurable outcome, but knowing that was not his choice.

"Good choice slut, pain it is then, now get sniffing on these as that tends to help you shrink doesn't it."

She passed him the new bottle of Pig Sweat and he opened it and started taking in long breaths to load his mind up and to help relax both his anus and his cock.

As he did so, Mistress Tegan took a very firm grip around the base of his cock and balls and squeezed hard, starting to crush him bit by bit.

"He moaned in pain as she pressed ever more firmly and his erection started to deflate."

Mistress picked up the chastity cage and admired it, cradling it in one hand, whilst crushing his manhood with her other.

"Ohh good slut, you've gone for the super small one, perfect with you being a grower not a shower."

Charlie could only moan and continue to sniff as much poppers as he could in response.

Mistress took the 40mm metal base ring and pulled each of Charlies big balls through and roughly then pulled the rest of his scrotum through and then carefully poked and prodded his softening cock through, pulling the whole package through as far as she could so that the base plate was snugly against Charlies pubic bone.

She then took the head of the cage with the ring that once locked in place would only allow a 8mm gap between the two rings trapping his scrotum between the rings and leaving his big balls hanging below and completely unable to be pulled through the gap, effectively imprisoning the balls and making it escape proof.

Then she pulled his foreskin back as far as she could between her thumb and forefinger and his glans began to swell a little, effectively trapping the foreskin under the head of the glans. She then took the head of the cage with the urethral plug and inserted the plug slowly into his urethra.

The plug was stainless steel and 40mm long and 4mm in diameter, she threaded it in slowly rotating it and using his pre cum as lube until it was all the way in. Charlie groaned as it went in. The length meant that it was actually inside his body as she compressed his cock back into his body and left only the livid purple head showing inside its new cage.

Once the holes lined up on the head cage and the base ring, Mistress Tegan put the locking pin in and removed the key. There was absolutely no way for Charlie to get out of the chastity cage without that key.

He made a bizarre sight, his big ball sack and balls hanging down, freshly shaved and ringed tightly in the stainless steel ring. All that was showing of his cock was barely an inch of purple throbbing head.

Just for good measure the smaller ring which housed his now miniscule cock was lined with spikes inside, should he get excited at all, there would be consequences.

Now Mistress Tegan cradled the cage in her hand, "Ohh that is simply perfect for you sissy, now no one will see you as a man, they'll see you as the pathetic sissy slut you are, with your angry clit ready to be tortured."

"Yes Mistress Tegan they will." He groaned.

Now take another good few pulls on the Pig Sweat, this butt plug is a big one and I haven't got time to fanny around, I want you full and off on your merry way."

Charlie took another 4 long breaths in, alternating each nostril, getting as high as he could to help with the intrusion he was about to feel.

"Now on your knees and pull those slut cheeks wide apart for me, it's time to fill your ass pussy up for the journey into town."

Charlie assumed the position, it was one he'd learned well over the years, he rested his head on the bed, reached back and pulled his big ass cheeks as wide apart as he could.

Mistress Tegan, poked one lubed finger in roughly and then added a second, working them in an out quickly and efficiently, widening his ass to accept its fate. Once she had three fingers in she began to rotate them and stretch them out until the fourth finger joined and she considered that her slut was ready.

"Now you can remove your hands and feed on some more pig sweat, you've opened up well but this will still take some force to get it in quickly, I only have a few minutes before you have to dress and get out of here."

Charlie knew what was coming and knew he needed more Pig Sweat to take this without feeling like it was ripping him in half.

As he snorted for the second time, Mistress removed her fingers leaving him gaping "Now bear down like a good girl slut."

He tried to shit as forcefully as he could knowing that would open him as wide as possible, with constant pressure Mistress T got the plug to the widest point but couldn't quite get it all the way in.

She placed one hand over his balls crushing them once more, to take his mind off the pain in his ass and dipped the plug to one side to get his anus over the lip of the widest part of the plug before rotating it to get it all in.

Charlie moaned out loud as he felt the plug conquer his ass and as his asshole contracted hard onto the snap back of the plug holding it firmly in place, both filling him up and keeping his asshole nice and wide open.

Mistress had only used a very small amount of lube so it would stay in place nice and tightly.

Mistress T slapped his ass cheek hard leaving a red hand print and then spanked the base of the plug a few times to stimulate his prostate.

"Perfect now up and into that PVC body quickly, he'll be here any second."

Charlie got up and put both legs through the leg holes, sliding one arm in then the other as Mistress pushed his balls up into his body to allow her to close the crotch zip tightly constricting his new cock cage, she zipped the body up and padlocked the under the crotch zips together, imprisoning the plug in place. The body had a boy short style cut at the bottom, so there no way he could possibly slide the huge plug out of his hole without having the key to the small padlock.

The next stage was she tightly closed the collar of the body, which covered the top zip not allowing access to undo it and locked the collar at the back adding yet another of the small padlocks.

"Now I thought about this for the last couple of days and I don't want you to even think about getting out of any of this outfit until you've walked through reception in the hotel like the little slut you are. I want you to have to do the walk of shame with the high pvc collar now locked in place. Your polo shirt collar will just cover the padlock if you turn it up."

"Yes Mistress thank you for ensuring my humiliation." He was nervous. But nothing for it now, but to get dressed and cover up as best as he could and get back to his room for an afternoon of fun.

As he was dressing Mistress was packing his bag. He saw her put the 3 padlock keys in first at the very bottom of the backpack along with the key to the cock cage.

"My final little thought to ensure that you keep everything in place for a little while at least is this..."

She held up the timer lock he'd bought and threaded the steel cable of the lock through the two zips on the backpack effectively holding it locked closed.

His heart sank, how long would she set it for?

Mistress Tegan set it for 1 and half hours, laughing as she did it.

"God you'll be desperate to get that plug out by then, it's filling you up so much. Hope you don't need to pee in the meantime, or you'll just have to wet your PVC body like a dirty little piss slut."

Just her mentioning the need to pee, made him aware that he had drunk a full water bottle on the way to her house. He'd purposely not eaten anything to ensure that he remained clean for the day. That did result in some light headedness especially with the combination of pain and poppers, but he loved that feeling.

She passed him the backpack and the opened bottle of poppers.

"Here you may need some more Pig Sweat to take the edge off that huge plug fucking your boi pussy with every step."

As she reached to cradle his cage, "Ohh and to keep you flaccid so the spikes don't dig into the head of your Sissy clit."

"Thanks Mistress." With that he took another two long snorts of Pig Sweat to help on the journey home.

"Now get out of here slut and send me some photos, have fun."

He walked down her steep drive, his head spinning and calling up an Uber Cab as he reached the bottom of the driveway, he looked up and saw a business acquaintance crossing the road and coming towards him.

Fuck they must have seen him come out and they couldn't miss the high PVC collar locked in place, even though he had turned his polo shirt collar up.

He was flustered and didn't know what to say or do as the guy simply said "Hi Charlie, have a good one." Smiling at him as he walked past him and knocked on Mistress Tegans door.

Shit thought Charlie he's into kink too, well I never.

The Uber cab came and for once the drive into town was quick, within 15 minutes he was back at the hotel, realising he couldn't go out and sit over lunch dressed as he was. He walked straight through the crowded lobby, most people checking out and concentrating on their own lives, although he did feel as though a couple of sets of eyes followed his slightly bow legged progress across to the elevators.

He got to his room and closed the door behind him with a sigh of relief, then he thought, shit I'm stuck like this for the next hour and a bit.

He couldn't do his make-up, try on the wig or anything, so he got out his own bits of gear from his suitcase, his collar, straps and more locks and decided to set up for the afternoon's scene and get his computer up and running for what he had planned.

Ever since he'd written his shopping list he'd had a plan in mind.

He was determined to put himself in self bondage that he simply couldn't get out of for a couple of hours, his cuffs held in place behind his back by the timer lock. Him sitting legs akimbo impaled on the smaller dildo, which would be suction cupped onto a smooth surface.

He'd be strapped or tied down upon it with all 10 inches deep within him so that all he could do was to rise up on his legs and get 6 inches or so of the dildo out of his ass pussy before his legs hurt and he'd have to again take all 10 inches.

No escape, just the option to fuck his own hole to gain temporary relief from the full depth of the dildo.

His aim was to watch sissy hypno videos, TS Seduction videos on a loop with his head phones on, so he'd be absorbing the messages as he fucked his own pussy with the ultimate aim of a hands free orgasm, or an anal orgasm as it was known, in some circles a sissygasm.

He'd never had one yet, but he hoped against hope that today was the day. He saw it as a rite of passage to giving up his manhood and being a true sissy slut.

He wanted this so much and to be fully made up as a kinky faggot slut whilst he was filming himself doing this.

But he had to pass some time before he could do much, so he set his computer up at the end of the bed and set the low coffee table just next to it so he could sit on that, now feeling the plug pressed deep within him. He opened his various accounts, Fetlife, Collar Space, Tmblr, his kink Hotmail account, Literotica so he could read stories and see if he had any messages and how his stories were being rated.

Report Story

byHis_fag_wife© 5 comments/ 33167 views/ 31 favorites

Share the love

Report a Bug

Next
3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel