Sissy Destinee

Jayce pulled his hands from his face and pushed them over his short sandy hair to hold the back of his head, he was really in a mess, stuck in a situation with no way out and he had nobody to blame but himself.

He had no idea what had driven him to pick up the lacy peach coloured pair of panties that had been sitting in a fifty percent off bin of men's clothes in his local superstore and stuff them in his pocket instead of just ignoring them. It wasn't until he got home and found them that he even realised that he had left the store with them.

Jayce had never shoplifted anything in his life before, he was a straight A student at school seemingly destined for higher education, but instead of going straight to college or university after graduating he had found himself a good, modestly paid job, moved out of his parents and was now living quite happily in a small rented apartment. He had never had any inclination to try on women's clothes and although there had never been any serious long term girlfriends he had always considered himself to be and appeared to all he knew as straight.

So as soon as Jayce found the lacy item stuffed in his pocket he had been wracked with guilt and embarrassment at the idea of taking them back and admitting that he had 'accidently' walked out with them, so he just threw them in the trash bin in his kitchen and resolved not to think about it again.

That was until the following morning when he found a large parcel on his doorstep with a folded note on top that simply said 'Read Me.'

Opening the note up Jayce saw a printed image and went white as a sheet, it was him in the store in the process of stuffing the clearly visible panties into his pocket and underneath was written.

'I know what you did and have video evidence, if you don't want anyone else to know that you are a sissy panty thief then open the box and switch on the phone you will find inside.'

Jayce looked up and down the corridor outside his apartment but saw no one, so he picked up the box and took it inside.

Placing it on the floor after closing the front door Jayce knelt down and opened up the lid, inside was a layer of white tissue paper hiding the contents and on top of the tissue paper there was a phone. Jayce picked it up and nervously switched it on as the note had instructed. He could see there was one message waiting so he clicked on the icon and began to read.

'Now you know I have evidence of your theft little sissy and as I followed you home I know where you live, so if you do not want everyone to know that you are a sissy panty thief and receive a visit from the police then you will do as you are instructed, reply to this message with yes if you understand?'

Jayce gulped and typed yes and pressed send, he waited a for few moments and then jumped as the phone bleeped suddenly as a response appeared.

'Hello sissy, as you desired those peach panties so much that you had to steal them I thought you might like the rest of the outfit, wrapped in the tissue paper below you will find the matching body and stockings to complete the set.'

Jayce looked down at the box and the white tissue paper now knowing what was hidden beneath, the phone bleeped again and another message appeared.

'There is also a pair of white high heels, I had to guess your size but I know they'll be close, I've had a lot of practice guessing a sissy's shoe size over the years.'

Jayce sighed feeling anxious about what had his momentary lapse of reason got him in to, then the phone bleeped again pinged.

'Underneath all that is a big box of cosmetics and what I want you to do my little sissy is to put on the lingerie, make yourself all girly and pretty for me, I'd advise watching a few tutorials if you haven't practised much before and then give yourself a good squirt of perfume. Once you've done that you will take a selfie and send it to me.'

Jayce looked at the phone in horror, he couldn't believe what was happening, he was being blackmailed into dressing up in women's clothes and not only that he was being told to take photographic evidence that he had done it and send it to a total stranger. As he stared at the phone another message appeared.

'Do you understand what I want from you?'

Jayce just looked at the phone in shock, he couldn't do this, he wouldn't do this.

Another message appeared, this time it was just a GIF file with the message 'watch this' Jayce tentatively clicked on the file and saw himself from the viewpoint of a security camera in the store stuffing something into his pocket, it then went to a close up and you could see it was the pair of peach coloured panties. As Jayce stared blankly at the phone screen another message appeared.

'Do as I tell you or in a few hours, the store owners, then the police will see this and then you will go to jail and for a sissy like you.. Well I think you can guess.'

Tears filled Jayce's eyes, he didn't want to go to jail, he gulped, he knew he would have to do as he was told.

'Do you understand now?' came another message.

Jayce slowly typed his response 'Yes I understand.'

'Good sissy, I expect to see a selfie from you within the hour, do you understand?'

Jayce wiped his eyes clearing away the tears and typed 'yes.'

'Then get to it sissy.'

Wobbling uncertainly on his feet Jayce stood up then picked up the box and carried it to his bedroom. There he dropped the box on the bed and pulled aside the tissue paper. As the texts had promised he saw the peach body and pulled it out along with a packet of stockings, beneath those was a pair of chunky high heeled strappy sandals. Jayce picked one up and examined it, from the label it was clearly a size too small and the heels looked precariously high, each strap had a little silver buckle and each would have to be secured to be able to wear them. Jayce put it down on the bed, took the other out of the box and placed next to the other shoe.

Pulling out the large red leather case that sat at the bottom of the box and placing it on the bed, Jayce looked at it for a moment then opened it up, it was full of cosmetics, he recognised lipsticks and nail polish but had no idea what the rest was for, he guessed he'd need to watch those tutorials, to figure out what everything was for. Glancing at the silky body on the bed made him remember the panties and where he had left them, he would have to get the them out of the trash.

Sighing Jayce headed back to the kitchen with the realisation of what he was about to do crashing over him making him feel sick to the stomach, fighting the sudden urge to throw up he rushed to the bathroom and knelt over the toilet bowl, he retched a couple of times and a trail of spittle dripped from his open mouth into the water below, but he didn't throw up and so pulled himself to his feet washed his face with cold water and buried his head in his hands.

Pulling them away and over his hair he stared at himself in the mirror, his reflection looked sad and a little afraid.

'You can do this' he said to his reflection, trying to convince himself 'You can do this and then it'll be over' he wasn't sure he believed that part but he needed something to grab hold of otherwise he wouldn't be able to go through with everything 'You can do this' he told himself a third time and then forced himself to walk out of the bathroom to the kitchen.

After fishing the panties out of the trash and giving them a quick brush to rid them of the few crumbs they had picked up from lying atop a few days' worth of rubbish Jayce returned to the bedroom where he just stood and stared at the lingerie and shoes laying on the bed with the panties clutched in his hand. Shaking his head mumbling 'no choice' Jayce dropped the panties on the bed and stripped off his clothes until he was naked. Being tidy by nature Jayce picked up his discarded clothes, hung up his trousers and shirt in the wardrobe and threw the socks and pants in the laundry basket before returning to the side of the bed and picking up the panties.

They felt soft and cool to the touch, different to his normal cotton pants which were slightly rougher in texture and always felt warm, sighing he stuck first one leg and then the other through the leg holes and pulled them up his legs, he spent a few moments adjusting himself so they sat comfortably over his genitals and then turned his attention to the body. It was a mass of straps and ribbons that once he had figured out how to hold it up correctly connected to a lacy peach coloured front panel with a short mini skirt around it's waist, from below the mini skirt dangled four suspender straps. Carefully he climbed into it and pulled the snug garment up over his body and hitched the straps up over his shoulders.

Then bending over he tugged and pulled at the suspender straps until they were dangling freely from underneath the mini skirt which barely covered his panty covered groin, Jayce felt ridiculous, he knew this sort of thing turned a lot of people on but it wasn't doing anything for him and his penis remained completely and utterly limp. Sighing he grabbed the packet of stockings, ripped it open and pulled them out, over the diaphanous nylon was a peach fishnet pattern and plonking himself on the bed making the box of cosmetics rattle he pulled one over his foot and up his leg.

Fortunately being blonde what little hair he had on his legs and body were barely noticeable so when covered by the pink nylon they totally disappeared from sight and once the stocking was up around his thigh Jayce fiddled with the suspender fastenings until he had them affixed, then he did the same with the other stocking. His gaze then went to the heels laying on the bed besides him, he picked one up and lifting up his leg he slipped his foot in and bracing it on the edge of the bed he tightened the straps and fastened the buckles, then doing the same with the other shoe he gingerly stood up.

Finding himself suddenly much taller and oddly balanced Jayce took one step forwards and fell flat on his face. he lay on the floor for a second slightly winded, his left ankle hurt intensely where he had gone over on it and as he sat up he pulled his leg in close and rubbed at it, his hand caressing the nylon. An odd thought struck him as he did, despite the pain on his ankle stroking the nylon felt quite pleasant. Rather than try to stand in the heels and risk falling over again Jayce unbuckled them and pulled them off. He could wear them when he was ready to take a photograph then hopefully he thought he would never wear them again.

Knowing what he had to do next Jayce pulled himself to his feet and sat back down on the bed, he picked up the box of cosmetics and balanced it on his lap, he picked at the various pots and brushes, looking at each and then putting them back, he really had no idea what half of it was, he knew he needed to watch some tutorials, so taking the phone he connected it to his internet and after a little bit of searching found a lot of tutorials on how to put on make-up from start to finish.

Jayce picked the first on the list and watched it from start to finish, he was frankly shocked at the amount of work that went in to putting on your face as the instructor called it, then he sorted through the box to make sure he knew what every item was and when it would be needed. Once he had done that Jayce picked up the box of cosmetics, dropped the phone in and then balanced the shoes on top and took everything to the bathroom where he had a large mirror above the sink and a long mirror on the wall that he could use to take a selfie.

Once in the bathroom and feeling a little bit cold due to lack of clothing Jayce shaved his face and then played the tutorial again and began to follow it step by step, putting on foundation, blusher and carefully applying liner to his lips before filling it in with a bright red lipstick. Then came the tricky part, his eyes, trying to draw eyeliner across the bottom of his eyes was almost impossible but after several attempts resulting in him having to carefully removed a black line that slipped down his face he managed to get an almost straight line under each, then using the dark shades provided he darkened his eyes and highlighted them with a silver eyeshadow.

Looking at himself in the mirror Jayce was sort of impressed, he'd done pretty good job considering it was his first attempt. Then he turned his attention to the box of false eyelashes, it took ages to get the fiddly things glued to his eyelids as they kept slipping before the glue had set properly but after some perseverance and a lot of swearing he managed it and added the finishing touches by swiping them with a mascara brush. Fluttering his now noticeably heavy lashes Jayce ran an eyebrow brush over his eyebrows making them a shade darker, then looking in the mirror he decided he was done.

All that was left was to squirt himself with the small bottle of flowery perfume Jayce had found mixed in with the cosmetics and as the final finishing touch clip on the long dangling earrings that had fallen out of the make-up brush bag when he was checking the contents. He was done and whilst it was something he had not even remotely wanted to do Jayce couldn't help but admit that he had done a good job, yes he still looked like himself and anyone who knew him would certainly recognise him but it was a good job nevertheless.

Neat as ever Jayce tidied away the make-up putting it all back in the box, but he left out the few bottles and jars of make-up remover that he had found intending as soon as he had sent the selfie to get it all off and throw everything in the trash and be done with this experience once and for all. With that in mind he picked up the phone and turned to face the wall mirror.

Looking in the mirror on the bathroom wall Jayce took in his transformed appearance once more shrugged at himself and took the selfie, then with more than a little trepidation sent it in reply to the last message on the phone. He didn't have long to wait until he got a reply.

'Not bad at all, you have a very sexy body and good work with the make-up. You are a very pretty sissy.'

Despite himself Jayce smiled to see the positive response to his selfie then another message came up.

'But you need to do something with your hair, it looks too boyish, you need to fluff it up, have you got any product?'

Jayce looked at his reflection, his hair did look flat and boring, typically male, as he was pondering another message appeared 'sort your hair out sissy, and send me another picture, you have five minutes or you know what will happen!'

Jayce shivered and not form the cold, he put the phone on the side of the sink and grabbed a tub of gel from the bathroom shelf. Taking a scoop he rubbed it into his fingers and began to run and pull them through his hair until it had more volume and body. Picking up the phone he saw that there was another message.

'One more minute to send me another selfie.'

Franticly Jayce turned to face the wall mirror and took another and sent that one off.

'You look much much better' said the message that appeared a few seconds later 'though you need to work on your pose, swing your hips to one side and jut that sexy little sissy butt out, then take another.'

Jayce wobbling on his high heels in the unfamiliar and awkward position did as he was told and quickly sent that one too.

'Good, now you are getting it sissy, take one as though you are about to kiss a man and send it to me.'

That instruction broke Jayce out of the moment and the realisation of what he had been doing for the past five minutes hit him with full force, he looked over at the pretty young thing in the mirror, the reflection could almost have been mistaken for a girl with a mannish haircut except for two obvious giveaways, the lack of any noticeable breasts beneath the silky body and the slight bulge distorting the front of the peach coloured panties.

The phone pinged in his hand and Jayce looked down at the new message.

'Stop daydreaming sissy and send that picture to me now!'

Jayce looked back up at his reflection and gave it a sad smile, held up the phone, pursed his lips and took the photo, he sent it off and waited.

'Take another and this time look like you mean it, like you are kissing the most important person in your life.'

Jayce sighed and rearranged his face, he smiled broadly, tried to imagine kissing someone he wanted to kiss but a mental image of his perfect woman wouldn't come, he kept seeing someone tall and manly, ignoring it he pursed his lips again and took another selfie.

Once he had sent that one off Jayce had to wait for several minutes for a reply.

'That was very good sissy, I've now added all your pictures to a page I have set up for you on sissyprostitutes.com, all I have to do is click upload and everyone will think you are a sissy prostitute, so not only would you be arrested for theft but eventually also prostitution when the police checked you out if you do not continue to do what I tell you.'

Jayce went as white as a sheet when he read the message and once again felt as though he was going to throw up, so much for this torment ending once he had done as his tormentor had asked.

Another message appeared 'Sissy, do you understand that you are now mine to do with as I please?'

Terrified of where this situation was going Jayce could only type 'yes' into the phone.

'That's good sissy, you've learnt a valuable lesson, now go sit down somewhere comfortable and wait, soon there will be a knock on your door soon, you will answer dressed exactly as you are, you will politely welcome your guest and then do exactly as you are told. Do you understand?'

Jayce was overcome with fear, someone was coming here and if he let them in they were going to see him dressed like this and who knows do what to him, his fingers hovered over the keys but before he could type anything another message appeared.

'Do not make me wait unless you want your life to completely over. I will ask you one more time sissy, do you understand me?'

Eyes beginning to tear up Jayce gulped, he could only do one thing and he quickly typed 'yes.'

'Good sissy' came the response 'now one last thing, from now on you will only answer to the name Destinee do you understand?'

With no other option Jayce responded 'yes.'

'That's good Destinee, now go and wait patiently like a good sissy and keep the phone with you, you will be needing it once your visitor arrives, have fun.'

Jayce stood there in the bathroom for several minutes just staring at the phone in his hand, his mind in utter turmoil, hopefully waiting for another message that would tell him this was all a prank and nothing more was going to happen, that he could go back to his normal life as if nothing had happened, but the phone remained silent, no more messages arrived.

So Jayce could only do as he had been instructed and went to sit in the living room, he wobbled unsteadily on the high heels which forced him to take tiny little mincing steps, the unfamiliar movement made him feel uncomfortable as it caused his hips to sway in an entire new and ultra feminine way, he felt a little cold with so much flesh on display but eventually he made it to the living room and sat down on his sofa.

He looked at the phone in his hand again hopefully, but there were still no new messages, he wondered what his tormentor had meant by needing it once his visitor arrived, every single idea that crossed his mind filled him with trepidation and he got more and more worried as the time wore on.

Without warning there was a loud knock on his apartment door and Jayce jumped almost falling off the sofa

Gulping Jayce stared over towards the front door and considered just not answering, but he knew he really didn't have a choice, he knew that perhaps he had had one before he put on the clothes and make up and then sent out all those selfies but now he was utterly trapped by the mysterious blackmailer and that he had walked straight into that trap himself.