Sissy in the Window-3
1540 Words
After a few minutes he turned and slowly peaked over the top of the window sill and was dismayed to see the girls still standing there. They saw his head and pointed laughing. He was trapped. He couldn’t resume the task until the girls went and he didn’t want them filming him in the act either as he knew they would share it across their social media and eventually it would reach someone who recognised him, even dressed up as a woman.
He waited for another ten minutes and again returned to the window for a quick peak. Not only were they still there but they were joined by another girl. He quickly retreated back to the far side of the living room.
After a few minutes he was horrified to hear the sound of a key in the door. Emma had returned.
He quickly scuttled back to the window and resumed the motion slowly moving up and down.
Emma walked into the living room strode over to her sissy slave and slapped him hard across the cheek.
‘You little bastard! I tell you to do one simple thing and you can’t even do that!’
His face stung he looked up with pleading eyes at his Master.
‘I warned you. You disobey me and I will expose you to everyone.’
She took out her phone and her slim fingers moved deftly across the screen.
He started to plead with her to stop.
‘Shut up or it will be worse for you. There. The video is now up online on a porn site. I won’t add your details . . . yet. But if you screw up one more time I will add all your personal details to it and make sure it is the first thing found when people look you up on the internet. Got it? If you perform like a good little girl for me for a month then I will remove the video.’
‘Please Sir, let me explain I was being watched by a group of girls I couldn’t stay in the window I could be arrested for exposing myself to them, please Sir you must understand. Please don’t expose me.’
‘You moron they are all eighteen and nineteen and they could only see your top half. But do you know what I think as you are so disobedient, they should see the bottom half of you as well, let’s get you dressed and looking sexy for your new audience.’
Justin was untied from the chair and looked thoroughly dejected. He was helpless and knew the ordeal was only just beginning.
Emma threw one of the shopping bags at him.
‘Put those on b***h lets see how you look while I fix the lighting.’
Justin pulled out the clothing his Master had bought him. He was shocked to see there was not a lot to what he was going to be wearing and everything was a bright pink.
He first pulled on some pink fish net stockings and a small lacey pink thong which caused Emma to squeal with laughter.
‘You can keep my bra on b***h but I bought you some spares cus that’s what you will be wearing now, even at work.’
He pulled out a short tight top that had “Barbie Doll” emblazoned on the front.
Again Emma loved it and laughed out loud. ‘Oh, now the boots they were expensive but you know what I think you are worth it.’
Another bag was thrown at him and he removed a pair of knee high pink plastic polished platform boots with a strap and padlock around the ankle.
‘Put them on, don’t worry about the lock I have the key. You will be able to get out of them when I decide you are ready to be released. Now walk across the room like a lady.’
He pulled them on, tied up the laces and with a sense of reluctance bucked the strap tight around his ankles and clicked the padlock shut.
He rose to his feet and wobble precariously on the platforms and thin stiletto heels. He managed to stumble from one side to the other while Emma was in fits of laughter.
‘More wiggle b***h, you’re a girly girl now.’
He tried again and swaggered and stumble with a little more decorum and sense of posture than before.
Emma then proceed to take the bulb out of the overhead light and replace it with a red bulb.
She then removed the spotlight by the window and replace that with another red bulb.
Turning on the lights Justin’s living room was bath in a warm red glow.
‘Perfect! Now you can sit in the window and people will instantly know what you are offering.’
‘I am sorry Master I don’t understand?’ There was a sense of panic in his voice.
‘Well I thought I am going to a lot of effort to get you looking nice and girly it would be a shame for others not to enjoy it as well. So, every evening between six and nine you will sit in this window with the red light on dressed in your finest slutiest clothes. That is unless you are not with a client.’
‘What, what do you mean client?’
‘Well now that you are my b***h and I own you I thought it would be fun to pimp you out. You are just such a little fun slave I wanted others to enjoy you. Don’t worry I have a few ground rules, no permanent marks, nothing illegal and everything stays inside these four walls. They can film the show if they want but they cannot share on social media unless I approve it. In return they can dress you up however they like, you will serve them food and drinks, dance or entertain them in whatever manner they desire. If they want you to clean their high heels you will, if they want to grind their boots into your face and stand on your neck you will let them and thank them afterwards. The only exception is you will not have penetrative s*x with them and you will not be allowed to c*m unless they command it. The best bit is I will get paid for your services. Sounds fun doesn’t it?’
‘Please Master you can’t do this to me.’
Emma marched over to her whimpering slave and slapped him hard across the face.
‘You don’t understand do you? I own you. You do whatever I say. But more importantly, deep down you really want to be my w***e, don’t you slut?’
Justin struggled in his mind to fight the idea that he actually could live as Emma’s cross-dressing prostitute, how the hell could he look her in the face everyday if she was making him do this every night? A part of him did like dressing this and he loved Emma being in charge and so dominant. He even got a thrill when she slapped him. What had she done to him? He could feel himself being aroused by the situation but deeply terrified of the future. Maybe it would be alright, maybe he could enjoy serving other girls that would abuse him as well and make him please them. Maybe, just maybe he could make his Master proud.
As these thoughts tumbled around his brain he heard a knock at the door.
Emma looked at her watch.
‘Ah that will be your 2:30 appointment. Pucker up girl its showtime. Well, off you go open the door and let them in be polite, address them as Miss and make sure you know your place.’
Justin scuttled off his heart beating faster and faster in his chest as he tried to walk elegantly in the high heels down the hall.
He opened the door and to his horror saw the four girls that had been standing looking up at his window about half and hour ago.
They all laughed as they saw the image of Justin framed in the doorway. His face went red as he lowered his head, thanked them for coming and asked them to come inside.
All four girls pushed passed him giggling. They were even more beautiful close up. They all had heavy make up and hair pulled up into a ponytail. They wore short skirts and they slim long legs ended in frighteningly sharp slim metal tipped high heels. Two of them were carrying bottles of wine while a third waved a large black dildo in front of his face.
‘Carry this for me will you honey.’
Justin extended his arm to take the large rubber black phallus.
‘Naughty, naughty not in your hands in your mouth. Open wide.’
Emma’s words were ringing in his ears. He need to do everything he was told to get that video taken down. As his lips parted the girl rammed the large dildo into his mouth making him gag. She pushed it harder and laughed. Justin was nearly crying with the humiliation and shame of being abused like this in his own home by girls half his age.
Justin closed the door and tottered after them. Although he felt humiliated and ashamed of his appearance he felt fear and anxiety about what would unfold in the following hour.
As he came into the living room he saw the girls all laughing and chatting to Emma.
‘Hey Emma, we got changed into our best shoes like you said. Here’s your money; now let’s bring on the gimp and let’s have some fun!’
THE END
- Writer
