This story is a work of fiction and should not be read by anyone who is not mature enough to separate fact from fiction.
I would love to hear any feedback or comments that you have.
Jason woke up at 10pm on the Saturday morning still in the same position he slept in the night before. He got up feeling something stuck in his ass; he reached around, finding the end of the dildo sticking out of his ass. Jason pulled the grey thong down to his ankles and threw it to one side of the room.
How did that get there Jason said out loud, he reached pulled the dildo out and looked at the size of the thing that had been invading his passage, It was covered in shit and lube, he dropped it on the floor in fright.
I put that there...why did I do that...what has she done to me? Jason thought.
Looking around the room at the various sex toys, which decorated his flat, he went to the shower, switched it on and took off his tranny clothes. Getting into the shower and trying to scrub the events of last night off his skin, he reached around to his ass and took the shower head, pointing the stream of water at his asshole, cleaning the lube and dried shit off his ass.
The phone started to ring but the sound of the phone was like electric to Jason, he got out the shower still wet and ran to the phone picking it up.
Hello,
Hello slave, very quick answer but I think that you could do better.
Yes Mistress (how did she get my number?)
What are you doing Slave?
Taking a shower Mistress, just got into the shower when you rang Mistress.
Oh you got out the shower just for me, that's so sweet my little slave.
Yes Mistress (what's she done to me...what's she going to do to me this time!)
Did you have a nice sleep slave?
No, Mistress, I went to sleep with a dildo up my ass Mistress
That's a silly thing to do isn't it slave, you must really be desperate to prove you really are not a man.
I am a man Mistress....
I don't think real men sleep with a dildo up the ass do they slave?
No Mistress...They don't Jason had to admit again.
That's settled then, from now on you will only refer to your ass as your pussy and you will refer to you tiny pathetic cock as your sissy clit, agreed slave.
Yes Mistress, your right Mistress.
Oh, one for thing Sleepyjason
Jason woke up still dripping wet the phone in his hand, he put the phone to his ear but she was gone and put the phone down.
He went back to the shower and picked up a can of foam that he had never seen before and started covering his body in it, he left it on for 10 minutes then washed it off with the shower head but looking down at the shower drain, to Jason's shock all his hair below his head had fell off.
Getting out of the shower and drying himself off on a towel, he went into the bedroom looking for some clothes to put on.
He picked a pair of pink satin panties out of the draw, looking at them closely, I don't have a choice, he thought, its that or go commando so he put them on. The moment the panties went up his leg, he got instantly erect, the feeling of the panties touching his sissy clit made his so excited.
Jason started stroking his sissy clit through the panties, feeling himself getting really horny; he lied back on the bed and was masturbating himself through the material of the panties. He lifted his knees up so his asshole and started teasing the outside of his asshole, starting masturbating harder. It didn't take long for him to cum into his pink panties.
Jason looked down at himself, what have I become.... this isn't me...is it? Jason thought.
Jason got up and took down the panties and put them in the washing basket then went back to his underwear draw and pulled out an electric blue pair of lacy thong panties and put them on. Once again the moment the fabric touched his cock he felt something inside him that got turned him on and excited. Jason was trying his bet to fight these feelings but he felt inside that he was losing the battle.
Jason looked in the mirror and felt a wave of humiliation hit him, He thought he looked like a very ugly woman standing there completely hairless from the neck down and wearing the blue thong that pushed his small ass up in the air.
Jason put on a pair of black tracksuit bottoms, a plain white t-shirt and went into the living room to switch on the laptop.
Jason switched on the laptop and that horrible wallpaper picture of him naked on the chair popped up but this time he didn't feel quite so repulsed by it.
An instant message window popped up on the screen from Mistress Sarah.
Don't you look cute, maybe you should lose the t-shirt and tracksuit bottoms smiled Mistress Sarah.
Jason threw the t-shirt to the side and dropped the tracksuit bottoms to reveal the blue thong.
Oh, that's much better, you really know how to pick some sexy underwear don't you my sissy slut.
Yes Mistress, thank you Mistress (thank you, where did that come from)
Turn around and give me a view of your sissy pussy purred Mistress Sarah.
Jason started turning around on the spot and with his back to the camera bent over and gave the camera a full view of his sissy pussy.
Very nice my little slut, you look very female with your hairless body; I think that you look like a little girl now. Mistress Sarah teased.
Thank you Mistress (stop saying that, I look stupid Jason screamed)
You must really love the way you look, your sissy clit's getting bigger.
Jason didn't need to look down, he already felt his "clit" get hard the moment he said thank you to Mistress Sarah, it was now so hard that the head was pushing out of the top of the waist band of the now tight panties.
I bet you would love to play with your sissy clit wouldn't you my slave? Mistress Sarah continued to tease.
Yes Mistress, I really would love to play with myself Jason admitted.
Have you cum today slave?
Yes Mistress, I have....... Jason's face was starting to go red with embarrassment.
Tell me about it slave, Mistress Sarah loved the humiliation that she was putting him through.
I had just come out of the shower and had put on a pair of pink panties when I got excited and laved on the bed and played with myself until I cum. (Jason was paying that this was a good enough for her and she wouldn't ask any more questions)
Did you do anything else slave asked Mistress Sarah with an evil smile.
Yes Mistress...I kind of played with my pussy hole at the same time I was playing with my sissy clit Mistress.
Mistress Sarah laughed, her programming was working better then she had ever thought it would. She had already left a few commands to make things difficult for him but she never expected for him to accept such sissy programming so easy.
That's very good slave, its nothing for you to be ashamed of Laughed Mistress Sarah. You are just finally admitting to yourself that you're a sissy and you love to play with your sissy pussy.
Thank you Mistress (please stop, no more, I really cant take anymore)
Mistress Sarah noticed something that gave her a very cruel idea.
Oh slave, just look at that, your leaking sissy slime all over your sexy panties.
Jason looked down at the head of his "sissy clit" which was covered in pre cum.
I think that you should clean yourself up and it would be a very good introduction to your new lifestyle Mistress Sarah said in a very strong tone of voice.
Use your fingers you wipe the sissy slime around your lips as if its lipstick, I want you to cover your hungry lips completely in your slime.
Jason's fingers of his right hand dropped down to his "sissy clit" and gathered as much as he could, he then raised his fingers to his mouth and wiped them around his lips, automatically puckering his lips as if he really were putting on lipstick. He then smacked his lips to the camera.
You can tell that you have been desperate to do that for years teased Mistress Sarah. Now lick your lips, I want you to clean them of all your sissy slime.
Jason's tongue quickly shot out of his mouth, licking all of the pre cum from around his lips and mouth.
What do you think asked Mistress Sarah?
It's horrible; I can't believe I just did that cried Jason.
My poor sissy baby, Mistress Sarah laughed, maybe you need more practice and a little motivation she teased.
Please no Mistress, I'm not gay, please no Jason cried.
Did you not happily go to sleep with a fake cock in your sissy pussy last night?
Yes Mistress, but I ....I didn't think.....I'm not a homosexual Mistress...
Its ok slave Mistress Sarah purred, your just finding yourself, let me help you Sleepyjason.
Jason awoke; Mistress Sarah's window on the computer was gone.
Jason was out for over an hour this time, he stood up and went into the bedroom and started getting ready for work.
Jason picked out a black suit, white shirt and a pair of black shoes, while getting dressed he did not notice that he was still wearing the blue thong.
Jason arrived at work and said hello to Stan the security guard on the front gate.
Stan is 45 tall with short grey hair, he is very well built for his age as he used to be in the army but had to retire after being injured.
I thought you had the day off asked Stan.
I need to be here today Stan said Jason not really understanding why he was at work; he just knew he had to be here.
Jason walked through the doors and sat down at his desk, in the office was Dave who was looking very worst for wear after last night, Stacy the receptionist and John who is the manager of the office.
Stacy came over to Jason's desk and said hello to him.
Stacy is 21, long blonde hair, big breasts, slender figure, Jason has had a crush on her for years but never could bring himself to ask her out.
Hi Jason, I am so sorry to hear you were mugged last night.
Oh that's ok replied Jason, I can't really remember much of it.
Dave said they stripped you naked and you had to walk home in some old clothes you found? Asked Stacy in a concerned tone of voice.
Yeah, was all Jason could manage as a reply.
Let me take a look at you Stacy said seductively, you could have concussion and not even know it.
Stacy took Jason by the hand and took him into the small office that was used as a first aid station.
As soon as Jason entered the room, Stacy pushed him up against the door and gave him a long deep kiss on the lips.
I couldn't handle it if anything happened to you Stacy admitted.
Stacy's hands went down to his trousers, unbuckled his belt and pulled them down to his ankles then stopped in surprise.
What are they? Asked Stacy as she looked at the blue thong.
It's my underwear Jason replied (no they are not, don't say that Jason's mind screamed) I like to wear them.
You like to wear girl's panties? Stacy asked
Oh yeah, I don't wear anything else (WHAT!! Shut up now)
Really? I would never have thought that you would be into that stuff.
You would be surprised what I'm into Stacy, how about you pull these sexy panties down and I left you put your tongue up my ass?
Stacy couldn't believe what she was hearing from a guy that she had secretly fancied since she started work with him.
Or you could take a dump in my mouth Jason said smoothly, I bet you would love that or let me piss on your head while you fuck your pussy? (Please stop talking don't do this to me)
I am so sorry, this is a bad idea said embarrassed.
Stacy pushed Jason to the side and left the first aid room as quickly as she could, Jason looked out the window of the room to see Stacy grab her bag and leave the building.
Why did I say those things Jason said out loud, I must be fucking crazy!
Jason did feel strange, why the fell didn't I get an erection, Stacy is everything that I ever wanted and when I finally get it offered to me nothing happened.
Jason pulled his trousers up and left the first aid room.
Dave walked over to Jason as he was leaving the first aid room.
What's the matter with Stacy asked Dave, she said she couldn't be anywhere near you and left.
I don't know Jason replied, she took my trousers down and saw my blue panties then ran off. (DON'T FUCKING TELL HIM THAT!)
Yeah that's weird...she saw you blue panties, your wearing blue panties to work?
Dave looked at Jason to see if he was joking.
Yeah, its like she never seen a guy in panties before Jason said in a calm voice.
Dave just stared at Jason in surprise.
Before Dave could say another word Jason walked away heading in the direction of the toilets.
When Jason entered the toilet he saw his boss John standing at the urinal.
Jason waited until John had finished taking a piss, as John was about to put his cock away Jason reached out spun him around and planted a huge deep kiss on his lips, with Jason's free hand he reached down and grabbed John's limp cock and started stroking it.
John pushed Jason away in total surprise at his actions.
Come on Jason said in a seductive voice, you know you want to fuck me (OH MY GOD, I'M FINALLY HAVING A NERVOUS BREAKDOWN Jason's mind screamed.)
Jason dropped to his knees and forced John's cock into his mouth.
John felt Jason clamp on to his cock, to his surprise he felt him getting erect at Jason's assault on his manhood. He wanted to stop Jason and push him away but he felt so good.
John is happily married with two kids, he had never looked at another man in that way in his life but having Jason between his legs giving him a blowjob that his wife couldn't compete with.
Jason was sucking John's cock harder than he had ever sucked anything in his life; He felt John's cock her harder and exploded in Jason's mouth.
Jason finally came to his sense's, he took John's cock out of his mouth, feeling the sticky cum drip out the side of his mouth.
John grabbed Jason and threw his against the wall.
Your fired, got that! John growled, you ever tell anyone about this and your dead!
I'm sorry John, I didn't know what I was doing Jason pleaded please don't sack me.
John grabbed Jason painfully by the throat.
Get out of here now before I lose all control John warned.
Jason practically ran out of the building, scared and terrified at the fact he has just destroyed his life in under an hour.
Jason arrived back at his flat.
The moment he got through the front door he dropped to the floor and broke down crying.
What have I done Jason cried; I fucked up my entire life.
Jason stripped off all his clothes except the electric blue thong.
Jason heard a beeping noise coming from his computer; He looked at the screen and saw several offline messages, all of them from Mistress Sarah commanding him to contact her the moment he got in.
Jason typed a reply and sent it; he waited for what seemed like forever for Mistress Sarah's window to pop up.
Did you have fun at work my slave?
I have been sacked replied Jason.
Have you been a naughty little girl? She asked mischievously.
I scared a girl I liked and made my best friend think that I am some perverted freak and sucked my manager's cock.
He fired you for that? You must not be very good at that then Mistress Sarah teased.
Jason started crying once again, tears rolling down his face.
Oh dear, I guess that just leaves you with more time to serve me Mistress Sarah laughed.
This made Jason feel even more depressed and started to cry harder.
Stop crying you sissy cunt Mistress Sarah shouted, its time for your next task Sleepyjason.