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From school bully to sissy slut
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By (user no longer on site) OP
over a year ago
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The following is entirely a work of fiction however is a fantasy of mine which I thought I would share....
I am a closeted bi curious crossdresser that just so happened to be a horrible bully at school. I have been talking to a guy on a hook up site telling him how much I love dressing and how I want to be a sissy sub slut but nobody can ever know and we exchange face pictures. Now it just so happens that the guy I am talking to is someone that I bullied a great deal, I made his life hell and he has never forgotten. He recognised me straight away but he has changed unrecognisably from a small y kid to a 6ft muscle bound personal trainer. It’s has been nearly 20 years since I left school so I don’t recognise him. He suggests we meet at a local hotel and says he is happy to pay providing I agree to wear the outfits that will be laid out for me when I arrive.
I arrive at the hotel, text the man I am meeting to ask for room number and at the reception desk is another one of my school day bullying victims. She has blossomed into a beautiful blond, I give her a glance and she smiles back. I receive a text back telling me the room number and advising the door has been left unlocked.... I am told to enter the empty room change into the outfit laid out on the bed including the blindfold....
I enter the hotel room and on the bed are breast forms, matching black satin bra, thong and suspender belt and with black sheer stocking and a pair of four inch heels, there is then a very short and tight black mini skirt, fitted white shirt, black cardigan and shirt denim jacket. I eagerly strip and change into the outfit. I then put the blindfold on and wait.
A man enters and guides me over to a chair. He tells me I am going to be lowered onto a butt plug. I slowly lower myself onto it, I then feel restraints attaching my arms to the arms of the chair and my legs to the legs of the chair, I am collared and this is also attached to the chair, there is no way I can move. I feel my thumb pushed onto something, it is my phone and it has been unlocked. The lights in the room are turned off and I am told that when my blindfold is removed there will be a bright light that I must look straight at and say out loud how much I have dreamed about sucking a cock being as slutty as I possibly can. I am then fed the cock and made to suck it, I go to town on it and am clearly enjoying myself when I feel the putt plug starting to vibrate and slowly expand. Suddenly the man stops and tells me to decide whether I am going to swallow or receive a facial, I eagerly both. He fucks my mouth and pulls outs just leaving the head sitting on my tounge when he cums, he tells me not to swallow yet. He is a heavy cummer so finds enough cum to wipe all over my face, I am then allowed to swallow.
The room light is turned on but I am still bound and blindfolded, that’s when I am told something which will change my life forever... |
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By (user no longer on site) OP
over a year ago
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‘So you didn’t recognise me’ I heard a voice say which immediately sends me into a panic. ‘You spent 5 years making my life hell’ he said and with that he proceeded to introduce himself and reminded me of the names I used to call him.
I suddenly felt a hand on my face, my mouth was being forced open and something attached... he had put an open mouth gag on me.
‘I have just recorded everything, that light you were looking at was a camera so here’s what’s gonna happen... you made my life hell for 5 years’ he said. ‘Now I don’t have 5 years so I am going to have to pack my retribution into 5 days’. ‘I have accessed your phone I will be keeping it for the duration of your ‘rehabilitation’ For the next 5 days you will do everything I tell you without question, if you do not that video will be sent to every contact on your phone, uploaded to you Facebook account and sent to all of your work colleagues... do you understand?’
My only option was to nod... that video couldn’t get out... it would destroy me.
‘Right I’m off to the bar for a drink’ he said and with that I heard him walk to the door and leave. Here I was, still bound and blindfolded with an open mouth gag, covered in cum and unable to do a thing about it. |
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By (user no longer on site)
over a year ago
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So I started writing this story under an old account... I thought it time I continue...
After what seemed like hours I heard the door open and footsteps enter the room. I was then set free and told to go to the bath room and clean myself up. Once I was finished I went back into the room and laid out on the bed was black thong and bra, sheer black tights, a red tartan pleated mini skirt and a white blouse which I was ordered to put on. ‘Right’ said my now master, ‘I want you on the floor on all fours, when you are told to beg you will beg for cock to be put in your ass and mouth, you better be believable and you better show how much you are enjoying it’. I did as I was told and at that moment was blindfolded. There was a knock at the door and I heard multiple pairs of footsteps enter the room. ‘Right beg’ said my master, I had no choice but to beg to be spitroasted! ‘Oh, and just so you know the reason you are blindfolded again’ said my master, ‘it’s because you know everybody in this room but you will never find out who they are... they could be friends, old school mates, colleagues... who knows, one of your ex girlfriends could even be here to watch you get fucked’. I heard a female giggle but before I could say anything I felt a still penis push against my lips and like a true slut I opened wide to take it. I then felt another cock push against my ass and slowly enter. ‘Remember I said you better enjoy it said my master’ so I began to push back riding the cock I’m my ass while I sucked the one in my mouth. I could hear laughing and camera clicks... what had I got myself into... |
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By (user no longer on site)
over a year ago
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I was now being pushed back and forth as the tempo was building, both cocks thrusting more aggressively in both holes. Eventually the cock in my mouth slowed and my mouth was filled with cum, ‘swallow every drop’ said master. As I did this the cock fucking me was plunged deep in one final thrust. It’s finally over I thought however at that moment I felt another hard cock push against my lips and an even bigger one push against my ass. The afternoon went on like this, I was spitroasted over and over again until the room finally emptied and everything went quiet. As I took off my blindfold I realised that the room was empty with just a note left on the side. ‘Be up at 7am and dressed in what I have left for you’ it said. |
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Great return for a wonderful story.
I hope those that were bullied properly break him and make him feel even worse than he made them while at school.
I’m wondering what will happen next. Holding they’ll upload it all online anyway afterwards just for fun as he was such a cock growing up 
Or is that just being a bit too mean  |
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By (user no longer on site)
over a year ago
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I hardly slept a wink that night and at 5am i decided I would start doing my makeup. I had no idea what was in store for me. I did my make up as well as I could and as I looked in the mirror I couldn’t help but think I was looking quite convincing... even attractive. I started to get dresses in what had been left for me to wear, dark red wig, leopard print bra and thong, nude sheer hold ups, blue body con denim mini skirt, pink glitter cami top with over the knee stretch black stiletto boots... my master had been kind enough to also provide a 3/4 length black fur coat.
At 7am there was a knock at the door. I opened it to find my master standing there. ‘Morning slut’, he said, get all your belongings together as it’s time for you to check out. I gathered everything together and sheepishly walked to the reception desk.... name please said the girl at reception... I checked in in my male name and as I told her I could tell she was trying desperately not to laugh. I met my master outside and was led to a car and told to get in. I was told to put an eye mask on and pretend I was sleeping.
We must have been driving for a good 2 hours until we stopped. I was allowed to remove my eye mask and I could see we had arrive at a beautiful country house surrounded by green fields and woodland. I was led inside and taken to a room where a women sat. ‘Hello sweetie, we are going to make you look beautiful this morning’. First I was given a spray tan all over my body, next was a manicure and pedicure followed by nails being painted. Next I was given a full makeover. Finally I was told to stand while a strange liquid was applied to my chest followed by two ultra realistic F cup breast forms. They were the exact same colour as my skin and even close up it was impossible to tell they were not real. All done said the women as she left the room.
My master re entered and laughed as he saw me. ‘Very sexy’ he laughed. Right time to go out he said leading me to the car. We took a 15 minute drive to a service station driving round to the lorry park. ‘Right’ said master, I want you to walk slowly across the truck park and stand outside the guys rest room... if any man approaches you and speaks to you I expect you to offer to suck his cock for £10... I will be near so I will be able to hear if you don’t ask... |
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