Payback's a Bitch

Knelt on my knees and taking a glance to my right at the sight of a woman counting cash whilst I sucked off a guy I started to wonder how this had all happened.

I had a good job and didn't have a huge problem with getting lovers. I was straight and loved women but here I was – nothing but a sissy prostitute being rented out for the oral pleasure of men I didn't know and the worst bit was I was loving it.

The thing is I have always loved sluts. When at high school and college I would always go for the easiest lay. They always seemed the most fun and seemed to enjoy the fun and games in the bedroom far more than anyone else. As I got older I noticed all my friends starting to settle down and all they seemed to do was complain how vanilla and boring their lovelives were.

I was thrust back into the past and how much fun those sluts I used to fuck and get sucked off by had and started to feel some envy about how enjoyable they seemed to have it. Like my friends I had settled down and whilst I wasn't married I was in a committed relationship with a woman who was my world. My only problem was our sex life.

I had tried to get her to embrace sex but whilst she would enjoy a good session she would never go anything that wasn't shall we say regular. Slowly I started to use the internet and I knew I didn't want to have sex with anyone else as that would be cheating and I did love my partner.

Whilst surfing I came across the website of a dominatrix and that seemed like the perfect idea. I wouldn't be having sex with anyone and I'd just get some spice. Even though I wasn't a true submissive it would at least be kinky and give me a bit of a thrill. So I sent her an e-mail and said I was a complete novice. She replied and said to come in for a taster session and she would see how I reacted.

So one day when I had some spare time I went along and met the Mistress. She dungeon was out of this world. Pretty much any fantasy could be played out here. She said that for complete novices she had a hat full of scenarios and I should pull out a piece of paper and that would be the taster scenario. I thought that sounded like a good idea as I really had no idea what I wanted. So I put my hand in and out came the word 'schoolgirl' – I tried to argue but she said that was the taster session or I could leave. I thought what the heck and said ok.

She instructed me to go into the bathroom and have a shower and said when I got out my uniform would be hanging up on the door and to change. So I got into the shower and had a good clean and when I got out I noticed my male clothes had gone and a female school uniform was hanging up on the inside of the door. I put on the uniform and wondered why I had no underwear provided but I stepped out and was beckoned over to a vanity table. There I was instructed to say nothing and had a wig placed upon my head which the Mistress brushed carefully and put up in pigtails. She told me that for the next hour I was to be known as Claire and then put some light make-up on me.

I looked into the mirror and whilst I could tell it was a man, I could see that with a bit more time I could actually pass as a schoolgirl. I noticed my penis lift and wondered if I was actually being turned on by this. Mistress said she was to be called Miss Oakes and that I was to do exactly what she said.

I was told to go and sit at a real looking school table and was instructed to recite my times table. It was a touch boring so I got one wrong and was quickly told to stand up and bend over the desk. Four lusty blows from a cane on my rear end later and I was told to start again. It hurt but I noticed my penis was still erect. I was then told we were doing some sex education and I was to tell Miss Oakes all about my best sex ever. I told her about the sluts I used to fuck and she muttered something about it being interesting and took down some notes. She rang a bell and asked if I wanted to come again.

Thinking about it for maybe half a second I said sure. She said she had learned a lot about me in this hour and that she thought she could give me a really good time. She said to shower and that my clothes would be returned to me and they were. I left and got an e-mail a couple of days later instructing me to clear out either an afternoon or evening to 'have a good time'.

So I did and went down to the Mistresses place. She told me to come in and she asked me if I trusted her. I said that I did. I have no idea why I did but I just did. She told me that I would enjoy the evening but she had to know if there was anything that I was unwilling to do. I lazily responded that I didn't want to get fucked in the arse but thought it was a joke. She said that was fine and instructed me to have a shower again and my clothes would be waiting for me.

After enjoying a shower I got out and was stunned to see not a school uniform but a short PVC mini-skirt, stockings, a suspender belt, high heels. There was nothing to put on the upper part of my body. Strange I thought but I got on with it and whilst the suspender belt was extremely fiddly and the high heels took some getting used to I stepped outside. The mistress looked impressed and told me to sit down again in front of the vanity table. She then glued on two false breasts that she said would come off after a hot shower and put a tight PVC top over my head. This time my make-up wasn't very light – it was actually very trampish and I realised I was looking like the type of slut I loved to get to suck my cock.

Mistress leaned over and said this was the last moment I could get out of this scenario. If I didn't back out now I wouldn't get to play out the whole scenario. If I wanted to back out now she would slap me and kick me out dressed like this and throw my clothes out of the windows afterwards. Considering she lived on a main road I didn't like the idea of anyone seeing me – even if just for a couple of minutes so I said I'd go ahead.

She put a dog-lead around my neck and put a padlock to lock it in place, she told me to crawl on all fours across the room and then out into her back garden. I was hesitant but I carried on and she lead me to what seemed like a small shed. I was taken inside and told to kneel down. I looked ahead of me and there was a large hole in the wall. Above the hole written in lipstick were the words 'Sissy Slut Gloryhole' and she laughed as the realisation of what was about to happen came across my face. Before I could do anything she fastened her end of the dog lead to a hook on the wall and told me I wasn't going anywhere.

'Ok then Claire, here is what is going to happen. I am going to post an advert of Craigslist saying that a Sissy is sucking at this very gloryhole for the next hour. The cost will be $20. For the next hour if anyone turns up and gives me $20 you will suck them off. You do not have a choice.' She then took out her phone and took a photo of me and placed the advert 'well we'll have to see how many people like sluts' she said as she lit a cigarette.

It seemed to take an age but still no-one turned up and I thought I was going to get away with it. Whilst waiting I was told to not say a word otherwise I'd get beat. She spanked me a few times to stop her from being bored but suddenly I heard the gate go and I could see a man walking up to the shed. My mistress walked out and took the $20 and came back inside and told me I had a punter. A cock came through the gloryhole and I was spanked until I took it into my mouth.

It was disgusting. I had never even thought about doing anything like this. I had a girlfriend I loved and had never had any gay tendencies. I was told to plays with his balls and lick the whole shaft. I thought if I took as long as possibly on this then I might only have to do it once within the hour. My mistress seemed quite relaxed about how long I was taking but suddenly she said 'face fuck him' and the guy outside started just fucking my face and stuffing his enlarged penis in and out of my mouth. I couldn't do anything and then I felt it twitch. I tried to get away but my mistress has the back of my head and forced it forward. Cum sprayed down my throat and I gagged.

The man groaned and kept spraying down my throat. It must've only lasted 20 seconds at most but it felt like an eternity. He seemed happy and as I couldn't spit out the cum as my throat was stuffed with his cock I had to swallow. He threw in a $10 bill as a tip through the hole as a tip and laughed as he walked away. My mistress said time was up and I was free to go if I wanted. Of course I wanted to leave I thought but then she quietly said 'you are a great cocksucker' and my penis twitched like anything and I came. She noticed and laughed and call me a sissy whore and she walked away leaving me kneeling in a pool of my own cum and still tied to the wall in front of the gloryhole.

She came back a few minutes later and showed me a photo of the outside of the shed. On it were the words 'Sissy Whore Claire's Gloryhole. $20 a pop. This bitch swallows and satisfaction is guaranteed or you get your money back' – she said she had put a photo up on Craigslist and I would be working there until midnight. I protested and said I had to get home to my partner. She told me tat she owned me now. Then she whispered in my ear and said 'Hi George, we used to go out in high school, so you thought I was a slut did you? Well now you'll find out what a slut really is,' and she looked sternly at me. It all came back to me now. I knew this woman and had used her in high school for my own means. 'Payback is a bitch...and so are you' she said as she went outside to see a long queue of men in her garden. I was about to find out that payback is a dish served stone cold and the worst bit was I wasn't unhappy...