"Sit down", said the hooker, as she stood counting the money I had just gave her. She seemed satisfied with the amount and tucked it away in her purse.
"So you are looking for domination ey? You want me to crush your balls for you boy?"
I looked up at her and gulped. I was already embarrassed about what I was going to ask her, and that she would assume I wanted to be hurt only embarrassed me further.
"No, Mistress. I was hoping for more of a-err- how can I put this. Like a bullying, mean-chick kinda experience. Where you like, humiliate and degrade me. Make me your bitch. Make me do things to get you off sexually. That kind of thing."
I shifted on the bed as I said this, not able to hold eye contact as she stared me down and pouted, her stunning eyes piercing me with the shame of revealing my desires.
"Go on boy. Tell me a few details of what you would like."
I cleared my throat.
"I was hoping to worship you Mistress. To eat your pussy, and your arse. I want you to use me like a dildo and make me do things you would make someone do if you wanted to laugh at them and make them suffer."
"Like...?"
I was scared to say it. My throat had gone dry and I was breathing fast. I took some confidence from her fine body before me and let out one of my most shameful requests.
"Well, I was hoping for something specific actually...it is something I find most humiliating. I feel so shy to say it but...I was hoping you would make me eat my cum. I know it sounds so stupid and-"
"Quiet now you disgusting cum eating fag," she spat, moving towards me and positioning her pantie clad crotch in front of my face.
"You like the smell of my pussy dont you boy? Start sniffing." I obeyed and moved forward, the soft material rubbing across my nose as I began inhaling.
"Now you listen to me. I'm not that interested in what you want and I don't want to hear it. You have said enough for me to have fun with and from now on you will say in answer to everything I say, either "Yes Mistress", or "Please Mistress", Okay slut boy?"
Looking up at her I wondered whether to object. She was intimidating for her small size and young age, only 20 and 5ft 3", but obviously no threat to me, a 26 year old 6ft male. But she was sexy. Sexy as fuck in fact. And I wanted this experience so bad. It had been over a decade I had been fantasizing about it. And only ever occasionally had I even strayed into the boundaries of what I had actually wanted to do, rarely being brave enough to talk about my fetishes with past sexual partners, let alone actually going through with it. That and the fact that the few girls I had brushed the topic with- well let's just say that two had seemed put off by the idea, and the one that had been keen was not really able to pull off the position as a Mistress to a pathetic fuckslave.
So with that in mind, I had only one choice about what to say. With a deep breath to compose myself, I said "Yes Mistress."
"Good. Now undress. And strip to your boxers."
I did as she asked and couldn't help but notice as I was doing so she was preparing some sex toys on a tray, spraying some disinfectant and wiping them down. I hoped she only wanted me to use them on her I thought as I pulled down my trousers, knowing there was no way to hide the tent I was pitching in my boxers.
Just as I thought this she turned around to face me. "Well you are aroused. That is good."
She reached behind her and pulled a piece of equipment I quickly realised was a strap on.
"Come and show me how much you want to please me."
She was buckling the contraption around herself as she beckoned me over. I was worried now though and quite nervous. As much as I wanted this I was scared with how far she would want to take it. She hadn't asked me anything about my limits or said what the safe word was. But I soldiered on, a mixture of arousal and a feeling that I had to get what I paid for driving me forward.
I began to walk towards her when she told me to crawl on my knees instead. I was suddenly thankful for the soft carpet as I made my towards her. As I came up underneath her, she rested the plastic cock on my face.
"Can you feel the weight of it? This is a 9" black mamba bitch. I am gonna wreck you," she said, unable to contain her laughter. "But seriously though. You are going to take this cock. Now, as you haven't got many words you can use, kiss my cock for yes, and lick my cock for no."
"Have you ever sucked a cock before?"
I hadn't. I had thought about it alot. But my mind was fixated on girls too much, and the shame of being labelled gay too strong. I licked the head of her cock and she moved on.
"Ever put anything up your bum little fag boy?"
Again, I licked her cock.
"Do you know, I actually believe you. It will make this all the more fun, so I am glad it is the case. Now one more before you do suck your first cock. Have you ever tasted cum before, yours or otherwise?"
I went to lick her cock again but as soon as my toungue touched it she pulled my head forward and began to force the cock as far down my throat as she could before releasing me and slapping me around the face with it.
"You are going to obey me aren't you boy?"
"Yes Mistress."
"You won't try and disappoint me by telling me no, will you, you dumb little pervert, you want to lick my ass so bad right?"
"Yes Mistress."
"Ok so turn around."
"I..I-."
"You better not be trying to tell me no slut", she said, cutting me off- "I am in charge now and everything you told me has been recorded and stored on a cloud drive. Now turn around and keep your face looking at the ground"
I turned around quickly, panicking about what she was telling me as I heard her open a bottle of lube behind me, but managing to get out a weak "Yes Mistress," as I continued the roleplay. That worrisome sound of the lube being prepared was actually a pleasant sound compared to the twisted tirade that came next.
"You should be more careful about what you wish for in life you sick piece of shit.
You saw me on a website. You called me up. Did you know how long I was up there for? Do you know how many happy customers I have had?"
She leaned down and whispered into my ear, "I have never had a happy customer boy." She ended the sentence by spanking my arse. Perfectly punctuating the silence that otherwise filled the room.
"You see Mark...," she said as she began to dribble a little lube onto my virgin arsehole, "My boyfriend is out in the living room, right through that closed door you saw when you came in."
My arsehole must have puckered from the lube hitting it as she said this, but in any case, suddenly I was really doubting whether this was a game at all. No one could be this good at acting, I thought. No one should be able to sound this convincing. She sounded convincing alright.
I went to turn around when she tutted, and so I kept my gaze down on the floor.
"He loves to break dumb little English boys like you. He truly thinks emasculating you freaks is a duty or something. Anyway...I know you haven't got the balls to even test whether that is true. So, I will now take your virginity for you. No warm up. No playing. I am going to roughly fuck your arse while you tickle your clitty and tell me how much you love cocks and want to eat cum from every nasty tramp on the street. You better make sure you say the filthiest things you can come up with and if you are slacking I will crush your balls and get a bigger dildo. Now, that's a lot to take in, but I'm sure you understand 100% what I expect you to do. Isn't that right fag?"
"Yes Mistress."
My mind was racing. I had expected fucking me might be something a hooker would want to do, being given free reign to take it out on their clients I imagine is a nice change of pace for any working woman. But straight away seemed too sudden. Was she really gonna fuck me immediately? I had expected this would be a moment where I noped out, where I said my safe word and told her I would maybe try again another time. Like some slut teasing her horny boyfriend.
But there was no way to get out of it. Instead all my mind could think of was things to say to keep her happy. I mean, as much as I tried to keep my mind on the experience and enjoying it, the claims she had made about being recorded, and how her boyfriend was waiting next door, were niggling at my thoughts quite a bit. If that was real then disobeying her could be a very big mistake indeed. The thought of being exposed or robbed made my cock shrink just as she began to press hers against my hole.
"Mmmm..do you want me to fuck your arse slut?"
"Yes Mistress."
She spanked me again.
"Do you want this cock of mine inside you so you can get fucked and used like a stupid sissy bimbo Mark?"