(I haven't written a purely erotic post in a while, so if this is too cringe then I apologize in advance...)
I will start by saying that everything that took place below, though fictional, was implied to be consensual by all parties involved.
I was in the play space. It was a safe space, I knew. But somehow, as I stood there blushing uncontrollably, fidgeting, nervously waiting for I don't know what was to happen next, I wondered how far She would take me. I stood next to the brick wall, dressed in drag, my little naughty school girl plaid skirt way too short for my comfort, as beads of sweat began forming under my sweaty blonde wig. This was a safe space. A private space, secluded enough- but I hoped to God nobody else could see me like this.
My ass still smarted from the flogging She had given me, and the cat-o-nine tails had made my back sting. Flogged to within an inch of using the safe word, tears in my eyes, it almost escaped my lips, but, perhaps sensing my limits, She had stopped. Then she said simply, "You are ready to be my little whore. Here's your outfit... put it on, ... and get out there." I obeyed, relieved at the reprieve but still under Her spell. "Whatever you want, Mistress!" I said eagerly.
Minutes passed, or perhaps time simply passed more slowly. Not knowing what to expect or wait for until I heard a whistle. I groaned inwardly as Kyle strode into the courtyard. He was Her stud. I had been introduced to him a few sessions ago. I loved that he could satisfy her sexually, but I hoped to satisfy her in other ways. To be a good submissive... and a good little slut. For Her.
I won't describe what happened next in too much detail. Sub space is like a drug, an intoxicating high, where you find yourself doing things you would never do in a normal head space. Even my memories are blurred, lost in the rush of adrenaline and the vague thought of what I was really doing. Let's just say that some money changed hands. Fifty bucks for a blow, a hundred for a throw, she had said. I knew She had arranged all of this, so I would not let Her down. Kyle seemed oddly satisfied too. "Thanks, you fucking ugly ho," he said, after I had finished with him. He pulled up his pants, then reached up under my tiny skirt and grabbed my behind, before sauntering away.
More time passed. How long, I don't know. I waited for Her there, as instructed. After a long while She appeared. Only, She wasn't dressed as she had been earlier, in that leather skirt that had made me such a submissive toy merely to see her wearing it. Now, she had cowboy boots, loose-fitting jeans, a loose-fitting Philadelphia Eagles jersey, and her hair was pulled back under a baseball cap. Like a typical bro, with one exception.
She was wielding a harness with a long strap on.
She approached me. "I wanna fuck you up the ass bitch." She said. "How much?"
"F-f-uh... I mean, uh, one hundred for a fling...."
"I'll give you fifty" she said. I didn't argue with Her; that would be a bad idea.
"Kneel and suck it!" She barked. "I see you've already been used. You got cum on your face. Now I'll show you how a real woman takes it!"
I knelt in front of Her, sucking her large strap on for several minutes. "You're a real pro at that! Now I'm hard and horny!" She said, in a fake-deep voice. Seemingly satisfied, she ordered me to turn around. "Now bend over!" She said, in the same deep fake-man voice.
I obeyed instantly, knowing what was coming. She lubed up, then roughly pulled my pink panties down. I felt it probing me gently, then felt the familiar tearing and pulling as it forced it's way into me. I began to moan as the full length pushed further and further in. It filled me, stretched me, splitting me. I even felt sudden pressure on my bladder as she finally got the full length of it inside me. She began to rock, gently, than progressively harder. In my mind, I was somewhere else. Neither bliss nor pain, watching almost detached as She took me from behind, violating me. I began to moan, which prompted her to smack me, so I tried to keep silent. I could almost feel her smiling, twitching, and hoping that She was getting off on Her end. She finally began to moan herself, as the thrusting rhythm I felt, as she rocked against my raised buttocks, reached a crescendo.....
.....back inside, I am kneeling in front of her, nose to her cowboy boots, wanting to touch them, basking in Her power and beauty, even dressed as She was. Like a "John." Only now, she wasn't the "john" but rather, she was now the pimp. She had donned some faux gold chains after she had momentarily gone into the other room. "You, bitch, gimme my money!" She said, and not at all playfully. Reaching into my socks, I handed her the $100, both the fifty she had given me, and the fifty I had received from Kyle earlier on.
"That's not all of it. Where's the rest? It was a fifty for a blow, a hundred for a throw! You only gave me a hundred! Where's the rest of it!"
"But but, you said..."
"GIMME MY MONEY, bitch!" She said, slapping me across the face. Stammering, I crawled over to where my street clothes lay piled in the corner, reached into my wallet, and gave her fifty dollars.
..... So, that's about it. I hope this short story wasn't offensive or cringey. Keep in mind that all of the fictional events described above were CONSENSUAL. I do not condone forced prostitution or any form of human trafficking. Rather, I just thought this would be an interesting play scenario.
