Ashley the Escort Ch. 03

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My escort website was designed by a nice young 18 year old that only wanted to play with my tits while I gave him a handjob. It was well worth it. But my email inbox was stuffed full of requests and I needed to pick someone out for Tuesday. It was early Tuesday morning and I had a headache. I’d broken out the Grey Goose and cranberry juice and had myself a party while dancing around the house to heavy metal. I wasn’t always stuffy and controlling. Sometimes I liked to let my hair down, so to speak, and let go.

I drank coffee and sifted through the emails and requests. Most of them were legitimate, but I was very careful to select new clients. I preferred to stick with ones I’d met before. I hadn’t been arrested, knock on wood, and I didn’t want to be. One email caught my eye from someone I hadn’t seen in a long time. We’ll obviously call him John Tuesday, but he had a fetish for being whipped on the back with a cat o’ nine tails and he also liked being lightly choked. Since I had a headache, I could totally see myself being the grumpy, punishing bitch for him. I emailed him back and asked him to call me.

He called back pretty fast and we set up a time to meet around 7:00 that night. It was time to go shopping for some leather. And a manicure. I love to get my nails done. I went to a local store that specialized in toys and leather and picked out a fun looking dominatrix outfit. I’d wear black lacy panties and bra to go with. And my shiny black heels, of course. After getting my nails done, I headed home to get dressed. I had to wear something over this or I’d be pretty conspicuous walking in to the hotel. I only met in hotels, never in personal homes. Just a preference I had.

I arrived at 6:53 and knocked on the door. My hair was pulled back tight in a pony tail and my makeup was heavy. I had a small bag with me holding my trusty whip. Tuesday, my soon-to-be whipping boy, answered and grinned at me.

“Please, come in,” he said and opened the door wide for me. I was instantly stopped in my tracks when I saw a massage table and handcuffs in the middle of the room.

“What’s that?” I asked quickly.

“Oh it’s not for you. It’s for me,” he explained, “I’m going to handcuff myself and lay on the table. Then I’m yours illegal bahis to punish. I’ve been a bad, bad boy,” he smirked and began undressing.

“Do you have something for me?” I asked, looking around for the donation.

“Oh! Yes, sorry,” he said and he dug in his pants for the arranged amount of $700.

“Just set it on the table babe,” I said and I began to take off my outer shirt and pants. He continued to undress and I finished up and we stood there. One of us naked and one dressed in leather, stockings and heels.

I walked over to the table and stuffed the donation inside my outfit and picked up the handcuffs.

“Lay down on the table, you piece of shit!” I barked at him. We had a relationship we’d built up over a few sessions and he always did what he was told.

He hurried to the table and lay on it face down, his arms dangling below off the sides, “Yes mistress.”

I took the handcuffs and put one side on each hand under the table so he was bound on top of it, his arms together underneath. Satisfied with my subject ready to go, I took my whip out of my bag and placed the donation in the bag. He’d never asked me to have intercourse, and I always finished him off with a handjob. I think we was secretly afraid of diseases and I didn’t mind our arrangement.

“I’m tired of your shit, Tuesday,” I started in with my angry voice. It was showtime and I had to play the angry bitch that was punishing him. I raised the whip. I brought it down, gently on his back. He shuddered. I raised the whip. I brought it down, a little harder. He moaned in pleasure.

“I’m sorry Mistress,” he offered.

“If you were sorry you wouldn’t have pissed me off in the first place, would you?” I demanded.

“Yes, mistre…uh, what did I do to piss Mistress off?” he asked.

“Shut. Your. Fuck. Hole,” I slowly said in my meanest tone. I raised the whip and brought it down on him, hard. He winced in pain and his breathing was picking up now. I decided to give him a little relief and ran my hand down his back softly. When I reached his ass, I squeezed tightly and ran my hand down between his legs. I began to feel his balls and caress them softly when he raised his hips, giving me better access. His penis came in to view illegal bahis siteleri and he was hard as a rock. He really got off on this.

“Do you want Mistress to pleasure you?” I asked quietly.

“Yes!” he blurted out.

“YES? YES, WHAT?!” I yelled at him and brought the whip down on his back again. That caused him to lower his hips slightly in pain.

“Yes, please, Mistress.”

I ran my hand across his ass again, teasing at the thought of pushing a finger in his asshole and decided against it. I lifted his hips a little more and he obliged. I reached under and began to stroke him softly, giving him full, long strokes. He moaned his approval of what I was doing. He told me once that I had magic hands and that they turned him on.

“Mistress, may I please turn over?” he begged with a slight whine. I thought about it and decided to allow him a little more pleasure. We hadn’t really gotten in a long pain session but he seemed to want release. I uncuffed him and he slowly rolled over and lay on his back. I thought I saw him wince as he did from the few whips I gave him. He asked me to cuff him to the table leg above his head and raised his hands up to it. I put the handcuffs around the leg and then cuffed each hand. Now he was sprawled out before me with a raging boner.

I ran my hands from his cheeks down his chest to his belly and then repeated the motion with the whip, slowly running the tails down his body. I could see goosebumps on him and that made me smile. I gave him the lightest whip on the chest and asked, “Have you been a good boy for Mistress?”

He nodded emphatically and I smiled at him saying, “Maybe you deserve a present.” He nodded again. I ran my hands down his body and around in circles around his crotch. I gently cupped his balls in one hand and squeezed slightly, watching his expression. He closed his eyes and took a deep breath. I continued to knead and massage his ball sack, then moved upward and ran the tips of my fingers along the shaft of his penis. It convulsed in reflex under my touch. I wrapped my delicate fingers around him, giving him the softest grip.

“I’m still fucking mad at you, do you understand?” I glared at him.

“Yes, mistress. I’m so sorry,” he nodded at canlı bahis siteleri me.

“I’m only doing this out of pity for your fucking ass. I ought to shove my whip up your asshole. Instead here I am giving you my magic hands. You don’t deserve it, do you, you little shit?” I went on. I felt a little exhilaration when I spoke like that to him. I made a mental note to explore more of that side of me later.

He shook his head no and looked at me with puppy dog eyes. I suddenly gripped tightly around his cock and began to stroke him fully. His eyes rolled back in his head and he tried to lift it up to watch me.

“Tell me before you cum, motherfucker,” I demanded. He was shaking a little and his hips were starting to move a little. I could tell he was getting close. Luckily for me, guys tend to cum quickly, giving me a break.

I continued to stroke, gripping tightly and my arm was beginning to tired. I never gave up when it did, though. Always finish the job. He spoke up, “I’m so close Mistress!” I thought I could feel him get harder and maybe a little bigger and I used both hands on him.

“Cum. Now!” I barked at him.

He groaned and raised his hips and I gripped as tight as I could with two hands, cutting off all flow mid-penis. He looked down at me and after a moment, I released, sending his cum flying into the air. I stroked him quickly, helping him finish off. There was cum all over his chest, going up maybe two feet. I was impressed.

I took a step up to the head of the table and leaned down as if to tell him a secret and kissed him softly on the lips, “You were a good, good boy, ” I whispered.

I left him cuffed and covered in cum and took my leather skirt off. I climbed up on the table and straddled it and his legs, facing him. I began to play with myself, giving him a show. It didn’t take long for me to cum in front of him since I was turned on by being a bitch to him. As I came, I shouted out his name for fun. He was smiling down at me.

“Show’s over,” I told him with a wink.

Later that evening, while I was laying on my couch, watching TV and drinking wine, I thought back through the day. I felt like I’d given a weak performance as a dominatrix and wanted more. I felt like lately I was too cold and unimpressive with all my clients. This was bad for business, if so. I drifted off to sleep, wineglass in hand, wishing I could put more energy in to it. Maybe I was burned out. Maybe I needed a real boyfriend to hold me.

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