I discovered over the next few months that Anita's favourite toy was John, she loved nothing more than to take his ass in her office at least twice a week. No wonder he had the evil eye on me, he must've thought I was trying to muscle in on his mistress. I also found out that he was gay, which made me wonder what he got out of the deal with her?
He explained to me, once he knew that I was no threat to him, that he was what is called a bottom. He preferred men but didn't care too much who did it as long as someone did. If it helped his career, then it killed two birds with one stone. It set me wondering if I was a bottom too, I had no inclination to liking men but I found that I adored the domination of women.
My relationship with Sandra changed after the incident in the office, I still looked upon her as a friend and we still had our breakfast together every day, but now it felt like were not equals.
In the space of three or four months I had gone from an innocent eighteen year old kid and a virgin to, well all I could think about was sex. Not that I didn't think of it when I still had my virginity, I just thought about it more now and not just sex, but kinky sex, the kinkier the better and my mind had no limits now the door had been opened.
I was not going to know at that time, but these women had shaped the way my sex life would be for the rest of my life, vanilla sex just wouldn't cut it. The way they had dominated me had really gotten under my skin, it was all I could think about and I found I was masturbating 2-3 times a day imagining what they might make me do next. I had grown up thinking that men had to be the strong force, and especially in the bedroom which was stupid now thinking back, my mother and aunt Alice were two of the strongest people I know.
My mother still cleaned for the Johnstone-Browne's and I was terrified that one day she might learn of my dalliances with JB, I had a feeling that aunt Alice knew something was going on but she never said a word to mum as far as I know.
JB really took me under her wing and over the next few months loaned me out to Anita for mentorship, she took me onto sets for filming and introduced me to all the right people. It was fascinating to watch how they would shoot adverts, I assumed that they only took an hour or two but some ads took weeks. During these longer shoots I would be treated to stays in all the best hotels along with being treated to sex with Anita, which was anything but vanilla. Her favourite thing was to tie me to the bed and tease me, riding me until I was on the verge then pulling off, she would do this for hours until I was begging, almost crying to be allowed to come. When she would eventually allow it, it was always inside of her. She would say that she enjoyed the feeling of me pulsing inside her body, but I knew it was the power she felt when she made me clean her afterwards.
I would always have to spill the beans with Sandra over breakfast, she lived for the gossip and the more I got to know her, I am sure she got off on the fact that a strong, fit boy like me liked to be bossed and even sometimes pegged by even stronger women.
To the best of my knowledge, none of my friends had these inclinations, but then, would they openly admit it? I know I would be mortified if any of my peers knew that I had been fucked in the ass by a woman.
On a few occasions JB sent me on private errands for her, on one of these occasions I had to pick up some paperwork and transfer a file off her home computer to her email account so she could retrieve it at work. I had met her husband years ago when my mother took me to their house to clean, but had not seen him since. She told me that he may be home but gave me a key and the access codes as to not disturb him. Sure enough, his Bentley was in the driveway when I reached the house.
Tapping in the code, I turned the key to an eerily silent house. He must be here somewhere and I was torn on whether to call out or just get in and out as quickly and as silently as I could. I decided on the latter and as I knew her office was at the end of the east bedroom wing, I crept up the grand staircase.
The house was huge, the open plan landing area looked over a balustrade to the large entrance hall below. Plush deep red carpets muffled any noise I would make so I crept as silently as I could towards where I knew her private office would be. I passed many doorways leading to the bedrooms in the wing and as I passed JB's bedroom I could hear muffled noises. Then from behind the closed door I heard a low groan and I froze.
For what seemed like an eternity, I stayed rooted to the spot holding my breath and praying the door would stay closed. Eventually I crept on, trying my hardest not to make a sound until I reached the office door. Quietly, I closed the door behind myself and resumed regular breathing. I knew I had reason to be in his house but for some stupid reason, I didn't want him to see me.
Inside the relative safety of her office I looked for the paperwork she had asked for, sure enough it was on her desk next to the pc monitor. I tapped the start button on her pc and it flickered into life, what came on the screen took a few seconds to register in my brain. A man, a naked man. He was bound face down to a large bed by his wrists and feet, he had a black hood on his head. A tall red haired woman stood beside the bed, she was dressed in what looked like a sort of leather cat-suit. She had a rattan cane in her hand, it was about four foot long and the thickness of her forefinger. She was tapping it into the palm of her other hand as she walked around the bed surveying the tied man. I couldn't take my eyes from the scene, there were no words spoken but I knew there was sound as I could hear the faint tapping of the cane.
I moved the paperwork to the side and saw the mouse, moving the curser I tried to bring the volume up only to have the picture go blank.
"Fuck!" I cursed softly, "where did it go?" I had minimised it by mistake. Bringing it back up, the screen had split into four sections. One of the original scene, others of the lobby, the front door from the outside and one of the large lounge area. There was CCTV of the entire house, cameras were everywhere and each showed different views of each room of the mansion.
Bringing the bedroom scene up again I saw she had started tapping the bare soles of his feet with the cane, it was obviously causing him pain because he was trying in vain to move his feet from her reach. She ran the tip of the cane up the backs of his legs stopping occasionally to give the calves and thighs a flick causing him to yelp and jump. I was transfixed and the file I was supposed to be finding slipped completely from my mind.
She dragged the tip across his ass and I heard him take a large intake of breath, he went ridged as if he knew something was about to happen. The woman raised her arm and held the cane aloft before bringing it down hard on his pale white fleshy cheeks. He screamed in agony, his ear piercing scream came through loudly over the speakers.
She crouched down to inspect her handywork, running her fingers across the red welt as it raised and formed under her soft touch. Slowly standing, she dragged the tip of the cane up the line of her victims spine. He twisted his body as she drew a line up to the bottom of the hood, she raised the cane again and held the same pose as before. I waited on the edge of my seat with bated breath for her to strike again, I found my hand had discovered my cock, it was ridged and I squeezed myself through the material of my clothing as I sat watching.
The sound hit me before the picture, she brought it down even harder and his poor fleshy ass shook and wobbled at the impact. The sound of his cries made me cringe sending a shiver from head to toe as she brought it down again and again at least six or seven times, each one harder than the last. When she stopped, he was writhing in agony below her, sobbing. She again crouched to inspect the damage and to my surprise, leant in and planted a kiss on each deep red line.
He was sobbing and his body was violently shaking when I heard her say.
"Well, what do you say?"
It seemed to slow his sobs, and between the ragged breath of them I heard a soft "Thank you mistress."
"Good boy." She said, and ran her fingertips over the raised welts that crisscrossed his ass, occasionally stopping to scratch at one or two with her long nail.
She moved out of sight of the camera leaving him, his sobs had slowed and he was breathing deeply, each deep breath was interrupted by a small sob trying to get out before the breath resumed as he calmed down.
My cock was alarmingly hard and I was desperate for the scene to continue, I clicked on different views trying find her until she reappeared with a jar of white cream.
"There, there my pet." She cooed as she crouched beside the bed. She dipped first one, then two fingers into the jar and applied it liberally to the welts, running her fingertips the length of each one as he shuddered and groaned under her touch.
The angry looking purple head of my cock appeared through the top of my fist as I slowly moved it up and down, a clear bead of fluid dripped from the slit as I sat in my bosses chair watching the monitor wishing it was me tied to that bed. I had never, ever had any inclination to be harmed in any way before and had no idea why I had these feelings now, but I wanted to be on that bed so badly it hurt.
'Ring, ring'
The sound startled me so much that I almost fell out of the chair, it was my mobile phone. Looking down, I saw it was my boss. "Shit, the file."
"Hi Bobby dear, did you find the file as I have not received it yet?"
"S-Sorry ma-am, I am just looking now." I said, hopefully convincingly.
The lady on the screen was now sitting on the side of the bed stepping into what looked like a strap-on belt, then slid it up over her leather-clad legs. God, I so needed to watch but had to get this file for my boss.
"Are you sure you are looking for the file Bobby?"
"Y-Yes ma-am," I said, very flustered. I quickly tucked myself away and clicked the mouse to her personnel files.
