It had been just over a year since Oliver had taken control over my life. And control it he did. I went from being a promising young salesman, to an assistant, who handled all of my boss' accounts, and also served as his cock slave.
Oliver had moved into a much larger penthouse apartment, while I was struggling to feed myself on a weekly basis. Not only was he benefitting from the commissions I was earning for him on his accounts, but he was now also charging me to be his slave. Every payday he'd call me into his office and have me slowly tongue bathe his balls while he looked over my pay slip for the week. He'd then decide how much of it I was allowed to keep. I usually went home with roughly 25% of my earnings.
Oliver's control was no longer confined to just our office space either. About a month ago he fitted me with a chastity device to prevent me from getting erections and playing with myself unless I was under his direct supervision. He also now had me arriving at his apartment at 6.30am to draw a bath for him. He'd then make me clean him from head to toe, including washing his hair, cleaning each of his toes individually, and making sure his ass was clean.
This wasn't just constrained to week days either, it was 7days a week. On Saturdays, after the bath, he'd stand in the water as it drained from the tub, and have me shave his balls for him. There I was, on my knees, with his thick flaccid cock in one hand, and a razor in the other, as I slowly and gingerly removed every hair from his heavy sac. It became an art for me, a passion. After finishing, I'd use a warm cloth to remove the excess shaving cream, and by this time more often than not, he'd have a semi hard cock. Without hesitation I'd look up into his eyes, and ask, beg almost, for him to let me suck his cock.
"May I Sir?"
"May you what slave?"
"May I suck on your cock Sir?"
"Do you want to?"
"Very much Sir"
"Do you need it?"
"YES SIR!"
"Do you love it?"
"Most definitely Sir! I love your cock Sir! Please let me suck your cock Sir!"
At this point he'd either tell me to make sure to swallow everything, or he'd tell me he was losing interest in me, and walked away. I'd always feel hurt and as though I was disappointing him when he'd turn me down. It made me want it more. Made me want to please him more!
After finishing up on him, I was to shave my entire body, from the neck down. When I was all cleanly shaven, he'd dress me in some girls panties, and have me clean his apartment and do his laundry while he'd read the newspaper and watch sports highlights. I'd also be responsible for preparing his breakfast for him. Freshly squeezed orange juice and all!
The weird part about all of this was that I no longer questioned it, I no longer wondered how to get out of it. It was who I was, and who I wanted to be. A slave to this little man, with a gigantic, monster of a cock. I was taller than him, stronger than him, and probably smarter than him, but because he was blessed with this huge gorgeous cock, I'd do whatever he asked!
He continued to have me work my own ass with the dildo as well. Every week he'd find a bigger, thicker one, or he'd have me sit on an ass plug for him. I started to wonder why he'd have me do this. After all, he's not gay. He doesn't fuck guys, he fucks chicks, and I've only ever sucked his cock, why would I be stretching myself if not for his pleasure?
On the Monday morning, after completing his bathing, he told me to rush into work and prepare our offices for meetings with a new potential customer. This is when things started to make sense. The new customers owned a nationwide chain of sporting goods stores that targeted the gay community. Apparently DINKS (double income, no kids) were the fastest growing market out there. If Oliver could secure this account, it'd almost double his commission income.
The customers arrived at 4pm that afternoon. The CEO, Felix, was physically imposing to say the least. About 6'5" tall, and stacked with muscle, and a shinny bald head. He arrived with his assistant in tow, and it was clear who was in charge the moment he walked into the room. The assistant fetched him water, took notes for him, prepared his papers before they were passed over to Oliver, or should I say me, as I was serving Oliver in the same manner.
Although his assistant was always neatly dressed in a tailored suit, Felix wore silky looking button up shirts, with the tops three buttons undone, exposing part of his massive tanned chest, and pants that were tight enough to see outlines of his powerful legs, and a clearly substantial crotch.
As the meetings went on, and we became more familiar with each other, I started to notice the way Felix would manhandle his assistant. From slaps on the ass, to pushing him down into his chair with a hand on the shoulder, to even grabbing his chin when asking him if he could fetch us some snacks. I also noticed how tentatively the assistant was sitting down. He'd ease into chairs with a look of pain on his face, and took very short strides while walking.
The talks had gone on for four straight days, before they finally came to an agreement on Thursday afternoon. With both parties happy with the outcome of the deal, they decided a celebratory meal would be appropriate. Oliver said he would be treating the four of us to the cities best steakhouse!
Felix and his assistant went in their car, and I rode with Oliver. When we got into his car, he reached across me into the glove compartment, and pulled out an ass plug. But this one was different than the others he'd had me use. After getting me to lube it up with my mouth, and push it into my ass, he informed me that it was a remote controlled vibrating plug that he'd bought as a gift for me especially for this occasion. To prevent me from removing it, he had me secure a set of chains to it. They fit like a thong would, but without anything to cover the dick area, and were fastened tightly. Strangely I thanked him sincerely, and felt special in the seat next to him.
After arriving at the restaurant, we were seated at a nice table in a quiet corner of the restaurant. It was a square table. Felix and Oliver sat opposite each other, with their assistants between them. When the waitress arrived to take our dinner orders, we were already onto our second bottle of wine. I ordered first, and asked for a nice thick steak. Oliver followed, and before ordering his own meal looked at the waitress and said "cancel his steak, he'll be getting some thick meat later. Bring him a light green salad, no dressing. I'll have the lobster."
I was mortified! This hot young blonde waitress stood there and giggled to herself, as she corrected my order. Here I was, tall, good looking, strong, and this meager looking little guy was telling her that I'd be getting some thick meat in my mouth later in the night. When he noticed my discomfort, he started up the plug. I jolted upright, and immediately had a smile on my face. He kept it on a low speed, teasing my body, and making my dick swell to fill the inside of my chastity device.
Felix didn't even let his assistant get a word in edgewise, he just said "give him the same as he's having (pointing at me), and I'll have the lobster as well".
After supper, I excused myself to go to the washroom. Oliver permitted me to leave, but added "I'll give you two minutes. If you're late, no supper for you." At hearing this Felix laughed heartily.
This was the first time that, while in public, Oliver had treated me like his bitch. Calling me names, giving me orders, and although I was embarrassed at first, I was getting turned on by everything. The vibrations in my ass weren't helping though!
"Well boys" Oliver started, "we're gonna head back to my place for some after dinner drinks."
Most of the restaurant was empty as we were leaving, but on our way out we did cross paths with our waitress who smirked at me and said 'enjoy your meal".
Upon hearing this Oliver laughed, and then invited her over to watch me 'eat'. Unfortunately, she obliged. He then turned the speed up on the vibrator, and asked if that was ok... I squirmed, giggled, and barely managed to say "uh, yeah... um.. sure.. please".
Shortly after we arrived, Oliver had me turn on some music, and serve drinks to everyone, including our new guest Jessie who was loving watching me and the other assistant getting bossed around.
