Kept Man Ch. 01

After a minute or so, Jennifer ordered me to stop, turn around and tongue-bathe Mr. Kingfisher's feet. I removed myself to fall on all fours on the floor before the vice-president. I took in one toe after the other as I massaged his feet gently.

Behind me, I heard Jennifer going through a box on the bookshelf, and removing its contents. I was aware of this, but took little interest compared to the task in hand, or task in mouth, as it were. My main attention was for pleasing Mr. Kingfisher's feet until I once more felt fingers cold with jelly sliming my asshole. I was only for a moment startled, and as I heard a jingle of clatter behind me, I realized Jennifer was buckling on a strap-on. I was going to be pegged.

I had been fucked by men before, of course, but something about the thought of having my ass violated by a woman in the man's fashion turned me on. This would be my first time being fucked in the backside by a female.

Jennifer rearranged me slightly, pulling my ass up while my face was down in the feet of Mr. Kingfisher. When she had me placed just right, I felt the lubed-up silicon cock pressing against my hole. As I felt the tip of the dildo slipping past the ring of my anal sphincter, my back arched and I gave a great groan. Mr. Kingfisher repositioned himself so that his cock was closer as I descended again. When I leaned forward and put my hands on his knees to steady myself, my face was in just the right place to give him head. I opened my mouth and sucked the head of his dick into my mouth with a loud slurp just as Jennifer rammed the rest of the dildo into my hole with the weight of her hips behind it. Once more, I let slip an accepting groan. Jennifer established a rhythm as she ass-fucked me, and I mirrored that metre in my cocksucking. My head bobbed over my vice-president's organ and I applied suction and tongue massage techniques in equal measure.

Jennifer had been steadying herself using her hands on my hips, but as she ground against me, I felt her hands slide down to my smooth buttocks, caressing me. I was pleased to realize that Jennifer was beginning to breathe hard as she fucked me. She wasn't tired; I was sure that her end of the strap-on was stimulating her clit as much as my end was stimulating the pleasure centres of my arse.

"Do you like having your sissy ass dominated, faggot?" Jennifer asked.

"Yes, Jennifer," I answered. She immediately slapped my ass hard.

"I'm not 'Jennifer' to you, fuck-toy," Jennifer declared. She never missed a thrust while she was speaking. "You'll address me as Ms. Gaetano. I'm your immediate boss under Mr. Kingfisher and you will treat me with the respect I deserve."

"Yes, Ms. Gaetano," I answered over my shoulder.

"Get that cock down your neck now," she said.

I obeyed, inhaling Mr. Kingfisher's cock again, servicing it with a will. Behind me, I heard Jennifer's breathing turn even more irregular and I felt her convulsions through the strap-on. I realized my immediate superior was fucking me through the throes of her own orgasm. When she came down, she withdrew the artificial penis from the depths of my ass with such force I thought my bowels would go with it.

"Okay, fairy-boy, we know you can suck and we know you can take a pounding, but can you dish it out?" She lay on the clean, carpeted floor beside me stark naked after discarding the strap-on. "Let's find out. Remember, it's your boss you're fucking now and your performance will be evaluated."

She threw a condom at me. Mr. Kingfisher stood up, terminating the blowjob I was giving him. He reached over to his desk drawer and withdrew yet another condom. He tore the foil and put the rubber on. I picked up the safe in front of me and followed his example.

When both of us had our organs under wraps, Jennifer spread her legs and urged me to fuck her. It was not the most romantic proposition I'd ever had, but I had no complaints. I positioned myself over her and began kissing her neck, fearful that she might pull rank again and condemn my familiarity, but in the end, this was part of the technique she was evaluating. I licked my way down from her neck until I could nip and suck at her nipples.

"Just put it in and get started, lover boy," she said. "I have a meeting at one o'clock. You have ten minutes to get me off. And while you're at it, be a good boy and let Mr. Kingfisher ride your ass."

It was a day of firsts. I had been in threesomes before, but I has never let a man fuck me while I fucked a woman at the same time.

I was feeling confident in the moment. I penetrated Jennifer without further warning, but she did not seem to mind. My one worry was that I might not last long in her tight pussy after all the stimulation I'd experienced in the last hour. In the meantime, even more stimulation was added as Mr. Kingfisher hovered over me, pinning me with his weight; I was still able to thrust effectively inside Jennifer as the executive pressed his lubricated, latex-skinned cock against my equally well-lubricated asshole. After the working my hole experienced under Jennifer's strap-on dildo, it was receptive to an easy penetration. Mr. Kingfisher slid into me up to the balls.

Soon, the three of us moved like a single creature of pulsing, undulating flesh. The V.P. fucked me as I fucked his executive assistant. I felt heat in my balls and worried I wouldn't last, but to my amazement, Jennifer's sighs took on a high note as my grinding cock drove her through a frenzied orgasm. I couldn't hold back anymore myself and with a grunt, I filled the condom deep within Jennifer with my semen. We came down from our orgasms together, and when she was satisfied, she said so.

"Alright, get off me, Tiger," she said, with the first smile she'd shown me since our introduction in the hallway.

I tried to obey, but I was delayed by the force of Mr. Kingfisher's ongoing thrusts. The boss heard Jennifer, but he was close. Before he could finish in my backside, he pulled out and turned me over so I was lying on my back with my head cushioned by Jennifer's wet pussy. He peeled off the condom and gave his cock a few more pulls before he sprayed my face and chest with his hot sperm. I had known what to expect when he rolled me over and I had my mouth open. His jism tasted as sweet as it was salty.

"What do you think, Jennifer?" Mr. Kingfisher asked over me.

"He ticks my boxes," she said. "Let's hire him on a three-month probationary status."

Remembering I was still there, Mr. Kingfisher asked if that was alright with me. I was thinking that if the job was as good as the interview, I'd be very happy working for the corporation. I nodded and gave thanks.

The two professionals got up and quickly made use of the towels from the laundry bin before dressing themselves. I followed their example as energetically as I could manage; I didn't want to be thought one of those guys who just rolls over after a fuck, but, together, they had nearly fucked my lights out. I wiped the trails of sperm off my face and body and quickly replaced my suit. On the window glass, I could see my reflection. I looked only a little rumpled. At Jennifer's direction, I collected the dirty towels and placed them back in the bin which seemed so out of place in a V.P.'s office. Mr. Kingfisher resumed his seat behind his desk and began checking his messages as Jennifer instructed me about starting date, corporate training and orientation (no, they weren't teaching me to fuck; just a primer on the corporation and its vision and some health and safety training), inspection of my new digs, assignment of the company car and the signing of my contract. It was determined my contract would begin the first day of the next month and I would be issued my formal work ID on that date.

When it rolled around, I was allowed to attend orientation in casual clothes. I set up my pre-authorized payroll deposit and was surprised as well with a live cheque paying me handsomely for my in-office day with Mr. Kingfisher and Jennifer Gaetano. I was not disappointed in the corporate world so far. By the end of the week, I was living in a two-bedroom hotel suite in a luxury hotel and driving a sporty car. My wardrobe was upgraded and my fashion advisor threw out all my old clothes with my blessing; I would have my advisor's insight into my choice of clothes before all my "dates".

Finally, a week after completing my official training, I was taking other courses sponsored by the corporation; I was actually being paid to earn new skills like sensual massage the art of cooking. A sex therapist was teaching me how to seduce men and women and the scientifically-proven ways to please them and their various fetishes and desires.

On day eight, my new work phone (a special private number) beeped and I blinked at the unfamiliar notification.

I had my first assignment. I licked my lips with excitement and acknowledged the message, accepting the task. I would be meeting an African government trade delegate for supper at the hotel at seven o'clock...