Taskmaster
Brian handed Rachel four sealed and numbered envelopes and then crossed the room, his shoes echoing on the hardwood floor. He sat in one of two adjacent easy chairs, the other occupied by the stranger they had agreed upon earlier -- a younger man -- very fit with broad shoulders and a masculine face full of confidence. A fireplace was glowing in the corner of the large room. On another wall, the king-size bed awaited.
The instructions on each envelope were from Brian's imagination. Rachel had been edging him for days leading up to this weekend getaway -- teasing him with lubricated hands some days until precum oozed from the head of his penis and he began to plead with her to finish the job. Tighter he would tell her or -- or faster. And Rachel was compliant with his demands and attentive to his needs -- but only to a point. Other days were worse -- it was her wet agile mouth -- taking his cock deep and teasing his glans with the slick warmth of her tongue. Brian wanted nothing more than to reach with his fist and pump the length of his shaft so he could spill hot white cum all over her waiting tongue. He begged for release, but Rachel knew him well and drew away when his balls began to tighten.
She had reduced to him to state of need greater than any he could recently recall. When he took pen in hand and wrote each small note, you could imagine the fever fueling his imagination. Cock-teased to the point of unbearability and yet so happy to be left on this edge of intense arousal. The devil was his muse as he imagined the scenarios to come and he crafted the notes to fit.
The hotel was rustic, but upscale. The suite was large -- hence the chairs in the room and the space for the fire. It was dark outside, but the curtains were open, and a full moon provided additional illumination to the room -- through the sheers across the large window. Rachel sat in a simpler chair across from the two men. Brian had watched her dress at home before they set out. He recalled the black thigh-high stockings -- the garter added for extra hold -- the almost sheer, small, black panties and the black bra -- also see through with the clasp front and center. The bra, deliberately it must be admitted, was a size too small and her breasts were pushed together with some cleavage above the clasp. All the above, covered - at least for the moment, with a short black dress fastened with snaps most of which remain closed as she sat facing them in the hotel room. Brian has seen her in that dress before. He'd pulled those snaps apart quite aggressively before and fucked her hard when she had teased him in the past.
The gentlemen are casually but smartly attired. Rachel had noticed the tight fit of the faded jeans on the stranger and, yes, her eyes had lingered on what was outlined inside. An outline that was very pleasing and promising, and her imagination too was beginning to spark with possibilities. He had a crisp white dress shirt, and she noticed the strain in the material as it stretched across his well-defined chest.
Rachel gazed into both men's eyes, smiled at each, and then opened the first of the envelopes. She read aloud:
Using any technique you wish, arouse both men until you're certain that each is hard with desire.
Just the reading of the note had changed the temperature in the room. Brian knew the instructions but hearing the confidence in Rachel's voice as she read and imagining the surprise of the stranger, excited him.
Rachel pondered the possibilities. Men are simple. Their cocks are simple. She knew a light grazing of her fingers over the material of their pants would do the job. But she knew there were three more envelopes to come. She thought for a bit. She wondered if she need do anything further beyond the simple reading of the note -- let that silence linger in the air. The stranger would be wondering about the envelopes to come. She expected Brian was beginning to breath faster already and would not be surprised if stirrings were there inside his underwear given the state she had left him in earlier. Blood pulsing in but with no escape -- the prick lengthening and growing.
She pondered and decided on the choice that had been left to her. She began to speak -- softly, slowly and with a certain huskiness of tone that let them know she was enjoying this:
"I want to tell you about the first time I tasted a man's cum. I remember it well. I was still a young woman myself, virginal but eager to escape that condition. We'd made out several times on the bench seat of his Dad's Chevy. He was a sloppy kisser, but I taught him to take his time and he improved steadily to the point that his tongue, now in my mouth, and his hands over my clothes made me very wet. I was often braless in those days and on this occasion. I hadn't stopped him as he slowly opened my blouse and touched my firm high-school tits. Sometimes surrounding them with his large hands and sometimes teasing my nipples with his fingertips. I was straddled across him. My skirt was pulled up and my panties, damp now, were firmly pressed into his crotch. He kissed me. He touched me. I ground against him. I felt his hardness against my panties. It was almost enough to make me come and I really, really, wanted to come. I reached down, undid his belt and zipper and he raised his hips for me. I pulled his jeans down so I could press my pussy against his underwear that were also slightly damp. It was much better now. I felt his length and his hardness. Even better I felt the heat of his cock against my own heat. I came closer still. In in the heat of the moment I reached between us and pulled his underwear down freeing his large cock. A new experience for me -- the sight of it overwhelming me. I stroked him -- amazed at the heft -- astounded by how hard he was. I pressed my panties against him again and rocked my hips against him. I came hard -- with a loud moan and gasp -- delighted by the intensity of pleasure -- vibrations from my clit, contractions of my cunt, pulsing of my asshole. All so, so good. I caught my breath. I wanted him to feel what I was feeling. I leaned back, took his cock in my hand, tightened my fingers, and began stroking him. He panted. Soft moans escaped his lips. I heard over and over "Oh Rachel. Oh Rachel. Oh". He gently placed his hand on the back of my head. Just a hint. I knew what he wanted -- what all men want. I doubted much expertise was required. I lowered my head. I parted my lips. I opened my mouth. I placed my tongue on the head of his cock and then drew him in. I stroked him with my hand and felt my mouth over him. I felt his cock tighten and then pulse and then whoosh -- his semen was exploding in my mouth. I'll never forget the feeling of power a woman has over a man. When he was spent, I opened my mouth wider and let his cum spill from my lips and coat his cock."
Rachel glanced over and there was no doubt task one had been accomplished. Two large dicks were clearly outlined -- even in the dim light. She drank in the sight of them for a moment and then opened the second card. She read it silently -- looked them closely in the eyes and then recited her next instruction:
Arouse both men until they cannot help but touch themselves. You may use any technique you wish but nothing you have already done this evening.
So -- no more stories then. As they were to touch themselves so she felt she should keep her distance still. Rachel knew how to excite men from a distance. She reached for her phone, browsed through her music selections, and played one of her old favourites. The voice of Chris Isaak filled the room:
"I've been thinking of what I should say
