I lay on Sterling's king-sized bed, with my hands resting on my bare stomach. Though I was blindfolded and unable to see my surroundings, I'd been in this room numerous times before and was familiar with it. Inhaling deeply, I detected a trace of Sterling's expensive cologne lingering in the air.
When my nerves started getting the better of me, I reminded myself of all the money I was making from tonight. Sterling, one of my best clients, had always paid me extravagantly for what amounted to standard, vanilla sex. Not that I was complaining about his ordinary tastes; the man knew how to fuck and make a woman come multiple times. But during our recent conversation over dinner, he'd offered me the opportunity to earn a shitload if I was willing to participate in group sex with him and three other men.
"These men will remain anonymous to you," he said before taking a bite of Wagyu steak.
I tried not to appear surprised by his words. "How will we manage that if I'm fucking them?"
"You'll be blindfolded beforehand." Sterling waited for my reaction, but I succeeded in keeping my expression neutral. In the candlelight illuminating our table, I couldn't help but admire the man sitting across from me. With dark hair and eyes, he appeared far younger than his fifty years. His body was lean and fit, a result of his dedicated workout regimen. "My friends are powerful men," he went on, "and their sexual proclivities cannot be made public. I know you'll be discreet, Shannon. You've always been the utmost professional." Lifting his wineglass to his lips, he added with a grin, "Not to mention you're absolutely incredible in bed."
"It's my job," I replied, flashing my own grin.
Sterling's gaze moved over me. I knew he preferred me wearing my hair down, so the chestnut waves spilled past my shoulders that night. My red dress fit perfectly, revealing a tasteful amount of cleavage. Later on, he would take me back to his place and sit in a chair while I slowly, teasingly, stripped for him. Delayed gratification always got him off.
But we had to talk business first. The figure he proposed for entertaining him and his friends was one I'd be a fool to turn down. "You're fine with having all your holes used," he said, stating it as a fact instead of a question. Still, I nodded my assent. "One of these men has asked if you'll consider double vaginal penetration. He's willing to pay an extra three grand if you agree."
I pretended to consider the offer for a moment, but I'd already made up my mind. "I'm amenable to that."
Sterling smiled at my response. More than once, he'd told me he'd never met a woman in her mid-twenties who possessed my maturity and poise. Of course, if he'd wanted me to act flirty and girlish, I would have indulged him. For the right price, I'd be whatever he desired.
I'd started doing this to pay for college, but after graduating, I didn't settle into the career I planned for myself. Instead, I kept building up my clientele. Now, I was the only one among my circle of friends who could easily make the rent each month.
"What about ass-to-mouth?" Sterling asked. "You okay with that?"
I always used an enema before anal sex to ensure I was as clean as possible, so Sterling's question wasn't as distasteful to me as it might have been to others. "For an extra thousand, I'm absolutely fine with it," I told him.
He didn't even blink at the increased fee. "Perfect. Now, let's agree on a safe word. If you use it, all activity will immediately stop so I can check in with you."
"My safe word is hazy." I'd used it with other clients in the past.
"Alright. And if you're unable to speak due to a cock being in your mouth, just hold up two fingers, and I'll know you want to stop."
Sterling and I went over a few more details. The men wanted to fuck me bare, so everyone would need to be screened for STIs beforehand. He would let me know when the men had provided their results, and I would be required to show him mine. None of this was a problem for me. In fact, I was glad he was so diligent.
"Hard limits?" he finally asked me.
"No spitting or slapping. No scat play, either."
He actually grimaced. "I wouldn't dream of it, sweetheart. These men won't be degrading, but they will be... insistent. They won't wait for your permission to do what they want. Is that acceptable to you?"
"Absolutely," I answered without hesitation.
As I now waited for Sterling and his friends to enter the bedroom, I did a mental scan of my body, making an effort to relax all my muscles. I was no stranger to group sex, but some of tonight's activities would be outside my comfort zone. I knew these men were paying for a ready and willing participant, and I was determined not to reveal the low-level anxiety I'd experienced for much of the day. Though I hadn't asked Sterling what made him and his buddies decide they wanted to hire me for the evening, he mentioned that they'd just secured a very lucrative business deal, and this was their way of celebrating.
The blindfold was very secure, almost uncomfortably tight. Sterling had instructed me to wear only a bra and panties. "I like the sheer black ones you had on last time we fucked," he said. "Don't bother with anything too intricate."
My sense of hearing seemed to grow more acute as I listened to the men enter the bedroom. "Gentleman," Sterling spoke, "I'd like you to meet Shannon, the guest of honor this evening."
I had to grin at his choice of words. The four of them would soon hungrily descend upon me, but Sterling made it sound like we were attending an elegant soiree. When his friends greeted me, I turned my face in their direction. "It's a pleasure to meet you."
"The pleasure's all mine," one of them said in a rich, deep voice.
I heard and felt them join me on the bed. It didn't take me long to discover that they were already naked. Someone eased me into a sitting position. "Up you go, gorgeous." At the sound of Sterling's voice, I smiled again. His presence would serve to anchor me tonight; as long as he was close, I trusted that I'd be safe.
"Let's enjoy her, shall we?" he said to the others. The suggestion served as a catalyst, for I immediately felt hands all over me. They were gentle yet insistent in unclasping my bra and pulling aside the crotch of my panties. A moan escaped my lips when one of the strangers sought out my clit.
"Oh, she's already nice and wet for us!" he said in a voice thick with lust.
"I know from experience how much she loves to play." Sterling's lips met mine, and I gave him a wanton kiss, full of tongue.
Moments later, my panties were yanked down my legs. Once I was completely naked, two men positioned me so that I straddled the face of another. His tongue was tentative in exploring me at first, but he soon pulled me firmly against his mouth. Tilting my head back, I basked in the feel of his eager licking and sucking.
Large, strong hands squeezed my breasts. It was surreal, even mildly disorienting, to be deprived of one of my senses. But the way I'd been rendered practically helpless as these men maneuvered me like a doll served to arouse me, too. I was shocked to be so turned on while at their mercy. It was a vulnerability I rarely permitted myself in this line of work.
As my cries filled the room, I began grinding my pussy against the stranger's face. My movements clearly excited him, for he ate me out with a fervor that stole my breath. Sterling kissed me again, his mouth hard and demanding. Another man circled his lips around my nipple, while someone else caressed my buttocks.
The attention of Sterling and his friends filled me with a kind of euphoria; I was high from their touch, and from the way they overwhelmed my senses. I'd always orgasmed easily, and at the hands of four incredibly aroused men, I now came with a fierce shudder. Someone kept me upright as my quaking continued, and I finally managed to lift myself off the face of the man beneath me.
Next, I was drawn downward until the same man's hard cock was directly below my entrance. With a knee planted on either side of his legs, I reached between my thighs to seek out his dick and guide the tip to my opening. Then, I slowly took him inside me.
"Fuck, yes!" the man groaned.
Fingers fondled my nipples and teased my clit. My skin had grown hot, and as I began riding the cock inside me, I could hear how wet I was.
"She's so fucking gorgeous!" a man said from behind me. The energy in the room seemed to intensify by the second, and I easily sensed how much each of them wanted to claim one of my holes.
I offered no resistance while being guided downward so that I lay upon the man beneath me. Immediately, I felt a hard cock at my lips, and I opened my mouth wide to take it. By now, I intimately knew Sterling's taste and scent, and he knew he could thrust deep without choking me. His hand was gentle on my head. "That's it, baby. Take it all!"
The sounds emerging from my throat grew increasingly pornographic. All around me, I heard groans and heavy breathing as Sterling fucked my face. "Christ, she's swallowing your entire dick!" someone exclaimed.
When I felt lube being smeared over my puckered hole, I strove to stay relaxed. Earlier, I'd worn a plug in order to stretch my ass, so I was prepared for the cock which now prodded my opening.