The 766 Club Job

"Jesus, what happened to you? You okay?"

Sly's left arm was in a sling, his left wrist bandaged up and a nasty cut over his right eye.

"Fuck that", he said. "I got a job for you for next Thursday. I promise you, you are going to love this one, Princess. It's just up your alley." Sly sat back with a shit-eating grin. I gave him a hard look. I'd heard this before.

"It had better be good," I said. "I'm taking a chance meeting you like this." We were meeting at the Starbucks a couple of blocks from the law office where my day job was.

On the plus side, Sly had already ordered a venti white chocolate latte for me. It's nice when someone knows your favorites. On the minus side, I bristled at the casual way he organized my 'second life'. I suppose he has to have some leeway in arranging dates for me when I'm not there. The circles he travels in and how he finds clients for me is a mystery to me. As his injuries attested to, there are dark parts to Sly's life that I don't know or want to know about, so long as he is good to me and treats me with respect.

"'S'matter, Princess? Afraid one of your uptight colleagues'll see you with disreputable ol' me? The suit ain't good enough?"

I smiled. "No, and actually I am impressed at the suit. Didn't know you owned one."

"I didn't until yesterday," Sly said. "But y'know, we're doin' so well these last few weeks, it seemed to me your agent needed to move up."

Well, I'd be damned. Sly actually referred to himself as my "agent"! For weeks I'd been bitching at him to quit calling himself my pimp.

A bit of explanation here if you're new to my tales. Yes, I do work during the day as a copywriter in a prestigious law firm, but before that job had gotten started, when I was about to graduate from college, I'd made a couple of shall we say 'moral slips', which Sly managed to turn into blackmail. To extricate myself I went to work for him servicing his clients for money until I could pay him off. When the debt was finally cleared, he pointed out to me what I had not been willing to admit to myself: I was good at the work and I liked it. Once I accepted that, we partnered up, and though I kept my day job, I've been handling clients for Sly at night for some time now, to a very nice profit for both of us.

Funny thing is, despite our very different backgrounds, me a traditional WASP and him raised on the streets, we've found a mutual respect for each other. Even so, I've been working on his vocabulary if for no other reason than for my own personal sense of who I am. And now, out of the blue, he's 'my agent'. Wow.

"Anyway, the suit looks good on you. So, what's this job I'm gonna love?"

"You know the 766 club?" he said.

"Sure. Bunch of rich guys formed a very exclusive club a couple of years ago. Near as I can make out, mostly for parties and to impress one another. So, what's that got to do with me?"

"Ok. I've got word from a friend of a friend that there's a john - er, 'client' who's looking for a sophisticated escort for an evening. And boy, is he willing to pay! I'm betting that you are just what he's looking for. And if that ain't enough for you, think of this as a chance to break into the big time."

"This guy, does he just want arm candy or is there more, here?"

"Honey, that's entirely up to you. Work it out with him. You in?"

"I'm in. Sounds like fun."

"That's my girl. I knew I could count on you. In fact, I've already fronted some of our cash on this one. Here's a reservation at the Arden spa for a complete workover next Thursday. Then meet me at my apartment."

"Hey, you think I need a workover??"

"Funny. Just do it, hunh?"

The next Thursday I showed up dutifully at Sly's, all properly spa'ed out. Rubbed down, tweezed, scrubbed and coiffured. I admit, I was impressed at myself. Every girl wants to look like this once in their life. I took the gown that Sly had gotten for me and went into the bedroom to change. I suppose that that bit of modesty sounds a little silly given the relationship Sly and I have, but it's part of the respect deal.

After some time admiring myself in the mirror, I came out. Sly sure has my dimensions down pat!

"Jesus! You look gorgeous!" he said. I had to agree. The gown was form-fitting and accentuated my trim waist and my curving hips. It was daringly low-cut and made the absolute most of my already generous bosom. Hell, a guy could lose himself in my cleavage and not ever come up for air. The gown was floor length, but the slit on the right side showed my long leg all the way up to the lacy top of my stocking with each step. The high heels shaped my legs beautifully.

Sly looked meaningfully at me. "Babe, if we had more time..."

Giving him my most fetching look, I smiled and said "Forget it. Price you pay for being management."

It seemed such a waste to bottle up all that pulchritude in a taxi, but on the plus side I sure made the driver's day. Twice I had to tell him to keep is damn eyes on the road before he killed both of us. He did finally manage to deliver me to a lovely brownstone in the upper sixties. He wouldn't take a tip.

The man who met me at the door was tall, very good looking, and beautifully dressed in an expensive tailored tux. I smiled inwardly. This wasn't going to be bad at all, whatever this guy might want of me.

He looked me over very carefully. His eyes lingered on my breasts. Clearly, I passed inspection, for he smiled and introduced himself and invited me in.

"You certainly are everything that your agent promised," he said. "I'm going to love showing you off tonight.

"But first, we need to deal with a preliminary. Tonight, you are going to be dancing with many men who will admire you. Some may even want to get to know you better. Many will envy me. I want to know that as I watch you with them, my sperm is in you."

Well, that was different. I know men can be possessive, but this seemed a bit much. Too much like wolves scent-marking their territory. However, given what he was paying me, I wasn't going to let a little foreplay get in the way.

Taking my hand, he led me to the bedroom. It was lavishly furnished, centered around a large bed. There were lots of mirrors, including the one over the bed. This was going to be fun!

"Charles," I said, I'm more than happy to be bedded by you, but may I suggest that you let me take the lead? That way I can preserve the look that you would want me to have."

"I like you," he said. "I see that you're not just beautiful. Sure, I accede to your control."

Excellent. I like a challenge, and getting out of this outfit as seductively as possible without wrinkling it or mussing my makeup and coiffure was certainly that. Luckily, the artists at Arden had left my hair long, just glossier and silkier, so I didn't have to worry about destroying their work.

I can say with some pride that I rose to the occasion. I submit as evidence that by the time my clothes were off and neatly folded, Charles had a massive erection and was already breathing hard.

I lay back on the bed, my arms raised to accentuate my breasts, my legs slightly apart, just enough to let him see what he was about to enjoy. I'd left my stockings on; guys seem to like that, and frankly, it makes me feel pretty sexy, too. It didn't take a written invitation. In a second, he was on top of me, and that massive erection was pushing at my pussy lips.

I grasped his ass and pulled him down while I raised my pelvis. Between his pre-cum and my early arousal, he slid into me easily. That cock felt just as good as it had looked. I moaned. He began to stroke into me. God, it felt nice. He kissed me and fondled my breasts. My nipples grew hard under his ministrations. Pretty soon I was ready. I pulled him into me and worked my pelvic floor muscles and perineum to massage his cock. He gasped with pleasure and came into me. My vaginal lips stretched as his cock pulsed and swelled, and then I felt the warmth and pressure of his semen as he pumped it into me. Lord, how I wanted to let go and squirt all over him, but I kept just enough control of myself so as not to ruin my hair and makeup. That was something of a bummer; I hope I never have to do that again! Still, it felt very good in spite of that.

"That was excellent," he said as he withdrew. "Now neither of us will forget whom you belong to tonight."

I'm not thrilled about the idea of 'belonging' to any man, but I am a professional, so I kept quiet. Sly always says that if it ain't gonna hurt ya none, give the client what he wants. Actually, Sly doesn't always call them 'clients'; he has other, more pejorative terms, but I'm working on his vocabulary.

Charles glanced at the clock. "We'd better get going," he said.

We dressed. I took a moment or two in the boudoir to make any necessary repairs, and we headed downstairs.

The townhouse had a garage, and in the garage was a limo and driver. We got in. Charles gave the driver the address, and then had him roll up the glass partition behind his seat.

We had barely left when Charles leaned into me and put his right arm around me. He drew me close and kissed me. He kissed very nicely, and while I was distracted by that his left hand went to my breasts. He stopped kissing and looked carefully at his hand, dark against the creamy mounds of my breasts gently rising above the low-cut gown.

"You have very beautiful breasts," he said, stroking them. He bent down and kissed them. Then he kissed me on the mouth again, even harder this time. Our tongues intertwined. I was enjoying this. I felt his left hand slide between the edges of the slit of my gown and caress my stocking-clad leg. His hand traced a warm path up along the inside of my thigh until I felt his fingers touch the silk vee of my panties.

His kissing became rather more intense, then, as his fingers first probed my panties and then pushed them aside. By then I was breathing hard, kissing or no kissing, and beginning to moan a little. Charles' head moved down to my breasts again and he started kissing the exposed flesh. My head lolled back against the soft leather of the seat. I entwined my fingers in his thick hair and encouraged his movements on my breasts. His warm breath there felt great.

One distant part of me wondered what the limo driver was making of all this. I opened my eyes long enough for a quick glance over Charles' head. Nope. His eyes were solidly on the road, his hands relaxed on the steering wheel. I guess this wasn't his first rodeo.

Charles' fingers found their way to the opening of my wet pussy and slid into me. Jesus, it felt good. I was starting to glow all over. I was moaning with pleasure. One more millimeter and he was going to hit my clit, and if he did it would be all over. I didn't care. I knew I was going to spurt all over those lovely leather seats and maybe wreck my gown, but I didn't care. The only thing I cared about was pursuing that incredible feeling that was so very close, almost within reach.

And just like that he pulled out of me and leaned back. I was gobsmacked! My mind was whirling.

"There, dear," he said in a very calm voice. "That's a taste, just a reminder of who owns you tonight. Don't forget it."

Jesus, I could cheerfully have killed him then and there, and I don't think anyone would blame me. It took every ounce of professionalism I possessed to keep my cool. I just shut my mouth and tried to calm down. In my mind, though, that was now two he owed me. By God I was going to collect, somehow. I forced a smile.

"I won't forget," I said between clenched teeth. "For tonight, I belong to you, and only to you."

Ok, the party was wonderful. It was way north on Fifth Avenue, in a very high-priced neighborhood. You'd never know from the elegant but bland exterior what a great place it was inside. The ballroom was on the second floor, and something out of the French Belle Époque. Lots of gilding, chandeliers, etc. There was a live orchestra, and all the guys looked great (and wealthy) in tuxes. Most of the women were beautiful and elegantly dressed. I worried about holding my own, but Charles seemed quite pleased to compare me favorably, and judging from the number of dance invitations I got he was justified. All in all, it was quite a night. Charles didn't mind my dancing with others; in fact, he seemed to enjoy watching me with them. Of course, I knew what was going on behind his smiling mask. To hell with him, I loved it. Got quite a few requests for my phone number. Damn, I wish I could have given it out, but I had to play the woman of mystery, which ironically got me more attention, not less.

Like I said, it was quite a night. All I needed was a glass slipper to leave behind at midnight. God, I love this job!

We didn't get back to Charles' apartment until three a.m. Thankfully, it was a Sunday, I'd never have been able to deal with my day job otherwise.

I was ready to call it a day, but unsurprisingly, Charles had other ideas.

"You enjoyed tonight, didn't you," he said. "I enjoyed watching you. Your body is marvelous, and I loved watching your legs and your breasts as you danced. I kept thinking about how jealous of me the men you danced with were, knowing that you were mine, thinking about how much they were wishing they could be me when I fuck you tonight. I'll be thinking of them when I do.

"Take off your clothes."

Well, after this, nobody can accuse me of not being a professional. I smiled at him and proceeded to strip, doing it slowly and as lasciviously. I watched the bulge in his pants grow as his eyes followed my every movement. When I was done, I approached him and undressed him, starting with his shirt and finishing with his shorts. I pressed my breasts against his bare chest, put my hand behind his head and pulled him down to kiss him. I stroked his erection and then gracefully knelt in front of him. I kissed his cock and took a few inches of it into my mouth. He moaned.

I backed off for a moment and smiled up at him, my lips still wet with my saliva from his prick. "Would you like to cum in my mouth?" I asked. "It would give me pleasure to feel you cumming in there, and to swallow your sperm." I'm rather proud of my acting skills.

I could tell he was torn. His wet cock hovered only inches from my mouth. I licked my lips and parted them slightly in invitation. I let my warm breath flow onto his prick. His hands moved toward my head. But then he shook himself with an effort of will and said "No. Get onto the bed. Kneel."

Uh oh. That sounded like a back door approach. Sure, I've done it before, and have gotten pleasure out of it, but it's not my favorite. However, he's the paying client, so I did as told.

Moments later I felt the bed sag as he climbed into it behind me. I felt the warmth and weight of his cock as he laid it between my buttocks. It felt nice and heavy. I felt a cool drop of his pre-cum drip onto me. He reached around and grasped my breasts and massaged them. That felt pretty good. I could feel my nipples harden and my pussy begin to milk. I began to sway my ass back and forth while still embracing his heavy cock with my ass-cheeks. I was starting to get into this. I decided that however he put his cock into me I was going to enjoy it. I figured that with just a little extra work on my part I was about to collect on what he owed me from earlier. He had his choice of entry into me. I waited for him to make up his mind.

I didn't have long to wait. The big tip of his cock soon pressed against my pussy lips. He released my breasts and grasped my hips, pulling me back into him. His swollen cock easily parted my lubricated lips and slid into me. It felt very good in there, warm and pulsing with life. I pushed back against him to get him in even deeper. His sperm-laden balls pressed against my pussy and hung between my legs. He stroked in and out. His breathing came faster and faster.

I was well on my way to heaven when he surprised me. He abruptly pulled out of me and moved his cock an inch or two and addressed it to my anus. Before I could react he shoved, and the thick head popped into me. He was well-lubricated from my own juices, so he slid in easily once the head was past my anal ring. Well, surprise it might have been, but it still felt very good in there. With all the goings this past night I was way more than willing to accommodate him so long as I could achieve my own ends. I pressed back into him. He gasped as I did.

He started pumping me in earnest then. Back and forth, deep and shallow. I loved it. His cock in me was so big, so warm, filling me up. I wanted his semen in me, to feel him spurt his load deep in my ass. Professional or not, I stopped caring about what Charles wanted and focused only on my own needs. Hell, he owed me! Soon I was bucking back against him in time with his thrusts and wagging from side to side as well. Both of us were gasping and groaning with effort and passion.

Suddenly as if of their own will my arms gave out and I collapsed forward on the bed. Charles' body fell full on my back. His cock drove deep into my ass. God bless him, he didn't miss a beat, but kept pumping, resting on his knees and hands to lift his groin on the outstroke and then using his weight to drive down and into me. With my newly free hand I reached under myself and fingered my clit. I was about to explode.

We came at the same time. I felt his cock swell and throb in me. He groaned and then gave a loud "Aaaah!" as he came. His hot semen shot under pressure into me, filling me with its warmth. That did it for me. I cried out and came, full force, spurting like a fountain. I buried my face in the pillows and yelled as I came, my fists pounding on the bed. Oh lord, it was wonderful. My buttocks and my perineal muscles contracted and milked that sweet penis of all that it could give as we moaned and gasped in synchrony.

After an eternity in paradise, it was over. Both of us were breathing hard, as if we'd run a marathon. The pillow was wet where I had cried and slobbered into it. The bedclothes were soaked with my discharge and Charles' copious cum that had backed up around his cock and run down over my wet pussy. I could still feel his semen's presence in me as it spread comfortably through my rectum. I was well satisfied that I had made up for Charles' earlier frustrating behavior. If I could have, I would have just closed my eyes and slept with his cock still in my ass.

Alas, though, the real world intruded. As his breathing slowed, Charles withdrew from me. I rolled over. Charles tenderly kissed my breasts, glistening with the perspiration from our exertions.

"You were phenomenal," he said, almost wonderingly. "I feel completely drained, and yet I hate to let go of you. Believe me, I'd fuck you again if I could."

"I appreciate the compliment," I said. "Sadly, I have to go. It'll be light out soon. But thank you for a wonderful evening."

"The pleasure was all mine. I'll have my limo take you home."

That was a nice offer, but I couldn't take him up on it. My address is one of my closely guarded secrets because of my dual life. So, in the end, this tired Cinderella put on her bedraggled gown, borrowed a raincoat from Charles and rode home in a cab. Some parts of life suck. Fortunately, not all parts do.