Money on the Side Ch. 01

Part One, the interview…

$$$$$$$$$$$$$$$$$$$$$$$$$$$

College Guys

Open Minded

Love To Party

$$$$$$$$$$$$$$$$$$$$$$$$$$$

Ok, from the ad, I pretty much knew this wasn't going to be a job delivering pizza, but after two years of doing minimum wage jobs, I was on the verge of having to drop out of college for lack of money. And to be fair, I thought, I'd fooled around with schoolmates once or twice over the years, and played with toys when I masturbated, so how different would this be?

I called the number and set up an appointment for a private interview. I was told the interview was that night in the penthouse of the local Hilton, and that I would be paid $200 for the hour it would take me to complete the interview, and that if I passed the interview I would be offered employment that paid in the range of $1000-$2000 per night.

I knocked on the door of the suite at nine exactly. The man who opened it, Jake, must have been 6 foot five of hard muscle, about fifty, wearing a silk robe, rose tinted glasses, hair slicked back, a cigar in his grinning mouth. "Dave? Great. Come on in."

He offered me a drink, bourbon and coke, which he poured generously, and which I downed half of in the first gulp.

"Easy, kid, I'm not gonna jump on you. Well, not just yet anyways. Have a seat." We sat on the sofa facing the big screen tv in the suite.

"ok, we're gonna watch a tape, and after that we'll have a little chat."

He popped on a tape that showed a large house far out in the woods. There was no sound on the tape as the camera entered the house and took a tour, so Jake narrated. "OK, see, this is the party house. Theres two large public rooms with bars, pinball, and a dance stage with a pole, raised platforms with mattresses for putting on sex shows, that sort of thing. Really it looks just like a big house party when we're working, which is what it is, just that our party is a private sex club for gentlemen who like a little meat for dinner, if you take my meaning."

I thought his meaning was pretty clear.

"The way it works is you come out on Friday afternoon, and you party Friday night, Saturday afternoon, and Saturday night. Yoo have your own room to sleep in, on the third floor, the second floor are private bedrooms to take the customers to for sex, and the first floor is the public rooms. You can have sex with clients on one or two, but no sex on three—well….."

"Well what" I asked

"Well a lot of these guys are in their 40's—a lot of tops, so sometimes you can go the whole night just sucking cock and getting fucked, and sometimes if you haven't come all night, you know, the guys will get each other off before bed on the dorm floor. Understand though, we offer a full range of services, so a lot of these guys will want to get a little kinky, tie you up, spank you, fuck you with dildo's, lots of dirty talk, that sort of thing, and once you complete a client, you need to shower up, get dressed and get back to the floor. You'll have anywhere from three to ten a day, depending on the client and what he wants, and you need to be looking really slutty when you are on the floor—thongs are good, butplugs with feathers or tails attached are good, and you need to be in leather—collar, wrist, and ankle cuffs at all times.

Really?

Really, a lot of them are kinky, and we don't want you tied with rope, to much potential for trouble there, so we have all the boys in cuffs and collars. You get paid on the number of hours you are on the floor and the number of clients you see. Worst weekend is about $750, best is about $3,000. If you can handle the work"

He stared at me for a long moment, and I realized he was waiting for a response.

"I—I'd like to try it."

He smiled at me. "ok, then, go into the bedroom, take all your clothes off, put on what's on the bed, and then come back.

"NOW?" I asked

Well, I have to know that you can do the work, that you can put out for a total stranger. So, Yeah, Now.

When I walked into the bedroom of the suite I was in for the surprise of my life. On the bed were a set of collar and cuffs in black leather, a cockring and buttplug. On the dresser we an assortment of dildos, paddles, nipple clamps, etc.

I put on the collar and cuffs, and using the lube on the dresser, got the plug up my ass, then put on the cockring, which poofed my balls nicely.

It was time for my audition

When I strode back into the hotel suite, he was standing at the bar, but the only thing he was wearing was the rose tinted glasses. His cock was hanging free, a fat seven incher, shaved with pink balls poofing up from the leather cockring he wore.

"C'mere, baby" he said.

I walked over and looked him right in the eye, and he put a hand on my shoulder and pushed. Taking the hint, I leaned forward and drew the head of his cock into my mouth. He as horny, as he already tasted of precum, and he immediately swelled to a gagging hardness in my mouth. I sucked him deep into my throat, working my tongue on the underside of his cock to get him off better and faster. After a few minutes I felt him swelling in my mouth as a played with his soft, full ballsack, and knew he was not far from cumming.

Just then he gently grasped my head, and pulled it away from his cock. "good boy, now get up." He took me over to the dining area in the suite, and leaned me forward over the table. I felt his fingers gently pull the butt plug out of me, leaving a cold gaping emptiness, an absolute yearning to be filled. "mmmm, pretty cheeks, pretty hole, I'm gonna enjoy having a piece of you boy. I know our customers will."

He placed the head at my gate, warm and soft in comparison to the rubber plug. Being penetrated is always a wonderful moment for me. Like a sigh that runs throughout the entire body, that perfect moment of submission when you allow yourself to be a vessel, and this was so much better than the toy, the warm hard/softness of him filling me as he sank deep into me, resting there with our balls touching.

After what seemed like an eternity, he began stroking in and out of me, a soft, sawing rythum. And I began to feel the warmth spreading through me, and the pre cum dripping from my cock. I reached for myself, but he pulled my hands away and locked the cuffs together behind my back. "Remember, now, a good whore has to save his cum for the paying customer that wants is, not waste it on himself—the cum stays in your balls till it's bought!"

And now that I was helpless he pumped away faster and faster, and I dripped and dripped onto the table. Just as I was about to come he pulled me back from the table, still fucking me.

"Lick it up, baby" I bent forward, and gingerly eased my tongue out to dip it into the puddle of precum that had leaked out of me during my fucking, moaning as the taste hit my mouth. Just as I finished, I sensed he was about ready.

"Kneel, baby"

Without a thought I dropped to my knees, and a second later the first of many jets of warm cum hit my face. When we caught our breath, he helped me up and led me to the sofa, still cuffed, and cum all over my face.

"Ok, kid, that's it. If now, right now, you could go clean up and do another guy,and then another, the job is for you."

In a daze I nodded.

"ok" He uncuffed me and motioned to the other room for me to go clean up and dress.

When I came back into the main room he was fully dressed in a silk shirt and linen slacks.

"Here's the $200, kid. Since this will be your first time at the house, you need to come out Thursday night so they can prep you, but you get another $300 for that. Be at the corner of Main and Vine at 7 pm Thursday, and a car will be there to pick you up. And don't jack off this week at all, Got It??"

Thursday couldn't come fast enough.