Short Story (983 words) Made as an Entry for the CAW SS Challenge on the forum side. A first person view of amateur prostitution
I open my track jacket, revealing my braless perky breasts. Sliding the jacket the rest of the way off, I use the same motion to quickly discard of my sweatpants, leaving me naked before him.
“Come here,” he beckons, grinning with his yellow and brown teeth that always made this feel dirtier.
I move into my position, kneeling underneath his desk like I do every Thursday night at seven. As expected, he paws at my twenty-year-old flesh–one hand grazing my pussy, the other roughly grabbing a breast as I bend down.
A sharp gasp escapes my lips as he roughly mauls the tender orb. He quickly releases me so I can finish getting into position.. I look up at the desk-mounted timer and set it for twenty-one minutes.
“Ready,” I say quietly.
He pushes his chair back underneath his desk, leaving me trapped with his cock staring me in the face. I didn’t realize he even pulled it out. Steeling myself, I start the timer and lean forward, taking his cock into my mouth.
He is pitifully short, so I easily take the whole length in my mouth. Now I wait.
I’m expected to wait twenty minutes like this, just using his cock like a gag. I don’t ask why, because it doesn’t really matter. Once the timer goes off though, I’ll get to work and finish him off.
Being stuck under this desk gives me a lot of time to think. I never imagined doing fetish acts for money, but finances are tight. I was browsing Backpage for jobs one day and for a laugh clicked the adult jobs link. Four guys and four different activities, each helping take care of my money issues for the quarter. This has become my Thursday night, and this is the first stop.
I’ll leave here to go clean a guy’s apartment–buck naked, and wearing what I call the “Butt Plug of the Week”. I’ll arrive, strip off, clean whichever plug he’s set aside for me, let him insert it and then get to my cleaning. Last week I wore a horse tail butt plug that also could double as a flogger. I wonder what he has in mind for tonight.
My time with him will last about an hour before I’m off to my third destination–where I will spend forty-five minutes dressing up and stripping off various clothes and being spanked, groped, and fondled while bent over his knee. My time with him is the most disconcerting–while being spanked is by far my favorite foreplay activity, I have a sneaking suspicion that the clothes I try on once belonged to his daughters. That implication always makes me shiver.
My mind wanders to the last guy, and as always I feel myself getting wet. He has a fetish nearly every woman would enjoy–he simply likes to watch women orgasm. He does it right too, strapping me down on top of a Sybian while he manipulates the controls. It varies a little every week, trying the different attachments to see how I react. It is bittersweet though, the orgasms are so good but the machine does its job so well I barely have enough time to enjoy it. All my self-control goes out the window when he turns it on, try as I might. Sometimes it’s just one, but sometimes he likes to push me to multiples–at least he gives me extra for cab fare back to the dorm on those occasions, since there’s no way I can walk properly afterward.
I do struggle with the thought of prostituting myself during my college years like this, but given the crummy minimum wage jobs around here, there are certainly worse ways to spend my evenings.
I’m brought back to the here-and-now by the timer beeping–damn daydreaming about the Sybian. I reach up and stop the alarm as I pull my mouth from his cock, enveloping only the head. I swirl my tongue around it, clockwise and counter. I dab at it with the tip of my tongue–teasing, playing. My hands reach out to grab his legs–not to hold on but to warn me when he’s close. I bathe his cockhead with my tongue as I start sucking as though my life depends on tasting his cum.
His legs start tensing up a little–had a minute even passed? I wiggle my head back and forth, which he probably takes as trying to get him off, but in reality I’m shaking my head at how easy this guy is. He doesn’t complain when I remove my hands and mouth from his body–he knows what’s coming next. I move my right hand into position, cupping his balls and gently dragging them forward. Two deep breaths fill my lungs before I stick out my longish tongue and move forward, devouring his whole cock quickly. The result is simple; I waggle my tongue across his balls while swallowing him whole. It’s also quite effective as I feel him explode into my throat.
I retract my tongue, closing my mouth to properly to swallow all his cum. His groans of pleasure tell me that my mouth had earned its keep.
Once again I wait, until finally he scoots his chair out to let me free. As usual, he traps my leg as I try to get out and throws the envelope on the ground. I bend over to retrieve it and as always he roughly probes my pussy with his finger.
“I love that sucking me gets you so wet,” he tells me with an air of smugness.
Too bad for him it was thinking about a machine instead of a man. Oh well.
He finally lets me go and I return to my discarded clothes. I check that the cash is in the envelope and quickly dress. One stop down, three left.