Anything for money (2) - Sex Stories

Anything for money (2)

The next week Simon eagerly returned, the promise of the 70 dollars occupying him all day.

When he entered the studio, Steve handed him an envelope with the money, which the boy gladly accepted.

“I really need some more cash, I’ve barely eaten since yesterday. Is there anything else I can do?” He asked.

Steve smiled, partly surprised at him asking unprompted but eager to continue with him.

“The next step is more sexual stuff, it would mean us really getting into it.” Steve responded.

The teen clearly was not enthused by this idea, but sighed softly, as if to reluctantly accept this proposal.

“If you take off your clothes, we can get started.” Steve said, trying to hide his eagerness.

With the speed of someone much more experienced than he truly was, Simon stripped down completely and tossed his clothes aside, where they were picked up by a camera man.

“Are you a virgin?” Steve asked.

“Yea, too shy to ask a girl out, I guess.” The teen answered.

“I mean anally, have you ever done it with a guy.”

Simon looked up, confused.

“The market for gay stuff with a kid like you is way bigger than doing stuff with girls, so if you want to be making more money that’s what we’d be doing.” Steve explained quickly, hoping the boy would agree to this.

“Well I guess I was always kind of curious what it’d be like,” the teen offered cautiously.

Steve pulled the boy onto the performance stage, and motioned for the cameras to start filming.

“Great, ...

... here’s some lube, I recommend using a lot of it in your asshole since you’re probably pretty tight. It’s gonna hurt no matter what, but this way it won’t cause any damage.”

Steve handed the boy the bottle of lube, who unscrewed it and tried squeezing it directly into his asshole.

“Here, let me help.” Steve walked over and squirted a generous amount onto his finger.

“Bend over,” he ordered. Simon complied. Steve inserted his digit into the boy’s hole, inciting a yelp from the surprised teen.

“Get used to this feeling, you’ll have to do this a lot in your future,” Steve added.

Gradually, Steve worked more and more lube into the teen’s little butthole, until finally he considered him appropriately prepared. From offstage he was handed a bright purple dildo, which he aligned with the teen’s asshole. Bent over at the waist and legs partly spread, the boy was in prime position.

“Breathe in and try to squeeze your butt out,” Steve helped. The teen did as told, but still twitched and screamed as the head of the dildo slid into his rear end. Steve put a hand on the boy’s back, steadying him as he prepared to give him its full length.

Steve worked the dildo into boy’s asshole, admiring the teen’s boypussy lips tightly gripping the penetrating object. He slid it in and out, each time putting just a little bit more inside the boy. Eventually, he was able to push the entire dildo in, but not without several whimpers from the teen.

At the same time, a videographer began ...