Babysitter Dilema

It was his sister who had hooked him up with the job to begin with. Looking over some kids on the weekends for a rich family in the comfort of their state of the art modern home. The job was well paid, allowed Rody to sleepover at the house and even covered the expense of his transportation to a from his own home. Really, the only issue was that the family explicitly wanted a female employee.

Rody had been disheartened. Even after all of his sister’s work, this small detail had been unearthen too late, her had even scheduled an interview with the husband, Mr Johnson!. It would be a shame but Rody simply didn't fit the role…unless.

Rody and his siter, AMelia, were twins. They had strikingly similar body builds. With just the right clothes and amount of makeup, Rody could, theoretically, pass of as Amelia’s twin sister, instead of brother. With nothing to lose and desperate to get out of his financial hell hole, Rody put his all into learning makeup, sounding girly and spent the remind of his savings into a dress. “Rina” was the person that showed up to the interview, and it went surprisingly smoothly. Mr Johnson was a smooth talking man, and once Rody got used to the awkwardness of being a girl, he was able to speak more comfortably. He went home with a sense of relief as he finally slipped out of the dress, knowing he would have a couple days until he had to wear it once more to start his new job. 

The job itself was very simple, since the kid of the family was a calm one. Mr. Johnson’s wife was delighted and her husband was generous, offering small bonuses for Rody. In fact, Mr Johnson seemed particularly fond of “Rina” but it meant more money so the babysitter complain. That was until the man had arrived on night a little earlier, it was just “Rina” and Mr Johnson under the moody lights of the living room when in one quick move, Mr Johnson had wrapped his arm around “Rina”’s waist and planted a kiss in her painted lips. 

ROdy had been to shock to even push back. the man’s kiss was hungry and needy, evidenced by the way he dug his finger into the babysitter’s wasit. One their lips parted, he slid a wad of cash into Rody’s hand, at least a months worth of his generous salary. 

“For your discretion” is what the man said before leaving. Rody should have been angry, furious, even. Yet seeing the amount of money in his hand, it was surreal. He went home that night, peeping quiet of the whole ordeal and in doing so opened the gates for something much worse. 

“Rina’s” tasks now not only included looking after a kid and house, but in the dead hours of the night ti also included making out with Mr Johnson. They made out in the living room, the kitchen, even his own bedroom. Wherever they would be hidden from the rest of the family. This also meant that “Rina” started going to work more often. his job started to fade from babysitter to secret mistress. He relished in the money–and the attention–this escalated. and Rina soon experienced the first taste of oral sex, though not in the way she had imagined. 

Rody had ran away after realizing what he had just done; sucking off a man–a married man–while dressed as a woman. It made him sick, so sick he had to take a seat. That’s when his phone rang and he checked to see an enormous amount of money had been transferred to him as compensation for his “service”. His stomach churned. anxious. He didn't like men, he wasn't a woman, and yet….maybe, just maybe he could endure doing this a couple more times.

Surely, once he had enough money, he could cut the charade and leave “Rina” behind. Surely, he could control himself. 

He texted Mr johnson, and bit his lip as the man replied; “See you again tomorrow, sweetheart”