Trees of Fortune

Amanda had brought her son the maid’s outfit from the closet. She waited for him to wake up in the quiet room with the displayed clothes on the chair. The bedroom was bare of any furniture with only a mirror at the corner, a dresser and an ugly painting of a potted vase with flowers. She and her son felt uncomfortable in this room but nonetheless safe for the meantime.

They were hiding from her psychotic ex-husband and had been on the run for six years. This job at the Island resort was the perfect hiding spot. He would never think about looking for them over here because he knew that Amanda hated doing menial work as a maid. The private detective she had hired had instructed her to be self-reliant, break her old habits, abandon her usual tastes and even change her appearance.

Together they had faced the threats to their lives and done so without panicking or breaking down in tears. They had experienced hardships, done odd jobs from being a waitress, scrubbing toilets, living in cheap motels—endured dangerous close encounters—and survived. It was living day-to-day. It was living with the realization that Riley’s dad might someday walk through the door and kill them both.

To keep her son safe Amanda had disguised Riley as a girl by making him wear a dress at all times. It wasn’t that difficult to disguise him as a girl. Riley was nineteen years old and he had an androgynous appearance about him that could make him pass as a girl even without his shirt on. In one incident when they were at the pool together the lifeguard politely asked Riley to put a top on because of indecent exposure. The lifeguard apologized for the mistake and moved on, but it had been there that she realized that disguising him as a girl would keep him safe from his father.

Her ex-husband was a notorious and dangerous arms dealer with connections all over the world. He had one of the world’s largest fortunes but even he couldn’t keep death away. Her ex-husband wanted Riley’s heart so he could live a little longer. The only reason he had had a child was so that he could take his heart for a transplant in the future. He had a rare blood type AB Negative which was almost impossible to find a compatible donor. So he had gotten her pregnant and waited for Riley to grow up to take his heart.

Her ex-husband was looking for a boy and woman. It was a clever plan and all they needed to do was outrun him for a few more years until he died. From the news she’d been getting from TV, it was just a matter of time before he died and then they would be safe. That disguise was his only protection.

She finished her coffee and looked at her sleeping son’s exhausted body. He looked like an angel. It had been years since she’d had sex with a man. Her own pussy was closed for business, for good it would seem. Her son lay there like a picture, not saying a word and not moving. Her eyes kept wandering over his body, and she had to admit he was quite beautiful. It was a delight to admire such a wonderful body.

Suddenly, the covers on the bed had slipped partly off the bed leaving Riley half uncovered, and when she reached out to straighten the sheet and blanket, her hand brushed against something very stiff on Riley’s stomach. He had slept with his phone again. When she slipped her hand under the covers to grasp the item, she was shocked to find her hand wrapped around an erection!

Riley was sleeping but she still kept her hand on his member. Amanda couldn’t hold back the moan escaping her when he grinned in his sleep. Holding her own son’s penis sent thrills of obscene temptation soaring through her body! She should stop this… She had to let go of his swollen shaft and not let it go any further! It was utterly indecent! What was she thinking of?

She put her hand on his chest and gently massaged him through his shirt. Riley moved back as if he were enjoying it. Amanda lowered her head and kissed him on the lips. It was a long kiss, a hard kiss. Her hand moved down into his underwear, circling slowly, and she felt his naked cock. He was obviously hard. Her fingers instinctively curled around his cock. Riley gasped in his sleep.

She squeezed it and started to slowly masturbate him. She found his mouth again, this time she stuck her tongue inside, and slowly kissed in perfect time with her moving hand. Riley lay motionless, enjoying his dream and unaware of what his mother was doing to him. His cock throbbed inside her hand. Even though he was unaware of her, Amanda began to lust after her son vigorously. She imagined how it would be to touch his beautiful body, to take that dick into her mouth and to feel it harden and swell, and to have him touch her. At the same time, Amanda tried to hold back her emotions. Her pussy was tingling, her nipples felt hard and ached for his touch, and it was all she could do just to lie still.

“Baby?” She spoke softly, almost in a whisper, so as not to wake him if he was asleep. No reply. “Riley, darling? Are you asleep?” Still no answer.

Riley wore a flimsy white t-shirt that contrasted wonderfully with his golden hair and made him look so young and effeminate. Amanda didn’t ever want to let go of her son’s hard cock, but she reluctantly she did. Then Riley stretched out on his back with his eyes closed and a strange expression of disappointment on his face. Amanda quickly sat up and covered his body with the sheet. She looked at the bulge underneath the sheets revealing his morning glory.

A feeling of shame overcame her. She’d just molested her own son. It was time for them to move on to a new hiding place. Maybe this time they would get separate rooms. He was growing up so fast and she knew that this disguise wasn’t going to last forever.

“Riley! Riley!” she whispered in his ear. She shook him gently by the arm. “Come on, wake up, sleepy head−there’s work to do!”

He, roused out from a deep sleep, sighed deeply and murmured something garbled; but Amanda insisted. And in a minute or so there he was, sitting up in the bed. He unintentionally rubbed his crotch.

“You look sleepy,” his mother said trying to avoid looking at him.

“So would you be,” he said. “I had to spend the whole night cleaning out the courtyard.”

She smiled sadly and said, “I’m so sorry, baby,” and then they sat a while longer looking at each other. “Why didn’t you call me? I would have helped you.”

“It’s okay mom, I’m not complaining,” said Riley with a shrug and a beautiful smile. “I have to get dressed.”

“I brought you breakfast,” Amanda picked up a coffee and a muffin and it seemed to have changed his mood. “A few more days, Riley, and then we’ll move on.”

“Why not now, mom?” He swung his legs over the bed and sat up. “Tyler is literally trying to get into my panties. What’s wrong with leaving now?”

“Two more days, I promise.”

“And then we leave?” he pushed.

“You won’t need to wear a dress… for a while anyway.”

He smiled at her and nodded. Riley moved to the dresser, bare of toilet articles. He opened the drawers rapidly and took a compact from it and closed it loudly. He stared into the boudoir mirror and drummed impatiently with his knuckles upon the dresser top. It was such a hassle to put on makeup every morning. He extracted a powder puff, squinted into the mirror and carefully began to make up his face. He finished with the powder and then went to work with a lipstick, accentuating the bow of his lips. He’d applied only a light lip gloss and a smidge of eye shadow. When he was finished, he inspected his varnished nails and seemed pleased. He tossed the makeup kit in his pocket and then turned to face his mother.

She handed him a dress with an elaborate apron. With a shrug he looped it over his head and tied it neatly into a big bow behind his waist, smoothing the skirt down in front. He put on his shoes. His high heel black shoes were barely more than crossed straps holding his feet in place, but they’d give him the height he needed to appear taller.

A quick glance in the mirror made him proud of how well he pulled off looking like a girl. The blue skirt swirled nicely over his hips and matched with the soft white apron. Despite everything even he had to admit that he had a great pair of legs.