Fish ran a hand over Oswald's back slowly, feeling her little umbrella boy quiver beneath her palm.
"Poor baby. Don't be scared. I'm gonna take good care of you."
Oswald swallowed, his hands pawing anxiously at the silk sheets of Fish's bed.
"Yes, Miss Mooney. T-Thank you, Miss Mooney." He replied obediently.
Fish smiled to herself, the kid was still nervous. She supposed that was only natural. Besides, even the 'toughest' guys could get a little antsy when it came to getting something up their ass. Men were funny like that.
A slim finger pressed into Oswald's hole, making him whine almost immediately. So he was a vocal little thing, Fish didn't mind that.
"Relax, honey. This is barely anything." She reminded him firmly, but not unkindly.
The finger worked in deeper, she moved it in and out and around, before pushing in a second to join it.
"Ah…" Oswald didn't want Fish to be disappointed in him, but it was hard not to whine and whimper at all of these new sensations. Then, when her fingers found his prostate, keeping quiet proved to be impossible for the inexperienced young man. He worried that Fish found his moans to be annoying, however it was quite the opposite.
It was a change of pace for Fish to have a guy who took to being submissive so naturally. Often their pride prevented them. Even if they were enjoying themselves while being fucked by her, they tried to retain their macho image, grunting and groaning in a gruff manner. Oswald was quite different. He moaned rather sweetly. Whines and whimpers rather than grunts and groans.
"I think you're ready now," she commented, removing her fingers from him and starting to prepare herself.
She tightened the harness around her waist so it wouldn't become slack. Oswald couldn't help looking over his shoulder slyly to watch her, his cock aching in anticipation at the sight of Fish getting ready to fuck him. The strap on itself wasn't ridiculously large, but it was definitely larger than two of Fish's slender fingers.
"Be a good boy and raise that ass for me," She instructed once she was ready, giving his backside a light pat.
He nodded, obeying her with flustered eagerness, his nerves still there but temporarily pushed to the back of his head by his lust. Fish held onto his waist, then slowly moved her hips forward, the slick rubber phallus breaching him. His breath catching in his throat and his fingers twisting the silk sheets in their grip as it did.
"Ah… Oh…"
"Relax," she reminded him.
"Y-Yes, Miss Mooney."
Fish wasn't rough with him, but she didn't coddle him either. She soon found her rhythm, he hips rocking steadily as Oswald moaned in response. He seemed to be enjoying himself. He probably wouldn't last very long. She could forgive that. It was his first time after all.
"You can cum, Oswald. Touch yourself. Go on, baby." She purred, her hips thrusting in more firmly, the little raven haired man curling his hand around his cock and giving himself a few fast strokes, which was all the encouragement he needed to be pushed over the edge into an orgasm. She let him ride it out, her hand running over his back again as he did so.
When he was finished, she removed the strap on from his ass and her umbrella boy flopped onto the bed on his stomach. He was spent, his breath heavy and limbs heavy. It was quite an endearing sight. However, Fish didn't want him to think she was getting soft.
She slapped him sharply on the ass, making him jump and turn around quickly in surprise. A startled look on his flushed face.
"'You have five minutes to get yourself together and get back to work, Oswald. Or a dick up your ass will be the least of your worries."
"Y-Yes, Miss Mooney!"