He is Your Master Now Pt. 07

"You want me to do it harder?"

She vigorously shook her head yes.

He spanked her much harder. This time she ground against him and breathed hard. Her 'cocklette,' as he began thinking of her dick, sprang to life. Ambrose' mind was blown. She might've been the type to merely pretend to like being spanked, but a hardon doesn't lie. She awkwardly conveyed to Ambrose that she wanted him to hold the leash taut, but not dangerously so.

He spanked the other cheek while being mindful of the leash, and again she gyrated her hips.

Her cheeks weren't quite red yet, but they were turning pink. Ambrose couldn't help but rub them. He began to see Andrea as his property to do with as he pleased, if only temporarily.

He spanked her again, four times in rapid succession even harder than before. And again he felt the movement of her hips, though the motion seemed more sensuous. When he went to rub her ass, he found that even his mere touch now caused her some discomfort. He rubbed harder and pinched here and there. He even raked his nails across the red expanse.

Ambrose wasn't sure if Andrea was a trans woman, or a crossdresser, in fact, he wasn't sure if there was a difference, the only thing he knew for sure was that she had a penis, and in his mind at that moment, he couldn't see her as anything but a male, although he still thought her/she pronouns. Thinking of her as a male made him feel superior; the use of female pronouns seemed more degrading to Andrea and enhanced that sense of superiority.

Administering punishment to this "MAN" only made him feel manlier, even brutish. It was a welcome change considering what Cassilda did to him last night, and Pippi's training today. He started getting aroused.

It was at that moment that Andrea offered him the paddle.

There was no reticence this time. He paddled her with the comingled feelings of lust and triumph, coming to his senses only when her cheeks were enflamed.

But still the little fagg--- he shut his mind against that word as Cassilda didn't like it.

But still, this little--- this little--- this little sissy bitch bucked him on. Apparently, he wasn't being cruel (manly) enough to suit HIM. Ambrose would show HIM who's the real man here.

He Paddled again, even harder. Andrea no longer writhed when he paddled her, she instead shook her legs vigorously and involuntarily as if trying to shake the pain away. The sissy bitch's body was reflexively rebelling against the assault, but still HE did nothing to stop from being punished.

Ambrose felt no sense of concern; HIS pain thrilled him. He paddled again multiple times, stopping just long enough between paddling just to enjoy HIS misery. The muffled squeals and half screams heard through the ball gag only spurred him on.

Ambrose was set to paddle HIM with all his might when HE started trembling, writhing quickly once more. HE was grinding HIS cocklette harder against Ambrose. HIS breathing became more ragged as heard through the scant holes in the ball gag.

Ambrose felt a sudden wet warmth coming from HIM and his immediate thought was that HE was pissing HIMSELF all over his lap.

He pushed HIM off in disgust, only to see that HE had ejaculated, not pissed HIMSELF. He looked at HIM as HE struggled to stand on wobbly knees, there were tears streaming down HIS face; HIS makeup smeared mascara trails as they rolled down HIS face. HE looked like a whore. A thing to be used for his pleasure and discarded.

They were tears of joy,

Andrea quickly took off her ball gag and spoke.

"Oh thank you sir. Thank you." SHE said breathlessly over and over again. She sank to her knees and began kissing the hand that delivered her ecstasy.

Then, before he could stop her, she stood to plant a soulful kiss on him. Aside from Cassilda, no one had ever kissed him like that. For the moment, he felt like a god.

She got on back on her knees and lapped up her own cum from his lap. When she was done, she gave him a passionate blowjob. When he ejaculated in her mouth, she opened it to show him the evidence of her happy debasement and gulped it down, after which she probed her tongue around her mouth to make she got every bit of it. She made a great show of this act.

"That was so delicious. Thank you, sir. Thank you. I can't wait for the next time I get to drink your cum." She loaded that statement with as much bravura wantonness as she could muster.

Moving gingerly, she packed everything up. As she headed out the door, Ambrose saw the evidence of his paddling. Now that he was spent and able to think straight, he reflected on the hard pit of ugliness within him that could make him lose such control--- and enjoy it.

He wasn't sure if he hated or loved that part of him, and that that was the most frustrating thing. He also didn't know how to process the idea that Andrea genuinely enjoyed herself to the point where she rubbed herself against the person who was hurting her, came as a result and was genuinely grateful to the man who delivered the pain.

He slept peacefully.