He ends up in bed with his sister.
I let one cute little boot move slightly up and down, "...please, I..." I can see his small erection poke up from between his folded legs, sitting back on them hands at his sides. I know all he can think about now is touching it. I stare at him.
"Shut up. Do it." I watch as he starts to masturbate. Think about my man and his very big cock, nothing like this less than average man. I think about wearing only these boots with white lace ankle socks showing just above the top, think about being made up, clean baby smooth and slippery when he comes through the door. I think about being pushed up against the wall and felt up, think about kneeling in front of him a real man...I start to get hard.
"I love you. Mistress, I love you." His eyes are closed and he's rocking slightly back and forth on his knees. He's pumping his dick with one hand, holding his other hand out in front of it, he breaks my thought, feel anger for a split second. I turn my attention to him
"Not one drop on the carpet, you spill any of that disgusting stuff on the floor and I will whip you! I'll send you home with stripes on your ass!" I uncross my legs, lean forward. "Not one fucking drop, baby!" I pick up the crop and slap the floor hard with it.
He pumps hard, struggles at it. I smile to myself. And then it happens. He cums into his hand, tiny spurts, more like it softly drips out. He catches every last drop. Makes me think, he really is a good boy. He finishes. His whole body goes limp, like his little dick. Then I see his head hang, looks down at his hand, his shriveled penis, I know what he's thinking. The whole think took less than three minutes.
"Good boy, very good boy. You please your Mistress very much." He says nothing. I know where he's at now and I'm going to exploit it. I know where he is in his head. He's ashamed of what he is, but powerless to stop it. After we cum, that's when we feel it.
I stand, walk to the front of him, "Show me!" He raises the hand full of his cum, keeping his head and eyes lowered. I walk around him, let my crop brush across his shoulders and down his back to the crack of his rear. "You feel shameful, isn't that right, baby?" He mumbles 'yes'. I pat him hard with the crop across his butt, pat the back of his balding head, "Say it, say it now!"
"I feel shameful, feel ashamed of myself, Mistress, for what I do, what I am." I drop the riding crop at his side. I reach down and run two of my fingers in the cum in his hand, bend forward and pull his chin up toward me. I smile down at him. I run my fingers around his slightly quivering lips, let them just tease inside his mouth...he wants to cry, I can tell. "You want to cry for mama, right, baby? It's okay. Come on, you're such a good little boy. Cry for mama." He starts to whimper and then cry softly. "Let it out, this makes your Mistress happy." I pat his head, watch him sob softly, real tears come down his fat cheeks.
"You know what your Mistress wants now, baby. You know." I watch as he licks the cum from his hand, tears in his eyes. He can't look at me. He truly is ashamed of himself. I say nothing, just watch as he cleans his hand with his eyes closed. When he finishes he keeps his head bowed.
I walk to the mini bar, pour a drink, bourbon. I check my make up in the mirror. Not a smudge, still the perfectly cute sissy girl I was when I walked in the hotel room a little over an hour ago. I look at him in the mirror. "You may dress, baby. I'm through with you for now." I look back at myself in the mirror. Black leather mini dress comes up around my neck at the top, shiny silver large hoop earrings, tight black spiky hair, curls up just around my ears, very nice. I look like a real girl. Just a hint of the sissy boy I actually am. I like that, really like that. I reach back and smooth the rear of my dress, check myself out in the mirror.
"You want a drink, honey?" I smile at him.