Yes

You do as instructed and step into the shower, hot water washing the sweat from your body. You could feel a squishy sensation in your ass, and so you put your hands against the wall and let the water run against your ass, coaxing out the cum. Rubbing your sore but you considered the events of the night, the image that formed made you feel funny. Your friend Matt had gotten physical with you and had fucked like a girl. The fact that he had used your butt to make himself cum made your stomach feel fluttery. You pictured the v line leading to his crotch. pressing up against your ass, looking back at him to see his hands on your waist and sweat dripping down his abbs.

Snapping out of your fantasy you noticed without thinking you had started massaging your hole while thinking of Matt, and you were rock hard. 'Fuck, this feels good...' thinking about Matt's cock and imagining his glistening abbs flexing while he fucked you. Him dressing you up like a girl, it drove you wild how nice and natural he made you feel in the feminine roll. You managed to stop playing with yourself long enough to finish your shower, after you finished cleaning and drying you stepped back into the bedroom where Matt was waiting. Wordlessly he gestured with his hand to his dresser where he had laid out more of his sister's clothes this time it was a pair of white panties, a pink turtleneck, and, now there was even a blonde wig. Matt was lying in boxers and erect watching with a smile.

For a moment it occurred to you that you could just walk away from this whole situation, obviously this had been escalated to a point where the bet didn't matter. But you were having fun, and there's no harm in any of this right?

You dressed yourself and got into bed with Matt. After the lights went out you nuzzled up to Matt's chest, in the crook of his armpit, and put a leg over him, using a hand to feel his chest and muscles. Breathing in you reveled in his manly smell, clean but the strong masculine smell of skin and sweat was there. He reached around your back with a big arm and groped your butt which tingled from the touch. Your breathing started getting shaky from the hot feeling that was rising inside you. Sliding your hand down you began playing with Matt's big dick through his underwear. After feeling your ass Matt moved on to your hole. Prodding at it gently with a finger you felt felt your stomach church with pleasure as he played with you. You brought your hand back and wrapped it around his cock, warm soft skin feeling nice against your cold hands. After a second of massaging it Matt's hands travelled from your curves to your head, where he began urging you beneath the sheets. "Time to learn how to suck cock ****."