The Fourth Blowjob

The next day you try your best not to touch yourself as you wait for Bob to change into his sissy clothes. It's harder than it seems, with him taking longer than half an hour while you're horny as Hell.

Then you hear the door shut and see him coming down the stairs. The white dress looks incredibly awkward on his muscular form, though it does seem to bring out a sort of boyishness from him. The wig is slightly better, accenting some of his more feminine facial features.

As he gets closer, you're disappointed to find that this is all he's wearing. No high heels, no makeup, no bra, probably not even panties. However, you don't feel strong enough to call him out on it. At least he did a half-assed manicure.

"Well, Bob, I certainly like your new outfit!"

"Yeah? I have a feeling you won't be liking it so much next game." He's short tempered, obviously embarrassed by the whole situation.

"Hey now, I want you to behave like a proper lady,"

He mutters something to himself that you can't hear, and then engulfs you with his mouth. Because of the half-assed job Bob did dressing up, you're **** to close your eyes as you try to imagine a real girl in his place. A young blonde, skinny body but fat ass, with nice B cups. And she's on her knees for you, trying to please her alpha.

Bob moves slowly, twisting his head with the motions, making sure his tongue can reach every part of your maleness. His hands serve as an extension of his mouth, pleasuring the parts that can't be reached.

You know that they can be reached, though, and you place your hands on either side of Bob's blonde head, slowly guiding him further and further down your cock, reaching and pushing past the entrance of his throat. He starts trying to fight back as his throat gags around your cock in protest, but there's nothing he can do.

"Damn girl, your throat is so tight," you tease as you move yourself in an out, not allowing him the luxury of a breath. "Now I know how you felt last time, a small sissy mouth round your cock, massaging it from all directions. You know I think I could get real used to this...."

He starts to moan loudly, but the vibrations just make you feel that much better.

"What's that? Did you say you're sorry? Is missy sorry for how rough she fucked my throat last time?"

Another moan. He's turning red now.

"No speeka Espanjol. Or is that an apology in pig latin?"

He starts nodding vigorously, and you let him go. Spit flies everywhere as he falls on his back, chest heaving with the effort of fixing his lungs. Almost looks like budding breasts.

"You know, I think you look better when you're all red. You should wear more makeup next time."

He vigorously shakes his head, unable to even speak.

"You should! It would help bring out your feminine side. Now, now, don't blush. We all have one, you know."

He's too embarrassed to say anything, and just gets back in position. Gently now, you let him get back to pleasing you. He's probably learned his lesson, and you wouldn't want him to get angry and treat you even worse the next time. After a few tries, using your manhood like a training wheel, he gets the hang of it and is able to more or less comfortably deepthroat you. In fact, his ministrations have gotten so good that you're about to cum.

As tempting as it is to let go now in Bob's throat, you remember the challenge and pull Bob off of you.

"Oh yeah," you groan "let me see that sissy face!" Shot after shot fires from your masculine balls as you mark his face with your fluids. That was incredible, you think, I need to win more often.

"I'm going to clean up," He says, getting up.

"You sure? I think you look prettier like this!"

"Fuck you."

"Again? Hmmm, maybe if you go take my makeup tips I can get it up again."

"Fuck yourself, you limp dick bitch."

Alone, you bask in the afterglow of your orgasm. No matter how many times you may have lost before, this moment more than makes up for all of it. You feel as equals, just like before you started this awesome game. Speaking of which, it's time you decide upon the next challenge.