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Chapter 21
by GuerrillaShark
What's the next challenge?
Anal Chastity
At night, you send shoot him a text:
- You feeling better, baby boy? What's the next challenge? -
You wait ten minutes, but he doesn't respond.
- Yo fag whats the next challenge? -
- I don't really want to play anymore -
- The fuck you say? You made the rules dumbass you said we play the whole month until mommy comes home so you can hide behind her skirt. -
- But this has gone in directions I didn't expect. -
- You bet yo ass! Don't you? If not I'm coming tomorrow to take it anyway. -
- Let's just do the same thing. -
- No. We adding chastity. Ima order it. -
This game has gone in directions I didn't expect, he says! What a fucking loser. He probably got that line from his psych class. The sucker thought he was gonna become some top dog like shit domming your ass. Instead he found out that deep down he's a sissy cuck.
And cuck's don't have cocks. That's where your last idea came from. He didn't respond, but he'll be too weak to complain when you lock his last delusions of maleness away. Then you'll own his ass forever. Needless to say, you have the most amusing dreams....
The next day, delivery rings the doorbell around 4pm. You grab the package and drive over to Bob's.
"I've got your cage ready." You show him his future.
He makes a face, but he lets you in. You set the device on the table before you as you start the game. It looks so small, you think, I don't think it would even fit me if I lost.
Fortunately, you don't have to worry about that. Bob is so anxious with fear that he can't even get it up! You take your time, even edging yourself to the busty blonde on screen before you blow your load 15 minutes later. Bob is still soft.
"NO! NO! NO!" He starts crying out of frustration.
"HAHAHA! Dude, can you even imagine yourself when you marry? ' Uh, wait a moment honey, just fifteen more minutes and I might have it up! ' "
He blushes at your humiliating comment as he just gives up, pulling his briefs back on.
"No, no, no!" You wag your finger. "Tighty whities come off - we need to put that pathetic thing between your legs into its new home."
"But I don't want to!" He stamps his foot, standing up.
"Have you forgotten the rules?" You turn serious.
"Fuck the rules!"
Now you're mad. "What kind of language is that for a lady to use? You look like you need another spanking."
He tries to fight back, but he's too upset to be effective. You lock his arms behind his back as you bend him over the couch - just like you fucked him yesterday. Pulling down the white underwear, you spank him hard. And again and again until he's a quivering mess, body so dry no tears are even coming out by now. Finally, when you think he's had enough you flip him over.
"Is there anything missy wants to say?"
"I'm sorry...." Again, he doesn't mean it, but again you don't care.
You take the chastity cage and fit it around his 1 inch shrimp dick. It looks a bit too big, but you know that Bob can grow up to 4 inches when he's excited. Could have grown, you correct yourself.
"I think you need a new name now," You muse. "You're clearly not Bob anymore. I mean the Bob I knew had a cock, not a clit. That's what you'll refer to this disgrace from now on, by the way - it's your clit. Now as for yourself, I think we'll refer to you as Brittany. How do you like that name?"
"Th-th-thank you for choosing such a nice name for me." He sobs. He's obviously furious, but he doesn't dare complain.
At night, you hold the key to Bob's (no - Brittany's) manhood up in the light as you once again find yourself wondering about your relationship. A month ago Bob was your tough guy best friend, now he was willingly letting you lock him in a chastity cage. Well, maybe not willingly, but he's certainly not calling the cops or anything. How far can you take this humiliation? How far do you want to?
What's next?
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From Friend to Girlfriend
Sexual game changes your sexual preference
Updated on Feb 28, 2025
by knight26
Created on Feb 14, 2006
by boywearspanties
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