Chapter 5
by
Fmbunny313
Who asked you the question?
Aaron
"What if we make a bet that you wont be able to last a week without masturbating." You and Aaron used to make bets all the time when you first met. One time you even made him run across a busy silk road. It was so funny at the time but when you grew up you both realised how horrible it could have ended. "What are the terms of the bet and how would you even know if I was successful." You say it half hoping they haven't thought about it but also half hoping they have and thid can be your ticket to finaly not masturbating every day. "What about, If you are successful Hannah and I will both give you £150." Your eyes shine bright with glee. You haven't had that much money in months, You could finally buy the games you want. "However if you loose you will have to be our maid for 1 month." You aren't shocked that he'd suggest this as you were starting to wonder if your lack of chores was bothering the two of them. "What about a chastity cage as a means of making sure he doesn't toach it." You were shocked that Hannah even knew what a chastity cage is, Yet alone that she would suggest it. "If you agree, me and Hannah have already bought one and its in our room, We have been worried about you for a while and have done alot of research. Everything is safe and ready." You aren't given a moment to think, It's all happening so fast, Not only have they worried about you for so long but waited so they could help me the best, But they spent there own time researching for my benift. "Okay deal, I'll do it."
As the three of you walk to Aarons and Hannahs bedroom, The sense of fear about whats going to happen starts to slowly build up. You were sort of aware of what a chastity cage was, But you never did much digging into the topic. You stand awkwardly in the doorframe of you friends room as Hannah digs around in one of her cupboards and takes out a small pink chastity cage. "Okay, Obviously it will just be Aaron in the room when you put it on." She says as she hands you the cage and walks out the room. This nudges you abit closer to Aaron in this odly sexual moment. Feeling quite uncomfortable and scared you slowly lower your trousers and underwear revealing you 3inch flacid penis. Thankfully he doesn't comment and watches as you slowly struggle with all the peices untill it's on nice and snug. It was only after you locked the cage that you realised you didnt have the key. Before you could even start to panic you tell yourself its so they know exactly when you have taken it off as they would need to give you the key. You stand there for a couple seconds in disbelief that you actually have a cock cage on and then you pull up your trousers. "Well i'll see you in a week." You often find that you defer to humour in awkard situations.
After exusing your self from their room and saying goodnight to them both. You make your way back to your room to watch some youtube and to fall asleep.
Did you have a good night?
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Horny Jail
A man makes a bet that puts his life in question
Matt makes a bet with his frind that causes him to re exam who he is and if hes even a he.
Updated on Jan 27, 2026
Created on Jan 27, 2026
by Fmbunny313
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