A Changed Man - Chapter 4

Once Tom had gone and she heard his bedroom door close, Maria said, "that was one of the best things I have ever seen! Well done! So I take it that you want him?" she asked directly. Maria was never one to beat around the bush.

Hank was shocked by that question being asked right away. Was he that transparent? Had Tom seen through him too? No, he couldn't have. If he had, he never would have agreed to put on the cage.

"Was…was it that obvious?" he asked, his face coloring a bit like he had been caught doing something he shouldn't have. The blushing face answered her question though.

"No, no Hank, not at all. I kind of figured it out. Don't worry though. I support you in this one hundred percent. I want to help you as much as I can,” Maria offered.

“You know,” Hank said, “you made a huge difference. He fucking worships you I think. Thank you so much for giving him that little push by sweet talking him. Between the two of us, he was kept pretty off balance. I don’t think I would have been able to do it without you here. But why do you want to help so much?”

“It…it just seems so fucking fun. He really does have a problem and now he is going to be helpless to do anything about it! How will that desperation affect him? I really want to find out. I want to be here to witness all of it, if you’ll let me and don’t mind? I promise to do everything I can to help, because I just want to see how he changes and whether you’ll be successful. I want you to be successful Hank. I have had my suspicions about Tom. Besides…I am fascinated by power dynamics and this is starting off with a big one,” Maria rambled excitedly.

Hank chuckled at Maria’s excitement, but was so glad to have her as an ally in this. Hank knew he was fairly charismatic himself, but that sometimes didn’t matter when talking to a guy who thought he was straight. Tom’s attraction to Maria would be something they could both use to re-steer him.

“Absolutely Maria, I will take your help gladly and include you in all of it. He has such a crush on you, but hopefully we can use that, and his desperation, to get him to start thinking of other avenues. Do you think I have any shot?” Hank asked, feeling a little unsure about the plan.

“I do!” Maria said enthusiastically. “I think he severely underestimated just how chronic his masturbation is. The state of mind that he will be forced to adopt will make him be open to alternatives I think. You guys would make such a cute couple too! Fuck, this is fun.” And with that she downed the rest of Hank’s vile mixture.

“What do you think will happen first though? I have never seen a guy in a chastity cage before, but I have read some,” Maria said.

“I think he is facing a problem right now as we speak. But maybe all of the fine alcohol we drank will help him, but it could just as easily hurt him. Guys that masturbate like that usually at least do it before going to sleep. Male orgasms come with a hormonal change that can cause drowsiness, so with how long he has been doing it consistently, I think it may be like an addiction that he will feel like he needs simply to get to sleep. There are ways to cum with a cage on, but I don’t think that will occur to him soon, or if he would even think of exploring them. No, he is going to reach down, wanting to stroke, and feeling only his tightly caged cock. I expect a lot of frustration and perhaps trouble getting to sleep for several nights at least,” Hank guessed.

“And tomorrow?” Maria asked. “Will the morning be as bad as you implied? What if he breaks from it and just wants the cage off right away?” she asked, concerned the fun would be over that quickly.

Hank replied, “the morning erection will probably be pretty rough for him. That will last several days too before he becomes adjusted. He will be awake early and very frustrated. I think the poor sleep can work in our favor though. As far as him completely breaking? I think if we play it right, we can prevent that. He can’t afford to lose after all, he doesn’t have the money. I think we can let him suffer with it for a while and realize he can’t quit. But then offer him a little relief. I have a plan, but if you just follow my lead?” he asked.

“Abso-fucking-lutely, I can’t wait,” Maria replied, smiling broadly. “I…I may wear something a little extra for Tom tomorrow and see if that helps too.”

Hank laughed, “Oh yes, anything subtle you can do in these initial stages to increase his arousal and frustration will definitely help.”

They finished their drinks, enjoying each other’s company for another hour, before going off to bed. They were of a like mind with Tom and were each looking forward to what might happen, albeit for entirely different reasons.

—

Tom headed off to bed, feeling weird even walking with this foreign device hugging his cock. He was feeling quite drunk too and a part of him was worried that he had made a very grave drunken mistake. There was nothing he could do about it now though. He had made the bet and his cock was locked. And he couldn’t lose. He just didn’t have the money and didn’t feel like he could even save that much in a year to pay off if he lost.

So he simply couldn’t lose and that was that. He weaved his way into his bedroom and then stripped for bed. He looked in the mirror and saw how the cage hugged him. He started to think about Maria’s eyes on his cock and actually felt it start to try and grow, but then not be able to. That caused some discomfort. He could get used to this. He could. He had to.

He got into bed and automatically reached down to grab his cock and was met with the cage. He let out a groan of frustration. He could still feel it trying to grow and becoming even more uncomfortable. Maybe he could reach through the bars of the cage and try to stroke? He attempted that, and it was very difficult, but his cock started to respond. It was enough to stimulate him, but would it be enough to orgasm?

Unfortunately, that little bit of stimulation caused his cock to try harder and the cage got uncomfortable enough that he realized the longer he went, the worse it would get, and the less likely it would be that he would actually be able to orgasm anyway. He stopped and groaned more loudly in frustration.

He grabbed his extra pillow and rolled over angrily on top of it, feeling his cock throb. Fuck, his head was swimming. He just needed to…but he couldn’t. Why the fuck had he agreed to this?! He could feel his caged cock pressed against the pillow and his hips started to move. He started to actually try to dry hump his pillow, but didn’t feel anything because of the cage. He nearly yelled out wordlessly with his frustration when he realized what he was doing. How was he ever going to get through 30 nights of this? He had no choice, that’s how.

He tossed and turned and grumbled for a while, not coming up with any solutions. He ended up putting on his headphones and putting on a podcast to distract himself. It was at least an hour before he fell asleep, and that was probably only because of how drunk he still was.

It didn’t last long though as he woke up at 4am on the nose with the worst discomfort he had ever felt from his cock…