D for Danielle Chapter 22: What Chastity Does to a Sissy

Daniel was thankful he didn’t have to fly home for winter break. He wondered what issues he might have encountered had he had to go through security at the airport. The steel chastity device he was wearing would surely set off the metal detectors in the 360 degree scanning machine. A TSA agent would then have to pull him aside, pat him down, and begin asking questions about the hard steel bulge in his pants. He’d have felt such humiliation!

Yet, if chastity was going to be a part of his life from now on, then those sort of situations were a possibility in the future -- in fact, they were a probability! Anytime he would have to show himself naked to others it would be risky. His predicament would be impossible to hide! And getting physical with a girl? How would he handle that? He couldn’t perform at all with his dick locked up. 

Perhaps I should stay away from girls… he thought. I wasn’t able to perform very well before being placed in chastity by Mistress Narcissa, and now, well, now it’s completely useless trapped in its cage. I keep thinking about that term: “Pussy free”. Would it just be easier to give up the idea that I’ll ever be with another female again? To accept the fact I will never pleasure a woman in that way?

He was taking the train home via a connection that picked up at 3am in the morning. He wanted to get some sleep but knew it would be impossible. His roommate had already left for the break leaving him alone in their shared room.

With some time before heading out, Daniel put his nightie and headphones on. He turned on his laptop and looked up a sissy hypnosis video using the hashtag #pussyfree, found one featuring one of his favorite sissy porn stars, and pressed play. It was a loop of the girl locked in chastity being fucked. Their useless clitty bounced in its cage as a real man with a huge dick used them like a cumslut.

Daniel felt his own penis leaking in his device as it struggled to get erect. The cage held tight. His cock was straining, pushing forward into its steel trap! There was a slight discomfort, then some pain, and the realization it wasn’t going to break free. Not without the key. The one Mistress Narcissa held under her very strict care.

He wanted to cum so badly!

Chastity was performing its purpose: Retraining Daniel’s dick and conditioning his mind. He would have to find new ways to achieve pleasure. Being locked meant he could not do so in the traditional masculine kind of way. No, he would have to use the dildo he got from the adult bookstore and milk his prostate. It was a sissy’s g-spot.

He queued up another training video entitled Anal Cum Sissy and spread his legs. He lubed up the dildo and pressed play. Images of sissies fucking their own asses and having sissygasms, which are basically hands-free orgasms through prostrate stimulation, penetrated his mind. He then penetrated his own asshole.

The training loops instructed him aurally and visually that this was how he masturbated now. That he was nothing more than a cumdump. Two holes to fuck and suck. But try as he could, over the span of an hour of working his tight asshole until it was slightly gaped open, no sissygasm happened.

He longed for Mistress Narcissa’s guidance. Perhaps this was her plan all along. To make him crave her control. He knew she could teach him how to release while under key and lock. He'd have to be very good for her to get that kind of training....