D for Danielle Chapter 21: Winter Break

The first few days and nights after Daniel’s visit to Mistress Narcissa’s mansion provided to be a difficult adjustment period. Over this time he struggled to accept his chastity. The sissy could barely get to sleep, he tossed and turned in bed, the imprisonment of his penis constantly on his mind. When he did wake, his tiny dick throbbed in its cage, trying to achieve a morning erection as it pushed for release. After the pain became too much to bear, it retreated and became limp once again.

Winter Break was just days away and students were taking exams. While at his desk he felt self-conscious. He wondered if his classmates had guessed his secret, if they knew his tiny cock was locked away. He was able to hide the device under baggy clothing, but he was always aware it was there. He had done his best to conceal it yet doubts remained. What if by some chance a fellow student pulled his pants down in front of everyone to reveal his steel-trapped knoblet? The fear was real, but the reality of it happening was slim.

A sissy’s mind needed guidance, assurance, firm direction...

Other factors presented some anxiety issues. One of the tasks Narcissa had given him was to wear satin panties instead of boxer shorts from now on. He was also instructed to continue shaving his entire body. The feeling of the smooth and slippery fabric against his chastised penis and freshly shaved skin was almost too much for him to bear. He felt as if he could explode at any moment.

Yet could he cum with the device on? He asked himself if he could he ever get used to being denied 24/7 -- to never feeling the intensity of a full orgasm ever again. Were there other ways to gain some form of release? A sissygasm, perhaps. He had heard of their existence, but were they possible to achieve? To spurt hands-free?

On the way back from one of his exams he passed by Billy Anderson. The star running back was chatting up a freshman girl outside of the Student Union. Once again Daniel felt that Billy took notice of him. He might have imagined it, but he could swear the football player gave him a wink.

Something inside him wanted to stop and turn around, to approach Billy. He knew he wasn’t ready, however. Perhaps if he was completely feminized -- transformed and made more pleasing to Billy’s eyes. But he quickly pushed those thoughts away and pressed forward.

He met Madison for lunch in the commissary. They chatted about what their plans were for Winter Break. They were both going back home to visit family and promised to text each other to stay up-to-date on events. 

Something was different between them, however. When a male student looked over at Madison and she looked back, Daniel wasn’t jealous of the boy. No, he felt envious of her. She was the one getting the attention. He wondered if Billy would pick her over him?

And then those thoughts came back. He dreamt of being dolled up to please Billy Anderson. Dropping to his knees and sucking the powerful alpha male’s big cock. Try as hard as could to resist, Daniel was sinking further and further. The idea of becoming a sissy full-time was becoming harder and harder to resist. 

Back at his dorm room he sat at his desk and tried to concentrate on studying, but his thoughts kept drifting. More erotic scenarios and ideals. He pictured himself dressed up like the cute girls who fawned over the football players. He imagined wearing a cheerleader outfit, supporting the team at the upcoming Bowl Game, then getting fucked afterwards by a big group in the locker room. 

Will any of these fantasies ever come true? If Mistress Narcissa exists then anything is possible, right? he thought.

The next day he took his final exam. Afterwards it was officially the end of the semester and the Winter Break began. Daniel packed up his bags and left before saying goodbye to Keith, his roommate. The one he had barely seen these past few weeks. He wanted to get as far away from school as possible, to retreat home to his own room, a place where he could have privacy once more. To be alone with the ideas that kept swimming in his head.

He knew Mistress Narcissa had more instructions for him. More than ever he needed her guidance, her knowledge, her control...