He gets out of the costume, but not out of being a sissy

Danny was pissed. Seeing his pride and joy locked away like this was too much, even with all the punishment and humiliation and ****, he couldn’t hold back his anger at his manhood being locked up. Danny stood and tried to give off an intimidating presence by crossing his arms, shrugging his shoulders, and giving Jessica a mean look. But in his new feminine attire, he looked like a petulant brat, more adorable than intimidating. Crossing his arms just made his breasts more pronounced and his angry look came off as a sexy pout.

“Now listen here, Jessica. This is too far! I’ve followed all your orders for your little game tonight. All the demeaning shit you did to me *shudder* was horrible but I did it! This cage is too much. Now give me the key or else I’ll….” Danny struggled to think of what he could do to her, as she held all the cards. He had no masculine clothes, she had the key to his locked dick, and most importantly all the **** material that would ruin his life forever.

“Or else what, sissy? You think you can go back to being masculine Danny again just by puffing out your chest? All that does is make your “girls” look bigger honey, which is a good look for you sweetie. You’re going to wear that cage until I tell you to, and you’re gunna be doing a lot more than just having your little clitty locked away. So fix your fucking attitude or I’ll kick you out on your satin covered ass and post all this for everyone to see! Now say ‘yes Miss I’m sorry I tried to be a man again. I’ll be a good girl.’” Jessica drew herself up and put a finger squarely in Danny’s prominent chest and pushed him back. Danny, not expecting the sudden movement and still unfamiliar in his new heels, fell back onto the bed letting Jessica lord over him as he gazed up at her submissively.

Danny, shocked by her sudden anger, gulped and submissively whispered “Yes Miss. I’m sorry I tried to be a man again. I’ll be a good girl and do whatever you say!”

“I was gunna be nice as you were such a good girl for “Daddy,” and how far you fell into your new found girlhood that you came from your sissy button, that I was gunna let you get dressed in your ugly boy clothes, but this outburst ruined that. So you have two options. One, you leave in your sexy little bunny outfit and make your way home through a drunken college at night. Orrrrr…. I dress you like a normal college sorority girl. What do you say, sissy?”

There was **** for Danny. There’s no way he would be able to make it home like this on his own. He’d either be found out as a sissy and humiliated, or worse he’d be molested and taken advantage of cause they thought he was a real girl! Looking at the slutty bunny with her tits popping out of her corset in the mirror, the second option was more likely. He’d have to accept the lesser of two evils and let Jessica choose a new outfit for him.

“I’d… I’d like to change, Miss” Danny said submissively, hoping she would take it easy on him if he turned up the girliness.

“Good girl, that’s what I thought. Alright then, little Miss Priss. What should we deck you out in” Jessica teased as she looked through her closet. “Aha! Perfect! Ok little sissy, let’s get you looking like a college slut rather than a playboy bimbo hahaha”

Jessica untied and loosened the corset as Danny breathed in a sigh of relief, thrilled to be out of the constricting garment. She undid his garters and had him step out of the body suit. She took off the gloves and bunny ears and choker collar as well. Unlocking his pink stilletos, she had him take them off and took off his sulking pink stockings. The electric feel on his freshly denued legs made him shutter and bite his lip as his cock tried to get hard in his cage. “Fuck why does that feel so good! Stop it, Danny! You’re a man, not some girly gay boy! Just get through this and get home!” Danny thought to himself.

Standing there in his matching pink thong and push up bra, Danny felt free from all the restricting clothes for the first time it felt like in forever. His feet ached from the sharply pointed pumps. His waist and chest finally felt free, but he could still feel how the corset had crushed him into an hourglass shape. Those feelings would go away, but the tightness of the cage around his cock remained, as well as the sore, slightly loose feeling from his backside.

The relief was short lived as Jessica returned with a pile of fabric in her arms. “Seeing your bombshell hour glass figure, I have to keep it going. And I know you love how it brings out all your curves! So arms up sissy!” Jessica teased as she wrapped a black underbust waist cincher around him. Danny moaned in displeasure, but kept his mouth shut not wanting to anger her once again. Danny grunted as Jessica tightened the laces one by one and let out a gasp of air as she put her knee into his back to really get it tight. Tying off the laces, Jessica was happy to see Dani’s curves on display again, his waist being reduced to 28 inches!

“Good, even tighter waist than with your bunny costume! I think we can get even smaller with continued waist training. Let’s get you into your cute outfit girlie!”

First she slid some thigh high white socks onto his smooth legs. While not as sensuous of a feeling as the silk stockings, they still caused a wriggle up his spine. Next was a black and white checkered pleated mini skirt, falling a few too many inches above the knee. The flouncy skirt would need to be handled carefully when he walked or he’d be showing his pink thong to everyone. Next came a black long sleeved sweater tucked into the skirt. The top was extremely low cut and showed off his generously enhanced chest. Finally, for a splash of color she put back on the pink rounded closed toe stilleto pumps. With a final click she locked them tight onto his ankles. She put a simple fake gold chain necklace and some bangle bracelets as accessories. Finally, she put a pink head band on his head.

“All set, sweetie! Ugh you look so cute im so jealous of you girlie! Now, take this bag with you but don’t open it until you get home. I’ll be watching your walk of shame, slut so you better be a good girl! Oh, and I completely forgot! Can’t have my girl walking without her signature wiggle now can we? Bend over sweet cheeks!”

Danny’s cheeks became even more pink at the humiliation of being bent over again to get plugged, but with how exhausted he was, he couldn’t put up any fight. So he simply bent over at the waist and rested on his elbows as Jessica flipped up his flirty little pleated skirt and pulled his pink thong to the side. With his asshole still lubed from his “fucking”, Jessica began sliding in the plug. This time, even with all the stretching, it felt big, bigger than before. Danny’s eyes began rolling back into his head, the same feelings of euphoria beginning to creep up on him. As his sphincter was reaching its breaking point, he felt his hole suck in past the widest point to the flanged base. With an eeep! Danny’s hole was once again plugged.

“Thought you’d need to go up a size, sweet cheeks. You will not take that out until tomorrow morning, do you understand me?”

“Yes, Miss.”

“Good girl, now get out of apartment, slut!” And with a sharp slap on the ass, like a common slut, Danny was pushed out the door.