(Com) Sissy's 1st Bday

Update: Finished

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Commissioner has written a short story to go with this drawing and the previous ones from this line:

The Game Begins

When the Dommy Mommy usually gets someone in her grasp to dress up as a sissy, it’s usually a simple case of catch and release. She finds her unsuspecting victim, she dresses them up, has her fun with them, and then sends them back out with some cute pictures to remember them by. However, this person was different from the others. For starters, this guy was already dressed like a girl to begin with. To the untrained eye you wouldn’t realize it, but the Dommy Mommy due to her experience was able to identify the trap with ease. She was also able to notice the mischievous glint in his eye, clearly telling her he enjoyed tricking people with his looks. If that was it, then it would’ve simply been a slight change of pace, but this one was different. After successfully convincing the trap to come to her penthouse, she was able to change him into the usual sissy attire she dressed everyone in. However, instead of the usual embarrassed looks or shy protests, the trap was openly annoyed with his new look. The Dommy Mommy was surprised by this, but was quickly replaced with irritation as the Trap continued to complain about how he looked. The Dommy Mommy decided that if the Trap was going to act like a big baby, then she would dress him up as one, so she quickly got to work on him. In no time at all, the Trap was now wearing a big puffy sissy baby outfit, complete with a big diaper and a large pacifier to keep him quiet. That’s how the Dommy Mommy left the Trap and she went into another room to think.

Usually at this point she would release her catch and simply move on, but she didn’t want to do that yet. The defiant attitude the Trap had made him a lot more fun to mess with than any of the other people she has had here before. She racked her brainfor ideas before one came to her. She remembered some of her friends in their circle talked about a dress up game simply called “Womanhood”. The idea of the game was to pretty much dress up your sissy during different stages of womanhood, and the goal of the game was for the sissy to succesfully complete the journey through womanhood to the satisfaction of the Dommy Mommy in charge. The length and extravagance of the game depended on the creativity and wealth of the person in charge, and the Dommy Mommy had both in droves. Figuring that this would be the best way to have fun with her new plaything, she decided that a celebration would be a perfect way to start the game. She went back to the other room to where the Trap was to give him the good news.

The Trap was right where the Dommy Mommy left him, stuck on the ground due to the big diaper he had on. The Dommy Mommy gave the Trap a smile, which he returned with an annoyed look. The Dommy Mommy explained that from here on out, he would be her sissy, and that the only way for that to end would be if he could beat her in a special game. She explained to him how the game would work, and that all he had to do was do a good enough job to convince her to move him up a phase until she successfully reached womanhood. He clearly was not happy with this, which was exactly what the Dommy Mommy wanted. She then told the Trap that they were going to start the game with a very special celebration, but he would need to change into a special outfit for it. With that, the Dommy Mommy pounced on him to begin his outfit change. Despite his poor attempts to fend her off, the Dommy Mommy successfully changed the Trap into a cake themed baby dress. She then managed to get the Trap into a stroller and began the journey to their destination.

After a nice stroll, they arrived at the family restaurant. The duo got some weird looks from the employees, but the large wad of hundreds she put down on the counter quickly ended that and got her some quality service. The Dommy Mommy explained that it was her sissy baby’s first birthday and that she wanted to make it extra special, with a whole celebration for everyone to enjoy. The employees excitedly agreed to help, especially when the Dommy Mommy put down a second wad of hundreds down. The employees got out a special birthday high chair and managed to get the Trap into it. They then began hanging up birthday decorations to make the celebration extra special. As this happened, the Dommy Mommy pulled out the Trap’s wallet and pulled out his ID. She then pulled out her phone and made some calls. She wanted to make sure that the Trap’s regular life was able to progress smoothly without him so that she could spend as much time as she wanted with him. Once that was done, she was able to come out just in time for the birthday cake to come out, so she was able to sing happy birthday with the employees and customers at the restaurant. As the Trap looked annoyed at this situation he was stuck in, the Dommy Mommy couldn’t help but smile imagining all the fun she was going to have with the Trap.

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Ive been commissioned to give a sissy their 1st happy birthday... again!

It's once again the Trap Sissy that you may have seen popping up here, first in their blue uniform, then in a pink sissy set and finally as a very big baby

The person who got the trap to be such a sissy is now celebrating by ofc holding a big party at a public place like a busy restaurant.