The Man Who Took Him In Pt. 03

This is the third installation of the feminization of Craig. I hope you enjoy and if you have any comments or requests for future chapters please let me know!

As always all characters are above the age of 18 and completely fictional!

Craig shifted in his sleep before waking up. For a moment he forgot where he was before everything came flooding back. The house, the slap, the deal, the clothes, all of it. Although it was all very weird and odd, he was drunk with luxury. He wasn't exactly thinking as a rational adult, rather one who could sit in a bathtub and eat caviar all day. The thought of food brought him back to the real world. The world where he was hungry again.

Craig sat up in bed. He looked over at the clock and saw that it was 6 A.M. He doubted that James would be up so he formulated a plan. He would go downstairs and grab water and a quick snack and James would be none the wiser.

Craig tore off the silk sheets and bounced quietly over to the door before slowly turning the handle. He paused for just a moment and listened for any sound coming from James' room or the downstairs dining room and kitchen. When he was met with nothing but silence he slipped out of the door and made his way briskly down the stairs in his silk women's pajamas.

He grabbed a glass of water and gulped it down with consummate ease. He refilled and sipped with less rigor. He then turned his attention to the food options. He grabbed a few easy things that wouldn't be missed by James and then closed the door.

It was then, as he walked back to the table to eat, that he saw the tall outline of someone seemingly carved into the wall. His heart nearly stopped as James lurched into motion.

"Well, well, well. Look what we have here. I mean I know I told you that I wouldn't judge but this is too funny!" He laughs. "Should I call you Crystal instead?" He questioned seriously before breaking out into another fit of laughter.

Craig's face was the color of the bright red thong he spotted earlier. He was petrified. He couldn't even stay in this man's house for one night without embarrassing himself completely. "Please, Sir! Please stop laughing at me!" He tried to say over James' voice.

James' eyes traveled up and down the boy's body. He looked over his shaved legs and pert butt and could even make out the slight outline of a penis tucked away in the panties. This was truly a sight to behold. But much more pleasant sights would be in James' future.

Calmly, James began to talk, "You know what... I'll play ball. Since you like dressing up in women's clothes. I can have you dressed as a female maid. I have everything you need. You can feel like the girl you really are and I will have a clean house! It's a win-win!."

"Sir... you can't be serious" Craig was shut down in horror. He didn't want to dress like a maid. "This is a complete and total misunderstanding" Craig pleaded as he tried to get himself out of this.

"I can't see what the misunderstanding is. I offered you women's clothes as a joke and you actually wore them" James laughed "Clearly, you are trying to tell me something that you can't vocalize. Luckily for you, I can see right past your lies and into your true desires."

Craig stood petrified. He should have stayed in his original clothes and waited for James to buy new clothes for him or something. Now he was stuck before a grown man with just panties and a nightie.

As he was thinking and reflecting, James left the room. About a minute later he came back into the room with a large box. "Everything you need is in this box. I know you will fight this so I will make this simple. I will help make your dreams come true. Dreams which you are understandably afraid to realize. So to aid you in your journey to this dream you will follow my orders or leave this house. Sound good?"

Craig was frozen. He couldn't lose the chance to stay in this house. Otherwise, he would be kicked to the street and would never find another opportunity like it. On the other hand, whatever James had in store for him all stemmed from this weird situation. It couldn't be could.

He spent the next 30 seconds or so debating what his future would be before speaking up weakly. "I will follow your orders Sir".

James' heart lept and his cock jumped. "So glad to hear that! You can start by putting on the contents of the box!"

With a bit of trepidation, Craig inched his way towards the box. He gingerly lifted the top off and peered inside. What he saw horrified him to his very core. Inside were the ingredients to a perfect french maid. Craig began to lift out the various contents of the box and put them on the table.

The highlights of the box were the following: A pair of 4-inch black heels, a pair of thigh-high black stockings, frilly white panties, a white bra, a brunette wig, and finally a french maid costume. A few other knick-knacks made up the rest of the box.

Craig was stunned. However, a quick smack on his supple butt from James kickstarted him back to life. "Well, what are you waiting for my blossoming sissy!? Get into your uniform for work!" James said laughing and taking in the gorgeous sight of Craig in front of him.

"Sir? Does it have to be here?" Pleaded Craig as he dreaded the thought of James seeing him more naked than he was right now.

"Of course it does boy! Now get to changing! We have a wonderful day ahead of us!"

Realizing that he would not be able to get out of this, Craig began to slip out of his nightie and panties. Once he was fully undressed he looked towards the table.

Meanwhile, James was looking at something else besides the table. He eyed up Craig's soft and silky smooth skin as he undressed. "This is going to be so good for you boy" He grunted as he shifted his hard cock within the confines of his pajamas. The loose silk material didn't hide much and Craig figured this out fairly quickly. He turned around to say something to James before locking eyes with the tent in James' pants.

With a slight squeak, he turned back around and grabbed the panties as his mind flooded with a million thoughts. Most of them revolved around James' intention with that large member.

"You have such a cute little clitty by the way. Not big enough to call a cock or even just a penis but it is still beautiful nonetheless. Suits you" said James as he laughed to himself.

Craig felt like he was about to die of embarrassment. Without thinking he bent over to slide the panties over his smooth legs. It gave James a front-row seat to his puckered asshole.

James let out a little chuckle but didn't say anything. Mainly because he wanted to soak in the sight of that little fuck hole that he would be looking to claim in the near future.

After 5 minutes and more body exposure to the amusement and happiness of James, Craig was done changing. James looked him up and down. What he saw was beautiful. The goal was not to make Craig look like a girl, although that idea was brewing in James' mind. It was to make Craig understand what he got himself into. With one look at Craig, James knew that he had succeeded. The boy was ashamed and beet red. James had won this battle but there was still a long road ahead.

"Well, you look like a proper french maid now! And that wasn't even that hard! Nobody will see you so you have nothing to worry about. Have fun living your dream today!" said James with a pleasant optimism. "Now run along to the bathroom right by the entrance. That is your first cleaning job." James finished that statement with a slap on the rear. Craig let out a little yelp before rushing as fast as he could to the bathroom. The heels were totally new and probably the most embarrassing part of the wardrobe. So quintessentially female and yet Craig would have to wear them every day along with the dress and wig.

Slowly, he clicked his way to the bathroom door and stepped inside, finally happy to be out of eyesight.

James turned towards the kitchen and started on breakfast. As the stove started to heat up he thought of ways to mix in his "special sauce" with the meal.