Field of Dreams Ch. 06: A Pleasant Surprise

When Cecil wakes up, the cage door is open and he has been freed from his restraints. He crawls out and sees that the door to the room is open. As he gets to his feet, Angela walks in. She does a body scan of his naked body. All he's wearing is the little pink chastity cage.

"Can you follow me, darling?" she asks in a surprisingly pleasant and soft voice.

"Of course, Mistress," he squeaks out and follows her into her bedroom. He searches the room with his eyes and sees nothing but the comfy bed. But surely, Angela has some sinister plans for him.

"Come sleep with me, you sweet little sissy," she says and gestures towards the bed.

As they walk towards the bed, she grips his hand and squeezes it.

"You've been a very good girl so far. Now you'll get a sweet reward from me."

They tuck in under the blanket, Angela behind Cecil. It's so satisfying to feel the warmth from another human again. It's been a long time.

It doesn't take many minutes before he falls asleep. When he wakes up, he strangely enough feels relaxed. He can feel Angela before, and she starts to whisper into his ear:

"You have been such a good girl, Cecilie. I'm so proud of you. I thought you were going to break into bits and pieces. But you overcame it. This is the hallmark of every good girl. They persevere. I said you were going to get a reward, and you will get it very soon. I want you to know it is to be fucked lovingly, without fear. Are you ready?"

Cecil has been broken down. He doesn't even argue about his new name. He likes it.

"Yes, Mistress. Cecilie is ready."

With that, he feels the strap-on trying to enter his new pussy. It fights back, it isn't yet accustomed to this.

"Relax, Cecilie. Breathe with me, and the reward will find you."

Seconds later, it pops in. It's a really strange feeling, filled up like that. Angela starts gently rocking back and forth. It's overwhelming as it touches the sensitive spots inside. He starts to lick his right index finger, while he slowly rubs his clitty with his left hand. His head is slowly filling up with pleasure, like a balloon. After a few minutes, he starts to rock his ass back and forth.

He starts to moan. At first softly in a low tone. Then higher and higher. As the volume increases, Angela increases the tempo. When he finally comes, it's a shriek like he's never heard before. It fills his head and blasts back from the walls.

This is what Nirvana must feel like, he thinks. It's breath-taking.

He opens his eyes and looks down at his cage. It's leaking now, but only some small drops. Not a whole mess to clean up, as it usually is when he jerks off.

He turns around and looks into Angela's face, which opens up in a huge smile.

"Welcome to our beautiful world, sissy."

The door opens and the other girls enter the room. They all kiss him on the cheek. Angela stands up and joins them, standing in a line watching him in the bed.

"You've earned the right to some privacy now. We'll leave the room and come back tomorrow."

They walk out and lock the door. Cecil is alone for the first time in a long while. The closet is locked. It's only him in the room. He drifts off to sleep again.

Several hours later, he wakes up when Angela enters the room again, dressed in a black leather catsuit with nude high heels.

"Did you enjoy last night, Cecilie?"

He nods. He almost starts to smile.

"I've never seen someone react that way. And that says a lot. I think it's meant to be that you joined us and our new little sorority here. Are you ready? I promise you: There will be no more restraints and domination. We'll train you and guide you to become our equal. Are you ready?"

Cecilie doesn't doubt it a second.

"Of course, Mistress. Please guide me to become a woman like you."

Angela claps her hands and giggles.

"I knew it! I look forward to this. Please follow me."

They walk down and into the kitchen. The other girls don't seem to be here. Maybe there at work at the mall? He sits down by the table, where Angela presents him with a smoothie.

"This is an extremely powerful cocktail which will do some new things with your body. You will start growing boobs, and I've mixed it so you'll end up with a J-cup. You'll look so good when you're armed with those missiles. Your hair will grow out longer as well. But you'll have to wear a wig for a while. We'll attend to the rest of your body hair later."

Cecilie drinks it up, and ponders about his future. What will it be like? He doesn't know, but he's looking forward to it.

"As for your little clitty there, you have to be in a cage for a while. It will shrink and we'll have to change into smaller and smaller ones. In the end, it will go limp and be so tiny that you won't even think about what you used to have. It will feel like nothing more than a zit. But before that, we have lots of stuff to do. Follow me upstairs."

They walked upstairs and into the bathroom, where Cecilie applied a permanent body hair removal cream to his entire body, except the eyebrows and the top of his head. He even applied it to his crotch, and Angela removed his cage under strict supervision. When it came back on, he was sure that I was just a tiny bit smaller. He enjoyed a relaxing hour in the bath while Angela attended to something in the bedroom.

When he entered the bedroom, it was redecorated. The closet was opened and showed a wardrobe with every item a sissy could imagine. Bunches of lingerie and hosiery, dresses, skirts, cute sweaters, shoes and boots. A whole section was devoted to dildoes in different sizes and colours, butt plugs and a nice looking collection of chastity cages. He picked at one of them, they all had printed the name Cecilie on it.

In the corner there was a desk with a computer, and on the wall beside it hung a full-size mirror. Next to it was a dressing table in a polished pink finish.

"As you can see, everything is set up for your training. We'll sleep together, and I promise you that we will repeat yesterday's pleasantries. The computer is devoted to research. You will read the most important feminist literature, as well as look for female role models. I've set up a few accounts for you on cam websites and dating websites as well."

She took a pause as she saw a slight hesitation in Cecilie's eyes.

"You don't have to worry. When the transformation has begun, no one will recognize Cecil. They will see a beautiful and sexy woman with a little zit in her crotch. Nothing to worry about. And I promise you, there are lots of big-cocked men who would do just that," she said and smiled.

The next hours, Angela taught him how to lay on the proper make-up. He got longer eyelashes, some rogue on his cheeks and a bright pink lipstick. He even got a pink wig matching it. When he stood up, he could see that his boobs had already started growing.

"Now I want you to pick an outfit to wear today. This will be your second skin, so to say. I'll leave you to it and be back in half an hour. Enjoy it, sissy!"

Angela locked the door on the way out, and he was all to himself. There was so much to choose from. He gave in to his inner lusts.

When Angela returned, Cecil was dressed up. He had chosen a lingerie set, complete with garter belt and stockings, in the same light pink as his lipstick. He was wearing pink platform high heels with an ankle strap and a very short pink velvet dress with white lace trims around his chest, which showcased his ever growing boobs.

"Damn, girl! If I was a man, I would fuck you at once. Nevermind, I want to do it soon anyways. But first, I have to lock those heels."

Angela bent and secured the ankle straps with small pink padlocks shaped as a heart. They had a little bell inside, which rang for every step he took.

"This is for your own good, sweetheart. Walking properly in heels is one of the most important tasks for a girl. And you will look hot when doing it, swaying your hips and showing off that cute bubble butt of yours."

She paused before continuing.

" You'll wear this outfit 24/7, getting used to it, loving the feeling it makes you get. You'll soon dread the thought of changing out of it. Before you get the reward you deserve, I want something in return. Lay down on the bed, please".

He did as he was told, wondering what he was going to do. Angela took out a dildo from the closet, which she attached to his cage. He now had a cock again.

Angela crawled on top of him and sat down on his "cock"..

"Proper girls give other girls the attention they crave. But you will not thrust as you are used to. I will ride until orgasm."

She started slowly, grinding, softly moaning, before suddenly changing the rhythm completely. Cecil felt he was being rocked by a girly sex-tow-shop-employee-hurricane. She came several times before easing down.

"That was lovely, Cecilie. And rewarding your girlfriend sure is a good thing, isn't it?"

He nodded.

Angela unscrewed the dildo and mounted it on herself.

"Please stand up and lean against the desk. And start a live session on the webcam site, okay?"

This was a huge step, but Cecil wanted the reward. Yesterday was so, so good. He started the session just as Angela entered him from behind. The same feeling as yesterday returned. The viewers soon started chiming it, edging Angela and himself forward. There surely was an audience out there.

Angela did it slowly, and Cecil was a long way from orgasm.He started biting his lip and caressing his nipples. He felt Angela upping the tempo and he was getting to the point of no return.

As the orgasm hit him, Cecil knew that the life as Cecilie was something he wanted.

Two years later:

Cecil Melton existed no more. But a woman by the name of Cecilie Melons now lived in the IT consultants former house, together with Angela, Daniella and Carmella. They had opened a new store at the mall called "Fab Four", and did huge success in providing everything a proper woman would need: Lingerie, shoes, clothes and sex toys, in addition to a small corner devoted to feminist literature.

All four girls ran successful accounts on webcam sites. In their spare time, they often had visits from men. They used to be well-hung. They often had big gang-bangs. No one questioned the little zit in Cecilie's crotch.

One morning Cecile walked to her car when she spotted a familiar face in the driveway.

"Excuse, miss. Do you know Cecil Melton?"

Melissa's eyes flickered as she waited for an answer. Cecilie took a pause of five seconds before answering:

"No, I've never heard of him. How come?"

"I left him two years ago. And it was a terrible mistake. I want him back," she said hastingly.

"Sorry, miss, but I can't help you. But I wish you good luck finding him. Sorry to be so rude, but I have to get to work. Byebye!"

Cecile strode past Melissa, making sure to wiggle an extra bit with his butt as he left her for good.