Field of Dreams Ch. 04: Training Day

"Good morning, sunshine!"

Angela's voice ringed through his head as she opened the sliding doors. Cecil wondered why it was still dark outside. It didn't look like morning to him.

"It's only 6 A.M., but we have to start early in order for you to complete your new routines before I head off to work. This journey isn't for the faint of heart, as you've probably already understood."

Angela rolled him out of the closet, and untied his hands. Seconds later they were tied again, but not resting on his crotch, rather down by his side. His knitted dress was soaking full of sweat, and he couldn't tell where the itchy material stopped and the skin of his body started.

She unlocked his necklace and took off his balaclava. Cecil could see again, and the sight was frighteningly stunning. Angela stood over him, her lean body dressed in all pink latex. Her top was unzipped so much that he could see some of her cleavage, but not too much. Her teasing appearance made him think of what could have been.

But now he was lying on the floor of his bedroom, tied and surrounded by the pink walls. In her left hand, Angela had a large pink vibrator. In her right an empty plastic bottle.

"For today's first task, you'll just lay down here for the next hour. This pink beauty will do its job as you fill up the glass with precum. When the bottle is filled up, the session is over. But only your imagination will help you understand it."

She pulled on the balaclava again, and locked the necklace. Then he felt Angela pulling up his dress and heard her putting down the bottle between his legs. She rested the vibrator on his cage, and felt the buzzing starting.

"It starts slowly, before ramping up. Now be a good boy and give mama some milk, will you?"

He heard her sit down on the chair in front of the computer. The feeling between his legs was strange. He felt the buzz, and a small itching in his dick, trying to escape from the cage. But it was not to be, as he knew oh so well.

He could feel himself leaking, as the dripping sound of his precum hitting the bottle merging with the buzz and Angela typing on the keyboard. The urge for a full release dominated his thoughts. He tried to get his dick to cumming properly, but the dripping continued.

As the vibrator upped the speed, the buzzing sensation pulsated through his body. Cecil felt his nipples get harder, and he had started sweating again. The other sounds were nowhere to be heard. It was just him and the buzz, almost like white noise.

Then the buzzing stopped, his mind snapped back to the bedroom again, and the sounds came back as well. He felt Angela remove both the bottle and the vibrator, before heading downstairs. He heard the opening and closing of the fridge door, before her heels signalled her imminent return to the bedroom.

"That's the most we'll get from that sorry little dick of yours - both for now and in the future. Milking will be the first task of the day everyday, and hopefully, as the tension and arousal builds up in your body, it will take a whole lot shorter. And maybe we will experiment with how the milking is carried out as well. But the video of it is marvellous, though. I've filmed the whole session, keeping it for my own pleasure," Angela said before untying him and undressing him.

Cecil sat up, resting his back against the bottom of the bed.

"While you enjoyed yourself, I've taken care of some important things. Firstly: You have now quit your job. Or, to be frank: I did it. By email. I was nice, though, telling them how wonderful the experience has been, but that you've decided to take a year off to think things through. Maybe travel abroad for a while, experiencing new cultures and getting to know yourself better."

With that his last lifeline to his old world was cut. Now it was just him and Angela together. Cecil felt both empty and excited. There was no way back.

"Secondly, I used your bank card to order a lot of things that we'll need in the future. I'll pick up the package at the mall afterwards, so you've got a little surprise treat waiting for you when I come home."

The excitement caused Cecil to drip even more, this time on his carpet.

"But first, we'll continue your training. I can see that you've sweated a lot during the night, and it's good that those pounds are coming off. And even though you have muscular calves and thighs, I guess your flexibility isn't that good at all. Men really don't care about that part of their workout regime."

She gave him some pink clothing and motioned with her eyes for him to put it on. It was a skinsuit in bright pink spandex, making him look like a soccer mom in one of those 80's aerobic videos.He got a blond wig as well. Underneath he still had his thong and bra on. Already they and the "tits" Angela had got him, felt like a natural part of his body.

"Before breakfast, you'll do a one hour yoga session every day. Follow the instructions in the video on the computer screen, and listen deeply to what the female voice is telling you."

He put on headphones and as Angela clicked play on the video, a sexy female voice started:

"You are not a man anymore. You are a girl now. And sexy sluts need their body to be bendable in ways a man cannot imagine. Push out that sexy butt of yours, and pretend you're getting fucked by a large cock," the voice said as Cecil started his workout.

An hour later, Cecil was in a trance focusing on the video and the voice in his ears. The movements didn't look difficult, but proved to be harder than he thought. These girls were some impressive athletes.

Cecil looked around the room and couldn't see Angela anywhere. He walked down the stairs, and felt the urge to escape. He couldn't do this anymore! He tried to open the door, but it wouldn't budge. He was trapped! What had she done?

Suddenly he felt a smack on his spandex-dressed butt.

"Where do you think you were going, slut," she asked in an angry voice, before immediately changing her tone.

"I know this is hard, and most sissies don't even make it through the first night. But I've seen your cock responding to my treatment, and it has liked it. You want to be here, and I'm going to make sure it happens. While you were doing yoga, the locksmith I ordered earlier arrived and changed all the locks. The windows have gotten extra security as well. Now follow me upstairs," she ordered.

Cecil hesitated for a moment, and felt a new smack.

"Now! Don't disobey me, you silly girl."

Cecil surrendered and he followed her upstairs to the bathroom.

"First, you're picking up your dirty laundry from the bedroom. It needs to be washed. The workout gear goes into the laundry basket as well as your panties and bra. Give me your "tits" and get into the shower!"

After a long and hot shower, Cecil stepped out, "dressed" only in his cage. Angela dried him with one of the towels.

"Follow me," she ordered and walked downstairs to the kitchen.

"Your "tits" is just a temporary solution. Each day you'll take oestrogen hormones, and soon your real tits will grow out. We will do it until we reach your proper bimbo tits size, before scaling down a bit to manage it. For breakfast there will only be bananas, making sure you get used to the shape of a dick in your mouth. You'll eat it slowly and think of sucking a dick while doing it."

After eating up, it was time for the final session with him and Angela before she had to go back to work in the clothing store at the mall. Secretly, Cecil hoped she would bring home some new knitted sweaters or dresses. A knitted skirt would be nice as well.

"Now, for each day you'll dress fully up in new clothes. Each week will have a different role, but you're changing into new sexy outfits every day. Understand? This week you'll be a secretary," she said.

On the bed was what he needed: Black bra and panties with a matching garter belt and black sheer stockings. Pantyhose and a nice pair of black stiletto heels went with it. His "tits" were there as well, in addition to glasses and a long, brunette wig. A thin red turtleneck top, emphasising his tits and a black mini skirt.

Besides the clothing was a toy he had tried alone, but not with Angela. A black butt plug with a shiny diamond at the end.

He did as he remembered from yesterday, pulling on his garter belt and stockings first. Then he reckoned it would be the butt plug, and plugged it in, a lot easier now than last time. His hole had expanded. It made a popping sound when it was firmly in place, and a hesitation travelled through his body, from the but up into his head.

The rest he knew how to do. Tits and bra, panties, pantyhose on top of that before the skirt and turtleneck.

Only the shoes were left. They looked hauntingly tall, and he didn't know if he could master the art of walking in them.

"You are not at a level where you can walk in those yet, sissy, but they look very good on you. Put them on, please," she said in a friendly voice.

He did as he was told and Angela quickly locked the small padlocks on each of them.

"Now, today you are going to be a proper secretary. You'll sit down in front of your computer, and I'll lock you to the chair with ankle bracelets. Remember to keep a good posture while doing your work," she ordered.

Cecil sat down, and Angela quickly locked him in.

"You are going to do some real work today. First: You will cancel all subscriptions of any sort. All your media intake is decided by me from now on. You'll unsubscribe from all your regular newsletters, in addition to changing all your bills so the money gets withdrawn automatically from your account."

That was a lot of work, but Cecil thought it could be done in a couple of hours. Angela proceeded:

"After that job is done, you will go searching online. You will look for sissy videos, femdom videos and big tit bimbos being fucked hard. If it's of the cuckold variant, even better. You'll download everything you see, photos as well as videos, building an archive of pleasure that you will reap benefits from in the future," she said as she picked up the headphones from the yoga session.

"While doing all this, you will listen to this sexy audiobook, which will surely motivate you. It's eight hours long, the same amount of time as my workday. I can check your log afterwards, and it's impossible to delete certain parts of your log, because I changed your password. If I'm satisfied with the work you've done, you'll get to try on the gift I'm buying from one of my friends at the mall. If not, I'll take it myself, only for you to hornily and lustfully look at me using it. Understood, dear?"

He nodded and felt the headphones land on his ears. Then she put on the necklace, and connected them with two tight chains. There was no way Cecil could do anything but what she desired for him.

Eight hours later Cecil's fingers and arms were sore. His ears were exhausted, listening to a tale of a dominant woman sissifying her husband and renting her out to her girlfriends, who used him as they pleased. His dick was numb after throbbing inside his cage, soon to go almost limp from exhaustion.

Just when the audio was finished, he heard the door downstairs creaking. The familiar sound of Angela's heels made their way into the house, soon climbing the stairs. Before he never would have recognized the sound of a particular woman in heels, but Angela had captured his world in a way he had never dared to dream of.

"Hands of the keyboard," she said in a loud voice. Cecil obeyed, and laid them in his lap.

"Now we'll see if you've done a good enough job, honey."

She grabbed the mouse and clicked through his quite extensive collection from that day's work. She smiled and nodded affirmatively.

"Very well, dear. You're going to be a wonderful secretary in my household," she said, pausing before she continued.

"Which means I've got two gifts for you. As you heard me say, this is my household now. I'm moving in permanently, and my belongings will arrive tomorrow. Your job will be, as the proper secretary you are, detailing all my belongings, sorting them and finding a place for them in my new house. You'll also do they same with your own belongings, but we'll come back to that later. All I can say is that this place will have a new look very soon."

Cecil had seen the move coming, and thought of all the stuff he had collected through the years. At the same time, he was looking forward to seeing what Angela owned.

Besides him, though.

"Now for the second gift, I picked up this at the mall. Each evening we'll have a session of a sexual variance," she said as he wiggled with a large strap on dildo.

"Both of us will benefit from this, but as I am the master of this home now, my pleasure comes first."

Angela unlocked him and pushed him down on the bed. She struggled a bit to mount the strap on on him, but she managed just fine. While on his back, he was yet again restrained, but this time with handcuffs with fluffy pink fur around his ankles and wrists.

"Your job is easy. You will fuck me with this strap-on, seeing my pleasure while not getting any of that yourself. Besides watching me, of course. You'll never fuck a girl again, but maybe your little clit will show signs of you enjoying yourself being dominated by me. Now start off slowly and obey my commands when I want a change of pace."

Her voice was commanding now. Not sweet at all, but firm and with a harder tone. After what felt like half an hour at least, they were still riding the same slow pace, but he noticed her groans getting louder.

"Now fuck me harder now, up the tempo," she ordered.

Cecil obeyed and picked up the pace. Just before climax she jumped off the strap on and moved forward now sitting on his face.

"Use your tongue now, slut, I want to cum on your face."

Cecil wasn't that well practised licking cunt, but twisted and turned his tongue as well as he could. He felt like a captive under her butt, was deep into her pussy with both nose and tongue when he heard her screaming and the cum dripping.

"I'm staying here until I'm completely dry. Use your mouth and swallow it now, bitch," she commanded him.

After another half an hour it felt like tasting sand and she moved off him again.

"Job well done, mate," she said in a giggle and took in the sight of him laying there on the bed.

Cecil was exhausted, and satisfied with his work.

"Let's see how you are doing yourself," Angela said as she lifted up his skirt. She was impressed with the sight, congratulating him on being a real sissy.

"You're done with today's training, and we will repeat the procedure from last night when it comes to your sleeping arrangements."

She took of the strap and unplugged his butt. She unlocked the handcuffs, and Cecil knew what to do, undressing and laying down on the floor, with only panties and bra on.

"Turn around on your stomach," Angela ordered before she put in a new butt plug on him. This one was definitely bigger. She gave him new woollen clothes, and Cecil put on wool pantyhose, a wool dress like yesterday.

There was some change from yesterday, though. He got wool socks as well, thick and chunky. Tonight there were two sets of mittens as well, in addition to the same balaclava. When the boots was on, Angela started tying him with ropes and the same locks as the night before.

He felt a growing sensation for every new rope. When he thought he was finished, Angela showed him what looked like a body bag made of wool. The colour was pink, of course.

"We're ramping up the excitement this time around!"

She placed him in the bodybag and zipped it up. It was a hole for breathing, but besides from that Cecil was wholly encased in the most outrageously delicious wool blend he had ever experienced. It was parts cashmere, angora, mohair and some proper sheep wool as well, tickling and itching.

From the inside, he felt another set of ropes tying him up further. She rolled him in, and closed the sliding doors. This time the open space was even smaller than yesterday.

"Your plug is also a wireless vibrator, controlled by bluetooth. It starts now, and I reckon you will be in for one hell of a night," Angela said, barely noticeable from behind the sliding doors.

He soon felt the buzz, but this time from his asshole. And it was a completely different experience compared to his milking session that morning. His ass exploded in pleasure with a twist of pain.

He could get used to this, he thought as the pleasure overwhelmed him. It was a long night ahead. One Cecil, if he was to be frank, looked forward to.