Rebecca's Ch. 08

On Monday morning, when I woke up, I was flooded with different kinds of thoughts. On one side, it felt like my life just started and I am at the beginning of this road, from the other - I have many thoughts if everything that I am doing now is right. Fortunately or not, I was curious enough about where this path leads, so I started my morning routine. Sitting on the toilet was completely natural after a few months wearing chastity, and now I had to adapt to applying makeup every morning.

I took the foundation from the shelf under my mirror and applied it to my face. "It wasn't hard," I thought, so I moved to eyelid shadow. Here it gets a little wild - applying the shadow wasn't easy, and I am sure that I didn't distribute it evenly like Rebecca did yesterday. Mascara was even harder than the shadows, and after good fifteen minutes, I had it smeared all around my eyes. After looking in the mirror at my masterpiece, I looked like one of the pornstars that were, dirty speaking, face-fucked. I decided that I won't do that without any tutorial, so I took special water to wash everything off and went to dress up.

I didn't feel particularly sexy after what I'd done on my face, so I had to compensate for that. The bra, garter belt, and panties were in light pink, and stockings were black, with matching pink ribbons at the floral pattern black tops. In a minute I was in my fresh lingerie, so I reached for jeans and a t-shirt. Here, I remembered about my completely new attire, so I've put back jeans with a t-shirt and reached to another shelf for a blouse and skirt. The first one was a chiffon style dark red blouse, and the second was a grey pencil knee-length skirt. I've put on both, to feel my clit twitching in its cage, But I thought that it was the last reminder of my life as a male. After clothes, I've put on my jewelry, which means white pearls on my neck and bracelet on my ankle. After everything, I ate my cereal and turned on the computer to look for some makeup guides.

The first tutorial seems to be easy enough after a quick reading of it. It suggested choosing some brighter colors at first, so the overall effect won't look like a cheap prostitute. It precisely described how to apply particular cosmetics, and how to use all the brushes that are part of the makeup kit. Armed with all the knowledge from the guide, I went to the bathroom to test it in the field. I have applied everything slowly, taking care of every detail. It took me an hour, but the effect was more than acceptable. At the moment when I was ready to start working, a doorbell rang, and when I opened the door I saw my mom. My sweet, loving mom.

"H-hi Daniel..."

"Hi, m-mom."

"Why are you looking like... woman?"

"Oh, mom... There is a long story behind it."

"I've come to visit my only son, so I have time."

"Of course, please come in, take a seat, I will make some coffee."

My mom entered my apartment and went to the bathroom for obvious reasons. It took her long enough, but she finally went out and came to the kitchen, to my small table.

"You have quite expensive cosmetics there. And they look brand new."

"Yeah..."

"So, tell me everything. How did it happen, that my only child, my only son looks like my only daughter now?"

"Well, everything started, with my weakness for women's legs. I loved to look at them, and if they were wearing any kind of hose, it made me..."

"Excited," Mom added.

"Yes, excited. So, one day, walking down the street, I saw a small lingerie store on the side. I've got excited enough to stare at the exposition for a few minutes, and the owner of the shop saw me and invited me inside."

"So you went inside?"

"Yes mom, I did. In this shop, I have met Rebecca, my current girlfriend. She slowly explored my... fetishes. When I entered the shop that day, she gave me lace panties to wear, which I did."

"You wore the panties? But you are a boy and only girls wear panties!"

"That's what I want to say, mom, after a few weeks, months maybe, I realized that I'm not the man you think I should be. My every relationship with a girl ended with a breakup, not to mention that I am not well endowed."

"So you are into men now?"

"No! Of course not! I said that Rebecca is my girlfriend now. Besides, she accepts who I really am, and she wants to help me with every aspect of it. We are both happy."

"Oh, I don't know Daniel. I mean, when you were really young, and maybe you can't even remember that you were playing with my clothes. I mean, you liked to take everything out of the drawer, inspect and put it back in. You liked my underwear in particular, but I didn't think that a child at that young age..."

"I get it, mom. I get it. But what do you think?"

"Well, you are dressed very fancily. I like your blouse and skirt, you have very nice pearls. But the makeup is... It needs some improvements."

"Thanks, mom. I've just started to learn how to apply makeup, so I think my skill will improve."

"If you want to look like a woman it surely needs to. Are you happy dressing like that, doing makeup and stuff?"

"I'm very happy mom. I wasn't that happy when I was living as a boy, but now I feel alive. Also, I am called Diana now."

"Then I'm happy for you, Diana. But tell me, how about your... You know, bed things?"

"Mooom!"

"What? Can't I ask my boy how is he doing?"

"I've abandoned 'bed things' as a boy a while ago. And I think it's for better."

"So how do you..."

"Mom, don't play hide and seek here. Just call it by the name."

"How do you have an orgasm?"

"Rebecca stimulates my nipples. And it feels way better than a usual orgasm from masturbation."

"Nipples, huh? I think I will have to sort everything in my head. I wasn't prepared for that." She pointed at me. "But, if you are happy, I think everything will be all right. If you will have any problems, you can always come back home. I don't care if you are a boy or a girl, you are my child."

"Thanks, mom."

"Thanks for the coffee. I will go now, be careful honey. See you soon - Diana!" She winked when she spoke my new name.

I've texted Rebecca shortly after mom left and told her everything.

"How did she react?"

"I think she was okay with that, she said that she need to sort it out."

"Are you fine darling?"

"Yeah, thanks. I did my makeup, look:"

*Sends a selfie*

"Niiice Diana. Maybe we will grab a coffee later?"

"Sure, when you are closing the shop?"

"Around 5 P.M."

"See you there then. Kisses!"

After a few messages with Rebecca, I started working. I had new, positive feelings while being dressed like that during my working hours. It was airy down there, and I need to get used to this. When my clock showed 4:40 P.M. I reapplied my lipstick, put on stilettos, and went to meet Rebecca at her shop. I reached my destination in fifteen minutes, even walking in heels. I was happy about that. We both greeted with a short, but deep kiss.

"Hello, Diana. How was your day?"

"It was very nice, I'm getting used to the new clothes and makeup."

"I see, and to be honest you did a very good job with foundation and shadows. Have you watched any tutorials?"

"Yeah... When you would see me my first attempt, you would presume I was facefucked like a cheap prostitute."

"Hahaha! Too bad I didn't see you!" She laughed. "But how about your meeting with mom today? She came unexpected or what?"

"Yeah, I didn't expect her at all, and suddenly the doorbell rang. She was shocked to see me like this."

"She will get used to it. Maybe she always wanted a daughter? Anyway, let's grab some coffee."

We both went to the small cafeteria to sit down and talk.

"So what do you think about living as a woman? You started to notice how many heads you turn when you are walking?"

"I notice something, but I think I don't care about that."

"Why not care, I love the feeling when I am attracted to somebody and so should you! I told you that."

"Yeah, but for now, I think dressing completely as a woman is enough for me."

"Okay, I understand. You need time to adapt to your new life. Anyhow, I think I've found a solution for your cum problem."

"You do? What is it?"

"I will show you tomorrow when the package will arrive. Maybe we will meet at your place?"

"Yeah, why not? I would like to finally welcome you to my apartment."

"So it's settled then. I think it's time to call it a day. Will you text me the address tomorrow?"

"Sure thing."

"Good. See you tomorrow then."

We kissed goodbye, and we both went home. I couldn't sleep that night, the curiosity of the solution for my problem flooded my mind. Eventually, I fell asleep and I had the weirdest dream in my life. I've dreamt about teasing a man, the one from the restaurant the last weekend. I crossed my legs, revealing the tops of my stockings, but in the dream, this man didn't turn his head, instead, he walked to me, pulled out his dick and I involuntarily grabbed it.

And I woke up. My panties were wet of precum and my clit was twitching inside the cage. With no other choice, I went to the bathroom to take a shower. After drying myself, I dressed in my green set of lingerie, with a black skater skirt and pink ruffled blouse. After breakfast, I've texted Rebecca with my address and started working. Just before 6 P.M., I heard the doorbell.

"Welcome my beautiful Mistress!"

"Good morning Diana. I hope you had a wonderful day."

"I did. I couldn't wait for you and your solution!"

"I bet you couldn't. You have a very nice place. It looks raw but nice."

"Thank you, Rebecca. How about your solution?"

"Are we impatient? I guarantee that you will love it. But you have to trust me completely. Are you ready?"

"You know I am."

Rebecca opened her purse and took out two boxes in the same size, and in the same dark purple color. She instructed me to open them. In the first one, there was new chastity. Definitely smaller, made of metal rings, with a small tube in the middle. It was in a chrome pink color, which looked very expensive. Rebecca explained, that the tube is going up to my urethra, so peeing and cumming will make less mess. In the second box, I have found a butt plug, made of the same material and color as the chastity, but something was moving inside the plug.

"It's Geisha plug. Inside, if you would cut it in a half, you would find a small metal ball, which shifts with your every movement. It will stimulate your prostate, so you will produce sticky white cum like before."

"Sounds nice. How long do I have to wear it?"

"At all times darling!"

"Oh-Okay. I see that the new chastity is smaller too."

"Don't worry about it. You will fit perfectly. Wearing chastity for longer periods has the side effect of shrinking the penis. But, you don't use it anyway, so I don't think it's a problem, do you?"

"No, of course not. If you want me to wear it I trust your judgment. Besides, I love nipple orgasms."

"That is wonderful to hear Diana! Now, pull down your panties, we will change your equipment."

I have pulled my panties down, and Rebecca unlocked my current chastity device. I was shocked when I saw my penis shrank to two inches! It became hard immediately, but it didn't change much, I mean it was semi-hard, but it didn't grow at all! Rebecca said that is an expected effect and it's completely natural. She put on a new cage, and I heard a loud *click* sound. I looked down, but I didn't notice any padlock or locking mechanism.

"How did you lock it, Rebecca? It was really loud, but there is no padlock!"

"This is the newest, custom-made model. It doesn't have a padlock, instead, there is an innovative locking mechanism built in the body of the cage. The only option to unlock it is to have a very small, and very strong industrial-grade magnet. And these are only available in few places in a world."

"So there is no option to unlock it at home?"

"No sweetie. Is it comfortable?"

"Yeah, even better than the old one."

"Good. Let's screw the tube inside it."

It hurt a little at the beginning, but when it was fixed in one position I literally didn't feel any difference between this, and the old one.

"Everything is ok?"

"Yeah."

"Ready for toy number two?"

"Yes."

Rebecca spread my cheeks and started licking the entrance to my bottom. It felt really incredible for one minute, but after that one minute, she slowly pushed the cold metal geisha plug inside me. "Relax Diana," she said, and I did whatever I could to relax my sphincter. I didn't have to wait much longer, as I felt my butt filled with a metal toy.

"Oh my my! Diana! Your asshole must be very hungry to swallow that plugin in no time! Another natural thing for you!'

"T-thanks, I think. I feel my butt filled up, and it's cold."

"It will warm up eventually. Walk around to test it."

So I walked around. Wearing heels, walking in a straight line, my hips sway and the metal ball bounces inside the plug. After a few steps, I only felt like I would need to a toiled, but after more steps, I started moaning quietly.

"I see that you like it, Diana."

"I-I d-do, but it's so i-intensive!"

"You will get used to it. Now your male g-spot is stimulated, so now your juice will be white and sticky. Maybe next time we will meet here, not in a hotel?"

"Works for me, but why the change?"

"The hotel was needed only to make you more confident about your feminity. Now, when you are living as a woman, there is no need for that."

"I see."

"Yeah. Wear the plug for long as you can, of course, you can, and have to pull it out for obvious reasons. Also, you'll probably need lube to plug it back, but you can buy it in the pharmacy. Gotta go love. See you on Saturday."

"Bye!"

This night was even worse than the previous one. I couldn't sleep at all. Even if I couldn't feel the new cage, the plug made all the work. I felt the movement of the ball with every breath I took. Eventually, I've managed to close my eyes and sleep a little.

Again, I had the dream of the restaurant happening. Last time, I involuntarily grabbed this guy's cock and I woke up, but not this time. The dream continued, as I started to stroke him, while Rebecca encouraged me to do it faster and faster. A few more strokes later, I felt that cock pulsates, as it coated my arm in white, sticky sperm. And I woke up after that incident, but my pink panties were soaked in the same thing as my arm in the dream. I was incredibly exhausted, and in the middle of the night, I had to take a shower and clean myself. The only positive thing about that was the thought of working buttplug.

After the shower, I've put on fresh pair of panties and get back to bed. I didn't have any trouble falling to sleep this time and peacefully I slept till the morning.

Everyday routine changed a bit now. The morning toilet was different, as I had to remove my buttplug as a first step. It was difficult as hell, as my sphincter adjusted to the thin base of the plug, and didn't want to let go of the thicker part of it. I finally managed to pull it out, and I sat on the toilet. Wiping my clit after was the easiest part now, as I had to wipe the end of the tube. Much less messy, as Rebecca promised.

After morning shower for me and my newest toy, I was trying to get it back inside, but with no luck at all. I had to go to the shop for something for breakfast, so I could jump to the pharmacy, which was next to the grocery. I chose nude stockings, a black bra, garter, and panties which I covered with a light pink blouse and black pencil skirt. I thought, that black stiletto pumps will match the rest of the outfit, so I chose them as well. Quick makeup, some accessories on my neck later, I was ready to go to the stores.

Walking out being completely dressed as a woman didn't raise anxiety anymore. I was super confident about it as I embraced my feminine side completely. After the grocery store, I went to the pharmacy for the lube. The queue was enormous, but I didn't have any other option than wait. After 20 minutes, it was my turn. I simply asked for a bottle of lube, and the saleswoman brought the sixteen ounces bottle of water-based lube. Also, she put a six-pack of condoms next to it.

"I didn't order the condoms, ma'am."

"They are for free when you buy lube in ten ounces or larger. The larger the bottle, the more condoms you get for free."

"I see, thank you."

I paid and went out with a large bottle of lube in one hand, and a six-pack of condoms in another. This clearly shocked me as I forgot to hide it in the paper bag with my groceries. I was lucky that nobody saw me like that because it seems like a girl is going home for some sex or at least a masturbation marathon. I've texted Rebecca about this.

"Nice, so you are ready for some action!" She texted me back.

"Yeah, but I don't know what to do with the condoms now."

"Yep, it's not like you gonna wear it!"

"I know, I bet they are too big for me after all."

"No worries honey, I'm sure we will use them somehow. Are you plugged already?"

"Not yet, I'm gonna eat my breakfast and put the plug in."

"Good luck girl! Have a nice day too!"

"You too. Kisses!"

As we stopped texting each other, I ate my breakfast and opened the lube. I smeared it all over the plug and the entrance to my ass hole. With a little gentle push, my chrome-pink geisha plug popped in less than a second. I felt full down there for the first two minutes, but as soon as I felt the ball inside it started wiggling around, the feeling disappeared as it started to give me more pleasure than discomfort.

I was working for the whole day, so basically I was sitting down. Every time I changed position on my chair, the ball bounced off the walls inside the plug, pressing my g-spot. In the beginning, I started to leak precum. My panties were wet very quickly, so I decided to clean up, and use a period pad.

Many hours later when it was already dark, I decided to call it a day. I have undressed, tossed my underwear in the laundry bin, and removed a pad, which now was full of gluey white cum. My whole crotch was covered in it and it was sticky as hell. Now, when I did a single move, and when a ball bounced in the plug, a small glob of cum leaked out of the chastity tube. I wiped it off with my fingers to quickly put it in my mouth. It tasted as it looked like - gluey, a little salty but not sour. A few minutes later, I realized that I'm moving just to taste another glob of my juice.

When I was back in reality, I decided to pull out the plug for a night. I didn't want to get a shower in the middle of it like yesterday. After a shower, I pulled on my babydoll nightie with matching panties and went to bed. The whole night was calm, I didn't wake up at all, but in the morning I had a strange feeling that something is missing. After the toilet, my toy was already popped inside my hole again. I texted Rebecca to tell her everything about my past experiences.

"It sounds like you are progressing faster than I thought. It's very good! Just keep wearing it, eat everything that comes out hon. On Saturday we will try something else."

"Ok, can't wait Rebecca! Kisses!"

But it was Thursday, and my day had just begun. I chose a red set of lingerie with black stockings for today. A red blouse with the same black pencil skirt from yesterday will work fine. I've finished my look with make-up, which I think I did too strong, and a pearl necklace. Not wasting today's panties, I've already put the pad inside.

An hour later, my pad felt sticky, so it was time to change it. Like yesterday, it was full of white cream and every movement produced another glob of it. I was so absorbed by the look of it, that I immediately started to wipe everything from the small pipe and from the pad. Before I noticed, I was licking my sperm directly from the pad, not forgetting to move and lick whatever comes out. 'I'm addicted to cum' I thought. 'I'm addicted to eating it was more precise, but I loved it and I couldn't stop, but it was time to get back to work, so I've put on a fresh pad and walked to my desk in a straight line, swaying my hips as much as I could.