Rebecca's Ch. 06

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"I bet you liked every drop of it Diana. But could you do me a favor?"

"Sure thing."

"Don't brush your teeth."

"Like ever? Or before sleep?"

"Before sleep honey. I want you to feel the aftertaste in the morning."

"That sounds wicked hot. No problem Mistress."

"Let's get a shower together."

And we did have a quick shower, where we kissed passionately. Rebecca praised the taste of my mouth, and she didn't brush her teeth too. When we came back to the bedroom, I've reached my backpack for a pajama, but Rebecca stopped me immediately.

"Oh Diana, you can't sleep in something boring like this! Every day you are wearing hot lingerie, so I have a surprise for every night of yours!"

Then, she pulled out a hot pink satin nightgown with lace pushup cups. It looked incredibly sexy, and then Rebecca put on the identical on herself, making an astonishing cleavage of her breasts.

"See? Tonight we have matching nightgowns. In the bag are three more, I hope it will suffice for now. Turn off the light and come to bed, my sweet little cum eater." She giggled.

I have turned off the lights, l lay down next to her, kissed her for goodnight, and turned to the other side. Soon she cuddled me like a little spoon, and we fall asleep.

In the morning, the taste of cum was unpleasantly strong, which of course I told Rebecca when she opened her eyes.

"Good morning to you too Diana... Now you know what the girl is feeling after swallowing a load at late night. You will get used to it, but you can of course brush your teeth now. Get dressed after that, so we could go to eat something."

For breakfast was light caesar salad with pineapple juice. Just like the last time. When we ate, I've noticed that Rebecca wants to say something.

"What?"

"I didn't say anything."

"But you look like you want to say something.'

"Okay, fine. Tell me - Diana - do you enjoy all of this? But be honest, you won't hurt my feelings."

"What do you mean?"

"I mean me, pushing you to the feminity, telling you what to wear. And you, a young guy, eagerly putting on female underwear every day. Is that what really turns you on?"

"To be completely honest with you Rebecca - I think I needed that push. If not you, everything would be in my head, and as you said yesterday when you were stimulating my titties - these were my wildest, deep buried dreams. Every step you are pushing me onto feels strange, embarrassing, maybe even humiliating, But I want to continue that. I love to put on lingerie every morning, I love when you hand me a cup of my own semen and want me to swallow that. I want to do all these things."

"Do you think this is something that would a man do?"

"A man?"

"Yeah. Do you feel like a man?"

"That's a tough question..."

"Listen, I don't want to offend you right now. But let's face the truth. You are no 'man'. It just doesn't fit you. But it's alright, not every guy has a big, fat cock to fuck a woman, some of them don't want to admit that they are small. But it seems you are not bothered by that."

"What should I say... You locked me in chastity, and after a while of wearing it, maybe it was a good idea? I don't know. But I love to please you, and yesterday orgasm that you gave me was the best that I had in my entire life, and I wish I could have more like these with you."

"That is amazing to hear! Really. I feel happy with you too. But it's not the end of our journey. I have so much in plans for both of us!"

"Really? Can you lift the veil of this whole secrecy?"

"No can do. I'm sorry, but you have to trust me. But for today I have another small surprise for you. A more pink-ish lipgloss!"

"Whaaat? I've just gotten used to the old one."

"Trust me. It's more pinkish, more girly, and most important - it will make your lips poutier."

"Do I really need that?"

"Oh, you do. Just apply it."

I did as instructed. After looking in the small mirror from Rebecca's purse, my lips truly looked poutier. I felt more girly, and I liked that.

"You don't feel diffident now?"

"No, why?"

"Last time you were so scared going out with almost invisible lip gloss, and now you are wearing a pink one."

"It's like you've said - no one care."

"Bloody right. But I do. And you look beautiful!"

"Thank you, Rebecca."

"I think it's time to go. I will text you tomorrow, ok?"

"Sure thing, my love. See you next Saturday?"

"Yes. Kisses!"

After that, I hid new lipgloss and ordered an uber back to my place. I didn't mind at all standing on the sidewalk with my pink, pouty lips. No one cared about that, no one noticed or commented. At home, the rest of the Sunday went very calm, so I wanted to set up a washing machine with my underwear. Of course, I didn't know how to wash hosiery, so I had to google it up. The guide said, to put them in a lingerie bag and then put it in the machine. Unfortunately, I didn't have a lingerie bag, but the next point in the guide said, that the pillowcase will work just fine. I've set the machine to a 'delicate' cycle and started it. Around 20 minutes later it was done, and following the guide, I straightened the stockings up and hung on a dryer. I did the same with bras, garters, and panties. Looking in the drawer, I had four more sets to wear, so I didn't have to worry about running out of underwear, but if that would happen, there were still some boxers in the trash bin, but since I am wearing lace panties, boxers are nasty, so I've decided to go throw out the trash. I fixed my lipgloss and went out with a bag full of male underwear. Standing in front of the large trash bin, I hesitated for a short while, but ultimately the bag landed at the very bottom of a stinky dumpster. I felt that part of my masculinity faded away irreversibly. Back home, the rest of the laundry was done, so I hung it next to the hosiery and called it a day.

The whole week went very fast because I was overwhelmed with work. The client wanted me to finish the project by the end of this week, so I had to do a lot of overtime. I have blinked my eyes to see it was Friday evening. Rebecca texted, that she want to go out for a drink, so we will meet in a local pub near the hotel at 5:00 P.M. on Saturday. Two hours before the meeting I took a shower and shaved my whole body, although there was not too much hair on it. After drying, I have opened the drawer with bras and took the only one that I didn't use, because it was green, and I am not the biggest fan of this color. The bra had a little lace rolled under the cups, but unrolled it was a ruby green bodysuit with garter belt straps. It looked amazingly hot, so I've put it on, to notice a small joint in the crotch. 'Smart' I thought locking it and seeing myself in a mirror, I quickly changed my mind about the color. Lace cups gently rubbed my nipples with every step, making me incredibly horny. I had to put the pad inside the panties because I was already leaking with precum. Stockings were evidently from the set because it was nude color in den fifteen, but the tops were made in floral green pattern, accented with big drawings of red roses. When I rolled them on and attached them to the bodysuit, I felt like a Poison Ivy from Batman comics, but way sexier. I've taken black jeans, and there was a '3/4' mark on the tag. I didn't know what does it mean, but when I pulled them on, I realized, that half of my calf is visible. With a blush on my face, I've put on the shirt, applied lipgloss, and went out.

The bar was full of people, but Rebecca was sitting on the stool in front of the bar counter, sipping scotch on rocks. When I approached her, she greeted me with a quick peck on the lips, which glued together for a second, because we both were wearing lipgloss. "Let's move to a table," Rebecca said, and we went to the quiet corner of the pub.

"So, how was your week?" I asked.

Rebecca made big eyes, exhaled the air, and said "Exhausting. very, very exhausting. I don't know what happened but I had a lot of women in the store every day, and I had to advise every one of them about sizing, colors, styles, patterns, and all other stuff. And because a lot of merchandise was sold, I had to do a small inventory every day to sum all numbers up. So I was working for at least twelve hours from Monday to Friday. How about you?"

"Poor you... I hope this whole madness ended and next week will be calmer. I had a lot of work to do too, the client wanted his project finished, so I did overtime as well."

"Yeah, that's what I thought. But we have to keep more communication in days like these, to support each other."

"Totally agree, it would be so much better to keep talking during the week, not catching up every Saturday."

"Yeah... Maybe you want a drink?"

"Sure."

"Waiter! One more glass of scotch, neat this time, and 'Sex on the beach' for my friend please!"

"Sex on a beach? A beer would be better."

"From beer, you will get your belly fat. Besides, girly drink for my girly boyfriend."

"So I am your boyfriend?"

"Sorry for that. Girlfriend of course!"

We both giggled about that, but I didn't feel offended, on the contrary, it was nice to be a significant other to someone. We chatted a bit more and sipped our drinks. Then Rebecca told me, that she has another surprise for me, but we need to go towards her shop.

Walking down the street, we finally reached 'Rebecca's, but she kept going. Rebecca's shop is located on one of the aisles of the local market, so there are multiple shops around, like a small bakery, grocery with fresh vegetables, or electronics. A few aisles further, she stopped in front of the Korean beauty parlor, turned around, and said:

"We are here, and this is a surprise I was talking about."

"A beauty parlor? What kind of surprise is this?"

"I think we need to reach out for something more than lipgloss, won't you agree?"

"I trust you about that. So if we want to get in, let's get in."

Inside there were two stations with Korean ladies. Rebecca led us to them, but from what I understood, none of them spoke English, so Rebecca did a few gestures, they nodded with smiles and showed us that we should sit on the chairs. We did as instructed, and Rebecca handed me a catalog with various shades of colors.

"What is this?" I asked.

"This is a catalog of nail colors. You can pick which you want, but if you don't want to flaunt around with them, I strongly suggest picking some shade of nude color."

"Good point, this will be my first time with painting nails, so..."

"Oh, you don't say, Diana! I thought you were painting them earlier!" She giggled.

"Ha-ha, very funny. What's your choice?"

"I'm choosing 'Rosso Corsa'."

"And what the hell is that?!"

"Oh darling, you need to learn a lot. It's a shade of red!"

"Okay, so I will take light nude then."

Which I've pointed to one Korean lady. She, on the other hand, asked another one for help, pointed at my feet, and said 'Diana shoes off' with a Korean accent. I think she might catch my girly name when Rebecca said it out loud, and it felt embarrassing being called like that by a stranger. When I took them down, she started saying something in her native language, but I quickly understood that she saw that I'm wearing stockings, and need them off, to paint my toenails too. I stood up from the chair, and she guided me to the small supply closet and pointed again at my feet saying 'Diana, off!' and closed the doors. So I took down my pants, unlocked the clasps of stockings, and rolled them down. When I was holding two stocking donuts when I was leaving the closet.

"I think I know what set you are wearing today. You could choose Ruby Green for your nails." Rebecca said smiling.

Two Korean ladies started to work on my toenails, both feet at the same time. I don't know what they were doing, but I saw a few transparent layers were applied, then my nails landed under some kind of UV light, and then again a light nude color was applied, and again the UV light. After a few minutes, they started shaping nails with electric nail files, and then they took care of my hands. Finally, nails on my fingers were in light nude, but what's more important they were thicker and 1/3 inch longer. I saw that kind of nails on women in real life, but in movies too, especially in porn, but I never thought I will wear them too, which I told Rebecca. She responded, that I will adjust quickly, the same as was with underwear and lipgloss. I couldn't disagree with that. When we left the parlor, my Mistress ordered an uber to a hotel, where we were supposed to spend the rest of the evening.

When we reached the lobby, a receptionist called Rebecca and said, that our usual room was booked earlier, and they only have a honeymoon suite, which was more expensive than the standard option. I have suggested, that we should split the cost then, and spend the night with champagne, celebrating my first nail painting. Rebecca smiled and accepted the offer. A few minutes later we were opening our room, to see the giant bed in a shape of a heart, a big bathroom with a shower, where we could easily lay down, massive TV on the wall, and a bottle of cheap champagne in the bucket with ice. Rebecca said that I look divine and very girly, and just now I have noticed what she was wearing.

Amazing makeup with dark eyelids, followed by extended lashes, seductive red lipstick, white pearls on the neck, tight, satin blouse in purple color unbuttoned enough to see her amazing cleavage, pencil skirt with lace finish at the bottom, a fabric belt around the waist with big golden letters 'D' and 'G', black stockings, and platform pumps, with pointed noses and beige soles.

"Thank you, Rebecca, I should say earlier that you look marvelous too, but I think the stress from the whole week just started to fade away after a couple of drinks. But I love you look."

"I have noticed that you eyed me from head to toe."

"Sorry for that, I didn't want to be rude."

"Oh, you were not! I take it as a compliment, and you should take it too when someone will eye you. By the way, what did you like in particular?"

"You look so sexy in general, your amazing makeup, the pearls, cleavage, a skirt with lace finishing, and these killer 'fuck me' pumps. I just love how you look."

"I love to hear that, but I would like to see you in these stockings and bodysuits. Would you like to give a show to me?"

"With pleasure!"

Rebecca turned on some music, and I started dancing slowly, making her laugh. I took off the jeans, just below my butt, dancing and twirling my lace-covered ass in front of her. After jeans and shirt, I sat down, to roll the stockings back up my legs, showing them off high in the air. When I've locked the clasps on green tops, Rebecca approached me, took off her pearls, and placed them on my neck, making my dick twitch in my cage. She undressed quickly too, walking out of the skirt, revealing no panties at all, just bra, garter belt, and stockings. Gently, she grabbed me by the pearls off the bed and pushed me down on my knees.

"I want this as the last time - I want to stand." She stated, and I immediately buried my tongue deep inside her pussy lips. I grabbed her by the buttocks, trying to push myself deeper into her juicy vagina. It took me a long time, to give her climax, which I felt was moderate at best. When she fell on the bed, I tried to try again, but she pushed me away.

"Diana, stop. Sometimes women are not in the mood for massive orgasms, sometimes I need just to cross the edge, that's all. Sorry for that."

"You don't have to be sorry, I always feel awesome when I give you an orgasm, I thought that you are disappointed by me or something."

"No, I'm not disappointed at all. And I'm sorry, but I think I'm too wasted to give you some pleasure too. Can we cuddle and fall asleep?"

"Of course Mistress."

I cuddled her, but she turned me over and cuddled me like a little spoon. I really felt like her girlfriend as we fell asleep. In the morning I was still in my bodysuit and stockings. I went to the bathroom for the morning toilet, to see that I am wearing Rebeccas pearls. I've brushed my teeth and felt her behind me, kissing my arms and my neck.

"You look so sexy in the pearls..." Saying that she grabbed my hand and placed it on my shoulder, gently moving down the lace cups of the bodysuit. She started circling around my nipples and said: "Look how girly your nails look. How many times have you seen a girl with the same nails as yours? I bet many, many times..."

I felt as she unbuttons the joint behind my groin, and fixed the cup on chastity.

"Look in the mirror. What do you see there?"

"Lovers..."

"Yes, but also, I see two women, having fun together. Can you name them?"

I nodded and said "Rebecca and... D...Diana."

"You hesitated. You must be sure about your name. What is your name?"

"Diana"

"In a full sentence."

"My name is Diana."

"Again."

"My name is Diana!"

"Again!"

"My name is Diana!!!"

Finishing this phrase for the third time made my body convulse, filling me with bliss and enjoyment. Rebecca turned me around and kissed me passionately, whispering to my ear: "I love you Diana", which made me moan loudly. When I gained back my senses, I replied "I love you too, Rebecca", and she was already holding a cup of warm, semi-transparent fluid in front of my mouth. I have stuck my tongue out, and she poured the content on it, saying:

"Play with it in your mouth as the last time and swallow when you will be ready. I want you to keep this taste for the whole day."

And I did. Even after breakfast, the pineapple juice I was still feeling the taste of cum in my mouth, but it wasn't bad. Around noon I got used to it, and to be honest, till I brushed my teeth in the evening it didn't bother me at all. When we were leaving the hotel, I was still wearing Rebeccas pearls. She told me to keep them and wear them, so for the following week, I've had to get used to painted acrylic nails, and the pearls on my neck.

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4 Comments
DianeRedfernDianeRedfern9 months ago

Again good pacing, hot story

AnonymousAnonymousover 2 years ago

i love the woman that diana is growing into. If i may make a suggestion, when my sister was training me, she used a butt plug to help me to walk like a woman. Perhaps Mistress Rebecca might want to try that too. i hope you will read my stories too. Love, pretty_sissy_julie

AnonymousAnonymousover 2 years ago

With Drew Becky getting in the way that she does is he going to finally get a guy's cock into his mouth and he gets breast

AnonymousAnonymousover 2 years ago

I hope with her conditioning that she is setting you up to suck off a guy

I love the lesbian aspect of this story and the possibility of strapon play, but if another guy was brought in not so much

I can see Diana become more comfortable in women's fashion that she might start helping around the shop or ???

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