Rebecca's Ch. 06

It felt incredibly humiliating walking to Rebecca's store wearing lipgloss. The thought of being constantly observed by other people stressed me out enormously. It was at minimum a 15-minute walk, but finally, we've made it, and Rebecca opened the store.

When I walked inside, I felt the smell of new, unused clothes. I never felt it before, maybe because I always came inside in the afternoon, not in the morning. Rebecca quickly guided me to the fitting room and told me to strip naked and wait for her. I followed her instructions, and when I slid down my panties, my dick was already hard, seeing all that sexy clothes on the racks. I looked at it, which was a second to me, but I only heard Rebecca snapping her fingers, bringing my head down to the earth.

"I see that we forgot one important thing this morning."

By saying that, she quickly reached for her purse, taking out my chastity device. She grabbed my penis with her cold hand and held it like this for a minute. Before I noticed, I have been already locked again.

"Is that really necessary Rebecca?"

"What? A chastity?"

"Yeah."

"Yes, it is. Also, you agreed to wear it for two days, for each pair of pantyhose you will take."

"Yeah, but you've said, that we will no longer fool around with pantyhose, so..."

"So you will wear it for a week, for each set of stockings."

"A WEEK?!"

"Calm down. A week in chastity is a fair price for pair of high-quality stockings. You will get used to it, and I promise I will figure out how to please you. Pinky promise?"

"Okay..."

"Right! So, this is your today's underwear!"

Rebecca handed me a few hangers with underwear. When I touched them for the first time, they felt much softer than the panties I was wearing earlier. I put the clothes hanger next to each other on the door to the fitting room, and I inspected underwear closely.

The first was the bra. The base color was magenta, but the whole lacing patterns on it were black. It was sexy as hell, moreover - it has a medium-sized ribbon in hot pink. The cups weren't big, but not small or flat at all. I looked at the tag, to see the 'Fredericks of Hollywood' mark. From what I knew, that was one of the best (and expensive one) companies that make underwear. Rebecca noticed my shock when I saw it.

"Now you understand, why chastity is a small price?"

"Y-yeah, I do."

"Go on, put it on! Try to lock it like a girl, behind your back."

So I tried and I tried. It took me a long while, but eventually, I've managed to lock it. I was really happy that I was able to do that, but my happiness didn't last long, because Rebecca quickly said that I locked it only on one joint, but there are three in this bra. She quickly helped me with another two and said, that I will learn how to do that properly soon. The feeling of wearing that bra and knowing, that from this moment this is my own bra made me very excited, my penis quickly filled the whole chastity, which caused a little pain. But it was constantly twitching like it was trying to escape from the metal prison.

"You can't hide THAT excitement. So, what you should put on next?"

"Stockings or a garter belt."

"So let's do it!"

And I took the next hanger, with attached garter belt. It was very similar to the bra - the basic material was magenta, beautiful black lace floral patterns on it, and hot pink ribbon in the middle. The lock was identical as in the bra - three joints in the back. I fitted the garter on my waistband and easily locked the joints behind me. Too bad that I cannot do the same with the bra, but simply it would look idiotic. I smiled, when my dick twitched a few more times in chastity after fixing the garter in the right position but waiting no longer I reached for the package with the stockings.

As previous parts of my new underwear, they were made by Fredericks. When I slowly opened and rolled them to the full length, I recognized them at once - whole black, with a denier of 20 yarns, tops made of seductive floral pattern. These ones were the ones I saw so many times on pornstars, and so many times I was hard instantly at the moment when I saw them on woman's legs. I can't lie - I've come countless times looking just at them in porn, but fate decided that I am the one who really should wear them. I have already knew how to roll on pantyhose, so I've prepared the stockings in the same way and slowly rolled them on my legs, which was pure bliss. I don't have to say, that my dick would explode if not for the cage, because it was twitching as hell, leaking with massive precum drops. Of course, Rebeccas eyes caught that and instructed me to wipe it with my fingers and lick them clean. This gave me another wave of pleasure, but I felt something similar to wearing lipgloss in public. Nevertheless, I fixed the clasps of the garter belt on the stockings and reached for the panties.

The panties were from the same set, base material in magenta, with black lace and a pink bow on the top. I wanted to slide them on, but Rebecca stopped me.

"What's wrong?" I asked.

"Your dick is dripping precum a lot. You will ruin your new panties at the moment when you put them on! We have to do something about it!"

"Maybe you will make me cum?"

"What? No darling that's the horrible idea. I think I have a better one."

She went to the bathroom and brought a small flat package. It was looking like a strange envelope.

"You know what this is?"

"Umm... An envelope...ish?"

"No silly, I bet you were living with a woman at some point and you saw the same kind of wrapping. This is a pad used by women when they have their period. In this case, it will work perfectly!"

A moment later, Rebecca fixed the pad in my new panties and slid them up to my bum. She made sure, that the pad is in the correct position, and all the precum will land on it.

"Rebecca, a pad?"

"Yeah, what's wrong with it?"

"You know a pad. Used by women during their period."

"You have a period too, but instead of blood, you are leaking precum."

"But it's..."

"What? Girly? Honey, I think you forgot what you are wearing. It's o-kay. When you stop leaking you can take it out, but if you won't stop, you need to change it for a fresh one. Let's get to the 'outer' clothes. I've already trashed the ones you were wearing this morning, and when you step out you will see your new ones on the table."

And I did step out. On the opposite wall to the fitting room, there was a full-length mirror, and I mean full. From floor to the ceiling. At this moment I saw my full figure dressed in sexy, pink, and black lingerie set from Fredericks of Hollywood. I stood there for a moment in complete astonishment, because I truly liked what I saw. Rebecca took this moment to reapply lipgloss on me and pointed me my new pants and shirt.

I started with a shirt, which was a simple black v-neck shirt. When I put it on, I had the feeling that it is slightly too tight, but Rebecca told me that it is fine. Next were the pants, but I've noticed that it was simple pair of blue jeans when I was taking the shirt. Unluckily it wasn't a simple pair of jeans. When I slid them on my stockinged legs and fixed their buttons, which were on the wrong side, by the way, I saw that they are ending an inch above my ankles, revealing the stockings I was wearing! But a promise is a promise. I told Rebecca about my worries, but she said that no one will notice and that I need more self-confidence. A second later we heard the doorbell and Rebecca handed me two big bags of new underwear. She gave me a quick kiss on the lips and said, that we will see at Saturday evening in the same hotel.

Walking home, again, with bags of lingerie, dressed in lingerie, new shirt and so revealing tight jeans, and the lipgloss... I never felt such a shame before, but thinking of what Rebecca said - maybe this is the way to build self-confidence? It didn't help when halfway I realized, that this tight shirt was revealing the shapes of my bra. Two round bubbles the size of lemons were sticking in front of me, and of course, straps on my shoulders created completely visible lines. But I have realized another thing as well - no one noticed, no one cared. This thought build my confidence a little as I was still walking home.

When I finally reached my apartment, I wanted to unpack the bags, but I wanted to do it in the proper way, sorting new clothes. Packs with stockings were on the top in the bag, so I took them first, and I was wondering in which drawer in my dresser I should put them, but then it dawned on me. I tossed all my socks! A strange feeling overwhelmed me because from now on I will wear only stockings, but on the other hand - I have a free drawer! That sorts one problem. I've put the packages with stockings of various manufacturers into the drawer, which day ago was full of socks. But there was still plenty of room, so I decided that garter belts will keep the company to the nice pairs of hoses. In the next drawer, I had my boxers mixed with panties that Rebecca gave me. I took them out, fondled nicely new pairs in the drawer, then I sorted the mixed pile, putting only panties in the panty drawer. The boxers visited the thrash bin quickly, but when I looked at my panty drawer, I felt like my masculinity is sinking in the drawer filled with lace.

I sat on the bed, thinking 'What am I doing? I'm a guy, a male! And guys shouldn't have a drawer full of stockings or panties!' But on the other hand, I felt my tight shirt, looked at my tight jeans, and touched the strap of my bra and the strap of the garter belt I was wearing. My senses reminded me at once, that my dick is locked in chastity, and I am wearing a pad because it's leaking! Nevertheless, I realized that these were my deepest fantasies, and one woman gave me a push to make them real. I looked down and grabbed my non-existing breasts in Fredericks bra, and I said on loud - I like it! And I do, I like the feeling of the bra on my chest, I like the weight of it, I love the floral patterns of the stockings on my thighs. I just do. And I already told Rebecca that I want to go further with this... Rabbit hole. So I stood up, closed the panty drawer, opened another one, and put there all the bras from the bag. When I closed the bra-drawer, I understood that part of my wardrobe is feminine, and I will wear it from now on. The afternoon felt short, especially with unpacking the rest of the usual clothes like shirts and pants. Which Rebecca put in the bags. The evening felt even shorter, so I showered and went to bed.

The morning brought new things this time. The feeling of sitting down to pee still amazes me, but after toilette, there is time for dress-up. And here are big changes. First, I took a fresh bra. The tag said 'Agent Provocateur' and it was completely black with lace accents, but in the middle of it, between breasts was a white pearl, and on the straps, an inch below the top of my shoulders were two small white ribbons. This one was classy, a perfect choice for a workday. I started to fight with the joints behind my back, just as Rebecca told me, but she wasn't here to help me with it. Finally, after 30 minutes or so, I've managed to lock it, and check in the mirror - I did it right! I've adjusted the shoulder straps and went to the other drawer to grab a matching garter belt and stockings. The first one was in the same color as the bra, fully made of lace, high waist, with small pearls attached to the clasps. With a smile on my face, I've connected the joints behind and fixed their position. After the garter belt, I've unpacked 'Provocateur' nude stockings with black tops and carefully rolled them up to my legs, attaching the garter belt. At this moment I had a glimpse of them in the mirror, so I've decided to look closer, and I was shocked by what I saw. On the tops, there were very simple drawings or shapes of sex positions! In front, there was a woman giving a blowjob, and on the back - reversed cowgirl position! They were obviously some kind of hose which women wear for a passionate time in bed. Stockings were already attached, so I've decided to leave them on.

Eventually, I pick the panties, and they shocked me even more than the stockings. Matching color to the bra, boyshorts style, but same full lace like the garter belt! When I slid them on, I have noticed a lack of material between my buttocks! But then I remembered one scene from porn. Woman, there was still wearing her panties, but she was having anal sex with a guy. And I'm wearing the same type of panties! An Anal Panties! My dick throbbed a few times and started leaking precum. I wanted to do the same as yesterday, which means putting a pad in my panties, but as a guy I never needed pads, so I had to figure something out with toilet paper. Eventually, I've picked tight jeans from yesterday and a fresh burgundy v-neck shirt.

I didn't have anything to eat, so I had to go to the local grocery for some supplies. Before I left my apartment, I took lipgloss and applied it as Rebecca told me. With confidence I went out, heading to the grocery. Walking down the street, I have realized, that this shirt has a very wide opening for my head and it's constantly sliding off my shoulder, making my bra straps visible to anyone. In the beginning, I was fixing it, but when I was finally in the store, I totally forgot about it. I only thought about what should I get for breakfast, and what should I cook for dinner. Walking through the alleys, I stumbled across the women's beauty section, and the first thing I've noticed there was a pack of pads. "This might be helpful," I thought, and I took one pack. After a short while, I had everything that I needed, so I headed to the register. For me, it was so stressful, with underwear like this, lipgloss, and buying pads. The young girl at the register didn't even look at me when she said how much should I pay, so I did and left the store. Self-confidence builds up again. When I came back, I saw that I have one unread message from Rebecca.

"Hello, darling! How is your day? I hope you like the new underwear! Show me what you are wearing today? xoxo"

Not thinking any longer, I slid down jeans a bit, to show her the tops of my stockings. "Picture sent and received" I read.

"I wouldn't mind wearing that for a date! Lookin' hot sweetie! Any leaks from pp?"

"Yeah, my penis is leaking from the moment I've put on the stockings."

"Did you do something about it?"

"Yeah, I was in the store for some food, so I've picked up a pack of pads."

"No, you didn't! You are a brave girl Diana! See you on Saturday?"

"Sure"

"Amazing! I have a surprise for you, my love! xoxo"

I was wondering what kind of surprise she has for me. The rest of the day I spent partially working, and partially cooking dinner, and the same was the rest of the week. Every morning I've picked a new set of lingerie in various colors, but when Saturday came, I had a similar set of Fredericks like I was wearing on Monday, but this one was red. Rebecca sent me a message with room number in a hotel, which was again five-one-five. I have dressed, packed a small backpack with pajamas, and took an uber to a hotel.

In the room, Rebecca greeted me with a glass of semi-dry wine, and instructions to pull down my pants and shirt. And there I was, only in my lingerie, in front of a woman of my dreams. She was wearing a very similar set of 'Agent Provocateur' which I had on Tuesday, but with different details. In front, there was a drawing of a woman holding a guy's chastisized penis, and on the back a drawing of her feeding him a load of semen. I had to stare a bit too long because she asked me:

"Do you like it darling? They are custom made, no company would release something like that."

"They are... us!"

"Exactly! Aren't they lovely? Maybe you would like to look at them closely."

And that was a hint for serving my beautiful Mistress orally. I loved to do that, so even when she was standing, I quickly took off her panties and dived with my tongue in her pussy. She has to be really horny during the whole week, because I've noticed, that her juices are soaking the tops of her stockings. I licked her for like five more minutes, and she started screaming in pleasure, grabbing and squeezing my head between her thighs. Eventually, she pushed me away as she collapsed on the bed. But I was eager for more. I waited a minute on the floor, then kneeled in front of her, spread her legs, and started licking her again. I think the first orgasm didn't subside enough, because again after a minute she was tensing and twitching in delight. I have collapsed next to her, giving her one of the deepest, most penetrating kisses that I ever did. I think she loved that because her tongue started to penetrate my mouth soon after that, and finally, we both collapsed, cuddling each other.

When Rebecca recovered, she took me in front of the wardrobe with a mirror, and she stood behind me.

"Do you like what you see?" She whispered. I didn't have the time to respond, because she continued.

"Do you like what you are wearing?" I've nodded.

"Yesss, nod like a good girl. Do you like what you are becoming?" And I've nodded again.

"I bet these are your wildest dreams. And they are coming true..." She intensively grabbed my 'breasts' and slid down the cups of the bra.

"Look at your titties Diana. Look how flat they are. I bet you would like to have boobs like mine..." At this moment, she squeezed my nipples and started circling around them with her fingers.

"I feel your titties are getting harder... Would you like me to continue?" I've nodded again, quietly moaning.

"Moan like a girl Diana... Don't be ashamed... Feel the pleasure..."

I felt that she took down my panties to the ankles and slowly reached to my locked penis. My arousal was getting higher and higher, and I bet that without chastity I would explode a long time ago. Suddenly she bit my ear a little, leaving a red lipstick mark on it and then she moved in front of me, looked me deep in the eyes and asked:

"Would you like me to suck on your titties Diana?"

"Y-yes.... I would love to"

"You have to say it. 'Suck my titties, please Mistress Rebecca'"

"Suck my titties, please Mistress Rebecca"

After that words, she started kissing, licking, and sucking on my titties. I felt that my excitement level is getting sky high, and after crossing the edge I felt wave after wave of pleasure, with the center in my nipples, but she didn't stop at all. She was sucking them for good five minutes, and when she stopped, I've sat down on the edge of the bed, totally besotted. After a longer, while I recovered, and Rebecca started kissing me as previously, penetrating my mouth with her tongue. Eventually, she stopped, reached down to my crotch to detach a small container, similar to an espresso cup. It was full of sticky, white sperm.

"Look how much you've made it!"

"It's really a lot, I never came in that volume."

"And you know what? This was a hands-free orgasm. You've come only by stimulating your nipples. Or should I say titties?"

"Haha! Titties sounds good to me. I think that was one of the best orgasms that I ever had!"

"It's so good to hear that. From now this is the one method that will make you cum."

"One method? The other one is when you unlock me?"

"Oh, you silly. There is no need of unlocking if you can cum like this. Maybe in the future, we will find another similar method? Who knows... Besides - you should get used to chastity by now."

"But Rebecca... Wouldn't you like to have normal sex with me?"

"I would love to. And I will. Soon. But enough talking. This cum won't drink itself. Bottoms up!"

For a normal guy, drinking his own semen is something disgusting, and being forced by a woman to do that - the most humiliating experience. For me, a boy wearing lingerie every day, it was like the natural order of things. I think I can proudly say that I like to drink my own cum, and I enjoy the taste of it, and this time, the amount of it went to every corner of my mouth, my teeth, and completely dominated my taste glands.