Femdom Watching Little Sister Ch. 05

It had been exactly a week since I surrendered the right to orgasm to my little sister now that Sunday had come round again. I still hadn't been let out of the cage and I was dripping all the time and every time I looked at my underwear you could see just how much I was struggling.

Since I'd been turned into a footstool Wednesday afternoon, I hadn't had many chances to be used by Cynthia, but I'd still managed to massage her feet every night if only for a short time and whilst wearing clothes. Being caught massaging my sister's feet wearing nothing but a chastity cage could not be explained away, but if I had my clothes on, we could just say I'd lost a bet.

We'd also managed to have a more serious talk about how things were going and if I was actually enjoying how mean she was being or simply enduring it. I had to confess that I was enjoying it more than I expected and I assured her that I had no objections to anything she'd done to me so far.

When she'd asked if there was anything I wanted I asked for a kiss and she turned me down. There was more I'd wanted to ask for, but Cynthia was my mistress and I didn't want to impose on her. Especially when I was genuinely satisfied by being able to serve her. And today was going to be a good chance to serve her; we were going shopping together and Cynthia had already made it clear that I would be doing the driving and holding all the bags. She had alluded to something else, but she wouldn't tell me what else she had in store for me.

We left mid-morning after breakfast and headed for not the closest city so that we wouldn't spotted and as far as our parents were concerned we were only travelling together and would largely be doing our own shopping. We couldn't suddenly appear to be friends and they would definitely wonder I would go shopping with my generally disagreeable sister, so as far as they knew we wouldn't be spending that much time together.

And the drive out there was fairly mundane. I was aware that I was sitting next to my little sister who not only had the keys to my chastity cage but was wearing it on a necklace that was very visible and I was serving her by doing the driving for our - mostly her - shopping trip, but she didn't do anything to mess with me. I think that was for the best whilst I was driving. We mostly just talked about hiking and the old video game I was going to be looking for.

When I parked the car, it was like a switch had been flipped and she ordered me to get out and open the car door for her and I was more than happy to oblige. She stepped out of the car looking fantastic in knee high boots that must have been adding three inches to her height. Tucked into the boots were denim jeans and finished with a white shirt and denim jacket. I thought she was pretty fashionable but I didn't exactly follow trends.

The first store we went into what I think was a boutique clothing store and I wouldn't go into it or its male equivalent myself. I'd been into nice suit stores before but I grew up when we weren't so wealthy as a family, so I was satisfied shopping in higher end chain stores. Honestly though, a store like this suited my sister. It made her seem more like a princess and that she was better than me.

When I saw that the store had relatively large and rather private dressing rooms, I suspected that Cynthia had something more planned than me just holding her bags. After she picked a few items out, she was asked by a clerk if she would like her help and she responded, "I have all the help I need." The help being me who was holding all the clothes she'd picked out.

After grabbing some footwear we went to the changing rooms. I started to take a seat out of the waiting room, but she pulled me behind the curtain with her. The changing room was about six feet each way with one of those backless chairs things that look like their own cushion.

She pointed to the ground and I knelt down in front of her.

"Now, you're going to need to be quiet," she said quietly and started reaching into her bag, "but I'm not sure you're going to be able to do that, so I'm going to make it easy for you." She produced a pair of pants that I assumed were hers and she pulled my mouth open with her fingers and put them in. Then she leaned down and whispered, "Now all you need to do is do as your told and you can do that can't you bitch?" I nodded. I could definitely do that, but I wasn't sure I needed to be gagged to do as I was told quietly.

After that she started trying on clothes, first it was the outerwear she'd picked up and helping her in and out of that was easy enough, but I did see myself in the mirror with my mouth open and my sister's pink pants visible. I really did look pathetic even if I still had all my clothes on.

After that she told me to take off her boots, then her jeans and finally her shirt until she was only in a matching set of white lacy underwear and my cock that had been confined to a cage for the past week was pushing against the cage and the jeans I was wearing. And for the first time since I'd walked in on her watching porn, she was wearing less clothing than I was, but between the key that was dangling freely from her neck and resting just above her cleavage and the pants in my mouth I still knew who was in charge and it wasn't me.

"What do you want to take off next, my key or my bra?" I noticed how she called it her key. I tried to answer but couldn't with her pants in my mouth. She laughed. "It doesn't matter, you're not touching either of them."

After that I helped her into her first dress - a crisp white one - and then on my knees, I put a pair of heels on her. Once I finished putting the heels on, using her foot she pushed on my chest and kept pushing until I was almost on my back and I got the point and laid flat on my back.

She stood up and looked down at me, pushing some of her hair behind an ear.

"How's the view?" I nodded furiously and gave her a thumbs up. She was elegant and sexy at the same time.

Then she leaned over me and undid the buttons on my shirt. She had ordered me to wear a button up, but I'd thought it was just so I didn't look too unfashionable for her when we were going around shopping.

"If you're so loud that I have to stop, that cage won't come off anytime soon."

I was confused as she stood back up, but I quickly came to understand as she brought her foot down on my chest. It wasn't too bad as she rubbed hard with the front of the heel. But then she started pushing down with the heel. These heels weren't so high and they were a little squat but it still hurt. I choked down the scream but could feel myself gagging on Cynthia's underwear. She pressed down in a few more places and my head rolled over and I saw myself in the mirror. I was a pitiful wreck. I was in pain but doing nothing to stop my little sister from stepping on me and causing me more pain.

In the mirror I could see her about to step on my caged cock. I went to stop her but it was too late and my god did it hurt with the metal cage pushing into my semi-erect cock - this kind of pain was not turning me on - I did my best to be quiet and if it wasn't for the pants in my mouth the store staff would definitely be coming to investigate.

And there was a break. The first of many as I helped her change into a new outfit and with each change she would step on me again. She would move me into different positions and try stepping on my back and the back of my head. The worst one was the stiletto heel, she only pushed the heel down twice but my eyes were watering after that and she did stop after I tapped the floor like a wrestler.

After that I helped her change back into the clothes she'd came in and she pulled me close and pulled her pants out of my mouth.

"How was that?"

"Please, don't do that again." I pleaded.

"The stilettos? All of them?"

"Definitely not the stilettos."

"The others?"

"I'd prefer you didn't..." I didn't want to just say no to her if I could help it. I would at least be able to bear the other shoes she tried on me from time to time.

"I'll save it as a punishment then, so you best behave."

I nodded.

She unbuttoned her jeans and took one of my hands and guided it down her pants.

She was dripping wet. "That's what doing that to you did to me. So I am going to have try other ways of hurting you until we find something you're better able to... endure." Not enjoy, but endure.

I nodded meekly.

"But you were a good toy today and good toys get played with more." Being called a toy was a reminder she owned me even though she sounded so sweet saying it.

She leaned in to kiss me and I closed my eyes and leaned in. And then nothing happened. I opened my eyes and she was smiling.

"Not yet."

I was disappointed but at least she wasn't saying never.

We got ourselves sorted out and she paid for the first dress and shoes she wore along with a top that I thought was cute. Whilst she was paying I couldn't help but look at the clerks and see if there was anything on their faces to suggest they knew what had just happened. Under my shirt there was no shortage of red marks and we'd been gone a while, but if any of the clerks knew something, nothing on their faces gave them away.

We had lunch at a very upscale restaurant that had tablecloths. Whilst we were waiting for the food to come she explained how she was planning to play with me under the table. She was going to make me give her a foot massage whilst we waited and then she was going to tease my caged cock whilst I ate. But she thought I deserved a break and said she could do that to me another time.

So I had that to look forward to. I think.

And then we went to a lingerie store and being in a lingerie store with my little sister felt wrong in a wicked way, but that only served to turn me on more.

It got more wrong when she started asking for my opinion.

"What do you think of this one?" She asked holding up a cute pink negligee. I just stood there like an idiot. "You know this is for you right? Nobody else is going to see me in them."

We'd spoken about exclusivity recently. Obviously, I was in a cage and was unable to fuck other people even if I wanted to - which I didn't. But I was also unwilling to share Cynthia which she had been happy about. The explicit terms of our exclusivity was no other sexual contact with anyone else, no dating apps and no other active searching for a partner - romantic or sexual.

So the lingerie was for me. "Still, shouldn't you get what you like."

She pulled me down gently by the neck so she could whisper in my ear, "I can torment you with what you like."

I gulped. "Right."

"So, what colours would you like to see me in?" She said cheerfully and loud not at all quietly.

A smarter man might lie in my shoes after what was whispered in my ear, but I wasn't going to lie to her. "Definitely red and black."

"Duh, now try some less obvious answers."

"I think maybe dark pink and dark purple could be good."

"Good answer, now what about white?"

I screwed up my face a bit. White was a classic, but I don't think I'd ever fantasized about being dominated by somewhere wearing white lingerie or white leather.

"What is it?"

I wasn't going to say it out loud, so this time I grabbed her by the waist gently and whispered into her ear, "white is going to make me want to fuck you like you're my girlfriend."

She laughed.

Honestly, I deserved that. I don't know where that came from honestly. And I wasn't sure what she would do with that information, but for some reason, I was confident that she would do something with it.

And then she started taking lingerie off the shelves and going to try it on. This time I was not taken into the changing room with her and just saw her coming and going. After a while she messaged me to go and wait outside and that she'll be out after she pays. I obeyed.

When she came out she passed me a bag that had been clipped shut. "Don't look inside unless you want to be stepped on again."