Several minutes later I was on the floor again, just barely able to catch my breath. Amber was still standing over me, watching me gasp and writhe on her bathroom floor. Seeing that I was able to communicate again, she pulled out her phone.
"I am withdrawing five hundred dollars from my little bank for the work that you did today. I think that's quite lenient actually."
"Yes Miss...thank you." I managed to choke out between gasps of air. I was lying on my back with my knees pulled up against my chest, my hands protectively over my crotch trying to assuage the pain coming from my crushed balls. Amber continued as if I hadn't spoken.
"Unfortunately, you made two mistakes in your cleaning, didn't you bank?"
I wasn't likely to forget that, I thought, after taking two knees straight to my balls to remind me.
"Yes, Miss." I said, able to speak a little clearer now that I felt like I was getting enough oxygen.
"I was planning on fining you one hundred dollars for each mistake. But you suggested I double that fee and I agree, so I'm adding four hundred total."
With that, she tapped her finger on the screen and almost instantly I heard a notification chime from my phone in my pocket.
Pulling it out awkwardly, still on my back on the floor at Amber's feet, I saw a Venmo pay request for nine hundred dollars. Shuddering slightly at the damage this is doing to my bank account balance, I hit send. Amber's phone dinged and she smiled.
"Very good, bank."
She crouched down next to me, keeping her knees pressed tightly together. She ran her fingers down the side of my face in a suddenly tender gesture. Despite my pain I shivered at the touch of her fingers.
"Remember this, bank. Remember what happens if you don't do your chores correctly. I'll take more from you each time you make a mistake like this - I expect my bank to learn from it's mistakes and strive to be better for me. Will you work hard to do better?"
Overcome with gratitude for her sweet caress, I could only nod.
She rose back to her feet.
"Ok bank, get yourself back together. You're going to take me to dinner and then shopping!"
Thirty minutes later we were at one of my favorite french bistros in town, sitting on a patio with a stunning view of the city. It was a really romantic spot, and it was easy to imagine I was here with Amber on a date. I could feel the eyes of every man and a lot of women on her. She looked incredible as always and was obviously in a great mood - she talked animatedly about her move, her friends, and her job. It was hard to believe that just a few minutes ago she was kneeing me in the balls and berating me, but I was ecstatic to be with her like this.
We ordered food and wine and enjoyed the view as she told me about her friends Sarah and Christy. Sarah was the tall red-head and Christy was shorter and more curvy and had black hair in a chic short cut. Sarah was a trainer at the gym where Amber went apparently, and they had met there a couple of years ago. Christy was between jobs at the moment but usually worked as an executive assistant. Apparently Amber was a little concerned for both of them - the recent pandemic had hit the gym industry hard, and Sarah was down to just a few clients a week - hardly enough to sustain her. I spoke about my company, and Amber had a lot of questions regarding how it ran, my employees, and how I was able to be fairly successful at a relatively young age. I was enjoying myself so much that I didn't want the meal to end, but eventually the waitress brought me the bill which I happily paid. I noticed Amber didn't reach for it, of course, and that gave me another slight shiver as I remembered the reality of what I was to her. I was happy that serving as her bank didn't exclude me from relatively normal social interactions like this, and I was already planning on asking her to dinner tomorrow night after my work for her was done.
After the meal I drove her to Southpoint - a collection of upscale clothing and jewelry stores on the far side of time. She led me directly to a high end lingerie store. The interior was dimly lit and very tasteful - not like the Victoria's Secret stores I had mostly been to with previous girlfriends. As she moved around the store looking at various lingerie sets, I did my best to follow along behind her. I reflected how it always feels uncomfortable somehow for guys to be in lingerie stores, and I felt the eyes of all of the employees and some of the other patrons on me whenever I got too far from Miss Amber, probably thinking I was some sort of pervert.
Amber picked up a particularly sexy pair of black panties - they had double sets of straps that would go around her hips, and the front was intricate lace. It wasn't a thong, but the rear was a very small bikini cut that would hardly cover any of her voluptuous ass. Turning, she held it up against her.
"What do you think, bank? Would these look good on me?"
I could only nod, overcome with desire to see her wearing these. I was acutely aware of the tight cage on my penis, momentarily forgotten over our normal dinner.
Amber laughed and handed them to me. I stood there holding them awkwardly.
"I think these are keepers. The girls and I are going out later tonight - I'd like to wear these in case I get lucky." She winked at me and continued browsing the display of outrageously sexy panties. Every so often she'd hold up a pair to ask my opinion, and she selected four or five to hand to me. I felt incredibly awkward walking around the store with my hands full of panties, and simultaneously I was in a state of intense arousal from Amber's gentle teasing. She had moved on to selecting some bras and I was already holding a couple when a sales associate came over to us. She was young - probably in her early 20s, and pretty, with straight black hair almost to her waist. She was impeccably dressed in a white blouse, black pencil skirt, and black heels. I noticed that her top was unbuttoned much lower than would be considered appropriate in normal circumstances, and I could see a bit of black lace from her bra peeking above the fabric of her shirt.
"Can I help you with anything?" She asked, with a professional smile on her face. "I see you already picked some things out - would you like a bag to hold those in while you shop?"
Amber turned from where she was examining a bustier.
"No thank you - he's perfectly fine as he is."
The associate - Claire, I could see, from her name tag - nodded with a slight frown. "Ok, sure. Are you and your boyfriend looking for anything in particular?"
Amber laughed and looked at me.
"Oh, he's not my boyfriend - just a friend."
I looked down at the floor, blushing.
Claire seemed to take this in stride.
"Ok - is there anything in particular you're looking for?"
Amber thought a minute.
"Well, i'm going out with the girls tonight, and I have some nice things here already, but...I was hoping I could find something really sexy in case things go well for me." She said with a big smile, which Claire returned.
"Certainly - I think we have something you might like over here."
With another small frown in my direction, Claire led her over to a different part of the store with me trailing behind. She pulled a beautiful, sexy teddy off of a display table and held it out. Amber whistled as she looked at it, and I felt more bite from the chastity tube. It was incredibly sexy with several sets of straps that would go around her torso, and had sheer fabric for the bust and a narrow thong panty. I almost moaned thinking of Amber's voluptuous figure with her hourglass waist contained by this lingerie.
Amber held it up against her body.
"What do you think? If you pulled a girl and she was wearing this, would you be a happy camper?" She laughed as she gave a bit of a twirl.
"Yes..." I breathed, not trusting myself to say anything more.
Claire nodded, and asked if there was anything else we were looking for.
"No - I think this is pretty good for one trip." Amber laughed, looking at the double handful of lingerie I was holding. We walked up to the counter and Claire rang everything up. I blanched at the total - nearly five hundred dollars! Shivering slightly, I presented my credit card as Claire looked at me questioningly.
"Not a boyfriend, but you're buying all this?" She looked at Amber with an amused look on her face. "Where do I get myself a friend like that?"
Amber smirked at me as Claire ran my card.
Claire winked at me conspiratorially and said in a slightly softer voice "I hope you are at least going to model some of this for him. Your body is fantastic - I'm straight and I'd like to see you wearing this bustier." She giggled a bit, and blushed slightly.
Amber's smirk deepened.
"You'd like that wouldn't you?" She said, directing the question at me.
"Yes miss...I mean, Yes." I stammered - horrified at my slip. I glanced up at Claire who was clearly trying to contain a laugh.
"Oh it's like that, is it?" She grinned at me. I felt myself blush two shades darker as I looked at my feet. Claire looked at Amber and I appraisingly, unconsciously chewing on her lower lip. Looking around and seeing no other employees nearby, she leaned forward conspiratorially. I could see even more of her cleavage and the beautiful black lace of her bra. Yet again I became acutely aware of the tight steel tube gripping my cock. She held a business card out in her delicate hand.
"Well you two are certainly the most interesting customers I've had all week" she chuckled softly. "Listen...next time you want to go shopping, you could leave your...boy? at home. I'd be more than happy to help you pick out some sexy things." Claire blushed a little and looked down at her hands for a second.
"I mean, I do work on commission" she laughed again, a little self-consciously. "I'm quite absent-minded and sometimes I completely forget to check ID when I'm running credit cards" she winked at Amber as she said this, and they both laughed.
"Deal." Amber took the card from her hand and gave her a quick hug over the counter, and then crooked her finger at me to follow as she walked out of the store. Grabbing the bags, I hurried to keep up. I could feel Claire's eyes on us as we left the store.