πŸ“š a demanding woman Part 4 of 8
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EXHIBITIONIST VOYEUR

A Demanding Woman Ch 04

A Demanding Woman Ch 04

by privatefirstclass
20 min read
4.72 (5600 views)
adultfiction

Neither Skye nor I (nor even Blake) wanted to have lunch and go swimsuit shopping with Tala that weekend, so I called her and put it off until the following Saturday.

"Of course, Madeline. If you two can't come this weekend, we'll just do it next weekend. But I don't want to delay too long. We have a vacation coming up."

Could there be anything remotely more like Tala than to assume that Skye and I wanted to go on vacation with her, that we could just get work off whenever she needed us to, and that Blake wouldn't mind the least me traveling with her for whatever she planned. Of course, instead of being infuriated, I just grinned. I'd get the details from her on Saturday over lunch. And I would figure out how to get out of work for it. And if she wanted to, I'd let her fuck me silly every day. Which is what Blake did when I told him about it.

The next Saturday, we went to a tiny Italian wine bar I'd never heard of. Over wild boar and a wine that was so good I plotted to steal a case if I couldn't buy it, she outlined our vacation. It was, naturally, at a resort on a Caribbean island I hadn't heard of, so exclusive it had only twenty huts. That's what the brochure called them. The word implies a rustic modesty. These, however, were large and luxurious in a way I hadn't imagined such things could be. Both Skye and I were giddy about it. If I was going to take a vacation without Blake, this would be the one I would want. If Tala happened to order me to eat her for breakfast every day, that would just be a bonus.

After she finished showing us the brochures and telling us when we would be traveling and all the other details she insisted on, she said, "I will book this tonight. Now, there can't be any of your disobedience again. We had plans for last weekend and you both chose to prioritize other things. This vacation cannot be jeopardized by such unthoughtful behavior. Am I understood?"

We both nodded and apologized. I slightly dreaded whatever punishment was clearly coming. At home with Blake or sitting and talking about the vacation, it all seemed like good sexy times. But with some unknown but certainly humiliating punishment looming, I felt the urge to abandon ship. What was I thinking? A vacation with Tala and Skye? I'd let this whole thing go too far.

On the cab ride whatever store she was taking us to, I fretted over everything. Nothing but luck prevented a stranger from witnessing my spanking at the lingerie boutique. Anybody could have walked it to see my red ass straddling Tala's lap. Even modeling the lingerie in front of Tala and the clerk was humiliating. And everything about what happened in her apartment wasn't just embarrassing, but a threat to my marriage. I thought about how close I came to really cheating.

This was all wrong, but when we pulled up to the Anthropologie store on Southport, I was sad as much as I was relieved. There would be no games here--it's a big, open store on a busy street. Putting me over her knee would get all of us thrown out. Nor would I have to put on anything especially skimpy. This was all family-beach approved, even if the target market were millennials like myself.

In the store, Tala's punishment became more clear.

"Come, girls. Let me get you something appropriate to wear," she said, leading us to the summer collection. She went through and picked things out for us. "Skye, this will be nice on you." "Madeline, this will be such an improvement in your casual wear." "No, Skye, put that down, that's not right for you."

The clerks were aghast as we obediently followed her about, holding on to the clothes she collected for us without speaking a word. When we both had too many clothes to carry, she had us bring them to the counter. The counter clerk was a college age woman with a dusting of acne under her make-up and those "invisible" plastic braces. God, maybe she was in high school.

"Madeline and Skye, I want to see each of these outfits before I pay for them. I'll sit out here."

She then addressed the girl. "They really have no sense with clothes. You might need to help them."

The girl looked at us and giggled.

Skye was smart--the first thing she put on was the skimpiest suit Tala had chosen, a little string bikini. It's design perfectly showcased her cleavage. However despite how embarrassing it would be to wear it in the middle of the store, everything would get better after it. As I peaked through the dressing room curtains, I noticed a college age guy staring at her as his girlfriend looked at Skye with contempt. Fuck.

She came back blushing, but she'd pulled the band aid off. I couldn't get myself to do it. I tried on the cabana trousers and beach caftan.

"Madeline, hurry up now."

I walked out, avoiding the counter girl's gaze--and the couple's.

"Oh, Madeline, dear, you can do better than that."

I sighed and tried to walk like a model. The boyfriend didn't bother to sneak a peak, which kind of hurt.

Skye modeled some cabana wear--an open knit top over a metallic maillot--to the chagrin of the boyfriend. Then I went out in loungers and a hippie blouse.

Skye alternated between the bikinis and other outfits, slowly gaining confidence. Of course, she had a lot to be confident about--she had a bikini-model's body and Tala was an expert at picking the right pieces to show her body off.

My confidence barely nudged. No, it flagged. Playing model at Tala's command was embarrassing and having the boyfriend all but drool at Skye but ignore me was another form of humiliation.

Five outfits in, I was out of anything that wasn't a swimsuit and had to just go for it. I picked the most conservative of the lot, something that would actually be good for swimming. It was also the cutest of the bunch, too: boy legs and broad shoulder straps. Its the kind of suit I would have spent a week looking for, something that flattered my usual figure and wasn't uncomfortably revealing. I took a deep breath and went out, trying my best to look confident.

Tala stood and walked around me, shooting her inspection gaze right into my nerves. "I suppose that will do. Let's hope the others are can do something to help your deficiencies."

The girlfriend gasped at Tala's rudeness. I blushed so much I probably looked like I'd spent the day on the beach without sunscreen.

I tried on three more suits, each more revealing than the last. Of course, this was Anthropologie, so none of it was even as indecent as Tala's critical comments. I sighed with relief when Skye went out for her turn and I realized I didn't have anything left. It was silly to be so embarrassed over a bikini in a store. On the beach, nothing I wore would have been uncomfortable. I laughed at myself and watched Skye take one last glory trip. And it was a glory trip. She'd gotten into it. The boyfriend and girlfriend were gone--I think she'd dragged him out in a huff--but even the staff seemed to be enjoying this odd impromptu show.

Skye came back and hugged me. "God, that was kind of exhilarating."

"Madeline, come on, I know there's one more outfit for you," Tala said in her calm but unforgiving voice.

I looked into the pile of outfits I'd worn, which I'd neatly folded and stacked into the "buy" and "leave" piles based on Tala's judgements. There was nothing I hadn't tried. The only thing left was a bikini bottom she'd forgotten to get a top for.

"There isn't anything left."

She sighed loudly enough for me to hear across the room. "Madeline, don't be obtuse. You're a smart woman and I know there's another outfit. It's the only one that has a chance of flattering you."

"You forgot the top." God, it was embarrassing to have this conversation across the room. I felt like a little girl talking about her first bra with her mom in the middle of Target. Okay, that was me, and it took me a long time to forgive my mom for that. I blushed remembering.

She sighed again. I don't know how anybody could sign so loudly. "You're hopeless. A top is wasted on you. Come on now. I don't want to come in there."

Skye covered her mouth and her eyes popped wide. "Oh my God."

"I can't..." I whined.

"Madeline. Really, dear, this is unacceptable." The entire store had gone quiet. I swear one of the clerks even killed the sound system.

"I can't," I said, loud enough for her to hear.

"You can and you will this instant. I cannot accept this insolence from you. It's very upsetting."

"Just, just do it." Skye bit her lip and looked afraid.

"Alright. One second." I took off my clothes and put on the bikini bottom. It offered fairly standard coverage--except that I had nothing above it.

I stood at the curtain.

"Madeline," Tala scolded.

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"I can't..." I whispered to Skye. And, just like the last time I couldn't, she pushed me. I stumbled out into the middle of the store. As soon as I had my balance, I covered my chest with my hands.

"That's no way to model. You wouldn't walk like that on a beach, would you? Do it right, Madeline."

I looked at the floor and put my arms down and walk towards her.

"Eyes up."

Everybody stared at me. The counter girl, the too-hip-for-you sales woman, six other customers, a stock boy. When I got to Tala, she put a finger in the waist band, pulling on it as if to adjust the fit, but really just pulling it into my ass crack.

"The fit is nice. This really makes something of your assets, dear."

"Yes, ma'am," I said through my tears.

"Ma'am," the counter girl said, "You can't do this in here. Go cover up. Please."

I covered my tits, and ran back to the dressing room, crying. The whole store started to laugh.

As Tala paid, the counter girl looked me in the eyes. "Ma'am, we appreciate your business, but please do your shopping online in the future." She was obviously addressing Tala.

Instead of leaving Skye and I to get an uber home, Tala hailed a cab. Once we were in, she gave the driver directions to her apartment.

"I can't believe you'd humiliate me like that, Madeline," she said with obvious sincerity and anger. "I should not have to ask you more than once for something so simple and straight forward. I can't believe I'm going to take you on this vacation."

She turned away from me and stared out the window, fortunately avoiding my WTF expression. Skye and I turned to each other and mouthed, "Oh my God!" And then held hands, using one of the Anthropologie bags to hide it from Tala. None of us spoke, even as we went up the elevator to her condo.

As soon as the door closed behind her, she said, "Miss Martin, strip to your bra and panties."

Before Skye had a chance to put down her bags and start, Tala snapped, "Now! I am so humiliated and angry right now. Don't test me."

Skye carefully but immediately put her bags down and began undressing. I put my bags down and started to undress as well.

"Mrs. St. James, what are you doing?"

"Don't you want--"

"My God you are willful and stupid today. Did I say undress? Stand there until I tell you what do do."

"Yes, ma'am."

"Both of you conspired against me last weekend, plotting together to cancel our plans at the last minute. For that, you needed to be punished. But your behavior in the store, Mrs. St. James, was beyond appalling. I've literally never been so humiliated. I am reconsidering everything."

"I'm sorry," I said, although from shock as much as actual regret. She'd always been strange and controlling, but this was plain crazy.

"That won't be sufficient."

She turned to Skye. "You, at least, were a model for proper behavior today. But after such an outrage, I cannot easily forgive your prior indiscretion. Get the chair"--apparently there was a The Chair--"and put it the middle of the room."

Skye didn't meet her gaze when she responded, "Yes, ma'am."

Chair in place, Tala sat and ordered Skye to undress me. This wasn't a sexy strip show. Skye was too anxious about disobeying to have fun with me. She did pull my panties off with her teeth. And I was, humiliatingly, very wet. Unfortunately, she didn't linger.

"My God, Mrs. St. James, I can smell you from here. You aren't only incapable of behaving, but are completely debased. Skye, get a ziplock bag from the kitchen and seal those up. I don't want them polluting my house."

Tala had me kneel in front of the chair, eyes level with Skye's luscious ass, as she delivered the requisite blows. She did not hold back. The first smack made me jump. By the third, Skye was sobbing.

"Quiet, Miss Martin, or I'll get a gag."

Skye stopped crying, although each blog caused her to grunt. I wanted to go to her and hold her hand or stroke her hair or something during her ordeal, but I didn't disobey.

After ten slaps, Tala stopped. "Mrs. St. James, there is lotion in the desk"--she pointed--"get it and help your co-conspirator recover."

She pushed Skye off her lap--sending the stunned Skye tumbling--and left the room.

Before I got the lotion, I crawled over and kissed Skye's panty-clad ass. I didn't do it to soothe her. My motivation was entirely lust. Her ass had never looked better. God, what a horrible person I am. But I kissed it and caresses her back as she cried quietly.

"Mrs. St. James. The lotion. Now."

I got it and pulled Skye into my lap. I slid her panties down and rubbed gently, letting my hands slip down her sides and between her tights until she was panting and wet. She slid off my lap and took my face into her hands and kissed me.

"Enough of that," she said, coming back with a laptop. "You are not here for rewards. Skye, help Mrs. St. James bring the ottoman over here."

Skye and I hugged, then got the ottoman set up.

"Good," Tala said. She pointed the the desk. "In the second drawer, there's a leather bit. Skye, get it and put it on your friend."

"I'm not--"

"I don't want to hear your thoughts, Mrs. St. James. All the more reason for the bit."

Once again I was in her condo and complied when the only reasonable thing to do was run.

Skye mouthed, "I'm sorry," as she gagged me.

"Bend her over your knees, Skye and do not be gentle. Twenty will be sufficient unless you lack the courage to use sufficient strength."

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I let Skye position me. As she started to hit me, Tala opened up the laptop and started doing something with it, not looking at us. Skye took advantage of her distraction to give my ass a soothing rub between spanks.

"Harder and faster, Miss Martin, or we'll need to start the count again."

Skye continued to pummel me, counting out loud. I jumped after every strike. She was far too strong for this and I had a hard time imaging this ever turning sexy. Plus, I was drooling around the bit and worried about choking.

Eighteen was unbearable. Nineteen was insufferable. And twenty. I wanted to die.

Tala didn't look up from her computer. "That will be enough. Get the lotion and apply it, Skye. But do not give her any sexual release. She's even more wanton than you, and I know she'll be begging you, but be strong."

Skye looked at me and giggled. "You are a very naughty girl."

She poured the lotion in spirals on each of my burning ass cheeks, letting the cool liquid help relieve some of the pain. Then she started gently rubbing it in circles. I was still in too much pain for this to be erotic, but the relief was immense.

Skye leaned over me and kissed my neck behind my ear. "I love you."

With the bit in, I couldn't speak, so I nodded. She laughed when she realized why I hadn't spoken.

"Ma'am, may I remove the bit?"

"Yes," Tala replied distractedly.

I was too tall for Skye to kiss on the mouth while I straddled her lap, but she kissed my shoulders and neck once she removed the bit.

She poured more lotion on my ass and caressed it, letting her hands venture between my thighs. I hurt too much to hump against her fingers but I mewed and reached up to play with my nipple.

I glanced over at Tala. She'd spread her legs wider than made sense to hold the laptop and her skirt had ridden up her thighs enough that I could see her panties. Except she wasn't wearing any. My breath caught. Would tonight finally be the night where she took us to bed? I looked up to Skye and nodded towards Tala. Skye's eyes went wide and she grinned at me, then pushed a finger into me. I tried not to moan, but couldn't stop myself.

Tala put the computer down, but didn't close her legs. I knew she could see what I was looking at. I licked my lips suggestively.

"Madeline, here's my predicament. I've planned this trip for weeks, working out every detail. I'm prepared to pay for it and let us enjoy an island retreat. But now I discover that you are unreliable and undisciplined. So either I abandon my hard work, or I put my faith in you, who are far from worthy. What should I do?"

"I could show you how worthy I am. I could show you very, very much."

She moved shifted, bringing her skirt further up her legs. It looked unintentional, but couldn't have been.

"Yes, that's what we must do. You must prove you can exert some discipline. Skye, pulls your fingers out of Madeline, for God's sake. I just sent something to the printer. Fetch it. And Madeline, kneel in front of me."

I did, holding my arms behind my back.

"No closer. Closer. Even closer. Okay, stop."

I was between her knees. I could smell her, although my height meant I was looking down on her skirt and couldn't see her cunt like I wanted.

She reached out and caressed my cheek. "My dear, did you learn your lesson today?"

I nodded, almost dizzy with desire.

"Good. You are enslaved by your sexual passions, like an animal in heat, aren't you?"

"Yes," I said breathlessly.

"Does your bottom hurt a great deal?"

"Yes."

"But despite that pain, you would like me to get on top of you and use you for my own gratification, wouldn't you?"

"Yes. Please."

She smiled and ran her thumb over my lips. I sucked it in greedily, but she pulled it out. She put her hand on the top of my head and pushed me lower, so I could see her cunt. I leaned forward, but she pushed me back.

"You must prove your discipline before our trip."

"Yes."

"For the next two weeks, you are not to have any sexual gratification. Not one release."

"But my husband--"

"I am indifferent to your husband, but you can provide him with all the release he needs. Or have Miss Martin provide it. She's almost as much a slave to her desires as you. He'll probably appreciate access to her body. Your virtues are elsewhere, what little remains of them."

My lip trembled as I digested this.

"Skye?"

"Here, ma'am."

"Fetch a pen from the desk," she said to her. "Madeline, this is a contract. It obligates you to pay for half of the trip--air, hotel, and all other pre-booked services. I expect you to sign it today. If two weeks hence, I am convinced you have not given in to your lustful nature, I will shred it and the entire vacation will be on me. If I don't believe you've been sufficiently disciplined, I will hold you to the contract, but deny you the trip. You'll pay, but not play. Decide immediately if you accept."

Of course I said no, it was an insane offer and I knew half the trip would cost much more than I could afford. So there was no way I was going to say yes. Except, I nodded. I didn't mean to, I just did.

"Give her the pen," she told Skye.

Skye held it out to me, but shook her head. The irresponsible one was saying no. God, this was so stupid. I skimmed the contract under the pretense of not being crazy stupid. Then I signed it.

"Very good. Go get dressed. Remember, you may not take any sexual release at all for the next two weeks. Not with another, not by yourself. You have only yourself to blame for this. Had you been more reasonable this afternoon, I wouldn't have needed to do this. But now, I need to know you can be trust."

She looked at Skye. "You've been unfair to your friend as well. Look at the state she's in. All worked up with her lascivious desires, and not husband or lover to take care of her. I think its only fair, since all of this is your fault, that you take care of her needs tonight. You definitely must do that. Just don't accidentally get relief yourself."

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