Made to Order: Tickling Anne

She was staring nervously down at her own chest, as I toyed around with the last button of her blouse. A single motion, and each half of her shirt fell down to her sides. Goosebumps spread like wildfire across the newly-exposed skin. Her cheeks turned bright red as I admired her body. She was quite nervous, like a mouse caught in a trap.

"Maybe you should play up the defiance, Anne? If you want to win, that is..." I offered.

"Okay... I'll do that."

I laughed silently at the irony of that statement. "Anne, pretend you are a powerful business woman kidnapped by a disgruntled employee. You have been restrained and exposed. I am going to make you laugh and scream against your will. What do you say in that situation?"

"Oh," she giggled nervously. Her smile vanished as she tried to assume her role. She glowered at me defiantly, furrowing her eyebrows.

"Let me out," she ordered. The affectation was clumsy, silly-- but neither of us cared about that. Voices were hard, and it was the effort that counted.

"You're going to be my little bitch, Anne. These walls are soundproof, no one is going to hear you scream." I traced my finger up her stomach, causing her to flinch against her restraints. The conviction on her face evaporated, replaced once again by nervous apprehension.

I glanced at a clock behind the chair. It was analog, so I had to do a quick calculation for 'five minutes'. "Alright, Anne. Here we go. Five minutes, you got this!"

She gave me a quick smile, which turned into a shriek as I dug my fingers into her stomach.

"Shit!" she yelled, laughing loudly.

I ran my hand up and down her stomach, finding her weak points and digging in deep. I was intent on breaking her quickly-- I would look like a fool if I couldn't get her to say 'mercy' at least once.

She bucked against the restraints, but the chair was reinforced by a skeleton of metal. It didn't so much as bend a millimeter as she pulled and fought with her entire body. She switched to twisting, as I continued my onslaught. Her arms rotated inside their straps, but could not slip free.

"Ahahahahaha!"

She had a cute laugh; snorting and wheezing as she fought for breath. Her eyes were wide and her eyebrows bent in a delicious pouting expression. She started shaking her head back and forth, saying "no" repeatedly.

"That's not the right word, Anne," I teased.

"Screw you!" she shouted between laughs. Finally, that anger I was looking for. Maybe she did have a chance, after all.

I redoubled my efforts, dragging the tips of my fingers up and down her belly. That sent her into a new level of contortion, she jumped up and down against her restraints, trying to get her stomach away from my hands.

"Please! Ahahahahaha! I can't breathe!" she begged.

"Say it."

"M- mercy!" she managed.

I smiled wickedly. I was impressed that she lasted so long. "Not bad, Anne."

"Was I... was I close?" she said between gasps. She was still giggling even though I had withdrawn my hands.

"Close," I lied. She still had two full minutes left.

I wanted to make sure she was handling it okay. "How was that? Tolerable?" I asked.

She gave me a quick nod. Her breathing was starting to calm down. "That was very intense. I'm not sure if I love it or hate it."

"Here, I'll help you decide!"

I put my hands back by her stomach. She screeched and tried to get away as she saw them returning to their posts. I started sliding my hands up, tracing them up her sides until they reached her armpits. Her blouse still hung by its sleeves, but that was no protection. Her armpits were clean shaven and soft as I wiggled my fingers into her flesh.

"No! Not there, please!" she screamed. Now that was a delicious reaction. I stayed in that exact same spot, having no trouble following her body as she jerked back and forth in the chair. She was trying desperately to close her arms down, but they were held up and out. It was almost too easy.

After a few minutes, her face started to turn red. Beads of sweat rolled down the side of her head, and her hair was getting damp from exertion. Her face was twisted in agony and desperation.

"I can't take it! Please!"

"What's the magic word, Anne?"

"Mercy!"

I gave her one last stroke, eliciting a final laugh, before sliding my hands out from her blouse.

"One minute, Anne."

She relaxed in her restraints, trying to get some energy back in her tired limbs. Her breathing was deep and heavy, her chest heaving up and down in the chair.

"I don't think I'm going to make it..." she whined. "Five minutes is so long... I can't breathe or even think..."

I thought about encouraging her, or giving her some strategies, but this was a battle she had to win by herself now. I was her enemy, a tormentor to be overcome.

"I won't go easy on you, Anne. You'll be here all night as my little toy unless you toughen up!"

She whined loudly, hanging her head forward. Okay, maybe it was time for me to say something. I grabbed her chin, pulling her head back up to look at her. She kept her eyes to the side, avoiding eye contact.

"Anne. Remember: tough, powerful, confident. Those are all you." She matched my gaze, and gave me a slight nod.

"Powerful and sexy. Okay, bring it on," she said. "I'm ready. Wait! I changed my-- AHAHAHAHHA."

She started flailing once again as I dug my fingers into her stomach. Her limbs fought with renewed desperation.

"No, no no no no no. AHAHAHAH. Stoppp! EEEeee!"

Her screeches were desperate and unintelligible. Manic. After only a minute of torture, I could tell she was about to break. I refused to relent-- I didn't want her to feel I had let her win, but she was seriously ticklish. I think we both overestimated her ability to withstand this kind of torture.

"M- m- muh-" she sputtered.

Damn. I was right. She was already giving up. I continued tickling her, waiting for her to say 'mercy'.

"M- MOTHERFUCKER! AHAHAHAHAHAHA."

I smiled at her determination. I decided to give her a reprieve. I moved my hands down to her feet-- still strapped into her stilettos. It took me a few moments to unstrap the first shoe, letting it fall onto the ground.

"Sorry, Anne. Only powerful women get heels, and right now you're just a struggling little bitch."

She would think I had made a mistake by letting her recuperate as I let my hands leave her body. In reality, I was intentionally giving her a few seconds to catch her breath.

She gave me a desperate look, sucking down air during the momentary reprieve. The second heel fell to the ground, and her feet started flexing apprehensively. Her toes pointed straight up and her soles were completely exposed, now. I set to work quickly, not giving her too long of a break.

"Oh crap!" she screamed, as I dragged my nails across her feet. Her hips thrusted up against the straps in a spasm that I thought for sure was going to bend steel. Her feet flailed in circles, trying to get away, but I followed them with ease. Her toes curled.

I had made a slight miscalculation. I switched to her heeled feet to give her a chance to recuperate, completely unaware that her feet were a serious weak spot. I suppose that she also was unaware of that fact, based on the shocked terror plastered across her face. After only a few moments, her face was red and she looked about ready to cry.

She gasped for air between laughs, then shouted "MERCY!"

I relented immediately, disappointed. She only had a minute left, but I couldn't blame her. Anne's head hung down in exhaustion and shame, arms limp in her restraints. She was sniffling.

"I give up," she said quietly. "I can't take another round. I lose... again."

I agreed that she probably couldn't take anymore. Her arms had been up for too long, and she looked really tired. I started unstrapping her. I felt bad-- she was so close, and despite how ticklish she had turned out, she had fought really hard.

"I'm sorry, Anne. You did amazing, but I think you are too damn ticklish!"

She laughed weakly. "I think so, too."

She slid her arms and legs down as I released them one by one. She carefully stood up, and started sliding her skirt down her legs. I could tell by her expression that she felt humiliated-- and not in the good way.

"Next time we can try a different amount of time... or an easier position..." I offered weakly.

"It won't matter. The only way I'll win is if you go easy on me. It's fine... That's just how it is," she said in defeat. "I'm going to go use the bathroom, I'll be right back."

I sat on a nearby bench and started contemplating my options. She was probably too tired to take any more tickling, and I couldn't think of any other games she would feel good about winning...

I looked at the empty chair-rack, and had a bad idea. There was one surefire way to make someone feel more confident... to make them feel powerful.

When Anne returned from upstairs, her jaw nearly dropped to the floor. I had removed my clothes and strapped my legs into the chair.

"What are you doing?" she asked in shock.

"Anne. You are powerful, and sexy. Just like me. And being too ticklish, or losing at these games, doesn't change that! I am going to show you that first hand. Torture me. We'll both be sexy and confident, despite being humiliated! It's a paradox, but it's true!"

She laughed in pure disbelief, hesitantly walking over. "I'm not sure I can... I mean... you look hot, but I want to be your sub, not your dom..."

"Who said anything about changing roles? I order you to tickle me until you feel confident!"

She giggled, walking nervously between my legs. "If it's an order..." she said with a smile.

"Will you do the straps around my arms, Anne?" I asked.

As Anne awkwardly fussed with the straps, I contemplated my rash decision. I would normally never submit to a customer like this, but I had known Anne a long time and trusted her completely. I hoped this would be worth it.

"Five minutes, or until I say 'mercy'. Ready?"

She gingerly placed her fingertips on my stomach, like I had done to her. She had a sly smile, but her eyes betrayed her apprehension. She looked at me fearfully, like I might slip out of the straps at any moment and punish her.

I tried to stifle my laughter as she started running her fingers up and down my stomach. I kept my mouth closed-- holy shit, that tickled!

"FUCK!" I blurted, as she dug her fingers deep into my skin, wiggling them around. This was pure torture! I flailed desperately against the straps. When Anne realized I was truly stuck, she doubled down.

She laughed and smiled, starting to get into the groove of things. Meanwhile, I was gasping for breath and flailing against the tight restraints.

"Holy shit! How did you do this for so long?!" I screamed. I needed out, but the embarrassment of screaming 'mercy' so soon kept me in check. It also helped that Anne was really enjoying herself. That 'flicker' was back in her eyes-- the determination I had seen only briefly earlier, now burned like a bonfire.

I twisted against the straps. I wanted to endure, but I yelled, "Mercy! Mercy..."

She stopped immediately.

I struggled for breath, before weakly asking, "How did I do...?"

"Oh... I forgot to check the clock. Not very long, I think." She started unstrapping my arms, and I helped her free my legs from the rack.

"I have a newfound respect for you, Anne! I can't believe you can endure that for so long!"

She smiled shyly at me, blushing at my praise.

I stood up and stretched my arms carefully. It felt good to be free-- I wasn't planning on making that a habit, but the smile on Anne's face was worth it.

"Alright, are you feeling better, Anne?"

She nodded her head.

"So you won't feel bad if I strap you back down and make you scream as punishment for losing the game earlier?"

She nodded her head vigorously. "As long as it's not screaming in laughter! I've had enough of that for today."

We both laughed. I was glad she was feeling a bit more confident. It was immensely satisfying.

A few moments later, I had her screaming in ecstasy. She was back in the restraints, and I had the gag in. I was using the vibrating wand and a dildo. Her pussy was already a sopping mess from earlier. Her neck craned back, her limbs twisting reflexively as the first wave of pleasure hit her body.

While she climaxed, I reminded her that she was a helpless toy, but still powerful.

That she was a worthless slut, but still valuable.

That she can be confident and humiliated at the same time.

I wasn't sure if she heard me over her own moans, but based on her smile, she was having fun either way.