Diane's Next Damp Adventure Ch. 01

In the four months since I last used Diane, I'd been buried with work and had thought about her only once or twice. With the constant pressure at work, I had little free time to think about sex. When I did, it was a quick phone call to the escort service, a couple of hundred dollars from the box in the bottom drawer, and a quick encounter with the flavor of the week.

Her connection in Madison emailed me once, about two weeks after we'd had our first session, but once I reassured him that she'd lived up to his expectations, he hadn't bothered to contact me again. That was fine with me. The last thing I needed was a distraction. Until now.

Once I delivered my final version of the project I was working on to our customer, I would have at least two weeks free while they decided whether or not to go on with the next phase of the project.

I celebrated that first night with a pretty, early-30's brunette. We went out for dinner, listened to some jazz, then back to my place for an overnight. Just under $3000, but worth every penny. She was intelligent, curious, and sexy. She made omelets for us in the morning, brought them to bed, and we enjoyed them with coffee before one last roll. After she left, I went back to sleep, waking just before noon.

By mid-afternoon, though, I was pinging Madison to arrange another visit with our mutual friend. As much fun as last night had been, I couldn't resist the thought of another "indulge your whims" session. In less than an hour, he'd responded to my email with a zip file of photos, two short video clips, and an update on the last few months.

The photos were surprising, the videos even more-so. Diane was going deeper and deeper down the rabbit hole, it seemed. The photos showed her in a variety of classic bondage poses, blindfolded in some, hooded in most and wearing nothing else but high heels in most of the shots. There were a series showing her bound from the rafters in a basement or garage, red stripes appearing in more and more spots as I clicked through the photos. Another series showed her bound face down on a St. Andrew's cross, leather straps securing her at several points up and down her arms and legs, leaving her back exposed. Again, more red stripes appearing up and down her back and legs as the photos advanced.

The videos went in a slightly different direction. Both of them showed her masturbating herself to orgasm with her fingers. I recalled that this was one of the few things she had really refused to do in our early encounters, but obviously someone had broken through that barrier. In both of the movies, she was holding herself wide open with one hand while she masturbated with the other. In both movies, she obviously got off before the camera stopped.

Madison's emails were even more explicit. She was letting herself go further and further with her fantasies, allowing him to send men her way who were more and more demanding each time. She was often not able to pull herself together to go home and had taken to planning overnight sessions rather than hours-long evening encounters.

Madison also forwarded me a series of emails in which even her language shifted. In the early emails - and the ones I'd swapped with her before - there was always a sense that she was an equal partner in the play. Boundaries and safe words were established, limits were honored. In the latest emails, she almost always talked about herself in the third person, as if her body was an object completely at his disposal. "It will perform to your expectations and if it does not, you will please discipline it however you see fit." Or "please let her prove to you that she is nothing more than a repository for anyone you wish to have her service."

I told him to continue with whatever plans he had for her, but that I would be flying out tonight. I would send him my hotel information and expected her to be in the hotel lobby when I checked in.

The desk clerk handed me my card key and I slid him a $20, told him to leave my bags in the room and to provide me with an extra set of towels and two long-neck bottles of Corona. He smiled and nodded.

I walked back toward the entrance. I'd seen Diane sitting alone in the bar when I came in but ignored her. I was certain she saw me, she kept her head still but I saw her eyes following me as I walked from the taxi to the door. I made small-talk with the doorman, looking toward her once or twice.

"That woman in the bar. A guest?" I asked him.

"I don't know, sir. She arrived about fifteen minutes ago and has been sitting there alone." He brushed a spot off of the sleeve of his jacket.

"Pro?" I asked.

He smiled and looked at her. "I don't know. A bit on the short side, but nice enough looking." I saw Diane's eyes, she was watching us as surreptitiously as she could. Good. That was the effect I wanted. She had no idea what I was saying but I'd bet she was expecting us to walk over together.

I shook his hand and laughed. He was a bit puzzled, but laughed as well. I watched Diane from the corner of my eye. She fidgeted. Better. My game was having the right effect. Keep her guessing.

I walked into the bar, sat across the table from her. She didn't move, sat with her hands in her lap, looked at me, her eyes lowered, gaze fixed somewhere between my chin and chest. "You've come a long way," I said, reaching for the glass of white wine in front of her. I raised it, took a sip, sat it back down. She hadn't drank anything, there was no lipstick on the rim.

The waitress came to the table. An attractive, brown-haired woman in her late 20's. Her uniform was tasteful but sexy - short, tight, dark brown skirt and a white men's shirt with a bright red, satin tie. Her legs showed off fishnet stockings, but her shoes were flats. A lot of gold jewelry, bracelets, necklaces, earrings.

"What will you have, sir?" she asked in a flirty voice.

"Well, I would like a glass of red wine. And for the lady, please bring her two large glasses of water, no ice." The woman looked at me with a puzzled expression, then looked at Diane. Diane remained motionless, eyes fixed at the same spot on my shirt.

"I would also like a plate of your mushroom appetizers, please," I said, eyes locked on Diane's face. "And please remove the lady's wine glass."

The waitress squinted her eyes slightly, but picked up the glass and put it on her tray. "Yes, sir, certainly."

"How nice," I said. "Diane, repeat that, would you?"

She took a short breath, then repeated "yes, sir, certainly."

I laid my hand on the table, palm up, then slid it toward Diane. She leaned sideways and picked up her purse, placed it in my open hand. It was a small, black purse, just large enough for a few things. I opened it and removed the contents one by one.

"Driver's license," I said, and laid it on the table. "Lipstick. Glide," I sat the bottle on the table and looked up at her, "anal lubricant, yes?" She nodded just barely. I reached into the purse again. "Ten...twenty...forty...sixty dollars cash. Ah..." I lifted the RC unit up, rested my elbow on the table, raised it in front of her face. "Ah, yes. Very good." Her eyes refocused, she looked at the small plastic unit, then I saw her eyes shift as she looked around to room. "Wondering if anyone's watching?" She lowered her eyes again. "Yes, there is someone watching. A man sitting at the bar has been looking at you since I got here. I wonder what he's thinking. I wonder what he'll think when he sees this," I continued, flicking on the RC device. Diane twitched slightly as the device between her legs began buzzing. "I wonder if he noticed."

The waitress came back to our table, sat the bottle of beer in front of me and slowly set the two tumblers of water in front of Diane. She tried not to stare at the bottle of lubricant on the table but failed. She opened her mouth to say something but I put a finger to my lips. "Shh..." To my surprise, Diane's face reddened visibly. I couldn't tell if the waitress heard the vibrator or not, but my "shh.." had the right effect on Diane. More humiliation.

The waitress gave me a disgusted look and stormed away. I pushed up the speed on Diane's RC and watched the thin film of sweat start to spread across her forehead.

"You look a bit distressed." I slid one of the glasses toward her. "You should have a drink of water." She raised her hand, reached for the glass. Lifting it slowly, she took a sip. "All of it," I said. "Now."

She raised the glass again, gulped and kept drinking until the glass was drained. She sat it down on the table and put her hands in her lap.

"The other one."

Diane closed her eyes for a brief moment, then opened them, picked up the glass, and guzzled the entire contents in one long drink. When she put the glass down, I noticed her hand tremble. Her shoulders were quivering slightly as well. I smiled and turned the RC off. She raised her eyes and looked at me, a combination of anger, shock, and confusion.

"Ah, you remember. How much I wanted you to cum for me?"

She didn't respond.

"The game's different now." I turned the RC on again, rotated the knob until it was on high. She slid down slightly in her seat. I pushed my chair back a few inches and looked at her. Her knees were opening, ankles crossed now to keep from shaking. I fluctuated the dial from high to medium to low, back and forth, watching her body move with the changes. Her lips were trembling now, she was getting close. I flipped the switch off.

"I want you to go to the bar. I want you to stand next to the man who has been watching us. I want him to smell you. If he talks to you, be polite."

She looked at me again, waiting for more instructions but I stopped there. I wanted to leave the ending ambiguous, leave the possibilities open. That way, whatever decision she made would be wrong. And she knew it. She was trapped. If he came on to her, should she say "yes" or "no"? Whatever decision she made would be wrong. And she would be punished for it.

Diane got up from the table, made her way across the room and stood about two feet from the man. He was sitting on a stool, sipping a double whisky. She stood against the bar, facing the large mirror behind it. The bartender came and asked her what she was having. She ordered another glass of white wine.

The man began chatting, Diane turned her head and answered him. After a few minutes, the bartender brought the wine. She took a sip. He raised his glass for a toast, she responded. They talked for a few more minutes.

Then, I turned on the vibrator. I saw Diane shift her feet one or twice in the first minute, then she pressed them together hard. He was still talking but her face showed she was distracted, not paying attention. I turned the speed up to about 5. She opened her legs a few inches apart. I saw her move her hips slightly forward and back. The man must have seen it too because he reached out a hand and toucher her forearm. She shook, nearly came. I turned off the RC and let her regain her composure. She put her hand on top of his, then reached for her wine and took another drink.

I flicked on the unit again, this time, rotated the knob to 8. I saw a puzzled look come over the man's face. He cocked his head slightly. Diane's face went red again, her mouth opened just a bit and the sweat along the side of her neck glistened. He hear something but didn't know what. I pushed the unit to 10 and watched her legs tremble with the effort to stay still. The man looked down the front of her dress. She was breathing faster now, he watched her belly rise and fall. I heard him swear, then he got up and walked out of the bar, shaking his head.

Diane leaned forward against the bar and steadied herself. After a few seconds, she made her way quickly back to my table and sat down.

"Nicely done," I complimented her. "Nicely done."

I motioned to the waitress. "Now, two more glasses of water and we will head up to the room."