Side Bet Bluff Ch. 08

"Jaycee," I warned, "we actually talked about this problem that very first night. I told you I was going to keep going when you said 'no.' This is a way around that."

"Will, why didn't you buy a whip?"

My head turned sharply towards her. Jaycee had pulled one of the books out of the bag at her feet and was flipping through it. "What?"

"Or a strap, or a flogger, or a crop, or"

"What? No," I answered.

"No? You bought the paddle," she countered.

"At Marie's suggestion as the best replacement for striking you with my hand," I explained. "I'm glad we didn't do that extra eight spanks earlier today, or I may have put my hand in a brace afterwards."

"Ok, what about nipple clamps? Or do you have clothespins you can use? Or needles?"

"Jaycee, what are you talking about?" I was completely bewildered. Jaycee continued to flip through the book.

"How about piercings? Or a tattoo? Would you like to brand me?"

"Jaycee, stop. No, I'm not going to do any of those things to you," I tried to assure her.

"Right," Jaycee said. "While you're getting off on the dominance and submissive part of our play, you're not into the sadomasochism part - only slightly with the spanking, but at least right now that's as far as you want to go. So there's really no need for a safe word, because even with the anal, what you want to do is never going to push me beyond what Marie called... wait, what did she call it? Oh yeah, a hard limit. Or even a soft limit."

"So you're basically saying you can handle whatever I'm comfortable in dishing out," I rephrased her answer.

"Yep," Jaycee agreed. Damn. I almost felt like a wimp for not pushing her limits. But that was a lie, anyway. Anal was most definitely a soft limit here, and probably a hard limit for her regarding anyone else.

And really, all of a sudden we're treating this like we're entering ... what did Marie call it? 'The Lifestyle.' We were just role playing. Weren't we?

"Jaycee, would you want me to do any of those things to you?" I asked hesitantly.

"No," Jaycee too quickly answered. "Well ..." she added.

"What?" I pushed.

Jaycee still took some time before answering. "If you had some nipple clamps, that might create some ... Eek! Will!" I whipped the car around in a u-turn before she completed her sentence. I knew just what aisle they were located on.

Once we got back to my apartment, we spent the next couple hours reading together. At first Jaycee had grabbed one of her newly purchased books and a pencil, and settled in on the sofa to have another of her written conversations with the next reader. Since the next reader was going to be me, we cuddled on the sofa together, her reclining against my back as I read over her shoulder. It was rather fascinating reading, and got us both a little hot. But it also prompted a good discussion. Jaycee and I were close to the same page on what we liked and didn't like. For a lot of the things described as falling under the BDSM lifestyle, our response was 'no, or at least not just yet.' Face it, we were both brand new at this and while the idea of many of the subjects got us turned on, I was wary of putting them into practice anytime soon.

The subject did promote an admission on my part — a story that I hadn't shared with anyone before.

"Have you ever had thoughts or fantasies of being in a Dom/sub relationship before?" Jaycee asked me.

"Oh, pretty much ever since I entered puberty," I admitted.

Jaycee laughed. "Really? You've always been that kinky? I can just imagine you as a boy, with all the little girls bowing before you as you walked into the school cafeteria."

"Now look who's projecting me into their own fantasy?" I teased. Jaycee giggled again.

"There was actually one event that sparked it all for me," I recalled. "When I was thirteen, my mother took me to Vegas."

"Vegas?" Jaycee asked, surprised. "When you were that young?"

"Yes, her company held their annual convention there that year and she took me along. She told me years later that she did it to keep herself out of trouble. She was known at her office as the hot, single mom and had received some not-so-subtle messages that her male co-workers were looking forward to spending some time with her at the convention."

"So you're saying that your mom was a MILF," Jaycee teased back.

"I guess so, but I doubt that word was around back then," I replied. "Ugh, I don't want to think about my mom that way."

"So instead of her getting into trouble, you got into trouble?" Jaycee imagined.

"No, nothing of the sort. I was a little, nerdy kid at the time, just entering puberty. And a thirteen year old couldn't do anything in Vegas. I mean, there were only so many times I could watch the pirate show or the water fountain. I begged for my mom to take me somewhere. So she finally relented and took me to see a comedian."

"Which one?" Jaycee asked.

"George Carlin."

"He's dead, right?"

"Yes," I answered. "I was so upset when I heard the news last year."

"And you saw him when you were thirteen? That must have been interesting."

"Yeah," I agreed. "He closed the show with a collection of two hundred and some words and phrases he'd collected that are used to describe the act of masturbation. I don't think my mother looked me in the eye once over the next two days. She was too embarrassed."

"So," I continued. "The theater was set up like a dinner theater, with open-sided booths where if we were facing the table we'd be perpendicular to the stage. Or maybe it was just our section where we were seated and not the whole theater. Regardless, you get the picture, yes?"

"Sure," Jaycee answered.

"So my mother and I were sitting on one side of the table, and then this couple comes and sits down on the other side, facing us. And they were such a contrast. The guy, well, I didn't really realize this at the time, but he was the spitting image of a mobster."

"What? What do you mean?" Jaycee prodded.

"He had slicked back black hair, heavy set, looked like he was of Italian descent, wore a suit but with a white mock-turtleneck underneath instead of a shirt and tie, and had gold chains around his neck. But the thing was, he was incredibly ugly. Really, there's no way I could accurately describe how ugly this guy was."

"Ok," Jaycee interrupted. "Mondo ugly. Got it."

"Sorry. Right. But the girl. And I call her girl because in relation to him she most definitely was. She was gorgeous. Not in a fake, plastic, Vegas showgirl kind of way, but in that wholesome girl-next-door kind of way. You know, like you."

"Me?" Jaycee asked surprised.

"Yeah, pretty much exactly like you," I confirmed. "Except she had a lighter shade of hair, and her boobs were better."

"Hey," Jaycee protested. "No one's boobs are better than mine!"

"I stand corrected."

"You'll pay for that later, mister," Jaycee grumbled.

"It's Master," I countered, "and no, I won't." And I grabbed her a little stronger with my arms.

Jaycee twisted her head around to show me the smirk on her lips. I gave her a quick kiss.

"Anyway, it was the nature of their relationship that was so mesmerizing. They hardly said anything to each other. But the way she looked at him. Complete adoration."

"Really."

"Yes, it was like he was the center of her entire universe. We didn't matter. The wait staff didn't matter. The show certainly didn't matter. The only thing that mattered to her, at all, was him."

"Ok."

"No, more than 'ok.' I gawked at her through the entire show. Really, I could barely keep my eyes off her."

"Did the guy do anything?" Jaycee asked. "Get annoyed with you or something?"

"Nope. I was beneath his notice. Maybe he thought stares like that were his due. I don't know."

"So what happened then?" Jaycee asked.

"What do you mean?" I returned.

"In your story. What happened then?"

"Nothing. That's it."

"That's it? You stared at them during a show. That's your entire story?"

"What do you think happened? He ripped her clothes off and did her right there on the table? No. It's what they represented. Here was, at least in my opinion at the time, the most perfect woman I'd ever seen and she was completely, helplessly, hopelessly, head over heels, gaga over this guy who looked like he had no business ever getting a girl like her. Yet, he barely noticed her. She was there for him. He wasn't there for her. It was that power dynamic, that study in contrasts, that idea that a beautiful woman's heart, her soul even, could be treated as a possession just like any other. A valued possession perhaps, but still something that could be acquired through money or power or even sheer personality, and then used just like any other item in one's possession."

"Oh. Wow," Jaycee breathed out. "Ok, I get it now."

"Good," I said, satisfied. "Then I hope it won't be too surprising to know that she became the focus of most of my sexual fantasies for the next ten years."

I stroked Jaycee's hair as I thought of all those late night fantasies where that girl knelt by my feet and looked up at me with those doleful eyes.

"So that's the standard you hold all women up to isn't it?" Jaycee concluded. "Complete surrender of her very soul to you?"

"Don't worry," I chuckled. "I realize it's a fantasy. It's not like I ever expect to actually find it."

Jaycee turned over in my lap so that she faced me. "Are you sure?" she asked. She batted her eyes at me a couple times and did her best to fake a look of awe towards me.

"Don't," I ordered. Jaycee stopped and looked at me questioningly. "Remember when I ordered you to be absolutely truthful with me? That incorporates this. Don't try to fake anything with me. It's insulting and disrespectful."

"Oh. I was just going to try to give you your fantasy. Isn't that what I should do?"

"Don't worry, Jaycee. You're more than enough of a fantasy come to life for me to have to fake anything," I tried to assure her.

That seemed to placate her and she rested her head on my chest. We both lost ourselves in thought for a bit

"I think," I shifted thought, "that it's about time we took a look at what trouble we can get into with this evening's purchases."

"I don't know if I should be excited-happy or excited-nervous, or maybe even excited-scared," said Jaycee.

"Are you inventing your own language now? Repeat after me: 'because I am;' as in 'excited because I am nervous.'"

"Lawyers," Jaycee muttered under her breath as she got up.

A short while later I had Jaycee spread-eagled and face down on my bed, arms and legs fastened one to each bed post. She had started off in an all-black lingerie set, featuring an impressive design of delicate ribbons. It looked spectacular on her, and quite expensive, and yet barely spent any time on her body before I just had to remove it. Meaning, I guess, that it had done its job superbly. Only the fingerless gloves, black and laced with ribbons, remained attached to her forearms.

"Jaycee, I don't want you to worry about the ramifications from anything you say. Until I release you, you can call me names, yell obscenities, whatever you want. Ok?"

"Ok, but what on earth for?" Jaycee asked.

"Because I want to get the natural reactions from what I do to you, and if you were holding yourself back then I wouldn't be able to tell just how you felt," I explained.

"So you won't punish me if I call you a dirty name or yell at you?" Jaycee asked.

"Nope," I answered. She looked like she didn't believe me. I tried to make my reasoning more clear. "Jaycee, before, I was trying to control you by getting you to control your own impulses, yes? Well, now I'm controlling you by having you all tied up. And you've got no safe word. So go ahead and yell and scream for all I care. It's not going to make any difference."

Jaycee pulled at her bonds. "Just remember," I added. "Rule number three is still in effect. Everything you say has to be honestly said. So how are you feeling?"

"Nervous. Really nervous. Exposed," Jaycee replied.

I began a very slow, full body massage beginning with her shoulders. I tried to remember the things that Jaycee had done to me a few days ago, and the things she had enjoyed from the previous massages I'd given her. This one, though, I planned to draw out as much as possible. I sat lightly on her rump, dressed only in a pair of silk boxers, and did my best to relax Jaycee as much as I was able.

I used a light amount of massage oil, just enough to ease the passage of my hands. I still wanted enough friction to work her muscles underneath her skin. I massaged her arms, and even her hands. Jaycee giggled when I sucked on her fingers for a minute. Even after I felt Jaycee relax completely into the mattress, I went a couple more minutes before shifting down towards the bottom of the bed.

This time I started at her feet and worked my way up, alternating between the legs.

"You, sir, are a very gifted amateur," Jaycee complimented following a particularly long groan of approval.

I paid particular attention to the backs of her knees. They appeared to be a strong erogenous zone on Jaycee. I could definitely smell a wonderful scent emanating from two feet north of where I sat.

As I edged my hands upwards, I stayed away from the inside of her thighs. I wanted to work Jaycee up as slowly as possible.

"You can get me off anytime you want to, sir," Jaycee hinted. I chuckled in response, and moved my hands up further but to the outside of her hips. Jaycee began edging her butt up in the air as an invitation to touch her sex. While I enjoyed the view, that wasn't in my plans just yet.

Instead I began long, hard strokes from her back, over her butt, and down to the backs of her legs. Reversing direction, I finally pushed forward up the insides of her thighs, causing Jaycee to move her butt further into the air in anticipation. But at the last second I veered away from her pussy, already open for me, and began a strong massage of her still slightly pink behind.

"Oh, you rat bastard," Jaycee hissed at me in frustration. That brought a smile to my face, especially since Jaycee didn't jump from her butt being manhandled. I swept my hands up to her back again and then repeated the entire process.

On about the fifth repetition, Jaycee started responding to her butt massage — as in pressing her butt up to meet my hands. Finally, a breakthrough. Now I began pulling her cheeks apart, and including in my massage areas closer to her little pucker.

"Oh, God!" Jaycee exclaimed, tensing up momentarily, but only momentarily. I continued for a few more minutes, continuing to both get Jaycee accustomed to my touching her in her most sensitive spot and in increasing her sexual excitement.

Finally I deemed the moment right. I worked my left hand downward from her behind until I cupped her pubic mound. Jaycee hissed a little when I refused to penetrate her, but instead slowly and lightly caressed her.

With my right hand I reached over and selected the smallest of the butt plugs I'd purchased earlier. This was roughly the size of a man's finger; actually, maybe a little thinner. I applied a good amount of lube, having difficulty doing so one-handed but I managed.

Jaycee by this time was fighting against her restraints, trying to move to force the contact with my left hand that she wanted. I finally gave it to her, gripping her mound with my palm while rubbing her clit with the pads of my middle and ring fingers. I then took the plug and eased it into her back passage. I don't think Jaycee realized I was penetrating her ass instead of her pussy until it was at least three inches inside.

"Oh shit!" Jaycee exclaimed and tried to buck me off. I kept the plug in and re-focused on her clit. It only took a minute to get the plug fully inserted, with just a small tab sticking out for easy withdrawal. Jaycee was now bucking and shaking constantly. I removed my right hand from the plug, wondering if it would stay in. After a few seconds I moved my hand lower to join his partner in getting Jaycee off. My left concentrated on Jaycee's clit while my right began fingering her.

"Master!" Jaycee screamed while coming. I kept at her for a full minute before allowing her to wind down.

"You are an evil, evil man," Jaycee said after a few minutes while looking at me out of the corner of her eye.

"I try," I replied. "Ok, time for you to turn over."

There were two ways to do this. I could release her completely and then order her to flip over spread eagled while I retied her, or I could move one appendage at a time until I'd made the correct sequence of moves to have her face up. I went for the latter, so that she would feel tied up and in my physical control as much as possible.

When I had her facing upwards, her wonderful nipples pointing straight at the ceiling, I got out the blindfold I'd purchased and placed it over her eyes.

"Now how do you feel, Jaycee?"

"Like I'm your complete prisoner. My entire existence is in your hands," she answered. It felt like half the blood in my body rushed to my prick. My dick felt like it wanted to grow another inch but was stymied by the physical walls of my flesh.

"Yes, Jaycee. You are in my complete control," I said. "Which means you cannot stop me from doing this."

I reached into the bag of goodies next to the bed and brought out the large feather I'd purchased. I started with light touches. Jaycee didn't know what it was at first. Her body would react with a jerk or a quiver, but even though she had a blindfold on, I could tell that her face was contorted with a questioning look. She finally clued in when I brushed the feather across her left armpit.

"Oh, shit. Oh, fuck. I hate being tickled," Jaycee exclaimed as her body jumped away from the soft feather. I switched sides and attacked her right armpit.

"Oh no. No, no, no, no, no," Jaycee said. Her body jerked, and she pulled strongly with her arms on her restraints. "Aiee! No!" she finally squealed. I had her now. For at least five minutes I tortured her with tickling. She laughed, squealed, screamed, and cried.

"Oh my god, my ass! I can feel it in my ass!" Jaycee exclaimed. Yes, she still had the butt plug inside of her. I guess it was giving her some interesting sensations as her abdominal muscles clenched and unclenched in response to the tickles.

She soon got to the point of laughing while crying. It sounded like I had broken her.

"Please, no more. Please, sir. I can't take it. Master, have mercy. I beg you."

Since she called me Master, I decided to end the tickling. Instead I went back to the massage, using Jaycee's own oils against her. I diligently avoided her sexual organs, though.

"Ohhhhh, this is nice," Jaycee sighed as her muscles lost their tension.

When it became obvious that I was touching her everywhere other than her breasts or pubic region, Jaycee became a little concerned.

"Sir?"

"Yes, Jaycee?"

"What are you doing?" she asked.

"Whatever I want," was my reply.

I started inching just a little closer to the untouched regions, brushing against the side of her breasts and touching just the top wisps of her pubic hair. Now the lack of sensation became its own tension. Her impatience got the best of her and she started twisting her body towards my hands to get me to hurry up. Instead I drew this out even further.

"Errrr," Jaycee groaned. "Please touch me, sir."

"I am touching you," I answered.

"You know what I mean. Get me off," she pleaded.

"Again? What a greedy, little slitch you are. I haven't gotten off once yet and you are demanding a second go?"

Jaycee whimpered loudly. I twirled a finger through her pubic hair and gave it a little tug.

"Oh!" Jaycee exclaimed. I just chuckled and unwound the hair from my finger. Then I moved up and sucked on her right tit. I sucked hard, right over the nipple. And then just a couple seconds later I released her. I repeated the random bursts of sensation upon Jaycee. I'd grab and twist the butt plug. I'd nip at her other breast. I'd grab her hair while giving a strong suck to her neck. And then I'd stroke up the sole of a foot with a fingernail. Her not knowing when or how I was going to strike next was driving Jaycee crazy.