My New Boss Ch. 20

This chapter is part of a continuing story. Although some chapters may stand on their own, for proper character development and story line intensity, this series is a continuous story and should be read as such.

It was a snug fit, but that plug had to come out. I wanted to fuck that tight ass, and to do that, the plug had to come out. So, that was the next item on my agenda...remove the butt plug. And, because it was such a snug-fitting thing, I was going to need some help.

It's like when someone has on some tight boots and they need help getting them off. This was similar, but more care was needed. More care and maybe a good scream silencing gag. It wasn't easy getting that thing to go in, but James got it in. And, because of the way those tapered plugs are made, the large part would be the first part to come out. It was much easier to push in, because of the cone shape. Something told me James didn't think that far ahead.

Lucy and James were ready to help and then Rita snapped out of her after orgasm trance, so she could help, too. The slut was just standing there, still naked and tied. The gag was still in her mouth but James removed the purple dong. He said something about it being in the way, because of its size.

I had Lucy and Rita hold the two sides of the spreader bar to steady the slut. And, James grabbed hold of her waist, to be the resistance to my pulling. I got behind the slut, and did my best to grab hold of the butt plug. I wiggled it around, and that got the reaction I didn't want. It made the slut moan, and she tightened up her ass around the plug.

I needed her to relax, so I could pull the thing out. "OK, slut, relax your ass, or it's really gonna hurt coming out. You can trust me on that."

Lucy giggled when she heard me. "And, why are you warning her it's gonna hurt?"

"Why is it always a woman who thinks last about the other woman's pain? She's my fuck toy, and I want her asshole to be just as fuckable tomorrow as it was an hour ago. You don't feel it with that strap-on you wear, but my cock feels it. And the tighter the fit, the more I enjoy it. I don't think I need to say anything more, do I?"

Lucy stuck her tongue out at me, and put her hands on her hips. "OK, then, let's see you get it out of her. I'm betting it's gonna hurt."

I bet it's gonna hurt, too, but if she can relax her ass, it will hurt less."

"We've been hurting her all night. What's a little more pain gonna hurt?"

"I enjoy inflicting pain, Lucy, but not when it can harm the person. I don't want to rip her asshole. We need her to relax, so I can get this thing out."

Typical Lucy. Thinking of her own pleasure before someone else's. She just lowered her head and nearly whispered her answer. "OK."

Come to think of it, that's the typical Rita, too. And, there's nothing wrong with that, as long as I'm there to control 'em. Some of their self-serving tendencies can be fun. And, those self-serving ways really come out, when they're in Domme mode. I like that.

So, once Lucy had taken her place, everyone was ready to go. Lucy and Rita on the sides and James was holding the slut around the waist. I started stroking the slut's clit and pussy, to get her to relax. It really wasn't that easy. She'd been our pain slut all evening, in one way or another. I think she was just waiting for the other shoe to drop, because I'm always giving pleasure before dishing out the pain.

I had an idea. I told everyone to step aside, but to be ready to move back into position, quickly. I bent over her, and reached around so I could finger her clit with my left hand. The first time I touched it, her legs nearly gave out. It was very sensitive, but that didn't stop me. I hunched against her ass, pushing the butt plug in with my body. That, and my rubbing her clit, was getting her attention.

With my right hand, I started pinching her nipples, first one, then the other. She was responding in exactly the way I wanted. I could feel that she was breathing heavy. Her body twitched, as my fingers probed her pussy. I started grinding against her ass, hunching that dildo as much as I could. The slut loved the attention. She was getting close to cumming.

I wrapped both hands around her waist and pulled her back against me. I heard her whimper from behind the gag. I was starting to enjoy it, too. My cock was getting hard and I'm sure she could feel it against her ass cheeks.

The ever-impatient Rita just couldn't stand it. "So, are you just gonna make love to the bitch, or are we pulling the plug out of her ass?"

"I'm helping her relax. Just hang on for a second. Your fun time is coming."

Like a couple of kids, that Lucy and Rita. Always wanting to play and they don't want to share their toys. Well, this toy was mine, so I was making the rules. We would share, but because she was mine, I didn't want her harmed. If it's damaged, there's a period of down time when I'd be without. A tight submissive asshole is a thing of beauty, I tell ya'. It must be taken care of!

I continued my quest of helping the toy relax. What I was really doing was helping her focus her thoughts on another part of her female body, and maybe that would cause her asshole to relax. But, that was difficult because she was such an ass slut. And, the butt plug wasn't made to conceal.

If I just touched the base of it, that sent sweet sensations though her body. But, I knew she would also respond to my rubbing her clit and pussy. If I could get her attention centered on something other than her ass, I might be able to get the plug out. I continued to lean over her, rubbing her clit with my fingers. She started wiggling her ass against me, responding to my advances. I decided I needed to stop leaning over her that way, because I was touching the butt plug, forcing it into her ass. She liked that too much.

I got Lucy and Rita to hold the spreader bar again, keeping the slut in position. Then, without touching her body in other places, I reached around and teased her clit. The reaction I got was a quick jerk from my initial touch and a little squeal of pleasure. I got more vigorous with my probing and I heard moaning from behind the gag.

I leaned down to her ear and began to entice her with some inspirational talk. "Well now, I see my little slut likes her clitty touched. She's not just an anal slut. You're also responsive to other sensations. I bet I can control you in ways you didn't expect. What do you think? Wanna try, slut?"

All I got was more moaning and a whimper or two. She was sure enjoying my touch. Maybe a little sensitive touching was just the ticket, after being our evening pain slut. Depriving her of orgasms had kept her excited and eager to the point a minimal amount of caressing went quite a long way.

I kept up the talk, as I slowly pushed my finger inside her pussy. "You know I could torment you like this for as long as I want. I can tell when you're about to cum." I could feel her legs shaking. She liked it. "Then, I just stop touching you, and let you calm down."

I pulled my fingers out of her, and stood beside her, watching her reaction. She groaned her disappointment. She really wanted something inside her. She was such a slut. I whispered for James to get me that bullet vibrator we had shoved inside her earlier. When he handed it to me, I turned it on low. Its humming sound was obvious, and the slut whimpered in anticipation of its touch.

I kneeled down so I could reach her better. First, I touched it lightly to each erect nipple. That wasn't where she thought I was going with it, but she enjoyed it, just the same. Back and forth, from one to the other, I touched them, just enough to let her feel the vibrations on those sensitive nipples. She wiggled slightly, each time I changed sides. Then, I turned the vibe on high and repeated it all over again.

Her movements changed to high, too. I was just touching the very tip of her nipples with the vibe. It was interesting how much that minimal touch was exciting her. Then, I started touching her body in random areas with the vibe. I never pressed very hard. Just as I had with her nipples, I just lightly caressed her body with it. She wiggled and whimpered in appreciation, each time I touched her. It was kind of like a cattle prod of pleasure.

I continued my torment. "I see how you enjoy this little thing. It can be amazing, can't it? This little humming cylinder can be very exciting." I was slowly moving down her body, touching stomach...ribs...belly button. Her legs were really shaking. She was quivering more and more.

I leaned down and whispered into her ear. "You can tell where I'm going with this, can't you, slut. I could torment you and touch you everywhere but your throbbing clit, or I could be nice and rub it right up against that hot little bud. I bet you'd like that."

She groaned so loudly, I thought she was about to cum. But, she knew that I knew how badly she needed that vibe pressed against her clit. She also knew I would milk her need and use it against her.

I touched it to her inner thighs and slowly moved it upwards, missing her clit by a very little bit. She nearly cried from her need and tried to twist towards the vibe. So, I took it away.

"No," I said, sternly. "You're not playing fair. I'm in control, not you. If you want me to continue, you will stand still. Do you understand?"

All she could do was whimper and nod her head. Even that was difficult, because her throbbing pussy was on her mind. She wanted it to be touched and I think she would have taken it any way she could get it.

"Stand still, like a good little girl, and I might let you cum."

When Lucy and Rita heard that, I got two very dirty looks. Of course, Rita had to say something, too. "I wanna cum, too. Why you thinking about her? Shouldn't she be sucking James' cock or yours? Shit, maybe it's my turn, again, but it sure isn't hers!"

Lucy was quick to agree. "Why does she get to cum? She's the fuck toy. She should be doing us!" If Rita hadn't said something first, I don't think Lucy would have been so bold. She might give you a dirty look, but her mouth stays shut. Well...most of the time it does. Lucy has her outburst moments, too.

But, Rita is more outspoken. She's also more of a Domme, so she really looks at that slut as someone who should service her. Seeing me service the slut just wasn't right, in Rita's eyes. She was down right hateful. "Lucy and I have to stand here and watch while you make her quiver and shake. You make such a nice couple. When do I get to quiver and shake like that?"

"If you keep up with the outbursts, you won't be quivering at all, let alone shaking," said James. "You just had a big orgasm. You both did. Don't be so selfish. We're guests here, and guests don't make demands." James knew how to handle her. After all, he lived with her.

But, Rita just couldn't shut up. "I just don't see why she..."

James took a step towards Rita and pointed his finger right at her. "I don't care what you don't see or want to see right now, Rita! We are guests here, and you can leave any time you want. We are taking turns. You just had your turn so I don't even understand why you're complaining. You weren't complaining a little while ago."

That shut her up. I don't know what it was, specifically, but something James said, or the tone in his voice turned her into a shrinking violet. Lucy wisely kept her mouth closed, too.

I had turned the vibrator off while Rita and James talked. I turned it back on and started running it over the slut's inner thighs, again. Except for the fact she was shaking in her need, she stood still, while I inched closer and closer to her pussy.

Rita and Lucy stood silently, holding the bound slut steady. I could see the jealousy in Rita's face. She sure didn't think the slut should be pleasured. I ignored the looks. Even if it was under protest, she was doing her part. And, I think understood her position more than James did. Maybe James had seen it more often and had just seen enough.

The slut was shivering from the vibrator's touch. I held it tightly in my hand and touched her clit with my extended finger. That finger was vibrating almost as much as the vibrator itself. And she really appreciated my finger. But, I didn't leave it there very long. I wanted that appreciation to build some more. I had a plan. And, it was a plan I thought Rita was going to like.

I looked up at Lucy. I looked into her eyes, as I played with the slut's pussy. I saw her expression change, as the slut's body wiggled around. I don't know what she was thinking. Maybe she was imagining herself in the slut's position, or maybe she was just enjoying the show. But, that wrinkled brow had melted somewhat and I saw a hint of a smile.

I looked up at Rita. It didn't take me long to see her expression. She clutched the spreader bar so tight, her knuckles were white. She was in one of her modes and I think if I had allowed it, she would have loved to get her Domme hands on the slut. And, actually, that was part of my plan. Being in that mode, she was very good at mental torment. I just had to keep her from any physical torment, if I wanted my slut's body to last the night.

I moved my vibrating finger back up to the slut's clit. It just lightly grazed the skin. I repeated this several times as the slut groaned her need to be satisfied. I knew she could feel my finger, but the way she was bound, she couldn't get closer to it, so I could spend as much time as I wanted at it.

She could move from side to side, but she needed to move her hips forward to get closer. She could only move her whole body forward. Lucy and Rita were in control of that. I got on my knees so I could get a closer look at what I was doing. I made sure the vibrator was set to low, because that gave a coarser vibration. Then, I did the same type of touching, but to her pussy lips.

Right in the center, just below her clit, I lightly ran my finger down her wet sex. Her legs were bound tightly together, so I had to twist my wrist a little to keep from touching her with anything but my finger. That was important. It made her mind center totally on my finger and what it was doing...and where.

I moved my finger down as far as I could, then changed direction and followed the same path back up. I ever so lightly touched her clit before removing my hand, again. I looked down at the slut's toes. I noticed she was wiggling them a lot, as if she was trying to keep her mind off of her pussy. If that's what she was doing, it was going to take a lot of toe wiggling.

With my other hand, I reached up and pinched each nipple. They were both hard knobs of flesh and very sensitive to touch. She reacted with whimpers of pleasure, but I knew she would. Then, my vibrating finger returned to her clit. But, I applied the finger with more pressure, and made circles around it. At the same time I was still pinching her nipples with the other hand. Again, she whimpered, and I could hear insistence in her whimpers. She had been watching me. I looked into her eyes. She looked back at me with such a delicious need. She wanted my finger deep inside her.

So, I gave her what she wanted. I shoved my finger deep into her pussy, but just as quickly, I pulled it back out. She first squealed when it went in, but that quickly changed to a groan, when I pulled it out. She knew I was only teasing her. To make that perfectly clear to her, I held my finger up for her to see. It glistened with her wetness. She so wanted to cum. Her eyes begged me to help her cum. But, of course, I only smiled back at her.

James walked over and handed me the little whip that we had enjoyed using on her. He didn't say anything, but I understood the look on his face. Sexual satisfaction could be obtained in various ways. Direct digital stimulation was only one of those ways. Stimulation from certain kinds of pain was also another way. And, when those two were introduced together, things happened faster.

It was a perfect implement. It was thin and sturdy, yet it was flexible as a new switch, freshly cut from a tree. I took the whip and poked it in-between the slut's legs, then snaking it up around her pussy and asshole. While behind her, I ran it up and down the crack of her ass, and again pushed it between her legs. I poked her pussy with the tip, and watched her jerk when it found those sensitive areas.

Then, I brought the vibrator back. Using my finger again, I started between her tits and slowly ran down her stomach to her belly button. Then, I used the tip of the vibrator itself and ran up and down the sides of her body, poking her ribs as I went. I poked and prodded her without mercy, and she jerked away with each one. She must have been ticklish. I never actually heard her laugh, but when someone is gagged, you usually don't.

I got down in front of her again and touched her clit with the vibrator. Then, ran it down her pussy lips, just as I had done with my finger, before. While she was reacting to that, I poked the whip in-between her thighs from behind and wiggled it around. Both sensations were easy to comprehend on their own, but together, they were difficult for her to take. Not only was she whimpering and wiggling, but she was soon gasping from the vibrator. I was using it to open her pussy lips, to allow the whip access.

Lucy and Rita were forced to hold her up, because her legs were giving out. She was reacting to every stimulation I gave her, and was very close to cumming. But, I wasn't ready for that, just yet. I stood up behind her and started whipping her ass with the whip. She jerked and tried to get away from it, but Lucy and Rita held her still. I could see her clenching ass cheeks and moving her feet around, but the girls were holding her in place.

After a minute or two of a good whipping, I let her calm down a little. That was a very large part of the plan. After she had calmed down, it all started again. The vibrator, the whip and all of the torment.

Again, I started with my vibrating finger. She was much quicker to respond that time. In fact, everything I did got a much quicker response than the time before. The need in her was quickly growing and I knew it would be only a matter of time until she was right where I wanted her to be.

I ran my finger up and down her pussy, I pinched her nipples, and I held the vibrator right on her clit. But, when I put that vibe on her clit, it started things going too quickly, so I had to add the whip as a counter measure. I pressed the vibe to her clit for a few quick seconds, and then I gave her ass a good lash of the whip. The vibe found her clit again, and then the whip found her ass, again. I had it orchestrated to be the good sensations and the bad sensations so her mind would get lost in it all.

I pushed the whip in-between her thighs, and let it tickle her pussy lips. Then, while running the vibrator up and down her body, I ran the end of the whip up and down the inside of her legs. I'm sure it felt like little fingers running up and down her sensitive inner thighs.

I decided it was time for one final addition to the plan. I asked James to bring me some tape from the slut's desk. I used it to tape the vibrator to the base of the butt plug. It didn't touch her ass at all, but just the plug. I had it turned off while taping it, and when finished I turned it on. I let it go on low for a short time, then turned it to high.

The vibrations went though the plug and deep into her ass. It wasn't a large vibrator, but it was powerful. The slut reacted to it, by wiggling her ass. I know she must have been clutching at it, with her asshole, but it was stretched so, I couldn't tell. But, that was the idea I had in mind. I wanted all sensations to be invading her mind at once.

I continued tormenting her mind, as I caressed her tits with my hands. I leaned down and told her she had no control over what she felt, and I could stop what I was doing at any time and just leave her with her need. Or, I could leave her in the hands of Rita, to do with her, as she wanted. "Wouldn't you like that, Rita? To be in charge of her, after she's been properly stimulated?"