Daily Assignment 11/23/10 A Steep Price

A Steep Price

11/22/10

I have purchased freedom – to an extent, and it was a pain in the ass.

As many of you might be aware, I’ve been stuck in my chastity belt since Friday morning. Sure, I’ve been allowed to take it off to use the bathroom, but since I was also required to relubricate both phalluses with Stinging O, I’ve been a little more circumspect about how often I take OFF my chastity belt. Of course that wasn’t the only complication. Every two hours I had to endure two minutes of intense vibration. Thank God I was allowed to choose WHICH vibrator was on. Had it been either the vaginal or clitoral one, I’d be getting punished right now because there is no way I would have been able to stand it.

Oh yeah. And I hadn’t cum since Thursday’s assignment, when I smacked my clit hard with a ruler.

So I was pretty desperate.

Master Barrett had plans to keep me in the chastity belt all the way through the Thanksgiving weekend, but offered me the ability to “purchase” my way out of it. All I had to do was come up with a few options; things I’d be willing to do in order to be allowed not just to take off the chastity belt, but cum.

The end price was steep and technically I haven’t paid for it all.

What was the price you ask? I agreed to the following:

1. I will strip naked and don only my duster and my vibroballs. I will take a black marker and find five different and separate guys. I will ask them to fuck me up the ass and then sign my rump.

2. I will go to a full parking lot and proceed to make breast imprints on twenty different dirty cars. After I’m done, I will find a ball trailer hitch and fuck it until I cum.

3. On Thanksgiving morning, immediately after I wake up, I will put the chastity belt back on. Once every hour of the entire day, I am to find someplace private and turn all three vibrators to their highest setting for ten minutes. It doesn’t matter if I cum or not. The vibrators stay on for the full ten minutes and not a second shorter or longer, no matter how sensitive or desperate I am.

I’ve done one of them already. Second tomorrow. The third one won’t happen until Turkey Day, but I’m not terribly worried. I’ve already masturbated a few times since yesterday evening and I feel much better and not to stressed about it.

But what happened yesterday? Well it all started with a phone call to Kari, who agreed to come along, cost to me yet to be decided. In the middle of the afternoon I headed over to her place. I was wearing a denim skirt, my chastity belt, and a tee shirt, not to mention flip flops. I brought my duster, but it was warm enough I didn’t need it. As usual, I padded up to her apartment door, dumped my duster on the balcony rail behind me, and stripped.

It didn’t take long.

When I was naked except for my flip flops and the chastity belt I knocked and was pleased to find Robert, Kari’s live in sex slave standing in front of me wearing even less. Only his cock was covered and by covered I mean it was stuck in a tube like sheath of black leather that seemed to be keeping him from getting an erection. Agonizing I’m sure. He smiled at me and stepped aside to let me come in. I gathered my belongings and headed into the apartment.

“Kari will be home in a few minutes, Breanne” he said. “Get comfortable.” He motioned toward the living room.

At that particular moment, getting comfortable would have meant ripping off the chastity belt, throwing Robert down on the floor, freeing his cock, and riding him until I exploded. Unfortunately, I suspected Robert’s current state of cock bondage was due to Kari’s concern that I might do something exactly like that. So instead I sat down on the couch. Robert came up, touched my shoulder, and handed me something. I held out my palm and he dropped a set of nipple clamps, connected with a silver chain, into my hand.

“Kari also said that she’d like you to be wearing these when she gets here.”

I rolled my eyes. “Have I not been tormented enough for that woman?” I demanded. Robert wisely didn’t answer, but just stroked my cheek down to the spot where my neck meets my shoulder. I shivered. It felt incredible.

“Want me to put them on for you?”

I looked up at him. Oh God YES. I nodded and handed him back the clamps.

“If I do it they’ll be really tight,” he warned me.

“Just do it, Robert.” I told him.

His warm hand cupped my left breast and then pain shot up through me as the clamp bit down, hard. It wasn’t the same type of hurt I feel when I’m wearing the alligator clamps. That’s a penetrative cutting hurt. This was more of a crushing pain. I looked down. My nipple was distended and had been smashed into something no thicker than a few millimeters wide. I hissed even as Robert’s hand surrounded my other breast, thumbing the nipple into turgid hardness before clamping it as well.

It took me a few moments to adjust, but I finally did and Robert sat down across from me. We talked sex, torture, sex torture, all sorts of things. Twenty minutes later Kari arrived. Robert immediately got on his knees and crawled over to her, helping her remove her shoes, holding her belongings, and then finally following her back over to the couch where I sat. Kari saw me, grinned, and planted a soft kiss on my cheek.

While grabbing hold of the chain between my breasts.

She pulled me up off the couch by the chain and I squealed and rose, hurt exploding through my breasts. I was tugged to the floor and told to get on all fours. I obeyed as she released the chain, turning back toward Robert. I hung my head, looking behind me as Robert’s cock was freed from the leather sheath. It was hard and glistened, as if it were coated in oil. Kari put her hand on him and pushed him toward me. I knew what was coming.

His hands went around my waist and found the buckle of the chastity belt. It came loose and I groaned as some of the pressure on the two phalli inside me relaxed. Then Robert was working the crotch belt loose and I winced as I was suddenly left empty, my pussy and ass both convulsing with tiny pulses, trying to understand what had happened. Why was the chastity belt gone? He set it aside and then I felt the tip of his cock on my still wide open and slight red ass hole.

And then Robert was the first guy to fuck me up the ass. After spending almost a full four days with a butt plug in my rear end, having a cock almost felt anti-climactic. Sure, it felt better than the plug, and the movement was great, but it wasn’t what I REALLY wanted. I can’t cum while being ass fucked. But Master Barrett knows this.

Kari had lubricated Robert with something thick and goopy, and I sort of suspect it was petroleum jelly but I’m not sure. He spent about four minutes back there while I just took it, bent over. Then I felt his cock harden and wham! My butt was filled. Just like that.

As he pulled out I felt Kari’s hand on my head. “Stay there sweetheart,” she told me.

She left the room and came back. I heard a click as the cap came off the marker and then Robert was signing my left butt cheek. I tried to hold still, but it tickled a bit. When he was done, Kari had me stand up and directed me to the bathroom to clean up.

Of course I checked the mirror. Reddened hole, some stretched and abraded skin, and a fucking SIGNATURE, like I was some sort of art work, on my ass. My little spurt of anger was enough to keep me from touching my pussy and I headed back to the living room.

Robert disappeared while Kari and I chatted. It was like old times. I was naked, except for the nipple clamps which were still dangling from my tits, and Kari was fully dressed and looking like a million bucks. I slipped right back into my subservient mode, listening politely, even offering to make drinks.

Robert joined up about ten minutes later, this time fully dressed. Kari kissed him once, gave me a smile, and then asked “ready to go?”

And I realized… I’m about to go get butt fucked four more time. That’s a sobering thought for someone who doesn’t like it. My nipples ached a bit and I nodded. Robert grabbed my duster and held it out for me. I slipped my arms in and then started to button it up.

“Just the bottom two buttons dear.” Kari’s look was very intense. I obeyed and we all left.

Being escorted by Kari and Robert felt much better than being out on my own. All I had to do was sit there, be responsive, and let Kari handle things. Kari drove. I sat in the front and Robert got in the back. We didn’t take the convertible this time; rather we took Robert’s SUV. He smiled at me from the back seat.

Kari drove us along Houston’s back roads for about fifteen minutes and then we pulled up into a rather well manicured business park. I’d never been inside the building before, but felt more than a little conspicuous as Kari and Robert escorted me in. I figured we’d end up at a bar. Evidently Kari had more auspicious plans for me. Up the elevator and down a long hallway we found ourselves in front of a solid door with a narrow floor length window. I won’t mention the name plate, except to say that this was the office of a guy named Richard. I won’t mention what he does either. While I’m sure he’d love the advertising, getting asked “what was it like to butt fuck Breanne” is probably not on his list of important questions to field on the phone.

In any event, we went in. There was a very small waiting area, but the door to the back office was wide open and Kari stuck her head in and waved. I could hear Richard speaking on the phone. I took the opportunity to look around. The office had Kari’s touch all over it. She’s an interior designer and I could tell she handled this one. It was a combination of old world antique with modern lines. Black leather, dark stained oak or mahogany (I can’t tell the difference), lots of burnished silver. It was… masculine and very rich. I liked it. In a lot of ways it reminded me of Robert.

“Kari!” Richard’s voice said in greeting. He was about five nine, and so much shorter than Robert, who is around six four. His dark brown hair was thinning slightly on top, but he was in good shape, without the usual paunch men around forty have. His shoes were patent leather and his suit, or what he was wearing of it, seemed expensive. He wasn’t wearing his coat, but the tie looked like silk. He kissed Kari on the cheek and then shook hands with Robert. Evidently they knew each other. I made like a mouse and sorta tried to look inconspicuous.

Which I suppose is hard to do when you’re naked except for flip flops, a mostly open down the front denim duster, with your breasts mostly on display, obviously sporting a chain connected to barely concealed nipple clamps.

“And this must be Breanne.”

I nodded, my heart racing.

He gave me a reassuring smile. He looked back at Kari. “And she’s okay with this?”

Kari laughed. “She’s the one who asked me to shepherd her. You’re the one doing ME the favor.”

Richard laughed. “Some favor!” He looked back at me and smiled again. “Well, come along Breanne. I hear that nympho humiliation pain sluts need a good fucking now and again. Oh… and I like the website.”

I’m sure Michael will be pleased. As for me, I stepped forward, took his outstretched hand, and was pulled into his office. The door closed, separating Kari and Robert from us.

He was gentle, which was nice, but it felt odd being naked in front of that huge window. I could see half of Houston, and I FELT as if half of them could see me. I was told to take off my duster and I stood there naked, being examined. Richard touched me practically everywhere, but it wasn’t until his fingers found my pussy that I relaxed, letting the sensation of his touch pleasure through me.

But evidently he had been told I wasn’t allowed to cum. I was maneuvered over to the desk, behind it, as if I were going to sit down in his chair. And then I was pushed down, bent over his blotter. The clamps tugged awkwardly at my nipples, but I didn’t adjust them. I endured.

Richard took a moment to take off his trousers and drape them over his chair. He was wearing green silk boxers. A minor adjustment exposed his cock and then he pulled me up OFF the blotter. I blinked, confused, but then he pushed me down onto my knees. Ah… blowjob first.

I was fine with that. A good blowjob would reduce the amount of time I spent with cock up my ass. So I did a good job. He actually ended up sitting back down in his chair and I worked him good. Finally I could tell he was getting close and I tugged on his cock, stood up, and then resumed my position on his desk.

His dick was still wet from my mouth, and my ass was still greased from my earlier fuck. He went in smoothly. Well… as smoothly as my muscles would allow. I have to really concentrate to let cock… or anything… go up my ass. He pistoned for a few moments and then exploded, filling me just like Robert did.



When he pulled out I helped him with the condom and through it in the trash. Then I spotted a cup filled with pens on his desk. I grabbed one of his Sharpie markets, black of course, and turned back around to let him sign. He did. Right side. Smack dab in the middle of my buttock.

I got back into my duster and Richard gave me a kiss. He thanked me for the experience and then I was back with Robert and Kari, who obviously had been getting into their own fun in the waiting room. They stood up, smoothing their clothes back into place and then Kari and Richard chatted for a bit and we left.

Our next stop was a little weird. It was a hole in the wall recording studio just south of the University. I’d never been there before but it looked cool. Kari waltzed in like she owned the place and Robert and I trailed behind her until we came to a small office. She rapped on the door frame, since the door was open, and I heard the typical Black American slang accent frame a greeting.

“Kari! What’s up girl?” Or is it “Kari, wutz zup, gurl?” I have no idea. I’m not racist or anything, but I AM inexperienced. I mean seriously, would a South Texas Cow Girl hang around with a bunch of… um.. I don’t even know the right word. Homies? Gangstas? Brothers? Dudes? I’m just so not good at this.

I was introduced to KC and never told what the K or the C stood for. For all I know that was his name. Or maybe his initials. I remember thinking “God, I hope his middle name wasn’t Franklin or something. Wouldn’t that be embarrassing? KFC?” As it turned out, I found out later that night that there is a D after the KC, so who knows.

KC was a DJ, a singer, a rapper, and a sound engineer. Talented guy. He came out from his office, which was nicely decorated and led us all toward the sound studio. This was where I finally realized how Kari knew KC. Once again, her soft touch made it obvious. While the studio was trashed with electrical cords or mic cords or whatever, the walls were obviously Kari’s design. Especially the lighting. It was… smooth is the best word I can think of. It made me want to sing. I didn’t sing, but I groaned a lot. Kari had me take off the duster and then I was pushed gently over a large carpeted speaker box. Then, to my surprise, KC positioned a huge sponge covered microphone in my face. He left the room for a moment, and then moved behind me.

KC was not an especially large guy, and I’m talking height and bulk. He was taller than me sure, but most of the planet is. He wasn’t as big as Robert, that’s for sure. But there was one part that WAS as big as Robert, and I found out rather quickly after bending over that speaker. And KC pushed. He wasn’t as gentle as either of my previous ass fucks, but since I was so accustomed to having stuff rammed up my ass, his penetration wasn’t anything to worry about. Sure, I whimpered. I groaned. And since I was obviously being recorded, I hammed it up. I moaned. I whined. I grunted. Then I begged. Very different from my two previous ass fucks. All in all, a very nice performance.

Which earned me a raised eyebrow from Kari.

When KC was done he sighed in satisfaction and pulled up his pants. I stayed in position, just breathing and trying not to think about my pussy. I was wrong. Getting ass fucked, while not a direct stimulation situation, DOES turn me on eventually. Of course, I was already so desperate that fucking a cactus would probably have gotten me off.

Kari held out the marker for KC to sign me. When he did, it felt rather odd. He signed on my left buttock, but I felt the marker go almost right up to my anus and I was pretty sure he drew an arrow. I found out later I was right.

Three down. Two to go. And it was getting close to five.

Back in the car I winced slightly as I sat down. My rear end was sore. Sure, I had spent the last four days stuffed with a four inch deep two inch wide vibrator plug, but there hadn’t been much movement. It’s having cock move in and out through your sphincter that really creates the stress in ass fucking. Trust me. I know.

Another drive of twenty or so minutes followed and to my surprise we pulled up in front of a strip club. A real strip club. It was off Westheimer, but I’d never been in the building before. Kari and Robert however seemed to know their way around and we proceeded to the front door. Rather than pay a cover charge and go in, Kari extracted her business card and handed it to the cute girl at the counter, asking to see the manager. It was only a few moments before a slightly overweight guy with sandy brown hair showed up, arms wide.

“Kari!” Hugs followed and I had to wonder if Kari had done the decorating at the strip club. That would be so… uh… cool? Yeah. Cool.

I was introduced to Brian (whose last name will remain undisclosed to protect the innocent… and the guilty, just like all the other guys I’ve mentioned today.) The four of us went into the main room and I got a couple of hostile glances from some of the half-naked lingerie clad strippers walking by.

Okay, let me make one thing perfectly clear. I am not, nor ever have been, nor ever will be, a stripper. The whole industry is questionable. Lots of drugs, lots of strange parties, and not very much control. I know it SEEMS like I don’t have control as a NHPS, but in truth I do. I can always say NO. The whole thought of fucking for money turns me off. Sure, I’ll accept a twenty waved in my face like the next girl, but I don’t have sex for money. I have sex because I love it.

Master Barrett asked me the other day what I looked for in a guy when I was out and about looking for targets. I thought about it. Obviously the first thing I look for is cleanliness. I don’t fuck slobs. Or seriously overweight people. Twenty to forty pounds overweight is one thing. Topping out at three hundred just doesn’t cut it. Then I try to get a feel for the guy. Does he smile? How does he hold himself? And then lastly, I try to look for geeks and nerds. These guys are usually sweet, gentle, and haven’t had a sexy girl in ages, if ever. Some might call me predatory, but what I’m trying to do is make them happy. Oh yeah, and give myself orgasms. But hey, why not spread it all around, right?

So stripper and whore I am not and I tried to ignore the looks I was getting. I guess my pretty much open duster was an issue. Hell, I wasn’t even wearing my stripper shoes! But we didn’t sit down in the main room. We were led to the back of the building and entered a plain door and then went up a narrow flight of stairs.

To the balcony. Wow. Very nice. And oh look! Private rooms!

Kari and Robert were shown to a table and a waitress came out and took their orders – complimentary of course. On the house. I was asked to take off my coat. I did, feeling a little less exposed on the second story than the first and left it draped over a chair. Then Brian took my hand and I was led away from Kari and Robert.

To a small VIP Room. It had a settee, a lounge chair, a wastebasket, and subdued lighting. I wasn’t sure if Kari had decorated. The room smelled like sex and citrus cleaner. Brian sat down on the chair and motioned for me to begin.

Uh…

I may not be a stripper, but I can act like one. And I did. I weaved. I danced. I swayed. I straddled his lap and did a lap dance. I rubbed myself all over his body. He tugged on my nipple clamps and things just went crazy from there. I ended up slipping down to the floor, my hands at his waist, freeing his cock until I was able to wrap my mouth around him. I did a great job too. He was putty in my hands. And then he grabbed me, pulled me up, turned me round, and sat me down in his lap. His hands guided my thighs over the seat’s armrests and then I felt him lift me at the hips, positioning me properly. I felt his cock against my rear and then I relaxed, letting myself slip down.

It was a porn position, and not really suitable for sex. I’m sure it looked awesome though. It only took him two or three minutes to literally pick me up and put me on the settee, where I was I was promptly penetrated again. My rear end puckered around his cock, and I was bent over with him banging me from behind.

When we were finished I was offered a moist towelette and escorted back to Kari’s table. I was asked to bend over and he signed my ass with the offered marker. Hugs were exchanged, I got back in my duster and flipflops. Brian came over to me, kissed me on the cheek, and then offered me a job.

Our next stop was an upscale apartment not far from where Kari lived. I was introduced to Alan Green who invited us all into his bachelor pad with a smile. Once again, I could see Kari’s design touch. This time by adding splashes of color to what would otherwise have been a very black dark shadowed cave. Kari has this ability to sense what style goes with her client and then work within that style to soften it and bring out the best. She is especially good with lighting.

My duster was taken from me after a few minutes of chatting and then I was taken to the back bedroom while Kari and Robert downed their drinks. The master bedroom was pretty large, with a full king sized bed. Alan wasn’t a terribly large man, but he was thirty something, and topped six feet at least. Not as tall as Robert. Not as short as K.C.

Alan was gentle. He touched me, caressed me, kissed me, stroked me, all the while staying away from the one part of me I really wanted touched, caressed, kissed, and stroked. Hell, I would have settled for a whipping at that point. He slowly undressed with my help and once again I gave an impromptu blowjob.

When he was ready he positioned me on all fours, in the very center of the bed, and climbed up behind me. I felt the tip of his condom covered cock on my rear and then he began pushing. He had trouble. I did too. The bed was very very soft, one of those space foam things and I kept sinking into it. Finally he pushed me to my stomach, straddled me, and I felt his cock slip through the crack of my ass. He pumped, enjoying the curve of my rear end under his hips and then the tip of his cock moved downward. I felt him against my ass, but I didn’t relax in time and his cock slipped farther down.

And then in.

I gasped at the penetration. My pussy convulsed around his cock. He began pumping obviously either unaware he was in the wrong hole, or not caring. The fire inside me roared into a blaze and I clenched my fingers around the sheets as I came, crying out, gasping in release and relief. It happened in moments and I had no control. No time. And then I just sort of went limp.

Alan came too and collapsed on top of me. His weight felt good and I was all smiles and deep sighs. Endorphins had rushed through my brain like bullets and I felt as if I had just had the absolute best sex of my life. Four days of orgasm denial can do wonders for plain vanilla sex. Usually I don’t cum like that unless I’ve been vibrated, whipped, clamped, waxed, and then force fucked with something inappropriately large.

It was awesome. After a few moments, Alan rolled off me, running his fingers up and down my back. I sighed softly and then turned and looked at him.

“Sorry about that. I didn’t mean to do it like that.”

I smiled at him. “Don’t worry about it. It felt incredible.”

He grimaced. “Yeah it did. It’s been a while for me. I know I was supposed to do your bottom, but it just sort of…” his voice trailed off.

“Happened,” I finished for him. He nodded.

“Think Kari will mind?” he asked. I shrugged. I knew the real question would be whether Master Barrett minded.

I gave him a smile and then sat up in the bed. His cock was limp and still a little wet. I leaned over, touched him, and gave him one of my million watt please fuck me in the ass smiles.

“You still need to fuck me in the ass. Let me get you hard again.”

And I went down on him. He groaned as I rolled his cock around in my mouth. I played with his balls, stroked him, sucked him, even blew a little. Lots of licking. It took another fifteen minutes, but with some concerted manipulation, a few soft sounds, and some naughty suggestions about what he could do to me, I soon had him hard again.

We tried again. This time he was successful. I groaned as his cock slid into my rear end and we pumped. It took him a long time to get off. Thank God for lubrication gel. It made things a lot easier. Finally he came and we repeated the whole quiet soft moment after sex.

Eventually we got up and I donned my duster again, slipping my feet into my flip flops. Back in the living room I saw that Kari’s face was rather flushed and Robert looked slightly pleased with himself. I said my goodbyes to Alan, which consisted of a rather passionate pleased kiss, and then accompanied Kari and Robert downstairs.

“That took a long time. Do you need to tell me anything?” Kari asked as we got into Robert’s car. I smiled and shook my head. When she reads this, I’m going to be in trouble.

We went to dinner then. I was allowed to button up my duster all the way, but otherwise I stayed naked, with the clamps on. Hibachi is awesome, especially when you’re still turned on and doing the flasher thing.

Back at Kari’s apartment we did one more thing. I think you know.



Hope you're happy. See ya tomorrow.