Ultimate Pleasure, Ultimate Pain

My underwear hit the floor on the next hand, and my rock hard, pre-cum slicked cock jutted bare. The head was an angry shade of purple I had never seen before. Despite my fear of what would happen if I lost, and the humiliation of the deal I had been forced to accept, I had remained painfully erect.

Amanda sat back and inhaled deeply on her cigarette. "Big or small, men are still slaves to their hard-ons, aren't they," she said as she let the exhaled smoke mingle with her words. Amanda lost two consecutive hands and removed her sheer stockings. When my pair of threes lost to her flush, Amanda reached into the bag for the first time. She held out a small box, about the size of a cufflink box. I looked puzzled, so she gestured for me to open it. The two chrome things in the box meant nothing to me. "Nipple clamps," Amanda said over her shoulder as she walked into the kitchen. I couldn't help staring after her perfectly sculpted behind sheathed in denim. She returned with a glass of ice. Extracting a cube, she held me against the back of the chair with one hand, and rubbed the frozen cube on my right nipple, watching it stiffen. She repeated this on the left side. She then took one clamp, steadied my erect nub, and clipped it on. I could have resisted if not for her breasts, just inches from my face, hypnotizing me. The pain shooting through my nipple quickly broke the spell of her magnificent flesh, and I gasped and nearly shot out of my chair. Amanda pushed me back into the chair and expertly applied the second clamp.

"Remove them and the deal is off," she barked.

"You said women's clothing," I gasped.

"I said the contents of the bag!" she retorted.

I twisted and writhed, gritting my teeth against the pain. Amanda sat back, enjoying the show. She knew the pain would slowly diminish but was warmed by the knowledge that the pain of clamp removal was much worse than the sting of applying them. Amanda took a long, deep inhale from a fresh Virginia Slim, letting the smoke slowly escape from her mouth.

"Remember what this game is about, ultimate pleasure or ultimate pain. You wanted your pathetic little dick to give you pleasure, instead your balls will give your indescribable pain. You spent the evening salivating over my breasts, now yours give you pain." Amanda laughed loudly at the irony, and dealt the cards.

I won the next hand, but now felt totally defeated, convinced that even if I won Amanda now had the power to do with me as she saw fit. I couldn't even enjoy the sight of her slithering out of her skin tight jeans, her lush, sculpted behind less than a foot from my face. Her tiny lace panties framed the pleasure spot that earlier I had been so sure would be mine. The chiseled muscles of her butt and thighs were designed to give men of her choosing boundless pleasure, but could not have been more inaccessible to me.

That was the last poker hand I would win that night. The balance of the game was a blur, I don't remember a single hand, just the continuing degradation. I was fitted with a 44 DD bra, with huge, heavy water balloons filling the cups. The weight of the balloons caused the thin straps to cut painfully into my shoulders, and continually rubbed against the biting nipple clamps. Noticing my discomfort, Amanda lectured me on my misguided ideas about women's breasts. My painfully swollen cock had already started to teach me that large breasts were for punishment as well as pleasure.

"I never understood why guy's with very small penises think that they deserve women with large breasts. I always make a guy show me the goods before he gets anything, and if he isn't at least more than average, then these things (cupping her breasts as I groaned) are off limits," Amanda explained. "Less than eight inches, he goes home with his dick hard. Guys think that they are just as good as any other guy just because they have a dick, but won't hesitate to rate women by their bra size. A guy your size should never hit on someone without telling her upfront how small you are, because unlike breast sizes, women can't tell what you are bringing to the party. I'm sure you've been told before that when it gets this small, we can't even feel it. A woman with large breasts is not here for your pleasure, not unless you bring something that can give her pleasure, a fair trade," she said as she glanced disgustedly at my undersized cock.

I felt completely degraded, more ashamed than I had ever known possible. It was painfully obvious that Amanda was a woman that I had no right to yearn for, she demanded much more than I was capable of giving. The water-filled brassiere that bit into my tender shoulders combined with the underwire chafing my chest was punishment for all the times I had leered at beautifully endowed women, and dared think that my puny, drooling cock would be adequate compensation for their magnificent charms.

Stockings, heels, crotchless panties, short skirt and a sheer, low-cut blouse completed the outfit, and emptied the blue bag. Lipstick, fire engine red, was the icing. As Amanda, now fully dressed, lit another Virginia Slim, she held out her snifter and commanded, "Brandy." Dressed as I was, I couldn't even pretend to have any dignity. Next she handed me her ashtray, sending me off to empty and polish it. I teetered dangerously in the 3" heels that were several sizes too small, and hurt terribly. Every step caused my clownlike breasts to pitch up and down, threatening to spring free from the scoop necked polyester blouse. The terror of settling up on my bet had me feeling nauseous, my testicles felt more exposed and vulnerable, swinging free in the crotchless panties, than I had ever felt before. Amanda watched my unsteady maneuverings and laughed heartily, the pain from my shoes and bra kept me from seeing the humor in my predicament.

"Amanda, you must know that you cannot kick a guy in the balls for two hours without causing permanent damage," I pleaded.

"Not my problem, you made the bet. If you had won I would have fucked your brains out." she answered.

It was hard for me to remember thinking of her as my next conquest, to even imagine being worthy of seeing her perfect body unclothed. Her tone told me that she was not even a little bit interested in the fate of my balls after she had her fun. "Amanda, please, I'm begging you, I will do any thing."

"Anything?"

"Anything!!!"

Six months later I am at Amanda's condo, just like every Thursday night. I spend from 7 to 10 PM scrubbing and cleaning every inch of the condo, every toilet, sink and floor. I am wearing the same outfit as that fateful poker night, nipple clamps, water balloons and all, struggling to maneuver on the heels. I hand wash my maids uniform after my work is done. Amanda leaves a list of chores, occasionally supervises, and delights in swatting my balls for shoddy work. Recently she has started having friends over. Any time she is in the room I must be on my knees with my eyes downward. This is so she never again will have to feel degraded by my staring at her magnificent bustline. Occasionally she taps the back of my head as I am kneeling, and on cue I close my eyes, lift my head and open my mouth to serve as her ashtray. As I swallow I quickly say, "Thank you Mistress." All of this and more was what it took to convince Amanda to show mercy after that fateful poker game. With no leverage, I pleaded my case, offered anything I could think of. After a very one-sided negotiation, Amanda agreed to the following deal:

The value of a kick in the balls was set at $500.

This was Amanda's decision, I had no recourse but to accept her number.

Three kicks could be worked off as her maid, totaling 2 years of weekly maid service. Amanda allows me to work off my debt at $5 per hour of cleaning. There is no limit to what I can be told to do as a maid, and this has even included being forced to orally service one of Amanda's dates who didn't make it into her elite over 8" club. More than once Amanda has invited her good friend Julie over on nights when I am working. Amanda loves to watch me lick the bottom of Julie's shoes clean. Julie then laughs as she orders me to place my balls into her cupped hand. She then slowly increases the pressure on my balls as she instructs me how I will be spending the next hour working my tongue into her ass. One hard squeeze means further, two hard squeezes means faster. She spends the evening using my testicles as a speed control to give herself several orgasms. She repeatedly reminds me that I won't be getting any pleasure this evening, I will only be used for her pleasure. This is only fair she points out, as I was the only one to get pleasure the night we were first together. The oversized breasts that I had been so critical of only months before are now cruelly taunting me as they stay hidden from my view. I would not even think of asking to be allowed to touch them the way I did a few months before. Knowing that I will never again have access to such generous breasts, and that Julie has promised me she will never allow me to do anything but service her ass with my tongue, has ensured that any time I spend with her I endure in a state of intense arousal.

A fourth kick was purchased for $500, a check I wrote that night.

A separate condition of the deal was that Amanda photographed me nude, including a close up with a modified ruler that make my dick appear to be 3" fully erect. She found this to be hysterically funny, and then insisted on photos in drag. This is her insurance on my maid service.

A side effect of my experiences with Amanda, what she refers to as a "freebie", is my extraordinary fetish for women who smoke. Amanda noticed that whenever she or a visiting friend lit a cigarette the front of my maids uniform would quickly bulge obscenely. While I was prohibited from looking at Amanda, if she was smoking I couldn't help but try to steal a glance. A deep inhale would cause a desperate surge in my loins. Worse, I soon found myself lingering outside office buildings, airline terminals, or any other public place where I might find attractive women smoking. I would return to my desk with tented slacks, and inevitably would have to slip off to the men's room for relief. Amanda often taunted me about my new obsession, but would only smoke if I was safely in another room and could not watch. When Julie found out about my new fetish, she made a point of meeting my advertising assistant for drinks and gave her the whole story of my fetish and my "arrangement" with Amanda. My advertising assistant Patty is a 25 year old, hot and busty red head. From the day I hired Patty I was guilty of occasional lewd glances at her fantastic figure when I thought she wasn't looking. She has a body that is made to be noticed, and revels in the attention. She dresses in a style that highlights her dazzling figure, and is just barely appropriate for the office. Everywhere she walks, men stare with lust, women with envy and resentment. Patty is a confident, unapologetic smoker who obviously feels more attractive when she is smoking. More than once she has pointed out that the women in our office with the best bodies all smoke, she being the finest example of this rule. The number of men who worship her smoker's body outnumber the men who complain about her smoking 10 to 1. Why quit when she can have any man she wants now.

After her meeting with Julie, Patty started leaving her pack of Parliaments on her desk. Just the sight of the pack caused my cock to stir. If she was away from her desk I would quickly find a window with a view of the smoking area and watch. Several times Patty has caught me looking, but would only smile a knowing smile. During meetings she would excuse herself for smoke breaks, occasionally asking me if I wanted to join her so we could continue our meeting. As soon as Patty placed a cigarette between her full, pouty lips my dick would extend to it's full length and breadth, bearable only because I knew to position it in advance. I could never continue our meetings without a trip to the men's room, and was sure I was being paranoid when she seemed to smirk when I returned.

My worst fears were confirmed when she confronted me on a business trip. After a day of meetings, we decided to meet in the hotel bar to review the day's notes. While I was busy pulling out materials from our meetings to review, Patty ordered drinks and removed her jacket. All day her jacket had hidden a scooped neck, skin tight white t shirt. The t-shirt strained to contain her large breasts, which were accentuated magnificently by the form fitting top. I stared blatantly at the outline of her nipples that emerged in the air conditioned bar, unable to help myself. Patty pulled out the clip in her full, red hair, and shook it loose so it hung down to her shoulders. In seconds she had transformed from a business woman to the hottest thing, by far, in the bar. She noticed my staring at her bustline, and used a long manicured finger to make a slight bra adjustment. After a few drinks, and over an hour of work discussion made difficult by the amount of cleavage Patty was now showing, I was disappointed that Patty wasn't smoking. Despite my disappointment, I had a semi-hard erection. My heart jumped when Patty finally pulled the pack of Parliaments from her bag. Rather than lighting up however, she placed the pack down on the table and ignored it.

After nearly fifteen minutes I couldn't stand it any more. "Aren't you smoking tonight?" I asked in an unsteady voice.

"Maybe, but it will cost you." she replied coyly. I looked puzzled. "What do you think, I'm stupid." Patty snapped. She stood from her chair and prepared to leave the bar. As she bent over to gather her things Patty watched me stare open mouthed down the front of her skin tight top. I followed her as she headed for the exit. Everyone in the bar watched her leave, and a waitress gave me a condescending smirk as I followed.

A half hour later I was nude, on my knees in Patty's hotel room, with my rock hard dick pointing skyward. I paid her $100 to allow me to jerk off while I watched her smoke a cigarette while still fully clothed. First however she made me write a letter offering her the money to allow me to watch her, and confessing my months of obsession with her taunting figure. Further the letter stipulated that I would not touch her, and would not see her unclothed in any way. She would watch and smoke while I masturbated, period. I was naked and intensely erect the whole time I wrote. "No stroking or smoking until I have my money and letter," Patty instructed as I wrote. Finally the letter was done to her satisfaction and tucked safely away. Patty sat on her bed, leaning back on her elbows, her heavy, full breasts straining the fabric of her top to the breaking point. Her pack of Parliaments sat beside her as she gave me my masturbating guidelines. "One fingertip, five stokes, then stop for one minute, then repeat. You've got ten minutes." she directed as my cock drooled helplessly.

"But I paid you to let me cum!" I protested.

"No, you paid to masturbate, you didn't stipulate that you wanted to cum. You can have your money back if you want." I knew without asking that the letter was hers to keep. Patty placed a cigarette between her lips and lit it. A plume of smoke was sent toward the ceiling. "Shall we start?" she asked.

Patty watched in amusement as my cock jerked helplessly at the sight of her smoking. Desperately, my finger took its first five strokes. For a full minute I was helpless to do anything as she smoked leisurely and chuckled at my painful frustration. Every minute, my five strokes only teased me further, not nearly enough friction for the ejaculation I craved. Twice she made me stop to hand her an ashtray, giving me a quick view of her cleavage as she bent over. My tenth set of five left me no closer to relief, and I found myself thrusting into the air. Patty laughed at my failure to cum and ordered me to get dressed. I dressed in silence, disgusted at how I had degraded myself in front of a direct report, but painfully aroused. I struggled to fit my stiff cock into my pants. Patty stopped me as I struggled, and ordered me to point my hard-on down between my legs before I zipped up. I protested that it was impossible when it is so stiff, knowing as I spoke that this just reinforced her power over me. She was unmoved by my pleas, and I forced my rigid pole between my legs, forcing me to finish dressing bent over.

"This way you can stare at something besides my chest," she pointed out as my head was now belt high. My erection only intensified as Patty's sensual smoking style, large taunting breasts, and her delight in the complete shift in power between us deepened my humiliation. I knew that from now on a lowly 25 year old advertising assistant would be in a position to call her own shots, could expect me to give her anything she wanted. When I was dressed Patty unlocked the door. I asked her if I could masturbate again, ashamed as my bent erection forced me to stare at the floor.

"I'll pay again," I stammered, "I'll pay extra if you let me cum," I pleaded as I stole a glance at her heaving bosom.

"Get out." was Patty's flat response as she gestured toward the door with the two slender finders cradling a freshly lit cigarette. "There is no way that I would let you squirt in front of me, not after I've seen that puny thing."

I would have given anything to touch her oversized breasts that had teased me so cruelly for months. As I reached for her, Patty's long fingers closed around my balls and twisted. She blew smoke back in my face as she glared at me. "I said get out!", she snarled, as the pain in my groin had me gasping. She didn't release her grip as she backed me up to the door, opened it, and lifted me by my balls as she tossed me into the hall.

I spent the night alone in my hotel room with my balls aching, jerking off to torturous fantasies of Patty smoking in the nude with her young firm breasts swaying before me. At the end of the night my dick was shrunken and badly chafed from my desperate attempts to satisfy my cravings. I knew then that my work life had changed for good that evening. While I continued to manage a department of dozens of people, Patty became my unofficial boss from that moment on.

That letter now safely in her files, Patty made two demands as soon as we returned to the office. Every day I now deliver a pack of Parliaments to her desk as soon as Patty arrives at work, regardless of who might be there or watching. I am not allowed to use the men's room without asking Patty out loud. This allows her to humiliate me further and denies me the opportunity to jerk off at work when she is there as she carefully monitors how long I spend in there. Patty now is perpetually working on "special projects", a do nothing assignment that requires me to work extra hard to cover for her lack of production, and only occasionally requires her to come to the office. Patty also receives two evenings of maid service every month until my contract with Amanda expires. She requires that I clean in the nude, with a half gallon milk container tied to my balls dragging behind me. Depending how good a job I did cleaning the last time, Patty decides how much water to put into the container. A night with a full container, eight pounds of water dragging behind me, leaves me with swollen balls that ache for days. The smell of smoke that lingers on her form fitting knit dresses continues to taunt me whenever I am close. More than once she has rapped her knuckles into my unsuspecting groin as she hissed, "Eyes up!", knowing that I am now a slave to her firm, youthful breasts. Every day I imagine her naked, full breasts gently lifting as her lungs fill with smoke, knowing that I will never be allowed to see or touch them.