Ultimate Pleasure, Ultimate Pain

Ultimate Pleasure, Ultimate Pain

by skip5236

Amanda is a the kind of woman that I am helpless to resist. Tall, about 5'9", dark hair with high cheekbones, a narrow waist and hips, and a set of what I would later find out were 34 D's that make it impossible to maintain eye contact. The short black skirt and tight white T-shirt made a package that could stop traffic. She appeared to be about 30. I had long been looking for an arm ornament and plaything like her. About five years older than Amanda, I have never had trouble meeting women. I'm tall and thin, with preppy looks that work well in my pursuit of fashionable career women. In my job as an advertising VP, I meet these women in abundance. Amanda and I met at a mutual friends' roof deck barbecue. Her superior, bitchy attitude had me staring, and not hiding it well. Finally I managed the courage to approach her, asking if I could freshen her drink. Without hesitation she ignored the drink offer, instead directing me to the store on the corner down one block with instructions - Virginia Slims, hard pack. There was no hint of an offer of money as she returned to a conversation with a very tall rail-thin redhead. She obviously had no doubt that I would follow her instructions immediately. I was left speechless by her assumption that I would do her bidding, but could not help but follow the orders of this woman who was obviously comfortable giving men direction. I arrived back breathless from the four story climb. Amanda took the cigarettes from me without making eye contact or acknowledging me in any way. I waited patiently over the next two hours for her to be free so I could approach her again.

As she was leaving, my much too desperate invitation for dinner was dismissed with a derisive chuckle, and "If I nothing comes up between now and then." I was desperately aroused all week thinking of her.

Our Thursday night dinner date finally came, and I arrived at the restaurant 20 minutes early, and 50 minutes before Amanda. I nursed a club soda at the bar while I waited. Amanda arrived and was seated immediately, changing our table from non to smoking. She sent the hostess to the bar with my instructions to fetch a pack of Virginia Slims while she was being seated. The hostess was a sophisticated looking, tall waif-like blonde. She didn't hide her amusement at the way Amanda treated me.

As I looked furtively about the bar, she smirked and said, "There's a corner store two blocks down."

I dashed to the store, and my return to the restaurant was greeted by the same hostess. She gestured to my table and condescendingly observed, "Back so soon?". Her tone praised my swiftness in a way that was intended to mock me, and was effective. She apparently enjoyed treating men with same disdain as Amanda. Her small, but firm and high set breasts poked at the fabric of her fitted dress. She carried them with a confidence that said "Sure they're small, but I know you want them bad." My attempt at sneaking a quick glance was met with an icy stare. Her stare told me that we both knew two things for certain at that moment. Like any healthy male I found her desperately attractive, and that there was no chance that she would ever give me the time of day.

She reached under the hostess stand as she told a co-worker, "I'll be back in five." Cigarette case in hand, the hostess slid by me out the door, telling me in a tone dripping with insincerity, "Hurry along to your table, you wouldn't want to keep her waiting."

By the time I arrived at the table Amanda had ordered a bottle of wine ($42 I later found out), and never lifted her gaze from the menu as she held out her hand for the cigarettes. Tight jeans, heels, and a silk T-shirt. My member started to twitch just looking at her. She offered no explanation for being late, and I dared not ask. She opened conversation showing no mercy at all. "Julie tells me you used to date."

Julie was the host at our barbecue meeting. A medium height, top heavy blonde, she carries about five extra pounds. It took three torturous dates before I finally got her bra off. Her breasts were enormous, but somewhat saggy. Lying on her back, they tended to fall to the side in a manner that was not attractive. I was disappointed, but pushed on. Despite my disappointment, my hard-on was quite urgent, courtesy of a six week dry spell. Julie slid her mouth over my pole, and after three strokes I did an admirable job of filling the condom tip. Julie didn't press the issue of her getting off, which was good as I couldn't have been less interested as I reveled in my post orgasmic laziness. As Julie continued to make small talk, I did a poor job of looking interested while I returned to the movie on the television. Finally, she started to gather her clothes. I made a point of scooping up her bra for her, only so I could note the size, 38-DD. I had long made a habit of remembering my conquests by their bra size. Like any breast man, I have always known that this is the only feature that truly matters in a woman. I pride myself on never forgetting the vital statistic, from my first grope (Beth, 32-B) to my friends wife who I accidentally walked in on in the shower (Victoria, 36-C). I never called Julie after that, having gotten what I was after, and was thoroughly tongue tied when she called me 6 months later with a barbecue invitation. Just a group of single friends, most of them women, gathering on her roof deck. She cut me off when I offered a lame explanation about traveling alot, with a blithe "So I'll see you Saturday?"

"Julie tells me you used to date." Amanda's tone made it obvious that she knew, her face was expressionless. I babbled, hemmed and hawed, while she silently let me suffer. Finally, mercifully, she cut me off by signaling the waiter. "I'm having the salmon," she announced and closed her menu.

Conversation actually flowed easily from there, as the wine relaxed us, and we talked about hobbies, jobs, and favorite travel destinations. Dinner was excellent, although I was almost too nervous to eat it. Amanda's beautiful face had me enchanted, I found myself desperately wanting to touch her. Over coffee she talked about a trip to Lake Tahoe. Mid-sentence, she reached across the table and lifted my chin, unsmilingly pointing out, "My eyes are up here." Those 38 D's were merciless, and I was semi-hard most of dinner. The Tahoe conversation turned to conversation about casino's, and great gambling experiences.

After relating a few meager stories of my trips to Las Vegas, each one topped easily by Amanda's experiences around the world, I decided I needed a victory in this conversation. Gambling is a manly pursuit, and I needed to show this goddess that I was indeed quite manly. "Those glitzy casino's are ok, but real gambling is a bunch of guys playing high stakes poker" I declared as she started gathering her things to leave. This was a bold statement, and made under considerable duress as I was recovering from the blow of the $150 dinner bill I had just signed for.

"Bunch of guys?" she questioned, in a tone that was both doubtful and condescending.

"Yes, bunch of guys, poker is a mans game" I announced sounding nearly certain of my ground on this issue. By now we were in front of the restaurant, her red Miata was pulling to the curb.

The nineteen year old valet gently handed her the keys. "The car's all set, Ma'am," he said directly to Amanda's left breast.

Without a word she walked around and climbed in, put the car into gear, and looked over her shoulder into traffic. "Well ..." she said, in a tone that was obviously an impatient command to get in. I jumped in before the valet decided she was speaking to him.

We roared down the highway along the river, exiting at the base of the hill downtown where old money and new money barely co-exist. Lurching to a stop in front of a waterfront high rise, she left the keys in the car and strode past the doorman. " Tomorrow at 9 Wilson" she instructed to older, uniformed attendant as he gaped openly at her long, denim clad legs. Not knowing what else to do, I jumped out and followed.

Without words, she entered the elevator, forcing me to scramble in as the doors shut. We rode in silence to the sixteenth floor, and I followed her into 1602. A large one bedroom with panoramic views of the harbor, probably close to a million. Furnished beautifully in contemporary black leather and chrome, dark and cold. Amanda poured a splash of brandy into a snifter, offering me nothing. Dropping comfortably into the overstuffed sofa, she gestured dismissively to the leather chair. "A man's game?" she mused, obviously fixated on my macho rantings from the restaurant.

"Well, uh, I guess women can play, but uh, well....".

"But uh, what?" she demanded. "You want to back macho words with action, little boy?"

I was both puzzled and offended, "How?" I asked in voice that was a little too high pitched.

"You and me, poker, with real stakes, not just the quarter ante nonsense you boast about."

Not knowing quite what else to say I stammered, "What are the stakes?"

"Ultimate pleasure or ultimate pain," she announced. "Strip poker, but we are honest up front"

"Honest?" I asked.

"Strip poker is nonsense, " she declared, standing up, in a tone that did not invite opinion. "If you win, you take your free peeks and then I get dressed, right? Yeah, right. Every guy expects that he is going to get laid if he gets a woman's clothes off. If she doesn't put out, she's a cock-teasing bitch. So let's just be honest about what we are playing for here." My dick was stiffening in my shorts just thinking about Amanda, bent over, with me driving my pride and joy into her. Her standing in front of me, her silk t-shirt barely containing her oversized bra, wasn't making it any easier. "From a woman's perspective, the game is stupid too." she continued. "Some prize we get, we get to see some loser naked with a limp dick, who is still expecting to get laid. What do we win?" I started to see her point. Amanda now put forth the stakes. "If you win, if you get all of my clothes off, I am yours for an hour. We set the timer, and you can shove your thing in my mouth, my ass, between my tits, my pussy, anywhere your pathetic tool wants to go. One hour, as many times as you can get off." I was rock hard just listening to her. "If I win, though, I get to do what I like." she continued. "You will stand naked in front of me, hands behind your head, legs spread, and I will kick you in the balls. We repeat the process every thirty minutes, a total of three free kicks in the nuts. Ultimate pleasure or ultimate pain."

I was dumbstruck by her proposal. "You like kicking men in the groin?" I stammered.

"More than anything." she snapped right back.

While I was horrified by her proposal, my stiff dick, her eye level swaying breasts, and my certainty that I would win left no doubt what my answer would be. She went to get the cards.

Amanda sat on the comfortable sofa, a coffee table in front of her. A straight back, wooden chair was dragged in for me. We sat across the table as she shuffled. She concentrated on shuffling the cards, I tried to use my slightly higher seat to gain a view down her T-shirt. The initial deal yielded three sevens, good enough to beat Amanda's pair of kings, and her watch fell to the far end of the sofa. Three hands later, my watch and both shoes were in a pile on the floor beside me. Amanda dealt the next hand, and after taking three new cards I had a full house, queens over fours, easily beating Amanda's pair of sevens. It felt good to win a hand, but I can't say I got too excited over one hand this early in the game. I waited for a high heeled shoe to join her watch at the end of the sofa.

Amanda stood up from the sofa and gazed down toward me. The smooth silk of her T-shirt strained across her full bosom. She purposefully reached across her body with both hands, and in one smooth motion pulled her T-shirt over her head and tossed it aside. Her two enormous breasts jutted proudly forward from her chest, each full round globe capped by a very large brown nipple that was only partially covered by a half cup white lace bra. The camisole like lining lay in a heap with the silk shirt at the end of the sofa. I was shocked by the suddenness of her action, and awed by the finest breasts I had ever seen. They were humbling, and the way she carried them was very powerful. Unable to help myself, I let out an audible gasp, and immediately blushed at my wanton admiration.

Amanda smiled a cool calculated smile, "Don't be embarrassed, every guy does that." I was brought back to earth by the painful discomfort as by member strained mightily to tear open my pant leg. I tried to relieve my discomfort with urgent, but discreet pocket adjustments.

Amanda smirked, and said, "I'm sorry, did I do that? It might be easier to fix if you stood up."

Humiliated and desperately turned on, I turned my back and made the necessary adjustments. Anxious to continue the game and collect my now obvious rewards, I grabbed up the cards. I tried to use my arm to hide my tented pants, but Amanda's smug expression made it clear she knew who really held the upper hand. The state she had put me in was obvious, and it was pointless to ask why she had chosen to remove her blouse at this early point in the game. I began to realize that I might be out of my league.

My concentration was shot as I dealt the next hand. Her breasts, the most perfect flesh forms ever created, rose and fell gently with each breath. I wanted to speed up the game, anxious to get Amanda's bra off as quickly as possible. I was already estimating it's size to add to my list. On the next hand, I accidentally discarded half of a pair of eights, and ended up with nothing. I quickly lost the next two hands and was now barefoot, in slacks and an undershirt. Amanda dealt me a full house on the next hand, and I confidently spread my cards on the table. Amanda glanced at the cards, smiled and laid four six's down. I was astounded, but resignedly pulled my undershirt over my head. It was becoming clear that I was not going to win, and a sense of panic started to grip me as I realized what my fate most assuredly would be.

Amanda leaned over to gather the cards for her deal, and looked up in time to catch me staring at those magnificent breasts as they hung loosely in her flimsy bra. She held my gaze, and smiled an evil smile. "Enjoy the view, they're 34 D's, and this is as close as you will get to seeing them." she sneered. "Don't feel badly though, as many times as I have played this game, no guy has ever gotten my bra off." She laughed and added, "I'm sure many more will try." From where I was sitting, I was sure she was right.

Winning the next hand was small consolation as a shoe landed on her clothing pile, and the second shoe joined it the following hand. My pair of threes on the next hand cost me my pants, and the humiliation meter started climbing. Removing my pants with my rigidly erect penis pointing skyward was bad enough, but the large, sticky wet spot on the front of my underwear told Amanda that her antics were taking their desired toll on me. My cock was as hard as it had ever been, and I desperately wanted to stroke myself to release, even if I had to do it here in front of her.

Amanda sat smugly, silently reveling in the power her body possessed when she chose to use it as a weapon. She had long ago learned that just her breasts could render any man painfully hard, and helpless. She let out a small laugh, gazing at my bulging, soggy briefs and said, "I guess Julie was right," as she held up her hand, thumb and index finger about two inches apart. Instinctively I held a hand in front of my crotch as I vainly tried to cover up my small endowment. I felt pathetic as she laughed at my underwear bulge. I knew I would soon have to uncover my erection, barely four inches when fully engorged. I had never felt self-conscious about the size of my erect penis before, but in the face of such a powerful woman it suddenly seemed obvious that I would fall far short of her standards. My now painful arousal, and the certainty that I would not be having sex this evening, had turned my intense hard-on into a weapon for Amanda to use against me. I knew that I could not even give myself relief without Amanda's consent, and could only imagine how pathetic she would make me feel as I tugged on my puny dick. My balls felt full and heavy, and horribly vulnerable now that I knew I would soon be paying up on my ludicrous boasting of earlier.

"Too bad you are playing so poorly, it looks like your little friend was planning on winning," Amanda said as she eyed my soggy crotch. "It looks like you haven't let little Mr. Happy out for awhile, how long has it been since he got to play with someone besides your hand?"

I somehow knew that I couldn't get away with lying. "Um, ah, about six months" I mumbled, sinking further into abject humiliation as I had not gotten any since that night with Julie.

Amanda laughed out loud. "No wonder macho man's hand is so callused." She then reached across the table with her bare foot and nudged my balls. "And how long has it been since you had to take matters into your own hands, stud?" she demanded.

"Four days," I mumbled again.

Again nudging my balls, she said, "Four days! Ooooh, these guys must be feeling pretty heavy then?" An evil smile came to her face. Amanda knew very well the most painful fact that separates men from women. While four days without sex is inconsequential to women, by day four any man is in fairly desperate straits. The cum build up in my groin had put me in that danger zone under normal circumstances. With Amanda now playing my sexual need like an expert musician, I was a slave to my painful erection and swollen balls. She held all the cards in this game, and this malicious cock teasing was just foreplay to the violent finale she had planned for my most treasured parts. The terror of the fate that awaited my balls was starting to take hold. I was desperately thinking of ways to avoid paying my debt, trying to buy time to think.

I was relieved when Amanda interrupted the fog of my racing thoughts. "Go into the kitchen and bring me my cigarettes," she said in a manner that was obviously not asking. My tented, sticky briefs led the way as I brought back the pack of Virginia Slims, then fumbled with the lighter hoping my chivalry would make her forget our bet. Amanda's sensual smoking style only inflamed my arousal further, as she sent a purposeful plume of smoke back toward my face.

"How about we make a deal?" she asked rhetorically.

"A deal?" I answered much too quickly, sitting uncomfortably in my sticky briefs.

"Double or nothing," she said. "Go into the bedroom and bring me the blue bag from behind the door."

I raced into the bedroom and fetched the blue bag as ordered. "Here's my offer. This bag contains an outfit, lingerie and all. I will let you continue to play after you have lost your briefs, but for each hand you lose you have to put on an article of my choice from this bag. If I lose a hand, I will continue to take off clothes." Amanda pulled deeply on her cigarette, hollowing her sculpted cheeks, as she let the first part of the deal sink in. "However, there are a few conditions. If you empty the bag, when you are dressed completely as a woman, your penalty becomes double. You will spend two hours, dressed in drag, getting your balls kicked. But, if you win as many poker hands as I have clothes before the bag is empty, you win your way back to even, meaning you have won your balls back. With one last condition. If you win enough hands so that I am wearing only panties and a bra, you will win the game if you win two more hands. The panties and bra stay on in this deal, you just win your way back to even. Accept the deal, and you have given up any chance of seeing these naked." Her hands cupped and squeezed together her cleavage causing me to inhale sharply. I was now defeated, faced with two humiliating outcomes. Either I was going to wear women's clothing, emasculated in front of the most attractive woman I had ever seen in her bra, so I could "win" and get to watch her put her clothes on. It was a foregone conclusion that I could never touch her, and the growing stain on my underwear made it clear to both of us how badly I needed to do that. Or, I watch this beauty laugh and enjoy two hours of pulverizing my swollen nuts. I had no doubt that Amanda had controlled every aspect of this game from the beginning, and my chances of "winning" were nil. I couldn't concede though, as this meant the ball busting started immediately and I had to take any chance necessary to avoid that fate.

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.

Amanda refused to deal the last two kicks. No amount of pleading or begging could change her mind. So, stark naked, I stood with hands behind my head and legs spread, whimpering. Amanda put her hands on my waist, and let her clothed breasts rub lightly against my chest. My penis involuntarily jerked at the touch of her breasts.

Amanda looked down and chuckled. Her smoky breath, as she chastised me in a low voice, only furthered my involuntary arousal. "You never learn do you. That's what got you in trouble in the first place." Looking directly into my eyes, she lightly stroked the side of my face. "I've done this many times, don't bother trying to be strong."

Her knee slammed into my testicles, crushing them against my body. For a moment I didn't feel anything. Then the dull, sickening pain radiated rapidly up into my abdomen. As I tried to crumble to the ground, nauseated and clutching for my flattened balls, Amanda briefly propped me up under my arms. She looked me in the eye and says, "See you in half an hour, there's more where that came from. I'm going to have a cigarette and enjoy the show." She steps back and watched me drop to the floor, writhing and clutching my balls, knowing that they are now hers.