Ultimate Pleasure, Ultimate Pain

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.