Strip Poker... Gone Badbyskip5236©
She arrived at my hotel room exactly as advertised. Tall, about 5'7", very thin with shoulder length coal black hair. She had mocha skin, and big brown eyes on a striking face. As she slipped her coat off she revealed a skin tight black t-shirt that struggled to cover an oversized, high set bustline. Most likely not all natural. "So, let me get this straight, you will pay me my full fee, and I might not have to do anything for it," she said.
I pulled her phone number from a local newspaper. The ad said all the right things. Young, very busty, thin, very attractive. I called her with a proposition. Up front I would pay her $200 fee. In exchange, she and I would play strip poker. No tricks, just a straight forward game of cards for clothes. If I won, she would deliver the blowjob I paid for. If she won, she could do whatever she wanted, including get dressed and leave. I would agree to do whatever she asked for the remainder of our hour together. It took some convincing that I wasn't a nutcase, but eventually she agreed.
Eight o'clock sharp she arrived, and I couldn't help but be pleased with her beauty. I almost thought twice about my offer as she tossed her coat aside, knowing that I would bitterly regret passing up such an enormous set of tits if I lost. However, a deal is a deal, and I handed over her money. "Call me Tiffany. So, how does this work?" she asked as she flopped onto one of the double beds. He boobs barely moved as the rest of her bounced lightly on the mattress.
"We play straight five card stud, dealer wins in a tie. We alternate the deal." I said, my eyes never leaving her chest. Her elbows propped her up, stretching the t-shirt across her bosom to it's limit. My cock shifted noticeably in my slacks, I was forced to make some pocket adjustments.
Tiffany watched coolly, long past being surprised by the effect her body had on men. I had already pulled a small table between the two beds for us to play on. Tiffany still seemed unconvinced of my sincerity, and pressed for more details. "And if I win I take your money and you get nothing, right?"
"That's right," I responded quite emphatically, hoping to dispel any doubt of my seriousness.
"So, let's play," she said with some conviction, obviously still a bit unsure, but willing to give it a try.
We did a quick clothes count comparison to be sure we were playing fair, Tiffany negotiated keeping her one extra garment due to her lack of experience with poker. We did quick rules review, and I reviewed what the order of winning hands are. Tiffany seemed a little confused by flushes and straights, but grabbed the deck and began to shuffle. She dealt five cards rather awkwardly, and dropped about a third of the deck off the little table. She scurried to pick up the cards as I enjoyed the view of her tight little ass. Finally we picked up our cards.
Tiffany rearranged her cards repeatedly, long after I had quickly discarded my three cards, keeping an Ace and a three. Discarding only one, she dealt me my three cards, taking one for herself. We each showed our cards, and my pair of fours easily beat her Jack of spades high. She discarded a shoe as I wondered if there was any hope of her playing a decent game. I quickly shuffled and dealt, amused by the look of extreme concentration as she picked up each card. Her concentration didn't appear to improve her game, as she again laid down a hand with nothing, my three sevens taking hand number two. I was amused as her second shoe slipped off, and prepared to start seeing some flesh with the next hand.
Her reclaiming the deal promised to be a tedious process based on her earlier performance, and while she did better this time, her shuffle was very crude and clumsy. She dealt me my five cards, counting out loud as she dealt. She took a deep breath, and scooped her cards up. I glanced at my cards, and almost felt a twinge of guilt as I found two pair, Queens over nines. I discarded one, and watched her take three cards. Finally Tiffany laid down a hand with something in it, a pair of sevens, which only added to her frustration as I sheepishly laid down my winning hand. I leaned back to enjoy the view as she stood and undid her tight jeans. Tiffany turned her back and slithered out of the snug denim, her black lace panty clad butt wiggling free. A chiseled butt and smoothly muscled legs showed a commitment to the gym. I could feel my cock extending to its full length as she tossed the jeans aside and stood before me in the lycra top and skimpy panties.
"This game isn't going to take long as this rate" she said in a tone thick with exasperation. Silently I reluctantly agreed, but managed to keep my disappointment in check as I imagined her naked body and full lips wrapped around my by now fully hard dick. I prepared to deal the cards., anxious to win another hand and add her t-shirt to the pile.
I quickly dealt a round of cards, and was surprised to find nothing in my hand. I didn't notice Tiffany's newly efficient manner of sorting and discarding her fresh set of five cards. My new set of three cards didn't improve my hand, and for the first time I tossed one shoe aside as Tiffany giggled with glee. My next hand wasn't any better, and I was now barefoot. Tiffany leaned in to gather the cards, and met my eyes as I tried to steal a peek down her shirt. Dealing the next hand my busty opponent seemed to have a newly practiced manner to her card playing, and I was suddenly nervous as my three kings was trumped by her heart flush. I removed my shirt, and resolved to focus and make short order of getting this woman naked and busy on my manhood. I just needed to focus, and get this game over with.
While I was enjoying the game, my dick pulsing beneath my slacks was anxious to claim victory. I dealt a fresh five, and found a pair of tens. Tiffany had already discarded, and waited impatiently for me to proceed. I replaced my discard with two threes. Before I could lay them down Tiffany had three queens on the table, and I disgustedly tossed my cards face down. "I started with a pair of tens, I thought I had it ," I snapped.
Tiffany snickered and squeezed her cleavage together. "This pair of tens always gets me what I want. At this rate, your not going to get to see them though," she taunted back. I started to get irritated with her cockiness, and was even more annoyed with her suddenly developed shuffling and dealing skills. Tiffany held my gaze as she efficiently shuffled and dealt. As she set the cards down, she slowly brought her right hand to her mouth. She extended a long manicured finger, and slipped it slowly between her full lips. Her lips parted slightly as her tongue snaked out and traced a long wet path down the lucky digit. Again, her lips sucked in the finger all the way to the knuckle. Slowly, ever so slowly, she withdrew the finger as her teeth lightly scraped it's considerable length. Tiffany's eyes never left mine as I stared hungrily at her beautiful mouth. Unable to help myself, I grabbed the front of my slacks and squeezed my aching cock. I was now helpless, and needed relief from my intense arousal. The growing stain on the front of my tan slacks caught Tiffany's eye, and her contented chuckle showed her experience as a malicious cock tease.
I grabbed up my cards and discarded, but in my haste and arousal, accidentally discarded half of a pair of tens. I reached for my discard, mumbling that I had made a mistake. Tiffany's hand shot out and grabbed my arm, digging a polished nail into my wrist, and the look on her face made it clear that she knew the rules. I yelped slightly from the pain from her nail, and snapped my wrist back. I once again had nothing in my hand, and had no choice but to add my pants to the clothes pile. I was strangely embarrassed by the obvious bulge my painfully hard cock made in my underwear. Glancing at the transparent wet spot at the end of the bulge in briefs, Tiffany smirked and said, "Looks like he was planning on winning." I blushed at my obvious arousal. "Too bad", she added, "because a date with your hand is all he has coming, and this mouth sure can suck cock." I was put off by her brashness, she only had a one garment lead in our game, yet sensed that she somehow knew the outcome already. Her finger sucking display left no doubt in my mind that Tiffany's boast was true. I ached for the blowjob I had paid for, and knew my hand would be a poor substitute.
Tiffany had already finished shuffling, and was now dealing a new hand. For a change I finally had a good hand in the deal, a pair of sevens and queens. My only discard yielded another seven, and my full house was bound to get me either her stretched lycra top or her skimpy panties. Tiffany's three sixes were tossed aside, and she stood before with her chest jutting forward. I hoped she would choose to discard the top, and the now soggy wet spot on my briefs showed my anticipation. Slowly she turned her back and started to fumble with her clothes. After some inordinately long fumbling, Tiffany turned back to me and tossed her bra on the pile. It was a bra like I had never seen, the cups were huge, and a vision in black lace. Each enormous bosom encased by the black lace would have been a magnificent sight. I felt cheated by her clever effort to rob me of my rightful claim to seeing more of her body. I opened my mouth to protest, but again she shot me a look that silenced me and forced me to accept that I had been outsmarted.. I couldn't help but stare at her enormous bosom, now straining the fabric of her top. Now unleashed from their bra, they sagged only slightly downward with a heft and fullness that I had never before seen. My cock strained to be freed from it's cage, it took all of my restraint to keep from reaching for the enormous bulge in her top.
I shuffled and dealt the next hand, and Tiffany snapped them up with a very slick style that showed many hours of card playing experience. I tossed three cards, keeping a pair of Jacks. As I prepared to deal again, I noticed that Tiffany hadn't discarded. When my new three cards gave me nothing more that my original pair. I could see I was about to have my back to the wall. I pulled my undershirt over my head and tossed it aside. Tiffany pointed to her purse, and I obediently handed it over. She pulled out a pack of Marlboro Lights, and without hesitation she raised a cigarette to her mouth and lit it expertly with a lighter. She inhaled deeply, and sent a slow purposeful stream of smoke over my head. "You don't mind if I smoke do you?" she asked in a voice that made it obvious that her question was rhetorical. It was obvious that my only hope of touching those magnificent breasts was if Tiffany chose to let me, so I didn't dare object. She gestured that I should run and get her an ashtray, an errand that I scrambled to do with my fully erect cock leading the way. It was obvious that Tiffany knew that I had to do her bidding, and she was now in no hurry to finish this game.
She next sent me to the mini-bar for a glass of vodka over ice. I reached for a glass for myself, but was stopped as Tiffany raised an eyebrow and shook her head. I brought her drink to the table, and stood with hardon jutting urgently forward waiting for her next instructions. Tiffany took a deep, cheek hollowing inhale from her cigarette, and reached for her drink as she sent a purposeful stream of smoke toward my face. She gestured for me to sit. I gathered the cards, and stared as her chest rose with her next long, cheek hollowing inhale. I accidentally spilled the cards onto the table and floor, it was obvious that I had been staring at her and not concentrating on my shuffling.
As I dealt the cards, Tiffany chuckled. "So I'm going to make $200 for making some loser's dick hard by not letting him touch my body, most fun $200 I 've ever made." She took a long sip on her drink, and watched me stare at her massive breasts. Again Tiffany extended her long manicured finger, and slowly stroked the end of one breast with her long fingernail. Her eyes slowly closed to a narrow slit and her lips parted as she enjoyed the sensations flowing through her nipple. The nipple slowly formed a large, hard crown extending the lycra top even further. Tiffany grasped the nipple between two fingers and rolled it slowly. Her other nipple was now fully erect, and she moaned quietly as she enjoyed pleasuring her enormous mounds. Helpless, I shoved my hand down the front of my soggy underwear and pumped my aching cock. Tiffany laughed, and jerked my hand away with her foot. She lit a fresh cigarette, and gestured toward the cards. I dealt the cards, just as sure as Tiffany that I would not win the next two hands.
Once again I found five cards that gave me nothing in my hand, Tiffany quickly looked and discarded one card. I gave Tiffany her card and took three for myself. Tiffany didn't wait for me to look, she immediately laid four queens on the table. She scooped up her bra off the floor, and headed for the bathroom. "I expect you to be naked and on your knees when I come out " she barked over shoulder. Knowing that I would do anything to touch even her fully clothed breasts, she closed the door behind her.
I stripped off my soggy underwear, and knelt at the end of the bed with my erection pointing toward my navel. I stayed in that position for nearly ten minutes, staring at the closed bathroom door. Finally the door opened, and Tiffany emerged with her bra on again. The beautiful piece of lingerie was once again covered by her top. She brushed past me, and reached for my phone and her cigarettes. She slowly lit another cigarette as she dialed the phone, and arranged herself comfortably on my bed. She reached what sounded like a girlfriend, and laughed as they made plans to meet. She made a point of making sure that I heard that she didn't plan on being here long. Her sensual smoking style only served to arouse me further. I started to stand from my still kneeling position, but an immediate hand motion signaled that I was to remain kneeling. As she laughed through her phone conversation, her enormous chest would bounce firmly up and down.
Finally she hung up, and reached for her jeans. I groaned as she worked her way into her tight jeans with an exaggerated wiggle. "This isn't going to be easy for you is it?" she asked. "I would have been happy to give you a hand job at least, but it's too much fun to leave a guy with a hard-on." She slipped on her heels, and stood before me. "I used to do this all the time in high school, especially when I dated college guys. I loved teasing. Guys would spend the whole night staring at my chest pretending to be interested in me. I would always get the last laugh when they would have to beg to touch me with their hard dick sticking out of their pants. None of them ever got their hands on these baby's." she laughed as hefted a breast in each hand. She once again took a long, leisurely inhale from her cigarette. Tiffany grabbed her purse, and walked behind me. She sat down on the end of the bed in front of me. She raised her left foot and slowly ran her heel the length of my drooling cock. I gasped and lunged forward. Tiffany laughed loudly, and pushed me back with the same heel. She then held up the bottom of the shoe before my face. "Kiss the shoe and thank me for giving you that puny little hard on." She ordered.
I kissed her food tenderly and gasped out "Tiffany please, I will pay more, just let me touch you. I will do anything." "Anything" she asked? "Anything" I said.
Tiffany took all of the money I had left, another $320. For that price she allowed me to touch her feet, legs and butt fully clothed. She then had me lay on my back on the floor and stroke my condom covered cock to one orgasm. When I protested that this wasn't a fair deal she shot right back. " Do you know how disgusting it is to have some guy you don't know pull on his dick while he stares at my breasts" she angrily replied. She picked up her bag as if to leave, but thought better of it. She slowly finished her chilled vodka as I stroked furiously. As I neared climax I arched my back. Suddenly Tiffany's toe knocked my hand away from my dick, and she knelt over me, pinning my wrists to the floor. She gazed coolly down at my pained expression as my hardon pumped harmlessly into the air. Her enormous breasts jutted out above me, taunting me further. As I gasped out my pleas for release, for relief from my relentless erection and swollen balls, Tiffany again reached for her bag and lit another cigarette in leisurely fashion. Her cheeks hollowed as she inhaled deeply. She gazed down between her unending cleavage and blew a long stream of smoke into my face. She slowly raised her cigarette to her full lips again, took another long inhale and sent another long stream my way. She took one long finger and jabbed my chin as she commanded "Open wide." I opened my mouth, and Tiffany laughed as she flicked an ash into my open mouth. "If a guy's dick is hard, he will do anything I tell him."