Canadian Doubles

Bill was a star. All through high school he had constantly won every tennis match he had ever played, and when he received a full scholarship to UCLA to play on the tennis team he couldn't have been more pleased. His talent however somewhat warped his personality and he was thoughtless, arrogant and rude. Despite these qualities his rugged athletic good looks always assured him of a steady supply of ample pussy and this too contributed to an ego that could choke a horse. Bill however was about to receive the most valuable tennis lesson he would ever take.

Every day at 1:00 PM, Bill would head down to the courts, fire up the ball cannon and practice his backhand. This was his weak suit and he knew it and if he wished to stay on the team, and thus keep his lucrative scholarship, he knew he had to work on this weakness.

He had his whole future planned out. First graduate, then hopefully get into the rankings, and make the US Open, and who knows maybe even Wimbledon. Ah, the dreams he had; covered in endorsements and hot Scandinavian lingerie models, it was perfect. Even if he didn't succeed this well, it was not hard to imagine a comfy life for himself as a country club pro, teaching tennis lessons to hot rich MILFS and thoroughly enjoying himself with lots of bored rich hot trophy wife tail. Yes, the future looked bright.

This particular day Bill, dressed only in his shirt, shorts, no socks, (jock of course) and shoes, headed down to the courts to begin his practice. He was furious when he saw that all the courts were taken and he would have to wait. Today was the inter-sorority tournament and all four courts were full up.

There were also at least 20 or 30 other girls in the bleachers cheering their teammates on and he was the only guy there. Now normally being surrounded by all this co-ed loveliness, would have greatly pleased Bill, but today he was especially focused as he had a few major tournaments coming up and he had to get some practice time in. His last match had gone bad and he had lost badly so he definitely needed and wanted to practice. Seeing the lineup and the large number of girls playing, Bill fumed as he sat down and decided to wait out the tournament.

After about an hour he grew very impatient and began to yell out disparaging comments to the sorority players.

"MY GOD! What kind of serve is that!" he sneered as Veronica shot a ball into the net.

"HA! You women are pathetic! Why don't you get off the courts and let some real players practice!" he yelled again as she missed the next shot.

Hearing the rolling heckles coming from the stands was enough for Veronica. It was bad enough that she was losing the game, but being harassed by some asshole was really infuriating her. The other girls in attendance also were annoyed as Bill, even for him, was being a GIANT dick.

"OK Big shot!" she yelled back. "If you think you are so good, why don't you come down here and play some of us. Or don't you think you can handle it?" she taunted.

The crowd grew silent at Veronica's taunt as they were all completely annoyed that Bill was ruining their tournament, and all hoped that maybe now he would shut up and leave.

"Right!" he yelled back. "I could beat all of you combined! You bitches SUCK! Why don't you all just pack up and go home so some real players can use the court! Just hurry up and lose so I can practice!"

Veronica, now absolutely livid carped back "What are you afraid of stud? Afraid a group of women will outplay your sorry ass! Mother fuckers like you are all the same. All talk and no action, I doubt you even know how to swing a racket!" With this last comment all the girls started laughing.

Bill, now having his male pride aroused, grabbed his racket and walked down to the court.

"Ok BITCH you're on! This is a little beneath my skill level, but I think I can slum today" he responded snidely.

At this comment the crowd erupted into long OOOOOOOOOOs.

"So, you really think you can beat us all do you? Care to bet on that?" she replied.

Bill was intrigued now. Back in his high school days he had won a lot of money sharking and he figured these rich bitches would be ripe for the plucking.

"Ok, I'm game. What do you say, $50 bucks a game and to show I am truly magnanimous, we will play Canadian Doubles! I will play your opponent here and will be glad to remove any extra cash you have."

Veronica fumed at his arrogance. "You really think you are that good eh? OK, we will take that bet. I frankly can't wait to humiliate your sorry ass all over this court, and let's up it a bit. In addition to losing your money, you will then have to LEAVE this court and NEVER return while we are around EVER. We are ALL sick of hearing your mouth, so you leaving will be our gift to the crowd."

Now Bill fumed but grinned. He was going to take this bet and up it too, as obviously this girl had NO idea how good a player he was. Looking at Veronica and her opponent (and now partner) Lynette, he licked his lips. They were stunningly gorgeous, and since they were making bets and obviously pissed, perhaps he could turn this into an afternoon to remember.

"Well, you are talking some REAL shit now girl! I say we up it more. I say if you win, you get the money and I will leave the court for you and your pitiful squad whenever you want it. But if I win, you and your gorgeous friend there get to come back to my dorm room and give me a special prize!"

The oooos of the crowd got louder now as the tension escalated. When Veronica uttered her next words the oooos turned to gasps, and Lynette herself looked on in horror as she had not expected to get caught up in THIS level of stakes.

"OK, I got one better Stud! I say that each game the winner gets to have the loser remove an article of clothing, winner's choice. Not only are you going to lose your money and have to leave but I am going to show your lily white hide to the crowd. I am afraid you might get a little sunburned playing naked all afternoon, but that is my bet, assuming you are MAN enough to take it." All the girls went wild when this suggestion was made.

Bill's mind raced. He knew he was good and also was completely confident that he would never get stripped. These girls were terrible and he would be able to easily defeat them and have their gorgeous naked bodies stripped before his eyes. The idea of having two girls totally stark naked in front of him was too tempting so he eagerly agreed.

The other girls sensed that there may be trouble as they saw Lynette begin to whisper protests to Veronica. She calmly whispered something in her ear which seemed to quiet her down.

"One thing" Veronica interrupted as Bill took his place "What if someone is already naked and loses?"

Bill chuckled to himself. "Well perhaps she should have to pay a penalty!"

Smirking, Veronica smiled. "Agreed! So, those who lose and are already naked have to pay a penalty. Now we will play 3 sets of 3 games, right?"

After shaking hands Bill nodded in expectant victory as he took his stance while Veronica and Lynette took their places.

Bill's serves were fantastic and he easily won the first game, firing his shots hard and fast, they never had a chance.

"OK Girls, lose the tops!" Bill yelled with glee confident that they would not get caught as the campus security guards NEVER monitored the back tennis courts.

All the girls who had gathered to watch the game moaned with disappointment as it now became apparent that their friends were going to be humiliated in front of them, and it was going to be much worse being humiliated by a giant asshole like Bill.

The second game too went his way and he confidently ordered the removals of their bras. Lynette's face flushed four shades of red as she shyly revealed two healthy 36 Cs. Veronica, with no shame at all, quickly unhooked her bra and flashed her quite impressive rack to Bill both to his and the crowd's shock.

Now in heaven as he gazed at their impressive and gorgeous breasts, glistening with sweat and bouncing wildly as they ran after his volleys it was like a wet dream. This particular day was absolutely scorching and the heat coming up off the concrete was like playing on a skillet, the heat radiating like an inferno off of the court and adding to the beautiful spectacle of these sweat dripping beauties. Bill did not think about one ramification of playing against four sets of bouncing naked boobs, and his concentration was so off by the erotic diversion that Lynette and Veronica easily beat him the next game.

Waiting patiently for their demand for an article of his clothing he was not worried at all. Nothing they could take would show anything so it was just a temporary pause on his continued stripping of the girls. He already was mentally preparing for the next game and trying to plan how he could avoid getting distracted by their female charms. Gritting his teeth, he willed himself to concentrate so that those gorgeous jiggling tits would not distract him enough to keep him from winning.

"Lose the shoes Bill!" Veronica squealed as the crowd gasped in astonishment.

Everyone had the exact same question running through their mind simultaneously; what on EARTH was she doing? Bill had a similar thought going through his head, especially in light of how he had their breasts exposed as soon as possible, but looking into her oddly serene face the gleam in her eye gave him a sudden sinking sick feeling in his stomach. After he dutifully removed his shoes and his bare soles hit the pavement, he knew instantly what she was doing.

To the increasing amusement of the crowd, he comically started jumping around madly in a desperate attempt to try not to burn his feet, but it was no use, the court was literally melting in the summer sun.

"Stop dancing and start playing shoeless boy!" Veronica taunted as Bill tried valiantly to look confident despite his flesh literally frying.

The next game they played was the worst he had ever played in his whole tennis career. With the combination of his burning soles and the continued delightful yet dangerous distraction of the bouncing tits on display, he was a goner. Veronica and Lynette easily won the next game.

Bill hopped nervously, trying not to scorch his feet as he awaited his fate and perpetually lifting his now blistering soles up in the air as he waited for what he knew was coming.

"Shorts PLEASE!" She commanded as the crowd went wild. Bill was a bit hesitant, but relented as his face turned as red as his soles. Humiliated that his naked ass was now going to be displayed for at least 20 college women, he openly regretted wearing the jock cut open entirely in the back today. Hearing the loud catcalls and hoots from the crowd as his white ass was uncovered only pissed him off now and increased his desire to strip these girls bare assed naked.

His embarrassment now totally focused him on his game and his will stiffened as he vowed not to lose again. His concentration improved, the next game went much better for Bill, and he barely squeaked out a victory despite his barefoot torment. When he now called for their shoes a collective moan went up from the audience.

Lynette and Veronica both winked at each other as they tossed their tennies to the crowd. The socks they were wearing were padded, and although not as effective as tennis shoes, they did prevent their feet from being burned like Bill. Now unshod, the game continued.

Bill was now completely demoralized as they played better than they had all day and obviously were not suffering on their feet like he was. Constantly roasting he played like shit and missed at least three serves he should have made and lost. Now it was serious as he stood on the court and the crowd cheered as the girls easily stripped him of his shirt. Now clad only in his jock he was almost completely naked in front of a crowd of women. The thought of losing now occurred to him and he grew very worried as up until now he had not thought it even remotely possible.

The crowd, as well as Veronica and Lynette, whistled appreciatively as he reluctantly stripped down to just his tiny open assed jockstrap. Veronica licked her lips as she gazed at his fine muscular body and tight dimpled ass come into view, made even sexier as he was dripping in sweat and looking adorable deliciously tiny and embarrassing jockstrap. Despite being a total asshat, she thought, he was certainly "doable" and she grew moist as she thought of the REST of his delicious bits that would soon be revealed and dangling and jiggling for all to see.

Being reduced to near nudity, and now worried about losing rather than winning, caused Bill to panic and in his panic played even worse.

This last game was the moment of truth, and although close, Bill missed his last return serve and now stood in dumbfounded horror as he watched the ball whizz out of the reach of his racket. The realization of his situation came crashing in on him as he heard Veronica call out in a sing songy tone "Jock strap time, Jock strap time!"

Every girl in the crowd now was on their feet cheering like crazy as Bill stood with his hand in front of his crotch and blushed. Slowly trying to preserve some dignity he covered his dick with his hand as he lowered his jock to the ground and kicked it over onto the growing pile of clothes. Now naked and humiliated he trembled with rage. His rage only grew when he heard Veronica speak her next words.

"Bill, we still have three more games to play. Do you want to know what your penalty is if you lose them all?"

Bill opened his mouth in shock as he had been concentrating so hard on the game he had completely forgotten about the penalty. His face burning with shame he meekly stared down at the ground as he knew his embarrassing day was not over yet. He still had not completely revealed his goods to the girls as he gripped his junk with his hands. Realizing he was going to have to continue to play while naked, he knew he would be flopping all over everywhere soon.

"If you lose one more game, you oil that baby up and stroke for the crowd in order to "earn" your clothes back."

The crowd went nuts now as Bill just stood open mouthed as he listened. Getting ready to protest, Veronica cut him off.

"Lose two more and we throw away your clothes and you will have to streak back to the dorm stark ass naked. If you lose three more, you will have your hands tied behind your back while you enjoy your nude romp!"

The crowd went crazy as the penalties were read out but Bill, horrified at the prospects, was determined not to lose anymore.

Luckily for him, he won the next game. Trying to cover his dick made it much closer than it should have been, but he just barely squeaked by. Bill smiled now as he heard the crowd groaning. He felt the tide was now finally turning and with a smug look on his face he ordered the girls out of their socks. Now THEY would suffer under the same conditions he was.

Hearing his command, Lynette turned to Veronica with a horrified glance as both girls knew they were in real trouble now. IN a straight game, they were no match for his skills so their plan was now backfiring and backfiring SPECTACULARLY. Without their socks it was their turn to toast their tootsies on the turf.

Bill chuckled to himself as he watched them hop wildly over the hot pavement as now it was their turn to suffer. The next game was easily his and he enjoyed seeing them wriggle out of their skirts as their faces grew red. Both girls had on white thong panties, and were sweating so profusely their nicely trimmed bushes were quite visible through the now sheer material. One more game to go and they would be naked!

The last game was quite fierce. First the girls won a point and then Bill won a point, going back and forth, it was tense. Finally, it was all tied when Veronica shot the ball right into the net and Bill leapt for joy. Temporarily forgetting about his nudity, the crowd enjoyed watching his long cock and heavy balls swinging wildly as he performed his victory dance as he no longer covered himself with his hands. Victory, although pyrrhic, was his as he demanded that the girls now lose their panties.

Slowly Veronica and Lynette peeled their sopping thongs to their ankles and kicked them to the side. Looking at their completely naked bodies he was entranced as their firm round asses came into view, he felt himself start to grow hard as they were astonishingly beautiful, now naked before his ravenous eyes.

Bill was completely mesmerized by the erotic sight and clapped as they were uncovered, but the crowd, obviously disappointed with the outcome, booed. As they stood before Bill in all their nude gorgeous glory he began wildly Grinning as he now had totally regained his confidence.

His smile growing, as was his cock, and since EVERYONE was now naked, he suggested they play one more game. If he lost, he would pay the penalties they had spelled out for him, but if they lost they would both agree to be his slave for the weekend. He was totally smitten with both of them as they were stunners, and little Bill was thinking for big Bill now as he made this lopsided bet.

Licking his lips, he felt his balls jingle in his hands at the thought of having two nubile young naked coeds servicing his every whim for two full days and his perverted imagination was already on hyper drive. Oh he had such plans for them, and in his mind they were already playing out. He would take that gorgeous top heavy Veronica and flip her over onto her stomach and ram his fat cock in and out her all night as he would pump into her sweet sweet pussy until she passed out. Lynette, and her equally unbelievable rack, would certainly look delicious on her knees, heavy hangers swinging, gobbling up his thick cock between her two full lips. Yes, despite the TINY risk of possibly losing, the porn movie running in his head compelled him forward. Besides, now that they were on equal "footing" so to speak, victory was certainly assured.

Lynette and Veronica on the other hand were visibly nervous the game having taken an obvious recent ugly turn. Embarrassed to be exposed in front of the ENTIRE audience, even if they were all women, was still humiliating. Seeing Bill smirk, looking as hot as a bonfire, licking his lips and staring back at them only seemed to make Veronica angrier.

Lynette was not convinced, but as Veronica whispered something into her ear she grinned. Bill could see them conferring and hoped and prayed they would agree, desperate to have both of them as his sole erotic property. It had been a VERY humiliating game, but if it could end it in a delightful threesome with these two, well, his embarrassment would be vindicated.

Veronica oddly winked up at the crowd but then approached the net. Somehow seeing her walking with her left hand over her breasts while her right hand hid her bush made her look even sexier to Bill. To his great surprise, and total delight, they agreed but only if they would get something equal from HIM if THEY won. So entranced by her gorgeous nude body he wasn't thinking straight anymore, his mind not able to get the image of she and her friend future fighting over his cock out of his head. Entranced and drooling, he nodded without even hearing the conditions.

As he walked back to his position he was shocked when he saw the naked Veronica turn and begin to announce the conditions to the crowd. They, like he, would learn EXACTLY what he had just agreed to now.

"OK, it is decided. We will play ONE more game in this battle of the sexes, winner take all. If BILL wins, Lynettte and I will willing go to his dorm room and do whatever perverted activities he wishes for the WHOLE weekend. IF however WE win, then he not only will put on his lubed up wanker show for us ladies, but he will then be tied up and drug home afterwards NAKED back to our dorm to act as OUR slave! What do you think ladies, do you think that is a good tradeoff?"