You arrive at the party in a pair of red swim trunks, a plain white tee and some flip flops. Everyone is drinking and having a good time, and for the first time in your life, you partake in some drinking yourself. You’ve had a couple shots and some beers, when you look across the pool and see the most beautiful woman you’ve ever seen. She was in a red 2 piece bikini, the top just a little bit too small, clearly struggling to contain her massive double Ds which jiggled with every move she made. The bottoms were cheeky too, a thong bikini that carved around the sides of her perfectly shaped ass. The liquid courage kicks in and you decide to shoot your shot at her.
As you make your way around the pool, you notice how big her and her friends are. Not in a bad way, just big, tall, Amazonian looking woman. You don’t think twice about it as your sole focus was on the beautiful blonde in the red bikini. You say hello and introduce yourself. She tells you her name is Beth and you guys get to chatting about where you’re from and other generic things. As you continue to talk the conversation becomes more flirty and eventually she asks if you want to play a game called “I bet you can’t.” Essentially, the game calls for someone to make a competition out of anything and the bettor chooses the stakes. “Sounds fun,” you think to yourself before agreeing to play.
The first bet comes from her, she bets that you can’t beat her in beer pong. When you ask what the wager is she explains that if you win you get to kiss her, but if you lose, you have to drop and give her 25 push-ups. Sounds like a win win. Either you get a kiss, or you get to showoff with some shirtless push-ups. The game begins and you catch fire, making shot after shot until there’s no cups left. After you win she gives you a peck on the lips.
Next is your turn, and you know you’re good at quarters, so you say, “I bet you can’t beat me in quarters.” She asks the wager and you explain that if she wins, you will give her $25 but if she loses, she has to make out with you. She accepts and the game begins. Same as before, you can’t miss. Bouncing quarter after quarter into a cup without missing, the game only lasts about 2 minutes before you win. You start to act a little bit cocky and grab her and pull her in tight. You lay your lips on hers and begin kissing passionately. Her tongue feels so good on yours that you can’t help but feel the blood rush to your cock. She pulls away after about 30 seconds and now it’s her turn.
She starts talking about how cocky you are and how you need to be put in your place. She points to the basketball goal and says, “I bet you can’t make a basket on me!” Now, the alcohol has already kicked in and your confidence is sky high. You tell her that you could never lose to a girl in a sport and that this will be easy. You can tell your comments rub her the wrong way as she opens her mouth and says, “if you’re so confident, let’s up the ante… If you make a basket, I’ll flash you my bare boobs right here,” then she leans in and whispers in your ear, “but if I win… I get to pants you in front of the whole party!” That made your dick twitch in your bathing suit. That’s a very scary outcome, and you hesitate. She says she will give you 2 try’s just to make it fair. Although you’re nervous, you think there’s no way you can lose, so you accept.
You check the ball up and the game begins. You start dribbling back and forth just to get a feel for it, but she stuck on you like glue. Her defense was way better than you ever thought. It also didn’t help that she was 6 foot with long arms. It was also very distracting watching her play defense in such a skimpy little bikini. You decide to try to drive towards the goal but she cuts you off, causing you to dribble the ball off your foot. You dive for the ball and save it just before it goes out of bounds. Now she’s talking smack, calling you “little guy” and even putting her thumb and index finger together
to mock you, calling you tiny. You’re nervous, but at least you still have two tries and you believe your motivation to see those knockers of hers will be enough to win. You drive right but she doesn’t let you by, she’s stronger than you ever would have imagined. You decide to hit a fadeaway and when your shot goes up it’s perfectly in line to go in. You watch with anticipation as the ball hits the inside of the rim, rattles around, then falls out. You barely missed. It’s your last chance and you know that. You tried to out power her but that didn’t work so you decide to try to surprise her with your speed and quickness. As soon as she checks the ball, you dart as fast as you can to the right. You get past her, the only thing that separates you from winning the bet is an easy layup. You jump as high as you can, elevating yourself as close to the rim as possible. You release the ball from your grip and out of nowhere, you see her long arm outstretched by the goal. Just before the ball hits the backboard, she slaps it away as hard as she can causing the ball to bounce into the pool. “HAHA you said it was going to be easy to beat a girl huh?!”
You can’t believe it so you try to plea with her, “look I’m sorry… I can’t let you do that, I-I think I’m just going to go home.” You stutter nervously. She reaches out and grabs hold of your wrist, “you can’t LET me do that?” She asks, “see that’s not how this works, a deals a deal!” You try to pull your wrist away and make a break for it, but she grips tighter. You’re not going anywhere, she’s stronger than you. She points back to her friends, the Amazonian’s, that you saw her talking with earlier, “those are my friends, we’re the Memphis woman’s basketball team.” She says threateningly, “and if you try to leave again, we will make this more humiliating than you can ever imagine… we’ll make you wish that the only thing that happened to you today was getting your pants pulled down.” You respond, “okay fine! Just do it already then! Pull em down and get it over with, please!” She looks at you and giggles, “oh no sweetie, that would take away all the fun and anticipation!” She says laughing, “now take your shirt off and go stand on the edge of the diving board, I’ll be with you shortly!” She exclaims before smacking you on the butt and pushing you toward the diving board.
You do as your told, removing your shirt as you hang your head and solemnly make your way to the diving board. You creep all the way to the front, allowing just your toes to hang over the front edge. You scan the party, the good news is, everyone is super drunk and not paying attention to you standing there nervously. Then, you look over and see her whispering with her friends, giggling as she points to you as you watch their eyes widen and smile at you. Your a glass half full kind of guy so you think to yourself, “well, maybe just they will see! It could be way worse, I just have to pull my pants up quick.” Beth starts to make her way over to you very slowly, almost creeping around the pool as if you can’t see her. Then, things take a turn for the worst as one of her friends pulls out her phone and starts recording. Beth turns to the camera and makes the “shhh” face
before continuing to creep around the pool towards the diving board. You feel your shorts getting tighter, pitching a little tent in them. “Why am I getting hard?” You think to yourself wondering if it’s from all the anticipation, or if it’s from watching Beth’s tits jiggle around as she makes her way to you. As she approaches you from behind, you decide to cross your arms in front of your now full on boner in an attempt to not be exposed as bad when she pantses you. Then you feel her soft hands grab your wrists and pull them to your sides. She whispers in your ear, “leave them there or I’ll make you cum in front of everyone.” You freeze up in compliance and feel your little cock twitch at the thought of orgasming in front of all these people. Without warning, the music gets cut off. Her friend was controlling the aux and this must have been pre planned. You’re stuck in your spot, forced to just stand there and do nothing but accept your fate. All of a sudden, Beth shouts at the top of her lungs, “HEY EVERYONE!!!” Everyone in the party turned to see what the commotion was about. Hundreds of eyes gaze confusingly at you as she screams, “CHECK OUT THIS GUYS LITTLE DICK!!!”
You feel her hands grip tightly on either side of your little sweet trunks and in one swift motion, she yanks your trunks down with all her might. You feel the shorts slide speedily right past your boner, causing it to bounce effortlessly into view. Your suit glided right past your thighs and shins and finally stopped when they plummeted to your ankles. You look down to see your stiff cock standing at attention as your swimsuit pooled around your feet. You look back up to see the crowd erupt with laughter, pointing and laughing at your humiliation. Your jaw drops and your face turns red hot with embarrassment. Your body locks up from the horror and shock of the situation as the onlookers laugh hysterically and make comments about your tiny dick size. You’re snapped back into reality when you hear Beths voice, “psst, pull your pants back up!” She says as you reach women and yank your shorts back up around your waist.
Everyone is still laughing as you gather your things and make a dash for your car. Beth chases after you and gets in the passenger seat before you have time to drive away. “Look I know that was humiliating,” she says, “but I can tell you liked it… and I liked it too.” She grabs your face and starts kissing you passionately. You’re horny and confused but you let it happen. She then slips her hands under your shorts and grabs a handful of your balls as she grips tightly. It both hurt and brought you closer to orgasm at the same time.
“Please stop, my balls are swelling, please let me go home!” You shriek out with pain. “I’ll stop once you admit that you want to cum in front of my friends next time!” She utters as she grips your balls a little tighter. “Agh, no! Next time?!? Why would I want that? I’m humiliated enough don’t you think?” You ask, moaning as your balls are throbbing, ready to explode. Her grip gets even tighter now as she says, “you better beg for it if you want me to stop… I’ll even finish you off right here if you comply.” “OKAY O-OKAY!” You stammer, “I want you to make me cum in front of your friends next time! Now please let me go!” She smiles and slowly releases her grip from your balls and slides her hand to your shaft. “My command is your wish!” She says as she starts pumping her hand up and down around your swollen penis. 3 strokes in and you explode inside your pants, a massive load of cum dripping down as she continues to stroke and milk you until your balls are completely empty.
You lean back in your seat, disoriented from the euphoria of what you just experienced. She then pulls her cum covered hand out of your shorts and slaps you on the side of the face with it. “Let’s do this again sometime.” She says as she writes her number down on your arm before getting up and exiting the car. As she jogs back to the party she stops and tells you to roll your window down. “Just so you know that it be worth your while…” she says flirtingly as she grips the bottom of her bikini top and slowly pulls upward on each side. Her beautiful tits spill out right before your eyes. Then, she adjusts her top and heads back into the party, leaving you confused, defeated, humiliated and horny.
Fin
Part 2 coming soon.