A week later
Penny and her close friends Wendy and Helena are playing poker with Tim. Wendy and Helena are both athletes like her, with Wendy being on the swim team and Helena being on the track team. Penny is the only one who is on both. The three girls are all far more experienced at this card game than he is but Tim is putting up a good fight, being a fast learner. He even won a couple of rounds. The thing is, the girls won a lot more rounds than he did. They aren't betting with money though, so everything is okay. If they were, he'd have lost a large amount of bucks by now.
The girls share a conspiratorial look and Penny turns to Tim. "I have a great proposal," she says to the boy. "If you win this round, then I will take you to Barnes & Nobles tomorrow and buy you any book you want." Tim visibly perks up. "But if you lose, you have to fuck me right here, right now, in front of Wendy and Helena." Now he freezes in shock as Penny's two tall teammates begin chuckling loudly. Tim just can't believe what he is hearing right now. "What do you say? Do we have a bet? Or are you too chicken for it?"
Wendy chimes in "Yeah, take it. Come on, don't be a little wimp. Take some damn risk, man." She looks at him and so does Helena. Penny has kept her gaze fixed on him from the start and is intensely staring at him, making his cheeks turn red again, just like they've been doing a lot lately for her. She is getting good and pushing his buttons, even better than Kath ever was. Not even her older sister could make him blush so often back when the two of them were still together. Both Tim and Penny know that.
Hearing the girls say that and seeing the other girls' expressions make him know that he's got no option. "Okay, we have a bet," he says. A minute later Tim reveals his hand. "One pair." The girls all snicker and he realizes that he lost. Somehow, he doesn't feel too bad about this though. As much as he wanted her to take him to Barnes & Nobles, the idea of getting fucked by her is more appealing. The problem is, Tim still got his shyness and isn't sure if he can have sex in front of other people like this. He has never thought about exhibitionism before in his entire life. Kath was never interested so they never discussed it.
Penny exchanges a smirk with her two friends, revealing her hand. Tim gasps in shock. He knew she won but the way she won is spectacular. "A Royal flush, and in spades too," she boasts, showing him that she has the best hand possible in the entire game. Seeing her almost predatory look makes him feel nervous about the fucking in front of Wendy and Helena part, especially since the two of them look quite predatory as they stare at his crotch, waiting for him to unzip. What on Earth is he going to do now? "Start unzipping, baby. I am going to ride your cock now."
"Hang on a moment," he sputters out in a shy tone as Penny begins taking her blouse and skirt off, revealing that she isn't wearing any underwear. Tim is now as red as a tomato. He has only seen one girl naked before and that was Kath. She had a good body but Penny's is even better. True, she has smaller breasts but her stomach is tighter with beautiful six pack abs. Her thighs are also more muscular from running and swimming. And Penny's clearly moist pussy is very hairy too. He has always fantasized about a hairy vagina, but Kath kept hers clean shaven. Penny's is perfect but he still is a bit nervous. "Are you sure you want to have sex in front of them? I know that they are your friends, but it could still be awkward."
"Baby, you agreed to the bet so pay up now, or I'll get them to hold you down so I can force myself on you," she says, playing with the large bush right above her cunt. Her pussy lips are glistening with the warm nectar of her arousal as she eyes him hungrily. Her friends look ready to help her rape him. That's why she brought them over for the game of poker. Her stupid sister is off fucking Tim's dad right now so she can rape Tim here if he doesn't consent to it. She does hope he will consent though, since deep down she doesn't really want to be a rapist that much.
"Okay," he mutters and begins to take his clothes off. His four inches cock is already hard at the sight of Penny's washboard abs and powerful thighs. She smirks at this and walks towards him, wrapping her fingers around his dick. Her left hand reaches up between his legs to cup his balls and squeeze them tenderly, not wanting to hurt the boy she loves. He moans and his hard penis gets even stiffer in her fist. Penny strokes it, tugging his erection gently. It feels so wonderful to have her caress him this way and his face shows it well.
She lies down on her back, telling him "Eat my pussy and me cum first, since your tiny cock won't be able to do that. I only want you to cum inside me when we fuck." The blushing boy kneels and buries his face in her hairy crotch. She traps him between her muscular thighs and thrusts upwards, pressing her cunt into him, grinding her clit against his nose. Penny moans as the love of her life services her, giving her head. He is quite good at oral, having worked very hard on it to help get Kath. From now on it's Kath's little sister who'll get to enjoy all the benefits of his hard work.
Penny writhes about in pleasure as he eats her out. "Yes, that's it you little cuntlicker," she hisses, grabbing the back of his head and enjoying herself thoroughly. This is perfect. She smirks at her friends who are watching and giving her congratulatory smiles. They both know how long she has waited for this moment. Tim is going down on her with gusto and she loves it. Her very wet snatch is leaking juices into Tim's mouth. She has never been so horny in her life. All he could taste is her perfect cunt. It tastes like the most delicious thing in the world to him.
Soon, she orgasms really hard. It is an intense climax for her and she squirts a lot. Once she is done, Penny makes him stand up and gets on her knees. She is now cupping his balls. "Please, stop," he says, embarrassed at how he's being fondled in front of Wendy and Helena. "Let go." Penny doesn't let go though and squeezes again, before kissing the tip of his cock. She then uses her free hand to stroke him and jerk him off slowly. Her hands have never touched another guy's genitals before but her friends taught her very well and she knows what she is doing with his hard prick and balls.
"I want you to cum all over my face after this," she says. Without any more warning, Penny moves her head forward and takes his manhood in her mouth in one go. She begins to bob her head back and forth. The brunette sucks his dick hard. She gives him the first blowjob for both of them, being the first time she is giving one and the first time he is receiving one too. Kath never gave him blowjobs, but Penny is giving him one right now, and it feels so amazing. Her lips sliding along the length of his cock and resting at the base and the way her tongue swirls around his spongy head is too much for him and he soon starts cumming in her mouth, filling it up with his cum.
