I love to win. Let me tell you about the last bet I won.
My friends and I were having a slumber party at Becky’s house. We were all cheerleaders, or at least we were before we graduated high school the week earlier. Besides Becky, who reminded me of short-haired Megan Fox, there was Kristin (a blond who looked like Ashley Spears), and me (I’m Chloe, I’ve been told I look like Jessica Alba). Oh yeah, and there was Madison. She was the hottest of all of us. She looks so much like Selena Gomez that she could be her long lost twin. Even though I like boys, I have sort of a crush on Madison, in fact everyone does. With her dark eyes, cute nose, pretty smile and perfect, hard 18 year old body, everyone wants to fuck her.
Becky’s house is a huge 7bed/5bath mini mansion. It’s so big that Becky’s father, David, has his own man cave with a pool table, juke box, leather couch; the works. That’s were I won my bet.
We girls were having our party in the spacious living room, and Becky’s parents were upstairs. We were talking about boys, and Madison admitted that she was a virgin. I couldn’t believe it. Madison was smoking hot! Her straight black hair always looked like she had just come from a salon, and her make-up looked like it was applied by a professional. Madison also said that she wanted to get her V-card punched before she left for college, so that she wouldn’t be hung up about it. No problem there I thought, and I told her so.
“Madison, you are so perfectly cute and hot, you can fuck any man you want. Heck, you could probably get Becky’s dad to fuck you tonight, if Becky’s mom wasn’t here. Hey Becky, how big is your dad’s dick? He’s only your step-dad, so I’m sure you’ve checked him out!” I was only joking, and we all laughed. Everyone but Becky, she took umbrage.
“First of all, talking about my dad’s you-know-what is just gross. And second of all, there’s no way my dad would ever cheat on my mom. Not with Madison, not even with Angelina Jolie. My dad would never, ever fuck any other woman. I’m 100 percent certain about that. He absolutely loves her too much to ever cheat on her. I’d bet anything.”
At that moment Becky’s mom hurriedly came downstairs fully dressed. “Becky, there’s been an awful car wreck and I’m needed at the hospital. Girls, try to keep it down so you don’t keep Becky’s father up all night.” Then she left. Game on!
“You’d bet anything, huh Becky? Here’s your chance to put your money where your mouth is.”
“What are you saying,” Becky asked suspiciously
“I think your dad would do Madison. She’s just turned 18 and has model looks. I don’t think any man can resist her. I say we do her hair, nails and make-up, dress her in some skimpy panties and tank-top, get her and your dad together and see if he makes a move. How about it Madison, would you let Becky’s dad fuck you?”
She was so cute and sweet as she said, “Yeah. I’d let him fuck me. He’s kinda hot.”
“My dad would never make a move on her, no matter how hot she is.” Becky stated. “You’re on. How much do you want to bet?”
“One dollar. A symbolic amount. We’ll set up your web-cam in your dad’s game room, get them both in there, and see what happens. Deal?”
“Deal.”
Kristin said, “I want in too. I want to bet too.”
“On what side?”
“I think he’ll do her!”
It was so much fun preparing Madison for her fuck date. First we had her take a shower, and I told her to shave her pussy. “Should I leave a landing strip?” she asked. We told her “No, shave it completely bare,” and she said she did. Then Kristin and I gave her long silky black hair just a touch or curl. We chose a pink lip gloss that I thought was perfect for cock sucking.
“You’ve give a bj before, haven’t you?” I asked as I gingerly applied the gloss. Madison didn’t reply, she just blushed. “You’ve never even had a dick between your lips?” She sweetly shook her head no. “Well, you’ve had your pussy licked before, right?” She bit her lip and again shook her head no. I was incredulous. This tasty little morsel with the china doll face and skinny, taut bod was so fuckable that I wanted to do her myself with a strap-on, and I like boys!
For her nails, fingers and toes, we chose cherry red paint, with white heart patterns on them.
In deciding what she should wear we picked out a pair of Becky’s hot pink cotton panties with a read heart in front, and a matching tank-top that showed her flat midriff. To top her off I put some silver glitter on her cheeks and nose.
Kristin and I stood back and enjoyed our handiwork. Madison was 5’5″, 105 lbs, super cute, petite, a little tan, and now made-up and dressed to rock any man’s world. “Wow. Look at her,” Kristin said, “Are you sure you want to go through with this Becky? I think you’re going to lose.” That made Madison giggle.
“I kinda nervous,” Madison said.
“I don’t blame you. You about to get fucked for the first time.” I replied.
Kristin chimed in, “And probably get your brains fucked out for the first time too! Married guys do that.”
“Kristin, you’re such a slut! And my dad’s not going to fuck her. He loves my mom.”
“There’s one more thing I want to do.” I got a temporary tattoo of a pink heart out of my purse and put it on her tight bottom. “She’s ready. Wait, here, put my gold toe ring on. Now, she’s ready.” We set up the web-cam so that we had a perfect view of the couch in David’s game room, then put our plan in action. To get David into the game room, we had Madison go up and ask him if she could watch tv in there. When and if he said yes, she was to ask him to watch tv with her.
“He’ll say she can watch tv in there, but he’s not going to watch tv with her, and he’s definitely NOT going to fuck her, no matter how hot she looks.” Becky predicted. “He loves my mom too much.”
“We’ll see.” Then I whispered in Madison’s ear, “Do you really want David to fuck you tonight, to take your virginity?” When she said yes I gave her one last bit of advice, “Then let him sit on the couch first, and you snuggle up close to him, okay?” I gave her a little pat on the butt. Madison scampered upstairs and we watched the web-cam and waited. Sure enough, only a few minutes later, Madison and David came into view. David was wearing a robe. He sat on the couch and turned the tv on. Madison snuggled up next to him. Good girl, I thought.
“OMG, I can’t believe he’s down there, watching tv with that little slut!” Becky was upset, and got up as if to go to the game room and interrupt them.
“No No! A bet’s a bet. Let’s just let nature take it’s course.” I demanded. Becky sat back down and pouted.
Kristin, Becky and I watched the web-cam. Right away, David put his arm around Madison. “He’s going to make a move,” I said. “Look! He’s got a huge bulge already!” After two more minutes he began stroking her back, first outside the tank-top, then under it. Madison snuggled up to him closer.
“His dick must be huge! Look at that bulge!” Kristin squealed. “What have we got that poor little girl into?” It truly was a monster bulge. I would’ve been scared for her too, if I wasn’t so horny!
Madison’s was holding onto David’s arm as they watched who-knows-what on tv. Saying nothing, he nonchalantly took her hand and put it onto his growing crotch. Madison, also saying nothing, began rubbing it. David began to squirm. He moved to kiss her, and she kissed him back. They made out like this for a minute. Then David pulled her onto his lap, so that she was straddling him. They were kissing and dry humping each other like mad. Soon David had his hands up her tank-top and was squeezing her tits. This just made Madison dry hump him harder.
“Wow. He’s really going to fuck her.” Kristin observed, as if in a trance.
Eyes riveted to the video, Becky, also trance-like, said “You haven’t won yet. Maybe he’ll just get a blow job.”
Not taking my eyes off the horny site, I said “I hope not. I want to see him fuck her senseless!” We laughed. Even Becky. I guess she was too horny to be upset that she was losing her bet. Or that her dad was going to fuck her pretty friend during her slumber party.
David then took Madison’s tank-top off. I caught a glance of her breasts and I thought she had perfect, firm B-cup titties. David must have thought so too, because his mouth went right to them. The web-cam had no sound, but we heard Madison squeal all the way across the house. And it was a large house!
I couldn’t take it any longer, and I began rubbing my clit, right there in front of my friends. Kristin, biting her lip, noticed me and shoved a hand down her panties too. “Oh god. This is hot,” Becky said and also began fingering herself. We were having a great time masturbating while watching Becky’s dad have his way with our gorgeous virgin girlfriend.
David stood up and took off his robe and boxers, unleashing a porn-star sized erection, waving it in Madison’s super-cute face. She took a hold of it in her tiny hand and shyly kissed it on the tip. Then she kissed it some more. And licked it a little.
“Suck on the damn thing, already!” Kristin shouted at the video. We laughed and rubbed ourselves harder.
Soon Madison was sucking on it, though she could only fit half of it past her pretty pink lips. David had his hands behind her head and he was loving his teeny-bopper blow job. He took her hand and put it on his pendulous balls, and she began squeezing and rubbing them. After a few minutes he put his balls in her mouth, while his huge cock throbbed on her forehead. Then he put his dick back in her mouth. And then his balls again, and so on. They went at it like this for a bit. Neither Madison or David were losing their enthusiasm.
“Is he going to fuck her or what?” Kristin yelled, then she leaned back, took her panties off and really began rubbing her clit furiously. She had a really cute, almost bare pussy, not shaved, but with the slightest tuft of truly blond curls. Becky and I locked eyes. We were kind of shocked that she would take her lacy panties off right in front of us. But we were also super turned on, so we took our panties off too and rubbed ourselves harder. We were quite a sight. Three cute, petite teens, with nothing on but t-shirts, rubbing our pussies while we watched our cute little friend have sex with Becky’s dad on the web-cam feed.
Finally David took his 9-inch throbbing red erection out from between Madison’s pink lips and positioned her so that she lay on the couch. He grabbed her panties and pulled them off. Madison assisted by lifting her legs up. Yep, she wasn’t lying when she said she had shaved her pussy bare. David took a long sniff of her pink, wet panties then threw them across the room where they hit his dartboard, and hung off a dart.
“Finally. He’s going to give it to her,” Kristin gasped. But it wasn’t to be. Not yet. David spread Madison’s slim legs and licked at her cunny. Madison closed her eyes, she was in heaven.
After five minutes of having her virgin, bald, teen pussy licked, Madison was obviously cumming. And so was I. And by the moaning sounds she was making, so was Becky. Kristin left no doubt, “Oh God! I’m cumming!” she squealed and rubbed her blond cunny faster.
David got up from between Madison’s perfect legs, wiped his lips with the back of his hand and helped Madison stand up. Then he sat down on the couch, his massive boner waving in the air, and helped our cute virgin friend sit on his cock. She straddled him and David tried to work his huge cock into her. She spread her knees to help him get it in. For a minute or two they made out while her tight little pussy was perched squarely on top of Becky’s dad’s bulbous cock-tip. They both gyrated their hips, but there was still no penetration. It was almost as if Madison didn’t even have a pussy hole.
David had had enough. He grasped her perfectly slim hips and pulled her down as he viciously thrust up, and his tip disappeared into her. She took her mouth off his and held onto his broad neck for dear life as David continued to work his huge cock into her virgin pussy. With each upward thrust, a little more cock disappeared. It took about five minutes and who knows how many thrusts, but eventually his entire dick was in our pretty little friend.
“Oh God. He’s totally in her!” Kristin shouted. Then she grabbed the hand I was rubbing myself off with put my fingers in her mouth and began sucking. I was startled for a moment, but then just went with it, and resumed rubbing my pussy with my other hand. Becky, not to be left out, grabbed Kristin’s pussy-juice covered fingers and began sucking them. Soon we were rubbing ourselves and swapping pussy-juice covered fingers with each other like we’d been doing it all our lives.
Meanwhile David and Madison were fucking like young lovers; well, one really young lover and one middle-aged lover with a massive cock! Her perfect butt was rising up and down that large dong, slowly at first, soon speeding up to porn-star speed. They were kissing each other again, lost in lust.
He sure gave it to our cute little friend real good. After the cowgirl position, they went to reverse cowgirl; Madison had a hard time at first keeping her balance, and we could see them laughing when she would fall off his cock. But they didn’t laugh for long as David got his dick back into her and began fucking her silly once again.
Then he got her missionary style, put her legs on his shoulders and really began plowing that tiny pussy good and thorough. He’d take it almost all the way out, then BAM!, thrust it all the way in, over and over and over and over. Then David had Madison get in the doggy position and had her firmly by the hips as he thrust into her and she thrust back like a pro, over and over and over. Last I saw of them, he buried himself to the hilt and gyrated like mad and pulled on her hair. We could hear his shouts as he obviously spewed buckets his married cum into her virgin pussy.
It was the last I saw of them because that really got Kristin going. She lay back and pulled me to her. I thought we were going to make out, but she turned me around into a 69. Whoa! Kristin’s tongue was in my pussy! I didn’t see that coming! What the hell, I thought, and I began licking Kristin’s hole, her sparse blond curlies tickling my nose. Becky wanted in and soon we had a pussy licking triangle going.
I was cumming every few minutes, losing all sense of where I was. Then I heard clapping. It was David and Madison, still buck naked, standing at the doorway watching us lick each other’s pussies.
“I guess they want to be left alone,” Madison laughed. But Becky took her mouth off my pussy and said “Wait!” She got up and said “Kristin, Chloe, you win the bet.” Then she took Madison by the hand and got her in a 69, Madison on top, Becky licking out her dad’s cum. Kristin got me on top of her in a 69, and I was just getting into a groove when I felt an impossibly large cock poke at my pussy hole.
“Oh God! I’m not on the pill!” I thought, but I didn’t say anything! I love it when I win!