The Bet
written by:
JL

THE BET

"I don't know about this," I said.

"Hey, you lost the bet." Jennifer ran her hand down my bare chest, down my stomach, and gave a quick tug to my cock. "It'd be better if you were hard."

"I will be. Especially if Chelsea wears the kind of mini she always wears."

Jennifer pouted. "What about me?" She had long red hair and a dazzling smile, and she was wearing a tight red T-shirt that showed off her firm boobs. Her hips were curvy in tight black jeans, and her feet were bare. She was the second most sexy woman I'd ever dated, and the first one had dumped me for some loser with a bank account bigger than his dick. I'd do just about anything for Jennifer. Even keep my part of this stupid bet.

The doorbell to her apartment rang. "You want me to get that?" I asked.

She looked me up and down, as if checking to make sure I looked ready. "No. Stay here in the kitchen. I want you to make an entrance." She ran to get the door. I sighed and waited, impatient to get this over with. And nervous about the whole thing.

I heard the door open. "Hi, Chels—come on in!"

"Hi, Jen." It was Chelsea, Jennifer's best friend. I listened to them chatting for a few minutes, my nervousness growing. Then I heard Chelsea ask, "So where's Craig?"

"Oh, he's in the kitchen opening the wine. Hey Craig! How about some drinks out here?"

Showtime. I took a deep breath. "Okay!" I picked up a tray holding two bottles of wine—one red, one white—and four glasses, and walked through the door into the living room.

I was stark naked.

Chelsea gasped. She was a blonde, and as usual she was wearing a miniskirt that rode halfway up her thighs, showing most of her long, tanned legs. Her tits weren't bad either, inside a snug blouse unbuttoned halfway down her chest. She stared at me—at my cock, of course—for five long seconds before laughing with delight. "What the hell, Jen? Hi, Craig."

"Hi, Chelsea. Red or white wine?"

"Uh . . . sorry. I'm kind of distracted here. Jen, what the hell?" she asked again.

"We bet on the Oscars," Jennifer said. "He lost."

She grinned. "Or what? You'd be doing this for his softball team?"

Jennifer laughed. "Something like that."

"Red wine, naked slave," Chelsea said.

I poured. "White for you, babe?"

"Well," Chelsea said, leaning back and sipping from her glass. "Let me take a good look." She ran her eyes up and down my bare body. My penis, drooping, began to stir a little.

"Let's see those buns," Jennifer said.

I turned around.

"Not bad," Chelsea said.

"I've been working out with weights for a week," I said.

"Not that he needed to," my girlfriend said.

"Thanks, but we both know that's bullshit." Then the doorbell rang again.

"You want me to make another entrance?" I asked.

Jennifer shook her head. "No, that was just for Chelsea. Get the door."

"I hope it's not your neighbor returning that CD." I went to the door and looked through the peephole. "Okay, it's them." My heart pounding, I opened up.

"Oh my . . ." It was Anna, a short, slightly plump blonde, and her friend Leanne. We thought they were lesbians but Jennifer wouldn't ask. Gay or not, they both stared at my nudity with wide eyes. Not shock, but definitely awe.

"Oh-kay," Leanne said slowly. "I can see you weren't kidding, Jen, but what's the occasion?"

"He lost a bet," Chelsea said.

"Well, his loss is our gain." Leanne smiled at me. Anna was still staring. "Nice to, uh, see you, Craig." She patted my arm.

I closed the door—quickly—as she headed for chairs in the living room. "Wine?"

"Yes, please." They sat next to each other on the sofa. Anna wore a skirt that wasn't quite as short as Chelsea's but still showed off her nicely-shaped legs. Her boobs bulged against her blouse. Leanne had white slacks and a loose T-shirt on her slender body.

I poured the wine and handed each of them a glass. It didn't matter who got what, they'd share. Anna still hadn't said any—

"How big does it get?" Anna asked abruptly.

Chelsea burst out laughing. "I'm glad somebody other than me asked that!"

Anna turned red. "I just—I wondered . . ."

"It's been a while for her." Leanne patted Anna's arm. "It's all right, honey. I like a look at cock every now and then."

Anna took a deep swallow of wine and then looked me in the face for the first time. "Very nice, Craig."

"Thank you."

"You should see his ass," Chelsea said. "Show'em, Craig!"

I turned again. Leanne said, "Oooh . . . ahhh . . ." and laughed again. Anna leaned forward and pinched me. I jumped.

"Okay." Jennifer waved her arms for attention. "This is only part one of the bet. Now for part two. Get the towel."

With a sigh, I pulled a bath towel from a dining room chair and spread it on the floor.

"Is this what . . .?" Chelsea looked at Jennifer. Anna scooted closer to Leanne on the sofa.

"Yup. You wanted to see how big it would get, Anna. Well, watch! Go for it, boy!"

Naked, nervous, I spread my legs and looked at Jennifer. She nodded with eager anticipation. I shrugged and took my cock in one hand.

I had to jerk off for Jennifer's friends.

At first I couldn't look at them. My dick grew hard automatically, but I wasn't feel horny at all. So I looked at Chelsea. Actually, I looked at Chelsea's legs. That helped. I felt a slight surge in my balls.

Chelsea saw me, smiled, and sat back, letting the edge of her skirt ride further up her legs. That helped more. She let her legs fall open, showing off the inner skin of her thighs. My cock twitched.

The sight of the growing lust in Anna's eyes helped too. So did Leanne's hand, rubbing her friend's leg unconsciously. I glanced at Jennifer. She licked her lower lip, a slow sensuous flick of her tongue, and smiled encouragement at me.

"Ohh . . ." I breathed as I stroked. This was starting to feel good, especially with three hot women—and my girlfriend—watching my cock as I jacked off. Chelsea opened her legs even wider, and I could see her pink thong between her thighs. Leanne was squirming on the couch. Anna had her hand on top of Leanne's, squeezing her leg, and her eyes were locked on my rigid cock.

"I can't believe—look at that!" Anna leaned forward as a drop of precum dripped from the tip of my prick. Had she really never seen a cock before? My heart was still pounding bow, but not from nervousness anymore. I rocked back and forth on my feet, my legs unsteady, and Jennifer reached out to hold my leg and help me keep my balance. Her touch added to the excitement.

I'd thought I'd have a hard time reaching orgasm, but this was turning out to be easier and more fun that I expected. I was going to spurt pretty soon. And as much as I wanted to get this over with, I was enjoying the attention. How often does a guy have four hot women watching his cock? I grinned and jerked faster.

"His face is all red," Leanne said.

"So's his. . . thing," Anna said.

"Yeah," Chelsea said. "You going to cum soon?"

"Yeah, I think . . . I think so," I answered. "Uhhh . . ."

"Make sure you hit the towel," Jennifer warned. "Or you'll have to explain it to my mother the next time she visits."

Chelsea folded her arms across her chest. "I think I'm going to enjoy this."

"Me—ohhh—too," I grunted. "Ah! Yeah! Fuck!"

"Look at that!" Anna yelled.

I was cumming, squirting sperm out onto the towel, my head spinning, my legs trembling. Jennifer ran her hand up and down my leg as I spurted. I grunted a few more times, still stroking my prick, and gasped as I finished. My cock twitched and shot a few more drops of sperm, and I wiped my sweaty forehead.

"Wow," I said. "That was—a lot easier than I thought it would be."

"Is it over?" Anna asked. "I was just getting, uh, interested."

"Oh, it's not over," I said.

Chelsea brightened up. "There's more?"

"That was only part of the bet," Jennifer said. "Unfortunately."

"I bet on Meryl Streep," I said. "She bet on the girl in Precious. I'm giving her a break by not having her do this in front of my friends."

"Do what?" This was Leanne, who looked even more interested now.

I grabbed a chair and another towel to sit down, since I was still nude. Jennifer grimaced, then stood up and pulled her T-shirt over her shoulders.

"You guys are crazy," Chelsea said.

Jennifer threw the T-shirt in her face. Chelsea laughed.

I sat back to watch Jennifer reach behind her back to unsnap her bra. I always enjoy watching her get naked. This was no exception: the red bra dropped to the carpet and her breasts bounced free. Anna giggled. Chelsea said, "Nice rack."

"Yeah, you ogle it in the locker room at the gym every chance you get." Jennifer smiled and bent over to peel her jeans down her legs.

I went to the kitchen for a beer. When I got back Jennifer was nude and the girls were staring at with almost as much curiosity as they'd been checking me out. Anna and Leanne basically ignored me as I sat down again, but Chelsea took another look and nodded with satisfaction as I crossed my legs and sipped my beer.

Jennifer was sitting in her chair, legs spread, looking embarrassed but a little turned on at the same time. And she looked good, naked and just starting to get aroused.

"Okay," she said, teasing the edges of her slit. "Not used to an audience—well, more than one." She winked at me, then closed her eyes. One hand began massaging her clit gently. After a moment, she ran a finger of her other hand over her pussy lips. "Mmm."

Leanne was staring intently at Jennifer's body. Anna kept stealing glances at my cock. Her short skirt had ridden up around her chubby thighs, and she was rubbing her legs together. They were holding hands.

"Ohhh . . ." Jennifer smiled, her eyes still closed, and pressed against her clit harder. One fingertip probed her moistness. She licked her lips, and then slipped a finger inside, rocking one leg back and forth.

My cock was starting to rise again. Even though I'd just cum, it hadn't been all that satisfying, and watching my girlfriend masturbating for her friends—and me—made me ready for more. Chelsea saw it, and nodded again, but she was watching Jennifer mostly, and her own hands were rubbing her legs, up and down her thighs. I saw Anna glance at her with hungry in her eyes.

Jennifer stretched one leg out in front of her and rammed two fingers into her snatch. "Ahh! Yeah! Ohh . . ." She opened her eyes. "You like that, Chels? You like my hot pussy? Yeah, I think—I think—you do."

"I do," Leanne said. "I mean--" She looked at her girlfriend.

"Yeah, me too," Anna said, squeezing her hand.

"I sure do," I said.

"You're sweet," Jennifer said with a sigh of pleasure. "Mmm . . ."

I sipped my beer and watched as Jennifer lifted one leg into the air and then stamped it down hard on the floor. "Uh!" she grunted. "Uh—uh—uh!" She leaned forward for a moment as if staring at her pussy, then rolled back, her red hair dangling over her shoulders as she looked up at the ceiling.

"Fuck it." Chelsea pushed up from the chair and with one motion yanked her thong down her legs. She threw it at Jennifer, who blinked in surprised. Then Chelsea pulled her skirt up to her waist and began rubbing her clit urgently. "Fuck it," she said again. "Who you going to tell? This is . . ." She looked over at Leanne and Anna and began to pump her pussy.

"OHH!" Jennifer shouted, her eyes wide, her leg muscles taut. "Yes! Yes! Ahhh . . ."

That did it. I got up and stepped to her chair, between her legs. Jennifer looked up at me, surprised, and then she smiled as I pulled her hand away. I smiled and grabbed her hips, yanking her forward.

Jennifer leaned back and lifted her legs as I sank my cock into her pussy with one quick thrust. Immediately she wrapped her thighs around my waist as I began ramming her hard and fast. "Oh yeah, oh yeah . . ." she breathed. She grabbed my shoulders and stared into my eyes for a moment with deep lust fogging her own gaze. She mouthed a quick silent "thank you" and then closed her eyes and let her head fall back, surrendering to my cock as I hammered her as hard as I could.

I couldn't see the other girls, but I could hear Chelsea grunting and swearing as she fingered herself. Then I heard Anna moan loudly, and Leanne laughed in response.

Then Jennifer opened her eyes suddenly and gave me a push. I took the hint and pulled out, and I sat down on the carpet, my dick sticking up. Jennifer lunged at me with a gleam in her eye. In a moment I was flat on my back and she was on top of me, her knees around my waist, lowering herself onto my still rigid prick.

I grinned and grabbed her hips, easing her in. Jennifer leaned forward, hands around my head, and let her tits dangle in my face as she began humping up and down on my cock.

I breathed in and out, enjoying the sensation of Jennifer's pussy squeezing and sliding up and down my shaft—and suddenly getting even more turned on by the fact that her friends were watching us fuck.

Turning my head, I saw that Chelsea had kicked her skirt off and unbuttoned her blouse, exposing a lacy pink bra that wobbled with each breath she took as she strummed her clit. Her eyes were locked on our joined crotches, and she licked her lips hungrily as she took in the sight of us fucking hard on the floor in front of her.

I couldn't see Anna or Leanne from where I lay. Well, I could see Leanne's butt and Anna's foot—Leanne was kneeling between her friend's legs, and the gasps I heard in that direction told me what was going on.

In the meantime, Jennifer's frenzied thrashing told me she was cumming, and cumming hard. Her tits bounced like wild fruit, and sweat rolled down her body as she writhed on my cock. She leaned back and let out a scream that made me worry about the neighbors, and then she bent forward again and kissed me, gently on the lips.

"Sorry you lost?" she whispered.

"I didn't lose," I said.

She lifted her hips and slipped my cock out of her. It was still hard, trembling with energy. "You didn't . . ."

"I jacked off about two minutes before we started," I said. "Remember?"

"Out of the way, bitch!" Chelsea shouted. "Horny bitch coming through!" I looked up in time to see Chelsea tear her blouse off and yank her bra loose. Jennifer backed away from me, laughing, as Chelsea got on the floor and scrambled up to my body.

"You mind?" she asked Jennifer.

Jennifer shrugged, still laughing. "Hey, whatever. You're a guest."

"What about me?" I asked. "Do I mind?"

"Shut up," Chelsea said, fondling my cock roughly. "You lost the bet."

"Damn Meryl Streep," I said, but I laughed. And then I groaned as Chelsea leaned down to give my cock a long lick with her tongue before swinging her hips around and planting my cock deep inside her pussy with one quick motion.

Her big tits seemed to shudder with pleasure as she impaled herself on me. "Ahh . . ." She sighed, smiling down at me. "Good boy."

"I want my girlfriend's pals to like me," I said, pushing up with my hips. "This is just a little . . . more than I expected."

"And you're loving it," Jennifer said.

"Well . . ."

I'd managed to move enough to see Leanne and Anna on the couch, and for a moment I forgot all about Chelsea. Anna was naked, on her back, one foot on the floor and the other on top of the couch. She was clutching her tits, leaving red marks on her skin as she squeezed and groaned, while Leanne knelt on the floor, between her thighs, sliding a vibrator in and around Anna's pussy.

Leanne paused occasionally to lick her lover's clit. Her white slacks were gone, and any panties she might have been wearing, and she had one hand between her bent legs, inside her pussy, working her fingers in a circular motion. She was groaning Anna's name as she worked the vibrator in and out, but Anna, in the throes of near-orgasm, was staring at me—or, really, my cock.

I smiled at her. Then, when Chelsea paused for a moment, I grabbed her ass and lifted her from my dick. She groaned, but my cock was still throbbing and she realized I wasn't close to finished.

Chelsea crawled to another chair, next to Jennifer, and hiked herself up, legs wide, ass in the air. "Come on, damn it," she ordered. "Give it to me already!"

"Incoming," I answered, and grabbed her hips. I thrust deep inside her as hard as I could, and she let out another cry of ecstasy. Jennifer was right next to us, and she winked at me.

"Oh, fuck," Chelsea moaned as I slammed and rammed her. "Oh fuck fuck fuck fuck ffffuck!"

"Yeah," I murmured, hands on her shoulders. "This what you had in mind, Chelsea?"

"Ahhh!" Anna shouted. "I love you, Leanne! Don't stop! I love you!"

"I love you," Jennifer whispered to me.

"I love you," I told her. "And I really like . . . uhhh . . . your friends too."

Leanne had to let go on the vibrator as she came, sitting back on her heels as she rubbed her fingers frantically up and down her clit. Anna grabbed the device and kept it inside her, cumming over and over again as it hummed, but she looked at Leanne and licked her lips with a lustful smile. "Love watching you cum."

"Love you," Leanne said. "Oh! Yes! Oh!"

"Going to cum," I warned Chelsea as I felt my body tense.

"Fucking cum," she said. "Fucking cum inside me with your fucking prick, you fucking . . . fucker."

Jennifer laughed. I saw her stroke her pussy as I began to tremble all over.

"Me too," Chelsea whispered, her voice shaking. "Me too . . . me too . . . me—too!"

I don't know if she came first or I did. I just knew that I pushed into her pussy one last time, deep and hard, and then I leaned back and let out a loud gasp as I exploded. My dick slammed sperm into her pussy like a pumping fire hose. I felt the muscles inside her body clench and release, over and over again just like I was shooting spurts into Chelsea's pussy one after another for what felt like five minutes or more until she wiggled her ass to slip free.

I tumbled back, panting. Jennifer laughed at me. Cum trailed out of my cock. Chelsea turned over, sat down, and smiled at me.

"Sorry you lost the bet?" she asked. "I bet you did it in purpose."

"I don't think I lost anything," I said, patting Jennifer's leg.

"Well, you're not finished," Jennifer said. "You were supposed to serve snacks."

"He did," Chelsea said.

"Uhh . . . can I touch it?" This came from Anna, sitting up on the couch. Her face was still flushed, and she was holding Leanne close in her arms.

"Fine with me," I said. "But you better ask my girlfriend here."

"Everybody wants my boyfriend's cock?" She pretended to be mad. "I suppose. After he serves the crackers and cheese."

"Coming right up, your highness." I stood. Anna stared at my cock and licked her lips, and I already began to get hard again.