Alex & Maggie: The Bet

Alex stared off into space trying to concentrate on something other than her mouth on his hard cock. They were having a contest to see if he could hold off from cumming before her jaw and mouth got too tired from blowing him. It was not easy for him to avoid looking down and seeing Maggie's mouth on him. She was also rubbing her clit and moaning more than usual, trying to make him cum. Alex really wanted to win, the prize was his big sister's tight asshole. She had let him finger her ass, and constantly teased him by bending over in her school uniform with no panties on when their parents were still at work. Every time she bent over like that, her tight little asshole was glistening like either she had just licked a finger and rubbed it or like she had gotten really wet and used her juices to lube it up. Knowing how Maggie enjoyed teasing him, he knew she was capable of either one. Suddenly Maggie turned her body so that her wet pussy and ass were facing him, peeking out from under her little red and blue plaid skirt, her mouth never leaving his cock. She began rubbing her clit again and Alex could smell the aroma of her arousal. He tried to look away, still holding out. He closed his eyes for a moment and tried to think of anything other than Maggie. He opened his just in time to see Maggie slide a wet finger into her ass. At that moment, she pulled her mouth off of his cock just as he erupted, his jizz covering her chin and tits.

"I win!" Alex yelled in a raspy voice, his cock still dripping cum on the bed.

"I think we should call it a tie." Maggie said, pulling up her left tit to lick his juices off.

"A tie? How in the Hell do figure that was a tie? Did my cum go in your mouth? Nope, I don't think so." Alex laughed.

"Umm, can we do something else? A 3some with Jenny?"

"We've already done that, a few times. I want something we haven't done before. I told you the rules beforehand and you agreed. You aren't trying to renege are you my sweet big sister?"

"No. But I'm just scared. I mean your fingers or my dildo are one thing, but your cock is so big."

"Flattery will get you nowhere here sis. I'm only like 6 inches. That purple dildo you love is at least 9."

"Yeah, but it's not as thick as you are."

Just then they heard the garage door start to open below them.

"Shit! It's 6:00 already. Go get cleaned up." Alex told his sister. 

She jumped off the bed and kissed him deeply before running to her room.

"We're not finished with this discussion, Maggie!" he called after her.

******

Alex and Maggie's mother Elaine had come home and called for her kids to come downstairs. "Just a minute." Was heard from both of them upstairs. Elaine began puttering around the kitchen beginning to get dinner ready. After a few minutes both kids walked into the kitchen and sat at the stools against the island. Alex was wearing sweats and a t-shirt and Maggie had on yoga pants and just a sports bra.

"Maggie, is it really appropriate for you to be showing off your bra to your little brother? This isn't the dorms."

"Ah, mom, it's not like i'm looking. She's my gross big sister." Alex laughed as Maggie squeezed his cock hard under the counter.

"Ouch! Mom, she hit me."

"I swear the 2 of you act just like you did in middle school. Be nice to each other."

"I try to be nice all the time Mom, but he's a little jerk! And, I wear less than this in the pool, so if he wants to perv on me, he surely does out there."

"Ok, ok, no more talk of anyone perving. Listen, I'm surprising your father when he gets home. Our anniversary is next week and I am taking him on a cruise. I thought about taking you guys too, but I'm sure you'd rather stay home than see your parents have a romantic trip."

"Aww mom, that's so cute of you to do for daddy." Maggie squealed.

"Yeah mom, very cool. So is Aunt Charlotte coming to stay with us?" Alex asked unhappily. 

"No, now that you're both over 18, I think it's ok for you to stay home alone. But you have to promise there will be no parties or funny business. I may make you sign a contract." Elaine laughed.

"I'll keep this little jackass in line mom. Don't you worry." Maggie said.

"Who's keeping you in line then?" asked Alex, poking his finger into Maggie's spandex clad pussy. She was still wet and the crotch of the pants was slippery.

"Ok then, it's settled. Why don't the 2 of you take some cash out of my purse and go have dinner and see a movie so I can tell your dad about our trip?"

"And give him a preview of the good times on the ship?" Alex asked, laughing. 

"Alex! It's not right to think of your parents, or any other family members like that." Elaine playfully scolded. 

"Now get on your way. Your dad will be home soon."

******

Alex and Maggie headed upstairs to shower and get ready to head out to dinner. When both were finished Alex went to his mother's purse on the table by the garage door and opened her wallet.

"Hey mom, it looks like all you have are hundreds in here." He called out.

"Yes, I know. Go ahead and take one. Have fun you guys." Elaine called back.

Alex snatched a bill out of the wallet and his car keys from the table. As he was turning around, Maggie came into the room in a short,tight red dress that definitely was not conducive to her wearing anything underneath. He let out an audible gasp.

"You like, little brother?"

"Umm, yeah. But now I feel really under dressed."

"You look fine. We're just going to dinner and a movie, remember?"

"Yeah, let's go. I'm starving."

The two yelled goodbye to their mother and went out to the garage to hop into Alex' black Mustang GT convertible. As Maggie slid into the passenger seat, her dress rode up on her legs revealing just a little bit of her shaved pussy. 

"Wow sis, that skirt is almost illegal." Joked Alex.

"As illegal as what you do to your big sister?" Maggie teased, leaning over the center console to kiss Alex on the neck and lightly rub his cock through his shorts.

"Umm, yeah. I guess not. And believe me, I wasn't complaining. So where should we eat?"

"Jennifer is working at Mario's tonight. I know she gives you a boner." Maggie continued rubbing him slowly as he got harder and the speed of the car increased.

"Mario's it is!" Exclaimed Alex.

Jennifer was Maggie's best friend, and had been pretty much all of their lives. Maggie and Jennifer spent countless hours teasing Alex when he was in elementary and middle school, but something changed around the time he was a junior and the 2 girls were seniors. Their teasing took a turn from being slightly mean spirited to almost a competition to see who Alex would pay more attention to. It took Alex a little bit to realize what changed. Alex had decided to play football and his body began to show differences from his workouts. He was no longer scrawny little Alex, he was now Alex the starting QB. Either way, he had always enjoyed the attention from the 2 girls, and always lusted after Jennifer. The day that he caught the 2 girls skinny dipping in their pool and they pulled him in with them was like a dream come true for him. He and Maggie had already been messing around a little, but he'd never dreamed that his sister and Jennifer messed around as well. Maggie was right though, Jennifer did give him a boner.

Alex pulled the Mustang into the parking lot and put the top and heavily tinted windows up. As he did this, he suddenly noticed how heavily the scent of his sister's pussy hung in the air. He looked over at her and then leaned in to kiss her deeply, his hand sliding between her thighs making her moan as his fingers entered her hot wet sex. Maggie gripped his cock tighter and unzipped his shorts with her other hand. She pulled away from his kiss and buried her face in his lap taking the full length of him into her throat. She giggled a little as he moaned which made him moan more from the tickling sensations her giggles caused in her throat. She sucked him hard and fast, rubbing his balls and shaft as she she swallowed his better than average sized dick. Alex's fingers continued to work their magic on her pussy as he stroked her clit with his thumb while sliding 2 fingers in and out of her pussy. He sent her over the edge when he removed his second finger and slid it deep into her tight little asshole. She moaned deeply on his cock as her orgasm rippled through her body. The combination of Maggie's mouth and the naughty feeling of fingering her asshole combined to make Alex explode into his sister's mouth for the second time in as many hours. He leaned his head back and pulled his hands away as his sister looked him in the eye, opened her mouth and showed him his as yet unswallowed load. She often did this and it drove him crazy. She giggled again and swallowed. The two straightened up a bit and headed into Mario's for a bite to eat. 

Mario's was a small pizza and pasta place where most of the local teens spent quite a bit of time. The prices and food were good and old Mario didn't mind the kids hanging out. Mario also had a reputation for hiring only the cutest waitresses in the area so there was always eye candy for the teen guys to ogle. Mario called out a hearty hello to Alex and Maggie as they walked in and ushered them towards a table in Jennifer's section. They sat down as Jennifer sauntered over to say hi and get their order, noting that it was odd for them to be there during dinner hour on a weeknight since the Warners were a family dinner time type of family.

"Mom is surprising dad for their anniversary and wanted the house to themselves. Maggie explained to her friend.

"You know what that means? Sexy time for Elaine and Tom." Jennifer exclaimed thrusting her hips in a bad pantomime of sexual activity. 

"It's a good thing you have more rhythm than that when you fuck, or you'd never get laid." Maggie joked.

"I'd never get laid more than once maybe, look at me, this is enough to get a first chance." Jennifer laughed, posing like a goofy model.

"Why are you so quiet, Mr.Alex?" Asked Jennifer. 

"I think he might still be in shock from the tongue lashing I gave him in the parking lot." Chimed in Maggie.

"Yeah, I think that's it, sis." Answered Alex.

"Mmmm...did you save some of his juice for me? It isn't fair that you have full access to him all the time."

"I share him with you when I can, but that's the perks of fucking your little brother, full access." Maggie whispered. 

"OK, you guys want your usual?"

"Yeah, sounds great. I'm starving." Answered Alex.

"I'm on it, and hopefully later I'll be on you, cutie." Jennifer said as she went off to put in their dinner order.

Alex leaned into his sister.

"About all of this full access stuff, you owe me from our bet this afternoon."

"Alex, I told you. I'm scared you'll hurt me. Tell you what, how about you fuck Jennifer in the ass so I can see how it works? She's done it before."

"But I wanted it to be special and be both of our first times doing it."

"That's sweet little bro, but I think that in this case it's best for you to have a little experience before I let you. I promise you'll be the first cock I let inside my tight ass."

"Let me think about it."

"OK. I'm going to run to the restroom. I feel like I'm dripping on the floor because of you."

Alex smiled as she got up from the table and thought about Maggie's proposal while staring at Jennifer's ass as she talked to another table. I guess it would be good to have a little experience before I get my prize, he thought. And it would almost be like fucking another sister since they were so close anyway. Jennifer turned her head and saw him staring. When she caught his eye, she stuck her tongue out at him playfully.

After a few minutes Maggie emerged from the restroom just as Jennifer brought their food to the table. 

"So, what are your after dinner plans, kids?" Asked Jennifer. 

"Mom gave us cash for dinner and a movie. I'm not sure what's showing though." Said Maggie. 

"Well, you guys are my last table and I don't have any plans. We could go to my house, my dad is in Boston for work and the garage fridge is stocked."

Jennifer lived with just her father since her mother ran off a couple years before. Her father had a lot of out of town business so she was often home alone.

"Yeah, I wasn't really up for sitting in a theater all night." Answered Alex.

"Sounds good to me." Agreed Maggie. 

They finished eating and waited for Jennifer to finish up then headed to her house. Once there, Jennifer invited them in and said she wanted to get out of her uniform, stripping off her clothes as she headed up the stairs. Alex couldn't help but stare as she peeled off her bra exposing her tanned 36C breasts. Just as she turned the corner to her room, she tossed her hot pink thong over the railing. It landed partially on Alex's head and he felt the wetness of the crotch on his forehead. He pulled them over his face, causing both he and Maggie to crack up.

Jennifer yelled down the stairs telling them to help themselves to the beverages in the fridge. When no one answered, she was a little shocked. Jennifer quickly pulled a baggy old t shirt over her head and sprayed some perfume to freshen up then headed back downstairs. 

"You guys, I said help yours- -" Jennifer called out, stopping when she saw the scene unfolding on the couch. 

Maggie had her dress hiked up to her stomach and Alex had his face buried deep in her cunt. Maggie was moaning softly as he worked his tongue and fingers. Jennifer jumped on the couch to get a closer view.

"Wow, you guys are like rabbits. Don't you know it's a little rude to start before the host is ready?"

Maggie pulled her best friend closer and began to french kiss her. Jennifer lifted the t shirt over her head, tossing it aside and pulling Maggie's head to her tits. Maggie wasted no time, sucking Jennifer's nipple into her mouth while moving her hand between her friend's thighs, slipping her fingers into her wet pussy. Alex pulled back from his sister's pussy to take in the vision of the 2 hot girls playing with each other, noting the contrast of his sister's blonde hair and slightly fairer skin against Jennifer's well tanned skin and dark brown hair. One thing in common was how smoothly shaved and pink both of their pussies were.

"You heard Jennifer, don't be a rude guest. We have to make our guest happy or she won't invite us back."

Alex swiftly moved his head between Jennifer's thighs and started licking her pussy like a starved man.

Jennifer began to moan loudly, enjoying Alex's mouth on her clit. She then pulled away and pushed Alex onto his back so she could straddle his face. Maggie moved down Alex's body in order to suck his hard thick cock while he continued to devour Jennifer. Alex moaned into Jennifer's pussy as he felt his sister's hot mouth on him. The three of them carried on for this way for a while until Jennifer began to scream out that she was cumming, her juices squirting all over Alex's face, neck and chest. Jennifer's squirting sent Alex over the edge causing him to flood Maggie's mouth with his semen for a third time that day. Maggie pulled her mouth off of his cock and laid back to get herself off with her own fingers as Alex and Jennifer watched. Maggie's orgasm was a smaller one than she'd had earlier in the day, but still satisfying. The two girls moved quickly to clean Alex up, their tongues licking off the mixture of his leftover cum and Jennifer's juices.

"Well, the tongue bath works ok, but maybe we should all go take a shower?" Suggested Jennifer. 

"That's probably a good idea." Agreed Alex standing up and pulling both of the girls up off of the floor. 

"Why don't you go get the shower warmed up, Alex? I need to talk to Jennifer about something real quick."

"No problem, Sis. See you in a few."

Alex headed upstairs to Jennifer's room and started the shower. Once the water was warm, he stepped in and enjoyed the feel of the water on his skin.

"What do you need to talk to me about, you little slut?" Jen asked.

"Alex and I made a bet today, but I'm scared to pay up. I was hoping you'd help me out."

"Maggie Warner is scared of something? Oh god, this should be good." Jennifer laughed.

"I bet him if he could hold out longer than my jaw could while blowing him he could fuck my ass."

"Really? That's all? Why are you scared of that? I know my fingers and dildos have been in your ass, as well as his fingers."

"His cock is so damned thick! I'm afraid he'll tear me open!"

"Oh come on, you just have to work up to it. Tell you what, I'll give you guys lessons. The shower will be a good place to start. Let's go." Said Jennifer, pulling Maggie up the stairs. 

When they entered her room, she grabbed a medium sized dildo and some lube out of her night stand drawer.

Alex was relaxing under the hot water when he suddenly felt breasts pressed against his back and a hand lightly grip his semi erect penis. He kept his eyes closed enjoying the feeling and not really caring which girl was currently touching him. It wasn't like he could lose either way he thought. As the hand began to grip him tighter, he felt a tongue on his nipples. He groaned a little and both girls began to giggle. He opened his eyes to see his sister licking his nipples and Jennifer's hand lightly stroking his shaft, her nipples poking into his back. Both girls moved in front of him and nudged him back towards the large shower bench. Jennifer turned on the rest of the shower heads to make sure the water kept them warm. Alex sat down on the bench and Jennifer practically bounded onto his lap. She slid his cock between her pussy lips and began to move back and forth teasing him as well as lubing him up. Maggie had also sat down on the bench and spread her legs wide rubbing her hard clit and watching her best friend and brother. Jennifer reached down and grabbed Alex, sliding the head of his cock inside of her and pushing down taking him deep. Maggie grabbed the dildo,turned it on and rammed it into her own pussy, matching Jennifer's movements on her brother's lap. Jennifer grabbed Alex's hand and moved it to her ass. As if reading her mind, Alex wasted no time and began rubbing the outer bits of her asshole with his finger. Alex turned his head and caught a glimpse of his sister with the dildo in her pussy and two fingers buried deep in her ass.

"I guess the sight of your sister playing with her ass gets you going, huh you dirty boy." Teased Jennifer as she felt him get harder inside of her.

All Alex could do was groan in response as he felt Jennifer's pussy tighten up around his cock. Jennifer lifted off of him and turned around, bending over slightly and sliding her own finger into her ass. 

"You want to put something in here, dirty boy?" She asked looking back over her shoulder. 

Alex just nodded, grabbing his cock and waving it a little. 

Jennifer moved backward and let him rub the head of his cock around her sphincter. Before he knew it, she had pushed back taking his entire thick cock into her ass. Both of them groaned loudly from the sensation and Jennifer sat for a moment enjoying being filled up by his cock. The sight and sounds of Alex and Jennifer pushed Maggie over the edge, her orgasm causing her to scream out loudly. Jennifer began to rock up and down on Alex, her tight ass milking him. Alex wanted to hold out, but knew he couldn't. His cock throbbed and spewed a stream of cum deep into Jennifer's ass. Jennifer began to tremble and then let out a low guttural moan as the orgasm ripped through her body. She collapsed back onto Alex's chest, feeling his cum drip out of her ass. Maggie moved so she could lean against Alex's side and kissed her brother deeply. 

"That was so fucking hot you guys." She whispered. "I say we rest awhile, then it's my turn. I'm going to text mom and tell her we're staying over."