Bet Your AssbyKrazy35©
Hanna placed her cards on the table. "Full House. Nines over Threes" She declared with confidence.
Samantha looked disappointed for a moment then a wide grin crossed her lips. Slowly she laid her cards on the table saying "four little tiny deuces" With that she reached out with both hands and dragged the large stack of chips toward her.
Hanna said "You cheated. I don't know how, but you cheated." She just couldn't believe it. Four hands in a row and now all her chips were gone.
Samantha said "Your just pouting. I beat you fair and square, and now for my pay off..."
Samantha Paused for dramatic effect, then said, "tomorrow evening my brother is coming into town for the weekend."
"Ick," Hanna said, "Not Pete, Please No?"
Samantha ignored her, smirking as she continued, "The 3 of us will go out to dinner, and when we return to the apartment, you will let him fuck you..."
"Ewww" Hanna interrupted
"in the ass." Samantha continued undaunted.
Hanna's face went blank. "Pete and in the ass." she stammered "I've never let anyone do that, and I'm NOT going to start with your disgusting brother." She folded her arms across her chest, gave Samantha a stern look and just shook her head.
"It will be Pete and it will be in your ass." Samantha said "Remember our last bet, when you made me suck ancient Mr. Meacham's cock, right in the middle of the biology lab. Someone could have walked in at any time. He was more disgusting than Pete, and I did it because I lost."
Hanna just smiled, she had to admit that was a good one. She uncrossed her arms and almost begging said "Come On. You got an 'A' out of that one. Please, don't make me do this, Pleeeaaassse."
Samantha just finished gathering her chips then walked to her room. As she reached her room she turned and said. "Wear your pink capris to dinner tomorrow, they really show off your ass." Then she turned and pushed her door shut with an evil laugh.
Hanna stomped her foot and re-crossed her arms wondering how she got herself into this one.
Hanna and Samantha were Juniors in college. They had met the first day of registration their freshman year. Both were standing in line for dorm assignment, and struck up a conversation. They got along fine, and since they didn't know anyone else at this school, when they got to the front of the line, they convinced the lady to put them in a room together.
The two of them were like peas in a pod. They liked the same music, the same food, even the same traits in men. Since they got along so well, the conversation naturally turned to sex. Both girls admitted to being sexually active but had no current boyfriend. This being the case they worked out a signal, so if they brought someone back to the room, the other would know they needed their privacy.
Months passed and they girls grew closer. Samantha was seeing a hunk named Vince and bringing him back to the room occasionally. One night shortly before the big homecoming game, Hanna mentioned how hot Vince was. Samantha said he was OK, but just so-so in bed. Hanna said she'd like to find that out for herself.
Samantha said "I'll bet you would."
"Bet you say?" Hanna answered "Who do you like for the homecoming game?"
"What are you saying?" Asked Samantha "If you win you get Vince?"
"Well just for the night." Hanna said coyly.
"And if I win?" Asked Samantha
"I'll set you up with that boy I brought home 2 weeks ago, that guy definitely passed the oral exam." Hanna answered.
Samantha quickly said, "Your on, but I'm taking our team"
Hanna won that bet and Samantha was right Vince was only so-so, but the stage had been set for their little game. Sometimes, if they won they would make the other fix them up. Sometimes the would make the other do someone or something they didn't really want to do.
They only bet a few times their freshman year but the next year when they got a two bedroom apartment, the games seemed to pick up. Now it seemed they were betting all the time.
Lately the wagers have gotten more and more odd. Samantha had to blow Mr. Meachum. Before that, Hanna had to do the football mascot, while he was still in his suit. And before that Samantha had to get a boy to eat her pussy in the middle of the quad.
But now Hanna had to let Pete, Samantha's 18 year old, pizza faced, skinny, gross brother take her anal cherry.
Hanna pounded on Samantha's door. "Samantha, there's got to be something else." She yelled "I'll do the A.V. geeks. Come on. Cut me a break"
"Your being a real tight ass," Samantha laughed "Pete will like that."
Hanna heard Samantha's stereo volume go up and new this was a lost cause.
The next morning Hanna told Samantha about the nightmares that kept her awake all night hoping that would change her mind, but no dice.
Classes were difficult all day. Her thoughts kept coming back to Pete. She was almost positive he was a virgin. Obviously he wasn't going to know what to do with her ass. Well at least it would be over quickly. She smiled as she thought to her self he'll probably cum before he even puts it in.
That was it. If he came to soon she had to be off the hook. It just might work.
That night she dressed in a black lace thong, very short black skirt, and a low cut blue silk blouse with no bra.
When she met Samantha in the living room Samantha looked her up and down and said "Looks like someone is getting into this."
Hanna grinned and said "If he cums before he enters, it's his loss."
Samantha snapped back "I see how your going to play."
Hanna gave her best innocent look and said "maybe."
Samantha left to pick her brother up at the bus station. Both her and Hanna drove little sports cars, so neither had room for 3. Hanna waited a few minute's then drove her car directly to the restaurant. She waited at the table only a few minutes, then Samantha and Pete arrived. As they walked towards the table Hanna thought to herself he hasn't changed. Same messy hair, pock marked face and sloppy out of style clothes.
When they got to the table, Samantha took a seat. Pete walked over by were Hanna sat and reached out to shake her hand. Hanna reluctantly lifted her hand and he gave it a feeble shake. He blushed beat red and his eyes never left her cleavage as he squeaked "Hello Hanna."
Hanna noticed one thing she'd never noticed before, a huge bulge in the front of Pete's pants. Quickly he let go of her hand and said "excuse me I need to use the restroom." Then shuffled off.
"Same 5 foot 5, 110 pound geek of a brother." Hanna said
"Be nice." Samantha said, "After all he is your date for tonight." She let out a little laugh.
Hanna leaned forward and said "You probably didn't notice but I think he's got a hard-on."
"Probably." Samantha said "You are dressed like a slut." then after a pause added "Besides I told him on the way over what you were going to let him do."
"You didn't!" Hanna yelled, then caught herself lowered her voice and said again "you didn't."
"I did." Samantha said proudly "I didn't tell him about the bet, but I explained that you wanted him to be the first in your ass."
"I can't believe you." Hanna said.
Pete came back to the table and both girls couldn't help but notice the wet spot on his wrinkled khakis where the bulge had been.
Moments later the waitress came to the table to take their orders. She was a big 300 plus pound girl with stains covering her oversized apron. "Hello Hanna" The big girl said, "What are you having?"
All three ordered, although Hanna ordered light, not feeling well as she continued to think about Pete and what was now only an hour or so away.
"Who was that waitress?" Samantha asked
"That's Annabelle" Hanna said "She's in my astronomy class."
"She's big as a planet." Samantha teased.
"She's also your next loss." Hanna said
Samantha was speechless.
Pete sat through the whole exchange quietly staring at Hanna's cleavage. As a matter of fact that's how he spent most of dinner. Hanna did her best to drive him over the edge again, leaning down so he could look further down her top, seductively licking sauce from her lips, and the ice cream for dessert was a treat for her and him.
As soon as desert was over, Samantha said "I guess we should get on home, what do you two think?"
Pete quickly nodded saying "Yep gotta get home." and got up to show he was ready to go. Hanna noticed the bulge in his pants had returned.
"Damn" Hanna said under her breath. Then aloud said "OK.OK. You guys go. I'll pay, then be right behind you.
Samantha and Pete went to her car, Pete almost dragging her to move her along.
Hanna took her sweet time paying the bill, using the restroom, and strolling to her car, then drove the long way home.
Samantha and Pete sat on the couch watching TV and talking over family matters. Samantha had changed into her flannel Jammies and Pete wore nothing but his robe. Pete checked his watch constantly.
After a half an hour or so Samantha said "Relax, she'll be here."
"What if she changed her mind?" Pete asked
"She won't." Samantha assured him. Then under her breath said "She better not."
Just then the door opened and in walked Hanna.
Pete jumped to his feet.
"Relax stud." Hanna said "I'm not ready yet."
Pete sat back down but only on the edge of the couch. He watched Hanna's every sway as she walked into the kitchen and putting her purse on the counter reached into the freezer and pulled out the bottle of vodka. Hanna poured her self a tall glass, took a drink, then refilled the glass. She left the bottle and cap just lay on the counter, grabbed her glass and headed for her room.
When she reached her room she looked back at Pete, who looked like a puppy waiting to be told fetch, and said "Let's get this done." then walked into her room.
Pete leapt up from the couch and all but ran across the room. He stopped just inside the door. His jaw dropped as he gawked at Hanna. She was bent over her bed and her thong was clearly visable. He dropped his robe and just stood there.
Hanna said "Well stud, How do you want to..." Hanna stopped short as she turned to face Pete and saw him standing there naked. It wasn't his nakedness that shocked her it was the foot long sausage standing half erect that had her speechless.
"What do you know. Pete's packing meat." She stammered. "Close the door, and bring that thing over her and let me see."
Pete pushed the door shut as Hanna sat back on the bed. Pete walked over and stood in front of Hanna. She reached out and began to gently stroke his tool. It quickly hardened to it's full length and Hanna was in awe. It was almost as skinny as the rest of this wimp but it was easily 12 or 13 inches long. "No way does Samantha know her baby brother is hung like this." Hanna thought.
She stroked it a few more times and soon had forgotten who this monster belonged to. She leaned forward and took the head in her mouth. Slowly she slid more and more of his meat into her mouth. She could only manage about half, then started back out.
"Wow." Pete screeched out, "Samantha didn't tell me you wanted this."
Pete's high pitched voice reminded Hanna of who she was with. She removed her mouth from his cock and said "OK stud. How do you wanna do this"
"My sister said you would call all the shots." Pete said blushing beet red.
Hanna got up saying "Don't worry stud. I'll take the lead." She walked over and turned on the radio. Slowly she danced around him stripping off first her shirt than her skirt. She rubbed her titties on his arm and watched as his hard cock twitched. "Don't cum too soon big boy." she thought. "You wouldn't want to blow this chance." Wait a minute that was the plan. Snap out of it Hanna, She thought.
That was the first time she noticed the heat radiating from between her legs. What was happening? Could she want this geek in her ass. "Yes." she thought "I kind of do."
She sashayed over to her night stand and pulled out a condom and a bottle of lube. She said, "Lay down on the bed."
He climbed into the bed and laid on his back with his hard cock pointing at the ceiling. "Like this." he asked.
"That'll do just fine." she answered, unpacking the condom.
She sat on the bed beside him and tenderly rolled the condom onto his cock. Then picking up the bottle of lube shot a generous amount into her hand then rubbed it all over his latex lined rod.
She stood up and removed her thong. She reached her lubed hand around and poked the tip of her finger into her ass to lube it up a little.
"Are you ready?" She asked as she climbed back onto the bed and straddled Pete.
"Oh Yeah! Really Ready." said Pate.
"Remember what your sister told you." said Hanna "I'm calling the shots. Don't you dare cum til I say to."
"I'll try." He promised.
Hanna moved into position and put the head of his dick against her virgin asshole. Slowly she eased down pushing harder and harder but it just wouldn't go in. A little more pressure had Hanna thinking maybe this just wasn't going to work. A little more pressure and Hanna was thinking it just won't fit.
Suddenly the head popped in. Hanna froze. The pain was much more intense then she had imagined. She didn't move as her sphincter involuntarily contracted around the invader, causing the pain to increase even more.
Pete started to push his hips up.
"No. No. No. Please just hold still." Hanna begged.
Pete did as he asked and held perfectly still.
After what seemed like an eternity to both of them Hanna's sphincter began to loosen up. Hanna knew from stories she had heard that the pain would ease up too.
Slowly she began easing more and more of his cock into her tight ass. It took some time but his long dick finally hit bottom. Hanna could take no more. "God your cock is tearing me in two." she moaned.
"I'm sorry." Pete squeaked.
"Don't be." was all she said as she began to withdraw her ass from his cock. Out she moved until only the head was still in, then back in until he bottomed out again.
The pain was starting to ease and was quickly being replaced with a full feeling that felt so good. Hanna began moving in and out faster. The thought of fucking her own nasty ass with her best friend's icky little brother's cock was really turning her on. She thought it should be making her ill but it was making her hotter and wetter.
Her pace kept picking up until she was ramming Pete's cock in and out of her ass with blind abandon. Suddenly she realized she needed something in her pussy. She kept fucking Pete with her ass and reached down and stuck a finger and then two in her own pussy.
Just a few strokes of her fingers in her pussy coupled with Pete's strokes in her ass pushed Hanna over the edge. Her orgasm shot through her like lightening. "Oh god." Hanna moaned "Do it! Cum in my Ass!"
It took a couple more strokes but Pete did what he was told. With a grunt he began filling the condom with his seed.
"Yes! Yes! Yes!" Hanna panted as she rode his cock through their mutual orgasms.
Hanna slowed her bouncing on his cock as her powerful orgasm began to pass. She collapsed down onto his chest. She laid there for a minute feeling his cock softening in her ass.
Hanna leaned down and kissed him letting her tongue dance with his. That's when she remembered that this was Pete and quickly pulled her mouth away.
Looking down into his face she saw someone new. He still was pock marked but he wasn't completely ugly. And was a pretty good kisser. Hanna leaned down and kissed him passionately again.
This time when she broke the kiss she said "That was pretty damn good stud." and slowly pulled off his still softening cock letting it flop down on his belly then she climbed off the bed.
"Thank you." Pete said
"The pleasure was mine." she said reaching down and putting on Pete's robe. Quickly she grabbed a deck of cards and headed out to the living room.
"How was it?" Samantha giggled as Hanna came around the edge of the couch.
Hanna threw the cards at Samantha and flopped down on the couch saying "Fuck you. Deal. I feel like getting even."
Samantha said "I'm sorry. Hey if your wearing Pete's robe what's he going to wear?"
"There's some nice dresses in my closet." Hanna snapped "Now deal."
"OK!" Samantha said as she started shuffling "But if I win, tomorrow Pete gets your pussy...bareback."
Hanna had to hide a smile. She was thinking about doing that anyway.
Twenty minutes and several hands later, Hanna laid down a nine high straight.
Samantha knew she was beat and threw in her cards. "You win." she said "what's my penalty?"
"This ones a surprise." Hanna said "but it's happening tonight." she grinned and picking up her cell phone walked toward the kitchen.
Before Hanna got out of ear shot Samantha heard her say "Hello Annabelle. It's on. Get on over to my place right away."