Pegged

"No, they didn't," Alejandra replied, "That's just some silly, bigoted idea that modern people have got stuck in their heads about how dumb and stupid people were thousands of years ago.

"Ancient people knew the world was round and even had a good idea of how large it was."

"But..." Jason stammered, "I mean, why was Columbus trying to prove the world was round then?"

"He wasn't!" Alejandra insisted, "He and everyone else knew it was round, but he thought the world was only like a third the actual circumference.

"People didn't want to give him ships because they knew they couldn't make it all the way to China without running out of food and water, not because they thought they'd fall off the edge of the world!"

"No way!" Jason said, "That's like... it's in all the history books and shit!

"I'll bet you they thought the world was flat!"

Alejandra rolled her eyes and went back to eating her bagel slathered in cream cheese.

"Oh, so you know I'm right and don't want to bet?" Jason asked.

"Fine, what do you want to bet?" Alejandra shot back.

Jason grinned from ear to ear and took a sip of his orange juice while he pretended to consider. Alejandra rolled her eyes again since she already knew that Jason's bet was going to be sexual in nature. Alejandra picked up her coffee cup and leaned back to watch as Jason continued to ponder, his square jaw covered in stubble and short black hair sticking up in spikes from having just woken up. She and Jason had been together for almost two years but had only recently moved in together in a small studio apartment, the novelty of being together all the time still fresh enough for Jason to take notice of her only wearing panties and a crop top casually around the apartment. Her lack of body modesty had also brushed off on him so that he was sitting at the breakfast table in just his boxers, his muscular chest covered in dark, curly hair that she loved to run her fingers through.

"Ummm, since I know I'm right it has to be something really good," Jason mused before suddenly looking up with a huge grin.

"Oh god," Alejandra said with a groan before taking a sip of coffee.

"Remember you telling me how you and your best friend Susan used to go on 'double dates' all the time?" Jason asked.

Alejandra brushed her fingers through her long, blond hair and nodded with a smile of her own. Her and Susan going out with the same guy, taking the same guy home for them both to sleep with, to have the three of them spend the night doing everything Susan's very creative mind could dream up really couldn't be called double dating, but she wasn't going to argue since she could already guess where Jason was going.

"If I'm right you invite Susan over for the night," Jason said with a huge grin.

Alejandra's smile was slow and assured as she stared back at Jason, his green eyes staring into her own pale gray and gave a nod.

"Ok, fine," Alejandra agreed, "But if you're wrong...."

Alejandra reached up to tap a fingernail against her teeth while she stared at Jason whose eyes had widened in surprise before smiling from ear to ear.

"If you're wrong," Alejandra continued after a moment, "Then I still get to invite Susan over but we both get to peg you."

"What?" Jason exclaimed in surprise, "What that fuck, no!"

"Oh, so if you're right you get to fuck me and my best friend, but if you're wrong you have a problem with me and my best friend fucking you?" Alejandra asked sweetly, "And you already know you are right, so why worry?"

Jason stared at Alejandra for several moments before shaking his head.

"You're serious?" Jason asked, "If I'm... when I show you I'm right you'll invite Susan over and we can do everything you told me you two used to do?"

Alejandra smiled and nodded, "Yes, I'll invite Susan over and she's already mentioned how cute you are so I know she'd love to spend the night with us.

"But when I show you how wrong you are I get to invite her over anyway and we get to take turns pegging you."

Jason continued to stare at Alejandra for several more moments and then stood up and thrust out his hand, "Fine, since I know I'm right!"

Alejandra smiled and reached out to shake Jason's hand and then took another slow sip of her coffee.

"Fine," Alejandra said, "Why don't you be a good little boy and go do a google search on if Columbus thought the world was round or not."

Jason popped up out of his seat and hurried over to the desk beside their bed, his boxers suspiciously tented out while Alejandra sat back and watched with a knowing smile. After several minutes and what was obviously several different searches Jason pushed back away from the desk with a deer in headlights look on his face.

"Son of a bitch," Jason mumbled.

"Oh, do I have a phone call to make?" Alejandra asked casually, "I bet Susan could drop by later today so we have the rest of the day as well as tonight to take turns fucking you."

Jason turned to glare at Alejandra who laughed in delight.

"Don't worry, dear," Alejandra said with a smile, "I'd love to have you fuck me while Susan pegs your cute, tight ass and I bet she'd let you fuck her while I take my turn too."

Jason's glare suddenly turned speculative as Alejandra stood up to walk over to the nightstand and pick up her phone.

Jason looked up a few hours later at the knock on the door, his freshly shaved face more than a little pale as Alejandra popped up from the bed where she had been relaxing to pad quietly over to the door. Jason's eyes followed Alejandra hungrily in her sheer dressing gown with the black edging and nothing on beneath. Alejandra had had him help her get ready for Susan to drop by, help her shave her mound and rube vanilla scented moisturizer over her entire body, but had also flat out refused to give him any relief or even to let him take care of his aching, painful balls himself. Now that Susan had finally arrived he stood up on shaking legs and tried to put on a confident smile. Alejandra glanced back at Jason and quickly blew him a kiss before turning to open the door.

"Alejandra!" Susan cried the instant the door was open and stepped in to embrace her before leaning down to kiss Alejandra's lips.

Jason could only stare at the slow, lingering kiss, his petite five foot four blue eyed blond girlfriend standing on tiptoe to kiss her six foot two brunette best friend with her smoldering brown eyes. The two women couldn't have been bigger opposites with Alejandra's small pert B cup breasts compared to Susan's enormous sagging D cups and nipples that always seemed to be tenting out her shirts, Alejandra's luscious curves and ample padding next to Susan's lean, athletic body that seemed to be all legs. But what instantly drew Jason's eyes and had his heart racing anxiously wasn't the outline of Alejandra's naked body through her sheer dressing gown, it wasn't Susan's equally revealing white pencil dress that left her shoulders bare while clinging to every curve of her body. What captured and held Jason's attention while he stared in trepidation was the enormous strap on purple dildo that Susan already had on and was now pressed awkwardly to the side between Alejandra and Susan.

"Ummm, I've missed you, love," Susan purred while staring down at Alejandra and then turned to glare at Jason, "But I hear someone's been naughty and needs to be put in his place!"

"Hey, Susan," Jason said nervously and then jumped when Susan snapped at him.

"Hey, Susan?" Susan yelled, "What, you think you can use me like some fucking cheap ass poker chip in a Las Vegas casino and get away with 'Hey, Susan'?

"Why are you still wearing clothes!"

"What?" Jason asked in confusion as Susan stepped into the apartment and Alejandra closed the door behind her with a smirk.

"I asked why the fuck are you still wearing clothes?" Susan demanded while she crossed her arms and the strap on dildo stood prominently out form her slim waist, "Get fucking undressed!

"Now!"

Jason looked at Alejandra in astonishment who only looked back with a grin.

"She's the one who's about to fuck you in the ass so I'd do exactly what she says if I were you," Alejandra said.

Jason glanced from Alejandra to Susan in astonishment while making an unbelieving sound in the back of his throat.

"What... the fuck... are you... waiting for?" Susan again demanded.

Jason could feel his heart hammering in his chest and reached down to unbuckle his cargo pants before pushing them down over his waist. His own erection sprang to attention as his shorts fell around his ankles, even in his anxiety Alejandra's teasing all morning still keeping him painfully erect.

"Not much to compare to mine," Susan said while staring at Jason's erection and stroking the dildo strapped to her waist with her hand, "But not too shabby.

"What is he Alejandra, seven inches?" Susan asked, "Does he feel good inside your tight little pussy?"

"Almost seven," Alejandra said and stepped behind Susan to reach around to fondle and squeeze her breasts, "And he feels wonderful inside of me, but he also absolutely loves eating pussy and lets me sit on his face for thirty, forty minutes until I cum allllll over him."

"Ummm, sounds like a good catch," Susan replied and reached up to place her own hand over Alejandra's who was still busy squeezing and kneading Susan's ample breasts, "Hey! Shirt too, Jason!"

Jason jumped and then quickly slipped his UnderArmor sports shirt over his head and tossed it onto the bed so that he was standing completely naked in front of Alejandra's best friend since college. Jason had wondered from time to time what it must feel like for a stripper to step out on stage in front of all those strangers for the very first time, to have all those men looking at you, daydreaming about you, wanting to fuck you, and had a tiny taste of that sensation as Susan slowly ran her eyes over his body. Jason's own eyes were again drawn to the purple strap on dildo Susan was wearing, her hand stroking its length as if it really was her own erection before finally looking up to catch her eye.

"You like my dick?" Susan asked, "Get over here and suck my dick, Jason."

Jason shook his head in disbelief and then saw Alejandra slowly raising the hem of Susan's pencil dress up higher and higher, working the tight fitting material through the straps of the dildo until he was sure he was about to see her mound exposed.

"He doesn't listen worth a shit, does he," Susan said in exasperation while Alejandra continued to work Susan's white dress up higher and higher.

"I'm sure he can learn," Alejandra said and then surprised Jason by giggling.

"Get over here and get on your fucking knees!" Susan demanded.

Alejandra managed to work Susan's white dress up another quarter inch and Jason caught a glimpse of Susan's inner lips between her thighs just before Alejandra's fingers slipped in to cover and conceal them. Jason looked up to catch Susan's eyes again and then almost as if it were someone else he took a step forward. As if that first step had been some sort of release Jason quickly found himself standing in front of Susan and after she lifted an eyebrow while staring at him he sank down onto his knees with the purple dildo only inches from his face. This close it was more than obvious that the dildo was close to the same size as Jason and covered in fake veins and ridges, the edge of the glans well defined. Jason leaned to the side and ignored the fake dick in his face to stare at Alejandra's fingers that were slipping between Susan's thick, dark brown wrinkled inner lips to tug gently down on them.

"Open up Jason," Susan said and reached down to take Jason's head in her hands.

"Hey, this wasn't part..." Jason began.

"I don't give a fuck what you think was a part of this or that," Susan cut in, "You do NOT get to fucking use me in a bet without even bothering to ask me first!"

Jason looked up to see Susan glaring down at him and then glanced once more to see Alejandra's fingers tugging on Susan's inner lips before slipping upward to disappear deeper between Susan's mound. Jason glanced up again when he heard Susan give a soft moan of pleasure and jerked in surprise when Susan gave him a sharp wrap on top of his hear with her knuckles.

"Open up!" Susan demanded.

"Fuck it," Jason said to himself and opened his mouth.

Susan quickly guided the purple dildo that she had continued to stroke until it slipped inside Jason's mouth, the smell of rubber and lube filling his nostrils as the soft, spongy dildo down his throat until he started to gag.

"There's a trick you're going to have to learn, Jason," Susan said and took Jason's head in her hands as she began to gently thrust back and forth, "You need to keep your throat relaxed and try to suppress your gag reflex."

Jason again tried not to gag and reached out to take Susan's thighs in his hands to steady himself, the feel of her smooth skin sending an electric jolt of excitement through him. He could still catch glimpses of Alejandra's fingers between Susan's thighs, Susan's thick, luscious inner lips being pulled and stretched two or three inches out before slipping between Alejandra's finger tips, could hear Susan's moans of pleasure even while Susan thrust the dildo down his throat. After a moment or two Jason was able to relax enough to stop gagging and glanced up to see Susan staring down at him while biting her lower lip, her fingers caressing through his hair while she thrust her dildo down his throat.

"Ohhh, good boy," Susan panted, "I think he's a natural Alejandra.

"I bet you've sucked dick before, haven't you Jason."

"Ungh ungh," Jason managed to say in denial and then jerked in surprise when he felt someone touch his painful erection.

The musky smell of a woman's arousal replaced the smell of rubber and Jason managed a glance down to see Alejandra's bare toes hovering close to his erection before managing to give his length a soft, quick stroke.

"Ummmm," Jason managed to moan, the feel of Alejandra's toes amazing on his overly sensitive dick.

"See, you love sucking cock, don't you Jason," Susan said and then suddenly pulled the dildo out of Jason's mouth, "I bet you're going to love taking it in your ass even more.

"Get on your hands and knees on the bed, Jason.

"Now."

Jason panted for breath and had to struggle to stand up before giving a quick nod.

"Alright, but do I get to make love to Alejandra at the same time?" Jason asked and started towards the bed.

"Oh, fuck no!" Susan instantly replied, "You'd like that, wouldn't you.

"Fucking your beautiful, smart, delicious girlfriend while I fuck you in the ass, so no.

"You don't get to fuck her, but since she said you were so good at it you can show me how much you like to eat pussy."

"Ummm, I like that idea," Alejandra purred and managed to beat Jason getting to the bed.

Alejandra took off her dressing gown and quickly climbed up onto the center of the bed, her legs falling open as she used her fingers to spread herself for Jason who climbed onto the bed after her. Jason adored Alejandra's pussy, just as petite as the rest of her body with smooth, pink inner lips and a prominent hood that hid her pearl a little larger than a pencil eraser. With Alejandra's excitement and her spreading her flower open for him to see the soft, pink, glistening flesh of her vulva that pearl was on prominent display as well. Jason could even see the moist skin of Alejandra's inner thighs and realized just how excited she must be.

"You smell delicious," Jason said as he breathed in Alejandra's earthy aroma and then bent down to run the length of his tongue across her prominent clit.

Alejandra's tangy flavor filled Jason's mouth as her back arched up off the bed, a soft moan of pleasure escaping her before he plunged his tongue deep inside of her sheath.

"Ohhh, I think she likes you devouring her," Susan said from behind Jason as he felt the bed shift, "Such a natural at sucking dick and eating pussy."

Jason took a moment to glance back and then did a doubletake as he saw Susan naked on her knees, her breasts penduluming side to side while she refastened the strap on around her waist.

"What the fuck, Jason?" Susan asked but also arched her back so that her enormous breasts were thrust out in front of her body, "Did I say you could stop eating pussy?"

Jason grinned and licked Alejandra's nectar from his lips and then turned back to her flower, quickly bending down to press his lips against her clit while he hummed and slipped his fingers into her silky smooth sheath.

"Ohhhhhhhhh," Alejandra cried out, her back again arching up off the bed as she gripped Jason's head in her hands.

"Ummm, I think Alejandra likes that," Susan said just as Jason felt something wet and cold splash between his ass checks.

Jason tensed waiting for the moment he had been dreading but jerked in surprise as he felt Susan's fingers spread his ass checks apart and then begin to stroke his puckered and very tight asshole, spreading the cold lube she had dripped onto him seconds before between his checks and liberally coating his asshole. He and Alejandra had tried butt play in the past with the tip of a finger or even licking each other's rosebuds occasionally so he wasn't to surprised when Susan slipped a finger inside of his ass, barely flinched when he felt her slip two fingers inside his body and never made a sound when he felt two more fingers slip in and then begin to gently work his asshole wider.

"Did you forget someone?" Alejandra said plaintively as she rocked her hips, Jason realizing that he had completely stopped eating his beautiful girlfriend's pussy while Susan worked on his ass.

Jason suddenly jerked in surprise as Susan smacked his ass hard enough to elicit a yelp of pain at the sharp crack that echoed in the room.

"Are you neglecting poor, sweet Alejandra?" Susan asked and then smacked Jason's ass once more with a sharp crack, "You need to make sure you're keeping Alejandra very very happy Jason."

Jason quickly slipped his tongue deep inside of Alejandra's pussy again, her clear nectar pooling inside her vulva for his tongue to dip into.

"Ummmm, yessssss," Alejandra moaned.

Jason tried to concentrate on doing everything he knew Alejandra enjoyed, sucking on her inner lips hard enough for her to gasp in pleasure and pain, tugging on those soft lips and stretching them out from her body, pressing his lips against her clit and humming, placing his entire mouth over her clit and sucking until her body was squirming beneath him, but the entire time he was aware of Susan's fingers working on his asshole, stretching him open and probing deep inside of him. It wasn't painful and the sensation certainly wasn't uncomfortable, but he couldn't decide if there was any pleasure involved either.

"Are you ready, Jason?" Susan suddenly asked and Jason felt her fingers slip out of his asshole quickly followed by a different pressure, "Are you ready for me to fuck you?"

Susan didn't wait for him to respond and Jason felt that pressure build, become uncomfortable and then something slip inside of his body. He could feel Susan thrusting, a little more of the strap on dildo penetrating him each time she pushed forward and then gasped when he felt her hand reach around his waist to take his erection in her hand.

"Oh, my, you are dripping precum aren't you," Susan exclaimed and then began to squeeze and stroke Jason's dick in time with her own thrusts.

Jason couldn't concentrate on eating Alejandra's pussy and simply pressed his tongue against her prominent clit to let Susan's thrusts rock him back and forth. Alejandra didn't seem to care, her fingers laced through his hair as she pressed her hips up to force her clit against his tongue and rocked in time with Susan as well. In moments Jason felt Susan's stomach slapping against his ass with each of her thrusts and knew she was all the way inside of him, the feel of the dildo strange as it pressed against places he had never imagined. Susan's hand continued to stroke his length, real pleasure building as he felt an additional pressure in his prostate and he knew that after the entire morning of being teased he wasn't going to last long at all.