An anal Odyssey
Chapter 1: Ripe and Ready
For Jenna Bailey life was as sweet as could be. A loving mother and wife with a successful husband and two beautiful children, she had a reputation as a pillar in the community. Jenna was a soccer mom, a P.T.A. all star, and one of the church going social elite. In her late thirties, she still retained her incredibly youthful beauty and a body that bordered on otherworldly.
It wasn’t the platinum blonde hair that fell across her shoulders like waves of sunlight, or the sky-blue doe eyes that others often lost themselves in that made her special. Her warm personality, amazing smile, and sweet southern sensibility were all traits that she wore with pride, but what truly set her apart from mere mortals was her killer body.
Stunning just wasn’t the word. Jenna’s wide hips, enormous breasts, and her thick smooth thighs of bronze were like obscene poetry given form. Her big beautiful ass was the stuff of legend. It simply had to be seen to be believed. Two juicy pillows of divine beauty that curved into her lower back and met at the tops of her thighs as though God himself had taken an eighth day of creation to concentrate on her spectacular ass.
Jenna knew she was attractive. She could have had anything she had wanted in life, but she was content. She loved her husband Harold and her boys, Scotty and Dalton. They were the men in her life that mattered most and she had given so many years to all three to ensure they would be happy and well cared for. Lately though, as her boys were finishing school and getting ready to head off to college and her husband was growing more and more distant and less and less romantic in his middle age, she felt something inside her left unfulfilled. She just wasn’t sure what that may be.
Saturdays were shopping days, and as Jenna parked her minivan and set out down the aisle of her local grocery store all eyes were on her. She wore cute little open toed mules to show off her perfectly pedicured toes and a form fitting skirt that covered her to mid thigh, hugging her incredible rear end like a second skin. Her top was a sleeveless cream colored blouse with a black lace bra underneath; custom ordered to contain her gigantic double H-cup breasts.
With her hair pushed up in a trendy bun and a string of pearls accenting her long swan-like neck, Jenna pretended ignorance as she strode down the aisle of her local supermarket like a runway model behind her shopping cart. She knew on some level that men liked to watch her; women too. It gave her a secret thrill that she would never have admitted to as she paused from time to time, posing just so with the arch of her back or the stretch of her neck. It was a naughty pleasure, but innocent.
As she guided her cart along into the produce section everyone around her stopped and stared. Grocery stock boys began to absentmindedly caress watermelons, female shoppers began to question their sexuality or abandon it altogether, and men tried their best not to pass out as blood relocated itself from their brains to other bodily locations. One other shopper however, took more notice than anyone else.
“Holy fuck!” A female voice caught Jenna off guard and a figure at her side caught Jenna’s attention as the scent of expensive perfume hit her at her core. She glanced up at a dark haired beauty of a woman approaching her, and faltered slightly as she felt intense eyes meet her own. “Are you aware what a world class fuck you are?”
Jenna turned, shocked. She was certain she couldn’t have heard the woman right. No one talked like that in middle class America and most certainly not to her. As she turned, she found herself at a loss as she took in the stranger’s body. She held a small basket at her side with her own items and met Jenna with a big smile that was much more intimate than it should have been.
“Pardon me?” Jenna asked, turning on her toes and looking the woman up and down. Not only was this woman very beautiful herself, but she had a body that rivaled Jenna’s own. She wore a one piece dress slit up the side to reveal a hint of bare hip. Her top wrapped around the back of her neck leaving her shoulders bare while straining to contain the gigantic breasts contained within. High heels, stockings, and a cute little sterling belt of hoops accented her look. She was lovely, she smelled intoxicating, and Jenna felt a building heat between her thighs as she admired her new friend. “Did you just say…?”
Jenna trailed off as the dark beauty moved even closer. The brunette tilted her head to one side, giving Jenna’s body a long slow look as she set her basket down and rested a hand on Jenna’s own, set on the push bar of her shopping cart.
“I’m sorry. Did I offend you?” The woman asked with a small chuckle. “I would think not a day of your life goes by without someone pointing out the fact that you are a walking wet dream. There isn’t a man in here that isn’t eyebanging you right now. My pussy is wet just being this close.” She added, grinning as she moved in even closer, inviting herself into Jenna’s space. “I’m Monica by the way.”
“I…” Jenna was at a loss. Never before had she met a woman that was so forward or so openly sexual. “I need to go.” She said at last, pushing her cart away toward the frozen food section.
Even as she made her retreat Jenna could feel Monica’s eyes on her body from behind. It made her feel different than it did when others looked. Monica wasn’t hiding the way she stared after her. She was studying Jenna’s body with interest. Jenna could almost feel her eyes taking in every line and curve. If she was honest with herself it wasn’t entirely uncomfortable.
Monica was nothing if not persistent. She kept pace, reclaiming her spot at Jenna’s side as she openly flirted.
“You’re shy? That’s cute.” Monica whispered with a warm smile. “That’s kind of like a lamborghini in a school zone though. Nobody has ever really revved you up, huh?”
“I don’t know…” Jenna tried to avert her eyes, but Monica was impossible to ignore. Try as she might to get away from her, she couldn’t help but steal the awkward glance at the busty dark haired woman who was so openly coming on to her. It was the first time she had seen another woman with a shape that mirrored her own. Her curiosity was building, but her upbringing and life as a small town homemaker was trying desperately to bring her back in line. “I don’t know you. You shouldn’t say things like that. That’s so dirty.” She added under her breath, biting her lower lip when another whiff of Monica’s heat hit her and caused her body to shudder with desire.
“What, admiring your smoking hot body and gorgeous face?” Monica asked. “If you think me complimenting you like that is dirty, you ain’t seen nothing yet darling.”
Monica moved around the front of Jenna’s cart, stopping her in her tracks as she grabbed hold of it. She leaned over the groceries so no one else could hear, a big smile stretching from ear to ear. Jenna stood with wide eyes as she tried not to imagine what that short-cut raven hair might feel like in her fingers, or how another set of massive breasts might feel pressed into her own. She’d never thought things like that before. Why now?”
“What would you say if I told you I’d like nothing more than to drop to my knees right here and let you back that majestic ass right onto my face so I could scrub your pink little butthole with my tongue til you cum all over my chin?” Monica challenged.
“Oh my!” Jenna gasped, covering her mouth with her hand. She wasn’t sure how to react. No one had ever spoken to her like that. She didn’t think people knew how to talk like that.
“Tell me how that sounds.” Monica insisted, arching her back as she leaned over the shopping cart and brought her own big beautiful butt up high behind her, so that Jenna could see it over her shoulder. “Don’t answer like you’re supposed to, Baby. Answer like you want to. Be honest with yourself and with me. Wouldn’t it be nice if I stuck my tongue up your ass? Wouldn’t you like me to fill your hot little butthole with spit as I coddled your gorgeous butt in my hands? Answer me.”
“Yes.” Jenna answered. Shocked at her own words, she took a step back. “I mean, no. That’s… I said I don’t know you. Please leave me alone.” She averted her eyes once more, pulling her cart back with her as she turned and started away at a quickened pace.
“Nope.” Monica giggled with confidence as she rejoined her quarry once more. “Too late. I knew it. I knew it the second I saw you. You don’t walk around with a body like that and not have the kind of twisted little desires that go along with it. Lie to your husband all you want, but I know you. I still haven’t got your name though.”
“Jenna.” Jenna answered, and her pace slowed as she grabbed a box of toaster pastries from a shelf as they passed. “I… You don’t know me. I can’t believe we’re even having this conversation. I wish you would just leave me alone.”
“I don’t think you do.” Monica argued with a wicked grin, moving in close enough so that their hips met. Each time Jenna would look her way she would meet her eyes with a knowing smile that brought a blush to both their cheeks. “I think you think that’s what you are supposed to say, but I think what you really wanna say is something else. You’re right though. You don’t know me. Why does it matter what you say to me then? Wouldn’t it be nice to let it out, just once?”
“Let what out?”” Jenna asked, turning to meet Monica’s big green eyes with her own and for a moment allowing her white picket fence barrier to fall away. “I don’t… I mean, there’s nothing I need to…”
“Whatever you like.” Monica shrugged. “It’s like they say. The truth shall set you free. You don’t know me, and I don’t know you. How about you throw caution to the wind and just say what it is you really want to, just to see how it feels; just once. Nobody is looking.”
“I…” Jenna considered Monica’s words. As she did, Monica moved in even closer. For the first time Jenna could smell something other than her sweet perfume. She could almost taste Monica on her tongue; the peaches and cream of her body wash, the salty tang of her long beautiful neck, and God help her the sugary sweetness of her pussy too. She allowed her eyes to wander down over Monica’s hips and across her voluptuous breasts. Glancing left, then right and seeing they were in fact alone in the pasta aisle, Jenna felt something inside her begin to respond.
“Nobody’s listening Baby.” Monica spoke into Jenna’s ear, her hot breath causing Jenna’s whole body to tremble. “Just say it. Let it out for me.”
“I…” Jenna hesitated, then saw Monica’s eyes once again, and there was no judgement there. All she saw was complete acceptance. She felt herself smile. “I… would love to eat your pussy.”
“Mmmmmm.” Monica groaned, pressing even harder into her new friend. “I know you won’t believe me, but I just came a little. My pussy is yours. You can eat me til I pass the fuck out. I’m gonna want some of you in return though.” She added with a devilish smile.
Jenna felt her whole body flush with excitement as Monica took her by her wrist and pulled her away from the cart. She followed as if hypnotized as they walked back through the frozen food, through produce, and right out the front door without bothering with their groceries. She didn’t even pause when Monica asked her where she was parked, pointing out her minivan right away as Monica continued to pull her along.
“Oh my God.” Jenna groaned in rising lust as Monica guided her into the minivan’s back seat and closed the door behind them. She came at her like a jungle cat, pouncing and bringing her hungry mouth down hard on Jenna’s own. It was the first time she had ever kissed another woman, and certainly the first time she had ever been kissed like this. “Oh my GAWD!!”
Monica was all tongue, groaning with hunger for her sexy blonde as she invaded her mouth like she intended to eat her alive. Jenna fought back, fueled by a desire that she had neglected for far to long as she took Monica between her lips and suckled at her, pulling her further into her mouth before introducing her own tongue in return, wrestling with her new lover as they smashed their bodies together and reached out, groping each other all over like their minds were lost to their shared sensual lust.
As Monica tilted Jenna’s head back. Jenna gave over control, opening her mouth wide as Monica rose up over her, pursing her lips and letting a long glob of sugary spit fall from her mouth into Jenna’s own. Feeding her like a mother bird, Monica caressed Jenna’s neck and face as she swirled her tongue, making more sugary-sweetness to add to the pool of slobber that Jenna’s tongue floated in inside her mouth. Finally she came down hard against her, kissing her once again and groaning as they began to pass the sweetness back and forth between them, paying little mind as it dribbled down their chins and into the valley of Jenna’s cleavage.
Jenna was on fire. What shocked her most was that the thought of Harold sitting at home in his slippers behind his newspaper only seemed to fuel her further. How dare he ignore her when this gorgeous woman was obviously so incredibly attracted to her. How dare he not notice the sexual animal that she was deep down. She almost laughed out loud as Monica reached for the buttons of her blouse, but she wasn’t freeing her big tits fast enough, so Jenna playfully knocked her lovers hands away and undid them in quick fashion.
Monica sat back, tugging the material of her dress up over her head and revealing her big tits; large beautiful bronze areola like pie plates with fat bulbous candy centers that cried out to be bitten and tugged. She shook them invitingly for Jenna as Jenna’s bra was tossed aside, forgotten in the floorboards, her own naked flesh laid bare for her lover in turn.
“FUCK!” Monica groaned, taking hold of Jenna by her waist and yanking her closer. She went down on Jenna’s big beautiful gum-drop nipple like a woman possessed, latching on and and giving it suck as she looked up into Jenna’s eyes and found her staring back in shared desire.
From one big beautiful tit to the next, Monica left behind wet glistening pink nipples as fat as her thumbs and huge areolas that puffed out and proved to be incredibly sensitive to the touch. She painted each juicy tip with her spit, and each time she would tug at Jenna’s beautiful tits with her mouth or teeth Jenna would toss her head back and groan with pleasure. When Monica was at last rewarded by a tiny spurt of creamy milk across her tongue she lost all self control and doubled her efforts to gobble down more. Jenna coddled her lover by the back of her head as she fed her mouthfuls of warm milk, her entire body shaking with pleasure as Monica nursed.
They were all hands, groping and caressing one another as they tore at each other’s clothes. Shoes fell off pretty little feet and Jenna’s skirt was tossed into the passenger’s seat along with Monica’s dress as they stripped bare, lost in the pleasure of their lust. Monica’s panties came down next; a tiny black thong that concealed a fat mound and gorgeous little button of a clit. She had a tiny tuft of fuzz just above her pussy that Jenna reached out for, her fingers delving deep into the downy fur and cuping the bald lips of her pussy with her palm.
Jenna’s panties were Monica’s pleasure to remove. She started to take them down herself, but Monica refused to allow it. Instead she guided her goddess over the back seat, sliding in behind her and taking black lace in her experienced hands. She mewled with desire as the string of Jenna’s panties was pulled out from the deep canyon of her bottom and she urged them down across her thighs and beyond.
For a moment Monica just sat back and stared in awe of Jenna’s big beautiful butt. She placed her hands on both cheeks and spread her open, groaning at the beauty of her asshole and the lovely pink peach of her pussy peeking out from underneath. True to her word, she licked her lips to get them nice and wet before she dove right in to wrap them around the sugary-sweet asshole before her.
“Oh my Gawd!” Jenna groaned as she felt her butthole under assault. She gripped the seat and trembled with pleasure as Monica dove between her cheeks and began to gobble her rectum with wildcat lust. She absolutely buried herself in Jenna’s ass, and Jenna could do nothing but whine and whimper as her lover stuffed her tongue as deep as she could manage, swirling it around the inner walls of Jenna’s virgin chute and pushing mouth fulls of spit up into her to grease the way for more anal pleasures.
“”Eat me!” Jenna groaned. “Eat my fucking asshole! Feels so fucking good!”
“There she is.” Monica came up from her feast, smiling as she licked her lips of Jenna’s flavor. “About time I met the real you baby. I told you I was gonna eat your ass for days, but that’s not all I’m going to do to it. Baby, I’m gonna fuck you soo good, right up that beautiful asshole.”
“Yes.” Jenna purred. “Oh fuck yes. Please. I wanna feel you fuck my ass. Oh Monica! This is sooo fucking hot.” She glanced back, eyes over her shoulder as Monica met her gaze once more. Jenna the housewife and mother were nowhere to be seen. The real Jeanna had emerged, and she was a gorgeus fucking sight to behold. “Please. Please don’t stop. Put your tongue back up my butt.”
Once more, Monica reached out to grab hold of Jenna’s big bottom with both hands, pushing her cheeks wide apart as she brought her mouth down over the twitching star of her lover’s rectum. She spat right onto Jenna’s hole, growling like a wild animal as she watched how Jenna’s pucker spasmed and puckered at the heat of her saliva. She swore she could hear it sizzle as it hit her steaming hot little opening, and once again she brought her mouth down onto Jenna’s asshole to gobble her some more.
Lips and tongue soon gave way to fingers as Monica eased into Jenna’s butt with a gentle penetration. Jenna took it without any sign of discomfort, and so she added a second finger, then a third as she began to openly saw them in and out of the tight pink of her lover’s velvet hole.
“You’re so tight.” Monica purred, rising up and pressing her pussy into Jenna’s flank as she continued to finger fuck her new lover’s tight butt, one hand tracing up and down the sexy blonde’s back and over her pretty shoulders as the other twisted in and out of her suckling anal hole. “He’s never even touched you here, has he? That fucking bastard doesn’t deserve you.”
Jenna looked back again, biting her lower lip as she felt Monica slide a fourth finger into her asshole along with her hand right up to her thumb. She looked deeply into Monica’s eyes, listening as her lover spoke to her in such a tender tone with such depraved words. She wanted to respond, and in some way defend poor Harold for being so inadequate in bed with her and never indulging this filthy hidden side of her, but her words faltered as she felt Monica’s thumb curl into her hand and slip in as well. She gasped out loud as her asshole accepted what she was given and it closed tightly around Monica’s wrist.
“OH MY GAWD!!!” Jenna shook violently, her entire body racked with a powerful orgasm as Monica fisted her butthole with slow sensual twists of her arm and pumps of her hand. It was a pleasure she had never even imagined her body was capable of, and as she came her pussy squirted a powerful torrent of juices across the seat and Monica’s naked thigh.
Any other lover might have stopped. In Jenna’s experience that was what most men would do once they knew the woman had cum. Monica only increased her efforts and rose up behind Jenna’s body, pumping her hole even harder, deeper, thrusting into her with as much force as Jenna’s body could take. Jenna felt her mind melting in her head from the most intense pleasure she had ever experienced in her life.
“Mmmmmm that’s my bitch.” Monica purred, leaning down and dragging her tongue over Jenna’s shoulder and up along her neck. She continued to stuff her lover’s butt with steady thrusts, watching her tremble and reveling in the way her body shuddered from head to foot. “My sweet sweet little sodomy bitch. You look so fuckin pretty with my hand in your bottom baby; your juicy anal-cunt. Oh my little ButtFuck Angel.”
There was no more minivan. The world outside was gone as well, and they were transported to a world of soft pink pillowy sweetness. The air tasted of sugar and sweat and everything around them was like wet velvet and warmth. When Jenna finally began to come down from her mind altering orgasm she was only just aware of Monica easing her hand out of her butt and leaning over her back, kissing her shoulder and the back of her neck with tenderness.
“You are incredible.” Monica said at last, smiling as Jenna slid down into the seat as she turned. She was out of breath, her huge breasts rising and falling as she tried to regain her senses, laying back against the van’s door as Monica climbed up over her, smiling with affection as she found Jenna’s mouth once more in a deep soulful kiss.
Both their bodies were slick and glistening. As they kissed, they reached out and ran their hands all over curvy hips and up between shoulders to hold one anothers necks and better crush their steaming mouths together. Monica moved as they kissed, scissoring their legs together and bringing their juicy pussies close. Jenna could feel the heat of her lover’s sex even before it pressed down against hers, and when it did she reached out, grabbing two hands full of Monica’s ass and pulling her in hard so their muffins could grind.
They seperated, turning their bodies so that they were at a better angle to rub their steaming mounds together. Monica mewled with pleasure as she looked down at her lover, guiding Jenna’s long leg up along her body and holding it to her belly, dragging her tongue up the length of Jenna’s calve and across the arch of her pretty little foot. As she took Jenna’s toes between her lips Jenna tossed her head back in lust once more, but she was not to be outdone.
With Monica’s sweet little pussy now openly humping away at Jenna’s own, her body was turned half toward the seat and so Jenna reached down between them, running her fingers over the cheek of Monica’s ass and then deep between her cheeks. She found the tight anal ring of Monica’s rectum and pressed her thumb against it, grinning wickedly as she saw her lover look down along the landscape of their bodies and encourage her with a wicked smile.
“Dirty girl.” Monica teased with a wicked grin, turning almost fully on her side as she held Jenna’s pretty leg close to her tummy and humped her muffin in a slow sensual grind. “Are you trying to get in my bottom?”
“You made me cum so hard.” Jenna groaned, for the first time feeling another woman’s asshoe on her fingertips and gently rubbing it in circles as she teased the sweet crinkled meat of it open and began to ease inside. “I never imagined my butthole could feel soo good or take sooo much. I’m gonna make you cum too. I wanna fuck your asshole too baby. Do you want my hand in your bottom?”
Monica nodded, turning even more to allow access and groaning as she took Jenna’s toes back in her mouth, slurping loudly as she allowed access to her tight rear entrance, arching her body to give Jenna everything she wanted.
Monica was losing her mind with pleasure by now, and bit softly into the flesh of Jenna’s leg as she felt fingers easing into her ass one by one. She intended to deny her new lover nothing, and gasped out loud as Jenna returned the pleasure of what had been done to her, finally cupping her hand and tucking her thumb as she pushed into Monica right up to her wrist. Monica shook as she was filled to her limit, but looked down at Jenna with a half lidded stare of pure sexual desire as she welcomed what was being down to her, stirring her hips and humping against her lover as Jenna began to fist her butt.
“Fuck me Baby!” Monica begged, her mouth wrapped around Jenna’s big toe; scrubbing away the nail polish with her tongue as she twisted her waist to better allow her girlfriend to fist fuck her butt. “Be mean if you want. I fucking love it. Make me your fucking bitch!”
Jenna nodded. She wanted nothing more than to please Monica for what she had shown her, and so as she propped herself up on one elbow she began to thrust and pump her fist in time with the movements of their bodies together. She laughed out loud, overcome by her own pleasure as their pussies crushed together time and again and she felt Minica’s asshole biting down on her wrist, taking everything she had to give and more.
“Oh SHIIIIITTTTTT!” Monica whimpered, clawing the seat as she was overcome by sensation. She felt Jenna punching in her butt by now, and was losing her mind as a huge orgasm washed over her; her own pussy spurting like a tidal wave between them, splashing back as their pussies rubbed furiously together. “Fuck Fuck Fuck Fuck!” She chanted, shaking all over as she came, looking down past her own body at Jenna looking back at her, a moment of intense bonding as they locked eyes in depraved lust.
For several long minutes, Monica quaked and trembled. Finally she began to relax, and let out a long whimper of pleasure as Jenna slid her hand back out from inside her new lover’s beautiful ass. She held her as she did, staring with delicious pleasure as she watched Monica’s butthole slowly close; still so pink and sweet looking. It was just to beautiful not to taste what she saw.
They crawled into a sixtynine together, both wet and dripping with each other’s cream as they lay on their sides in the soaked seat and made a feast out of each other’s creamy pussies and assholes. Jenna had never before eaten another girl’s sex, but found Monica’s delicious mound was an easy task to master. She spit into it, and swirled her tongue around the fat little clit, but was almost always tempted to slide her mouth past the slippery lips of her girlfriends sex and seak out the pink pucker just beyond it.
Monica was likewise a depraved anal slut, and soon enough the pair were stretching their necks and arching their backs to get at one anothers buttholes, tongues slurping hungrily and spearing in and out of one anothers salty-sweet rectums like they starving for juicy anal meat.
“I knew you were special the second I saw you, Baby.” Monica groaned, slipping two fingers back into Jenna’s ass and opening her slightly so she could spit into the hole and let it close up with her gift inside. “You are so fucking incredible I can hardly believe it.”
“You’re pretty fucking intense as well.” Jenna said with a giggle, dragging the flat of her tongue across Monica’s pucker and rubbing it with her pretty chin. “I can’t believe we did this. I can’t believe how incredible it felt. I never dreamed. MMmmmm Monica. I came so hard.” She paused, trailing off with a slight pang of sadness. “I’m married though. I have children.”
Monica sat up, pushing her lover aside for a moment and then climbing up over her, tenderly taking Jenna’s face in her hands. “Don’t think about that, Baby. This has nothing to do with that, and what they don’t know can’t hurt you. Do you wanna get dressed and forget this ever happened?” She asked with a wink.
“No.” Jenna said with a blush, feeling suddenly far more comfortable at the sweet tone of Monica’s voice “I mean. I’d like to see you again…”
Monica laughed out loud, rising up between Jenna’s legs and giving her big tits a shake. Jenna couldn’t help but smile up at her, wrapping her long legs around her lover and running her hands up and down the soft sweetness of Monica’s thighs.
“You’re never getting rid of me now baby.” Monica smiled brightly. “Now let’s go get a motel room and take a shower. Once I’m done soaping you up and washing you clean, I’m gonna get you in a bed and show you what buttfucking is really all about.” She promised.
“Yes Ma’am.” Jenna grinned, giggling like a schoolgirl with a crush as Monica fell down on her and invaded her mouth with a kiss once more.