It Started With a Kiss

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A tale of longing, insecurities and sibling love.
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ZenZerker
ZenZerker
4,979 Followers

Author's note: This is a work of fiction. All characters are eighteen years or older. This story features anal sex, so be warned in case that's not your cup of tea. Don't expect realism and you won't be disappointed when you don't find it! Enjoy!

*****

Squirming and tingling all over in anticipation, Annie tried to sit still on her bed, waiting. The room was dark and silent, only the pounding beat of her heart filled her ears. She had turned off her bedside lamp when she heard the car pull into the driveway, wanting them to think she was asleep. It worked.

She heard their careful steps as they passed her doorway on the way to his room. She listened to them walking down the hall, whispering. Her brother Eric's deep warm voice answered in a hushed tone to his girlfriend Carol's chirping murmurs, assuring her that yes, it was okay, everyone was asleep. Then came the sound of Eric's bedroom's door closing.

Annie bit her lips as she counted the minutes, knowing she should give them some time to get started before she acted. She ached to jump off her bed but she restrained herself, not wanting to spoil it all by rushing things.

She crossed and uncrossed her legs, brushing her naked thighs together. Her thick pebble-hard nipples were brushing against the cotton of the flimsy T-shirt she wore to bed, teasing her already inflamed senses as she tried to picture what was happening in Eric's room. She imagined them kissing, groping at each other as they fumbled to take their clothes off. She pictured them rushing and stumbling through his room, tearing off one another's underwear, caressing and grabbing and licking the other's naked flesh, hungry for more as they fell in a tangled heap on his bed.

Annie could almost see her brother's strong hands running all over Carol's smooth body, his lips on hers, his body pressing her down against the mattress, pinning her to the bed under his toned chest. The mere idea of Eric's touch, the imagined feel of his fingers, of his closeness, of his labored breath; it was all so hot, even just in her head. It made Annie shiver, compelling her to get up and go.

Fighting the impulse to move, torturing herself by waiting yet knowing that it was better this way, Annie reached a slender hand between her legs. She was already wet. The heat and moisture of her pussy were obvious even through her panties. Her digits trembled. The instinct to pull her underwear aside and rub her clit to get a modicum of relief almost overpowered her resolve to do things right.

Sighing, feeling her arousal bubble and simmer inside her, Annie waited. Staying as still as possible, she gave them another couple of minutes, counting down the seconds. When she reached zero, she got off the bed and crossed her room.

Quiet as a mouse, Annie entered her en-suite bathroom, the bathroom that served both hers and her big brother's bedroom. It made her snicker, half in self-pity and half in excitement, to think that for eighteen years this had been just a bathroom while lately it had become the setting of a secret ritual she couldn't get enough of.

Walking on her tiptoes, Annie crossed the cold tiled floor and reached the door leading to Eric's room. She could hear low groans and wet gurgling sounds as she pressed herself against the door-frame. Her heart was racing as she slowly, ever so slowly, pushed on the door. Careful not make it creak, her hand trembling with barely contained excitement, millimeter by millimeter she cracked the door open just enough for her to peek inside.

From where she was looking, Annie could see right across her brother's room. His bed was exactly in her line of sight. She strangled a moan in her throat as she took in the scene before her.

Eric was sitting on the edge of his bed, naked, his head thrown back, his handsome face distorted in pleasure. Kneeling on the floor between his legs, wearing only a blue thong that rode up between her firm taut asscheeks, Carol was sucking his cock. She was slobbering saliva all over his big pole as she slid her lips up and down his length in a slow bobbing rhythm, her hand pumping him at the base. Carol's mouth looked obscenely stretched as she tried to take more of Eric's girthy meat down her throat at each plunge.

Watching her brother getting a blowjob from his slim, pretty girlfriend made Annie crazy with desire. In a flash, without removing her eyes from the fellating action, she pulled her panties down her thighs and stabbed her hand to her needy pussy, dipping her fingers in her creamy moisture. As soon as her fingertips made contact with her clit, Annie shook all over, the bottled-up desire she had strained to control so far finally overflowing in a mini-climax. She sighed in long-awaited relief and kept rubbing her clit while she feasted her eyes on her brother's spit-glossy cock disappearing into Carol's mouth.

As Eric's moans got louder and he started pumping his shaft up into his girlfriend's face, so did Annie's digits whirl faster on her slick engorged nub. The squishy choking sounds coming from Carol's cock-clogged mouth turned Annie on immensely, as they did Eric. While Annie neared her climax, her brother started humping his girlfriend's face with abandon, his hands sinking in her brown hair as he held her head down on his twitching shaft.

"Oh yeaaahh, I'm gonna cum... Ahhh fuck!"

Carol's eyes bugged out as the fat cock in her mouth throbbed and pulsed, unleashing a torrent of thick cum straight down her throat. She tried to remove her mouth from Eric's ejaculating pole, but her boyfriend held her head down, forcing her to swallow his load.

While her brother groaned in climax and bucked his hips into his girlfriend's face, Annie shook and leaned against the door-frame, orgasming on her clit-strumming fingers. Through lust-glazed eyes she watched Carol squirm and finally manage to lift her face from Eric's lap, spluttering and coughing as his last spurts hit her face, painting her cheeks, chin and nose in white gooey seed.

"Damn it, Eric!" Carol barked, her lips curled in disgust, "I told you I don't like it!"

Hearing that, Annie cringed. Her tongue was unconsciously licking her lips as she basked in the lewd sight of her brother's creamy sperm dribbling down Carol's face. Thick ropes of cum and saliva connected Eric's slippery and still plump cock to his girlfriend's lips as Carol reached for his discarded T-shirt, cleaning off his abundant semen with it. Seeing her brother's milky seed wasted like that shocked Annie, who, not for the first time, wished she could trade places with Carol.

"Sorry," Eric said as Carol sat beside him on the bed, looking annoyed. "I just... I got carried away, your mouth feels so good. Let me make it up to you."

Without preamble, Eric flipped his sulking girlfriend on her back, took off her thong and spread her legs wide open, exposing her pussy. A long, low groan of frustrated longing escaped Annie's lips as she watched her brother dive face first between Carol's thighs and start slurping away.

Those licking and lapping sounds, combined with the visual of her brother's tongue working relentlessly on his girlfriend's pussy, made Annie's fingers rub faster on her own clit. As Eric devoured her slit, Carol reached her hands to her perky tits, cupping her ripe mounds and tweaking her long pointy nipples. Annie did the same, pawing at one of her plump boobs through her T-shirt with her free hand, wishing she could work both her breasts like Carol was doing.

Of course that was just a minor inconvenience compared to the fact that, unlike Carol, Annie didn't have Eric's face stuck between her thighs, eating her out passionately. As good as her fingers felt on her clit, Annie's knees trembled as she imagined how much pleasure her handsome brother's lapping tongue might give her instead.

Soon, Annie's restrained whimpers matched Carol's throaty moans as both girls neared their climaxes. Unlike her brother's lucky girlfriend, Annie could only bite her lips as a warm crashing wave radiated upwards from her abdomen, claiming her in orgasm.

"Ooooh yes, lick me, Eric! Eat my pussy! I'm cummiiiiiing!"

Annie shook all over as she came, closing her eyes and murmuring under her breath the same words that Carol was moaning out load. Annie's orgasm was so strong and the situation was so erotic that she felt her head spin. Her legs felt weak and she didn't trust herself to stay upright, so she got on her knees, her legs as spread as her panties allowed, soaked and bunched up around her thighs as they were.

When she turned her gaze inside her brother's room again, a soft mewl escaped Annie's lips as she took in the sight before her. Automatically, she brought her nectar-wet hand to her mouth to silence herself, fearing they may have heard her. She needn't have worried.

Eric's grunts and Carol's wails filled the room as he pumped her pussy with long hard strokes. He was on top of her, relentlessly plunging his thick cock deep inside his girlfriend's slit, cramming himself balls-deep inside her at every thrust. Her legs were splayed open for him, her little feet straight in the air, her toes curling and uncurling as he pumped his hips hard and rammed his dick into her wet entrance, plowing her cunt fast and deep.

Annie watched Carol with undiluted envy. Her breath was ragged and her face burned red as Annie licked her nectar-slick fingers and returned them to her engorged aching clit, circling it. A familiar mixture of anger and frustration assailed her as she masturbated to the hypnotic, irresistibly sexy spectacle of Eric's meat filling Carol's leaking pussy over and over again. While she diddled her clit with one hand, Annie slid two fingers of the other inside her drenched needy pussy, finger-fucking herself furiously, trying to match her brother's pounding tempo.

While he slammed away into his girlfriend, Eric growled in pleasure and muttered obscenities to her, telling her how tight her cunt felt around his dick, asking her if she liked how he split her pussy open, demanding that she come on his shaft like a good little slut. Carol never replied with more than a throaty mewl of delight, her mouth constantly open in a perfect O. A high squeal escaped her lips when Eric leaned down and sucked hard on her wiggling perky boobs, nibbling viciously on her pebble-hard nipples, forcing his cock harder into her pussy, making her twitch.

Hearing her brother talk dirty to Carol made Annie's head spin. He was so sexy, so manly. Carol was so lucky to have him, to get that amazing cock all for herself. And yet, judging by the way she just lay there passively and considering the fact that she didn't even like drinking his cum, Annie doubted that her brother's girlfriend appreciated what she had. This only served to confirm to Annie for the umpteenth time that Carol didn't deserve Eric in the first place.

Lust and longing, burned inside Annie. Her eyes were getting moist from the stinging jealousy and impotent frustration that clouded her mind, while the warmth from her tight pussy radiated upward through her kneeling body. Her bitterness added a tormenting intensity to her pleasure, making the whole experience feel like she was grabbing onto a thorny rose she just couldn't let go of.

While her brother kept reaming his girlfriend's welcoming hole like a beast in heat, Annie gloried and suffered in voyeuristic delight, fingering her pussy and working her clit to match Carol's multiple climaxes. As she came on her fingers time and again, marveling at Eric's stamina and getting more and more jealous of his lucky and now blissfully surrendered girlfriend, one obsessive thought resounded through Annie's arousal-addled mind, amplifying both her pleasure and her pain: 'He should be fucking me.'

Girl-cum was tricking in rivulets down Annie's thighs by the time Eric slid his glistening pole out of Carol's pussy and repositioned her on all fours before spearing her cunt again from behind. Carol was putty in his hands, cooing and murmuring incoherently as he rammed his twitching shaft deep into her, his thighs clapping against her upturned little ass in a fast fleshy cadence.

Eric's wild fucking tempo soon made Carol fall face down on the bed. She repositioned slightly when she got back on her hands and knees, so that now the rutting couple was slightly out of Annie's line of sight: she could only see her brother's muscular legs and humping buttocks as he hammered into Carol's pussy with renewed vigor. While Annie's vision was reduced, something happened, something that made Carol squeal out.

"Ohhh Eric no! Aaaaahh no, n-noo-oohhh," Carol yelped in protest, "pleeeease don't... Ooohhh! "

Grinding her teeth in frustration, her heart hammering in her chest, Annie pushed the door open a little more. She tingled all over, scared and excited to take this risk, but she wanted to regain her line of sight on them as soon as possible, her need to watch her brother overruling her carefulness. When she could see the bed again, her breath caught in her throat as the reason for Carol's broken groans became clear.

While he kept packing her pussy with his cock doggy style, Eric had inserted his thick thumb inside his girlfriend's little asshole. In a trance, Annie watched her brother reach into his nightstand and retrieve a tube of KY from the first drawer. Applying a huge gob of lube on Carol's anus, Eric started spreading the gooey gel all around her tight crinkled hole. A rush of sudden warmth engulfed Annie's already flushed face as she realized what she was about to witness. As if of its own volition, her clit-frigging hand strummed her button faster.

"Nooohhh, Eric, please," Carol moaned as her boyfriend slid his index and middle finger in and out of her sphincter, plunging his digits all the way in, coating her asshole with lube. "I'm still sore from the other day... Oooohh! Even your fingers feel big in my ass, aaaahhh!"

Carol's words were strained and tinged with worry, her body shaking with the increasingly powerful thrusts Eric was inflicting on her battered pussy as he got ever more turned on by the prospect of sodomizing her. While Annie stared in awe, her brother slid his nectar-coated pole from Carol's well-fucked pussy and pressed his bulbous cockhead to the entrance of her greased up rosebud.

"I want your ass so bad, Carry," Eric said, reaching one hand under Carol's slender frame to rub her clit while he held her firmly by her hip. "I'll cum fast anyway, you're so tight."

"Ooohhh, no... Oooh!... I'll let you cum all over my face and tits," Carol replied, her reluctance somehow muddled by the feel of Eric busy fingers working her clit just how she liked, "but please, don't put it in my ass. It hurt so much when you popped my cherry..."

Undeterred, his powerful cock twitching as Carol begged him not to sodomize her, Eric leaned over his girlfriend's body until he could kiss her neck. Her protests diminished and she squirmed as he peppered her skin with kisses and whirled his fingers on her clit. All the while, he kept sliding his thick meat along her slick asscrack, his glans poking against her oily anus.

"Please, let me do this. After tonight I won't see you till classes start again after the winter holidays..."

"Aww all right," Carol sighed in resignation, resting her head on the bed and looking back over her shoulder at Eric, a worried expression on her face, "but you must stop if I say so. And don't hold back, just cum quickly and pull out, okay?"

"Sure, Carry," Eric said, grinning, grabbing harder onto her slim hips. "Now try to relax."

Still rooted in place by the spectacle unfolding before her, Annie felt her mouth go slack as she watched her brother guide his bloated purple tip against Carol's slippery anus and start pushing. Carol whimpered as Eric's fat glans popped inside her asshole and he began slowly wedging his shaft up her butt.

Without thinking, feeling drunk, Annie frigged her clit with one hand in time with Eric strumming motions on Carol's nub. Sliding the fingers of her other hand out of her soaked pussy, Annie reached behind her. Her eyes glued on the dilating ring of Carol's sphincter and Eric's thick, slowly disappearing cock, Annie leaned forward and pinned her shoulder against the door-frame, bending down on her knees and tilting her plump ass up.

Annie cooed under her breath when her pussyjuice-wet digits reached her asshole and started circling it, massaging it into relaxation until she could ease a slender finger inside her own tiny anus. The feel of her finger entering her warm rectum, mixed with the visual of her brother's hard cock opening up Carol's supple butt, caused Annie to twitch in pleasure. Panting silently, she sank her digit deeper inside her ass.

Watching her brother gradually cram his fat dick up his girlfriend's tight little butthole was the most erotic thing Annie had ever seen. She was no stranger to anal porn but to actually watch two people having anal sex right before her eyes drove Annie wild with desire. She had never seen Eric fuck Carol in the ass before, so she assumed he had taken her anal virginity recently, in her dorm room. Fleetingly, Annie bemoaned not having been the one to be anally deflowered by Eric, but there was little space for regret in her lust-filled brain.

By the time Eric had forced half of his veiny pole inside Carol's ass, Annie had already cum once, sawing her index into her anus and tormenting her engorged clit mercilessly. She was entranced by her brother's slow buttfucking motion, she couldn't tear her eyes from his girthy meat invading Carol's stretched little hole. Annie's slack mouth was practically drooling as she anticipated seeing the full length of Eric's cock buried inside Carol's ass, her ears ringing and full of her brother's grunts of pleasure and his girlfriend's strained whimpers.

Annie's mind was reeling, overcome with the unexpected eroticism of the sodomy she was witnessing. The unbound virility radiating from Eric's humping frame; the dominant/submissive dynamic implicit in the act of cramming his cock in his girlfriend's tiny forbidden hole; the unique transgression of using the 'wrong' orifice as a gateway to pleasure; the unreadable, intense expression on Carol's face, that inextricable mixture of pain and ecstasy painted on her visage: it was all so intoxicating, on so many levels.

To her own surprise, Annie realized that she had never wanted to trade places with her brother's girlfriend as much as she did at that moment, while witnessing Carol getting sodomized by Eric.

A sudden squeal from Carol broke Annie's trance-like state and brought Eric's anal assault to a halt. "Uuuhh stop, Eric, stooop!" Carol shrieked, her hands clawing at the sheets, her bent-over body tensing up. "I can't take any more ooohhh! Please, pull it out! Uuhhh... It hurts!"

Panting, flustered with desire, Eric stayed still, his half-buried cock pulsing inside his girlfriend's cramping rectum. "Aahh fuck, you're squeezing me so hard... You need to relax, it will feel better."

"I can't, Eric, even with you touching my clit," Carol whimpered, looking back at him over her shoulder, a plea for mercy in her widened eyes. "I'm too scared you'll rip me apart... Please pull out of my ass, Eric, pleeeease!"

"Okay, how about this: I'll just stay still and you'll squeeze your asshole around me. I'm so close and you're so tight, I'll cum any second now. Can you do that, Carry?"

"Ooowhh okay... Just cum fast and pull out, please."

Eric moaned and threw his head back, grinding gently, barely moving inside his girlfriend's ass while Carol milked him with her clenching anal muscles. Annie watched in mild disappointment as her brother neared his climax. This restrained assfuck wasn't the savage rump riding she had wished to witness, but still she wanted to get off. She had two fingers buried inside her snug butthole now and she was masturbating her little anus faster, frigging her clit like Eric was frigging Carol's, wishing to cum when he came in his girlfriend's ass.

ZenZerker
ZenZerker
4,979 Followers