Sonny and Jill’s First Anal Night

by Alexa Chamberlain

1

“Get comfortable,” Jill offered to Sonny as she showed him to the sofa. It faced a large gas fireplace, its flames flicking in and out of the realistic logs.

Sonny relaxed as he waited for Jill, who seemed to be taking a while. It was worth the wait when she walked in, though. She was barefoot, a see through mesh thong allowing full view of her pussy, wispy curls of black hair poking through. Her breasts were supported with a black leather cage bra, exposing her impressive nipples on her full DD-cup natural breasts. Sonny noted the faint tan lines that complimented the crossing straps of leather. Around her neck shone a silver choker, a heart shaped pendant pressing gently against her throat. The silver contrasted against everything black – her hair, with its streak of purple on one side, her outfit, and her black eye makeup.

He caught a flash of something at her pussy, a small silver hoop pierced through on the lower right lip of her pussy.

2

“When I said ‘Get comfortable…’ “Jill said, as she reached under Sonny’s black turtleneck and lifted it over his head. “Lie back”, she instructed as she went to work getting his jeans off of him. Sonny himself anticipated a romantic evening himself, so Jill was pleased to discover black, sheer underwear wrapping around him, his cock visible through the soft, sheer, shiny fabric.

Lying down now, Jill climbed onto Sonny, kissing him before slowly spinning over him and working her way down his body as her pussy inched closer to Sonny’s face. Jill worked her hands under the sheer fabric that stretched over his cock and balls. Freeing them she fisted her hand around his cock with one hand and massaged and cupped his balls with the other. She pumped her fist gently, happy at seeing precum escaping the head of Sonny’s cock before leaning down to taste it. She rubbed the clear liquid over her lips, ran her tongue over them to taste, and then slid her mouth down the entire length of his cock.

3

Sonny gasped as he reached for the thong and pulled it down over her ass, smelling her aroma as she lowered her hips so he could easily French kiss her already wet pussy.

Sonny licked long licks up and down Jill’s pussy, eliciting moans of pleasure. He flicked her silver hoop with his tongue on the way up towards her clit, stopping there to close his mouth over it and gently suck in a pulsating rhythm. He felt a small flood of release as Jill came, making her wetter yet as he sucked her juices in as they flooded his lips.

As Jill continued a slow pace on his cock, she let her saliva trickle down onto Sonny’s balls, to his ass. She circled his asshole with her index finger, and slid her middle finger in.

Sonny was surprised, but moaned at the pleasant feeling. With his hands around Jill’s ass he pulled up a few inches so he could kiss the insides of her thighs. He worked his way skillfully to her asshole, where he circled it repeatedly with his tongue. Then licking both sides, he probed the tightly closed hole with his tongue.

Jill released Sonny’s cock from her mouth long enough to exhale an “Aw yeahhh ” from her lips.

4

When she returned her mouth to his cock she sucked it faster, alternating her mouth with her fist as she pumped him closer to orgasm. “Come on, come on…” he heard her whisper in between breaths. Sonny clamped his mouth over both her ass and lower pussy as he came wave after wave into Jill’s mouth. High-pitched “mmmms” escaped her as she felt her mouth fill with his warm, silky passion. She loved the taste and viscosity of his cum, and she rubbed the head of his cock all around her lips and face after she swallowed. Panting now, she put her head down, her face on its side, gently sucking Sonny’s softening cock. She finally rested, his cock relaxing on her cheek as he went back to slowly eating her pussy.

She purred and they stayed this way for several minutes. Finally she pulled her head up, and massaged Sonny’s balls in both her hands. His cock was red, and she noticed it starting to swell again. She wanted to feel it get hard in her mouth, so she closed her mouth with his cock fully inside. She gently moved, and her heart jumped when it increased in size quickly. She slowly withdrew, watching as the full length of his cock escaped her lips.

5

Jill spun around and kissed Sonny, until he pushed her up so he could suck on her breasts. Full of lust and desire, he got as much of her in his mouth as he could and sucked hard, Jill crying out “Ow, ow! Oh yeah!”

She sat up and cupped her breasts, fingering her sore nipples before finally reaching under her, grabbing Sonny’s cock, lifting her hips, and guiding her pussy down the length of his shaft. She leaned forward again, lifting a breast to Sonny’s mouth. “Hard.” was all she said. He sucked her, biting down into her breast, raking his teeth across her nipples. Jill yelped as he finally freed her nipple from his teeth, allowing her tits to bounce as she began to fuck Sonny harder and harder.

Jill soaked Sonny’s balls as she came with a melted fury as she slid her pussy up and down the full length of the cock inside her.

6

Finally, Sonny lifted her off of him and without saying a word spun her over, exposing her ass. She scrambled onto her hands and knees and spread her legs. She loved being fucked doggy-style, she loved how deep it felt. Sonny parted her ass until his cock found Jill’s pussy. He started with short, slow strokes and then slowly went full depth, feeling her tighten around him. Then he fucked her hard. Then harder, her ass bouncing with each collision of her ass and his hips. He loved feeling his balls slam into the base of her pussy, a wet slap with each thrust. Jill’s tits swung back and forth, nipples erect and raw from sucking. Her tits were a flood of colors melting together, white skin with patterned blue veins, red scratch marks from teeth raking and sucking. The colors hinting at mild bruising.

Sonny loved how her tits would build a tunnel for his cock, as he doggy fucked her for another ten minutes before rolling her over. He straddled her now, and Jill took his cock into her mouth for long, deep throat pumps before taking it out and holding it down to her chest, trapping his cock between her breasts as she held them against both sides of his cock.

7

The only thing left on Jill was her pussy hoop and the heart choker around her neck. It glinted in the firelight as the flames illuminated both the silver and the pearly cum that shot out across her chin, lips, and cheek. She closed her eyes just as another line of cum landed across her face, almost parallel, forming two distinct, and sexy wet lines across her face. Sonny continued to cum in waves, hitting the underside of Jill’s chin, running down her neck to form a pool of cum in the hollow of her throat, the silver heart now swimming in the opaque liquid.

“Aw, holy fuck, Sonny, ” Jill cooed. “You are fucking beautiful. Your cock, your face, I love how you fuck all of me.”

Jill rolled over and collapsed onto her stomach, with Sonny on top of her, his relaxing cock nestled comfortably between her ass cheeks. Her ass was still slick with the elixir of cum they both produced.

8

Sonny relaxed, Jill actually nodded off, awakening only when she felt a cock swelling between her cheeks.

“Mmmm…” Jill murmered as she spread her legs slightly beneath Sonny.

Sonny backed himself off of her, trailing his hands down her back as he did so. When he reached her ass, he caressed and kissed her there. Jill instinctively raised her ass while leaving her head down on her crossed arms. Sonny trailed a finger down the center of her lower back, and down to her asshole. He spread her a little there, enough to place a kiss directly on her cute, closed hole. He ran his tongue along the insides of her cheeks as she let out soft moans. He circled her asshole with his tongue, gently and softly with great affection and care. He massaged some anal lube around and just inside her tightly closed pink ass. He filled his palm with lube, dipped a finger in it, and continued to gently lubricate Jill’s ass. Jill knew what was coming, she couldn’t wait, as her breaths came quicker now with the approaching act. She had never been fucked in the ass. Well, not with a real cock, anyway. She had at all times wanted a cock in her ass, and finally it was a sure bet Sonny wanted to fuck her ass, too.

9

Sonny took the remainder of lube in his palm and closed it around his cock. He stroked his cock, and lubed his balls also just because he loved the feel of it against his shaved manscape.

He spread Jill’s ass with his hands, and ran his cock up and down the valley that formed on Jill’s rear. Jill felt his cock ride over her asshole and anticipated what was next. She felt him pause, then suddenly felt her ass start to open as Sonny’s cock pressed against her hole. She felt the head of his cock slip past, and felt her ass close around the ridge that formed the head of his cock. He paused slightly, and then slowly and steadily watched his cock disappear into Jill’s ass. “Ahhhh!!” was all Jill could manage. “Ummmm…, oooohh,” she continued as Sonny stopped at full depth, just to admire the view in the firelight. It was sexy, and he slowly withdrew, but left the head of his cock inside. Jill instinctively pushed back against him, her ass swallowing up the full length of the cock fucking her.

10

“I love your ass, Jill,” Sonny said.

“Tell me you love fucking me in the ass, I want to hear you say it.”

Sonny responded in kind, driving into her ass harder now. Back up on her hands now, Jill was able to brace herself for harder thrusts. Sonny fucked her ass hard, again feeling his balls smacking against Jill’s pussy.

He brought one leg up, outside of hers, so he could brace himself and get more power. He reached for a fistful of her hair, and catching it twisted it to the side, so Jill was now looking back at him. Her mouth was open, only pants of breathing escaping. She reached a hand under her to fondle her breasts. She was surprised when an orgasm crashed over her, as she hadn’t even touched her pussy. Yet the sensations pulsing from her ass pushed her to a sudden climax.

Sonny increased his pace, the two of them lost in an anal fantasy they both wanted.

11

Sonny had slowed his pace every time he neared climax. Jill’s ass clamped around his cock so tightly he was beginning to lose feeling. He finally backed out of her ever so slowly, and thrusted just the tip of his cock in and out. He marveled at how his cock could open her ass gradually to allow him in. It was sexy and taboo all at once. Jill arched her back in anticipation, softly telling Sonny “Rain your cum on me.”

Sonny grabbed his cock and finished exiting Jill’s ass. He pressed it down in the curve of her body between her ass and the small of her back. He stroked back and forth while Jill looked back at him, her softly freckled face aglow in fire light. Her eyes of blue now darker and sultry. Sonny came with such force it surprised both of them, the sudden burst of cum shot over her arched back, slapping onto her left shoulder. He thrust his cock again against her skin and another stream rose and fell, showering her upper back, droplets of pearly cum landing on her cheek as she continued to look back, her eyebrows rising up in exclamation of pleasant surprise.

His cum continued to rain down on her ass, back, shoulders and face. One last line of soft white, contrasting against her black hair framing her face.

Jill swiped the cum on her face with two fingers to her lips. She brought it to her open mouth and tongue, tasting Sonny’s cum, which was naturally sweet.

Sonny massaged his cum softly around Jill’s skin, watching the swirls in the dimming firelight. He rolled over next her, and Jill leaned over onto him, her breasts resting on his chest. He massaged her shoulders, softly glistening with cum as she looked down and smiled at him. She leaned in and kissed him, Sonny tasting himself on her lips. The cum on her face was drying, leaving a soft, powdery residue. It looked both sexy and cute on her. Jill kissed him deeper, swirling her tongue in his mouth. As she crawled on top of him, Sonny felt the cooling wetness of her pussy against his cock. He was soft now, but still stretched long, the result of the warm fire and marathon fucking.

“Mmmm, that was awesome.” said Jill. “Now I’m not an anal virgin now, am I?” She smiled as she reached back and felt her ass, slipping a finger in her still lubricated hole.

“That was soooo nice…” she continued.

Sonny spoke, “It was beautiful to see, to disappear inside your ass.”

“I want to see, next time.” Jill replied. She already knew whom she wanted as their camera girl.