Freaky Fuckday

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Chris reached down to grab Emily's cock and point it straight up in the air before he lowered himself down upon it.

~Chris~

Chris reached down to grab Emily's cock and point it straight up in the air before he lowered himself down upon it. Chris sat on Emily's dick and slowly slid down her pole until it was fully inserted inside his pussy. Chris threw back his hair and stared up at the ceiling as he groaned with satisfaction. He could feel Emily's entire length within him and this time he was in total control of its insertion.

Chris held himself still for a moment while impaled on Emily's shaft so he could enjoy how full his body felt. Chris began rocking back and forth against Emily's erection before lifting himself off her cock and slamming his pussy back down upon her stiff member. Chris rotated his pelvis as he wiggled around on Emily's cock for a bit before lifting himself off her and descending again.

Emily stared up at Chris openmouthed as Chris used her cock to fuck himself. Being on top used to be her favorite sex position but Emily adn't made love that way for a long time. Being on the other end of that position reminded Emily how much she loved and missed it. If Emily ever got her body back she was going to ride Chris's dick like she was taming a wild horse.

"Oh God, Chris," Emily moaned. "This feels so fucking good."

"Good," Chris replied as he found his rhythm of fucking Emily while sitting on top of her.

"You look so damn sexy like this, Chris," breathed Emily as she enjoyed the sight of Chris's messy hair billowing around his head and his bouncing breasts jiggling in the most obscenely delicious manner.

Chris noticed that Emily's hands were lying against the bed unmoving except for gripping the bedsheets beneath her. A pity to waste those playful fingers when they could be accomplishing so much more.

"You should play with my tits, Em," Chris suggested to Emily. "Touch me."

Emily grinned at him and lifted her hands to his chest as she complied. She squeezed his breasts hard and the stimulation of one of the erogenous zones of Chris's body increased the pleasure he derived from riding Emily's cock exponentially. The way Emily cupped, caressed, and kneaded Chris's breasts just how she would have liked her own teats stimulated felt fantastic. But Chris wanted more.

"Pinch my nipples," Chris begged, short of breath.

Emily lightly squeezed the buds of Chris's breasts between her thumbs and forefingers, making Chris groan.

"Harder," Chris insisted as he worked his pelvis against Emily's crotch with greater urgency. "Oh fuck, pinch me harder."

Emily squeezed the areolas behind Chris's nipples, knowing full well that pinching that portion of the breast provided the actual stimulation while pinching the tips of Chris's buds only caused pain and discomfort.

"Harder!" Chris demanded loudly.

Emily pinched as hard as she could and stretched Chris's nipples out as far toward her as they could reach. Chris squealed and then made a gurgling sound as he started fucking Emily even faster. Their cries harmonized together and increased in volume as Chris slid all the way up and down Emily's pole. Emily jerked her hips upward every time Chris lowered himself upon her shaft so she could thrust herself even deeper inside him.

~Emily~

Emily jerked her hips upward every time Chris lowered himself upon her shaft so she could thrust herself deeper inside him. Emily felt a mounting pressure welling inside her testicles and penis that signaled she was near climax. Finally. Emily loved the sight of Chris's breasts swaying back and forth and up and down as he fucked Emily and the high-pitched noises Chris made whenever Emily pinched his cute, puffy nipples. Her crotch and thighs were sticky wet with Chris's draining seepage. Emily loved everything about this experience as she took it all in.

Chris tried pulling his body nearly all the way off Emily's cock with only the very tip of her penis still inside him before slowly pushing downward to take all of her up his cunt. Doing this felt fantastic but without a proper grip on Chris to help guide him as he lowered himself Emily accidentally slipped out of him. Drat. Just when Emily was close to cumming too.

Emily and Chris both laughed together at their predicament and this time Emily gripped Chris's buttocks tightly as he descended onto the head of her cock. They went slower this time, their bodies in a perfect harmony of push and pull. Thrust and withdrawal. Though Chris still controlled the pace of their copulation and the depth of Emily's penetration, her hold upon Chris's asscheeks helped guide his movements. Their breathing became labored as they enjoyed each other's bodies in a way only lovers who possessed a vast amount experience with their partner could.

Emily squeezed Chris's ass tightly as she helped him slide his vaginal canal up and down her cock. Had Emily actually thought once that her butt was too big? She was in love with how her posterior felt when it was on Chris's body. There were just so many curves to caress and so much flesh to squeeze. Touching it felt enjoyable in a way that Emily knew would be impossible with a slim ass. Chris's body felt perfect. Did that mean Emily's female form was perfect then too?

Emily slapped Chris hard on his right buttock and chuckled as she listened to her husband giggling girlishly. It was hard to believe Chris was actually making those noises so just to be sure Emily spanked him again even harder. This time he moaned instead, evidently enjoying the pain mixing with pleasure. Emily rubbed his bottom soothingly where she smacked him while they continued fucking.

Emily had a sudden thought of watching the magnificent globes of Chris's ass up close. Of feeling his asscheeks pressed against her thighs and crotch while Emily entered him.

"I want to fuck you from behind," Emily said suddenly.

Chris looked down at her and said, "Well, then I want you to fuck me from behind."

Chris lifted himself off of Emily and her cock flopped around before steadying itself. It remained perfectly erect though it was starting to feel kind of sore. Emily's penis and crotch were soaking wet with Chris's leakage and Emily wondered how many orgasms Chris had experienced since they started fucking. One definitely occurred when she fingered him, then again while they were fucking missionary, and yet another time when Emily pinched Chris's nipples while he was riding her dick. Perhaps more? Chris seemed in no mood to stop though he had been satisfied multiple times. Emily assumed he was being courteous and waiting for Emily to have her climax, which she hoped to do soon.

Once Emily withdrew from Chris she got up and allowed him the room to roll over and get on his elbows and knees in front of her. Chris pushed his ass up and out to present himself to Emily like a beast would for its mate. He wiggled his bottom back and forth for Emily which drew an appreciative murmur from her lips. Emily slapped Chris's ass playfully and took position behind him while he cooed. She placed her hands on his buttocks and clenched his humps tightly before pushing them apart so that both his holes were spread open. Chris's pussy was so wet that it was literally dripping fluid onto the bedspread. Emily licked her lips at the sight of a thin, stringy line of seepage slowly leaking out of Chris's opening. Chris's hair-rimmed anus looked tight and puckered and Emily felt a strange thrill of excitement when she peeked at it. That was an odd feeling, Emily thought.

Emily let go of Chris's buttcheeks and lowered her cock until it pointed horizontally toward Chris's sloppy slit. She felt Chris's wet opening parting for her as the tip of Emily's cock entered him. Emily's hands found a firm hold upon Chris's wide hips and she readied herself for fucking her husband good and hard. Chris screamed as Emily inserted the entire length of her member inside him with a single pelvic thrust.

~Chris~

Chris screamed as Emily inserted the entire length of her member inside him with a single pelvic thrust. Due to the altered angle of entry at being taken from behind, Emily's already large cock felt double its size to Chris and Emily seemed to penetrate twice as deep. Chris was so wet that Emily's penis made loud squelching noises as it moved through his tunnel and nearly reached his cervix. The penetration was so complete that Emily didn't just seem to pierce Chris's body but rather she pierced his mind and soul as well. Chris would be her devoted slave if Emily wanted. Her mindless little fucktoy. Chris had never thought this way before but he was becoming so turned on by the idea of being used by Emily for her pleasure that couldn't get these ideas out of his mind.

Emily held herself perfectly still once she had filled Chris's womb. Chris felt Emily's thighs warming his asscheeks and her dangling testicles bouncing between his legs. Chris rotated his pelvis around and shook his bottom back and forth with Emily still inserted fully inside him. Chris grinned as he heard Emily's groan from behind while he used the tight muscles of his vagina to play with her cock.

Emily pulled out of him agonizingly slowly before pushing back into him at the same sluggard pace. She continued fucking him like this; nice, slow, and gentle while Chris gasped as he felt his cunt being filled and emptied over and over. Being fucked like an animal felt far more pleasurable to him than the last two positions they'd tried. Chris secretly got a thrill from assuming a subservient and submissive position for Emily. With her hands holding his hips tightly, she was in complete control of his body and the idea made Chris shiver in a good way.

The next time Emily thrust inside him, Chris pushed his bottom back against her. They moaned in unison as their bodies moved together in a wondrous unity. The emptiness and disappointment of withdrawing from each other would always be mitigated immediately by the happiness of joining together again. Emily and Chris worked together, controlling their bodies and responding to each other's needs so that they ascended to a higher level of pleasure.

~Emily~

Emily and Chris worked together, controlling their bodies and responding to each other's needs so that they ascended to a higher level of pleasure. Emily soon discovered during her inspections that spanking Chris hard on his ass would make him wiggle for her on demand. She loved watching his plump bottom weaving back and forth so that her cock was stretched and pulled from side to side within him.

Emily pulled the tangles of Chris's long brown hair into a fist and tugged backward on the makeshift ponytail she had created until Chris's head was pulled back. Chris's body looked so sexy with his back arched so his spine looked clearly defined with the vertebrae sticking out of his skin. Emily used her grip on Chris's hair to hold him in place and gain leverage while she started fucking him relentlessly. Chris's groans and pleas for more made it clear he enjoyed such treatment.

While Emily fulfilled her wish of fucking her husband from behind she found her eyes wandering again down to the star of his anus. Whether due to arousal or because of the current position he was in, Chris's asshole had dilated open enough to be barely agape. The tight pucker of Chris's anus winked at Emily as she stared into it and his asshole seemed to invite Emily in.

Emily had never before thought of touching her husband in that spot. It was just not something she'd even considered. Very seldomly she allowed Chris to finger her down below and sometimes she even enjoyed it. Usually she begrudgingly allowed Chris to touch her asshole toward the end of one their increasingly rare marathon sex sessions when she was sore and ready for him to finish soon. Emily knew that when Chris fingered her asshole it turned him on and up to eleven which seemed to speed things up for him and move things along toward their inevitable conclusion. Really get the juices flowing, to put it crudely. As Emily stared down at Chris's sexy ass she couldn't dispel the possibilities her mind conjured and she relinquished the hold on Chris's hair to let him fall back forward.

Chris became so wet from his multiple orgams that his crotch, upper thighs, and buttocks were slick with his ejaculate. Seepage had even gathered within Chris's asscrack which Emily decided to slyly take advantage of. Emily tickled Chris's perineum just above where Emily's cock penetrated him and directly below his anal opening. Chris's body quivered and he gasped in shock as Emily touched him in such an intimate area. Emily gathered his accumulated seepage with her thumb and spread it liberally around the rim of his anus. Chris shuddered and groaned as Emily touched him on the most taboo part of the human body.

Emily pushed the tip of her index finger inside of Chris's asshole. His anus was so wet and ready for her that the muscle of his sphincter surrendered without resistance and allowed the unimpeded penetration of Emily's finger. Emily ceased fucking Chris for a moment so her finger could push all the way down the knuckle inside Chris's ass. The sight of Chris's tight little butthole swallowing the length of Emily's finger turned her on like nothing Emily had ever experienced before. The tightness of Chris' anus clenching and unclenching around Emily's intruding digit felt delicious. Chris's body jerked as Emily's finger penetrated his anal cavity.

~Chris~

Chris's body jerked as Emily's finger penetrated his anal cavity. This was a wholly different sensation than having his pussy fingered. His anus was far tighter than that nearby orifice and his asshole clenched snugly around Emily's violating digit. Chris gasped as Emily pulled her finger out of his ass and then pushed it back in again. Being fingerfucked in his ass actually felt kind of good, Chris admitted to himself. Better than he had expected. The kinkiness and wrongness of being touched somewhere so dirty made Chris feel aroused again. He had assumed he was finished climaxing for the night and had shifted his focus to making Emily cum inside him, but now he might need to rethink that presumption.

Emily began moving her pelvis back and forth to fuck Chris again with her finger still buried deep inside his rectum, making him squeal loudly for her. The sensation of being doubly penetrated was ridiculously intense. Unfortunately, with her finger all the way inside Chris's ass Emily was unable to insert her cock as deep inside Chris as they both would have liked with her hand impeding her access. Emily solved this issue by rotating her finger around inside Chris's ass so that her palm pointed upward instead of downward. Chris squirmed as he felt Emily's finger moving within his rectum. Just the slightest change in how Emily's wrist positioned itself provided enough centimeters of room for Emily's cock to slip all the way inside Chris while her finger hooked itself inside his rectum.

Emily fucked Chris at an upward angle so that her cock slid across the floor of his tunnel that was nearer to his ass. Chris felt Emily's finger and cock brushing against each other with only a thin membrane separating the two. Chris grunted as Emily worked her finger around his rectum until she could angle it downward so that the point of her finger rubbed against her cock as it entered and exited Chris's other hole. Emily was doing dirty, wrong things to Chris and he was loving it.

"Do you want to fuck my ass?" Chris whispered as he stared at the bed's wooden headboard in front of him. He had no idea what Emily's reaction would be to this prospect.

Emily stopped thrusting against Chris and thought about how to respond to his question as her body sat unmoving with the exception of her finger curling against the inside of Chris's ass. She decided to be completely honest.

"Yes," Emily stated truthfully as she worked a second finger into his anus until it squeezed in alongside her index finger.

Emily's ring finger slipped inside Chris's ass with surprising ease. Chris groaned as he felt two of Emily's fingers stretching him open and defiling his asshole.

"I'd let you do that to me if you wanted," Chris offered as he pushed back against Emily's fingers and encouraged her to fingerfuck his asshole. Her touch was transforming him into an anal slut.

"Are you sure?" Emily asked with genuine concern as her fingers moved deep within him. "You don't have to just because I said I wanted it."

"Yeah, I'm sure," Chris replied. "I want this and if it makes you happy, it makes me happy. Just do it quickly before I change my mind," added Chris

Emily pulled her fingers and her cock out of Chris's holes. She slapped him on the meatiest part of his ass and ordered, "Spread 'em then."

While balanced on his knees with his head turned to the side and laid against a pillow, Chris reached back and spread his buttocks apart to open himself for Emily. He never thought he would be giving himself to his wife in such a way, but then again there had been a lot of "I never's" that had already happened since waking up this morning. Chris worried about the discomfort and potential pain from his first anal se. but his excitement at surrendering himself totally to his wife and her nasty desires overrode his hesitancy. Emily had shown almost zero interest in assplay before tonight but now she was all over it. That in itself was enough reason to go through with this.

Chris felt Emily's cock passing along the inner slopes of his buttcrack until the head located his quivering asshole. Chris spread his cheeks even wider apart in an attempt to open himself as much as possible for her. They didn't have any lube; Chris only hoped that he had become wet enough from his multiple orgasms to make Emily's cock nice and slick for him. Chris looked back at Emily and saw her licking her lips as she stared down at Chris's ass. He was going to give her everything, every part of his body was now hers to do with as she pleased.

"Take me now, Em," begged Chris. "I love you."

"I love you too," Emily whispered as she squeezed the tip of her cock through the closed ring of Chris's anus.

Chris's body twitched as Emily started to penetrate him and his sphincter wasted no time before clamping down tightly around Emily's cock before the head could pass all the way through his anus. Chris gritted his teeth together as he experienced the pain of anal sex for the first time. It felt like the most intense burning sensation centered around the entrance to his rectum. Emily became frustrated by the delay and tried to squeeze her cock further inside Chris's ass but he couldn't take it. Chris cried out in agony as his anus prevented any further access.

Emily rubbed Chris's back soothingly and said, "You have to relax, baby. That's the only way we're gonna make this work."

Chris nodded and took a deep breath. He tried pushing his ass back and raising it up a little to provide Emily with a better angle of entry. Emily gathered saliva in her mouth and drooled a thick line of it down to the shaft of her cock. She stroked the fluid all over her dick while Chris overheard Emily talking to herself and lamenting the lack of any lubricant in their household.

Emily tried a second attempt at inserting her penis inside Chris's asshole. When Emily's cock knocked on his back door, Chris flexed his anus like he was using the toilet and felt Emily's penis slip an inch or two further inside him than she had the last time. Chris gasped and grunted as Emily slowly pierced the entrance to his rectum. At least the head was all the way in now and the part after that doesn't feel quite so painful, Chris thought. Chris closed his eyes and spread his cheeks farther apart with Emily's cock already a couple inches inside him. He surrendered to her totally, allowing her to penetrate him in the most intimate manner conceivable.