The Horny Sister-In-Law Pt. 03

"I know, sweetheart," Jack replied, "but think about it..."

Daniel began stretching the rim of her asshole with his cockhead. "It's so fucking tight, my god," he muttered under his breath. Despite almost every muscle in her ass in total resistance, he pushed forward relentlessly causing Jessica to begin her humming again.

"Are you sure?" Jessica asked as naturally as she could. "I don't think it can fit..."

"Oh, I'm sure it would...I mean, we've handled cases like this in the past..." Jack said. Daniel smiled and leaned forward and whispered into her ear, "Your husband's right, you know."

Still concerned, Jessica looked back to see his enormous dick beginning its descent into her tiny anus. Daniel was lewdly positioned on top of her, like he was predator on top of its prey, his cock pushing ever so slightly into her asshole.

"Take a deep breath, baby," he whispered. Jessica took in one wavering breath and immediately Daniel felt her muscles relax, only just a tiny bit, but enough for him to make some progress.

"UHHHHHH..." Jessica hummed. Daniel watched gleefully as the muscles around her anus begin to loosen, trying to allow his fat cockhead to pass through. To be honest, Daniel was genuinely surprised that she was actually allowing him to make any progress. Of all the girls that Daniel tried anal with before, they had been unsuccessful of even managing to fit a single inch of him in. But then again, Daniel remembered that Jessica was a resourceful slut like no other. She was, hands down, the most talented and beautiful woman that Daniel had yet to bang.

Jessica's face began to screw up as he succeeded in pushing the ridge of his cockhead up inside her anal cavity. It was definitely the thickest part in his entire cock, and Jessica knew this too, the corners of her lips curling slightly in pride. So far so good, Daniel thought, and with a bit of luck, he just might be able to anal-fuck his sister-in-law just as he had fantasized.

"...and I was thinking, if we can get this contract..." buzzed the phone, now receiving zero attention whatsoever. Jessica's eyes began to water, blocking out everything Jack was saying. Her asshole was so delicious and tight that Daniel felt that all of their previous fucking wasn't worth one stroke down her sexy rectum. With her ass pointed upwards towards his crotch, Daniel's stiffened the entire lower half of his body and concentrated all his strength on his cockhead.

"AHHHHHHH...That's so fucking big!" Jessica hissed into the pillow. Thankfully, Jack was too enthusiastic about his next contract to notice this. The coating of cum around his cockhead served as excellent lubricant and Daniel was able to move millimeter by millimeter into her. Slowly, but it was good enough for them both. A thick mixture began to lather around the brim of her asshole, forming a creamy white circle.

"UUUUUUUUUUUUUUUUUUUUUUUH!" Jessica grunted loudly into her pillow as Daniel forced his cock down her anal cavity. Daniel's eyes widened as his cock slowly and steadily disappeared into her asshole. The tight muscles of her anus clenched around his cock like a vice and it felt incredible. Holding her ass cheeks wide apart with both hands, Daniel drilled more of his massive manhood down into her minuscule hole as firmly as he could. Jessica was positively yelling into her pillow and Daniel thought it was a bloody miracle that Jack couldn't hear her.

"Um...Jessica?"

Your wife's too busy to respond, Daniel thought in glee. Jessica turned her head slightly to look back at his cock ramming into her ass. He could only see the whites of her eyes now as she was absolutely lost in pleasure. Jessica had been screaming so loudly that she now had her mouth open with no sound coming out. Daniel paused his descent as he listened to Jack calling her a few more times from the other end. He knew that she couldn't possible get away from what was coming up next and he quickly reached over and turned it off completely. Even though the call had ended, Jessica was still in no position to make any sound. Jessica's anus felt like a thousand pair of lips sucking at every tissue of his cock. Now working hard to suppress his own moans, Daniel pushed the last inch of his cock inside her rectum and felt the tip of his cockhead flatten against the end of her anal cavity.

"Oh my god," he groaned.

It was a blissful moment. Daniel was in heaven -- his entire cock was lodged in Jessica's vice-tight rectum. Her tits positively jiggling with her labored breathing, she climaxed as soon as her brother-in-law's massive spongey cockhead hit the end.

"FUCKKKKK!" she exploded, drawing in a huge breath. "AHHHHHHHHHHH! IT'S IN! YOU DID IT, YOU BASTARD!!" Daniel wasn't sure she knew the call had ended, but she obviously didn't care anymore as Jessica began howling at the top of her lungs. Trembling with pleasure, Daniel squeezed her ass cheeks, waiting patiently for her orgasm to subside. He closed his eyes for a moment, enjoying the feeling of her wetness trickling against the underside of his balls. Completely impaled, Jessica's whole body froze as if she was afraid that if she moved, her rectum would rip. Daniel wiggled his cock slightly in encouragement and when she felt that her asshole was still intact after his movements, she let out a long breath.

"Ahhhhhh....." she gasped.

Daniel gave her left ass cheek a light slap. "You like that? My big cock in your ass?"

"Fuck! You feel so big! You're ripping me apart!" Jessica reached behind her and began to dance her fingers frantically against her throbbing clit. Daniel grinned, watching the housewife momentarily lose herself in her newly-found anal pleasure.

"Are you not going to say goodbye to your husband?" he teased. Gasping in horror, her eyes shot open as she looked back at him.

"Is he still on the call?" she squealed, flushing with embarrassment as she thought about her husband whilst having his brothers cock buried inside her asshole.

"Nope," Daniel reassured her. "The battery's dead," he added with a smirk.

"Fuck you, Dan..." she gasped, closing her eyes relief. "You bastard... I've never did this before..."

Daniel's smile vanished as it only just dawned on him. "Wait, you never did this with Jack?" He asked, astonished.

Jessica shook her head, lost for words. Daniel groaned in pleasure, taking deep breaths once more, knowing that he had just taken the anal virginity from this beautiful cock-hungry slut. "Then how come you can fit it in?" he asked. "No one has ever been able to!"

Jessica gasped and poked her tongue out at him, obviously proud of herself. "Because I'm good," she giggled, but careful not to shake her body too much in case her rectum might just rip around his massive cock.

Daniel groaned. "Fuck, you are one talented bitch," he observed, still finding it hard to believe that she received all of his length in her first anal attempt in her life. Jessica took a deep breath and opened her mouth. "I've used a dildo plenty of times before," she admitted. "I've tried big ones too...it's just that we never did it...he said anal was disgusting..." she added with a blush.

"What?" Daniel gaped. "Are you kidding me? Damn, he must be an idiot! This asshole feels absolutely incredible..."

"He said he didn't want shit on his dick..."

Daniel laughed. "I don't mind you shitting on my cock, Jess." He grinned, suddenly having an idea. "In fact, that's exactly what you're going to do."

"Wh-what?" Jessica spluttered, looking back at him. "You—you're not into that kind of stuff are you?"

Daniel laughed again. "Of course not," he said. "But you see, my cock's not coming out of your asshole if you don't push. You have to push like you're trying to poo. You have to push my cock out."

Jessica eye's widened at this. "Can—can't you pull it out?" she asked cutely. "Can't I pull on my side?"

Daniel shook her head. "Nah, besides, you have to try pushing. It feels a lot better."

"Really?" Jessica asked, but believed him already. Both of them knew that she was willing to do anything as long as she was satisfied. Turning her head away from him, she gripped the sheets underneath her and began to hold her breath. Daniel waited impatiently, still unsure if this was actually happening. Finally, he felt a little vibration of her rectal muscles around his cockhead but nothing else. Instead she humped her hips backward, causing both of them to tilt back a little.

"Uh-uh," said Daniel. "Not like that, you see how you're pushing me with you? Just concentrate on your rectum, not your entire body. Keep everything else still."

"Okay," Jessica said. Beads of sweat appeared again on her slick skin, evident to her effort. Daniel was quick to give her reassurance, reaching down and giving her clitoris a rub. "Good girl," he breathed.

She tried again, but still nothing happened. "I can't!" she gasped. "It's way too fucking big!"

"Remember, imagine you're taking a shit," Daniel said. "You know how to do that, don't you?"

Jessica blushed. "Yeah, of course, but..."

"Then, push me out," Daniel said with a grin, thoroughly beginning to enjoy the struggle of Jessica around his cock.

"Okay..." She held her breath and her face screwed up. Her mouth opened in a silent groan as she began to push his cock out of her ass. Daniel watched in pleasure as her entire body tensed as she worked her ass around his member. Faintly at first, but definitely distinguishable, Daniel felt the end of her rectum scrunch up against his cockhead. He groaned as he felt a bulbous face of flesh press against the tip of his cock and begin to rise, slowly but steadily. It felt absolutely incredible: Daniel felt as if someone was deflating a balloon around his cockhead, the pressure tugging at every muscle.

"UUUUUUUUGH!" Jessica groaned, her knees pressing together hard in effort. Daniel watched her abdomen square as she began to push harder. "UUUUUUUUUUUUGH!"

"Fuck, yes Jessica, just like that..." Her anus felt amazing -- two inches of his cock popped out of her anus. Jessica paused, gasping for breath.

"Is it out?" she asked anxiously, looking over at him again.

Daniel shook her head, his own face scrunched up in pleasure. "Not yet," he said. "But soon."

"How much more?" she asked, seemingly disappointed.

"You've only pushed out the base, babe," he grinned.

"Fuck," she said reproachfully. "But you're so fucking big!"

"I'm not blaming you," said Daniel. "You have no idea how good this feels. Now, push for me, Jess, push my cock out of your ass like a good girl..."

"Okay..." she panted. Holding her breath once more, she began pushing again. "UUUUUUUUUUUGH!" Jessica pushed hard and the muscles of her rectum began contracting, pushing Daniel's cock out in the process. "UUUUUUUUUUUUUGH! Fuck!" she gasped.

"Fuck...Jessica...good girl..." Daniel breathed, now beginning to rub her clitoris rapidly. "I told you this was going to feel good..."

"Fuck yes! You're right, it does!" Now half of his cock out of her asshole, she began working with renewed vigor. "UUUGH! FUCK! UUUUGH!!"

"Oh my god." Gradually, Daniel watched as his shaft slowly emerged. She tried two more times -- now only his cockhead remained. He watched proudly as his slut was enjoying quite basically the biggest shit in her life. "You're nearly there, Jess," he said with a slap on her ass cheek. "...you can do it..."

"FUCK!" Jessica yelped and pushed again. Slowly, Daniels cockhead began to emerge. Jessica's asshole felt like a hot, tight vacuumed pack around his cockhead and god, it felt better than any mouth or pussy. "UUUUUUUUUUUUUUUGH!"

POP! With one last push, his cockhead popped free. A farting noise escaped from her opening as the pressured air released from within. The exhausted pink hole winked rapidly at Daniel, the inner red folds engorged and hot with blood. Daniel quickly replaced his cock with his tongue, firming the bridge of it and shoving it deep in her anus, tasting her rectum with pleasure. Daniel had licked a handful of assholes before, but Jessica's was hands down the best anus he ever sucked on. The skin was tender and soft, and above all, her asshole was delicious. It was lightly sweet and salty at the same time, and it opened and closed slightly with her breathing. Eager to compensate for its loss of a big cock, her anus clutched his tongue tightly.

"Oh my god," Jessica gasped. "I did it..."

"Yep," said Daniel, his voice slightly muffled with his face pressed against her ass.

"Why are you so fucking big?" she asked almost accusingly. She reached behind her and grabbed at her cheeks. "Ah...that hurt...so good..." She closed her eyes for a second, enjoying her sore anus being orally massaged by Daniel's skillful, hot tongue. He smacked loudly at her pink tender star, sucking at her delicious rectum, the stubble on his chin grazing her engorged clitoris.

"Your asshole is amazing, Jess..." Daniel managed. He slurped, sucked and swallowed as hard as he could, eager to repay her for the blowjob that she had given him a while ago. Jessica moaned as she bathed in the stunning pleasure of her anus being passionately serviced. Daniel worked some saliva and spat it at her anus then shoved the bridge of his tongue deep inside her. Keeping the spine rigid, he flicked his tongue rapidly up and down, causing Jessica to squeal in delight.

"Ooooh!" she cried. "That feels so good!" With both of his hands on her ass cheeks, pulling them wide apart, Daniel was able to lick and suck at her gorgeously tender pink star as enthusiastically as he wanted. The asshole of this spectacular blonde was simply amazing, and Daniel enjoyed every second of tasting his perfect sister-in-law's freshly-fucked rectum. Jessica squealed and squirmed under his oral service, crying out in pleasure, raising her butt nice and high for him. Soon, she began thinking about his cock again, and became eager to revisit the feeling of his cock buried inside her once more.

"Can we...do that again?" she asked tentatively, with a blush.

"Do what?" Daniel teased, giving her ass cheeks a slap each with his hand, never pausing the flicks of his tongue in her pink star. Jessica giggled and looked back at him, her mouth opened slightly in pleasure.

"Fuck my asshole again with your big fat cock," she murmured sexily at him. Daniel's cock pulsed at her sordid words. It was no use playing hard to get with this perfect sex-tool after all. Removing his face from her ass, he straightened again and leaned forward onto her.

"With pleasure..." he growled. He aimed his cock at her anus, pulling the sides of her cheeks wide apart with his hands. Jessica arched her back and raised her ass invitingly like the good girl she was. This time, Jessica was ready. Or so she thought.

With a good push, Daniel sank his cock downwards, and, with the help of her pushing ass, he was balls deep in her ass in no time. He groaned out in pleasure and Jessica yelped, taking fistfuls of the sheets again.

"UHHHHHHHHH....GH! Ah fuck, that's so fucking deep!" she screeched. "YOWCH! Wait! Don't move yet!"

Taking her trembling body as a good sign, Daniel pressed himself deep into her rectum, allowing her to catch her breath. Jessica began to hum even when he was stationary, trying to get used to his enormous member in her tiny asshole. Her left eye was closed and Daniel could see the other begin to fill with tears and realized maybe he had hurt her by going just a little too fast.

"Are you okay?" Daniel asked.

He watched as one single tear rolled to her chin. Jessica was breathing deeply, keeping her body absolutely still. Finally after a good five seconds, she nodded and looked weakly at him. Her bright blue eyes were wide. "Yeah, I'm okay. Sorry, you were just so big...Just go slowly okay?"

"Good girl," Daniel encouraged. "I knew you had it, Jess...I'm pulling out..."

She nodded. "But you have to push," Daniel reminded her. Jessica nodded again.

Daniel began to pull on his cock, tensing the muscles of his pelvis. Jessica's eyes closed again as she squeezed at her bowels with all her might. Aided with the squeezing walls of her rectum, Daniel's cock was forced gradually upwards.

"UUUUUUUUUH!" Jessica groaned. Daniel moaned as his cockhead popped out of her rectum and quickly jammed it back in. Empty for only half a second, Jessica grunted, pleased to be filled once more.

"I'm going to go in and out, Jess..." he told her. "Are you ready?"

"Fuck yes," Jessica breathed at him, unable to resist the idea of a good anal fuck any longer.

"Hmmmm..." Daniel groaned. GLLLLRRRR.....SH! Daniel rammed his cockhead against the end of her rectum and in one motion and then pulled his cock completely out. This immediately pushed Jessica over the top and she cried out, tossing back her head.

"OH MY GOD! HYAAAH!"

"Fuck yes, Jess...your ass is incredible..."

Jessica began to pant. "Shit!...you bastard...you did that so fast..."

"Can we try two?" Daniel asked her.

"Yeah, but go a little slower...!" Not waiting for her to finish, Daniel pushed down, ramming his cock back into her anal cavity.

"One..." he counted, and began pulling back out. GLLLLRSH! ("UUUUUUH!" Jessica screamed). "And...two..." he counted once more, sliding his cock in and out as quickly as possible. GLLLLRSH!

"AHHHHHH! OH MY GAWWWWD!" she howled. "Oh my gawwwwd...."

Jessica's asshole felt heavenly. Never before had Daniel felt so good and his cockhead was positively twitching in pleasure. "You like that, huh?" he moaned. "Fuck, Jessica, your ass is hot..."

"Oh my gawd, Dan!" Jessica gasped. "That's so good! Keep fucking my ass like that!"

"Let's try five?" Daniel asked, leaning his chest in. Jessica couldn't reply, her back arched in a 'C' as hard as she could, lost in the invasion of his cock inside her rectum.

"One..." GLLLLRSH! "Two..." GLLLLRSH! "Three..." GLLLLRSH! "Four..." GLLLLRSH! "...and fucking...FIVE," Daniel growled, ramming his cock inside her ass with every number. GLLLLRSH!

"UUUUH! UUUUH! UUUUUH! UUUUUH! UUUUUUUUUUH!!!" Jessica's screams were now purely animalistic as she climaxed at five. Daniel barely noticed her pussy cumming hard against the bottom of his ball sack until some of her cum sprayed onto his legs. He felt her gush of warmth spew against his thighs and decided to use this opportunity to add a fresh supply of lubricant to her anus. Pulling his cock out, he pushed it deep into her pussy. Her vagina felt incredibly easy to penetrate compared to her asshole which was amazing considering it was extremely tight as well. Jessica cried out, with another cough. Daniel gave her pussy a few good strokes with his cock, making sure it was dripping wet with her natural lubricant before forcing it back into her anus. His hands were now looped around her abdomen, preventing her from collapsing belly first onto the bed.

"There you go," he growled. "I knew you could take it, Jess..."

"OH, DAN! AHHHHHH!" Jessica's body trembled with delight.

"Did that feel good, Jess, huh? You like that...?" Daniel couldn't blame her for not replying as her breathing was cut short when he resumed his strokes into her rectum. Daniel kept his thrusts deep but slow, giving her some time for her orgasm to subsidy. When it finally did, Jessica's hair was all across her face, her beautiful face half-obscured, fully washed with blushing lust.

"Dan, you're fucking my brains out!" she exclaimed. Daniel laughed to himself as he gradually began to increase his speed, her anus now relaxed enough for him to move without much friction. GHLOP GHLOP GHLOP! Went his cock.

"Just what you asked for, you slut," Daniel told her throatily.

"Yes, Dan...Fuck me! Fuck me tiny asshole with your fat dick!"