Manhattan Madness

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

"Climb on, stud boy," Julie said as she capped the bottle and threw it back toward the nightstand. As he swung his leg over her reclining figure, Julie used her hands to pull her long, wavy black hair back off her shoulders so it hung down over the side of the bed.

Jim leaned forward and kissed her as his hands stroked the outsides of her voluptuous, leather-harnessed boobs. Straightening back up but keeping his hands on her tits, he said, "That was for thanks in advance."

"What a polite one, you are," Julie replied as she stroked the outside of his hips with her hands. "Ready to stick that big dick through my tits, stud?"

"Yeah...you want to put it in?" Jim asked, hoping she'd play along. He loved it when girls got so hot they would position his dick for entry. Back home, most of the girls were so uptight, he'd almost have to take their hand and show them how.

Julie just smiled again and her right hand came around to take control of his stiff cock. Her left hand mopped up some of the excess oil that had run onto her stomach and she transferred it with her fingers to the top side of his cock-shaft. After a few transfers, her right hand stroked and twisted around his dick until it was slick with oil.

Satisfied that he was ready, she pushed the head down toward the open triangular area in her top that lined up with the bottom of her super cleavage. Jim leaned forward so his hand rested on the bed on either side of the pillows that she reclined on and he scooted his hips forward as Julie directed his cockknob against the soft undersides of her tits, right in the oily groove.

"Give it a strong push," Julie said as she looked up at him.

Jim pressed his hips forward and felt the head of his organ delve up into Julie's slick tit tunnel. The harness she was wearing kept her tit-flesh wrapped around his sliding tool as he fed more and more of it through her silicone domes.

Grunting in pleasure, Jim watched the head of his cock appear out of the top of her marvelous mammaries as his groin hit the bottom of her harness. His young throbbing cock was securely sandwiched in his sister's lover's tits!

"Oh, man, does that feel great!" he exclaimed down to the top of Julie's head. She'd looked down as he'd shoved forward but now she looked up at him again.

"Fuck 'em, stud. Show me how long you can last...I bet it won't be long!" she practically taunted him. Jim had wanted in the worst way to show her he had some staying power just for his ego's sake; now she was laying down a challenge.

"I might surprise you," he said without a lot of conviction as he began to fuck her tits. He began with long slow strokes, pulling about four inches down into her hot cleavage before pushing the head back into the open. He thought he could do that for quite awhile...but Julie seemed insistent to win her bet.

"Come on...fuck 'em hard! Do it like you mean it, big boy!" she taunted him as her hands gripped his asscheeks.

"If I do, it's gonna be a short fuck," Jim complained.

"I don't care...I want you to screw my tits as hard as you can!" she ordered him. "Then I want you to fuck me before your sister gets home."

She wants me to fuck her!Jim rejoiced silently.I got her so horny, she's gonna let me do her pussy, too. So much for the no-touching-the-kitty!

"All right, Julie, here you go!" Jim said as he quickened his pace, making his strokes shorter and harder. Her enveloping tit-skin and hard sternum bone welcomed his driving cock as Julie encouraged him further.

"Oh, yeah...harder..harder...God, your dick feels so hot!" Julie exclaimed as her hands pulled his buttocks toward her firm tit valley. She lowered her face to look again at his cockhead which was appearing and disappearing between her swaying breasts.

Jim, too, was watching her tits shudder under his hard thrusts. Julie's head hid part of the erotic display as he had leaned further over her but he could see the outside halves of her jerking jugs as they, in tandem, absorbed the energy of his lewd screwing.

"That's it...ohhh, you like titfucking, don't you, stud?...yeeaaahhh...bang 'em, baby!...come on!" Julie's hands left his pumping ass and she began playing with her small stiff nipples, pulling and twisting them with her long fingers as Jim's powerful titfucking continued.

The sight was too much for Jim; he closed his eyes and raised his head and began counting his strokes as a way to prolong the fabulous feeling of fucking a woman's tits.

..6...7...8...

"Oooooooooo, that's it!...ah, yeah...yeah...really fuck 'em!" Julie began ranting. "Just like that...Oh, God...yeah...oh, yeah...not much longer now...don't hold back, Jim...come if you want, stud!"

..11...12...13..14..15..16..

Jim found himself really laying into her bosom, fucking the round mounds of pleasure on Julie's chest like a crazy man.

.18..18..19.20.21.22.

"Come you, fucker! Come!" Julie's husky voice coaxed him. Jim knew he couldn't take much more; less than 40 seconds into his first titfucking and he was ready to blast off.

..24.25.26.27.

Jim's right hand, which had been digging into the bedspread, suddenly slipped off the mattress. Wildly, he flailed out and his fingers caught in Julie's long hair, his momentum pulling her head back sharply.

"UUUNNHH!"

Jim's eyes flew open and he looked down into Julie's excited eyes as he momentarily slowed his fucking.

"Oh, yeah!" Julie said lustfully, "I like it! Pull my hair!...use both hands." Julie's right hand slid down his straight supporting left arm and pushed it toward her head. "God, you know what I like!"

Jim realized he stumbled into something that Julie apparently got off on. Damned if he was going to tell her it was a mistake! He tangled his fingers in her wild, wavy ebony mane about six inches below her reclining head and pulled down on it as his arms rested on her shoulder blades. Julie's head went back again and her face simmered with a mixture of arousal and discomfort.

"Yeeaaaahhh!" she groaned.

34.35.36.37.38...

Jim began driving his rod back up and down her oily clutching cleavage as Julie's hands slid back to her tits. She squeezed the outside of her leather-crossed beauties and it was Jim's turn to groan as Julie's firm knockers tighten all along his slipping shaft.

"God!" Jim croaked as he began wildly humping into Julie's tit vise. The added friction, the hair pulling, the look in Julie's eyes...it rushed up on Jim like a freight train and Julie must have been able to tell that he was close.

"Come on me! Shoot all over me!" she panted as he dug his fingers tighter into her reins of hair.

"AAAHHHH, AAAHHHHH!" Jim gasp as his balls tightened and rocketed his sperm up and out in a gout of whiteness. Jim saw the first spurt splatter just under Julie's chin and saw it joined by a second, he kept thrusting, pulling his gushing cock down into her tit canyon and felt a third spurt coat the inside of her tits. Then his vision went blurry as his eyes tried to cross; they always did during a particularly strong come.

"Mmmmmm, oh yeah..." Julie said through clenched teeth as her shooting lover jerked above her.

When Jim's vision cleared, he looked down into Julie's smiling face and then down at the mess he had made on her neck and chest. He'd never been so proud of himself.

He let go of Julie's hair and sat upright, moving his hips back, drawing his slimy cock from between her heaving breasts. He slumped against the headboard, watching Julie look down at his cum load.

"Baby, you came in buckets," Julie complimented him as she ran her fingers through his pearly discharge. "I hope those balls can recharge themselves 'cause that was only Round One."

Julie sat up and reached behind her, unfastening her unnecessary top. She pulled the leather straps off her shoulders and peeled the top off her body. Her fresh-fucked silicone breasts barely sagged as she threw the top on the floor.

"Fuck, I love your body," Jim said as she lay on her side by him, "Did you ever dance like Beth?"

Julie laughed, "No." Then continued, "That was never an option for me." Her hand dipped down between his splayed legs and began stroking his deflated balls. "I prefer being in the background, pulling the strings."

Jim turned his body so he was on his side facing her and let his right hand begin massaging the underside of her breasts, enjoying the firm heavy weight of her fake tits.

"Why are we doing this tonight?" Jim asked, sincerely curious, "I mean.. is it because I'm Beth's brother."

"Now why would you think that?" Julie said, that wicked smile beginning to creep back onto her face.

"I sort of get the idea that would be something you'd go for...I should be off limits since Beth is your...girlfriend...but I think you like wild stuff like that."

"I'll admit that that was part of it." Julie conceded as her hand squeezed his nut sack lovingly. "I also can't resist young men; you're always so hard and eager to please...but, I could ask you the same question. You knew Beth and I are lovers and it didn't stop you."

Julie had a point there. Here he had gone and slept with his sister's lover. It was a real turn-on in fact, sharing Julie with Beth. Still he didn't want Beth to find out; it might ruin her thing with Julie.

"I hope we can keep this to ourselves," Jim confessed, "I'd hate myself if Beth found out and it caused any problems between you two."

"Our secret is safe with me...you know, if you want to fuck me, we better stop talking and get down to business." Just like that, Julie slipped back into her temptress voice as her hand slid up along the bottom of his half-hard dick.

"Oh, man, am I going to fuck you!" Jim chortled, "Just get me hard and get those pants off."

"First things first...I've got your cum on my chest...I'd really like it if you'd rub it into my tits."

"With pleasure!" Jim moved his fingers up into a puddle of his juices and then went to work smearing her left nipple with it. Encouraged by the way her hand began beating his rising member, he was soon using his entire palm to knead and rub his spunk on both her tits. Julie was loving it, too.

"Mmmmmm, feel how hard my nipples are!"

"I can't believe how small they are," Jim confessed. Julie must have had a pretty small pair of tits before her surgery.

"Suck on 'em!" Julie sighed as her she arched her back, lifting her left melon-like mammary toward his lips. Jim lowered his face and took her pencil-thick nubbin into his mouth and began swirling his tongue against its stiff rubbery surface.

Julie began almost immediately to vocalize her pleasure, "Oh, that's it, stud!...Mmmmm...oh, you hot fucker...lick your cum off my nipple."

Jim almost pulled his mouth away; he hadn't been thinking about that since he'd rubbed it into her skin but that salty taste wasn't all sweat. He was tasting his own cum. Back in Nebraska, that would be homo activity so he had some natural ingrown trepidation. But it was turning Julie on, so he forged ahead.

He let his hand start sliding down between their prone bodies, down her stomach and under the top band of her short skirt and the tight pants underneath. He wanted to diddle Julie's puss before he peeled her pants off and dropped between her thighs...

In a flash, Julie's hand was off his dick and pushing his hand away. Again surprised by another denial of entry into her holy of holies, he raised his mouth from her succulent teat and leaned away from her.

"What now?!" he asked, breathing hard. "If I'm gonna fuck you, I should be able to finger you."

"Oh, you poor boy...I must have given you the wrong idea." She leaned toward him and kissed his chest, then continued rolling onto her stomach. "Did you think you were going to get my pussy?"

"Christ, you said you wanted me to fuck you!" Jim said exasperatedly.

"I do want you to fuck me," Julie assured him, "just not where you had in mind... I want you to fuck my ass!" Her eyes danced with a wicked mischief as she knew the proposal would be unexpected.

"Holy...are you serious?" Jim asked excitedly. He'd seen a girl in those blue films take on two guys at once, one of them taking her up the ass, but he'd never dreamed he'd be in bed with a woman that wanted it there. Of course, Julie was just the kind of woman that would -- no sexual hang-ups at all.

"Pull off my skirt and you'll see just how serious I am."

Jim did just that. He moved onto his knees, straddling the back of her knees and pulled down on the skirt to reveal an oval-shaped slit in the bottom of her tight leather pants. Julie's voluptuous ass filled the pants so completely that the slit was naturally spread wide, revealing the deep cleft in her buttocks.

Julie's leather-strapped top had been made to accentuate titfucking and her pants were made for backdoor sex and backdoor sex only. The slit did not dip low enough that Jim could get any view of her pussy; Julie's stinginess even went that far.

"Niiiiiiiiiiice," Jim said as his hands began to stroke her ample ass; he loved the contrast of the soft leather and the even softer skin of Julie's asscheeks.

He'd always gone for girls with small, tight butts; school cheerleaders or even cruising some sophomores. But Julie's ass was...substantial. That was probably the best word to describe it. It was a full-grown woman's ass...and she wanted it fucked!

Julie twisted her upper body to look back at him over her left shoulder. Her left hand came back and pulled her ass open. Jim found himself looking at her sweaty, lightly-haired asshole. The dimpled area surrounding it was darker in color and striated.

"Finger it...go ahead, it won't bite you!" she prompted him.

Jim used his right hand to pull her right cheek apart and he slid his left index finger down onto her puckered opening. He ran his fingertip around her hot, damp entrance a few times and Julie hunched her hips back at him to spur him to investigate further. Slowly he stuck his finger against her sphincter and it slid through her elastic barrier.

"Yeah, stick it up there," Julie hotly demanded. "Mmmm, I like that."

Jim was amazed at the heat that surrounded his probing digit; it felt like it had been inserted in an oven on low heat. It didn't feel particularly tight around his single finger except at her sphincter where it gripped his knuckle. Experimentally he began thrusting his finger in and out, watching it draw out her moist butthole slightly before it slid down his finger. He wondered if he'd be able to get all of his cock up her ass; Julie was large in stature, so his money was on yes. There was no time like the present to find out.

"Ready for some cock up your ass?!" Jim put on a confident tone as he looked up at Julie's watching face. He knew she liked hot talk and he wanted to show her that he was eager to try it.

"Always," Julie said sexily, "Pull my skirt all the way off."

Jim did so and as soon as he cast it on the floor, Julie grabbed a pillow and slid it under her hips, raising her derriere slightly as she spread her legs wider on the bed. Jim kneeled now inside her legs instead of straddling them.

"Now, before you go plunging in there, I want you to use some spit to get your knob slick. The rest should go in without much trouble," she promised.

Jim spat several times into his hand and rubbed the slippery wetness all over the flared head of his renewed erection. He scooted forward until his knees were against the inside of her thighs. That was Julie's signal to lower her chest onto the bed, reach around with both hands and pull her cheeks wide for him.

"Man, I wish I had a camera," Jim told Julie as he leaned over her stretched out frame, supporting himself with his left arm as his right hand guided his glistening dickhead down into her asscrack. It really was an erotic sight - this lovely goddess holding her ass open for him, inviting him to sample yet another new sexual activity. She was being

a great tour guide; it appeared she liked everything under the sun except straight sex.

He ran his dick cap slowly down her crack until it fed into the deep indentation of her asshole. He pressed downward and had no success at first.

"Shove it a little harder," Julie encouraged. "Get the head in and we're home free, baby."

Nervously, Jim hunched forward, then tried even harder. All at once his cock helmet disappeared through her tight sphincter ring.

"Oh, God, that's tight!" Jim gasp. Her sphincter squeezed his shaft just behind his buried knob like a vise.

"It'll loosen, baby, just let it sit for a minute...don't tell me you never had to let a girl adjust to your big dick?...I've bet you've stretched out quite a few teenyboppers back in Nebraska!...feel it, it's not so tight now, is it?"

"No, that feels a lot better," Jim had to admit. The muscle ring had loosened to the point that it was still tight but not so tight that it hurt.

Julie released her ass, brought her arms back up under her body and raised herself up on her elbows. She whipped her long black hair to the side with one of her sexy head tosses and twisted her upper body to look back at their union.

"Ooh, look at that big fucker sticking in my ass!" she said like a X-rated porn star, "Okay, give me the rest!"

Jim kissed her shoulder, then moved his mouth to nibble her earlobe. He slowly began pushing his hard dick down into her musky hole, leaning further over her to get the right angle instinctively.

"Oh, yeah!...God, shove it in, baby! Aaaaah...mmmmmm...open my ass right up, lover!" Julie throatily whispered, her mouth so close to his own ear.

Her ass felt like a hot, tight, oily glove; it seemingly sucked him inward until the top of his hand, which clenched the base of his half-buried prong, pressed into her soft ass cheeks. He took his hand away, sliding it under her stomach as he worked another inch into her gorgeous rear.

"Fuck, this is wild!" Jim groaned as he moved his mouth forward along her jaw line, until his lips were on the side of her mouth and her tongue was coming out to greet him. Their kiss was awkward due to the way her body was twisted but her heat was transmitted. She was getting really turned on now, there was no faking going on.

Like an excited, anxious stallion, Jim lunged forward and the final two inches of his throbbing cock pushed into Julie's seemingly bottomless shithole. The front of his hips and dangling nuts lay on her slightly trembling, leather-covered ass.

She moaned into his mouth, the vibrations coursing through her captured tongue. After another moment, their lips parted with a wet smacking sound and it was Julie's panting voice that filled the still bedroom.

"God, I love it!...I love getting fucked up the ass...come on, do it, Jim!"

"Okay, okay," Jim rasped and he dragged several inches of cock out of her hot depths and then sank it back in. "Oh, man, I could get used to this! Shit, I can feel your muscles squeezing me. Are you doing that on purpose?"

"Mmm hmm," she sighed as he began fucking her ass. "Feel this?"

"Aaaah, Christ!" Jim grunted as her shitter tightened up, then relaxed again. He took the opportunity to begin screwing her butthole faster, enjoying the series of sexy clenchings that Julie began with her tail muscles.

"That's the way to fuck that ass!...aaahh...aahhh...Fuck it, you horny bastard... oh, yeah, uunnhuhhh...mmmmmm!" Julie was using her voice like she was using her inner muscles.

Jim attacked her ear with his tongue, worming it in there, knowing that he loved it when a girl did that. Julie sighed and then shook her head to make him stop. Either it was too sexy or she was ticklish.

Undaunted, his right hand slid up the front of her body and began groping her fabulous tits, the tits he'd fucked about fifteen minutes ago. His fingers slid into the bottom of her cleavage and he could feel some of his spunk hiding in there.