"Relax. Don't be nervous. You're doing great. I'm enjoying this. It feels... Tunny... this feels really, really right to me. Is that weird?"
Winston chuckled nervously. "It's your hormones talking. You'd say that to the twelve year-old kid who delivers our newspaper if he was in my place right now."
"Maybe," she giggled again.
"I love you," she said simply. She turned her head to softly kiss his nose. It was a sweet but absurdly chaste gesture given where his hand was.
"I love you too, sis."
She closed her eyes and settled herself. He watched her lick her lips, her little pink tongue darting out to trace their outline. It made Winston wince. He watched quietly as his sister began to masturbate. His eyes darted between her flushed face and the outline of her hands moving beneath the concealing blanket.
At one point, on pure instinct, Winston began to move his fingers in and out a little without realizing it. Jessica's eyes immediately flew open and she shook her head. "No," she whispered hoarsely. He nodded and held still.
A minute later, his sister's body began to move jerkily. Her breathing had become quick and shallow.
"Tunny, tell me to cum?" his sister whimpered.
"Go ahead and cum, Jess."
"More. Tell me more."
"Let it out honey. Let it out and be happy."
Winston blurted out what he was thinking. "Cum on my fingers, Jess. Let me feel your perfect little pussy cum all over my fingers."
"My brother's fingers," she moaned. That did it. She groaned and spasmed. Her twitching walls clutched at the two fingers just inside her. Winston had to bite his own lip to keep quiet as he watched her vibrate through her release.
"How was that?" he asked as his sister finally relaxed.
"Wonderful," his sister opened her eyes and looked at him. They were glazed and her pupils were huge and dark.
"I'm glad." He gently eased his fingers from her. "Maybe now you can get some rest..."
Jessica frowned. "Not yet, I need more."
"What can I say? I'm not really a one-and-done kinda girl. I usually go at least twice. Do you have any condoms, Tunny?"
"Whoa, no I don't. Do we really need to..."
"Shit. And, yes, I know what I need right now. How's your willpower Tunny? Oh god, why am I even asking? You're like a walking pyramid of willpower. That's half our problem..." she muttered that last part to herself only semi-cryptically. "It doesn't have to be a big deal, I'm just going to borrow the first inch and a half of your grade 'A' thing for a couple of minutes. Got it?"
"Let me see if I have this right, you're going to use my real thing as a substitute for your fake thing which you need in order to properly fantasize about getting the real thing and have another orgasm so you can sleep."
"Right. Great. This makes perfect sense," he said sarcastically.
"Don't be mean. It'll make it harder for me to relax."
"You're serious... why do you need me to do this?"
She turned to look at him. A lock of her dark hair covered one eye. Her ivory skin glowed in the light of the television. "Am I pretty?"
She had to know the question was rhetorical. "Yes," he said softly.
"Do you love me?"
"Did you lose at stolen kisses?"
"Do you want to help me?"
"Then let's stop talking about the 'why' and get down to the how." She looked at him a little more seriously. "Besides, frankly, at least one part of you is really enjoying this. I felt your nice, big thingie poke me in the side a few times."
She reached down and gently inserted her hand into the waistband of his pajama bottoms. He didn't move to stop her as her fingers circled his erection. The unfamiliar and illicit contact between his sister's hand and his cock made his head spin. His eyes slid tightly shut. So wrong. So very wrong. She stroked his end a few times, distributing his pre-cum, then grabbed the waistband and hauled it down over his hips. His erection sprang free.
The boldness of her move made Winston's eyes fly open and fix on his sister's face. She was staring at him intently, her mouth hanging open. She pursed her lips and exhaled as she drew his cock beneath her raised leg and towards her opening. He felt the heat radiating from her entrance before she placed him to her hot wet sex. They were just barely touching.
"Hunch into me a little?" she whispered.
He curled more tightly into her. Slowly, painstakingly, she rubbed him at her opening. She was warm, slick, and tight. So tight that he had to help by pressing into her steadily. It was the most intense feeling of his young life as he entered her. She gently but insistently stopped him before he was two inches inside her.
She was panting already. "Wow. That's good. You're ah... don't take this the wrong way, but you're nice and meaty in the way it counts. I feel stretched."
"Sorry, but it's true. Okay, seriously, no cumming, Tunny. As bad as this is... as bad as what we're doing is... if you come it would be really bad. Okay?"
"'Kay," he choked out. This was going to be even more difficult than he thought. He might as well never had sex before. The sensation of being inside of his sister made sex with other women pale by comparison.
He felt her hand moving above his shaft, playing at her clitoris again. Periodically, she traced a few fingers down around his girth to gather moisture from their leaking intersection to continue her masturbation.
For the first two minutes Winston forced himself to think about anything not sexual.
His sister interrupted his focus. "Tunny? Can you get on top of me? Please? It feels funny from this angle. It's unbelievably good though. I'm going to cum really hard, I can tell already."
He slipped out of her briefly then rose and slid between her legs. She carefully pulled him back into her, no further than before, and went back to masturbating. He looked down at his beautiful kid sister's face, flushed with excitement. He fought the urge to lean down and press his lips to hers. He made the third and fourth minutes by exerting his considerable willpower.
Moving into the fifth minute, he starting formulating a way to tell his sister that he needed a break before...
Hallelujah! She rescued him with her second orgasm. Moaning a steady series of softly grunted "Ugh hugh ugh hugh, yeah," she jerkily rocked forward and back in her enormous release. To his relief, her orgasmic rocking caused him to pop free from the warmth of her vagina.
Unfortunately, his respite was brief because on one of Jessica's downward rockings his slickened shaft slid up between her asscheeks and skidded up along the crack of her ass. Instead of objecting, Jess, still cumming wildly, rocked herself up and down further, trapping his cock between her firm buns. She continued touching herself, riding out her orgasm.
Winston couldn't help himself. His resolve was already in shambles from holding out inside her. No harm could be done like this and it felt too damn good. He began to push forward to meet her.
Jess finally came to her senses and realized her brother was moving against her urgently. She continued rocking up and down gently with him. "Can you come like this?" she asked softly as they hunched together. She clenched the cheeks of her ass, massaging his cock with her sleek, muscular buns.
"Definitely," he groaned, looking down at her hungrily.
"Then do it," she said, her expression soft and affectionate.
"Are you sure, sis?"
"Absolutely, it's only fair. You were was so good, so patient, for me just now. I know it probably just about killed you. I owe you. Go ahead, hump my little teen butt and get off too. We'll be Steven evens."
"Yeah yeah," she grinned a little, "keep humping, buddy. Just not too rough. It hurts my boobs when they bounce." She carefully held her chest in place with her arms.
It was barely another minute before he came, and dear Lord he came, he jerked himself back and away from her and quickly grabbed the towel off the bed to wrap himself in its terry-cloth. Immediately, he was wincing with the force of his own orgasm. He pulsed into the towel in heavy throbs of thick semen. It felt like he was ejaculating molasses. He couldn't remember ever coming this hard before.
When he finished, he was panting. His head hung limply from his shoulders.
"Was it awesome for you too?" his sister finally asked, looking up at him. Her voice was already sleepy.
"I'm glad. Good night, Tunny," she turned her head to rest on the pillow and closed her eyes. "And... thanks."
"Good night, sis."
He gingerly removed the now cum-soaked towel from them both and looked away as he fixed her blankets. Given what they'd done, he'd seen very little of his sister's nude body. He flung the towel into the wash basket on the other side of her room. He padded barefoot back to his own room and threw himself on the bed. Guilt gnawed viciously at him for what had just happened.
He must have fallen asleep because he woke up to daylight and the feeling of his sister's lips pressing softly into his. "Hey, I was sleeping," he groused. "No points for a sleeping smooch."
"I know," she replied softly. He didn't need to open his eyes to know she kept her face just fractions of an inch from his. They traded a few breaths. It was an intimate moment and Winston's cock stirred involuntarily. When he opened his eyes finally, her bright eyes - hazel at the moment - occupied his entire field of view.
She rubbed her nose against his in a quick Eskimo kiss then retreated. He blinked as he looked at her. She was wearing his green cotton bathrobe. "I smooched you because I'm happy. I finally got a great night's sleep and today is New Bra Day!"
No mention of what they did last night? Winston wondered if they could ever put that completely behind them.
In the meantime, Jessica was right. It was the third day after her surgery and she was supposed to switch from the tensor bandage to a non-underwire bra. She dragged him out of bed and led him over to her room where she pulled the top drawer of her dresser open.
"Look, sis, about last night..."
She didn't even look up. "What about it? I needed help and you were there for me. You're a good brother, Tunny. Always have been."
"Yup," she said simply. "Feel free to beat yourself up about it, but that's how I see things. Now, can we talk booby-holders?" she cried gleefully picking around the drawer's contents. It was filled with nearly two dozen sets of new underwear. The bras were sized for her new breasts - she'd clearly gone shopping beforehand.
Jessica's eyes were darting everywhere. "I can't decide. You pick. Which one is going to be the first to hold my new superboobs?"
He was at a loss, still reeling from her casual acceptance of last night's - what was it? Mutual masturbation, he guessed. He also didn't know much about bras. "Uhh... how about this one?" He pointed at a pretty, white lacy one.
Jessica laughed. "A push-up demicup? You're such a boy. I'll wear that one for you later. Right now I need something with support, dummy."
She rifled through the drawer and pulled out two bras. Both were full-cupped lacy affairs but one was black and one was electric blue.
He'd always liked blue. "That one." He pointed to it.
She turned her back to him and loosened the robe. Then she careful donned her new bra. "Oh this is awesome," she chimed, pulling it gently into place.
"I used to have trouble filling out an A cup. It was annoying having gappy underwear. I had to be careful matching some sweaters with the right shaped bra. Ugh, I hated it," she grumbled. "But now, I am seriously filling out this bra. I've got extra cleavage in a C-cup!"
She spun to face him, holding the top of the robe open. "Check it out."
"Whoa." It was all he could get out. The roundness of her creamy white breasts overfilled her bra slightly, pressing together into a tight cleavage above it. Her pale skin against the electric blue was... well... electric.
"You like?" She shrugged her shoulders and her chest swung minutely.
He gawked a little and found his voice, "I think you could hypnotize people with those things."
"Really? People? Anyone in particular? Like you perhaps?"
No point in denying it. "Yeah, I'm afraid I'm 'people.' "
"Good. Now hand me the matching panties."
He did. They were small and lacy. There wasn't much fabric to them.
Bending over slowly, painstakingly, she stepped into them and pulled them up and on beneath the robe. She flung the robe off to stand in front of her brother.
"How's the whole package?"
He gave his best, cheesy wolf whistle. "You'd have your pick, but I'd go with Perfect 10."
"The magazine. Don't get me wrong, Playboy and Penthouse would take you too, I'm just saying."
"Dork. Want to be the first to get a new, big boobie hug?"
"Sure," he said as she slid the two steps into him and pressed herself gently against his body.
"How's that?" she giggled.
"Nice." He looked down over her shoulder at her ass. The lacy electric blue panties weren't a thong but they were quite brief. Half of her buttcheeks were uncovered. Her tush looked delectable. "You're tarting up the panties a bit there too sis. Mom might freak when she sees them in the washer."
"You said that if I got big boobs that people wouldn't notice the rest of me. You had a point, so I'm emphasizing my sweet little tush a bit extra."
"That wasn't the point I was trying to make."
"I know. But I derive a certain satisfaction out of twisting your honorable intentions to my own devious ends."
Her cheeky response rang so true that it made him pause for a moment. "Sis, I'm having that printed on a t-shirt for you to wear around. It could be your life's slogan."
"And I'd wear it," she snickered. "But for now, here's your fair warning Tunny, I'm not putting any more clothes on than this for today. I want to enjoy my spiffy new body. Think you'll survive?"
"Sure. I'm a... what did you call me?"
"A pyramid of willpower."
"And you're gay," she reminded him with a smirk.
"Sure, I'm a big ol' gay pyramid of willpower."
She giggled. "Speaking of which, there's a bone I've been meaning to pick with you for awhile now."
"Hmmm?" he covered his mouth against a stolen kiss as she leaned into him.
Instead, she whispered into his ear, "Why didn't you tell me that cum tastes so good?"
"Dammit it, Jess!"
"Haha. Gotcha. Come on, I'll make you breakfast. When is the last time you had my patented oatmeal?" She ducked out her bedroom door and down the stairs.
With Jess gone, Winston's eyes sought the cum-soaked towel from the previous night. It was his very own Tell-Tale Heart, he could practically hear it throbbing: "Bad brother. Bad brother. Bad brother."
It took him a moment to locate the towel because it wasn't in the wash basket he'd tossed it into last night. Jess must have moved it. It was on the bed now. "Wait a second, had she been talking about the taste of his cum?" he wondered before crushing that down with a heavy mix fear, revulsion and disbelief. He shook his head and followed his sister down into the kitchen.
Jessica's patented oatmeal had less to do with oatmeal and more to do with the maple syrup, brown sugar, honey and assorted dried fruits (raisins, cranberries and chopped apricots) that she added lustily. Oatmeal was just a binder. The stuff was essentially sugar-based rocket fuel. Winston loved it, but then his sweet tooth was almost as big as hers.
He sat at the kitchen table and watched while his gorgeous, half-naked teenage sister stirred the oatmeal on the range top with a wooden spoon. Her small blue-pantied ass swayed back and forth enticingly. She glanced back at him occasionally to smile and, he began to realize, to make sure he was still watching her. If she'd been wearing high heels too, the scene would have looked like the improbable beginning to a porn movie.
"She's going to wear you down," the thought bubbled into his head, unbidden. Like an enormous burp, it belched up from his subconscious. This part of him knew what the rest of him was denying vigorously. It made him bite his lower lip. His sister wanted to do things with him. Well, they'd already done things. But she wanted to do more things. Things brothers and sisters shouldn't do. Now she had a new and improved body working for her.
He wondered what would hurt her feelings more. Giving in to her seduction? Or resisting it? He pushed these thoughts away too.
They ate their oatmeal at the kitchen table, chatting about their plans for the day. Jessica was supposed to lay low for another 24 hours. She'd be able to venture out tomorrow. In the meantime, Winston had errands to run: grocery shopping, drugstore, post office. He offered to swing by the video store and pick up a few movies for her.
"Yeah, get something I would like?" Jess brightened.
Winston knew what that meant: chic-flicks.
"Anything else you need while I'm out?" he asked. His mind was on last night's plea to buy her a new vibrator.
"Nah, I'm good." She shrugged as she picked up his empty bowl and hers and moved to put them in the dishwasher.
Winston was relieved. He had not been looking forward to purchasing a sex toy for his sister.
"Hey, when you get back, can we figure out a way to wash my hair?"
Winston ran his errands. He came back with groceries and two sappy movies for his sister.
"Up here!" Jessica called from upstairs as he finished putting stuff away in the fridge.
She called him into the bathroom. She was still wearing nothing but her bra and panties. She'd switched into the identical black set. Apparently she was serious about being barely dressed for the foreseeable future. The black stood out against her perfect ivory skin. It also looked a bit sluttier. It took him a moment to tear his eyes away from her and realize that she had set up a plastic folding chair backed up against the tub.
She waited patiently without comment as his eyes raked her body. She enjoyed her newly acquired ability to distract him. "Do you think it will work for a shampoo? I can lean my head back and you can use the hand rinser."
"Looks good to me. When do you want..."
"Right now please. I can't stand myself any longer."
He chuckled and reached past her to turn on the water and let it warm up. After a minute, he told her to lean back and let the hand rinser's spray touch the back of her neck. "Good?"
He wetted her hair down with the warm water and squeezed a good-sized glob of his sister's rosemary-mint shampoo into his palm.
"Oooohhhh," Jessica cooed happily as he began lathering her hair from the back of her neck, standing next to her. He soon realized why salons have setups where the shampooist can stand behind the basin. It was awkward shampooing from just one side. He couldn't see what he was doing on the opposite side.
He swung a leg around the front of the chair and easily straddled his sister. Being tall had a few advantages. When he glanced down he was looking directly at her cleavage. He wondered how long it would take for him to stop noticing it.
For her part, Jess didn't move. Her eyes were still closed. She looked ecstatic at finally getting her hair washed. And the truth was, he was enjoying it too. It felt intimate without being sexual. He liked being close to her. He lost himself in rubbing and lathering his kid sister's pretty hair.
When every strand had been soaped squeaky clean, he began rinsing her down. He started at her front hairline and worked downwards. As he made his way down towards the back of her neck he lifted her head. They repeated the procedure with the matching conditioner.
Towards the end, he noticed his crotch was getting warmer. He tried to ignore it. With her hair sexily wet and smelling of fresh rosemary-mint, Jess's attractiveness was getting to him again.
He wondered what it would be like if he'd had an ugly sister. Would he feel the same way? No point in wishing for the impossible. Without meaning to, he glanced down for another peak at her barely clad body and...
"Jess!!!" he cried.
She had leaned her head forward into him as he straddled her. Her face was millimeters from his denim-covered crotch. Her mouth was open and she was panting warm breath into the fabric over his groin.
"Aaahhh, sorry!," she said. "I was just... I'm sorry. It was just right there and I... I'm sorry."
"What got into you?"
"Come on, I didn't actually touch anything!"
"Look Tunny, the truth is you started getting hard before I started breathing on you like that. It's what caught my attention. So you're the one who turned this into a sex thing. I was just enjoying a nice wash." She wrapped her hair in the towel. "No harm. No foul. Thanks for the shampoo. Once again, you prove you're the world's best brother." She smooched him, a quick peck on the lips, and then left.
"No points for the kiss," he called after her, "I saw it coming."
"I know," her answer echoed down the hall, "but you didn't cover your mouth or move out of the way did you?"
She was right. He hadn't. She was winning the larger game.
He hid in his room and read for the next few hours until dinner.
They made a quick supper of pork chops and instant stuffing then sat down to watch one of the movies he'd rented for her, Chocolat. He'd seen it before and figured his sister would enjoy the blend of romance and imaginative story. She did. She teased him about being pretty good at picking out chic flicks.
They raided their parents' liquor cabinet to make rum and cokes then stretched out on the family room's two couches to watch the next movie, Shakespeare in Love. Again, he had calculated it to be satisfying for Jessica but survivable for him. He hadn't seen this one.
An hour and two stiff, icy rum and cokes later, the still barely-clothed Jessica crawled onto the floor and towards Winston's couch. The view of her swaying bra-clad breasts and lace covered ass as she made her way over was hot as hell.
"I'm cold," she whispered from the floor, her face inches from his. He smelled her rummy breath.
"You're not wearing any clothes. Of course you're cold. Want this blanket?" He lifted the large throw blanket under his feet.
"Yeah." She took it from him but instead of returning to her couch, she wedged herself onto his. She pulled the blanket over both of them and turned onto her side to see the TV.
"I'm freezing. You're warm. This is much better and you know it," she said tipsily.
Winston didn't have a lot of options, he could either stay on his back and stare at the ceiling or spoon in behind his sister and resume watching the movie. And it was a pretty good movie. He spooned.
He was so engrossed in the movie that he didn't notice when Jess got off the couch to get them a third round of rum and cokes. He was pretty buzzed. She must be getting hammered by now.
He definitely noticed when his sister got up and fixed them a fourth round because, on her return, her naked ass went by as she settled back onto the couch to spoon with him. She also smelled of coconut. He recognized the smell. She'd been moisturizing. Her smooth, uncovered butt wiggled against the front of his pajama bottoms as she got situated and pulled the blanket back over them.
When she settled, he asked the obvious question. "Sis, you're not wearing any panties are you?"
"Nope. The sexy new lacy ones I was wearing felt itchy. I'm used to the soft cottony or satiny kind. It'll take some time to adjust to the new ones."
"Right," he said sarcastically.
"Don't be such a prude. Wanna take your jammies off, Tunny?"
"Nooo... I'm good." As tipsy as he was, he smelled trouble.
"Sure? I won't mind."
"Honestly, I'd go completely naked right now if I didn't have to wear the bra what with the surgery and all."
"You're killing me, Jess."
"With kindness, brother dear. With kindness." She grabbed his hand, smooched it, and pulled his arm around her. They watched the rest of the movie. For a chic flick it was pretty good. Winston finished his fourth drink and Jess got up to fetch him yet another.
He got up to put in another DVD and stumbled. He was even drunker than he thought. He hadn't had rum in awhile and it was hitting him harder than he realized. The movie he stuck in was a classic James Bond film. He figured Jessica had a good run of girl movies and that she'd be asleep soon anyway. It was after midnight.
They were a third of the way through the Bond flick and he thought she'd fallen asleep when she whispered, "Tunny, I'm horny."
Winston's attentions were split between fighting off a vicious case of room-spins and trying not to get a complete hard-on while watching a scantily clad Britt Ekland work her on-screen magic and having his sister's bare ass pressed against him. "Generally or specifically?" he replied absently.
"Specifically. Like right now. I don't suppose you got me a new toy while you were out?"
"I asked you if you needed anything this morning and you said no."
"I didn't think of it. I don't think of vibrators while I'm having my morning oatmeal."
"I'm not going through what you put me through last night," he said preemptively.
There was a long pause.
"Actually, I don't think you have to. You know what we did after I got off?"
"Yeah," he'd never forget grinding along the smooth tight crease of his sister's perfect ass.
"I really liked it. I think I could come just doing that. If I hadn't had two humongous orgasms just before, I probably would have gotten off again." She wiggled her ass back into him until his hardening, pajama-covered cock was caught between her firm little buns.
"Sis?" he slurred the question.
"Please? You can leave your clothes on this time if you want, I promise. The rum and the romantic movies and snuggling with you for the last couple of hours has me pretty wound up. Just hold still. If you feel like it, you can help by humping back against me."
She ground back against him for a few minutes and, against what was left of his judgment, he found himself pressing back into her. They humped for several minutes. He was soon panting into the back of her neck.
She turned her head to ask him something and in his inebriated state he misunderstood her intention. He kissed her - a long, hard searching kiss that made her gasp into his mouth. It was their first lovers' kiss. She parted her lips in invitation and he slid his tongue into her mouth, playing it across her teeth. She teased him back with her own.
He broke their kiss. "I'm getting raw," he whispered, "need to take my pants off okay?"
"Do it," she said hoarsely. Actually she'd been about to ask him if he minded taking them off when he kissed her.
He shimmied free of his pajama bottoms and spooned back into his sister. She wriggled back against him until he was trapped again between her ass cheeks. The flesh-on-flesh contact was intoxicating in a way rum could never be. They resumed humping. Her crease was soon slick with his pre-cum. By the way her elbow was moving beneath the blanket, he knew his sister was rubbing her clitoris.
Jess said something so softly over her shoulder that he had to ask her to repeat it.
"I said, 'do you know where you are right there?' "
He had only been following the roughened texture on instinct. He realized now that he had been twisting against her rosebud during their humping. "Oh, wow, sorry."
"No, it's okay, it actually feels kinda good. I just didn't want you to get grossed out."
The late hour and the rum made him honest: "Jess, there is absolutely no part of you that I find gross."
"That was sweet, Tunny. Okay, more humping please. I'm most of the way there."
They resumed their grinding. Soon, the tip of his erection caught on the dent of her sphincter and he was lined up perfectly. They both froze.
It was Jess who broke the silence. "Push a little, Tunny?"
He gently hunched towards her, barely able to breath, barely able to believe what she was asking him to do. His cock was pressed firmly against her backdoor. Even through the rum haze he knew this was wrong on multiple levels. It just helped him not care enough to stop.
"Little more?" she whimpered.
He felt her rear entrance begin to give way. Felt the barrier spread into a tiny circle. Felt that tiny circle yield to their combined pressure as she helped by gently wriggling backwards into him.
His sister grunted a soft "ugh" just as the head of his cock slowly slipped into her ass. Her clit hand moved in a frenzy between her legs. The penetration was enough to bring her orgasm on in a rush. She went rigid, her hand continuing to circle her clit. She curled into a ball, heaving a delighted "God yes!" as her orgasm rolled over her. Her curling motion pulled her away from him and he slid free of her ass.
Winston waited patiently as she caught her breath. She turned her head and she kissed him.
"That was sooooo good. Thank you." She looked at him, her eyes glinting happily. She saw his distress, it was written across his face. "Steven evens again?" she asked, kissing him, her tongue tracing along his lip wantonly.
When he finally nodded, she wriggled her ass back against him and he resumed grinding up between her asscheeks.
Inevitably, his tip was rubbing at the loosened, rougher flesh of her rosebud again.
He angled into it instinctively to maximize the contact and he caught himself at her entrance.
"You want to go inside again, honey?" she asked, her hand drifting to his hip.
"Yessss," he hissed softly.
She reached back and took his warm hard length in her hand. She centered him on her ass.
"Push a little again, Tunny."
He entered her more easily this time and she released her hold on his shaft.
"Can I have more this time?" she asked over her shoulder. "I… I kind of like this," she whispered.
He slid almost three inches of his eight inch length into her. Her rectum was furnace-hot and absurdly tight. It was also slicker than he expected, but then again he didn't have much experience in this department.
"Does this feel good big bro?" she asked, her voice was strained.
The question had to be rhetorical, he realized even in his drunken state. "Uh huh."
"Want to try more?" she offered quietly.
She pressed back against him as he pushed into her. Inch by inch, he slowly slid his cock another three inches into her back passage.
"Oh my god you feel huge," Jess whimpered and paused, "Tunny, honey, I want… I want all of it… all of you inside me, okay? Hold still."
She resumed her backwards press and together they drove his entire length into her until his groin was pressed into her buns. They both realized that they'd been holding their breath.
"You okay, Jess?" he asked, just now worrying about hurting her with his slightly over-sized tool.
"Uh huh. You're so deep. So very, very deep. Gimme a sec," she panted. "Okay, now do me."
"Like, gently or..."
"However you want. I've already come and I can tell I'm going to come again pretty soon no matter what you do. This feels fantastic."
He began sawing a few inches in and out of her tight rectum gingerly.
She urged him on, reaching back to pull his hip into her. "It's all right Tunny, I won't break. Take me. Take my ass. Your little sister's ass. It's yours. I know you like it. You've been admiring it for years. I've been saving it for you."
"I don't want to hurt you, sis. I have no idea what I'm doing. Wait, you haven't done this kind of thing before have you?"
"No, but it's okay. I... err.... I prepared. The coconut you smell, I put some of my lotion up inside me... where you are. Thank god I did. You're really big. And it feels really good like this - all nice and slippery."
"Why you little..."
"Yell at me later, Tunny. Right now, fuck me."
He began to sodomize her steadily. Jessica slid a hand between her legs and began to touch herself again. Winston watched the blanket move as she masturbated. Then the moving stopped and he felt something slender rub his cock from inside her. She was toying at the entrance to her now-dripping vagina. She teased herself and him through the thin membrane that separated her pussy and ass. She slid her other hand down between her legs and used it to frig herself at the same time.
The utter depravity of their joining and the fantastic sensations raced through them both. They came together. Winston lurched forward to bury his full length into his sister's ass, Jessica grind back against him to hungrily accept every inch. He spurted his seemingly endless supply of cum inside her as she used his cock in her ass together with her fingers in her pussy and on her clit to stretch out her orgasm until she couldn't stand it any longer.
The intensity of their release, the late hour, and the rum had them both fall asleep immediately. Neither of them so much as stirred when, a few minutes later, his softened cock finally slid free of her well-used and no longer virgin ass.
Winston woke up first. He fidgeted slightly and realized that they were literally stuck together. The brief but painful tearing sensation he caused peeling his dried, cum-coated cock off his sister's butt cheek woke her up too. She rolled over to face him and cuddled into his neck, kissing it softly.
She was demonstrating none of the horror that Winston almost hoped she would unleash over what had happened. "Jess, we need to talk."
The nonchalant routine again? "About what we did last night."
"I needed you again and you were there for me. You're very dependable, brother dear." Her hand slid down his muscled stomach and bumped against his morning wood. "Feels like you're the one in need now, Tunny."
"Stop it. That's just a morning thing."
"Suit yourself, I'm going to take a shower then, I'm all covered in..."
"I know what you're covered in!"
"Come... join me," she grinned at her own pun, "in the shower. We can have more fun if you want."
"No more fun!"
"Okay, okay. But I'm still going upstairs to shower. If you want to keep yelling, that's fine, you'll just have to follow me."
He did follow her. As they climbed the stairs behind her, he fought not to stare at his kid sister's perfect adolescent ass. He followed her into the bathroom and watched as she carefully removed her bra and turned on the shower and stepped inside, closing the glass door behind her.
What words would make her understand that this was all terribly, terribly wrong? He ended up sounding more like a parent than he intended.
"Sis, this is incredibly irresponsible. On both our parts." He watched as she soaped her body and he continued to rant.
Jessica went about her showering as if nothing was wrong. When his ranting slowed, she calmly replied. "What's irresponsible about it? Nobody got hurt. We both enjoyed ourselves. I have a particularly large patch of evidence that you enjoyed yourself dried on my butt cheek over here."
"Jess, you are my sister for God's sake. Look, that first night, I wanted to help you. Last night, we got drunk. Sis, seriously, it's wrong. Really wrong. We have to stop."
"I don't see it that way. We love each other. We're attracted to each other."
"It's not supposed to be like that..."
She finally paused in her shower routine to look at him directly. The perfect, ivory expanse of her body was covered in soap lather. It ran down her flat, smooth belly, dribbled down her long tapered legs. She was an erotic dream. If only she weren't his sister!
She leveled her surprisingly serious green gaze on him. "Things have changed, Tunny. You've been in me. In fact, two out of three holes now stud." She turned and braced one hand against the shower wall then bent deeply at the waist. "Two days ago, you were here." She ran her forefinger up and down the smooth lips of her pussy. "You were there just a little. But just enough." She shivered. "It was the largest orgasm of my life. Well, until..." She traced her fingers upward and circled the fleshy knot of her sphincter, "…until last night when you were here. All the way in." She slipped the tip of her forefinger into her own ass briefly and pulled it free. "I liked it. A lot. Deny it all you want but you liked it too."
She stood and looked at him through the water beaded glass. The shower was cascading down her shoulders and streaming over her beautiful new breasts. Her eyes were emeralds, bright and fierce and beautiful. "Look at me, Tunny. I love you. I'm in love with you. And I want you. We can't take it back. I wouldn't even if I could. Would you?"
Winston didn't have an answer.
"Are you coming in with me?" she asked softly. The invitation meant more than just this one shower.
It was several seconds before Winston whispered hoarsely, "No."
Jessica's shoulders fell. She sighed sadly and shut off the water. He waited for her to open the shower door then handed her a towel. She quickly pressed her dark hair dry than wrapped her long slender body in its terry cloth.
She stepped out and stood in front of him. "If I misread you, if I am really and truly wrong about this... about us... and I've hurt what we are... I'm sorry." She leaned in and kissed him softly, gently, chastely on the lips.
"No points," he smiled weakly as she pulled away.
"That one was free," she reached up and carefully traced his jaw with her hand. She turned and left him alone in the bathroom. He heard her footsteps come back and her smirking face appeared through the doorframe. "But, Tunny, you really ought to get in the shower and wash yourself off. You stuck that big thing of yours in your little sister's dirty place."
"Jess!" he cringed as she disappeared again. But he was glad for the humor. It felt more normal, this kind of teasing exchange between them. He was smiling to himself as he took her advice and stepped into the shower.
He was rinsing off when his sister peeked in. "I'm headed out on errands. I'm looking forward to actually getting out and about for a little while. Be back in a bit."
The house felt emptier as soon as she was gone. He had one errand of his own but was back before her. He ended up whittling away the hours reading, watching TV, and checking e-mail. He sat at the kitchen table to eat a slice of leftover pizza, brooding as he chewed. As tortured as he felt with Jessica around, he was now miserable without her.
She breezed in through the back door, wearing a short denim skirt and a tight red V-necked t-shirt that put her new cleavage on display. She was carrying a few bags. "Wow, it was nice to get out of the house." She paused and smiled brightly when she saw him. "You look sad, Tunny. Don't be sad."
She plucked one of the bags from the rest and slid it across the kitchen table in front of him. "Here, I picked up a few things."
He peered inside. It held a new vibrator and a pack of condoms. He looked up at his sister and rolled his eyes.
She smiled. "Take me to bed."
"No," it came out with a little less conviction than it should have.
"Come on. Upstairs. I'm not doing it on the couch again." It was like she didn't even hear him.
"I'll be in your room waiting for you. You go ahead and have your last little internal struggle down here. Then come on upstairs and make love to me. I'll be the half-naked girl on your bed."
She brushed past him and left him to his thoughts. He did struggle. It took nearly five minutes before he followed her.
True to her promise, she was there waiting for him on his bed. She was wearing a matching red satin bra and panty set. She looked like the world's best Christmas present.
"When did you know? That I'd cave, I mean." He asked her meekly.
"The first night. When you started humping against me after I started coming. That wasn't just my selfless big brother. It wasn't for me. It was for you. After that, it was just a matter of time. I was willing to work on you the whole summer, honey."
"Don't beat yourself up. I do win our little struggles now and then. And I put an enormous amount of energy into this one." She slid her crimson panties down her legs, revealing her smooth, bare pussy already beginning to glisten. She slipped out of her bra, freeing the large perfect teardrop breasts that now lazed on her chest. She stretched out nude on his bed and smiled. The sight of her like this made his knees rubbery.
"The good news is that I have a pretty good consolation prize for you, Tunny. Me. Come here."
He shuffled to the bed and his waiting sibling. She helped him off with his t-shirt then unbuckled his jeans and pushed them down with his boxers until she was eye level with his stiffening cock. She looked up at him as she closed the distance and touched her tongue to its tip. She grasped it with one soft hand and took its first few inches into her mouth. Her tongue swirled around it delicately.
She spat him out to give him a wicked look. "You're three for three on holes now. From here on out, we're only going to be arguing about depth."
"No more arguing," he sighed. "Where's that new toy of yours? Let's make sure it works."
"That a boy!" she beamed. She reached into the bag next to her and handed him the vibrator.
He realized now that it was out of whatever package it must have come in and the batteries were already in it. She knew what he was thinking. "It was a long drive home." She shrugged.
She spread her legs lewdly and ran her own hands down her smooth, flat ivory belly as he slid onto the bed and settled himself between her legs. His sister watched hungrily as he kissed the inside of each of her legs and then zeroed in on her smooth little teenage sex.
"Tell me," Winston teased her, his face millimeters from her sex. She could feel his hot breath across her delicate flesh.
She knew what he was after. "I want it."
"What do you want?" In for a penny, in for a pound - Winston was going to play her game.
"I want your mouth... on me," Jess panted.
"Here," she ran a finger between her legs and along her smooth pink lips.
She snickered. He was mirroring the prompting she'd given him their first time. "Eat me, Tunny. Lap my little clit. Make me cum. You always make me cum so hard."
He barely and briefly brushed his lips against her pussy. His tongue grazed her clitoris. Her body jerked in reaction.
"Have you pictured this?" he asked.
"Mmmhmmm..." she moaned.
"Dreamt of this?"
"Yeah..." she whined, eager for his touch.
"Lied for this?"
There was a long pause. "Yesss..." she finally hissed, "Now please, Tunny, please…"
With his sister's admission, he began working her clitoris with his tongue. Flicking at her little bud, he brought the vibrator to her opening. She was already dripping wet. He slowly twisted it into her. She was tight. He had to press firmly. At a little past two inches, he felt the vibrator push up against something. Something pliable. Some sort of barrier.
Holy Mary, Mother of...
His head snapped up to look at her in disbelief. She smiled weakly, "That's why I didn't let you all the way inside me before."
"So you want me to?"
"I don't know what to say."
"Say you'll do it. I want it to be you."
"Wow, okay, errr... any particular way you want me to do it? I mean, do you want me to do it now, with this thing?"
"You know I never want to wait. Yes, do it. Just like this."
"Oh boy, I was right, you are a kinky little mess."
"Yep. But now that you brought up kinky, I do have one improvement to what you're doing. Remember when I asked you to inspect my goods last week?"
"Remember what I asked you if you would lick?" She carefully pulled her knees up towards her chest, it rocked her hips forward and exposed her pale little rosebud. "Do it," she whispered.
"Say what you want," he demanded again.
She didn't need prompting this time. "Lick it for me, Tunny. My ass. Lick me and rim me and fuck me open with my toy. Then fuck me for real. Take me tonight, Tunny. I've waited so long for this. I want your big dick wedged in me before the night is over."
She watched him hold the vibrator pressed gently against her hymen and duck beneath it to lap delicately at the small rose of her backdoor. She groaned and reached a hand down to circle her abandoned clitoris.
"So good," she sighed.
He continued lapping at her tiny, soft ring and began to fuck her with just the end of the vibrator. The combined sensations had her humping up and down instinctively. After a few minutes, he wormed the tip of his tongue into her ass and she started moaning at the new sensation.
At her third moan, he steadily drove the vibrator home through her hymen. Jessica gasped through clenched teeth but continued humping up and down.
"Turn it on," she whimpered.
It took a moment for him to understand what she meant. Then he hastily twisted the vibrator's base and it hummed to life in her. She jerked at the suddenly intense throbbing deep inside her. "Tunny, I'm going to come now... really big... you're still going to fuck me after this right?"
"Mmmhmmm," he confirmed from between her legs, still teasing her rosebud with his tongue.
"Good," she panted. Barely a minute later she peaked, mauling her clitoris and jerking her hips up to swallow the vibrator's length. Her upward motion speared her ass onto her brother's tongue as her body rolled in orgasm.
When her ass came back to rest back on the bed, he slipped the vibrator from her drooling pussy and tossed it to the floor. He crawled up the bed to stretch out next to her. She curled into him, still catching her breath.
"More," she whispered finally, looking up at him through dark hair that had fallen across her eyes. She rolled onto her back again and pulled him on top of her. She took his hard shaft in her hand and pressed it to her battered little hole.
Winston barely remembered the condoms. "Sis, protection first right?"
She nibbled her lip and shook her head. "I lied Tunny. I'm on the pill - been on it for the last year. Be gentle? I'm still a little sore."
He nodded. Together they carefully eased his larger than average cock into her near virgin pussy. She was tight and swollen but slick from her orgasm. She winced as he slid into her, filling her up completely. He felt his tip just brush her cervix. The contact made her shiver. They held motionless like that for several long moments. She willed herself to relax, to accept the oversized cock she'd wanted for so long. He marveled at the beautiful woman beneath him and waited for some sign to continue.
"Tunny, when my chest is healed completely I want you to fuck me from behind. Bent over your desk like I was when you were inspecting my goods. I was fantasizing about that at the time."
He shook his head with a smirk and leaned down to kiss her. When he broke the kiss, she saw him glance down at her chest.
"And I want you to fuck them too. My boobs, I mean. I want to kneel down in front of you and press them together for you to fuck with your big dick. I want your cum on my new tits."
He withdrew from her slowly, experimentally, and she groaned happily. Only half way out, he reversed and thrust back into her. She exhaled forcefully, hazel eyes wide and wild looking up at him. "So good," she groaned under him.
They fucked carefully, never building past a steady rhythm. On his downward thrusts, she rose up to meet him, grinding his full length into her. She found she liked the contact when he bottomed out inside her. When he retreated, she experimented - squeezing down with her muscles. He felt her tighten down onto him and smiled, moaning out a happy "very nice." His compliment made her glow even more.
They continued like this for several minutes until Winston leaned back to sit upright on his heels, still buried in her. "Feel like coming for me?" he asked.
"Always," she purred, and reached up to toy with her own nipples.
He brought his hands down to their juncture and centered both of his thumbs on her clitoris. He began to brush her little bud upwards with each thumb, essentially twiddling his thumbs backwards in an unending circular motion he suspected she might like.
He was, of course, right. How long do you have to love someone - how well do you have to know them - before you sense with near-certainty how to please them best without them asking? Without them even knowing how to ask or what to ask? Five years? Ten? Fifteen? How about your entire life? Winston brought this to bear now.
Jessica's breath caught in her chest at this last touch. Her brother's thick cock, the one she'd fantasized about for far too long was wedged - no, crammed - inside her. It stretched her more perfectly than she imagined because she couldn't imagine it until now.
She looked up Winston, her sweet Tunny, and her head replayed memories from their joint childhood. Thousands of shared secrets and little intimacies. Years of love, of laughter, of trust. When her brother touched her in this last, perfect way, everything rushed together. She felt something huge shift deep inside her - something so large she didn't think it was possible.
"Tunnnnnnnyyyyyy...." she keened, almost alarmed at the intensity of what was coming. "I can't..." she sobbed, actually choking a little.
"It's okay, sis, don't fight it..." He watched the muscles in her abdomen clench, release, and re-clench violently - the faint image of a six-pack appearing and disappearing beneath her pale taut belly. Her new, large breasts rocked with the clenching.
She jerked as the spasms radiated from her torso into her long slender legs and arms. "Alm-m-most ...too... too... b-b-biggg," she stuttered and wailed, arms and legs suddenly twitching, eyelids fluttering madly. She felt the undertow of her impending orgasm dragging at her, sucking at her insides. The sheer magnitude of the looming climax blotted out all thought.
"I love you, Jess," he whispered, "and I always have."
Her wave crashed, rolling her under.
"Wuu ahahahahaha," she shrieked, her slender chest heaving off the bed as her vision went white. Her smooth ivory hips jerked upwards at the same time, mashing into him, grinding up onto his cock until it crushed against her where it bottomed out. Her body remained arched like this for several seconds, her jaw clenched tight, panting through her nose loudly. Her body shuddered The rippling walls of her seizing sex dragged him along towards his orgasm. When she collapsed back to the bed, still peaking, he thrust into her twice and jerked his cock from her to fist it viciously. He grunted as he erupted mightily, jetting cum up across her belly, then onto her breasts, then up to her neck, then into the dark hair splayed across the pillow beneath her head.
He fell forward next to her on the bed where they both lay gasping for several minutes.
"You got your stuff in my hair," she finally laughed, giddy in the aftermath of the lovemaking she'd wanted for so long.
"Complain too much and I'll aim for your face next time," he threatened, reaching an arm around her and pulling her in to his chest.
"That might not be so bad," she replied cheekily. They rested a few more minutes until, lifting her head, she kissed him. She recoiled in mock horror. "Don't take this the wrong way, but you need to go brush your teeth. All I can taste right now is my ass."
He chuckled. "You weren't complaining earlier."
They clambered out of bed and into the bathroom. He brushed his teeth while she relieved a post-coital tinkle.
When she was done, he paused his brushing. "Jess, you said you put an enormous amount of energy into this..." He raised an eyebrow.
His sister sighed. "I got you drunk on purpose last night, Tunny. The drinks I fixed... mine were just Coke. You got a double dose of rum."
He nodded, not entirely surprised.
"And you know that I actually lubed my own butt with coconut lotion just in case I could convince you to take me that way. But... I also broke my vibrator on purpose and left it out for you to find the night before. And it was my idea to show you my breasts and have you touch them before the surgery."
Winston closed his eyes and shook his head as he processed what she'd said.
"How long, Jess?" He finished brushing and rinsed his mouth while waiting for her to answer.
When he looked at her in the mirror, her eyebrows were knitted together with worry.
"How long have you been feeling this way? Working on this? Working on me?!" he said more sternly.
She winced. "I planned this whole thing. I scheduled the breast implant surgery for now so you would be home from school. So we would be alone and you would have to take care of me."
"Yeah but Mom and Dad would have been..."
"I orchestrated Dad's trip to Africa. I just had to plant a couple of seeds in his head about the British colonial period, the summer being the perfect time, their 20th wedding anniversary, yada yada."
Jess was talking in a rush now, trying to blurt it all out and get it over with.
"It started before you left for college, I saw you with your girlfriend in the backyard one night. I watched her blow you. You both looked so happy. For only a moment, I was horrified like I should have been. Then, I don't know, something else happened? I got really turned on. Then I got jealous. Seeing you like that made me realize how I felt about you. That you were more than just a big brother to me. So I started talking nasty to you. I needed to wear away at your image of me as your innocent little sister. The gay accusation stuff was a ploy too. I wanted to goad you a little - make you want to prove to me you weren't gay. I also did it to throw Mom and Dad off."
Winston finally found words. "They don't think I'm gay."
"No, but they think that I think that you're gay. And that's almost as good."
Again he felt the magnitude of his sister's effort. "Wow, okay, that's so scheme-y that it's a little scary.
She looked up at him through her mussed dark hair. "Look, I wish I could say I feel bad about all this but the truth is that I don't. Well, except... Tunny, I'm not on the pill. That was a silly last minute fib. I just really wanted you, without a dumb condom in the way. I'll go on the pill, I swear."
Winston allowed himself a little satisfied smile. "I can at least contribute on that part. I'm reluctant but I'm not dumb." He opened the medicine chest next to him and pulled out a vial. He shook a pill out onto his hand and handed it to his sister. "Morning after pill. I picked a few up at the store this morning."
She stared at the tablet a long moment. He could feel her weighing the decision.
"Kids someday Jess, just not yet. We're young. We have plenty of time to work that out. Together. No scheming, okay?"
He could tell that it wasn't what he'd said that made her put the pill in her mouth and swallow it. It was the way he'd said it. Casually. Comfortably. They were going to be together for the rest of their lives.
She knew that as soon as he said it, she could count on him. He was, is, and would always be, dependable. He was her rock. Her immoveable object - well, nearly immoveable object. That last thought made her smile to herself.
She filled a cup with tap water and took a gulp to wash down the pill. When the cup came away from her lips, he was waiting. She hadn't seen it coming because she couldn't see around the cup and she didn't think he really liked their old game anymore.
She was wrong.
He stole his kiss quickly, his lip curling up just a little smugly at one end like it did when they were kids.
"One up," he grinned.
Jessica eyed her brother carefully. Stealing a smooch in broad daylight, standing right in front of her, in a bathroom with a huge mirror in it was pretty slick. It had required a perfect sense of timing, a subtle shift in his posture to make her turn towards him and away from the mirror without her realizing it, and a keen awareness of her line of sight.
Maybe he wasn't so rusty after all. No, perhaps not quite as rusty as she'd thought.