#745) Traveling Over the Holidays

(I wrote this story over a year ago, updated it a bit so as to publish it during this special time of year. I hope you enjoy!)

Covid and its variants have fucked up the world in a myriad of ways, but Jane thought it did her a favor. Jane met Jim in February of 2020. They dated several times, knew they got along well, were attracted to one another, and compatible as Top and bottom just when the world was shutting down. The pair took a risk and moved in together. Staying isolated from almost everyone else solidified their relationship. They each got their vaccines and boosters, played it safe by playing only with each other.
So, even though the omicron variant was still virulent in December 2021, Jim and Jane thought it was worth it to travel, to take the significant step to introduce their significant other to their respective families. This would entail several significant changes in their lives for the duration of the trip. They’d be sleeping in separate bedrooms for the first time in nearly two years. There probably wouldn’t be an opportunity to have sex, and as importantly to these two spankos, there almost certainly wouldn’t be the chance to play at D/s together for about a week and a half. Almost as challenging, because the lead-up to the holidays was typically hectic, as it used to be before the virus, Jane and Jim didn’t get around to having a special night of sexual fuckery and sinful frolic in the week before their trip.
“We’ve never gone longer than a few days between sessions before…” Jim lamented. (By “sessions” he was using the word they had adopted to mean both spanking, their usual form of foreplay, and sexual intercourse, the de rigor result from their slap-and-tickle play.) “What’s happened to us?”
“Life…” Jane answered truthfully. She hated it as much as he did, but was more a realist and less the romantic.
“Do you wanna play now?” he asked plaintively, as they packed their suitcases, the night before their flight.
“Let’s save it up for a big blow-out when we return,” she answered. “I can’t afford to have a bruised bottom when sharing a bedroom and bathroom with my sister. We’re both exhausted now and would be doing it just to do it. It’ll be so good as a reward after we return…”
Jim wasn’t happy, but he had to agree, so didn’t argue further. Their itinerary was to visit Jane’s family first in Charleston, South Carolina for Christmas, then fly to just outside Washington, D.C. in Alexandria to see Jim’s family for New Years. Jane came from a big family with four sisters, where she was the baby, and all of her siblings had already married and started families of their own, all staying in the huge home they’d all grown up in. Then the couple would catch a series of flights to the nation’s capital to stay with Jim’s parents, where he was the only child and the apple of his mother’s eye. There is no need to describe the minutia of their trip, the relevant details are these. Jane’s next older sister had a child, a seven-year-old boy named Justin. This boy was a hellion, undisciplined because he rarely heard the word “No!” His parents put him in time-out whenever he misbehaved, but he remained defiant, usually just walking away to do as he pleased. All the other members of Jane’s family seemed to turn a blind eye to Justin’s many offenses, and more importantly, to the serious personality problems the child was exhibiting. The couple’s travels to our nation’s capital were uneventful by comparison. They did go into the city to sight-see the wonderful architecture.
“God, it’ll be so nice to sleep in our own bed!” Jane exulted as soon as they dropped their luggage back in their bedroom.
“God, it’ll be so nice to sleep together in a bed!” Jim replied.
“God, it’ll be so nice to do stuff besides sleeping together in a bed!” Jane smiled and wrapped Jim in an embrace, kissing him passionately. In a moment, they were pulling off each other’s clothing. “Do you wanna spank me before we fuck?”
“Is the pope a Catholic, does a bear shit in the woods…?” Jim retorted.
“Is Justin a total brat?” Jane smirked in retort.
“God, that kid drove me crazy!” Jim exclaimed.
“I’ve been thinking about that…” Jane smiled lasciviously as she pulled off her underwear and laid back on their bed. “Did you ever read the children’s book, The Whipping Boy, in grade school?”
Jim shook his head, joining her in the state of nudity, joining her on their continent of a bed, but unclear why she was bringing this literary topic up now. He wanted to explore the geography of her body for the first time in too long. Jane felt divided because she really wanted to make her point, but to do so had to fend off Jim’s advances, advances she dearly wanted to receive.
“Listen to me for just a second,” she persisted. “It’s the story of a poor boy in medieval times who is hired to be a surrogate for the heir apparent…” Jim nuzzled her neck, which drove Jane crazy with lust, so she moved back a bit on the bed. “But he wasn’t hired as a food taster or page for Prince Horace…” He kissed her right nipple, which hardened and protruded noticeably under the affectionate attention, so Jane pushed Jim’s head to the side playfully. “He was made the whipping boy for the guy they called Prince Brat, he was designated to take the beatings the prince rightfully earned from his many misbehaviors!” the school teacher summarized in this impromptu book talk. Jim looked his lover in the eye for the first time. “I was thinking…” she now continued with his full attention, “Justin drove me just as crazy as you, he was totally infuriating with HIS many misbehaviors… I was thinking I’d like to be Justin’s whipping girl… take out all your righteous anger at him on my deserving ass…” and she turned over and wriggled this pert and perfect portion of her posterior anatomy at her lover, a big, white, round red flag waved in the face of her bullish Top. Jane didn’t need to seal the deal any further, but it pleased her to describe it, so she added, “I want you to give me a memorable punishment. I want to remember the thrashing you’re about to give me and wince, even cringe at how hard it was. As an old lady in a retirement home decades from now, I want to vividly recall how you wore out my ass on this day. Every time you are about to relent, to show me mercy, remember that insufferable incorrigible little fucker Justin, and whip me with renewed vigor…”
Jim had heard enough. He seized Jane by the wrist and resolutely pulled her across his lap at the edge of their big bed. He started with a hand spanking. He loved the ass before him across his knee! It was so round and firm and feminine. It started out so pale and cool, as he warmed her pink, then cherry red with brisk spanks with his large right hand. He listened to Jane’s endearing little yelps and mews, heard them turn to moans and gasps. It touched something deep inside when his relentless slaps brought her voice to break, as he heard chortling sobs and sniffles. “Cry, little girl,” he thought to himself as he watched her bottom bounce and ripple, as she concertedly sobbed with plaintive boo-hoo-hoo’s. “It’s been too long, I’ve wanted to do this for over a week. And if you want to pay the penalties for precocious Justine, so be it…” He spanked her hard, deciding not to take a break between sets, just wear her out with his hand. Jane’s bottom was now tomato red and bordering on magenta. Time to take a reading. Jim jammed his middle finger into the space below his lover’s magnificent ass, between her thick thighs and into her labial lips. Jane was very wet, her sex engorged. That was enough with his hand. Good thing because his palm was really smarting. Jim could only imagine how Jane’s fanny felt. He lifted her off his lap and placed her over the edge of the bed while he went for the implement he wanted to use next. From the steamer trunk they used as a toy chest for all their weapons of ass destruction and sexual aids, Jim extracted two.
He put one on the floor by her knees, showed her the other, a short leather multi-tailed flogger. Jane looks stunningly beautiful to Jim at this moment, with her pretty face wet with tears, and her sweet mouth still softly sobbing, and her big wet eyes seeing everything like a kaleidoscope of rainbowed, prismed colors, and her normally quaffed hair in disarray. She is just starting to enter her sub-space, hyper-sensitive to all around her, he surmised silently. She’d be heaven to fuck right now, so responsive, so invigorated, with just the hard edge taken off her, as he had so many times before. But not this time. This would be pure punishment tonight.
“I love that implement!” she whispers.
“I know, that’s why I chose it. I’m going to use it on you long and hard. When you can’t take it anymore, you have my permission to touch yourself, to make it bearable. Remember what you said about wanting to be the whipping girl…?”
Jane nodded, then buried her face in the bedclothes and arched her ass out invitingly. Jim whipped it across her cheeks, it was just long enough to reach across both of her curved orbs as well as deep into the crevice between. Her muscles flinched. The flogger was magical. It could viciously bite tender flesh, as well as comfortingly lick the wound, as it first stung and then warmed. Jane found it exquisitely erotic to be whipped with this flogger. It was already working on her mind as perniciously as it was punishing her bottom. True to his word, Jim gave her fulsome bum a bottom-full of strokes; he gave her a beating that covered every square inch of her large, round tush. It must have been after about the hundredth lash when Jane reached beneath her hip to touch her crotch, open her pussy, finger her clit, make the unrelenting pain manageable. Being the expert Top he was, Jim watched Jane’s every movement, reading her body-language avidly, in the Braille she was using on her sex, as well as all the other signs. The lattice-work of marks that now graced her buttocks from the multi-tailed whip declared loudly that the girl had accepted a thorough thrashing, but it wasn’t enough. He parted her, exposing the inner curves of flesh including the dimple of an anus. Jim whipped her just as hard here, making the girl squirm, flinch, moan, rub her nearby sex all the more furtively. Neither man or woman kept track of the orgasms Jane went through, some were subtle, some were screamers, all of them enabled the submissive to bear the burden Jim was laying into her. Only when she sprawled across the bed, wrung out like an old dishrag, covered in glistening sweat and jism and tears, too worn out to cry anymore, did Jim stop whipping.
Jim picked up the limp form of his lover and pulled her onto his seated lap to cuddle and caress and comfort. He kissed her tears away then kissed her mouth. He stroked her mussed hair, then stroked her oft-stroked savaged rear. Jane hiccupped, was contrite and content.
“If it were up to me, I’d stop now, hold you for a long time, then fuck you the rest of the night… but you said you needed it to be monumental, memorable…” he whispered in her ear.
Jane nodded. When she could again speak, she whispered back, “You haven’t completely exhausted this whipping girl… The Prince Brat is so naughty… I need more…” With her help and like-minded intent, he turned her back over his knee. That’s when she saw the paddle he’d put on the floor. Of all the implements they owned together, Jane hated this paddle most of all. It was thick wood with holes drilled through it. It hurt like a motherfucker even when Jane was fresh and ready for it; now she was worn down, down to her submissive essence, sensitized and sore. Jim reached down and picked it up off the floor. Jane caught his hand and kissed it, then kissed the tool that was going to kiss her backside cruelly. “I want this…” she whimpered so softly it was barely audible, “I need this… give it to me…”
They both knew that the paddle would bruise her. She wanted the see the bruises blossom, feel them restrict her choices. She wouldn’t be able to sit comfortably for days. She’d be reminded with every movement of her lower half that she’d been beaten mercilessly on Monday evening, the third of January, 2022. She feared what was coming, but also longed for it. Beating’s bruises made her proud, proud to be a submissive to the core of her soul, proud that her cast-iron butt could take such a fearsome whipping, proud that she was owned and cared for by Jim. Part of her wished that both of their families could see them now, her in the ignominious position over his knee, her bottom well and truly pummeled, enflamed but desirous of more, both of them naked and aroused and doing a mating dance particular to their specific tribe. She wanted to shout to every member of her conservative and repressed family, “We’re spankos! We love this! It looks scary, but it’s actually divine! I mean that exactly, I believe God made me this way, and Jim worships at the altar of my ass! We’re in-touch with our bodies and love expressing our love in this way. Heaven forbid you even think about reprimanding little Justin, but we like physical corporal punishment, the yin and yang of it, the give and take, the white-hot sexuality of it all!” Jane arched her bum up, gave Jim a good look, waggled it in his face. She felt a second wind, felt energized, ready for round three. She was high on endorphins and deep in her sub-space. She looked back over her shoulder at Jim’s face. He was staring, mesmerized by her enchanting derriere, as far away from the reality of this moment as she was in his own Dominant way. She waggled her red cheeks all the more, all the more lasciviously and wantonly articulated, “Paddle me, please, hard…”
Even though her cheeks were nearly numb, she felt him tapping her lightly back there with the dreaded paddle. Her mind drifted for a nanosecond. Who first thought of drilling holes in a paddle? Was it school principals? She’d always heard that her principal had a big wooden paddle in the bottom drawer of his desk for paddling errant students. Victims swore that it hurt more. Jane thought that it was more aerodynamic, lighter in weight. The holes made a faint whistling noise as it blazed through the air.
Whomp! All thoughts flew out of her head as her brain was filled with unspeakable, un-process-able pain. Jane felt her mouth drop open, the only response possible in light of the blinding, white hot pain.
Whomp! Yes, that first smack wasn’t a fluke, a one-off. It hurt like holy hell, as two welted areas now bloomed on her poor butt, one on each cheek. She found her voice. “Yeow!”
Whomp! “OWW! Fuck!”
Whomp! Tears filled Jane’s eyes, easily overbrimmed her long lashes, coursed down her cheeks. She’d been taught to take her medicine stoically, no matter how large the dose, but these trainings flew away in this instant. Jane kicked her legs as Jim continued to punish her, hammered her toes and fists against the floor as Jim continued to punish her, screamed as he continued, begged as he continued, pleaded as he relentlessly continued. All to no avail, he didn’t miss a beat (excuse the pun). Jim trapped her legs between his, and just kept walloping her. He’d given her twenty resounding swats, planned to administer five more. But then Jane went too far. She reached back behind her behind, trying to protect her bottom from the onslaught with one hand and catch his punishing, weaponized hand with the other. She was not successful only because Jim froze with his arm raised high.
“What are you doing, young lady?” he admonished.
“I… I… I was just…”
“Has it ever been permissible to reach back like that?”
“It just hurts so fucking much…! I HATE that paddle more than anything…If I was getting punished with anything else…”
“So it’s my fault for choosing the implement you really need to taste for punishment?” he asked quietly, signaling that he was very mad.
“No! I mean…”
“Do you determine when you’ve had enough?”
“No, sir,”
“Do you think Justin’s misbehaviors have all been adequately addressed? You yourself said you needed it. Hard…”
“I just lost myself… I’m sorry, I…Please let me make-up for my error in judgement, beat me more with that fucking thing…”
“I’ll be interested in hearing your sincere apology when your punishment is through. Right now, I think you need a taste of the cane.”
“I… Yes, sir, as you wish…” Oh, God, now you’ve done it, Jane thought to herself, you’ve earned a session with the cane!
Jim placed Jane on her feet. Her knees were wobbly and she found it difficult to stand. She found it more difficult to grasp the fact that she’d just been defiant. It was an impulse that she couldn’t explain, but she also couldn’t justify. Jane didn’t have a lot of experience with this penultimate of punishment implements. Once, after a warm-up spanking, Jim had bound her to the padded punishment bench, with her bottom elevated and her ability to move even an inch taken away from her. Jim had given her fresh and pristine buttocks “six of the best” stripes on that occasion. Each stripe was laid on hard enough to leave “double tram lines.” The thin cane had reverberated as it landed, increasing the pain. The welts were livid red and raised on the otherwise smooth surface of her curved orbs. That beating had taken everything out of Jane. The only positive was that she had a set of marks that burned brightly across her pale moon for nearly a week afterward.
“Bend over at the waist, grab your ankles, stick your bum out,” Jim instructed. Just as she’d expected and dreaded, but this time she wouldn’t have the support of the bench, and this time she wasn’t fresh and pristine.
“How many am I to get?” she asked, anxiety filling her voice.
“I don’t know yet. I’ll determine that somewhat depending on how you receive them. I must say that I’m very disappointed in your behavior, Jane, so am not inclined to be lenient. Can you understand that?”
“Yes, sir.” And she took a deep breath and bent over. She’d wanted this to be memorable, and it would be. Jim had used this time to replace the two other implements in their toy chest and bring back the cane to where Jane was, in the center of the bedroom. He tapped her lightly with the rod at the summit of her cheekiness. She remembered thinking that the whistling of the holed paddle had warned her of its immanent strike. That was nothing compared to the swish she heard, raising all the little hairs on Jane’s nude body.
Thwack! Jane gripped her wounded rump, stood bolt upright, danced in place, rubbed, cried, all within an instant after the cane had landed. With all her willpower, she commanded herself to bend back over and provide her Top with the target. As she did, she heard Jim’s modulated voice say, “Count them, please.”
In contrast, her voice sounded far away and disembodied and very shaky as she enunciated, “One. Thank you, sir. May I have another?”
The cane answered her. Swish, THWACK! It was other-worldly how much the cane stripes hurt across her already well-thrashed ass! “Two!” she blubbered through her tears. Jane reminded herself that she was the whipping girl, deserving of a colossal beating due to the impudence of Justin. She reminded herself that she’d have striped welts to admire on her ass for days to come. She reminded herself to count each lash, even though it was more like inarticulate wailing. Salty tears flowed out of her eyes and fell to the floor, clear and viscous snot flowed out of her nose, needing to be sniffed back with every breath, her Judas of a body made clear, viscous jism flow out of her excited, submissive pussy with each lash. When it couldn’t pool behind Jane’s labia any longer because of the quantity and pressure, it trickled down her thighs. Somehow, with lots of dancing in place and rubbing her welts and cursing the heavens, Jane made it to eight, and Jim put the cane down and took the wrecked girl in his comforting arms.
It took a long time for Jane to be consoled and return to full consciousness. She realized that she probably hadn’t actually entered her sub space until Jim started to cane her. That’s what made her able to commit the sin of reaching back to deflect the paddle. But having gone there, she was deep in it from this, the hardest disciplining of her life. Jim just held her as she was wracked with sobs, sobs for the pain in her backside, sobs for being a bad girl during her punishment, sobs for the unsuccessful experiment of being a proper whipping girl, sobs for sobbing sake because it felt so good, until her breathing was fairly normal once more.
Jim spoke softly to the little bird of a girl nesting in his arms, “We’d planned to fuck, but we’re both beyond exhausted. Let’s think about doing it first thing tomorrow morning, okay?”
Jane teared-up all over again. It’d been so long since they’d done it, she wanted it so badly, Jim had gone so long without it, it was all her fault… But she saw that he was right, so let him tuck her into bed, and was soon sound asleep.
Jim slept soundly all night long; Jane slept like a baby, awake and crying every hour on the hour. She got up and looked at her buttocks in the mirror. It was glorious! Swollen, so sore, bruises overlaid with cane welts, it was so sexy Jane could not resist the temptation to masturbate over and over again. She finally, fell into slumber at dawn. “First thing in the morning” turned out to be close to eleven A.M. Her eyes fluttered open to see Jim looking adoringly at her. “Fuck me…” she implored.
They lay on their sides facing one another as he entered her. They rarely did it in this position, and she found it sublime to be able to grind into him as she stared into his eyes. She came quickly and explosively.
“Now fuck me up my butt, please… I need it…”
Jim rolled over to reach for the lube in the bedside table. Jane rolled over and waited. She felt him take a painful pinch of fanny flesh to part her buttocks. He lubed her up thoroughly, and Jane had to work hard not to cum from just these preparatory ministrations.
“God, I love a finger up the ass!” she exclaimed as a mantra over and over, trying to keep from climaxing.
“We haven’t done it this way for a while,” he observed, “you’re tight back here…”
She felt the truth of this when he pressed his cock head against her backdoor. He was a very considerate ass-fucker; Jim always knocked gently and waited for admittance. As soon as she adjusted and relaxed, she pressed back against him. Jim watched his circumcised head disappear into his lover’s rectum, Jane felt it, every glorious centimeter of it, as it inched into her tightest recess. “Fuck me…” she again whispered as an image invaded her mind, as Jim’s cock possessed her in the rear. On their trip, she’d seen the Washington Monument for the first time. That’s what this felt like. Her rectum was out of practice due to lack of recent sexual use. His cock felt sharply pointed at the prick-tip as it cut into her tenderness. It felt rock hard. It felt huge as she took its length up her tooter. It seemed to be a square-based prism with edges that burned as she accepted it into her core. And it seemed to get ever larger toward the base, as it invaded the tiny orifice. “Fuck!” she now whispered over and over. Then, after what seemed like an eternity, she knew Jim was balls deep inside her, she could feel his short-curlies tickle her crack.
“Are you ready for me to fuck you…?” he breathed in her ear.
“Just give me a minute… it hurts so fucking good…!” She took some deep breaths and reminded herself to relax. “…Yes, fuck me, lover… fuck me up the butt!”
Slowly he withdrew. It was excruciatingly delicious. He pulled out until his cockhead breeched her hole. Jane had once taken an ocean cruise and they’d encountered a heavy storm in the middle of the Atlantic. At the crest of every huge wave, the ship seemed to shudder, then swoop down the trough. It made Jane seasick back then. Her body remembered, it seemed to shudder at this juncture, and then he was filling her again, plunging back into her. It wasn’t sickening or scary now. It was intense and fantastic! “Fuck me like your dirty whore…” she encouraged. He did. In and out, the friction building and starting to burn her sensitive ring, over and over, making her swoon, making her climax.
Jim sensed her orgasm’s approach. He fingered her pussy, found her clit, circled it and flicked at it and felt her stiffen, and cry out, and spend copiously all over his hand. Her rectal muscles gripped Jim’s cock like a velvet vice. The storm raged, then passed. Jim slowed the pace but didn’t stop and didn’t withdraw, and after a few moments respite, he began fucking harder and faster.
“I want you to cum again,” he told her.
“I want to! But I want you to join me, so fuck me, fuck me ‘til we cum together!”
Instead of side-facing spoons, Jim rolled Jane onto her tummy while staying conjoined, then seized her by the hips and rogered her feverishly. Jane felt the next orgasm approach. She reached underneath her and found her erect clit, stroked it, and came. The spasms that convulsed her tight rectum were extremely pleasurable, but still not enough to make him cum. He let go of her right hip and brought his hand up high. He slapped her already marked orb. Hard. Jane yelped, gripped him all the tighter and started to climax yet again. He spanked the other cheek, harder. Jane’s hips bucked, she cursed her lover, but came harder than she ever had. Her vag not only squirted, it gushed. Her buttocks flexed, as did all the internal muscles, so hard that Jim thought she might pinch his cock off at the root. But it felt incredible, and he came, in similar gushing jets, filling his woman’s bowels with sticky spunk.
Jim collapsed in a heap on top of Jane. Jane fainted dead-away in what the French call “le petite morte” or little death. She was unconscious for a full minute. They revived together, as Jim’s shrinking cock popped out of Jane’s tush
“Fuck, it’s good to be back home!” Jane sighed. Jim just smiled at her and cuddled close.
It occurred to her at this sublime moment that they had some unfinished business.
“I was wrong to reach back and interfere with my paddling, sir. I apologize, I know better. I hope you feel, as I do, that my total punishment absolves me of any lingering guilt… Are we good?”
Jim nodded. Jane kissed him, the buss becoming a passionate exchange. When their lips finally parted, she continued.
“I’m not finished thinking about that ‘whipping girl’ concept. I think it would’ve worked better if we did it like they did way back then…”
Jim was intrigued. “What’d you mean?”
“They used to whip people at the public whipping post in the town’s square. If I was being punished in public, bare naked and paddled humiliatingly, I think I would’ve been a good girl for it…”
Jim now smiled slyly, “What’re you suggesting?”
“That the next time we visit my family, and Justin misbehaves, I suggest you spank me in front of him and his parents, model for them a better course of action… And until we can do that in-person, we take photos of my punished ass to send them over the Internet…”
Jim wasn’t sure whether to laugh or not because he wasn’t sure if she was kidding or completely serious.
She continued obliquely, “And the next time we visit Washington, D.C., that we go up inside the Washington Monument… where you should butt fuck me good…”

2 responses to “#745) Traveling Over the Holidays”

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