The Dating Site Ch. 02
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Warning: This sequel contains deviant, public acts of illicit incest between a 31-year-old brother, and his 22-year-old college aged sister in Central Park; including graphically depicted anal sex of an incestuous nature as well as consensual BDSM spanking and panty fetish play. Do not read this if you are offended by first-blood incest between a sister and a brother, or amateur corporal punishment. Obviously, everyone involved in this interlude is over 21 years of age. Sincerely, Leonard
“What happened between you and mom?” Jessica asked her brother inquisitively, and her softly-spoken question, delivered like a statement, fell through Rick like a dark echo as they strolled together on a cold, wintry pathway in Central Park.
Rick, whose suave and gentlemanly approach to women, convincingly hid the ruthless attorney underneath, often gave his cherished little sis, Jessica, time to meet up on her days off school. Blossomed into a swan at 22, Jessica’s beauty was alluring. The young woman was in her final year of majoring with honors as a Fine Art undergraduate at NYU, and like her brother, was as talented as she was wild.
Wild; without regret.
Wild enough to have a male roommate like Ivan, who regularly brought rough trade back to the apartment she shared with the gigolo in the city, while Jess made her tuition, and rent contributions, not by selling her body, but her hugs. The seductive college girl ran a professional cuddling business from the apartment, where on weekends she advertised clothed cuddles to guys on Craigslist, mostly white collar types who craved a cuddle, and a soft female touch.
It was a good relationship. While Ivan fucked every man-hole with a pulse on campus, and reveled in gay bondage with his political studies lecturer; Jess turned a blind eye, in return for some lines of cocaine, and Ivan’s services as a makeshift security guard during cuddling sessions from their Greenwich dorm.
Pro cuddling in New York can pay well, if you’re a girl like Rick’s little sister, Jessica.
Usually before the close of business every Monday, her afternoon sessions with lonely forty- and fifty- something men passing through her bed, had more than paid next week’s rent contribution in full.
And shopping trips from sugardaddies.
With no sex asked for, and none given.
Meanwhile Rick, who was beginning to develop a taste for burying struggling homeowners for his corrupt banking employer, as his own bank balance rapidly expanded, knew all about Jessica’s cuddling sessions.
A man who had little time for chivalry, his uncharming response to Jessica’s paid dalliances was every bit as provocative as his sister’s cuddling ads.
Instead of chiding his wayward sister, Rick, a legal wordsmith, in fact derived a sick pleasure from helping his sexually attractive sibling weave invitations for her cuddling services into her dating profile on Todd and Clare, the dating site that put Rick’s cock into his mother’s cunt; and so many needy, older male clients into Jessica’s bed.
The memory of receiving a message from his mommy’s pseudonym, Susan, on Todd and Clare—the dating site where she pretended to be that younger woman, bound Rick to his sexual experiences with his mother, and his own sister’s edgy sexual excursions.
Her undeterred zest for life.
Rick truly treasured Jessica as one his dearest friends. Jessica’s continual positivity radiated from every part of her glowing soul. And his affection for her was reciprocated, implicitly, with the trust she’d formed with her darling brother.
An unusual closeness in both Jess and Rick’s childhood; the extended time they spent together when they were young, sealed their relationship with a rare level of trust, and confiding privacy, that many siblings would envy.
For a start—they never fought, and barely ever remembered having an argument.
This brother and sister’s profoundly deep connection of adult sexual intimacy found its first fruition 2 years ago, when at the tender age of 20, Jessica, presented unannounced at Rick’s apartment door, near the Javits, at 10pm at night, asking the only man who she knew how to trust, to do something for her that many wives would find difficult asking of their own spouses in the marital bedroom.
Jess asked for Rick to be more than a brother and best friend. To be, more than a boyfriend, more than a surrogate father, more than a shoulder to cry on—but the loving, authoritarian male figure in her life who would cater to her intensely deep and emotional need to explore consensual, domestic bare-bottom spanking play with a man who cherished her and didn’t misunderstand her, like so many men did.
Jessica craved to be punished. She craved to be spanked, hard, ever since her dad first warmed her seat, for lying. And the punishment became a dark, intimate, fetish that sated her brain chemistry even more relievingly than full vaginal intercourse.
Knowing how dangerous the New York Rick knew could be for a young woman, out on the streets eryaman escort trying to find that kind of solace from a stranger, Rick agreed to his little sister’s wish. He loved her too much, and couldn’t have his precious sister, Jessica, taken advantage of or abused while she inevitably tried to seek a spanking partner outside the home.
He didn’t want her to be, for example, exposed to the ridicule of a jilted college boyfriend, after the cruel rumor of a young woman craving such a childish punishment spread on campus, potentially affecting the degree for which she had worked so hard.
9 years older than his sister, Rick formulated and gave safe passage to Jessica’s stunning request, and as a result, every Thursday night, found himself postponing even dates he knew would end in sex, to find the naked contour of Jessica’s lower back as she positioned her exposed bare bottom across his seated knee.
Rick smacked hard, and as their spanking relationship grew, rarely did he not break a sweat with the spanks that resounded through his apartment walls on a Thursday night.
His consenting adult sister’s bare bottom across his knee every week, him having lowered her delicate, fragrant pantyhose and thong panties to the oval grooves of her milky thighs. A sadomasochistic routine that made him feel more of a man.
And, with time, the duo made their sexually charged routine, that didn’t include any sex, run like clockwork.
At 8pm, on the dot, every Thursday, Rick would interrupt his work for the bank, to await the soft knocking sound of a young woman’s knuckles, tapping on his apartment door.
He would open that door, the same one, Chloe, his mommy, had led him by the hand when they had sex last week, to find Jessica standing there. Her meek, doey-blue eyes widening with baited breaths for Rick’s appearance.
He always noticed her neatly groomed long, dark hair. She was so beautiful and elegant. Her gracefully high cheek bones and curvaceous body, that craved to be held and cuddled, him falling for his sister with each new encounter.
The rush of oxygen as he unlatched the door.
Just 22-years old.
Rick’s sensuous and voluptuous sister standing in her pink NYU hoody. Her sleeves rolled up to her elbows on both arms.
Hr white crepe skirt hugging her curvaceous, gym toned tummy, and, her dark Wolford pantyhose; lain bare against the white skin of her beautiful hips—a strap of her pink and white G-string thong that had crept, with her subway journey, out and above the brunette’s exposed naked left hip bone.
Jessica’s pinky, white flesh that Rick held so gently.
She was utterly delectable, and the reality of satisfying the disciplinary wishes of such a mature, sophisticated, and intelligent young woman as Jessica, blessed Rick emotionally; and, made his cock very, very hard.
Jess would step silently into his apartment, removing her elegant worn ballet shoes, without being told, and he’d smell the subtle fragrance of her femininity diffusing into his lounge, so much like mom’s, a loving glance at his submissive little sister’s countenance.
Rick wearing his work suit trousers.
His tie-less shirt portraying the authority Jess imagined. He was, more than fleetingly, the loving male authority that his sister had sought for her entire teens so ardently.
That made her feel submissive, in the mental place she needed to be.
Standing there, her wet nose, pink from the cold outside, pressed against the corner wall of her brother’s lounge room.
Jessica needed to stand like that for a whole hour, on her big brother’s carpeted floor, in pantyhose, and in silence.
Jess craved this.
Rick’s cuddling warmth, being bathed in his strong arms afterwards.
After tears had streamed down her face, from the grueling session that always ended her hour of corner time, when he put her across his knee.
When he undressed her, lifting her skirt.
Her bare flesh lying exposed to the loving, hard spanks from the flat of her brother’s hand. His stings landing visible palm prints upon her buttocks, repeated until each of her soft butt cheeks were rosy pink.
In their weekly routine, Rick granted Jessica’s wish again and again, unlocking the emotionally complex Rubik’s cube of his little sister’s heart. Her need to cuddle, and be cuddled, in a way that only he could fulfil.
Jessica’s need to be held at the waist as her beautiful tummy found the curve of his lap; to struggle with all her might against him, and buck her legs, and kick, and scream blue murder, as each hard, uncompromising smack thrilled her bare bottom, her dress riding way above her crotch; her wrists clamped around the legs of her brother’s wooden chair as she cried real tears.
Rick had spanked Jessica horizontally across his knee, so many times, he had proved in her agony, that no college boyfriend or stranger could ever placate and nourish what escort eryaman his sister needed as much as he.
To be in the flow of her loving rhythm of pain.
To be gentle, but firm, as Jess struggled in the arranged violence—a consensual interlude—22 year old brat and sassy rebel, against Rick’s vice-like grip around her naked hips. She often called out for her mommy just before the tears came.
Jessica, his loving little sister, calling out for their mommy, in the apartment Rick had fucked Chloe. His burning, seething stings from unmetered hand spanks, searing into his sister’s need to be a good girl.
Spankings defined the changing relationship Rick enjoyed with Jessica. One that any psychiatrist would have a field day in clinical analysis.
Wave after wave of her brother’s spanking arm, reigning down control over his gorgeous little sister’s pert bottom.
Ironically resolving, with every hard full palmed spank, Rick’s own deep seated insecurity that their mommy had wanted a daughter, more than a son.
Jessica’s dribbling, wet oyster clam.
Her pink slit of fleshy labia pressed together between her legs, oozing in the vibrations of the incestuous spanking that engorged her tightening clit with endorphins from a magical place.
Then emerging through her thick, natural pubic haired bush like a horse’s mane, the orgasm that wasn’t. A cerebral turning, transcending Jessica’s womanhood and making her feel like the loved woman she sought through these spanking sessions to be.
Tears flowed naturally.
When she finally was allowed up to cry like a baby in his rocking arms, at her request, she felt the nurturing of her 31-year-old brother’s stability. An attorney. An independent, strong man, who could, as Rudyard Kipling’s poem goes, keep his head in a crisis, when all about him were losing theirs and blaming it on him.
Though however much Jessica deeply loved her brother, up until this day, the siblings had never felt ready to cross the line of vaginal intercourse.
Usually, after the tearful spankings ended every Thursday night, Jess would return home to her apartment with Ivan. Her very sore bottom, glowing red as it pressed onto the rough seat of a New York subway car.
Jessica outwardly, just like any other girl her age; but inwardly freed of the guilt and sorrow her spanking arrangement with her brother absolved.
Her emotional kaleidoscope of feelings that no psychiatrist or art teacher or anger management class could ever even begin to heal, totally resolved through being thoroughly spanked like a naughty brat across her brother’s suited knee.
Rick’s bare bottomed treatment like an ice pack crushing the throbbing excruciation of a badly bruised knee, hitting the core of all Jessica’s fears and problems, saving her from mental illness; stopping her from descending into a dark clinical depression.
Incest beckoning relief. Her creative passions as an artist saved from being stifled by the traditionalism of the course at NYU.
Jessica indeed attributed her good grades to the many spankings she’d received over her brother’s firm, strong knee, and Ivan’s coke.
Rick, her brother, who put aside law and judgmental neighbors, to collude in Jessica’s physical humiliations. Having her delicate skirt raised like her dad used to do. Having Rick expose the natural wetness of her anticipating, dark haired pussy to her brother, before his painful, bare-assed hand spanked the naughty 22 year-old in earnest.
Half naked over her big brother’s knee. It made her feel alive, and weep with joy as an artist of her own destiny. Brave enough to go out there and fulfil her edgiest fantasies. To ask those she trusted for what she really wanted and needed inside.
A college age girl and a submissive woman, taken in hand. The context with which Jessica’s curiosity, as she strolled down this cold, wintry Central Park gravel way, now delved into her brother Rick’s secret with his mother.
Events she needed to know, as a whiteout painted the sky above Central Park, in preparation for heavy snow.
“What do you mean, what’s happened between me and mom?” Rick repeated as they strolled together through the park’s trees.
He hadn’t told anyone about the secret.
That he’d bedded mom while she posed as the profile of a younger woman on the Todd and Clare dating site; mommy’s subterfuge, a maternal link to gain entry to her son’s perverted sex life.
“Well, clearly, something’s happened,” Jessica replied matter-of-factly, still feeling the glow of her naked bare ass flesh where she’d thoroughly enjoyed Rick’s hand burning her nude behind only hours ago.
“She won’t tell me,” Jess sighed, and she crossed her ballet shoes as they walked on the path, then continued.
“In fact, mom asked me to ask you,” Jessica said, looking over at Rick to see if he was ready to divulge all.
Above the siblings, the branches of overhanging oak trees, naked from Winter’s blessing, guarded eryaman escort bayan the archway of their walk, and the shame Rick felt inside drew like entrenching waves from his sister’s inquiry.
“What do you, mean?” Rick replied quickly… too quickly… revealing the insecurity of the incestuous secret he was keeping from his little sister, Jessica. The uncomfortable trust that he had fucked their mother.
“You’re a really bad liar,” Jessica said, looking across at her spanking partner, barely suppressing the smirk that ignited her beautiful, blue eyes and lit up her face.
The prospect of making her older brother squirm.
“Did you know it’s a leap year this year?” Rick replied, with a tone that suggested someone trying to avoid a delicate question.
“Hey!” Jessica laughed, fingering her brother’s attempted diversion. “Don’t do that. Try and change the subject on me! I know something’s happened!” Jessica demanded, refusing to let the moment be platonic.
“Mom got goose bumps when I said your name yesterday,” Jess continued, and Rick stopped on the path.
“It’s something to do with that dating site. The Todd and Clare one that I told her about. Isn’t it?” Jessica replied nodding, and her words about that dating site in particular, that had started this whole ball rolling, made Rick draw a deep breath.
“Should I feel bad for telling her about it?” Jessica said looking daintily at his eyes on profile, trying to second guess Rick’s difficult-to-read expression.
“Oh, no. It’s not the site, this would have happened anyway,” Rick replied. “Besides, I deleted my Todd and Clare profile, too many college girls on that site, way too young for me,” Rick scoffed, trying to avoid the word, sex.
“Tell me then!” Jessica grinned playfully like an excited little girl. “I hate it when you and Chloe keep a secret from me,” Jess insisted, referring to their mom, Chloe, by her first name, and she put her arm inside her brother’s elbow as they walked, to ease the moment.
Rick stopped again on the path, a confession hanging in the open air, and the white snow coating the park’s fields baring the staccato in his hesitation. Sensitively, he gently turned to look at his little sister, noticing as he turned, how deserted the Ladies Pavilion looked up ahead in the distance.
Jessica’s flattering long, dark brunette hair falling subtly into her cashmere scarf as he stopped to look into his sister’s smirking eyes.
Her girlish charm, abound with excitement as Rick raised his arms to button up her coat at the neck.
“If I tell you,” Rick said, pausing solemnly as he hooked the top button of Jess’s brown coat. “You have to promise me that this will never be repeated.”
Jess’s face, her complexion imbued with her family’s freckled lineage, changed from one of frustrated excitement to that of the serious artist capable of winning awards at NYU and embracing deep, immense understanding, as she looked up into Rick’s troubled eyes.
“I agree,” she replied, in a graver tenor.
He paused, and the wintry isolation of Central Park’s expanse bought Rick the unapologetic space he needed now, to make this confession.
“The other night,” Rick replied, breaking gaze with his sister to slowly look down at the park’s pavement, and he drew a deep breath. Rick’s eyes catching the lined fabric of his sister’s dark pantyhose as it wrapped around the tops of her feet in ballet shoes, in the chilly outdoors.
“The other night,” Rick said again, this time meaning to finish his sentence, and he raised his head to engage his sister’s piercing blue eyes once more.
“Chloe contacted me on Todd and Clare again, under a pseudonym,” Rick said, and his first admission was palpable. Jessica’s eyes though, born of the same maternal intensity, reminded him at once of his mommy; her courageous daughter standing in front of him then.
“Mom sent me a Kik message through the site, and met me at the apartment last week,” Rick said, and he watched his sister’s brow crease in contemplation, wondering where this was going.
“This was the night of the court case I told you about with the mother Allison, the mother that made me think a lot,” Rick prompted, to give Jessica some context and ground his confession for her understanding.
“Yes,” Jessica whispered, remembering that difficult conversation about his employment for the bank, and she put both her arms up to her brother’s shoulders.
“Well,” Rick paused.
“We had sex.”
“I had sex with mom in my apartment,” Rick told his sister, and in the veiled balance of Jessica’s subtlety, he confronted his sister’s intuition as she raised her eyebrows; her face just inches from his delivery.
For Rick, a son and a brother, it was that confusing moment when a beautiful adult woman whom you know well does something you don’t expect.
Jessica’s intuition finding her brother’s guilt, then.
Rather than being dumbfounded, or disgusted, or angry, to Rick’s utter amazement; Jessica simply, smiled.
“I thought it was that,” Jessica replied, and she let it sink in enough to notice her brother’s stunned reaction. Her smile, bringing absolution to Rick’s admission as she turned her body on the Central Park pathway, and continued to walk toward the snow-caked pavilion ahead.
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