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Blind Dates #8

"X meets Jill and they finally see eye - to - eye"

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Ten minutes into the Uber ride, the driver breaks the silence. “This is one of those perfect sunny days where I’m not sure if spring is springing, or if summer is slipping away.”

“Hmm…” X replies thoughtfully, then says to the driver, “Could you just drop me here at the park, please? I think I’ll take advantage of this weather and walk from here.”

“Sure thing. Here you go.”

X, hoping the fresh air will bring some much-needed clarity, takes off with his ever-present black bag for the last half mile to Jill’s home. Strolling through the park, he thinks to himself, how did I get myself into this position? I know better than to get emotionally drawn in! In nearly 30 years of sex work, this has never happened. But why? Why? Why? Why? What am I missing?

Jill positions the chair directly in front of the window bench of the reading nook, then glances at the ship’s clock across the room… “Just ten minutes,” Jill says out loud.

Sitting down on the bench, her mind drifts back to what she has been thinking about all week—X screaming her name as he orgasmed during last week’s phone-sex session. Of all the Gods, Jesuses, and the legions of undecipherable guttural sounds that have come out of lovers’ mouths, Jill says to herself, hearing X yell “J-I-L-L” from the core of his soul hit her on a totally different level.

What is it about him? Why am I so drawn in? How can I feel so deeply rooted and grounded, yet untethered and free to fly with the winds? How do I trust him so fully and deeply?

Ding! X’s phone signals that Jill is ready.

X enters the front door and immediately feels a tinge of disappointment that the staircase is not adorned with flickering candles leading up to Jill’s playroom for another session with leather cuffs, twisted sheets, and the cuckold chair.

Perhaps she’s on the kitchen table awaiting another Amish spanking, he thinks as he closes the door.

“In here!” Jill calls, breaking the silence from the reading nook off the foyer, where they spent their first date in her home.

The echo of X’s black bag hitting the floor reverberates, sending a familiar tinge of foreplay through Jill’s loins; she already knows it will not be needed today. Lying back comfortably in just a silky blouse and the requisite blindfold, framed perfectly by the picture window overlooking her gardens in the late-afternoon sun, she waits. The overstuffed chair, directly in front of the window bench, gives off a mano-a-mano vibe—perfect for an audience of one.

“You look stunning,” X whispers.

“You always say that,” Jill replies with a teasing smile.

“As I recall, the last time I saw that silky blouse, it was sliding off your shoulders and down to the floor.”

“You have a good memory,” she says. “But this time, I’m not wearing a thong.”

“Mmm…” X hums. “I trust this chair is for me.”

“Please,” Jill says, gesturing with her hand.

You really are stunning, Jill Robinson, X says to himself as he watches her subtly hike her blouse up her thigh. Her wry smile suggests she senses his appreciation.

“Tell me—why have none of my checks been cashed?” Jill asks, her tone shifting.

Her frankness startles X.

“Cat got your tongue?” she asks playfully. “The deal, as I recall, is that in exchange for ‘intimacy’ counseling, I pay you a fee and agree to remain blindfolded during our sessions. Am I missing something?”

X thinks, Jesus Christ, money? Most widows I deal with are concerned about overspending.

“No. That is our agreement,” he responds.

“Hmm… but the checks haven’t been cashed,” Jill says.

To himself X pleads, C’mon, Jill, don’t press me on this. This is a slippery slope.

Jill continues, “Why do you do this—with blindfolds?”

“What? Sex work?” X asks, grateful for the shift from money.

“Yes. Do you require all widows to wear blindfolds? How did you get here?” Jill asks.

“It’s just where I landed. It’s very effective, don’t you agree?”

“I’m not criticizing; I’d like to understand you better. You are a very skillful lover, as I’d expect. And patient. But your empathetic selflessness doesn’t drain you; it somehow empowers and softens you. How do you do that? Even the most tenured gigolos devolve into codependency. But not you. How?”

“Lots of therapy,” X quips flippantly.

Jill remains silent.

Well, Jill, if it’s authenticity you seek…

X continues, more solemnly, “My whole life is a therapy session, quite frankly. The short story is that I had a rough start with a mom who abandoned me and a dad who buried himself in work. Rewards from school and sports filled in for the lack of hugs and attention. I did well—got an appointment to a fancy military school.”

“Like… Annapolis?” Jill asks.

“Yeah, but I didn’t stick with it. After drifting a bit, I ended up in sex work. A few years in, I found a niche with widows. Who knew confronting grief pairs so well with sensory deprivation? What can I say—widows dig it.”

“Haha! Yes, we do,” Jill replies, then asks, “How many other clients do you have?”

“Now? None,” X says quietly.

“None?” she repeats, surprised.

“I, uh… I wrote a book. It’s done well. I pick and choose. This is not about the money…” X cuts himself off, wishing he could swallow the sentence back.

Jill lets it hang in the air.

“But you chose me. Tell me something I should know—but you don’t want to tell me,” Jill says.

Holy fuck, X thinks.

Then aloud: “What do you mean?”

“Tell me something you don’t want to tell me. Something a lesser man would be embarrassed to admit.”

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What are you, my therapist? My shaman? My muse? X thinks.

Jill waits.

“Okay,” X stammers, then inhales and exhales audibly. “I chose you because something tells me you can help me figure myself out. My biggest fear is…” X’s voice cracks, “that you will figure me out before I figure myself out.”

The silence absorbs his words.

“Thank you for that,” Jill says sincerely. “Your turn.”

“Mmm… what would you like me to know about you?” X offers.

“That’s fair. My short story is that my parents divorced when I was eleven.” Jill continues, “My father was in the Navy—submarines—and was gone a lot. After a horseback-riding accident, I found out I probably wouldn’t have children. My mother was more devastated than I was, I think. She snapped, left my dad, moved us to Bozeman, and remarried. She died when I was seventeen, and I moved back east with my dad for a short while.”

“I’m sorry you had to go through that. What was your dad like?”

“I don’t remember much from when I was young, except the smell.”

“The smell?”

“Yep. Something about the air in a submarine leaves a distinct odor on his uniforms. When I was little, I used to sit in his closet, soaking up that smell and playing with my Barbies.”

“I’m sure that was difficult,” X says.

Jill shifts the conversation. “Do you think about me—when we’re not together?”

“Yes,” he answers coyly.

“A lot?” she presses.

“Often.”

“Tell me.”

X inhales and exhales again. “I think about our dates, about your experience. You are a connoisseur—a healthy connoisseur—who appreciates that the physical act of sex is merely a metaphor, a vehicle for a grander spiritual journey.”

“Sex is easy,” Jill says. “Intimacy—not so much. I sense you know that. You embody that.”

“Intimacy,” X says, then slowly articulates, “Into-Me-U-See.”

Jill smiles and nods. “Into-Me-U-See.”
A moment passes. Then she says softly, “I’d like you to undress me,” and stands up.

X rises, saying nothing, his thoughts swirling. Button by button, he unfastens her silky blouse, letting it slip to the floor in slow motion. She places one arm over his shoulder and the other beneath his arm, pulling herself into his fully clothed body and lifting her lips to kiss his coveted bearded mouth.

The sensation of X’s cock growing hard against her hip inspires Jill. She sits back on the edge of the window bench and says, “Now, I want you to undress.”

“Very well,” X says.

The teasing sound of his belt buckle compels Jill to touch her wet sex.

X, now standing naked and facing the reclined and blindfolded Jill, glances at the empty bench in the garden and silently honors her deceased husband’s memory.

He sits. “I’m undressed,” he whispers.

“Tell me about her,” Jill whispers.

“Who?” X asks.

“The one who hurt you. The one who made you feel as if your mother left you again.”

Jesus fucking Christ, Jill! You are the one to figure me out, X thinks. Then aloud: “I never knew her name. We met at a dance, then went to a bagel shop on Main Street. I told her I was quitting the academy. She stood up and walked out on—” His voice cracks. He buries his face in his hands, feeling the loss of every woman who walked away.

In Jill’s blindfolded silence, she feels X’s unarmed heart, splayed open between their nakedness. You are so vulnerable, yet incalculably brave, she thinks. Jill basks in the glow of X’s honesty, feeling respected, trusted, and loved in a way she thought she never would again.

Then a forgotten guilt rises and washes over her.

At that moment, the toes of Jill’s left foot touch X’s right shin and slowly slide down to rest on his bare foot. Blinking through teary eyes, X looks up at Jill as she scooches over, extending her other foot to his left leg, then sliding down just as the first did. Their knees touch. X closes his eyes, savoring the simplicity of toes-on-toes intimacy.

“Would you like to close your eyes and listen to what I think about you?”

“That would be wonderful,” X breathes.

Jill pauses, her mind racing. If I unmask, will this be the end? Or the beginning? Fuck it. We’ve come this far.
She slides her blindfold up and sees the naked, goateed man before her. Besides, how many other Captain’s daughters have forgotten broken boys’ hearts at those Navy mixers?

“When you touch me, I feel like I’ve never been touched before. Like a girl’s first experience with a loving hand and mouth on her body, and she rushes home to masturbate under the running bath faucet,” Jill says.

She continues, “With all the toys and props and experiences I can draw on, your fingers grazing up my thighs, your breath on my wetness, the skillfulness of your tongue darting over every cluster of nerve endings… it takes me right back to my bathtub and the old-new way of satisfying myself.

“I think about your cock in my mouth, gently gagging me as you hold the top of my head and slowly thrust down my throat.”

“I don’t know what I believe about the afterlife or reincarnation, but it feels like you are an angel sent by my Billy to experience you and all your skills.”

The clicking sound of her wet pussy being massaged echoes through the room. X slowly tugs on his hardening cock.

With a blend of confidence that this could be a new beginning and a fear that it could be the end, Jill whispers, “Tell me your name.”

Without hesitation, he replies, “Alexi.”

“Open your eyes,” Jill says.

The shock and awe of peering into Jill’s uncovered eyes floods him with memories of every lover he’s ever lost, now returning—with toes on toes and knees against knees—for a shot at redemption. Hearts and souls collapse and expand in a twirling dance of perpetual death and rebirth. Every effort made, every journey taken, finds peace deep in the emerald-green eyes of the woman in jeans.

X pounds his rigid cock with intense veracity, matching Jill’s possessed self-stimulation; both are on the verge of exploding.

“Ahh… J-I-L-L!!!”

Published 
Written by Dapchek
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