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Fifteen Shades of Role Play

"An older man, a beautiful young woman, and the lesson of a lifetime"

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I was driving cross country and had pulled off Interstate-80 in search of something more satisfying than a chain-restaurant meal.

I really can't recall much about Rick's Café in New Paris, Indiana. But I will never forget the woman I met there.

"I hate eating alone," she said. "Don't you?"

"Why not join me?" I asked, gesturing to the empty chair.

Rachel was in her mid-20s. She had pale green eyes, an unruly mane of auburn hair, and a lithe, dancer's body that turned half the heads in the room as she walked to my table.

"As Time Goes By" was playing on the jukebox and I remember thinking, "Oh, that's from 'Casablanca.' How appropriate." And when she sat down, the first thing I noticed about Rachel was her gift for putting people at ease. Within a few minutes, it seemed as if I'd know her all my life.

We ate grilled steaks, drank Argentine Malbec, and chatted about everything and nothing at all. By desert, we were flirting shamelessly. At some point, I may have mentioned I was staying at a nearby hotel. She confessed an attraction to older men who knew how to 'put a girl over their knee.' It was a phrase I hadn't heard in decades, but I understood exactly what it meant.

When the bill arrived, she offered to pay half. I refused.

"All right, then the next bottle is on me," she announced. Within half-an-hour Rachel was at my door with two bottles of Pinot Grigio.

Even before I'd popped the cork, we were flirting more intensely than ever. She sat so near I could see the the green highlights sparkling in her eyes and smell the rich floral fragrance of her perfume.

Rachel complimented my physique. I praised her 'charms.' When she tossed her head back in laughter, her sweater stretched across her breasts, accentuating taut nipples. When she crossed her legs, her skirt rode up her thighs, revealing an enticing glimpse of white lace panties.

Although I was nearly twice her age, I couldn't help but fantasize. How would it feel to kiss Rachel's lips? Were her breasts the same pale-porcelain hue as the rest of her complexion? Would having Rachel's impossibly long legs wrapped around my shoulders be the closest thing to Heaven that I had ever known?

When the first bottle was gone, I stood up to open the second and noticed her eyes roaming up and down my body.

"You've added some weight," she said with a shy smile.

"I know," I said, looking down and patting my stomach. "I shouldn't have eaten the fries."

"Oh, not there," she replied, her eyes focused lower, on my crotch.

She was right. I wasn't fully erect, but I was well on my way. I gazed into her eyes, a little embarrassed. I didn't need a second glance to recognize her look of undisguised lust.

"Can I see it?" she whispered, nodding to the front of my pants.

Not knowing how to respond, I hesitated.

"Please?" This time her voice had a pleading, almost desperate edge.

Without speaking, I unsnapped my trousers, unhooked my belt and slowly lowered my zipper. She bit her lower lip, but her gaze never wavered.

The pants slid off my hips and down my legs to floor accompanied by the soft hiss of fabric against flesh. I felt goose bumps forming and the familiar tingle of sexual arousal coursing along my spine.

The contours of my cock were clearly visible through the thin cotton briefs. It hung down, arching over my balls. I could even see the hard ridge just below the tip.
"Will you strip naked for me?" She asked.

I nodded.

"Will you touch yourself while I watch?"

Again, I nodded.

"Will you make it cum for me?"

"If you want," I replied softly, hooking my thumbs under the waist band and lowering my briefs until my cock popped over the elastic, bouncing slightly.

She caught her breath, then asked: "Where do you want to cum?"

I didn't know what to say.

"On my tits?" she asked, cupping her breasts as if to offer them to me. "How about my face?" Her hands moved to her face and she made small, circular motions as if applying some kind of facial cream.

"Or in my mouth?" she continued, swirling the tip of her tongue across her lips.

"Or, maybe, in my pussy?" she whispered, deliberately parting her legs so that I had an unobstructed view of the panty-clad space between her thighs.

"All of those," I sighed. "Even if it takes all night."

Gradually, she lifted her gaze to meet my eyes, and I was shocked by an abrupt metamorphosis. Moments earlier her words, her expression, even her body language, had been confident, even sexually aggressive. Everything about her screamed arousal.

All that had turned on a dime. Rachel was slumped like a rag doll and the face that now looked up at me, framed in a halo of tangled curls, wore the expression of a wide-eyed child whose lips trembled with apprehension.

"I… I've been bad… haven't I?" she asked in a tiny voice that had nothing in common with the worldly, womanly contralto I had just been hearing.

If Rachel were acting, she deserved an Oscar. For a moment, I considered ending this strange dance. Rachel seemed to sense my hesitation.

"I… I know I've been naughty," she said, her voice still small and childish, but with a sparkle in her eye that let me know she wasn't completely possessed.

"Yes, Rachel, you've been very naughty. Very bad," I said, improvising the best that I could. "Tell me why you've been bad, Rachel," I heard myself saying with uncharacteristic forcefulness.

"Because I had... wicked thoughts."

"You are to call me David," I ordered, catching on to my new role. "What thoughts, Rachel?"

"Bad thoughts, David," she said, her body squirming as if in a struggle with some inner demons.

"What bad thoughts, Rachel. Tell me!"

"I was thinking about your.... your..."

"About what, Rachel? Say it."

"Your cock, David. I was thinking about how your cock looks when it gets big."

"You wanted to see my cock, Rachel. Is that all?"

"No, David. There was more. Bad things. Naughty things."

"What else, Rachel?"

"I wanted to see you touch it, David. To make it grow hard."

"And?"

"I wanted to watch you make yourself cum, David. I wanted to see you squirt."

"You wanted me masturbate for you? Is that everything, Rachel?"

"No, David. I wanted to feel your cum on me... and in me."

"Where, Rachel?"

"On my breasts, David. And my face."

"Where else, Rachel?"

"I can't... can't say."

"Tell me, Rachel. Where else did you want me to cum?"

"In... in my mouth, David."

"And?"

"In my pussy.

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Deep inside my pussy, David."

"You've been very, very naughty, Rachel," I said sternly. "Now you say it."

"I've been very, very naughty, David."

"You know what happens to naughty girls, don't you Rachel?"

"Yes, David," she said in a barely audible voice, her head hanging in resignation.

I moved to the armchair. I had gone from half-mast to one of the hardest erections I could remember. My cock not only bounced when I walked, it angled upward toward my stomach.

I ordered Rachel to remove her skirt and panties and to fold them and place them on the bed. She had narrow, almost boyish hips that framed a thin triangle of dark brown pubic hair. As she walked toward me, in the gap between her thighs I could clearly see her engorged labia.

I patted my knees and she reluctantly lowered herself over them, her beautiful, smooth ass cheeks pointing toward the ceiling and my cock trapped against her hip.

"You've been a very, very naughty girl. Say it, Rachel!"

"I've been a very, very naughty girl, David," she said, her voice trembling.

As she spoke my name, I brought my hand down from shoulder height. There was a loud crack, like the sound of a small-caliber firearm, and almost simultaneously, Rachel squealed, as much in surprise as in pain. As I removed my palm, I saw a white imprint, which quickly turned an angry, dark pink.

I repeated my demand. And each time she reached my name, another blow fell, slightly more forceful than the previous one. With each slap she squealed and whimpered, her body trembling, her breath growing deeper and more ragged.

As we approached the 15th stroke, my hand stung, and Rachel's body tensed. She was almost unable to speak.

"I've... I've been... very... very... naughty..." she stammered. Before she finished, I brought my hand down with as much force as I could muster. There was a resounding slap and almost simultaneously a low wail emerged from deep in Rachel's throat.

Rachel's body tensed and shuddered in a series of involuntary spams. Her cry built to a piercing crescendo, then gradually subsided in a series of ragged gasps. Simultaneously, her hips thrust and ground into my leg and I felt a sudden release of warm liquid gush across my thighs.

She reached up, hooked her arm around my neck and her body went slack as her head tumbled into my chest. My fingers stroked her hair and tears streamed down her cheeks. My erection had subsided, and I felt a sense of pride at having apparently succeeded in the role that Rachel had in mind for me.

She clung to me like that until her breathing returned to normal.

"I'm so… so ashamed," she sobbed, looking up at me with watery eyes. "I'm so… so twisted."

"Why?" I asked as softly as I could, my eyes searching hers. "Because you feel pleasure and pain so intensely?"

"Yes! It's so twisted!"

"Then you are beautifully twisted," I agreed. "And I'll tell you a secret. All the best people are!"

She smiled, then sighed, and pressed her face tighter against my chest.

"You have a fetish. So what! You already know what most people will never discover–that pleasure and pain are two sides of the same coin. The thing is Rachel, I can't imagine you ever squandering a single instant by letting time go by unobserved and unappreciated."

"I'm not… some kind of freak?"

"Only if living your life to the fullest is freakish," I said.

"Thank you, Davey," she whispered. "I never thought of it like that. It's always been a shameful secret."

I leaned over, put my mouth over hers, and kissed her into silence. Our tongues touched, swirled and explored. I stood, hoisting her in my arms, and then I gently lowered Rachel onto my bed, her legs open and hanging so that her toes touched the floor and her swollen lips were exposed to me.

Spreading her knees with my fingertips, I leaned closer until my tongue found the salty liquid on her inner thigh. I licked and nibbled and moved inexorably closer to her pouting labia. When my tongue reached her entrance, she moaned softly, and I felt her entire body relax. With that, I began a long, slow dance aimed at bringing Rachel to one more gentle climax.

When the orgasm arrived, it was not with the frenzied paroxysms of an hour earlier. This time there was only a soft moan as I felt the muscles of her vagina contract around my tongue.

In that instant I knew we belonged to each other, and that we could never be together. I could teach her to accept herself, but I could never give Rachel what she deserved. That could only come from someone closer to her own age. Someone with who could be there for her, not just for a few years, but for a lifetime.

When the afterglow subsided, she looked deep into my eyes and seemed to comprehend the bittersweet sorrow she saw written in my expression.

"You're not going to make love to me, are you?" she said.

"No," I said simply. "I can't."

"I understand," she whispered. She closed her eyes and a single tear found its way down her cheek. When she opened them again, the room was ablaze in her brilliant, mischievous smile.

Without warning, she lowered her head and her lips wrapped around my soft cock. I may have been emotionally exhausted, but physically I was as horny as I could ever remember. When I came in her mouth, it was with the kind of massive release I hadn't experienced in years.

After that, my memory blurs. I recall her kissing me, softly and lovingly from head to toe. I must have drifted off to sleep. I have a vague recollection of Rachel laughing and holding her camera-phone at arm's length with an LED-strobe repeatedly going off in my eyes.

In the morning, when I awoke, the only traces of Rachel were the faint scent of sex and floral perfume and a pair of white lace panties folded neatly on the pillow beside me.

As I drove west, I began wondering if perhaps Rachel hadn't been a profoundly vivid figment of my imagination. But when I reached San Francisco and collected my mail, there was a lavender envelop with a distinctive floral scent. Inside, was a black-and-white "selfie" photo of a radiantly beautiful and naked young woman with her head on the shoulder of very familiar looking older dude. On the back was an inscription:

My Dearest Davey,

You taught me to trust myself,
and that love is more than lust or gratitude.
Someday, I WILL find the kind of love you want for me.

And, Davey, you must remember this,
a kiss is just a kiss,
and you and I will always have 'Paris.'

Love,
Rachel

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Written by ThisOldHippie
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