Annie's First Anal

by Carlos Malenkov

Copyright© 2005 by Carlos Malenkov

Erotica Sex Story: Casi, the hero of "The Most Intimate Part," returns and initiates a woman into the mysteries of...

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/Ma   Consensual   Hypnosis   BiSexual   Heterosexual   Celebrity   First   Anal Sex   .

She had set her sights on the world's richest man. He had the hots for her and that should have given her the opening she needed. There was one little problem, though. She hated sex.

Just imagine living the good life, she told herself. Never having to worry about paying the rent and where money for the fall wardrobe was going to come from. Weekends in Paris, vacations on the sandy beaches of Thailand, emerald-encrusted jewelry. Always the best of everything... and all she had to do was let him stick his thing into her. Ugh!

It hadn't always been that way. As a schoolgirl she'd had the conventional romantic fantasies of swooning and melting away in some man's arms, of getting married and living in an ivy-covered cottage, of having kids and backyard barbecues, and all the rest. But, reality got in the way. Sex. Horrid, unclean, messy sex.

She had lost her virginity the night of the Junior Prom. Her date had been very insistent. And very clumsy. It had hurt, and she had cried -- out of disappointment and grief as much as from the pain. And afterwards he had started ugly rumors that she was a slut. And a frigid slut, at that.

Her second attempt wasn't much better. She'd been in college by then and thrilled that the captain of the basketball team had taken an interest in her. An interest that extended no farther than an occasional quick bang or a blow job. No affection, no tenderness, no technique. Just brutal rutting -- satisfaction of male lust. Filthy animal lust.

Sometimes she felt an emptiness deep inside her, a profound loneliness, a longing to be filled, a hunger for human touch. But, if it meant submitting to the carnal embrace, she'd take the emptiness. Still...

Now at 32 years old, this might be her last chance. Her very last shot at happiness. But, at what price?

This was a final blowout before the school year started. Before she had to go back and face hordes of squealing preteens with all their petty problems and ingenious ways of avoiding anything resembling learning. Before she had to slip back into her accustomed role as teacher and animal tamer.

A Caribbean cruise was just the ticket to forget what a rut her life had settled into. A life lacking in excitement and surprises. A dull, grey, meaningless, juiceless life. But, then she had met this man, this man unlike any she had ever known. This man who invited her to dine at his table, who placed his hand over hers, who made tingles run up and down her spine when he gazed into her eyes. This man who made her turn to jelly when she thought of being in his embrace. His embrace. Dirty! Dirty!

"And so, I'm at my wit's end. Not that I'd presume to impose upon our friendship, but I was thinking that a famous author of a steamy erotic memoir could... "

"My dear girl, why must you assume that I'm an authority in the arcane arts and dark mysteries of the sensual realm? That I could free you of your anxieties and hangups? That I could liberate you sensually and sexually? Sorry to disappoint you, but I'm just another hack writer, and I haven't any idea why the cruise line chose me as the Creative Genius in Residence on this boat. And, because I've been known to scribble a thing or two about certain matters now and again, well, that doesn't necessarily make me an expert. Not that even an expert could offer much in the way of useful advice."

"Advice wasn't exactly what I had in mind, Casi. I've read your book -- in the special leather-bound gold-embossed commemorative edition, no less -- and it seems to me that you've confronted some of the same demons that I'm facing now. So, maybe... "

"Oho! I think I see what this is leading up to. You've known me how long? A week? And now you're hinting at... sex therapy? Well, I'm by no means immune to the charms of a beautiful lady, but the memory of a certain doomed relationship still haunts me. That damned woman took with her a huge chunk of my heart when she left me, and I've long since abandoned all efforts to recapture that grand feeling of being simultaneously exalted and tormented by love."

"Oh, my poor boy! And I thought my own situation was tragic. Come here and share the pain with me."

How good it was to have his head resting between a woman's breasts again. It aroused in her maternal instincts, and in him certain other ones. His hand strayed downward, as if by accident, and began exploring.

Amalya! How long has it been since I laid my head between your breasts and savored the spicy-sweet aroma of female arousal? How long since I've run my hands down those never-ending curves and lost myself in that bounteous burning-hot flesh?

At his intimate touch she stiffened and tried to push him away. He released her from the embrace and softly kissed her forehead.

"No, Annie. I'll do nothing to hurt you or transgress your boundaries. And, if it's what you want, I'll leave you now."

"Don't go! I need you to teach me how to make love, but I just... can't bear it."

"You want to, and yet you don't. Torn between the natural desires of a healthy body and the taint of diseased memories. Quite an interesting problem. Let's see now..."

Annie lay prone, her chin nestled in the quilted coverlet of the plush bed in her cabin. Through the open porthole came a refreshing sea breeze with a tang of salt spray. Her naked back lay exposed, all the way down to ripe swell of hip and buttock. Casi was massaging and applying skin lotion.

"Easy does it. Relax. Loosen up."

He was gently caressing and kneading the softness of her hind cheeks. She sighed as she sagged into a puddle of languid bliss and he detected the faint characteristic odor of female arousal.

Entry through the rear passage. It was the one sure way he knew of that could shatter pain-encrusted barriers of fear and inhibition. But, it had to be done with finesse. How well he knew that from his own experience.

 
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