by Carlos Malenkov

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Ma/Ma, Consensual, Romantic, BiSexual, Heterosexual, FemaleDom, Anal Sex, Sex Toys, .

Desc: Sex Story: George has a secret fantasy of having a woman make love to him with a strapon-dildo. He finds a willing lover, but gets a little more than he can handle.

Copyright© 2003 by Carlos Malenkov

"Because you're the man and I'm the woman. That's why I'll never, never strap on one of those sick dildo contraptions. The very idea of it makes me sick. You make me sick."

And that was the end of that. Asking Jennifer to fulfill a fantasy had turned to be a major mistake. And they had been talking about setting up housekeeping together, too. Ah well, maybe it was for the best.

George figured he'd better clear up any misconceptions right from the start before beginning a new relationship. He placed a personal ad.

Dreamest thou perchance of fondling a man's posterior?
Ever entertained
the deliciously secret fantasy
of penetrating into forbidden recesses
of sweet hidden Mystery?
In me find fulfillment
of deepest, darkest desires.

Replies began trickling in. One of the more bizarre ones was from a woman who claimed to have been born in the wrong gender. Well, why not give it a shot? At the very least it would be entertaining...

Miranda was the most physically imposing woman he had ever seen. Six feet tall and well-muscled -- the result of years of body building, she said. They met, at his suggestion, in front of a popular restaurant, and she greeted him with an enthusiastic hug. So enthusiastic, in fact, that she lifted him a foot off the ground and nearly cracked a couple of his ribs.

"Good to see ya finally, Georgie. Gotta love a fella who wants to experience the bottom side. Oh, did I embarrass you? You're actually blushing."

"Well, Miran-"

"Call me 'Randa.' I despise the full version. Makes me sound so frilly-feminine. And, you betcha, I'm anything but that."

"Randa, I'm pleased to make your acquaintance."

"Acquaintance, huh? If I have my way, and you'd better believe I will, we'll be much better acquainted before long."

She was right.

Two hours later they were in her apartment. In bed.

She had all the requisite female equipment, all right. He'd had ample opportunity to study it in exquisite detail while deep-tonguing it according to her detailed instructions. It was just that she was bigger and taller than he was. And stronger. By maybe a factor of three.

"Now we get down and dirty," she was saying. Buckled around her hips was a wickedly gleaming chrome chain-link harness and protruding from its frontal accessory bay was... was the biggest dildo he had ever seen. Seen, hell, the biggest he had ever imagined.

"To answer your unspoken question, Georgie, it's fully twelve inches long. And two and a half inches wide. A person could mistake it for a footlong hotdog in a different context. Only this hotdog will be sliding straight into your hot buns. All the way in."

She was squeezing something out of a tube onto the dildo.

"I sure hope that's not mustard," George managed to croak.

"It's lube, silly boy. Get on your hands and knees. And hop to it!"

"You know, a hotdog just doesn't hit the spot without the right condiments."

"Shut the fuck up and spread your legs."

The hotdog was beginning to hit his spot as she adjusted her aim. His rear entrance dilated and stretched wide as the dildo pushed into him. Now she was pressing past the rings of muscle guarding the entrance to his guts -- his innermost self. All his defenses were down and she was pounding into his tunnel.

Her metal-harnessed thighs jingled as they whacked against his buttocks. She joyously plunged the entire silicone rod into him, all the way up to its base. He felt its tip impacting the far wall of his rectum, but the sheer sensual pleasure of fullness and sliding friction overwhelmed any momentary twinges of discomfort. Her powerful hands steadied his hips to lock him in place as he absorbed her deep thrusts.

Once more she cried out in what must have been yet another eruption of pleasure. The towel beneath him was sopping wet with sweat and semen. His hole was getting abraded, but she didn't seem to be tiring. How long had his captive ass been hosting her dildo? Half an hour? At least.

"Randa, please, let's take a break. You're wearing me out. Let me catch my breath at least."

"Hush, little one. Just a few minutes more. Lower yourself down on your belly now. Carefully -- I don't want to slip out of you. I'm gonna lie flat on you with my full weight, my front on your back, and my cock all the way up your ass. I'm gonna press you flat and penetrate you far up past the gut line. I'm gonna fuck you like you've never been fucked. I'm gonna stretch your asshole to twice its normal size. I own your ass. Not to mention that I own the rest of you, too."

She let him up a short time later. The absence of her weight pinning him down gave him mixed feelings of relief and regret. His flesh remembered the feel of her sweaty breasts squashing down into his back, and the hard metal harness grinding deeply into his buttocks, imprinting a repeating pattern of diamonds onto his naked cheeks.

Damn, his ass was sore. On fire, it felt like. He had just gotten off the pot after a painful bout of diarrhea. His bowels hadn't shown much appreciation for the churning they'd been subjected to. It was way past time to head home.

He aimed a quick kiss in her direction and thanked her for a wonderful evening as he walked toward the clothes closet. She pulled him into a tight embrace and drove her tongue into his mouth. How very nice of her to give him an affectionate sendoff.

"How 'bout a little quickie before you wander off into that cold, cold night, Georgie?"

No amount of pleading availed him, and his weary, worn out ass had to endure yet another assault before she let it... and the rest of him escape out into the night.

There was a knock at the door. What? It was 6:30 a.m. the following Sunday, and he sure as hell wasn't expecting visitors. Still in his undershirt and boxer shorts, he pulled open the door a crack to look. She pushed it the rest of the way open and marched right in.

"Good morning, my sweet. All dressed up for action, I see."

"Ah, Randa -- "

"No arguments, darling. Shuck off the underwear and bend over."

This time she used a hi-tech dildo with an external fluid reservoir. At random intervals she squeezed its bladder to inject gushes of warm water far up into his intestine. This simulated how a man's cock would ejaculate, and it rather felt like it, he supposed, but the pressurized squirts of pseudo-come were having the same effect as an enema. He quickly disengaged himself from the impaling shaft and dashed to the toilet, where his cramping bowels painfully emptied themselves in noisy and smelly eruptions. When he returned she insisted on continuing where she had left off. This had turned into a ritual of domination and humiliation.

"Bye, Georgie. 'Til next time."

He double-locked the door and staggered back into bed.

Randa pursued him relentlessly. She kept a spare strapon in her purse, and whenever the urge came upon her, she'd pull him into the bushes or a vacant stall in the nearest public restroom to bend him over and do his ass right then and there. The risk of discovery only seemed to excite her more. It got so George had to hide out from her to give his sore, aching butt a rest.

The last straw was when she insisted on dressing him up in a bra and black lace stockings with garters, so she could "feel more like a man taking a woman." Now that was too effin' much. She wanted to make him into a sex toy, a object to gratify her lust with, a receptacle for the silicone penis she should have been born with. No way.

He let her have one final bang "for old times' sake," and even that ended in tearful, screaming recriminations. She just couldn't get used to the idea that he wasn't her property, or more precisely, that his ass wasn't her property.

Katherine was quite a different kettle of fish. Her reply to his ad seemed a bit hesitant, as if she were unsure of of exactly what she was getting into.

"Long walks to the backdrop of crashing surf, and getting to know each other better across the flickering candle light can certainly be the prelude to greater intimacy. I'm looking for one particular man, to have and to hold, to build a family with. Might you be the one... 'hidden mysteries' notwithstanding?"

She seemed to be angling for a long-term relationship... and maybe willing to make a few compromises for the sake of same. At best, he might be able to work out some way of accommodating his special needs, and at worst, at least his long-suffering ass would get a rest.

It was "like" at first sight. Her warm smile put him instantly at ease.

"My gosh, you're the spitting image of all the cheerleaders I fell hopelessly in love with in high school!"

And she was. Conventionally pretty -- almost photogenically so -- with that cute little button nose and the short-cut dark chestnut bangs. The overwhelming impression she radiated was clean-scrubbed all-American wholesomeness. She was the girl next door, his best friend's sister, the straight-A student with braces on her teeth. In short, just the sort of woman a mother would pray for her son to marry. And marriage was exactly what she had on her mind.

There is more of this story...
The source of this story is Storiesonline

For the rest of this story you need to be logged in: Log In or Register for a Free account