The Silk Scarf

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"Yo... you're a guy..." he finally gasped. Catherine smiled down at him. "Do you really believe that?" she asked.

The expression on the bewildered young man showed that he didn't know what to think. Time stood silent as he tried to understand.

"Think about what you've been feeling." she continued. "Think about your fantasies and desires."

It was obvious that was exactly what he was thinking.

"Remember, you're in control here." she reminded him. "If you want to end it here, all you have to do is relax your hands and let that scarf fall to the floor."

It was that simple. Michael knew it. A simple relaxing of his hands and he was on the way out the door. Why couldn't he bring himself to do it.

Staring at the cock hanging just before his eyes, Michael thought of the times he and Jimmy Craig had jerked off together back home. A few times they'd even jerked each other off. He remembered that it had felt pretty good. Just as good as when Sally Hayden, his first real girlfriend, had done it later on. There were nights that he had wondered that if he hadn't become involved with Sally, would he and Jimmy have gone any further.

"Decision time." Catherine said, breaking a prolonged silence.

Michael knew he should let go of the scarf. Just relax his fingers and stand up. That was the right thing to do. Instead he found himself leaning forward and taking Catherine's cock into his mouth.

Surprised at his own actions, Michael couldn't really put words to the thrill that ripped through his body as he felt her hardness fill his mouth. A tangy taste so much like his own, which he had tasted many times, covered his tongue. The fact that it wasn't his own brought a special excitement to it.

Catherine stood motionless, letting her young lover adjust to the new experience. Michael could feel her cock growing to a new hardness as he let it slip between his lips and ran his tongue around the bulb like head. He drew in a breath of air through his nostrils, reveling in the thick scent of cock and balls.

The now fully erect cock jerked to life, hitting the back of his throat. Michael worked his vibrating tongue across the length of his prize, nuzzling her naked balls. Once he started, Michael knew he couldn't stop. Confident now that Michael had made his decision, Catherine began to slide her cock in and out of his mouth, taking control of the experience. Her action seemed to add to his excitement.

Faster and faster she began to pump his virgin mouth, offering suggestions to him as he eagerly followed every one.

The young man's technique was crude, but no more than Sally Hayden's had been the first time she had sucked Michael off. As with Sally, he more than made up for lack of experience with enthusiasm.

A few hours ago, Michael would've never believed he would enjoyed the feel of a hard cock sliding in and out of his mouth. His own cock was harder than he could've imagined. This was a fantasy that he never would've even admitted to himself.

Catherine held the back of his head tightly as she felt the familiar pressure building inside of her. Seconds later Michael's mouth filled with a creamy whiteness.

"Oh God yes!" Catherine exclaimed as she felt her energy drain into the young man.

The excitement of a virgin mouth added to her climax as she pumped every last drop of her orgasm into Michael. The young man gagged a little until he opened his mouth wider to let some of her seed splash down his chin. It felt strange, it felt forbidden...it felt wonderful.

Drained, Catherine let her now softening cock slip from Michael's mouth. She wiped the sticky residue from his chin with her fingers and then licked them clean as well. Pressing her lips again against his, she reached into his mouth with her tongue and sampled her own fruits. "Now it's your turn." she whispered into his ear in her sexiest voice. "I'll be right back."

The tall woman moved over to a night table and removed a small jar. She coated her fingers with the clear greasy gel from the container and then smeared another generous helping of in on Michael's rock hard cock. With all the excitement of the last hour, just her touch was almost enough to cause him to explode.

"Not yet lover." Catherine said as she squeezed the base of his cock in a way as to stem a rising tide.

Once more Catherine straddled her young captive and lowered her ass against his rising cock. She placed a soft hand alongside his hardness and guided it to her tight hole. Michael felt a great tightness press against the head of his cock as she pressed down against his manhood.

The pressure increased dramatically as Catherine took more of him within her. Michael couldn't believe the tightness of her ass, or how good it felt around his cock. No girl had ever felt this great - not even Sally that first time in his father's pickup.

Catherine's pace began to increase as she rode his cock faster and faster. With it grew Michael's pleasure. She slammed her ass against his balls again and again, driving him deeper and deeper inside of her.

"Fuck me lover!" she called out. "Fuck your woman!"

In every aspect of his mind, that was exactly what she was to Michael. She might have a slightly different anatomy than he had expected, but she truly was the girl of his dreams.

The tension in his cock could be felt all the way down to his toes as the rising tide Catherine had paused a few minutes before returned with double the intensity. His lover recognized the tightness in his groin as she pressed against it once more.

Catherine pulled Michael's face against her breasts as she slammed down once final time. An action that burst the dam within him, sending a raging torrid into the tight confines of her ass.

The sudden release caused Michael's entire body to relax. Like a rag doll he lost all strength in his extremities as it was replaced by a crashing wave of euphoria. He opened his mouth to speak but didn't have any energy to do even that.

The young man collapsed against the back of the chair, his head resting in the bosom of her breasts. She wrapped her arms around him and held him close, even as she felt him grow soft inside of her.

He had been fun, as the smile on her face attested, the best she'd had in a very long time. Michael had genuinely believed in their little game, something very rare in her conquests. He might very well be the one.

Normally, Catherine preferred virgins, only playing the game once with each new lover. This time however, she was sure there would be a second act.

END

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13 Comments
curricdcurricd8 months ago

Great story! It stands alone very well but if you ever get around to it more chapters would be great. I like your womanly perspective.

AnonymousAnonymousalmost 2 years ago

Very sweet story! Highly erotic!

paulthewetcdpaulthewetcdalmost 4 years ago
Wow!

The intense passion of these characters is palpable....

Although I knew from the start that this was a transgender story, I was captivated by Catherine and her femininity...

There is no doubt that I would have made the exact same choices as Michael...start to finish!

And, oh, what a finish!!!

Your writing is clearly emotional, sensuous, and sexual....erotically fulfilling.

And I impressed that you made it so wonderfully compact ....

Thank you for giving me this...beautiful feeling!

AnonymousAnonymousover 4 years ago
Beautifully erotic

A really lovely, well written and erotic story. Your ability to empathise with the male experience is impressive. This is an exciting fantasy for me, and reading it brought me a lot of pleasure. Thank you x

oldpantythiefoldpantythiefover 4 years ago
Over the top!

So much feeling and passion in such a short story. Well written, as always, and so hot! Thanks again.

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