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Shemale Sex Storie

His First Time 1ยบ pt

Michael sat at the table playing with his drink. He’d gotten his first real paycheck today and decided he deserved a dinner in the best restaurant he could afford. Of course which what they were paying entry level trainees at Donaldson & Rhobes, his choices quickly narrowed to a few. So he found himself on 11th Avenue instead of Broadway, but still he felt like he was on top of the world. Not bad for a kid from the sticks now living on his own in New York City.

The 21 year old was looking as to where his waiter had vanished to when he first noticed her, sitting at a table over in the corner. Two things immediately caught his attention. First were her eyes, vivid blue pools which seemed to sparkle even at a distance. Second were a pair of spectacular legs which although partially obscured by the table, seemed to go on forever. As best he could, he followed the line of her legs right down to the stiletto heels at the end of them.

The young man knew he was staring but couldn’t bring himself to turn away, even when he realized that he was also now sporting a first class hard on. She was older than him, late twenties or early thirties he would guess. Her dark hair was done up and she was wrapped in a sexy red dress which showcased those fantastic legs at one end and full rounded breasts on the other. All in all, Michael noted to himself, she was one very hot woman.

At first he thought it was his imagination, but then he was certain of it. She was looking right back at him, dangling one of those killer high heels off her foot. Michael couldn’t tear his eyes away and she knew it. A little smirk appeared at the corner of her soft lips as if she could read his mind and knew exactly how hard she was making his dick.
Then, unbelievably, she crooked her finger, motioning for Michael to come over to her table. Long seconds passed as he sat petrified, then like a zombie, he grabbed his drink and lurched across the room to her corner. “You look like you could use some company.” she said with that same smirk playing across her lips as she motioned for him to sit next to her at the small table.
“I certainly could.” Michael replied, feeling for the first time since he had arrived in the city like a small town rube.
“My names Catherine.” she said as she ran her gaze up and down his body. “And it seems to me that you’re getting extremely excited just by looking at my body, hmmm?”
Michael flushed a deep red, unsure what to say. His mind was a blank as he searched for the right phrase.
“You’re legs are magnificent.” he blurted out, feeling incredible stupid the moment he’d said it.
“Oh, is it my legs that made your dick so hard? She said, gazing down at the large lump in his pants.
Michael was now totally speechless. He’d never felt so embarrassed in his life. He wished he could just run for the door and disappear.
“Don’t worry honey, I consider that the finest compliment.” she whispered as she leaned over close enough for him to smell the scent of her perfume.
Relieved, Michael started breathing again.
“In fact, I have a certain weakness for young men like yourself.” she went on. “In fact, I have this knack of knowing just what a young man like yourself needs. What you fantasize about and what you really crave. Just think how excited you’re going to be when I take you home with me and make all of those dirty dreams of your’s come true.”
“W-h-at do you mean?” Michael stuttered.
“What I’m offering you is a chance to live out your most secret fantasies. A chance to let your secret self out for a night.”
Michael was becoming lost in the mixture of those captivating eyes and the music of her voice.
“What’s your name?” Catherine demanded.
“Michael.” he answered.
“Well, Michael, shall I tell you what it is that you want me to do to you, my little boy.” she asked, again with the little laugh.
“Yes, please.”
Catherine leaned forward and looked deep into his eyes, drawing him deeper into her spell. Then, quietly, graphically, she proceeded to detail his most secret and powerful fantasy.

“My guess is you’d like me to take control, to take you home with me, tie you up so you couldn’t move a muscle, and then tease you for hours until you spurt globs of cum. Make you do all those nasty little things you would never have the courage to do on your own.

If he had been red-faced before, his hue now paled as Catherine whispered in his ear. She had repeated things he had never spoken out loud to anyone in his life. Desires so secret he was sometimes even afraid to fantasize about them.
“There’s no need to be embarrassed.” Catherine whispered into his idea. “No one else can hear us.”

Michael felt like she had read his mind, his dick had gown so hard he thought it would burst from his pants. It felt like all the blood in his body was rushing from his head to his groin. Catherine didn’t help matters any by slowly rubbing her leg up against his thigh under the table.

Color slowly returned to Michael’s face as he composed himself. He still felt more than a little lightheaded with the revelation of his darkest desires. It was as if he was wearing a sign on his forehead that screamed pervert.
“So what do you think my little man?” the older woman asked. “And I do hope I’m only using that phrase figuratively. Do you have the courage to live those desires?”.... to be continued!
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