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He was nervous as he approached her.  He almost chickened out and turned around, but he didn't. She was so hot, he had to try. So he walked up to her and asked if he could her a drink. She smiled and said sure Honey, and sit here beside me. He looked at her and was amazed she was big. Not the 6'0" to 6'4" of so many of the Cross Dressers, and Trans women in the club. She was big, as in like an Amazon, average height, but built like a bodybuilder.  Wearing black tactical boots,  pantyhose, and a black and red skirt that looked like a kilt. A red compression shirt that showed a small waist, with a big back and chest. The chest was so big and muscular as to not need fake boobs to look good. And she had big nipples that pressed out against the shirt. She had large biceps, and Triceps.  There was short salt and pepper hair on her head and some eyeliner around her eyes. She even had a short trimmed beard. But he didn't care. He just wanted her. He fantasized about her being able to make him do whatever she wanted him to. And doing whatever she wanted to do to him. That made him start to swell.
She looked down and saw the bulge in his pants smiled and said, "Well, I can see that you're happy to see me." And giggled. She saw he was in his mid to late 20's. A nice size cock, by the size of the bulge, and a good looking ass. The typical young man that wanted to think he was straight, but if he really was he wouldn't be here. He told himself he was here to fuck   a CD, and that was all. But really, he was hoping to get a cock shoved down his throat, then take it in his ass. He wanted to know what it would feel like to have a cock in him, to be treated like a woman. And he was attracted to her because he knew she could take charge and do whatever she wanted to him.
She put her arm around his shoulder, leaned in and said, "Don't worry Baby, I'm going to take good care of you." She put her other hand of his crotch, and felt him get even harder. She smiled to herself. She knew what he wanted, and decided she was going to give it to him tonight. She was going to give him 8 inches of fat cock.
They had a couple of drinks, then she told him she lived in the apartment building across the street, and asked him if he'd like to come up for another drink. She squeezed the inside of his thigh as she asked him, and he stuttered, and moaned as he said yes.
They walked across the street and went up to her apartment.
They settle on the couch each with a bourbon and coke.  She leans over and kisses him. He moans, then  starts rubbing her chest and sides. He can feel the separation in her muscles and it excites him. He squeezes her big nipples, and now it was her turn to moan. She pulled off her shirt and pulled his head to her left nipple and told him to bite it. He did, and she moaned even louder. He had been rubbing he pantyhose, and now ran his hand all the way up under her skirt, and found the large bulge at her crotch. Huge testicles and a big fat cock. It scared, and excited him, because of how big it was. She took of her skirt, and boots but left the pantyhose on. With a quick rip she could make them crotch less at the right time.  He took off his pants, and she led him to bedroom.
On the bed , she made a small hole in the pantyhose and put her cock through it.  Then she straddles his chest and puts her cock in his mouth. She grabs his head with both her hands, then starts rocking her hips and fucking his face. As she works more and more of her cock into his mouth, he starts to have trouble breathing and tries to pull his head away. She grabs his head tightly, and says, " No! Just relax and breathe through your nose. Relax, you can do this." He relaxes and is able to breathe. She starts fucking his mouth again, getting her cock deeper and deeper into his throat.  He starts to moan and she can feel the movement of him jacking his dick off. She pulls her dick out of his mouth and says, " No, you're not going to cum that way. She grabs some lube from the nightstand and slides down his body. She licks his cock, and his whole body shivers. She puts some lube on her finger then starts working it around the edge of his ass. Then slowly let's the tip of a finger barely enter his ass. Really more of a just pushing against it. He moans loudly, and arches his back. After a couple of minutes of this, she slips the finger in to the first knuckle, and moves it in and out. In and out. Slowly working the finger further and further in to his ass. Once it's all the way in, she continues working it in and out, and starts moving it around. After a while his ass relaxes enough for her to slip another finger in.  Slowly working his ass into a relaxed state with it. His moans grow louder and louder. She whispers into his ear, " You don't really want to fuck me, do you? You want me to fuck you, don't you? You want me to make you my little girl, don't you?"
" Yes, please!" He says. " Please fuck me!"
She smiles and says, "Anything my little girl wants.
She rolls him onto his stomach, and add a little more lube and starts working the fingers into his ass again. Rougher and harder. Then she grabs a dildo from the nightstand and works it in. It doesn't take long till his ass handles it without a problem.  "We're almost there Baby," she tells him, as she rolls him over onto his stomach. She works him over with the dildo some more, then whispers in his ear, time for the real thing my little girl.  She lubes her cock up then straddles him.
He loves the feel of the pantyhose rubbing against the outside of his legs. He's feels the head of her penis pushing at his ass, and it makes him moan with desire. The head finally pushes in and he gasps in slight *** and discomfort. The head of her cock is bigger than the dildo was. She says, " I'll go slow, relax, breathe, and relax your anal muscles. After a minute she pushes a little more of her cock into him. She keeps slowly doing this for about five minutes till she gets all of her cock in him. She just leaves it there for a couple of minutes, and stimulates him by rubbing the pantyhose against his legs. He moans in our pleasure and that let's her know it's time to stay riding his ass. Slowly at first, but then s***ding up the tempo.
She pressed her her legs against him and squeezed her whole body against him, pinning him tight against the bed, so he couldn't move. His stomach and dick pressed hard against the bed. She felt his prostate against the head of her cock and started moving so there was constant pressure against it.
He started moaning. The pressure against his prostate made him feel like he was about to cum. It didn't let up, it went on and on feeling like he was on the edge of an orgasm. Finally he came, and he came, and he kept cumming. He'd never came as much in his life before. He tried to squirm to get her to stop, but she wouldn't. She whispered, "I know you came, but I'm not done with you yet." She started pumping harder against him and that pressure against his prostate made him groan with delight and he felt on the edge of an orgasm all over again. He kept moaning, started talking in a feminine voice saying please fuck me, I'll be a good girl, anything you want.
She smiled, and with her body held him down against the bed in a pool of his own cum on his cock and stomach. She took his arms and pinned them down over his head.
He could feel the muscles in her large arms pressing against him. It was so hot and sexy, like being controlled, and ***d to do this by a big strong Amazon woman. He just learned that he like being dominated, controlled, and ***d. God, his dick was so hard. He kept riding waves of orgasmic delight, feeling like he was about to cub the whole time.  And then he did. He came, and came, even more than the first time. He wondered, how was this possible? He thought she has to be done now.
Knowing what he was thinking, she laughed and said, " Third times the charm, Baby." And she started pounding him again. After another ten minutes or so of bliss, he had his third prostate orgasm. This time his ass muscles clinching from his cock throbbing, squeezed her cock so hard she shot a hot large load of cum in his ass. Feeling her cock throb in his ass as she came, made him cum even harder.
She rolled off of him, and grabbed her drink and lit a joint. He just laid there for a few minutes, unable to move. When he could finally move, he rolled over and could believe the amount of cum that had come out of him.
She looked at him and smiled, " Kid, you familiar with Roxy's Dungeon around the corner? I'm Roxy, and I can teach you how to make some real ***. You've got a nice cock and a great ass, and I can teach you how to do to others, what I just did to you.  Are you interested?" And by the way, what's your name?
"James, Mam," he said "and he'll yes I'm interested, especially if you're going to be teaching me.
" Well, you're Jamie now. Be back here tomorrow at 5:00 and we'll get started."

Posted

Love it ! The sexual tension is intense! 🧨 Can I come over to Roxys dungeon and watch? 😈

Posted
3 hours ago, TAROTT said:

Love it ! The sexual tension is intense! 🧨 Can I come over to Roxys dungeon and watch? 😈

Of course you can. Roxy loves an audience. She’ll probably make you participate before it’s over with. Roxy has 8 full time doms on staff, and her cock has been in everyone of their asses. Male, female, Trans, puppy, whatever you want it’s available at Roxy’s. You can meet them in future stories, and see how Jamie’s feminization and training goes.

Posted
Saturday at 12:20 PM, Roxy1957 said:

Of course you can. Roxy loves an audience. She’ll probably make you participate before it’s over with. Roxy has 8 full time doms on staff, and her cock has been in everyone of their asses. Male, female, Trans, puppy, whatever you want it’s available at Roxy’s. You can meet them in future stories, and see how Jamie’s feminization and training goes.

I must find this Roxys Dungeon! I’m hot and bothered reading that!!

Posted

I’m a quiet, shy, insecure man, but Roxy is a slut that became a Domme, because of being approached by submissive CD’s and guys turned on by the femininity and muscles. She will ride you hard, and if she lets you ride her, you better do it right.

Posted

Looks like it might be a busy night at Roxys as the pace of interest starts to pick up 😀

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