tagTransgender & CrossdressersDon Juan With A Twist

Don Juan With A Twist


A Celebration

Stephanie thought that Halloween was the most romantically delicious of the holidays. She celebrated every year since her 21st birthday by going to a costume ball, picking up a masked stranger, and letting things happen as they may.

Not knowing who was behind the mask was more exciting than opening a birthday present. There was something about anonymous sex and not knowing what to expect.

It was perhaps the excitement and spontaneity of it. Or maybe it was the idea of a masked gothic character such as a vampire, monster, or other masked romantic character, letting his animalistic urges take over, and controlling her, taking her and letting her know in no uncertain terms who was in charge.

This Halloween Stephanie would be 25 years old. She wasn't a virgin, by any means, but neither was she jaded. She had lots of fantasies that she still had yet to fulfill.

For example, she imagined what it would be like to have anal sex. And she had always been curious about women. She was afraid to take the plunge, though. There was something forbidden about both subjects, and she was a little frightened of the consequences.

What if she liked it too much? What if she lost interest in vanilla sex altogether? It seemed silly to be frightened, but her traditional upbringing kept her from feeling total freedom to explore her sexuality.

Maybe that is why the costume ball held such an appeal. It was her chance to explore in anonymity. Noone need know who she was in real life.

Stephanie had chosen to arrive at the party in a belly dancer's costume with a veil. She thought that the soft sheer fabric felt wonderful against her round hips, and accentuated her voluptuous figure.

The bra top left little to the imagination, and her ample breasts looked poised to pop out of the little bra like two pieces of ripe fruit. Her voluptuous ass jiggled and jingled as her natural feminine sway shook the belly jewelry around her waist.

Her large green eyes peeked out of the veil winsomely. She liked the protection of the veil. It gave her comfort as she coyly flirted with a handsome vampire, or stared provocatively at a handsome looking man in a presidential costume.

Half the fun of the party was in studying the costumed figures and imagining how they would be in bed. Her mind wandered aimlessly thinking naughtily about presidential wet spots and cigars.

She unashamedly studied the package of one particularly well hung wolf man. "Hmm.... Very tempting." She thought to herself. The spell was broken as a very hairy man minced by in a Tutu. She giggled.

Then she saw him. He was standing in a corner by himself. His dark good looks attracted her. His hair was elegantly coiffed. He wore the costume of a Spaniard and was of obvious Latin heritage. He embodied the poise and charming character of Don Juan.

His slightly silvered hair and aquiline nose were distinctively handsome. The hooked nose gave him the appearance of a nearly tame lion. She admired his long muscular legs, the coiled power barely hidden by his pants. His ass was a case study for a sculptor and he moved with the grace of a cat.

And his eyes were definitely that of a feline predator. His eyes pinned her, staring intently, and ready to pounce. She felt herself blush, and wondered if he could see it through her thin veil, or read her thoughts for that matter. If he could read her thoughts then she was definitely in trouble. She blushed a deeper shade of pink.

Don Juan walked slinkily over to her and asked if he could have a seat.

"Of course," Stephanie replied nervously.

His catlike grace unnerved her. She stammered, "Don Juan spent time in a h-h-harem. And here I am dressed as a harem girl. It is ironic."

"Yes, the women of the harem needed to be loved and tended to just as all women need love and attention. Wherever there is a beautiful woman in need of attention, Don Juan is prepared to give of himself."

Don Juan seemed to be as suave as his namesake as his eyes took in her beauty and he caressed her with his gaze. His gaze implied that he found her very sexy and that he wanted to give himself to her.

Stephanie laughed at his cute Spanish accent as well as his obvious ploy to make himself available to "service" her needs. His sense of humor and ability to laugh at his human nature made her feel a little more bold.

"I definitely need the attention of a handsome lover like yourself. I hear you are very experienced at pleasing women. How much would the services of an experienced gigolo like yourself, cost?" Stephanie flirted with him. She was definitely feeling chemistry with this dark haired, masked stranger.

"Si, I am a very experienced lover and you will not be disappointed. My services are free to a woman as ravishing as yourself. Why don't you come to by place, and I'll show you exactly why Don Juan became famous for his ability to please women." His dark eyes seemed to sparkle with humor.

He was cocky but genuinely confident, and something inside Stephanie responded to his warmth. She wanted to give him the chance to prove his prowess as a lover, even though it was not the first time a stud had offered her his services.

In a moment the chemistry had decided for her. "Yes, let's go to your place."

Don Juan's Love Nest

The modest one bedroom apartment was as warm and charming as her lover. As he drew her into his bedroom, she smiled at the warm colors and simple style he possessed.

Red candles lit up the room and cast romantic shadows against the walls.

Don Juan's enormous king sized bed took up nearly the whole bedroom and was covered luxuriously with red pillows. The bed looked inviting to a little harem girl.

"Now, my lovely, I can show you what it means to be at the mercy of Don Juan."

He gently removed the veil, and Stephanie felt strong, masterful hands slide expertly around her. He bent his head to hers, his eyes hard and passionate, and her green eyes closed as she felt his tongue insinuate itself inside her mouth, pushing and probing hungrily as he kissed her.

"Young harem women want to be possessed, do they not? Your costume suggests that you want to be owned as a master owns a slave." He growled hungrily against her throat.

Stephanie could not respond to the question, though every fiber of her being wished to answer yes. All she could do was whimper as his strong hand curled around her buttocks and pressed her firmly against his manhood. She felt the extremely large bulge that was his package press against her firmly.

Her knees turned to rubber as she melted in his arms. Before she realized what was happening to her, she was on her stomach on the bed and her hands were handcuffed behind her back.

"Now my beautiful harem girl, you will serve the sexual whims of the greatest lover of all times. If you do not wish to serve Don Juan, I will give you a safe word and you can say it at any time and you can walk out of here of your own free will." He whispered a word in Stephanie's ear.

Even the feel of his hot breath on her ear excited Stephanie. She had heard the safe word, but she did not wish to escape. The idea of being forced was causing her nipples to get hard and was creating a slow throbbing ache between her legs.

"Yes, I thought you would not try to escape, my lovely." His words caressed her like a feather.

He unsnapped her bra top with a single snap of his fingers, and pulled down her harem pants with a single hard tug. His caressing fingers slid under her and rolled her nipples expertly between his thumb and forefinger.

His hot tongue began a rolling exploration down her neck, back to her ear, down her back, over

the curve of her lower back, down her buttocks, and teasingly over the crack of her ass.

She squirmed and tried to turn her head to see what he was doing.

"Eyes straight ahead, missy," He said sternly.

Stephanie obediently shifted her eyes away. But she longed to look back at him and see those commandingly dark masked eyes. But the idea of having to face forward and not see the man who was possessing her was an incredible turnon. It was almost as if she had been blind folded and forced to take whatever dick, tongue, etc. happened to be available without seeing or knowing who was doing the probing.

"This will never do. Your legs are too tense. You've got your legs clamped together. I'm going to make sure your legs stay open for me so I can tease and torment your naughty pussy until you beg me for release, Stephanie."

Don Juan pulled out a bar from somewhere under the bed. There were ankle cuffs on either side and it was adjustable. Stephanie gasped as he forcefully spread her legs and cuffed them apart. Now she could not pull her legs together and she felt like her pussy and ass were exposed to him.

She imagined what if he were to leave her in the bathroom at the costume party. What sorts of ghouls and goblins might have their way with her like this, as she was splayed wide open by the spreader bar? The thought made her whimper with excitement.

Don Juan responded to her whimpering and trembling by spreading her pussy lips and sliding his hot experienced tongue down the length of her wet pussy. He slipped one finger inside her pussy as his talented tongue pushed her swollen clit back and forth.

He felt Stephanie tighten up, then relax around his probing finger and tongue. Soon she was moaning and wiggling against him, knowing that she was completely defenseless against his lightly flicking tongue.

As she tried to wiggle away in fear, the tension of the bar between her legs just increased the ache and excited her even more. The more she struggled, the more turned on she was getting, as her thigh muscles and ass muscles squeezed and increased the friction to her clit and her pussy.

"I'm going to own every inch of your flesh little harem girl," Don Juan said wickedly. He made good on his promise by lightly kissing down the back of her legs and licking the back of her knees, bending up her legs and sucking on her toes, and leaving no inch of flesh untouched by his hot tongue, steamy breath and stroking hands.

"I bet you've never had that delicious little rosebud rimmed, have you my lovely?" Don Juan said with a low chuckle.

Stephanie was not absolutely sure what he meant until she felt his strong hands part her cheeks and his hot tongue started licking slowly around her asshole. Stephanie gasped in shock at Don Juan's wicked mind and probing tongue as he took her virgin ass, but she didn't say her safe word.

She tingled at the unknown sensation that was building inside her. She was more turned on that she had ever been in her life and she could feel her pussy tightening in response to what was happening to her ass. It was a feeling which began deeper inside of her than normal excitement. The taboo feeling of his tongue wiggling and probing in and out of her ass was exciting her so deeply that she couldn't control the motion of her hips as they began to push back against his tongue.

"Oh, I see you like it, little slave. That is good, because I am going to have both of your naughty holes tonight."

Stephanie yelled out, "NO, you aren't going to fuck my ASS are you?" She objected despite her curiosity.

"I don't think you are in a position to object, do you? And besides, if you really wanted you could use your safe word, couldn't you? I'm giving you every opportunity." Don Juan paused, listening.

"No, I didn't think you would say the safe word. Which means that your tight virgin ass is mine tonight." Don Juan laughed, a low sexy rumble in his throat.

"Does the slave need a reminder of who owns her? I am sure I can make you remember who is in charge here. I'm going to get you up off of the bed now. And I'm going to put you over the back of the sofa. You are not in a position to walk on your own, but you'll have to help me by not fighting me."

Don Juan physically lifted Stephanie off of the bed and bent her over the back of a large stuffed sofa like a large rag doll. She lay limply against the sofa, unable to move because she was so overcome with excitement.

"Yes, that is better. I like seeing your ass exposed to me. Good little harem girls should learn to bend over for their master at the snap of his fingers and push their ass up high for his pleasure. PUSH YOUR ASS UP FURTHER little harem girl." Don Juan said masterfully.

Stephanie was too nervous to move.

"I said PUT YOUR ASS IN THE AIR!" Don Juan shouted. She never expected his next action as his hand came down with a smack on her beautiful round ass. There were pink marks where his fingers had been.

"OW!" Stephanie obediently lifted her ass like a kitty in heat.

"Yes, that is more like it. You will assume this position, on command. I think you need to be reminded that naughty harem girls sometimes need a spanking to be kept in line. Your ass is mine whenever I need to cum, you little slut. And I will use you whenever I need you."

Stephanie's mind reeled at the thought of having to bend over and raise her ass to his throbbing dick whenever he demanded. She blushed as her quivering pussy throbbed and tightened at the thought. Don Juan proceeded to spank Stephanie's round bottom with his hand, watching it jiggle as he spanked first one cheek then the other.

Stephanie wiggled and squirmed as the hand kept coming down. She could not move much because of the spreader bar, but she could tense her ass muscles a bit to stimulate her clit and that is what she seemed to be doing.

The more Don Juan spanked, the hornier it was making her. She was surprised at her response to the spanking. The warm tingly feeling on her cheeks was making her hornier than hell and she started begging.

"Please lick me again, Master. Pleeeeease." She begged and whimpered.

"Beg for my cock, slut," replied the stern Master.

"Please let me have your cock, Master. Please, please, please, I need it."

"What do you need, slut?" The Master asked her patiently.

"I need your cock, Master," Stephanie replied.

"Do you want my dick in your horny little pussy?" The Master asked teasingly?

"Yes, Master, I want your dick. I want to please you." Stephanie replied.

That was what Don Juan was waiting to hear. He would definitely steal pleasure from this sweet harem girl tonight. He slipped his hand around the harem girls round hips. What sweet delight he would take from her round bottom.

He slipped a hand around his large throbbing cock and pressed it firmly against her pussy lips. She pushed back against him simultaneously as he thrust the full length of his throbbing cock inside her velvety softness. He watched as she swallowed him up and gripped him tightly.

He fought the desire to hump her like an animal as he began long sure strokes in and out of her sweet velvety wet hole.

But Don Juan had a unique surprise for this little slut. She whimpered as he paused in his penetration of her, thinking that he was teasing her.

She heard rather than saw him fumbling with the harness, although she didn't know what he was doing. She heard the click of the metal rings as he inserted the dildo into the strap on harness, although she still had no idea what he had in mind. She heard the flip of the top of the KY cap as he lubricated up the dildo.

She felt him pull out his cock, and then she felt round head of his cock at her pussy again at the same time as the dildo pushed up against her ass.

She gasped as both fat mushroom heads penetrated her at the same time. Her ass ached as the huge dildo stretched her virgin hole wide.

Don Juan chuckled low in his throat as the harem slut wiggled and sighed as he double penetrated her slowly. Inch by inch the slut's two holes were filled. Her pussy was filled with his dick, and her ass was being stretched wide by the juicy strap on.

Stephanie gave herself over to the sensation, being unable to move. She was spread wide for him, and could only wiggle a little as she was impaled and pinned to the chair by the two probing dicks.

Don Juan reveled in the sensation of tightness as he fucked her virgin ass and her pussy at the same time. He grabbed her hips and thrust fully inside her, his balls gently bouncing against her ass. He humped her steadily, watching her ass jiggle as he jammed both of her holes full. She moaned against him and squirmed against the two huge cocks.

"You are mine now, little harem girl. How does it feel to be filled so thoroughly little girl? A bad girl like you deserves to have both holes filled, hmm? I've taken some of your innocence and your anal virginity tonight. Now I'm going to give you what you need."

Don Juan's fingers flipped a switch and the vibrator inside the dildo in her ass began to vibrate. Stephanie moaned low in her throat.

His fingers reached around her and found what they were seeking. He began to skillfully rub her clit as he slowly jammed the two thick cocks inside of her. He licked her back and growled against her skin as he pumped her with long hard strokes.

He began to see her sweet pussy tightening around his cock, massaging it. Her pleasure was building. Incredible waves of pleasure were sweeping over her. He was in control and he would make her cum like a nasty little whore on the two juicy cocks. She couldn't help it.

He reached around with his other hand and pulled and rolled her nipples as he thrust repeatedly inside her. He began to talk dirty to her.

"I'm going to fill you up with my hot cream, baby. Cum on and squeeze your Master's dick hard, baby, when you cum. Wiggle against my big dick baby, and show me how much you love being fucked in the ass. Yes baby, I am going to stretch your tight little virgin ass wide with my rod. Cum with that fat dick in your ass, CUNT."

The vibrator was sending Stephanie over the edge. She was so embarassed that she was enjoying the dick in her ass, but she couldn't help her reactions. He could feel her begin to buck under him, struggling against the spreader bar as her muscles clenched him tightly. He thrust hard inside her, filling both her tight holes as she came violently against him. She couldn't stop the violent spasms rushing over her and her screaming and moaning combined with the feeling of thrusting into her pushed him over the edge as well and he began to cum as he rode her wildly bucking orgasm.

He lay there on top of her for a moment, totally spent. Then he uncuffed both her hands and her ankles. He turned her around and pushed her to her knees and told her to clean his cock of her pussy juice like a good little cocksucking whore. She obeyed quickly, grateful for his knowlege of her and his ability to touch her so deeply. She looked curiously at the strap on dildo which was eye level, and reached under it to take his cock in her hand. And was totally shocked to find another strap on dildo in a second harness.

She looked up at the now grinning dyke eyes, or was "he" a dyke? Don Juan de Lesbians??? But it had all felt so real. For the first time she noticed "his" breasts were taped under the shirt. For the first time she looked at his face and she noticed that the catlike grace that she saw was almost feminine, but not quite. She realized that this might not quite qualify as a lesbian experience. She guessed that he was transgender and not a "dyke" at all.

Come here my lovely. He drew her gently to the bed, curling up in a spoon with her. He caressed her and held her and told her what a beautiful woman that she was and how exquisitely she had submitted. He told her how brave she had been and how proud he was of her that she had not succumbed to using her safe word. He told her that he knew this was her first experience with someone like him and that he understood that it might be confusing for her.

In truth, she wasn't so much confused as shocked at the depth of her response to him. And she was shocked that someone born without a penis could be so utterly male.

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