[MTF FTM TG Domination Story]



{10,000+ Words}



*Disclaimer/Spoiler Alert: Contains Crossdressing, Male to Female and Female to Male Themes, Willing Domination, Hidden Roles, and Sexual Themes. This Story is Explicit.



*From the Author: "Hello, I'm Xarek.

This is a short story I wrote about an Idea I had for my last story, sort of as a follow up. Though it might change how the story is really taken, it doesn’t necessarily affect this story if you wanted to read something more bite sized. 

If you do want the context, read this first: https://www.deviantart.com/xarek-of-the-c3verse/art/AC-2i-11-Int-11-Miyuki-s-Birthday-1200504677 

Enjoy.

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Thursday, March 14th, 2019

A Hotel in Downtown Seattle

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Alex was feeling as nervous as he normally felt for a first date, especially as he had no idea what to expect from a woman he had heard little about.

The only things he had been told about her were that her name was Megan and she was a little more on the domineering side than he was used to. But his friend Miyuki had made him promise to let Megan do whatever she wanted to him tonight, also telling him that he and Megan would really get along well while Megan would easily become infatuated with the charming Multi-Billionaire.

Communicating through Miyuki, Megan had told him exactly what she wanted him to wear and the fact she didn't like bearded men.

It had hurt Alex to shave off his facial hair for the first time this year, but justified it by telling himself it was needing to be refreshed and regrown anyway. 

Not that he really believed himself as he scratched his itchy lip that used to hold his mustache, then his chin that held his anchor goatee.

Finally finding the hotel room number that Miyuki had texted him, he knocked on the door and made sure his black suit, red button up, and red blooming tulips all looked nice as he heard the door unlock.

To his surprise, the well endowed woman that opened the door was only wearing a set of black lingerie that consisted of a black garter belt that didn't have stockings strapped to it yet, a black lace bra holding her busty chest with her erect nipples visible in the sheer fabric, and her sheer lace panties that curved around her large hips and held the obvious erection in it.

Alex had known from the start that she was a trans-woman, but the sight of her proudly displaying it with the door open in the public yet gratefully empty hotel hallway made him regret even deciding to do this.

She was about Miyuki's height at five-seven with pale skin and very straight long blonde hair pulled back into a ponytail. Her face was triangle shaped and had a perfect dark makeup look with long eyelashes that framed her narrow and twinkling blue eyes, while she actually looked slightly older than Alex did.

While the shocked Alex zeroed in upon her eyes to avoid looking at anything else, her blank lips broke into a smile and she leaned sexily against the door and spoke in a low and sultry voice. “Hello, handsome.”

Alex could practically hear his heartbeat quicken.

“You must be the sexy young billionaire my friend Miyuki has told me so much about. Come on in.”

She turned and sauntered into the room, her hips rolling erotically to try and draw Alex's eye, but he quickly heard the elevator down the hall open and quickly stepped into the room, shutting the door behind himself.

The woman was upon him in an instant, taking the flowers with one hand while she leaned up on her tippy toes to give Alex a kiss on the cheek.

He finally got the courage to ask, “Megan?”

“That's me.” She said with a grin. “Not what you were expecting? You aren't either, Alex.” She practically purred his name. “You are way too sexy looking to be the nerdy guy Miyuki had promised me.”

Knowing he was going to be in for a wild night that he didn't know if he was up for, Alex swallowed while she went over to the desk where she had a vase, slipping the tulips into it before smelling them and telling him, “You got my favorite color right.”

Alex managed to say, “And you had a vase?” 

She shrugged. “Miyuki told me you like to be a gentleman. I thought I would come prepared and you didn't disappoint. Thanks for the flowers.” Still smiling, she beckoned with a finger as she stood next to the bed where three dresses lay. “Pick your favorite.”

A little embarrassed to be alone with a woman he didn't really know while she wasn't fully dressed, Alex did find a little excitement within himself to pick out what she would wear for him on their first date. He stared down at the spring dresses and pointed to a white one with lady bugs to match her nails, and yellow and blue flowers to match her eyes and hair.

Megan was quick to put the other two dresses in the closet and then put on the one he had suggested, having him zip her up. Then she quickly moved to the bathroom.

Megan returned a moment later after having applied red lipstick to match the lady bugs and asked, “Pull out your phone. I would like a picture of us together.”

Alex was a little confused by the strange request until he remembered that one of the main reasons for the date in the first place was because Miyuki didn't want her parents to think Alex and her were a couple when Alex met them for dinner tomorrow night. Claiming he already had a girlfriend who Megan would pretend to be for the pictures.

So he pulled out his phone, Megan stepping up to him while her sultry smile suddenly became cute and warming as she pressed herself against him intimately. 

Before he could take the picture, she said, “Come on, Alex. Pretend you like me. I don't mind you holding me one bit. In fact, I would appreciate all the intimacy tonight from you. Don't be shy. Hold me like you have a beautiful and sexy woman who wants to take you to bed tonight.” She tapped his nose playfully. “Because you do.”

Still hesitant and even more nervous, he took a moment before pulling her closer till she laid her head on shoulder as they took a groupie together, looking exactly like a cute couple and making Alex feel strange to be doing this to a woman he had just met a minute ago.

“Perfect.” She said with a kind smile as she looked at it. “We look so cute together. You should make that your screen saver to make Miyuki jealous.”

Alex raised an eyebrow at the request.

Megan laughed heartily, gently pushing into Alex. “Oh, you. Let's take a few more pictures. This is pretty fun.”

Megan made him take three more pictures, one of her kissing his cheek, one of her squeezing him tightly with her whole body, and finally one of them kissing each other which made Alex turn bright red in the picture when she instigated the surprise kiss.

But as soon as all the photos were done, her cute and innocent smile and demeanor instantly changed back into the sultry and teasing woman who pressed herself against Alex, wrapping her arms and leg around him.

And that's when he felt the bulge under her dress.

The bulge that still gave him pause as she stroked her body against his.

“You know… Miyuki didn't do you justice when she described you. I was thinking of some skinny nerd the way she told me you love comics and video games. But you are truly handsome. Maybe a little thin, but this is a face that shouldn't be hidden by a beard. And you have made me so hot and bothered.” She stroked his chest as her erection slid on him. “I don't think I've been this hard in weeks. I might have to do something about it now.”

Alex said nothing as her hands ran down his narrow waist until one hand went behind to grasp his butt while the other slipped directly into his pants and discovered the satin panties that Megan had asked that he wear, along with Alex's extremely moistened vagina.

“I've never been with a trans-man before.” She teased as she stroked Alex's covered mound. “I find that so sexy. I might just have to take you here and now, especially now that I know how wet you are for me.”

Alex swallowed as he knew he was indeed wet in his panties having been aroused by the beautiful and sensual woman coming onto him from the moment they had met.

It was then that Alex realized that though he had his eyes under control by not staring at her lingerie-covered body earlier and the cleavage of her large bosom directly below him, his mouth and brain were clearly not working properly so he told her, “It's probably because of how beautiful you look.”

Her smile brightened until she looked like she was touched by his words. “Awww, thank you.” Her hand finally slipped out of his pants and she turned around, offering him her back. “Unzip me.”

A little confused, he did as she asked while worrying about time, so he simply said, “We have reservations.”

Turning to him, she let out a forced yet devious laugh. “Oh, honey. A woman does not like to be rushed one bit. Beauty takes time and effort.”

Having removed the cute dress Alex had picked out for her, she took it back to the hotel room’s closet. Then she went to her suitcase and removed a pair of fresh black stockings and sat on the bed.

“Put these on for me, sweetie.” 

It seemed more like a demand than a request, but Alex obliged anyway, kneeling in front of her and opening the bag.

After bunching them up, she stopped him with her red nailed foot on his chest. “Wait. Make sure you do it as sexily as possible, I want to make you remember putting these on me all night.”

Swallowing, Alex took her foot and gently worked the sheer fabric over her toes, then slid his hand up her smooth calf until he could work the stocking over her foot with one hand.

She slid her leg through his fingers until her covered toes rested on his groin, teasing him there while he slowly slid the stocking up her shin, then knee, and finally to rest on her thigh which Alex hesitantly kissed.

“Ohh, that was a nice touch. But why don't you lick the other one when you are done.”

After Alex repeated the process to her other leg, he sinfully slid his tongue from her ankle and up her leg until Megan grabbed his head and gently moved it higher up her thigh until his tongue was forced to lick the satin panty covered dick.

She let in a sharp intake of breath. “Perfect. A little foreshadowing of what you will be doing.”

Before Alex could stand, she did so, still holding his head near her crotch as she put one leg on either side of him.

“Pull my panties down. I may need easy access later so I want my panties over the garter straps.”

Alex hesitantly slid his hands up her stockinged legs until he could hook his fingers on her thong, pulling it down to free her large and erect penis.

Ignoring the dick inches away from his face, Alex clipped the stockings to the belt and made sure they were perfectly tightened.

Then she told him, “Since I don't want to humiliate you in public… yet.” She winked. “I think it best if you tuck me in. But as you can see, I may have a little issue with that. The faster and better you work, the less likely we'll be late.”

Alex knew that this was the turning point. If he did as she hinted, he would be doing this with her the rest of the night, stuck with this crazy sexual woman who seemed desperate to have him.

But he had made a promise to his best friend, and he wanted to make sure Miyuki was happy with him.

So he took the hot length in his mouth.

Megan moaned as he met her lips, smiling down at him like she owned him. “Very good, Alex. Thank you for doing this. I was a little worried you wouldn't, but your soft mouth feels so perfect.”

He slowly began bobbing on her, wanting to get this done and over with as soon as possible, and she helped by grabbing his head and gently guided him as deep as he could without gagging.

He could taste her unexpectedly delicious precum on his tongue as he gave her the best blow job he could while she did most of the work.

“There's a little present for you a little lower, Alex. Between my cheeks. You may play with it now and if you are a good boy, I may let you play with it more later.”

His hands slid up her soft legs and shapely hips, pulling apart her curvy derriere to find the anal plug he was looking for.

Grasping it, he started to slide it in and out of her, the large end forcing her open anus wider with his thrusts while she moaned more and more loudly, and forced him deeper and deeper on to her.

Where before, Alex was focused on pleasuring her with his mouth, now he could only focus on not doing anything to gag as her dick entered his throat with his hairless face pressing into her groin. 

“Oh, yes… Alex… Your… mouth… feels… so… good!... Take… my… cum… every… drop!”

She felt like a jackhammer in his mouth while Alex barely managed to do anything to her anal plug, only able to be used as a toy for this crazy woman.

With a scream, she thrust her dick once more and came down his throat, holding Alex there while he had to hold his breath and let it happen.

Finally she finished and she gently slid out a little to where Alex could breathe harshly with his nose.

“Thank you. Now why don't you do yourself a favor and make sure I am well and thoroughly cleaned off. I don't want to get my cum on that sharp suit.”

Even though Alex struggled to catch his breath, he did as she asked, making sure she was sufficiently cleaned off while her fingernails combed through the hair she had messed up like she was just a casual stylist.

When he was done, he finally pulled away, having to lock the final bit of saliva off before looking up at her.

She patted his cheek as though he were a puppy. “Good boy. Now tuck me in please.”

Regretting even agreeing to this date, Alex gently took hold of her silky and soft manhood to gently take her testicles and pushed them up until she let in another sharp intake of breath and they didn't come out of the cavity inside of her.

Then he put her length between her thighs and pulled up her panties again until they rested on her now flat mound.

“Make sure it's smooth all the way.” She teased. “I don't want it slipping out as I think it may get too hard to go back in without you sucking me off again.”

Alex slowly slipped a hand between her thighs to make sure the crossdressing thong held her penis in place, continuing to slide up and between her cheeks, passing over her anal plug before pulling away.

Smiling, Megan demanded, “You can stand now.”

He did so and she was immediately upon him, kissing him passionately with her tongue in his mouth, before breaking away. She went into one of her bags, and returned with another large anal plug. 

“Would you be kind enough to allow me to put this in you for tonight? I would love to share a little secret pleasure with you.”

She didn't seem as forceful about it as earlier, but Alex was now fully aware of what she was capable of.

As her eyes seemed to beg up at him, Alex accepted his fate as her plaything for the evening and undid his jacket, setting it on the bed. Then he undid his pants, pulling them down along with his red satin panties and presented himself to her.

To his surprise, she dropped to her knees and licked between his cheeks, making him shiver uncontrollably.

“You cleaned yourself out for me, good boy.” She said as she lubed the plug and carefully worked it inside of him.

The plug was much larger than he was used to and took a little effort, but when she teased inside Alex's vagina with a finger, the plug slipped in him which made him gasp.

“Excellent. You may rise and face me.”

He pushed off the bed and turned only to have her playfully lick his wet vaginal lips like she had his anus, her own lips far from him to not ruin her lipstick.

“Just wanted a taste. You are very delectable.”

She slid his panties into place, flattening them against his groin and sliding a finger between his cheeks and on his plug before helping bring his pants up, tucking his shirt in and doing up his belt.

Then she held her hands to him, and he helped her up so she could peck his lips. “Thank you, Alex.”

Then she held up a little fob remote and pressed a button.

The anal plug inside him vibrated violently and expanded more, making Alex jump.

She smiled deviously as she deactivated which also shrank back down. “Just making sure it works.”

She moved to her closet again and removed a set of black leather thigh high platform boots with a six inch heel, and the boot tops coming a few inches below her stocking tops.

After she slipped them on and zipped them up, she surprised Alex again by removing her bra, letting her bountiful breasts free that Alex barely saw before glancing away.

He heard her devious laugh again. “Don't be shy, sweetie. I'm not ashamed of my body and I am already wanting to have sex with you later. Here, come help me with this.”

From the closet came a red accented black leather corset top that was sleeveless and had a built in bra. 

She slipped it over her head and pulled it down to rest on her, before offering her back to Alex.

Alex slowly came to her and gently took hold of the corset ribbon to tighten it against her while she held her silky straight blonde hair up.

“Tighter Alex.” She demanded. “I want to make every man jealous that you get to have me tonight, while imagining what I'm going to do to you.”

Pulling on the ribbon more, Alex really collapsed in Megan's already thin waist until her grunt made him give a tiny amount of slack before he tied the ribbon up.

She checked herself out in the mirror, winking to Alex in it before removing a short and tight red leather pencil skirt that she again had Alex zip up for her, the bottom of the skirt barely reaching over the top of her stocking and barely covering her groin that would easily reveal her true nature if it became free.

After making sure everything was perfect in the mirror again, she turned and struck a pose for him, her eyebrow raised in an obvious question.

Swallowing nervously at going to a fancier steak restaurant with her dressed like this, he told her, “You look very beautiful.”

Her lips smiled again. “Thank you. I picked this out especially for you. Miyuki told me you like domineering women.”

Alex didn't really, but he had promised to be open minded to the woman he knew loved to dominate men, tie them up, and use her dick on them.

She went back to her suitcase and returned with a small black gift bag, grinning as she gave it to him.

Completely surprised at her giving him something especially as he already had a toy inside him, he told her, “You didn't have to get me anything.” As he removed the red tissue paper and removed a black leather tie.

“Oh, I wanted to. I figured you didn't have a tie like this.”

Alex definitely didn't as the tie had a feature that he would have never imagined a tie to have, and never would have bought for himself.

The black leather was already in a fixed patterned knot that looked like a rose with the tie length coming from it and the tail in a slip device. But the knot also had a gold key sticking into the center of the flower with a gold chain necklace attached to it.

Alex guessed what it was immediately, but Megan told him anyway. “This is a locking slip tie. Kind of like a secret leash. You have been such a good guy so far with me, but I can see your hesitation. You don't like this kind of thing. But I promise that I will give you quite the night to remember if you let me put this tie on you. Or, we can just have a simpler night dressed as we are, and I will still give you a wonderful evening, though it definitely won't be as fun. Your choice.”

Alex stared at the tie in his hands and took a deep breath before handing it to her. “I'm yours for the night… Mistress.”

She smiled. “You can call me Megan in public, but I want you to call me Miss Megan in whispers all night.”

Taking the tie from Alex's grasp, Megan did up his top button, flipped the red collar up, and threw the tie over his head until she could tighten it around his neck and fix the collar while she smiled deviously the whole time. 

After removing the key that clearly locked the tie to him like he now had a secret collar and leash, Megan slipped the key onto her neck between her generous cleavage and grasped the tie to pull Alex into a firm kiss before breaking away to say, “I'm ready for you to take me to dinner and as you are now mine for the rest of the night until I decide to release you, I expect you to be on your best behavior.”

Alex could only look at her confused as he wondered why and how she expected him to be bad.

Smirking, she said, “By ‘best Behavior, I mean that I want your eyes and hands all over me tonight, just like mine will be all over you.”

Grabbing her clutch purse and the fob that controlled Alex's vibrator, she drew Alex's eye as she slipped it between her breasts with a smile before helping him back into his jacket and wrapping her arm around him so he could take her to the door and to the restaurant that Alex hoped he wouldn't get kicked out of for too many sexual advances from his sensual date.

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After Alex had felt aroused for their whole dinner with the domineering and teasing Megan sitting directly next to him and toying with him all night, Alex didn't protest when their sexual foreplay began before they could even get out of Alex's sports car, with the ravenous blonde climbing over to sit on him, grinding her groin against his while she forcefully kissed him and pulled his tie to the side like she would a pet with a leash.

Breaking away, she wordlessly opened his door and got out of the car, pulling him out with his tie while a nearby mom gave them a strange look before pushing her child away from them.

Megan didn't seem to mind one bit as she pressed Alex to his car, sliding a hand along his groin as she pressed herself to him again. 

“I can't believe how sexy you are.” She whispered to him as she licked his face. “My panties are barely keeping me in check and you already got me off before we left the room.”

Alex swallowed again as he remained frozen, allowing himself to be Megan's plaything while she continued to pleasure his groin.

Releasing his makeshift leash, she grabbed his hand and pulled him to the hotel garage’s elevator, throwing herself at him again to press him to a wall inside of it and kissing him more forcefully than any woman he had ever been with.

Then she pulled him to her room, where he was pressed into the back of her door, with her tearing off his jacket and taking hold of the leather tie again before their lips continued their makeout session.

After gently biting his lip, she pulled back to demand, “Remove my skirt.”

Alex's hands slowly slid up the leather to find the zipper, pulling it down to remove it and reveal her panties again.

Breaking her normally domineering demeanor, she simply asked, “Pink pill?”

Alex had to bend to grab his coat and remove the pill needed to make this night even better for them from an inside pocket.

Megan took it from him and pulled him by his tie to the bathroom where she got a glass of water before demanding, “Tongue.”

He nervously stuck it out only to have her step up to take it into her mouth, practically giving it a blow job while playing with it with her own tongue. Then she pulled away and deposited the little pink pill upon it, offering him the water to drink.

After he swallowed, she was kissing him again and pushed him backwards back into the main room. 

Breaking away, she grabbed his shoulder and pulled downwards, silently demanding him to kneel before her, which he hesitantly did while looking up at her.

Raising an eyebrow, she simply pointed to her groin with a long red nail, this command obvious as well.

Alex slid his hands up her legs, coming around her wide hips before tugging her panties down and over her boots so they were free of her.

She had to separate her legs to free her dick which immediately became erect, already leaking pre-cum. Reaching between her legs, she also released her balls and fondled them before coming up to stroke her dick, moaning as she slid her hand along it.

When she finally let go, she demanded, “Now suck me off like a good boy. I know you've wanted it all night since you had a taste earlier.”

Alex wasn't sure he had, but he obeyed her anyway, slowly licking her hot length and tasting her again.

Her hands grabbed his head as he continued to please her with his tongue, his hair pulling as her fingers intertwined into it for a good grip.

Then she moved him to the tip of her length, letting him kiss it before sliding it between his lips for the second time.

Slowly at first, she did all the work of easing the dick deeper and deeper into his mouth, Alex using his experience to make sure she had a pleasurable experience while only able to control his tongue, the suction, and the pressure of his cheeks.

Then she became more forceful while she used him, thrusting her dick deep into his throat while he could only focus on trying not to even gag.

“That's right… billionaire boy.” she said in between thrusts. “Suck my cock… You really know… how to treat… a woman.”

Alex prayed that she would come quickly as she used him like no one else ever had. This time, however, he had an advantage that she had given him as he removed her red fob from his shirt pocket. 

Pressing the button he had used whenever she had asked tonight, Megan gasped as her insides were suddenly assaulted by a strong vibration that he also knew expanded the plug into her.

“Naughty, boy. Catching me off guard like that. Are you that eager for me to cum?”

It took all Alex's willpower not to roll his eyes.

“Then keep going then.” his tormentor told him as she began picking up speed again.

Alex was finally rewarded when she gasped and shoved her dick all the way into him while she came down his throat.

When she released his head, he pulled back with a gasp, wiping the semen and spit from his mouth  and caught his breath.

She gently stroked his face and demanded, “Clean up your mess.”

 He slowly leaned forward enough to begin licking her dick off while she teased him with her fingernail until he had cleared her soft tool.

Then she beckoned him to rise before throwing herself on him again, kissing him passionately with her tongue searching for any of her remaining semen.

Pulling away, she removed the Keychain from her neck and unlocked Alex's tie so she could remove his shirt and start stroking his narrow body and chest, even playfully nibbling at his nipples. 

She broke away to tell him, “They did a good job operating on your chest. I Imagine that you had quite the breasts for your build. If I didn't know better, I'd say you were born a man. ”

For the first time that night, she nearly made him laugh and Alex had to suppress a snort of laughter while Megan giggled and played with his erect nipples, which was becoming more and more sensitive with how often his sexual partners played with them.

Then she broke away again to say, “They did a great job on mine too. And I really wanted to go big.”

Reaching behind herself, she unsnapped part of her top that Alex hadn't noticed had snaps, and freed her breast from the built in bra so she was now only wearing her boots, stockings, garter belt, and shoulder strapped underbust corset.

“Make them feel good.” She moaned as she offered her large bosom to him.

Alex slowly stepped up to her to hesitantly take her breasts in each hand, making her moan as he gently squeezed the flesh and rubbed into them.

She sensually whispered, “Suck my nipples.”

So, Alex obeyed, clamping down on her soft and erect flesh and drawing his breath in to suck them.

His hand was moved away to be replaced by her own so she could roughly squeeze her mound while Alex continued to play with her hot nipple with his tongue and lips.

Then, to his surprise, hot milk began to pour into his mouth.

He nearly choked from the unexpected fluid, but she held him tightly to her breast with one hand while the other milked the liquid into Alex's mouth while moaning.

“I paid a lot to have them prepare my breasts in a fashion to have good milk glans. I loved the idea of breastfeeding my playthings. Do you like mommy's milk?”

Alex could barely nod on her while drinking from her, before she made him swap nipples to even out the pressure release from her large milk mammeries.

She finally released Alex who gasped for breath and had to wipe his cleanshaven mouth again, never expecting to be with a woman who wanted him to do something like that.

“Now, what do you say for giving you such a treat?” She reprimanded him in a demanding tone.

Swallowing from nerves, Alex told her, “Thank you.”

“Thank you, Mistress.” She corrected him. “We aren't in public anymore.”

“Thank you, Mistress.” Trying to appease her, Alex added, “You were delicious."

She smiled brightly and nodded approvingly before she stepped towards him, removing his belt in a fluid motion to snap it threateningly together. “Take off your shoes and pants.”

He quickly did so, setting them out of the way only to have her toss his belt around his neck, pulling him to her so her dick and lactating breasts pressed into him, both of which were leaking enough to spread white fluid on his chest and his panties.

“You are so sexy.” She said hungrily. “I think I may have to keep you for a while… make you my boy toy who buys everything I want.”

He hoped she was kidding slightly, but her tone was still enough to make him feel submissive and at the smaller woman's mercy.

Tossing the belt to the floor, she slid a hand down his hairless leg until she could pull up his knee, demanding him to, “Wrap it around my sexy butt.” While she continued down to his foot to remove his sock.

The entire motion was repeated with the other sock, but this time she kept his leg in her hand and pulled it up to drive him to the bed, where she continued to stroke her dick against Alex's smooth groin.

Her voice was sensual as she said, “Thank you for wearing the red thong I wanted you too… I love a man in lingerie. And seeing you without a dick has made me so hot… I should have done this ages ago.”

Throwing his leg to the side, she dropped on top of him, kissing him into the bed as her hands were all over his chest, grabbing his nipples painfully while she thrust her tongue into his mouth to catch his moan of pleasure and pain.

She broke away with a gasp. “I have so many plans for you tonight… but you look so figging sexy under me…”

Her dick was practically pressing into his vagina already as the soaked fabric from his vaginal fluids was ready for her to enter him.

Letting out a carnal growl, she tore off his panties and dove between his legs, pulling his legs as far apart as she could to eat at his pussy.

Like she hadn't had water for days, she attacked his vagina mercilessly, lapping his fluids, gently sucking his clit, and burying her face and tongue as deep as it would go as Alex gasped loudly in pleasure, gripping the sheets tightly to not grab onto the woman and force her head deeper.

But then his grip discovered something, making him look at the made bed that had something bound to it under the sheets.

She caught his curious pause and jumped on top of him again, forcing his hands apart as she leaned over and clicked her tongue. 

“Naughty, naughty boy… you discovered my surprise. Well, now that the cats are out of the bag, I don't have to hide my true intentions any more.” She leaned in to growl. “You are mine.”

She suddenly grabbed one of his hands and locked his wrists into a cuff that was beneath the sheets, grabbing his other hand and intertwining their fingers. 

“So, Alex.” She said in a devious tone while her free hand slid to his vagina to begin playing with his labia. “Swear yourself to me tonight, and I promise to make you feel an incredible amount of pleasure. Tell me you are mine and I will mercilessly make you orgasm for the whole night. Kiss me, and I will give you a night to never forget… Or… you can free yourself by finding the key to this lock somewhere on my body.”

Having previous experiences with this kind of thing, Alex suspected that the key was probably inside the butt plug she had in her.

But he wasn't sure he wanted to be free and thought that this might be the only chance he got to try something like this.

He had been submissive before, letting women tie him up and use him for pleasure. But it had never been with a woman so erotic and forceful, and definitely not with a woman that seemed this into him.

And it only was for one night.

So he threw his freedom away, hoping she wouldn't abuse him more than in a playful and sexual way and told her, “I'm yours.” Before leaning up to press his lips to hers.

He could feel her smile as they kissed, her finger finally entering his hole to explore it.

Pulling back, she smiled before cuffing his other hand to the strap attached to the bed. Then she slid down his body to strap his legs too, leaving him spread eagle on the bed while she went to her purse where she removed the remote she had playfully used on him several times already that night.

The toy began expanding into him and vibrating, making him test his restraints while he squirmed in pleasure.

Megan hoped on top of him again, sliding her dick between his labia lips as she smiled excitedly at him.

“It's been a long time since I had a pussy to fill. And your's looks so amazing and wet. You must want it bad. Tell me you want me to stick it in. Beg me to thrust my cock into you.”

Nervous again, Alex said timidly, “I want your cock inside of me.”

“Ohhh, you can do better than that. Beg me for it. Tell your mistress you want her big juicy cock in your tight manly pussy.”

Throwing his inhibitions out the window while his body ached from nearly getting filled but still unable to be, he begged loudly, “I want your cock, mistress! Fill me please! I need it!”

Megan smiled more deviously than ever before in a triumphant way, telling him, “That's a good boy. You can have it then.” 

Then Megan slid her cock deep into Alex's hole, making him gasp in pleasure and strain against his bindings.

She slowly worked her way into him, picking up speed as he was overwhelmed by the pleasure of having her inside him, moaning and gasping with almost every thrust as he silently begged her to never stop.

“That's… a… good… boy… take… my… cock.” Megan struggled to speak in between thrusts, pounding into Alex as he felt the incredible pleasure coursing through him.

It wasn't too long before he could feel his climax near from the assault of both of the anal plug expanding and vibrating inside of him and the beautiful blonde in a very sexy leather outfit between his strapped down legs.

Things became worse when she put one hand on his chest to balance herself and toy with one of his nipples with her thumb, as her other hand went near their connection point to rapidly flick against his clitoris, where he didn't hold back his scream as he came to a squirting orgasm, his fluids flying everywhere.

But his tormentor showed no sign of slowing her thrusts or sensual flicks, going deep inside Alex as he kept on the edge of a near orgasm for several incalculable moments.

Megan let out a cry as well, giving one more strong thrust as hot fluid flooded into Alex who was grateful he had no risk of getting pregnant.

Collapsing atop him, Megan kissed him passionately again, her hands firm on his head as her hips continued to thrust her slightly limper dick around his filled pussy.

When she broke away with a devious smile, she booped his nose with a finger before getting off him and moving away to her bag.

Alex watched her as best as he could from his tied down position, knowing it was far from over as the last session seemed just a warm up.

She came back and straddled him with a bag in her hands and a grin on her face.

The first thing she removed from the bag was a small two inch dildo with a flat base. Usually it was meant to be attached to a strap for a gag, but she didn't use one as she  thrust it into his mouth. "You were really loud a moment ago when I was pounding into you. I'm glad the room was advertised as soundproof. But right now, I don't want you moving and ruining my work. Not that you were saying much anyway, which I find kind of cute to have a man with few words.”

Alex nearly rolled his eyes as Megan had been just as vocal as he was in their play, but he ignored it to see what she would do next.

Then from the bag she removed a make up kit, Alex's eyes widening as she began putting simple make up on him.

“Miyuki told you I love crossdressers, right? I love making up men to look more feminine while still appearing mostly male. Kind of like this femboy I love to dominate named Keegan. He makes a pretty cute girl in public, but I think I like having a guy I get to make up just for my pleasure is pretty sexy. It's hot to be in public looking like a normal couple while I can remember that I can make him so sexy with makeup and what I can make him wear under his manly clothes.”

She paused her blushing brush for a moment as she seemed to reconsider her choices.

“I guess that it might be a little insensitive of me to not accept your choice to become a man by making you wear makeup again.” Then she smiled and leaned in to whisper conspiratorily, “But we both know you don't care about that, right big boy?”

Alex shrugged his shoulders and didn't argue or agree with her. Mostly because he couldn't.

She continued to make him look feminine, applying pink lipstick, mascara, and eyeliner to his face as she said, “I wonder how long has it been since you've been in makeup. What made you decide to become a guy? I guess we never talked about that.”

They never really talked about anything for dinner as she was the one to deflect any small question he asked her about herself, while she distracted him with sensual touches, whispers, and demands for his affection. 

But that didn't matter now as he was at her mercy, tied to the bed and beneath her while she took a makeup pen and applied it to his cheeks to give him whiskers.

“Miyuki told me you like pet play, so I went to this really big costume shop that I think Miyuki mentioned that you own, and bought you a costume earlier today. I think it's poetic that you own the shop that will lead to your humiliation tonight. I hope you like it.”

After she applied a pink pen to the tip of his nose, she kissed him again over the gag, her red lipstick now holding his new pink one, then she got off him with a grin and moved back to her suitcase. 

Alex watched her as she removed the bagged costume and pulled out a white furry Kigurumi style romper with a pink belly, an attached hood, and oversized attached paws that had some padding to make them large and cartoon-like.

She held up the hood so Alex could see the white bunny ears with pink insides, before turning it to show Alex the pink bunny tail.

“Cute, huh? I think you'll look adorable in this.”

Alex wasn't so sure as he didn't expect her to change any more of his appearance while he still looked mostly male with just makeup on him.

But he couldn't protest as Megan also opened a pair of pink fishnet tights that had a crotch opening, which she bunched up and undid one of his legs to slide the tights onto him, stretching it up his smooth hairless leg which she caressed and stroked teasingly. She also released his other leg to repeat the process.

Then she grabbed a set of white furry stockings with what looked like thin slippers attached to them that had larger pawed feet.

She slipped them onto him, getting his size correct as she made sure they went all the way up to his thighs.

Then she took a moment to stroke his leg that was now covered in fur. “This is so sexy… I love seeing a man like this. Especially because I see how much you are enjoying it by how wet you are and how heavy you are breathing.”

Alex was indeed breathing heavily and he knew he was wet. With the sexy woman with what she was wearing, to what he knew he would be in soon, he was forced to admit to himself that he was enjoying this.

She slipped the unzipped romper over his large and long feet, bringing it up his legs until it came to just below his butt.

Then she sat on him again and demanded, “You promise to be good?”

He nodded and she smiled to release him from his cuffs, helping the romper completely on him as his hands slipped into the heavily padded paws.

He noticed a zipper on the inside of the soft pink interior that would allow him to pull his hands out if he needed to.

After zipping the romper to him she playful threw the hood over his head and now he was her bunny.

“Aw… you look so cute. What would all your friends and employees think if they could see you now?”

Alex was very grateful they couldn't, but still felt a bit of a worry as Megan sat on his lap and took a groupie picture with his phone.

“Perfect. Something to remember this night with.”

Getting off him, she suddenly flipped him over and attached the cuffs back to him, this time unhooking them from the bed strap to bring them closer to the center so Alex's forearms were closer together so he was leaning on them.

She started playing with what he guessed was his tail. “Look at that cute little bunny butt.”

She slapped his butt hard, the padding of the furry romper saving most of his rear end from the blow.

Then she got off the bed and he heard the sound of Latex. Glancing back over his shoulder, he watched her put on a pair of red latex gloves that nearly came to her shoulder, covering them with lube.

His heart racing in slight panic, he knew what was going to happen soon, as she took a collar with a chain and attached it to his neck. Her hand moved to the dildo and slipped it from his mouth as she said, “Good bunnies don't talk and are really quiet. I hope you are a good bunny, but I wouldn't mind a few appreciative moans for me.”

Then he felt her unzip his groin, freeing his pussy and buttplug.

One of her fingers teased his wet sex, easily slipping inside of him as she stroked his mound and he bit his lip to muffle his moan.

“You look so sexy and vulnerable like this. I love it so much. I always wanted a bunny as a little girl. And now, I have the best one ever.”

Her fingers suddenly pulled the anal plug from him, making him gasp as his anal opening felt empty from having the large tool in him and expanding in him all night.

It was quickly replaced by two of her cool wet fingers that worked deep inside his widened hole, the lube easing his rectum.

“Shall we see just how deep into the rabbit hole I can go?” She asked as she added a third finger, pressing them against him to make him gasp.

She continued slowly to make sure he could handle it, adding more lube to her hand as she opened him up for her fourth finger.

Soon, she was palm deep into him, slowly working his anus to prepare it for the final finger.

He could have stopped. He could have protested. But her fingers felt so good, he wanted more.

“Ready or not, here we go.” She said before her thumb eased into him.

He had most of her hand inside of him now, and she kept pulling it back and pressing forward, stretching him out more than he had ever been before as she pleasured his insides. 

“Good, bunny. You are doing so well.” She cooed while her free hand applied even more lube to her hand. Then it went to Alex's vagina to gently tease him. “I think you are finally ready.”

Then she put her weight on her arm and drove it into him.

Alex yelped and orgasmed a little as he felt her hand further in him than anything else had ever been. He couldn't believe he had been able to take something so large that opened up and rubbed his insides in a way that nothing ever had.

“Good, little bunny billionaire boy. You took my whole hand in you. That's a good bunny.” She tickled his rectum with a finger, making him squirm around her wrist.

Then she twisted her arm, and pulled backwards, not pulling out, just maximizing his stretched anus.

“Now comes the fun part.” She said before she began to fist into his stomach.

Alex could do nothing but kneel there and gasp as she jammed her hand into him, his sensitive walls translating their pleasure to his vagina that hummed as Megan played with that too.

It wasn't long before Alex let out a closed mouth shout and orgasmed, his vaginal fluids sent flying by Megan's violent strokes and thrusts.

She finally slowed and Alex came down, catching his breath from one of the most intense feeling he had ever had.

“Good bunny. You did so well. I'm really proud of you.”

She was just as slow and careful pulling out of him as she did going in, Alex grateful that it didn't feel as bad as he was worried it would. 

But it appeared Megan wasn't done with him as she replaced her arm with her dick, easily sliding it all the way in one push.

“My turn to cum from the pleasure of your cute little bunny butt.” She said before not even hesitating to go into a straight ram as she lay fully into Alex's butt.

Alex just sat and gasped as she went into him rapidly, her balls slapping hard into his vagina as she gasped with each thrust. 

Pausing momentarily to free his arms, she pulled him up on his knees so she could play with his vagina while she worked, rolling his clit in her fingers and shoving her fingers into his dripping hole.

Then she finally gasped and came into Alex, filling his already raw rectum with hot fluid that was now in each of his holes and stomach.

____

AFTERWARD

____

After they had laid together quietly for a long time, Alex with a new anal plug that felt much smaller than anything else he had in there tonight but was necessary not to make a mess, Megan turned to look at her pet bunny that she had been stroking.

She smiled and leaned up to kiss Alex on the nose. “Be right back, my cute bunny. I have to tinkle.”

She quickly got off the bed and headed to the bathroom, Alex noticing her grab a bag on the way.

A moment after the door shut, Alex heard his phone receive a notification.

He struggled to remove his hands from the pawed gloves that had a zipper on the inside so he could use his hands if he needed to, then he went to where Megan had left his phone after taking more pictures of them together.

Taking it to the bed, he rolled his eyes when he saw that it was his friend Miyuki texting him.

-Miyuki< I don't really need to know all the details, but how did it go with Megan tonight?

A little amused, Alex replied:

-Alex< I'm still on a date with her. Why are you texting me?

He heard a quickly stifled snort coming from the bathroom, but ignored it.

-Miyuki< I'm just checking in on you. Did you enjoy the night?

Alex considered the question before responding, which gave Miyuki a chance to add:

-Miyuki< Megan texted me.

-Miyuki< She thinks that you didn't really have all that fun.

Alex sighed heavily as he considered the night.

He had enjoyed some parts of it, but others had hurt him and made him feel like he was only there for Megan's pleasure and not as a couple trying to find mutual romanticism and respect while they had a date and sex together. 

Megan was everything that Alex didn't want in a girlfriend. She seemed to want to take advantage of every part of him and his vulnerabilities as someone shy around a woman he didn't know. He preferred to get to know a woman before doing something like this with them.

-Miyuki< She says you were quiet most of the time and didn't seem to enjoy her advances. She does like to be playful, but she didn't mean to push you too hard.

Alex hesitated, worried about hurting his friend before he finally replied.

-Alex< I wish you hadn't told her I was a billionaire. I didn't like her calling me that all night and you know I have no desire to be with someone who takes advantage of my wealth in any way.

Miyuki must have been a little surprised at what he said because it took a moment for her to type her reply.

-Miyuki< I'm Sorry. I'll remember that if I try to set you up again.

-Alex< There were some parts of tonight that were fun, but I'm not sure if this is going to go anywhere. She practically threw herself at me the entire night and didn't hold back at all. And I feel like she wasn't honest with me or herself. I would like to get to know a woman and actually listen to her, but I still don't know a single thing about her besides that she loves to dominate guys. And she was way too into that. Some of the things really hurt and she didn't really ask if they were okay. I think it was honestly fun to experience it for one night, but I would prefer it with someone I'm more familiar with and trust while there is a little more intimacy between them.

-Alex< Someone like you.

Miyuki was quick to respond again.

-Miyuki< She isn't normally like that. I promise. Megan just likes to see if guys are willing to sometimes do that with her. I'm sorry she was so mean and pushy about it. 

While Alex didn't know how to respond, Miyuki did so again.

-Miyuki< Don't tell her we talked, but can you please give her a second chance? For me? I think she might open up to you more. No need to reply.

After Alex rolled his eyes again, this time in frustration, he heard the toilet flush and quickly put his phone back before quickly moving back to the bed.

It was still a few minutes before the door opened and Megan came out again, while Alex had calmed his frustrations and decided to see how things would go with her.

To his surprise, Megan had changed into a full bunny costume almost exactly like Alex's, with a black romper kig-like furry outfit, the loose sleeves with the huge attached paws, the floppy bunny ears, as well as the black fishnet tights and bunny foot furry stockings.

She had even done her make up to give herself a bunny nose, whiskers, and pink lips to match Alex's.

Smiling awkwardly to him, she said, “I didn't bring anything else to really wear to bed.”

He asked her seriously. “Then why did you put on more makeup if you are just going to be in your pajamas?”

Looking sad, she just shrugged and came to the bed and crawled on it to sit next to him on her knees and the loose paws of the costume. 

Then she surprised him by removing her hands from the paws to take off his collar and toss it to the floor, before putting her hands back.

Smiling kinder now, her seemingly always devious personality gone, she said, “I think you passed the test.”

Confused, he asked, “What test?”

She nervously bit her now pink lip before replying. “If I'm going to date a guy, I like to see if he can handle me when I like to be a little rough. But I think I might have gone a little too hard on such an amazing guy today, and I'm really sorry for that.”

Alex considered Megan to see if she was finally being genuine with him, and gave her a small smile. “Thank you for the apology.”

She surprised him again by gently laying atop him and gently kissed his lips before telling him, “I promise I don't always act like I did tonight. And though it is really cool you are rich, I don't need anything from you. I don't enjoy being showered with gifts, or whatever. What I do love is being all dominant and sexy, but that isn't really me. I'm a little shy about myself and how I act around men. I kind of force myself onto them because I'm insecure about myself. Which probably isn't a good thing.”

“Tying them up and thrusting a hand inside them on a first date probably isn't a good thing too.” He told her.

She nodded sadly. “Sorry… I just really love doing it… and you were so wonderful about it. You didn't even say the safety word I gave Miyuki to give to you once. She was supposed to say that if you didn't like anything I did at all, you were supposed to use it. I kept waiting for it, ready for you to stop me from going too far, but you never said it.”

Alex sighed deeply with her on top of him while he felt her penis pressing into his groin. Then he admitted, “You just seemed so happy to do this, I didn't want to disappoint you… Plus.” He finally grinned at the sad looking woman. “I probably would have said no to the makeup, but that was the time you decided to gag me.”

Megan smiled apologetically. “Ya… sorry. But I think you look so cute as a bunny. Sorry I made you shave for just this one dumb thing.” She kissed his lips again. “I kind of wish I had let you keep the beard. You look pretty handsome with it.”

She was silent for a while while she stroked his fur covered chest intimately with her paw. Which was when Alex finally put his own paws around her waist, making her smile and say, “I really am the kind of girl who loves petting and hugging all the time. I know you didn't enjoy it as much as I would have liked, but I am very happy you played along until now.”

Taking a strained deep breath with her atop him, he joked, “I did enjoy having you all over me tonight. It sure made a lot of men jealous of me.” 

That made Megan giggle, a very cute noise that made him like her more.

He smiled in return before becoming serious. “To be honest with you, I think I like this Megan more than the dominant one. The more intimate Megan. The vulnerable Megan. Yes, there were some things I liked tonight, and I don't mind being submissive for someone I can trust, but there were other things that were a little hard to handle and I was pushed into without getting a chance to talk through it. Just ask next time before you shove your whole hand in me. I might just say yes.”

Megan seemed guilty as she nodded, which made Alex start to feel a little bad for ruining her fun. 

It was always hard for him to say no to a beautiful woman.

He decided to offer, “Maybe we can go on a normal date this weekend where I can meet the real you. Just a nice dinner where we can both open up to each other. No lies. No hiding our true selves behind a dominant mask. Just a date having a nice time talking.”

Breaking into a bright smile, Megan nodded. “I'd love that.” Then she asked. “Can we keep being a little intimate, too? I loved having your arms around me. We can tone it down. 

He smiled. “As long as we forgo the toys too, I'm on board.”

She pretended to pout before she giggled. “Okay. And as for the rest of tonight, I think we can just have a friendly cuddle night together.”

As if to emphasize it, she hugged him tighter, pressing her furry body into his more.

“I'd like that.” He told her with a smile. “But there's a problem I think I have to take care of first.”

She looked worried about something else she had thought she had done wrong.

Alex rolled both of them over until he was atop her and teasingly asked, “Is that a carrot in your fur, or are you just happy to see me?”

She became excited again as Alex unzipped first her crotch to free her erection, then his own zipper so he could slide his vagina onto her penis, his wetness being enough of a lubricant as he let her enter him again.

Then he poked her on her nose with a furry finger, and said, “You, my cute little bunny, can just sit there and enjoy yourself while I do all the work.”

“Yes, bunny boy.” She said with a giggle before pulling him into another kiss and to whisper, “Thank you Alex. You are amazing.”

He smiled at her in return, before slowly beginning to ride her.

____

____

“Dear Reader,

Megan's milk and cum were strawberry flavored while Alex's squirts were minty. In case you were curious. (If you know, you know 😉)

-XAREK