The Ongoing Conflict

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A cross dressing short story.
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AlexBailey
AlexBailey
167 Followers

The Ongoing Conflict.

"You never complained when I've dressed like this before."

Michelle stood in front of the floor-to-ceiling mirror in the four-star hotel room, preening and admiring herself in a beautiful new red silk and lace lingerie set. She could see Michael's eyes lusting all over her in the mirror's reflection.

She fluttered her freshly done lashes for his benefit. "I know how much you like seeing me this way."

Michael sighed. "It's not about that. Come on, you know we shouldn't be spending so much money on frivolous things. I've got to save up to get my own place. I don't want to be renting from my parents anymore. It's lucky my client is so generous with this room, but that still doesn't mean I should be blowing so much cash on all of this stuff for you."

Michelle frowned. "I hate it when you're like this -- it's such a drag. What's wrong with getting nice things? It's not like you aren't getting paid for this trip, and besides, you know it's for both of us." She pushed her bra up and took on on a flirty pout.

Michael shook his head and looked away. "Why can't you ever be serious? All you want to do is spend money and have fun."

Michelle ignored him and looked back to the mirror. She knew he wouldn't be able to help himself for long. His is eyes were soon drifting up and down her thigh-high stockings and the silky red thong that hung so sweetly on her hips. She struck a pose so he could admire her athletic figure and beautiful ass.

"Oh babe, I love seeing you in that stuff..."

"You're the one who spotted that store and saw this outfit on the mannequin. You knew I'd like it. I got so turned on when you told the clerk it was for your fiancee." Her eyes sparkled. "It was a nice touch to find it gift wrapped on the bed when I got out of the shower."

"That was very expensive set, but wow! You look so unbelievably fuckable right now."

His arms wrapped around her delicious and familiar body. It was always such a comfort to hold her, especially when she was dolled up so pretty.

"I'm sorry I have such expensive tastes. I just don't know what else to do sometimes. I feel like I need to keep things exciting to keep you interested. What would become of me if you didn't want me anymore?"

"Want you? I think I need you. You're like my perfect partner. We've been together forever and you know me so well--it's hard to imagine hooking up with anybody else."

"Is that what I am to you, just a hook-up? It makes me sound like some sort of home wrecker."

"That's not fair. I don't want to just hook up, I mean..." He sighed. "What I really want is to meet a nice girl in my home town, someone I can introduce to my mom and dad. If only I could bring you home... This is our compromise -- I can only be with you while I'm away on business."

He turned away and went to room's mini-fridge and took out a bottle of Heineken. "Damn it. Still warm. I called maintenance about this fridge last night!"

He popped open the warm beer, took a long pull, and set it down on the dresser. He sneered at the foamy mess it made as it overflowed onto the dresser. He turned his attention back to Michelle and grabbed her ass and thighs.

She watched him fondling her in the mirror, her breath growing ragged as she melted under his touch.

"You just need to find a wife who can be open to me."

"We tried that. It almost worked with Cheryl. God, that was fun, best times ever."

"Cheryl was fun, too bad she decided she was a lesbian."

"Yeah? That was probably your fault. She'd never been with a girl before I introduced her to you." He chuckled. "At first I was scared that she wouldn't be into it, but it wasn't long before she lost interest in me. I almost thought she was going to leave me for you."

"Ha-ha! Very funny." She smiled at his compliment. "I could have gone for that. If it weren't for you maybe I could be a lesbian."

"Oh? So what am I, just a bunch of dead weight? Is that what you want? To be a lesbian? It would make sense the way you went down on Cheryl, made her come over and over again."

"You just need to find a girl who likes it both ways."

He laughed and smacked her on the ass, then went back to take another long swig of the warm beer. It was gross but the alcohol was soothing. He often drank when he spent time with Michelle, knowing that he had to be mindful not to make alcoholism another one of his many anti-social issues.

"Look, I want a family someday, that's really important to me. I'm sorry, maybe if we could have kids of our own..." He chuckled and took another disgusting swig.

"I know. It's just... why can't you find someone who would be open to me? Just put everything out there on a dating app or something. If you find the right girl, we can all been happy together."

He scoffed and emptied the bottle. "The closest I ever came to a serious relationship was with Jessica -- when you weren't around."

She stopped preening and looked away. "You think I don't remember? You didn't want me around at all back then. That was when you kicked me out of your life and got rid of all my stuff. You were a complete asshole to everyone then, it's no wonder she left you..."

"Look, I'm sorry I got rid of all of your stuff, but honestly, I thought I'd be okay without you. I had to do something, I want a family and you can't give me that. You were taking up so much of my time and I was having trouble with money..." He shook his head. "Too bad you can't just go get a job."

"I could if you'd let me. They'd probably hire me at that lingerie shop, could you imagine everything I could bring home? Or maybe I could find a rich sugar daddy..." She grinned and laughed. "Maybe then I could bring home enough so you could quit your job." She pursed her lips and blew a kiss into the air. "I could have fun pleasing men for a living."

He seemed to consider this for a minute. The thought of her pleasing other men was a huge turn on for him. His arousal inspired her and she started rubbing and tugging his swelling manhood. He swooned and let her have her way as they fell back onto the couch. He caressed all of the softest parts of her luscious body with an insatiable hunger. Why? Why did he need HER?

"I wouldn't want you going out there sleeping around just to bring home cash, it's not just gross, it's... I don't know... it crosses a whole bunch of lines for me. I could never look at you the same way."

"But that's my greatest fantasy! To be an object of desire, to have guys wanting to be with me, to get inside of me..."

"Arrgh! Why do you have to be such a slut?" He stood and walked across the room--disgusted and unable to look at her. He stared out the window, off into the bustling lights of the city.

He was slipping away from her. She desperately wanted him to accept her on every level. Maybe it was his upbringing, maybe he was just too socially conditioned to embrace a sex-positive lifestyle.

She stood with him at the window. He wanted to resist but she had power over him. He held up a finger for her to take in her mouth, to run her slutty lips and tongue all around it and get it all soaking wet and smeared with red lipstick.

He needed her now! He threw her roughly onto the bed and set her up on all fours, pulled her silk thong aside and rammed his finger in her ass as far as it could go.

She whimpered and collapsed onto the bed. "Oh fuck yea! Fuck me, baby!"

He held her there while she desperately grabbed his cock, writhing on his finger and tugging him, trying to please him with all of her tricks, pulling on his cock and rubbing along below it's base, firmly squeezing his balls... but he got frustrated. He fell back onto the bed and tried to turn his back to her.

"Fine," she said, "maybe I should just go then, we'd probably both be better off." She scoffed and fidgeted, trying to keep her tears from messing up her lashes.

"That's not what I want and you know it," he growled. "I want us both to be happy, it's just that..." The conflict within him was boiling.

"Just what? What are you going to do? You're never going to take me out, are you? Not even just one night -- somewhere that I get to choose, where I can get dressed up all nice and have some fun with everyone looking at me. You'd love it as much as I would. You love the idea of other guys checking me out, it's a fetish for you, isn't it?"

His frustration was eating him alive."You know how I feel about that. It's one thing when we do this in private..."

"Yeah? private time is fine for you, but what about me? What about my dreams? Am I'm just a girl in a bottle? You don't have to worry because I'll always be here for you no matter what. Even if you lock me out again, you can just say the word and I'll come right back. Just don't be stupid and throw out all of my stuff again, okay? Please?"

He couldn't bring himself to give her what she wanted, but it was ridiculous to deny her--he'd tried, he just couldn't do it. What did she see in him?

She put her hands around his cock again and started tugging and rubbing as only she knew how. If she could get him off, all of the stresses would fall away. It might not be the solution they needed, but maybe it would kick the can down the road for a little while more.

For a few minutes, he let himself fall into her carnal embrace. She knew exactly what he liked and she wasn't holding anything back. He started getting carried away but his thoughts took over and snapped him back out of the spell.

"I can't keep doing this. I wish we could pursue your dreams, but my life is going in another direction. I'm sorry! You're welcome to come along on these business trips, but I have to focus on my big plans and not on this dead-end relationship -- or whatever it is."

"I'm not a dead end. You can still pursue you dreams. Why can't we be together? I can travel light, just one bag. I know it sound's desperate but what else do I have?

He was at a loss, even though he couldn't commit, he had real feelings for her. "You can't move in with me. What if I brought someone over and she found my closet full of your stuff?"

"Just be honest and up front."

"Fuck that! What nice girl would understand this?"

"The right girl!"

He jumped off of the bed and paced the room madly. He finished the warm Heineken and opened another.

"Fine! You can keep one bag at the house and you can stay with me while I'm working out of town, but I don't have time to take you out anywhere."

"So I can come along but we can't go out at all?" She pouted and bit her bottom lip.

He stopped pacing. He studied the sad lines of her face, wondering why she'd chosen him. He couldn't give her what she needed. He'd tried to exclude her from his plans but she always found a way back into his life. Sexual fantasies played a huge part of their relationship, but she also kept him mostly satisfied. He struggled with meeting new people, being with her on business trips made it so he didn't feel the urge to go out for random hook-ups. The truth was, he liked spending time with her.

His mood softened and he held her close again.

She sighed and curled up into a ball. "I guess it's better than getting locked out again."

He stroked her hair. "You make me sound abusive when you say that. I won't lock you out again. You've just got to promise to stay out of the way when I'm dating and you can't distract me from work...and you definitely need to learn to travel light."

"Okay." Her lip quivered and more tears threatened her eyelashes.

She threw herself into trying to please him again. He gave in to temptation, already seeping pre-cum, her hands were just too much. She used a thumb and forefinger to draw a pearly white rivulet from his tiny little slit and let it melt on her tongue. She swooned with delight, she loved the way he tasted.

She couldn't understand why he so often chose to please himself in the shower when she was so willing to give herself over to him completely. She was a master with her hands and was always able to get him off faster than any other lover. He was getting red in the face and was about to come when there was a sound at the door.

-Knock, knock, knock!

"Shit!" He pulled himself away.

"Maintenance, here with a new fridge."

Michael looked around the room, it was a mess. His head was pounding from the interrupted orgasm. Intimates and gift wrappings were strewn everywhere. He jumped off of the bed and desperately tried to gather things up.

The latch beeped and the door began to open. A broad-shouldered man in a hotel uniform backed his way through the entry, pulling a hand-cart with a new mini-fridge strapped to it. The spring-loaded door slammed closed behind him.

"Hey, I didn't say you could enter!"

"Oh, Jezz! I'm sorry, I didn't hear you. Didn't think anyone was here."

The startled maintenance man tried to go back the way he came, but the loaded hand-cart was between him and the door. He desperately fumbled about trying to get things turned around but it was no use.

Michael sighed. "Okay, it's okay. Just... just take care of it and go."

The handsome older maintenance man looked sheepishly over his shoulder. He turned to see the one and only occupant in the hotel room. Michael stood there fully made up with an annoyed look, wearing nothing but a fine matching red silk lingerie set, complete with stockings, garters, thong panties, and a stuffed bra.

Michael resigned to his fate.

The shocked maintenance man quickly set to his task. Stealing occasional quick glances as he pulled the old mini-fridge from under the counter and unloaded the remains of Michael's six-pack.

"Can you hand me one of my beers? You want one? They're kind-of warm."

The maintenance man handed one to Michael and opened one for himself. He took a drink and swallowed hard, forcing a smile that looked more like a grimace.

"Thanks a million," he said. "So you're a cross dresser, hey?" He looked Michael up and down appraisingly and cracked half of a smile. "You actually look pretty good." His eyes stayed on Michael as he took another drink.

It seemed to take forever as he strapped the bad fridge to the hand-cart.

As he turned to leave he said, "You know, I've see all kinds of stuff here at the hotel. It's the city, after all. No kidding though, you look great. I wish my old lady would've worn that kinda stuff..." He blinked and swallowed hard. "I just gotta say, you pull it off better than she ever could."

He propped the door open and pulled the hand-cart out into the hallway. He reached in to release the door, but before it could close he said, "Hey, if you need anything else, anything at all, just ring the desk and ask for Don from maintenance." He winked and a warm smile spread across his face.

Michelle straightened herself up and returned a nervous smile. "You could bring me up some cold beers."

AlexBailey
AlexBailey
167 Followers
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AnonymousAnonymousabout 2 months ago

I liked it. Nice plot twist. Really clever.

MaryannePetersMaryannePeters10 months ago

This was really clever. We have to talk!

AnonymousAnonymousover 2 years ago

Well done! Keep up the good work!

SilkeeSmoothSilkeeSmoothover 2 years ago

I started to see where this story was going, and immediately thought of Fight Club, except with a sexy girl in lingerie 😀

Very creative story!

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