It All Goes Wrong, Pt. 02

It All Goes Wrong, Pt 2

(Crossdressing, FLR) Crossdressing victim

By ChangeYourPassword

Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you enjoy this story and the fetishes involved, great. If not, please forget the whole thing.

Read the previous part of Wrong, first.

It had been such a long and disastrous day, and now when she was feeling just a little bit better, Andie was terribly afraid she was about to make her life even worse. But she just had to take the step off the cliff.

"Keira, I have a confession to make." She whispered, hesitantly. The place wasn't crowded; she doubted if anyone would hear, but she was very nervous and afraid over what she was about to do.

Keira, sensing trouble tried to laugh it off. "Oh? You're not going to tell me you're an axe murderer, or a Chinese spy, are you?"

"No, no. Nothing so sinister," she replied with a sick smile. "Um, ya see, this was my big vacation trip to enjoy my fetish, and live out my fantasy."

"Oh really? What fetish and what fantasy?" She smiled, both intrigued and entertained.

"Keira," she sighed. "I'm really a guy, a crossdresser."

And then, hurriedly he added, "I'm not gay, I like girls, I just love women's clothes, and their, um, lifestyles."

He watched her intently for a reaction. Afraid of seeing disgust, or anger, or laughing contempt. But what he saw was a gentle smile and, she thought, perhaps interest or even affection.

"Well, that's a surprise. Tell me more. I never would have guessed." And she actually reached over and rested her hand on hers.

"Your voice is a little deep for a girl, though."

"I know. That's one thing I haven't been able to fix," she mumbled, still nervous.

Andie paused, unable to continue. She was relieved by Keira's reaction, or lack thereof. She had been hugely afraid the woman would freak out and abandon her. But she didn't know what to say next.

Keira solved her dilemma. "Okay, so tell me everything. How did you discover your fascination with women's things? I've met plenty of trans people. Around here they're common - no big deal. Some of my best customers are girls who were born boys. But I've seen very few crossdressers. I'm not sure if they're just not that common, they don't come out, or if I just never knew."

For the next twenty minutes, Andie opened up about her fetish, for the first time in her life. It all came spilling out. From his normal upbringing, as a boy doing boy things, through his dating years chasing girls, to when he discovered his fascination with women's clothes, girl power, and girly things.

Throughout his ramblings, Keira sat quietly, nodding gently, smiling supportively, and Andie, relieved, continued on and on.

"So, you just now decided to actually try it? To try living as a woman?"

Sadly, she nodded. "Yes. This was supposed to be my big adventure. Out in public as a woman, for an entire week. I practiced and built a wardrobe and everything. And look what happened." And she actually started to cry, like a girl.

Keira instantly started feeling even more sorry for her girlfriend. And she did think of her as a girlfriend.

Her sadness too was different from what it had been. Before she felt sorry for her as a mugging victim. But now there was a different flavor to her feelings. Andie was truly screwed.

Keira sat quietly for a few minutes analyzing her feelings, further. She was indeed both surprised and intrigued by it all. She'd never really talked to someone like Andie before - a crossdresser, at least not one who admitted and lived that particular kink. And she had already decided that she liked the girl, Andie. Now she was wondering if she'd like the boy, Andy - or if she even had to...

Wiping at her eyes, Andie continued. "I never thought about sex with men. I still wanted women, but I got the most turned on when I dreamed about all of the wonderful things girls did with their clothes and makeup, and with their beautiful bodies." She explained, still trying to explain.

Realizing that she was repeating herself, rambling, she just stopped, and waited for some response. A verdict on her future.

Keira looked at the pitiful girl for another minute. "Andie, relax. I have no problem with you enjoying dressing as a woman, or behaving like one.

"Actually, I think it's fascinating. And I like you, a lot. I'd like to know more. Why do you think it fascinates you so much? Does it turn you on?"

Surprised and feeling incredibly better, Andie sighed. "It does turn me on."

Andy, the guy, had never tried to explain his fixation to anyone before, not even to himself. It took him a while to formulate an honest answer.

Keira sat attentively and waited for her.

Finally, he shrugged and tried to describe his feelings. "Girls have so much fun. They can change the way they look, and dress and be so pretty and sexy. Guys can't.

"That seems so, um, powerful. The control they have, and how they can use that power to get better treatment. To get what they want."

"Power? Like magic?" Keira asked, with a soft smile.

"It is a kind of magic. And I find it enchanting. It really turns me on. I know it's weird."

"Oh nonsense, it may be a fetish, but it's not weird at all. There are plenty of other much more bizarre sexual fantasies.

"But would you rather be a woman? Instead of a man, I mean."

That was a tough question, especially there and then.

"I'm not sure."

Andie had to think about it. She decided to go with her initial reaction. "I suppose, not really. I'm happy as a man, and like I said, I enjoy sex with women. Actually, only with women, but I love dressing like this." She couldn't find anything else to say, except. "I guess you could say it's my favorite hobby. I practice at it a lot."

Keira giggled. "Some hobby. But it makes you horny, right? Isn't that the way fetishes and sexual fantasies are supposed to work?"

Andie smiled and nodded. "Yes. Absolutely."

They lapsed into silence, both evaluating the situation. Andie, again started worrying about what she was going to do to get out of the mess she caught up in. While Keira was reviewing everything that the girl, or was it guy, had said. She did find it intriguing in a captivatingly kinky kind of way. And she realized that she was very turned on by Andie, and the whole idea of, what did they call them? 'Transvestites'

Her libido was definitely excited by the idea of sex with a girl who was also a guy, and that one most important aspect. She had a cock.

She preferred sex with other women, more so than with some hunky guy. Girls were so much more loving, softer and more in tune with what she enjoyed when in bed with them.

But she did occasionally miss the feel of a hard cock, a real one, inside her. Bree had hated her for that.

Here though, was Andie, who just might be a happy combination.

She was getting very excited about trying that out, when Andie, with tears in her eyes, broke into her reverie.

"I'm really sorry. I've led you on, like this. You've been so kind and helpful, and, uh, loving." She said, sadly.

Keira was touched. Along with everything else, Andie seemed to be sensitive and concerned. More like a woman than a man. She loved that!

And based on her response to that last big question, she didn't think Andie was really certain whether she preferred living as a man or a woman. That was intriguing as well.

Keira looked over at her fondly.

"Now I really do have to invite you to stay the night at my place," she said, smiling radiantly.

Surprised and relieved, Andie replied flippantly. "Because I'm homeless and screwed?"

"Well, that, but more because I'm fascinated and want to get screwed." And she broke up, laughing.

Andie perked up. "Really?"

Keira smiled excitedly. "Yes, really. It sounds like great fun. And I do like you, Andie."

She stopped and stared for a moment, then chuckled. "Andie, the girl, I mean."

They were both thinking happily about next steps, when the waitress came by and brought more wine.

Happily, they sipped for a while.

Then Keira shifted her chair around the table to sit close beside Andie, and gave her a kiss. Excitedly, Andie kissed her back, and the little session lasted for quite a while.

Eventually Keira broke it off, and leaned back.

"Now tell me more about your escapade, here. It's your attempt at really living your favorite fantasy? Is that what you said?"

"Yes, I've been building up to it for months. I had a full week of playing as a woman all laid out. And then..."

"And then it all went terribly wrong. Right in front of my store."

"Exactly."

"Seems like fate." Keira said, smiling.

"Huh, karma." Andie replied, unenthusiastically.

Keira chuckled. "Good or bad?"

"Both?"

"Good, I hope. We can work past the bad." Keira replied.

"I hope that, too." Andie said. She wasn't sure how, but she hoped Keira was correct.

They again paused for a moment, sipping their wine and scanning their surroundings. Andie was relieved that no one was paying them any attention. Apparently, her secret remained safe.

Keira resumed her curious questioning. "Back to your adventure, you mentioned challenges and rules."

"Um, well..."

Keira could sense that Andie was embarrassed, and didn't want to go into those details, but she was intrigued, and wanted to hear more. Actually, she wanted to hear everything.

"Come on, give. Be a good girl. You owe me."

Sighing, understanding that she did indeed owe Keira the entire story, she began to list the challenges and rules she'd established for herself. All of them. Even the humiliating ones.

She was relieved that Keira only giggled a few times.

"You have indeed set yourself up for an exciting time. And from the sound of it an uncomfortable one, as well. But we women must suffer for our beauty. Right?" Keira asked when Andie completed her list.

Andie, chuckled, "that's what I decided."

"Well, my dear, we'll just have to make sure you do." Keira said. And Andie wasn't sure, but she thought she detected a bit of mischief in her tone.

"What? Suffer?"

"Perhaps, coupled with enjoyment, of course."

That answer thrilled Andie, beyond anything she had heard all night.

+++++++++++++++++

They finished their drinks and Keira paid, before they got up and headed out. Andie was now anxious for a whole different set of reasons.

She'd never made love to a girl, as a girl. And she didn't want to disappoint lovely Keira. What she really wanted to do was make love and make her savior, host and new girlfriend a very happy woman.

She just didn't know if she was up to the task.

As they were walking back toward the shop, and Keira's apartment, holding hands, Andie asked, "do you have any men's clothes for me to change into? In your store, I mean."

"Andie, silly girl, you were in the store all afternoon, did you see any?"

"Um, no. How about in your internet store?"

"Oh, there's nothing like that on there. And besides, I don't like men. I liked cocks back in high school, but the boys all seemed to be pricks." And that description cracked her up. She paused to laugh, and Andie joined in, tentatively. What did that mean for him?

When she finished giggling, she added, "I'm only into girls, now. But I have to say, a girl with a cock does seem interesting.

"You need to stay a girl, and follow your rules, if you're going to sleep with me."

And she emphasized her point by stopping and pulling Andie into a hug, and then kissing her on the mouth, energetically and lovingly.

When she broke it off, and stepped back, smiling, Andie smiled back. "That works for me."

After that, they resumed walking at a faster pace. Both anxious to get somewhere with a bed.

Keira took her around the back past a small parking and unloading area, where a solid door led to a small storeroom. It included a stairwell with steps leading both up and down.

"I keep my inventory down there," she said casually as they began climbing up.

At the door to her apartment, Keira turned to face her. "You can stay here, with me until you get things arranged."

Then she leaned in and gave her a very pleasant kiss. And Andie kissed her back.

It only lasted for a few seconds, but Andie, was both relieved and overjoyed, and she could feel her cock, bent back between her legs, start to swell uncomfortably.

"Thanks. You're being so very good to me."

Keira giggled, "my pleasure, I hope."

Inside, after locking the door, Kiera led Andie by the hand straight into her bedroom. It was a very nice room; large and lovingly decorated with a fashionably feminine touch, and with a big bed.

Kiera then grabbed her and they hugged and kissed, for real. Andie was floored. For the first time since the mugging, she felt happy. More than happy. Her savior was astoundingly wonderful!

"Turn around." Keira requested, and when she did, Keira unzipped her dress and let it fall to the floor.

Andie stepped out of it and turned to face her girlfriend, standing in her bra, corset, panties, shoes and stockings. She thought she looked very sexy and feminine like that, and she hoped that Keira would feel the same way.

Keira did appear to like how she looked. She smiled and nodded. "Wow, that's a fantastic corset."

"It's awfully tight and stiff."

"Why did you commit to wearing it then?"

She sighed. "I made myself promise to be as shapely and sexy as possible for the duration of my adventure. It's part of my fantasy, female life."

"I like it. I like all of your rules. Although I may want to add a couple more. Will that be okay?" she asked, with a playful smile?

Andie thought she looked and sounded cute and affectionate. And the idea of the enticing woman adding more rules, made her even more excited. She smiled back, "of course. I owe you."

Keira giggled and began running her hands gently up and down her body. The gentle scratch of Keira's nails sent shivers up and down her spine.

Standing there, caressing and kissing, Keira began removed pieces of her own clothing, revealing her beautiful body, bit-by-bit.

By the time Keira was naked, Andie was quivering and stammering, and her poor cock was aching, jammed back by her gaff.

Keira leaned in and gave her another beautiful kiss. "I have a new rule for you."

"Oh really?"

"Yes. Now tell me how's your cock feeling. It's tucked back between your legs, right?"

"Yes. And it wants out." She replied, with a nervous chuckle.

"Well, that's my new rule for you Andie. That thing stays between your legs, until I take it out. Got it?"

"Um, yes."

"Promise?"

"Yes."

"Good. And don't; worry, I do intend to put it to use, but you're first and foremost a woman, so you'll always start out making love like one."

That actually made Andie's cock hurt even more, as it swelled even more. She moaned.

"Problem?" Keira asked, merrily.

"Um, no." Andie replied, not wanting to admit how excited her cock was.

"Excellent. Now come here. First, we need more kissing and cuddling, and then you need to make love to me like a woman, with your mouth. That's how we'll always start our love-making."

While Andie was still focused on her comment about 'always', Keira dragged her onto the bed, and sprawling on top of her, she began kissing, licking and nibbling on her new lover's mouth.

Andie loved it, and did her best to return the attentions. She also let her hands wander around on her host's bare body. Wonderful!

They kept that up for quite a while, but stopped when Keira rolled off to lay next to Andie, on the mattress. She folded her arms up behind her head and spread her legs.

"You can thank me for real, now." she mumbled, as she nudged Andie with her hip.

Andie was more than willing to oblige. She felt she owed the woman, was anxious to pleasure her, and was very much looking forward to enjoying herself, too.

"My pleasure," she muttered as she rolled over on top of the woman, and then slowly slithered down to lay between her legs. She paused at Keira's breasts which were perfect and had large, aroused nipples which she just had to suck on. For a moment she was jealous. It would be so much fun to have real breasts with pointy nipples sticking out and tenting her tops, erotically. She knew how that turned on every red-blooded man.

She was able to elicit several moans from dear Keira before she lifted her arms and used them to gently push her downwards, toward her sex.

While she slithered down, she stifled another moan. Her cock was killing her! It wanted out of its padded prison, and into Keira's pussy.

Andie paused again to tickle Keira's navel. Pierced by a delicate little ring.

"This is cute." She mumbled.

Keira giggled, "a gift from a friend. "

"Must have been a very good friend."

"She was. And still is, actually.

"I would consider the same for you, but as you'll always be wearing your corset, it wouldn't be worth the effort."

Andie moaned at the thought, and then continued her movement downward, and at last arrived at her new lover's pussy. It was glorious. Smooth, soft and hairless, and Andie was excited to see just the tiniest tip of her clit nestled in its hood.

"Oh God!" she whispered, only just loud enough for Keira to hear.

"You like?" she asked giggling.

"I love."

"Well?"

"Hmmm," Andie mumbled as she began kissing, then licking and sucking.

Then it was Keira's turn to moan and groan, as well as shiver and squirm.

It took a while, but Andie was pleased, proud and relieved as well, when Keira let out a squeak and orgasmed, while her mouth was still covering her very wet pussy.

Andie was pretty sure her lover had orgasmed, he breathing and her little sounds certainly indicated that she had. And, of course her pussy was indeed very wet, and it wasn't all from her mouth.

She continued to kiss and lick, gently while Keira slowly caught her breath and relaxed.

"That was lovely." She finally sighed.

"Good."

"But I think you can do better on the second one."

"Oh really?" Andie said, only a little disappointed. "A second one?"

Keira giggled. "Of course. You know us girls can enjoy multiple orgasms, back-to-back. I'm afraid that's one aspect of womanhood that you, dearest Andie, won't be able to enjoy.

"Now keep licking gently for a while, and then I'll coach you through my second one, and it will be much better. You'll learn."

"I'll try."

"You're good, but I'll explain how you can be so much better."

By the time Keira had enjoyed two more orgasms, each better than the previous one, all due to improvements in her technique, Andie's tongue and mouth were tired and feeling weak and sore. She was happy though that she had succeeded in giving Keira so much pleasure.

But her cock was begging for use.

Keira seemed to understand, as after she caught her breath, she instructed her to shift back up and when Andie arrived, Keira positioned her on her back, head on the pillows.

"Oh my, you're a mess," she said as she reached over onto her nightstand and grabbed a handful of tissues, using them to wipe away the liquid smeared around Andie's mouth.

Then she kissed her, passionately, and Andie loved it.

Several fun minutes later, Keira climbed up onto her knees and then crawled down to squat next to Andie's knees.

There she first stripped off Andie's panties. Of course, she had arranged her garters to be underneath her panties, like any sexy woman would.

When she began pulling the gaff down, Andie automatically reached to help, but Keira swatted her hands away. "Hands off, lover. My fun."

Andie chuckled as she pulled her hands back up. "Yes, miss."