A Perfect Match

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Derek wasn't sure why he was going to the speed dating place. He'd never successfully found a girlfriend in his life. He'd been on a few dates during his college years, but nothing ever lasted. It wasn't just the girls, either; Derek had never really "felt it" with any of the girls he'd dated, hence why it never lasted longer than one or two dates. By this point, he'd basically given up on dating anyone. He didn't think the human race would be missing much if he failed to reproduce.

Derek had graduated college and was now working as a sales pitch. He lived alone in a smallish house, but he was still in contact with his family. Just yesterday, he had called his mom for some support. For all his successes, there was something inside Derek that didn't feel complete. His mom suggested he go to the dating club, hoping he could hit it off with a woman. Of course, she didn't know the real reason Derek didn't enjoy life...

However, Derek went to the dating club anyway. He got a name tag from the front booth and was told to find Booth Number Twelve. "Twelve, twelve, twelve," Derek muttered. "I wonder what kind of girl I'll meet there."

Derek wasn't really watching where he was going. A blonde girl about his height, wearing extremely short shorts and a shirt so small it might as well have been a bra, ran right into him. "Oof!" Derek exclaimed.

"Ohmygosh, I'm so sorry," the girl said. "Ohmygosh, why do I keep saying ohmygosh?" she gasped. She looked down at her boobs. "Holy smokes. Look at the size of these things!" She felt her boobies, then looked at Derek. "Eep! I'm so sorry, I gotta get out of here," she said. "You're really cute, though. You wanna go on a date sometime. Ah, did I just say that? Sorry, gotta go!"

Derek just stood there, flabbergasted, as the girl ran away. He should've been flattered that an attractive girl called him cute, but he didn't for some reason. She had seemed so...dimwitted, and even kind of flirtacious. Derek had met girls like that before, and they were most definitely NOT his type.

But Derek just shrugged it off and went to Booth Number Twelve. Waiting for him was a twenty-something year old woman, with a tight white shirt, wavy brown hair, and coffee-brown skin. Her expression, though, was the strangest of all. She had a seductive look in her eyes, but she looked at Derek rather judgementally. It was as if this girl was a fortune teller, and was looking Derek up and down for clues about what kind of person he'd turn out to be.

"You're late," the girl said in a smooth, almost bored voice.

"Sorry," Derek said, sitting down.

"You must be Derek Phillips. Part time geek, full time sales pitch," the girl said.

"Uh, yes, that's me," said Derek. "What's your name?"

"My name is Carmen," said the girl. "But it's you who's important right now. You're modestly well off, but you still don't enjoy life. Do you?"

"How...how did you know that?"

"Relax. I know all. I know you better than you know yourself." Carmen leaned back in her chair. "I could lean back like this all day and you'd never once stare at my rock hard nipples. Would you?"

Derek glanced at the nipples bulging through Carmen's shirt, and quickly averted his eyes. "No. I want to, but I can't."

"And why is that?"

"It's out of respect, I guess."

Carmen shook her head. "Come on. You and I both know that's not true. You're jealous. You dress up in those lacy panties every night now. You've even gotten a thrill out of wearing them to the mall."

Now this girl was creeping Derek out. "But...how did you know that?" It was true, Derek did have a secret stash of women's clothing. He'd always been curious about how it felt to be a woman, wearing different kinds of clothes and doing different things with his life. How he wished he'd been born in a different body.

Carmen smiled. "Let's say I had the power to turn you into a beautiful young woman. Is that something you'd like me to do for you?"

"Yes," Derek said without thinking. Even after he said it, he felt no regrets.

"I knew I found the right guy," said Carmen. "Now, how do you imagine yourself as a woman?"

"I guess I just see myself as a plain version of me," Derek said. He didn't notice his facial hair fading away, or his hair growing out, or his butt getting bigger, or his waist shrinking. "And with boobs."

"It's always the boobs," Carmen sighed. "And you don't want to be plain. I don't do plain."

Derek smiled as his hair turned red and reached his shoulders. "Well, yeah, I do fantasize about being sexy sometimes," he said as his two lumps of fat appeared on his chest. "Maybe a hot redhead librarian type." The changes were completed when Derek's manhood shrank down until it was nonexistant. "Wait-my voice!" Derek said as his voice cracked and became higher-pitched. The name on his name tag blurred out and was replaced with Debbi. "Ohmygosh...that girl who ran into me earlier-you did this to her, too?"

Suddenly, Derek looked down at her new body. She saw her boobs, just as big as she'd always wanted them. "Oh my! Hello, girls! Can I, uh...you know..."

"Go ahead," said Carmen. No one is looking." Derek immediately got to feeling her new perky boobs, and running her fingers over her crotch and feeling her new vagina. "And yes, I did make an adjustment to that girl earlier. He was a total jerk, and he deserved it. But you, every record of your life has been swapped. You're Debbi Phillips now."

"Am I going to become some dumb blonde like the other guy?" Debbi asked.

"No, no, no," said Carmen. "I only do it to people who deserve it. Plus, I know one more secret about you."

"You've batted a thousand so far," said Debbi.

"You're gaining a lot more self-confidence, and motivation to continue in life," said Carmen. "And there's one more thing."

"What is it?" Debbi asked. A thought was forming in her mind already as she stood up.

"You're still attracted to women," said Carmen, standing up herself.

"It seems so. Is that it?"

"You're attracted to me. The feeling's always been mutual," Carmen said as she put her hand on Debbi's shoulder and looked at her seductively. "But even more so now..."

Debbi bit her lip. She could feel her sexual instincts kicking into overdrive. "Are you gonna do something about it?"

The answer came with Carmen pulling Debbi into a tight kiss. The two women indulged themselves in kissing, relishing each other's moist lips and boobs rubbing against each other. It felt better than anything Debbi had ever experienced. When the two parted, it was almost painful.

"Debbi, go back to your home. Check out your new life," Carmen said as she left. "I'll be by to see what you want to do tomorrow..."

"Wow," Debbi said as Carmen left. All along, there had been a lesbian woman inside of a depressed man's body. Now that her true personality had been freed, Debbi felt even better. "Now this is something I could get used to," said Debbi. "She's so attractive, and powerful. She's the perfect match for me." Debbi left the dating club, already looking forward to the stuff she'd be doing with her new partner.

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Comments

That was nice!

Monique S's picture

My dream all through my youth until I realised I live in the real world and did something to become more real myself.

It nevertheless is a nice fantasy and even with female hormones for a long time it is possible that the sexual orientation does NOT change.

Thank you for a pleasant read,
Monique.

Monique S

Orientation

I firmly believe that sexual orientation is separate from gender orientation and birth sex. Just consider, there are plenty of born women that have been saturated with female hormones their entire life that are lesbian. There is even anecdotal evidence that mature women are switching from heterosexual to bi or lesbian, so it would seem that the female hormones don't have as big an effect on sexual orientation as many believe. The same seems to be true of men.

I enjoyed the story, except for a fear that his/her fate was tied to the big-busted (apparently bimbo) blonde in the scanty top and shorts. The witch (?) could have a TERF that was offended by male crossdressers and was punishing them. I do agree with Carmen, the big boobs fantasy is kinda cliche. Big breasts, like anything big, require more effort and maintenance. A decent "B" is plenty, and they don't get in the way. LOL, I saw a cartoon online that showed two very large women (DD - DDD) trying to kiss each other on the lips while standing up, in public. They were having to deal with some big obstructions!!


"Life is not measured by the breaths you take, but by the moments that take your breath away.”
George Carlin

Male Lesbian

Daphne Xu's picture

A het man is internally a lesbian. Then he gets a date with a lesbian, who transforms men. This was his lucky day, at least in his view. Someone designed it that way, of course.

Nice story.

-- Daphne Xu

-- Try saying freefloating three times rapidly.

fun story

Patrice_Blu's picture

Enjoyable fun story

I am Me, a crazed soiled senior dame

Living the dream...

She is now living the dream that 'he' always hid away.
A short little story that ends sweet and is on point.
On that front well done.

However, as a fellow writer I try to give a few creative pointers.
These are for one subjective and on the other hand not meant to diminish or belittle your story.

About writing:
-You have a few passages that are very front heavy. Often starting the same or similar.
(Derek wasn't sure..; He'd never successfully...; He'd been on...) Try to vary it a little more to break a monotonous rhythm and entertain your readers more.
- Dialogue is hard to write. It is easy to fall into the "he said"/"she said" rhythm. You mostly avoid it, but there are a few passages that reduce to he/she said/asked.

Characters:
- We don't know much about the characters which is, of course, understandable as it is a short story. However, Derek is more fleshed out than Carmen. Which is fine if you play Carmen as the "mysterious woman" type. But I would have hoped a little more detail on Derek. You know, I bet there are a ton of secret cross-dressers out there that aren't really happy with their life. The story makes it seem that Carmen waits especially for Derek to arrive, yet we don't really get a glimpse what sets Derek apart. What character traits of his has Carmen select him and not someone else?

- At the beginning Carmen appears a little bit stand-off-ish and dismissive. Despite that she admits not very soon alter that she was expecting him. If her goal was from the beginning to find someone to be her perfect girlfriend, I reckon she would have tried for a friendlier approach.

- The middle part is mostly about how Carmen already knows what type of girl Derek would be and that is what attracts her, right? So, she works with what she got before her. But in the last part it appears that she plain out uses her powers to bend Debbie to her will. I imagine Debbie would have been grateful anyway and a more seductive teasing approach would have suited Carmen better, I think.

That is all.
I hope this constructive critique helps you.

Hugs and kisses,
Cassy