The girl of your dreams is gay... "It's too bad you're not a girl," she adds... What would you do?
"Your girlfriend is gay and you want to dress as a girl for her sake?" Rose asked in a look of curious astonishment. Her boarder, Rick had just asked her if she could help him dress up as a girl.
Dress as a to ask a girl out on Friday! Dressing him as a girl wasn't a problem, she'd said, with no small amount of laughter in between, but his reasons for doing so had to be the oddest she'd ever heard. "If you'll pardon my astonishment, the answer is yes, I can help." Rose said.
"She's not my girlfriend yet, and she'd not actually gay. She's bi-sexual and right now, or so she says, she's simply leaning towards females. Actually, the way she put it was and I quote: '...if I wore dresses she would be interested...". So, I just thought, for the humor in it at least, that I ask her out again, only this time I'd be dressed female. A sort of 'what's your excuse now' kind of thing." Rick said.
"Honey, I think that statement 'if you wore dresses' part was meant that if you were a girl she might be interested?" Rose said smiling at her young boarder's naivety, courage and even that tenacity to even consider these steps.
"Yes, that's what I thought, but I'm not so sure now! Truth is I think she really likes me." Rick said and then laughed as he added: "Anyway, it couldn't hurt? Right? So I thought, since you're an expert at this sort of thing, that I ask you? Can you make be beautiful enough to turn a woman's head?"
"Honey, I can make you beautiful enough to turn my head but are you sure you really want to do this?" Rose asked hoping he's say yes while suddenly realizing what she had just said. The thought of transforming her young boarder into a girl did appealed to her and she laughed.
Rick assumed she meant that girl's head and his landlady's laughter just the humor in this which was most likely a good thing. A good thing because at that moment his landlady's thoughts would have scared him nearly senseless.
"So that's a yes then?" Rick asked.
"That's a yes, but I've got to warn you or at least caution you that some of this, I suspect, you're not going to like?" Rose said.
"Like? Like what?" Rick asked not really hearing that warning as he tried to image what she meant.
"Like your transformation for one thing. Just slapping on a bunch of makeup is easy. So is putting you into a dress for that matter, but creating something another woman who likes women might like is going to be difficult." Rose said.
"I don't follow?" Rick said.
"Honey, covering your body with girl's clothes and your face with makeup is going to make you look like a girl but you clearly won't be. Of course she knows that and you know that, but what you're asking is that she suspends what she knows. You go to her without a little preparation and you might as well not do this, because she won't be able to ignore the fact you are a boy!" Rose said.
"So how do I do that preparation? I mean you're going to do the makeup right? And you've got the clothes or at least you can get them so what else do I need?" Rick asked confused.
"A mother!" Rose said laughing.
"A mother?" Rick asked completely ignorant of what that meant.
"Do you know how girls know they are girls?" Rose asked.
"I can guess at the obvious? I mean I think so?" Rick said.
"No, that's not it. You're thinking of female. I'm talking about being a girl. Girl's know about being girl's because of their mothers! It's their mother's experience at being a girl passed along on how to be a girl that makes girls really know they are girls." Rose said.
"OK, so you can do that... I mean you can teach me to be a girl in under a week?" Rick asked still not clear what that meant but willing to give in to it for the sake of the rest of it.
"Not really, but I can teach you to suspend some of what makes you a boy and give you a little insight into pretending how to be a girl! But that's about it! OK, look, let me put this a different way: You are going to present a plausible fantasy to her, so you actually have TO BE that fantasy." Rose said.
"You mean like an actor? Like when an actor watches an old person so he can act old?" Rick asked as he tried understanding.
"You know honey, that's close enough I suppose. Yes, it's like being a actor studying for a part that he's going to play. You are going to play the part of a girl so yes, in a way, you'll have to study girls!" Rose said feeling giddy over the prospects of what she was thinking.
"Sure! I mean I can do that?" Rick said.
"Not sure you can, but if you pay attention I think we could get you through the basics!" Rose said almost licking her lips. This girl, whoever she was, wasn't going to reap what she was about to sew and she was having all sorts of images of what she could sew.
"Now, you are being serious about this right?" Rose asked.
"As serious as a heart attack!" Rick said laughing.
"No! I mean truly serious because you are asking me to provide you with clothes? Right?" Rose asked.
"I was hoping you might have something in the boutique that you can let me have cheap. You know, like an old dress or something. Anything?" Rick said.
"Honey, it's a boutique! It's not old stuff and definitely not cheap! And it's not big girl stuff but young girl and little girl stuff. Although I just had an idea." Rose said working her plan on the fly.
"What? Come on, what?" Rick said enthusiastically after his moral fell a little over her comments. Getting his landlady behind him on this was a stroke of genius.
"A young girl look! Not too young mind you, but young enough to capture a lady's heart. You men don't know this, but we, as in women, are push overs for that innocent little girl look. It's the mother in us." Rose said touting a wisdom she was making up as she went.
"Really?" Rick asked.
"Absolutely! You've seen how mothers dress their daughters? Always something cute! Well, that desire we have we're most likely born with so it's in almost every woman and we can't do anything about it. Can't resist a pretty little girl!" Rose said.
"Then that's it! That's the look!" Rick said confidently and in his state of enthusiasm. There was a definite hopeful tone as he added: "Can you help me with that then?"
"Sure can! That's the look then!" Rose said and added: "And luckily that's most of what I've got in the store."
"So you'll help me then?" Rick asked bubbling over with excitement.
"Honey, consider this carefully! OK?" Rose warned.
"What? I will! Consider what?" Rick asked.
"I'm about to spend a substantial amount of my time and no small amount of money on inventory helping you do this! I'm not going to start this and have you suddenly decide it's not worth it or that you no longer want to do this. So I want your word that you'll do everything I ask and wear whatever it is I chose. I'm the teacher and you are the student! Understood?" Rose said with emphasis on that last.
"Absolutely!" Rick said.
"I want it in writing!" Rose said.
"You want what in writing?" Rick asked.
"I want you to state, on paper, that if you walk away from this, you owe me for my time and for the things I've provided." Rose said.
"How much am I looking at?" Rick asked cautiously.
"Four to five hundred for the outfits and accessories and I'm guessing at least two thousand to perhaps three in consulting fees!" Rose said doing a quick calculation on two weeks at forty hours at twenty five dollars an hour plus two dresses, slips, shoes and the rest of it at retail.
"I have to pay that?" Rick said surprised at the amount.
"No! I mean not if you do this! You only owe me that amount the moment you say you're finished which is anytime before I say you are finished. If you last out your training time then you don't owe me a cent. If you don't do this that amount becomes due and payable over... Let's say a twelve month period and as part of your rent." Rose noted as she decided the rough total by twelve.
"I wouldn't be able to pay that much each month!" Rick said doing his own calculations.
"Then reconsider your request carefully, because I'm serious about helping you and just as serious about charging you every dime if you walk away from this." Rose noted.
Rick did! He saw no down side. He saw himself all dolled up knocking on Jennifer's door and watching her heart melt at his effort to win her over. He saw a light at the end of his tunnel.
Rose, on the other hand, and in her vision saw a very cute little girl in the beam of her light. She waited those seconds for Rick to say no way or, as she hoped, it's a deal.
"It's a deal!" Rick said happily.
"Then put it on paper and we can start tomorrow when you get out of school!" Rose said.
"How long?" Rick asked.
"Two weeks. Give me two weeks of your undivided attention and, in return, I'll turn you into the sweetest, cutest little thing this woman has ever imagined." Rose said as truthfully as she could.
"Done!" Rick said happily. He really had no idea what was waiting for him, but at that moment he didn't care. Two weeks was nothing compared to the visions of landing that woman of his dreams in his bed. It wasn't too unlike dressing for Halloween or as he and Rose noted... Acting. He could do this! He was going to do this!
Rose smiled as she took Rick's hand to seal their deal. She meant every word of it. The agreement took a couple of hours to work out, type and take that short trip to the notary public. The two women that worked for Rose's boutique were promised an explanation when Rose was alone as they added their signatures on the witness lines.
"He's going to learn to become a little girl!" Was how Rose started off the conversation that Monday morning. As she imagined her two employees stood speechless and gave Rose their undivided attention. It took about fifteen minutes for the whole thing to be explained and roughly another ten to get the women to stop laughing and back to work.
Rick meanwhile watched the future love of his life move between their two classes. Jennifer was as aloof as she had been and Rick as happy as he'd ever been over that. "Your heart will soon be mine my love!" Rick whispered to himself.
Meanwhile, Rose was shopping for Rick in her shop. She and the girls decided on a Disney Princess print that seemed fitting and tea length for it's formal appeal. If Rick was going to be a proper acting young lady then that dress fit the bill wonderfully. Besides it had an adorable pair of lace bloomers and needed a sizable petticoat to give it a little "bloom".
As Rick was nearing his last class Rose was gathering the last of his clothes. He would sleep in a satiny Barbie nightgown over Disney Princess day of the week panties. Before bed he'd be that little princess she promised or at least dressed like one.
If you liked this post, you can leave a comment and/or a kudos!
Click the Thumbs Up! button below to leave the author a kudos:
And please, remember to comment, too! Thanks.