Shopping with Jamie

Back in September, we had some painting done in exchange for a little dressing up and a makeover. Jim, or Jamie as he likes to be called,  did a fantastic job and we all had a great time helping him become the girl of his dreams. I recently gave his number to a friend and he called to thank me. He had a very interesting proposition and asked if I was interested.

“So how have you been you sexy thing?”

Oh really good Miss Teresa, really good. In fact I just finished a very large job and have all this extra money!”

“Great! What are you planning on doing with it?”

“Well, thats kinda why I called, I mean, besides to thank you for the reference. I uh, I want to blow it all on clothes.”

“Well that sounds like fun. I just love to shop for new clothes.”

“Well, uh, I kinda was wondering if you’d like to go with me. I mean take me. I mean, uh, help me sorta.”

“Come on boy, I think you’re trying to tell me something. Go on, spit it out.”

“I want to buy myself some lingerie, and dresses, and makeup.”

“That’s nice.”

“I, I uh, I have trouble going into the stores by myself. I, get very excited if you know what I mean and have to leave.”

“I think I do know what you mean Jamie. I know how excited you got as soon as I handed you your panties last time! Have you considered wearing something to hold you in? Maybe a body shaper of some kind?”

“I didnt think of it, no, but I’d have the same problem buying that too. I was wondering if, if, oh nevermind.”

“What is it? You can tell me honey.”

“OK here goes. I have a fantasy about being taken lingerie shopping and having the salesgirls all know that the stuff is for me. If, well I was thinking that maybe you could help me out. I have about $400 I’d like to spend, and if you go with me I’d be happy to spend half of it on you.”

“Let me get this straight. You’d like me to take you shopping, tell the girls that you want to buy lingerie, and that you love to wear girls clothes, and you’ll buy me two hundred dollars worth of things for myself?”

“Yes.”

“Sounds good to me! I’ll tell you what. I’ll get you a nice body shaper in your size, and you can come over and pick me up tomorrow. We’ll get you panties, bras, nighties, makeup, dresses, whatever you want. You do realize that for two hundred dollars you may not get all of that though. The body shaper alone is about fifty dollars.”

“That, that’s fine! That’s great! What time can I come over?”

“How about 3:00 or so, is that good for you?”

“YES! I mean, yes that will be great. You are a wonderful person Miss Teresa!”

“Oh, thanks honey but I think you are too. I’ll see you tomorrow.”

“Thank you, I’ll be there exactly at three!”

“You’re not gonna get all weird on me are you?”

“No, no, I’m just looking forward to it. Thanks again. Goodbye!

YES-YES-YOWZA! THIS WILL BE AWESOME! YEE-HAW”

Uh sweetie-you might want to hang up the phone. See you tomorrow.”

“Oops, sorry. Bye!”

Update: Jamie and I had a ball at the mall!

Becoming A Girl

I’ve been reading some feedback about my hypnosis recordings, and it started me wondering about the long-term effects. Are you sure you really want to become a woman? I want you to promise to think this thing through.

What will you do with all your old clothes and shoes?

Are you going to be happy wearing a bikini at the beach?

Do you know how expensive a good bra is?

Are you prepared to be whistled at and hounded by construction workers?

Can you apply mascara while doing 60 on the way to work?

Do you realize how hard it is to bait a hook with long nails?

Do you know which outfits to never wear on a date?

Now I know that for many of you none of these things present a problem. You already have a drawer full of panties, read fashion magazines, and put your makeup on in the car. But for those weekend warriors that come home from the construction site on Friday, and slip into a silky skirt on Saturday, I just want you to be warned. You may find yourself showing up at work in heels one day and walking into the ladies room. If you do, please wear something tasteful. And NO panties with sayings on them!

Go Ask Teresa-Fear!

Go Ask Teresa

B: I really, really want to order your Beauty School CD Miss Teresa, but I cant risk having it sent to my house! I am so afraid of my wife finding out! I only go to your website when she’s not home, and then I clear all the history! Now she’s been asking me why I’m doing this! I have to have it-its my complete fantasy! What can I do?

Me: GET A GRIP! What are ya, a sissy? Oh yea. How old are ya kid?

B: I’ll be 47 next month.

Me: Listen kid, I have a plan. Now shut up and pay attention. First of all its a download, not an actual CD that would be sent to your house. I send it to your email, see?

B: Oh, I didn’t realize that. But my wife!

Me: SHUDDUP!

Now the first thing ya wanna do is download Firefox. You can have it clear your history every time you sign off, it even asks ya?

B: But…

Me: SHUDDUP!

Now you’re gonna get an email in another name see? They’re all free, just pick a name and remember it. If ya want, ya can write the name and password in a book that nobody reads, get it?

B: Yes Miss Teresa.

Me: You can use a credit card, or if you’re still yeller, an e-check. No traces. Then I send the file to this email that nobody knows about, see?

B: Wow you’re really good at this.

Me: Yea, I been around.

B: But what about downloading and saving the file? How can I hide it?

Me: Here’s what you’re gonna do. Ya download it when no ones around, and save it in a folder. Ya name the folder like another one, but add a letter. Then you put that folder in a different folder that never gets used, see?

B: But what if she finds it and listens?

Me: Ok, lets play it safe. Ya burn it onto a blank CD and stash it somewhere. Drive out to the dessert, get comfy and play it in your car.

B: Not bad, you’re very sneaky.

Me: Thanks kid, but I’m only helpin ya cause this stuff is harmless. So ya like to wear panties and prance around like Cinderella? Who gives a flyin rats ass?

B: My wife actually.

Me: YER A SISSY! Oh yea, that’s what this is about huh? Well, there ya go kid. Now ya can have a party in your pants. Play some pocket pool, adjust the antenna, baste the ham, badger the witness, buff the banana, cuff the carrot, flog the dolphin, milk the moose, oil the glove, rope the pony, yank the yo-yo, knock yourself out.

Just one more thing. Yer not gonna do anything illegal are ya? Anything strange or sick?

B: Oh Lord no Miss Teresa, I just want to wear pretty things and act like a beautiful girl.

Me: That’s what I figured. This conversation never took place, ya hear? Now go grow a pair.

B: Thank you Miss Teresa, but I don’t want to grow a pair because…

Me: SHUDDUP

Prance around eh?

Disclaimer: I do not normally talk like this. I am in no way encouraging anyone to do anything illegal or immoral. Its just that in my experience many crossdressers do not want their friends and family discovering their little fetish. Right Mr. Madoff?