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?”


“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!


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!

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