Friday, October 8, 2010

I Caved In

Between some of the posts on here and talking to Sheila's friend Amanda, I decided that the least embarrassing option was definitely to go ahead and beg to go dressed up.  I thought of dressing myself up, but I'm just not that good at it.   It would have been the worst of both worlds to go out in public after I did my own dress, wig, and makeup.  Amanda promised me, she wouldn't put me in anything too ridiculous since she'd be embarrassed too if I was read while she was with me.  Amanda's a lot more reasonable.  I tried to get her to promise me no heels, but she said Sheila would never go for it.  She did promise nothing impossible to walk in.  I'm scared to death about tomorrow.   I wrote down every outfit suggestion you all gave me.  I probably should just get to bed.  It's going to be a long day.


  1. I am glad to her you desided to go as a girl, will help you alot not standing out. And I cant wait to hear about your shopping trip, I am sure it will be sooo fun.


  2. Smart girl. (Yes, girl. Get use to it.)

    It sounds like you have found a friend. Stay close to Amanda. Hold her hand when it gets scary and don’t worry. You can be completely passable.

    I don’t know what your voice is like but let them do the talking if you can.

    When they finish dressing you, give them both a kiss on the cheek and say thank you. Go with it. How hard or easy this is is up to them. Be appreciative.

    I know that you think that you already know all about women. But no man does. You are definitely about to learn about life from a different perspective. Maybe they are not lesbians. Maybe they are just looking for a guy that understands life from their point of view. You may wind up better off as a guy when this is over.

  3. I think you'll be glad you gave in. Have fun.

  4. You probably made a sensible choice. The email may be used as leverage at a later date. I assume you are back from your shopping when you read this. I would wager you have way more clothes than you expected. What do you think the girls long term plans for you are? How far are you willing to go with this?