Thursday, October 7, 2010

Rough Day

This morning I was forced to give up the keys to my place so that the girls could make copies for themselves.   I was sleeping in and while I was distracted by one of the girls, the other two put a pair of my pantyhose, a bra, and panties in my briefcase.   I was needless to say shocked when I opened the case before class today and found the undergarments.  They giggled and waved at me.  I was able to keep the items hidden and pull out what I needed. 

Later in the afternoon, Sheila came over with her friend Heather and told me it was time for more modeling.  I was a bit surprised because they had no clothing with them and I have very little myself left over from previous modeling sessions.   They proceeded to have me model my roommate's clothes.   Everything was put back neatly and she was none the wiser, but it occurred to me just how powerful these pictures are.  I refused, but they told me if I didn't agree, they'd strip me to my panties and hose and leave me hogtied for my roommate to untie.   I called their bluff, but Heather got me face down with my shirt off, my hands crossed behind my back and Sheila was looking for something to tie me with so I reluctantly agreed.  I literally had to beg to wear my roommate's clothes before they agreed.   They now can show her proof I was wearing her clothes.   They swore to me that she wouldn't see the photos unless I wanted her to.

I am starting to think that shopping this weekend may be easier dress.  I don't want people to see me enter a dressing room male and leave female or hold a dress up to me so the girls can decided how it looks on me.

UPDATE:  I just got off the phone with Sheila.  I called her to tell her, I'd like to go shopping made up to avoid embarrassment and she told me that they had changed their mind and that I should have agreed earlier.  I asked her to reconsider and she told me that if really wanted to have their help looking passable for the shopping trip that I would have to write her an email begging to be dressed up to go shopping and to be enthusiastic and not sound coerced at all.  She said, if my email was good enough she'd reconsider.  That's just not something I'm going to do.   She had told me it was my choice and now she's asking me to beg to be dressed up and act like this is my idea.  It's just not going to happen.  I'll go as a guy and take my chances.


  1. Yeah, shopping as a woman is obviously the path of least embarrassment. I have a sneaking suspicion that this whole thing is some kind of a Halloween stunt, and these women are in some sort of contest. If I'm right, you're probably going to be off the hook come Nov. 1st, so you might want to play nice with them until then. Again, going along with their plans without resisting---or even pretending to be enthusiastic---will probably lessen the fun for them and make things easier for you; I know, I know, that's easy advice to give to someone in your situation, but much harder to actually follow.

    Also, I just have to ask: how, exactly, did Heather get you face down with your shirt off with your hands crossed behind your back? Are you saying these girls physically coerced you? Are they that big and scary or are you that weak and girlish? Judging by the pics, I guess I know the answer... Anyway, good luck this weekend.

  2. Just show up dressed. Borrow some clothes from your girlfriend/roommate. Fix your hair and nails as best you can

  3. You might want to reconsider that thought. If someone you know goes by and you're dressed as a girl, you can ignore them and pretend you don't know them. Dressed as a guy, in the womens dept, you're going to draw attention to yourself like a magnet. Anybody you know going by is going to notice, stop, stare and tell everybody they know what they saw. Then what? I would suggest sending Miss Sheila that email. Soon. LB

  4. Send the email. Don't say too much. Just tell her how much more comfortable you are in girls clothes and ask her to help you become passable

  5. It seems inevitable that your roommate will discover your cross-dressing. How do you think she will handle it. You make such a pretty girl I hope she isn't jealous.

  6. You could always just make yourself up as a woman without their help. Then you don't need to beg.

  7. Wow, I think I'd prefer to go out as a woman (of course I'm a crossdresser). Well, it will be an experience for you. I can't wait to hear how it goes.:)