Monday, October 11, 2010

I knew this would happen

Today, I was told that in addition to having a modeling session for all the girls this week, I didn't buy all these pretty clothes to have them just hang in my closet.  When my roommate is gone they want me to dress up at home more often.  They have keys and they have told me they will be checking.   I'm really not sure how much longer I can hide this from her.   When I complained about how much shopping I had to do this weekend, even Amanda told me that we had just scratched the surface.

There is one good thing.  One of the girls who is in on this told me that she thinks I'm cute and she meant in male clothes not female clothes.   Her name is Amber and she's a red head which is hot and she's got a very nice body and a great smile.   I'm really impressed that she is able to see passed the dresses and I have asked her out for Friday night.  I am surprised to see that this has opened up a dating possibility for me.


  1. So they are not all lesbians.

    You say that Amber is hot. Well, take it slow. There are lots of girls that would be turned on by your situation, believe me. But meeting them might not be so easy.

    So take it slow. Let her make the first move. Hold hands, gentle kissing. If she is into you in your situation, she is probably horny as well. Good luck.

  2. Xiu -

    I think you'll enjoy your dates with Amber.... I suspect she'll play hard to get, yet end up being a very friendly person. Treat her like a lady, someone you'd bring home to mother, and you'll have some very enjoyable evenings together.


  3. Xiu -

    Once you're used to wearing feminine clothes, consider going out with Amber as two ladies... You'll have a lot of fun - and she'll protect you and your little secret from being exposed. Heck, going out for drinks can be much easier when an occasional man pays.....

  4. Wow, it does sound like you've been on quite the shopping spree...and you certainly seem to be happy and smiling in the pics; well, you know what they say, girls just love to shop! Just kidding. It does sound impossible to keep this from your roommate for much longer. Do you think she will freak out? Move out? New roommates can always be had. Or, are you just thinking about the embarrassment at someone else knowing about both of your personas?

    The Amber thing sounds great, so congrats on that. A very nice body is a very nice body, and redheads are indeed superhot. It sounds like she's the only one of the group who is interested in you being in male clothes; may Friday night go well for you (it sounds like a rare chance to be as manly as you want to be). Of course, I've actually heard of women who groove on the whole transvestism thing, even forced transvestism (if the rumors are true...), so you're probably covered either way.

  5. Oh yeah, one more thing: are you sitting on a Toronto Maple Leafs rug? That's fine, but it kind of clashes with the whole beautiful China doll image. Just sayin'.

  6. Who is our roommate? Is she a lover? A long time friend? Did you just answer an ad? Are you close?

    Would you be tolerant of your experimentation?

    You do need to start thinking about these questions. You wear a bra and panties all the time, right? She may already have a clue.

  7. Xiu -

    Get used to it.... You're going to get hooked on feminine finery.

    Think of how good those clothes feel when a woman wearing them is next to you. There are a lot of women who secretly desire men with whom they can share this sensuous experience. And you may end up having a greater choice of women after this experience, because of this experience.

    So go with the flow - you may find that you'll have some very enjoyable experiences because of it....


  8. Xiu's

    You have no idea what kind of spiders web you have ben caught in. There will be no harm to you other than you male ego. You are in loving hands but demanding hands. I look forward to watching you gain the understanding of how deep you really are in this.

    Kisses Kim

  9. You really don't have to do this. You have to choose if the potential embarrassment and possible university sanctions are worse than cross-dressing and being dominated. You can stop this at any time. Your choices up till now will probably surface. If you continue the hole you are digging will only get deeper. It's up to you to decide.