Why I Was Running?

First, I have to say that those boots have about a 3 inch heel and it's a narrow heel. Even without heels, boots are made for walking, not for running. Still, I was blushing when it was pointed out to me exactly how feminine I looked from behind when running. I didn't have to run away. In fact, the guy at the deli really thought me kissing Santa for the camera was funny, but we were in a rather silly mood.

My sister knows about what's been going on now. She's always been really tight with Mistress Susan and while, I don't expect her to be like Colleen has been with Jill, her reaction wasn't sympathy or laughter. It was more like, "what a common sense solution to a guy with a roving eye". That's not what she said, but she seems happy with the arrangement as she's happy Mistress Susan and I are still together. She has made a few comments about me looking like one of my aunts and of course wanted to see me in a dress, which Mistress Susan arranged. My sister is at a different college and we don't see each other a ton and with Mistress Susan and I spending most of our breaks together, she won't be needed to keep an eye on me or anything, so it isn't a major change, but it was still a bit embarrassing for her to know.

I need to pick up a New Year's Eve dress, but I haven't really started looking. I'm supposed to pick up one and take it back to college with me. Mistress Susan suggested that we go shopping tomorrow as we're going to head back to school Wednesday night.

Last Posting

Wow! I was going to talk about Christmas, but I thought I'd talk about my last posting instead. It got a ton of responses and I noticed that they were extremely contradictory with each other. The ones that jumped out at me were the ones who were angry at Mistress Susan for the switcheroo she pulled on me for Thanksgiving. I did in fact arrive dressed male and found myself as the maid shortly after. It was not a huge party all told there were 8 of us, but I always find it interesting when the blog readers get more angry about something than I did. I think that's because I left off a few details.

Mistress Susan is close to her sister and as a result, her sister took a strong dislike to me because she knew of many occasions in the past I had been a pretty crummy boyfriend. I think it was important for Mistress Susan to show her sister just how much things had changed. Yeah, it was tough to be put in that situation. but hopefully it'll break the ice a little between her sister and me.

Things are Changing in a Big Way

Thanksgiving was not what I expected. We went to Mistress Sue's older sister's place to celebrate with her and her husband and some cousins and another sister. Mistress Sue's older sister is nearly 30 and trying very hard to have her first child. She's older and more mature. Unfortunately, we were in her home 5 minutes before Mistress asked her if she minded how I dressed. I expected a lot of questions, but evidently the sister not only knew, but had seen pictures as had her husband. It took all of 5 minutes from me to go from guest to maid and while I didn't make Thanksgiving dinner or anything, I did most of the serving and all the dishes. I felt so small, especially with the real men watching football while I whipped cream for the pumpkin pie.

I'm now considered passable enough to start thinking about a job. I've dated several times now and while Mistress Susan has promised me, she would follow her own path with me, I am so unmistakably girl, that I don't doubt if I was released to be a boy again, it'd be difficult to remember how. There's a part of me that dreads knowing I will be receiving some feminine items for Christmas, but another part that is thinking, I need some new bras anyway.I hope that makes sense.

Found Out

As most of you know, Xiu found out my little secret. I had to make it through four dates with her and that was three and we will be doing Homecoming so I definitely made it. She swears she knew and used her hands to confirm, but I'm pretty sure she was aggressive and got a surprise.

Halloween is coming and that's one Halloween Costume, Sexy Bat Girl minus the cape and mask. We will be having a contest, but I don't have all the costumes together yet. The first parties are tomorrow and like all the sissies I will be going as a fairy. It's definitely weird seeing Halloween from this end.

First Date with Roger (Xiu)

The date went OK. Obviously, he's not my type--and the problem was I knew that and he didn't. I think he was also very intent on proving to both of us that he was the man in the relationship. However, he can be a bit overbearing regardless. Very early on in the date, I started realizing I picked the wrong top because if he was aggressive enough, he'd find out that I was wearing breast forms very quickly. I did flirt and we did kiss several times. The girls saw to that. There will be another date. The key for me is to get the practice they want me to have without leading Roger on too much. He did put his hand on my knee and felt how smooth it was in the pantyhose. I asked him if he liked his pantyhose as much as mine and that stopped that, but I am sort of not supposed to treat him as anything less than 100% masculine.

As for why he isn't furious with me about the feminization--he's not happy about it, but I've mostly stood back and watched. He knows I'm part of the girls who did this, but I haven't been the one giving orders--they've been careful about this.

You'd have to ask the girls why it's so important that we date. It's sort of a right of passage and I guess it is the ultimate passing and a bit of a head trip, but it's not like Jill or Cindy are dating guys all the time. I think if we had steady boyfriends or dated guys on our own or something, they'd be very unhappy.

Xiu and I

By now, you probably should have seen that Xiu and I will be going out on a date this Friday. It seems not long ago I was the unaware guy going out with a crossdresser without realizing it. The trick is, this isn't Susan loaning me to Sheila to embarrass Xiu. This is Sheila loaning Xiu to Susan without him knowing it because it is a very safe way for me to date a boy. I'm going to have to string Xiu along by flirting, teasing, and even kissing. Susan wants to see if I can make it through 4 dates. She said the first 3 are easy. It's funny because despite the supposed stress free nature of things--I'm more nervous about dating Xiu than any date I ever went on with a girl. I'm going to take Friday morning/afternoon to get a new outfit and visit Wendy for hair and makeup talk--which will be it's own kind of embarrassment as she asks me questions about the big night.

Dating

The new background freaks me out. That picture of me floating on the top half of a chair is just weird. Anyway, I wasn't the bait to lure Xiu, but she's seen me as Amber a lot and remains oblivious that there is another rooster in the hen house. I have been subtlety flirting with her though and the plan is that Xiu and I will go out with him unaware that I am actually male. The plan is that it would be great practice for me and it would certainly be a safe way to date a guy who doesn't know my secret. I don't have much say in this and I think this is better than dating some guy off the street who doesn't know.

Redheads get a lot of attention. I never noticed this as a guy. It's weird seeing another sissy taken in. I know what she's in for and frankly she deserves it. Maybe I did too for cheating, but what she was doing was far worse. People pay too much for their education to have a TA messing with it. I guess she's learning a new definition for T&A now. When she finds out about us, we will take her into our little group. Nobody else can understand what we're going through. She is going to be a looker---she's so tiny for a guy and I think could almost pass without makeup.