The Makeup Chair

Today really wasn't supposed to be such a rough day for Cindy. It was cold and rainy all day, which isn't unusual, but things were looking up this week. Unfortunately, Cindy was invited by some friends to go to a party and we had actually given her last night off with the agreement that today she'd spend the whole time working on her makeup. When she asked me if she could go I told her that I bet her friends would love to see one of her new outfits and let her know that she'd be staying home. She would have none of that and we actually had to handcuff her ankles to a chair so that she would be stuck at the makeup mirror. We also had to make sure somebody was there babysitting her at all times. Tonight we turned the responsibilities over to Jill as we all had places to go.

Somebody had asked about having Cindy photograph different looks, but Cindy isn't quite there yet. Her makeup skills are that of your average 11 year old girl. Clumpy lashes, smeared lipstick, poked eyes are all par of the course. If Jill is any indication, she'll pick it up pretty quickly.

Makeup Sites

Wearing makeup is an important part of being a sissy and when we want Cindy to look her best, we're happy to make her face our palette, but I think it is much more feminine and much more powerful for her to apply her own makeup.   She's gotten a lot better after walking on her heels this week and while she's not there yet, a lot of my girlfriends aren't either.   When you wear heels 4 or 5 times a year, you're not going to be real graceful in them.    I think this weekend we're going to make her sit in front of the mirror and keep practicing her makeup until she's competent.  Do any of you sissies have any suggestions for good websites with tips, especially videos that she can watch.

A Few More Answers

I got some great comments so I'm going to go ahead and give more insights.  It's sometimes tough to remember questions so I don't always get to answer:

Tying up the sissies - Thanks for the helpful links.   When we starting to feminize Jill we practiced on each other and used some videos to figure things out.   I prefer using the lark's head method.  It makes for a good knot and it isn't too hard to do.  We found some Youtube videos very useful from Ropeworld.

I really enjoyed some of your ideas for a web page.   Sissy advice or beauty advice could make for some great columns and it would embarrass them to have to write them which is a big bonus.

Dating Update - They will start having bi-weekly date nights on Friday nights.  As Cindy gets better in the feminine roll, they will start alternating, but for now Cindy will be the guy all the time.  I know what some of you are thinking, why let either of them be the guy?  We thought it'd make it much more fun if when they were acting romantic, they couldn't always just imagine that they're with a girl.  We're still not going to make them go real far, but some hand holding and a little kissing doesn't seem too much to ask.

It's possible we'll do a joint sissy blog too or we'll just have the web page take care of their together posts.  It does make sense that it's more difficult for people to message them individually about things that effect them both.

Come Summer they will have no access to boy clothes.   However, we did decide not to do anything that would be permanent to them.   I also just don't like permanent makeup--I don't wear a ton, but I believe makeup should be different depending on the occasion.  

Stephanie--we're in the midwest not in Texas.  The snow is just about off the ground except for some tiny little patches.   It won't be time for shorts and thin shirts with bra outlines for another 6 weeks.   I'll definitely get pictures like that come Spring time.  So far we've let some of our friends know what's going on and they've loved it.  Our friend Michelle has let us use her sorority a few times for fashion shows and a few of her friends know about it.   Jill's roommate knows and he's very open minded--he's a good guy.  There are a few girls on campus who work at shops that Jill has got her clothes at.   In general, everybody's been real positive, but then again we haven't told anybody that we thought would react negatively.

You Guys Are Tough

I love the comments you post here and on their blogs.  I don't want to slight anybody, but I wanted to answer a few things.   Don't expect Jill or Cindy to be jumping for joy over their progress.   They're both new to the whole feminization thing and as soon as they get comfortable we push them past their comfort level--mean, but fun.   Cindy has a lot to master in a short time.   The biggest reason we decided to femme her is that Jill needed a roommate for summer if she was going to stay down at school.   We've got some fun ideas for their summer and we'll be looking for a place for them for summer soon.  Most of you post anonymously which I know saves time, but it makes it harder to tell you all apart:

I'd never say never about additional sissies, but we're not planning on more.  Two is a lot of work, but opens up interesting possibilities too.
I could see maybe doing a book sometime, but we're enjoying the doing a lot now.  We'll worry about chronicling it all later.

Cindy knows that she has to describe anything she's asked and answer any questions she's asked so if you want her to talk about her lessons, just ask her.

Cindy's blogging complaints--we decided when we were doing this with Jill that their blogs should be honest so that we could follow their reactions and see changes in attitude.

Now a question for you, what do you want to see on their web page?  We're looking to put a good web page together for them and we're looking for ideas.

What a Great Day Friday Was

We had a lot of fun Friday. I read Jill's diary entry so I won't double up her entry information, but I was kind of shocked when Heather got the bright idea of tying Cindy up and taking her to the mall regardless of what she wanted. My original thought was to allow her to go in male attire and gradually feminize her from store to store, but this worked better.

We always get excellent service at the mall once the sales people see we're not there on a goof, but that we're actually spending money and lots of it. The makeup people at Sephora didn't show any apprehension and Cindy dropped a lot there as she needed everything. Jill needed a lot of clothes too. With the warmer weather it's going to be even harder for her to pass as a male. Her bra will show through a t-shirt, her shaved legs will be obvious in shorts, etc. Cindy doesn't have to worry about showing up to class as Cindy yet so they were looking for different things.

Taking any beginning sissy to Victoria's Secret is a blast. Cindy turned bright red, just like Jill did way back in September. We got her some cheap breast forms until she can save up for a nicer set. She also got her first bras. From now on, she'll be wearing the bras to class and the forms whenever she's home. We've got a little over 2 months to make her very passable for our summer plans to work.

Last night, Cindy gave a fashion show and that was a lot of fun for all of us. We hadn't had Jill give one in months. I think having the two of them model together would be a fun idea for next week.

Shopping Trip Coming Up

Things have been going very well with Cindy, so we've decided that this weekend is an ideal time for a shopping trip.   It'll be a little tougher with Cindy than it was with Jill because Jill's family is loaded while Cindy's is just comfortably middle class.  She needs some bras, some makeup, and a few outfits of her own.  A pair of shoes that fit her properly would be nice too.  Beyond that, we'll just see what's on sale.   Oh yeah, definitely want to get her something pretty to sleep in.  She's really antsy about this and with good reason.   She knows that shopping with us is going to be quite an experience.

Working Her Hard

We worked our little Cindy very hard this weekend. Not only the blogging, but also trying to figure her way around a pair of heels. She was pretty fed up today so you can imagine being told that starting with Wednesday's class she had to be wearing pantyhose as well as panties from now one didn't go over very well. I've read a lot of great suggestions from you all, but some of them are way too advanced. I don't know where we're going to take things between Jill and Cindy, but no matter where things go they have to go very slow. Both of them think of themselves as strictly heterosexual. Making them kiss or hold hands is extremely fun, but beyond that will take a long time if at all. Any suggestions for improving Cindy's appearance are appreciated. She's looking great I think and it's fun having one blonde and one brunette.

We're working on a new web page for both of them, but it's going to take time and that's something none of us seem to have a lot of at the moment. I will confess that part of the reason for feminizing Cindy was that Jill needed a roommate before her parents would consider allowing her to move out of the dorms--voila problem is solved. I know she's gotten a ton of comments and questions and that's great. If you want to push some buttons, the following things really get her goat:

1. How were mere females able to so completely overpower you?
2. How does it feel knowing that the girl you thought was so hot turned out to be a guy?
3. How does it feel knowing other guys are checking you out and think you're hot?