Sunday, September 27, 2009

Jill's Night on the Town

We took Jill out for drinks on Saturday night and had a great time. She was dressed extremely casually as she should be.  We wanted her to look like any other girl at the place and not draw unwanted attention so we left the sexy dresses at home and even let her wear a pair of Amanda's jeans.  She needs to stay away from jeans because she doesn't have the curves for them, but with a sweater it wasn't that bad.   She did wear full makeup and heels.   She interacted with our waitress on a limited basis, but passed with flying colors.  A few guys came over to talk with us and we made sure she talked too.  It was a very successful night.  She's pouting a bit now because we insisted that after a night in jeans, she needed to really dress up to the nines today.

Saturday, September 26, 2009

Sissy's New Website

We started a little website for Jill.   It isn't fancy and frankly, it's about all we have the technical nohow to do, but I hope you like.

Sunday, September 20, 2009

Attitude Adjustment

We've been very disappointed with Jill's attitude and she will be paying for it a little today.   She's going to have a very simple task--to walk from our place to the Walgreens where she will browse at the magazines for 20 minutes.  She's going to pick up a Cosmo Girl and some presson nails.  This is a very minimum risk outing and of course we'll be following at a distance to watch, but this is going to be her first real voyage out in public.   We were definitely looking to do something like this for awhile, but she's definitely given us motivation to do it today.   I'm extremely proud at how far we've taken her.  We have a lot more planned too.

Friday, September 18, 2009

We're Getting Very Close

Our big focus is to get Jill out in public. That will open up a whole lot of fun possibilities. Her movement and walk are really good and her voice has gotten decent. Her big problem now is that she has no idea how to think or act like a woman. We're going to start her out slowly and safely, but I'm setting October 1st for a goal date. I'd like to see her spend a day in the college library just hanging out in a skirt. Do any of you have fabulous Halloween ideas for her? I have a fun one, but I don't want to say it yet because I don't want her to read it.

Wednesday, September 16, 2009

Our Motivation

Kimberly Anne Love wrote in the comments section to ask why we do this? Is it power? Does she pay us? Is it some sort of redemption for our own sweatsuit and no makeup ways? We don't get paid for this, but you did hit on some of the reasons.

All of us have a different motivation. For Amanda it started as revenge. For me and Heather we totally love the power. Karen really enjoys having a doll to play with. Speaking for myself, I love my power over Jill. I have a very strong desire to make her think, act, and look as girlish as possible. This makes me sound like a total bitch, but the fact she fights us and doesn't want to do this makes it more fun not less fun for me. There's power. There's control. I am not a slob in sweats and no makeup all day, but the gender switch is kind of awesome. Having a maid, which is what Jill is becoming, is pretty cool too. Did that answer your question? If not feel free to follow up.

Tuesday, September 15, 2009

Jill and Us

In Jill's blog she had a request for pictures of us with her.   Frankly, most of the pictures of Jill have been posing her and taking a picture.   They make great blackmail, but there isn't much purpose for us being in them.   Also, we're usually in sweats when she's all dolled up--nobody wants to be upstaged by their sissy.  As we start getting more exciting pictures of her, you'll see more of us all together I'm sure.  If we can be patient, I surely hope you can.

Sunday, September 13, 2009

Wearing Down Resistance

We're slowly, but surely wearing down resistance. Before she finally backed down and went shopping, there were many tears shed. Sorry Jill, but we told you how things were going to be. We won't go out of our way to hurt her, but we're not going to let her dictate things. Her resistance makes this more fun, for me at least. Sometimes it is tough to be firm, but so far what we've had Jill do is pretty simple stuff. If we let her have her way now, we'd never be able to get her to do half the things we want.

She had to wear long sleeves yesterday because of the rope marks, but they're pretty much gone now. I think next time we really need to just use duct tape. I prefer tying, but I don't want her to have to hide her wrists all the time. She was left tied up for 3 and a half hours before finally giving in to the inevitable. That's probably why she looks so pissed off.

We're working on a Jill website. Of course we'll post a URL when we get it up. Please leave comments. I love reading from those of you who are enjoying our little experiment this year. Jill is still fighting, but she's really getting better at things.

Saturday, September 12, 2009

Damsel in Distress

She'd been doing so well lately, but Jill absolutely refused to go shopping with us today. It may have been the money, it may have been the embarrassment, it may have been my own fault. I was encouraging her to go dressed as Jill by reminding her that we'd be having her try on a lot of things. I may have scared her. Anyway, as much as we prefer doing things the easy way, Jill required the hard way today. She's been hogtied for an hour and a half now and won't get released until she's ready for shopping. If she's not ready today, I'm sure she'll be ready by tomorrow. Sometimes, its tough to be mean, but I have to admit there is a real thrill to breaking through her resistance and such a feeling of power. We really did try and give her the easy option first. Hopefully, we get the shopping done today.

Friday, September 11, 2009

Shopping Day

Tomorrow is the day. I'm expecting that by the time we get back, we'll have spent $500+ and 5 or 6 hours minimum. Jill will be coming home with a large number of shoes, dresses, skirts, blouses, accessories, and possibly a nightie or two. After this spree, Jill will be able to dress fully in the afternoon or weekends. It won't be full time at first, but it will enable us to have her start getting used to dressing fully and get more comfortable in skirts or dresses. I expect she'll be making public appearances as Jill within a month's time. Wish us luck :)

Monday, September 7, 2009

In the Lap of Luxury

Well, I certainly thought our slide show would get a bit more response.  Anyway, today was wonderful.  My apartment is spotless including the floors, bathroom, and windows.   We had a great dinner too.   Jill is quite a good griller and it shouldn't take too much effort to teach her how to be an expert at other types of cuisine as well.  She's not great at cleaning, but neither am I.  The important thing is that she does the work.  I kind of feel sorry for Amanda and Heather.   Jill will clean their room too, but there is much she can do.   I hope everybody had a great labor day.

Sunday, September 6, 2009

Our Movie Starlet

Stateu1 from SheSheila on Vimeo.

We made a little slide show for our Jill. I hope you like. She's quite the movie starlet now.

Saturday, September 5, 2009

What a Saturday

It is the kind of beautiful Fall Saturday that comes only a couple times a year.   I've been outside most of the afternoon just to be afternoon.   We were unintentionally cruel to Jill today by making her stay dressed up all afternoon.   We not only took her dress shopping today, we went early enough that the stores were kind of empty and Jill was able to try dresses on.  I think the saleswoman was a bit shocked when she stepped out of the dressing room to model her purchases and you could see her bra straps and her pantyhose encased legs lol.  Jill was blushy bright crimson, but the saleswoman didn't react and instead discussed the dress with us.

Thursday, September 3, 2009

Bras for Jill

We had a delightful shopping trip today to buy bras for Jill.   Beginning tomorrow, she will be required to wear bras in addition to her panties and pantyhose at all times she is awake.  We could have made her get a really humiliating bra fitting, but that didn't really make sense.  For one thing, these bras are to wear underneath her boy clothes. They're A cup to be worn without any kind of padding or underwire.  It was quiet enough that at one point we made him put one on and model it in the store.   He purchased 5 bras that he can wear during the week.   When we get him some breast forms, we're also going to get him some far more noticeable curves.  Keep dropping me lines folks.  It keepsme interested in writing our experiences down.

Tuesday, September 1, 2009

And the Winning Cup Size is....

We debated on this one for awhile tonight.  We definitely need to get our Jill some boobies.   Stuffing with underwear is just too junior high for a sophisticated woman of the world like Jill.   I wanted C cups, but got outvoted by the B contingent who decided that while the C cup would certainly garner Jill a lot of attention, at her size a B cup would look more realistic.  Now, that doesn't mean we won't have some alternative arrangements in the future for a more stacked Jill, but for the time being we want realism here and the smaller size should make it easier for her to get used to it.  Now the only question is who makes the best forms? 

House Bunny

Our friend for Michelle (above) hosted us over at her sorority house last night.  She thinks that Jill's predicament is hysterical and she had a bunch of great clothes for Jill to model including a hysterical pink bunny costume (see Jill's blog).  Jill was livid that she had been told about him, but as I told Jill, "you got to tell Eddie, we should be able to tell our friends too."   We will most definitely be limiting the people we tell about Jill, but letting some of our friends know is going to be important to us.  Yesterday, definitely got me thinking about Halloween costumes for Jill.  I am sure we can come up with something good.  Don't forget to congratulate Jill on her new eye brows.  She's very self-conscious about it, but if she's going to be any kind of sissy she needs to get over herself.