Wednesday, June 30, 2010

Amber and Jill

Allow me to clear up one thing. Neither girl is on a diet, but we definitely like to have them eating in a more feminine style. Believe me, a lot of us have tried losing weight on a diet of salad with dressing and ice cream--it doesn't work. They'll be stuffing their faces with popcorn tonight at Twilight which was a brilliant idea of Amanda. It's great bonding and what better way to get them to see a chick flick that none of us had the slightest interest in. Amanda is great at finding ways to make the routine humiliating for them and fun for us.

It was a difficult decision on what cup size to get for Amber. She got a set of size 3 Transform forms from This should give her a very nice 36B rack, which seemed to look the most normal on her when we experimented. They are designed for a perky look and I think they'll look great on Amber. We didn't stop there though, we also had her order a pair of 36C forms with adhesive for when Amber needs to get a little extra attention. She was so embarrassed ordering them. She was so red and actually begged to be allowed to keep stuffing for awhile longer. Eventually, we'll get her a pair of swimmers like Cindy and Jill have too. She literally has so much to buy.

She hasn't been taking her makeup very seriously. She's got until Thursday to impress me with what she's learned or she's going to have a very unhappy weekend. If she puts her mind to it, I'm sure she'll do a great job.

Tuesday, June 29, 2010

Meeting of the Sissies

Today Jill, myself, Sheila, and Amanda visited Amber for lunch. Amber was quite an excellent hostess although, we had to pull her aside afterward and give her a bit of a talking to about the value of good housekeeping. Amber made club sandwiches for Sheila, Amanda, and I while Jill and Amanda shared a delightful summer salad. The weather was beautiful.

Afterward lunch, there was a little modeling session, but nothing like we have in mind for when Cindy returns and we can get all three together. Jill and Amber put on quite a show for us and a good time was had by all. Amber seemed timid and almost frightened of Jill in the beginning, but as they helped each other get ready to model, things warmed up. Nothing brings sissies together like modeling.

It is important for Jill and Amber to get along as Jill is going to be Amber's voice tutor. Jill has a very convincing voice and a pleasant speaking manner that Amber can definitely gain from. I know Amber probably found today to be another mind fuck as she likes to call it, especially when we made them kiss and hold hands and I kept asking Jill about what she did to turn Amber on. It was quite an exciting afternoon for all of us.

Sunday, June 27, 2010


Cindy's trip home has been going remarkably well based on the reports from Cindy herself, as well as Colleen, and Kristine. She definitely looks effeminate as a boy with his thinned eyebrows, smooth skin, and occasional girlish mannerisms creeping in. However, she han't had much trouble with her parents because of this.

Colleen and Kristine have come up with some fun ideas. She's been taking ballroom dance lessons--something Jill and Amber should be too. She's been out shopping several times and has a few new outfits to bring back with her, but has tried in literally dozens of different dresses and skirts. They've taken her to get professional photos done, which I am dying to see. They've made Cindy flirt, and Colleen loves the vibrating plug. They have made arrangements for Cindy to spend far more time en femme than I would have thought possible. Cindy is the most beautiful sissy, but probably the least feminine. Colleen has decided that she will be working on that this summer and make it her project in the fall as well.

Saturday, June 26, 2010

Sorry for the Weird Week

With Jill's blogging resposibilities temporarily eased, Cindy visiting her family, and Amber sick in bed there haven't been a lot of posts.  I apologize for that, but they'll be posting again before you know it.   Amber should be making a post today actually. 

Cindy is home and she says her parents haven't freaked.  I guess her father and mother were into The Cure in college, so she's not even the first guy in her family to wear makeup in college.  Colleen has charmed them as well.   Kristine and Colleen have had a lot of fun having their own little Cindy doll and have managed to find time to play with her a lot.   I'll let her give you most of the juicy details.

Jill has been enjoying her "time off", but she's still been required to dress up and to work as a waitress.  She's gotten quite good at it.  We try and go in at least once a week and sit in her station.  That lets us be waited on by her, but also to hear how she does at her other tables. 

Amber is sick.  Sue tried to help her pass the time in bed by giving her movies to watch.  We're trying to decide what size her breast forms should be.   B Cup or C Cup that is the question.   Any ideas?  I don't think we'll go as big as D.   What do you all think?  What's your favorite breast size for a sissy?

Monday, June 21, 2010


Amber had two big things to worry about today--pardon the pun.   This was her first day of daily bra wear.  She'll be very self-conscious for awhile I'm sure.  Cindy had it the easiest of all the sissies as she got to get used to bras during the winter.  I'm sure Amber will manage.  There was a great link somebody sent her about how to hide a bra--well it was about bra training guys, but the part on hiding them was very useful.  

Amber also went for her first trip outside dressed.  She had to walk 5 blocks to the drugstore to pick up a Glamour, press on nails, clothesline, and tampons.   She passed with flying colors.  Sue was nice enough not to make her wear stilettos so her feet survived.  What a cutie she's going to be.   The Glamour is actually going to be useful because it had a big section on great clothes under $50 which every sissy building up her wardrobe can use.

Jill continues to adapt quite well to being a working woman.   Don't look for too many posts from her until July 1st, but hopefully she'll do some.   We gave her certain freedoms in exchange for her help with Amber and I think it was a worthwhile trade.   It is still amazing what sets her off though.   It's hard to believe she hasn't been living as a woman even part time for a full year because she's become so feminine looking.  We need to work on feminine thinking and acting however.

Cindy is about to go home where Colleen and Kristine will have some fun with her.   Wendy is going to give her a more masculine style tomorrow, but in exchange Cindy will be wearing extensions and finger nails when she gets back.  Wendy is so useful and was a great source of wigs for both Cindy and now Amber.  Some of the things Colleen has asked me about with Cindy sound like so much fun.  I can't wait until she's down here.

Saturday, June 19, 2010


I'm sure some of you will be disappointed to learn that we don't have a lot of really juicy photos from today.  Remember, Amber has been doing this about a week.  She can't pass at all in public regardless of how she looks in a still picture.   So for our big shopping day it was Susan, Karen, Amber, and myself.   We took her to Victoria's Secret and were able to replace the lingerie that she threw out.  Pink is going to be her scent for awhile too.

From VS we went to Bebe's, Ambercrombie & Finch, Forever 21, Macy's (which also had a huge sale), and Kohl's.   We'd all love it if Amber could have a completely name brand wardrobe, but she needs EVERYTHING so she shopped on a budget and got I think 4 dresses and a variety of skirts, blouses, shorts, and a pair of girl jeans.  We also took her to Baker's for a couple of pairs of shoes.

We broke for lunch and Susan gave her a choice of getting a makeover at the makeup counter or getting her ears pierced.  She chose the ears as the lesser of two evils.   Tonight there should be much some fun pictures as she models her new clothes for us.

Friday, June 18, 2010

What a Relief

I was terrified of Amber finding the whole story behind Jill and Cindy. Well she knows everything now. Fortunately, our confrontation was something I had been rehearsing in my head forever. I think her position is unchanged and possibly even more submissive now that the truth is out there. I flat out told her that I would be making her just as feminine and Cindy and Jill are and the fact that she didn't want that made it even more fun for me. We have some shopping to do tomorrow. She had a bit of a tantrum before our conversation, but I think things are going to work out just fine.

Wednesday, June 16, 2010

Best Time to Own a Sissy

This is one of the best times to own a sissy--especially one like Amber who needs everything, but all three girls will be making their way to Victoria's Secret for the Semi-Annual Sale.  I'm looking forward to letting Amber in on Victoria's Secret.  The beginning with a sissy when everything is new for them is so challenging, but so much fun and Amber is already becoming a beauty.  The trade off has been great for us because the job is perfect for what we wanted for Jill.  She's become so much more passable this summer--not in looks, but in attitude and personality and mannerisms. Jill has been lazy on her blog and I've seen a few comments about it.  I'm sorry, but I agreed to give her a bit of time off on several tasks for her work with Amber.   She'll be posting again very soon.

I guess I'll answer a few questions myself, but don't expect this blog to turn into the Q&A that Amber has.   Ranko, passing is overrated, just be safe and enjoy yourself.   CR we cherry pick the best pictures. but Amber had the perfect bone structure for this.  We got lucky with all 3 girls.  Connie thanks for the links--I bookmarked them.

Tuesday, June 15, 2010

Amber Waves of Grain

The first days of training a sissy are so exciting and also so crazy. It's a new thing everyday and it takes a lot of discipline to let things develop and not rush through everything. Sue is a natural at this. She's got Amber hard at work learning how to walk like a lady in heels and Amber now has her own makeup to practice with. Please share any links you may have for good makeup tutorials. I never really did find any for Jill or Cindy and I think watching a tutorial will probably help Amber pick it up faster. Amber has such amazing eyes, she'll have to learn how to emphasize them properly.

Monday, June 14, 2010

Don't Break My Toys

If I let you borrow my toys, please don't break them. Somebody sent Amber a note saying "run for your life" and including links to all 4 blogs. Nice try, but I check his comments nearly hourly and he checks them when I make him so it wasn't really difficult to intercept. I know there are some people who are going to take Amber's side, but if I'm being nice enough to let you in on things, I wish you'd respect that.

Sunday, June 13, 2010

Amber's Disappearing Blog

We don't know exactly what happened. I think Amber did something, but Blogger has been changed a lot this weekend so she may not be lying, but we could not access the blog after her first post. We took the link away and closed the blog. We opened a new one and cut and pasted her first posting. It should be no harm no foul and it gives me a good excuse to make her practice in heels today. The link is on the blog roll and she doesn't think anybody will follow her. Please say "hi", just don't let her know about Cindy or Jill's plight. One guest was impressed at how Amber and all the girls turned out, but didn't think that they looked much like they do as guys. It's funny because I've been having the opposite worry about Amber being spotted and recognized as Tom. I do think she makes a very cute girl, but she still looks like Tom to me.

Saturday, June 12, 2010

Amber's First Blog Post

 Sue asked me to pass this on.  She's set up a blogger account for Amber and Amber has already posted.  Please feel free to comment and tease and embarrass, but don't let her know about the other blogs.   She still believes that this is going to last a week or two tops and showing her the future in the form of where Jill and Cindy are at could make it harder for us.  She currently thinks Jill was already a crossdresser and she doesn't know about Cindy.  As far as she knows, she's the only one being forcibly feminized.  I will put her blog link in the blog roll.

Introducing Amber

Well, the majority has spoken. I think Amber is a great name and one that Tom is guaranteed to hate answering to. Cindy swears to me that getting a feminine name had a huge effect on her. I plan to have Amber set up with her own blog as soon as I can--hopefully this weekend.

I have kind of a funny attitude about this, but since I gained so much by having the sissy blogs to read, I think it only fair that Amber share as well. She is really amping up the resistance, but I think she's come to reallize just what I can do to her--not just with her friends, but the university and her parents. Tonight is the last fashion show before she takes a shopping trip sometime mid-week.

Friday, June 11, 2010

What Happenned - My POV

I'm sorry that I haven't been able to write much about this. I've kind of had a choice between committing the time to feminizing Tom and writing about feminizing Tom. Can you really blame me for being a doer? I won't start at the very beginning. I think Jill did an excellent job of that already, but I do want you to know she was extremely seductive and she had him wrapped around her finger.

After Tom get an email with a few choice pics--which you'll get to see very soon, he saw that he didn't have much choice but to cooperate. He did go along with us at first. The girls had a pretty good idea when he'd balk and balk he did. We had him in a bra and panties, but when he saw the razors he immediately started to try and unfasten his bra. As we had planned Heather was on him very quickly and got him in an arm lock on the floor. I quickly grabbed the clothesline I had purchased for just such a location and while she kept control of him, I tied him securely--I felt extremely empowered and proud of myself.

I think we overdid it on the boobies, but I guess it's good to see so we can figure out a good size for her breast forms. He's definitely better looking than I thought he'd be, but not in Jill or Cindy's class.

From there we were able to shave his legs and arm pits and do a little shaping on his eye brows. Tonight will be a fashion show and we should soon have enough pics to have him good and trapped soon. Please vote in the naming poll. I'll let you pick the name. I definitely do intend for him to start blogging as early as this weekend. I think I'll have a much easier time calling her She once she gets her new name.

Thursday, June 10, 2010

Let's Get Serious

Tonight was a great night. The new sissy is currently restrained and I'm sending some pictures to the Amigas so that we have plenty of secure evidence. Her legs were shaved tonight, but they will be allowed to grow back before she has to start shaving them regularly. When I send her home (in the pictured outfit) she's going to be informed that her days in boxers are over and it's time for her to buy some panties. Let's get serious about her new name. I'm like Sienna and Amber the most right now, but I'd love to get some other ideas.

Wednesday, June 9, 2010

I'm so Happy for Sue

 I'm so happy it worked out well.  I will insist that Jill tell the story, but she's really deserving of praise for a job well done.  We sent Tom home in his little dress and he was none to happy about it.  He'll be less happy tomorrow when he finds out we're not done. Sue did tell him to hang up the dress because he'd need it again.  Not in Cindy's league or even Jill's, but with some makeup there's definite potential.

We Got Our Girl

Updates are coming when time permits. The main thing is we got our girl. I'm a bit sad that he didn't surprise me and pass the test I gave him, but he didn't. Things worked really well and he didn't have a chance. I couldn't have done it without Heather, Amanda, Sheila, Karen, and Jill.

Monday, June 7, 2010

We May Have a New Girl This Weekend

Things are getting real close between Jill and Tom.  They've been talking daily and their talks are getting more intimate.   I think the process has been good for Jill.   When they've talked about Jill's previous boyfriends she tried to take the role of girls she dated.  Putting herself in their shoes is something I doubt she ever did before.  Jill is actually a fairly nice guy beneath it all, but he's got way too much bluster and from talking to her and to Kristine I don't think she was a very good boyfriend.  Jill met some of Tom's friends which is necessary so that they have seen the two together, but they didn't meet long enough for his friends to really feel fooled by Jill.  This is important.

Wednesday, June 2, 2010

What Jill Said

We've mentioned this before, but you don't get the whole story.  Anything we post here is viewable by Jill and Cindy.  What that means unfortunately is that when some of you get a little nervous, we can't always put your minds at ease.  There are things that we have done with our sissies for our amusement.  It's actually quite fun to take one of them way past their limits.   Some of you may remember back in September when Jill was never going to wear pantyhose or a bra.  We have limits too.  We've set out to not do things that will permanently damage them.  We will not put them on hormones to grow their breasts, but we also won't put them in situations that could damage them permanently  psychologically either.   We're making them walk a very difficult path and do it in high heels, but there is a tomorrow for both of them when they go back to living totally as guys...if that's what they want.  I really don't want to get too deep with this.  It isn't what the blogs are supposed to be about, but I want some of you to know that you don't have to worry without posting all our plans for the sissy to see.

P.S.  Somebody just asked me if it was them I was talking about--it wasn't.  I've just had a few comments of concern and wanted to set some minds at ease.