Saturday, December 25, 2010

Merry Christmas

I know, it was pretty cruel to do that to Jill, but that's actually one thing that Kristine wanted for Christmas.   There is going to be a big change for Jill in 2011 that some of you will absolutely hate us for and some of you will really enjoy.  I will leave it to either Jill or Kristine to explain it. 

You may have picked up on some issues with Colleen and Cindy.  Colleen had an attitude of poor pitiful slave girl and while, Colleen certainly has enjoyed having a slave girl and making Cindy do things she might not want to do, she's been a bit bummed by Cindy's attitude, which has left Colleen wondering if their relationship was just one more duty for Cindy.  Cindy came through in a big way this week and danced and flirted with a guy in a bar that everybody's eyes were on, but he went home with Colleen who was very appreciative.  I think they're going to be alright.

Xiu has a lot of freedom over break with nobody there to watch her, but she made a huge mistake in putting off New Years dress shopping until after Christmas when she couldn't possibly convince anybody it was a present.  Then again, trying it on as we're requiring would probably make that a bit tougher.

Finally, Sue and Amber are having a happy holiday.  They spent Christmas with Amber's family and now Amber has a sister who knows her little secret.  Sue is beloved by Amber's family and while chatting with the sister things came out.  Amber was kept in appropriate lingerie the whole time and made several trips to the mall.  There was a little makeout session with a Santa Statue at the mall and a great shot of how Amber runs like a girl.

Both of us are having a wonderful time this Christmas with our respective families.   I have the greatest parents in the world and though I may be a stern mistress, it's an awful lot of fun to just have my daddy treat me like his little princess.   I hope you all have a wonderful Christmas and expect plenty of pictures of the Christmas festivities at home and school soon.

Monday, December 13, 2010

The Best Time

This really is a great time of year for us. Finals are over and we're on Christmas Break. However, there really is no need to go home in the second week of December for Christmas so we're all still hanging out and enjoying ourselves. It's been fun helping the sissies shop for each other. There are a lot of boxes under the tree and between what we got them and what they got each other, I'm predicting a lot of lingerie in the sissies' futures. We're also just genuinely enjoying some quiet time. Of course there are parties too, but we had a great time tonight just sipping cocoa with a tiny bit of peppermint schnapps and talking.

I'll keep an eye out for that workout CD---sounds fun. I'm starting to think Sheila made the right decision feminizing Xiu. With Christmas, it's been very nice having our own sissy while Jill, Cindy, and Amber were occupied. I'm sure I'll write before I head home, but I hope everybody has a very Merry Christmas and thanks for following us this year.

Thursday, December 2, 2010

Not Too Upset

We've been busy too, so we required that the sissies simply post once this week. The result was 3 out of 4 complied. Xiu is going to be in for a rough time if she doesn't get her act together and soon.

It was brought to our attention that Colleen and Kristine's blog wasn't set to allow anonymous comments. I showed them how to fix it, so feel free to comment there.

I love the above picture because both Jill and Cindy look so cute. One of our friends who isn't a mistress, but enjoys what we're doing brought those outfits back after Thanksgiving break. It does show off the weakness of breast forms though. They worked a long time with foundation, but you can still tell if you know what to look for. Still, these cat costumes were too good to waste. This picture was taken in the freshman guys dorm at 2AM. They were sent on a scavenger hunt including a shot glass, a pair of boxer shorts, a condom from a bathroom machine, a phone number each, and a picture of their lipstick prints on a mirror. They completed the challenge in just over an hour. Those girls are getting very creative. I think we'll have to top them if Xiu needs to be reminded who is boss.

Sunday, November 21, 2010

Halloween Winners

The voting was both close and difficult, but we have winners:

Best Portfolio
Cindy 11
Jill 11
Xiu 3
Amber 1

Best Individual Costume
Jill 11
Cindy 7
Amber 5
Xiu 3

They will be rewarded after returning from Thanksgiving.  You get rewarded now with some higher resolution costume pictures.  Just click on the picture.  It'd make a great wallpaper for next Halloween too.  I think they all should take note that showing a lot of leg seems to be key to winning.

Sorry, we've let the sissies take advantage of us a bit on the updating, but grades come first and we have all been a bit busy.  Things will come down a little after Thanksgiving before getting really crazy just in time for the end of the semester and Christmas. Our Homecoming montage hit a snag when the good computer lost all audio.  We have a sound card coming from Amazon because we can't hear anything on the one computer capable of doing the cool stuff.

Tuesday, November 2, 2010

Halloween Costume Contest

I'm sure the sissies will be electioneering on their own blogs and you may see some slightly higher res photos. Getting all their pics in one place was kind of a nightmare so we went for expediency and made a slide show. For this Contest, we let the sissies pick the photos, but told them to try and show off the whole costume because that's what voters would want to see.

If you don't mind, we'd like you to participate in our poll:

Who had the best 4 photo Halloween portfolio?

1. Jill
2. Cindy
3. Amber
4. Xiu

Who had the single sexiest costume? What was it?

Thanks, polls will close in a week. Remember, it's your patriotic duty to vote.

Monday, November 1, 2010

Halloween Contest Coming

We're setting up a Halloween Costume Contest where you will all get a chance to vote, but it requires all 4 sissies and 2 of us to get things done on the same day.  We hope to get things posted tomorrow.   We had quite a busy weekend as you can imagine.

Monday, October 25, 2010

So Much Shopping Fun

Homecoming dresses and Halloween Costumes need to be purchased!  Everybody is busy even the mistresses helping with this and of course making our own purchases.  Xiu startled Amber a bit when her hands went roving, but it depends on who you talk to whether she already knew or not.  I'm believing Amber on this myself.  There doesn't seem to be any lingering hostility though and they should be a great couple for Homecoming.  It's kind of funny that Jill has never done a Homecoming as a guy.

Amy: I don't know about a timeline, but Bill became Jill in September of last year, Cindy joined our little group in February,  Susan brought Amber into the sorority in June, and Xiu came along in September. 

Xiu will be dating, but not for awhile.  She's not ready by any means.

I love the Halloween costume contest. We have plans for that and you'll all get to vote.

Saturday, October 23, 2010

She Figured it Out

Well, Xiu figured out that Amber is a guy and has figured out a lot of things that are going on. We're not disappointed because we knew this day would come and we got a lot done before then. We've been holding back on a video until she could enjoy the attention. No need to wait now.

Wednesday, October 20, 2010


 We have decided to have the sissies find dates for Homecoming this year, which should be a lot of fun.   It's always fun when we can send them all to a formal or semi-formal.  Of course, Xiu isn't ready yet to go en femme, so the plan is for Xiu to go with Amber.  We gave Amber the goal of four dates without being discovered and she's halfway there.  Jill and Cindy of course will have to flirt their way into dates.

Xiu is beautiful.  There's no other way to say it.  Her looks require so little work compared to other things.  Kristy should work out real well.  She's not exactly a mistress, but she's agreed to make sure that Xiu is doing what she's supposed to and that's probably better.  I'd rather not have to share.  Kristy had some great ideas for Chinese themed costumes and props we could use too.  I think Xiu is very close to figuring out just how stuck she is so it's important that we get every ounce of control we can get out of this we can.

CR - I'll check out the tramp stamps.  I love it

Bill - You're overthinking.  We didn't have to dress and tie Xiu.  She was already dressed.

Anon - We really need to update the Wix pages.  Sorry for the delay.  For higher res photos try the backgrounds on their blogs

Friday, October 15, 2010

Big Hurdle Crossed

We probably came as close to torturing Xiu as we ever have, but it was unfortunately necessary.  I felt a bit guilty afterward, but there was now that Xiu would be able to practice the skills she needs without a roommate knowing.  There was no pain or anything, but a lot of bondage and threats.  I will make it up to her a bit, but if she's going to be my sissy she needs to know that things will be done my way.

It took a lot of convincing to get Xiu to reallize her best option was to tell her roommate that she was experimenting with her gender and would be dressing up around the apartment, but would not do so in anyway that would embarrass her.   Her roommate's name is Kristy and she strikes me as a very serious girl, but I have only had one brief meeting with her.  I can't see Kristy ever participating, but I'd love to have her watching to make sure that Xiu does what she's supposed to.  I can do it subtlety by asking questions and pretending it's just curiosity as in "Did Xiu dress up last night?"  I think that may keep Xiu on his toes.

Xiu went out on his date with Amber and it seemed to be going pretty well.  Cindy and Jill are keeping an eye on them as Xiu really doesn't know them. 

Xiu is pronounced the same way as au jus.   It's like the J in Jacque followed by the ew sound.

Sunday, October 10, 2010

Shopping and MORE

Shopping went a lot longer than I planned.  When the dust cleared early this afternoon, Xiu had spent over $1000 between her and us.  She has heels, flats, dressy clothes, casual clothes, her own makeup, and even fake nails.  She has the clothes now to look like a debutante or a girl gone wild depending on our mood.  Things went so well that I made her order her breast forms today.  We even took her to Chinatown to shop for a few things traditional to her Chinese heritage.  The shop was recommended to me by a Chinese salesgirl who said there was absolutely nothing wrong with playing up the mysterious Asian woman thing because it drives some guys wild. She's figured out it's not ending at Halloween.  I really liked that one, but she still doesn't get just what she's in for or how much power she's given us.

Saturday, October 9, 2010

Today's The Day

Right now, Amanda is in her bedroom with Xiu giving her a makeover.   She's got a plan to get her in heels and a miniskirt by letting her wear a t-shirt by telling her I was insisting she show off either her non-existent boobs or her legs.  Amanda is amazingly good at playing good cop and while I don't think Xiu completely trusts her, she is looking at her as her best chance to get out of this with any dignity left.  I've been playing up the bad cop and even told her I'm carrying handcuffs in my purse and if she doesn't cooperate we'll leave her in one of the dressing rooms.  Amanda immediately defended her by saying, "He'll cooperate".  Thanks for all your help with this too.

Xiu still doesn't really get just how much leverage she's given me.  We've got so many pictures already and now I've got an email from her account begging us to make her over without any mention that it's even the slightest bit under duress. 

Bobby I don't have a read on the roommate yet.  I don't think they're particularly close, but I still don't think she'd approve of our project and it's a big risk.  However, when Jill started out she had to dress in front of a male roommate. There's no reason Xiu can't do the same in front of a female one.  I wish I knew anything about her.

Today won't be the day as both Cindy and Jill are off.  However, I definitely intend to have her shop at Cindy's store when she's there and can take advantage of her discount while adding to her commission.  That's a definite. Having Jill wait on her is a plus too of course.

Before Xiu becomes totally feminized, I think it's time for Amber to make her move.   We thought dating Xiu in male form would be great dating experience for Amber.   Well, we're off to shop.  Of course I'll post pics and details.

Thursday, October 7, 2010

Xiu's Big Day

Xiu is slowly, but steadily realizing just how trapped she is. I must say she's been slower on the uptake than either Amber or Cindy. Amber found out about the other blogs right away. Xiu hasn't even figured out why we keep taking pictures of her yet. Things are very tricky with Xiu. She has a female housemate, which seems to be more a financial arrangement then anything else. Several have commented on her eyebrows giving her away and we do need to neaten them, but we don't want to have her looks make it impossible for her to work as a guy (with female undergarments naturally).

One nice thing is that like Jill, Xiu comes from money. Her parents are both doctors and that means, they won't look too askew at their son taking out a few hundreds bucks and start wondering why. Keep mentioning to her that she'll be less embarrassed if she shops dressed up. I've been nicely offering to help her pass while Sheila has been laughing about how she's going to hold dresses up to her in the middle of the store when she's dressed as a boy. If we can take her shopping dressed, we can take her to the makeup counter, which is always a lot of fun.

Sunday, October 3, 2010

Xiu and the Other Sissies

Xiu is getting all the attention now because she's new, but that will be changing.  I've got more to talk about her now, but first I had an amazing birthday party last night.  They even brought a stripper who had a lot of fun at a party that was 80% girls.   Amber, Cindy, and Jill all got to participate, but Xiu wasn't ready so she spent the night watching videos that I found on Youtube from somebody named Bubz who is Chinese and exactly the look and attitude that I want from Xiu.  I have such great friends.  

Thanks for all the comments for Xiu.   It helps to see her attitude and it does help to break her. I especially like those of you working psychology beautifully.  She's very prideful and getting her to talk about how she feels being bested and controlled by a woman is great.   I can't cover up the profiles so if you can post anonymously that's even better.  I think we can set him up on a date or two with Amber, which kills about a half dozen birds with one stone.

Just remember that we don't have do Xiu the same way we did the others.  There are advantages with Xiu that we didn't have with the others, but also different obstacles.   I'm just enjoying things as I can. Yesterday we had an early morning modeling session and I honestly think Xiu may be our hottest sissy yet.   My friend has been a huge help as I want her to have that cute anime-type girl vibe, without being racist or having her going around saying, "Me rove you long time."  Even though Roger is very Americanized and not very Chinese, there's no reason Xiu has to be.

Our boyfriends aren't scared we're going to feminize them.  I don't think they think we could (They're wrong lol), but some of this has changed us a bit.  We've talked about it.  I think I'm more sexually aggressive than I used to be and while I wouldn't force my boyfriend to put on one of my nighties, it might spice things up a bit.  The link to was interesting, but not quite me.   I do understand the feeling of harvesting sissies though. 

I love you guys.  Just remember my life isn't your life or your fantasy.  We may be much nicer to the sissies or much crueler to the sissies than you would want.  We definitely have limits, but they aren't your limits necessarily.  By now, you should know where we're coming from.

Wednesday, September 29, 2010

Xiu's Beautiful Kingdom

I'm excited and I can't help it.  I picked the name Xiu for her Chinese name or Michelle for her Americanized version.  I brought another woman into our circle who could answer some of those Chinese questions I had. 

Thanks for the advice anonymous.  That's very much the way we've feminized the others, but I was looking more for questions about feminizing a Chinese guy. 

If you do go visit her blog, just remember she's still at the nervous and wondering if she should cooperate stage.  She doesn't need extra reason to fight like finding out about the other sissies.   She'll learn in time.  We're all checking her blog though so most of the time we'll see any comments before she ever does.  

Wow!  This is fun. 

Tuesday, September 28, 2010


OK Sheila has her new toy and dressing her up for some new photos today, I have to admit it was pretty fun. Maybe it's because of her Chinese features, but she really feminizes easily and she's so slender. she's going to turn out pretty well from the get go. Her feet are small enough to wear my shoes, but actually I'll probably be borrowing the fabulous heels she buys rather than her borrowing my flats. The fact she deserves it makes it more fun too. I understand some of the worries that were expressed in the comments, but we haven't taken her anyway near that far. We'll deal with problems as they come. Some of the problems you mentioned are way off.

My problem is I've never dealt with a Chinese guy before. Any Chinese crossdressers out there that can help? I don't know how to handle the shape of her eyes, what colors to use for makeup or pantyhose, or a good girl's name and Sheila is more clueless than I am. Help us out please.

Monday, September 27, 2010

Greatest Gift I Ever Got

So I got back from my morning class at 9:30 to an empty place except for a note on the door wishing me a Happy Birthday.   I was a bit alarmed since today isn't my birthday.  I opened the door to see a Chinese girl tied to a chair in the middle of the room.  I'm more than a little confused, but with all the bondage we've been practicing lately, I wasn't really alarmed.  As I got closer, I realized just who this Asian beauty bound before me was--Roger, a TA who by now is a legend for hitting on girls and trying to use his power over them to get them to go out with him.

As I looked at the card, it was signed Colleen, Kristine, and Susan.   This is probably the nicest gift I have ever received.   Roger and I had a lovely conversation and I think he may very well become the newest filly in our little stable, but it remains to be seen.  He still seems quite uncooperative.  Then again that's some of the fun.   He has plenty of reason to behave too.  I frankly have no idea how they arranged the capture, but I'm dying to hear.  He wasn't very up front about what happened even after I took the tape off his mouth.  They enclosed a few pictures so if you'd like a better view en femme, here you go.  He's Chinese American and very petite for a guy.   I may go with a Chinese name.  I like Jiao which means delicate or lovely.  I may do an American name, but that's all a bit in the future.  Now, I have to get permission to keep him first :).  It would definitely be fun having a sissy of my own.

Sunday, September 26, 2010

A New Contest - Karaoke

The thing I've noticed about college--not just here mind you--but everywhere is that professors tend to follow very similar calendars when they produce their syllabus.  What that means is papers, tests, and in general work fall at the exact same time in any semester.  This past week, we got hit hard. Hopefully, you'll see more posts as we clear this first hurdle. 

We did have time for our second big sissy contest, which was won by Cindy with a stunning rendition of Like a Virgin at a local karaoke night.   She beat out Amber's Man I Feel Like a Woman and Jill's California Gurls.   Cindy didn't have a better voice than Amber and only a little better than Jill, but her choreography was top notch and she always seemed comfortable and happy while performing. After two competitions the score is Cindy 5, Jill 4, Amber 3. 

Wednesday, September 15, 2010

Three Lovely Bridesmaids

Don't get too excited.   These aren't the dresses for Wendy's wedding.  Who says you can't find a use for old bridesmaid dresses though.   Things are going great, but we're very busy.   Keep in mind that with all three sissies having a girlfriend at school now they don't have quite as much time as they did over summer, but we're going to make sure they update a bit more regularly.  I'm so excited that Cindy has got her job.  The sissies are under the impression that we are trying to humiliate them with the choice of work.   That's not really true.  Cindy will emerge from this experience much more feminine plus she gets a discount.  It just kind of defeats the purpose for them to take jobs where they can't dress up pretty.

Tuesday, August 24, 2010


CR and actually everybody had some wonderful suggestions for competitions.  We will be doing an America's Top Sissy contest after we get all the rules worked out.  We have always slutted the girls up from time to time, but we still expect them to be ladies just as we always have. 

We're starting to really get a good look at what we have to do to update the website.  There's a lot needed.  Even Amber's blog doesn't have a link.  We'll start working hard on this soon.

As for getting a new sissy, Amanda is against it, but I think I have Heather and Karen won over.  The target I have in mind would be interesting, I think he'd turn out great and he's really already trapped if I want to push it.  He's a TA that did some very unethical things last year.  I love all our sissies, but I don't want to do anything their girlfriends wouldn't approve of.  Having a sissy of our own means that we wouldn't have to worry about that.  

Thursday, August 19, 2010

Interesting Suggestions

So Amanda decided to ask some questions and she got some very interesting replies.  First, some are just too extreme.  However, I think we have the beginning of an awesome competition shaping up.  I like this very much!!  Also, the Disney Princess isn't for room decorating, although having a pillow or something would be sweet.  Let's see--here are some ideas for the sissy competition:

"Have an ongoing series. Let them earn points in different categories. Some that have to do with boys (best kisser, most dates with the same boy, things like that) Bonus points for specific accomplishments (first to ride on the back of a boy’s motorcycle, the first to get a boy to lend her a shirt or jacket). Other categories could be skill related (best cook, sew their own costumes for Halloween, learn a traditional feminine skill like knitting) Have them volunteer to type or file for some charity-points for hours.
Most overall points wins something big – like a weekend trip somewhere with a date. Let them win something smaller for each category and they all have to earn a minimum number of points so they all help the last one over the finish line."

This is awesome!!

who could collect the most phone numbers from boys at a crowded party/bar, lingerie wrestling matches against each other, a simulated female orgasm contest (ideally filmed and recorded). If you want to go more extreme, the erotic dancing ideas sound fun to watch, or perhaps a simulated blow job contest (performed on dildos...presumably).
Some really good ideas here too.  

2-A lap dancing contest. If some of your guy friends want to be on the receiving end all the better.

If we can get some of our guy friends in on this, I think it'd be a keeper.

So what do you guys think?  Any other competition ideas.  This is really shaping into a fun competition.  I like things like this because the sissies wanting to win, will try much harder than in we simply make them do something and they go through the motions.   

I really think we're going to want to add one more sissy.  Jill, Cindy, and Amber all have a primary mistress now.  We're all happy to help, but we need one where we are in charge.  I have a candidate too and an easy way to get him into dresses too.   We'll see.  I'm hearing from some of the others that 4 is too many, but I really want at least one sissy totally under our control.

Finally, Colleen and Kristine have their blog up.  I'll post a link to it in our blogroll. 

Tuesday, August 17, 2010

We're Back

Well, we're all back. It's good to be back. We have a lot of things to take care of including a few things that should have already been done. We have found a perfect little place for the three sissies and made sure they had permission to paint. We're toying with giving them each a different Disney Princess theme for each of their rooms. This Fall is really going to be sissy boot camp as we want each of them to take things to another level. Jill is so close to being able to live and act totally as a woman without anybody ever knowing. Cindy is ready for a girl job and to interact with others as a woman everyday. Amber will be the full time maid and she needs to work on her domestic skills as well as being able to pass in her classes. We're not going to slack off and we made it clear to the sissies. They will be spending very little time in men's clothing this semester and they will be expected to talk, move, and act like the women they will appear to be--where possible we even expect them to think like women.

Does Amber interact with boys? Do the maid's clean up after boys? Not much. Peter and Dan are friends of ours who get maid service in their apartment. Tom is a boy that Cindy dated that gets maid service and Matt is Karen's boyfriend--also on the maid list.

Somebody said we should have them rush. Unfortunately, when you go through the process the sororities get all sorts of info on you and they would stand out as guys pledging right away.

Are the sissies just projects or do you see them as friends now? What do you think will happen when they're released? They are friends now. Yes, they started as projects, but we've spent a lot of time and they do grow on you. Release--and I don't know that I've ever said this to Jill--is not total freedom. It's freedom and not having to follow orders or dress up daily, but it doesn't mean I won't call her up when she's thirty and tell her I want her to get her maid outfit together and serve at a party. Sorry, but that's how I feel about it.

Dating boys is a must for the feminine experience. Amber is almost at that point and will do so under Susan's watchful eye. I think Kristine and Colleen would love to double date with their sissy boyfriends as well.

How about some questions for you.

1. Which Disney Princess does each sissy remind you of?
2. What would be a good category for a top sissy contest?
3. Do you think we're too nice, too mean, or just right?
4. What is the outfit you would like to see each sissy wear the most?

Wednesday, August 11, 2010

Odds and Ends

I hope you like pictures of Amber because that's all I really have on my hard drive. The other maid with Amber in the previous picture was Cindy--somebody had asked.

One comment I read, which I'm leaving unposted for the others said, that we despised the sissies when they were men. That's really not true. Speaking for me, Amber was my boyfriend and even though he admittedly had some character flaws and a roving eye, I still cared enough about him to want to do this. If I despised him, when I put him in the dress, I would have duct taped him to the big statue in the middle of campus ala Veronica Mars (Great show by the way).

I can't speak for the other mistresses, but before I became involved I read all the blogs from start to finish and I have had a chance to see how things with the sissies and mistresses are now. Jill was just a freshman who thought she was God's gift to women and to the university in general. They put him in a dress to take him down a peg and were shocked how much fun they had and realized they could keep doing it. He was an annoyance, but I don't think they despised him. Cindy was more convenient than anything. They really only saw him in one class I think, but being smitten with Jill is what got him turned.

We do root for our girls and they have grown from the experience. I have thought a bit about how things will be with Amber and I, if we do eventually get married. I will not be keeping her in dresses 24/7. However, there will be a few outfits, a paddle, and some sturdy, but soft clothesline for those moments when she forgets who wears the pants and who wears the pantyhose in this relationship.

Finally, the mistress summit was more than anything just a girls night extended over a couple of days. We did discuss things this year. One thing that we discussed, I could definitely see them taking another sissy at sometime just because they are losing some control over Jill and Cindy to Kristine and Colleen. They also know that four sissies is a lot of work so we'll see. I think we may get the sissies matching sorority sweaters if they're living together. Anybody have any ideas? There already is a Sigma Iota Sigma.

Tuesday, August 10, 2010

Keeping the Home Fires Burning

Wow, what poor communication on our parts. The school year will be starting for us very soon. A money saving trick that a lot of us use is to get an apartment lease through August 1 instead of September 1 and then go visit the parents and avoid paying double rent for August. There is a lot of new news. I'll try and give you the highlights of what I heard and what I learned.

Mistresses Retreat - We took 3 days together at a cottage to party, drink heavily, relax and discuss plans for the sissies moving forward. All the mistresses were there including our mistresses in training Colleen and Kristine. We agreed three sissies is plenty for now and that isn't likely to change. We agreed that the three of them would move in together in a slightly larger place. We agreed that Cindy is ready for a job, but that Amber isn't ready to go to class en femme yet. She's very close though and we will be giving her plenty of incentive.

Jill - Big news, I'll let her tell you about, but her family knows a little about her experimenting with crossdressing and they are supportive. They don't know the full extent, but they handled it really cool. I think I like them.

Cindy - The chastity belt returned from Germany and is working much better. She is locked away. At this time we will not be doing this to Amber or Jill. Cindy's family really likes Colleen and that takes away some of the worry about his more feminized appearance. She did have to give up the silk nails before going home, much to Wendy's disappointment.

Amber - Amber isn't ready to pass yet, but that's mostly a voice issue. Her mannerisms are getting more feminine and she still is resisting, but she is getting more cooperative.

Me - Stuck here because of my job. I miss my folks, but I really miss my puppy. People will be returning soon, beginning with Amber this week. I wish I could have gone home with her. No telling what bad habits she picked up.

Saturday, July 31, 2010

New Amber Video

Sheila and Amanda aren't thrilled with the video because of the software they used, but I think it's awesome. I think it's great that Amber gets to be a video vixen now too.

Friday, July 23, 2010

The Newest Video

Colleen is having fun with Cindy. Kristine is just plain having fun, but I don't hear Jill complaining about it. Our effort lately has been with getting Amber in line. The more I get to know Amber, the more I find her attitude a lot like Jill's. Cindy was resistant about the same from day one. She was kind of smooth and steady. With Colleen here, even that resistance is fading a bit. Jill was more fits and starts. She'd fight you on something and then you'd be ready for the next big fight and she'd go along with you. That's how Amber is. Unfortunately, for her video we don't have access to Pinnacle over Summer which is what we usually use. We're trying to make do with Microsoft's free movie maker. It's a lot simpler than Pinnacle, but it also can't do as much and we'd gotten really good at Pinnacle. I always liked to use Pinnacle to zoom in on a good leg shot of the sissies, but there are very limited zoom controls on Movie Maker. I hope we'll have that up in a few days.

Thursday, July 15, 2010

Sissy Bliss

We have some big plans to get some nice photos of the 3 sissies together, but here's a little sampling of what's to come.  I'm really excited to see them as bridesmaids.  I don't think they have any idea what they're in for.  It's more than a one day thing.    I really love Colleen's girlie points idea and I think it may be something to use on Amber and Jill as well.   It's fun watching Cindy try and find ways to be more feminine.  Amber has sort of reached an impasse this week.  She does what we tell her, but she's not putting the extra work in that she needs to do if she's going to be passable.  She certainly is good looking enough, but as soon as she moves or talks she will give herself away.

Sunday, July 11, 2010

Something Big

Something big is coming and I think it will be amazing. It'll definitely have some elements of humiliation, but also a lot of femininity. The bad news is I'm sworn to secrecy. The good news is you'll find out very soon. Oh I hate keeping secrets :) We had an awesome time at a local festival. Had fun at 80s night last night with our new Material Girl. Life is good. I've enjoyed meeting Colleen and Kristine. They're going to be a lot of fun to have around next year.

Wednesday, July 7, 2010

Most Humiliating

I had an interesting question about asked today about what the most humiliating thing we've ever done to the sissies. Hmm, I'd say the coming out party was probably the most embarrassing night. Finding out all those people knew their secrets and being the focus of such a party, had to be humiliating.
However, each sissy has their own humiliations and I think a lot of times they're small. Jill has confided that the most embarrassing moment for her was the first time she shaved her legs. She said it felt major and she was the one doing it to herself. I think Colleen has found far more humiliating things to do to Cindy than we ever have. Cindy had some public appearances when she really couldn't pass yet that I'm sure are up there for her. Amber's biggest humiliation is rather unique. She is most embarrassed by wearing things that Sue owned. They're not quite the same size, but some stuff fits including shoes--though Amber already has more heels than Sue does. That gives me a good idea for Amber's scent.

Saturday, July 3, 2010

Saying Yes to The Dress

One of the most fun things we have done with each of the sissies is to take her to one of our fine local bridal shops. We're surrounded by them and by and large, they don't mind if the sissies try on a wedding dress or two. I think we enjoy it too much because we waited for Jill to be passable, Cindy got to go when she was barely passing, and Amber was taken without regard to anybody thinking she was female.

The salesperson was wonderful before getting distracted by another customer, at one point asking us if we were all her bridesmaids. I think she was even trying to sell us a corset, which I wouldn't be surprised to see Sue go back to pick up. Amber was of course mortified to be seen in her wedding dress, which of course was the point. For somebody like me who likes to think of the psychological impact of feminization, dressing like a bride is such a feminine thing. It's such a power trip to see a guy doing it.

Cindy's surprise posting got a lot of questions raised. I don't know everything, but I do know the chastity belt was Colleen's idea. She spent a boatload of cash on getting one from Germany that's supposed to be designed especially for crossdressers. It will leave Cindy flat in front, but they've had major problems with it. The belt is currently on it's way back to Germany for adjustment and Cindy had a rather awkward rash. The belt may be returned. There are other ways to ensure that a guy is chaste, but the belt had possibilities.

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.