It's Not As Easy As You Think

I know how hard my current situation is for you all to understand, but if you're one of the people who keeps saying, if you wanted to, you could get out of this please think for a second. Usually, right after telling me that if I stood up to the girls, I could get out if it without any trouble, they'll tell me they don't think I want to get out. That is exactly the attitude that my friends will have. That's exactly what I'm nervous about. My friends, family, and people at school will always be wondering if I wanted to do this.

The girls responsible for feminizing me are all very attractive, but they're also extremely cunning. They have so much to blackmail me with now. Some people have even told Jill and I that 4 girls can't overpower one guy. Even when the guys in question aren't that big. That's a picture of Heather. She's now a blackbelt in judo. She doesn't use physical force on me or anything, but it sure we no trouble for the girls to get me tied up or to control most any situation. Now, don't get me wrong they don't physically threaten me or anything, but that's just another thing that makes escape hard.
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New Video

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Tonight Will Be Humiliating

I really am still not so sure if I made a good deal by going so far with the girls in exchange for not having my friends shown pictures of me. I asked Jill about it and she told me, it isn't a question of whether your humiliated or not. If you have any male pride, you are going to be very humiliated. What you need to ask yourself is do you want to be humiliated in front of these girls and some of their friends or do you want to be humiliated in front of your own friends.

Jill and I took off from class today to get manicures and pedicures. Jill even had some work done on her hair and we had our eyebrows neatened as well. It was a major embarrassment even if Jill had been there before and had at least something of a rapport with the stylist. The girl who took care of me was only 18 and couldn't have been sweeter. I actually felt kind of bad and gave her a big tip, but I just felt so embarrassed as I saw that brush go into the polish and come out dripping red and watched my fingers one by one receive the treatment.

Jill and I then spent all afternoon working on looking our best. Scented bubble baths, painstaking making application, you name it. Now we'll be heading out to set up the party. I have received instruction on how to curtsy and say "Yes Sir" and "Yes Ma'am". I can't think of anything more humiliating then doing this party and trying to act so feminine. I just keep thinking these girls have shown absolutely no tolerance for piggish behavior. Their friends can't be too bad...I hope.
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My New Blog with Jill

I wanted to give a plug for my new blog Sex and the Sissy which I will be doing with my girlfriend Jill. The blog will be flirtier and lighter than either of our individual blogs and we'll be writing about the things that interest us most like guys and shoes and parties. We'll also have sissy advice and it'll be a great place to ask us both a question at the same time. I'm currently working on an article that should be up soon:

Sex and the Sissy

I have a few questions to answer from the blog:

"are you saying that the feeling of your skirt brushing against your stocking-clad legs does not give you a frisson of sexual excitement? I would be most surprised if it did not...Please let me know. You have lovely, shapely legs by the way." -- Sissy Isobel

I do know what you mean, but they are such a bother and so uncomfortable sometimes. If I was sexually excited by wearing pantyhose, I'd be walking around aroused 24/7. Thank you for the compliment on my legs.

"is that your real hair cindy? its soooooooo girly? i'm surprised you can ever pass as a guy?"--Mandy

I did not have real long hair when this thing started. Maybe a bit long for a guy, but certainly not feminine length. I have several very high quality wigs that I wear. The girls keep telling Jill and I that over Summer, we can go together once a week for new hairstyles, but I don't really have enough hair yet. Jill does have passively feminine hair without a wig now, but wears one for more exciting styles.

"Cindy, congratulations on looking so cute, you have come a long way in such a short time. Could you please expand on two of the comments you make?

1)....is pantyhose going to matter that much or do you face the consequences?

2) I have resisted at times, but they're always prepared for it.

What are the consequences you mention and how are the girls prepared?

On a related note, if your at college do you have a room mate (if so what's their take on things) or are you lucky enough to have a place of your own?

On the bright side, you do look cute in your new clothes and at least you have great girl friends.


1. It does matter, but I can't win so they go on in the morning.

2. The biggest threat is public exposure and they have more than enough. They can completely embarrass and humiliate me if they so choose, but there are also enough of them to simply overpower me. Both Jill and I have been threated with being tied up to a statue in the middle of campus in just our lingerie and heels.

3. I am lucky enough to live on my own, but it is still difficult to be undetected. In some ways, the summer apartment with Jill sounds like it would simplify my life a great deal.

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Sorry I Got Behind

I'm sorry that I haven't updated in awhile, but I got hopelessly behind on some of the questions and this weekend was rather busy. I know that you heard about my makeup misadventures which are most notable because I could have gone out with my friends instead. I also had a major shopping trip in my week and I'm starting to see my closet fill up with dresses, tops, and skirts the same way that my underwear drawer filled up with bras, panties, and hose. I've heard a few people say that I must love this or I would have stopped it, but it all happens so fast. You're already wearing panties, is pantyhose going to matter that much or do you face the consequences? What difference will adding a bra make? It beats the alternative. The next thing you know, you're completely and unmistakably feminine. I don't claim to have had no choice in the matter whatsoever as much as the alternative has usually been much more attractive then resisting. I have resisted at times, but they're always prepared for it.
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Bra Day

Today was bra day and no this isn't how I looked going to class. Even though the thermometer edged 50, I was still able to wear a light jacket and a heavy shirt and keep the light blue front clasp bra hidden. I didn't have any say in what bra I wore, but they didn't go out of the way to pick a tough one. I was very conscious of sitting in class and wearing a bra and matching panties as well as pantyhose. As each item has been added, I've felt more and more trapped. Everybody seemed to snap my bra at some time or another. Heather kept tracing it on my back with her pen cap. It was a pretty exhausting day and tomorrow it'll be another bra and another difficult day.
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Makeup and Bras

It has been a tough tough weekend. I've had three trips out shopping and I'm still trying to get used to the rather realistic breasts and bra I'm now sporting. Come Wednesday I'm going to have to wear an unstuffed bra under my male clothes. I'm not really well endowed. They made Jill a C cup, but decided I'd look fine as a B. B is still very noticeable.

This morning Amanda was over at 8AM for 2 hours of makeup practice. She calls it tutoring, but she mostly just says, "no" and tells me to do it over. She fixed my makeup before she left and I'm now stuck dressed like a school girl until one of them returns and gives me permission to change. Heels have been a huge problem for me. They keep telling me that I'm shuffing like a guy, How do I make them see that I am a guy?

After this weekend, my closet has dresses and my drawers have lingerie. I should not have let things get this far.
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Shopping List

Tomorrow is the big shopping trip after class. I've been advised that I have a choice between going to the mall dressed as a girl and going to the mall dressed as a guy and then having to try on dresses and high heels. I don't know which one is going to be less humiliating. I was told today that they were sure I would be totally embarrassed today, but that I could control how much by cooperating. I do need to ask, what you would like to see me add to my shopping list.

Cindy,I think both you and Jill are beautiful. How ofen do you girls "get" together?

They've been making us pose and model together a lot this week. They've told us both that they have plans for us and if one of us screws up, we'll both be in trouble.
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It's Happening So Fast

Today, I had to show up for class in pantyhose. 10 minutes into the lecture, Jill brushed her hand up and down my leg to check. There was a lot of note passing in class today. This weekend they intend to take me shopping. I feel like such an idiot to be trapped this way and I keep digging myself deeper and deeper. I've also been instructed that we're going to need to find me some breast forms so that my clothes will hang more naturally. Onto the questions:

Hello Cindy, You don't seem to happy being able to spend time with 4 beautiful girls, who seem to be hard working bright and very helpful and supportive of you? I'd have thought it would be great spending time with them and Jill? In your first post you said "I've been in panties all week and I had to purchase most of them myself." where did you purchase them and what styles fabrics and colors did you decide on?

This is not something I would ever choose for myself. Walking in heels and pantyhose and trying to do everything perfectly feminine for their satisfaction isn't a lot of fun. I bought my panties at Target. They're simple cotton panties. I bought 3 packs to make things easier.

Have you started to wear long night gowns or short baby dolls yet? Once you start, you'll never want to stop!

I have not. I'm sleeping in just my panties.

Cindy, you just look hotter every time I see you. So, how do you feel knowing that guys, and gurls like me, are looking at you thinking what a hot sissy you make?

I really try not to think about that. I'm not a big fan of guys checking me out.

Cindy, you look so hot dressed as a ballerina, and your smile is so cute. I think it was nice of Sheila to teach you to dance but I'm not sure why you say that "The girls have come up with some exceedingly humiliating things to do" why would teaching a pretty ballerina to dance be humiliating?

Oh come on. You can see why wearing a tutu and dancing like a ballerina is humiliating for most guys I would hope.

Hi Cindy,
I really love your pictures, you look so beautifull all girled up. Where can we find those 50 pictures? I'd love to see all of them

Gradually the good pics will make their way onto here. They're also putting together a website to replace the one that was up. The ones online are naturally the best ones.
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There are a lot of questions that you have left me to answer, but I really need to get to class so I'll have to wait until later. In the meantime, I feel extremely trapped. The girlshave come up with some exceedingly humiliating things to do and if I refuse, the result is that I wind up even more humiliated. Last night, Sheila decided to teach me how to dance in heels and when I objected she told me I could try a different type of dancing that didn't involve heels. I think the picture of me looking like a ballerina is the hardest one to live down yet. There is so much that I am expected to learn.
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Anonymous said...

Hello Cindy, (thats a nice name)your blog sounds interesting to say the least, especially where you say that you have posed for at least 50 pictures?
What would you say were your top three and would it be possible to post them?
I hope you update things on a regular basis'

The three up top are the top 3 that I have posed for so far that I have. I don't have all the pictures I've posed for.
Anonymous said...

Hi my name is Stephanie and ive been a cross dresser all my life and I love it. I think you make a very cute girl. I have a question for you.
Do you like the feel of girls cloths on you and do you like looking like a girl? xoxo steph

Sorry, but I don't like the feel of girls clothes and I definitely don't like how I look.
Anonymous said...

Hi Cindy,

I am really looking forward to reading your blog and wanted to ask you what you most enjoy about your transformation into a really, really cute sissy.


sissy isobel xx

I really haven't enjoyed any of it. I have cooperated because I don't have a choice, but that's not the same thing.
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