A Sissy Master for the real world.

I have been contemplating the real world implications of my instructions and directions to my sissies. Separating and integrating fantasy and reality is an important primary goal for my sissies.

For example, I posted my own fantasy of sending my sissies to work with a chastity belt and attached butt plug. I doubt this would be a good idea unless the sissy had already proved she could wear an unattached plug all day at work with no problems, both physically and work-wise.

Right now, at least, the fantasy doesn't meet reality, and is understood to be separate.

Another reality meets fantasy issue: I can threaten a sissy's personal information going to important people if the sissy does not take a punishment as instructed. Will I do it? If I do, it would probably mean the end of my hold over the sissy. If I don't, in response to rebellion on the part of the sissy, the sissy will realize that my hold over her is weak. Since either way would end our Master-Sissy relationship, I suppose that my decision would depend on how upset the sissy has made me with her behavior.

I also understand the stress of wearing a sissy's hair at a family reunion, for example. I would expect my sissy to get permission ahead of time to not wear her hair to the event. There would be a penance to pay, to be sure, but I would likely relax my rules for this occasion. And the penance would be nothing compared to the punishment for not getting permission ahead of time.

Here's another real world issue: I have important things to do that I have to neglect my sissies to take care of. A project or two is due soon, and I have a friend dying of cancer. I hope my sissies understand that I am still watching them, even if they do not hear from me as often as they have recently. I find great pleasure in interacting with them.

On sissies who need wigs...

Sissies who cannot have styled hair because of work or some other issue are going to have to get a nice looking wig. The wig must look good, and will be mandatory every waking hour not at work or traveling to or from work. This does not include business travel, unless traveling with a coworker.

The wig must approximate your natural hair color and length. So if you are a short-haired blonde, you must get a short haired blonde wig. Here is an inexpensive example. Here is more expensive darker haired example. So Sissy Tracy, now you know what type of wig you're getting, and you know you're going to wear it all the time, except for work. You will not get a longer wig until a year from the point you get the short one, and it will only be up to six inches longer. We are simulating natural hair growth, if you haven't figured it out by now. The wig will then be considered your "hair."

This means you are wearing your hair all day on weekends, on workdays when you get up in the morning until you step out the door, and immediately back on when you get home. You will not go anywhere else without your wig with you, so if you are at work, and you need to run errands, you will first come home, put on your wig, and then go do your errands. You will do it every time, you will not slip up, and if you do, you will inform me ASAP. I promise there will be an un-fun, and un-sexy punishment.

Isn't it sad that we live in a world where you have to leave behind your true self in order to earn a living? This sissy will be seperated from her hair all day long at work. How distressing! I can tell that my sissies are getting to the point that they would feel naked without their lip-gloss, shiny nails, and panties. Without them, they would lose confidence in who they are! My girls are growing into their real selves. I love it.

My own fantasy

Here's a fantasy of mine. I have my sissy locked into a chastity belt, with no rear guard, and underneath the chastity belt is this.

What is it?

It's a silicone butt plug attached to a cock ring.

Implication?

The chastity belt would make it impossible to remove the cock ring, and my sissy would be plugged any time she didn't want a used butt plug hanging between their legs, or put another way, when she isn't making number 2 or being used roughly by her master.

This is the only solution I can think of to the 'locked in a butt plug but has to go to work problem."

This way, when not in the bathroom, there is no place to put the plug but where it belongs, in the girl's butt, but she can go to the bathroom when she needs to, without being unlocked by the Master.

What do my sissies have to say about that? I think it's a wonderful idea, and I wish I could be in the same city as my sissies so I could personally administer its implementation. I would put the ring on the sissy. I would insert the plug. I would lock on the chastity belt. I would keep the only key. Does anyone want to try it!?

Hair cuts for mid length hair...

I am much delighted to share these pictures with you. I scoured the web looking for these examples of simply beautiful hairstyles.

I want my sissies of mid length hair to have haircuts and styles similar to the below. I think a page-boy style bob, with a blunt cut and soft tapering at the ends, just SCREAMS "I'm a sissy."
I also think subtle highlights add a little something, too. See how it adds dimension and depth to her hair? Don't you just want to run your fingers through it?

Yes, it looks good on blonde girls too.

This one has a little more taper than I like, but it's still very tasteful AND feminine.

Not a perfect bob, but damn sexy. I wish the picture wasn't cut off at the shoulders. Remember this picture when you're posing for pictures you're sending me...

This pic (above) is perhaps difficult to see, but a good example.

The same picture brightened, contrasted, and desaturated (except for the face) in GIMP. Close up, it looks like the face is peering through a cutout!

Yes, a bob looks professional too!

This one is practically bubbling with confidance. Look at the smirk on that face. It says, "I'm sexy, and you can't have me!" Remember this picture when you're posing for your pictures too.

Master X.

Email exchange of note...

It was a fairly typical set of updates from Sissy Tracy (who must email me when she updates because of her recalcitrance.)

"Master,

I have posted my panties to my blog today.

On another note, I am heading to Indiana for work the week of August 9th through the 15th.

I've no idea if I will have internet access or not. But if I do, I will be on a loaned laptop from the company. Hopefully, I can use that.

Sissy Tracy"

My response:
"Sissy Tracy,

You aren't exempt from your duties while you are out of town. In preparation for your trip, you will call ahead to determine if internet access is possible.

If it isn't (or even if there's a possibility it isn't), you will purchase a little girl's journal, and a girly pen, and you will keep two pages of notes per day you do not have access. The first page of the journal should be decorated with the words "Sissy Tracy's World." The next pages will have your rules. Then, each day you are gone, one page will be filled with your thoughts about wearing your panties, following your rules, and submitting to your Master, and one page filled with naughty girly drawing of hearts, flowers, cocks, lips, bikinis, and you and your Master. When you get back, you will take pictures of the journal pages and upload them, summarizing the most interesting parts.

You will also take pictures of your luggage with your panties and waist cincher packed in them, of you in your panties while traveling, and of you every day with that day's panties, all to be uploaded when you get back.

Now, regarding your hair: you will take pictures of the wigs you are considering buying, and we'll determine together, on your blog, which one you'll get. You'll be getting just one, and the selection of it is very important, because you'll be wearing it every waking minute you are not 1) traveling to or from work, or 2) at work.

If you are unclear on any of this, or have a problem with any of this, I expect you to let me know as soon as possible.

Master X"

Outside observers, do you think I am being fair to Sissy Tracy?

Sissies, do you think I am being too nice to Sissy Tracy, or should I insist on Sissy Tracy finding internet even at the library or hotel lobby?

I'm asking purely out of curiousity, because I think the extra work with the journal is a fair trade-off. I'm sure my sissies would agree I am incredibly fair, if not mostly.

Master X.

A short, but exemplary post

Though it is a short one, Sissy Tracy writes a most exemplary post in her blog.

The entire text is:

"I have been spending time going through Master's rules to ensure I haven't missed anything. Here is an example. I am able to insert the plug entirely now. But it still takes a few minutes to do so. Here I am trying to squeeze it out on my own without any hands. But it is to large to remove without intervention. The hard part still is eating my own cum when I inevitably orgasm from it. I cannot believe how good it feels inside me."

A picture paints a thousand words, however, and her picture makes this post. I responded:

"Of course it feels good inside you. Doing what's right feels good, and a good sissy should be plugged.

I must say, this is a picture perfect post (pun intended). Most exceptional, indeed. I really enjoy your panty pictures as well. I want to see all the feminine undergarments your wearing in the photos, and I want to see more of your delicious ass. It is SOOO cute.

This type of work makes me proud to be a sissy master."

I hope all my sissies can learn from this post. I don't mean to neglect them, but Sissy Tracy needs a little "extra" attention. Please comment on her post how much you like it (or the picture!)

A little reading material

Here's a little reading material for my sissies. Think of me while reading it, and tell me how that made you feel...

Kudos where kudos is due.

To her credit, Sissy Tracy did perform an excellent service in creating a report on feminizing foods. The only criticism I had is that there is a bit on imitating girls, that doesn't come off quite right to me.

If the rest of my sissies want to summarize this in a shorter version with their own additional research, that would be a nice thing.

I really want Sissy Tracy to succeed as my sissy, I hope everyone else is rooting for her too!

Power... over sissies... ahhhhh...

Why do I feel like laughing evilly and maniacally? Probably because I have power. Power over my sissies.

If my sissies don't do as I say, they won't be my sissies much longer.

Khrissi has virtually abandoned her blog, and refused to make the changes I told her to make. I will boot her from my sissy wagon if she does not comply shortly.

Sissy Tracy is under, shall we say, probation, and will comply, or else she faces worse complications. She is now required to post daily photos of her in her panties for the day. As a bonus, this allows me to track her grooming.

Sissy Annika is pleasing me greatly with her posts. I love her photos of the cocks and mouths, especially the one on this post. I am very glad she is showing us the parts of her assignments that are complete. I want that to be each and every one you. She already has her list of rules in the side column of her site. Oh my! What a good sissy!!

If you want to join my sissy wagon, please let me know, my email is on my profile page. If you've requested, but you've slipped through the cracks, I apologize, but email me again. I think at least one sissy may have slipped through my fingers... and I want to make sure I give each sissy the attention she deserves.

If you think you'll need to be blackmailed to comply, this is negotiable, but I won't break any laws. Sissy Tracy is facing a certain amount of leverage... and I am finding a great deal of joy in applying it.

Assignment 6 (with optional parts)

This summary is not available. Please click here to view the post.

Housekeeping part 2

I have changed my blog's layout a bit. I have widened the text columns and added some adverts to possibly generate some return for my blog's effort. I had to remove the obnoxious ads, but I hope that the rest of the ads are viewed as a good thing, because they will encourage me to continue the blog. If there are any problems anyone is having with the blog, please note here or email me and I may make a change to it.

Also, I have been in communication with an extremely advanced sissy who wants me to set a deadline for you to start sucking actual cocks. Will it go that far? That's up to me, not you.

In the meantime, I'm not seeing enough updates from my sissies who have started with my program. If I'm not seeing an update at least every other day, I'll be very unhappy. - Master X.

A little housekeeping

Here's a little housekeeping stuff, my sissies. I know that some of you who are following me are intending to begin your blog, but you just haven't started it yet. Here's some motivation: if you're a sissy who wants to start, but just hasn't, no cumming until you start your sissy blog!

And some of you who are doing your blog aren't spending nearly enough time on it. Here's a tip. I want you to spend five minutes per day writing a note on your blog, if only a very short one, about your sissy life. So I'll add that to the rules list as soon as I get a chance.

If you're feeling overwhelmed with all the rules, email me, and we'll chat about it. I know some sissies need to move at different speeds than other sissies, so maybe we can work out some small compromises that move you along without feeling too overwhelmed.

Sound good?

Master X

Assignment 5

I had one sissy mention that she was starting to settle into her little schedule. I think that's a good sign that it's time for assignment number five...

If you're new to this site, and you want to get involved as a sissy in training, go to the first assignment and work through that assignment before you move to the next one. Most importantly, if you want special attention, you will demonstrate that you are worthy of it by creating a blog here on blogger and keeping it up-to-date.

As for your ealier assignment regarding the gloss, it does seem difficult to find a Clear Matte Gloss, but if you look hard, they are there. Until you find it, it is NOT ok to simply use a chapstick. You will simply have to do with tinted, or shiny gloss, which must be on your lips at ALL TIMES.

I want my sissies to put out a fresh face to the world. I want you to have eyes that seem to pop. Part of that can be accomplished with mascara, but mascara is a bit further than I want to take you at the moment. It can be distracting if it's not done right, and we want people to see your beauty, not makeup. Instead of mascara, I want you to invest in a good lash tint. A good lash tint won't clump up your lashes or look like you're wearing a bunch of makeup, while emphasizing how pretty your eyes are.

Now I don't think all of my sissies are ready for tiny clutches and handbags, but it's high time you bought a few nice messenger bags. I saw some excellent ones at Target, particularly a pink and brown plaid one by Mossimo next to the purses. I wouldn't mind if instead you got a tote bag, but it just seems like the messenger bag is so much more functional for my sissies. The one in the link is also very acceptable, but I don't want you to buy a black one, you should really look for several in different colors to coordinate with your outfits. Once you have one, you should have it with you EVERYWHERE you go, except work (unless appropriate for your work). They are so handy you'll find you won't know how you lived without it!

Finally, now that we are done (for this lesson/assignment) with the outer sissy, we're going to work on the inner sissy.

You need to buy a dildo (as lifelike as possible), preferably made from cyberskin, though if you're on a tight budget, a cheapo will do. But if you're really taking this seriously, you'll get a cyberskin one, because it will make your experience much more realistic, which is what we all want, right sissies? ;) Here's a hint as to what's coming: you'll also need flavored lube.

Now, every week for 30 minutes, you're going to simulate oral sex with this dildo and a few drops of the flavored lube reapplied as frequently as you like. You will spend five minutes at least attempting and learning to deep throat it. You will masturbate with a condom on your little clitty while you practice making love to the dildo with your mouth. You will practice until you cum, or until the 30 minutes is up, whichever comes LAST. Then you will take your condom full of your cum, and spill all of that cum on the head of the dildo or inside your mouth, and suck the head with your pretty fingers around the shaft as if it just came inside your mouth. The cum should still be warm as the cock you've been sucking is warm from your throat and the cum should be warm from being in the condom on your clitty. So now you are eating cum you have sucked from the cock, and you notice how good it tastes. You want to spent at least a few more minutes sucking that head until you know you've sucked all the cum down.

If you get turned on again by finishing the job, tough luck baby, slip your little clitty back into your panties and savor your turned on state. You are not allowed to cum again for at least another hour. Why am I not letting you cum again? Think about it and let me know why you think I'm doing that to you.

Now for your rules (maybe you should print them and put them on your fridge or keep a copy with you):

1) If you cum, you must swallow it, all of it, and with a clear voice verbally thank me your master for allowing you this freedom. When you have your dildo, you must cum with its head in your mouth, and you must consume your cum from the head of the dildo (unless it is too copious, in which case, use your mouth to catch the rest of it!)

2) You must keep your body hair off with an epilator and trimmer, keeping absolutely smooth your hands, feet, thighs, underarms, chest, butt, pubic area, etc... trim your calves and arms to a #1 1/2. When you go to a hair stylist, inform them to be careful to give you soft and tapered sideburns "like a girls' cut" and to do the same in the back.

3) You should now be wearing only panties, thongs, and short boxer briefs. If you have loose and baggy clothes, begin replacing them with fitted clothes that fit your body (Banana Republic, The Gap, H&M, Zaras, all have fitted clothes. If you need bargains, go to TJ Maxx or Ross.)

4) You should be tanning your sissy butt and posting your progress on your blog.

5) Use a black lash tint at least every three days. Tweeze, trim and shape your eyebrows. Use a concealer to cover blemishes. Have a lip gloss for everyday (all the time!) use and tinted gloss for special occasions, like every time you go out for dinner. Whiten your teeth. If you wear glasses, find a more feminine/delicate pair if possible or switch to contacts. I want you to have facial features that stand out in a good way when you enter a room.

6) Use a femininely scented lotion regularly to keep your skin smooth and silky. Use a stone or something to get rid of callouses. Push back your nails cuticles and keep your nails smooth and buffed.

7) Your goal is to stretch your pussy so it can take a real man's penis. You will spend at least an hour twice a week stretching your pussy with a butt plug. If your current one is too small to have an effect, move up a size.

8) If you break the rules, your punishment is as follows: Set a timer for 30 minutes. Go put a penny on the wall at shoulder height and hold it there with your nose. Keep your legs straight, and keep your hands above your head and not touching the wall or your head. Keep in this position until you hear the timer go off. I am serious about my rules, and breaking them will bring humiliating punishments that will not be fun or entertaining.

9) Keep a blog to document your journey into becoming a sissy. Document everything, including sexy close-up pictures of you (face optional, but not skanky, or shitty, but sexy, because the idea is to humiliate you, not me), and maintain it at least monthly (if you want me happy, post a blog weekly). If I catch you letting it go, I might just give you a punishment that will leave you crying and wishing you had never done this in the first place, and I don't care how masochistic you might be, you won't like it. Post a link to your blog in the comments here.

10) You are to be exercising and counting your calories!

11) Take a cute, colorful, or light colored messenger bag with you everywhere! (You might want to keep your gloss, concealer, and lash tint in it!)

12) Practice your cocksucking skills as described above at least once a week.

Who knew that living more like a girl everyday would be so much fun?!

Desires of the Sissy Master

Part of why I get off on feminizing boys is deep down they crave it. And deep down, I love satisfying that craving. I love making them feel so turned on. And I love making them cum. And then I love making them consume their cum.

New followers are great, but I have been getting about one new follower per day, and I'm a little depressed I haven't got more followers. I want more followers. Most importantly, I want more sissies following the regimen I've laid out for them and blogging about it. This is interactive training! The best training is interactive!

My goal for my sissies is to have them become beautiful shemales that desire to have romantic relationships with other shemales and men. This training is a long-term commitment for my sissies, and a long-term commitment from me. I may have sissies that drop out of their training, but that means I have brought them as far as they are willing to go and then they will know where they are comfortable being. Thoughts?

Looking for assignment 5?

If you're caught up on your assignments (excluding optional assignments), comment here that you're ready for assignment 5. ONLY if you're really and truly ready for your next step.

Some have complained about gloss at work. You're not excused from wearing gloss at work, but you may get a matte gloss. For example...

Also, I want to see more activity on your blogs. Honestly, daily posts would make me happy. I want you to post about your success in following your rules for the day, and how it made you feel, and if you needed to take your punishment.

Here are your rules we've accumulated so far:

1) If you cum, you must swallow it, all of it, and with a clear voice verbally thank me your master for allowing you this freedom.

2) You must keep your body hair off with an epilator and trimmer, keeping absolutely smooth your hands, feet, thighs, underarms, chest, butt, pubic area, etc... trim your calves and arms to a #1 1/2. When you go to a hair stylist, inform them to be careful to give you soft and tapered sideburns like a girls' cut and to do the same in the back.

3) You should now be wearing only panties, thongs, and short boxer briefs. If you have loose and baggy clothes, begin replacing them with fitted clothes that fit your body (Banana Republic, The Gap, H&M, Zaras, all have fitted clothes. If you need bargains, go to TJ Maxx or Ross.)

4) You should be tanning your sissy butt and posting your progress on your blog.

5) Tweeze, trim and shape your eyebrows. Use a concealer to cover blemishes. Have a lip gloss for everyday use and tinted gloss for special occasions, like every time you go out for dinner. Whiten your teeth. If you wear glasses, find a more feminine/delicate pair if possible or switch to contacts. I want you to have facial features that stand out in a good way when you enter a room.

6) Use a femininely scented lotion regularly to keep your skin smooth and silky. Use a stone or something to get rid of callouses. Push back your nails cuticles and keep your nails smooth and buffed.

7) Your goal is to stretch your pussy so it can take a real man's cock. You will spend at least an hour twice a week stretching your pussy with a butt plug. If your current one is too small to have an effect, move up a size.

8) If you break the rules, your punishment is as follows: Set a timer for 30 minutes. Go put a penny on the wall at shoulder height and hold it there with your nose. Keep your legs straight, and keep your hands above your head and not touching the wall or your head. Keep in this position until you hear the timer go off. I am serious about my rules, and breaking them will bring humiliating punishments that will not be fun or entertaining.

9) Keep a blog with sexy close-up pictures of you (face optional, but not skanky, or shitty, but sexy, because the idea is to humiliate you, not me). Post up to daily posts if you are able. If you let your blog go, I won't be happy...

10) Exercise 15 minutes a day, and count your calories.

Wordle

Wordle of my blog. Nice, no? Get busy on your blogs girls...

Blogs I have really enjoyed

I have really enjoyed a few blogs out there that I think really deserve some kudos on being excellent examples of blogs I want my sissy followers to have. I want my sissies' blogs to be all out, extreme, "I am sissy, hear me PURR!"

Julie's Slutgirl is a blog that really celebrates being a sissy. I mean it, this blog is no-holds-barred, 100% sissy empowerment, with not just pictures, but beautiful edifying videos to meditate your sissyness on. Julie, I want to hand it to you, it's a great blog.

Sissy Cockmilker is another one that I want to really applaud. No other blog I have seen celebrates the most fulfilling act a sissy can partake in: having a thoroughly sucked cock explode with cum in her mouth. High five, baby girl, you've got something for my girls to look up to.

Sissies: I have a feeling you don't really know what I mean when I said I want you BLOGGING about your sissy life. I want more blogging, more pictures, more accounts of your days (however mundane), more celebrating your life as a sissy. I want to see proof that you are really working hard at improving your sissy lives.

Highly suggested optional assignment

How is everyone's fourth of July going? It's Independence Day (in the US)! Why don't all you sissies declare today your independence from the inhibitions and self-imposed restrictions that have kept you from becoming all the sissy that you can be.

Girls, I highly recommend that as you are working on cutting a more feminine figure through your diet and exercise, that you also work on other ways of having a more fit figure. I want you to find a waist cincher, and begin to use it on a regular basis.

This needn't be an expensive endeavor, although you could spend hundreds of dollars on it. If you go to ebay, you can find options shipped to you in the States for less than $10. (While you're at it, put in the word "sissy" in ebay and see what else you can find that's worthy of being added to your wardrobe...)

This sort of foundation garment will teach you to hold your waist in, and slim and slenderize you, so that you can cut a more striking figure.