Sunday, May 29, 2016

My “Original” list of Sissy Ideas and Humiliations

Okay people.  Once again I’m setting the Wayback Machine for the end of December in 2001, that time when I was a lot younger and so was the internet.  Back then, there were things just beginning to appear in the on-line netherworld that dealt with the fantasies that had consumed my mind for my entire life. 

Actually, for this posting, most of the items below were conceived of and were included when my site first opened, but over the years the list was added to, up until my website suddenly disappeared, probably back at the end of 2005.  I don’t remember the exact date anymore, even though it broke me up pretty badly when I was suddenly gone.

I wasn’t the first to post sissy ideas out on the internet.  Not by a long shot.  But I did read whatever ideas people had posted avidly.  I “consumed” them hungrily!  So with that in mind, when I opened my little website, I decided to create my own list of sissy ideas and humiliations.  Just to be different, I divided them up into categories of mild, medium, and hotter.  The number of ideas started small, but over the years, it did grow a bit.  Down below, some of the items listed are links to more extensive postings of those ideas.  Hopefully, I’ll bring you a few of them in the future. 

My original site seemed to draw an amazing number of followers, and surprisingly they often sent me their ideas and humiliations that I was very happy to add to my site.  Most of them though were included as separate pages in my site so that the authors of those things could receive proper credit for them.  I’m not sure if I’ll ever be able to present any of those extended ideas to you or not.  I’m also not sure exactly how I will go about it.  But that’s a worry for the distant future. 

And for you diaper lovers out there, yes, I had a list of sissy baby ideas and humiliations too, but that’s an entirely different list. 

So here’s my “original” list of sissy ideas and humiliations, mostly as it was at the end, when my hosting site disappeared.


These ideas are divided up into three categories - MILD, MEDIUM, and HOTTER.  The ideas may not necessarily be in the category they belong.

  1. Decorate your house in a very feminine style.  Get expert help if you need it.
  2. Take up a traditionally feminine hobby.  Sewing, or needle work are always good and can be useful.
  3. Start a doll collection and make sure you display them in your home.
  4. Learn to write with very feminine penmanship.  Use it all the time.
  5. Buy some simple but obviously feminine jewelry (necklace, bracelet, ring) and wear them while shopping.  Make sure they show.
  6. Replace your watch with a feminine one.
  7. Rule of Sums!

  1. Carry a purse whenever you leave the house.  Replace your male wallet with a feminine one.
  2. Start wearing nail polish whenever you go out (not to work).  Start with clear polish and then move on to subtle, pale shades.  Gradually make the shades darker.  How dark do you dare go?
  3. Go shopping for women's shoes.  Wear pantyhose but no socks.  Wear the shoes out of the store.  If they are ones that could almost pass for men's shoes, wear them while shopping for at least another hour to get used to them.
  4. If leaving the house just to get a meal from a fast food drive through, don't change out of your sissy clothes - go just the way you are.
  5. Or for another similar idea, go through the drive through wearing a very prominently filled bra under a tight fitting feminine top.  Your fingernails should be painted, and wear a bracelet on your left wrist.
  6. Go shopping wearing a decorative hair clip or ribbon in your hair.
  7. Go to the mall and have your ears pierced in a very public place.  Make sure your earrings are nice and feminine.  Don't forget to take proper care of them.
  8. Go shopping wearing a light touch of makeup.  Not too noticeable.  Stop and have a snack in the food court.  Before getting up, check your makeup in a compact mirror and reapply your lipstick.
  9. Spend the day shopping wearing panties, pantyhose (no socks), male pants, male shirt, male shoes, and a bra.  Kick it up further - pad the bra.
  10. Spend the day shopping wearing panties, pantyhose (no socks), male pants, male shoes, and an obviously feminine blouse.  Kick it up a notch - wear a bra under your blouse.  Kick it up further - pad the bra.
  11. Spend the day shopping wearing panties, pantyhose (no socks), male shirt, male shoes, and feminine slacks.  You can go easy and wear jeans that look like male pants, or kick it up as much as you like by wearing ever increasingly feminine styles of slacks.
  12. Spend the day shopping wearing panties, pantyhose (no socks), male shirt, male pants, and obviously feminine shoes.  Kick it up a notch - high heels.
  13. The next time you are going to have some time off from work, the day you leave work, go and have your nails done.  Have some long acrylic nails applied.  Enjoy your time off by doing all the things you like to do and go everywhere you want to or need to, but don't remove the nails until the day you go back to work.
  14. So You Don't Want To Carry A Purse!
  15. Carry A Purse

  1. Go shopping wearing panties, pantyhose (no socks), a bra, and women's shoes (they can look like men's shoes).  Go into a store, try on a skirt and buy it.  Wear it home.
  2. Never buy any male clothing.  From now on, the only clothing you may buy must be female.  Won't it be fun, when your stock of male things is gone.  Optional - every time you buy a new piece of feminine clothing, throw out something male
  3. The next time you go out to get gas in your car, do it in a skirt and high heels.  Pump the gas yourself.
  4. Join a sewing class.  Make only female clothing.  Be sure to wear all of your creations to class.
  5. Go to a hair salon and have your hair styled in as feminine a fashion as they can do.  Let the hairdressers have full control over what they do.
  6. Shopping Trip -
    1. Go to the mall wearing panties, pantyhose (with socks over top of them), and the rest of your clothes all male.
    2. Stop in a lingerie shop, try on and buy a bra.  Take your socks off and stuff them in your bra.  Wear it out of the store.  If the store doesn't want you to wear it out of the changing room, go to a public rest room to put it on (this goes for other items on this list too).
    3. Go into another store, try on and buy a pretty feminine blouse, wear it out of the store.  Have the store throw away your old shirt, or if they won't, throw your old shirt in the nearest trash can when you leave the store.
    4. Go into a jewelry store and buy yourself a nice necklace, bracelet, and woman's watch.  Wear them out of the store.
    5. Go into a nail salon and have your fingernails painted in a nice feminine color.
    6. Go into a shoe store and buy yourself some women's shoes.  Pick some with at least a 1 ½ inch heal.  Wear them out of the store.  Have the store throw away your old shoes.
    7. Go into another store and buy yourself a purse.  Put all the contents of your pockets into it and carry it.
    8. Go into another store and buy yourself some women's slacks.  Make sure they're feminine and will go with your blouse.  Wear them out of the store and have the store throw away your old pants.  By this time you should have no male clothing left at all!
    9. Go to a store where they demonstrate makeup and have them do your face for you.  Buy everything they recommend.
    10. Go into another store and try on skirts to go with your blouse.  Buy one and wear it out of the store.
    11. Treat yourself to a nice dinner out somewhere.
    12. Be sure to take some pictures to remember the occasion.
    13. Email me about how it went!

Sunday, May 22, 2016

My “Original” Sissy Diaper Period Rules

Once again, let’s set the Wayback Machine for the year 2001.  December 28th, 2001 to be exact.  As you remember from last time, that was the date where we were exploring the beginnings of my original Sissy Rules website that is now long departed and forgotten.

Once again I’d like to bring you some of the material from that ancient site.  Last time, if you remember, we looked at my original list of sissy rules.  And if you remember, there was a mention in the last rule of a list of sissy diaper period rules.  Today we’re going to look at that list. 

As before, if I had the opportunity to engage in this type of activity anymore, I’m sure that this list of rules would not work for me.  Although there might be a few that could be built upon.  Remember, this is all fantasy.  Nothing like this ever existed back then.  All I’m trying to do here is present some material that I had come up with in the distant past, when the internet was a lot younger, and so was I.

So here it is, just as it was way back on December 28th, 2001. 

The following are some of the diaper period rules.  A woman has her period for about 7 out of every 28 days and has to put up with many discomforts, problems, and potential problems.  These rules will mean that you too will have to put up with discomforts, and problems, and because you're a sissy, you must put up with some potential extra humiliation too.  Please note, you may wear diapers any time you wish when you are not on your period, but during your period, you must wear them.  Women have no say over when their periods start or end, or what they have to do at that time... and now neither do you.
  1. For 7 out of every 28 days you will wear a diaper when not at work.  Diapers are to be worn from the time you go to bed the night before your period starts to the time you get out of bed the day your period is over.
  2. When not at work, you may never pee in a toilet.
  3. If you leave the house for any reason (other than work), you must still wear and use your diapers.
  4. If you go out, you must carry a large diaper bag designed for a baby girl and keep it no further away than the car (see rules for mandatory items to be carried in the diaper bag).
  5. If anyone asks if you are wearing a diaper, be honest and tell them you are a sissy baby, and for your period you must wear and use diapers.
  6. If you are out and your diapers leek and wet your pants, you must change into your jumper, skirt, or dress before you go home (see rules for mandatory items to be carried in the diaper bag).  This will help you to remember to keep your diapers changed before they can leek.
  7. If anyone over the age of 18 offers to change your diaper for you, you must let them - weather or not you need changing.
    1. Remember, this person is taking on the adult responsibility of changing you, and you are a sissy baby (if you have any questions about that, think about who's wearing the diapers).  The person who changes you is in charge of you.  The calls and decisions are theirs - not yours.
    2. Changing place and time is at their option, not yours.
    3. If they offer to change you, you must get your diaper bag and bring it to them.
    4. They have the option of diapering you and then dressing you any way they wish.
    5. They can use cloth or disposable diapers.
    6. They can dress you (even in public) any way they wish, including in a dress (and don't forget the mandatory clothing items in your diaper bag), or have you wear just your diapers.
    7. They can require you to suck on your pacifier, or drink from your baby bottle.  Having you drink from your bottle while holding it with both hands keeps your hands out of the way during your diaper change and also puts more fluid back into your body so you can wet again.
    8. They are the adult and have gained this right by changing your diapers for you.


The following is a minimum of items to be carried in your diaper bag at all times.

  1. A complete list of your rules to be kept in the lid for easy inspection.
  2. 4 disposable diapers.
  3. 4 cloth diapers.
  4. 2 pair of plastic panties.
  5. diaper pins.
  6. plenty of baby wipes.
  7. A plastic sheet to change you on.
  8. plastic bags to hold used diapers.
  9. baby powder.
  10. baby lotion or oil.
  11. A pacifier.
  12. 2 baby bottles filled with anything you like, but they must be filled.
  13. A girls jumper, or skirt, or dress (ones that don't take up a lot of space and don't wrinkle easily).
  14. In warm weather, frilly girls socks.  In cold weather, girls tights.

Sunday, May 15, 2016

My “Original” Sissy Rules

Once upon a time, I was younger (obviously), and so was the internet.  There was no Blogspot.  There was no Twitter.  Believe it or not, Facebook didn’t even exist!  Imagine!  How did we ever survive?  But in those young fragile days of the internet, I had an idea to create a website dealing with some of the all too secret things that had always occupied my mind.  And so I chose a FREE website platform, where I created my fledgling site and uploaded it for all the world to see (it was on December 28th 2001 to be exact).  The website’s name?  “My Sissy Rules Fantasy.”  Guess what it dealt with!

Anyway, the basis of the entire website was a list of sissy rules that I created.  And trust me, nothing like it existed anywhere on the web at that time.  What still boggles my mind, was how popular that website became.  I still can’t believe that I continually received emails from literally all over the world!  Wow!!! 

And then I noticed that my list of rules started to get copied on other websites (mostly without credit to me).  Sometimes they would be changed just a bit from the original to fit the user’s intentions better, but most of the basic rules were always there.  Oh, I’m not angry about that, I’m very flattered.  What the heck did I start? 

Along with my list of rules on the website, I also had lists of humiliating sissy ideas and suggestions available.  And to my amazement, readers started sending me emails of their own experiences and sissy ideas for me to include on the site as well, and of course, I always posted them.  The site was actually starting to get a frightening number of pages to it (for the time). 

And then of course, the nice free web platform where I had my website posted, suddenly went away, and so did my site.  So, so sad.  Cry!  Cry!  Cry!  I can’t tell you how bereft I felt over it.  It was like I had lost a major part of myself – or like a close relative had died.  Question, is my Karen persona considered a relative?  I guess she’s relative to me – in one way or another.

I no longer see those rules posted anywhere on the internet anymore.  Of course, I don’t go looking for them either (hey, I’ve got other things to do).  But it’s been a long time now since that website went away, and since it’s been gone so long, I’m wondering if anyone out there might be interested in seeing what my “original” set of sissy rules looked like.  So I’ve decided to try occasionally posting some of the material from my old website, just for the “education” and “amusement” of anyone interested. 

Naturally, to start things off, I’m presenting my original list of sissy rules.  Would I use this list if I had the chance today?  Probably not!  But…they might form the basis of something that really could work for me. 

Oh, by the way, further down near the end of the list, you’ll see what I refer to as my list of diaper period rules for sissy babies.  That list I’m afraid, will have to be for another posting.

So without further ado, here’s my list of sissy rules, just as I first penned them back in 2001.


1.       You must always wear panties.  Sissies are not allowed to own men's underwear.

2.      You must always have your toenails painted.

3.      When at work, you must always wear panties and have your toenails painted, but you need not wear any other feminine items unless they won't show – or you want to.

4.      Never, under any circumstances, stand to pee – ever, even at work.  Sissies only sit to pee.

5.      Your face and body must be free of hair at all times.

6.      Use only female deodorant, shampoos, and conditioners.

7.      Get some very mild perfume and wear it – even when you go out (but not to work).

8.      Take frequent scented bubble baths (you might as well enjoy yourself).

9.      Read a book about nail care and buy yourself a complete nail care kit.  Your fingernails don't always have to be painted, but they should be well manicured at all times.  You must keep your toenails painted always.

10.  Whenever you sit down, you must always sit with your knees together.

11.  You must keep yourself in shape by working out to an aerobics videotape while wearing a feminine leotard and tights at least three times a week.

12.  For bedtime, a nightgown or some other type of feminine nightie must be worn.

13.  Subscribe to several women's magazines and read them.

14.  When leaving the house (not to work), besides your panties, you must always wear at least one other feminine item.

15.  When shopping, never make up an excuse that you are shopping for anyone else.  You are a sissy.  The items are for you.  Be honest.

16.  When shopping for clothes, if offered a chance to try on clothes, take it.  You should also always be wearing pantyhose under your clothes when you go out looking for new clothes.

17.  For 7 out of every 28 days you must have your period.  Keep a calendar clearly marked.  You must buy all your period needs yourself and be honest about them if asked.  If you are a sissy baby, see the rules for a diaper period.  If you're are not a sissy baby, during your period you must wear a maxi-pad at all times (you can wear this to work too).  If you use a maxi-pad, you must find a way to keep a spare one on you at all times and change your pad at least four times a day.