Heidi Kessler

THE SINGLE MAN’S GUIDE TO SISSIFICATION

by
Heidi Kessler
 Sissification

It’s a process and one that true Sissies need and crave.  

If you are one or you fantasize about becoming one you will
appreciate and enjoy this book. This is just a soft

introduction of becoming a Sissy on your own.  Buying new

clothes, going into chastity, learning how to follow the rules

to help you reach your goal of beoming more of a Sissy..

 
Chapter 1.  Underwear – First Week of Training

 
Underwear.  If you are working on becoming more of a Sissy

on your own than you will need to get rid of all of your
boxers and other male undergarments.  Ideally the best

option would be for you to go to a lingerie store and pick out

your own colorful array of women’s panties.  To make the

experience even more humiliating and exciting than I would

suggest asking a sales associate what they think would fit

you. Do not pretend you are buying this for a girlfriend or

wife. Getting matching sets of bras and panties.  Get at

least 7 pairs of underwear and two or three bras.   You will

also need stockings, buy a few different sizes to find the

right fit.  After you have done this you can return for the

next chapter.  Until than you may not continue reading. 

 
You got it?  Excellent.  Was it embarrassing? I hope so. Did

your face turn red? Did the other women look at you funny? 

Did they giggle? 

Rule 1.  You must wear your new panties every day beneath
your boy clothing.  This means going to work, errands

whatever.  When you are home and alone you must put your

bra and stockings on.  In bed, you must keep your new sexy

panties on.  You will wear your new undies for two weeks. 

During these two weeks, you can begin looking forward to

what will happen at the beginning of the third week.

 
 

Chapter 2.

Rule 2.  Remain fully shaved at all times.

 
You may shave now.  I am assuming you have worn your

girly undies for the past two weeks daily.  If you have done

so you may proceed with this step.  If not, you may not

continue. You must shave your entire body except your

arms.  Toes, calves, knees, thighs, private areas, bottom,

chest and face.   You must do this every two days or as

often as needed to remain smooth.  After you remove all of

that gross hair from your body you must moisturize your

entire body and put your panties, stockings and bra back

on. Now, you get to feel how nice and sexy it feels to wear

girl’s undies and be completely shaven.  No more nasty man

hair.  You are trying to become as good of a Sissy as you

can.  You must do this for two weeks before you are allowed

to proceed with step three – but you MAY begin your

shopping now. 

 
Chapter 3. Shopping for your new wardrobe

Rule 3. You must be dressed for 10 Hours every week,

minimum.

 Now, you are wearing girl’s undies and completely shaven. 

If you have accomplished this you may continue.  Your new

rule is that you must be fully dressed in women’s clothing at

least 10 hours a week.

You will need to do some shopping now.  Measure your feet

and buy yourself a pair of high heels – many sites including

amazon sell large sizes in heels.  The higher the better. 

Every evening you will need to practice wearing them

around the house. A corset or waist cincher to help give

your curves, a woman’s nighty, some very short skirts and

stretchy tops (keep in mind men have broader backs so you

will need to buy these in larger sizes that stretch. Shoes of

Prey offers some higher end shoes in very high quality.  For

the clothing, I would PREFER you bought it in person.  The

entire humiliating experience of buying a bunch of sexy

clothing for yourself would be good for you.  On your days

off you will need to designate time to being dressed. You

may dress only after you have completed two weeks of

undies and two weeks of being fully shaved.  If you have

completed that you may begin to dress.  You may start

shopping for your new chastity device but you may not try it
on until you have completed two weeks of dressing at least

10 hours per week.

4.  Chapter 4 Chastity

4. Rule 4 Lock up your manhood and throw away the key!

You must wear your device as much and for as long as

possible until you wear it 24/7

Obviously, I don’t know your measurements but I can make

a few suggestions on the TYPE of chastity device you need

to purchase.  It should be clear, plastic and have a lock on

it.  Some of them are made to go through metal detectors

for constant wear and others are more of a torture fest. I

want you to find one that you can wear ALL the time.  They

are made of plastic and are designed so you can go to the

bathroom and not take them off. You will start out slow,

wearing it a few hours every day, working your way up to

every night. Before you know it, it will be on 24/7. 

Showering is the same deal – simply soap up the entire area

and make sure you sanitize it.  Expect that you will not find

the PERFECT chastity device upon first selection – my

husband and I have purchased at least 6 of them.  Do not

buy cheap ones, they will rub you raw and you won’t be

able to wear them. Before you know it, it will be constantly

worn day after day, night after night. Your manhood will be

useless.  Please note, common sense must be used with

this.  If the device is irritating, rubbing marks or hurting you

than take it off!  You are not wearing the right size, a good

quality one or one that is meant for your body.  Its primary

purpose is to prevent you from having an erection.  It is not

meant to hurt you.

5.  Closet Space

Rule 5.  Designated area for all of your girly things

Nothing will make you happier than when you open a closet

or a drawer and you have multiple skirts, bras, tops and

heels to choose from.  A designated area for your Sissy

wardrobe is a must!  Treat your clothing with respect,

meaning if it gets wrinkled bring it to the dry cleaner.  Do

you think they will wonder if it’s yours?  Either way, it

doesn’t matter.  You are to designate areas in your home for

your new Sissy wardrobe.  Dresses should be hung properly,

undies folded neatly in a drawer...

6. Scent

6.. Rule 6. You must wear perfume...

So, have you been doing as you have been instructed?  If

so, you may treat yourself.

Go to any large department store that has a great selection

of women’s fragrances. Begin smelling them until you find

the one that makes you feel the sexiest, the one that turns
you on the most.  This will become your scent; all of your

clothes will have this scent.  When you get home, lightly
mist your new girly wardrobe with perfume. When you dress

up you must always put your fragrance on.  Real Sissies

wear perfume.  You are definitely a Sissy if you have gotten

to chapter 6 of this book.

 

7.  Maid’s Outfit

Rule 7.  Your house must be clean at all times
A true Sissy would do their best to keep a nice house for

their Mistress or Master. Even if you are singly now, you are
practicing.  You must train to be the best submissive Sissy.
Once a week you will put your Maid’s outfit on and

thoroughly clean your home or apartment.  You will do this

on your hands and knees and with a toothbrush if need be. 

Your purpose in life is to please and if you find the proper

Mistress or Master - don’t you want to show them you have

some value?  Obviously, your manhood is useless at this

point.  So, if you have dishes in your sink, or a dirty shower,
get up now, get dressed and begin cleaning.  You are not

permitted to continue with this book until you have finished

your domestic house duties. You can purchase cute maids

outfits right here on amazon!  How convenient is that.

 

8.  Anal plug

8. You will begin wearing plug when you are dressed

Since you have lost use of your manhood you have two
other openings that you can use to please and offer.  When

you dress you are to lube yourself and place your plug in. 
Buy one that is smaller at first and work your way up.  You

need to keep yourself stretched for your new Mistress or

Master.  If they decide they want to use a dildo or offer your
bottom to someone that is a true man than you must be
prepared and willing.  Sissy’s don’t have choices.  They

serve and do as they are told. 

 

9.  Watch Video’s on how to give pleasure

Watch video’s on how to give proper oral sex to both male

and females.  Also watch videos of Sissy’s on the receiving

end of anal sex.  You will be dressed and wearing your

chastity device and have your plug in so this will become

very frustrating for you.  Oh well…  you are just a Sissy after

all.  Learn from these video’s.  Purchase a dildo and practice

oral sex, buy one that you can mount on the side of the tub

so you can practice humping it.  Your chastity device is to

remain on at all times.  This is about pleasing others, not

you.  You are a Sissy and your purpose is to serve in all

ways. To be as sexy as possible and to please as much as
you can.

 
10.  Get a wig & makeup

Online has many videos of makeup tutorials.  Practice

makes perfect and it will take time for you to find your
perfect look.  Get to it!

 
10. Take some photos of yourself all Sissified

This will help you determine what you need to work on.  Do
your Sissy clothes make you look sexy?  Do you feel sexy? 

If not, change your look, take more photos and study the
results.
 

11.  When you feel like you have reached your potential,
months of being dressed, cleaning, being as sexy as

possible and you feel more like yourself dressed than you do
any other way you may move onto this step.   Start joining

Sissy groups, talk to others like you.  Find out about meet
ups or dinner parties.  IT DOES EXIST you just need to find

it.  Many successful business people have “double” lives. 

Place adds, go to “parties”.  If you have done your work

than you will not be recognizable.

 

I will be adding more books about specific experiences and,

outings, dungeons in NYC…please if you enjoyed this book
give me a good review and that will encourage me to post

more.  Thank you and enjoy your new found Sissification