The title sissy implies some degree of service to others, females in particular. The second
type of sissy is introduced to panties, lingerie, and possibly other women's clothing in late
teens, 20s or even later in life. The person who introduces him is typically a girl friend or wife.
A few late bloomers discover such on their own, but there are few in this category.
Today, we will focus on the start of training for the most common type of sissy. Usually, his
desire to wear and play with panties and other lingerie is a very private matter that he has not
shared with anyone. If he goes off to college or the military, his desires will be suppressed for
the time being. Once he is on his own, the desires may blossom or he may just dabble in them,
while focusing on dating females. He will likely keep his stash of panties, bras, hose, and etc.,
wear privately and play with them regardless of his relationships with females.
Sooner or later, he becomes involved in a relationship that leads to marriage, living together,
or some arrangement that makes storing his stash of lingerie difficult. He will manage somehow
to hold on to it.
His significant other (SO) will learn that she is living with a sissy when one of two things
happen: she comes home early and finds him dressed up, surfing the web, looking at pics
of females with a dildo in his mouth, and possibly a butt plug in his butt (rear pussy for sissies).
He may be about to cum in the panties that are wrapped around his clitty (short for overgrown
clitoris) - not his cock or penis. The other way of discovery is to be looking for something in
the attic, basement, or garage and finding all his lingerie and possibly porno magazines (at least
before the Internet) along with CDs and floppy disks which contain similar images and possibly
stories about sissies. In either case, it's time for a talk!
Since you have caught sissy all dressed up, you might as well keep him that way. If you found
his stuff, you can bring it up with him later, in a proper setting. Assuming he's dressed, take
him out of the room where you found him and make him stand in front of you in a room of
your choosing. You might as well assume the worst since you found him with a dildo in is mouth.
Feel free to call him a dirty, disgusting pervert with plenty of expletives. Ask him directly if he
is a faggot, cock sucker, queer, or whatever. Tell him to pull down his panties so you can see his
clitty. (If you prefer, make him take off everything.) Watch his clitty's response as you question
him. It may become erect or it may be so frightened that it will shrink. Don't be surprised if
Make him answer ALL the questions that you want to ask him then. Ask about not if but
HOW OFTEN he dresses up and wanks off while sucking on dildos. Ask him how often
he shops for panties and how many he has. (Same with bras, slips, etc.) Ask him how much
he has spent in the last month or year. If he admits to any male-to-male encounters, ask him
how often, does he have a boyfriend, or pick up guys in the parks and restrooms. Also, if
he used condoms. Finally, when you are through your questioning for the day, tell him to take
you to his collection. Take possession of ALL of it. Tell him YOU will decide when and if
he can wear any of it again. Also, you will make sure that YOU control when and if he cums.
And finally, you will make sure he is properly supervised, so he can't be playing with himself,
dresses as a sissy, while you are away.
A note on sissy sex: most sissies only have sex with themselves and occasionally with their
SOs. Most sissies are not very good a sex with females as they wank off too often, have
fantasies that are different from traditional heterosexual relations, often have small clitties
(under six inches), have trouble maintaining erections, etc. Various studies have suggested
that about 75% of cross dressers are heterosexual and many gays want nothing to do with
sissies. My own estimate is that of the 75% claiming to be hetero; about 50% are
probably bi-sexual or wish to be.
Next steps are up to you. Store his stuff under lock and key or give to a trusted friend
to store. As you told him, YOU will decide what he wears when. You will decide if and
when and how he cums.
I strongly recommend chastity devices for sissies as most are compulsive wankers. Don't
be surprised if he wanks off in the office restroom. Until you can lock him up, you may
want to have his time away from you supervised as much as possible. To do so, you
may enlist help from any female relative living nearby, a trusted friend of neighbor, or
whomever you like. They will serve as a "sissy-sitter" when you are not there. If you
don't want to tell them why, make up a good story about how he's under a lot of pressure
at work, has been depressed lately, or whatever. You just want someone to be around
him when you are not there. He will assume you told them he was a sissy.
Once the chastity device arrives, it should be installed as soon as possible. You will
order him to comply or else everyone will know that he is a sissy. He will comply.
Next, you will make sure he wears panties ALL the time. For the most part, they
will be full-cut briefs, in pastel colors (nothing red or black), and some will have flowers
and lace. You will purchase a few pair to start him off, but he will purchase others,
under your supervision. You will donate to charity ALL his male underwear. You will
save his jock strap or one pair of underwear for a little ceremony I will describe later.
When he starts to get dressed in the morning, he will open his underwear drawer
and find a few pairs of panties. He will likely complain that he can't wear them to work,
and he wouldn't be caught dead in them at the gym. You will tell him that since he
wants to play dress up, he will wear panties ALL the time as women do. It's a good
idea to have him wear panty liners or thin pads all the time to catch his sissy drippings. Once
he is locked up, pads become even more necessary. Finally, one qualification: if he works
in the public safety field and has to change clothes in the locker room, you might
consider letting him wear cotton Hanes or Jockey for Her to work. He might have
some difficulties if he was found to be wearing panty looking panties in the firehouse.
In addition to wearing panties, you will insist that he use ALL female cosmetics with
the exception of a male razor for shaving his face. So it's female deodorant, soap,
powder,etc. and NO masculine aftershave.
He must also sleep in a ladies' nightgown. You pick the style that suits you.
Since he must learn to serve, you will make certain that he does ALL the housework
and the shopping that he can be trusted to do. You will train him properly to shop for
anything your need at a later date. He is to wait on you hand and foot. That's the
price he pays for not sharing his secret. Remind him of it if he questions you. Unless you
have children or other adults in the home, he may do his house clearing while wearing only his
panties. Later, he may be given a maid's outfit.
There will be times when his cleaning is not what it should be. You should keep a
hairbrush or paddle available for those occasions. If you choose to spank him while
he is over your knee, be sure to keep a towel between his clitty and your clothing.
Sissies have been known to cum while being spanked! If he is really bad,
another punishment is Ben Gay ointment on his clitty and testicles. Of course, the
best punishment is to play with his mind. For example, he must have permission to
participate in any outside male activity. So, if he wants to go to the game with his
buddies, tell him he had better clean properly. Of course, there is no reason
why a sissy should engage in such activities. I simply use it as an example.
In addition to catching sissy dressed up or finding his stash of sissy clothing, there
are other offences that may justify compulsory sissy training.
1. Infidelity is certainly one such case. If he's thinks its ok to get into another
woman's panties, he certainly needs to be put into his own panties. Locking up
his clitty becomes a very high priority.
2. Being caught with a porno collection that is especially debasing and degrading
toward women. This collection could be hardcopy, on his pc, CDs, or videos.
3. If he has developed a habit of staring too long and repeatedly at other women,
or if he has been repeatedly making sexist's comments. You are the judge, of course.
4. Any accusation of sexual harassment that appears to have a reasonable
amount of credibility.
5. Realizing that sissy has been dressing up in YOUR clothes. Bras are
stretched; panties and slips have stains on them. You are outraged!
I know of at lest two cases in which the wife decided that his offence,
short of infidelity but listed above, was sufficient to justify sissy training.
At another point, I will discuss situations where the SO simply desires to
sissy train her guy, without his committing one of these offences.
The switch to panties needs to be immediate. As part of that change, you may
wish to have a little ceremony to celebrate that sissy will be wearing panties from
now on. You may wish to invite a close friend or friend(s)
to add to his experience. The invitees could include any males, including gay males,
who might be sympathetic with your decision.
Sissy will be wearing a jock strap or his last pair of male underwear. Wearing
nothing else, he will stand in front of a small table or the dining room table that has
two candles. On the left side of candles will be a pair of scissors. Between the
candles will be a nice silky pair of pink panties. On your command, he will remove
his last pair of male underwear and place them to the right of the candles. He will
then put on the pink panties. He will then state five times,
"I am a sissy and will always wear panties."
When he is through, he will pick up the scissors and the male underwear. He will
first cut out the label which will be saved for lamination and then posted in a place
where he will see it daily. He will then cut the underwear into little pieces and deposit
the pieces on the table. You should now congratulate him on accepting
his sissy status and recognizing the need for him to wear panties. If you have other
guests, you may want to serve refreshments while sissy stands in front of the table in
After learning that he must wear panties, his next step as a sissy is to learn to shave
his legs. He will later shave the rest of his body, except his head, if you desire and if
will not cause problems in his job or with other family members. Shaved legs are easier
to explain. Maybe he has a medical problem or your simply got tired
of his hairy legs scratching your nice smooth legs in bed. He will shave them or have
them waxed in a salon as needed. Of course, the lady who waxes his legs will likely
see his panties.
Sissy now needs a sissy name. Ask him the names of some of the girls from high
school who really got him excited but would have nothing to do with him. He will
mention a couple names. Ask him which one he liked
best. He will respond, "Debbie". Fine, your name is now "Sissy Debbie".
Another adjustment he must make is learning to sit whenever he pees. If he is
locked up, he will have no choice. Otherwise, you must insist that he sit and
always leave the bathroom door open.
Sissy will need new clothes so you will take him shopping. First stop will be the
lingerie department of a major department store where you will purchase more
panties: full-cut nylon in pastel colors. You may also want to purchase hose, both
pantyhose and thigh highs, when they are on sale. He will not be wearing any garters
and hose, at least not at this point. You will point to the panties you want him to purchase.
He will pick them up and hold them in front of his waist, so that you can approve. Be
sure there are other people around to see this. Then take the panties in your hands
and stretch it from his navel to the middle of his back. You will hold it there and say
loudly enough to be heard, "These panties should fit your properly". After that, let him
purchase the panties using his credit card or personal check. Then the clerk can say
if she chooses, "thank you, Mr. Smith. I hope you enjoy your purchase." He will respond,
"Sissy Debbie thanks you for helping him today and he will enjoy wearing his new panties."
Whenever sissy goes shopping, he will ALWAYS ask for assistance from a sale
clerk. He will ALWAYS tell her that the item he is looking for is for him, since he
is a sissy. He will ALWAYS thank the sales clerk, using language similar to that
used above. Hopefully, after he had visited the store a few times, the clerks will
recognize him and say hello to him using his sissy name.
For bras, it would be nice for your sissy to have a professional fitting. If you make
inquiries, you will probably find some lingerie specialty shops that will do the fitting,
suggesting you come at a time when they have few customers. Of course, bras
purchased at such stores are more expensive. So you may have to simply measure him,
take him to the discount or department store, and pick out ones you think will fit. He can
always return them if they do not, explaining that they did not fit him properly. Select bras
that are lightly padded since he has nothing to put in them at this time. Hormones,
natural and synthetic, will be covered later.
Now it's time for sissy's outerwear. Since summer is almost over, it's a great time to
purchase the short-shorts, tight tees, and tank tops he will be wearing now and next
summer. Look for light colored short-shorts in white, yellow, and pink that will show
his flowered panties. You will probably find them in the junior department since they
are intended for teenage girls. The best ones, made by Derek Heart and other companies,
have little holes in them, and a liner. When you very carefully remove the liner with scissors,
sissy will be wearing short-shorts with little holes that will show off his flower panties
nicely. Be sure the panties have a light colored background and dark flowers for maximum
Sissy tees and tanks should also be light, pastel colors either solid or with designs
that only a sissy would wear. They should fit tightly enough that his bra will show
nicely. You may allow sissy to wear a ladies hat or baseball cap to keep the sun
out of his eyes. Sunglasses may help hide his embarrassment.
Until he purchases sissy tennis shoes, his own may do. When he purchases his
first sissy shoes, he will do so in a store where clerks help him, as described above.
He will wear them out of the store, with his old shoes in the bag. Be sure his socks
are distinctly sissy too with little designs that are color coordinated with his outfit.
Since these shorts will not likely have pockets, sissy will need a purse to carry
his wallet, keys, sanitary pads, lipstick, and condoms. (Sissy should always be
prepared for that time when he finds the guy of his dream, but more on that later.
Now the condoms are there to make him wonder what's next.) The purse should be
the small but distinctive kind carried by teenagers. The color is up to you.
Now it's time to take sissy, sissy shopping. I good place might be a discount
mall that's not too far away. Outlet stores have great prices and they have been
known to be sissy friendly. So, he gets to try on ladies clothes in the store, even
bras. Many people will have the opportunity to see sissy in his splendour, with his
panties showing through his shorts and his lightly padded bra pressing out the tee
or tank top.
Purchasing sissy's wardrobe does not have to strain the family budget. Don't forget
about the consignment and second-hand stores. You can find some real treasures there,
including great tees and maybe even shorts for sissy. For winter clothes, it is the place
to go. Your ultimate goal is to have enough sissy clothes for all seasons so that he
will only wear men's clothing to work and when with family. His sissy clothing will
occupy the major part of his closet with his male clothes in the back. His dresser
will hold sissy clothing only.