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 their late teens, 20s or even later in life. The person who introduces him is typically a Girlfriend 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. 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) 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 either happens.
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, or 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 neighbour, 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 hard copy, 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!
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 Girlfriends, co-workers including Female members of your family, 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 his panties.
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. If he responds, "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 then 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 hosiery, 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. 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 Female sales 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 coloured short-shorts in white, yellow, and pink that will show his flowered panties. 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 coloured background and dark flowers for maximum
Sissy tees and tanks should also be light, pastel colours 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<br /> are distinctly sissy too with little designs that are colour 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 sex, 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 colour 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.
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