Do you need to enroll in Sissy School? 

Are you a sissy?  Are you the BEST version of your feminized self?  If you don’t know or answer “hmmm, I don’t think so” then you should consider enrolling in Sissy School. Today, Mistress Olivia and Ms. Erika talk about how to best get the perfect femme girly girl. Listen to ideas for sissy assignments, how to practice being feminine, what to buy and wear and so much more! 

Listen to the Feminization and Sissy School episode.

Ms. Olivia: Welcome to The Weekly Hotspot. Kink conversation, advice and insight from the worlds of distance domination and phone sex. I’m Ms. Olivia and I’m here with Ms. Erika.

Last week, we talked about putting a man in panties and said wearing panties doesn’t automatically mean you’re a sissy, a crossdresser, or trans girl. We promised that this week we would talk about sissy training, which often starts with panties, right, Ms. Erika?

Feminization usually starts with panties

Ms. Erika: Oh, absolutely. Most of our sissy girls will attest that their first attraction to exploring their sissy self happens with panties.

Panties are very sexual. If you think about it, they’re wrapped around our pretty pussies. So of course they’re interested in that and whether they want to be with a woman’s pussy or have a woman’s pussy, panties are the way to start. 

Ms. Olivia: I love that. And remember folks anything to do with anything erotic, one size does not fit all.

So whether you say you’re a crossdresser or a sissy or trans girl, you don’t have to be one thing all the time. You can be a crossdresser most of the time and then a sissy at times for certain play. 

Ms. Erika: I love how you put that. There is no one size.  

Ms. Olivia: I’m not a fan of boxes and we human beings do not come with instruction manuals. Sometimes I wish we did.

Ms. Erika: It might make things easier with some people and their interests, but how much fun is it to learn about each person’s individual desires?

Each girly gurl is unique 

Ms. Olivia: It would be boring for it to be, “Oh, you’re a sissy. We’re going to do this, this and this.” Phone sex is not like a McDonald’s hamburger. It should not all be the same. And we probably don’t want to put onions and pickles on a phone sex call

Ms. Erika: But you can hold my pickle, if you know what I mean. 

Ms. Olivia: Now, before you get hungry and certainly before we go shopping, we have your very first sissy training assignment.

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Encouraging your feminization

Ms. Olivia:  There are various things or actions we can do to feminize a man: encouraging or humiliating. Your Mistress will know what works for you and how to motivate you effectively.

Let’s talk about encouraging a sissy first because this episode is inspired by Yvonne. No, she doesn’t identify as a sissy. You know Yvonne, Erika. 

Ms. Erika: Yes, she’s adorable. I love her Twitter too. 

Ms. Olivia: Yvonne also does great Twitter.  You should follow Yvonne on Twitter.

You can hear our conversation with Yvonne where she talks about self acceptance as a crossdresser.

It is one of my favorite episodes here on The Weekly Hotspot. You can hear me cry. I get all teared up about my relationship. I tell people, Mistress does not mean “bitch” no matter how rough we get in scene play.

Sharing your feminization journey

Ms. Erika: I honestly don’t think some people get it or understand exactly how vested we are with some of our girls. It is a beautiful thing.

You almost brought me to tears. I could hear the energy in your voice because I felt it too, when you’re able to give that person that safe place to be who they are.

They often don’t have any place else to share. It is just sometimes overwhelming and completely sad, but you also feel pride as they bloom into their feminization.

Ms. Olivia: And Yvonne has bloomed! 

We were talking and shopping and we got all distracted and there is only one thing wrong with Yvonne.

She is a Red Sox fan. I am a New York Mets fan. So we should not be friends. We should not be in love, but we are planning on having a mixed marriage. It will be a Red Sox and Mets marriage when we get married. 

Ms. Erika: If you two can get along, it bodes well for Washington DC; you can lead the way, show them how it’s done, Olivia. 

Ms. Olivia: I’m not going to be friends with anybody who’s a National’s fan. Oh, you mean politics! 

Ms. Erika: Differences can get along and have a great relationship.

Feminization finishing school

Ms. Olivia: Yvonne sent me this email and she said:

“After my wedding and honeymoon, Mistress decides to send me to a finishing school to eradicate any lingering maleness.”

Ms. Erika: I love that idea. Morning to night, encouraging her feminization. It’s really identifying the encouragement part. 

Sometimes people take the word sissy and think it’s very emasculating. Others embrace it as a badge of honor and both are okay. 

I love the idea of a finishing school where you are immersed in a feminine existence. You don’t have a chance to even look at your masculinity. I love that. 

What type of things would be in that school? 

What goes on in Sissy School?

Ms. Olivia: That total immersion that you mentioned, that’s really about full socialization as a woman. It offers a mental transformation and getting rid of all of those little lingering male traits.

Yvonne says “Each week, there is a formal dance and I am escorted by a gentleman.” As an aside, Yvonne is a lesbian. She is not interested in men, but she is escorted by a gentleman. 

Her reasoning is fascinating. She says:

 “This part is to make sure I do not revert to being male. When in the company of men, it is imperative I remain a lady. If, at the end of the six weeks, I exhibit even the smallest of male traits, I stay another six weeks. This way I will be completely socialized as a woman. Then there is the graduation ceremony where I will be presented to you in my wedding dress.”

Male to female transformation

Ms. Erika:  I love how we still need the masculine energy to make sure Yvonne stays a lady.  I love that idea.

Ms. Olivia: Isn’t that perfect? 

There’s this great quote by D.H. Lawrence that says, “Men are the stars. Women are the spaces between the stars.” 

Now I would flip it around. Of course, women are the stars and men are the spaces between the stars, but I think it points out that you need both. If you look up in the night sky and it’s only stars, you have a different experience than if you look up and see only blackness, right? 

It’s a different experience than when you look up and see a variety where one kind of helps to define and further illuminate the other. 

Ms. Erika: You’re absolutely right. We need that other energy. Whether or not we engage intimately with that energy is another thing. But we need that masculine energy in this situation to highlight Yvonne’s femininity.

Ms. Olivia: I think it’s really important to remember there are so many different ways that femininity can be expressed. 

In this particular podcast, we’re going to be using the term  “sissy training,” but it can also be called “feminization training.” It can be a transwoman who is looking to transform from male to female. 

It can be a variety of things. Take what you can use in this podcast and just simply ignore the rest because we’re going to be concentrating on the term “sissy.” 

What is a Sissy?

Ms. Olivia:  What exactly is the definition of a sissy?

Ms. Erika: I think the easiest definition of a sissy is a submissive male who enjoys dressing in women’s clothing, but how that expands from there is different for each person. 

Some like the very frilly, girly look; the petticoats and ribbons and knee socks. Still other males who consider themselves sissies prefer more of a slutty look: the tight dresses, the thigh highs and the big, enormous breasts. 

Advice for breast forms

Ms. Erika: To go off the track for a moment, I know one little sissy slut who did not consult me before she bought her inserts and spent the next week complaining about how heavy they were. They were DDs, and silicone! They could have been DDDs. 

Ms. Olivia: I’m a 34DD, welcome to my world, bitch.

Ms. Erika: And I said, well, that’s what you get for not consulting Mistress, knucklehead. So now you get to wear it for a week straight and I don’t want to hear about your shoulders. 

Ms. Erika: She’s going from her male self to DDDs? How about we work up to it with some stretches and exercises. Do they think our breasts are filled with air and weigh nothing?

Difference between a crossdresser and a sissy

Ms Erika: Usually the distinguishing characteristic between a sissy and a crossdresser is the submissive nature of the sissy. Sissies often seek guidance and training from a Mistress.

Crossdressers, in my experience, want an understanding, welcoming personally on the other end of the phone that understands them. They’re not necessarily looking for training or guidance. They already have that put together.

Ms. Olivia: Yvonne is one that already had it put together when I first met her. I asked her how old she was and she told me her age and I was looking at her on Skype, how beautiful her skin was. I said to her that she lives in Florida with all the sun! How does she keep her skin so beautiful?

We talked for a long time about her skincare regimen, which is very simple and she has gorgeous skin. So she didn’t need training. We have girl talk. 

Conversations with Yvonne and other crossdressers tend to be like the ones between us, Erika. “What kind of bra do you like to wear? What one highlights your boobs the best?” That kind of girl talk. We share stuff, tips, all kinds of things. But there is not the level of a power exchange like there is with sissies.

When you have that power exchange with a sissy, you are not just in training, but you have a Mistress in charge of your sissy transformation.  And we know here are difference between ways to define your gender.

Ms. Erika: What’s nice is sissy training is not one size fits all because sissies are not one size fits all. How they play or how we play is different with each girl.

Preparing for this podcast, I was searching for things regarding sissy and almost everything that came up in the searches brought up some sort of bi-curious or homosexual undercurrent.  Although that is a common factor, it’s not true for every “sissy” who would identify as a sissy. I love to get to know the people that come to me for training and devise a program specifically for them. 

Does every sissy want to be with men?

Ms. Olivia: It is quite common that the sissy either likes men or likes to be told to be with a man. Being a sissy can be a fabulous way to experience cock-curious and bi-curious tendencies or even to totally immerse yourself into your feminine self as a heterosexual woman.

I think all people have gradations in their erotic pleasure and sexuality.

I identify as bisexual not on the gradation of “only heterosexual” to “only lesbian,” I would say I am in the middle, but slightly more heterosexual. For example, if I was trapped on a desert island and could have only one gender with me, I think I would take a man. But that is not a guarantee of who I would choose because it would depend on the mood of the day I was asked.

I don’t want to be monogamous and settle on just one male or one female. I’m bisexual and greedy. I don’t want only 50% of the population. I want the whole shebang. 

You know, I think for a lot of women who get into sissy play for their partners, it’s a very common question, “Is my sissy boy actually gay.”

Dan Savage did a fabulous Savage Love column called “Is Her Sissy Boy Actually Gay?” What I loved about this article is he understands the nuances about all of this. A sissy might like boys or a sissy might like girls. 

Yvonne is certainly one of those, although she is a crossdresser and not a sissy, she is lesbian and is serving a Mistress.

Ms. Erika: I know a trans girl and you probably know her, too, Olivia. I have not talked to her about sharing her name, so no names are mentioned. Discretion is very important to us. So if I did not get your permission to reference you, I won’t.

But this trans girl we know is at a stage of her exploration where she’s struggling with her identity as a woman. “Sometimes I feel like a sissy,” when she’s feeling particularly submissive and wants direction from Mistress. She thinks, “I don’t want to be with a man, but I want to have the experience of a woman as far as lovemaking is concerned.”

Gender identity and sexuality

Ms. Erika:  That is a common conversation we’re having nowadays. And it’s so important for people to understand that however you identify as your gender does not speak directly to your sexuality. Sometimes males enjoy sissy play because it gives them permission to be with men. But that’s not always the case. You don’t have to want to be with a man in order to be sissy-like or if you are serving Mistress. 

Ms. Olivia: There’s gender play, and then there’s submission and dominance. Then there is BDSM, which is more of a kink and the sissy is tied up and often coerced into doing certain things.

Then there are all of these other layers that can be mixed and matched. Think of feminization and sexual pleasure as an erotic buffet. You don’t want to go to the buffet and only eat the garbanzo beans from the salad bar. You want the entire salad! Especially if you don’t like garbanzo beans.

Ms. Erika: I’ve talked in a previous podcast about how, when I go to a restaurant, I don’t order the same dinner because that is the one I liked before. I like variety.

Having someone who is able to be my submissive sissy girl or sissy boy or my sissy maid is fantastic because next time we may play in a different way. We might have a little more coercion, or a little less. We might just have girl talk.I like a variety. I think a lot of people like variety. 

Humiliation

Ms. Olivia: Part of that variety is when Mistress enjoys humiliating a sissy. Humiliation is not one size fits all.

When someone comes and says, “I want you to humiliate me,” I always ask, what do you consider humiliation? Because it might be a gentle, sweet humiliation. “Oh, honey, you look so pretty in that dress.”  It can be petticoat discipline humiliation. “You naughty boy, you’re going to have to wear girls’ clothes,” and have them do certain tasks and jobs.

The variety of humiliation scenes is often a big part of sissy play, don’t you think?

Ms. Erika: Oh, yes. It is to emasculate, although everybody has their own tolerance for humiliation. I find the tolerance increases over time; the more you play with humiliation, the more you need in order to get the same result. 

Each sissy humiliation task, each act that Mistress commands of you, is specifically meant to strip you, ounce by ounce, of that masculinity and transform you from your former male self to what we have now.

I also wanted to mention corset torment. They love to feel that tight corset around them. They have to breathe differently, hold themselves differently and cannot forget for one second what they are wearing.

Ms. Olivia: I think what you were talking about in terms of stripping the last vestiges of any sense of male self that is part and parcel of a sissification program. Submission can be to a dominant woman, and then maybe even presented to a dominant master. Domination can take place over a variety of ways of play.

Sissy cuckold husband

Ms. Olivia: One of the scenes I love most is turning your husband into a cuckold, for whatever reason. Then turn the cuckold husband into the submissive for your lover. So he becomes the sissy cuckold husband.

Ms. Erika: And that falls right into that progression of humiliation. A cuckold getting those behaviors set in there, being submissive, being dominated. Then you don’t have a choice. “You’re going to be wearing your girly clothes and you’re going to be a little sissy now.” That just ramps up the humiliation and makes it very exciting. 

Ms. Olivia: Emasculation, not only through feminization, with or without chastity, but the realization that you are no longer your wife’s lover.  There are so many ways to be a cuckold. Maybe you are just pussy-free for life. 

You’re “what-used-to-be-called-a-penis” is now completely out of the picture. Duties have changed. Maybe if she engages with you in any sense in the bedroom, that has dramatically changed, too. 

Ms. Erika: Traditionally, conventionally, women are made to be penetrated and men are made to penetrate.

A dominating part of that sissy play, whether or not it includes a dominant male in this situation, is strapon play. I recently did a blog on Five Reasons Why Sissy Needs Strapon Play over at Sissyville. It is much more emasculating than even dressing you up or giving you tasks as a sissy. 

Then, finally, you are the one taking my phallus deep inside. I just got chills!. 

Ms. Olivia: Let me also point out that strapon play can also be an incredibly intimate, sweet, sensual bonding kind of gender play. It doesn’t have to be humiliating. But when you have a sissy slut or a who’s a submissive sissy, that strapon play is fun. 

Ms. Erika: Come on, ride the pony. 

Sissy Maids & Sissy Housewives

Ms. Olivia: So let’s talk about a couple of other kinds of sissy themes, overarching sissy themes. Since we’re talking about sissy being very submissive and being trained, I think that goes part and parcel with the sissy maid training. 

Ms. Erika: A sissy maid and sissy housewife are very closely related. It’s fantastic to dress up your sissy as the housewife or the maid and have her be given a honey-do list. Often, it could be very strict or very lenient depending on the play.

Ms. Olivia: I think of those two as different. The sissy maid training is more subservient, more submissive.

The sissy housewife can almost be on equal footing with the wife. When I think of sissy housewife play, I think of the traditional 1950s housewife. She is expected to always be beautiful, always put together, her makeup perfect. She does the vacuuming in high heels. She sleeps in curlers or pin curls. Then when I get home from work, my drink is ready. She is there with whatever I need or want.

Whereas with a sissy maid, I think of the serving girls, for example, at a play party. She’s dressed in that frilly sissy outfit. She might be used and abused by people at the party, by my Mistress friends, or even my male dominant friends and always wearing crotchless panties.

Ms. Erika: More objectification included. I like that distinction. I’m glad you brought that up. 

Ms. Olivia: Plus you know, me, I love that 1940s, 1950s style. I love the fabrics. I love retro styles. I really think in another life I’m going to be reincarnated as Dita Von Teese. 

Ms. Erika: I like the imagery. I like the idea. I like the sensuality.I like the eroticism. Have you ever seen The Marvelous Mrs. Maisel? The Marvelous Mrs. Maisel?

Ms. Olivia: Oh, the outfits.

Ms. Erika: The actual mindset, I would not be very good at.

 Ms. Olivia: I don’t want it for me, but to be on the receiving end, having a 1950s housewife. I mean, no wonder men liked it.

Ms. Erika: “How to Be a Good Wife (1950s Style)” from the 1950s playbook, we’re going to include that link. For those who are thinking of being a sissy housewife or playing in that way, it is a really good guide. Memorize it.

Ms. Olivia: You know what? That’s going to be an assignment for your Yvonne. I’m going to send her the link to that playbook because she is very much my 1950s housewife. Now I’ve told her that she’s going to be in charge of the house, but I don’t want her ruining her hands by scrubbing things. 

I actually play in the kink world, the fetish world. And I have had a sissy maid before. They suck as an actual maid.

Ms. Erika: They want all the fun and none of the work.

Ms. Olivia: And they’re so distracted. It is really hard to actually clean the floor if you are wearing six-inch, ankle strapped, locked, pink, platform high heels and a pink latex sissy maid dress. It’s just really hard. 

So here’s what I do. I have an actual maid service. So these are actual people that come in and do the cleaning. And then the sissy maid is for playtime. I’ll say things like, “Okay, crawl around on the floor with your little crinolines under your sissy maid dress.” And if it’s humiliation play, I might put her in backless panties and then stick a feather duster in her ass.

Isn’t that wicked? Now, you don’t want to do that if you actually want your floor cleaned

Ms. Erika: Now dust everything with your ass, slut.

Ms. Olivia: Let me be very, very clear. I would not do that with Yvonne. I told her she will not be doing the actual cleaning, but I expect her to run the household. 

Ms. Erika: That is fantastic. Just like The Marvelous Mrs. Maisel. 

Sissy Slut

Ms. Olivia: We’ve talked about some of the different styles. You mentioned sissy slut. Oh my God. Isn’t a sissy slut absolutely the best?

Ms. Erika: You can just throw things at them and they love it. They absolutely love it. The sluttier the better. It’s amazing to me, sometimes. I love it. 

Ms. Olivia: We’ve got a couple of sissy sluts that call us and we’ve seen the smudged lipstick right after either sucking a dildo or sucking a cock. And even the smudged eye makeup from tearing up after gagging. All that black mascara running down their faces.

Petticoat Sissies

Ms. Olivia: You mentioned the mascara running down. That’s also a fabulous part of petticoat discipline.

Petticoat discipline is turning a man into a woman. It’s coercive. It’s disciplined. It’s saying various ways of, “You have to stay a girl for X amount of time. Once we turn you into your femme self, you will not be able to go back to your male self.”

Ms. Erika: No escape. No turning back.

Ms. Olivia: “You will have to stay this way.” The poor sissy is all dressed up and made up, looking almost perfect, looks at you and says, “No, Mistress. What do you mean? I have to stay this way forever?” 

Ms. Erika: It’s also very hard to get to the naughty bits when you’re wearing all those petticoats.

Ms. Olivia: Petticoat sissy chastity.

Petticoat discipline is fascinating. I think it started in England, but was very popular during the Victorian Era. 

Petticoat discipline has been employed all these years as well. “This is what happens to naughty boys. Naughty boys are turned into girls.” So if they display rowdy boy behavior, then he is dressed by their Governess and put into petticoats.

Ms. Erika: I see the image of the governess and those tight button down shirts and pencil skirts and the classic pumps. She has that stern look in her eyes, her arms folded and a scowl on her face saying, “You’re naughty and this is for your own good.” 

One of the favorite scenes I like to do is when boys are being naughty and teasing girls. “Oh, you think it’s fun being a girl. You think it’s fun to chase girls? Well, this is what you’re going to get.” And all of a sudden, once they’re dressed, they understand the challenges that we girls have to go through to look as beautiful as we do, so they are going to stay that way forever.

Ms. Olivia: Once they are in their place as a sissy who’s been disciplined with petticoat training, they are ripe for the next level of sissy training tasks. 

Sissy Training Tasks

Ms.Olivia:  I was talking to Christina Gizelle and she asked:

“Well, what would you have me do? Would you make me go into a salon and get a manicure and pedicure?”

I said, “Well, yes. I would send you into a salon, but I don’t want you to take off your nylon stockings.” She asked, “How would I do that? I would have to take them off for a pedicure.” There are nylon stockings that have a stirrup instead of covering the whole foot so you can wear them with sandals. It leaves your toes free. Send a sissy into a salon with stirrup stockings and she has to leave them on for the pedicure.

Ms. Erika: There’s no guessing about who the person is in front of you, no question who is sitting in that chair. The pedicurist knows exactly who you are, darling. 

Ms. Olivia: She knows you’re a sissy!

Let’s talk about some specifics. Sissy training tasks. For sure, shopping. That’s the number one thing, right? 

Ms. Erika: Absolutely. Shopping. Not only just going into a store and looking at things and considering them, but asking for help from the clerks. Now that may be advanced for the first time shopper. But, that’s where we’re going to go. “You want to be a sissy? You want to be feminized? I want you feminized. You will be doing this.” Asking for help is fantastic. 

Public humiliation

Ms. Olivia: Let me throw in a caveat. If somebody is interested in humiliation and erotic humiliation, I actually don’t send them into a store and try and get a vanilla store clerk to laugh at them and humiliate them while they get hard in their panties.

I am adamant about safe, sane, and consensual. I don’t want someone under my thumb or my guidance to force their kink onto someone who is not there for kink. 

Ms. Erika: 100%. Olivia, I didn’t mean to insinuate otherwise. What I’m envisioning is something we’ve all done.

Professional makeup for feminized men

Ms. Erika:  There are specific stores like Victoria’s Secret that help crossdressers all the time. They’re very familiar with guys going in and asking for bra fittings. Also stores like Sephora or Ulta and Mac Cosmetics are all familiar with males who want to be feminized. 

Ms. Olivia: Make sure to say Mac Cosmetics; not Apple computers. I had a guy I sent on assignment to Mac and ask what colors looked best on him. He went to the Mac Computer store and asked “What colors would look good on me?” and left with a pink cover for his iPhone. 

That’s one interpretation. That’s not the one that I meant. 

Ms. Erika: I don’t mean to bring these people into your kink. You’re not doing anything other than saying, “These are my measurements. What size do you recommend for me?” Just like any other girl talk. 

Shopping for women’s clothes

Ms Erika:  I have a Canadian girly girl, miss peg, who has gone into a woman’s clothing store and bought gifts for their significant others and actually created a friendship with a couple of the clerks. Peg finally said, “I really like that dress. What size should I get?” and once she said that, just as girls do when they talk to each other, the salespeople knew. They were enthralled and so happy to help.

I’m not suggesting that anybody go into a store and yell, “Hey, I’m a sissy! Come humiliate me!” No, these are things and activities that women do all the time, going and asking for sizing help. Women also ask about the sales or getting color suggestions.” Just asking those questions can impact you greatly, but leaves that other person in their whole self as being a clerk in that store.

Ms. Olivia: You bring up a great point. As long as you are not skeevy and pervy in an uncomfortable way, the clerk will help you. Sometimes the clerk will play along. If it feels fun, then they’re into it. If it feels sexual, then they’re not. 

I also have to tell you, Yvonne told me this. She was in a department store and she wore high heels. Now, Erika, you and I both know you don’t wear high heels to a department store because you’re walking on marble floors. It hurts. So she was limping along because her feet were hurting and a clerk just looked over at her and said,  “Yeah,” pointing to Yvonne’s feet and said, “You’ll learn.”

Ms. Erika: Always be respectful to those people when you’re out and about. Pretend these ladies are your Mistress. You wouldn’t force something on your Mistress. You’d always be respectful to your Mistress. You would always ask your Mistress for permission, “Mistress, may I talk about strap-on play?” Not that you’re going to say this to the clerk, but say, “If you’re comfortable, could you help me pick out a signature color?” If the response is anything other than “Absolutely darling, let’s go take a look,” then maybe they’re not comfortable with it at all. And you have to respect that and move on. They’re not part of your kink. They’re just helping you become more feminine. 

Feminizing power of color

Ms. Olivia: I love that idea of asking for help for a signature color. 

You and I were talking about how we wanted to design a wheel to help a sissy decide on tasks to work on or complete. That brings an element of chance into it. 

One of the things you came up with, which was amazing, was go pick out a new signature lip color. I just loved that idea.

I have signature colors. I talk about my signature toe colors all the time. Christmas Red and Malaga Wine from OPI.

Why shouldn’t a sissy have a signature color or several signature colors? You mentioned pink and lavender as two ideas. 

Ms. Erika: Your signature color can be just something that you really love. But on the other hand, one of the tasks that we can put on the wheel is to find out what colors go best with your skin tone. Are you warm? Are you cool? And that will help direct you to your signature color as well. 

Again, the people at the Mac or Sephora cosmetic stores can help you figure out what your coloring is and what looks best on you. 

Ms. Olivia: I also love bringing a sissy to various places online and say, “Let’s go virtual shopping.”

A virtual shopping trip can be so exciting as we go through different stores, looking at this or that style and asking, “What do you think about this? What do you think about that?” Then it goes right into complete girl talk. 

If I called you and I said, “Erika, what do you think about this dress?” and it’s not obvious where I’m going, your first question is “Where are you going to wear the dress?” Right? So that’s the first question for the sissy. 

If a sissy wanted to buy shorts, I might ask, “Where are you going to wear the shorts? What kind of reaction do you want? Do you want men to look at your pretty little bottom? Oh, aren’t you a naughty girl. I think you should get the shiny, hot pink, skin tight, booty shorts so that you could twerk your pretty little bottom.”

Ms. Erika: You brought up a good point. Where are you going to wear it? Because certainly we wouldn’t suggest they wear those pink booty shorts if they were going to a family gathering, a church social, or some place like that.

If sissies need help deciding what to wear to those events, we are here to help direct them.

The sissy slut

Ms. Erika:  You know, Olivia, our sissy sluts, they get out of their minds and they do some really silly things that they shouldn’t do sometimes. Reason number 407 why you need Mistress because we will help keep you safe, sane, and consensual for wherever you are going. 

If you’re going to a fetish play party, let’s go, let’s dress you up and go for it. 

But if you need something a little bit more subtle, maybe a pair of straight-leg jeans or pedal pushers with a little t-shirt would be more appropriate to go into the park.

Ms. Olivia: There was a news story a while ago about a man in bra and panties who flew somewhere and because it was not in the rule book, apparently, he got to stay on the plane, but a couple of days earlier, a man was asked to leave the plane for wearing pajama pants that kept falling down. It became this huge, huge, huge thing. We do not suggest you wear a bra and panty set on an airplane ever, however.

You can wear a bra and panties set underneath your clothes. That’s fine. 

feminization training while traveling

Ms. Olivia:  That brings up something else. Sissy training while he’s traveling. This is a popular topic.

For the guy who is a businessman in panties, travel is the perfect opportunity to explore your feminine side or your sissy side. You can pack your feminine things.

If you travel to a city often, you can get a post office box. Get a storage locker. Have your sexy items sent to the post office box. You can get them when you arrive in the city, go back to the hotel room, play to your heart’s content with Mistress and then pack them back into the storage locker and then go back to your regular life. 

It’s like what you say about feminization and sissy play being an erotic vacation. 

Hiding your crossdresser clothes

Ms. Erika: May I add another option? In the US, there is something called “General Delivery” with the United States Postal Service.

When you are buying or shipping something to your destination, you would put your name on the shipping label, underneath write “General Delivery,” then the city, state and zip code and the box will stay at that post office until you come to pick it up.

If you are in another country, you might want to see if something like that is available to you, too.

A second thing you can do also is ship your box to a local UPS store where you’re going, addressing the box with: “ship to a UPS Access Point” and it will stay there until you pick it up. 

Always double check with the post office or UPS store. This has worked for many people that I know of, but I’m not an expert. So, call the post office and ask about General Delivery to that area.

You can say something like, “I’m sending something to my sister in Nebraska and I don’t want it to go to her house because it’s a present. May I send it to the post office and pick it up when I get there?” 

You do have to use your name because, in order to claim the box, you will have to show identification. But the good thing is, nobody knows what’s inside. 

Ms. Olivia: Even if you are picking up something from Victoria’s Secret, you can say, “I’m here to pick up a package.” People don’t care. They’re not going to be looking at the box and say, “Oh, are these panties for you? Did you get panties?” People have busy lives. 

Ms. Erika: They have better things to think about than what’s in your box. Except when they come to us. Everybody’s wondering what’s in our boxes, Olivia. 

Ms. Olivia: It’s true. I love that we both went there. 

Sissy Lips

Ms. Olivia: Speaking of makeup and being very discreet, I have a suggestion for any sissy: go to the Burt’s Bees section in the drugstore or the grocery store and get a flavored chapstick. You can put it on and every time you lick your lips, you taste that vanilla and it can get you grounded again in your femme self or your sissy self and it’s completely discreet.

Then when you want to go a little bit further, a perfect sissy task is go back to the same place and get a Burt’s Bees lip shimmer. It’s very sheer and it’s like a light lip gloss, but you’re still not buying lipstick, right? 

We’ve got a whole podcast episode: “Crossdresser Makeup for Feminization and Sissy Looks,” and there are all kinds of suggestions and tips that help you with your sissy tasks.

Ms. Erika: I was going to suggest sissies can look for lip plumpers. You can get a matte gloss. When you put it on, it tingles so you’re reminded, for quite some time, that you’re being very feminine and nobody else needs to know. 

It doesn’t make your lips go from Kim Kardashian 10 years ago compared to Kim Kardashian now. It’s not that dramatic of a difference. But it does plump your lips a little bit and it makes you feel very sexy and very naughty.

Ms. Olivia: That’s a great idea, especially if you’re a sissy that is either bi-curious or knows that she is a sissy slut or a cock slut, having your lips tingle can create that, “Oh, my lips want some cock. I want cock,” feeling. Then if you can bring dildo with you and we don’t recommend this during the board meeting, but at other times, you can just get dildo out and suck on it.

That could be a fabulous sissy training thing. We’ve got to put that on the sissy training wheel.

Ms. Erika: Even if you’re not bi-curious… yet…,because sucking a dildo does happen when serving Mistress and her strapon. That’s very important. 

Ms. Olivia: It doesn’t have to be a male cock, it can be a Mistress cock.

Sissy training assignment

Ms. Olivia: We have a sissy training task for you right now.

Go to Apple podcasts, like, subscribe, and leave a review. That is your sissy training task. If you are at all worried about leaving your name or your email, go to Protonmail.com, sign up for Proton mail. When you go to subscribe to Apple podcasts, like and leave a review, use your Proton email address. We’re also on Spotify and most other podcast platforms.

Contact Mistress for feminization and sissy school classes

You can also email us, and follow our blogs, and follow us on Twitter. 

Ms. Olivia:  olivia@enchantrixempire.com / @MistressOlivia1 / Experienced Mistress blog

Ms. Erika:  erika@enchantrixempire.com / @ErikaEnchantrix / Intelligent Phone Fantasy blog.

Ms. Olivia: A reminder. folks can email and Skype us with questions. Email is best for me for questions because I generally use Skype for texting sessions and Skype sessions. Send me an email and I will send you Skype information. 

Ms. Erika: I will do the same.

Questions for femme girls and sissy girls

Ms. Olivia: Questions for all of these girly girls and sissies. 

I’m always curious about the sissy name or femme name. Do you have a sissy or femme name? If you do, what is it? And tell us the story of your name. 

Ms. Erika: It’s so fascinating to find out the origins of the names. 

My question is, when it comes to feminization and emasculation, and they don’t always go together, of course, but what words do it for you? What are those trigger words? Being a sissy maid? A cuckold? A sissy husband? Everyone’s different. I want to know what terms get to you and get that feminine energy flowing.

Ms. Olivia: I will follow up on that. Your final question, sissies, is what item of clothing gets you into the sissy mindset? You can only pick one. Just one. Stockings? Panties? Bras? When you put that item on, you’re there. 

Ms. Olivia: Thank you so much for joining us for The Weekly Hotspot. We want you to stay pretty, stay sexy, answer the questions, obey Mistress, all of these things and we will see you next week. Erika, always a pleasure to be with you. 

Ms. Erika: Oh, you’re so much fun, Olivia. Thank you. And bye everyone. 

Ms. Olivia: Bye.

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