The hosts of The Weekly Hot Spot podcast are joined by Ms Daphne for this episode on Sissy Training Assignment Scenes. Listen to this sissy podcast episode while you read the transcript. These transformation and feminization scenes include:

  • shaving 101 – how to shave and why it’s important to have a sissy all nice and smooth!
  • How a Sissy Mistress creates her transformation assignments.
  • Dildo Training
  • cock sucking training for the slutty sissy

BDSM kink feminization podcast The Weekly Hot Spot Sissy AssignmentIf you want to listen to the podcast, here’s the Spotify link to the Sissy Training Assignment episode and you can find The Weekly Hot Spot on any podcast platform. Feel free to scroll through this blog for transcripts like the Feminization and Sissy School episode.

Ms. Olivia: Welcome to The Weekly Hot Spot. Kink conversation, advice and insight from the worlds of distance Domination and phone sex. I’m Ms. Olivia here with Ms. Erika and joining us today is the fabulous sissy Mistress Daphne. Welcome Ms. Daphne glad you’re here. 

Ms. Daphne: I’m so thrilled to be here, so glad you invited me. Thank you. You two, both of you, know, sissies are my thing and I can’t wait to offer assignments today. This will be so much fun.

Ms. Olivia: We are thrilled that you’re here and we’re going to do something a little bit different because we like different. It’s going to be Sissy Training Scenes.

Sissy Training Wheel for sissy assignment scenes

sissy assignment training wheel on The Weekly Hot Spot podcast on sissy feminizationErika has created a Sissy Training Wheel. We will post the wheel on our blog so you can go take a look at it and can play the wheel itself. So you go (clicking sound) and it spins. It doesn’t come with sound effects but if you do it while listening to this podcast (clicking sound).

Here’s the format. We will spin the wheel. It will land on some particular instruction and each sissy Mistress will do a training scene with whatever things the instructions come up with. 

Ms. Daphne: That’s going to be so much fun. 

Ms. Olivia: I know, right? Can I say, I love you for making the fucking wheel. 

Ms. Erika: Thank you. It’s a lot of fun and my devious mind is busy making wheels for all kinds of kinks now. I’m thinking about putting a page on my blog, Intelligent Phone Fantasy, dedicated to wheels and maybe password protected. So when you get an assignment from me, go spin the wheel. 

Ms. Olivia: I love that idea. I’ve been sitting on the wheel idea. Lexi told me about the wheels. She said, “Hey, go check out Ruby’s blog. She has assignment wheels.” What the fuck is that? I went over to Ruby’s blog and sure enough they’re stroking wheels. I sent an email to Ruby. She was so gracious and said, “I don’t have any special skills, go here. You can make your own wheel.”

This was a month ago. Obviously I’m a tad behind on a lot of things.

Before we do your first sissy training assignment, we have a different kind of assignment for you. We want you to go to Apple Podcast and subscribe to The Weekly Hot Spot podcast or wherever you listen to podcasts. We want you to Like it, leave a review, and we are charting! How great is that?

Ms. Erika: Getting the word out!

Ms. Olivia: We appreciate everybody’s support. Thank you. Thank you. Thank you.

Let’s see. I love all the colors on the wheel, Erika. (spinning wheel)

Oh! Shaving 101.

Sissy Shaving 101sissy training assignment on The Weekly Hot Spot podcast

Ms. Olivia: Sissy doesn’t know he’s going to be a sissy. I tell sissy we are going to take our relationship to the next level and ask future sissy if sissy wants to come on vacation with me, and of course, he says, “Absolutely I do, my goodness!” I say, “Listen, I’m going to do the packing, leave absolutely everything to me.” Let me tell you, when a Mistress says, “Leave everything to me,” be very careful. Be afraid.

We get there, and I say, “I saw sissy stuff on your computer, and you are now going to be my sissy. I am a woman who will decide to make you my sissy. Go get settled in your room, and the first thing you need to do is be smooth.” 

I run a bubble bath and future sissy soaks in that bubble bath for 10, 20 minutes. Then, sissy shaving. “I want you to shave, at the bare minimum, all around your clittty and your balls. Extra points if you do your legs. Lots of extra points if you do your armpits.”

This is the key thing: Use high-quality women’s razors. You will go through several razors, that’s okay. If this is your first time shaving, shave in the direction of hair growth, otherwise it is easiest to go in an upwards direction.

I personally like sensitive skin shaving gel or cream. Lather it up. Lather, lather, lather. 

Go slowly, especially around the ankles, behind the knees. Take very short gentle strokes. Rinse off your razor often. Don’t be afraid to change razors often. Like I said, the two areas I definitely want shaved are around your clitty and your balls. Go slowly!

Someone who shall remain nameless, decided to shave without asking me and without getting any tips. He pops up in Skype and says, “I’m bleeding.” I said, “What? what? what the fuck? What did you do?” To make a long story short. I said, “The skin there is very, very thin. You might want to go to urgent care.” He did. He went and had it taken care of.

I have never had anyone who has come to me for shaving tips go to urgent care before… unless they had a nurse fetish. 

If you can’t shave your legs, that’s okay. We get it. What I want you to do is get some tights because tights are a little bit thicker than stockings or pantyhose. Get some opaque tights, shiny opaque tights, put them on and your legs will feel smooth, but still have hair on them. It’s a nice work around. Then you will have nice smooth legs. 

To have some really nice smooth legs, get some silky pantyhose or stockings. It feels so good, now that you’re all smooth. 

If you get razor burn, use cold press aloe lotion, that’s what I recommend. If no razor burn, coat your body with scented feminine lotion and you are all ready for the next training path. 

That’s it for now. You have to save something for your session. 

Each personalized sissy training program is unique to you

Ms. Olivia: Ladies, how do you choose what to add to the scene? 

Ms. Erika: That’s a very good question. If we’re talking training, then the inspiration comes from the caller. 

custom feminization training by Mistress ErikaThere are so many things to be trained on as a girl. I think you both will agree, if we went from soup to nuts, from morning to night, everything it is to be a woman we can go on for hours and sessions. I really look for a little direction from the client for their custom feminization training.

Are they interested in sexual sissy training? Are they interested in making their body feel as feminine as possible? So that’s where I take it from. 

Ms. Olivia: Soup to nuts? You are talking about a sissy.

One of my absolute favorite lines comes from the movie Steel Magnolias and Dolly Parton is Truvy, the beauty salon owner, where all of the women gather. Truvy says, “It takes a lot of time and effort to look this natural.”

Daphne, how did you choose what to put into a scene? 

Ms. Daphne: Like Miss Erika said, it’s definitely asking the client what it is that he or she wants, because there are endless places to go. When I know exactly what it is she’s looking for, then it makes it a little easier.

If we talk about tips on getting smoother legs and underarms, I like talking about other ideas including waxing or sugaring versus shaving. There are so many different ways to get that feminization done. It doesn’t necessarily have to follow one formula. Being able to explore all the different ways is a fun thing to do. 

As a little side note, if we talk about waxing, I like to make sure our girl knows what it’s going to be like at the waxer. When that waxer says, “Honey, spread your cheeks,” I don’t want our girls to freak out and get up and run half waxed. It’s just good for girls to know exactly what’s happening.

Should a sissy get a Brazilian Wax?

Ms. Olivia: Let me just say, the first time I got a Brazilian Wax… um… wow. Here’s what happens with waxing. The hair is pulled out. Now, it goes fast, but you fucking feel it. 

Ms. Erika: The first time I had a Brazilian wax was the last time. Oh yeah, this is a fucking temple. You’re not doing that shit anymore.

Ms. Daphne: When I got a Brazilian with strips, that’s blood-curdling-scream painful, but when you do it with sugaring or with hard wax, a green wax or blue wax, it doesn’t hurt a quarter of what it does with strips.

Ms. Erika: Well, maybe I’ll get myself back in that salon chair sometime before I pass from this earth. I was… it was a trauma. It was a trauma. “What are you doing to my delicious little vajayjay?”

So trimming and razoring is just fine for Mistress Erika.

Ms. Olivia: Let me say, lasering is not without pain, but it is more permanent. I’m not a super-fan of completely bald. I like a landing strip, a triangle. One time, I got a wild hair up my ass and I had someone shave a heart shape… and dyed it pink!

Ms. Erika: I hope they pull the wild hair as well while they were at it. “Just one moment, Olivia… one moment… (plink!) – you’re good.”

Ms. Olivia: Erika, you should spin the wheel. 

A Sissy’s First Dildodildo training for sissy The Weekly Hot Spot podcast

Ms. Erika: Spinning the wheel. There it goes. 

Dildo training! Yay! What girl is a girl without having dildo training? No girl at all, right?

Ms. Olivia: Sissy lips. We call them cock pillows.

Ms. Erika: I love that. I’m going to use that: cock pillows.

For my little sissy training scene, it’s going to come with a little sweet humiliation. Part of your assignment is to show your dedication and your commitment to the project.

I would wake you up my little sweet tart, and in this little scene, I am fantasy and reality at the same time. I imagine you sleeping in the extra room because that’s where my sissy sleeps in her pink little chemise. It’s morning time and Mistress Erika is a morning person, so I come in singing and so happy it’s a special day for you. You are very confused. You know you’ve handed your entire being over to me to do with as I wish. You never know what’s coming. And today it’s going to be delicious. 

We get ready, having a little light snack like girls do in the morning, maybe some yogurt and fruit; got to keep that shape up. It’s Florida, so we’re going to put on a couple of cute little flimsy dresses and head on over to the adult bookstore. I see that you’re nervous already. 

When I go in, one of my favorite clerks greets me, and she might be a little bit in on it, too. She asks if we need any help. Of course I say, as loudly and positively as possible, “Yes, we are here for a dildo training set!” She smiles and looks right at you sissy. I love making you nervous like this. It really does excite me.

As we walk down the aisle of various girl cocks and dildos, long and short, squirting ones and thick ones, you try not to stare so much. But as soon as I pick up the Gigantor 2000, a beautiful,12 inches long and thick as a soda can, your eyes are as wide as saucers. 

I start stroking it like the naughty little fucker that I am and I smile and wink at you. Now, the clerk is just a few feet away. She could hear me if I talk in a regular voice, so I lean in and whisper to you, “You know baby, once you have a big one like this, you’ll never go back.

You gasp, which draws the attention of the clerk. She sees what I have in my hand and she says, “Oh, no, no, no, Miss Erika, that’s for somebody who’s very advanced. I thought your girl…” and she points right at you… “Was a virgin. Unless she has really huge goals.”

You’re literally moist with nervous sweat.

Ms. Olivia: That’s not sweat, Ms. Erika. That’s moisture in her panties. You can powder it, but you’re powdering the lower 40.

Ms. Erika: Me being me, I decide to let you off the hook and I put Gigantor down and select three lovely toys in three different sizes because size does matter and you should start small. Of course, we have to get a gigantic bottle of Slip Sliding Away water-based lube. Be careful what lube you use girls with your toys. 

As we finish the transaction, the tension in your face relaxes, the screaming in your mind starts to go away, because you knew this day would come when you agreed to be trained and feminized by me.

Ms. Olivia: Anybody’s first or second or a new experience going into an adult bookstore is priceless. Absolutely priceless. 

A friend of mine had recently gotten divorced and I was living in Washington, D.C. at the time. They have the Pleasure Chest there on Connecticut Avenue. She wasn’t sure if she wanted to date. I said, “You don’t have to make any of those decisions. Just get a vibrator.” I don’t know why she hadn’t come to that thought herself. Most of my friends are like, “Oh yeah, a vibrator, let’s go!” But she was a little bit shy. 

We walked down the steps into the Pleasure Chest, go inside, and I said, “Hi, my friend needs a vibrator and I’m thinking she needs a Rabbit.” Around Dupont Circle is a huge gay area and this was a gay guy. He said, “Oh!” and grabs a Rabbit from under the counter, turns it on, puts it on the counter. The rabbit buzzing on the glass and moving around.

My friend lost her mind. She turned the most adorable colors. Really quite spectacular. 

I took us on an excursion. Daphne, Ithink it’s time for you to give the Sissy Wheel a whirl.

Ms. Daphne: You’ve got it. I see it going round and round and round and round. Oh. Oh, it stopped on cock sucking training.

Cock Training for Sissiescock training for sissies by Enchantrix Daphne

Ms. Daphne: Oh, one of my favorites. You know what? Because this sissy just acquired three brand new dildos with Mistress Erika. That’s perfect. Isn’t it? That’s just absolutely perfect so  I can do some cock sucking training. 

The first way I do this with my girls, what I’d love you to do as an assignment, is to find the cock sucking tutorials. Some of them are really good. I don’t mean regular porn videos, but actual cock sucking training videos. If you’re able to find them on any of the porn sites, that’s a really great way to begin learning.

While you’re watching, here’s some cock candy to suck on while we watch you. You’ve got to suck hard. You like cock candy, don’t you? Oh, look, look, look. See how her lips go over her teeth? Men don’t like to feel your teeth. Always remember to cover your teeth. 

I look at you and you’re sweating and I love it. Here we are again, sweating right below the waist, as well as on your forehead. I ask you, “What in the world is the matter?” and you tell me you’re scared. “What if I can’t do it? What if I gag? What if he cums in my mouth?” I pat you on the head and tell you there’s a solution for all of those things, honey. Then I remind you that not doing it is not an option, so that one is already covered. 

I go and get those three dildos in that pretty velvet bag that Miss Erika gave me that she keeps those pretty wonderful dicks in. I lay them on the table. We’ll start small and work our way up. I’m not going to push that 10-inch cock down your throat yet. Maybe later. 

I see you shaking. I think that’s so adorable, but I just keep going and telling you that I know you’re worried about gagging, but gagging is fine. Everyone gags. I’m telling you, when you’re sucking a cock, gagging is sexy. I love when you look at me with those wide eyes that say, “What?” I just pat your hand, comforting you. “It’s really, really, really okay. It’s okay.” 

Then I tell you all the other things that are going to happen because it’s not just a dick in your mouth, it’s a whole visceral experience. 

Your eyes are going to water. You’re going to start drooling and you’re going to slobber a little bit, so make sure you keep your pretty little hanky, maybe even embroidered, with you to mop up that dribbling down your chin. 

I know you have makeup on. You got pretty for this situation, didn’t you? Don’t smear your makeup; dab it. Don’t wipe. If you wipe, all your makeup gets onto the hanky and off of your face. So make sure that just pat, pat, pat very gently. 

Now your last question. What if he’s going to cum in your mouth? What happens? What do you do? Darlin’ you swallow it. There is no other option. You may not spit it out. I swear, if I’m sitting there with you and you try to spit it out, I’m going to scoop it up and put it right back in your mouth.

You swallow that cum. You are a sissy, cock sucking, cum eater. That’s what you’re practicing for. I know! I’ve looked at your history on your computer. I know you look at cock sucking videos. It’s what you want. I know it is.

I love after I’ve done all of that training and looking at you, I love asking you, “Are you ready?”

Ms. Olivia: Can I take us on just another little excursion?

I was talking to someone on the phone last night who is not a sissy, but does suck cock. And he said,  “(making coughing, clearing throat noises).” “Are you okay? Do you have allergies or something? You’re clearing your throat a little bit.” And he said, “His cock was really big.” His throat got pounded for hours. I introduced him to the glories of Throat Coat Tea. He said, “Oh, thank you.” I said, “We have to keep those pipes ready.”

Erika, spin the Sissy Training Wheel. 

Sissy Walking, Sitting and Curtsying 

Ms. Erika: Here we go. We’re spinning… and… beautiful. Girly walking, sitting, and every sissy should be able to curtsy. I love it. 

The last scene I did was a little mix of fantasy and reality as if my sissy was right here with me. A lot of training, whether it is in fantasy or one-on-one, you are really transforming yourself into a sissy or a feminized male. I treat it the same.

When I go through a scene, it’s as if you were here for this scene. I think I’m going to pick a delightful sissy named Brianna because we recently did this. We cannot have you lumbering about in your pretty frilly things. Men walk differently than women, and we have to get that style and grace ingrained in you.

“This week is going to be very difficult for you, Brianna.” I have you gather your two inch heels to start with because you’re going to work all the way up to six, darling. But today we’ll start with two. You come back with them and you’re so quick and so prompt. I’m just smiling ear to ear because when Mistress is happy, everybody is happy. Isn’t that right, darling? 

While you’re wearing your little shoes, I’m going to give you the links for some really nice walking, sitting, and curtsying videos that I want you to watch, over and over. Here’s a perfect video for any sissy who wants to put a little wiggle in her walk. When you are ready, we practice, practice, practice. You get up, walking from one end of the room to the other, from one chair to the other, practicing, keeping your head up, shoulders back, tits up, girl, that’s it. Don’t look at those feet. 

Of course, we can’t let one little thing slide. So, in your videos, you were taught to stand upright, tits out, but also put your feet one in front of the other heel toe, heel toe, very short heel toe. It’s not like you’re wearing a sneaker, but instead of keeping your feet wide and stepping next to each other, it’s almost like you’re walking a line, crossing your heel in front of your toes, nice and slow. 

I’m very encouraging and this is what you’re going to be doing for the next week. Five times a day, five trips each. Practice, practice, practice. You know what I think will help you is doing some yoga to loosen up those hips.

Ms. Olivia: Downward dog, bitches. 

Becoming a sissy Princess

Ms. Erika: When we finish our first walking session, I make sure you were paying attention. I ask you to do a Sussex sit. Don’t know what a Sussex sit is? It was brought back by Meghan Markle, but originally done by Princess Diana. I encourage you to click on those links and find out, girly, what is a Duchess sit? What is a Sussex sit and how to walk more femininely.

Ms. Daphne: I think I’m going to need to go see what a Sussex sit is, and a Duchess sit.

Ms. Olivia: I was just thinking that. I’ve never heard of a Sussex sit.

Ms. Erika: You know, when ladies sit, when you have a dress on, you can’t open your legs or fold your legs over. 

Ms. Daphne: You can, but only in certain situations.

Ms. Erika: I’ll give a little hint away because I know the girls that listen to this are going to be dying to watch the videos. A Sussex sit is sitting with your feet together, so your ankle bones can almost touch. Then you cross your ankles, one behind the other, and then lay it out to the side. Your leg is almost at a 30 degree angle. Your feet are towards your left shoulder with your knees in front of you. Like a princess. A pretty, pretty princess. 

Ms. Olivia: Yes, I think a sissy should emulate a princess because sometimes with a sissy we’ll call them, “Oh, princess!”

And then others, oh my gosh, I’m thinking of Yvonne. She actually looks like a princess with her ball gowns, wedding gowns, and her tiaras. I often call her “princess.” Only, with the wedding gowns, you can’t tell what both her legs are doing under there. An entire small family can live underneath her ball gowns.

Ms. Erika: She does post some lovely gowns. I’m not the kind of girl who’s really into weddings, but Yvonne really makes me yearn for a beautiful gown.See that inspiration we get from our callers?

Ms. Olivia: I used to be a wedding photographer, so I love her gowns and because of her, I have gotten way into ball gowns. I used to take ballroom dancing. I was always poo-pooing the gowns. “This is so restrictive. I just really want to do this in a mini skirt.” Well, you can’t do ballroom dancing in a miniskirt. 

Ms. Daphne: Well, you can.

Ms. Erika: But everyone’s gonna see whatever God gave you.

Mistress Daphne: I love gowns.

Ms. Olivia: We’ve already established that I’m shaved, but I have a little landing strip. Maybe nobody even needs to see it. They’ve got that visual in their minds.

Okay, Daphne. Get us back on the sissy training highway. 

Measuring Up as a Sissy

Ms. Daphne: I’m going to hit that wheel and it’s going to go, oh, there we go. There we go. Stop on… yes! Take your measurements. 

It’s really important for all of us, sissies included, to know our measurements. There are a couple of reasons why. Whether you’re thin, whether you’re a plus size gal, whatever it is, it’s really important to know your measurements.

One of the main reasons is that women’s clothing is not standardized. You might be a 12 in one brand and a 16 in another. It’s not that you gained weight overnight. When you change clothing brands, I promise it’s the clothes that are just fitted really odd for women. It’s one of the things that happens for us.

Knowing those measurements is what’s going to get you by. Whether, and especially, if you’re ordering online. If you’re ordering your clothes over the Internet, having the measurements is really important. Most clothing sites will have measurements for you to go by and that is how you can make sure to get the right size.

I know we all hear how often girls will order clothes and they don’t fit. Either they’re baggy or they’re so tight they can’t get their toe in. They have to send them back and start over again. In order to stop doing that, having your measurements help. 

But here’s another thought. If you don’t have your measurements, which I want you to have, is to order one piece of clothing and then a size on either side so you can try on the one you think you’re going to need. Then if you’ve got a smaller size, you can try that on. And if you’ve got a larger size and you can try that on. Then you send back whichever ones that don’t fit you.

It can be expensive, so it’s easier to just get your measurements, isn’t it? 

Ms. Erika: Keep an eye on the return policies too. I think even experienced ladies make those mistakes, Daphne. I saw the perfect pair of purple pretty panties. They were satin with a little ruffle around and they had the cutout bottom, which was shaped like a heart. I thought, “I have to have those panties!” I usually wear a medium, but I knew they were coming from overseas, so ordered a larger size. They came in, I couldn’t fit it up my leg. Now. I am not a tiny girl and I’m not a big girl. I’m like who’s making these? No bigotry intended, but Asian styles and Asian made clothes tend to be a little bit more petite. 

Ms. Olivia: Petite? I ordered a baseball jersey. And I’m chesty, so I figured, it’s coming from Asia. I’m going to do an extra large just to make sure. It’s a jersey. It’s better if it’s bigger and I can always take it in and get it altered. 

It was so tight! I didn’t even bother sending it back. It took 2 months to get here. So, I ordered another one. This time, I said, okay, maybe the men’s sizes. It’s not as cute. It’s not as fitted, but what the hell, it’s a baseball jersey. I ordered a medium and it was a ball gown. I saved that baseball jersey and wore it to a Halloween party, put a belt around the waist and I wore it as a mini skirt. 

Ms. Daphne: That is hilarious. What’s really good about us talking about this is that sissies see that even we have this issue.

Ms. Olivia: And we’re experts! We’ve been doing this our whole lives.

Ms. Erika: Don’t let the frillies distract you because if I would’ve paid more attention, I would have probably thought “Those are really cute, but I’ll never get them around my ass.” If you don’t get all excited about the pretty colors, ladies, focus on the size.

Ms. Daphne: This is one reason why we need measurements from all over our bodies, not just our waists and hips and busts, but we also need them for our thighs because of pants and jeans and our upper arms for sleeves. Sissies tend to have bigger arms and bigger chests. 

Bra shopping for feminization and sissy training assignments

Ms. Daphne: Your bra size needs to be especially measured as well. There are YouTube videos that show how to measure all over. But I would love you to go get a really accurate measurement by a person in a store. That makes you nervous. I can tell already. I can feel you’re shaking thinking about going out to be measured. 

What I encourage people to do is find the oldest woman in the store. If you go to a specialty store or a big department store, find the oldest woman. She has seen everything. It will not bother her at all. I know you think that younger people might be more open-minded, but I have found it’s the older women. When a sissy goes in to be measured, they do much better that way. 

Ms. Olivia: Let me also just, if you’re a sissy who wants to be humiliated by being measured, don’t fucking go into a regular vanilla store and bring anybody into your kink. Like don’t. But if you are trans or you want some help and you’re sweet about it, absolutely. 

Daphne’s right. Get with a woman with a little age. I suggest going up and saying, “Listen, I don’t know if you’re willing to do this, but I would love to get my measurements right. Would you be able to do that?” Then if the woman is at all uncomfortable, or if the store has a policy that they don’t serve people who were labeled male at birth… some stores do have that policy… then they’ll say, “No, I’m sorry, we can’t do that.” Do you not spend your money there. There are stores that are friendly. Spend your money there. Get a friendly store.

Ms. Erika: Another suggestion is to call ahead. You’re not putting them on the spot. You’re not staring them in the eye. And they feel more comfortable saying “I’m not comfortable doing that.” With that said, I have called Victoria’s Secrets all around the country for people and said, “I have a special friend who would like to come in for a bra fitting. I just want to make sure that you’re comfortable with that.” I get the name of who I talked to and I’ll tell my girl, “Go ahead and ask for Clara over at Victoria’s Secret. She’ll be happy to give you that bra measurement.” 

Olivia’s right. We don’t want to bring anybody into the kink. But you also want to make sure that the other person is comfortable, even in a vanilla everyday, I-need-a-bra, please-measure-me type of situation. 

Ms. Daphne: It can be, especially the first time, kind of embarrassing, but you just power through it. If you are serious about having the right measurements, it’s a really great project to do for yourself.

Ms. Olivia: I used to manage a lingerie salon.

Ms. Erika: Miss Olivia, is there anything you haven’t done? I am learning so much about you, I am just in awe.

Ms. Olivia: I want to tell people I didn’t get fired from all these various jobs that I’m talking about, “We know how she ended up at phone sex. She was down at Baskin Robbins dishing out ice cream and they said, ‘You ate all the cherries!’”. 

Ms. Erika: She was licking the product!

Ms. Olivia: That’s why I do what I do now because I do lick the product.

Anyway. Bra fitting.

Ciswomen are mortified at bra fittings, right? Absolutely mortified. I can tell you from personal experience, none of the bras fit; they just don’t fit. So with any of us, get on Skype, we will walk you through it. It’s possible for you to do your own bra fitting. You don’t need to have somebody else do it, but just know that being mortified is part and parcel of the female experience. Welcome to the club, bitches. 

Ms. Erika: We have all kinds of mortifying experiences.

Ms. Daphne: Oh, yes we do. Now one last tip because Ms. Olivia is correct that we don’t necessarily need somebody to help us unless you are a really large size girl. I find it is the same with putting on a bra, that if you’re not able to reach behind yourself, then it can be a little more challenging to measure.

Having a trusted friend with you at your house, in your room, if you’re a really big size girl (sexy, sexy, sexy!), then having somebody help you can be a lifesaver. It can be really easy to get your bras made to fit, and you can go from there.

Ms. Olivia: Those are great tips. All right, let me spin the wheel. Oh, my God, this is perfect coming after Daphne! Sissy shopping! Measurements and shopping go hand in hand. And of course now I think of Forrest Gump, “Me and Jenny go hand in hand, like peas and carrots.” Daphne and Olivia go hand in hand, like peas and carrots.

Ms. Daphne: I love all your movie references, Olivia. You’re hilarious.

Ms. Olivia: And especially the horrible sounds and accents. I listen to way too much Kevin Smith and Ralph Garman’s Hollywood Babble-On, because he does these great impressions and it’s going to be okay, now we know Olivia’s a Kevin Smith fan. She’s a freak!

Ms. Erika: In the best kind of way.

Ms. Olivia: I love shopping. Sissy shopping excursions can transform a sissy like very few things. It doesn’t have to be like Yvonne’s wardrobe of 16 million wedding dresses and ball gowns.

Ms. Erika: I thought you were going to stop at 16. Are you sure? 

Ms. Olivia: Truthfully, it might be close to a hundred. Yeah, she really does, but she’s been doing this for ages and she has impeccable taste. This is not a whole bunch of trash ball gowns that she’s hoarding. These are gorgeous. 

You can begin to transform in really small ways. I talk about this on a recent blog, Big News for a Little Sissy

This is a perfect example of a sissy training assignment. We were talking on the phone and sissy said, “I’ve stopped wearing panties.” I said, “What the fuck? I didn’t tell you to do that. I know none of my friends would tell you to do that.” And sissy said, “Oh, I’m sorry, Mistress.” I said, “Okay, we’re going to rectify that. So the first assignment. Go out and buy a couple pairs of panties.” 

Then the next time we talked I said, “Okay, so you’ve got a couple pairs of panties, now throw out one pair of male underwear and replace it with sissy panties.” The next time he has to throw out two pairs. Oh, what the hell? Toss them all. So all of the male underwear got replaced by sissy panties. 

So here’s the assignment… I knew this particular sissy, I knew what size and style and all of that stuff would be perfect. For people listening to this podcast, here is your assignment. Buy one pair of panties in the following styles: High-waisted with French cut legs. French cut legs are the ones that are higher up so it looks like a one-piece bathing suit. If you are a well-endowed sissy, you’re going to need the room unless you really want to dress left or really want to dress right.

Get one of each of these styles: High-waisted French cut legs, bikini, boy shorts, and thongs. Then your next foray into sissy lingerie shopping can include all sorts of lingerie… bra, garter belts and Ms. Erika mentioned the chemise.

Yvonne  found the most divine, sheer robe with feathers. On Amazon.

Ms. Daphne: Marabou! You can’t go wrong with marabou.

Ms. Olivia: And it’s well-made. It’s always a crap shoot with Amazon, but she bought it and it is beautifully made. She’s got two, one in black and one in white. No, she has one in black and I think one in red because she’s a Red Sox fan. I’m not going to take us on an excursion for baseball. You can move on to dresses, skirts, tops, shoes, all of that kind of stuff.

Other sissy shopping assignments are really tailored to each individual. For example, a slut will not be buying a ball gown. You’re going to want a really short club dress. The secretary sissy is going to want skirts and blouses. The little sissy in my recent blog post was told to get penis candy. Sissy can only have a cock in sissy’s mouth.

Your sissy assignments are really the best when you get one designed for you. So give any of us a call 1-800-356-6169 and keep in touch:

And if you know Kevin Smith, can you tell him that we did a shout out. Kevin Smith, Hollywood Babble-On, the entire Smodcast network here on our sexy, climbing the charts, sexuality podcast.

Erika, how do people keep in touch with you? 

Ms. Erika:

Ms. Olivia: And Daphne?

Ms. Daphne:

  • Email:
  • Twitter is @DaphneTease
  • Personal blog: Enchantrix Daphne 

Ms. Olivia: Now, before we end the podcast, we want to remind you, go to Apple Podcasts or wherever you listen to your podcasts, we want you to subscribe, Like, and leave a review, do this, and we will send you penis candy or panties.

That’s not true. But, we will send you links to penis candies.

Daphne, this was super, super fun. Thank you. You have got to come back. You are the sissy Mistress extraordinaire, but you’ve also got all kinds of fun stuff to say. This was very fun. 

Ms. Daphne: Thank you so much to both of you. 

Ms. Olivia: We always end the podcast with questions for our listeners. I want to know what is your favorite sissy assignment of all time?

Ms. Erika: I like that. My question is kind of similar. It doesn’t necessarily have to be an assignment though. What is it that gets you excited about being a sissy? Is it all about the sex or does being feminine and doing feminine things really excite you? 

Ms. Daphne: What I would love to know is who do you tell about your sissy behaviors and your clothes? Every girl should have a girlfriend to talk to, even if it’s us. That’s what we want to know. If we’re your girlfriends, let’s be girlfriends! 

Ms. Erika: We do have a lot of girlfriends who come to us for girly advice. Don’t we ladies?

Ms. Olivia: Absolutely. 

Ms. Daphne: Absolutely. 

Ms. Olivia: And let’s just also say that the relationships we form with crossdressers who call us, sissies, transwomen who call us… these are really important, intimate relationships. Sometimes,  we’re just shooting the shit and talking about girl stuff. Like the first time I met Yvonne. She was on Skype and I asked, “How old are you? Your skin is amazing. What do you use?” And we just went off on this excursion about skincare and it is a true friendship

Like Erika and I would be talking. Daphne and I would be talking. Or all three of us. “Oh, have you tried this lip gloss?” You know, whatever, whatever. Right? That can keep a cross-dresser or a sissy sane. 

Thank you to everybody. We want you to report back. We want you to tell us how you did with your feminization assignments and your sissy training tasks.

We will look for you on our next edition of The Weekly Hot Spot. Stay sweet. Stay sexy. And if you’re being really naughty, make sure you have bail money.

Bye ladies!