Sissy Anal Training In Chastity Cage

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Mistress Olivia and Ms Delia interview sissy Becca about being feminized, sissy training, sissy chastity and more sissification!
Ms Olivia: Welcome to The Weekly Hot Spot: kink conversation, BDSM advice, insight from the worlds of Distance Domination and phone sex. We are your hosts, Mistress Delia and I’m Ms Olivia. 
Ms Olivia: Ms Delia and I have a very special guest joining us. We’re so excited. Ms Delia, why don’t you start by telling people why we have a guest on today’s podcast. 
Ms Delia: Oh yes, we are so excited. During our Femdom Guide to Chastity podcast, I mentioned that there is a new sissy training tool. 
I think that sissy sex toys can make all the difference for training and I love, love, love the sissy lover remote chastity cage. We’ll talk all about virtual key holding and more with our very special guest today, Sissy Becca, welcome!
 Let’s get to know you Becca. You identify as a sissy. Talk about the difference between a sissy and a crossdresser.
Sissy Becca: Well, I mean I think that a sissy is probably something a bit more kind of sexual and fetishy. 
So kind of a crossdresser wants to dress as a woman, whereas maybe a sissy wants to dress as kind of a more idealized kind of woman. Like a vintage kind of housewife kind of woman that aren’t kind of an overtly sexual kind of woman. And that kind of feeds into how kind of they interact with things sexually and kind of then unique elements of sissy submission and dominance and kind of all that kind of thing. 
Ms Olivia: Oh sissy, that’s genius; I love it. Wow, that’s a beautiful description. So I’ve got to ask, what kind of a sissy are you?
Sissy Becca: Well I, I did kind of give it away that I do like, well love, the kind of vintage glam fifties housewife kind of style. So yeah. 
I love browsing kind of vintage fashion blogs and that kind of thing. The heavier kind of makeup look and the kind of stronger, less natural looking makeup and kind of a little bit over the top and kind of sexual and cheesecake and that kind of thing.
Ms Olivia: I’ve got to ask, do you peep at October Divine? She’s across the pond. She’s English,
Sissy Becca: Well as am I, so she is on my side of the pond. Um, have I seen her? Cause I don’t think so. 
I follow a lot of blogs on Tumblr where they kind of just repost vintage fashion with pictures normally with modern models and that kind of thing. 
You can just spend hours kind of just going through those kinds of things and kind of maybe working out kind of what works for you and kind of how that would be done. 
So yeah, I can see with October Divine is that kind of thing. Like I said, the kind of older vintage style lingerie. Maybe it sounds a bit silly, but kind of where the clothing is a kind of bondage almost; f that kind of thing makes sense where it’s kind of corsets and layers and you know it kind of forces you to stand up straight and kind of have the right kind of posture and everything like that.
Ms Olivia: I have to tell you, the 1950s housewife look for a sissy is my personal favorite. Ms Delia, do you have a favorite sissy look?
Ms Delia: I think my very favorite sissy look is the helpless sissy maid: the dress, the pinafore, the hat, the innocence, the blushing cheeks. I love that for a sissy.
Ms Olivia: Sissy innocence. Hmmmm Is there such a thing?
Sissy Becca: And probably not for long!
Ms Olivia: So Becca, what’s the best thing about being a sissy?
Sissy Becca: Well, I mean for me it is kind of how happy it makes me.
We can get into it, but how I kind of came to it, but when I kind of discovered it and kind of started going into it and doing things for it, it just kind of makes me feel more like myself. 
It might be a bit weird, but it’s like there’s male and female that kind of society defines certain ways, but people tend not to really fit into them. And it’s kind of explore and experiment and find out what kind of whereabouts you are; how much you are in one part, how much in the other and kind of whereabouts you fit into it. 
For me, I just find that I’m a lot more comfortable and kind of a lot happier being more feminine and you know, makeup and dresses and kind of watching things like The Marvelous Mrs Maisel, which is, obviously, one of my favorite shows. And it’s just so much fun as well. 
Sissy Becca: You know, I’m happier, I feel, you know, more in touch with myself, no pun intended. And all of it is just so much fun – dressing up and doing the makeup.
Girls get to wear lingerie and get to wear costumes and bright colors and whereas boys are generally in kind of utilitarian clothing and normally dark colors. It’s loosened up a bit now, but kind of that kind of thing. 
And it’s just something more appealing about expressing yourself a little bit more with color and kind of that side of thing with makeup, nail polish and everything.
There’s so much that men normally don’t get to use or have any experience with.
Ms Olivia: Men who wear male clothes get sold short shrift, right? Because you’re right, male clothing sucks.
Ms Delia: I agree with that so much.
Sissy Becca: And it is a modern thing. If you go back and look at it in history, men would always, you know, like peacocking when the peacocks, it’s the males have the big tail feathers. 
Throughout history men would always be the ones that dressed ostentatiously kind of with colors. And then more recently, probably Victorian times, it kind of all became more set and men became more sober and dour and clothing followed suit. It just became black or gray with maybe white shirt and just kind of dull and boring.
Sissy Becca: Why would you want to wear boxer shorts?
Ms Olivia: How did you become a sissy? And as you’re telling that, talk a little bit about whether or not you think being a sissy is a sexual orientation or gender identity or maybe a little bit of both. 
Sissy Becca: I do think it’s a little bit of both because, well, I was always very into Female Domination, Femdom. That kind of led to (coerced) feminization. I used to kind of read stories. I’ll look for videos on the internet. I would read Femdom stories and notice I was reading more of the (coerced) feminization stories and that led to the sissification stories.
Maybe there’s some “forced” in there but really it is what I want anyway so I might as well go ahead and do it myself if no one else is going to kind of push me.
I started exploring that and kind of pushing through. 
A couple of years ago, I think I was on the sissification Reddit and there was a post about the Sissification Academy, which will start in a training course for sissies.
And then the head trainer put a note on the Academy Reddit saying they always look for new staff members and just get in touch. And I was very, very shy at that point. I think it took me about two weeks to make an account on Reddit and work up the courage to message her and say, I’d like to help out, you know, I think this is something worth doing. 
Ms Olivia: Oh cupcake, why were you so shy?
Sissy Becca: I don’t know, I’ve just always been kind of introverted and shy. It’s kind of easy, once you do that, to just keep it all separate, locked away, entirely personal and never do anything with it. 
But I realized that was getting more and more into it and I wanted to push a bit further and a bit further. I kind of worked up the courage, got in touch and obviously it was, it was really good.
And then I joined the Academy on as a staff member as kind of Administrator. So I moderate Reddit, deal with support queries in the mailbox and kind of moderate the discourse as well. Doing that and being part of that has really, really helped me.
And so now I speak to 25 students a day, maybe more, answering emails, chatting with them and kind of working with the staff there. 
If you’d have told me a couple years ago that I’d be doing a podcast about it, I’d have wondered, you know, what you’re talking about. Obviously now I’m here and I’m kind of doing this. 
For me it’s part of my identity, part of my sexual identity definitely. And it’s just part of my life really because I normally spend an hour or two every day doing some kind of work for the Academy and kind of interacting with people. And like I say, it’s just been so good for me.
Ms Olivia: So we’ve got to ask, are you dressed right now and if so, what are you wearing?
Sissy Becca: I am dressed right now. I would be wearing makeup as well, but I just got out of the shower before we started recording so I didn’t have time to put anything on. 
Obviously, given the subject and the fact that I’m talking to two Mistresses, I’m in chastity which we can talk about in a little while.
Ms Olivia: Good sissy! Thank you, Becca.
Sissy Becca: You are welcome Mistress.
From the ground up, I’m wearing six inch high heels, red stockings. Um, although they did get a little run in them because I was pulling them a little bit too quickly. 
Sissy Becca: I’ve got plenty of other pairs so it’s not the worst thing. 
I’ve got a black knee length skirt and then a pair of blue panties. And then I’m wearing my leopard skin kind of off the shoulder top. 
Obviously, I have my boobs on which I have two different pairs. One of them is kind of inserts that go into a bra that I’m wearing.  
And, I’ve got like a proper silicon kind of upper body suit that is the same bra size. That takes a little bit of time to get on and take off so that’s normally for when I want to spend a longer time wearing them. 
And then obviously I have a wig on as well. So I’m kind of fully, fully dressed, if you will. 
Ms Olivia: What color is your wig?
Sissy Becca: ~laughs~ I thought you were going to ask me how big my boobs are, cause that’s the normal question.
Ms Olivia and Ms Delia: Both! We want to know both! ~laughs~
Sissy Becca: That might just be where my, yeah, where my mind’s at the moment. 
So yeah, it’s kind of a brown just below shoulder length wig. I do have blonde ones but I tend to be colored better in dark hair. 
Um, and then the boobs because I mean like sissification is kind of pushing things a little bit further, my boobs are E cup or DD, depending on which ones.
Sissy Becca: And like say for me, I would like bigger. ~laughs~ But these actually I think suit me pretty well cause I do have quite a big frame and I think they look pretty good on me.
Ms Olivia: I have 34 triple D breasts, but Delia’s breasts are way bigger. So you want to know about bigger boobs, you should ask Ms Delia.
Sissy Becca: I’m very jealous of both of you!
Ms Olivia: Ms Delia, what is your size?
Ms Delia: My breasts are a 36 G cup.
 Sissy Becca: That is pretty big. I think I’m 34 DD with my boobs on.
Ms Delia: Becca, you sound just really like that vintage pinup that you had been talking about earlier. You sound adorable.
Sissy Becca: Thank you Mistress. I do have my toenails painted as well because they, they almost always are. They’re painted red. 
Ms Olivia: Nice! Ms Delia’s Mistress colors are purple and black. My Mistress colors are red and black. So I for one am really thrilled about all of the red that you’re wearing.
Sissy Becca: And a black skirt and stocking so kind of a little bit for both of you.
Ms Delia: And I love a leopard print. So that off the shoulder top. Ooh, that makes me very happy.
Ms Olivia: Let’s talk a little bit about the importance of sissy training and sissy support. 
As we talk about sissies and crossdressers, we interact with them all day long everyday as well, and we hear this time and time again. It was a huge part of our interview with a crossdresser: Yvonne talks about acceptance as a crossdresser.
It’s the idea of finding your own and getting support and acceptance and love and kind of walking through some of the practical things. So talk to us a little bit about sissy lover and the LGBTQ supporters and the sissy trainers. I love that they say our goal is to have a less judgmental world when it comes to sissification, transex and crossdressing. I love that.
Sissy Becca: So obviously that is the goal and very few people would argue kind of with that goal.
A big part of it is finding the people that’s why the internet is so good that you can go and find other people doing the same thing.
We have a Reddit that has about 16,000 subscribers. 
We try and keep it positive and kind of light and girly because kind of that’s what people are looking for. Especially with something like this where um, a lot of people wouldn’t understand it. 
Having kind of somewhere where you can go and be accepted for it is kind of, it’s, it’s a big deal to a lot of people, especially if it’s something where you’re new to it or even if you’ve had it for a long time and you’ve kept it completely private and you’ve never told anybody. 
Then you find out that other people there who are going through the same thing. 
Sissy Becca: And then maybe after a while you’re comfortable reaching out and kind of talking to people. You find out you’re not alone, you’re going through the same kind of things. You’re not a freak, you’re not the only one that is kind of a big deal for a lot of people. 
Like I say, for me, finding that was kind of big, even though I knew there were cross-dressers. Obviously if you look at the internet and read or watch sissification porn then it’s pretty obvious that sissification is a thing.  
But then when you find out where the people who are in the same category and go for the same things you are it kind of, it just gives you a little boost and kind of lets you know there’s support there and you’re not going through this on your own. It lets you know that you’re not a freak or an outcast or anything like that. 
It’s maybe less common than some other things, but it’s nothing particularly unusual. And who knows how many people would really like to explore something like this but just never actually do because they just dismiss it out of hand or bury it down because they just think no one wants that, no one’s interested. It’s not, you know, it’s not right or whatever that means because of that we try and be welcoming and positive.
Erotic Humiliation is kind of part of it but it has to be done in the right way. It can just be mean, but ultimately it has to be kind of coming from a loving place. 
Sissy Becca: If not, that will just turn people off and turn them away completely. 
Ms Delia: Oh, I think that there are a lot of ways to kind of help you and other sissies become a better sissy. That’s the feeling, the sense that I get from sissy lover. 
One of the things that I liked was the sissy school and the sissy training assignments. And I think that spoke to both me and Ms Olivia because we each do a lot of sissy training, a lot of sissy training every day. We’re involved in some kind of sissy betterment. 
Tell us why the sissy lover Academy and the assignments that they have are important to you and to other sissies.
Sissy Becca: Well, the other part of it is you realize you are a sissy; you maybe watch some videos, read some stories, kind of that kind of thing, but what does that mean? Where do you go from there? 
How do you shave your body? How do you do makeup? It’s all the simple basic things that girls learn naturally and where you just don’t know where to start. So the course is kind of a year long thing that assumes pretty much no knowledge or experience and then kind of works to do a lot.
Sissy training starts with kind of basic wellness. So it’s kind of set up a sleep pattern, drink enough water, some exercise and maybe a little bit of a diet, that kind of thing. 
And then it brings in exploring the sexual side of things. Obviously because it’s a sissification course, there are kind of masturbation assignments in there. And then kind of buying sex toys.
Each module kind of builds up a little bit further, a little bit further and pushes certain different things. 
And then we explore makeup, fashion, body language so you can walk like a girl, sit like a girl and kind of carry yourself in a feminine manner. We try and cover everything.
For a lot of people, you kind of start out and do kind of like, well as I did. You maybe buy some panties and some stockings because why wouldn’t you? And you try them on, but then you can think, well how do I take a little bit further, what’s the next step?
That’s kind of what we’ve tried to do with the course. We try and kind of show where you can go.
You don’t have to do everything. You can pick and choose what you want to do and follow or not follow it, but it’s kind of fun and it kind of gives a lot of ideas and kind of a lot of training. 
And so if you want to completely femme yourself up and grow your hair long, if you can still do that, dress and you know, pass as a woman, then we want to be able to show people how to do that. 
Obviously they need to practice to students need to practice and kind of work for everything. But you know, we, we want to show them,
Ms Olivia: Becca, you mentioned sissy sex toys and I have to tell you one of my all time favorite sissy training assignments is learning how to walk like a woman with a sissy pussy anal plug in.
Sissy Becca: That is a classic one.
Ms Olivia: With remote control! So a remote control sex toy so that you are practicing in your six inch pumps, your six inch heels, preferably with a locking ankle strap.
Ms Olivia: Pink or red heels. And then you are just kind of practicing doing that cute little walk as I’m just moving the remote control vibe up and down. ~laughs~ That’s a tough assignment. 
Sissy Becca: I can imagine what you really need. They need something that can give small electrical shocks or if they’re doing it very badly wrong, you can just give them a little zap or something to punish them and keep their mind on what they’re supposed to be doing. And there may be a little mini vibrators to reward them if they’re doing particularly well.
Ms Olivia: Oh yeah. With the little spanking, you know, something like, a little swat!
Sissy Becca: If you’re sitting there watching them when they come back to you, you can just reach out with the crop maybe and just kind of give them a little spank.
Ms Olivia: Ooh. Delia loves the fucking machines.
Ms Delia: I do; I’m a big a fan of the fucking machines. And you all have one on the sissy lover site that I just love. Hmm. Have you ever tried it?
Sissy Becca: I haven’t. I must admit I would be quite scared to try it. I’ve talked to quite a few students who have, I know following one of our recent sales, one of the girls who works in this store said that we sold so many fucking machines you couldn’t believe it.
Sissy Becca: Yeah. I mean, so fucking machines are cool. I love them.
Ms Olivia: I also have another question. There’s something else that I’m curious about. The chastity device. So talk to us about chastity. Why is chasti
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