Let’s make him a sissy!
Welcome to The Weekly Hot Spot: kink conversation, BDSM advice, inside the world of Distance Domination and phone sex. We’re your hosts, Mistress Delia and I’m Ms Olivia. Thank you for joining us. Let’s make him a sissy today.
Ms Delia: I love turning men into fun, flirty, sexy sissies. I really do.
Ms Olivia: I love it when a Dominant Woman puts her man in women’s lingerie. Oh, isn’t that so much fun?
Ms Delia: It really is just so much fun because there’s that interplay, right? Maybe he’s dressed up to go to work, but the very first thing that is touching his skin is panties. He could be in a suit. He could be in construction pants. He might be an Alpha male and still be feminized under his work clothes because the first thing touching his skin is a beautiful silky pair of panties with a little bit of lace in front so he feels that all day. And he also feels fabulous because panties just feel great.
Ms Olivia: Yes, they do! Cross dressers often call me and call themselves sissies. After talking with them, I’m like, no, you’re not a sissy. Sissy is a little bit different from a trans girl or a cross dresser. Why don’t you go into the differences? Not all panties are the same, are they?
Difference between a crossdresser and a sissy
Ms Delia: As a general rule, I think sissies tend to tend to be more over the top.
A crossdresser can have a certain fetish or just be into maybe panties or camisole tops or really have a fetish for nylons or just the general look or womanhood. But I think sissies tend to be more over the top.
With a sissy, there’s that feeling of frilliness, of big skirts with petticoats underneath bows and ribbons and satin shineyness and bubblegum pink lips. Sometimes there’s just a little difference. But often there is that kind of freely over the top difference that I noticed.
Ms Olivia: Let’s talk about coerced feminization or sissification. There’s one sissy that I was talking to and her name is Christina. Sissy Christina says she classifies herself as a sissy even though she doesn’t think she fits that mold perfectly. Now, isn’t that interesting?
She says that being tricked or coerced is her thing because she’s submissive by nature and she respects and worships women. So for her, being coerced gives the level of acceptance of who she is and what she likes. It’s also a bit of Dominance and submission, the power exchange.
The emasculated man turned into a sissy submissive
Ms Delia: Oh, I love that. I love that. I think, as a general rule, to be a sissy you have that sissy submissiveness inside you. You yearn to kind of give into a Mistress, right? It’s the wanting to do just what she tells you to do. There’s something about that with sissification and I think that is pretty consistent.
Ms Olivia: And think about it. A sissy knows he’s a man not a woman. Can a woman be any more Dominant or take power exchange to any greater level than actually switching his gender from male to female?
Ms Delia: Oh, that is an excellent question. And I’m just going to agree with you that that is so incredibly intense. It can even be a mind fuck for a man. Right?
Ms Olivia: Absolutely. Have you noticed that a lot of sissies still identify as men?
Ms Delia: Yes. I’ve noticed that too. They don’t really switch gender per se, no matter what they look like.
Ms Olivia: There’s an element of submission to the Dominant Woman and there’s also an element of humiliation that can be gentle teasing or pretty extreme humiliation. You’re not a man. You’re not a real man. I’m going to put you in panties and this whole little sissy outfit.
Ms Delia: I love that. I was talking to a wonderful sissy in Second Life last night. Her name is Sarina and she is fabulous. The outfits that she puts on her avatar, I mean it just makes her look so fuckable I can’t even tell you. It’s amazing. They’re very like high-quality, sexy, amazing stuff.
We were out, dancing at a T-girl club in Second Life and we were just sort of chatting in our instant message box. You mentioned something about, you know, the look and everything. There’s another sissy that we are both friends with and she has her real-life picture as this fabulous woman. She is an over the top gorgeous diva; a sexy supermodel looking woman. And Sarina also has something very similar and we were talking about that last night. We kind of came to the conclusion that for sissies, they sometimes have a picture of their ideal woman.
What is the ideal sissy look?
Ms Olivia: That’s really interesting. I hadn’t thought of that. Don’t you think that that’s part of dollification or being turned into a bimbo? You know when the sissy is looking at those big bimbo lips and the big butt, the bimbo tits, and you know, the eyes all wide.
Ms Delia: Exactly. Some of the old celebrities, Marilyn Monroe, have that kind of vintage pinup girl kind of feel. Rita Hayworth is another and just the sexiness that kind of just drips from them. I think that they capture that essence in, you know, the low cut tops or the teeny waist and the big lips and the big boobs and those big booties and the heels and the wiggle. There’s just something about that. It just exudes sexiness.
Ms Olivia: It also sometimes exudes sluttiness. You were talking about sissies and frills and looking so super sweet and stuff like that, there are also some raunchy ass slutty sissies. I’m just saying.
Ms Delia: It’s true. It’s true. I have shopped with one sissy online and we’ve done these long intense kind of conversations where it’s almost been like a competition. She’ll send me a link, I’ll send her a link and we’ll just go back and forth looking at the dress and kind of looking at the booty shorts and the corset at top and all the sexy, almost clubwear slutty types of things we find. And just talking about how that makes her feel.
Ms Olivia: Sometimes the sissy will want to get super slutty. I think part of that sluttiness is what Christina said, being made to do something that perhaps you wouldn’t otherwise do. Of course I’m talking about first make him a sissy and then make him suck cock.
Ms Delia: Oh, I love that. I love that so much. The interesting thing too is a lot of sissies love to suck cock but not all of them do. Every sissy does not suck cock or is gay. I think for a lot of sissies there is a lot of sexual fluidity.
I’ll give a quick example of that talking about Sarina, my Second Life sissy again. I have had sex with her in Second Life and she absolutely is a lesbian and at that point.
She’s working with me personally on chastity goals and talking about cum eating and sucking cock for sure.
Then the other night when we were in Second Life walking around at a different dance club, she goes, “I’m going to go fuck this woman over here. I’m going to take her home.” That was another sissy. Their avatars were both very female. There’s that fluidity which is really kind of fascinating to me. You can just go anywhere with it you want.
Ms Olivia: I think that outfits almost give permission to go places because it’s sort of like you’re in costume. What’s the line? What happens in Vegas stays in Vegas. You know, it’s like what happens to me in this butt revealing club dress stays here and doesn’t bleed out into other areas of life. A lot of these sissies wouldn’t dream of sucking cock in their male mode.
Ms Delia: I completely agree. I really think for a sissy, it’s a preference, a personal preference. I talked with someone, Jane, who is a woman and is completely just into women and would have nothing to do with cock at all, ever. So I think you are so right, Miss Olivia. I really do.
Why would a cis woman want to make him a sissy?
Ms Olivia: So speaking of women, would a woman want a sissy?
Ms Delia: Personally, I love sissies and love hanging out with sissies. It’s so much fun. Why not?
Ms Olivia: I agree with you. You and I are both Dominant Women, so we really enjoy the power exchange that is kind of inherent in all sorts of sissy play. Even if it’s not overt sex play, it’s still kind of, you will get these pairs of panties, you know, it’s still power exchange. The woman is in charge. It’s a Female Led Relationship.
Ms Delia: Absolutely. I’m actually in a Female Led Relationship with my husband Jack. From time to time, just for the play as we’re talking about, I do put Jack in panties. I do some lacey, pretty sexy panties. They’re red by the way. He’ll also wear a little plaid skirt that is scandalously short, a sexy red bra with all the lace and a top that ties just under the bra. No breast forms, no nothing. Thigh highs and black high heel pumps. I put on my strap on and I turn him into my little sissy slut, my little sissy bitch, making him suck my cock and take it any other way. I want maybe for an hour or so.
Female Led Relationships and what happens after sissy play
Ms Delia: Then, you know, he showers it off and we go grocery shopping. Right. Because that’s what Female Led Relationships are all about.
I mean, as much as I joke with him, I am that woman who goes up behind him when he’s bent over and loading the dishwasher and I do the hip thrusting while grabbing his back. But I, I think sometimes I will make more comments in the grocery store and he just kind of blushes and rolls his eyes and smirks cause it’s fun. It’s endearing really.
So I think Dominant Women love playing with the sissy because not only is it all of the dressing, but like you said, strap on play. Pegging. and the Dominance of bending sissy over.
Strap on with a sissy versus a crossdresser
Ms Olivia: That’s a very Dominant position, taking sissy from behind. I personally enjoy taking a crossdresser with a strap on with her on her back and me in the top kind of missionary type position. But with the sissy, when I’m wearing a strap on like you, I want her bent over and preferably wearing a skirt that can be flipped up.
Ms Delia: Oh yeah. It just is the sexiest I think, for a Femdom woman to just have exactly what she’s looking to do right there in front of her because she’s looking to do that sissy in one way or another. It’s all about the sexiness right there. I love it.
When his wife decides to make him a sissy cuckold husband
Ms Olivia: Let’s talk about cuckolds. So if a woman has a cuckold husband, there is sort of a logical extension from cuckolding to eating cream pie, to licking her lovers cock. One of the things that often goes on in that sort of situation is that she or her lover puts her husband in panties and then she or her lover can turn her husband into a feminized husband who is a sissy cuckold.
Ms Delia: That is so absolutely perfect.
Ms Olivia: The wife says, look at you, you’re just in panties now. I’ve got this real man, this alpha man over here. She’ll say something like, you’re just a sissy in panties anyway so I’m going to go have my fun and then you can maybe clean up after. That can be combined with some small penis humiliation that gives it that bite of humiliation.
But there’s also kind of sissy play where the husband is the sissy husband and the wife is like, “I want you to dress me. Why don’t you help me bathe, help me pick out my outfit.” So it’s more like two girlfriends getting her ready to go have sex with her Alpha boyfriend. The sissy could either be left at home or participate.For example, by sitting in the bed and looking at his wife and watching her expressions and realizing that he can’t make her feel that way. Sometimes a sissy will say, “I’ve never been able to make her feel that way. I’m grateful that this man with this big cock can make her feel that way because I can’t.”
Ms Delia: I love that gratefulness and respect. It’s, it’s really such an intense feeling.
Ms Olivia: I think the depictions of cuckolding in popular culture do a disservice to the nuances because cuckolds have feelings and a lot of those feelings are very tender and very loving towards their wife.They know they don’t measure up and they need to be in the friend zone. They are grateful there that she’s even still with them and they want to do anything and everything to keep her happy.
Ms Delia: Exactly. And she is a hot wife, but there’s nothing saying that she can’t really love her husband. She can love to tease him and kind of play with him. She’s got a little bit of that Dominant attitude but not a cruel or mean streak at all.
Ms Olivia: Exactly. And yet it can get mean!
Ms Delia: Yeah. Oh fuck yeah.
Ms Olivia: That’s the thing about power exchange. It can go from sweet and nice teasing. Humiliation can be gentle and firm all the way to extreme and mean degradation. A humiliation scene can be like really grinding someone under your foot, really putting them in their place.
Ms Delia: Oh fuck yes.
Ms Olivia: So let’s talk about sissy training. We mentioned a kind of timeline for a cuckold. I’ve noticed there are levels of sissyhood training. Sissy training by Mistress can help any sissy become the best sissy possible. I know you do training to make him a sissy and you absolutely love it.
Ms Delia: I do. I really, really love it. I really do. Yes. Yes.
Ms Olivia: What do you do in your sissy training?
Ms Delia: For 2019, over on my feminization blog, FemFebulous I had outlined a plan, a year long sissy training plan so that each month we had a different topic to go through. Make up I think is one of the biggest ones. Makeup, just making it really fun and looking at things but also touching upon skin care and body care, clothes, sissy exercises, I mean you name it.
More sissy training assignments
Ms Delia: I am going to be putting together a program for our assignment site. It’s going to be fun. It’s going to be fun because really if you don’t know where to start, just starting with one thing and getting really good at it can really help you to progress and become the sissy you have always dreamed of being.
Sissy cock sucking lipstick
Ms Olivia: You bring up a great point, getting good at one thing. So for example, one of the things that I love is when a sissy is cock curious but may or may not be gay. Or maybe sissy will find herself in the position where she will need to lick a cock or serve a hot wife as a fluffer or even be sent out to work for Mistress by sucking cock. Whatever the scene is one of the best things is going through all the options for sissy makeup.
Ms Delia: Oh, I love that. I love discovering when talking to a sissy, you know, sometimes it’s even the different mood. If it’s like cock sucker red one day and then another day it’s a certain look of gentle sweet sissy shopping kind of pink. It’s so much fun just choosing and going through all those options.
This is the only lip gloss you need
Ms Olivia: You can do cock sucker red lipstick with an overlay of pink glitter lip gloss. I personally think that’s the best of both worlds.
Ms Delia: It really is that shiny, glittery pink gloss. Oh yeah.
Ms Olivia: I have an absolute favorite lip gloss, especially for sissies. It is Mac cosmetics lip glass, because it goes on thick and it is super, super, super shiny. Here’s why it’s great for a cock sucking sissy. The lip glass is a little bit sticky and viscous. That means when you put your lips on a cock, it kind of tugs. It doesn’t just glide. It kind of tugs a little bit.
Ms Delia: Oh, that sounds just so naughty. I like how you did that. I’m getting a little warm here.
Will a vanilla woman make him a sissy?
Ms Olivia: I think it’s nerve wracking for someone who wants to be a sissy, say a sissy maid or serve or be the very submissive person in the relationship with or without any of the coerced bisexuality.I think it’s hard if they are in a relationship with a vanilla woman who suddenly looks and says, wait a minute, what are you doing at rhumba panties? Where the hell is my boyfriend?
Ms Delia: Very true. If you have a woman who is kinky and a little naughty and you can approach these things with her, absolutely, that’s fun. Remember she might not want you to be a sissy as much as you want. Sometimes it’s best to talk to your Mistress. Talk to us because you know we love this. We are not judgmental and maybe you cannot bring this up around your wife or girlfriend. You can’t fully be yourself around her. So you need that outlet, that special friend to guide you and talk to you.
Ms Olivia: We do end up being emotional support because each person has a secret life of being a sissy. We are also practical support. For example, how to avoid purging. I feel so sad when a sissy purges because they’ve spent hundreds of dollars on clothes and breast forms and toys and you know, all of this kind of stuff and then they purge.
Tip to avoid purging
Ms Olivia: So my personal tip to avoid purging is to go and get a locker. You probably have to use your driver’s license, which is fine, but either pay for six months or a year in advance or buy a gift card and put enough on the gift card to use that for the storage locker. One tip: Do not give the storage company your home address. I have a sissy whose wife looked at this and said, “Why do you have a storage locker?”
Ms Delia: Right, right. I have had experiences with that too. And I think you are so smart to say this. You can even try paying cash if you have to once a month go up to the office and give them their next month’s payment, whatever it is. This may seem secretive and just like, Oh, if I have to just hide this so much, why am I doing it? But that’s not the case. You’re doing this very secretly because you do care about the other people in your life and you understand that it might not be something that you could share with them. So you’re honoring them by not putting your kink right out there and you’re also honoring yourself by giving yourself a safe space to maybe walk into and look at all your pretty things.
Ms Olivia: That’s beautifully said. Thank you. Perfect ending. Ms Delia, thank you so much for being with us and for doing these Hot Spot episodes. I learn something and I just love talking to you.
Ms Delia: I think every single time we do one, it’s wonderful.
Ms Olivia: You can also tell that we’re besties because we post on each others blogs. Be sure to check out the comments section!
Ms Delia’s feminization blog: FemFabulous
Ms Delia’s main blog: Beg for Mistress
Ms Olivia’s main blog: Experienced Mistress
Ms Delia: If anybody really wants to have some personalized training or ask about the sissy program, just shoot me an email. I’ll always answer.
Ms Delia’s email is: firstname.lastname@example.org
Ms Olivia’s email is: email@example.com
Let’s do some sissy play while we’re going shopping on the phone or on Skype. Give us a call. (800) 601-7259 ask for Delia or Olivia or even better, ask for us both if you think you are sissy enough to handle us.
Okay, my friend, time to go — It’s always a pleasure to talk to you.
Ms Delia: Same here. Bye everybody. We’ll see you next time on The Weekly Hot Spot.