Sissy dating: listener wants help with a new relationship with Goddess Demi

Welcome to the weekly hotspot where Kink meets conversation.

Each episode we explore the psychology of power exchange, share real-world BDSM dynamics

and explain the art of distance domination.

I'm Mistress Olivia here with Mistress Erika and our friend goddess Demi.

Demi, welcome back. We love having you here on the podcast.

Thank you. Thanks for having me.

For the listeners, Demi brought today's topic and said,

huh, you know, I think this would be a really good topic for the podcast.

So I'm going to have her tell us more exactly what she said when she brought it.

But first, I just have to tell folks listeners.

Erika's ignore slave listening and I feel very battling about this

because now he's not being ignored because I mentioned that he was listening to the podcast.

So that's all I'm going to say about that.

Oh my god, it sounds like fourth dumb.

Well, actually, all there is about that.

That's all there is about that.

But here's the fun part.

He won't know any of this until the podcast comes out.

I answer the phone and put him on mute.

Fuck yeah.

He's totally being ignored by all three of us.

So, seven minutes.

So you put, well, I mean, obviously you have to put him on mute,

but you put you on mute for him.

Correct. He can know, if I pick up my headset right now,

I could probably hear if he's moving around.

He just can't hear me.

Typically, I would leave the phone in the office

and then just go out of the office

because he likes dark room sessions.

He just said in the last email,

we're exchanging some emails.

The best phone sex I ever had was in your office.

I love that.

And then called my office's best friend.

Oh, yes, kid.

Right.

Oh, he loves it.

He loves it.

I give him purpose and reason to serve.

So he's happy as a clam and so are we.

He gets to serve me while I record this podcast.

I love that.

And you know, that is a lesson in multitasking ladies.

Right.

I need, you know what?

I don't need an ignore slate because we've talked about this before.

I suck.

I'm like, so now I'm going to be recording the podcast.

I narrate whatever this one is doing.

I'm doing blah, blah, blah.

It was my blog.

Now I'm going to the kitchen.

Walk with me.

So and ignore slaves.

Unless you're into like hearing narration and not talking.

I wouldn't work.

But I think we all need to have podcast slaves.

Yes.

Just kind of like, you know how small indie bands touring around the country,

they will sell mileage.

They'll be like, do you want a sponsor from Washington DC to Roanoke?

And then you pick up sponsorship things.

We should do sponsorship.

I love that.

Opening up the podcast to slave sponsors.

Oh my gosh.

We have totally gone off safari.

I am completely, like I've taken us off on safari.

But you know what?

This was just so funny when Erica said this.

So I had to tell Demi as well.

And now ignore slave.

Goodbye.

And listeners.

Hello.

Yes.

Welcome.

Okay.

So Demi, you brought the topic.

Yeah.

People are looking in there like,

Sissy Daning's listener wants help.

Tell us specifically what happened and why you came to us and said,

you know what?

I think this would be a really good podcast.

Yeah.

Well, somebody who also listens to your show and met me actually through your

show, um, reached out and asked me for some advice.

And I was like, you know, I have some ideas,

but you know, I wonder if Erica and Olivia have a podcast

episode about this that I can send you.

And that's when I reached out to you and and asked.

And I think this is a really good question.

This person was in a long term,

a Nogamous relationship and they got out of that relationship.

And you know, when you get out of something,

you are ready to start over.

You're ready to do all of the things that you felt like you weren't doing

or weren't able to do when you were in that relationship.

And this person was ready to fucking slide it up.

And I was here for it.

Um, so we explored a lot.

And Dating was one of those things.

So they met someone who's awesome.

She's not naturally dominant,

but she does feel comfortable around him to try to be more dominant with him.

And she she did bring up using a strap on an anal doing some anal play.

But she wants to go into to dive into that with them

in a committed monogamous relationship.

And remember, this was initially their slut era.

They were stepping out and going to explore all the things that they didn't before.

So with that said, this person is wondering, what should they do?

What do they do?

They want to be dominated by this person.

They want, they want to have fun.

They want us let it up.

Monogamy's not on the table at the moment.

Maybe in the future, who knows?

Right now, they want to have a good time.

So the question is, is there an ideal time frame for sharing the quote-unquote

dirty details about your king's indoor fetishes when you start dating?

Wow.

And how do you how do you approach this conversation?

How soon?

Let's see.

How do you approach the conversation?

I think probably your best bet is an elegant ball gown with perhaps

heels that aren't too tall.

Maybe maybe four inches, three, four inches, subtle makeup.

And don't go into it with a dick lollipop in your back.

But that's just me.

Okay, so all joking aside, dating is tricky.

And I'm just talking about finilitating, finding someone who is compatible.

They don't have to like everything the same as you, but it can't be the opposite.

So for example, I'm not sure if I could date a Yankees fan.

No, that's not true.

But I would prefer to date a med span, right?

So there's things that are deal breakers, and then there's other things that are, you know,

kind of negotiable.

So let's unpack this.

A woman isn't naturally dominant, but she's willing to try for him.

Second thing I heard was she wants to be in a

committed and monogamous relationship.

Before she tries all of that,

Sissy either isn't sure or flat out doesn't want monogamy.

And Sissy is a total butt slut, but wants to be dominated by this woman.

And then the overall thing, when do you tell someone about your kinks and fetishes?

No, when do you tell someone?

Let's start with that question first.

Yeah, Amy, what do you think?

When do you tell someone?

I think as soon as possible, I think with any relationship that you're getting into,

you have that, I call it the small talk phase, I fucking eat the small talk phase,

but you have to struggle through it to get to know each other.

And that's, you know, that's a big thing for me.

My sex life is a big part of my life.

And it's not something I'm willing to, it's not something I'm willing to suppress.

So I know what I want.

And I have that conversation the first, second date.

Usually the second date, that's only when you learn.

Oh, yeah.

That early.

Oh, yeah.

Interesting.

Interesting.

I used to kind of wait, feel out the person.

No pun intended.

But like, 4th, 5th, 6th, see if we were even like in the ballpark and then bring it up.

Like, you know what?

Getting into the fetish, saying and stuff, now I'm way more like you.

I don't even wait for the date.

I'm like, okay, perhaps coffee, but you need to know this.

I'm dominant.

I'm in charge.

I will be bossy.

If you're bossy, this won't work.

I'm not monocamous.

I'm polyamorous.

I have lovers.

Right.

You know, and some of these guys are like, and girls are like,

oh, that sounds great.

They're mind like a couple of weeks into it.

And it's like, I thought I wanted a freak.

But no, I don't.

I want a tradwife.

And I'm like, buttercup.

Yeah, that is not me.

I do not think that prairie dresses are attractive.

No, Erica, what about you?

I am much like the both of you.

But I do want to elaborate on something that Demi just said.

She hates small talk.

That just that type of thing.

You're right.

It's like, well, you know, go through the paces.

But let's, now Demi, you could correct me.

Back on one of the femdom Fridays that I was in the hot seat,

didn't you mention your word of the year is intentional?

Or somebody did, right?

Yeah, that was my word of the year last year.

Last year, okay.

Let's be intentional with our small talk.

Instead of saying, what's your favorite color?

Do you like to go to the beach?

What is your view on sexuality?

What is your view on homosexuality?

And really dig in to see if this person is open-minded.

If they're open-minded, then you can go to the next step and say,

I'm glad to hear that because I'm pretty kinky bitch myself.

You want to hear about it?

But here's something that very just landed in my lap,

literally 15 minutes before we started this podcast.

I just did a fabulous session with Missy Jane.

She is new to our universe.

She bought my long-distance teased toy package.

And we had several delicious sissy gassons and she was worn out,

but she still had time on her package.

So we started talking.

She's a lifelong gangster, sissy.

And I asked her, I said, we're doing this podcast.

When do you bring it up and dating?

He says before the first date.

So they got out of a long-term relationship.

They knew somebody that they're interested and then said,

look, before we go on this date and fall in love, you know,

kidding, I just want to let you know.

I am a cross-dresser.

I do like to wear women's clothing.

She's like, fabulous.

She was not dominant, but Missy Jane said,

she fell into it like she was a natural.

So there you go.

And I find it difficult and a challenge to admit to the fact

or agree with the fact that women aren't naturally dominant.

I think we're just naturally dominant in a different way

that does not catch the patriarchy eye.

That's well said.

Yeah.

Now, if she says, I'm not naturally dominant.

Maybe she's thinking of them dumb porn.

Maybe she's like, you know, that latex looks hot.

And by God, it is.

Right.

Or if I'm wearing six inch heels trying to kick him in the nuts,

then I'm probably going to break an ankle.

And that can be them dumb, but not necessarily.

So I love that she's willing to try that specific one.

But I caution that there is a difference between something

that she is doing to satisfy you.

Please, you keep you around.

And it's at the beginning of a relationship.

There's a difference between that and a woman who actually gets wet

making you beg with or without the sissy aspect.

And I agree with Erica a lot of women

when given permission and shown the myths of femdom.

Really love it and kind of step into it.

But this is the fantasy from a lot of people.

How do I make my wife or girlfriend dominate me?

Like you say, in distress.

How do I turn this woman that doesn't know anything

about being dominant into Demi?

So that's what happens from the bottom right?

Topic from the bottom.

Stop it right now.

Yeah.

But we actually did a podcast episode in title

to how do I get my wife to dominate me.

So Erica, I'll start with you.

Your thoughts on the girlfriend who isn't naturally dominant

but willing to try.

Right.

And you know, while you were talking Olivia, I thought,

yeah, that word try is problematic.

People sometimes don't use the exact perfect word.

And I'm going to assume that might be here.

What I would love to have heard is,

ooh, I'd like to explore that.

Trying means, you know, very doubtful.

You're not in it.

I'll try to make that stake for you.

Oh, have you ever heard, sorry for jumping in.

Have you ever heard the Yoda quote?

Try or try not.

That's him thing.

Yes, do or do not.

There is no try.

Yes, absolutely.

I'm hearing this particular different situation.

She's saying, I'm willing to try it.

But here's my requirement before I put in the time energy

vulnerability of doing it.

So I think she actually might mean maybe

and work on a negotiate and see where we end up.

Right.

And ladies, if you think of our own personal journeys,

even though I, you know, I fall into,

I love responsibility.

I love to lead.

That's just part of who I am.

There's always been a part of our journey.

Maybe very in the beginning when I realized,

oh my gosh, I course this guy into panties.

That I didn't necessarily feel dominant.

I didn't identify it as necessarily dominant.

Right?

So it's a matter of understanding what that means to you.

Yes.

Like you said earlier, Olivia,

a misunderstanding what that actually means.

It just might mean she needs the opportunity

and the atmosphere to bloom

and to who the dominant she will become.

And we have had to learn how to communicate,

how to be very clear in what we're saying

and what we're doing.

And civilians, I call them, so-called normal people.

People who are not sex workers are not comfortable,

frankly, talking about sex.

And, you know, I'm all of us are completely,

cheerfully, hey, if you've been tested,

I'm a condoms girl.

I'm a dental dam girl.

Are you okay with that?

Yeah, we have experienced with that,

but I have to tell you at the very beginning,

I was kind of, how do we bring up condoms?

Demi, were you ever like that?

No.

Yeah, no.

No, no.

I want to go back to the try.

You know, her trying to be dominant.

For one, I think there's different flavors, right?

There's different flavors of dominating

and domination in general, different ways to dominate,

different ways to be dominant.

And no flavor is better than the other.

In my opinion, so for this person to help support her on this journey of her trying,

for me, I would go back to, so I love the power dynamic.

And if the subby's not doing anything,

what the fuck it, like, where's the dynamic?

Like, where's the give and take?

It's not there.

And I think that's a common misconception

that the dawn's going to take care of everything.

I think, I fucking love to, right?

But I don't want to always be like, I have to.

The subby has to give me something.

We were talking with another guest

and he said,

do me subs are really irritating for all the doms that I know,

pro doms or not.

And yeah, don't be a do me sub.

I mean, especially if it's in a relationship.

You know, I want to touch on the committed emanogamous.

Now, she's saying very clearly, yes, I'll try,

but this is what I want.

And I'm hearing you say, Demi,

that he does not want to be monogamous.

Right.

What do you both have to say about that?

Demi, let's start with you.

So if I were her, I would say, all right, well, I don't know.

So I, I don't want to be monogamous.

I don't.

But I do have people that like monogamy.

So if they want to be not monogamous with me, that's cool.

As long as they're cool with me, not being monogamous with them.

Right.

Yeah, like how, how important is it to you?

And is it a deal breaker?

For me, it's important.

And it is a deal breaker.

So yes, actually, that's the beginning conversation to have.

Yeah.

Right.

Absolutely.

You'll break her for either of them.

And the first thing, if she is looking for a committed

monogamous relationship, perhaps marriage fairly quickly.

And this Sissy wants to run around and do whatever, whatever.

Then they might not be compatible right now.

They might be compatible six months from now.

If she's still single, and if he's maybe ready to calm down a little bit.

Absolutely.

I agree with both of you ladies.

I mean, it's a compound issue, right?

So it's not just as easy as, well, one do I tell her, I'm a Sissy.

That first committed, non-committed fork in the road is a full stop for me.

Don't go further.

Nothing else needs to be discussed because that's the most important thing.

Yes.

You need to plainly let her know that you want to explore,

that you don't want to put strings between you or expectations.

And by all means, don't play games.

Don't hedge your bets for a few rolls in the hand.

Go, well, you know what?

I don't want to commit a relationship.

But before you make that decision,

I want you to listen to what she is saying.

For whatever reason, I am really good at understanding what people don't say.

Right?

She's saying she wants monogamy, she wants that.

But what I hear her saying to you, honestly,

is that she needs more trust, more intimacy,

in order for her to be vulnerable and explore this with you.

Okay?

And a dominant can be just as vulnerable, especially if she's just starting out

in her inexperience.

And if you're not willing or wanting to give her that,

to give her, let her build that trust,

let her build that ability to be vulnerable with you,

then it's not fair to either one of you.

But that's what she's saying.

She's not saying I want to lasso you and rank you into a new,

you know, full-time relationship.

She's saying I'm interested,

but this is what I need emotionally to go forward and to enjoy myself.

That's a great point.

And people think that all three of us just kind of woke up one day and said,

I'm going to go be a femdom and I'm going to dominate Sissy's.

Let me tell you, it's a fucking learning curve.

At the very beginning, as I was learning about cross-dressers,

I thought every single cross-dresser was gay.

Then when I learned about Sissy's, I'm like,

oh, every single Sissy is gay,

every single Sissy wants to suck cock.

Well, no, this is one of the most nuanced fetishes.

And she may not even realize how much she's going to need to learn,

but she may have an idea and say, you know,

I don't want to invest 100 hours learning to please you

if you're not going to give me what I want to need.

Yeah, I have, this is not Sissy.

I have a Subby who, we have a great relationship,

a fucking amazing relationship and they wanted to explore something that I let them know.

I fucking want to, I love this, but I'm not as experienced as I'd like to be.

And, you know, they were like, I love that you said that.

I am and they are.

They've been very, very down deep with this for a long time.

And they're supporting me in my journey of learning more.

So Subby's can do so much for their dogs so much.

I love that. Now, here's where that is different from this Sissy,

because what I heard was this Sissy is just learning to explore as Sissy.

The Sissy can't come in and say, this is what I like, etc, etc.

I love when the Subby and the dominant learn together.

That's so much fun.

That's when it turns into an actual relationship, right?

And it's fabulous, but what do you think? Demi, do you think the

monogamy is a deal breaker for each of them since they're kind of far apart?

I think this, this is a, this goes back to my small talk.

This should have been something that was already known before they had a date.

And I just started dating recently.

And that is one thing that I make very known, that I am not looking for a monogamy.

If you are, that's totally cool. I support you, but I'm not looking for that.

So don't expect it from me. I'm very open about that.

I'm open about being a dumb and wanting to dominate the things I'm interested in with domination.

So those are for me, the small talk. Let's talk about like what the fuck we're going to do.

That's a better combination.

But in all fairness to this sissy, getting out of a long-term monogamous relationship,

that's exploring this new side. I mean, is this person a sissy? Is it,

are they a cross-dresser? Are they a day? Are they?

Bye.

When I finish, I mean, there's all of these things.

So it's kind of, I think it's kind of hard to say this, for this particular instance,

should have been fun even before the date because the sissy cannot know these answers to these.

Well, that's, so when I met this person, they were very, I can tell, our first conversation was

fucking amazing. They know who they are. They know what they want. And I fucking loved that.

And we explored a lot of different things with that. But I think that they're willing at this

point because it has been, you know, they got out of a long-term relationship and kind of

waited a bit but then jumped deep into a lot of different things. I think they're willing to

overlook some things in hopes that this turns out right for the two of them. And I don't think

that's going to work. If you're willing to sacrifice something, especially after you waited so

fucking long to find this part of you and explore this part of you, don't fucking settle, don't

ever. I absolutely agree. Erica, what about you? Oh, absolutely. I don't think knowing what I know

from talking with Demi that they are very compatible. And I would either do one of two things. See

if she's willing to develop a relationship but not necessarily anything monogamous. If she's not,

like Olivia said, okay, let's stay in touch. Let's be friends and, you know, who knows what happens

in six months. But the little things, you know, how you fluff your pillow, how you put the

silverware right. That stuff is not important. The fact that it's commitment versus non-commitment

should be your biggest and only thing to say, look, you're not a bad person but we just want

different things at this time. Absolutely. I'm the same as Demi if someone says, no, I'm actually,

I'm looking to get married and you're a great woman and, you know, whatever I'm like, if you

have marriage on the mind, I promise you, I am not going to change. We are not compatible. And then,

you know, graciously and nicely just kind of move apart. Wow, this has gone by really bad.

I do think this as he can maintain this relationship with this woman and help empower her exploring

if she still wants to continue exploring her dominance side because it does seem like she does.

And at the same time, explore their sissy side more. And who knows where where they'll end up,

you know, I have to keep us updated. Yeah, I will. Absolutely. Perfect. And you know what,

we would love to hear the next time you talk to sissy, oh, I heard the podcast, whoa.

So, um, final thoughts, I'll go first. I love that you say that this sissy knows who they are

and what they want. That's half the battle. What is really important here is, can you be in a

non sissy mistress relationship? Or do you need someone who facilitates your feminization and

butt stuff right away? Now, if she decides, nope, it's not for her, would you want to stay with her?

And is that the compromise that sissy is even considering? Listen, if you are making compromises

at the beginning of the relationship when everything is fucking fabulous, yeah, um,

what's going to happen when things cool down when you have your first fight?

Like, um, sissy goes in and gets it your expensive panties and stretches them like,

yeah, right? Erica, what about you? Well, a final thought for the listeners, intimacy is

much more than just banging the uglies, okay? Or stuffing, or stuffing fun stuff in them.

It starts early in a relationship. If you meet somebody vanilla style, like you go on a few dates

versus just a quick romp in the hay, um, that's when you're exploring each other, that's when these

conversations should be happening. And if you're not comfortable having these conversations about

sex and sexuality on a first, second date, or as you lay there with your wet pussy and his dick

limping, um, then call us. We will help you be comfortable talking about sex and sexuality.

Oh, now, uh, Demi, I, you might have a final thought, but I just thought of something.

Would sissy feel comfortable doing a, um, call with you, sissy, and this woman? That actually

might be something to suggest, because I've worked with couples. And some of the women are saying,

I have no idea what I'm doing. Now, here's another thing to suggest. If she wants to talk to you

so low, have sissy pay for it. She should not have to pay for any of this.

Fuck yeah. Have sissy pay for it. And then leave the house. Yes, give her some total privacy.

Because then she can say, Demi, these are my concerns. What do I do?

Right. Yeah, I love that. I fucking love that. I think that's a really good idea.

Thank you. So folks, get in touch. Now, I've had a couple of people say, I'm sending you an

email because you told me to get in in touch. And now what I really want you to do is free

sexting with me. That happened to kind of both of us in the past couple of weeks, didn't it?

Yeah. Okay. So get in touch means send a question, say I like the podcast, say I'm interested

in learning how to get a session. You can write and say I love the meds, but I'm a little bit

concerned about this. That other thing or I'm a red socks fan and I'm sorry, I don't like you

anymore. I thought I don't. I mean, whatever. But listen, sessions are different from those

get in touch free emails. Yes. And I mean, I hate to like say it that bluntly, but

dude, come on. You know, and for all of the other people who are like, oh my god, but I've been

sending emails to all of these mistresses for years because I love them. You're already ours.

These are the ones we don't have age verification on you. I don't know you. I have no relationship

with you. It's like sending random dick pics. So no. Yeah. Yes. When we say get in touch, give us your

thoughts about the podcast, ask questions or suggestions or just say I love you ladies. That's

all you need to do. Yes. Yes. That's sad. Debbie, how do they get in touch with you?

Yeah. You can find my blog, sensualcockties.com or email me, dummy at enchantrixempire.com or find

me undescoored at LDW, dummy or on Twitter, DOM, D-O-M-M-E, dummy. And I'm on Blue Sky too, but it's

I don't know. I think it's God is Demi. That sounds like a living. Oh my god. Yeah. That sounds like

me. Erica, what about you? My email address is Erica, E-R-I-K-A, at enchantrixempire.com, Twitter

and Blue Sky, Erica and Chantrix. I kept it simple for you and me. And of course, like Demi said,

we're all on discord LDW, Erica one word or LDW, Olivia and you heard Demi's profile name.

And my email is Olivia at enchantrixempire.com. Twitter is Mr. Olivia one. Blue Sky is different,

Miss Olivia and then the socials for the podcast, FEM, DOM, podcast, F-E-M, D-O-M-M-E, podcast.

And my blog is experiencedmystress.com. Demi, we love having you as a guest and this was coming

here. This was such a great topic. Thank you. Thank you. And I hope it was helpful.

I hope so too. Would you talk to Sissy and see if it was helpful?

I will. Yeah. And then let us know. Thank you to all of the listeners for joining us.

We will see you next time for the weekly hotspot. Bye. Bye.