Masturbation May

It’s Masturbation May 

Princess Cassidy joins Ms Erika and Mistress Olivia for everything about self love: stroking, edging, delay and denial – tease and denial and even chastity as part of Masturbation May.  Today, you’ll hear how the ladies celebrate and how they plan to tease you. 

Listen to Masturbation May on Spotify – or anywhere you listen to your podcasts.  A new episode posts every Monday at 1 pm eastern time on Cock Radio on Spreaker.

Ms. Olivia: Welcome to The Weekly Hotspot, kink conversation, BDsm advice, and insight from the worlds of distance domination and phone sex. I’m Mistress Olivia here with Ms. Erika and our friend, Ms. Cassidy, Princess and boob-i-licious.

That’s what we’re going to start calling Cassidy, Princess Boob-i-liciousness.

Ms. Cassidy: That’s perfect. The boobs are nice. I like them.

Ms. Olivia: And you’re a beach bunny!

Ms. Cassidy: For sure. California girl.

Ms. Olivia: We are so glad that you’re here. Think about it, an entire empire created on masturbation. So it’s perfectly appropriate that we’re all here because it’s Masturbation May. 

This is our time of the year. We celebrate it all 12 months. For the vanilla world, it is a month dedicated to wanking, edging, jerking off, jacking off, jilling off for the ladies. It is definitely our time of year. I love that there are a bunch of slang terms for masturbation.

Celebrate Masturbation Month

Ms. Olivia:  What do you both like and how do you celebrate Masturbation Month?

Ms. Erika: I love that there’s a month dedicated to promote healthy sex practices and masturbation is certainly one of them.

I love encouraging a positive outlook with your body, your sexuality, and that includes self-love.

In addition to positive messages and blogs and tweets that I’ll be doing throughout the month, I actually have a special running. Everyone who calls me will get one entry into winning your own free Jerk Off Instruction audio.

Check out my blog IntelligentPhoneFantasy.com, “Strokers Rewards” to get more details. 

Ms. Olivia: Or call you at 1-800-356-6169 and ask for Ms. Erika and tell her you want to jack off for her.

Ms. Erika: There’s an assignment. You do have to do an assignment when you call in order to gain entry, but you’ll see it over at the blog. I love that idea, Miss Olivia.

Ms. Olivia: Cassidy, you’ve also got some news about Masturbation Month as well, right? 

Ms. Cassidy: First of all, let me say you can go to our EnchantrixPerks.com website and see our Enchantrix Weekly every week that will also have this information in it with a direct link to Ms. Erika’s blog as well as any other promos going on. So you can check that out. 

For me, because it’s Masturbation May and I love to celebrate, even though I’m pretty busy, finals are ending, so I’m going to be taking some calls this month.

If anyone wants to talk to me, you can always email me to see when I’ll be on or, fingers crossed, I will get something up on my blog with some details on that.

My blog is FirstClassPhoneSex.com. We also have a new Mistress of the Month for this month. It’s Miss Tia. We thought it was perfect because her blog is MasturbationMistress.com. She loves Masturbation May. So Ms.Tia is our Mistress of the Month for Masturbation May. It’s perfect. 

Mistress meeting in Vegas, what could possibly go wrong?

Ms. Olivia: I hope I’m not speaking out of turn, but I’m going to take us on a little excursion, which I do.

Several years ago we would have Mistress meetings and we would go to Vegas. A whole bunch of Mistresses would go and I remember one time we were celebrating a success that Tia was having.

We were in a strip club and Ally was there and she bought bottles at Patron for all of us. They were on the table with shot glasses.

Strippers were coming over and bumping and grinding and… strippers with women… oh, we got to touch, and they were touching our boobs, kissing us, and just bumping and grinding.

The poor strippers on the stage, all of the men gathered around us and we were in a little circle with a whole bunch of tables and a whole bunch of strippers.

And the guys just started throwing dollar bills, $5, $10, $20 bills. Money was just raining down. I’m not sure I’ve ever been that blind fucking drunk, but you know, I think of Tia and I’m like, “Tia, I love you, but you’ve ruined me for tequila.”

So Cinco de Mayo, I will not be celebrating with a margarita. 

Ms. Cassidy: I think of tequila and Tia as well because the time that I was with her, I got so drunk, I literally sat down in the hallway of the hotel and dumped my purse out because I could not find my hotel key and I didn’t even have it.

I was staying in a room with someone and they had the key, but I was sure I had it. I dumped my purse out, sat down on the floor in the hallway, and was determined to find the key. Oh my goodness. And I always think of that. I think, oh my.

Ms. Olivia: Listen, Tia is really fun. We don’t want to give the impression that if they call they’ve got to get blind, fucking drunk. 

Ms. Cassidy: Oh, God, no. She is fun. And you guys have to hear her voice. You have to go listen to her voice. She has the most amazing voice. Every time I hear it I think, “Why don’t I sound like that?”

Ms. Olivia: Seriously, I love your voice, Cassidy. You have like the quintessential Princess, college, bop around, sweetest girl-next-door voice.

I have heard you, when you’re on a call and you are humiliating someone.  The juxtaposition of your sweet face and your sweet voice and then some of the stuff you say. It’s amazing!

Ms. Cassidy:That is always my favorite because it’s so much fun to sound sweet and be really mean. 

Ms. Olivia: Or really naughty. I think both of you know Yvonne. We did an interview with Yvonne and about Acceptance as a Crossdresser.

Yvonne is a regular listener of the podcast. When she started listening to the podcast, this was when Ms. Delia and I were doing the podcast, Yvonne said, “Oh, I have to tell you ladies. You have potty mouths.” I said, “We fucking do!”

An assignment for our kinky podcast listeners

Ms. Olivia:  We are asking you to support us. So we want you to subscribe on Apple Podcast. We want you to Like the podcast and leave a review on Apple or any place where you listen to your podcasts.

We are moving up on the charts. The Weekly Hotspot has charted. It’s fucking amazing to get this kind of support. Thank you!

Ms. Cassidy: That is awesome. Oh my God. 

Ms. Olivia: I was shocked. You know, I got this little email saying, “Hey, you charted.” I’m like, “Oh, thank you. I don’t know what that means.” Erika researched it. We are on the front page of sexuality podcasts and our podcast on strapon sex is number five in Qatar. 

Ms. Cassidy: That is awesome. You guys are kicking ass. That is amazing. 

Celebrate self-love with the best masturbation

Ms. Olivia: Yup. It’s something to celebrate. And speaking of celebrations, celebrate Masturbation Month. This month is so much fun. It really is. Although, we have Masturbation on our minds pretty much all the time, right? 

Ms. Erika: You’re not kidding. It’s a daily topic. Don’t get me wrong. I’m not complaining. I love it. Bring it on. 

Ms. Cassidy: Masturbation? Safest sex! You can do it anytime. Anywhere. Don’t have to worry about social distancing. Perfect.

Ms. Olivia: I live in New York State and the New York State health department got in huge trouble because they put out a thing at the very beginning of COVID saying, “Okay, we want you to have safe sex and the best way to do it is masturbation.” People said, “Oh no. You shouldn’t say that.”

But it’s true. Everybody masturbates. I don’t care what people say. Everybody, guys, girls, everybody. 

Ms. Cassidy: Well, I know out here in California, there was a whole thing on the news because they recently started encouraging teachers to incorporate into all their sex ed classes, information about masturbation and why people should not be ashamed to do it and how it’s not something dirty or bad. There’s a huge uproar about it, but it’s so cool. 

Ms. Olivia: The history of Masturbation May is bringing masturbation to the mainstream by talking about it. Everybody does it, but not everybody talks about it. It started as Masturbation Day, May 7th. Then it ended up Masturbation Month, which is just fabulous.

Before coming to LDW Group did either of you know there was something called Masturbation Month? I didn’t. 

Ms. Erika: Well, I’d heard of it, but I didn’t really pay much attention to it other than to say “Yes, please. I’m in.” Now I’m a little bit more involved outside of my own bedroom promoting healthy sexual habits. 

Ms. Cassidy: I didn’t know about it at all. I had no idea until my second year here that it wasn’t something Ms. Ally made up. I just assumed she made it up and said, “We’re going to celebrate it.”  Everyone said, “Absolutely! Let’s do it!” 

More masturbation slang

Ms. Olivia: I love the names for cum, for the penis, vagina, and for masturbation.

There are some very funny slang terms for masturbation!

• cuffing the carrot
• saucing the taco
• beating the Bishop? What the fuck is that about?
• burping the worm
• buffin’ the muffin.
• choking the chicken. Where did that come from? That is like, so not sexy. 

Ms. Cassidy: No, it’s not. And it’s the one I’ve actually heard of so far out of these. I’ve heard people say that. 

Ms. Olivia: Me, too. Painting the pickle. Have either of you ever heard painting the pickle for masturbation?

Ms. Cassidy and Ms. Erika: No, no.

Ms. Erika: Jerkin’ your gherkin, yes, but not painting the pickle.

Ms. Olivia: That’s especially if he has a small penis. Oh, and this one… flicking the bean. 

Ms. Erika: Yeah, we’re not going to be flicking too many beans on this side of the keyboard. 

Ms. Olivia: Now here’s the thing. This is a personal pet peeve of mine and Erika’s… Cassidy, feel free to weigh in. Don’t fucking flick my clit. Don’t use it like a light switch. And (fast flicking sound)… NO!

Ms. Cassidy: I completely agree. If you don’t know what to do with it, just keep your fucking hands off it.

Ms. Olivia: Or ask us. We’ll tell you.

Ms. Erika: Now with that said, there may be the woman out there that does enjoy it, but don’t go there first off guys. Don’t go there. 

Ms. Olivia: Oh, at the very tail end, so to speak, maybe. Maybe. But at the very beginning, I know it’s popular in porn because it looks interesting, but oh, ow! Guys can call us and ask us how to make love to a woman.

Live help for a phone sex service? What?

Ms. Olivia:  Now, Cassidy, you are a Cock Concierge. I love that LDW Group has a help desk called Cock Concierge. What that hell is that?

Ms. Cassidy: It’s really cool. We started it by riffing off some of the bigger names, regular sites where you can go and you don’t know how to find something, you can click on a button and ask.

Usually it’s an automated question and answer, but for us, we thought “We don’t want to be automated. We want them to be able to talk to somebody.” 

That’s where our Cock Concierge comes in and we’re there.

If you come to our site after hearing this podcast and you can’t figure out how the hell to find Ms.Olivia or Ms.Erika.

On every one of our sites, you can click on Live Help, or you can just go to EroticConcierge.com and just ask us, we can tell you how to find blogs, tell you the number to call, talk to you about pricing, anything like that. 

Find the perfect erotic playmate for you

Ms. Cassidy:  If you come and think, “I really want to talk to somebody, but what I really love is for a woman to cover herself in balloons and fucking pop them until I cum.” We’ll find you just the right person who would absolutely love to talk to you about that. 

Ms. Erika: I love that aspect of what you do, Cassidy, suggesting who to talk with because it’s daunting to try this and connect with someone. I mean, look at all these beautiful women, which one do you talk to?

You guys are really a great gateway of helping them feel more comfortable. “Oh yeah, Erika would love to do that!” Or “Olivia would love to do that! Go right ahead. Give them a call.” 

Ms. Cassidy: Exactly. That’s exactly what we do. If someone comes in and says, “I really love cuckolding, but I looked at this blog and I don’t see a current post about cuckolding,” we can say, “You know what? Just because she hasn’t written something right away, check out our website and you can see that she loves cuckolding, or let me help you find something she’s written on her blog about it.”

There are search features on our blogs. It really isn’t that hard to find, but when you’re overwhelmed or you’ve got your cock in your hand, it’s really hard to think.

Ms. Erika: Cock brain equals no brain.

Ms. Olivia: It is so difficult to think when you’re rock hard. Speaking of rock hard, let’s talk about all the different types of Masturbation. Some of the different types, Erika, why don’t you start.

Different types of masturbation

Ms. Erika: Any way to simulate yourself for an orgasm is what I’m interested in. I like all kinds of masturbation and I love showing men how they can stimulate themselves differently, that they might have never thought of, or where they were scared to try.

Orgasm is a learned response. The more ways you learn to cum, the happier I am. If you were interested in pleasing a Mistress, being diverse and being able to get to that point of no return and allowing me to say yes or no any way I wish, is fantastic.

Ms. Olivia: All of us actually know more about a penis than the owner of said, penis. We have played with more cocks.

He’s got way more history, but however you started masturbating (in a sock that’s lubed up, on a pair of panties that you stole, lubed up with lotion, or dry stroking)… whatever it is, that’s his go-to. “Oh, that felt amazing. I’m never going to do it any other way.”

And so if he’s been doing that for decades, well, fuck me running fellows, you need to call us. 

Ms. Cassidy: You are in a rut. 

Masturbation Games

Ms. Olivia: We’ll spice it up with all kinds of things, including Cassidy. You like games.

Ms. Cassidy: Oh my gosh, I do. Masturbation games are one of my favorite things. I’ve used dice, a deck of cards, a metronome. Sometimes I just pick random numbers and that’s how much they have to stroke.

Whatever the tease and denial game feels like is going to work with who I’m talking to, is what I love to do. 

It does the same thing you ladies both mentioned. It mixes it up for them. Then guys, believe us, your fucking head is going to blow the fuck off because what you think is working, there will be something and you’re going to think, “What the fuck? I never did that before. That was a blast.”

Ms. Erika: The best review is, after the grand finale, all you hear is, “Oh, fuck. Oh fuck. Oh fuck.” I said, “I take that as a good thing, honey?” 

Ms. Olivia: Speaking of reviews. I got this quote from a stroke pet. We did this really intense and psychological role-play edging scene.

He said:

“I was a bit scared and still am, but the slave mentality towards this type of play suits me and I truly enjoy having my cock worked without regard for what is going on with the rest of me. I was dripping, leaking, convulsing, throbbing, and shaking.

“None of that mattered. The task was to keep working towards the next edge, no matter how fast the next one arrived, and not stop until a ruined orgasm was granted. It was a delicious torture scenario. I hope to enjoy it again with you again soon.”

Isn’t that the best? I love Tease and Denial. Tease and Denial or Tease and Delay, edging. We did a whole podcast episode about the paradox of arousal by sexual denial. And it is a paradox. 

When people start masturbating, it’s jerk jerk jerk jerk jerk, right? So they get the quick jack off. I think that’s awesome with the 10-minute calls, some of which are three minutes. 

Ms. Erika: (Talking fast) I’ve got places to go and people to see, let’s go!

Edging and stroking – how to have a big orgasm

Ms. Olivia: But, it’s so much more fun when you do things like games, Jerk off Instructions, edging, stroking, stroking for hours. 

Erika, you are brilliant at this. Having someone do a stroking session that can last all day or multiple days. 

Ms. Erika: Oh, absolutely.

The paradox you speak about is true because if you understand what happens to your body during sexual arousal, when you have an orgasm, your body goes into full reverse mode. Like a jet when it lands, it reverses engines. That’s what happens to your chemistry.

You have all these feel good hormones pumping your body up. This is when you say, “Hey, sticking that in my ass sounds like a really good time. Let’s do it.” But as soon as you orgasm, it’s like, “Oh yeah, no, wait, fuck, what’s going on?”

It’s because your body naturally throws hormones into your body to reverse those effects. So without that orgasm, I’ve had some describe it as a sort of sexual high and they become addicted to it and they don’t want it to end. That is fascinating and fabulous. 

How long can you stroke your cock?

Ms. Olivia: What is the longest stroking session or the longest call that either of you had that was continuous stroking?

Ms. Cassidy: Okay. So mine is… oh, oh, that’s hard. I’m trying to think back.

Ms. Olivia: It is hard. Hard and slippery and wet and tight balls. Yes, Cassidy, it is hard.

Ms. Cassidy: I’m going to say probably right around an hour. It’s a little shorter than some people can keep them really going, but I tend to decide to entertain myself by ruining something for someone.

Ms. Erika: The continuous stroking is one thing. These past few months, it might have even been longer than that, but it’s so right there in the front of my mind. I did a two hour session and 43 edges in those two hours. Did we have a break or two to have some water, reposition? Yes. So, it’s not necessarily continuous.

The reason we got to 43… okay, I’m going to give away some of my secrets. Hopefully not everybody who calls me listens, so this is a little bit of how my mind works. 

Leading up to the session, he contacted me. “I’d love to do a session. Here’s my toy list.” And he’s looking for instructions up to the session which was four days away.

I said, “Okay, great. I want you to wear your chastity cage and I want you to track how many hours you were in that chastity cage.”

He proudly came to sessions saying, “Mistress, I wore that for you for 43 hours this past week.” I said, “Great, we’re now going to do 43 edges before I will even consider an orgasm.” And he did it.

Ms. Olivia: I have some people in a chastity cage for six months! You both know Lexi is currently in chastity. I talked to her the other day and I want to say she is at a month and a half into her chastity experience. 

Ms. Erika: That is fantastic Lexi, congratulations. 

Ms. Olivia: And there’s no end in sight. So Lexi is not going to get 40 edges after 40 days. Lexi is locked the fuck up. 

Tease and Denial – to the best orgasm ever

Ms. Olivia: Masturbation May, you “may” or “may not” have an orgasm and Cassidy, you mentioned ruined orgasms. 

Just like there’s this huge broad category of types of masturbation play, there’s also multiple types of orgasms.

Just the regular jerk jerk jerk-squirts orgasms, timed orgasms, stroke-stroke-stroke-stroke, with or without role-play.

Ruined orgasms

Ms. Olivia:  Then I’ll say, “Okay, if you can come in 20 seconds, you’re allowed to have an orgasm.” I’ll start and say, “20, 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5-4-3-2-1,” and he’s had those 10 seconds at this slow pace and I’ve had guys yell, “NoNoNoNo!”

Isn’t that wicked?

Ms. Erika: It’s a great way to judge a true edge because a lot of guys think just because they got their cock hard, that’s an edge. No, no, no, no, no. That’s not an edge. If you’re truly on the edge, you’ll be able to come in 10 seconds. 

Ms Olivia: That’s true. That’s why you pick 20 seconds and count the first 10 seconds slowly. Because he’s thinking, “Oh, I’m on the edge. This is awesome. I’ve got 20 seconds to just, I don’t have to worry. I’ll shoot my load. I’m going to paint the fucking ceiling with my semen.” And then it’s 10 seconds, not 20. Or, as Cassidy mentioned, a ruined orgasm. 

Ms. Erika: Ruined orgasms are magical.

Ms. Olivia: Did you know about ruined orgasms? Had either of you ruined orgasms before you came here? I’ve got to admit, I never had. 

Ms. Cassidy: I had, but it was more of an accident. I wasn’t purposely trying to, but like I said, I get bored and decided to entertain myself. 

Ms. Erika: “Look! A kitty cat. Oh, I’m sorry. Weren’t you finished, honey? Well, I guess you are now. Okay, let’s move on.” 

I think I’m in the same boat as Cassidy. I ruined an orgasm  through bad timing, but I never really understood the power, the magic of a ruined orgasm until I started doing this regularly and coercing them.

There are many ways to do a ruined orgasm as well. Simply abandoning, a little pee hole pinch, and for those who like a little pain play, a little CBT. Just smack that fucker to orgasm. 

Masturbation Hall of Fame

Ms. Olivia: Putting a stroke pet through his paces is really the point of a huge stroking and edging session. It can be multiple times through a day, multiple times over a week, but there is at the end, some kind of orgasm, whether or not it’s ruined.

I think that qualifies as a Masturbation Marathon. I think that gets the caller into the Masturbation Hall of Fame. Erika, you’ve got some people that are in the Masturbation Hall of Fame. 

Ms. Erika: Oh, absolutely. Between those edges, how many strokes between orgasms? You can go a week, two weeks. “No, you said you wanted to masturbate. You didn’t say you wanted to orgasm. So there’s a big difference.”

I mentioned earlier about having people masturbate in different ways.

One of my favorite guided masturbation sessions, and we’re going to include a little bit of humiliation here, is humping masturbation. Training that cock to cum while it’s humping. Not a little pocket pussy. Oh, no. That’s the easy way, putting the pocket pussy between two cushions or two pillows and humping away. No, no, no, no. I mean, riding that thing like a donkey and getting off.

Cock envy

Ms. Olivia: I’m going to take us on a detour.

If I had one wish, I would probably go for world peace or something like that. But if all that was covered and I had one wish, I would want to have a cock for about one week.

I want all of my girl parts. I don’t want them going anywhere, but I would want a real, attached, male cock for a week and I would masturbate like a monkey for the entire fucking week. 

I think the penis is just the most fun kind of thing. 

Ms. Cassidy: There’s so much they can do with it. There’s so many places to stick it. Granted, some of them need a Penis Safety Announcement: Don’t put it there. 

Ms. Erika: Do not masturbate with Soft Soap. You’ll be chafed for a week. 

Ms. Cassidy: “That vacuum cleaner is not what you want, dude.” But, it’s so much fun. There’s so many things they can do. 

Mistress, May I Cum?

Ms. Olivia: Orgasm is not the goal, a lot of times. Orgasm control, orgasm delay or flat out orgasm denial. One of our most popular assignment sites is MayICum.com. Let’s talk about MayICum.com.

I love that site. It’s great for assignments like my posts: Masturbation Phone Sex with a Porn Chaser. It’s an assignment and he gets all worked up and then clicks on the audio and the audio answers: May I cum? 

One of the most popular masturbation instructions ever.

Ms. Olivia:  I did 30 second little snippet audios. That is one of my most popular audio efforts. It was 30 seconds where I say, “No, no, no, no, no. No, no, no, no, no, no. Stop it. Put your hand down. No, no,” for 30 seconds or so. 

Ms. Erika: I love that. I think I did one, but not that long, but it was just for a joke. I just said no in different ways. No! Ah said, “NO!”

Ms. Olivia: Isn’t that epic?

Ms. Cassidy: It’s one of the best things about our May I Cum site, because there are so many different things on there. You can have an assignment, a ruined orgasm, sometimes just some details about a specific way to masturbate. 

I love, love the posts like what Olivia just said, where you can read it and then you have to listen to that audio to find out what happens. That is my favorite.

That’s what I used to do all the time. I would record an audio and I would just record what I wrote so they would start out thinking they were just listening to whatever I wrote. But the only way they would know if they got to cum was if they listened to the whole thing. Love it. 

Ms. Olivia: Sometimes, I will say, “You have to cum, but you are only allowed to cum after doing this, this, and this.” It’s like sending them through a treasure hunt. Then I’ll get this email, “Mistress, I did everything you asked. Now may I cum?” 

I’ll say, “Well, let’s see.” And I incorporate the tease and denial games like you were talking about, Cassidy. I’m going to go to Random.org and we’re going to do this with a dice game. 

I’m going to roll one dice, we’re going to do over/under. 

Ms. Erika: I’ve also done odds and evens. Pick one.

Ms. Olivia: Or flip a coin. I sit there and say, “I really was going to let you cum, but you chose tails and I chose heads.” 

Ms. Erika: Your odds don’t look good.

Ms. Cassidy: Oh my gosh. I have to tell you, in case anyone doesn’t know, I also Dispatch.

There is a guy who has called in the middle of the night when Olivia’s not here. He’ll say, “I think I completed all my assignments and I don’t know what to do.”

Until you said that, I thought he was just trying to get Dispatch to tell him what to do, because I always tell him, “Well, if your assignments are from Olivia, then you’re just going to have to wait for Olivia.”

But he has called over the years, it’s been a couple of times and he’ll, they’ll, it’s usually the same guy, but it’s been a couple different ones that will say, “Okay, Miss Olivia, I did these assignments and I don’t know what to do.”

Ms. Olivia: “No, no, no, no, no. Absolutely not. No.” That’s what you tell him. You send him to my blog and I will repost the No audio. “No, you’re not allowed to cum. Not yet. Nope. Not yet.”

Ms.Cassidy: That would be perfect. I can’t speak for any other dispatchers, but, and not all of our dispatchers have taken calls, so some of them might not be quite as playful, but I always tell him, “Hey, you know what? Olivia’s not here. So guess what? That means. You have to wait even longer.” He just sounds like, “Oh, no! Oh, no!”

Ms. Olivia: Oh my God. Erika, what do you love about orgasm control? May I Cum, StrokeForMe.com.

Ms. Erika: The hotness factor of doing sessions and feeling that energy on the other side of the phone is fantastic. Anybody who knows me or knows any of you ladies or any of the ladies here, it’s the absolute hook to have that power, to have that control. “No, you will not come today. You will keep that cum in those balls, boy.” Fuck yes! I just got chills.

Chastity – the ultimate in orgasm control

Ms. Olivia: Keeping the cum in the balls. Chastity is the ultimate form of control and submission and our Dominance. 

Ms. Erika: I am a big proponent. If you consider yourself a submissive male, but you’ve never been interested in chastity, saying, “Oh, that’s not for me. I can keep my hands off my dick.” There is something that happens in your brain when you are locked that just explodes that submissive feeling. 

Before I came to LDW, I played around with it, just on a personal basis. “Oh, you’re going to stay locked while I tease you,” and then the grand finale. But there are those out there that are addicted to that sexual high. They absolutely love it. 

Some feel that masturbation should have a higher purpose. They shouldn’t just cum because they’re horny. There should be a purpose behind it. Chastity checks off all those boxes. 

Ms. Olivia: I put one man in chastity so he would finish remodeling his bathroom. Perfect motivation. Seriously. He stopped fucking around with the bathroom. He got it. He got it done so fast and told me his wife said, “What gotten into you? You’re really working hard on this.” He answered, “Yes, I am.”

We did a podcast on it. The Femdom Guide to Male Chastity. I love chastity. 

Ms. Cassidy: I have to admit that I did not know very much about chastity when I started LDW. It was one of those things that I had heard about, but I really didn’t know that much about it. But after I did a couple of 2 Mistress calls with Mistress Cassandra….

Ms. Olivia and Ms. Erika in unison: The DICKtator.

Choosing a Chastity Cage

Ms. Cassidy: She knows everything about everything chastity, I swear. I thought chastity was amazing because it focuses them in a way that nothing else can. 

I have to tell you, I hate picking out cock locks. Don’t come to me and ask me to pick one for you. I want you to choose. And then I’ll either: make you use it in a way that is going to make it so much worse for you, or I’ll laugh at you for picking the wrong one.

Ms. Erika: It’s an assignment. You want them to be in chastity or they want it all, so they want that experience. Part of your assignment is learning about different chastity devices, learning how to measure correctly and finding a device that suits your lifestyle. Why is that our job? That’s the submissive’s job to do the work. 

Ms. Olivia: I’m a control freak and a nerd. So I’ve researched all of it. The crème de la crème is Mature Metal. My favorite one is the Queen’s Keep because I’m the Goddess and the Queen does keep her small minions, or her large minions, locked up. 

We did an amazing podcast Chastity Interview with William from Mature Metal about how to choose the right chastity cage.

Now we’re going to measure. Measure flaccid. 

Ms. Erika: “It’s hard to do when I’m talking to you, Miss Olivia.” 

Ms. Olivia: It’s hard to do. 

“Go and get some ice. We’re gonna put the ice in a bowl of water and get a washcloth wet. Now we’re going to wrap it around your cock and balls. I guarantee you will lose that hardon.” 

“There you go. Now get the measuring tape. Okay. All right. We’ll keep working on it.” I love that.

Ms. Erika: I have my preferences. I love a metal cage for a cock. I just think it’s the sexiest thing.

Ms. Olivia: Or pink! 

Ms. Erika: For a little added humiliation. 

Ms. Olivia: Oh, absolutely for sissies, sissy in chastity. Oh, those little adorable… little chastity cages are just gorgeous. Sometimes they even come with sparkles.

Ms. Erika: (puff of air) Glitter bomb. 

Ms. Olivia: I was talking with Lexi the other day and I mentioned that we were going to be doing this podcast in celebration of Masturbation Month.

She said, “Well, you know, you ladies always leave something out.” I said, “We do not. We talk about masturbation techniques. We give us assignments, we do this, that, and the other thing.”

Then she says, “Well in your blogs, you never tell him or her to think for herself or himself to see what happens.”

Now we do definitely talk about using sex toys for masturbation and anal pleasure, but Lexi has a good point.

I’ve never done a blog saying, “Stick your finger in and wiggle it around,” although I have done that on calls.

Ms. Cassidy: That’s a good point. I don’t think I have either. Like you said, I’ve done it on calls because it just sort of is part of it. I don’t think I’ve ever actually written anything about it at all

Ms. Erika: Inspiration. 

Ms. Olivia: Lexi is inspiration for sure.

Jilling – masturbate and orgasm as a woman

Ms. Olivia: So with Lexi, we talk about lady orgasms or jilling. That can be with a sissy, a crossdresser, a trans woman… or us. 

Ladies, I’m gonna put you on the spot. I’ll go first. Sometimes I masturbate on calls. Sometimes I tell the guys, sometimes I don’t. How much do either of you want to say about your personal masturbation habits… on calls or just in your personal life.

Ms. Erika:  Good question. In my personal life, I’m very well taken care of. So, alone time there is far and few between.

But when it comes to calls, not all calls lend to me having self-pleasure. I get very selfish, very distracted, and my focus is usually on the caller, not myself, even if I’m turned on.

Honestly, if I cum, it’s just like, “Okay, I’m done with you now. I don’t care what you want, go away.” 

With that said, there are a few lucky callers that have been able to experience that side of me. So my question to you is “Are you feeling lucky?”

Ms. Cassidy: You know that all of them now are going to say, “Please let me be the one, please, let me be the one, please.” 

Ms. Olivia: Sometimes I tell, and sometimes I don’t. Cassidy, what do you do with callers and your personal life?

Ms. Cassidy: With callers, it’s similar to what you guys have already said and to what Erika said about choosing. It completely depends on the caller.

I always imagine a new call with someone like I’m meeting them at the club. We start talking. If you ever do a call with me, you’ll see that I’m interested in you. I want to know about you. I want to talk to you because that’s how I imagine it. 

We’re getting to know each other. You find out about them. They find out about you. You dance a little, it gets a little sexy, and then you decide just how far you’re going to go.

Mutual masturbation on a call is like that for me. I might, but I also might not. It just depends on if I’m feeling some kind of connection, even the smallest one, then I might go there. If not, you’re still going to have fun. You’re not gonna know, but it definitely depends.

Ms. Erika: And the type of session too.

Does a Domme have an orgasm?

Ms. Erika: If you’re being called to be a strict Mistress, although that may be arousing to you, it’s very distracting and you need to focus on your pet and taking care of them. So I use that as motivation and energy to stay in the game. 

Ms. Olivia: Domme space is the exact opposite of subspace. So Domme space, when I’m in that space, it’s not sexual in the sense of “I’m so aroused, I’m going to have an orgasm.” It’s an alter-space, but it’s not the same. 

Oh no. I’ve got to tell you. I have masturbated thinking about a session after the fact. 

Ms. Cassidy: Yes. You’re exactly right.

That Domme space is a specific feeling mentally because your doing it really is a power exchange.

Anyone who has never tried it, realize that if you’re in subspace, you are not completely powerless, it’s a power exchange. And if you are completely powerless, your Domme maybe isn’t doing what they should be doing. 

In Domme space, you are focusing on letting the sub feel completely powerless and yet still making sure that they’re enjoying the session and you’re moving it along.

I can’t focus on masturbating when I’m making sure that all the pieces are working.

Masturbation even when you have regular sex

Ms. Olivia: Do either of you ever masturbate, even when you’ve got a partner right there? I’m polyamorous, so I have a regular male partner, regular female partner. So I’ve got all the bases covered, but sometimes I just want to give myself a hand. Do either of you do that?

Ms. Erika: Like I said earlier, rarely do I do that because I have such an attentive partner myself. Orgasms are great, but having my male partner inside of me when I orgasm is the best orgasm. They just seem to go on forever. So, I prefer those. 

So I think, “Okay, I can get off right now. Then I’m going to work all day. Am I going to really feel up to that later on?” So I may hold it. Most times I do, sometimes I don’t. 

Ms. Olivia: Cassidy, what about you?

Ms. Cassidy: For me, my boyfriend, who I’ve been with forever and ever is amazing, I don’t often, just on my own, get off. Plus we have sex enough that I would totally run out of time to do homework, take finals. If I was also gonna masturbate, I would think, “I don’t have time for this,” because we do it enough that it uses up my time.

Mistress Olivia wants to know

Ms. Olivia: Am I just the fucking freak?

I like watching porn. Lesbian porn is awesome. POV blowjob porn. I don’t really like Femdom porn so much. I also love reading erotic stories. You know, I got into phone sex because I love Literotica and I don’t know if they still have it, but they had private chat rooms.

I would get into the private chat rooms and I would hook up with somebody and I would say, “Okay, I’m going to call you.” I would be calling and talking to these random guys and doing phone sex. I was bitching to a friend of mine. I said, “The motherfucker came, I was still all amped up. He came and fucking hung up!? That’s just rude.”

She said to me, “You know, you can get paid for that.” I said, “Paid for what?” And she said, “Paid for phone sex. You’re doing it for free anyway. You need to get paid. Then if he hangs up, it’s not going to bother you.” Some guys do hang up. Well, I’ve got to tell you, a lot of times after a call, I finish it. 

Ms. Cassidy: I am picturing all the dudes in the Literotica chat asking, “Where did the fucking hot woman go?” They’re still out there somewhere.

Ms. Olivia: Hopefully, they have found us here. If I talked to you on Literotica and you want to contact me again:

Olivia@enchantrixempire.com / @MistressOlivia1

My blog:  Experienced Mistress.

Ms. Erika:  erika@enchantrixempire.com / @ErikaEnchantrix

Ms Erika’s blog:  Intelligent Phone Fantasy.

Ms. Olivia: And Cassidy, you’re taking calls this month. Yay!. 

Ms. Cassidy: I am. And even if I’m not, you can always contact me. I always do appointments. So you can always email me Cassidy@EnchantrixEmpire.com.

If you want to check out my blog, it is FirstClassPhoneSex.com. My Twitter is @EmpressCassidy. 

You can also find me on our Dispatch Twitter, which is @LDWDispatch.

I do most of the posting there and tend to interact just like I would interact in any other situation. Feel free to check us out there. 

Ms. Erika: That’s a great idea, Cassidy. I love the Dispatch Twitter posts. They are really fun and there are even interesting things. I encourage everybody listening to go ahead and follow them on Twitter as well. 

Magic Pussy

Ms. Olivia: Dispatch Paula, @PaulaPimptress on Twitter, posted that she had this guy who called in and he was like,

“What the fuck is Olivia still doing on a call? Get her off the call. I want to talk to her. I talked to her a long time yesterday and I had a great time get her off the call. She needs to talk to me.”

Paula, who has a great sense of humor, says, “Olivia has a magic pussy. You’ll just have to wait.”

I did a series of blog posts about Olivia’s magic pussy after @PaulaPimptress tweeted about Olivia’s magic pussy. Because he called back the next day and said,” I’m looking for the magic pussy.”. 

Ms. Cassidy: Oh my God. I have to give a huge shout out to Paula. She is amazing. And she’s amazing when you call into dispatch, she’s one of our dispatchers who has not done calls, but she is fun. She’s great on our Twitter, too.

Ms. Olivia: I keep trying to get her to do calls.”You need to do a call with me, you would be fantastic.” And she said, “No, no. I couldn’t possibly do that.” I say, “Oh, come on!”

Ms. Erika: She said she would just end up laughing. I said, “That’s what they want. Sometimes Paula, they want you to laugh.” 

Ms. Olivia: Exactly. Oh, exactly. 

So last year, because of COVID lockdown, there was a Worldwide Masturbation Session.

I’m going to research it and see if there’s going to be another Worldwide Masturbation Session. Maybe we should just have something like that here at LDW in honor of Masturbation May.

Ms. Erika: Fantastic, Ms. Olivia.

Ms. Cassidy:  We absolutely should!

Masturbation questions for listeners

Ms. Olivia: We always end the podcast with questions for our listeners. I want to know what is your favorite masturbation technique? And listen, if up-down-up-down is your favorite….

Ms. Erika: Expand your horizons. 

Ms. Olivia: Expand your horizons! Extra points if you’ve got something other than the typical up-down.

What questions do the two of you have? 

Ms. Erika: I want to know if you’ve ever engaged in mutual masturbation with a partner.

Ms. Cassidy: I want to know where the craziest place is where you have masturbated?

Ms. Olivia: I’ll answer that one. I took flying lessons and this was when I was a student pilot. I masturbated in the little Cessna. I’m not sure I should admit that.

Ms. Cassidy: Extra points if theirs is wilder than yours.

Ms. Olivia: I also gave my instructor a blow job while we were flying. He had the autopilot engaged.

Ms. Cassidy: Throttle up! Throttle up!

Ms. Olivia: Flaps down, baby. Flaps down.

We have come to the end of our conversation. Give yourself a hand. We’ve got a happy ending.

Ladies, it was awesome to be with both of you. Erika, it’s always fun. I love you to pieces and Cassidy, you have got to come back. You are a hoot! 

Ms. Cassidy: Thank you so much for inviting me. I had so much fun. I’d love to come back anytime. Just let me know. 

Ms. Olivia: Thank you to all of you for listening. Remember, move us up the charts! Subscribe, Like and leave a review wherever you listen to The Weekly Hot Spot. If you do this, we might let you cum. But …. maybe not. 

All 3 Mistresses: Yeah, no, no, no, no, no, no, no, no. Not going to happen. Not going to happen. 

Mistress Olivia: Don’t cum until next week when you join us again for The Weekly Hot Spot. Bye, guys.

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