Cocksucking 104th EpisodeTWHS

The new design for the Sissy School site is the inspiration for this episode.Mistress Olivia and Ms Erika talk about all the LDW Group sites for the girly girls: crossdressers, sissies and trans women.Sissy SchoolSissyvilleSissy Style MagazineGet Girlie The ladies share questions from several sissies. Topics include:How to come to terms with your sissy desires, feminine side or crossdressing activities.How to avoid purging all your pretty feminine clothes.How to explore sissy desires.Ways to honor your feminine self when you need to dress in male clothes.How to handle things when your partner knows but doesn’t want to participate.How the Sissy Training Calendar can help you on your feminization journey.And, why it’s important to have support in your feminine journey.

14 Nov 202229min

Hurricane Ian slammed into Florida knocking Ms Erika off line for a bit during LockTober. The ladies decide to continue chastity during No Nut November.Mistress Olivia asks Ms Erika about her chastity pets. This leads to a conversation about the mental and emotional parts of chastity, including how a Chastity Keyholder decides how long someone will be locked up.What is a prostate orgasm and why does a Mistress do prostate milking for someone in long term chastity?Speaking of long term chastity, the ladies go from Locktober to No Nut November to Denial December … then, perhaps, Jerk Off January.We’re (maybe) joking about extended orgasm denial. The ladies talk seriously about expectations around chastity, concerns, and common questions.One reason why both Femdoms like chastity is for the behavior modification. It’s perfect for sissy training, enhancement of submission, and more.

7 Nov 202228min

Duchess Willow says, “Every year, at the Monster’s Ball, something supernatural happens to the guests.” Today, you get just a taste of a sexy, spooky story by Duchess Willow, the Ebony Femdom. What happens at the Monster’s Ball? Ohhhh just listen!Ms Erika and Ms Olivia talk with Duchess Willow about writing erotica. She’s been writing Ebony Femdom erotica for years and you will be surprised at the reason why she started exploring that creative side of herself. This leads to a conversation about writing and the ladies come up with a plan to publish erotica.Ms Willow is well known for her love of all things Giantess. Ms Olivia has an off the cuff idea to do a Christmas tree covered in tiny men - Ms Willow adds, “...and their tiny erections.” Sexy, smart and very fun - Ms Willow is one of our favorite guests. She has her own podcast on Anchor FM - you can find all her links on her blog: EbonyFemdomPhoneSex.com

31 Okt 202229min

What really makes Halloween fun for you? Is it the sexy, naughty costumes? The chance to be and look slutty in public? The candy? Something else?Mistress Olivia and Ms Erika have a special Halloween series of podcasts.First up, Miss Constance tells us about the blog train and what that means for you.Maybe you get a treat, or you might get tricked. The very lucky ones might get all that and more.Ms Brighton thrills with a spooky, sexy, and very sticky story. You’ll never read the words “drip, drip, drip” without thinking of this yummy tale.Miss Mandy has a transformation story where a lovely and shy trans girl has a BFF who pushes limits. Here's a hint, the skirt will be very, very short!The ladies all talk about storytelling, creativity, chocolate, and sex.

24 Okt 202245min

“You’re so smart, what’s a nice girl like you doing sex work?” We sometimes hear questions or comments like that so we decided to talk about it. What exactly is a ‘nice girl.’Is phone sex something ‘nice girls’ don’t do?Does a woman in the sex industry need “saving”?Mistress Erika and Ms Olivia talk about the importance of business acumen and professional skills for anyone doing Distance Domination.Why do these smart, successful, creative women choose to do phone sex?Is there a social expectation that women should provide sex or emotional labor for free in order for it to be appropriate or real?The ladies tackle the stigma of sex work, judgment, and much more in this episode about why 2 successful women choose to phone sex as a career and a calling.You also get real answers to questions about what we do:Do you work off a script?When do you think of someone as a regular caller?Funny, thoughtful and mostly irreverent - we’re glad enjoy our kinks and kindness.

17 Okt 202224min

Who pays for an online domination call just to be ignored?Meet the sissy that pays for an ignore call while the ladies talk about …. Whatever we want to talk about!Only kidding. (maybe)Erotic humiliation, control and mindfucking are some elite Femdom moves - the Ladies talk about BDSM and the joy of being the woman in charge.Mistress Olivia brings up the 30-day sissy training calendar. Ms Erika mentions the blow job training. Ignore slave sissy is busy sucking a dildo while the ladies discuss cock sucking, cum eating and why one pet will always think of his Mistress when he eats a pudding cup.Lots of talk about erotic humiliation, small penis humiliation, and embarassing tasks for the submissive to do.

10 Okt 202237min

Kay Marie is a self proclaimed suburban MILF. Mistress Erika and Ms Olivia get with Kay Marie to talk about her podcast, Happy Hour with Kay Marie. We all go off topic right from the start of this episode and Kay Marie says that’s the perfect way to showcase her podcast because it’s organic and just flows without a topic or outline.Her podcast is also a bit different in that she does her show live and interacts with her fans live in the Community Kink chat room.In this episode you’ll find out about Kay Marie’s style on a phone sex call, what calls she likes to do and calls she does not want to do.

3 Okt 202233min

Mistress Olivia and Ms Erika talk about podcasting, sex and random silliness with Mistress Hunter. What makes a sex podcast sexy?Why did Ms Hunter start a podcast called Sexy Story Time?Is it better to structure a podcast or do an organic, stream of consciousness podcast?This episode ranges from sexy to sweet to smart along with a dash of naughty.

26 Sep 202236min