Are you a sissy looking for guidance and support? I know everyone wins when a Mistress takes on your sissy training. There are several areas where feminization can be tricky or lonely on your own. First, it’s the basics of dressing en femme and looking your best. Then, what will happen once you’re looking hot? Finally, I’ll tell you why every submissive girl needs a Dominant woman in her life. Here are some resources to navigate your feminization experience.
Sissy training to look your best
Each sissy is different. I like helping you discover or refine your feminine look. There are all kinds of practical feminization tips on the kink podcast I do with Mistress Erika. It’s called The Weekly Hot Spot. I think you should start with these episodes:
Sissy has questions about nails, makeup and Femdom feminization advice.
Do you need breastforms? All about boobs for a sissy, crossdresser or transwoman.
Remember, if you’re worried about looking your best, you’re not alone, as you can hear in this episode that is in response to a sissy worried about her femme style. Mistress Fiona is the guest on that episode as we talk about self-image, gender, and societal expectations. While every Mistress will give advice about things like spring makeup tips for sissies, we do want you to be gentle with yourself and who you see in the mirror.
Looking good and feeling great—what’s next for a sissy?
When I meet a new sissy, I’ll ask about sex. Erotic pleasure is a huge part of life, and I want us all to be happy and fulfilled. What happens once you’re all dressed in your sexy best? Let’s talk about sex!
Should all sissies learn to masturbate like a woman?
I don’t require all my submissive playmates to suck cock. That’s a common worry for girly gurls who ask: Mistress, am I still a sissy if I don’t want to suck cock? The short answer is yes, you are still a sissy.
It is true, though, that many feminized males love to be told to suck cock or serve men as part of their sissy training. What I do with you depends on many things.
Remember, even though you are submissive, you still have a say in what goes on in your sissy training. (At least at the beginning of our BDSM journey, as we get to know one another and develop our connection.) If you’re unsure of your cock-sucking desires, take this sissy test and report your results.
Mistress takes control of your sissy training
I believe that every submissive needs a Dominant. You need to be controlled, and I like to control subs. It’s a symbiotic relationship where we both need one another to be fulfilled.
There are some submissives who can float around for (what those of us in the fetish scene call) pick up play. There’s nothing wrong with that, but I think there’s something special that happens when your Mistress really gets to know you, your life, and your circumstances.
Remember, your feminization takes place within your life. That is a life that includes all sorts of other activities and responsibilities. You probably need help keeping your femme life separate but still accessible. Don’t worry. There are ways to get that balance between all aspects of your life. Mistress can guide, support, and encourage you. There is more to sissy training than the porn types of depictions of the Mean Mistress ordering sissy to do stuff (although that can be very fun!).
Now, I have some questions for you.
- What fashion or style questions do you have?
- How do you express your sexuality when you are en femme?
- What role has a Femdom or Dominant Woman played in your feminization journey?
Leave a comment here, or simply give me a call. I can’t wait to get to know you even better.
Your Experienced Mistress,
Ms Olivia
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Hey Ms Olivia!!! Long time no chat/calls-lots going on but will get back into calling/dressing as a girl soon. Decided to do laser hair removal from neck down. OMG I’m soo girlish soft and it will be permanent. This will be better as I can wear bras/breast forms/and not have to worry about body hair. The slips/dresses/bras/panties will feel soo good!!! I’ve turned into a sissy girl forever now!!!! Hope all is well and will call you soon!!!
You ARE a sissy girl forever Carli – you’re our cream puff girl!
thank you . You made me enjoy being a sissy cock sucker
Ohhhhhhhhhhh tell me more!
You mean you didn’t enjoy being a sissy cock sucker before?
What????
Yes Olivia it’s confusing
If I could get a pussy that
is very compatible and lived with me full time and everything is totally cool l would have no dick desires. Dicks are ugly sometimes. But being without or just talking with you makes me want to suck cock for you and tell you about cocks I like and suck.My last sexual adventure on the beach I wore a tiny pink g string wig & bandanna was totally hairless .I strutted past a man playing with himself. I went up to him smiled and he smiled back I touched his dick . Pulled down my g string and I let him push his cock into me from the front pushing my clitty back inside my self . The first time I have been fkd in the front like a woman. I have diddled before and used a dildo in front before
and had orgasms. I had an orgasm with a mans dick in my front. After that I sucked him and he shot a load. But now my knee has arthritis and it’s too much of a walk to get to the beach area where the actions is. I lost my phone in the beginning of may till just a couple of weeks ago . So in stead of being an internet sissy faggot I was getting a lot of real sissy action at the beach. Until my knee made it impossible to get the dick the way I like it . So I am back on internet . The visuals are a turn on and for most masturbate to this but I prefer spontaneous jizz when arousal so I don’t masturbate. You are such a hottie .I would want to want you but if you wanted me to suck dick for you and I love telling you about dicks I suck.
Oh April, I’m so sorry to hear about your knee and health.
Boooooooo
And I know you’re a good sissy — you really DO need to suck dick for me!
grins
Oh yes Olivia I will suck dick for you. The men on the beach give me the most arousal . I don’t get turned on like George Michael doing the restroom sucking. But maybe I may go for a night crushing at the gay beach parking lot there is action there but at the moment I have a bad cold and my knee hurts which means I should get to nudist Resort hot tub but problem there is too expensive to get in as single man I want to go in as a couple pay her way and save $100. on grounds fee bring a date.I did this twice with women I had no interest in they got to suck as many dicks as they could while I sucked toes and ate pussy all is good just waiting for next opportunity
That’s true for a lots of swingers clubs — and other alt. sex clubs — single males pay WAY more or don’t get in at all.
It’s a lot of fun telling you I suck cocks.How ever I can’t get into the George Micheal thing and suck cock in men’s rooms or other places . Seeing dicks on g strings thongs or nude on the beach drives me to sucking COCK.And then telling you wow so hot
I love hearing about all your sissy cock sucking escapades!
I do have a cold and really don’t want to suck any dick but hearing that you love it when I suck dick is giving me some thoughts about sucking cock for you. Maybe tonight? At night at the gay beach men will sit on benches get into conversations some walk into the woods some get in cars. One time I seen a gang bang guys one guy could not cum while being sucked he was very large. So another guy fucked him in the ass and made him cum while I watched.During these type of episodes I don’t dress sissy . I have cross dressed at times down there but no more
I pretty much have my style. Formals formals and more formals. You decide how I express myself sexually as I am in chastity going to the academy and beginning to plan our wedding. You have played a major role for me to learn how to express myself as a woman.
xxxxxxxx
Yvonne
Actually Yvonne, you will HELP with the other ladies at the Feminization Academy – many don’t have a sense of their own personal style and you can encourage them to find what makes them feel really great and feminine. Now, they might not choose formal gowns and bridal wear and that’s okay. But I want them to feel as confident as you do in what they DO choose and you will be so important for that part of things!
In so interested in becoming a sissy!
Right now I just Crossdress and ride my dildos
Ohhhhhh Amanda, tell me more. Have you found the podcast I do with Ms. Erika? It’s called The Weekly Hot Spot and we have feminization and sissy training episodes about every other week. What questions do you have in terms of wanting to become a sissy? You might inspire a blog or audio or podcast episode.
Stay pretty m’dear!
God this is so beautifully and wisely written… I bow to you again Mistress Olivia.
It is wonderful to have my Mistress to serve and at the same time be guided in training for Sissy… I love the symbiosis of DS and how they complement each other…
Thank you also for saying that not everyone has to suck cock and can still be a sissy.
Love your article.
Thank you from the bottom of my heart….????
Have a wonderful time.
Casandra
Hi Casandra, thank you so much! There is some debate in the sissy community about a variety of things and sucking cock is one of those … I understand that sissy porn really emphasizes cock sucking, and that’s fun but definitely not a requirement.I want everyone to understand that no matter what they/you see in porn or on the internet, the reality is that people are individuals and lives are nuanced.
I have a question is it hard for a sissy to shave theie clit and ass areas. I am a beginner sissy here and need help
what a great question … Actually, that would be a great topic for the podcast I do with Ms Erika.
Are you a fan of The Weekly Hot Spot podcast? We have lots of feminization and sissy training topics and we’re always looking for more so THANK YOU for the suggestion.
I have a short blog post on sissy shaving tips that has some general advice — take a look and see if this helps get your started.
hello olivia i have been trying to find a true mistress that will properly train me in feminization and being submissive as well as humiliation. i have a little experience in bdsm and sadomachism from past experiences. my issue is the past aka mistresses ive had have been frauds or fake but i would like real true training and experience from you or someone you know and trust i hope to hear from you and are willing to help or give advice also i am wanting to do skype or video training and over phone as well
Hello there pet!
You’re at the right place.
And you are correct – just because someone ‘says’ she is a Femdom or feminization Mistress doesn’t mean she has skills and experience … I’m not going to call others frauds but I do know that there are various skill levels and it sounds like you are looking for someone with experience.
Is that right?
We should connect!
Good morning, I recently found the weekly hot spot podcast a few weeks ago and I fell in love with it. It was actually the inspiration I needed to wear my wife’s/Domme’s panties longer than a few minutes, I wore them all night and even went to work in them. Such a thrilling experience. I have since purchased my own set of 10 panties from VS which come in tomorrow, and I bought thigh high socks, a pleaded mini skirt, and leggings. First off I wanted to say thank you to you and Ms Erika for helping encourage me to explore this feminine side of me. As a beginner in all of this I’m curious on thoughts of shaving my body hair, I want to see that clean slick look when I wear female clothes but I’m nervous about how I would look after I get back in my regular clothes particularly the legs since I wear shorts every day, I don’t like the look when I’m in panties and I see lots of hair I want to feel and look sexy like someone could run their hand up my leg at any moment ????, is there a good balance between the two or a way to have both? I have considered going full latex cat suit but as a beginner I want to explore more before investing so much.
Thank you so much for your kind words about our podcast The Weekly Hot Spot.
Ms Erika and I do feminization and/or sissy training topics about every other week.
CONGRATULATIONS on your 10 new pairs of panties!
woo hoooooooo
How does it feel to have sexy panties?
Hmmmmm?
Okay, now to your question. You’re not alone with the issue of balance – ie how to balance feminine presenting and masculine presenting sides of yourself.
Here is one idea … look up flesh colored tights … those tend to be wayyyyy less expensive than something like a catsuit (you’re right about that).
Try that and then let me know how it goes … and other questions you have.
We’re got your back!
please mistress make me a good sissy
Are you READY to be a good sissy?
Hmmmmmm pet?
im such a loving sissy who loves to feel fem inside and out. I finally got up the nerve to confess to my sister. she is so supportive and I got the advise form all you great mistresses
You DID ????
Oh my Josie that is AWESOME …. I’m so glad your sister is supportive of you … that’s super important.
That takes a lot of courage to do that.
What inspired you to take the ‘plunge’ now?