I am Mistress Holland. Send Me the weak, the wealthy, the closeted, the sissies, and admirers of all genders. With over 10 years of experience as a professional TRANS GODDESS, I cater to cock craving kinksters, sissies, and fetishists, I understand what makes you tick and I love digging into your mind to extract the fantasies that have been driving you wild.
My devotees adore Me. They either want to worship, serve, or in many cases, they want to be Me. Which type of devotee are you? I look forward to using you soon.
slaveboysmith: Today at DommeAddiction finds this slaveboy on his knees once again before the beautiful and sensual Mistress Holland of Chicago. I say again, Mistress, because we have previously spoken on NiteFlirt and I am well aware of your power as a Dominatrix! Welcome to DA and thank you for this audience today.
Mistress Holland: Thank you and thanks for revealing that we’ve talked before. I was unaware of that until your confession. You can send me details after the interview.
sbs: Yes Mistress, of course. Your calls are amazing and you are perfect at digging into those fantasies many of us supposedly straight men try hard to suppress. For those who have not yet experienced a session with you, how would you describe your style as a Domme?
MH: For me, it’s all about connection and gaining trust. The psychological aspects of kink in BDSM are far more important and interesting to me than the physical.
Sometimes it starts as a conversation but it can quickly become an interrogation without them realizing it. From there, I use their answers and confessions against them to fill in the missing gaps. I usually hit the right path leaving them coming back for more.
That is how I approach a Typical cam or call session. For in person, I am starting to shift towards more feminization. Those are the kind of submissives that I want to attract. I want to provide a glamorous aesthetic while breaking them down emotionally. I want them to reveal the side of themselves that no one else sees.
sbs: The slaves that see you, or like I have, call you, are most exploring fantasies they struggle with trying to repress? And as a Trans Domme, are you the perfect person to guide that journey, perhaps even forcing it a little Mistress Holland?
MH: Some are trying to repress it. They have secrets to keep from family, girlfriends, wives, friends, etc.. I find those that repress it, tend to come back repeatedly, but not before deleting their account.
Some are ashamed and embarrassed about their desires, which often revolve around sucking cock or getting fucked. I think it’s healthy to admit that out loud as it gives me a chance to help poke holes in their belief system. For example, asking a question such as “why are you ashamed of wanting to suck cock?” will get them to open up and reveal themselves. I can take that info and continue to break them down until I’m ready to build them up.
I’ve been doing this since 2008 and I found that people aren’t as ashamed as they used to be and people are far more open today.
sbs: Your role sounds like part Dominatrix and part counselor, Mistress. I can relate to the secrecy and some shame, though I’m working on it. Are many of the man who submit to you married?
MH: Yes. The majority are married or or are in some type of relationship and no, their wives rarely know about their husbands sexual appetite.
sbs: Whether in person, or online, are there particular fetishes you enjoy most Mistress Holland, and what are some of the traits of your “ideal” submissive?
MH: The fetishes that I enjoy the most, are feminization or transformation sessions. Sploshing sessions are a lot of fun but too rare for my taste. I’m partial to leg and foot worship as well.
My favorite type of roleplay is therapist/patient but since so few request that, I tend to incorporate it into my calls.
I appreciate submissives that understand basic power exchange dynamics. Some think they’re submissive but they’re bottoms. I’m happy to play with bottoms but they are not exactly the same. I also value those that listen and pay attention to details. Lastly, loyalty will get you far with me. Actions over words every time.
sbs: You’ve produced some seriously hot clips as well. In looking through your store I couldn’t help but be drawn to your clip “Gay Whispers”. What can you share about this hot clip and why everyone reading this should be buying it right now?
MH: Thank you. I look forward to hearing which ones you’ve purchased lol. First off, “Gay Whispers” at least the vocal delivery was inspired by Goddexx Daphne. We both make a lot of encouraged or “forced” bi clips. I’ve created a handful of clips in this style but in this one, I’m specifically referring to gay sex. Man on man. Down and dirty but with a soft, sensual, whispery voice.
I understand that there is complexity surrounding trans attraction. I see it as it’s own type of attraction. Personally, I love watching men fuck especially if at least one of them is straight. Enthusiasm can be fun, don’t get me wrong. What excites me is the fear and trepidation in someone’s eyes along with their willingness to overcome it to indulge in their fantasies. To see them overcome that fear, with my encouragement of course, can be super fucking hot. This clip stemmed from this mindset.
sbs: I think there are a lot of men reading this who might find themselves willing to do things they would normally not, under the watchful eye and encouragement of a beautiful Mistress. Have you had the opportunity to orchestrate two men as you describe Mistress?
MH: To an extent, yes but based on the way most of these guys sucked cock, it seems like they were downplaying their experience.
sbs: Do you allow your slaves the privilege of such an experience if they earn it with you Mistress? And if so, is it more exciting to have a nervous newbie exploring their desires, or an experienced cocksucker pleasing Mistress properly?
MH: Whether it’s a newbie or an experienced cock slut is irrelevant. My pleasure has nothing to do with getting my cock sucked. Hungry mouths are in abundance. This comes back to power exchange. This is why I do what I do. The power over others to help guide them down the path they wish to explore.
sbs: Power is intoxicating. Can you describe how it feels to hold such control and to lead men deeper into their deepest fantasies as you do?
MH: Intoxicating is an appropriate word for it but everything in moderation to stay grounded. I enjoy seeing my submissives grow. It doesn’t happen with everyone but seeing my sluts remove their self imposed chains is a joy to watch. There’s too much stigma around men’s sexuality when they stray from the norm. If I can help liberate a few along the way, it’s worth it.
sbs: Absolutely there is, and well stated Mistress. Speaking of power, if you could choose one celebrity, or well known person to explore fantasies with, to have kneeling before you, who might you choose and why?
MH: This is tough because two names came to mind. Since I adhere to the rules, I’d choose Ryan Gosling because he’s handsome, funny, charming and I love to incorporate humor into scenes. His performance in Only God Forgives reminded me of so many subs over my career. Breaking down that type of exterior can be a challenge. Nicolas Winding Refn and Gosling seemed to get this type of submissive man.
sbs: I imagine you would have fun with anyone you had before you. For those slaves dreaming of submitting to you, exploring their fantasies with you at the helm, what advice might you offer as they plan to make the best possible first impression on Mistress?
MH: That it’s OK to be nervous. Exploring “taboo” sexuality can be difficult at first but I find vulnerability to sexy and exciting. And most importantly, never call me “baby”.
sbs: It’s hard to imagine from where I kneel before you ever contemplating calling you by that name, Mistress Holland. Your power and beauty ensure nervousness and submission. With all that you have already experienced as a Dominatrix, both real time and online, what comes next for you? Anything on your Domme “bucket list” that you have yet to satiate?
MH: I want to continue to push myself creatively with my clips. I recently discarded many of my clips from 2020 as I was dissatisfied with them compared to my current clips. I shoot and edit everything myself while mostly working alone. I’d love to collaborate and shoot with other Dommes and clip artists. I’ll have that chance as early as November 2022 with some other talented Dommes and clip artists at Goddess Alexandra Snow’s Wicked Retreat.
I’d also like to improve my skills when it comes to styling and makeup for my crossdressing clients. Painting and dressing myself is one thing but it takes skill to transform others. There’s few places left like this in Chicago which is a shame. I’m in the process of determining where this type of session will take place though. Acquiring my own space is out of the question right now due to the real estate market but I have a place in mind. We will see if it comes to fruition. Keep your fingers crossed.
sbs: All of that is intriguing, sexy and something to eagerly anticipate, Mistress Holland. Thank you for the privilege of this interview. I hope I’ve been a good boy and asked you about anything Mistress wishes to talk about.
MH: Thanks slut. Now that we’re done, message me and let me know your screen name on NiteFlirt.
sbs: Yes Mistress…I will do that right away. Before I do, with your permission, may this slaveboy please ask one final question of you before crawling away and getting to that task?
MH: Yes you may.
sbs: Thank you Mistress Holland. If we were conducting this interview in person, me kneeling at your feet, nervously asking my questions, how might such an interview conclude?
MH: It would conclude with the coffee shop manager approaching you to ask you to get off your knees so you can sit in your chair as you’ve made numerous patrons uneasy and concerned.
