The very first time I put a loved one into panties and a matching bra, and watched the way their face lit up from within, I was hooked. Holy shit y’all, it turns out that helping people find joy, bliss, and ecstasy in their gender presentation is hot as hell! So now, every time I help someone else explore a little lingerie, or a dress, or the perfect pair of shoes, and it makes them giggle and maybe get turned on? I fucking love it. So let’s talk about first time feminization basics for everyone, so you can get a head start on exploring yourself and your gender.
First Time Feminization
For those who have never explored their gender presentation in any way before, I recommend doing a little surfing on the internet first. Go look at some images of fashion and lingerie, and see what appeals to you! The sorts of things you find most appealing on other people’s bodies is likely to be the sorts of things you’d like to see on YOUR body. If you’re into knee socks, grab some for yourself and give it a try! Maybe sexy lingerie and panties in specific colors and cuts are your cup of tea. Give yourself the gift of something silky and sexy and try it on. You may like it.
Shopping For Sissies
If you’re worried about going out and shopping in the real world for sexy things for yourself, I’d suggest the internet and shopping online instead. From the safety and comfort of your own home you can browse all sorts of fun and sexy offerings and have them delivered directly to you. And most online retailers offer returns, so if something doesn’t fit, you aren’t stuck with it. If you want to try on panties in a store, you can, just wear something form fitting under the potential undies, so that they don’t come into direct cloth to genital contact. Same goes for other items that may touch between your legs, like bodysuits or unitards.
Got Boner?
Do not worry if you try on something femme and sexy and wind up with an erection!
A lot of folks try on something gender affirming and fun and wind up with a very confused boner in the fitting room. This is so common, it even got misdiagnosed and used by TERFs to try to invalidate people’s experiences! For a while, getting aroused when trying on new clothing of a gender presentation other than the one society says you’re “supposed” to wear was considered a perversion or fetish, and a sign that a person wasn’t serious about their gender exploration. For trans women who became erect when wearing a dress, this can make them think they just have a fetish for femme clothes, and can bring up a lot of shame and guilt. The term for this experience was autogynephilia, and was the medicalized term used to discriminate against gender non-conforming persons. Now we just call it gender euphoria and accept that sometimes feeling good makes penises stand up.
Feminization Leads to Trans Identity?!!!
Just because you put on a pair of panties and get turned on does not mean you’re a trans woman. That’s a journey you need to take for yourself, as you further explore your gender presentation and gender identity. We do not crack eggs around here! If it turns out that your first time feminization leads you to a lifetime of exploration and euphoria, great, but it’s also ok if you put on panties and decide it’s fun but not for you. Oh, and if you put on panties and get turned on? No need to waste a perfectly good boner, you can absolutely masturbate in panties and enjoy the sexy fun feelings. Sometimes a cigar is just a cigar, and panties are just fun. No need for a full identity crisis here!
Ready To Explore?
If you’re ready to explore your gender presentation (and identity?!), you know you can give me a call and ask for some help. From how to figure out what size bra you need, to sites that offer clothing in sizes appropriate for most adult male bodies, I know a few things that can help you, and I have feminization tips for you. I can also talk you through what to do with that panty inspired boner!
Don’t forget that the entire month of November you can add five minutes for free to any paid session with me, because I’m the Mistress of the Month for November 2024. I’ll be available all day on Thanksgiving and Black Friday, so if you need a break from the holiday shenanigans, give me a call for a quickie!
Your First Time Feminization Mistress, Harper
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That’s the physical reaction I had when I was young and first played (secretly) with my redacted’s lipsticks.
The gender euphoria will get you! and when it hits, it’s so good. ❤️❤️❤️
Every time I tried on some seductive lingerie for the first time there was that reaction. After wearing it for a long time it was not the same because I got used to it, but it always gives me immense pleasure. I remember when my wife bought me my first satin nightie, how pleased she was to see how hard it made me. And actually, she’s happy about it even now 🙂😊 Thanks for the nice read!
I love to see that sort of a reaction to lingerie from folks! It’s always so hot to me
bra&panties were my first gender presentation my pleated skirt always keeps me on my journey
I love that you’ve got your pleated skirt as a friend to keep you company! and now you also have the Ladies of the Empire too!
I have never gone down the road of a feminization lifestyle but I am definitely a confirmed panty boy beta and, as you know Mistress Harper, I’m always in slinky panties or a pair of pantyhose when I call for LDW SPH therapy.
I absolutely love the feel of slinky material on my little cockette.
Besides, it’s so small that it just feels wrong in men’s underwear and I really can’t get turned on unless I’m in something humiliating.
And perhaps that’s where it’s different for me? I can see that feminization isn’t necessarily about humiliation, whereas cross-dressing is definitely about humiliation for me.
I think for this situation, thinking of the humiliation fetish and the love of femme clothes/crossdressing/feminization as completely separate things is probably best, at least for you. Erotic humiliation, to me, shouldn’t be mixed with the process of becoming more female, because being femme isn’t an embarrassing or humiliating thing. I know, some males find the idea of being feminized humiliating, because they’re stuck thinking that being masculine is “better”, and that becoming more femme is a reduction, or lessening of their status. Silly creatures, becoming more femme is a privilege and joy! lol
Thank you for such an insightful reply, Mistress Harper. This makes so much sense and I will remember to focus the humiliation on my small penis and celebrate my cross-dressing and dildo sucking as my emancipation.
It is a privilege to be an LDW beta and express my true sexuality!
I am humbled and honored that you allow me to engage in conversations with you.
Hi Mistress Harper. Haven’t commented on a your blog for a bit but must ask, was it your loved one’s very first time in a bra and panties? I only ask because if others are like me, my first time was alone and in the secrecy of the laundry in the basement. The knowledge of what I was doing seemed so wrong, yet the thrill of doing something so taboo was irresistible.
Yes, during the initial years of my donning dresses and stepping into silk had a masturbatory purpose, leading to immediate shame (and clumsy cleanup which no doubt, led to suspicions)
Perhaps if these initial forays hadn’t happened in a previous century but in a more accepting era, my pangs of guilt would be less whenever I purchase another blouse or skirt or cute heels. My activities no longer have the original end goal. Of course I won’t stop, but I want to thank you for such a wonderful and informative and empowering blog post. It is right for me to escape and express my feminine side when I do get the rare occasion. What is more right…I am accepted here.
It was their very first time! They’d been curious, and asked me if I’d help them explore their desires.
And yes, it’s much more accepted now, over the way it was in the past. I’m glad for that, because really there shouldn’t be anything to be ashamed of in trying something new.
a female friend I had a total crush on made me do it the first time. I cannot totally explain “made me” – but it felt like I had to – I was curious but did not want to – she made me feel like I needed to do it to have her content about me (let me hang around with her) – it really felt that “simple” – like if I failed (to amuse her) then – I would be banished in some way. She was also one of the first girls I knew who spoke very openly about her preference for endowed guys (strong preference) – all that went into my feeling I had to do what she told me. I will never forget the “frozen feeling” when she go things out of her dresser drawer. I literally “froze” and when I did she began it for me as though I was a total redacted. It was not like I “agreed” or “disagreed” – I just froze and she decided. The whole thing caught me off guard and changed her with me basically forever – I could tell she was far more automatic in telling me what to do after that (and she already had been in charge). We were “just friends” but she made me a kind of “girlfriend”.
I’m glad you had someone to experience that with! It’s so much more fun with someone to help guide you.