Meet Andi: A Gen Z US Sissy on Leather and Lace, Chastity, and Neurodivergence

Andi is a Gen Z sissy from the US with an obsession with pink leather and lace, and a sizzlingly honest take on Chastity and Neurodivergence. Her answers to my Crossdresser Survey were vivid, brave and brilliantly honest, and I had to share them. What follows is her story, edited into a Q and A so you can read her in her own words.

Meet Andi

Q – Andi, tell us a bit about yourself and your girly side.

Andi – I enjoy her because of the feeling being her gives me. The feminity excites me, there is more sexual freedom and pleasure, submission feels more natural, and the clothes and lingerie are amazing and really excite me.

It helps me explore and open up more, especially sexually, where it feels correct and more expressive compared to “normal” life

Q – If we went out together tonight, all dolled up, what would the perfect evening look like?

Andi – Very few people know the girl inside me, so to explore that with someone, both on an intellectual/conversational level, as well as a deeper intimate level, would be wonderful

Q – Your style, what is it about your colours and fabrics that fires you up?

Andi – I chose pink because of its femininity. Wearing pink awakes my inner girl the most. Lace is nice for similar reasons. It’s feminine, dainty, and delicate.

Leather indulges in the power dynamic. When I think of leather on myself, I think of being bound and serving others. I also picture alphas and dominants in leather sets/outfits, and they have power I want to worship

Q – And your favourite fantasy clothing — paint us a picture.

Andi – I love lingerie and hosiery. The hidden, but very powerful sexual energy it has is addicting.

I also enjoy dresses. The flowy, free access is really nice. And short slips and mini dresses can get me wet.

Pair them all with clean shaven legs and some stockings/tights. Mwah. Chefs kiss

Crossdressing origins: early experiences and first sexual memories

Q – Do you remember your first orgasm while dressed as a girl?

Andi – My legs were weak for days. It was a feeling like no other. I have anally masturbated with a dildo while wearing lingerie and it was amazing.

Q – And the first time you had any sexual contact with someone while dressed?

Andi – I haven’t gone all the way while dressed as a girl with someone, but I did give a blowjob, though I couldn’t bring them to completion. It felt freeing being dressed a girl and then accepting and welcoming that. And it felt really good to kneel down in front of them, submissive to them, and suck their cock for their pleasure (although submitting and blowing them gave me mental pleasure too). I know I will be making my way to full on sex as a girl.

Out in the world: Andi’s public dressing

Q – Do you crossdress in public? Do you wish you could, more often?

Andi – Once or twice

Q – Tell us about your most intense encounter while dressed.

Andi – Blowjob, no full intercourse yet. It was really nice and surprisingly comfortable.

They were nice about it and had a tasty cock, though I did not get a creamy reward.

Q – Shopping. Does going clothes shopping with another girl excite you?

Andi – Get you excited

Andi’s fantasies: body swaps, deepest desires and dress-up dreams

Q – Your most vivid or exciting crossdressing fantasy?

Andi – I fantasize about meeting a dominant woman who can instantly see the inner girl inside me. She sees I am submissive and just need a push. We hit it off and maybe even have some fun as a hetero pair.

But as we undress, she notices my shaved legs and body. We make out a bit but the power dynamic is clear. She is driving this encounter. Her hands on my chest and neck, her legs brushing mine. My hands are to the side; I’m too nervous to touch her.

She guides her hands to her breasts and squeezes them for me. Then she pushes me down on the bed. With her on top and in control she confronts me about the shaved body. She can see through my stutters and lies and tells me, not asks, that I am a sissy.

She ties me to her bed and tells me she’ll prove it. She leaves for a minute and comes back with a nice sized strap on and a leather harness that accentuates her features. My cock twitches excitedly.

She oils me up then stares into my eyes. We hold the gaze until I bit me lower lip, nod, and whimper “please, fuck me mommy”. She slides her body up mine until she is at my ear then whispers “that’s my good girl”. My whole body twitches and my clitty leakes precum.

She retreats, put her legs on my shoulders, and spreads me open. I moan and whisper like a good girl. She continues to fuck me, twist me nipples, and call me a good girl until I am beyond spent. She did not once touch my clitty.

When finished, she asks “what are you?” and I reply “your good girl”. She smiles, unties me, then we get clean in her shower together. She then cages my clit, gives me a thong and slip and tucks me into bed. I don’t resist. I am a good girl after all.

Come morning, there is no trace of masculinity, just what my body needs time to change. She gives me a flowy, midi skirt. And we go out shopping. I am nervous, but her sternness and being by her side was it all away. We buy new clothes and lingerie, being very direct with the sales lady this is for me. We continue life as girls.

She has been feeding me hormones until we go out and meet a guy. We chat and he takes us back to his room. Once inside he gets right to work, dropping his pants. I instantly drop to my knees. This is my first real cock, but I have been trained well.

My mistress forces my head down and I work his cock like a good girl. He then lifts me up and bends me over the bed. He lifts up my dress and sticks his cock right through my crotchless panties into my sissy pussy. He fucks me good. I feel him tense, push back on him to take him deeper.

I look over to my mistress sitting down. She winks, than says “good girl”. He then twitches one last time and breeds me deep.

Q – If you could body swap with anyone in the world for 24 hours, who and why?

Andi – I would do like a model/pornstar. Maybe someone like Naomi Swann.

We do a nice, girly photoshoot. Beautiful dresses and heels. It slowly becomes a lingerie shoot, and I strip to the lingerie below.

It then become a porn shoot, as the guy behind the camera come out and fucks me and I have sexy as a woman.

Q – And if a fairy godmother made you the object of someone’s deepest desire for 24 hours?

Andi – I would rather have the inverse, where I serve someone else. They would provide me clothes, shoes, lingerie, and all things girly and sexy. And I would show them otherworldly appreciation.

Q – If you could spend an evening playfully dressing up with anyone, who would it be?

Andi – A genetic girl When I crossdress I am the girl. No boy bits allowed. It drives the fantasy deeper and makes it more real.

Neurodivergence and crossdressing: is there a connection?

Q – Have you been diagnosed with (or do you suspect) anything in the neurodivergent family? I’ve wondered whether there’s a higher incidence in crossdressers — your thoughts?

Andi – ADHD. I would say having ADHD allows us to think about the benefits of crossdressing more freely.

Q – If you could go back in time and offer your younger femme self some advice, what would it be?

Andi – Don’t be afraid to embrace it. You can still take your time, but don’t be scared.

Thank you so much for taking the time, Andi. Honesty is everything to me, and you delivered it in spades.

You can find her at @tubberwarecalculator – instagram.

If reading this stirred anything for you, gurls, you know what to do. Drop your thoughts in the comments. And if you haven’t filled out the survey yet, what are you waiting for?

Jenny xx