Meet Melissa Jones: A Millennial Australian Crossdresser on Nylon and Lycra and Mistress Worship

Melissa is a Millennial crossdresser from Australia with an obsession with pink nylon and lycra, and a sizzling take on Mistress Worship, dressing, sex, and identity. 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.

Q – Tell us about your dressing up.

Melissa – The thrill of dressing up turns me on so much in a strange way. I don’t get an erection I just feel an unstoppable horniness. The feel on the skin, the feeling of those materials rubbing against a lover wearing the same. I love tight corsets, hip pads, breast forms, then pantyhose and a tight gaff to tuck my sissy clit and balls away, usually with an easy to move g-string back and some carefully removed stitches in the pantyhose. That gives me a foundation to build any outfit.

Sometimes it’s a leotard and tights. Other times is a maid or schoolgirl outfit.

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

Melissa – I used to dress up in dresses pre puberty. I would climb into clothes recycling bins and pick out any sexy women’s clothes. One time I found a vibrator and took that home and washed it.

That time I’d also found a pink one piece swimsuit. With new batteries in the vibrator I tickled my cock but found myself tickling my perinium. As it got closer to my ass I felt so excited.

I put some moisturiser on it and slid it under the Lycra, pressing it against my anus. As soon as I slid it a little bit inside I began consulting with my first ever orgasm. I collapsed on the floor unaware of what had happened.

My first 50 or so orgasms were dildo induced with a flaccid cock. Then eventually I got my first erection and learnt to masturbate with that.

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

Melissa – I tried to bring it up with a few long term girlfriends but was clearly dating the wrong kind of woman.

I asked one girlfriend if she minded if I got a full body wax and she got me one for a birthday. I then got sent to the other side of the country for work for a few months. After finding an apartment I left my luggage there one weekend, flew home, packed all my girl stuff in another suitcase and took it back. I stated wearing my corset at all times outside of work and gradually trimmed my eyebrows back.

After pleasuring myself multiple times a night I was so horny that I looked up dominatrixes in the area. Chatting to one she told me she was away for the month but suggested I try trans women. The idea scared and excited me. I bought a new SIM, withdrew $1000 in cash, and began texting.

I soon had what looked like a beautiful trans woman lined up that evening at 10pm.

I got back from work, moisturised my whole body, douched my ass, showered, spent a couple of hours doing my make up, then put on my favourite maids outfit with panties with the back open. I then used a bunch of lube and my favourite toys to loosen my ass up.

Petrified when I heard a knock at the door I timidly opened it. A beautiful Asian woman was there and she came in. I paid her $300 to get it out of the way. She seemed genuinely impressed with my make up and did a quick lap around me. She slid a finger between my cheeks.

“I’m guessing you’re a bottom then.” She said.

I just nodded, too shy to speak.

She led my to the bedroom and sat on the bed.

“Kneel down here” she said lifting her skirt and showing her bulging panties.

She gently guided my hand onto her panties and I could feel her cock underneath. I’d never touched another cock in my life. She slid my hand in the top of her panties so I was holding her cock as she lowered them. She then stopped and stepped forward so that her cock was touching my lips. I opened my mouth and her semi hard cock slipped in. I remembered reading about giving head so was careful not to use teeth and make use of my tongue. Soon I had a hard cock sliding in and out of my mouth.

She then put on a condom and got me on the bed on my back with my knees up, and slid herself inside me. It felt amazing and I tried to hold on, but the thought of an actual cock inside me cause me to cum in a few minutes. Thankfully she kept fucking me and I lasted another ten minutes or so before cumming again.

She then pulled out and went to take a call in the next room, leaving me lying there wrecked with my panties full of cum.

I soon called her a cab and she left.

Q – Your most vivid or exciting crossdressing fantasy?

Melissa – I’m a tall, muscly guy, so being feminine takes a lot of work and isn’t very passable, but I do look quite feminine in shape and appearance, just not size.

My ultimate fantasy is an ongoing relationship with a tall dominant trans woman.

I often fantasise about her sitting on a couch with me on all fours next to her, sucking her dick as she begins fingering my ass. She then takes me a makes me face a wall as she comes up behind me and slides into me, pressing me against the wall. She fucks me hard and I cannot move anywhere. She’s kissing my ear and neck and whispering encouragement about what a good slut I am. Just as I’m about to cum I hear her moaning and feel her shooting cum into my ass as I fill my panties.

After this initiation she begins training me as a pornstar. She teaches me how to make eye contact while deep throating her cock, teaches me to be more confident and ride her cock while she lies back and relaxes, and teaches me to arch my back when cumming and lift my skirt to show my panties filling.

Then, on my birthday, she comes home with a trans friend. She asks me to show her how well I can suck her friend’s dick. I kneel down and begin rubbing her panties before taking it in my mouth, looking up at her as I take her growing cock deeper and deeper into my mouth.

She then sits down so I go on all fours and keep sucking, while my mistress slides her cock into my ass.

As my mistress and I begin cumming, so does her friend, who grabs the back of my head and forces her cock right down my throat. Unable to get the cum out of my mouth it spurts out my nose.

I then collapse, exhausted, with my panties full of my cum, cum dribbling from my ass, and cum dribbling out my nose.

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

Melissa – I would swap with a trans porn star who does lots of trans lesbian porn and have as much sex with other trans women as I could.

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

Melissa – I would become the sissy toy for a group of beautiful trans women and have them fuck me over and over again.

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

Melissa – A trans girl There are so many beautiful trans women, I couldn’t pick one!

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

Melissa – Come out sooner. Find the right person to share it with.

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

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