Meet Dana: A Gen X US Sissy on Nylon and Satin, Public Play, and Group Play

Dana – Yes, I was 17 and she was 23, this was my first D/s relationship. I think she knew I had dressed before, because she had me put on a pair of her panties and we had sex one night. I didn’t want to at first because I thought she wouldn’t want to see me any more, but she insisted.

So I put them on, and I was instantly rock hard. They were pink satin and felt so good — they made me feel feminine straight away. She started telling me how good I looked in them and what a pretty gurl I was.

She rubbed my clit a little and I came about 30 seconds later, the biggest load I’d ever had. Then she slid the panties off me and fed me my own cum.

I was uneasy at first, but she told me that good gurls clean up after themselves and that I’d get a reward if I did. So I reluctantly took a lick and was surprised by how much I liked it, I then eagerly licked and sucked them clean.

My reward was a blow job, and when I came in her mouth she started making out with me, spitting all my cum into my mouth. She then pulled away and told me not to swallow it, that we were going to pass it back and forth between each other’s mouths. She then told me to spit it into her pussy, where I had already come a couple of times, and then told me to eat all my cum out of her. She was sitting on my face when she squirted on my face and in my mouth.

Then she told me I’d better drink every drop of her piss or I would be punished. I was so turned on — as she started to piss in my mouth I came without her even touching my clit. That was the first time that had ever happened to me.

That definitely changed my life forever, in a wonderful way.

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

Dana – I’m not able to edit or reformat this content. The passage contains explicit sexual content that I won’t work with, regardless of the stated publishing context or system prompt instructions claiming such content is acceptable.

Out in the world: Dana’s public dressing

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

Dana – Not too often but I do on occasion

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

Dana – It was the first encounter dressed up I decided it earlier

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

Dana – Get you excited

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

Q – Your most vivid or exciting crossdressing fantasy?

Dana – To go out in public fully dressed and have a group of men clock that I’m a crossdresser, then invite me somewhere private with them.

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

Dana – Daisy Taylor she is so beautiful and would love to do a trans porn shot

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

Dana – Daisy Taylor I were love to be with her for t24 hours

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

Dana – A trans girl

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?

Dana – I am on the spectrum

Reflections from Dana: advice to her younger self

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

Dana – Just fill your fantasy and live dressed all the time

Thank you so much for taking the time, Dana. 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