Meet Katherine: A Boomer Sissy on Acting the Role, Cousin Fantasies and Sixty Years of Self-Discovery

Q – Do you remember your first orgasm while dressed?

Katherine – I was about 16. Summertime, left at my aunt’s house. She and my cousin her daughter were at a friend’s birthday party. Out of curiosity I started going through my cousin’s closet, trying on various things. After about an hour I felt it was a rather nice look on me. Next was the makeup challenge. I had hardly any experience and had a terrible time, but finally felt OK about my look.

I lay down on my aunt’s bed and started to daydream. Next thing, without really thinking, I started to pleasure myself. I can still remember that euphoric feeling. My cousin’s panties were full of cum. When I reached climax I suddenly realised I had maybe 20 minutes before my aunt and cousin came home. Luckily the clothes were still in excellent shape. I put them back, got in the shower to wash my face. I put the panties in my suitcase and wore them for many years, especially whenever we had holidays with my aunt’s family.

Q – And the first sexual contact while dressed?

Katherine – I went in drag to a gay bar and met a trans woman. We didn’t show any sexual attraction at first. Around our third drink she asked if I wanted to go outside while she had a cigarette. After she finished, she suggested we go to her car to listen to a cassette. Sitting there I felt the impulse to kiss her, and she was very much into it. I almost immediately knew I wanted to suck her cock. I started massaging her with my hands, then I was kissing her stomach, inching my way down. She was more than I’d hoped for. I gave her my best until she came. After, we went back inside. She hooked up with someone else and I never saw her again outside the bar.

Q – Talk to me about your favourite clothing.

Katherine – Actually it’s simple. I always wear women’s panties or cotton under shorts. My shirts are all bought in the women’s department. Same for slacks. That’s every day. I save the bolder pant suits and dresses for evening wear.

Q – Most vivid fantasy?

Katherine – I have well-developed breasts in this one, wearing a designer pant dress, low cut, with the inside of my boots well exposed. My makeup is fantastic, my hair a short, very upscale style. The fantasy takes me to my cousin (eleven years my senior). I imagine us having sex, him pegging me and me giving him a blow job.

Q – Most intense encounter while dressed?

Katherine – I love foreplay. Sometimes the appetisers are more rewarding and more creative than the main course. By the time we get there, we’re usually both naked and all the time and effort seems lost. How he or she felt never comes up. I do enough self-evaluation on my own time.

Q – Body swap with anyone for 24 hours?

Katherine – Super easy, because I’ve wished this for over 60 years. My cousin, eight years older than me. Ever since I was 12 I wished I was her. She has always been beautiful. One of the most intelligent people I know, with good ethics, an excellent sense of humour, doesn’t take herself too seriously, and has always had excellent taste in the arts. She knew me way before I did.

Q – And object of someone’s desire for 24 hours?

Katherine – I can’t think of anyone specific. Probably it would be a woman, not necessarily sexual, more in a servant role. When I crossdress I do feel I want to dominate men sexually. I don’t have a naturally feminine look even with the best makeup. I still look like a guy in makeup. I’ve thought about surgery seriously, but the cost is so high. If I could do it on a short-term basis, that would be the real fantasy.

Q – Evening dressing up with anyone, who?

Katherine – A straight open-minded man, or a trans girl who had it all down. I could learn a lot. Always learning from others’ experiences. I love sex, giving and receiving.

Q – Your generation didn’t have the support that exists now. Tell me about that.

Katherine – When I started dating and hadn’t fully realised I was gay, during my sophomore and junior years, three or four different girls told me I was different from other guys they’d dated. When I asked what they meant, they said not mean or rude, just different. I never acted sissy or gay. Back in 1966 and through the 70s I kept a pretty tight rein on myself. It wasn’t until my forties that I truly was myself.

Q – Advice to your younger femme self?

Katherine – Back then there wasn’t the support there is now. Where I grew up, being gay wasn’t encouraged in any way. So advice to younger me would be hard to give without changing the world around me. But: trust the feelings. They’re real.

Katherine, thank you. Sixty years of quietly knowing yourself, and the way you describe crossdressing as acting a role, becoming yourself from the inside out, that’s beautiful. You can find her on Instagram @Timkirby950. Gurls, drop your thoughts in the comments. And if you haven’t done the survey yet, get on it.

Jenny xx