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Milestones: Love’s Young Dream

Here’s another painful milestone in my castration fetish.

It should come as no surprise that I’ve never had much luck with girls. The bitter irony is that I was an unusually attractive young man, although I was never that conscious of it. In my early 20s girls were literally throwing themselves at me but I just couldn’t respond.


One day when I was almost 16 I was walking home from school when I was stunned and totally blown away by the heavenly vision of a tall, stately girl my own age with long blonde hair walking majestically a few yards ahead of me. Unfortunately, she never wanted anything to do with me. I became obsessed, similar to a stalker. Her face was what you’d call handsome. She was androgynous like Jamie Lee Curtis in the first “Halloween” movie. Jamie Lee has also been rumored to be intersexed.


Debbie had a similar tall, androgynous build as Martha but was more feminine. We dated for a couple months when I was 16-17. She was my first real girlfriend. She gave me the opportunity for my first intimate grope during a screening of the movie “Performance”. I was disappointed how flat her chest was and that her outer genitals felt squishy.

She was from a big city and was staying with her cousin in our small town for a year. She turned me on to a lot of hippie culture that was so popular at the time.

“Performance” is a crazy, fucked up movie, by the way. Awesome and beautiful.


Julie was my first sexual experience. She was a casual acquaintance of my, not-yet-out, lesbian cousin from a big city who came, along with her mom and sister, to visit for a week every summer. I was 17.

Julie came on to me and I jumped at the chance. She apologized for not being ‘fresh’ the first time since she hadn’t showered for a few days.

She was definitely the most attractive girl out of the handful that I’ve had sex with. She had a really sweet, nubile body. Her skin was a little rough, though.

She wanted to continue the relationship after she went back to the big city but I rudely scorned her. I was an immature, momma’s-boy asshole. I was truly beastly to the poor little bitch.

Decades later I found out from my cousin that my mother had angrily lambasted her for corrupting her sweet little angel boy.

Pot Zombie

At this point I started dropping acid, drinking beer and smoking pot. But the acid trips were pretty painful so I gave them up pretty quickly.

Adolescence was just too painful and I thought I was being ‘hip’, so I let myself sink into becoming a ‘pot zombie’ for the next several years.

Still managed to squeeze in a couple more girlfriends before meeting my wife-to-be at 23.

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