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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.

Martha

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

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

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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