Short story… or maybe not so short.

After reading the article by my friend Hannah titled “I Want to Be a Crossdresser,” a memory came rushing back. In her post, Hannah makes an excellent point:

“Forced crossdressing is so interesting to me. It’s not really being forced if you seek out someone to 'make' you do it”. Personally I think she is absolutely right.

Back in my college days, I dated a girl who was bi. For me it was great because in my mind, if things worked out and we eventually tied the knot, it would probably be easier for her to accept me whether I was presenting as a man or as a girl.

So one day, I decided to pitch her a "wild" idea. I looked at her and said, "I’ll give you one full day to do absolutely anything you want with me". Of course, my true, hidden intention was to bait her into "force” feminize me. I wasn't sure how she’d react to such an idea, so I kept the proposal intentionally vague, praying she would take the route I wanted. And wouldn't you know it? She took the bait.

The moment those words left my mouth, her face lit up with pure joy, like a little girl who had just been handed a brand new doll. After composing herself, she looked at me and asked if I was sure I meant "anything".

Suddenly, I felt a little nervous. This had the potential to go in a very different, non femme direction. "Yes", I replied nervously, "anything". I can't quite remember if I dropped a subtle hint to steer the situation, but she finally smiled and said something like, "Okay, I want to feminize you".

On the inside, I was screaming YES! YES! YES! Hallelujah!, on the outside, however, I was playing dumb. I honestly think I missed my calling as an actor because none of my internal excitement showed through. Instead, I pulled off a WTF face and gave her a bewildered, serious look.

But I played the part too well and it backfired. Seeing my shocked face, she immediately backed out and looking apologetic she said something like "If you don't want to, it’s totally fine! We can do something else". I quickly scrambled to save the situation and told her "No, no, it's okay, I told you that you could do whatever you wanted, and I’m sticking to my word".

A massive, ear to ear grin spread across her face, and she immediately got to work. My plan was to go all out, let her do my makeup, and then get all dressed up, probably even go out of her dorm room. We were very close in body shape, so there was a very good chance that she would have something I could fit onto. Unfortunately, my theatricality ruined everything.

When she finally finished the makeup and turned me towards the mirror, I saw the result. And instead of showing the genuine, awe I was feeling, I decided to overact again. I went for an exaggerated look of shock that turned out to be another huge mistake.

Seeing my reaction, she thought she had gone too far and decided to end the experience right then. Inside, I was banging my head against the wall. Why did I do that?! If she was clearly enjoying herself. But I don't know... I suppose I was just terrified of looking too eager. I was so desperate to hide how badly I wanted to be feminized that I ended up completely sabotaging my first opportunity ever.

She wiped the makeup off my face, and just like that, the magical experience was over. I told myself I’d give her some time and at a later moment propose the idea back and repeat the moment since I had “ruined it for her” yeah right, I had ruined it for myself. But shortly after, we broke up, and that was that. 

Over the years, I tried proposing the exact same "wild day" to subsequent girlfriends, but I never had the same luck again. Most of them just looked at me with utter confusion, wondering what kind of bizarre mind game I was trying to play on them, so I just drop it entirely.

Fast forward to a couple of years ago. I received an invitation to a high school reunion. Honestly, I had zero interest in going back to make small talk about careers, families and such. But then, a crazy thought formed in my mind, What if I go... but as Blanca?

I spent days analyzing how I could possibly pull it off. And the best plan I could come up with was to reach out to one of my old female classmates with whom I'm still in touch. I figured I could propose the idea as a "prank". I'd tell her, "Hey, help me get all dolled up so we can pull off this prank on everyone who hasn’t seen me in decades! We'll tell them I've been living as a woman this whole time!"

I figured most of them would just have a good time, we'd have a wild story to tell, but most importantly I would get to have my night out in the real world as my true self in a relatively safe environment.

Well, this will be very anticlimactic, but in the end, I didn't do it. My mind did what it does best, it flooded with pessimistic "what-ifs". What if it goes horribly wrong? What if my friend thinks I'm a complete weirdo for even suggesting this? It wasn't like I was known as a prankster back in high school, so the cover story felt flimsy. Once again, I let my fears win, and I stayed home.

that brings me back to what Hannah wrote: “Sometimes someone just wants someone to help them start”. I honestly don't know if I will ever find the courage to take that first step out of the front door all by myself. The idea of doing it under the "safety" of someone else’s idea whether as a prank, or a Halloween costume just makes that obstacle so much easier to overcome... I guess.

But until that “someone” comes along with a fun idea, or invites me to a costume party where I can finally let Blanca breathe in public, I will keep doing what I’ve always done, enjoying her beauty and her spirit in the absolute safety of my own home.