I Took A Huge Step Today

So I have lately been struggling keeping this whole crossdressing/gender issue thing a secret, it’s eating me alive. I feel I needed to talk to someone about it. So I decided to think outside the box and talk to my boss.

For context, I’m a lifeguard. I work at a gym. My boss is great, only like a few years older than myself. I thought she would be the perfect person to talk to.

I was very uneasy and often had to take deep breaths just to get the words out of my mouth. Eventually I just sucked it up and I told her that “I’ve been having gender issues” she seemed unfazed. She reassured me that everything was alright. As we were talking she asked me what I liked to wear, my favorite style etc. I told her I loved skirts and dresses and she again seemed unfazed. She was support supportive and that alone made me happy, she said if I needed her, to contact her. But, it gets better.

I decided to take the gamble and I decided to ask my boss if I can potentially dress at work. She said absolutely. None of this feels real. I can’t believe I managed to gather the strength to do this. I’m just so happy I almost burst into tears and hugged her. Obviously I have to wear what the female lifeguards wear if I choose to come in dressed. So that means I have to wear the usual unisex shirt with leggings or shorts, my boss even suggested I wear a bathing suit underneath in case I ever had to make a rescue. Not only did she give me the okay to dress femininely at work, but she also complimented my eyelashes which I thought was funny, she said “girls would kill to have eyelashes like yours.” She also proceeded to tell me the CEO of the place I work at is a lesbian herself. So that means that I know I’ll be okay. My boss said if I decide to change my attire, she’d back me up 100%.

Theres also usually a water aerobics class that lasts a few hours and I told the teacher of the class of my idea to change to feminine attire. She was also extremely supportive and told me her daughter was a lesbian too. The amount of support I got from both my boss and coworker were incredible. I remember shaking and feeling extremely uneasy during both exchanges. But both couldn’t have gone better.

I have already ordered two pairs of leggings, shorts, and two bathing suits. I’m just stunned at the support I got today. I still feel so overjoyed and happy. Well, guess it’s time to give it a shot!