Diary entry for Aug 19 2023

As a closeted crossdressed truck driver, I've had a lot of fun. Yesterday was a lot more fun than I would have dreamed.

My day starts at 3:30 am as usual. I get up and make sure my chastity cage is straight and quickly shave what little wiskers I may have, then I get dressed. Nothing overly noticeable, a simple underwire bra with C-cup breast forms and panties under my work clothes. Today however I decided I wanted to wear lipstick. I have no idea why but I did. So I applied a simple red lipstick. Nothing too flashy or too noticeable. I left for work at 4 am. On the short drive to work, I thought I probably shouldn't have worn lipstick but Lisa, the woman in me, said to do it.

Five after four I arrived at work and performed my pre-trip. I started the truck and waited for it to air and warm up.

My co-workers arrive as I'm leaving the yard. I do three round trips a day for a total of just over 800 km a day. It takes me 10.5 to 11 hours.

It's usually dark outside when the loader loads my first load of gravel, then I scale my truck, trailer and load to make sure I'm legal weight. I get my scale ticket and head for the concrete plant.

The drive is kinda boring so I usually squeeze my fake breasts a few times just to get my imagination going. Dreaming up some scenario where I'm giving head or getting fucked somewhere a lot more public than most would.

Fast forward to the last trip of the day. By now I'm leaking in my panties and all I can think of is cock. It's usually hot so I'm sweating anyway but I'm sure it's more noticeable as a large wet spot is showing in my sweatpants.

After I dumped my last load I had to go inside and time-stamp my weight tickets. Even though it's an office, I never encounter anyone in there.

Yesterday that changed.

A woman saw me come in and asked me to come into her office.

She's a safety boss and wanted to make sure I was compliant.

I could see her eyes scanning me over. When she got to my chest, she stopped. She stared at my fake breasts for a bit more than a moment.

I cleared my throat and asked if there was a problem.

She quickly looked up at my face and was about to say something when I'm sure she saw the lipstick.

She smiles and sits back in her chair.

"Please close the door and have a seat if you don't mind", she says.

I did as she asked, thinking what was going on.

"I'd like to thank you for being compliant with all your PPE. And I would like to offer you some advice if it's not too personal".

"What's your name"? She asks as she looks down at the papers on her desk.

Hesitantly I say "Todd, and you are?"

"I'm Linda, I just have a few questions for you. Then you can go."

"Are you sure your name is Todd dressed like you are?" I mean you don't exactly present as a male right now, do you?"

I instantly blush as my mind knows I'm caught.

"No, I guess not. I'm Lisa." I responded.

She looked up with a huge smile saying, "It's very nice to meet you, Lisa. Tell me, why are you dressed like you are today?"

"Just for fun, I guess," I say nervously.

"You look like you could use some advice. Are you open to some advice Lisa?"

At this point, my mind was all over the place. Was she going to report me to my bosses? I didn't know.

"I'm open to any advice you can offer," I said.

She writes her name, phone number and address on a piece of paper and hands it to me.

"Be here at four pm on Saturdays from now on and I'm sure you won't regret it, and bring all Lisa's belongings with you," she says with a smile.

"Belongings?" I ask.

"Yes, you know. The secret stash of anything that belongs to Lisa!"

I look her in the eyes. She's unflinching.

"Oh come on now Lisa, I know all about girls like you and I love to help."

I just sat there looking at the paper she gave me thinking, do I really want this? I've been in the closet all my life. Lisa answered for me. "Of course, I'll be there."

"Linda's eyes lit up, there she is! I knew you were in there. So I'll see you at my place tomorrow then!"

I stood up and said thank you.

"Oh, just two more things. Please give me the keys now." Linda says in a seductive but demanding invoice."

I turned to her asking "Keys?"

She points to my crotch and smiles.

I don't know why but the next thing I know I'm handing her the keys to my chastity cage.

"Thank you and now I'd like to do a spot check if you don't mind."

I look at her again puzzled. "Spot check?"

She stood up and walked around her desk to me. Her face showed no emotion. She stood a mere inch or two from my face. I thought she was going to kiss me but instead, she said, "A spot check also known as a cage check to make sure you are securely locked away."

At that moment I felt so submissive, I knew she was the boss and I had to do as she said.

I pulled my sweatpants away a few inches but she kept staring into my eyes.

I pulled them away a few more inches but she still didn't look.

In a weak voice, I ask what I need to do.

She looked deep into my eyes for an awkwardly long time, like she was looking for something but I didn't know what.

She stepped back a step and looked down at my pink panties and the outline of my chastity cage.

She looks back into my eyes and asks, "It better be secure or I'm not going to be happy."

"It's secure, I assure you of that," I say.

"Good, you can go. That was all she said.

I went back to my truck and sat there for a few minutes. Then went to fuel up and park for the night.

When I got home I packed everything girly-related into a suitcase. I showered and ate dinner then went to bed.

I woke up at five am the next morning to a straining cock in my cage. I wanted to jerk off so bad but Linda has the only keys I had. I tried to pull it off but it was too tight.

I took a cold shower to relieve the swelling and it worked for a while. But the more I thought about what Linda could do and show me the hornier I got.

It's now three pm and I'm getting ready to go to her place.

---------------------------------------------

This is more of a diary entry than a story. Everything written here is true except I've changed the names