Dress like Mia when She's Gone Pt. 03

Summary: I begun crossdressing when my wife left for a seven month deployment. Around the second month of her being gone I thought it would be fun to go for a drive. Any hour and twenty minutes later I was in San Diego.

My wife was deployed on a ship in South East Asia. She had a few days off when they arrived in the Philippines. That same day I decided to go on this adventure, Mia had either lost her credit card or had it stolen. This was a joint credit card account that we shared with our bank. She called the bank to have them cancel our credit cards.

So now I'm stranded in San Diego with an empty tank of gas and dressed like a woman...

-

I have a plan. I'll drive as close to home as possible and then pop the hood up on my car and maybe a cop or a someone else can help me.

It was really my only option.

I started the car and turned onto the highway. The car went about thirty minutes before the gas ran out.

I checked my makeup again, adjusted my wig and my bra, then reapplied my lipgloss.

I don't think I'm 100% passable but I'll just play along as a woman when or if someone stops to help.

The cars on the highway were zooming by. I had my hazard lights on and waited.

I saw a State Trooper drive right by me.

I figured I'd have to hop out and prop my hood up.

Stepping out of the car, out in the open, was a thrill. I walked around to the front and opened up the hood.

I returned to my seat and waited again. Still no help.

Maybe if I stand outside, looking clueless, maybe someone will stop.

I opened the trunk of my car and sat on the back bumper. Within a minute a car slowed down a stopped up ahead in front of my car.

A guy stepped out of the driver's side door and began walking towards me. As he got closer I could see that he was a older than me, probably late twenties. He had dirty blonde hair and a chiseled jawline. He was clean shave and dress casually.

I got really shy. I considered going out character for a second. If it was a woman or an old man stopping to help, I wouldn't be so timid about keeping up this act.

I brushed the hair out of my face as I stepped toward the front of my car.

I noticed his forearms as he got closer. They were really masculine. I hope it doesn't anger him that I'm a guy dressed as a woman with my long exposed legs sticking out of these booty shorts. He could easily break me in half.

"Hi, having car trouble?" He said.

My heart wanted to pounded out of my chest, I was so nervous.

"Yea," I nearly squeaked, trying to speak as little as possible. "I ran out of gas."

"That's no fun," he said with a smile. "I can give you a ride to a gas station. There's one just two exits down."

"That's so sweet," I said. I don't know why I said that, I just imagined that's was a girl dressed like am right now would say to a guy. "But I don't have any money... That's my real problem."

"Oh," the guy answered as he looked at me. "I can spot you ten bucks."

I couldn't tell if he found out I wasn't really a woman. I'm pretty sure he could tell but was still being kind.

"Really?" I said, "Oh my god, you're so nice."

My hero, I thought.

"Hop in and we'll get you some gas."

We walked toward his car and he opened the door for me. Well, he either doesn't realize I'm not a real woman or he's knows and is still just a gentleman. No one has ever opened a car door for me. I sat down in the leather passenger seat as he shut the door and walked around to his side.

"I really appreciate you doing this for me," I said. "I promise to pay you back."

"Yea, no problem," he answered, as he turned and looked at me. I noticed his eyes glance down at my legs. I had my knees touching and both legs leaning to the right. "How far do you have to drive?"

"I live about forty minutes away," I answered.

"Forty minutes," he started, "I'll spot you some more for gas. Plus we'll need to buy you a gas canister, they run around ten dollars."

"Thank you," I said. I would gladly pay this guy back for getting me out of this mess.

"My name's Jay," he said.

"I'm Mia," I blurted out, it was the first name that came to mind.

Jay reached for his phone and handed it to me.

"Put your number in my phone, that way you have a way to contact me when you can pay me back."

I took his phone and plugged in my number. Did I just give a guy my phone number? That move he just pulled sounds like something I would have done to get a girls number. My wife, Mia has cluelessly given guys her number like that before.

"Here you go," I said, as I handed him back his phone.

When we pulled up to the gas station, he got out of the car and said, "Wait in here, I can pump it for you."

He bought the gas canister and filled it up for me.

"Thank you," I said again, after he got back in the car.

"No problem." He looked at me and said, "Don't you to get your pretty hands dirty."

I looked at my hands. They were pretty, I thought. Definitely feminine. The shiny beige nail polish helped.

When we arrived back to my car he open the gas tank cover and poured the gas in for me. I noticed the muscles on his triceps flexing beneath his T-shirt.

His blonde hair was blowing in the light wind.

When he closed the gas tank lid I got into the driver's seat and turned the key to start the car but it wasn't starting.

"I'll start the car up for you," he said. "They take a minute to start up when your gas tank goes dry."

He offered his hand to help me out of the car. I put my hand in his and with his other hand he held onto my elbow for support. His hands were so soft but masculine and firm at the same time. He was really strong too as he practically lifted me out of the seat.

After a few moments he was able to get the car running.

"There you go," he said, as he climbed out of my car.

"Thank you so much," I said. I wanted to hug him, it felt appropriate in this sort of feminine to masculine dynamic we had going on. I was clearly playing the damsel in distress. A part of me also wanted to feel his hands on my arm again.

"No problem," he said, with a smile. "I'll shoot you a text so you have me number."

Out of excitement and relief, I leaned toward him and opened my arms for a hug. He was taller than me so I wrapped my arms under his and reached my hand around his back on his shoulder blades. His back was so firm and large. His arms wrapped arm my head and he squeezed me gently.

But as he squeezed, my wig was pulled back a little bit off of my head. I nearly had a heart attack.

"Oops, sorry your hairs coming off," he said, with a grin.

"It's ok," I said, shyly.

Well at least he knows the truth about my identity, and is OK with it, I thought.

-

Jay sent me a text that read: '"It's Jay, let me know when you make it home safe."

I replied with a traditional smiley face, :)

As I drove home, I kept replaying the moment he helped me out of the car. Damn, it felt good to be treated like a proper lady. No wonder my wife takes advantage of it any chance she gets.

When I got home I text Jay, "Home safe! I can repay u asap. Let me know how much I owe and how I can pay. I can mail u a check."

"Great to hear :) I'll be near ur area next week for work. I can pick up the $30 from u in person. Does thurs work???"

"YES!" I replied. I wasn't sure about seeing him again, but he's been so nice that I can't just be distant and say no.

"I'll text u next week when I'm off," he wrote back.

I answered with a, :)

-

Next time I go out crossdressing, I'm going to bring a ton cash on me. Lesson learned!

I didn't dress up for the rest of the week. That trip to San Diego nearly scared me out of crossdressing.

I'll just plan to dress up again on Thursday when Jay comes into town, or so I thought.

The following morning I woke up to a text from Jay, "U on FB or Insta?"

I was on Facebook and Instagram, but not as a woman. I didn't know how to reply. He's so nice and I owe him money, I didn't know how to say no to him.

"I don't really have one," I answered.

"Bummer... U should start one, I almost forgot what u look like."

"Maybe..." I texted back, and began work on my new Instagram page.

"Maybe? At least send a pic so I know what u look like :)

"Ok," I replied.

I had a few pictures of me on my phone from the many times I've dressed up. I started editing the photos and uploading them onto the new Instagram account.

I made the account public to start, that way I can add followers right away and so that Jay doesn't know I'm making this entire account to satisfy his request.

The sexier the photos the quicker I'll get followers, I thought. So I went into the shower and began prepping for another day of dressing up. I put on a thong of Mia's but it ripped when I pulled it to hard over my legs.

So I went online and ordered my first pair of woman's underwear.

I found another thong and put it on, then I found these sexy shorts made out of linen. I looked at my ass in the mirror; they were tight on my backside. I wish I had a bigger booty.

I did a quick google search for 'how to get a bigger butt.' A ton of tutorials and exercises came up: squats, heel raises, hip thrusts, etc...

I immediately began doing all of these workouts. I definitely overdid it that first day, but I was determined to have a fatter ass by Thursday.

After my workout I put on a cute top over a stuffed bra, did my makeup, put on my wig, and found some knee high stockings to try on.

I then snapped a ton of photos, trying to capture a sexy one to send Jay. I didn't want the photo to be suggestive, but I did want it to look sexy, and that's a little hard to do.

I found a photo that captured what I was trying to achieve. It was a photo of me sitting down facing the mirror with my knees together. I had a drink in my hand with a straw in it. The straw was up against my lips and I looked so innocent.

I sent him the photo and instantly remembered that I was a married man and shouldn't be letting this happen.

It be pissed if Mia did something like this. In fact, Mia has done stuff like this before, even since we've been married. She likes the attention and I'm liking it now too.

If she thinks it's OK to do it then I should be able to do it to.

I remember when we last spoke and she was going to a resort town in the Philippines for a couple of nights with a group of guys. This made me feel ill. She was going even without any other women from her unit, which she promised she wouldn't do. The whole thing made me sick, so I stopped thinking about it and hoped for the best.

Jay texted, "Nice pic. I remember those legs now :)

Where's he taking this conversation, I thought. I was a bit flattered by that text. I had been taking care of my legs now for weeks and thought they looked pretty sexy myself.

This guy can't be trying to flirt with me can he?

"haha, is that all you remember?" I replied, to try and gauge what Jay was thinking.

"Of course not, haha, I also remember those shorts you were wearing," he replied.

I laughed out loud at his response.

I did't know how to reply. I liked these texts from him, but didn't know how or where to draw the line.

He replied with a picture of himself and wrote, "In case you forgot what I looked like."

My eyes went wide at the sight of this photo. He was in swim trunks, at the beach and laughing. He was shirtless and muscular.

So many thoughts and feeling were running through my head. I'm not gay, that's certain. But when I'm dressed as a woman I feel like I fall into this feminine role where I'm supposed to like things that women like. I listen to and actually Taylor Swift and Katy Perry when I'm dressed up. I like romantic comedies more and baking and decorating.

Now, men are starting to look more appealing. Even when I'm watching porn, I fantasize about being the woman instead of the man.

It's odd because when I'm dressed as a guy I don't ever have these tastes or fantasies.

It took me a while to respond to Jay. I didn't know what to say so I took a picture of just my legs doing this Marilyn Monroe pose in the mirror.

"Doesn't look like you're wearing those shorts in this pic," he text back.

"I am," I responded, and took another picture. This was a picture of me standing up straight with my side to the mirror and arching my back as much as I could to stick my ass out.

"That's the view I remember... Great pic btw. Where do u want to meet up on thursday?"

I was originally planning to just hand him a check near my place.

"Not sure," I answered.

"If u buy me a drink I'll call it even."

A drink? The only place I've got out dressed was a thrift store. I had so many mixed feelings about this.

"Ok," I reluctantly replied

"See u soon ;)