tagTranssexuals & CrossdressersDress like Mia when She's Gone Pt. 04

Dress like Mia when She's Gone Pt. 04


Summary: After my wife left for a seven-month deployment I began to surround myself with her belongings. Soon after I was wearing her lotions, trying on her clothes, and listening to her music.

This crossdressing habit became a weekend ritual. I ventured for a drive while crossdressing and got stranded with an empty tank of gas after my wife canceled our credit cards. She lost her credit card in the Philippines, and called the bank.

As I was stranded along the highway a guy named Jay, came to my rescue. He bought me gas and now I owe him $30. I'm meeting up with him on Thursday, and he said if I bought him a drink then we're even. Our text conversations have gotten somewhat flirty.

My wife, still in the Philippines took a trip up north to a resort town with a bunch of her male co-workers. I'm hoping she calls me soon.


Monday mornings I was back to guy mode, back to college, and back to the reality that my wife was in a resort town known for partying. I trusted her for the most part, but I've heard horror stories about infidelity within the military.

Most units have spousal support groups that get together once a week when the unit is deployed. My wife told me to stay away from the group, she said all the group does is gossip, spread rumors, and cheat on their spouses. There also weren't that many male spouses married to Marines, so I didn't really have much of an interest in going.

I usually just hit the delete button when I see an email from the group but I didn't this time. The subject line read: "The Cancun of the Philippines?????"

I clicked open the email and began to read.

"....this resort town is known as the Cancun of the Philippines. As many of you may be aware, some of our husbands are taking a much needed vacation. We, as a group would be very grateful if everyone could share any insight or knowledge about their time there..."

I stopped reading. It just seemed like gossip, just like my wife had said. Yet there was still a part of me that felt uneasy about her being there.

I was also uneasy about seeing Jay on Thursday. I'd be going out for the second time, dressed as a woman. Jay doesn't know I'm married, or straight, or that I'm under 21. He's sent me text commenting on my legs, and then I sent him a picture of them, which is so strange for me to do.

I was definitely flattered. And getting my legs noticed, which I had done a lot of work on, was such a nice compliment. I didn't have anyone else to share pictures of me dressed up, and I never get comments about my appearance when I'm in guy mode, so why not enjoy it?

Before I went to class that morning, I did what I started to call my 'booty excercises'. My guy butt didn't fill in my wife's jeans like hers did, so I was working on changing than. Everyday for 45 minutes I did heel raises, squats, and an assortment of other moves to get a nice round bottom.

This crossdressing habit was temporary, I told myself. As soon as my wife returned I didn't plan to continue doing it. I was mainly doing it as a means of coping with her absence. So none of these changes or habits were permanent, even this meeting up with Jay thing will be a one-time thing.


While I was sitting in class my phone was vibrating like crazy. I had missed several calls from this woman in the spouse support group. Her name was Amanda and her husband worked closely with my wife. She had also sent several text messages.

I checked the texts and Amanda had sent me pictures.

My heart sank.

The first picture is one of my wife letting someone take a body shot off of her stomach while she was flashing her breasts. Then she sent another one that showed her sitting on a guy's lap, who happened to be Amanda's husband.

"I have more pictures... I wish I didn't and I don't think you want to see them," she texted.

My body was shaking so hard from greif that I could barely hold onto my phone. I wanted to throw up and scream. My wife was my life; I'd do anything for her. In the back of my mind I was worried about something like this happening.

I walked to my car and called Amanda.

"Hi, thanks for calling me back," she said.

Amanda was furious and a little histerical. She was married and pregnant with her husband's child, yet there he is cheating on her.

"Cheating?" I asked, "But these pictures don't prove that they actually went through with it, right?"

One of her husband's co-workers and rival, snapped the photos and sent them to Amanda.

"He told me they both went to the same hotel room that night," Amanda said.

My world was shattered. I got off the phone and drove home. I went into my wife's closet and wanted to throw all of her things in the trash. Her shoes, belts, dresses, skirts, etc...

I threw them in a big pile on the bed. These were clothes I wouldn't dare use to dress up in because they were more delicate and expensive.

I spent the rest of the day laying on the bed on top of her clothes, wondering if she would call me. I was miserable and had no idea how to deal with this crisis until I heard a text notification from my phone.

I opened the text and saw that it was from Jay. All he wrote was, "Legs???"

I smiled a little, didn't think I'd be capable of smiling on a day like this.

Sending Jay another photo of my legs is what got me out of bed. I definitely felt less bad about sending him the first picture.

I looked at the pile of clothes on the bed and picked something I wouldn't of worn had my wife not cheated on me.

It was this gorgeous floral patterned dress. It showed a lot of leg.

I went into the bathroom to shower and shave my legs. It then applied some shiner to them to make them look extra good. I put on my makeup, the wig, the bra, the panties, and finally the wig. I loved this dress on my wife, but now I preferred wearing it myself.

It was very comforting to be dressed up. It made coping with my wife's infidelity a little easier. It kept me busy and focused.

I snapped some pictures to send to Jay but wasn't satified with how they came out. I needed shoes on my feet. I found a pair of my wife's rose colored heels and squeezed my feet into them. Although they were a tight fit, I loved walking in them. It automatically changed my posture. I felt way more feminine in these heels than I felt in pink sandals.

I snapped a photo I finally liked. It was from the hips down, I had one leg standing straight and the other leg was bent inward with my heel flared out and my toes pointed down. I sent it to Jay and waited for his response.

"That's hot," he responded.

I'd never been referred to as hot before. I really liked it. Jay was definitely in full flirt mode now.

So, I text him back mischievously, "Forearms?"

He another photo of him without a shirt on. His forearms were flexed and his veins were bulging.

I thought about responding with, 'that's hot,' but I wasn't sure that I wanted to enter that territory. I was fine with getting flattered by a guy, but to reciprocate it, I wasn't so sure.

I still identified as a straight male but being dressed up made me see things from a woman's perspective. I was also really pissed at my wife cheating on me. I was in this odd sabotage state of mind, where I didn't feel like caring about our relationship.

So, I texted Jay back and wrote, "Hot... u must be so strong."

"Strong enough for lots of things... Hey, I'm actually in town today. I'll be here all week if u wanna grab drinks tonight?"

Tonight? Sure, I thought. I wasn't planning on going to class at all this week anyway.

"I'm not 21 yet, fyi," I text him.

"Bummer. I can bring a flask to the bar ;) u like vodka?"

"Ur such a rule breaker :) I like that and vodka too," I responded.

I was being such a flirt, but I also didn't want to lead him on too much.

"I can pick u up. Don't want u running out of gas ;) text me ur address, I'll be there at 8." he wrote.

I sent him my address and responded with, "Cool, it's a date."

Shit. He doesn't really think this is a date, right? Maybe I should back out? I don't want him trying to kiss me or anything. I'd be flattered as hell, but I can't imagine wanting that to happen. I can always just turn away if he tries.


I was excited and nervous to be going out again dressed up. I wanted to look really good, obviously, so I spent the whole day perfecting my makeup and styling my wig. I picked a cute high-waisted skirt to wear, a tight top with long sleeves, an extra padded bra to make my chest look nice and firm, knee high stockings, and a black woman's cardigan. I put on a pair of my wife's brown shoes and I even put on a straw brown boater hat on the back of my head.

I check myself in the mirror and got really excited at how well I was getting at passing.

I shoved some personal belongings into a small purse and took some photos of myself for my new Instagram account.

At 7:55 Jay knocked on the door. I jumped out of my seat and opened up.

"Hi," I said, shyly, in my best female voice.

"You look good," he said. "Nice to see you in person again."

I shut the door behind me as I walked out of my house and Jay reached his arms out to give me a hug. He wrapped his big arms around me and my hands travelled across his back to his shoulders. I squeezed him tight and held on a little longer. He smelled surprisingly good.

"You smell really good," he told me.

I smiled and said, "You too."

He led me to his car and opened the door for me. The drive wasn't very far to the pub/restaurant. We could have walked.

"How long have you been... going as woman?" Jay awkwardly asked.

I knew this conversation was eventually going to come up.

"Um, not very long," I answered. "Like two months."

"That's it? You're really good at it. I didn't notice until I filled your car up with gas."

I smiled really big, I didn't believe him, but appreciated the compliment.

"Thank you," I said. "I'm really a beginner at this, I guess. I was terrified to be stranded on the highway dressed the way I was. Thanks again for saving me."

Jay laughed, "When I saw those legs I couldn't just drive by without stopping to help."

I laughed and said, "I still get nervous, I was nervous walking from my front door to your car."

"You don't have to be nervous around me," he said. Then he looked at me and said very kindly, "If at any point you feel uncomfortable and want to go home or leave, just let me know. I want you to just be yourself, ok?"

It was really comforting to hear him say that. He definitely didn't seem to want to take advantage of me.

When we got to the parking lot Jay offered me his arm like a gentleman. I reached my hand to hold his muscular forearm. It was such a different feeling to experience than any I had ever felt. I felt like arm candy and like I was being guided around by a real man.

Inside, the hostess sat us down at a table for two. Jay order a vodka tonic and a tonic water for me.

When the drinks came out, he pulled out his flask and smiled, "I told you I'd bring it."

His strong arms reached across the table and he poured some vodka in my drink.

Being only 19 years old, the vodka was a little strong. I hadn't eaten all day either, after I found out about my wife. The drink made me so relax and comfortable. Jay was really funny, he was telling me all about his work and his hobbies.

I didn't want to talk about my life so I kept asking him questions. The server brought out a second round of drinks, and then a third, and by the fourth round Jay and I think she was getting suspicious about because I was getting tipsy.

"We should probably go before we get busted," Jay said, laughing.

We paid our tab and left the bar.

"I probably shouldn't drive right now," Jay said. "How about I walk you home? By the time I walk back to my car I should be sober enough to get to the hotel room I've got booked this week."

"Ok, let's do that," I said.

Jay offered me his arm again and I took it without hesitation. I liked our conversation, we were having a great time. I could smell him again as we walked side by side.

It was good he let me have his arm because I was in this tight shoes that I'd never worn before and I was a little tipsy.

When we got to my front door it started to feel weird. It felt like a romantic comedy scene where the guy walks the girl to the door and has to decide whether he's going to kiss her or not.

I'd been in this position before, but as a male.

I also didn't know what I wanted. I didn't want the night to end because I was having fun. I also didn't want to lay in bed thinking about what my cheating wife was up to tonight.

"Do you think I can use your bathroom?" Jay asked, before anything awkward could happen.

"Yea, sure," I said, and let him in.

Luckily, I cleaned the house that day, thinking Jay would only see it from the front doorway. I went into the kitchen to pour Jay a glass of orange juice, which is something I would have done for my wife if she were here.

Jay came out from the bathroom and I handed him the glass.

"Thanks," he said, "Is there any booze in this?"

"No, sorry about that," I answered as I poured myself a glass.

"Do you want some booze? I still have some vodka in the flask."

"Um, sure," I said.

Jay poured some into both of our glasses. I was really glad to have more time with Jay this evening. Although I wish we were still walking, that way I could have my hand touching one of his arms.

"Let me put on some music," I said, and walked over to my stereo. I bent down to reach the power button.

Jay walked right up behind me as I was bent over. Music starting coming out of the speakers as I stood up and felt Jay gently press his body against the back of mine. His crotch was up against my bottom and with one firm hand he grabbed my right arm, and with the other hand he grabbed my left hip bone.

I didn't resist when he pulled my body into his. In fact, I arched my back to stick my butt out more so that it pressed better against his groin.

He brushed the hair to one side of my head and placed his lips on my neck. It sent shivers down my spine. I arched my back even more and reach my hand behind me to grab at his pants and pulled him tighter against me.

His hips began to grind against my backside. His jeans rubbed up against my thin skirt. I could feel an erection starting to take place as he continued to press it against me.

He started breathing through his mouth, the warmth of his exhales ran down my neck. I reach my other hand to grab his left hand that had a firm grip on my hip. I ran it up to that forearm of his, the one I had been holding earlier. This time I could run my fingers up and down it. I could feel all his muscle fibers twitching as he gripped me so good.

He pulled off a little bit and I could feel him unbutton his jeans. I longed for his now absent hands to manhandle me again. I then heard him unzip his jeans and drop to the floor. He only had his underwear on now.

He held me again and pressed his now solid dick against my rear. Although my skirt and his underwear were still on, I could feel the mass and girth of his dick.

Jay lifted my skirt from the back and then pushed himself up against my rear. I was only wearing thin panties. It felt so good.

He rubbed up and down against me. I was now breathing heavier; maintaining an arched back for a strong man isn't easy.

I then felt his hand reach into his underwear as he pulled out his dick.

He let the weight of his dick lay on top of my lower back. Then he picked me up suddenly and carried me into the bedroom. The room was a little dark and he didn't bother turning the lights on when he tossed me on the bed. I was on my stomach but before I could turn around he had his bare dick pressed up against my ass.

I still had my panties on as he lifted my skirt and let his body grind his dick onto me. I arched my back and felt his balls rubbing against the back of my thighs.

This was incredible, but I don't know if I can keep going through with this.

It felt so good and exciting but I had to pause for a second and think this through. Did I want to cheat on my wife? With a man?

"Jay," I said, between labored breaths.

He didn't respond, instead he lifted a bottom part of my panties and put his dick in between the panties and my ass.

I gasped. It felt like I wanted more. He slid his hard dick up and down my crack with the weight of his body.

"Jay," I said.

One of his hands then slapped my ass cheek.

"Oh," I almost moaned, "fuck."

That was hot, and Jay meant business.

He must have known I enjoyed the slap because he slapped me again across the ass, harder this time.

He then grabbed my panties from the top and pulled them down, exposing my bare ass.

He slid his dick up and down my crack again. It rubbed up against my hole, making me arch my back even more. It felt so good.

I felt his warm spit land on my crack. It dripped down onto my ass and then down to my balls.

He spit again, then grabbed his dick, and rubbed the tip of his cock around my asshole. His spit was all over my crack now and I could feel his dick was all wet.

The tip of his dick rubbed all around my hole. I arched my back and even lifted my ass off the bed a little as he straddled me from the back.

He stopped rubbing his dick everywhere and started pushing it against my asshole. I'd never had anything go up my ass before so it must have been tight.

"Relax, baby, relax," Jay said. "I need you to push out with your ass. That's the easiest way."

I pressed out with my asshole, to try and relax it like Jay said.

"That's it baby. Good work, keeping doing that."

I like doing good work for Jay. Pleasing him pleased me.

The head of his dick was now wet and pressing up against my hole. I could feel the tip starting to make its way in. It was a slow process but felt so satisfying.

He spit again on my ass and kept pressing his dick. I felt my ass suddenly give way as his head entered me. Damn, it was amazing. It did feel a little strange and painful but Jay was pushing it in really slow.

Once the head was in he kept shoving his dick deeper in to my ass.

"Ah!" I gasped as it got real deep.

Jay grabbed a pillow and put it under my arm so I could bit it or grab it.

"Oh!" I moaned loudly in mild protest. I still hadn't even felt his balls hit me body yet, so I knew he had more dick left to shove inside of me.

He pressed in further and I could feel the tip of his dick pressing up against my insides. When he was all the way in he let all his body weight press on to my ass.

He pulled his dick half way out and then back in all the way. I flinched several times. This was so new and a little odd; I wasn't quite used to this feeling.

I flinched and moaned less and less as he slid his wet dick in and out of me. He then began to increase his speed and force.

I felt like I was being pummeled as he brought the weight of his body down against my ass. The bed start bouncing rhythmically as he pounded my behind over and over.

I could feel the head of his slide as far deep as it could, then he would slide it back out, almost to the point that it would come out but it never did.

He kept pounding away. Jay lifted me off my stomach to where I was in the doggy style position. His hands were now on my hips and he would pull my body with all his might onto his, as his dick slid in and out of my virgin ass.

My arms were so weak and tired that I let the front of my body lean down onto the bed with my ass still in the air for Jay to have.

I was moaning in pleasure and pain. With each rapid thrust into my ass, my moans would shudder.

Jay reach for my shoulders with his strong hands and put me in the doggy style position again. They gripped me really hard as his breaths got faster and faster.

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byaideneikona© 6 comments/ 19391 views/ 22 favorites

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