Dress like Mia when She's Gone Pt. 06

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An amazing date night as a woman with a Masculine man.
3.5k words
4.7
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35

Part 6 of the 7 part series

Updated 06/12/2023
Created 12/15/2016
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Here's a quick summary of the first 5 parts:

My high school sweetheart Mia, joined the Marine Corps right after graduating High School. We got married right after she finished Boot Camp, so that I could move out to be with her in California. She left for a seven month deployment, on ship in the Pacific. Struggling with her departure, I began to wear her clothes. It began innocently. I'd wear her nightgown to bed because it smelled like her, then I'd wear her thong under my jeans. Before I knew it, I was wearing her outfits everyday after I got home from Community College. I began venturing out in this persona, even using the name 'Mia', as my alter-ego. I met a guy, Jay, on one of my outings and he's been so hard to ignore. I stopped ignoring his advances after I found out my wife was cheating on me during her deployment. I was devastated and took it out on her by getting drunk with Jay. Well... we slept together and the next day I gave him a blow job. Now we're supposedly hanging out tonight after he gets off of work.

-

Jay walked out the door after stopping by during his lunch break. I was originally going to tell him that my crossdressing is temporary and that I'm going through a rough time. The rejection was supposed to come from me, but instead he seemed stand-offish. I don't know what got into me but I ended up on my knees with his dick in my mouth about twenty minutes ago.

I could still taste his cum every time I licked my lips. The taste grew less noticeable with each lick, making me a little sad. I hope he comes over after work.

I walked into the bathroom and looked at the smudged lipstick on my face through the mirror. It was so difficult not to jerk off right in that moment. In fact, the entire time I sucked Jay's cock, I fought the urge to touch myself.

Every time I after I ejaculated while crossdressing, I felt ashamed. I don't know what it was, but I'd immediately get undressed and felt so emasculated by my CD habit.

So I began resisting the urge to jerk off. It was such a challenge, but sometimes I'd spend two hours getting dolled up, just to jerk off ten minutes after I was done getting ready, and it would feel like I had wasted so much time.

Today, I wouldn't jerk off, instead I'd stay dressed like Mia all day and hope for Jay to text later.

I put on a Lady Gaga album in the background and put on a makeup tutorial video to watch. I'd skip breakfast so that I could lose some weight.

My waist trainer came in the mail yesterday. I cinched it on really tight. I wanted to get that hourglass shape without having to wear a garter belt. I knew these habits weren't good for my health, but I was young and I wasn't planning on doing this forever. After my wife cheated on me, this was a good way for me to cope. Better than doing drugs or drinking myself to sleep every night.

My phone buzzed and my heart skipped a beat in excitement. Was it Jay? I thought.

I checked my phone and it was just Amanda. Her husband cheated on her with my wife on the same deployment. She had been texting me every other day, wanting to meet up. I can understand how hard it is for her, but I can't be someone she should be leaning on. Plus, I've pluck my eyebrows in a very feminine shape, and I pretty much always have nail polish on my fingernails.

"Can we chat sometime? I know you probably don't want to see me. But I just want someone to talk to," she texted.

I felt so sorry for her. I can't imagine how she's coping. She'd probably feel sorry for me if she found out what I was up to.

I was a little fearful that my wife would find out that I was dressing up like a woman while she was gone, but I was so upset that I didn't really care. I answered Amanda with, "Sure. :) want to meet tomorrow?"

"I'm in the area, if you can chat now?"

I can't chat with her now, I thought. I'm dressed like a woman. But who cares? I'm sure Amanda is such a wreck that this wouldn't phase her. She'd probably see how much I'm suffering too. While I don't consider my behavior damaging, I do see it as a bit of a cry for help. Without any friends in the area, it would be nice to be able to chat with someone while I'm dressed up.

"Sure," I replied. "But there is something you have to know, and don't freak out."

"What?"

"I'm dressed like a girl."

"LOL," she responded. "I won't judge :) "

I texted her my address. It made me really nervous to know that I'd probably spend the next hour with someone who knows my wife and has never seen me dressed up.

I checked my blouse and high-waisted skirt in the mirror. My thigh high stockings held up after being on my knees earlier. My makeup was on point and so were my nails. I actually felt really confident for once. Maybe because I knew that my makeup skills were getting much better and that they were probably better than Amanda's.

When my doorbell rang I got a bit nervous again. I really hoped she wouldn't be weird about how I'm dressed, or by the fact that my wife slept with her husband.

I answered the door to see her with a big smile. I could tell she was masking her sorrow with overbearing kindness, but I liked it.

"You look, fabulous!" she said.

I was really surprised at how cool she was, despite the circumstances.

Her eyes looked me up from head to toe, as her mouth grinned widely.

"Thank you," I said, in my most female voice.

She gave me a big hug and said, "You smell great too."

I led her inside and gave her a glass of ice tea. She pulled a bottle of wine out of her purse and said, "I'll pass on the tea, but bring two wine glasses and let's split this."

"I don't have wine glass," I said, "I'm still under 21. But I'll bring some cups."

"No worries girl," she said.

Amanda and I had a really fun time. I was acting like such a girl and it felt great.

Being dressed up like a girl when you're alone is fun, but when you put on that persona with another girl and just chat, it's one of the best things.

We went on and on about movies, music, recipes, and even the kind of makeup we use.

We didn't talk about our significant others until Amanda brought up the military spouses group that she was a part of. Apparently she had been shunned from those ladies. They think that her husband is a bad influence on their husbands, so out of fear they shut Amanda out of their social gatherings. It's part of the reason why she reached out to me, despite her not openly admitting it.

"So tell me about you. Have you always dressed up like this for fun?"

"No," I said. "But after the deployment started, I started wearing some of my wife's things and now I do it everyday."

We both started laughing.

"Everyday?" she said. "How do you get groceries?"

"I dress up like a guy," I said. "Next time, I'll go dressed like this, but to the grocery store two towns over!"

We laughed again. The wine was really getting me comfortable. I wanted to tell her about Jay, I felt like I could tell her anything.

"Well you look great, and if I saw you in public I would be so jealous of those legs and that makeup."

"Thank you, that's so sweet," I said.

We hung out for an hour and then ran out of wine.

"I'm having so much fun right now," Amanda said. "Let's get more wine. There's a place within walking distance."

"Oh, um," I said, before checking my phone, incase Jay texted me. "I actually need to clean up my place. I might be having company tonight."

I said that in such a way that intrigued Amanda. Maybe she could sense the excitement in my voice or the look in my eyes that people get when they're excited and nervous about someone.

"Oh my God, ok!" she sounded elated and smiled real big. "I'm gonna bring back some wine and you're gonna clean up your place while I'm gone, then you're gonna tell me all about this, 'company'."

"Ok, hurry," I said, all giddy.

When she left, I tidied up the place. I vacuumed, did dishes, dusted the table and cleaned the bathroom.

Amanda came back with a grocery bag and three wine bottles.

"Hear," she said, as she hand me the two extra bottles with a wink. "These are for you tonight."

I laughed as I put them on the kitchen counter and opened up the third bottle. We chatted some more about small stuff, but I really just want her to ask me about my plans tonight.

She could see the look in my eyes and finally said, "So who's coming over tonight?"

"I thought you'd never asked," I said, with a laugh.

"I'm dying to know. Tell me."

"Well, his name is Jay," I started.

"What? A guy! This is great! Tell me more," she said, as she sipped more wine and leaned forward on the couch.

"Ok, so there is this guy that I kind of like. Like, I really kind of like him and I'm freaking out."

"Oh my gosh. I had no idea that you were into guys," she said.

"Well, I'm not really into guys. Just Jay, I guess. I don't know. It's just that when I get all dressed up like this, I feel sexy," I said. "Especially when I look at myself in the mirror."

"Well you are definitely a babe," She said.

"Thanks," I replied. "So Jay gave me this sort of look that made me feel like I looked attractive. And when I'm dressed up, I don't really know if I pass for a woman unless someone else says so. And girls can be nice and say I look like a girl, but only a guy can really affirm that, you know?"

"I know exactly what you mean," Amanda said. "A girl telling you that you look pretty is like your mom telling you that you look pretty, it doesn't matter what they think, what matters is if the guy wants his hands on you."

"Exactly."

"So? Has he been here before?" she asked, with a smirk.

"Um... I don't know if I should tell you that."

"Bitch," she joked. "I got you wine, you have to tell me now!"

"Ok, but promise you won't tell anyone?"

"Promise," she said.

"Yes, he's been over," I said, with a guilty smile.

"And...?"

"And he spent the night."

"Oh my God, girl, that's wild. What's he like?"

"He's got blonde hair, a tight muscular body like a swimmer, and his forearms are so sexy. I never thought I'd be attracted to a man, but I feel like Jay is the ideal masculine man. Like, he doesn't even realize how hot he is, and that makes him so much more attractive."

"Ugh, he sounds dreamy," she said.

"He is," I said, when my phone text notification went off.

"Is that him?" she asked.

"Yes," I smiled and got all giddy.

"What did he say, girl?"

"He asked if we're still on for tonight at 6."

I replied to his text with, "Yes, I have wine, so come thirsty ;) "

"You have to tell me more," Amanda said.

Amanda stuck around until 5:50p. She wanted to meet Jay, but decided to scope him out from the street. She is so funny. I can't wait to tell her how the night goes.

She text me, "Good luck, and keep me posted!"

When Jay arrived, I reached to hug him, but he grabbed my lower back and the back of my neck and pulled my lips onto his for kiss. It was not what I was expecting, but I really really liked it.

Our lips pulled apart, but he kept a firm grip on my body. Our faces were inches apart when I opened my eyes and he kissed me again. We made out by the doorway. He lifted me up and pushed my body against the wall as he kissed me.

My fears about him not being interested in me totally disappeared.

I reached for the back of his head and gripped his hair. My left leg reached behind him and hooked his leg and pulled his body into mine. It was an intense make out session with heavy breathing. His hips thrust once into mine, and I moaned.

I moaned like such a girl.

"Oh baby," I whispered between kisses.

He thrust again, saying, "You like that?"

"Mmmm, hmmm," I moaned.

He carried me to the couch where we kissed more and more. Now I was straddling him, as he sat on the couch. I was grinding myself over his bulge. I reached down and undid his belt and pants, revealing his erect cock.

I wanted it in my mouth again, so bad. The look of his dick made my mouth water. Before I could make a move, his hands reach around the back of my skirt. He lifted it up and searched for my asshole with his finger.

The tip of his middle finger moved the narrow thong out of the way as it began rubbing my hole in small circles.

"Oh, baby," I moaned, as he rubbed harder on my ass.

He pulled a small tube of lube out of his pocket. I was happy to see that he had planned for this evening.

He put a squirt of lube on his finger and his cock, and then reached his hand around for my ass again. The lube felt cold when his finger touched my ass. His middle finger rubbed up and down around my ass before he pushed the tip inside of me.

I wanted the whole finger. I began arching my back, to make it easier for him to finger me.

His mouth and lips went down to my neck. He bit the skin on my shoulder as I reached down to feel his cock. It was covered in lube as I stroked it up and down.

He pulled his finger out and pulled my ass closer to his body. My ass was over his cock as he held it straight up.

I felt his lubed dick beneath me, gliding around my ass. I slowly lowered my asshole onto the tip of his thick solid penis. I sat down on the tip, putting more and more pressure on my tight asshole.

Suddenly the tip slipped right up inside, causing me to gasp and then moan in relief and pleasure. I sat further and further down, feeling his lubed dick slide into my ass. His powerful hands grasped my legs and pushed me down all the way. It felt a little rough, but I liked feeling his strength.

When he was fully inside of me, he kissed me as I began to grind on him. I started bouncing up and down, increasing the speed and rhythm each time.

He then lifted me up, with his cock still inside of me, and carried me into the bedroom. I wrapped my arms around his neck like such a girl.

We were now in the missionary position on my bed, as he started to thrust himself into me. I held onto the bed railings as much as I could. He tossed me around with his powerful arms and kissed me gently with his lips. Sweat poured down his face. He took his shirt off and I rubbed his sweaty muscular chest. It was so hot to see my red painted fingernails against such a masculine body.

He was pumping into me faster and faster. He grabbed my shoulder to hold me still and pushed harder than before. His breathing got intense. I loved hearing his breaths get faster, knowing that I turned him on. I moaned out of pleasure.

To be on the receiving side of such a powerful man was such a treat. Despite my tight ass getting slammed hard, I wanted more.

His balls slapped against my ass each time he thrust himself fully into me. I was such a lucky girl, I thought.

"I'm about to cum," He said, between breaths.

"Cum inside of me baby," I managed to whimper.

"Oh, baby!" He almost screamed.

His hips pounded my body into the bed. Warmed cum filled up my insides.

"Fuck, yes," he said, as he pumped his last remaining drops of cum into me.

He kept his cock inside of me and kissed my lips. His hands caressed my face and he smiled at me.

I smiled back, shyly. I looked away and he moved my chin to face him. He kissed me softly.

I kissed his collarbone and shoulder, tasting the his sweaty skin. It was delicious.

"I tried to resist," he said, "But as soon as I walked into your place and saw you, I couldn't keep my hands off of you."

"You'll have to buy me dinner now," I teased him.

"Let me take a shower and then I'll take you out."

"Ok, but let's have some wine first," I said. "Before we go."

"Deal," he said, before slowly pulling his cock out of me.

Jay got up and went into the bathroom to shower.

I lay in bed staring at the ceiling fan. My wife and I used to have sex on this bed, I thought.

I got up and clenched my ass, wanting his cum to stay inside of me.

I changed out my now wrinkled skirt and blouse. I put on a gorgeous flower dress that I ordered off of Forever 21. I also changed my bra and lube covered thong.

I poured a couple of glasses of wine for Jay and I.

"You look beautiful," he said, when he walked out of the shower.

"Thank you," I blushed, as I sat on the couch.

Jay sat right next to me and kissed me again.

I put my left hand on his inner thigh and took a sip of my wine.

We chatted all night and never did make it out to dinner. We did open up the second bottle of wine though.

At one point Jay surprised me and said, "I live about 45 minutes away, you know. I wish you lived closer."

"Me too," was my natural response.

I was really enjoying myself, but Jay was starting to sound like he wanted to get serious. Dressing up like a girl was just a thing I started to have fun with, but I didn't think it would get this far.

"You know, I have a two bedroom condo?" he said. "I live alone, you should come check it out."

Fuck it, I thought.

"I'd really like that," I said.

It didn't take long before we were kissing again. I unzipped Jays pants and started stroking his dick again. Jay then got up and grabbed his backpack. He pulled out a can of whipped cream.

"I almost forgot about this," he said, and then sprayed the tip of his dick with the cream.

He walked over to me, with his dick erect, and stood in front of me. I opened my mouth and sucked the whipped cream right off of his dick.

"Mmmm," I moaned, "More please."

He sprayed cream on the base of his dick, so that I'd have to deep throat him to get it. Not wanting to disappoint, I bobbed my head up and down on his dick until I could get it into my throat without gagging.

I kept deep throating him over and over. I could see that he really liked it. The whipped cream and his pre-cum made for a great taste.

His cock began pulsing harder and harder. I cupped his balls and increased my sucking speed. With my other hand I started jerking his dick.

He started to blow his load into my mouth. I opened wide and slide my tongue all over the tip of his dick as semen hit my tongue and the roof of my mouth.

I swallowed all of it and sucked his dick dry.

-

Jay spent the evening and left for work again the next day. I woke up in a pink night gown. I need to get lingerie, I thought.

Jay text me later that morning, "I'm coming over for lunch, if that's cool. And I still owe you dinner btw ;) "

I couldn't wait to see him.

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AnonymousAnonymous9 months ago

As long as everybody's happy it's a good one Maybe Joe and Mia the mail Mia could get married after Mia and Mia get divorced

AnonymousAnonymousalmost 3 years ago

I loved this story but I wish it was longer. I would have liked to have read weather the dress like Mia moved out of his wife's home with all her clothes and to live as Mia with Jay in his home.

AnonymousAnonymousover 3 years ago
Love it

Please continue this story. Absolutely love it

AnonymousAnonymousover 5 years ago
More please

Just found this story and I love it. Please continue it.

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