Telling Her Pt. 02

We walked out to the car with some clothes on hangers, my makeup bag, a bag of shoes, and a small case with underclothes. I slid into the passenger seat, and realized I kept my knees together doing it as lady-like as I could imagine. She slipped me her purse as she got in, started the car and we were off.

The drive to her place was exhilarating; exciting; comforting; amazing; all at the same time. I felt oddly comfortable dressed like this with her, and could not stop looking at her and smiling. It made me excited in another way too and I became a little worried that was going to become obvious, at the same time not afraid of it either. I wanted to cuddle with her.

"No turning back now."

"I guess not," I said, starting to feel a little panic. What would happen? We drove down the street as all kinds of possibilities floated through my mind. Situations where I would have no choice but to navigate dressed in a skirt and blouse and heels. Maybe we would get a flat tire? Or pulled over for some light out and have to give the police identification. Maybe she has drugs from a previous boyfriend and we go to jail. Or, I know this is crazy, but trust me you would entertain this too, she was a serial killer taking me to my doom. Or maybe she knew all along and finally had me in a vulnerable state to display before her friends for a good laugh.

I have kept this secret for so long afraid anyone would find out, and now here I am having revealed it to someone I like, and afraid it's going to blow up in my face.

She reached over and put her hand on my knee. "You look so cute, I can't believe you have kept this from me!"

"Well, we have not been together for that long. I never intended to keep it from you. I just wanted to find the right time."

I paused.

"And I was not really sure how you would react."

"Well, don't worry anymore! Let's have some fun with it!"

We drove in silence for a bit, but she kept looking over at me and smiling. I was shaking, thinking I should say something but at a loss. My heart was pounding. My mouth was dry. But there was no thought in my mind about escaping or talking my way out of this or even asking if we could go back because I was scared. And I was more than a little turned on by it all.

Her house was dark. "My mom and dad are away for a week. They are coming back next weekend so we have the run of the house."

After parking in the driveway, she got out, taking her purse from my hands, and opened the back door to get the clothes and the bag of shoes. I looked around first, afraid there were people in the neighborhood who might see me.

"Relax," she said, "No one is going to recognize you and you just look like one of my girlfriends from the distance."

I grabbed my makeup and the suitcase, closed the door, and followed her to the front door.

Suddenly the porch light came on. "Motion sensors," she said, fumbling in her purse for her keys. I looked around again. No one. At the same time, I was aware again of being outside with someone who knows me, dressed pretty, and loving it. I looked at her and then at myself, and just thought "maybe I am dreaming?"

"Follow me," she commanded and we went upstairs straight to her bedroom. "It's where me and any of my girlfriends would go first when we got to my house!" She exclaimed! "Put your suitcase on the bed and the makeup case over there next to my dressing table."

She hung the clothes in her closet, which was quite large I will say! She dropped the bag of shoes on the floor at the foot of the bed. The room really is large. It's big enough to fit four king sized beds, but her bed is a queen. There is a corner with the clothes rack, on which were hanging two dresses and a pair of jeans. There was a chair by the rack, and a little table next to that. The door to the closet brought you to a walk in the size of many small bedrooms. Two walls of hanging clothes, a large mirror, and a chest of drawers with knick-knacks on top of it. My dresses and skirts were hanging now closest to the door.

"Can I do your make up?" She asked.

I was nervously smiling at her, looking at how cute she was and thinking I wished that I could be that cute, and simultaneously that I was very happy that I was in her company, and that I was dressed like her. And she wanted to help make me be pretty!

"What should I do? Should I wear something over my clothes? Or maybe just take off my blouse?" That idea seemed particularly interesting to me. Picturing her the same way, and having her so close and putting makeup on my face...well let's just say I liked the idea.

"I'll put a cape over you. It'll be fine. Sit over here."

She sat me at her makeup table in a wooden armless chair. I put any hands in my lap, laying one on the other, palms up.

"Can I take your wig off? Just while I put on the makeup. It will be easier. We could pin it up but I think that would be more trouble."

"OK." I said. I pulled it off my head and let her slip it over the corner post of her bed.

"Now look up at me." She put her hand under my chin, and looked my face over. She gently brushed over my eye lashes and quickly blinked and said "I think I can work with this."

She worked on me for a half hour. My eyes, my face, my eyebrows. She had them all lined and highlighted and plumped and thickened and smoothed, with a broad brush here, a pencil there, a scrap or buff there. She finished with touch of red on my lips.

Touching my face was such an intimate feeling. She saw me, looked at my eyes, into them, scanned over my face. I could smell her perfume and her breath. She squinted her mouth and eyes as she applied color and definition to my features.

I was acutely aware of how I was dressed and her closeness and it was making me very excited. I could feel the warmth of her body radiating and it occurred to me she could feel mine. I squirmed in the chair a couple of times and had to adjust to, well, keep the thing under control if you know what I mean.

"There, have a look," she smiled widely. "But let's put your wig back on first. Careful! Don't mess up your face. There." I looked in the mirror.

I could not believe my eyes. I had done my own makeup before but it did not look this good. She knew what she was doing.

"You have some nice naturally feminine features so it was not hard to accentuate those and hide the rest. What do you think?"

"I love it!" My lips were fuller and a nice pale red color to match my complexion. My face was smooth and evenly colored. My cheeks were faintly highlighted without being obvious. My eyebrows were not like I had seen them before. She had plucked a little and filled them in with a soft brown. And my eyelashes were longer than I thought possible, and made my eyes look...well, positively girlish!

"I love it! You know what you are doing!" Was all I could say. But inwardly my fantasies were in overdrive. I was thinking about femininity, and dressing, and being with her, and pretty things, and a flood of images. And there was a stirring in my panties that was unmistakeable.

"You really like this, don't you!" She exclaimed. "Yes, I do. Is that bad?" I asked?

"Well. It's not usual, but you want to know what I think?"

"Yes."

"I kinda like it too. You look attractive and feminine, and I am interested in spending time with you like this. Is that OK? I mean I don't want to push you into anything you don't want."

"No! I love it! And the more time we spend together, no matter how I am dressed, is fine with me!"

"OK then! Let's do something together. Right now. How do you feel about going out somewhere?"

"Uh...I don't know. I mean, I have been out before but not exactly to public places. I mean, I got gas at a gas station a few times, but I did not have to talk to anyone. And I have taken walks in the park when I was alone. I did go shopping a few times out of town, and tried on clothes at some dress shops."

"Well then, let's do something! We could go to the mall. Or go shopping together. Or just take a drive. I want to get you out of the house for a little while!"

It was only 6:00PM. I should set the stage a little. She and I had been talking at my apartment. She had come to meet me after her last class so we could plan an evening together. It was Friday. Classes for the week were over. We had the whole weekend, and actually the whole following week to kill. It was Easter holidays. Her parents were away for the week. I was not planning to go home. I don't know why I picked this weekend to tell her but I did. It had been weighing on me. I loved her but knew I could not keep this secret for long and I wanted to be completely honest.

Now here we were with more than a week to kill. I was confessing my crossdressing to her. She seemed to like the idea. How in the world did I rate this?

"I'm hungry. Why don't we get something to eat." I was lying. I wanted to kiss her and knew where that would lead and I would mess up both our makeup. But I couldn't think of anything else.

"Chinese?" She asked. "We could get something at the China Wok at the mall and then go shopping."

"Wow! Uh.. We might run into people we know! Why don't we get take out and eat here? We could watch a movie?"

"No silly. I think you really want to go shopping. Besides who do we know that will be out shopping for clothes on a Friday night?"

I think I was going to lose this argument. So I might as well go along. But I was going to have to calm down some because there was a bulge that could give it away.

We were standing facing each other as we discussed this. We paused as we looked at each other thinking about what to do. She moved closer to me and put her hands on my waist.

"This excites you doesn't it!"

"Yes. A little," I lied. It was a lot. She came closer. I put my hands on her waist and felt her warmth. She brought her lips close to mine.

"You'll mess my makeup." I giggled. Then we kissed. And I was in heaven. It was a soft kiss. I could taste her lipstick. I could smell her perfume. I reached to the front of her waist and started trying to unbutton her jeans. She slipped her hand around to the back of my waist and began unzipping my skirt. As it fell to the floor, I finished unbuttoning her jeans. She stepped back from the kiss and pulled them down to her ankles and just stood there smiling.

"That was a switch! Did you like it?"

My mouth was dry and I was not thinking straight. "Yes," was all I could muster. She managed to remove her feet from the puddle of jeans and came back to me and we kissed again as we fondled each others panty covered hips and moved together towards the bed.

"I love you," I managed to whisper, and we backed up to the edge of the bed. We did not even try to take off our blouses as we kissed and touched. I laid her back on the bed and looked at her beautiful face, touching her breasts through the fabric of her tee shirt. Her hand stroked my side, my hip, squeezed my bum, then reached around from the front of my panties.

"You are so excited!" She whispered.

I reached down to touch her panties and let my finger slip in the side of the leg hole and reach her soft love mound, and I could feel the stiffening of her clitoris.

"You are too," I whispered back. We were both smiling and I was enjoying licking and kissing her beautiful lips. We were both taking care not to ruin our makeup which was going to need touch up anyway if we were going to do anything after this was over.

We began to shift on the bed. I pushed up with my arms to let her slide up completely onto the bed, her knees up, feet apart with me kneeling between them. I bent down to kiss her again and our hips touched. My hardness against her wetness.

"Mmmmm," she moaned. I pressed the thumb of my left hand gently against her clitoris, lightly massaging it and enjoying the movement of her body against me and her moans of pleasure.

"I want you in me," she said.

"Help me," I said, and she gently pulled my swollen penis out through the leg hole of my panties and guided it to her wetness as she pulled her panties to the side. I felt myself slide in and gasped. We were making love without removing our panties.

"Oh baby, I love you so much, " I managed to say as I pushed slowly and gently deep into her. Her eyes were closed. She was breathing in short gasps and arching her back, her head turning up, her hands in my back. My knees were under her legs and I could feel her hips on my inner thighs, My lower legs and feet extending toward the end of the bed and her knees coming up under my armpits. We were a ball of twisted flesh hungry for sex as I slowly moved in and out as much as our position would allow. The feeling was so intense. I could feel both our panties against my penis as I moved in and out of her, and it felt so romantic and sexy and I was in love and she liked this and I was just filled with amazement and ...

Then I came. And she came. And I moved in and out a minute more until I felt myself getting soft.

"I should get a towel," she said.

"I love you," I said and I kissed her and smiled broadly. "You make me very happy!"

We cleaned up a bit. She changed her panties. We smelled like sex. We both peed. I sat down.

"Let's fix up our lipstick. You don't look like you need anything else."

"You have a little smudge on your left cheek," I said.

I pulled my skirt back on. She decided to change into a skirt, a cute, short denim skirt, and Birkenstocks.

"Where to, lover?" She grinned as she said it, like she already knew where she wanted to go but just wanted me to resist a little so she could plead with me and convince me. Which I did, and then she did. Then we giggled, got our purses, and went out the door.

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This has been fun to write. I like the story line and the characters and would love to continue it to see where it goes. I want it to be as realistic as possible, making it something I would actually enjoy myself. As I picture myself wearing the clothes and thinking the thoughts of the main character, and the "he" in a dress. I would imagine what I might want to happen, then write it down.

If you want me to continue please let me know. I am open to plot suggestions. Just leave them in the comments. Or email me.

Thanks,

Laci