Telling Her

I couldn't look at her.

I was looking down, at her lap, my hands, the floor. I was nervous. My hands shook. My mouth was dry. I was trying to find the words to say to her.

"You're scaring me now. Are you sick?"

"No!" I blurted. "Of course not. Nothing like that."

"OK. Then what is going on?"

"I like to dress like a girl."

The diminutive came out and I immediately regretted it.

"I like to wear women's clothes."

Next I would have to tell her how much I liked it and how often. I looked up at her, and heard her sigh. She was smiling.

"Thank God!" She exclaimed. "I thought you were going to break up with me or say you were seeing someone else, or you had committed murder or something!"

She paused, and put her hand on my knee. We were seated on the couch facing each other.

"How often do you do this? When?"

Should I tell her I was wearing panties right now? I put them on before she came to the apartment. I had never worn anything feminine around her, but this time I felt like it would give me courage, or make me feel like this was the right time or that I was committed to it.

"When I am home alone. That time you went to visit your sister over the weekend? I did it then."

"The whole time?" She looked surprised?

"Well, no. But a lot of it. I had to go to the store, and went out for beer with my friends."

I was not sure I should tell her yet that when we are not together, I sleep in a nightgown.

"I slept in a nightgown." Well, ok, maybe now is the time. She has to know the extent of it.

"I want to see it! Can you dress for me?"

"Wait...what? You don't mind?"

"No, of course not silly! You aren't cheating on me and I love you. Besides I think it sounds fun and I once thought you might look cute in a dress! Do you hate me for that?"

"No. I... when?"

"You are the only boyfriend I have ever had who doesn't mind coming with me to shop for clothes. And you always have such good fashion sense. That time we were in the little consignment dress shop and you pulled out some dresses for me to try. I don't know why the idea popped into my head. But it did."

"Which dress?" Now I was getting bold and to be honest the fear had left me completely. But I was still shaking. Sort of like I was cold. And my voice was getting a little squeaky.

"That short blue floral dress you pulled out for me. I liked it but it didn't fit, remember? It probably would not have fit you either, but... well, it crossed my mind."

"Wow."

"This is so cool now, don't you see? I have a great guy who loves me and is devoted to me, and he can sometimes be my girlfriend too!"

I don't remember now how exactly it happened. We chatted about that for a few minutes and suddenly we were up in my room with my totes of clothes that I had stashed away to keep her from seeing them. I had up until I met her been keeping them in my drawers and closet. But I packed them away in the basement where I could still get to them when I wanted.

"Do you actually dress completely? With underwear and all?"

"Yes." I said. "And I am wearing panties right now."

"Really? Do you always do that? I want to see them."

"No. This is the first time. Well, I mean...the first time when I was around you."

"Let me see."

At this point I was getting a little excited and was embarrassed about this whole thing. What had I done? How would things change? Would she hate me? Was I just going to strip naked for her right here? Was that a little creepy?

"You have to show me your underwear too."

"OK, " she said. "Let's see if you have good taste in women's clothes. And maybe I can help with that too." She started to pull her jeans down, so I did the same. We sat on the bed, pulling our feet through the leg holes, and she looked at my panties and said,

"Cute! You have good taste! What are they? Victoria Secret?"

"How could you tell."

"Do you have a bra that matches?"

"You are liking this way more than I expected! Yes I do." I rummaged in the tote and found my favorite lace trimmed bra that actually was part of a set with the panties.

"Let's get that on you..."

"First you have to take your top off. Just like me."

As she did that, I put the bra on, and she was surprised at how quickly I was able to do it. I fastened it in front of me, turned it around and slipped my arms into the straps.

So here we were sitting on the bed, both only wearing bra and panties, her with a beautifully filled out white lace bra, and me with a peach colored VS bra with nothing in them.

"You are a little flat" she said.

"Hang on." I reached in the other tote and pulled out my breast forms. They were attachable but I did not plan to glue them on, but just slid them into the bra against my skin. Voila!

"Wow, you really are into this. Where is your wig?"

They were not in the totes. Wigs suffer pretty badly from being folded and squashed even in a box so I had carefully stowed them away in a closet in the basement.

"They are in the basement."

"They? Let's go get one."

So here we are, padding downstairs to the basement in our underwear, to get one of my wigs. It felt comical and dreamlike to me. I thought an hour ago that this whole scene might end up with me alone and her either disgusted or laughing her ass off as she drove off, never to be seen again.

I unlocked the closet and pulled out my shoulder length light brown wig with the soft curls.

"Ooooh, that is pretty! Put it on. I want to see what you look like in it!"

I didn't have my brushes and stuff but I held it in front of me upside down, and flipped it onto my head, snugging the back down and adjusting the front to where it felt right. I could not be sure without a mirror.

"Oh, my darlin'" she said, "You look GREAT! Let's go back upstairs and get you into an outfit."

I was willing to be led to anything at this point. I was with the girl of my dreams, and I was wearing panties and a bra, and so was she! And I have to admit my excitement was hard to hide at this point.

We got back to the bedroom. She was ahead of me and started pulling out clothes from the totes.

"Is this the nightgown?" She asked holding it up with a smile?

"Yes" I said. "That is one of them."

"It is pretty! I think I would like to sleep in this sometime! Could I?"

My goodness this was going so much better than I hoped! "Yes of course. Do you have any I could borrow?" I grinned?

"We can see when we go back to my place tonight."

She pulled out a blouse and skirt and said "Try these on."

The skirt was calf length, cotton, with a kind of multicolored pattern like paisley. The blouse was a cute white peasant blouse I had bought at a yard sale several years ago. I put them on, and found my Birkenstocks to wear with them.

So now I was full dressed and she was not. "You should get dressed." I said.

While she pulled her jeans and top back on she said

"Get your makeup together. You do have makeup right?"

"Yes."

"Get it together and put it in a carrying case if you have one."

"Of course."

"I am going to pull out some more clothes, and this nightgown. If there is anything you especially want tonight, get it. And let's go back to my place. OK?" She was giggling, and I wondered what she had up her sleeve.

"With me dressed like this?"

"Yes. You look great! And no one will even notice. Come on. And no boy clothes, alright?"

Wow this was turning out MUCH better than I had hoped.