To Be a Woman

Katie must have realized something because she stopped me from entering my little car. "Why don't you and I grab some drinks at my place?"

I told her that I was done for the evening. She grabbed my arm and pulled me in close and whispered in my ear. "You know the night doesn't have to end Greg."

I froze. I looked at her with a helpless look in my eyes. Embarrassed, I told her that it would be fine to have a glass of wine with her at her house. As I drove to her house, following her SUV a thousand things were running through my mind. What could I say, and why not just go home? My worst fear was to have her call Debra and then all shit would break loose. I loved Debra and didn't really want to go through all that. As I pulled into her driveway of her cute little townhouse, I felt like throwing up.

Katie once again slipped from her SUV and I, again, felt a twinge of sexual attraction as I once again tried as womanly as I could step from Debra's convertible. Katie smiled and took my hand as we entered the house. I plopped down on the couch and realizing how unlady-like it was crossed my legs.

"So how long have you been like this?" She asked.

"Today was my first day dressed in public." I explained in my regular voice. I resigned to telling her the entire story and the lie I told her in the car. She poured some wine and listened as I told her what I had done.

"When did you find out?" I asked.

"When I called you from the car, I saw you talking on your cell with me. You can talk to me as Ginger."

I cleared my throat and started again, "So you knew at the bar."

She smiled, "Yes, and I have to say I was surprised that you kissed another man." She paused, "are you gay?"

"No," I said. "I didn't want to blow my cover as a woman. And..." I trailed off.

"And what?" she asked with a raise to her eyebrow.

"And I wanted to see if I was woman enough to turn on a man." I said it quietly.

"I see, you are very passable, maybe some more work on you makeup. Does Debra know?"

"No." I was feeling embarrassed and sad, and I was getting drunk as the wine continued to flow.

"Did you like kissing your man?"

"No, he was a horrible kisser."

Katie began to laugh and she sat next to me on the couch with her wine. Her hand lay on my knee. It felt comforting.

"Well, your secret is safe with me." She said almost as an after thought. I was confused, and look at her with fallen eyes. "Look, most of my girlfriends are married. None of them want to stay single anymore."

I didn't really know where this was going.

"For the first time I felt so free to just..." she was trying to find the words. "You saw me with that guy." I nodded, she continued. "I have never been able to do that in a while. There is just something so sexy about making out with a strange guy. And with you there, I felt safe. I knew nothing was going to happen." She leaned in and kissed me fully on the lips. I loved it. Her hand on my leg was moving up. My head was swimming and my cock was finally coming alive.

Our kiss was passionate but not overly active. The mix of her lipstick and mine made the kiss slippery, but not wet. Her lips were full and beautiful and I felt as if I was in heaven. Her hands reached as far as the tops of my black stockings and stopped. Although, I would have let her go farther up my leg as she wanted. The smells, the feeling were all intoxicating.

When Katie had finished kissing me, which seemed to last for minutes, she looked at me deep in my eyes. She gave me big doe eyes as she began to ask. "Would you be my new girlfriend?" Shocked, I stood up. I was coming to my senses.

"Look, it really was a mistake doing this. I just did it to get off tonight. I never expected to go out really, or run into you. Let alone kiss some guy." She listened very intently as I continued. "I want to have sex dressed like this with a woman, but I really don't want to cheat on Debra. I just don't want to jeopardize that, not now. Really this just was an opportunity to be a pervert."

It took her a while to digest this information. I wanted her so much, to lean her back on the couch and hump her with my nylon covered legs around her. But it turned to be a serious conversation. I was ready to go home. She stood up and gave me a big hug. Our heels click together and our legs rubbed. Her perfume and my wife's were mixing in the air. She pulled away and looked at me.

"I can understand. I mean I guess I know what you're going through, but I am turned on by you right now. And this could be our little secret. You don't have to kiss guys if you don't want to." Some how what she said comforted me and turned me on. I leaned into her and gave her a peck.

"I should go home."

"Are you dressing tomorrow?" Katie asked.

"I don't know?"

"Please do, and call me." She smiled and hugged me again.

I walked back to my Debra's car and again slipped in as a woman. The drive home was relatively quick and my head was heavy and my body felt it had been in a fight. I parked in the garage and my heels clicked as I entered the house. My hair and clothes smelt of cigarettes and a tinge of Katie's perfume. My feet felt some relief as I slipped out of the heels, and I looked at myself in the mirror. I was still aroused at the figure looking back. My legs looked so good, even out of heels, and my hands began to rub over my body. I started to strip until I was naked except for my pantyhose were around my ankles.

I stood there with my cock in my hand looking at my face framed in blonde hair and in makeup. I didn't jerk hard like I used to, but instead kept a slow and deliberate pace until I relieved myself. I relived all the events of that evening. Thoughts ran through my mind about dressing up, kissing Adam, getting caught by Katie and the deep kiss we shared. When I was done, I cleaned the mess up and took a quick shower to wash the makeup off. Then I slipped into some of my wife's panties and went to bed.

The next morning I called Katie.