Little Black Dress

It all started with a good-natured argument between my wife and her sister. Emily bought a little black dress on sale and she had put it on to show her sister. Her sister, Rose was a 'name label' person and to her by just being on sale, if for no other reason made the dress not worth wearing.

"Emily I'm telling you it hangs on you all wrong, it's not cut right and it's too baggy."

"Oh stop it Rose, it'll be fine, it's not like I'm the one walking down the aisle."

They were going to the wedding of one of Rose's friends and she felt as if her sister would embarrass her by wearing a bargain basement dress. When Rose told Emily that her husband would look better in the dress than she would, she took it as a challenge. She called me into her bedroom and asked me to put it on. I didn't ask questions, when Emily has that look in her eye I know better than to argue with her. As a man that is slight of built, my wife is just about my height and I would say we weigh within ten pounds of each other; I fit into the dress with ease.

I looked ridiculous and both girls began laughing as I walked out of the bathroom with the dress on. However, that didn't stop Rose.

"Of course, he looks silly dressed that way, he has to be in the whole package. Let me fix him up and then we'll judge."

She sat me on the end of the bed and began putting a pair of nylons on me. She teased her sister that she was looking up my dress and could tell I was a brief over boxer type of guy. This made my face red but also I found this talk strangely erotic. The feeling of the stockings on my legs was even more erotic and I began to feel an erection coming on. When she began to talk of a garter belt was when I put my foot down and said no more silliness.

I did not look better in the dress that Emily but I think her sister had shamed her enough that she agreed to go shopping with her for another. They grabbed their purses and left me there still dressed in my wife's clothes. I took off the dress and I happened to notice my reflection in the mirror, as I stood there still with the nylons hugging my legs. I looked silly but not because of the stockings but my underwear. I went to my wife's lingerie drawer and my world changed in that instant. I couldn't believe all the colors and they all felt so soft and feminine. I couldn't stop myself I had to try on a pair but which ones, it was worse than the ice cream store. I took a pair of white laced silk out and held them up against my briefs. I remembered my wife calling them boy shorts and somehow that made it all right to try them on.

By now, I had a raging hard-on and it stuck out the top of the panties. I forced it down between my legs and held it in with my thighs. It all felt so sexy and I wanted more. I found one of Emily's garter belts and strapped it on, than I attached the nylons to it. My wife always says she is a B-minus cup so she has little foam inserts to fill the cup out. Even I know she is only an A but this makes her feel better about herself. I put on her bra and the small foam insert made me look as if I had breasts. I now slipped the dress back on and as far as I was concerned, I was a vision of loveliness.

Ever since that fateful day I try on my wife's clothes every chance I get. If I get home and she's not there I head straight for her lingerie drawer. I pick out something that looks sexy to me and try it on. I learned that one should put the garter belt on before the panties, to make relieving one's self easier and now when dressed as a proper lady I always sit to pee. I've also found I enjoy dresses with a fuller cut than the shift I wore the first time. I have practiced so many time walking in Emily's high heels I feel quite comfortable with them now.

When Emily announced that, she and her sister were leaving town to visit their mother I looked forward to a weekend dressed in drag. As soon as I put them on the plane, I rushed home to play. I drew a luxurious bath and sprinkled it with Emily's favorite bath oils. I pampered myself as I soaked, then I washed my hair. Lately I have let my hair grow longer and I was sure if I blow-dried it right it would pass for a pixie cut. I walked naked except for a towel around me to our bedroom. When I passed the mirror, I noticed I had, without thinking, wrapped the towel completely around me as a woman instead of around my waist as a man would.

I looked in Emily's closet and the first thing I saw was that little black dress. Now that I was so much more experienced, I wondered if I would look better in it than before. I grabbed it and threw it on the bed, for tonight I was to find out. First, I put a garter belt on and as always, I got that tingling feeling as I rolled the nylons up my legs. Next I took a pair of French cut pink panties and put them on after forcing my dick between my legs. After practicing, I had learned how to hold it there so it wouldn't show. I put on the matching pink bra with the foam inserts already feeling sexy as hell. Staring at myself in my wife's dressing table mirror, I thought about make-up. I had not tried make-up before as I worried about not being able to clean it off before she came home. I remember my mother telling my sister, 'Less is more' so I applied a touch of color to my cheeks. Then some color for my eyes and them a light pink for my lips.

I let the dress fall down over my body and admired my reflection in the mirror. I added a strand of pearls and clip on earrings from Emily's jewelry box and grabbed a black clutch to match my black, 'oh so' high heels. Wow I not only felt like a woman I looked like one too and cute if I may brag. This was killing me, I had to show off to someone I wanted the world to see how pretty I had become.

I knew right away that I wanted to see if I could pass for a woman, I had to try it, even with the risk of humiliation I had to find out. With just one more glance in the mirror, I grabbed my bag and left the safety of my home for the outside world. I hurried to my car and headed for the other side of town. I parked in front of a coffee shop as it looked safe and maybe it would be just right for my coming out party. As I got out of the car, I noticed a bar next-door and all thoughts of safety went out the window as I headed that way.

I sat at the bar and ordered a cosmo without feeling guilty about it being a girly drink. Just as I drank it down another was put in front of me. The barkeep told me it was from the gentleman at the end. Feeling brazen, I looked over his way and smiled as I held up my glass. I had seen this scene in countless movies but never in real life and had only thought about it from the man's point of view. As a man, the fear of rejection had always stopped me from trying to pick up women in bars. Now as a woman I felt in control as I could either ignore him or be nice to him it was up to me. I felt his presence as he slid down the bar to the stool next to mine. I turned to him, smiled, and in my most feminine voice thanked him for the cocktail. He said his name was Hank and I introduced myself as Teddy. He was from out of town and only here for the weekend. After another drink I could feel my head start spinning and when he asked if I wanted to go somewhere for coffee I agreed.

Once out in the night air I realized what kind of a situation, I was getting myself into and I began to worry. I had to be careful, if Hank found out I was really a man there was no telling what he might do to me. I wanted to flee but knew I'd had too much to drink to drive. That meant I was at Hanks mercy and I wasn't sure I could fight him off if he started making advances to me. I knew I had to think fast and come up with some kind of plan. When I climbed into his car not only was my head spinning, my wheels were turning also. I knew it was now or never, so as he got into his side I made my move. I put my hand on his thigh than said,

"Hank I want to be up front with you, we can't do anything you see because I'm married."

As his answer he leaned over and kissed me, I couldn't stop myself as I returned his kisses. I was surprised at the difference in being kissed by a man. His lips firm and almost chapped teased my lips and his hint of a beard was something I'd never experienced before.

Before I knew what was happening I was becoming aroused and I could feel my loins start to stir. I made no resistance as hank moved my hand up his thigh to his erection. I thrilled as I squeezed its hardness and I yearned for more. Yet when he put his hand on my breast, I woke up and knew I had to stop him before I got into trouble.

"Hank I told you I'm married I can't do this."

"But baby, you got me so turned on you can't stop now."

I made a decision and as I continued to stroke him through his trousers, I said the only thing I would do was to put him in my mouth. Before I could even think about what I had said, his fly was open, and his cock was in my hand.

"If you want me to do this for you can't touch me OK. Promise me you won't touch and I'll do this for you."

He was so excited he would have promised me anything and as I held my first cock other than my own, I leaned down and kissed the tip. It felt oddly erotic so I opened my mouth and let it slip in further. I tried to think of what I might want as I toyed with him with my tongue. I kept as much saliva as I could in my mouth to keep him nice and wet. I held him with my hand as my lips went up and down along his shaft. I wanted to do a good job, I wanted to please this man, I don't know why. When I felt my saliva running down onto my hand I used it as a lubricant and masturbated him as I held him in my mouth.

When he came, I was so surprised I almost spit him out but still I held him in my mouth. I tried to savor the taste of his sperm but it was not something I enjoyed and yet maybe the texture or maybe it was just the act itself, I wanted it to last a little longer. When his erection waned, I took him from my mouth and only then did I swallow his load. Next, I took great care to clean him with my tongue and then I tucked him back into his boxer shorts and pants.

With Hank now sated and tired I knew now was the time to make my break. I told him I had to leave and jumped from his car, running back into the bar. I asked the bartender to call me a cab and hurried to the ladies to hide from Hank. About ten minutes later the bartender knocked on the door to tell me the taxi was here. With one last look in the mirror to check my makeup, I left the ladies room and went with the cabbie.

All the way home, I let the night run through my thoughts. Did this make me gay, before the events of the evening I hadn't thought about it? I mean I know I was dressing in women's clothes but I was still making love to my wife. It was all so confusing and once at home I undressed but left Emily's panties on as I went to bed. I began to masturbate with fantasizes of Hank using me for his pleasure. In my fantasy, every thing worked together as somehow I had both penis and vagina. When I came, it was hard and fast and I filled Emily's panties with my spunk.

Since that wonderful night with Hank, I have not dared to be in public dressed as a woman. When I think about how much I could have lost if things had not gone well it scares me too much to try again. Yet in my head I've played that evening over and over until it is perfect in every way. I keep telling myself that's all I need, I had my fling, and now I should get on with my life. And still I know that it's not enough and that someday I must venture out again as Teddy

As for Emily and I, we have had some problems as of late and I know she wonders why. I know I could never tell her of my adventures, she'd never understand. Of course, I still love her but our sex life has gone downhill and sometimes even as I close my eyes and think of other things, I remain unaroused and flaccid. My poor wife blames herself and there is nothing she can do. As she lies in bed silently crying I find I only have one thought and I keep saying to myself, ' My darling Hank if only we can meet again.'