All of my life I have had the occasional thought of being dressed like a girl. None of this frilly pink stuff, and nothing I have dwelt on, but the occasional passing thought of being dressed like a girl. I am the youngest of 3 children in our family and I have 2 older sisters. When we were kids I had macho boy stuff to play with, but when I played with my sisters it was with Barbies, tee sets, and dress up; so I knew a lot about girl stuff.

Let me put this straight: I have never wanted to be a girl, and I enjoy women very much.

One night just before New Years, this year, my gf and I were doing kind of a truth or dare the of play where we would ask each other: "have you ever" type of questions. I think we were being honest with each other. She asked: "Have you ever wanted or actually dressed like a girl?"

I told her: "I have never dressed as a girl."

But she pressed it and said: "But have you ever wanted to?"

We were being honest, so I told her that I had, on occasions, had the thought of being dressed like a girl run through my mind. After that her focus became what I thought of when I had thoughts of being dressed like a girl. What type of clothing, shoes, makeup, and etc. After several more minutes of this type of questioning, she gave me a thoughtful lool and said: "You'd look good dressed as a girl. Would you allow me to show you? Think about it."

I thought ya, ya, dress like a girl; blah blah blah... She much have known what I was thinking because she said: "No. Seriously. I would do this with you. Will you let me show you?"

I didn't see her for a couple of days, but we text and sext al the time. She sent me some links on "transformations" along with messages of "I want to do this with you."

I decided, what the hell. She looks like she really wants to see me dressed like that, and I'm sure I'll get some good sex out of it. So I texted her back that I was willing to try it. She said New Years Eve day would be good for her. We planned to spend the entire day together, so it was good for me too. I agreed.

I don't have much body hair and what I do have is blond and very fine, but she waxed it all off, tweazed a bit of my eye brow so I have less of a unibrow now. She helped me exfoliate my body--that was well worth it by itself, I left a couple ropes of cum on her shower. She even gave me a facial, manicure, and pedicure. She did the works, finger and toe nail polish, full makeup, eye liner and shadow, lipstick, and that is about all I could recognize of what she was doing. I have to admit the stockings felt really nice as she put them on me, and the silk and lace panty too.

This all started in the morning abot 10AM and she didn't let me take a look until almost dinner time. I was dressed head to toes as a girl--starting with a blonde wig and all the way down to my painted toe nails when she finally said: "OK. Take a look. You are gorgeous."

When I looked in the mirror I couldn't believe what I saw. She was absolutely right, looking back was a nice looking blonde girl. All I could do is stare, and say: "Wow."

She handed me one of those little keep in your hand type of purse and said: "Let's go."

I looked at her and said: "NO FUCKING WAY IN HELL!"

That's when I noticed. She had done all this same stuff to herself too--she was not only totally gorgeous, but I could tell she was completely hot to go. She stomped her 5 inch clad foot and gave me a little pout: "I wanna go have fun. I'll make it worth it later."

She just spent like 7 huors getting ready to go out. I reluctantly agreed, but only on the condition we went someplace I wouldn't be known. She agreed.

Shit! We ended up at a lesbian dance club. I was not known there alright. My gf just told me don't talk and they won't be able to tell. Well, that was mostly not true, but the girls were good sports about it and many of them were intrigued that I made such a good looking woman. All in all it was a good time at the club. We danced, ate, drank, for a few most of the night. The girls that thought it was cute or cool or whatever danced with me, they danced a lot, and ordered drinks a lot. All the while my gf just kept getting hotter, more excited, and after a while of this I could tell she was ready to go. She was well ready to be bedded, I could actually smell her readiness.

About 11-ish I noticed she was hanging out with one of the girls that thought it was cool that I was doing this. All 3 of us got really chummy--dancing close, hands in friendly places, kissing, and etc. As the countdown started for the new year we started making out--the three of us--and when the new year arrived, my gf told me: "Let's go, we are ready."

I was instantly sober, and my cock was trying to rip out of the lace panty! Nobody had to tell me twice. Two beautiful women in tow, we all but ran to my gf's car. We got to her apartment and clothing started coming off. Things were left in the hall, in the elevator, and by the time we were in the door, bare breasts were being sucked and fondled. We made it to the bedroom and things really went crazy. My gf was laying naked on the bed, the woman from the club was nude and they were in a 69 type of position; I got behind her and started my dick into her. She went wild on my gf's pussy and my gf took my balls in her mouth as I slowly grond into the girl from the club. That set the tone for the entire evening. I fucked the girls as they made out. During my recoupe times, we all made out, licking and sucking my cock, fingering my bottom, me licking their pussies. It was a blur until I passed out from exhaustion.

I woke sometime after dawn to the two girls starting up again. We fucked a couple times more, and spent most of the afternoon together--mostly in bed.

True to her word, my gf made it worth my while: oh, it was so worth my while. Now she is asking if I want to do it some more.