Costume Contest

"What's it like to be a beautiful woman all eyes on you?"

"How would I know?" I responded with a laugh.

"I'm serious, sitting there in your white blouse, black blazer, matching skirt & those classic heels you could have any man in here."

That's how it started just playful banter over drinks after a long day. We were both interns at the same law firm having a chance to experience hands-on work with attorneys and investigators, interact with scores of clients, assist with case organization, research, prepare motions and attend a variety of court hearings. We often went for a drink at the end of the day to unwind and compare notes. Over the six months we had worked together we had become a good friends.

Kevin is 5'6" light build, he had soft features, blond hair with blue eyes. I always enjoy talking with him about our days, the cases we were working on, the hearings we got to attend but today the conversation was different. I was not sure where he was going but decide to play along.

"You think it is easy being a woman?"

"That is not what I mean, look around at all these men in dark suits we all look the same interchangeable you on the other hand get to express yourself wear different colors pants or skirts, tidy dresses, blouses people tell you how nice you look not to mention the make up."

"You are forgetting all the work leg shaving, manicures, pedicures that it takes coordinating outfits finding heels that look good and are comfortable the effort it takes is exhausting."

"I would gladly go through all that to be has gorgeous as you I've seen how the lawyers and judges respond to you."

Laughing, I let it pass and changed the subject, talking about our plans for Halloween week-end. Kevin didn't really have anything planned so I told him about a band I wanted to see on Saturday at a costume bash at a local bar, first prize in the costume contest was a thousand dollars

"Join me cut loose have some fun."

"I don't have a costume."

"Leave that to me."

The next day I could hardly concentrate thinking about my plan. Leaving work I headed to Macys to pick up the supplies I would need to execute my plan. Guessing at the sizes I bought a skimpy black skirt, a silk blouse, heels, padded bra, thong & a blond wig along with make up. Could I really pull this off? Would he play along."

Saturday finally came, I awoke early, excited, it was going to be a busy day, I showered dressed and rushed out the door. I rang Kevin's buzzer at 9am, he buzzed me up, opening his door, "Is something wrong."

"We have a busy day ahead of us to get ready for tonight." I said pushing past him.

He looked at me confused "sit down I'll explain" laying out his costume.

"What!" he said laughing

"You'll make a gorgeous woman, Kevin."

Squirming in his seat, rubbing his sleepy eyes, I was sure now I was crazy, what was I thinking of course he never do this. "You think I can win?"

"When I'm done with you." We laughed "Today you get to be Kelly, strong independent career woman by day, a gorgeous slut by night." We laughed

I grabbed his hand leading him to the bathroom running him a bath.

"Start with a bath, shave your legs & underarms you want to be smooth."

I returned to the living room to wait amazed he was going along. My panties were wet has I sat on the couch sliding my hand down inside my panties I spread my legs rubbing my clit.

He emerged from the bathroom in a towel and I motioned for him to sit on the couch next to me my hand still working feverishly. With my free hand I slipped under his towel stroking his cock which was growing in my hand. Kevin laid back his head moaning has I worked us both toward orgasm. Erupting together his hot white cum covering my hand.

I buffed, shaped and polished his nails making small talk as I did. Kevin/Kelly had soft hands and small cute feet I was having fun hanging with my new girlfriend. Painting her toenails a bright red, blowing on her beautiful toes, admiring my work.

"All done"

She look a little amazed at her beautifully painted nails.

"They look so good." he smiled.

" try to make your voice come from your throat instead of your chest, you will sound more feminine."

We went to the bedroom and I laid Kelly's outfit on the bed he walked up picking up the blouse "Nice."

"I guessed at the sizes, let's get you dressed and see how they fit sweety."

Handing him the thong he stepped into it pulling it up, standing there in the black thong, with painted toes. Handing him the padded bra next, he slid it up his arms and I helped him clipping it, he looked down. "Wow I have breast." We giggled like little girls. "Sit down honey I'll do your make up." I applied foundation, concealer, blush, eyeshadow, eyebrows, lip stick and held up a mirror. "I look good." Kelly smiled.

"Your Gorgeous."

I removed the wig from my bag and fitted it in place handing the mirror to him he stared at his reflection smiling. The blouse and skirt followed I had to admit he look good. I brought the heels to him he eagerly grabbed them putting them on he admired his feet. "Walk around honey." He stumbled at first but was soon strutting around feeling his self or was it herself. Kevin or Kelly.

The transformation had taking awhile "I'm hungry let's go get a bite to eat."

"I can't go out like this in broad daylight"

"Your gorgeous Kelly"

"You really think I can pass?"

"I do"

Walking to the restaurant I could tell she was nervous but seemed to gain confidence has people walked past us. Has we came to the entrance to the restaurant a man opened the door saying "ladies first." We ate and talked, I instructed Kelly to talk from her throat instead of your chest, and thus it shall sound more feminine. A man walked by our table and smiled Kelly gave the slightest smile in return. Finish we ask for the check. "The man over there picked up your check ladies." the waiter explained. We smiled and waved.

Arriving back at her apartment she said "I can't wait to hit the bar tonight." I smiled. My plan had worked beyond belief Kevin had become Kelly and to my surprise was really enjoying it.

I showered and dressed at his place emerging from the bathroom.

"where's your costume?"

I fumble through the bags I had brought finally finding my black mask tying it on.

"Not much of a costume."

"Tonight is abought you, honey."

We had been in the bar for a couple hours drinking, dancing Kelly was really getting into her new role. Two cute guys approached our table, a cop and a clown, asking to join us. they bought us drinks which we accepted, taking seats next to us. They said there names were Eric(cop) and Ryan(Clown) as we laughed, talked, flirted and danced. Kelly was a good flirt, touching Eric's arm he leaned in kissing her I almost spilled my drink. Much to my surprise Kelly was responding kissing him back her hand rubbing his leg. My eyes transfixed on the scene playing out in front of me has their tongues darted in and out of each others mouth. Breaking my trance Ryan asked if I wanted to dance so we hit the dance floor looking back with amazement.

When we returned they were gone worried Kevin mite be found out I walked to the back of the dark club by the bathroom looking for her. Passing a hallway that led to a storage room I saw Kelly on her knees cock in her mouth sucking away. Mesmerized by the scene I was frozen WOW she's really getting into to it. Devouring Eric's cock, squeezing his balls Kelly was a good cock sucker. I smiled walking back to the table I took my seat. Kelly and Eric returned holding hands, so sweet, she took her seat next to me I whispered in her ear "You have a little cum on your chin honey" grabbing a napkin to wipe her chin I whisper.

"Now you know what is like to be a woman."