Crossdressing Stories


I am a young man of mixed heritage. My father was black, my mother Asian. My features reflect that mixed heritage, my skin like coffee with two creams, my eyes are dark and my hair is straight. I keep my hair at shoulder-length and cut in a modern fashion. I’m very slim, have almost no body-fat and almost no body-hair. My name is Sean. I had been quite feminine since my childhood but never really exposed it outwardly.
I’m not trying to sound arrogant, but I’ve been told by many people that I’m quite attractive. Never handsome, just “attractive.”

I had just reached my 27th birthday when my best friend Shauna said, “Sean, I want you to come to my house tonight for a special birthday present.”

Shauna is white and a few years older than me. We’ve been friends for years and love to laugh and gossip. Shauna is also a bit of a slut. She loves to tell me who and how she got laid the night before. She is a kind and wonderful friend, someone I could not live without.

I answered, “Alright, alright, what’s this ‘special present’?”

She laughed and said, “Wait and see.”

I got to Shauna’s house around 9 p.m. and had brought a bottle of champagne of all things. She met me at the door and laughed at my gift. “Come on in. Let’s give this a try.”

I entered her house and we went to the den. The bottle was fairly cold, so she brought glasses and we popped it right there. It was a very good champagne, something I’d spent a bit of money on.

I said, “The gift, the gift, what is it?”

“Wait, wait, don’t be in such a rush.”

We laughed and gossiped about people we knew and the bottle was soon finished. I could feel the alcohol in my system, but neither of us was really buzzed. Finally Shauna got to the point, “OK Sean, time for your gift.”

She stood up and took me by the hand. She led me to her bedroom and had me sit in a comfortable chair in front of a brightly lit makeup table.
I was confused. What was going on?

She said, “Tonight I’m going to give you something special. Tonight I’m going to make you up.”


She started laughing and went on, “You are my very best friend and I know you very well. Somewhere in that dark mind of yours, I know you want to try being a woman, or at least for one night.”

How could she possibly know that one of my fantasies was to be made up?

To be a woman even if for a short time?

I said, “No way.” pretending to be miffed at her suggestion.

“Liar, you know you want this.”

I also laughed and said, “OK, OK, let’s try this. How do we do this?” “Just sit back and let me do take care of things.”

She then began to change my life.

She slowly and carefully began to apply makeup to my face. She stopped and explained each step and function. Face-powder and rouge, lipstick and mascara. She spent a lot of time on my eyes and they popped with beauty. She said, “I picked out these dark colors to match that beautiful skin of yours.”

In an hour or so, I saw myself become transformed from an ‘attractive’ man to a very beautiful woman. Damn I was hot. I turned my head back and forth trying to take it all in. I was really good looking, really beautiful.
Shauna brushed my hair and pulled it into a ponytail. I looked like a very young Halle Berry. I mean I was really stunning.

I said, “Wow, wow, how did you know, how were you able to do this?”

She laughed and laughed, then gave me a big hug. She said, “Happy Birthday Sean. I love you.”

I stood up and twirled a little and we both laughed. She said, “Want more?”

“What do you mean?”

“Want to go further, maybe try on some of my clothes?”

Oh my God, what was happening?

I said, “Alright, I’m really getting into this.”

She dimmed the lights very low as she sensed I was slightly embarrassed.

She said, “Strip, get out of those clothes.”

I slowly undressed in the dim light and was soon naked in front of my best friend. Shauna reached put and began to stroke my special part. “Wow, much nicer than I’d have thought.”

“Cut it out, what do you want me to wear?”

She went to her dresser and looked through her lingerie. She found a black pair of panties that were slightly larger than a G-string. She said, “Try these on. You’ll have to tuck your buldge in to get into them.”

She handed me the panties, then I attempted to tuck . No luck, it was pretty hard at the moment.

We both laughed at my predicament, but I put the panties on anyway. She said, “Wait’ll gets soft, then you can try and tuck it back in.”
She went on, “Hmmmm, a bra, a bra. Here, try this on, it’s got a lot of padding.”

I put the bra on and had a little trouble with the clasp, so Shauna helped me. By then my private part had softened, so I pushed it back and in place. Shauna said, “Shoes, shoes.”

She went through her closet and pulled out a pair of black stiletto pumps. She said, “These are my biggest pair, so you might be able to get into them.”

She was right, the shoes were very tight, but I managed to get my feet into them.

I was teetering as I stood, so Shauna held my hand and helped me to the mirror. Wow! The reflection I saw was that of a very tall, very slim super-model. I was fucking hot!

“You like?”

“I like.”

“Turn around and look at your ass.”

I turned around then peered over my shoulder. What a great ass.

She said, “Follow me.” and took me by the hand. She led me to the den and we sat on the sofa. She said, “Does this turn you on?” I could feel myself try to harden in its tucked away position so I said, “Yes, very much. Much more than I thought this would.”

She said, “Look, you are my very best friend, so don’t be weirded out at what I’m going to do.”

“What are you going to do?”

“Just go along with whatever I do.”

She then reached down and begun to massage my body. I could feel the sensation harden and strain. She pulled my panty down. “Wait a minute.” she said and dashed out of the room. She returned with a hand-held mirror and gave it to me. She said, “Look at yourself as I massage your body.”
I held the mirror in one hand and looked at my beautiful made-up face. Shauna stroked my body. I was excited as she touched me and I looked at my stunning reflection. How well did Shauna know me? Pretty damn well.
My life was now very different than it was a few hours ago. I was enjoying my feminine sensations.

The days and weeks that followed were wonderful. Shauna helped me find new clothes, new outfits, and new makeup. I totally surprised myself with how much I enjoyed dressing and acting like a woman.

Shauna was an excellent teacher and gave me many, many instructions on how to act, talk and even walk. Many nights were spent at Shauna’s house playing dress-up. God I just loved it. That is how I started to become Amy.

The End

Facebook Comments


  1. So LUV 2 b Amy. SO need a MISTRESS 2 train me PLEASE

  2. Love to play and share stories

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