The Chameleon

This story is a work of fiction but is based on some true incidents. Names and places have been changed for obvious reasons. I would love to hear back from you.

My boyfriend Tony burst out laughing upon hearing my experience at a local bookstore that morning. I pouted. That made him laugh even harder. He responded by saying "Hmm... that gives me new ideas!".

That morning I was browsing for some books at the local bookstore. A little while later, I heard the sales assistant say, "Sir, can I help find you any books?" I figured he was talking to someone else, so I ignored him. I heard his offer of help again, followed by tapping of my shoulder. I turned around and looked at him and he was taken aback. He was all red faced and apologized profusely. When I went the counter a few minutes later, he apologized again and even offered me additional discounts.

Tony said, "Its obvious why he made a mistake. You are almost 6 feet tall with short hair and you were not wearing a bra." "True, " I said, "but its still not very funny." I have a very small bust, I am 30A and hate wearing a bra. Because I work out, I have a very muscular body.

My boyfriend Tony is actually much shorter than I am. He is only about 5'6" tall and has a fairly compact body - no flab but no bulging muscles either. He has gorgeous blue eyes and shoulder length blonde hair. He is an absolutely wonderful person, very artistic, great cook and best of all a great lover. He is not bothered by my sexual preferences at all. After being with him I learned that size really does not matter. His penis is on the small side, just over 4 inches when fully erect. But I have had more orgasms with him than ever before. He uses his mouth, fingers and even toes with great skill. He also stays erect for a long time.

Later that evening, Tony asked me "Have you ever dressed up as a man?" When I said no, he wondered, "Would you like to try?" Always ready for an adventure, I said "YES." Tony went out shopping. He laid out new pair of mens underwear, pants, shirt and a sports jacket. He sat me down and cut and styled my hair even shorter. He help me get dressed and showed me the basics of walking and the way of carrying myself. He coached me on my voice, to help me speak with a deeper voice.

We went to a local bar like two friends out for a drink. The dance floor was crowded. Tony asked me "Would you like to dance?" When I nodded, he said, "Lets go find us some chicks." There were two women sitting at a table and Tony and I joined them. One was a brunette, her name was Lisa, while her friend Sharon was a gorgeous blonde. She had lovely green eyes and a beautiful smile. Tony asked Lisa to dance and off they went. Sharon and I sat nursing our drinks and watching them dance.

Feeling awkward, I asked Sharon, if we could dance. Her smile lit up the room, "I thought you would never ask." So far so good, I thought. We went to the dance floor. There was a fast number playing. A few times, my hands touched Sharon's body and I felt the familiar ache in my pussy. We had a great time. The only hitch came when I had to use the rest room. Luckily I have trained myself to pee standing up, so I was able to use the men's room.

When we got home that night, I was so turned by the experience that I asked Tony to fuck me in the ass like a man. Later, I made Tony lie on his back at the edge of the bed. I lifted his legs up and using my finger for a penis, shoved it up his ass. The orgasms that followed were explosive.
We repeated my dress up experience a few more times. After each such experience, I became the more dominant partner. I loved to fuck Tony in the ass with my fingers and loved the way he treated me,

On the evening of my birthday, when I returned home, I found a post-it note on the microwave, asking me to go up to the bedroom, Tony had asked me to get dressed up and be ready by the time he got back.

I went up to the bedroom and found a set of men's clothes laid out. Beside it there was a gift bag. I opened the bag and found a double headed dildo and a harness. The dildo was beautifully made and matched my skin tones as did the harness. There were instructions on how to wear that. I dutifully followed the instructions. When I looked at myself in the mirror, a young man with a hard-on looked back at me. I stroked my erection and found that the head inside me moved and gave me intense pleasure. By the time, I wore the underwear and rest of the clothes Tony came in. He kissed me and said, "Mmmm. You bring out the bisexual in me." He groped at my hardness and ran his hands over it. Next thing I knew he had unzipped my fly and was kissing my new penis through the underwear.

I lowered my pants and underwear. He kneeled before me and took my cock in his mouth. He gave me blowjob and brought me to a climax. He applied lubricant to the dildo generously and made me lie on my back. He then lowered himself on the erection. While moving up and down he stroked himself and blew his cum over my shirt. We both lay exhausted, then we changed and went out.

After dinner, we went to a night club and spent the night dancing away with other women. One of the women seemed to have taken a liking to me. Cheryl would stay close to me and let me feel her. Finally I asked Tony, if Cheryl could come with us. Tony drove, while Cheryl and I made out in the back seat. Cheryl slipped her panties off and waved it in front of my nose. It was wet and the smell drove me out of my mind. She then took her blouse and bra off as well, her lovely breasts and hard nipples in front of me. By the time we reached home, I had eaten Cheryl's wet pussy and brought her to multiple orgasms.

We rushed inside the house and headed to the bedroom. Once I had my clothes off, she realized I as a woman. Her first reaction was one of horror, then she said, "You know, you are the first one with whom I came so many times. What the heck, fuck me with that big cock of yours."

She caressed my breasts, "You have such beautiful firm breasts. I can cover them fully with my mouth." She turned to Tony and said,"Hey why don't you join in the fun? Two cocks are better than one." The rest of the night we spent in ecstasy.

Next morning we woke up with Cheryl in the middle. Soon we were going at it again, the three of us.

Cheryl has now moved in with us. Sometimes she and go together as a couple, while other times, we go with Tony. While their gender is set, I am the only one who seems to be changing like a chameleon. Lately Tony has been talking about dressing up - like a woman. May be thats a story for the next time?