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July 28, 2007

A Bra For Mickey

story categories: sex stories,transsexuals
[full story is 2,206 words]

It was a hot June day. The kind of day that made you feel that you were swimming in the air rather than breathing it. I was sitting in front of the fan trying to stay cool. I was completely naked. I looked down at my body examining the source of my greatest shame. I have an o.k. male body except for the size of my chest.

From the time I was 10 years old I had always been embarrassed by my chest. I remember how free I had once felt being able to run around at the pool with my shirt off, no more. Where a perfectly flat chest had been as a little boy now I had developed larger breasts than some women I knew. I found it hard to buy clothes that fit because of them. I always have to get a large chest size even though the neck and waist is always much too large.

I remember the day at age 13 when it finally hit me that I was different. I was playing happily in the local pool with some friends. I was oblivious to anyone’s looking at me, I had convinced myself that I was too self conscious. It was then that a 16 year old girl called me over to her and said, “Hey Mickey, why don’t you buy a bra!”, I ran back into the pool–crushed. I felt like I had been hit by a cannon ball. I thought to myself, “I wish I were a girl, I would be accepted, even admired for my chest, my breasts, my boobs… if I were a girl.” I stopped going to the pool. Even now some 20 years later I can still feel the pain of that day. I started to sob softly as I remembered it. It was only in private that I felt comfortable with my shirt off and my large breasts exposed. I wonder what they would look like in a bra? Or wearing a dress that was designed with a full cut top and a narrow waist? I wonder what it would be like to get completely dressed as a woman and go out on the town wearing a bra and a dress, and jewelry and having long silky sensual hair? I had never shared my fantasy with anyone, although the thought of it felt thrilling.

As the fan continued to whir, I was awakened from my daydream by the doorbell ranging, I wiped my tear streaked face with a towel and slipped on my shorts. When I pulled open the door a friend of mine, Wendy, bounced in full of excitement and life. Wendy had just been shopping and thought that I could use some company. She said that her apartment was full of the day’s purchases and she wanted to model everything for me. Since her hair was now cut very short she said had even bought a long wig for a more soft feminine appearance on special occasions. But even with her short hair there was no doubt that Wendy was all woman, her curvaceous body was the envy of every woman and the lust of every man who saw her. She had an athletic body that told you she worked out, but she didn’t allow herself to become all skin and bones, you could see her womanly figure tugging at her bra, and her full hips filling her skirt. Even at age 35 she looked like a fresh yet sensual teenager.

Wendy was a beauty parlor operator and her appearance was the best advertizement for her trade. “Hi Mickey” She said in a singsong voice as she entered into my warm apartment. She chattered on about the mall and all the things she had purchased. Then, she noticed that I had been upset about something. Wendy asked me what was wrong. I looked at her afraid to say. Then, as though a dam had broken inside of me the whole thing tumbled out, the years of hurt, of insecurity, the teasing at school, and even the fantasy of actually being a girl (or now a woman). I told her that I had never told anyone and asked her to please keep my secret. Wendy took me in her arms and held me as my tears came again, she was being strong for me in my personal weakness. With Wendy holding me I felt someone at last understood. She was like a sister in whom I could confide my deepest secrets.

After I quit sobbing Wendy told me that she had an idea of how I might find some help for my inner pain. She said, “What if I could make you into your fantasy?” “What do you mean?” My voice trembled. “What if I could transform you into a buxom beauty that would be admired for your ample attributes? I’ll bet that I could make you up and dress you so that no one would know that you weren’t born a woman, you could proudly display your breasts for all to see.”

I didn’t know what to say. Wendy knew I wanted it even though I was afraid to say so, she instructed me to follow her down the hall into her apartment, It was much cooler in her apartment with the air conditioner running. As we entered Wendy began to open the boxes that she had brought that day and pulled out articles of clothing, a bra, panties, a long flowing floral dress and a beautiful long blonde wig. “Well” she asked, a smile crossing her face. “Strip out of those old boy things and I’m going to get you ready to knock some eyes out, you’ll be a gorgeous sex kitten before I’m through with you!” My breathing was getting more rapid, I couldn’t believe what she was saying, I was a little scared, but I obediently followed her instructions.

After I stripped, Wendy lead me to the bathroom and shaved my legs, and my chest. As she shaved my chest she teased me by saying, “When I’m done with you honey, these sexy titties of yours are going to make people sit up and take notice.” If I blushed Wendy didn’t seem to notice. She acted with a professional air that calmed me. I felt as though I was one of her clients at her chic uptown beauty boutique. She even began to call me “Michelle” and engage me in “girl talk”. Telling me how Men don’t understand what “we women” go through getting ready for a date.

After the shaving was done Wendy sat me down in the bathroom and plucked my eyebrows so that they formed a feminine arch. She said, “Now Michelle I didn’t want you to look until she I’m all done, I want you to get the full effect.” With that she continued the process, putting on eyeliner, mascara, and blush. She asked me to pout out my lips more and she applied a pink lipstick. I was getting anxious to see. “Now Michelle” Wendy said, “You are getting there but there is still some more to do, tonight there are going to be some broken hearts about you!” I wasn’t sure what she meant but I sat there obediently. To my fingernails she added some long tips so that my hands looked beautifully feminine. Wendy did my fingernails in a pink frosted polish and did my toenails in the same color. She fussed for about an hour over all the details of my makeup until she finally smiled and kissed my forehead. “There you are little sister.” she said lovingly. Then she went over to her jewelry box and produced a pair of long earrings and clipped them on my ears, then she put a gold chain around my neck with a little heart pendent. Finally standing back admiring her work said “done.”

Before I could look in a mirror Wendy pulled me out into her living room and made me slip on a pink garter belt and panties. The satin material felt deliciously soft against my naked skin. Then she produced a light pink bra that matched the panties and garter belt. I began to tremble slightly. Wendy knew, I had always wondered what it would be like to wear a bra but I had never dared to try one on. Silently as though she was holding a wounded sparrow Wendy stepped in back of me, slid the straps over each arm, and pulled up the cups of the bra over my… eh, breasts. There I said it, they were now breasts, titties, my boobs. I felt glad not ashamed to have them. As the bra cups surrounded my breasts they comforted me, they felt right. My titties filled the cups. Wendy hooked the back of the bra into place and turned me around. Wendy looked at me with a professional eye, “Michelle, I’m surprised myself, but the fit seems just right. Without any help from padding you fill out to a 38B! With this padded bra on you look like a C cup.” I was surprised too. Looking down I saw that my bra not only surrounded my breasts but perfectly supported them and pushed them up forming a deliciously feminine cleavage. I felt my whole body tingle as I looked down. I felt my breasts wearing what they were made for. I felt proud of the way they looked.

I didn’t have time to ponder my womanly proportions, Wendy now produced a pair of light brown tinted hose and told me to slip them on, as I pulled them on they encased my legs in the most deliciously soft material that I had ever felt. My legs were always without question more like my mother’s then my father’s. Wendy snapped the clasps closed on the garter belt, straightening out the nylons.

Then she pulled out a long flowing sundress, “Michelle, I think that this dress will look beautiful on you on a warm summer evening and the top will make the most of you fabulous figure”. She was right, the dress was utterly feminine, with a purple floral print on a white background. The long flowing skirt rested lightly on my legs and the daringly low neckline exposed my new cleavage in a most provocative way. Wendy told me to spin around a few times and say, “I’m Michelle, I’m a woman, I’m Michelle, I’m a woman.”

At last came the wig, a womanly crowning glory. It was long lightly curled style, that cascaded down my back and over my shoulders. It felt delicious. Wendy spent some time with a comb brushing it out and styling it. It began to feel like it was my own hair. From the reaction on her face, I could tell she was excited. She finished me off by having me step into a pair of 3″ pumps. I was surprised how naturally I was able to walk in them.

At last Wendy walked me to a full length mirror, I couldn’t believe what I was seeing- an ultra feminine woman, who was definitely all woman from her high heels to her long tresses flowing over a full curvaceous pair of breasts. The face alone would make a man cum in his pants wanting to feel those pouting lips around his cock. But the breasts were sensual beyond compare. Any man would love to be with a woman who looked like this, to let his hand slip under the blouse, to slide in under the pretty pink bra and expose the woman-flesh underneath.

That evening Wendy and I went out to a movie then to a disco, where I danced almost every dance with a group of admiring men. I enjoyed the feeling of my dress spinning, my hair tumbling down my back and over my shoulders, and most of all I loved the feeling of my breasts bouncing sensuously for all to see and admire. And for some to feel, and for some special friends to suck on. In the weeks and months that followed Wendy taught me more and more of the joys of the feminine roll, how to be all woman. I’ve lost a few pounds and my hair has grown. I no longer need the wig, my own silky hair, now bleached blonde and frosted in a most flattering, feminine way falls over my shoulders. Wendy of course cuts it and styles it for me, we are having the time of our lives, and share many special secrets.

That was the beginning of what would be for me a new life, a life that included what was, and opened new possibilities.

by Terri Merritt

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