From Boy to Man, A Transvestites Story

by Michelle Rose

 

After many years and much heartbreak, I am finally able to look in the mirror and be happy with who I am. This was no easy task, you see, I am a cross dresser. At times I fantasize about how lovely it would be to have been born a girl, but, I have no desire to make the transition to womanhood. It's very difficult for me to tell you this, but since this is a web site dedicated to transgender community, I thought some of our sisters might benefit from this story. I just want to tell you, you are not alone.

As I learned in therapy, I was destined to be a transvestite from an early age. My memories of wanting to wear girls clothing begins when I was 7-8. Too young to understand my infatuations with feminine things, I would fantasize about wearing frilly cloths and playing with girls. I remember lying in bed, playing with myself thinking about doll's, playing house and wearing the prettiest dresses. Dresses of the day for little girls were very feminine and women were just starting to demand "dress codes" permit slacks. I couldn't understand why a girl would want to wear pants, but I was certain I should be in a dress.

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In those days, boys were not allowed to play "girl" games and I was sent away, to play "ball", on many occasions. I would find myself more interested in being with the girls, than playing with boys. As an adult, I continually find myself sitting with the women. It seems to me, I belong there; it's where my true self feels at home.

As I grew a little older, I was attracted to my mother's closet. Who wasn't? When ever I could, I would sneak in there and touch all the natural silky fabrics of her undergarments and cloths. When I found some stockings or panties drying in the bathroom, I would always caress my face and body with the sensual fabrics. One day, I got the courage to wear a pair of charcoal black stockings, I found in the bathroom. That is one of my most vivid memories and since that day, I have been unable to keep away from women's clothing. When all dressed up, proper undergarments, comfortable cloths and well applied makeup, I feel so natural. Sure, I get a sexual euphoria from dressing, but, I can spend the entire day in a skirt and heels and just enjoy being feminine.

When I was 13 or so, I started to enter puberty and instead of becoming "manly" I just grew a few inches and put on a little body hair. My muscles didn't "beef" up, as did my friends and I stayed rather puny with slender arms and legs. Now, this was not as bad as it seems, by growing little, I soon learned that moms clothing fit me rather well. By growing a little older, my parents began to leave me home alone. This is the time I began visiting mom's closet as a boy and leaving as girl! The transition from touching the fabrics and wearing the cloths was a time of self-discovery. It was the first time I met the girl in me and I got to tell you, I couldn't imagine who I'd be without her.

This was the early 70's and it was a great time to be young. The cultural revolution was in full swing and society was getting very permissive. Articles about transvestites and transsexuals were becoming more frequent. Finally, I was stimulated to learn more about myself. Any newspaper or magazine article I found on the topic was devoured. I went to the library and located what little there was to read about these subjects. From this scant information, I learned an awful lot. Yes, I was a boy, yes, I liked to wear women's clothing and yes, I was sexually attracted to girls. I am a transvestite.

As I matured the trips to moms closet continued. She never said anything at the time, but recent comments lead me to believe she knew what I was up to. During conversations, with my wife and mother, my mom would make comments like, how much I enjoyed being married to such a feminine girl, or how she could tell, I liked a particular skirt or dress. If my women's intuition is correct, mom knows and has never said anything. Thanks mom. Your taste in fine dressing will be carried on for another generation. She always dressed elegantly and very ladylike. When I dress, I'm usually in long skirts and knit tops, well ok, I do have several miniskirts and sexy dresses. My wife helps me dress appropriately, but sometimes, she wants a sultry girl to dominate and dresses me accordingly.

All this time, I never thought anything was wrong with me. I felt and still feel that there are only two ways to experience life, as a man or as a woman. Who is to say I'm wrong if I prefer one over the other.

At 18 or so, I was getting ready for college and I looked forward to getting out on my own and enjoy life a little. When I left for my freshman year, I was only 5'9" and weighed about 155 lbs.; my body hair was blond and very thin. Although I would dress in mom's cloths from time to time, I wasn't very womanly, but my talent for passing was yet to manifest itself.

Once at school I found dorm life presented no privacy and no chances to dress up. Another problem, was the fact that moms closet was 1500 mile away! I began to think about the situation and realized I needed an apartment where I could have some privacy. My family couldn't afford to set me up, so, I started looking for work. Jobs were scarce and I was finally able to find some hours as stock clerk in a department store. While this didn't give me enough money to rent my own place, it did provide with a substitute for moms closet. My hours were after the store closed, when the night shift would clean and restock the merchandise. I just loved it when we worked women's apparel. Lingerie, sweaters, skirts, dresses and shoes, It was too bad my living arrangements didn't permit me to dress, because now I had access to wonderful women's clothing. Now, employee's received a 20% discount, so it was not unusual for workers to buy cloths for friends and family. With an active imagination, "fantasy dressing" was my favorite pastime.

One evening at work, I was putting knit dresses on hangers when my coworker Gail, commented on how I kept feeling the material! What started out as a joke, gave me away. Flabbergasted and not knowing what to say, I told her "yes, I enjoy the soft and sensual fabrics women get to wear". Looking me in the eye, I knew I said too much! From this wise ass comment, I found my first women into cross dressers.

We became friends and in no time I was invited over to her apartment. I nervously accepted her invitation and arrived exactly at the proper time. She opened the door and was wearing the very dress she had caught me fondling. Motioning me to come in, she asked how long had I been a transvestite?

We shared some dry white wine and talked for three hours. I felt so comfortable with her, I found myself telling her my whole tale. We went for dinner and I knew we had hit it off, when she invited me up for some "fun". We made love three times that night and in the morning, once again. After a shower, she asked if I would mind wearing her short silk kimono robe. I readily accepted her offer.

While we ate breakfast, she told me she was very turned on by everything and wanted to teach me how be a girl. From what I told her about myself, she knew I would love to have sex with a very pretty gal and get to dress just like her!

That first weekend, I learned many things a girl must know. Makeup, hair, jewelry, clothing, shoes and perfume were introduced. We talked about how to wear lingerie; stockings, garters, panties, corsets, chemise and slips. Gail measured me and determined my sizes, later, we would go to store and she would do some shopping for me. She pierced my ears and placed a little gold ball in each lobe. The little body and facial hair I had was easily removed with a depilatory and razor. A little plucking and my eye brows had that shapely feminine arch. By Monday, I was well on my way to womanhood.

I spent about 3 years with Gail and we had a marvelous time. Although I practically lived at Gail's apartment, I maintained my dorm room and put in a cameo appearance every now and then. I continued to work and school as my male self and as long as I was vigilant, I didn't have any problems.

Over that time I learned to walk, talk and adopt female mannerism. I had to be careful when dressed in" boy mode", to suppress my new feminine traits, I wasn't always careful and had some pretty close calls. Whenever I was with Gail, I was in a skirt or a dress; she really liked heels and made sure they were on my feet. The higher, the better, but, don't expect me to walk in anything over 5". By the time we parted ways, I could easily pass as a 20'ish woman.

Very early, she began to dominate me, which was enjoyable in bed or when alone with her. I really enjoyed her strength and accepted her dominance without a care. After I could pass for a woman, she would dress me very provocatively and take me to lesbian clubs and introduced me to her friends as her "boyfriend". All too soon, she began to humiliate me and send me home with her gay friends. At first, this was fun, but soon I tiered of being a whore for her friends. Towards the end of our time together, she wanted me to have sex with a man and wanted to watch while he fucked me. This became a problem and our relationship began to suffer. When we called it quits, I left her apartment in my favorite skirt and sweater with two suitcases full of women's cloths.

That weekend I checked into a hotel and cried for two days. On Sunday afternoon, I bought myself some jeans and a tee shirt and a pair of sneakers. I realized after leaving, I had left my male cloths at Gail's and couldn't return to the dorm in a skirt! I saw her on and off for the remainder of my college days. We had wonderful sex and still enjoyed each others company. But, her sexual needs were that of a lesbian and wanted another woman. I guess, before she realized she was gay, cross dressers were very exciting for her. I know she enjoyed my feminization and my submissive nature. We parted after graduation and I have not seen her since. Where ever you are, I hope you are happy and with someone who loves you.

My next girlfriend became a born again Christian soon after learning of my special needs. As you can imagine, this ended any possibility of a relationship.

After, I dated several gals over the next 5 years or so. Looking for that connection I had with Gail, but, never able to find the right girl. I dressed a lot in those days and with the popularity of mail order catalog shopping had an extensive wardrobe. By this time, I felt comfortable shopping while dressed and never got a second look. I still loved knits, the clingy and snug feel of a sweater or skirt still gets me excited. I stayed current with style and had more ladies cloths than man cloths. I grew my hair in college and every now and then had it styled and colored. I kept my eyebrows to slight arch, but not to extreme, I still needed to pass as man for work, family and friends. I'm sure some perceptive people may have guessed my passion for dressing in women's cloths, but it never interfered with my life.

I met my wife 18 years ago. She was beautiful, friendly and about 5 years younger than me. The magic and the connection I was looking for bloomed very quickly. She was a "girlie girl". She knew her body and understood how to show it off. Her makeup was perfect, never heavy or over done. She let me hold the door for her or pull out a chair. She was some kind of lady. The only mistake I made, was not telling her about the girl in me before we were married. I wanted to tell and knew I should tell her, but, remembering the disgust the born again felt, I couldn't.

We were married in a small ceremony and settled into life rather easily. For the first three years things were great, I never felt the need to dress, I threw out my entire wardrobe. I thought I was cured; all it took was the right woman. For the first time, I thought that, this is what it feels like to be a man! Well, after about 3 year's, life in the bedroom feel to pieces. We seldom had sex and when we did, it was very mechanical.

Now as I told you, she is no ordinary girl, she is very special. She arranged a weekend away for us and asked me straight out, what was wrong. She didn't accept any BS, she kept pulling and pushing me until my secret came out. To my surprise, she was very cool about it. She told me it was my feminine side, which she found so attractive. She found my comfort around women charming. She told me that the intimacy we shred early in our relation drove her not to accept the coldness of our current situation. The understanding and support of her emotional needs was like an old girl friend she could tell anything. She also told me, I was Fucking Ass Whole, for not telling her before we got married and stormed out of the hotel.

I thought we were finished, but she returned later that evening and crawled into be next to me. She kissed me and told me she loved me, but, if we are going to be together things must change.

In the morning we ate breakfast and took a long walk. We sat by a lake and I poured my heart out to her. She absorbed everything, but was confused about my sexual identity. She was very scared I would leave her after learning I was gay. Despite my assurance I was not gay and had never been attracted to men, we agreed to begin counseling when we got home. It was like a bright sunny morning after a storm, we made love with passion on the banks of lake, hardly caring if we got caught. The weekend was a great success; I told you she was some kind of lady.

Back home our relation continued to grow, we spent seven years in couple and individual therapy. She now understands that many cross dressers are very much heterosexual and just need to be dominated and dressed by their special lady.

About 2 weeks after the trip, she surprised me when, Fed-Ex delivered a very large box from Fredericks of Hollywood. Inside were all sorts of goodies for both of us!

Since that day, the passion we have for each other has never left either of us. We have a very active sex life and nothing is taboo. Sometimes, she needs a man and I can be that man. Sometimes, she wants a woman and I can be that woman.

 

Look at the time. My love is taking me out to dinner and a movie and I'm still in my robe. I think pink will be the color of the night. I just bought a lovely silk crape skirt; it's very sheer and has an underskirt, although I will wear a slip underneath. I love the flirty lettuce hem; it will feel great caressing my stocking clad legs. Tonight will be a cool fall evening any my favorite cashmere, turtle neck shell and sweater set will look lovely with my new skirt. I have a great pair of pumps that will go nicely with the pink details in the skirt. My hair is a mess and my nails look horrible. So much to do, so little time to do it, what's a girl to do?

  

  

  

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