My Early Story

Pats First Time

OK. This is the story of my first time going all the way in womens clothes. And why. It all started because I was a bedwetter. I had tried everything. Not drinking anything for hours before bedtime. Nope. Wet in the morning. Standing there with the water in the sink running trying to pee just before bedtime to make sure everything was well drained. Nope. A neighbor friend even tried giving me little prizes when I woke up dry, but that did not work every time. I finally got it, entirely by coincidence.

It happened one time when I went to take a shower. My sister had showered just before me, and she had left her clothes on the floor. There was her school uniform bunched up in the corner. I was curious, so I went thru them. She had a plain pair of panties and a lightly laced bra there, suitable for a twelve year old Catholic school girl. I noticed that the panties were different from the ones that I wore as a ten year old boy. No double seam to pee through. A lot thinner and softer. So I tried them on. They felt good. I took them and hid them under my pillow. That night I put them on under my pajamas. And woke up dry! I took them off before I went to school, but the fact that I woke up dry was on my mind all day. I wondered if the panties had something to do with it. That night I wore them again. Dry again. I did that every night for the next week. Dry every morning. On Saturday, laundry day, I put them in with everything else. Mom did all the laundry at the same time, so there was no problem with getting them into the laundry. The problem was getting them back. I did not think about wearing panties on Saturday night, but woke up wet the next day. That seemed to confirm it. I needed panties to wake up dry. But I had put the only pair I had in the laundry, and of course did not get them back with the rest of my clean clothes. They were in her drawer.

So I had to get them from her dresser. I waited until she went out with her friends after church, and sneaked into her room. Going thru her dresser, I discovered her underwear drawer. There were many different kinds of panties there! Not just the plain white brief ones that I had seen before. There were many different colors and styles. I went thru them all, and decided that I was going to keep a pair of pink bikini cut ones. I happened to see the matching bra, so I took that too. That night I put on the panties and bra. It felt so right. It seemed that I should be wearing this underwear instead of what I had to wear. I put on my pajamas over the lingerie, and went to bed. That was the best night sleep I had had up to that point. I woke up dry and refreshed and ready to handle anything that a Monday of school and the nuns could throw at me. I really really wanted to wear that set of undies under my uniform, but thankfully sanity prevailed. That was my routine for the rest of the school years. I always was very careful to put her things in the laundry Friday evening and pick them up Sunday afternoon. There were times during the summers, when I was alone in the house, that I would put on her entire uniform. I liked that look and feel too. At the time I thought I was getting away with it, that she did not know about me, but I found out several years later that she did. I also enjoyed going into her closet and wearing her dresses. They made me feel so feminine and nice. Somehow complete.

As she grew up, so did her underwear. When Liz turned fifteen and I was thirteen, we left Catholic school and she started High School, and I started Jr High, in the local public school. So she got an entire new wardrobe to take the place of the old reliable black and white uniform. By this time she was in a 36 C bra and size six panties, not a single one was plain or white. All colors and styles (mostly bikini panties and full cup bras tho) and lots and lots of lace. Skirts were shortish and tops were either sheer or bulky. But always soft and colorful. Dresses were nice too. Not that she had many of those, but what she did have were nice party dresses that were very feminine. She was a mostly jeans and t shirt girl at home. She did have to wear nice stuff to school. Sixteen is when she got to start wearing makeup. And stockings and pantyhose. Wow. I still love the feel of nylon or silk caressing my legs. I prefer pantyhose, but a nice garter belt and seamed stockings can do the trick sometimes. Makeup was a different matter. I did not get to indulge in that very often, as the potential to get caught was enormous. The risk (at first) just did not seem worth the effort or effect. Was I wrong!

I finally got a chance to try makeup one weekend when the entire family went to visit grandma. Mother's mother. It was in the Spring break of that first year she had real clothes to wear. She would have been almost seventeen, as I recall, and I was a proud (still virgin) fifteen. Of course she had been studying Cosmopolitan and Sixteen and the other “how to” magazines for teens, so we knew what to do. She did anyway. She had real female help. But I managed to learn enough by reading and following what I had managed to overhear in her lessons with mom and eldest sister, Marie, to be confident enough to try it that weekend. A light bulb induced fever was the excuse to not go to grandmas, so mom let me stay home alone. I carefully waited an hour after they left to make sure that they did not return to get a forgotten something. I took a hot bath with her bubble beads that always made the bathroom smell so nice when she was finished. Now I knew why. My skin was so soft when I was finished. I did not have much hair on my legs then, but shaved them and my armpits anyway, just because the magazines said to. I never shaved my face before then, but took no chances. It was a very careful thing to do for the first time, but I managed it without a single cut. Not on the legs. Not on the face. Just very very smooth skin.

A thorough dry and off to Liz's room! I put on a pair of her purple bikini panties, careful to tuck my **** back under out of the way. Over those went a nice pair of tan pantyhose. On went the matching bra. Another first was filling the cups. It had never been a problem with me before, but today I was determined to do it up right. So I filled two water balloons with just enough warm water to fill the cups. After carefully making sure they were the same size, I tied them off and put them in the bra. A little adjusting, and I had cleavage! And bounce! Now I have to say that up to this time, I never got a sexual thrill from cross dressing. The feel and look and bounce of my new boobs got my juices flowing and I started to get turned on. Not paying much attention to the nice feelings radiating from my panty region, I surveyed the makeup table. Yep. She had a whole table dedicated to applying makeup. he top of it was covered with various tools of beauty. There was a huge mirror on the wall behind it. And a largish, comfortable chair in front of it. I sat in the chair and reached for the foundation. It was just the right color, as we both get the same amount of sun and have the same skin texture and light color. Careful to get it on smooth and even, I was satisfied enough with it to go on to the eyes. I was not brave enough to pluck my eyebrows, but I did use the tiny brush to shape them. I did use the mascara. And the shadow. My eyes are a real shade of blue, so I went with a dark blue between the brows and lid. Then a lighter shade on the lid, with a line of silver as a separator. Use of the blender brush made it come together nicely. Then more mascara. Some blush powder and more blender brush. The choice of lipstick was rather easy, as I knew just what dress I wanted to wear, and knew the color to use. It was another crotch tingling moment when the lipstick went on. It is the most sensual feeling to apply lipstick. I enjoy it very much. To me it is the essential touch of femininity. The smell of all the makeup products combines to alter my reality to female. After the lipstick, I was ready for the dress. Hair first though. Hair was easy, as this was in the early seventies, and boys could wear their hair however they wanted. I wore mine longish, not too long, just long enough so that when I combed it back, it looked male, and combed forward and to the side, it looked nicely feminine. I considered nail polish, but was not ready for that step quite yet. I did put on the clip earrings that had been saved from before she got her ears pierced. On went her spare watch and a few bangles.

Intentionally not looking in the mirror as I got up, I went into the closet and took the dress from the hanger. It was a beauty. One of those creations that fool the eye. When you are wearing it and standing absolutely still, it is solid red. Move just a little and the purple and black highlights stand out. Dance and twirl in it, and it is mostly black. With a scoop neckline that showed just enough to see that a real girl was wearing it, and short cap sleeves to show off shoulders and arms, it was eye catching. Not too short, just a few inches above the knee, it was perfect. Made of a stretch velvet material, it was flattering from the neck to the princess waist, with a flirty flair to the skirt. Nice dress. Wish I could find one like it today! I got the shoes at the same time. Still in the closet, I slid the dress over my head and adjusted it to feel right. The strappy shoes only had a two inch heel, so were not a problem to put on. I had worn them before and had lots of practice walking in higher heels, so these were easy.

There I was. Standing in Liz's closet. Ready for something. A debut of sorts. Proving something to myself perhaps. But I was very happy and content in my skin. I felt very right. Confident. So I put one foot in front of the other, just the way it said to in the magazines, (I had been practicing,) and walked out into her room and toward the full size mirror behind the bedroom door. As I approached, I was stunned by the fox walking toward me. She was all that I had hoped for. Me. Female. So right. I stopped and just stared at her. Then I gave her a big hug. I twirled and danced and watched that dress do its thing. And watching and doing I started to get turned on again. This time I let it happen. I ran my hands down my arms and felt the tingle. I ran them up from my belly to my boobs and squeezed. My **** was so firmly tucked back in the bikinis and pantyhose that it did not have a chance to show, but it felt hard as a rock. I turned the chair and sat in it to see what I looked like sitting down. I sat like a lady, sweeping the skirt flat first, knees together, and liked it. The nylon casing my legs was sparkling and shining. I crossed my legs, like a nice girl should, knees on top of each other, and felt the nylon caress my legs. I caressed them with my hands, running from the ankle to hem, slowly, on each leg. There was a lot of leg showing! That skirt was short sitting like that! My **** was pulsing in my panties. Uncrossing my legs, I opened them like a **** and looked up my dress. The sensation was incredible. All the times I had done this to real girls, I was finally getting a good look up a skirt! I felt light headed. I could see the little white patch of the panty part that covered my crotch. I could see the darker shade of nylon around the top of the leg parts of the hose. Entirely on its own, without me even touching anywhere near it, my **** exploded. My whole body locked up. All I could do was watch as the little white patch pulsed with a life of its own. The feeling was incredible. That was the best ****** I had ever had. It seemed to go on forever. That little patch of white was soon soaking in ***. I could see it seep right thru. It puddled up between the panty and skirt. The puddle just kept getting bigger and wetter. I think I was making some very strange noises, but did not care. This was what I had been born to do. ****** as a woman.

I must have fainted or passed out to another reality, because the next thing I remember was sitting with my head back on the chair. It must have been awhile, because my crotch was cold and wet. Heh. Time to clean up. Luckily, the dress was machine washable, so all I had to do was take off the shoes and get in the shower. That was a nice sensation also. All girl and all wet. I washed the dress while I was wearing it, taking it off only to rinse it. Carefully peeling the pantyhose off, I rinsed them out too. The panties were a real mess. It took special attention with the soap to get them clean. I popped the balloons and flushed them. There had to be a better solution to the boob replacement problem. (Which I eventually discovered.) Off with the bra, wash skin, rewash face, and I was done. Everything went into the washer for a quick spin, then the dryer. All was put away and innocent when the family got home.
Dawn262 Dawn262
51-55
Jul 10, 2010