Date: Wed, 12 May 2004 13:00:53 -0400 From: Andrea Smith Subject: My Future Is In My Sisters Drawers (TG) My Future IS Inside My Sister's Drawers A True Narrative Story By Andrea Smith It is difficult to think about the last 15 years. When you are 13 you hardly think about what will happen at 20, or at 30 years old. You never consider the consequences of your actions. At least the thoughts of the future ramifications of one day, one moment never crossed my mind. A mind which was to be awakened by sensations that are hardly ever considered by the public at large. Certainly sensations that are hard for the average person to understand. Part I: Typical My early years would be characterized as fairly consistent with most boys. I played little league baseball. I played soccer. I was into the usual cops and robbers thing, and pretend things with stuff like Lego. I hated my sister for teasing me. I had my usual ups and downs at school with kids knocking me around and making fun of my curly hair. I had parents who cared and loved me, and lucky enough to have grandparents who I admired and taught me as much as my parents. As I entered 5th grade, the first "sexual" feelings began to develop within me. Boys and girls were different. You dated girls, hung out with guys. Holding hands was a big deal, and sent a shiver up my spine. I was the first fellow out of my friends to experience a girls warmth and affection. Christine had moved to the area and didn't know a sole. For some reason that is still strange to me today, she developed a crush for me. Thinking back, it was the first turning point for me in many ways. Of course as the first guy to have a girl like him, I was ridiculed by my "friends." "Andy and Christine sitt'in in a tree, K-I-S-S-I-N-G. First comes marriage, then comes kids, then comes Andy in a baby carriage." they would taunt and laugh. It drove me nuts. Christine never understood why that bothered me so much. "They're just jerks. We should just do what we want. Who cares about them." "But they are my friends Christine. I just can't go out with you,' I would reply. we ended up apart for the remainder of our Middle School and High School years. Why was this a turning point you ask? Every time I passed her in the halls, I would see this beautiful, young girl pass me by. As we got older, all I could do was wish I could apologize and go back, but it was never meant to be. I remembered thinking how awful I must have made her feel back in the fifth grade. All-in-all, a pretty typical beginning. Now once I ended it with Christine, the same jerks who were making fun of me because I was "going out" with her, now were accusing me of something I took as much worse. "You must be a fag or something," said Michael. "Guess I will have to be the man and handle things from here Andy." "Fuck you. I am not." That was the only response I could muster. Michael was more of an casual friend then a "friend" but it cut me deep none the less. I had no desire to be with a boy. I never even considered it, nor had it crossed my mind. the thought actually repulsed me. Little did I know how things were going to change. It was around this time that we were require to watch the Health Ed film on sex. So, they split us into boy and girl groups. After watching the film, and learning about masturbation, I figured I should go home, and try it. We were all discussing it and laughing about it anyway, so why not? Leaving the details out, I can only say that it was fun, and I enjoyed it quite a bit. Who wouldn't? From then on, Masturbation was typical for a 11-13 year old. This whole episode over Christine continued with my so called friends for a little while. Throughout much of the next few years, life remained fairly standard. That all began to change after my 13th birthday. Part II: The Beginnings Summer came after a busy and boring 7th grade. It was all pretty standard stuff to this point. I spent that summer at the grandparents which was also standard. That was about to change. By the end of this summer, life would be anything but standard. My sister was still a giant nag and a huge pain in the neck to this point. Also pretty standard for most baby brothers. She was 18 and this was her last summer before college. She was going out of State which was a blessing for the obvious reason. But it was also a major factor in what was going to happen to me early that fall. One summer day in August, I remember my family was outside of the house. It was a perfect summer day, and the family wanted to lunch outdoors. After eating quickly I asked to be excused from the table to use the bathroom. I went inside, and passed by a photo which had been on the side table for more then 3 years now but for some reason it caught my eye for the first time. even so, I just walked past it, as I always must have done, but as I was in the bathroom paying homage to nature, I kept wanting to get a better look at the image. I completed my deposit, washed up, and went back to the image. It was a photo of my sister. She was 12 or 13 and was wearing a light blue tank top in the photo. I wasn't focusing on the puppy that was in the photo with her, or her face, or how happy she looked. I was drawn to the two small bumps protruding from the tank top. I must have stood their for a good 30 seconds just looking at it. For the first time in my life there was something sexual about my sister. Don't get me wrong here. I didn't "want" my own sister. Besides, at 13 years old, the concept of incest was lost on me. But the thought of breasts just raced through me. What did they feel like? What did it feel like to have them growing out of you? Does it hurt? Does it feel good? the door opened and shut quickly. Someone was coming. `Snap out of it kid,' I thought to myself. I started walking again, and passed my mother. She was carrying dishes to the sink. Neither of us said a thing to each other. When I got back outside, I flashed very quick glances at my sisters breasts. It was clear they had changed from the time in the picture to the present. She never knew what I was doing, nor did anyone else. That night, as I was lying in bed, all I could do was wonder what it must feel like. The thoughts began to cause some stirring in my groin the erection made its way into my conscienceless. I remember masturbating that night. I came not once, but twice. I was surprised that I was able to do so without any stopping or breaking. Usually, after one time, I was fast asleep. This was the strangest thing I ever felt. I drifted off to sleep with the questions about breasts in my head. I awoke with the same thoughts. These feelings did not subside. I began masturbating daily for the next few weeks. the thoughts of being a pervert crossed my mind. `What's wrong with me?' was a regular question in my head. Every time I finished jerking off, I would tell myself, its the last time. Then I passed by that damn picture again. `The last time? Ha!' The routine continued as my sister prepared to leave for school. she would be gone throughout the fall until Thanksgiving holiday. "I finally have this place to myself," I would say to her and the family. "I'll be back," she said, "and I'll keep torturing you when I am back." We returned home after dropping her at school. The thoughts from the summer were still with me. The regular masturbating was also still occurring. `What does it feel like to have breasts?...' the thoughts were reverberating, stronger and stronger. The answer seemed like a lost cause. `I would never know; would I?' Part III: Open the Draw and Take a Peak My mother had her own routines. By the time I was 13, she was comfortable leaving me alone at home while she ran her errands. so when I got home from school, and she said she had to run out, it gave me time to jerk off before starting homework. When I did jerk off, the thoughts about breasts, and breast development continued to dominate my mind. I wished I could do something about it, even if it was that I would never think about it again. "Oh, I am glad you came home early," mom said. "I have to run out to the store for about an hour. Will you be okay?" What a silly question I thought. "Of course. I'll see you later," I said. She grabbed her purse and out the door she went. I watched as the car pulled out of the driveway and she left. Like the other afternoons that I was alone, I went upstairs to my room, stripped and began to masturbate. As usual, the same thoughts came to me about breasts. `I wonder what it feels like to have breasts,' my mind raced on. `It must feel cool...yeah and you can wear a bra and everything, and that makes them stand out and........ Whoa, what did you say?' I stopped masturbating and opened my eyes. A bra. What does a bra feel like? I started to wonder more and more. Now I was just sitting there naked. `Yeah but where could I get one?' my mind asked. `and I have no clue how to put it on.' On cue my brain seemed to answer, `get one from your mothers drawer stupid.' Almost immediately I thought, `yuck!' `Then what about your sister? She might have left something here for when she returned home.' My brain wasn't so dumb. For some reason the thought didn't revolt me. To this day, I don't know why. I tried to talk myself out of looking, but the voice inside became louder, and clearer. I got up, and snuck into her room. It makes me laugh a little to think about how I snuck into the room. No one was home, yet I was careful not to make a sound. She has one of those long dressers. I started on the left top drawer and began to quietly open it. Sweaters. Shit. Next. Jeans. Fuck me. Next. Shorts. For the love of Pete. On an on. Until... It was the second to last drawer. I gently opened it, and found it half full. I looked down at the bras, and panties folded neatly. My limp penis suddenly began to spring to life. The thought that here was my sisters bra...was I actually going to put it on? After all this was not leaving fantasy and becoming reality. Plus, this material I was looking at actually touched my sisters body. I picked out the bra on the top. It was beige. I saw that the tag said 34C. I had no idea what that actually meant at the time. I continued to think about how my own sisters breast touched this bra that was now in my hands. the same bra I was considering wearing. there was no way I could do this. I actually put the bra back, closed the drawer and left the room. But the mind continued. `You have to try it. All this time you have wanted to know what breasts feel like. Here's your chance. No one will know.' My answer to this part of my brain was that I agreed, but I couldn't get past the part where my sisters bra -- the same bra that touched her breasts, her nipples, her shoulders and back -- as now going to be on my chest, shoulders and back? No way. But my mind, quickly becoming sicker with the fantasy, suggested that I wear an undershirt, then put the bra on over it. It is absolutely amazing what the brain creates. I went back to my sisters room, this time wearing an undershirt. I didn't know it then, but as I opened the drawer, I was looked at my future. Part IV: I Am Not Gay? It took a little while, but once I placed the bra down on the bed, it became clear how it was to be put on. With my undershirt already on, I took the bra and wrapped it around my torso. My heart pounding like a race car engine, I hooked the catch, and gently turned the bra around. I was raging. My cock was harder then it ever seemed to be in the past. I slid the left shoulder strap up and onto my shoulder. Then the right one. I practically sprinted to the mirror. I was wearing a bra for the first time. The first thought that went through my head; `It feels so good. Like you are being hugged all the time.' The second concept was; `My god you are wearing an item of women's clothing and it is your sisters bra.' Lastly, the ideas of what breasts feel like began to dominate. With no one home for at least another 30 minutes, I thought I may want to see if there were any baseballs, or tennis balls I could stuff into the bra. I had come this far, why not see if I could experience the feeling and sight of "breasts?" I went downstairs carefully. I went to the closet and did find tennis balls. I also found softballs. Back up the steps in a flash, I first put the tennis balls in the bra. This caused the straps to tighten a little, which made it all feel so much better. then I graduated to the softballs. Wow, how great it felt. I masturbated and came three times. What a fabulous feeling. For some reason, I glanced at the clock through the fog of three orgasms. `Holy Shit!" My mom was probably on her way home. I carefully stripped out of everything. Returned the balls, the bra as best I could and cleaned up. I had just gotten dressed when she returned. "I'm back," she bellowed. That was close. Later that night, all I could think about was what I had done. My mind took over. `Didn't it feel great?' It did feel great. And I loved it but the question came up for the first time and I had a quick and definitive answer. I am not gay. It was the truth. I had no thoughts of men, or desire to be with men. but, I sure had a desire to wear my sisters bra. I again drifted off to sleep with the thought of that bra and what it looked like on me and how it felt. When I awoke, I got dressed as per usual and went to school. I said nothing about what I had done. The thoughts of it didn't enter my mind. I went through the day, and came home. I had a small bite that afternoon, before going up to do my homework. As I walked past my sisters room, the thought of that bra, and how it felt hit me like a bat across the head. My cock begin to stiffen in my clothing. But as I put my things down, I realized that with my mother home, I could not do it. I could not risk getting caught in my sisters room. I tried t concentrate but my now fully hard penis needed attention. there must be a way. I went back down and using sound noticed that mom was in the dining room reading a paper. This was a supreme benefit. she was far from the room below my sisters and could not see me if I went to the closet for the tennis balls and soft balls. "What's wrong?" she called out. "Nothing, I forgot my notebook down here," I lied. She continued to read as i heard the pages of the New York Times turn. I quietly got the balls, and carried them up to my room. I put them down and extremely carefully tip-toed into my sisters room and pulled out the same bra I had warn the day before. I stripped except for the undershirt, put on the bra, and put the softballs into the bra. It was another 3-time cum event. But this time it ended a little differently. `No one knows you have the bra and the balls. Keep them here so you can wear it tonight,' my mind said. It was an easy sell for me, and I placed the bra and balls in the closet for later use. The evening passed with out a problem. I had dinner, did my work and watched some TV. When I did go to bed, I again put on the bra and stuffed the bra with the softballs. This time, even though I was hard, I drifted to sleep wearing it. I finally awoke at 3AM and discovered what had happened. I took everything off and drifted back to sleep with the same pesky question in my head; `Are you Gay?' I awoke for and went to brush my teeth. I was wearing no shirt, and as my vision came into focus, the red lines around my torso and on my shoulders were clear. the bra was a little tight, but to still have the indentations and red marks was astonishing. As I looked in the mirror, the question again became prevalent in my head; `Are you Gay?' I hesitated for a moment and then simply laughed it off. It was ridiculous to think I was gay. `I adore women, the idea of women and want women. I just happen to like the feeling of a bra. No one knows, and who cares? It's just a phase right? Right!' I went to school that day, and every day after that with the same thought after a night of wearing my sisters bra. But it was only the first step. There was much more that was going to happen over the next several years. Part V: The Birth of the `Girl' Inside Wearing my sisters bra when I masturbated became the norm. Sometimes I would return the bra, other times I wouldn't. I enjoyed it very much. There were times when I would just do it once at night, and other times when I came home from school. I confined it to my room alone, always keeping the door closed. This went on for several weeks and months. There was little deviation from the process, but that would change too. My sister returned home over the Thanksgiving holiday. I had returned her bra the day before she arrived, but then realized that she would never remember which bras she left home and which she took with her. I went back and took the bra for good this time. She came home and the first time I saw her I remember feeling a little strange. I had worn this girls bra, and she was my sister. I pushed the thought out of my head even if only for a few hours. The next day she announced that she had to run to the store to but a bra for a dress she was planning on wearing Thanksgiving day. "What kind of bra?" asked my mother. "A t-back bra. the dress has no sleeves and is high on the shoulder. I can't have the straps show," proclaimed my sister. What in the world is a t-back bra? this peeked my curiosity. There was more then one kind of bra? Wow. I can't wait to see it, I thought. When I saw her the next day in the dress she was putting make up on in the bathroom. I watched from a distance as she leaned forward to apply her eyeliner. The outline of the bra became apparent. It was basically a racer back bra. The straps are in toward the center. I wondered how it felt to wear. "I'll be out in a minute," she commented my thoughts of wearing what was now on her breasts. "Its okay Amber. take your time. I am not in a rush," I responded with a slight grin. "You feeling okay Andy? I thought you would be biting my head off for taking my time in here." "It's okay Amber. Really. I have no trouble with you." Little did she know what I was doing or thinking. I remember feeling a little guilty about that, but after wearing her bra and masturbating over the last 2-3 months, guilt was an after. After she left to go back to school, I was amazed to see that she had left the t-back bra behind. I thought how fortuitous to have this bra in my hands. My penis began to rise as I struggled out of my clothes. I became so excited so quickly that I began to put the bra on me. this one had a front closure. I thought how great and easy is this? I clipped the front together and noticed the extra tightness around my back immediately. Then I slid the left shoulder and right shoulder up. Gosh what a tremendous feeling. Suddenly, I felt a gentle breeze from the open window on my shoulder. this tipped me off to a scary realization, and I began to panic as I raced to the mirror. Oh my god! I had forgotten to put on the undershirt first. I couldn't believe my own carelessness. I began to fumble with the shoulder straps as I raced out of my room for the first time, and into the bathroom. The same bathroom where my sister stood 3 days earlier wearing the same bra. I got to the sink where I began to lower the shoulder straps of the bra. As I began to try to open the clasp on the front closure on the bra, I looked up at myself. Naked, except for the bra, with the shoulder straps dangling around my midsection. As I looked at myself, the panic began to subside. The bra has already touched me; touched my bare skin. It was already too late. the look of panic began to shift in my eyes to a look a calmed acceptance. I began to realize that even if I took the bra off, put on the undershirt and then put the bra back on it wouldn't matter. It had already touched my bare skin. My calm acceptance began to shift to a warmth I had never felt before. I became faint almost. Slowly I realized what needed to happen. I reached for the left bra strap and slid it back onto my left shoulder and I then did the same with the right strap. I then went back to my room where I picked up the softballs and inserted them into the cups of the bra. I felt suddenly feminine, and suddenly wanted to feel like my sister. My erection was raging and I began to stroke it. After cumming, I began to feel guilt in earnest for the first time since I began with my sisters bra the first time 3 months earlier. The night was filled with very mixed emotions of pure pleasure and acceptance, and guilt. I knew the next afternoon, when school let out, the answer would reveal itself. The day was normal for all intents and purposes. However, for the first time in 3 months, the thoughts of what I had done the night before, and everything that led up to it, began to creep into my normal time at school. I spent parts of that day in a fog. All the while I realized that what I did when I got home would begin to shape my future. When I finally arrived home, I was lucky enough to hear my mother tell me she had to run out for the next 2 hours. "First I need to go to the grocery store, then I need to see Grandma to go over some paperwork." I couldn't have been more excited about her not being home, but it was also a partial curse. I soon realized that had she have stayed home, I may not have rushed into my sisters drawers. I did hesitate for about 5 minutes. I tried to avoid it, but the feelings began to overwhelm me. I soon found myself stripped naked, and looking into my sisters drawer. I went right for the t-back bra. This time, while standing in her room, standing in what was most likely the same position my sister stood in every day, I put on the bra. i then adjourned into my room, where I promptly placed the softballs into the cups of the bra. After looking in the mirror in my room, I felt like I need to confirm what I was wearing in my sisters room. I crossed the hallway into my sisters room wearing her t-back bra, bare to my skin. I looked in her mirror as she had done so often, and realized the reality of what I was wearing and where I was standing. My erect cock was pulsing at the reflection in the mirror. My mind began to take over. `You look great,' it said. `Ever think about trying on something else? After all you have tried on different bras and loved them both. Maybe you should try her panties? Maybe you should try her skirt or dress. Ever think about that?' I couldn't help but think about it. What else was in her drawers that she had left behind? Was there something else? What about her closets? Maybe there was more their. My mind was raging. As I considered all of this, I could also not get past the thought of ruining Amber's things. I began to wonder how I could get around that. At that point my eye caught a pair of ballet toe shoes hanging on the wall. They were Amber's shoes when she did ballet. That reminded me of the leotards, tights and costumes she used to wear. I began to look for them but to no avail. I realized she hadn't warn them in years. Maybe they were thrown out. Perhaps they were in storage in the basement. What a stroke of luck that would be. I carefully went down to the basement. Wearing just the t-back bra stuffed with the softballs. I went to wear mom kept the storage. In the second box I checked, I found it. All of it. Leotards, body suits and stockings. What a break, and who would miss all of this? Nobody. I picked out a teal long sleave leotard with a deep v-neck and a black leotard with a turtleneck collar and zipper in the back. I went back up to my room, and careful stepped into the black leotard. As I pulled it up my legs, I became very excited. I seemed to be crossing into a new level. As the tightness around my hips and buttocks became apparent, I rolled my arms into the sleeves. I pulled the leotard on and began to zip up the back. The feeling was heaven. Although I struggled a little, I managed to get the zipper to the top. I race to the mirror in delight. I loved what I saw. The way it looked, the way I looked, the way it felt on me. Again the question came up; am I gay. Again it was dismissed immediately. this time the answer was also, "I just like to wear bras." But the mind again kicked in. `You like to wear women's clothes.' That thought gave me pause. I knew it was true. I liked to wear women's clothes. There was no denying it. I liked to dress as a girl. I looked in the mirror again. "Say it," I expressed to the reflection. In a moment of clarity, and absolute comfort, I saw the reflection respond, "I am a girl." I was stunned at the reflection, but I thought what I heard was that I was a girl. "Say it again," I said to the reflection. "I am a girl," was the clear response, except this time I said it, and I knew I said it. My mind quickly figured out what had just happened. `Did you like the sound of that?" it asked. I knew I did. In fact, I loved it. My cock was throbbing, and it was begging to be stroked. I obliged, but only for a while. I knew if I came the guilt would prevent me from trying on more clothes. I struggled out of the leotard and new courage gripped me. I kept telling myself that I was a girl. I opened my sisters underwear draw again and peaked inside. This time, I picked up one of her panties. I knew now how serious this was becoming. I was about to put on the same panties that had touched my own sisters ass. Her pussy. My god, I could not believe what was happening to me. The desire was so intense. I put them on and slid them up my legs until they were snug around my waist. Before I knew it was I was rubbing my cock through the panties. More and more and it felt better and better. "I am a girl," I kept telling myself out loud. the intensity in my cock built and built until there was nothing left. I exploded with determination into my sisters panties. The guilt began to creep in as I began to undress. I began to wonder about everything I had done and said. It replayed in my mind as if on tape. Was this what my private life was to be? I could not escape the thought of it. As I cleaned up, it became clear that I could not just return the panties I came in. I washed them out and hung them in my closet, confident that I would return them when they were dry. I went to bed later that night still feeling guilty, but also feeling good. The experience continued for the remainder of the school year. I found myself being kinder to my sister. Somehow, I felt more in tune with her. I felt as though I was now a part of her, and she was a part of me. As the warm weather came, the thoughts of my sisters return became real, and dressing in her things while she was home would be difficult. How would I do it? Could I even risk it? Time would tell. It wasn't a simple answer anymore, because I slowly began to realize I couldn't stop. I didn't want to stop. Part VI: Nurtured Over Time. Developed Through Patience The time passed slowly on some day and fast on others. Summer came that year and my sister returned. I did return everything to wear it had been. I was hoping no one would notice. I fantasized about how good it all was while my sister was away and I was able to wear her bras, panties and leotards. I felt like there was no way I could risk it during the summer. at least not while we were under the same roof. I would be going to live with my grandmother again, and knew I could keep my secret from her. My breaking point came within a few days of my sisters return. Masturbating without the clothes was no fun. I got dressed to go to school that day -- the first really warm day in late May. Even though it was 7:30AM, my sister was at the breakfast table in a bikini. I was a little taken aback to say the least. This was the first time I had really seen my sister in a bikini as a fully developed woman. I will confess that it did turn me on for a second. "Why are you dressed in that," was the only thing I could muster. "I'm gonna lay out today. The sun is going to be perfect," she said as she bit into her morning banana. I fumbled out a few more remarks, but just grumbled out the door. Once I got out the door, my thoughts were filled with that pink and black leopard skin pattern bikini. The thought was not only of my sister, and what my eyes had scene, but also the concept of wearing the bikini myself. When I arrived home that afternoon, there was my sister sunning on the chaise. But, she wasn't wearing the pink and black bikini. She was wearing a one piece black and white checker pattern bathing suit. Her eyes were closed as I walked up, and I was looking at every detail of the bathing suit and how it hugged her curves. I just said hi as I walked by. Once I got inside, and noticed my mom was again reading the Times, I knew I could go up to the room and sneak something. I couldn't take it. I just had to do it. when I got upstairs, and I snuck into my sisters room, I realized that the room looked down on where she was laying out. I quietly went to the window. I looked down on Amber as she was turning over. Her back was now facing me as she was lying face down. What a sight. The curve of her ass looked so good. The bathing suit was a little loose around her breasts so as she was lying on her tummy, you could see the breasts push outward, although you certainly could not see nipple. I could not believe what I was seeing, nor that I was watching my own sister, and seeing her sexually. I turned away to leave and saw a pile of her clothes on the floor, including the bikini from the morning. I grabbed the bikini and went to the bathroom where I promptly and without hesitation put it on. It was a tie string in the back on the neck, and I could feel the sun tan oil that was lingering on the cloth. The feeling was very intense. I was careful to slide my ever hardening cock out the side of the bikini so I could jerk it off. I came very quickly. I removed the bikini, and returned it to the same place and position I had found it. Three days later, my sister left for the Jersey Shore, telling us she and her friends rented a house for the summer. When she left, I checked her drawers and found many bras, panties and other fun things like panty hose and slips. I also noticed the pink and black bikini and the checker one piece were left behind. Knowing my sister was gone through August, I quietly packed the one piece and brought it, and the t-back bra with me to my grandmothers. It was going to be a fun summer. The summer passed, and I returned the clothes I had borrowed from my sister in late August. No one knew what I was into. I had been dressing in my sisters clothing for almost a year and I realized that there seemed to be no desire to stop. Over the next several months that feeling became stronger. Despite those feelings and the occasional questioning of my sexuality, I continued in my dressing. Eventually I began to enter my sisters closet and find some of her skirts and dresses. It wasn't just the underwear but the desire to wear more and more female clothing. As I turned 16, my secret was still safe. I had begun to seriously date a 17 year-old. Carrie was cute enough girl. She had "done it" already and was very much attracted to me and I to her. She had no idea about my desire to dress as a woman. We had a typical boyfriend-girlfriend relationship despite the fact that I continued to dress in private. Carrie was the first girl I had been involved with romantically and sexually. I enjoyed the sexual activity but it was strangely unfulfilling. Part of me thought that once I became sexually active with a woman, I would masturbating, and my desire to dress as a girl would cease. I graduated high school with little fuss or fanfare, and went on the a 4-year college. During my 4-years, I was involved with a fraternity and had the normal college experience. I continued seeing Carrie through most of my college days as well. My dressing continued, but it was much less often. I couldn't dress in the dorms after all. Regardless of less time to devote to dressing a few things happened that planted the seed for perpetuation of the dressing. The first was that I found a wig at school that was part of a stage costume. When no one was looking, I took it. It was blonde and was about shoulder length. When I did dress and include the wig, it really made me feel and look more feminine. Another key incident that occurred involved Carrie. We had stayed at her place overnight while her parents were out of town. When I awoke in the morning and went to the head, I came across a Frederick's of Hollywood catalogue. As I went to the bathroom, I began to thumb through it. Women's clothes through mail order and what clothes. A nice mix of slutty and sexy. I said nothing but snuck the catalogue out of the house. When I got the chance, I place an order, the first time I purchased my own clothing. I bought a set of "falsies" for breasts, and a padded girdle to add curves. The first time I tried these items on, I was in total heaven. Together with the wig, I began to see a girl looking back at me in the mirror for the first time. The second key factor also involved Carrie. We were joking around a little about the rockers who ware make-up. After some discussion she asked me if I would let her make me up. I hesitated a little, but the girl inside me liked the idea. I let her do it. While I had no other women's clothing on the site in the mirror was a real turn-on. I realized almost at first glance that I now had all of the tools to look like a girl. It was strange as to how the tools had developed at a time where I was dressing maybe only 2 or 3 times a month, but nonetheless, there it all was. As my senior year in college approached, and I was living alone in the dorm room, I did manage to sneak a few items from my sisters old wardrobe, mixed with my wig, and padded extras. I would jerk off while wearing it on average once a week. While Carrie and I had split, I still dated a few girls and had sexual relations with them. No problems, and my secret was still intact. Upon graduation, I moved to a relatively remote area in the form of my grandparents summer home. This was to become my home. I packed up all of my things, including my large stash of my sisters clothes, and a few of my own things. I figured that I would have the luxury to dress, but it wouldn't be that often. How wrong I was. The girl inside had been nurturing and developing over the last several years. She was ready and going to show through. Part VII: The Truth Penetrates Deeply That first summer after school proved to be similar to my time in school as far as the dressing went. I spent a little time as a girl, but it did not dominate my life. The occasional girl that would visit would "lose" a thong, even a pair of jeans. But I would explain how these things happen. The fall came, and I was working in the city. Midtown Manhattan had tons of sex shops. Once or twice after work I would stop in, maybe buy a video. I saw all the toys on the shelves, but never thought I would have any use. During this time, Carrie and I reunited. It was strained, but the sex was good. as we talked more openly about experimenting with different positions, we also talked a little about toys. I decided to see if she would go for a toy. so, with the anonymity of the city, I went into an adult shop and purchased a penis shaped, tan colored dildo. It was 9" long and 1.75" in diameter. I presented it to Carrie. She was surprised by it, but we still tried it. She found it mildly curious, but not too fond of it. Watching her masturbate with it, seeing it go in and out of her, was more then just a curiosity for me. The thoughts began to rage in me as I watched. `Doesn't it look good going in and out of her,' my mind began to say. `That's kinda what it must be like going in and out of an asshole too. I wonder what that must feel like? Does it feel good? Does it hurt? All these gay guys do it and rave about it. How bad could it be? And since you dress like a girl, why not give it a try?' My head was spinning. But I gave her the toy. I couldn't just ask her if I could use it. she would think I'm gay or something. I still answered that question as absolutely not by the way. Then the opportunity presented itself. She and her parents were going to be away for 2 weeks and needed someone to water plants and asked if I would do it. I agreed, knowing about the opportunity I had before me. I could try it then, I thought. Later that month the opportunity came to fruition. I had the key of course, given to me by Carrie's mom. I went into the house and right to Carrie's room. She had told me where she kept the dildo, so it was easy to find. I watered all the plants, and then, stripped naked. I found some vaseline and put some on my asshole. Then I put some on the dildo. I was very nervous and excited too. I squatted down in a catchers position, feeling it would give me maximum control and the best opening. I placed the dildo behind me, and noticed the coolness of it. I just began rubbing the head of the dong in small circles on my asshole. I was surprised at the pleasure of it. Moving the dong back and forth on my asshole for a little while really spread the lubricant around well. I then realized how ready I was to experience penetration for the first time. I began to gently push on the dildo, and I was surprised that it began to ease in. I continued to slowly work it. A little in at a time. Before too long I had the head all the way in. It felt very good with very slight discomfort only. I continued to push it deeper and deeper. as it got a little deeper it became a little painful, so I would stop pushing, but would leave it in to stretch out my anal opening. eventually, my opening began to accept the girth of the dong, and I was able to proceed deeper. After some time, and without realizing it, I was very slowly sliding the dildo in and out, in and out, in and out. I experience the build up of a very intense orgasm. As I began to pump the dildo faster and harder, I stood and bent forward, placing my foot on the toilet for leverage and balance, while I placed my had around my own cock and began to stroke it vigorously. I came incredibly hard and all over the floor of the bathroom. When I took out the dildo, and I washed it, and cleaned up, I had some guilt, but surprisingly little. I went home, and remembered the intensity of the feeling of the dildo in my ass. The sliding of it in and out. I wanted that feeling again. The next evening, knowing no one was home and that Carrie didn't use the dildo, I went back and took it. I brought it home with me, and it became my dildo. After a short time, and using it much the same way as I did the first time, the thought of it being my dildo settled in on me. Again the thought of am I gay began to creep into my consciousness.Again, I hesitated, this time for a little while. For the first time I considered that I might be bi-sexual, although the thought of being with a man repulsed me. But I had to admit that I sure loved having that "dick" in my ass. Now I had to try it with the girls clothes on. I decided I didn't want to hold the dong. I wanted it to be still so I could mount it, like a girl would mount a real cock. I created a solution by rigging it to a chair. I went and got dressed. Bra with the softballs, the black leotard and wig. It was dark outside and I kept the lights off in the house as I made my way into the spare bedroom where I had set up the chair and dildo. the moon illuminated the house enough so I could see where I was going and what I was doing. I had also set up a mirror in front of the chair so I could see myself as I got fucked by the dong and one positioned behind me and slightly below my ass, so I would see the dong at the moment of hands free penetration. The moon lit up the room perfectly. My ass and the dildo were fully lubed. I straddled the chair and began to lower myself onto the dong as I slid the crotch of the leotard out of the way. Again the head of the dong was cool, but as I rocked back and forth it warmed. Soon it was beginning to slide into me and this time there was no pain at all, only pleasure. I watched as the head passed the opening, and the shaft began to disappear into me. In the standing cowgirl position, I began to ride the dildo. Slowly at first but building speed and depth. Before long I was fully fucking the dong. Furiously I pumped it, and watched every thrust enter my ass. I then shifted my gaze to my face in the mirror. The hair of the wig dancing around like a real girls. The softballs in the bra also bouncing some. I felt more female then ever. After intensely cumming, I went back to the room, leaving the dildo and room set up, knowing I would be back to use it again and again. When I returned and looked at the clock, I saw that I had been fucking my ass for more then 30 minutes. I realized that the penetration into my ass was more then just physical. It was emotional. I also realized for the first time ever, that the dressing as a girl was no longer just dressing, and it was not a phase. Still I refused to consider myself bi or gay. But the truth was in my own mind that I was something else. I accepted myself as part female for the first time that night. At the time, it was a small part. Maybe 15% at the most, but it was undeniably there. The penetration into me showed me that much. The pleasure of that dildo, and that night led me to purchase my own vibrator. I also worked up the courage to get my own makeup, and false nails. With winter around the corner, I began considering the possibility of altering myself more physically. So, with a weekend approaching, and the seclusion of the area I lived, i began to make plans for my first physical foray as a woman. I'm talking about things that wont be undone after an orgasm. I knew I had reached the next level in what even I was beginning to call, my transformation. Part VIII: Take a Walk As summer continued, my anal experimentation expanded and became more frequent. Getting fucked every night was becoming commonplace. Part of the excite was watching myself in the mirror. There were times where I couldn't believe what I was doing, and other times where I couldn't comprehend how far I had come. Going back to the adult store and buying my own vibrator was no big deal. Walking in to Macys, and buying my own bra, was also no big deal. Playing with the vibrator was awesome. I loved the way it felt. I wished I could leave it inside of me for hours. That's when I caught an episode of some talk show or another. The topic was men who want their women to get breast augmentations. Most of the women on the show refused the idea. As part of the show however, the men had to wear a bra, and then fill water balloons and stuff their bras. This was so the men could "feel" the weight of their "breasts" and what they were asking of their girlfriends and wives. "What a great idea for me," I thought to myself. I went out and bought some balloons. When I used them, it was fabulous. The best look and feel I had experienced. I knew this was to be the norm for me. As Friday of that week rolled around, I began to think about what it would be like to be a girl for more then just a few hours, or just to get fucked. I began to think about what I would need to do to make myself look more convincing. After all, I may need to go out at some point. I had the wig, the make-up, the faux nails and now perfect "breasts." I also had a fair wardrobe. A mixture of my sisters things, ex-girlfriends things, and a few of my own items. My mind began to interceded yet again. `You have come a long way since you were 13. Its time to take the next step. How will you know what its really like to be a girl if you don't actually stay dressed like one for a while?' I decided I had to try this. That Friday when I arrived home from work, I decided to begin. I stripped naked and stood in front of the mirror. I wanted to be as female as possible. `You better start by shaving your legs, chest and underarms,' said my mind. I had never considered that but I knew that my mind was right. It took some time, but I went ahead and shaved my body smooth. The sight of smooth legs and chest, and the feel of it was very sensual and exciting. I loved what was happening to me. I got dressed, put on make-up, the faux nails, everything. After watching a little TV, I went to bed. I awoke Saturday morning to a bright sunny day. Wearing the bra and panties and night shirt, I got up and went to the window. "What a perfect day," I thought out loud. It was also true because I had been dressed as a girl for more then 12 hours. As I went to brush my teeth and walked past the closet something pink caught my eye. Buried in the pile of girls clothing was my sisters black and pink leopard pattern bikini. I picked it up and looked at it. Then the idea hit me right in the face. `It's high time you get some color on you girl,' announced my mind. Oh my god, I thought, how could I do that? That would be so...it would be something that I couldn't hide. Then again shaved legs and armpits were something that would be difficult to hide in the summer on the beach anyway. I stripped down and put oil all over me. Then I put the bikini on. The house was secluded so I had little fear, but still this was the first time I was exiting my home as a girl. With some tentativeness, I opened the door, and out I went. The warmth of the sun hit my body immediately. As I lay there, covered in oil and wearing my sisters bikini, I felt like there was no turning back to full masculinity ever again. The rays of the sun were burning that fact into me. I remained on my back for a good 10 minutes, then flipped over onto my tummy like I saw my sister do a few years before. I waited another 10 minutes. I got up slowly, and went inside. The excitement of seeing myself in the mirror was excruciating. I went to the mirror, and took a look. everything looked normal enough. Then, I removed the top of the bikini. I was disappointed that the 10 minutes did not reveal any tan lines. I reapplied some oil, and re-tied the top. I poured myself a cold drink, and returned outside with confidence this time. I stayed outside for longer. Approximately 40 minutes. As the sun burned into me, I knew it would work this time. I returned indoors and removed the top and bottom of the bikini. The sight of clear female tan lines was amazing. I felt more female then ever before. More female then when I was riding the dildo, or wearing my sisters bra. My erect cock needed attention. I began to stroke it until I came. But something was missing after I came. There was no guilt. My cock shrank down to its original size, and I still had no guilt. I waited for it, but it never came. I took a shower, went to the mirror to view the tan lines, again waiting for the guilt that never came. `You see,' said my mind, `you are becoming a girl.' It was undeniable. No guilt about what I was seeing -- female tan lines. Now I just had to keep it hidden. good thing it was the end of summer. I left the nails on me that weekend, and after a little while got dressed up again. I went about my days at home that weekend as a girl. It felt great. I had no guilt the entire time, and felt bad when Monday morning came. That winter, I periodically shaved my legs and chest. I enjoyed the feeling of femininity. The tan lines eventually faded and things remained steady for a while. I continued my anal adventures, and expanded my visits outdoors especially at night. I began to work up enough courage to walk to the street at the end of my driveway. Eventually I continued forward, walking to the corner. Then down the next street, and the next. Soon, I was inserting the vibrator inside of me, then wearing panties to hold it in, then jeans, a bra and top, the wig and make-up. I would walk down to the main road late at night with the vibrator quietly buzzing inside of my ass. The occasional car would drive by and I would subtly turn my head. People were now seeing me as a girl. I was never stopped or talked too, but there I was. Late night became a little earlier, and earlier as time went forward. The spring and warmer weather came, and it started staying light out, longer. I eventually began to go for drives as a girl too. Sometimes during the day. My confidence was building and I was becoming more comfortable with my female self. It dawned on me that may want to come up with a female name. God forbid I meet someone and they ask for my name, I would try to fake it. It was a simple decision to go from Andy to Andrea. As Andrea began to really take a more prominent role, I started to wonder again about my sexuality and at what lengths I was willing to go as Andrea. The thoughts may have been encouraged as I had met the girl who eventually became my wife. Part IX: I Can't Stop My wife-to-be Abbey had no idea about Andrea. We led a very conventional courtship and got married in a very traditional way. Once I proposed to Abbey, I figured that I had to stop dressing as Andrea. I knew with several months to go before our wedding that I should enjoy my time as Andrea. I never considered exposing Andrea to Abbey. She was fairly conservative in her personal views although somewhat moderate on her social views in general. We got married, went on our honeymoon, had great sex and returned to our new life together. During our honeymoon, I considered Andrea to be dead. I had a moment or two of weakness while Abbey was in the bathroom, and her bra was laying out on the bed, but I did resist. We continued together for a couple of weeks at home without Andrea and there seemed to be no trouble. Part of me felt relieved that Andrea was gone. This complication in my life was over. One morning that changed. Abbey left for work early. I was able to stay in bed until 7:30 however. Through the fog of half sleep and half awake, I began to stroke my cock. As it became erect, my thoughts began to shift to bras, and panties. Flashbacks of peaking into my sisters drawers became vivid. The sight of myself riding that dong also came to focus. Suddenly I awoke in ernest with a very hard cock in my hand. I stopped myself and got up. "I have to stop before its too late," I told myself aloud. As I began to walk to the bathroom, still with a hard penis, my mind began to comment. Softly and distant at first but becoming louder and more pronounced every second. `Remember how your sisters bra felt across your back and shoulders? the feeling of that vibrator deep inside your ass. The weight of breasts, even thought they were water balloons? Remember Andrea?' I couldn't take it. I did remember all of it. My cock was raging, and I began to sweat a little. I had discarded all of my clothing, so there was no way I could dress. `What about Abbey's bra Andrea? You could put it on, and its just your size,' said my mind. Just my size? I thought to myself. Abbey is a 36DD. There is no way that that is my size. But deep down Andrea was coming back, back to life within me. I began to slowly walk to the drawer where Abbey kept her bras. I took out a dark green bra from Victoria's Secret. As I held it out, I saw the size of the cups. I knew Abbey was bigger then my sister by 2 full cup sizes, but to see the bra in front of me like that showed me the true nature of large breasts. Before I could stop it, Andrea reared up and the bra was on me. After nearly a month without it, I felt like what a drug addict must feel like. The old feelings of femininity rushed through me, and washed over me. I came almost instantly. The guilt returned. In the shower, I thought about what I had just done, and what the consequences were. I realized that this was the rebirth of Andrea, and that I could never stop her again. This sobering thought rang through me for weeks. I continued to wear just my wife's bras and dirty panties. I knew that one of two things were going to have to happen. Either my wife was going to have to be told and she would leave me, or I would ease her into it, and she could be okay with all of this. I choose the later. I carefully watched and waited for an opportunity. the opportunity arrived when we were watch "Real Sex" on HBO and after the show we talked about vibrators. My wife had never seen one or used one. I asked her if she wanted to try it. She hesitated and eventually said, "why not." I was happy to oblige and got her a black one. 9" long and 1" in diameter. She used it, and enjoyed it very much. I thought for the first time, that she would be welcoming to Andrea if presented with it correctly. I was hoping because I couldn't stop. Part X: Meet Andrea The opportunity to introduce Andrea to my wife began to take shape one afternoon after about 3 months together as husband and wife. Not to be gross, but I had pretended that my butt was a little raw from using the head a little too often. "Put some vaseline on it Andy," said my wife. "Are you kidding me Abbey?" was my response. "what are you trying to do, lube up my ass so you could shove something in it?" "Be serious," she said. "But if you really want too..." I was stunned she even made the comment in jest, but I jumped on the opportunity. "well, it would be interesting to know what all the hubbub is about." "Okay, I was kidding Andy." "I figured you were Abbey, but i'm just saying." "Andy, do you really want too? I mean cause if you do," she hesitated a second, "I would be willing to see your reaction to it." I had to wonder if she actually knew anything about the real me. I decided that she couldn't. I made it seem like there really was no way and I was just kidding, but eventually agreed. We got naked and she got the vibrator. A little fooling around, and some lube on my ass. She made me put it in while she watched. She didn't want to be responsible if it hurt. Little did she know. I slid it in making a good acting pitch that it was my first time. Before long she was pumping it in and out of me. I was in heaven, but down played it a little. I came hard and then we cleaned up. We said little for the next hour, but then she asked me. "Did you like it?" "I can't believe I am saying this, I said, "but I did. It felt good." "So you like getting fucked in the ass?" she asked again. I hesitated and did a little back peddling but I told her it felt good. "Are you okay with that Abbey?" She said she was fine with it. If I enjoyed it she enjoyed it. We continued doing it in my ass every now and then. I still dressed in her bras privately. This went on several weeks. I noticed she was deriving much pleasure from fucking me with the vibrator and I knew I could introduce the next phase. She was wearing a thong and was getting dressed one morning. "I have to ask Abbey, what does that feel like?" "What?" she said. I pointed to and said the thong. I asked her what it felt like. Did it hurt, or chaff? "Well if you really want to know, come and try it on." Again I was in stunned surprise, but still loved it. She again cooed me to try it. "Come on, lets go. You want to know here you go." And she took it off and handed it to me. with some debate and hesitation, I obliged. Of course it felt great. I described to her how it felt, and she said it felt the same for her. she then began to rub my growing cock through the thong which felt great. We went on to have sex with me wearing it. That too became a part of our sexual routine. The real test was yet to come. I eventually revealed to her that I had become curious about what a bra might feel like, and other women's clothing. After all I did like the panties. she dared me to try some of it on. I hesitated and said it was just cheap talk. But then I went up stairs and proceeded to dress up fully. I used socks to stuff the bra, put on a pair of her jeans which fit perfectly, and a sweater top. when she came up several minutes later she was shocked. "Oh my god, I can not believe you fit in my jeans," was her first statement. She wanted to know how I liked it. I told her it was comfortable and I rather enjoyed it. "Am I going to come home one day and see that you have had a sex change?" she asked. I swallowed hard. "Are you fucking nuts. Of course not" Little did she know how close to home she had hit. I didn't even realize how close to home she had. Sex change? I had never thought of that, or heard those words in my own head let alone from someone else. After much discussion and debate, we had agreed that if I was to dress fully she didn't want to know about it, or see it. I was disappointed though. I liked being dressed around her. It made it all so real. For the first time, I was interacting with someone else as a girl and I loved it. As time went on my anal experience with Abbey continued. We started experimenting with more toys, and different toys. The best was the two headed dong, because we shared it together. One end in her pussy, the other in my ass. She also had me sucking on a cock shaped dong one night. I asked her why. She said why not? That too became a part of the routine. Eventually, Abbey asked me point blank if I had a name for myself as a girl. I told her I had never thought about it. "I think Andrea is appropriate," she said. the fact that she had thought about it at all was a good sign. That she had chosen the same name was miraculous. "Okay," I responded. "Meet Andrea!" With all of these remarks and actions by Abbey, I was beginning to feel confident that Abbey was welcoming Andrea. plus with the combination of the anal toying with me and now the sucking of the cock shaped dildo, part of began to wonder if she wanted me to be with a man. The feelings of being gay or bi again rose up in me. This time the result was different, and effects of that response would be the final step in my entrance to womanhood. Part XI: Andrea Takes Over `My god, maybe I am bi,' I thought to myself. It was the first time the response was not repulsion. Sucking on that dildo felt great. Abbey seemed to be getting into it all. Maybe this could all work out. With my confusion, I turned to the internet. I looked up and researched "sex change" and that led me to "transgender" and "crossdressing." As I read, and researched I began to realize that I was not alone. I started to enter chat rooms so I could talk with others about all of this. I learned a great deal about myself, and what had happened to me. I began to understand that what began as a masturbation fantasy had become a real part of me over time. The future was looking light on one side, and dark on the other. I was scared of all of the whole situation. Then with the tragedy of 9-11, I lost my job. I was staying home, and alone and continuing my research about transgender and transexual. I began to look at photos and videos of "t-girls," and this was a turn on. After a short time, I stopped wanting to fuck those t-girls. I wanted to be one of those t-girls. I began spending more and more time as Andrea while my wife was at work. I began building my own collection of clothes. I bought a new wig, and for the first time ever, a pair of 5" heels. My sex life with my wife continued to evolve. Eventually, she agreed to let me have sex with her while I was wearing her bra, and water balloons stuffed inside the cups. To my surprise the next night, she asked me to dress up. Eventually I told her I had purchased a wig, and make-up and heels. she became more and more accepting of it all. "I want two things from you," she said. "First, if you really want to be a girl, then start hormones and do it already. Second, just give me fair warning." I was stunned and pleased. She eventually had me begin life experience while at home as a girl. "You will never know if you like being a girl if you don't stay dressed for long periods of time." I hesitated about this for real. "I am scared of doing that Abbey. What if I really like it? What if I did want to try hormones?" "So, what if you did? Then you start hormones and begin your transition." Was this for real. She was seemingly allowing me to transform and seemed okay with it. But I had a few problems with it, and told her what they were. "First of all Abbey, Society is not keen on the idea of t-girls. second, I couldn't give you up to become a girl. I love you. Lastly, what about our families?" "Andy, that is all for you to judge. If you want it bad enough, then you should do it. True, our families would be outraged, and society isn't too hot on the idea. I love you too, and I want to be with you, but I don't think I could remain married to a woman. But, like I said, if you want it bad enough, then do it." I knew she was right. Part XII: The Coming Years I am not ready to give up my current life completely which is what a transition would require. I started out just dressing, but that has become more of me then I ever imagined. Out of a 7-day week, I spend 4 of those days fully dressed. Some of those day with my wife present. I have thought long and hard about actually visiting with a therapist to see what their professional opinion is about me. Abbey has been very supportive. She has plucked my eyebrows a little and helped with some make-up tips. She encourages me to keep myself shaved smooth year round. I know she wants me to be happy and she meant what she said about my choices. The coming years will tell the rest of the tale. I don't think my sister ever knew about how my future was in her drawers. Little did I know what the repercussions of that first day in her bra would mean. If I do transition, she will have to be told of her role in the process. It will be hard to explain it to her. Like this story? It is totally true. Send comments to andreabreasts@hotmail.com