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Beginnings by Tricia

I started experimenting with cross-dressing at a very early age (pre teen). As with many crossdressers my first experience was with my sister’s lingerie. After trying on several items, I dismissed it as curiosity, and figured that it was normal to some extent but never mentioned it to anyone. Several years later now in my early teens, I had my first taste of female superiority, my sister who was four years older than I and two of her friends were teasing me as usual but this time they used force while doing so.

They wrestled me to the ground and held me there until I stopped struggling to escape. Fatigued from the battle I just lay there helplessly and took their verbal abuse. The tears that began to roll down my cheeks seemed to give them even more power as they increased the barrage of insults: pussy, weakling, prissy, sissy pants, and telling me I was more like a girl than a boy, teasing me about how I would never become a real man.

Finally they released me and allowed me to walk away as they all giggled and laughed at me. This was the first of what became a weekly routine for the girls. They would stop by our house randomly through out the week with each girl enjoying their time controlling me in there own way.

I will never forget the fateful Saturday that forever changed my life. I was lying on the floor watching television when my sister came down the steps from her room after getting ready for a date.  As she walked past me, I could not resist glancing at her stocking clad legs and high heels. She must have noticed as I heard her make a sound in disbelief (uhh), as she turned around and ran back to her room.

Figuring that she forgot something, I was already positioning myself to get a better view of her legs when she came back down. As she entered the room she approached me, pausing for a second as she stood over me and then she slowly removed one of her shoes and started to push her stocking covered foot into my mouth.

I grabbed her foot and tried to resist, but I realized that she was too strong as her toes began to enter my mouth. Once they were in, she wiggled them about while telling me in a demanding tone to suck her toes.

As I did, she began encouraging my action by saying “that’s a good little sissy boy.” When she was satisfied that she had humiliated me enough she removed her foot from my mouth and told me to run to her room and get her purse. I quickly obeyed her. As I entered I noticed that she had a pair of stockings lying on her bed. I resisted my urge to try them on while grabbing her purse and quickly taking it to her. She said nothing more to me, just a quick look and a devilish smile as she headed out the door.

As soon as the door closed I ran back to her room, stripped off my clothes and put on her stockings. They felt so good against my skin, soft, satiny and silky. I closed my eyes and began running my hand over my legs until I was fully aroused. As I began to slowly stroke myself I heard the door followed by my sisters voice instructing me that I had to go to the mall with her. I jumped to my feet and pulled my sweat pants over the stocking as I heard her approach. She asked me what the fuck I was doing in her room; I just lowered my head, said nothing, and followed her to the car.

When we got to the mall, she headed straight to the shoe store and told me that I was to get a new pair of shoes for a wedding that the family was attending this coming weekend. She picked out an extremely expensive pair and suggested that I get fitted before trying them on due to the cost. That’s when I realized that in my rush to get dressed, I forgot to put on my sox.

I started to shake with fear as she motioned to the clerk for assistance. The sales woman approached and she instructed me to remove my sneaker, which I reluctantly obeyed. Once off she immediately began to smile as she sized up my stocking covered foot. My sister smiled and said to her; “Please excuse my brother, she uh, well he just loves playing dress up.” The saleswoman smiled as she left to get my shoes, when she returned she had two boxes.

She handed me the first, which I tried on and they fit perfectly, although my sister still insisted that I walk across the store in them to make sure. I followed her command as I had been trained to do. When she was satisfied that they fit, she told me to take them off and handed me the second box.

I opened it and inside was a pair of red pumps with three inch heels just like the ones she was wearing. I just looked at them in amazement and asked what do you want me to do with these. She smiled and said try them on of course. I did as she asked and again they seemed to fit perfectly.

She then told me to walk in them to make sure they fit, as I walked through the store I noticed that my sister and the saleswoman were headed to the checkout talking and laughing. Before I could catch up to them my sister paid and exited the store with my sneakers in hand. The laughter from everyone who saw me was too much for me to bear, and I started to cry as I walked through the mall.

When I got to the exit, my sister was waiting for me and as I approached her, she smiled, asking me if I had my both of my new dress shoes. I shook my head no, and replied just the ones I’m wearing. She then informed me that I would have to go back to the shoe store and get them, I wiped my tears and begged her to not make me walk back through the mall.

She said that she knew of a way that it would not be so embarrassing for me if I were interested. I jumped at the opportunity and followed her as instructed. We entered a store filled with women’s apparel; I stood behind her as she methodically picked out several item of clothing. She handed me the clothing and pointed to the dressing room while instructing me to try them on.

I entered the room and removed my clothes and started putting on the outfit she had picked out for me which consisted of; matching pink lace bra and panties, thigh high black stockings, a red long sleeve mini dress made of a stretchy type material and of coarse my red pumps. I was just about finished when I heard a knock on the door. It opened and she tossed me a mid length platinum blonde wig. I put it on, opened the door and was suddenly greeted by three saleswomen all smiling and encouraging me while laughing.

They quickly walked me to the middle of the store, sat me in a chair and started to apply a full makeover, complete with pre-finished nail extensions. It did not take long before all the women shopping gathered around and watched my makeover. When they we finished I stood and walked to the full-length mirror. I looked in amazement; I was beautiful, although I was dressed a little sluttish, but I was defiantly passable, no one would ever suspect that I was a man.

Satisfied with my transformation, I went back and retrieved my other pair of shoes without incident, except for a few catcalls by some boys hanging out by the stairs. My sister was thrilled by the attention I was getting and told me that we were going to celebrate my coming out. We walked through the mall and headed for her car. I was amazed at how many men were hitting on us; I asked her do men always act this way? She told me to get use to it and that the one good thing about it is that I would always be able to pick up a date on short notice because men are ruled by their head (not the one on their shoulders) and they naturally become weak in the presence of a confident woman. She said that she would prove it to me at our next stop.

She drove to a local eatery, which is a popular hang out spot for a lot of the local teens. I am sure I was overdressed because as we entered all eyes became focused on me. The boys were all staring and it didn’t take long for several to come up to us and ask us out on a date. Before I could say anything my sister answer for us both telling them that we would love to. The next thing I knew she introduced me as her friend Tricia and went on about how I had just moved here.

Dan who was to be my date stood there just staring at me, and by the size of his ever-growing bulge I was guessing he liked what he saw. He put some money on the table to pay for our meals, reached out for my hand and arm and arm we headed out the door to their car.

They drove us to a local park. I was sitting in the back seat with Dan and I was very nervous not knowing what to expect or do if he made any advancement toward me. My sister and Steve were already going at it pretty good, kissing and groping each other, which seemed to encourage Dan. He put his hand on my stocking covered legs and began to caress them. It felt so good I looked at him, smiled and subconsciously began to rub the bulge in his pants.

He began to gently kiss me and I returned his advances. My sister looked back with a smile saying you two seem to be hitting it off; you really make a cute couple. Empowered by her I began to unzipped Dan’s pants and was now face to face with his manhood, after a brief pause I slowly began to kiss and taste him. He must have noticed my inexperience and gently placed his hand on the back of my head and began to guide me to his preferred rhythm. Before long I was devouring him in his entirety and enjoying every inch.

Then without warning he exploded in my mouth I did my best to swallow as he firmly held my head now with both hands. Satisfied that I had cleaned him to the best of my ability he released me, as I sat up and began to wipe his remains form my face I looked up only to see my sister smiling at me and saying; “well Tricia, that was sure quite the beginning, I think you are really going to enjoy your new life….”

To Be Continued….

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