I guess it all started on a Saturday afternoon. My mothers bra was on top of the laundry pile. It caught my eye and I instantly became fascinated with it. I stole the bra and ran to my room to try it on. I remember the rush it gave me. I loved it and I decided to continue. I did everything I could to get my hands on more clothes. I stole bras, panties, pantyhose, slips and dresses from my mom. Swimsuits and bras from my cousins and grandma. I couldn’t get enough. I strained to look and feel more and more like a woman. I refused to be the typical person stuffing their bras with socks and tissue. It just didn’t look, but more importantly, feel like real breasts. So I got the bright idea to fill rubber gloves with water and use them as breasts. It worked for a long time until I learned what a breast form was. Then every cent of my pay checks were going to clothes and underwear. And that is where my story begins.
It was Thursday afternoon and my family had just left for my brothers baseball game somewhere south. I really didn’t care, the house was mine until Sunday. It wasn’t more than 2 minutes after they left the driveway that I was already in my room getting dressed. I had my breast forms glued to my chest, an expensive corset which was the pride and joy of my collection, with the attaching garters and nylons on. I continued to put my slip, and dress on completely oblivious to my surroundings. Unbeknownst to me my cousin had been recruited by my mother to check on me while they were away. She had let herself in with the key she had been given. She made he way down the stairs to my room where the music was playing and I obviously was, singing and dressing away. She turned the corner and we both let out a started yelp and of course I jumped to hide. There was no where to go, I was trapped. I stood there with my back to her trying to hide my shame.
“Trent? What are you doing.” she asked. Nervously keeping her distance from me.
“Nothing,” I replied nervously, “what the fuck are you doing here anyway?”
“Your mom asked me to come check on you, so I stopped by to see if you wanted to go get some dinner and you’re here dressed up like a girl. What are doing dressed up like that?” I turned around to face her. She had a mixture of emotions on her face. Im sure I had the same look on mine. I was blushing with embarrassment, but trying to hide it.
“I just like the way I look when I dress like a girl. I just… I want to be a girl,” I said hanging my head. For some reason Amanda always sympathized with me. I guess that’s why she was my favorite. We did a lot of things together aside from the usual thanksgiving and Christmas dinners. We hung out a lot, went to movies and had grown really close. And it had always been her that I had looked up to when I would dress up and play lady. It was here clothes that I had started my collection off with and I wanted to tell her so much but in that situation I figured the best thing to do was keep my mouth shut. She could I was being sincere. She moved closer to me and put her arm around me.
“Well maybe you could stay a boy a little while longer for me,” and then she did the one thing that surprised the hell out of me. She bent down and kissed me. I was shocked and instinctly pulled back.
“What are you doing?” I asked.
“I want to see what this is like. I know you have always wanted me and I’ve always wanted you too. So this seems like a better time than any doesn’t it?” she began fondling my breast with her hand as she bent in again for a another passionate kiss. Only this time I didn’t stop her. She stuck her tongue in to my mouth and we twisted and tangled. The grope session became a more furious and she and I began feeling each others breasts and rubbing each others bodies all over. I started to lift her sweater off so I could feel her big natural breasts. She took it eh rest of they way off with only a brief pause in the suck fest being created between out mouths. She wore a beautiful red satin bra over her huge 30DD breasts. Her skin was soft and silky and warm just the way I wished my skin was. But do to the hormone difference, all I could do was shave and lotion up. I unbuttoned her pants and she helped me shimmy them down her legs. The tiny red thong she was wearing was so hot on her I didn’t want her to take it off. She tore it off anyway. There she was, the only woman I admired enough to emulate, standing in front of me naked, kissing me and feeling up me fake female body. I was shaking with excitement and passion as she guided me over to the bed and lay me on my back. The pink silk slip I was wearing slid down around my waist when I bent my knees slightly and opened up my groin. The bulge of my penis was very obvious through the skimpy piece of cloth covering it. She maneuvered the garter and panty to free my penis and put it in her mouth. The warm and wet sensation of a beautiful girl softly sucking your penis was had me in a trance. I lost track of time as I lay on my back fondling my fake breasts with both hands. Thousands of images were running through my head imagining she was licking the swollen clitoris of my non-existent vagina. I longed to feel the deep penetrating power of a large penis enter me. I wanted it so bad.
She finished me off and rolled onto her back. I instinctively knew it was my turn. I got up and headed for her vagina. It was sopping wet when I got to it. I began by licking her swollen clit and tasting her juices. It was so sweet. I inserted a finger into her and began to stroke it back and forth. She began to squirm in ecstasy as I continued to singer fuck her. After a few moments of letting her wiggle I decided it was time to fuck her. I arched her legs and pulled her toward me. I gently pushed my penis into her. Enjoying every moment of it slowly sliding deeper and deeper into her. I reached my maximum depth in her. It was wonderful. But I still wondered what it felt like. I could only imagine. I was jealous of her. I started stroking in and out. Slowly at first but getting faster and faster. I reached the point of no return and spilled my cum all over deep inside her. I let out a deep sigh as I leaned forward and lay on top of her, still inside of her. The events of the day had exhausted me and I was tired as hell. I kissed her once more and she kissed me back. As we lay there together she whispered in my ear something I still remember. “I love you Trent. And if being a woman is what you want, I’ll do everything in my power to help you get there.” she kissed my neck and we fell asleep in each others arms. Girlfriend and cousin.
I’ll continue this and finish the story if I get a good review from this. Let me know.
