This story is somewhat of a historical fiction. Most of it is true, with embellishments and color added.
1:51 PM 9/12/2010 Beginnings Everything that is me began innocently enough, I mean what little boy doesn't like to steal a peek under a little girl's dress. Still, it seemed as though there was supposed to be more to it. As a child, and even as an adult, I think that I was a little more preoccupied with sex than most. I remember masturbating as a small child. I loved the texture of plastic pants, and would frequently pleasure myself with them. Plastic pants were worn over cloth diapers to contain moisture, before disposable diapers were invented. I had been caught numerous times 'laying on my hands' by my mother as a boy. Though she was never harsh in her admonishments, she never told my father. From the first grade and all through school, I became an accomplished voyeur. And from the age of eleven until fifteen I made it my mission to know what lay beyond the white, pink, or blue triangle! At fifteen, I met a girl named Susan, and soon, after intense persuasion, I found the holy grail that is a warm pussy. She would often wear silky nylon panties, and I found that petting her pussy over them took my breath away. She as well was aware of my fondness for her silky panties and wore them whenever she could. Susan was the first, but certainly not the last in my exploration of pretty panties. I began 'borrowing' my mothers panties to play in. She, as most girls at the time, wore silky bikini hipsters,for herself and her boyfriend. My father had since passed when I was eleven,but that is part of a different story. I would go into her 'pantie drawer' and carefully select which pair that was 'me' at the moment. The memory alone hitches my breath. Still, silky panties and warm pussies, weren't enough, and soon my 'explorations' began to grow. I began to wonder what it was like on the receiving side of the 'magic pole'. Cross dressing was that beginning. I began selecting other delectables from my mothers panty drawer. Soon I was in her closet trying on skirts and dresses. My mother was attractive and shapely, and could wear the style of the day. In the early 'seventies' mini skirts and dresses, hip hugger jeans, and 'hot pants 'ruled the womens clothing racks. Whenever I was alone I would 'model' and pose in the mirror for myself. This went on for a period until I got careless and was caught by my mother in full regalia. I was mortified, though she almost seemed to be waiting for the moment. Looking back, I think she knew and set me up to be caught. She said she wouldn't mention it to her boyfriend Tom and that I would have to be more careful in the future. She didn't need him to know that there was a crossdresser in the house, although he always showed a restrained regard for me. When I was seventeen I began hangin' out with a guy my age, actually he was a year older, named Rick. Rick was interesting in that he had interesting hobbies. Girls didn't seem to be one of them. That wasn't unusual as a lot of guys were afraid of girls at that age. They simply did not know how to approach them. Nevertheless, we began hangin' out together. I was in between girlfriends at the time, or so I thought. Rick's dad was an outdoorsman and let Rick do more than most fathers at the time. Ergo, the interesting hobbies. Rick and I would camp out in his back yard on some summer nights and smoke cigarettes and drink cheap wine. It was the thing teens did as a form of rebellion. Rick always seemed interested in showing me his cock. By that I mean he always seemed to have to urinate in my presence. On more than a few occasions I was treated to an eyeful of his member. It was definitely bigger than mine. I would have guessed around four inches flaccid. It wasn't long before I began to wonder what his cock would look like at full mast. I was surprised to find myself fantasizing about his stiffened cock being pressed to my lips. I also wondered how it would feel to be pushed passed my satin panties and into my sissy place. Rick began to notice how my eyes were always drawn to his trouser zipper, and began to purposely handle himself more. Soon my curiosity grew to obsession and I was now on a new mission. The end of October was when I was going to satisfy this obsession! Halloween is always the best time to play 'dress up', and with my new obsession I was going to dress to take. Rick's neighbors were hosting a Halloween party this year and he asked me if I would like to attend. He told me that he was going rent a 'Batman' costume. I said that would look cool, but I could not afford to rent a costume, and wanted to surprise him with my costume. We both agreed and looked forward to the party. I had grand designs for that evening and had no idea how it would change the course of my sexuality. This would be the night I would discover the 'other side' and the 'magic pole'. The week of Halloween I told my mother about the party and the costume that I had wanted to wear. Although she agreed to help me dress for the occasion, she was a little wary. "You'll look like a cheap whore", she had said. I told her that it was all for the fun. I didn't tell her that that was my intention. My mother and I are of similar stature, so it was not hard to decide which outfit to choose. We won't forget that I had pretty much worn all of her clothing at one time or another. I chose a blue polka dotted miniskirt, they were called 'Sizzler' skirts at the time, and a white rayon crepe short sleeved blouse, that tied together at the mid drift. Underneath I wore a white lace garter belt to suspend thigh high stockings. For panties I chose a light blue satin front, sheer rear polka dotted hipster bikini. The brazier matched the panties. Mother helped with my make-up. She exasperatedly sighed when I insisted she apply the make-up a little heavy. After a complete self inspection of my dress, to make sure that my garter and stocking tops werent showing, I was ready to go to a party. I couldn't believe that I was going to go through with this insanity. I arrived at the party around 8:00 p.m and was greeted warmly, though a little skeptically. Rick's father by then had a drink in his hand and remarked about how I was dressed a little too convincing. He nevertheless told me that I looked sexy, and gave me a wink. Rick's mother wasn't as accommodating but remained cordial. The other guests either raised an eyebrow(women), or smiled to themselves(men). When Rick greeted me, his jaw went agape. He surveyed my dress completely as if to take inventory. "Nice costume", he said, and unconsciously adjusted himself. My glance instinctively was drawn to his crotch. This did not go unnoticed by him as he restrained a smile. His costume consisted of a set of top and bottom tights. The 'Batman' insignia on the chest with 1/2 length satin cape. The mask covered his eyes and the bridge of his nose. The bottom tights came complete with satin brief and utility belt. His package defined itself and seemed to grow in those satin briefs when he adjusted himself. My eyes were immediately drawn to his cock when he did so. This did not escape him as he suggested we go into the kitchen and have a drink. As teenagers we weren't permitted to drink alcohol, unless by special occasion. This evening was special enough. We continued to eye each other wondering what the other might be thinking. Rick said " Let's go across the street to my house, there's something I want to show you." "OK. You lead the way." I said. “No, you lead the way." he said. We left without incident and headed to his house. I turned to see if he was behind me and caught him looking at my behind and rubbing his cock. "What are you doing?" I asked. Startled, he released himself and smiled sheepishly. When we reached the house he let us in and said"In my room." We went into his room where he closed the door behind him. He went to a chest of drawers and took out a small pipe. "What is it?" I asked. "A little bit of pot" he replied."Cool" I said. He then motioned to a small sofa to sit. He then took out a lighter and lit the pipe. We sat quietly and passed the pipe between us. We were a little buzzed and I stood to look at the models he displayed atop of his dresser. "Is this what you wanted to show me?" I asked referring to the pipe. I turned to find him rubbing his cock again. "Yes" he said. My line of sight was again averted by him rubbing his cock through his satin briefs and I then offered" Would you like to see the rest of my costume?" He seemed to understand my direction and pointedly said"Yes." I crossed the room and stood before him, and looking at him directly, I began to lift the front of my short skirt. His gaze was riveted on my skirt as I slowly raised the front. H leaned back on the sofa and began to rub his cock through his satin briefs. My own eyes were then directed towards his stiffening cock. I continued to lift the front of my skirt revealing my stocking tops and garter. " Would you like to see more of my costume?", I offered. "Yes" he sighed as he rubbed his thickening member. I pulled my skirt up now completely showing him my satin panties, polka dotted with little hearts. "Oh my god." he moaned. I swished my hips a few times so that the light would play off the satin fabric of my panties ." Would you like to see my hiney?", I asked. His response was to adjust his cock so it would have room straighten. " Now if I show you the rest of my costume, will you show me the rest of yours?", I asked. "Yes", he breathed. I then turned and bent slightly over and stuck my butt out just a bit. "Do you like my sandals and anklets?" I asked, as I began lifting the back of my skirt. "Yes." he managed. I now had the back of my skirt raised above my waist revealing my sissy cheeks through the sheer back of my panties. I wiggled my hiney for him. He then sat forward and began to rub my sissy cheeks through my sheer panties. I then stood up straight and turned to sit on his lap." Do you mind if I sit here?" I asked as he leaned back in the sofa again, now stroking a fully erect cock. "Mind if I try?", as I put my hand on his thick member, replacing his hand, and began to pet his swollen cock. His hand then moved to my stockings. He began to rub my thigh. His hand then moved to my blouse to explore my satin sissy brazier. I continued to stroke his burgeoning member and was astonished by its size. I knew that it was large, but it seemed to grow larger still. " I'd like to see the rest of your costume now." I said. Rick then sat up and kissed me. I returned his kiss and he offered his tongue, which I accepted. He then pinched my butt to stand up. I stood and sat back down on the sofa. He began rubbing his cock again and said, " If you want to see the rest of my costume, you'll have to take it out yourself." He then took my hand and began rubbing his cock with it. The feel of his thick member through the satin fabric was intoxicating. I waited years for this moment and could wait no longer. My fingers took the elastic waist of his tights and began to pull them down around his hips. At first they didn't want to let go but then they yielded. The elastic caught on the head of Rick's cock pulling it down with the fabric until his cock sprung free. "Oh my." I managed. His cock all eight thick inches stood alone throbbing to his heartbeat. I wrapped one hand around the shaft that left room for my other hand. I slowly began to stroke his beautiful stiff cock. "Do you like the rest of my costume?", he offered. Clear cum was beginning to leak from his cock's swollen head. I responded by kissing the head of his cock. He then took himself in his hand and began to brush my lips with his leaking cock. He then cock slapped me while asking me if I liked the rest of his costume. "I do." I moaned. Show me how much you like it, as he pressed his member to my lips. I accepted the head of his cock into my mouth, at first kissing it, then French kissing it. " You're gonna be my girlfriend." he said as he pushed himself deeper into my mouth. I nodded my head and moaned with his cock in my mouth as to affirm his suggestion. I then took his cock in my hand and fed it to myself as deeply as I could. I could almost swallow it. God knows that I wanted to. I then began to lollipop his cock alternating between deep throating him and lollipopping his cock, moaning repeatedly to show how I felt about having his stiff cock in my mouth. " I can just about wait to put it in your sissy cheeks". He said. The thought of his huge member being pushed into my sissy place made me moan loudly. He then put his hand on the back of my head and began to thrust himself in and out of my mouth. Not forcefully, but enough to convey his urgency. His pace began to quicken as he pushed himself deeper into my mouth. He then said," Here it comes". It was at that moment I began to withdraw him from my mouth, while stroking his cock, he released, at first erupting, then spasming ropes of jism on my lips. cheeks, and chin. I didn't know a guy could cum so copiously. Pete North had nothing on Rick this evening. I continued stroking and lollipopping his cock until the cascade subsided. Sticky cum coated my face, and dripped off of my chin as well. Rick then took his still erect cock and began to swab the cum from my face and feed it to me. It kind of burned my throat, but the taste was wonderful. Cum is a flavor that I never grew tired of. By now my face was smeared with stickiness as I finished satisfying his cock. I was still sitting with Rick's cock in my hand when there was a knock on the bedroom door and his father poked his head in to see where we had gotten off to. Needless to say that what he saw, was not what he expected to see. “What the hell is going on here?", He boomed. " It's not what you think it is dad." Rick said. " It's exactly what I think it is." he said. He looked over at me, my face still wet from the cum bath that Rick had just given me. "So, you are a little cock whore aren't you?" he said. "Please sir, don't tell my mother." I pleaded. ............Part one of a series to be continued.