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Cumming clean...  

bobmattg

2/26/2011 7:24 am

Last Read:
3/8/2011 5:23 pm

For as long as I can remember, very possibly this would mean my whole life, I have been fascinated by women. I am captivated by every aspect that the phrase “being a woman” or the term “feminine” would imply. It would be no stretch to say I am in love with all women. Very true, but my infatuation goes much deeper than that. I love that, in my mind, any woman could make any man beg for them. True, there are probably large holes in my vision, but that is a world that I would love to inhabit. As you probably could have guessed, a large part of me wishes I had born a woman. So, in my younger years, I guess I was confused about my sexuality; I believe I did a pretty good job keeping this hidden. I did nothing that would make me seem different than my other male classmates. I had girlfriends, went out on dates with girls, attended parties with the other youths, doing everything that you would expect a kid to do. My fantasies mainly involved me, with a girlfriend, and her transforming me into a woman, usually against my will. To be truthful, this is when I know this isn’t real, because she wouldn’t need to force me, I would beg for this dream to be fulfilled. Once I was a “woman”, I dreamed that I would be accepted by the group of my girlfriends then do anything and everything they wanted. I would love to be completely made over and transformed into a woman. When I first started cross-dressing, while I obviously wanted to become irresistible to men, it was more about realizing my dream of being a woman, than sexually living life as a woman. My early dreams and fantasies generally involved me, as a Crossdresser, joining a sorority or other group of women, and just being a woman. I would know my role, I wouldn’t be allowed to have sex with the women. I would be told to assist the men, who knew about my situation and I believed were turned on by the circumstances, that were serviced by my sisters by helping them undress and helping them put a condom on their cocks. Next, I would kiss her lover with passion while we held each other securely, his hands firmly caressing my ass through my skirt and panties. Then I would stand with my arms above my head, so that I couldn’t pleasure myself, and watch to learn how women make love to men. Following their sex, I would help remove the condom then wash his cock and dry him. I then would make out with him until he was finished with me. I have had dreams about being a bride or in any other situation where a woman is all dolled up with complete make-up, jewelry, and perfume. I would love to go to a beach and tan in a bikini. Sure, people would know, but I’m certain there are beaches somewhere where I would be accepted. In my earlier days my idea of being a woman was missing one important element. Over time I have learned to appreciate more and by doing Internet research about tips and techniques with performing fellatio, I now see the beauty in receiving and consuming fluids from your lover. Another aspect of me becoming a woman which I haven’t mentioned, because I guess I’m a bit apprehensive seeing that as a woman I am still a virgin, is that I would make sure he knew that he was taking my virginity and I would always have him with me in my heart. I would ask if he wouldn’t mind starting off slow, lots of kissing and holding each other tightly. Then I would fall to my knees as he would fuck my mouth for a couple minutes before taking his cock from my lips and slapping my cheeks with his penis. Then after picking me up and pushing me stomach-down on the bed, it would be obvious to me what was going to happen. He then would have me stand and take my panties down to my ankles and get back kneeling on the bed. Then I would be told to put my chest flat on the bed so my ass is available to him. Obviously, I want this to happen. I want to be face-down, ass-up on the bed then hear that he would like me to grab my ass and spread my cheeks making his target, my asshole, available to him, I would do this as I would feel the head of his cock brush against the outside of my virgin asshole. I would try to pull my cheeks open wider, thinking that was what he wanted from me. He would want to hear from me that this is what I want; I would say “Yes, please”. Before the words had completely exited my mouth, and in one motion he grabbed each wrist in one of his hands and pulled back. This caused my back to arch as his cock plunged deeply into my ass. Had I not expected it, I would have called the pain intense, but the pain was lessened by the thrill I was experiencing while I listened as he told me, his slut, how hard he was going to fuck her. I loved how much I felt like a woman as he rode me, quick short strokes at first, followed by slower deeper strokes then he would deposit inside my body. He would be turned on as I would squeal in pleasure and repeat his name while telling him that he owned me. I want my lover to be sure of this; while he may think that he’s fucking me, I’ll be making love to him. The age of my lover is not that important to me, except I would prefer him not to be younger than I am. I do have my daddy/daughter fantasies, where I am used by a much older man, and these really excite me. I don’t want us to be equals in the bedroom, in my fantasies my lover usually is in control, and I am at their mercy, this seems the way things should be.

My intentions for this masterpiece of fiction, if this could be true even in the smallest way life would be so magnificent, was to start with a short paragraph to explain my state of mind, then reveal the fantasy that I think of all day and dream all night. Well, my introduction ran a bit long, and here’s my feature…

I was so excited about the upcoming weekend because I actually had plans which didn’t involve my daily occupation or yard work. Although I wasn’t sure about the specific details, other than I was going somewhere with a good friend, and he promised that we would have a great time. Ken, my friend, was a man who I had known since we were kids. After our school years when people usually headed out to start lives, a few of us stayed around home and found satisfaction here. Ken is probably the friend who I trusted the most, the person who knew the most about me, as well as about my many fantasies/fetishes. He was the only person who knew my deepest, darkest secrets; such as my crossdressing interests and my other unmentionable wants and desires. As I said before, I didn’t know the details, other than he asked me, above all else, to trust him, and I did. So I expected something big, and I didn’t ask why when he told me to shave my complete body. I did as I was told.
So, all of Thursday night I, very carefully and over the course of four hours, shaved off all my body hair to begin my change into a woman. I spoke to Ken during the day on Thursday and he told me not to wait until Friday, he wanted me to consider myself a woman, his woman, from that point forward. I was to answer the phone, if it rang, in my “sweet little girl” voice. Ken and I usually played around with me doing that voice, and it needn’t be said how hot that voice alone got me feeling. He told me to start practicing peeing without pushing my penis down. He told me that I should sit, spread my legs and let my fall down aiming into the bowl, then squeeze my legs together and pee hands-free. Surprisingly, this worked, as this did make me feel womanly.

(Unfinished)

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