Sissy Miss Debi free porn video

Sissy Miss Debi Penned by Miss Deborah (Debi) Leigh Johnson One I did not know who to curse, or who to praise for the predicament that I was in. I knew only a couple of things for certain, and my mind and emotions were all addled about everything else. One, this had to be the most erotic experience of my life. Two, there is no way in the world that I should be in this circumstance. It was not explainable. It was totally wrong. It is not justifiable. But I loved what I was feeling. I snapped back to the reality of the moment as the camera flashed again and again. Jeff was walking around me and praising me for being so pretty and so feminine as he recorded on film what I looked like as I followed his explicit instructions. He told me to do this and I did it. He told me to do that and I did that. No one in my entire life had ever paid so much attention to me before. No one had ever been so admiring and praising of me either. I was wondering if I was falling in love with Jeff. That could not be. It was too wrong. It was against everything that I had ever learned in my life. And yet, so was wearing such a pretty outfit and letting the man photograph me as I slowly peeled away one item at a time, down to nothing but delicate pretty lace peach coloured satin lingerie. It was wrong because I am not a girl. It was also wring because Jeff soon saw that I had an erection in my pretty panties, and he had seemed to be delighted by it too. He told me that it was really cute the way the shininess of the satin highlighted it. Boys were not supposed to have cute erections that were highlighted in satin panties. But, rather than blush in shame, put my dress and slip back on, and run out of there, I had blushed in pleasure at hearing his words. He liked me in the pretty clothes of a teenaged girl. He also had a bulging in the front of his khaki pants. It should have repulsed me. But I was finding that rather than being repulsed, I felt kind of flattered that as girl, I could turn a guy on like that. I need to explain how this all came about, okay? Two Sandy and Dave were my best friends, if not my only friends. We had all grown up together, gone to the same schools, the whole nine yards. In our remote rural setting, there were three homes and that was it. Our respective families each lived in one, and we were close to each other. There were no other homes within miles of where we lived. Naturally, since we were the only ones there, and we were the same ages, we hung out together. We had no choice, or we could be all alone. Sandy is a knockout cheerleader candidate type of chick. She has thick blond hair that she can never manage to keep under control, but on her the wild fly away look is absolutely devastating. She is gorgeous. She stands a full 5' 3 3/4" tall in her bare feet. She is a walking wet dream, if you want to know the truth. And she knows how she affects guys too, and she relishes the power that it gives her to make guys do anything that she wants. Dave is her opposite, not to also mention mine. Of the three of us, I am far more like Sandy than like Dave. I am a quarter inch taller than she is. I have the same colour of long hair, but mine never looks unkempt. Mine is always neat, shiny and thick like hers, but it is always neat. I usually wear it back in a loose ponytail on my neck to keep it out of the way. I have wanted to cut it many times, but Sandy loves to spend time playing with it, and practicing her hair dressing skills and she threatened to kill me if I ever let anyone but her cut it. Where as her eyes are green, mine are hazel. She tells me that I have bedroom eyes, the kind that would drive men crazy if I was a girl. She always talked to me like I was her girlfriend, I guess because I was so much more like her in stature and in temperament than Dave was. She'd often just roll her eyes at me and explain simply that Dave was a guy, and he could not understand her like I did. I never commented that I was a guy too. Now Dave, he was a guy all right. He was gentle, but he was all male. He was really masculine, just like his dad. He had thick curly shoulder length shiny black hair and devastatingly light blue eyes that made you think that he was looking deep into your soul whenever he looked at you. He often gave me the shivers when he looked at me. So, we grew up going through the school system year after year. By the time we had reached twelve, it was obvious to us that Dave was going to be all man, Sandy was going to be a beautiful woman, and I was going to be more like her than like Dave. It was about the time that she had taken strong interest in things like hair and makeup that I sort of became her model. I was cajoled almost everyday to let her try this out on me, or to let her try that out on me. Heck, I was even cajoled into wearing the new dresses that she was making for her home economics projects. So after the first few initial embarrassments, Dave sort of got used to the idea of every once in a while seeing me wearing makeup or of seeing me wearing a dress while Sandy pinned up the hems or measured the shoulders or something like that. I got to the point where I really did not mind it too much either, because it seemed to be so important to Sandy that I was willing to help her in that way. Dave did not seem to care either way what I wore. But by the time that I'd reached fifteen, I knew for certain that Dave treated me more like I was his sister than like I was his best guy friend. I turned seventeen in my last year of high school. My parents died too that year, killed in a hit and run accident on the highway. I was devastated to say the least, and I have no idea of how I could have gotten through the grief if it was not for Dave and Sandy, who had developed a romantic relationship by that time. Because I was of the age of majority, when all the stuff settled, I found that I owned our house that was all paid for. The car insurance company paid out a lump sum settlement of $200,000. Both my mom and dad had life insurance as well, as they owned a small engine repair company that I had not interest in. The suppliers all took back their stock in my parent's business when it was soon realized that there were no ready buyers for the business. So because I had not mechanical acumen and because I had no desire to run that kind of a business, it closed. I found that after all was said and done that I had a net estate of about $350,000, mostly made up of the insurance company pay outs and a small investment portfolio that my dad had dabbled with through on line investing. Sandy had helped me more than anyone. She practically lived at my place for about four months as she helped me to get myself pulled back together. It was at that time, which as a distraction to try and pull me out of my grief that she first suggested that I try dressing up like a girl for real. I had let her put makeup on me before, and sometimes I had worn her dresses and skirts while she made the adjustments but I had never really dressed up completely for the sole purpose of trying to look like a girl. The idea did seem to appeal to me for some strange reason. Actually it was not the idea of dressing up like a girl that appealed to me. What appealed to me was the idea of being a feminine person like Sandy was. I knew that her clothes would fit me, and after letting her nag at me for two hours one morning, I agreed to let her dress me up. So while she went home to get me something to wear, I went to the bathroom and I took a bath, and denuded my body of hair in the process. I could not believe how wonderful my skin felt, hairless, in the oily scented water, and I loved it. It made me feel sensuous, but I also knew that it made me feel girlish. I also knew that I liked how feeling girlish felt to me. It was exciting. By two that afternoon, I found myself walking around my house, wearing Sandy's clothes. I had not wanted to give myself completely over to effeminization, and so we had compromised. What Dave saw when he walked in on his way home after his summer construction job just about did him in. He was not critical in any way. I had thought that he would make fun of me, but he did not. He told me that I was really cute, and if he did not know who I was, he would have thought that I was a foxy chick. When Dave saw me as a girl for the first time, I felt utterly vulnerable, weak, and very feminine. Worse, I had loved how it felt too. I was wearing a pair of pink and white Keds' sneakers, white knee socks, a pair of white girl's shorts through which I was not realizing that my pink panties could clearly be detected. I had on a white sleeveless halter-top with a wide ruffle adorning the V-neck, through which could also be detected the pink lace on the bra that I was wearing. She had done up my hair in a curly coiffure so that it did not look as long, but it sure looked fuller. It was like a halo of curls around my face. It made me look really cute I knew. She had also insisted that I wear a necklace, rings, earrings, bracelets and a girl's watch, and she had done my nails in pink as well. Anyway, to make a long story a bit shorter, I had spent the day as a girl. Between Dave and Sandy I was dubbed Deborah Leigh Johnson, but I was to be called a more informal Debi, spelled with one "e' and one "i", because it was so cute. I spent my first afternoon in the presence of a hunk boy, and a foxy girl, as another girl. It was soon revealed to me that Dave had always thought of me as being more of a girl than I was a boy, though he had always treated me like a guy, because he thought that that was how I preferred to be treated. He said that he had no difficulty relating to me at all when I was wearing Sandy's clothes as a girl, because it seemed somehow to be more like the real me. Suffice to say that over the next few weeks, I began to wear girl's clothes more and more at home. Sandy had even gotten me dressed up one Saturday when Dave was away with his parents. She had made me go with her to a mall that was about three hours from where we lived, and under her guidance and encouragement, I went home with a complete feminine wardrobe. I was lucky that I could wear clothes off the rack, and that they did not need alterations. By the end of that summer, I was wearing girl clothes nearly all the time. I just did not feel comfortable anymore, wearing boy clothes. Besides, I loved how feeling pretty felt. School time rolled around again, and we had to make career decisions. Dave, no surprise to anyone chose to study business management, as we all knew that he desire was to own and operate his father's construction company some day. I knew that he would be very good at it too. Sandy decided to go into a graphics arts course, as she wanted to either be an artist or a clothing designer. I decided that the best thing that I could do for myself was to go to college and learn as much as I could about financial management, so that I could make my little nest egg grow, so that I would always have some financial security. I knew that the way that I felt about wearing ladies clothes meant that I would never really be able to get a guy's job anyway, as I did not want to have to live as a guy unless I chose to. Sometimes I wore guy clothes, but even under them, I usually wore lingerie. I just grew more and more in tune with being a feminine person. So Dave and Sandy and I grew apart as we were going to different schools. Over the next four years, we saw each other once in a while on vacations or summer breaks, but we were not close like we used to be. As for me, I had learned some really useful strategies with mutual funds and life insurance, and so I had made my little nest egg grow to the point where I was drawing about $50,000 a year after taxes in dividends yields, and my principle was still growing. I did not have to work at all. School had been kind of hard, as I had no friends to speak of. Most guys did not want to be around a fairy, who wore girl's clothes to school, and most girls while they liked me did not really seem to be interested in my friendship, and they were certainly not interested in me as a potential husband. I always looked like a guy, but everyone knew that the clothes that I wore were not guy clothes. I tried to buy mannish looking girl clothes but they were still not male clothes, and there was always some little trace that could be detected in the designs. I was happy though, and the courses offered a challenge to me so I did well and I was always busy. On the weekends or at home at night, more often than not I wore skirts or dresses though. It was just the way that I was. I accepted myself as a feminine male. That was all. I had no real close relationships, for the reasons that I mentioned earlier. Guys did not like hanging around with guys like me, and girls so no potential future with a guy who might become their competition, but I was pretty happy. I spend lots of time on the phone talking with Dave and Sandy. Sandy treated me more and more like I was her best girl friend. I liked that role with her. I learned all about how horny and hard to handle Dave could be, and what she did to please him and slake his attitude without risking him losing interest in her. She did not hesitate to tell me how she loved having sex with him. She especially loved giving him blowjobs. I had no idea of why she would want to tell me things like this, but I was certain that I knew how to give a perfect blowjob too, not that it ever entered my head to ever want to do such a humiliating thing with another guy. She seemed to delight in telling me whenever she would try something knew on Dave, and how he liked it. I swear that I think that she had forgotten that I was ever a guy, from the way that she treated me. I liked it though. I really did like the way that she treated me. She never referred to me as Derrick any more, only as Debi, unless she was mad at me, then it became Deborah. She wanted to marry him and have his kids. I admit it, okay? I was kind of jealous of her. Because she was a girl, she could be free to enjoy that kind of life expectancy. Because I was not a real girl, I could not. I did not give it a lot of thought, but I had sort of resigned myself to being an old maid. Three That led up to Dave and Sandy getting married earlier this day. Sandy had asked me to be her maid of honour. How could I refuse? Jeff was her long time friend from college who specialized in photography. Jeff soon took a liking to me, a liking that I had never experienced before. It was the liking that a good looking virile young man has for an attractive young lady. When I noticed that he was having the maid of honour in almost all of the pictures, I knew that he was really trying to pay attention to me. I went with Sandy once to refresh her makeup, and I commented on what I thought Jeff was doing. She wanted to know if I liked him. I admitted that he was a very nice and attentive gentle man. She giggled and said that I knew darn well that that was not what she had meant. She wanted to know if I liked him enough to go out on a date with him, if he had asked me to go out. Shyly, I admitted that I might, if there was not fear that he would find out my secret, and maybe beat me up or something like that. I was too much of a sissy to enjoy pain, I sighed as I admitted that I liked Jeff. She giggled and told me that I was the reason why he was there. She told me that she had found out when they were in their third year after unsuccessfully trying to set him up with some of her girl friends, that he had a peculiar taste in romantic partners. He liked very feminine pretty young men who enjoyed being girls. Naturally, she had told him all about me and had shown him lots of pictures of me. She had also warned him that she was pretty sure that I was not a fairy, in that I had never expressed any kind of interest in boys, aside from normal girl kind of observations from time to time. He had pleaded with her to introduce us as he claimed that he was smitten with me. She knew that if she told me that she had arranged for me to meet a man who was interested in me in a romantic way that I would never have agreed to be her maid of honour. So, she just told Jeff to go slow and easy with me and to try and make me like him. If he did that, she would try to get me to go out with him. She told me that she was starting to get worried about me because I did not have a special someone in my life, and she was certain that Jeff would be very good for me. I sighed, and I told her that if Jeff asked me out, I would go out with him, for her sake. She smiled that secret smile that she has that tells you that she knows what you are really thinking, and she told me that she was going to tell Jeff that I really liked him. I stamped my foot and raced after her, well if anyone could race in pretty floor length gowns, but I did not catch up to her. Before I knew it, Jeff was spending most of his time beside me. He would run and fetch me wine or punch or do any little thing that I slightly indicated that I wanted. I had to admit that no one has ever been so infatuated with me that they wanted to impress me into liking them. I liked the way that he was treating me. He made me feel like a princess. So, when the limo pulled away, and most of the guests were leaving, Jeff was standing by my side. "Debi, I would love to photograph you." "You would?" I was amazed. "I think you would be an excellent study. Yes I would. What are you doing now?" "Well! Nothing I guess? Why?" "I have a small studio, and I would like for you to go there with me." "Okay, I guess?" That was how it started. We entered the studio and Jeff put on some soft music, and he hung up a silky looking pink backdrop. He told me that my white linen and lace dress would look wonderful with the pink as a contrast to it. He directed me to slowly sway as though I were dancing for the private pleasure of my imaginary lover. Somehow, that did not seem strange to me. Soon I was swaying to the music, caught up in the soft strains. It was quite romantic, I sensed. I heard the gentle whirring and clicking of his camera. Once in a while he would comment about how pretty I was, or how he liked that particular cute expression or some such a comment as that. Then he asked me if I would be willing to be a little racier. I blushed and admitted that I might. He had me remove my hat and gloves, slowly. Then he had me raise my skirts to show off my legs. Then he asked if I would be willing to take of my dress while he photographed it. I did not know what was getting into me, but I was hornier than I had ever been in my life. This was the most erotic experience I had ever had. I felt so alive, so tingly and ever so sensuous, knowing that this good looking young man was really turned on by my effemination. That was when I first saw the bulging in his pants. That was the first time that I had ever thought of myself as being in a romantic relationship with another guy. Jeff just seemed to make it seem so normal for me as a girl to like him as a girl likes a guy. My cockette was so hard that it was almost painful. The only nice thing about it was the soft caress of my satin panties on it. And so, I reached behind me and lowered the zipper slowly, and carefully allowed the dress and full satin petticoats to fall from my body. I had never let a guy see me before in sexy lingerie, and the fact that me in lingerie could excite a man was like some kind of heady wine for me. I had been taking some female hormones, so I had developed small breasts, and Jeff talked me into taking off my lacy bra when he saw them. I heard him suck in his breath, and mutter about how beautiful my breasts were when he saw them. Soon, he had me also agreeing to lowing my panties so that he could shoot my little cockette too. Four At last, I stood there naked, excepting for my garter belt, super sheer nylons and my high-heeled shoes. For the first time in my life, a guy was looking at me in my state of dishabille and it was terribly exciting for me. My little cockette was standing out at full attention, almost crying for the man to come over there and take care of it. Jeff finally lay down his camera and walked over to stand in front of me. He made me feel so small and so delicate. He made me feel weak and strangely, he also made me feel as though I was somehow under her control, and I liked how that felt. I wanted him to take pleasure in me. I wanted for him to take control of the moment, and to make me do what girls willingly do to men they love. I wanted to feel him having his way with me. I wanted him to take me in his strong arms, and to crush me as he hugged me. I looked at his dry thin lips, and his beard stubble, and I wanted to know what they felt like on my face. He stood close in front of me for a very long minute, gazing deeply into my eyes. "Debi?" "Ummm?" "Uhhh... Sandy tells me that you have never been with a guy before." "Yes, that is right." "She tells me that you are not a fairy." "No. I do not think that I am..." "Even though you have this, you feel like a girl right now?" As he spoke, he reached out and he gently took my cockette into his right hand, and he squeezed it ever so gently. I sighed, and nearly dropped to my knees, the erotic intensity of the moment was so overwhelming. I gazed back at him, and I could see by his countenance that he knew how this was making me feel. I knew then that Jeff was seducing me, making me want to be a girl for him. "Yes, I... Even with that, I feel like a girl..." "Ummm... That is what I was hoping that you would say. Do you have any concept girl, of how seductive and alluring you are to me?" "No..." He took a hand of mine, and placed it on the front of his pants. I felt his cock throbbing. It was so hard. It was so very hot, even through his clothes. He pressed my hand against it, and then took his hand away. I knew that I should have hated this. I was not a faggot. Yet I felt a desire to leave my hand there. It was like some kind of super confirmation that I was a woman for him, even though he had my cockette in his hand. I felt every inch like a girl about to be seduced for the first time, and I loved how it felt. "Do you like how I feel about you Sissy Miss Debi?" His words seemed to crash deep inside of my psyche. Yes, it was true. How could it not be true. You cannot get to be much more of a sissy than I was at that moment, can you? I felt compelled to answer him. "Yes Jeff=85 I=85 I like how you feel about me." Then he stepped closed and placed both of his hands lightly on my shoulders. He bent down and for the first time in my life, a man kissed me. It was so sweet. At first, his kissing lips brushed mine so lightly that I was wondering if he was really kissing me or not. After a second though, I felt his big tongue start to lick my lips. I nearly swooned; he made me feel like I was melting. Not know what else to do, I parted my lips as I reached up to put my arms around his neck, so that I would not fall to my knees. I had to hang on to him, or I would surely sink to my knees out of sheer emotion. He pushed his tongue into my mouth, and I locked my lips around it, and I sucked him deeply into me. His fingers lightly explored my back, from my shoulders to my bum cheeks over and over again, and the moment seemed to last for hours. He was such a good kisser, and he kept pressing his erection against my tummy. I loved how his hard flat chest felt. I could feel his heart beating though his shirt, on my cheek when I lay my head on his shoulders. He held me tightly in a sweet tender embrace for a long time. "Debi?" "Yes Jeff?" "I need you." "Yes?" "I need you to take care of me and I need you to do it now. You are driving me crazy. You make me have pain, you are so fuckin' sexy." "What do you want me to do Jeff?" "I want you to suck my cock sweetheart." Suck a cock? I had never dreamed of sucking another guy's cock. But, I was a girl, was I not? Isn't that what girls do for the boys they love? Jeff certainly made me feel like I was his princess. Isn't that how guys are supposed to make a girl feel? It is if the guy loves them. I stepped back for a moment and looked up into his eyes. They were filled with his lust for me. It made me feel so special to him, and it made me want to submit to him in whatever way that he wanted me to do so. Suck his cock? If he, as my guy, wanted me, as his girl to suck his cock, I would try. "Jeff, I never did anything like that before." He kissed me lightly on my lips again. "I know babe, but you are so fuckin' hot that you better learn how, or you are going to drive some idiot to raping you. You are so foxy, I can't stop wanting to take you. I want to make love to you, but I want to know that you accept me honey. They only way that I will know that you really and truly want to be my woman, is for you to show me how much you want to be my woman, to show me how much you accept me as your man. You can do that by sucking my cock honey." I felt such an overwhelming sense of effemination and a sweet sense of humiliation tinged with a sweet sense of submission as I felt his hands on my shoulders apply light pressure. I could hardly believe it. I slowly sank to my knees in front of my man. This was the position of abject surrender to a man. It made me feel so feminine and I recalled how Sandy had told me how she loves to kneel down in front of Dave, just as I was kneeling in front of my man, Jeff at the moment. She had told me of how it makes her feel weak and submissive to him, and very feminine. Yes, I understood her words now. Now I knew first hand what she had felt. I also knew now why she had liked those feelings. I loved them. These were womanly feelings, and I felt strangely completed and whole to be able to feel them too, as had my best friend. I watched, nearly mesmerized as he opened his pants and let them drop to the floor. There must be a heavy wallet in them, the way they dropped. Then he pushed his under wear down, and his cock sprung out and hit my chin, then it slid up the side of my face, and came to rest on my nose. He smelled so masculine. My own little cockette throbbed excitedly at the very thought that the next time that I looked in the mirror, that I was going to be looking at a cocksucker. Could I be one? Did I have the strength; the courage to over come the last vestiges of the male upbringing that I had lived with, and do what Sandy got so much pleasure from doing? He reached down and took his hard shaft in his hand. "Open your mouth Debi." I did not think about it. I obeyed him. He placed his cock on my lips and ever so slowly, I felt his cock enter into my mouth. I was astounded. I was at long last, getting to know all those intimate feelings that girls get to know when they make love to their boy friends. His cock was so hard, and yet the skin was so satiny soft. He entered into me. I felt it fill my mouth, bulging out the sides of my cheeks, from the inside. Then he stopped, just as I started to gag. He just stood there, his cock buried in my feminine mouth. I felt him throb and grow even harder, though that did not seem to be possible. He just stood there, as though he were waiting for some sign that I wanted to receive this as badly as he wanted to give it to me. I moved my lips and I started to lick his cock. I also looked up at him. He looked down at me and his face and eyes were filled with a look that I will never forget. He looked victorious. He looked so superior. He looked smug and superior to me. He was the man, and I was not. His expression made me quiver with delight. Yes, this was how a girl feels, and what a girl see when she looks up too. I was all girl. Jeff was my man, and he wanted me to make his cum come out of him, and into me, the way that a girl and a guy do for each other since the beginning of time. I realized for the first time that I really wanted to be his woman. I wanted to make that cum come out of him. I wanted to receive it. I wanted to know what his cum tasted like. I wanted to make him give it to me. I locked my lips, licked him and drew my head back till only the head of his cock was still inside of my lips, then I moved forward again, sucking him deeply into me. "Ohhh... Sissy Miss Debi, you are one fantastic sweet cocksucker you are, young lady. Ohhh you are going to make me explode in a second. Ahhh... Suck my cock you sweet bitch... Yeah... I can see how you love to have my cock in your mouth... Suck me sweet heart and make me cum into your sweet cunt mouth... You are such a hot bitch, girl... You are a wonderful cock sucker..." His words should have been demeaning and humiliating. They were not. In my ears, they were like praises. Yes, I wanted to be the best cocksucker that this lovely man had ever met. I wanted to be so good that he would never want to let another girl get her lips around him like I was. I wanted to make him want me. I reached up with my fingernails I scratched his balls. Sandy told me that Dave loved that. I soon learned that Jeff loved it too. I moved my head back so that just his cock head was inside of me, and I started to masturbate him. It was as though sucking his cock was just not enough in some way. I felt a need to do something to let him know that I willingly wanted to make him give it to me. I wanted him to know that I was his devoted girl, and that I wanted it all from him. I wanted him to know that I was willing to do whatever it would take to make him give it to me. Jeff did not disappoint me. In a second, I heard him yell and he began to shudder and tremble all over, and I soon felt hot semen spurting into my mouth for the first time. It was thick and it was salty tasting. It seemed to drip in big gobs from the roof of my mouth. I felt the pressure on the sides of my lips, and I knew that he was giving me more than a mouthful. I did not know what to do, so I did what Sandy told me that she loves to do. I swallowed all of his semen. I felt so wonderfully feminine as I thought of his male essence being drained from him, and taken into my feminine body, where nature intended for male sperm to go. He made me feel so wonderfully submissive to him, and I wanted him. I wanted him to love me and for him to want me to do this over and over again. It was such an intimate and feminine thing that he was letting me do, I loved him for it. At long last, Jeff stopped spurting and he just sort of seemed like he was loosing all of his strength. He removed himself from me, and he sank down to his knees in front of me. "Gawd, you are such a woman Debi. I cannot believe that some guy has not gotten to you before this. Man, you are all the woman a guy like me would ever need. You are my fantasy come true, Princess." "I am?" "Debi, I know that we can not get married like a regular guy and a girl does, but I would be so happy if you would agree to become my wife, to move in with me and let me make love to you every night. I promise to treat you like a princess all the time, and to make you feel so special to me." "I already feel special to you Jeff. You have made me feel like a pretty and cherished princess already." "Will you become my wife? Hey, maybe Sandy can be your maid of honour, and Dave can give you away when we have a wedding ceremony? Would you like that baby?" For an answer, I kissed him and sucked his tongue into me. I wanted this man to take over my life and to let me love him the way a woman is supposed to love a man. Suffice to say, Sandy made a beautiful maid of honour. The End Miss Debi's fe-mail address is: [email protected] Drop her a line if you like. She'd love to know how you feel about her.