Raymond My First Man! free porn video

RAYMOND MY FIRST MAN! I work from home and I am a transvestite, it is wonderful to be able to dress as I want and just enjoy life and my work as Joanne. The other day I did something I had never done before and it was so astonishing. I would often rent hotel rooms to dress and spend the night as Joanne and enjoy myself. One such night, a Monday, I was at a hotel and I felt lonely, I decided to call a friend, a long-time friend that did not know about me but who I knew had often offered me such things as skinny dipping with him but I had never taken him up on it. I told him where I was and if he wanted to come he had better be prepared for a surprise as I had never divulged that to him. He told me he would come right over; I had about thirty minutes before he arrived. That night I had dressed carefully and while waiting for him I made sure I was as perfect as I could to impress him. As I looked at myself in the mirror I felt quite feminine by my reflection. I had on my white dress with the black accent on the collar, sleeves and pockets. This dress was really sheer and my black satin lingerie could be seen through it. I wore my black satin bra and panties set, with my black satin garter-belt, with my black seamed stockings and my six inch black patent high heels. My make-up was perfect as were my nails also. I also had put on my jewelry, necklace, earrings, bracelets, watch and rings and also my ankle bracelet. All the jewelry was gold. My hair was also perfect and my perfume just added that special sense of femininity that I loved so much. Although I would divulge to him a part of me that he had never seen I was aroused at what was about to happen and also a bit anxious at how he would react. Just before he arrived I looked again and through my dress all my lingerie was visible and so were my stockings. I unbuttoned one more button on my dress and took a deep breath. I said "Joanne the night you have dreamed has arrived! It is your time!" I said it with the hope that it would be as wonderful as I had dreamed for a long time. When he arrived I opened the door and stayed behind it so he would not see me until I closed it, his face registered his surprise at seeing me dressed like that. He did not know what to say. He placed his small bag on the floor and looked at me. I walked to the centre of the room and slowly turned so he could look at me properly. I looked at him and said, "Well Raymond, do you like what you see?" He smiled and came to me and took me in his arms he looked intently at me and kissed me on the lips. I felt so feminine at that point. He held me in his arms and asked what he should call me. I told him, "My name is Joanne Raymond Dear!" "Nice to meet you Joanne," he said and brought me closer to him as his lips were on mine. This time his tongue teased my lips and I parted them to allow him entry into my mouth. Soon our tongues were dancing languorously together and he kissed me passionately and sensually. Raymond put his arms around me tighter and held me close to him as I placed my arms around his neck as we continued kissing feverishly. I realized that my left leg was bending at the knee as he kissed me and caressed my back. Then I felt his hands on my buttocks holding me tightly against him as his tongue seduced me. He held me so tight that I felt his cock hardening and I felt so feminine and held him even tighter against me. He broke the kiss and whispered in my ear, "Joanne do you know what you are doing to me?" I whispered back, "Yes Raymond Darling and do you know what you are doing to me with your passionate kiss?" "Let me order something to drink Darling Joanne and then we can talk." He picked up the phone and ordered champagne from room service. I went into the adjoining bathroom to refresh my make-up and perfume as we waited, and made sure the bedroom was also ready as I hoped we would come here together. I walked back into the living room and Raymond looked at me seductively. Just then there was a knock on the door. Raymond told me to go and open it; I was a bit apprehensive as it was my first exposure to a stranger. I opened the door and the waiter came in with a roll tray, he looked at me and smiled as he handed the invoice to Raymond. He signed it and then the waiter left. Raymond got up and led me to the sofa; I looked at his crotch and saw his cock was still very erect. He then lowered the lights and poured the champagne. He then sat close to me and we toasted to each other and our evening as we drank the champagne while looking at each other. As I drank I felt his gaze upon me and was even more excited. He put his arm around my shoulder and brought me close to him, I let my head on his shoulder as I looked at him and he looked at me. "Joanne Darling, are you gay?" "No Raymond Darling!" "Are you bisexual then Darling?" "I think so Raymond Darling." "Darling Joanne I am gay and love being with someone of my own sex even if he dresses!" "That is wonderful Raymond Darling." "Remember when I invited you to my place when my parents were out for skinny dipping?" "Yes Darling I do." "Do you know why I was inviting you Joanne Darling?" "I think so Raymond." "Tell me Joanne Darling!" "You wanted us to be naked and you would seduce me into being with you intimately." "Yes Darling I always fancied you as a man and now even more as a woman. Why did you not come when I invited you Darling?" "I guess I was not ready Raymond, and maybe a bit scared of what might happen." "Thank you for being truthful Darling!" "Raymond Darling I must confess something though." "What is it Joanne?" "Remember when your parents went away for a month and you invited me to stay with you. You told me I could sleep in your Mother's bedroom as you would sleep in your Father's?" "Yes I do Darling." "Well one night I was rummaging through your Mother's drawers and could not resist trying on some of her lingerie, I put on one of her bra, panties garter-belt and stockings. Even a pair of her highest heels." "That is quite a confession Joanne Darling." "I even put on some of her make-up and perfume, I felt so feminine." "You must have as she did have some exquisite lingerie." "I did and after I did all that, I went out of her bedroom and walked over the house as you were sleeping." "Oh Darling, you should have come into the room I was sleeping in." "I did Raymond Darling and you were sleeping tightly and I admired you and slowly sat on the bed before going back to my room. I still remember seeing the shape of your cock under the sheet and your head was peeking, it was beautiful. Your cock appeared so beautiful and manly. But I did not know if you would accept me as I was." "You know that if I had awakened I would have taken you with me in the bed." "Yes and I was hoping that you would wake up a bit, or even woke up as I was walking around the house and caught me, but it did not happened." "Oh Joanne that is the past we are together now and that is what is important, and I must admit I fancied you as a man but even more as a woman, especially knowing your secret Darling!" "Yes My Darling we are!" "Wonderful Joanne, tell me have you ever sucked a cock?" "Just when I was young experimenting but never went all the way Darling." "Have you ever been with someone when dressed as Joanne?" "Yes just once another TV but it was not that good Darling!" "Joanne you told me you are not gay but you think you are bisexual, have you ever been penetrated?" "No My Darling I have not." "So you are a virgin Joanne Darling?" "Yes My Darling I am!" "That is wonderful, I am curious as to why you called me tonight Darling." I blushed and he held me tighter against him. "I was dressed and enjoying a glass of wine when I thought about you and those invitations in the past." "Oh I am surprised, what did you think about for those invitations?" "I was just thinking what would have happened if I had accepted one of them Darling." "Darling every time I invited you I had only one thought in my mind, to teach you about gay love, as I said I fancied you and I thought you would be a romantic and sensual partner." "Oh Darling Raymond, seriously you really thought that?" "Yes Darling I did!" And he held me closer as he kissed me passionately. He brought one of his hands to my breasts and caressed them as I also caressed his torso, my hand working on his nipples and all over even his lower torso. I was feeling so feminine at that point. His hand caressed my back and went to my buttocks holding me tight against him, then his other hand went lower towards my legs, soon I felt him caressing my stockinged legs slowly and sensuously. He was kissing me as I had never been kissed his tongue dancing with mine and his saliva invading my mouth, he tasted so good as his hand on my legs was making me feel so much more feminine, then he went under my dress and soon I felt his hand on the skin above my stockings. He moaned and kissed me more passionately. We broke the kiss and looked at each other as we took our champagne flutes. I could see that he had a special look in his eyes. "Darling Raymond let me go and get more comfortable!" I said. "Please do Darling but I would like to use the bathroom also." "Of course Darling just give me a few minutes and when I step into the bedroom you can use it." I stood up and smiled at him as I made my way to the bathroom feeling very feminine. I refreshed my make-up and made sure all was perfect, before taking the door to the bedroom and he came behind me holding me tightly as he helped my unbutton my dress as he kissed my neck passionately, sending shivers through my body. I stepped into the bedroom as I turned my head and looked at him seductively, a bit nervous as to what I was about to do but nevertheless eager. I removed my dress and hung it in the closet, then I adjusted my lingerie and verified my stockings were taut and the seams straight. I took my perfume and sprayed it at the proper areas. As I did that the scent made me feel even more feminine but I knew it was not over. Once that was done I went to the closet and removed my black negligee from its hanger. It was the first time I would wear it for someone and I was eager to slip it on. It was long and totally sheer so my lingerie was entirely exhibited through it. I slipped it on and felt even more feminine and seductive. As I looked into the mirror to refresh my make-up, I was aroused at the sight that looked back at me. As I redid my lipstick I felt so feminine and the thought that I was about to give myself to a man made me shiver and I felt my clit and rosebud tingle. I wanted everything about me to be prefect as I seduced him into making me a woman! Raymond knocked on the door, "Yes Darling." "Are you ready Darling?" "Almost my Darling Raymond." "Wonderful My Darling, give me a minute or so, I will knock on the bedroom door when all is ready." I wondered what he was doing but since I had called him I decided that I would accept what he wanted, after all after being kissed by him I was already decided. "It is all perfect Darlings you can come out." I took the door handle in my hand looking at my feminine hands with my red nails, knowing that soon they might soon be on his cock and it made feel even more feminine. I opened the door and there he was, he smiled and so did I. He had put candles in the room to make it more romantic. He was standing there almost all naked only a small G-string held by strings on the sides, hiding his cock but it was so tight I could see its outline through the shiny black material. He had that look in his eyes that told me he found me beautiful. He came to me and took me to the large sofa; he sat down and sat me beside him. We sat facing each other and he took my champagne flute and gave it to me as he took his. He said, "Here is to us Joanne, you are beautiful and so desirable!" "So are you my Darling Raymond!" I answered. And we clinked our glasses before drinking. He looked at me intensely. "Joanne My Darling, you told me that you had never lost your virginity and that you had never had a cock in your mouth properly My Darling!" "Yes My Darling it is all true!" "My Darling does that mean that you invited me here tonight so that you could indulge what you have missed?" "Raymond as I told you I was dressed and was also lonely, I wanted to be with someone and you were the one I thought of." "You did not answer my question My Darling!" I lowered my head and blushed, then brought my mouth to his ear as my hand went to rest on his thigh close to his cock. I licked his ear and then whispered, "Yes Darling I did!" He brought his mouth to my ear and whispered, "Joanne were you hoping that something intimate would happen?" I moved my hand closer to his cock and whispered, "Yes My Darling Raymond!" "I hope you are sure of this My Darling," he answered. "My Darling Raymond I was never more sure!" And I let my hand cup his cock through his underwear. Immediately I felt it harden and loved to see my long nailed fingers holding it that way. "Oh Joanne Darling, you are quite special and I love the way you touch my cock." I kept caressing it and it kept getting harder. "Raymond Darling I love how you react to my caresses on your cock." His cock appeared to be huge compared to my little clitty. I was eager to see it. He brought his lips to mine and we kissed passionately as we caressed, I could feel his cock still hardening in my hand and he started caressing my nylon clad legs until he got to the skin above and it made me moan as he did. It was so wonderful for me to be in his arms that way. As I caressed the length of his cock he kept moaning and then I felt his head come out of his G-String. When my fingers touched it he moaned louder and I felt he was quite aroused as some pre-cum was leaking. I was quite aroused myself and I used my fingers to spread his pre-cum on his cockhead. He moaned and took a deep breath intake that took my breath away into his lungs as he held me tighter. I was so aroused I could not resist anymore, my hand went to his side and pulled on the tie that held his G-String together, he moaned as I did so and then let my hand remove the small patch of cloth that hid his cock. As soon as my hand touched his cock, again he took a deep breath as he moaned louder. I caressed its length and then held it in my hand, I was enthralled as I held it by the size of his cock and the softness of the skin as he was hairless. I caressed it from the base to his cockhead feeling his pre- cum leaking. He broke the kiss and looked at me. "Joanne Darling do you like it?" I smiled and looked at it seeing my red nailed fingers around it and was simply hypnotized by his cock. "My Darling Raymond I do not like your cock I Love it, it is so beautiful!" I felt his cock quivering in my hand and it made my clit harder and I felt it leaking also. He told me to stand up and he opened my negligee and caressed my panties, slowly he slipped them off along my stockinged legs and then took my clit in his hand while the other caressed my balls. He lightly kissed the head of my clit. Then bade me to sit close to him. I did so and cuddled as my hand went back to his beautiful cock. He kissed me passionately as we both caressed each other. His cock was leaking generously now and my hand was wet with his pre-cum which I lovingly spread on his cockhead as he moaned and took deep breaths. His cock was quivering under my caresses I loved it. "Joanne Darling do you really love my cock?" "Raymond Darling, yes I do and I find it so splendid and marvellous!" "Oh Joanne Darling that is lovely, but what makes you find it so?" "Raymond My Darling maybe it is that after all this time I really see it, and also because as my female side it is quite exquisite to see my hand caressing it, with my red nails and rings!" He looked at my hand caressing his cock, "Yes Darling I must admit that it is quite arousing to see your hand on my cock. I also love to see your clit framed by your garter-belt and stockings!" "Thank you My Darling, you are so hairless it is so sensual!" "I know I love it so I can feel the caresses better My Darling!" "My Darling I shave because I want to be as feminine as possible but I agree I love shaved genitals! And your cock is so magnificent without any hair My Darling I love it!" "You really think so Darling?" "Yes My Darling Raymond I do!" My clit was leaking now and I felt one of his fingers spreading it on the head, then his hand left my clit and he brought a very wet finger to my lips, "Taste yourself Joanne Darling"! I opened my mouth and took his finger in licking it clean my tongue tasting myself and I moaned. "Do you like Darling?" "Oh Darling I love the taste of me!" He took my hand off his cock and brought it to my mouth, "Now Darling taste me!" My fingers were very wet and I licked every one clean as I moaned my pleasure. "So Darling did you like my pre-cum?" "Raymond My Darling I loved it, your taste is luscious and appetizing!" "I am elated that you like it My Darling as I hope you will taste more of me"! I put my hand back on his cock with a sigh of pleasure, "Yes My Darling I want to taste more of you!" He kissed me again passionately as his hand moved back to my clit, and he had his other hand on my breast caressing it, I felt so feminine. As he caressed my breast, even though it was a falsie, it turned me on more and he slipped his hand under my falsie and caressed my nipple, I quivered and moaned. He caressed my nipple and pinched it, I moaned even louder. He whispered in my ear, "My Darling your nipple is so sensitive, I love that, so much more to give you pleasure with!" "Darling Joanne, did you really love the taste of my pre-cum?" "Raymond Darling, I really did!" "Was it your first time tasting pre-cum Darling?" "Yes Darling as before when I experimented and with the other TV it did not leak enough for me to taste, so yours is the first and it is marvelous!" "Do you want to taste more Darling?" "You read my mind My Darling!" I lowered my head to his crotch seeing his huge cock grow as I got nearer. I let my tongue out and put it on his cockhead, it felt so soft and spongy and the pre-cum flooded my taste buds. I loved it. I licked his cockhead clean as he caressed my clit and teased my nipple. Once his cockhead was cleaned I took his cock between my lips and let myself swallow it, it was not that thick but so long and it filled my mouth nicely. I sucked on it as Raymond moaned and took big breaths; I knew I was pleasing him even though I could not take all of him in my mouth. I sucked him and held his balls in my feminine hands and I felt so womanly and sensual with his cock in my mouth and he tasted so heavenly as he was leaking precum copiously. I was so happy that I ate his cock with desire and wantonness. "Darling Joanne if you keep going you will make me cum!" As he said that I knew I wanted him to cum in my mouth. I kept going until I felt his cock start quivering and suddenly it pulsed and the first jet of cum filled my mouth. It made me so proud and excited as he kept filling my mouth and moaning his pleasure. To feel his cock pulse each time was marvelous. He had so much cum and I loved it. I held his cock in my mouth as I cleaned it and then looked at his face. His eyes were closed and he looked so peaceful and satisfied. I let his cock slip from my lips and he opened his eyes. He looked at me so lovingly and passionately. I looked at him seductively and ecstatically as I swirled his cum in my mouth wanting to taste it completely. I sat beside him and opened my mouth to show him his cum before swallowing it. "Darling Joanne I cannot believe it is your first time sucking a cock, it was so good for me and so sensual also. I loved when you showed me your mouth before swallowing it, I felt so special knowing that now you have me inside you Darling!" "Darling I loved it when I felt your cock pulse and your first stream of cum invade my mouth, I felt like a woman. And to know that you are inside me is so wonderful and I feel so feminine now! Thank you My Darling Raymond!" He held me tightly against him as we basted in the glory of his orgasm. It was a wonderful feeling. We just laid against each other feeling each other's warmth. "Joanne Darling, did you really feel like a woman as you sucked my cock?" "Yes Darling I did, the way I am dressed, seeing my feminine hands holding your cock and balls and feeling you in my mouth was magnificent and so special. I so wanted to take it all in my mouth but you are so well endowed I could not My Darling, I am sorry!" "No need to be sorry My Darling it was one of the best oral sex I ever had and I am so happy that you did it, and it makes me ever more ecstatic that I am the first to enjoy your first time sucking a cock and tasting cum! If we see each other regularly you will learn how to take me completely My Darling!" He stood up and went to his bag, "Just give me a minute Darling." I watched him walk into the bedroom and admired his beautiful body making me palpitate as I realised how beautiful and masculine he was. He soon came back and as he walked towards me I looked at his beautiful cock and saw it was not as soft as before, I was amazed at how fast he could recuperate. He took the bottle of champagne and refilled our glasses. He handed me my flute, easily recognisable by my lipstick, and sat down very close to me. He raised his flute and our arms intertwined as we each brought our flutes to our lips. "My Darling to celebrate your first time sucking my cock and making me cum, and hopefully for much more!" "yes Raymond, to much more between us tonight!" We drank our champagne as we looked at each other lovingly and with desire. He took another sip of champagne and swirled it in his mouth, then he brought his mouth to mine and as I opened my lips to let his tongue in he let the champagne invade my mouth as his tongue followed, we shared a champagne kiss, it was so romantic and erotic. "Oh My Darling Raymond it was such a wonderful kiss, I loved it!" And I lay my hand on his cock and felt him getting erect again. "My Darling I love to share with my lover. Shall we go into the bedroom My Darling, I am sure we would be more comfortable!" I smiled at him, knowing full well the meaning of his words and look. I blushed lightly as I bent to pick up my panties. "Darling allow me to freshen up before!" "As I started to put my panties back on he stopped me as he put his hand on my clit, "No My Darling let me appreciate your beauty!" I kissed his lips and went to the bathroom. Once in there I looked at myself in the large mirror, I refreshed my make-up and my lipstick, made sure my stockings were still taut and the seams straight, and refreshed my perfume, feeling somewhat sexy I sprayed some around my clit. One last look and I thought tonight is the night, I looked perfect. With some nervousness I shut the light and opened the door. He had brought the candles in the bedroom and he was laying there half his body covered by the bed sheet. He looked at me with desire and so did I. I walked seductively to the bed and lay down beside him, immediately he took me in his arms and kissed me passionately as his hands caressed my body and my clit. I returned his kiss and caressed him also. He whispered in my ear, "Joanne you are so beautiful and sexy, my desire for you is so excruciating!" "My Darling Raymond I am elated to hear those words, as tonight for the first time I felt like a woman when you came into my mouth, sucking your cock was a dream come true! I should have accepted your invitations years ago and reveal Joanne to you, or I should have awaken you that time when I walked into your room dressed in your mother's lingerie!" "My Darling there is so much more I want so much more with you!" I moved my stockinged leg to his crotch and I could feel his cock hard. "Raymond My Darling, I know I can feel your cock so hard!" And I kissed him passionately invading his mouth with my tongue as I caressed his cock with my stockings. I felt his hands on my clit and my buttocks, he was caressing me and one of his fingers went in between my buttocks and caressed lightly my rosebud. He caressed it slowly and I felt so good, especially when he put a little pressure and my rosebud quivered. "Oh Darling you are aroused and your rosebud seems to love my caresses!" "Raymond Darling you do not know what you are doing to me by caressing me there! You make my rosebud quiver from your caresses Darling!" He slipped his other arm between us and caressed my clit. "Joanne you must be quite aroused as your clit is so hard and leaking!" He brought his hand to my mouth and placed his middle finger on my lips, "Lick it Darling let your saliva flow into it!" I took his finger and licked it properly leaving my saliva on it. Then he brought it back onto my rosebud. He circled it and then slowly pushed it in slowly. I moaned loudly as he did so. "Is it wonderful to feel like a woman Joanne Darling?" And he pushed his finger deeper in my rosebud. "Yes My darling Raymond it feels so exhilarating! Give me more My Darling!" He pushed it in deeper and started moving in and out as I moaned louder. Then he pulled out and brought two fingers to his mouth as he let his saliva onto them before resuming on my rosebud, I felt his middle finger go in and then the other one, I moaned loudly at his penetration of my body. "Oh Joanne Darling, you are shivering, are you cold?" Breathlessly I told My Darling, "No Darling it is from your caresses and your penetration of my rosebud it is so magnificent!" "You are so tight Joanne Darling that is why it is so good, does it make you feel like a woman?" I moaned at his words and his penetration of my rosebud, "I told you Darling I have never had any penetration of me!" "I know My Darling you are a virgin, and I love being the first one to give you the pleasure of being penetrated, even if it is only my fingers." "It feels so stimulating My Darling, please do not stop!" "I do not plan to My Darling do you want more?" "Oh yes Raymond give me more!" I felt him insert another finger in my rosebud and I moaned loudly and shivered from the pleasure. He kept penetrating me as he caressed my clit and I thought I was in heaven and kept moaning. He was so expert at caressing my rosebud and clit. "Joanne you are so beautiful as you enjoy my caresses, I love giving you that pleasure My Darling!" "Oh My Darling is it so wonderful to feel you caress my clit and penetrate my rosebud, give me more My Darling?" "Oh My Darling Joanne you want more fingers in you?" "No My Darling I want more than fingers in my pussy-ass!" "Joanne Darling tell me what you want in your pussy-ass!" "Oh Raymond My Darling I want your cock in my pussy-ass!" He plunged his fingers deeper in me, "You want me to make you a true woman My Darling?" "Oh My Darling, yes I want to be a true woman! I want to be your woman Raymond!" As I looked intensely at him and I saw him smile, that special smile that showed he wanted it to. "Caress my cock Joanne; I want you to feel it!" He let the bed sheet fall from his lower body and I saw his beautiful cock all hard. I noticed he had something around the base of his cock and I reached my feminine hand to caress it and feel what he had put on. It was made of leather and felt nice against his skin and to my touch. I caressed his erect cock and what he had put on as I moaned at the pleasure of holding his cock in my feminine hand. "Oh My Darling your cock is so hard and beautiful. What is it that you placed at the base?" "My Darling it is a cock ring." "Oh!" "Yes My Darling it is to make me harder and last longer also. I think your first time should be special!" "My Darling you are so thoughtful, I am sure that after all this time it will be." I kept caressing his cock fascinated by his cock ring and how hard his cock was getting. "Darling your cock is even harder and more erect than when I sucked it." "The cock ring does that by preventing the blood from coming out My Darling, and if I put my cock ring even tighter then it will be even harder and more erect My Darling!" "But is it not painful for you My Darling?" "No My Darling it just enhances my feelings and my partner's of being filled even more." "Sounds wonderful My Darling, how tight do you have it now?" "Since it is your first time being penetrated by a cock, I have it at the lowest My Darling!" "I caressed his cock and cock ring, "Have you always used a cock ring My Darling?" "Not at the beginning but since I discovered them yes and this one is the tamest one I have My Darling." I was amazed at the effect of his cock ring, "What do you mean the tamest one My Darling?" "I have some that will give me a most erect cock My Darling." "Oh! Darling I am surprised by your hard cock and you say it can be harder and more erect if your cock ring is tighter?" "Yes My Darling it is harder and more erect." Still caressing his cock and him caressing my pussy-ass I whispered, "Darling, would you put it at the tightest?" "Joanne Darling, it will be painful for you the first time, since you are a virgin and so tight, and if I tighten my cock ring, it will be even more painful for you My Darling." "Is it not supposed to be painful for a woman the first time My Darling?" "Yes it is but if I put it at the tightest it will be so much more painful for you My Darling." "Darling do you desire to make me a woman? To make me Your woman Darling?" I saw his eyes light up and again that special smile. "Oh Joanne Darling, I do so and knowing I would be your first man would be simply magnificent! Do you want me to be the first and to take your virginity My Darling?" "Oh My Darling I do but please make your cock as hard and erect as you can." "Oh My Darling is that is what you desire I will do so but it will be more painful as I take your virginity!" "It is all right My Darling be gentle and I am sure that I will enjoy you taking my virginity even if it is painful. My first time as Joanne must be special if you want me to be your woman!" "I will My Darling, let me prepare myself and you!" He got off the bed and took a tube of lubricant from the night table. He put some on his middle finger and then spread my buttocks to apply it to my rosebud and inside also. Then he looked at me lovingly as he re-tied his cockring and immediately I could see the change in his hardness and erection. He then took a condom out of his pants pocket. I looked at him and smiled, "Darling Raymond, please I want you natural in me." He smiled and put the condom away as he then applied some lubricant to his beautiful cock. As he applied the lubricant I could see his cock expand even more and I could feel my rosebud quivering. As he walked back to the bed he looked at me with lust in his eyes and I did the same, he placed me on my back and got in between my legs, he opened my negligee and caressed my clit lovingly. He sensuously took each of my legs and raised them. He asked me to raise my buttocks and placed one of the pillows under them. "Joanne Darling you are so beautiful and so desirable, I long for you! I want to make you my woman!" He moved in between my raised legs and I saw his wonderful hard cock looming to my rosebud. "Raymond My Darling I want you, please make me a woman, your woman! "Joanne Darling I will!" I felt his cockhead on my buttocks and shivered as I knew it was time for me to become a woman. He lowered himself and looked at me intently as I felt his cockhead contact my rosebud. I put my arms around his neck and brought him close to me, "Yes Raymond Darling make me a woman, and it is long overdue!" "Yes My Darling Joanne it is and I hope you enjoy it all even the pain it might cause as I make you my woman!" I felt his cockhead push against my rosebud and he kissed me passionately. I felt his cockhead penetrate my rosebud and it was a bit painful but as he progressed slowly inside me allowing me to enjoy the feeling of my first penetration. The pain was there and it became much more but, he kept kissing me passionately as he pushed his cock into me. I moaned in his mouth from the pain but also the mental pleasure of being penetrated. I felt his cockhead fully in me and it was wonderful, even the pain of my first penetration reminded me of my feminity. I lowered my legs and put them around his waist, with my high heels I pushed his buttocks so his cock would slide in me. The pain was subsiding, and it felt wonderful as I kept driving him into me with my high heels on his buttocks and he moaned louder as he delved into my pussy-ass. I felt him penetrating me slowly and I felt myself being filled by his hard cock, my mind was in total feminine mode as I felt like a complete woman! I brought my hand between our two bodies and felt his cock, it was not even half-way in and the largest part was slowly sliding into me, I moaned loudly as I felt the cock continue its journey inside my pussy- ass, it felt so wonderful to be a woman! I felt his marvelous cock keep penetrating me and even though there was some pain it had subsided and the pleasure was now taking over, making me feel like a true woman. I felt his balls on my buttocks, he was fully in me. "Oh My Darling Joanne your pussy-ass feels so good around my cock, you are so tight, it is wonderful!" "Oh Darling I feel so feminine now that you are fully in me, it is wonderful My Darling Raymond!" And I kissed him passionately. "Joanne Darling it feels so good to be inside you! And to know that you feel feminine with my cock deep in you!" "I do My Darling and your cock feels so good in me, it makes me feel so womanly!" "I am happy to hear that My Darling now to fully be a woman one more thing My Darling!" "What is it my Darling Raymond?" "Since you have sucked my cock properly now I must fuck you properly and leave my cum in you My Darling! "Oh My Darling yes I so want your cum in my pussy-ass!" "You will My Darling, but I just want you to feel me fill you and get trained to my size." And he pushed it more even if he was completely in me. I moaned. I felt one of his hand slipped under my bra and tease my nipple, it was so marvelous and I kept moaning from the pleasure. I felt him pull out of me and my pussyass lips felt on fire. I moaned loudly as he slowly pulled out and felt my pussy burning. "I know My Darling it is painful but it will go away soon trust me." "Raymond My Darling I trust you and I feel the pain but it is also wonderful to finally feel like a woman!" He kept pulling out of me slowly until only the head of his marvelous cock was in me. "My Darling I will make you a woman my woman!" He kissed me passionately and I felt him enter me completely in one plunge, it was painful but also wonderful. I screamed and moaned at the same time as he kissed me, his mouth and tongue shushing those. He started the rhythm of penetrating me slowly but deeply and soon the pain was replaced by enormous pleasure as he also fondled my nipples giving me sensations that I had never had before. "Joanne Darling it feels so wonderful and sensual to penetrate you like a woman, I feel so manly and virile as I take your virginity My Darling!" "Oh Raymond Darling, it is such a nice feeling to have, feeling you make me a woman I feel so feminine and yielding to your masculinity My Darling!" "Joanne My Darling, I will make you a woman soon, and I will cum in your pussy-ass as a man should for a woman!" I moaned at his words and then he kissed me even more passionately as he increased his rhythm of penetration, soon I felt myself dizzy with sensuality and sensations that were overcoming me and making feel like a true woman. I felt his cock plunging into me and it was so wonderful and erotic for me to have those feelings. I suddenly felt My Darling plunging harder and deeper and grunting as his tongue danced with mine. My pussy-ass was on fire and I knew that he soon would complete my being a woman! Even though I knew I was not a woman, I had all the feeling and sensations of a woman being made love properly. His fucking of me was so magnificent and so intensely passionate and dominating as he was taking over my whole body with his gestures and caresses. He was plunging in me passionately as his glorious cock was now spasming and I could feel it, I know the time was close as his moaning was getting more sexual. He was about to cum into me. I felt his cock expand and his cockhead swell as it delved deeply into my pussy-ass and his kissing became even more passionate, I held him tightly to me. Then I felt it, his silver seed pouring into me it was so warm and wonderful as he plunged completely and let his seed fill me as his orgasm took over. And so did mine. I had never felt like this before and I held him close to me with his cock deep inside me filling me completely with his seed. He put his head on my shoulder and I felt his cock starting to soften, I caressed his beautiful hair and felt so satisfied and womanly finally. We were both breathing hard and fast and it felt wonderful, I gently kissed his forehead as I realised what I had missed all those years. He raised his head and looked at me lovingly; he kissed me with passion and then looked at me again. "Joanne I have always wanted you as a man but now that I have discovered the woman that you are it is even more wonderful and taking your virginity was also magnificent, I have never cummed like that before, you are wonderful." "Raymond My Darling, it was wonderful and you were so masterful as you took my virginity I loved it and to feel your seed flow into me was as wonderful as feeling it fill my mouth earlier. And you know that I loved to taste you My Darling!" "Yes I know My Darling. And even thought it was painful for you; you were so special and marvelous. You gave me a special part of you and I am so grateful and feel so assertive as I took you and made you a woman!" "Yes Raymond My Darling and to think that I could have lived that many years ago. I regret that I did not act on your invitations and tell you about Joanne or that I did not wake you up that night I was dressed in your Mother's lingerie and high heels. But maybe in those days it could have been a disaster and tonight was heavenly My Darling!" "Yes Joanne, it was wonderful and I want more with you!" "You do Raymond My Darling?" "Yes My Darling Joanne, there is so much more for us, I am sure!" "Oh Raymond My Darling, you think so?" "Yes Joanne I do!" I looked at him and kissed him passionately! He returned my kiss and held me tight against him his flaccid cock still in me. "Raymond Darling, I have always wondered every time you invited me what it would be like to be with you, but I was afraid of how you would react to me being a TV. I did not want to destroy our friendship. Often when I dressed and gave myself some relief I would think of you, and how you would be as a lover, tonight I found out My Darling!" "Thank you for being so honest My Darling, and I also found the man I fantasized about even better as a woman!"