Transition Decisions free porn video

Transition Decisions by Vivian Bird I met her at an art gallery. We happened to be looking at the same painting and she sat down on the same bench that I was on. She looked like a goddess, tall, thin, beautiful and sexy. Her tight skirt was black, with a kick pleat in the back. Her long sleeved, white blouse was billowy, with ruffles in the front. She had two buttons undone, showing just the hint of cleavage. Her blond hair cascaded around her shoulders and she used her hands to move it off of her face. When she did so, I noticed her long fingernails, painted a bright red, matching her lipstick. Her feet were encased in four inch black pumps. She crossed her legs and her skirt rode up just enough for me to see that her sheer nylons were attached to a garter belt, before she tugged her skirt back down again. Her perfume was intoxicating and I knew that I could sit there forever, just smelling and admiring her. "Do you know who the artist is?" she asked suddenly. "No, I'm sorry, I don't," I replied, turning to look directly at her. "Maybe the name is on the little plaque on the wall," I suggested. She rose and walked over to the painting, as I stared at her derriere rolling in her tight skirt. With her four inch heels, she was close to six feet tall. She walked back, and reseated herself, saying "It just mentions the name of the painting, not the artist." I am pretty thin myself and I was wearing jeans, a short sleeved polo shirt and running shoes. I am five feet seven inches tall and weigh about 150 pounds. My longish, brown hair was tied into a pony tail. Underneath, I was wearing red panties, which were straining to encase my engorged cock. You see, I am a transvestite, but I never dress in public, other than for lingerie that cannot be seen. I would have loved to wear a bra as well today, but it would have shown through my thin shirt. Actually, I would like to explore my feminine side a great deal more. I would love to wear dresses and skirts much more often, perhaps in public, but I have been afraid to because I have nobody to advise me on how to proceed. I have had thoughts about starting a program of female hormones, but although I would love to become more feminine in appearance, I desire women sexually, not men. I work at a large software house, programming apps for phones, tablets and the like. I'm certainly not rich, but I do make a good salary. The woman and I began to engage in conversation. I gauged her to be similar in age to myself. When she touched my arm, I felt an bolt of electricity go through me. Her blue eyes were made up expertly and seemed to bore right through me. To say that I was enchanted by her would not be strong enough. I was mesmerized. "I'm going to get a cup of coffee in the cafeteria," she mentioned. "Would you care to join me?" she asked. I was dumbstruck, but managed to mumble something almost intelligent, like "sure." Walking over to the cafeteria, she said that her name was Wendy and I mentioned that mine was Jim. I paid for our coffees and sat down as close to Wendy as I dared, still intoxicated by her whole persona. Her figure, enclosed in her blouse and skirt was quite trim, with the exception of her chest. Although her blouse was fairly loose, I could tell from her cleavage, as well as the way the material was straining somewhat to enclose her breasts, that she was what I would call voluptuous. We talked for an hour or more, discussing art, politics, movies and personal likes and dislikes. I discovered that Wendy owns her own home and is a writer who has had several articles and books published. Eventually, Wendy said that she had to go. I told her how much I enjoyed our conversation and that I would really like to see her again, possibly for dinner whenever she was free. "Jim, I've enjoyed our conversation as well," said Wendy, "and I would like to see you again as well. However, before we go any further, I want to tell you something that might change your mind in terms of seeing me again. I don't want to start any relationship without being totally honest and above board." Many thoughts went through my head. Was she married? Did she live out of town? Is she telling me nicely that she doesn't like me? Did I do something to offend her? Is it possible that she realized that I was wearing panties under my jeans? All I finally said was "I admire honesty, Wendy. What is it?" "Rather than beat around the bush, Jim, let me just come out and say it. It is obvious that you find me attractive. But would you find me as attractive if you knew who I really am, or would I disgust you? You see, I am a male to female transsexual. I have used surgery and hormones to greatly alter my appearance and I know that I have successfully reached the point where nobody can tell that I am not a generic woman. However, I still have a penis and testicles. I plan to have sexual reassignment surgery and have my male organs transformed into a vagina sooner rather than later, but it is a very expensive procedure. It is essential that you get a surgeon who has achieved great results over and over again, for there are no second chances. Obviously, those type of surgeons command the highest fee." "I live as a woman full time now and have done so for the past few years. I started taking female hormones four years ago and will probably do so for the rest of my life. I have had several surgeries on my face to reshape my nose, alter my forehead and shave my trachea. I have undergone extensive hair removal laser treatments on my face and body. My breasts are the result of both hormones and implants. Fat has been redistributed from my waist to my hips and butt. So what you see in front of you now might be very attractive, but I certainly did not achieve my appearance naturally." "I might add that I usually prefer men to women, sexually, although it turns out that I am quite bisexual. Strangely, I was drawn to you because you seem to have a androgynous aura about yourself. You are obviously a male, but I detect many female characteristics as well, such as the way you cross your legs, the way you walk and even the way you gesture with your hands. You don't impress me as being gay, but it wouldn't surprise me if you have some experience at wearing women's clothes, at least in private." "I hope that I haven't totally turned you off by all of this, but I felt I must be completely honest with you, before we go any further. You seem to be a very nice person and I would really like to know much more about you, but we must be able to accept each other as we are to have any sort of relationship at all." "Wendy," I said, "I can't thank you enough for being so honest with me. I did not have any idea that you are a transsexual, but believe me when I say that rather than turn me off, it enhances my attraction to you. I have never met anyone as insightful as you are. You saw right through me immediately. I wear women's clothes almost every day when I am home and I guess the gestures you noticed are a result of habits I have gotten into that have become natural to me." "Right now, I am wearing frilly panties under my jeans and I would wear more feminine undergarments if I felt that I could get away with it. I really seem to come alive when I am dressed as a woman. However, looking at you tells me how far away I am from ever being able to dress in public." "Prior to meeting you, I thought that I was only sexually attracted to females. I was strongly attracted to you immediately and I thought you were a genetic woman. I assure you that I am every bit as attracted to you now, perhaps even more so, because of your honesty. I have never had sex with a transsexual before, let alone a male. However, when I am fully dressed, I must admit fantasizing about how it would feel to have sex with a man." "I would really appreciate your help, Wendy. You are now in a place where I would like to be eventually and quite frankly, I don't have the confidence, or knowledge to do it alone. If I could ever get to the point where I could be half as feminine as you are, or half as attractive, I would be thrilled. Could you at least give me some pointers to get me started in the right direction?" "Jim, I would be more than happy to help you. I think that I know how confused and vulnerable you must feel now and hopefully, I can be of some assistance. Tomorrow is Sunday. How about if I come over to your apartment tomorrow afternoon, say about 3:00 pm. I would appreciate it if you were fully dressed as a woman when I get there so I can see where we have to start at." "I would love that, Wendy. Thank you so much. I'm so excited about this. I'll spend the entire morning getting dressed and ready for your visit. Let me give you directions and parking instructions." I wrote down the directions to my apartment and as I gave them to her, she said "By the way, Jim, do you have a female name that you think of yourself as when you are dressed?" "Yes, I answered. It is Joanna. "What was your name before you transitioned?" "It was Bill. But nobody has called me that for quite awhile. If you don't mind, I would prefer to call you Joanna and please call me Wendy. I'll be looking forward to seeing the real Joanna tomorrow at 3:00 PM." With that, she stood up, smoothing her skirt as she did so, and walked out of the cafeteria. I noticed that she had no trouble whatsoever walking on her high heels. I was not the only man there who stared at her delectable derriere as she walked away. That evening I tried to decide what to wear the next day. I didn't have a great supply of women's clothes and it was far too late to get any more from my favorite mail order places. So, I decided to wear my most girly things, a wide, knee length print skirt with a thin belt, a sleeveless pink blouse and sandals with a two inch heel. I would also have to wear my pony tail higher on my head, instead of the accustomed lower spot that it was in when I was dressed as a male. I would have liked to have it styled, but that would have to wait for the future. I had enough makeup to at least make an attempt at looking feminine. Of course I would have to shave my underarms, legs and chest, in addition to my face. The next morning, I awoke early and after washing my hair in the sink, I took a hot bubble bath, with lilac smelling bath salts. I took care of the shaving in the tub. I moved my testicles up into their accustomed hiding places and pulled my penis back between my legs, before securing both with a pair of tight panties. After putting on a B cup bra, I stuffed the cups with plastic bags filled with rice. Then it was time for the blouse and skirt. I cinched the belt as tight as I could around my waist and decided to not wear pantyhose, or nylons. I put on my two inch sandals and I took a look at myself in the mirror. Not bad, but nowhere near what Wendy looked like yesterday. It felt so good to be wearing female clothes again. Every time I put them on it was not only incredibly exciting, but it seemed to make me feel complete, like this is what I should always wear. I felt vulnerable, yet pleasingly so. I couldn't really make any sense of that, only that these clothes were more than a turn on, they were a catharsis, a realization of who and what I really am. After eating breakfast, it was time to make myself as attractive as I could. I put my makeup collection on the kitchen table, propped up a mirror and went to work. Although I had done this before many times, I was only doing it for myself before. This time Wendy would be appraising my abilities. It took a long time to put on my face with coverall makeup, rouge, eyeliner, eye shadow, mascara and lipstick. Several times I had to redo portions, especially around the eyes. By the time I passed my own inspection, it was almost time for lunch. I looked in my jewelry cache and pulled out a string of non cultured pearls, clip on pearl earrings, a beaded bracelet and a couple of rings on each hand. I decided to only have some yogurt for lunch, so that my makeup wouldn't be damaged too much. By the time I was finished, it was almost 1:00 PM and I still had to practice sitting, walking, hand gestures and talking in a higher voice. Although I have practiced each of these many times, I wanted to be as proficient as possible for Wendy. Afterwards, I redid my lips, redid my hair, checked myself in the mirror and sprayed on some Channel Number Five perfume. I nervously sat on my sofa and wondered how a beautiful creature like Wendy could be interested in me. Of course I now knew that she was a transsexual, but I hadn't known that when I met her and became entranced by her. The fact that she had a penis didn't seem to bother me at all. In fact, I wondered how big it would be. 3:00 PM came and went and by 3:15, I began to wonder if Wendy wasn't coming after all. Just then the doorbell rang and I quickly went to the door. Wendy stood there with a light coat over her dress, her purse over her shoulder and a big smile appeared on her face when she saw me as Joanna for the very first time. "Hello Joanna, it is a real pleasure to meet you," she said. "I'm so happy to see your real persona, rather than the male that I met yesterday. I enjoyed your male side as well, but I can see already that you are quite attractive as a woman." With that, she walked in and after I closed the door, she came over to me and gave me a big hug. I couldn't believe how relieved I was to see that Wendy accepted me as a woman, rather than as a man in drag. "Let me take your coat, Wendy," I said as we disentangled from the delicious hug. "Please come in and have a seat," I said, gesturing to the sofa and chair in my living room. I helped her off with her coat and went to the closet to hang it up, as she walked over to the sofa and sat down, putting her purse down beside her. Wendy was wearing a light beige dress, with buttons down the front. The skirt portion swirled around her legs as she walked and ended just above her knees. Her matching high heels were at least three inches high, with a stiletto heel. They were slightly open in the front and I could see that her toenails were painted the same bright red hue as her fingernails and lipstick. Her blond hair fell around her shoulders as it did yesterday. Her scent was as intoxicating as it was the previous day. I walked over and sat beside her on the sofa, trying to move and sit as a woman would. To say that I was very self conscious would not be exaggerating. "Joanna, I can see how nervous you are," said Wendy. "Please try to relax a bit. I can understand how you feel since I was in the same place several years ago." "I'll try," I replied. "I could hardly sleep all night worrying about what I would wear today and what you would think of me. I am so thankful that you have offered to help me. Before I met you yesterday, I thought that I would be living the rest of my life wondering who and what I really was. Now perhaps, you can help me discover the real me." "OK then, lets get started," said Wendy. "I can already see how much you enjoy dressing as a woman and you seem fairly comfortable doing so. Your choice of clothes is good, and when you are dressed, your mannerisms are quite feminine, even more so than I alluded to yesterday. Of course several things could be improved upon, such as your makeup and hair style. It would also help greatly if you found another method of forming your breasts, since whatever you are using now does not look realistic enough. You also have to get rid of the hair on your arms and probably on other parts of your body as well." "First, however," she continued, "we have to determine where you really are in terms of your true sexual preferences. I told you that I am bisexual, but it took me awhile to discover that. I think that we can do some simple experiments and find out where you are at very quickly. You mentioned your confusion yesterday, so lets see if we can clear some of that up." "Joanna, I would appreciate it if you would pull your skirt up to your waist and take off your panties." I couldn't believe what I had just heard, so I said "Wendy, if I do that I will be totally naked up to my waist except for my shoes. Why would you want me to do that?" "Because, I want you to show me your penis, that's why," she answered. "Just do it please and don't ask a bunch of questions. I promise not to hurt you in any way. In fact, I won't even touch you." So, I hiked my skirt up and tugged my tight panties completely off. My penis and testicles moved back to their accustomed positions and were totally on display. "Do you see how flaccid your penis is now, Joanna," Wendy asked? I imagine that is at least partially due to your discomfort at being on display and being embarrassed by it all." "Of course I'm embarrassed," I said. "Now that you have seen me, can I put my panties back on and lower my skirt?" "Not quite yet," she said. First I want to see what effect this might have on you." With that, Wendy turned towards me, unbuttoned the top four buttons of her dress and slipped it off her shoulders. Underneath, she had on a black demi bra, which lifted and shaped her large breasts and left nothing to the imagination. I must have been staring at her, because she said "Do you like what you see, Joanna? These are implants, but they feel very real and I assure you they bounce and jiggle just like the real thing. She demonstrated by lifting and massaging her breasts through her bra. "Would you like to touch them now," she asked? My hands darted to her chest and my fingertips started to massage those portions of her breasts that were protruding over the cups of the demi bra. "Why don't you unhook my bra, Joanna so you can really feel them." I leaned over to her and unhooked her bra. Her boobs were large and firm, jutting out proudly. I started to massage them with both hands, paying special attention to her nipples which were at attention. "They are beautiful, Wendy. I wish that I could have breasts like that." "You can, silly," she answered. "You can get implants if you really want them. But now, take a look at your cock. I glanced down saw that my penis was as hard and stiff as it has ever been. I continued rubbing Wendy's breasts, relishing their shape and firmness. "You must have really been turned on by my breasts, don't you agree," she asked? "You are still wearing women's clothes, yet you got very excited at seeing another woman's breasts. I would think that is proof that you still sexually desire females, however you are dressed." "I guess that you are right," I answered. I always thought so, though. I've always been in love with the female anatomy and I've made love with quite a few women. So, it doesn't surprise me that my desire for women is still there, however I am dressed. The big question in my mind, is how I will react to men. I have never had any experience in that regard, except recently in my fantasies, while I have been dressed as I am now." "No time like the present to find out," said Wendy. She removed my hands from her breasts and reaching under her skirt, pulled her panties completely off. Then she lifted her skirt and her penis and testicles were revealed. Her penis was slightly smaller than mine, but not by much and was not erect. She had removed all of her pubic hair, leaving her looking bare and vulnerable. I immediately had an urge to reach over and touch it, but I hesitated. "Would you like to touch my cock," she asked? "I, I guess so," I stammered. "I've never touched anyone else's cock before." She took my right hand and placed it on her penis. It was quite warm and twitched slightly as I touched it. It was the first penis other than my own that I had ever held in my hand. For some reason, my hand started rubbing it up and down and my other hand reached over to caress her testicles. I could feel her cock start to grow in my hand, until it became fully erect. I continued to massage it, now with both hands. "Do you see the power you have over men" asked Wendy? "You literally have them in the palm of your hand. You could probably get anything you wanted from them by this point." I could hear a soft moan escape from her lips as she squirmed on the sofa. "Now lets take a look at your cock," she said as she reached over and lifted my skirt. "Take a look at your cock now. "It is just as erect as it was before. Do you think it would look like that if you were turned off by seeing and touching a man's penis? I don't think so." Then she moved even closer to me, so that our thighs were touching. "You can lick it if you wish," she said. I couldn't resist, since I had been thinking about getting her cock in my mouth ever since she removed her panties. My tongue snaked out and touched its prodigious head. It felt very smooth. I licked down the length of it and could actually feel the protruding veins on each side. It tasted a bit musky, but not bad at all. "Now put it in your mouth and suck it, Joanna. Be careful with your teeth, but try to get as much in your mouth as you can without gagging." I did as she asked, feeling it twitching and getting even warmer and stiffer if that was possible. Wendy started to make throaty sounds and tried to push more of it into my mouth. "Move your head up and down on my cock," she said. I did so, until I felt it hit the back of my throat, so I backed off a bit. I was sucking as I moved up and down her cock and her squeals of delight were an obvious sign that she was enjoying it immensely. Her cock felt so hard and warm and I realized that I loved doing this. I felt so sexually stimulated that I put my left hand on my own penis and found that it was still as erect as before, if not more so. Wendy suddenly remarked "Joanna, I'm going to cum very soon and I want you to keep sucking when I do so. Is that OK with you?" I nodded my head up and down as well as I could with a mouth bulging with rigid cock. "Alright, when you feel it spurt, start swallowing as quickly as possible and continue swallowing until you feel it stop spurting." Wanting her to cum in my mouth desperately, I sucked even harder and lightly touched her balls again. Suddenly, I heard Wendy moan loudly, her cock twitched violently and it was all I could do to keep it inside my mouth. Then I felt a copious amount of liquid spray the back of my throat and I swallowed as fast as I could. This was repeated three or four times, until Wendy's ejaculation finally ceased. Some of her cum that I couldn't swallow, dribbled down the sides of my mouth and some was still in my mouth. It felt a bit slimy and sticky, but the taste was not bad at all. I wouldn't call it delightful, but certainly not in the least bit offensive. I immediately realized that I was now a true cocksucker and I had enjoyed every bit of the experience. I not only enjoyed it, I was looking forward to sucking cocks in the future. Here I was, a male, with a penis of my own, dressed totally as a female, and loving every second of sucking Wendy's cock and swallowing her cum. After a short while, her cock shriveled and fell out of my mouth. I licked the last drop off its tip and leaned back on the sofa. Wendy fell to her knees in front of me and said "now its your turn, baby." She opened her mouth and a second later, she had my entire cock inside of her mouth. Her nose was in my pubic hair. Now I have had blow jobs before, but nothing like this. Wendy's mouth was like a vacuum, urging the sperm in my balls to emerge. Less than two minutes later, I came in torrents. Wendy dutifully swallowed it all quickly, then sat on the sofa next to me and we started to kiss. Any cum that remained in either of our mouths were mingled. It all felt so good to me and so comfortable. After kissing and snuggling together for awhile, Wendy said "Joanna, I hope that this session has been helpful to you. It is quite obvious to me that you are at least as bisexual as I am, but I'd like for us to go a bit deeper into what you really want. You have made a few statements today about going much further into becoming a woman, into really transitioning. However, you must realize that each of these further steps, such as hormones, breast implants and sexual reassignment surgery will require great sacrifices on your part. You won't be able to continue as you are today. It will necessitate you being much more than a part time transvestite." "Here is what I suggest," said Wendy. "I would like you to spend this next week thinking about what has happened today and what you have learned about yourself. Consider the implications of going any further into your transition. For example, would you be able to give up your current comfy arrangement of being a girl only in your apartment and just during evenings and weekends? Could you announce to the world who you really want to be?" "What I further suggest is that you come over to my house after you finish work this coming Friday afternoon and prepare to spend the entire weekend with me, as a woman. Don't even go home first. Come to my house directly from work. I have everything there that I need to help you continue your journey. We are very similar in size, so you don't even have to bring any clothes with you. Mine will fit you quite well. I took a look at the size of your shoes and we are the same size there as well. Thank you for shaving your unsightly male body hair for today. I would also appreciate it if you would remove all of your pubic hair before Friday as well. At the end of the weekend, I guarantee that you will know a lot more about yourself and have at least a partial game plan in mind for the future." "That sounds wonderful, Wendy," I said. "I'll follow your directions and I'll be looking forward all week to our next meeting. Today has really been an eye opener to me. I can't thank you enough for helping me. It has been my first time for a lot of things. I think that the best part of all, was just snuggling with you. Two girls just cuddling. Please give me directions to your house and what time I should be there next Friday." The week couldn't pass fast enough for me. As usual, I wore my suits to work, with panties underneath and changed into dresses when I got home in the evening. On Thursday, I shaved my body hair off again, so that I would be as smooth as possible, this time including my pubic hair as Wendy suggested. I did a lot of thinking about the future and what I wanted. I knew now that dressed as a female, I was attracted to males as well as females. Therefore, if I became a woman, I could have the best of both worlds, sexually. The big question that I was having a hard time answering was did I want to give up my comfortable, although boring, existence and start on the dangerous path of transitioning. All day Friday, I fantasized about becoming Joanna again. I had spent other weekends dressed entirely as a female, but those were weekends spent entirely alone, in my apartment. This time, someone else will be there. Someone whose cock I amazingly have already sucked and enjoyed. What else will Wendy have me do tonight and for the rest of the weekend? Will tonight begin a turning point in my life? Or, did the turning point already take place the moment I met Wendy? Finally the workday ended and I drove over to the address that Wendy had given me. She answered the doorbell immediately and as soon as I was inside, she grabbed me and gave me a very intense kiss. Her tongue circled the inside of my mouth and I felt my erection throbbing in my pants. I felt her hands pulling down my zipper and pushing my pants and panties down and taking them off. "Thank you for doing as I asked, my love," she said, as she ran her hands around my hairless crotch. The next thing I knew, Wendy was on her knees before me, greedily sucking on my cock. I wanted to experience this for a longer period of time, but my excitement won out and I came into her beautiful mouth way too quickly. "That was my little welcoming greeting I thought you might enjoy," said Wendy, as she got up from the floor. "Just leave your pants there on the floor. Please take off the rest of your clothes and leave them there as well. I'll take good care of them for you, but you won't be needing them for the next few days . I think that you will find the weekend I have planned for you to be quite exciting and filled with new experiences. Now, I would like for you to go into the bathroom and get into the hot, scented bath I have already drawn for you. After you finish your bath, please call me and I'll get you ready for the next stage of your adventure." I luxuriated in the tub for awhile. I could feel the hot water and lavender scent oozing into my pores, making my skin feel softer and more fragrant. As I got out of the tub and started to dry myself with the big, pink fluffy towel I found there, I called for Wendy to come in. When she entered she was entirely naked, the first time I had seen her this way. She was gorgeous. Her large breasts jutted outward and jiggled slightly with each step she took. I noticed that her dark nipples were standing at attention. The rest of her body looked very womanly, with soft curves replacing the hard musculature of the male body. The only distraction was her bare cock, jutting straight outwards. I felt an urgent desire to explore her body with my hands and mouth. I hugged her and kissed her eager mouth. Then I worked my way down her body licking and kissing as I went. When I finally arrived at her cock, I greedily took it in my mouth and sucked until I was rewarded with her nectar. "Mmm, that felt so good," she murmured. "Much more later, sweet Joanna. But now, we must get down to business. Have you ever given yourself an enema?" "No," I confessed. "I've never had any serious constipation problems." "I'm not thinking about constipation," Wendy continued. "One of the things I have planned for you this weekend is to get you ready for anal intercourse. To do so, it will be necessary to prepare your body to receive the intrusion of a large object, human, or otherwise. Basically, we will have to loosen your orifice and sphincter muscle so that you will not be injured when the actual object is inserted. Have you ever had anal sex before, Joanna?" "No, certainly not, I answered. "As I think I mentioned to you, I have fantasized about it, but I've never done anything like that. Wendy, do you mean you want to screw me in the ass this weekend?" "Only if you want me to," she answered. "Anal sex is very common with transsexuals, especially those who desire male companionship. You certainly did not shy away from oral sex with my penis, nor did you object when I sucked your cock. Please understand, Joanna, I won't do anything that you don't want me to do, either today, or in the future. I just want to start preparing you for what will lie ahead if you continue on the transition path to femininity." "Well, I guess that it would be alright," I answered. It would certainly give me some additional information. But won't it hurt, especially since I've never done anything like that before?" Perhaps a bit," said Wendy. "The way I suggest we proceed, is to insert smaller items at first, such as fingers, with a generous amount of lubricant, then larger ones until you have been sufficiently loosened. As you probably noticed, my cock is a bit smaller than yours, because of all the hormones I have taken. So, I should be able to put it inside you without your experiencing a great deal of discomfort." "Would I be able to enjoy it at all ," I questioned? Would it excite me, make me feel more feminine if I have a cock in my ass? Would I be able to cum that way?" "I sure do, when it is done to me," answered Wendy. I love being fucked that way. I cum almost every time. But your mental attitude will play a big part in the amount of enjoyment you get from it. You have to be open to it. You have to be willing to be the subservient partner in the relationship. Your lover will do the leading and all you have to do is lie there and enjoy it." "So how do we begin," I asked? "What do you want me to do to prepare myself?" "First, let me show you how to clean yourself with an enema, Wendy answered." Then after allowing your anus to recover from the enema for a few minutes, we will go into the bedroom and begin. Once we were in the bedroom and lying together naked on the bed, Wendy asked me to touch and suck on her breasts. While I was busy with her large nipples, she had reached over to the bedside table and took a jar of Vasoline out of it, opened the jar and placed her index and middle fingers of her right hand into its slippery contents. Soon thereafter, I felt her spreading my ass cheeks and suddenly, her index finger easily slid inside my virgin asshole. It felt strange, but not at all painful. It gave me a feeling of fullness, of vulnerability. Then, she slowly inserted her second finger alongside the first. More fullness, but little, or no discomfort. Then she pushed both fingers into me as deeply as she could and started to wiggle them around. Suddenly, I felt a sensation inside me, as if I had been hit by a jolt of electricity. Wendy kept rubbing the same spot and I began to feel sexual excitement. I felt liquid starting to drip from my cock, as she slowly pulled her fingers out of me. I sighed and lay back on the pillows. "I guess that you enjoyed having your prostate massaged, didn't you," said Wendy. "I sure did," I exclaimed, still rubbing my legs back and forth against each other, trying to recreate the friction I had just felt inside me. "You took two fingers very easily," she said. Now I'll put in a butt plug for you to wear for awhile." Wendy again leaned over to the bedside table and withdrew a five inch long dildo with a flat base on it. It was made of plastic and was ribbed along its sides. It was fairly narrow, certainly no wider than her two thin fingers had been. She coated it with vasoline and inserted it into me. It was longer than her fingers, and I felt like I was stuffed, but no real discomfort. Actually, the feeling of fullness was quite pleasant. "Keep that plug in yourself for awhile," she said. "Get used to having something that size inside you. My cock isn't much bigger than that dildo, so if you can tolerate that butt plug, I should be able to enter you without too much difficulty. But now, it is time for your male persona to disappear, hopefully forever and your girly side to come out." "Tonight will be your unveiling, so to speak," she continued. "I am going to dress you, make up your face and make you look as feminine as possible. Then, I'll top it off with an alluring wig and some jewelry. I wish that I could style your hair, but we don't have the time. You have an appointment at a beauty parlor for early tomorrow morning for a complete makeover. The stylist can work on your hair then. For tonight, the wig will do." "Do you have something special in mind for this evening," I asked, tentatively? "After you make me look like a woman, will we be doing anything else?" "Oh yes indeed," said Wendy. Tonight I have reservations for us at a restaurant in town. We will go there as two women. It is high time that you showed yourself to the outside world, as the female that you feel you are. "Don't worry, Joanna. When I finish getting you ready, nobody will be able to guess that you aren't really a woman." "To start with, you will need some nice big boobs. Go to the bathroom and clean yourself up a bit. Keep the plug in though." When I returned, she had two large breast forms sitting on the bed, along with a tube of adhesive. "Once I apply this adhesive to them, these breast forms will stay on your chest all weekend. I have a solvent to remove the adhesive whenever you want to. " Wendy rubbed the adhesive on the undersides of the forms and one by one, carefully affixed them to my chest, pressing them firmly on me. "Put your hands on them and hold them tight for a couple of minutes while the adhesive dries. It won't take long," she said. I had used breast forms in the past, but nothing like these. These looked like real breasts, complete with nipples and they were very large. I guessed that they would make me the equivalent of a 38D. They felt soft to the touch and gave when I squeezed them slightly. When Wendy told me I could, I removed my hands and the forms stuck to my chest quite nicely. I couldn't believe their weight. I would definitely need to wear a bra to support them. Next, she gave me a gaff, which I discovered is basically a very tight pair of panties. She asked me to push my testicles into their natural body crevices, and bend my penis down and back between my legs. Then I pulled up the gaff and my crotch area was as flat as any females. My butt plug was also held very securely. Of course I would have to pull the gaff down to pee, but I already knew that I wouldn't be using any urinals wearing a dress. A black lace garter belt was next and a pair of thigh high nylons followed. I was fairly experienced with rolling them up my legs and attaching them to the garters, so I didn't need Wendy's assistance with them. At least I didn't think so. After I completed my task, Wendy reminded me that the garters should be under the gaff, otherwise, I would have to unfasten the nylons to go to the bathroom. Obviously, I still had a lot to learn about dressing as a female. A black bra was next. My guess about the size of my breast forms was correct. The bra was also a 38D. Here again, I was pretty experienced in fastening bras, but once I had it on, Wendy adjusted the straps for me so that it fit perfectly. The bra was pretty low cut and showed a good deal of the tops of my forms. It also pushed my faux breasts together, creating a very nice cleavage. The only problem was that the forms and my skin were close in color, but not exactly alike. Wendy took care of that problem by applying makeup to my chest and blending the two together. She handed me a black, silky half slip to pull on, which barely covered my garter fasteners. Patent leather, four inch black pumps followed. Wendy was true to her word. They fit perfectly. I had worn heels in my apartment, but they were only two inches high. These four inch stilettos would take some getting used to. I walked around the room, somewhat unsteadily for a few minutes, until I got the hang of it. I realized that they would take some getting used to. Next, Wendy had me step into a black dress. She pulled it up over my hips, put my arms in the small sleeves and zipped it up in the back. It had a low cut, scoop neckline in front and in back. The hem ended several inches above my knees. I could see the tops of my boobs spilling over the neckline as well as a generous amount of cleavage. The dress obviously made my breasts the center of attention. It was makeup time, so Wendy had me sit in a chair with a drape over my shoulders so the dress would not be soiled. She started with foundation. As she was spreading it on my face she said "Joanna, if you decide to go ahead with your transformation to womanhood, one of the first things you should do is get rid of your facial hair. I can suggest a woman who is marvelous at it and who is not as expensive as others. Be aware, though, it is a long, painful and tedious process, which is why I am suggesting you get it started as quickly as possible. You certainly don't want to use this beard covering foundation for too long. It clogs your pores and has been known to cause skin problems in girls who use it extensively." After the foundation was applied, Wendy took out a tweezers and plucked a few stray hairs from my eyebrows. "I can't really give you the thin arch that women desire since it would look strange for you to go to work on Monday with a woman's eyebrows. If and when you come out at work, we can take care of your eyebrows at that time. For now, we will stick with a reasonable facsimile. Then she took out eye liner, mascara and eye shadow and spent considerable time on my eyes and lashes. She said "wait until you see your eyes, Joanna. They look fabulous, if I do say so myself." She also applied some rouge to my cheeks with her finger and finally, used bright red lipstick on my mouth. She had me blot the lipstick on tissues. "Now hold out your hands, Joanna. I'm going to put some inexpensive press on nails on your fingers. You will get a proper manicure and pedicure tomorrow morning. For tonight, you won't need anything on your toenails since you will be wearing closed pumps." She proceeded to glue press on nails to each of my fingers. There was no color but they made my nails longer. Then she used an emery board on them to smooth any uneven surfaces. I had never used these before and it felt strange to have longer nails. I would have to get used to these as well. Next, Wendy took a wig from her closet, brushed it and fitted it on my head. It was an auburn color and reached to just above my shoulders. It was very full in body and quite wavy. Once she was satisfied with how the wig looked, she brushed it again. Then she removed the drape from my shoulders. The next step was jewelry. "I wish that your ears were pierced, Joanna. There are so many more beautiful earrings that I will be able to loan you if and when you get that done. For now though, we will have to stick with the few clip on earrings that I still keep around." She hunted in a jewelry box and took out a pair of pearl earrings and clipped them on my ears. "They might hurt a bit after a couple of hours. Just unclip them, rub your ears and put the earrings back on. That is about all you can do until you get your ears pierced. It is up to you, but you can easily get your ears pierced tomorrow morning at the salon. Lots of men have pierced ears nowadays as well as women. But that will be up to you to decide." Wendy also found a single strand of pearls in another of her jewelry boxes, along with a pearl bracelet. "Joanna, this is just costume jewelry, so in case something falls off and you lose it, don't be too worried about it." Wendy then sprayed some delicious smelling perfume on my neck, wrists and cleavage. She put the bottle in a small, clutch purse, along with the lipstick, a makeup compact, eye liner, eye shadow and mascara. She also put twenty dollars in the purse along with a couple of condoms and gave the purse to me. When I raised my eyebrows at the condoms, she said "you never know what the evening may bring. It is best to be prepared for all contingencies." "Joanna, now is the time for you to see what you look like as a woman. I think that you will be pleasantly surprised and like what you see." She took me by my arm and led me over to her closet and opened it, revealing a full length mirror inside. I couldn't believe what I was seeing. I looked like a real honest to goodness woman. I wasn't beautiful, but I was quite attractive. What really stood out were my breasts, the tops of which were quite visible and my cleavage was remarkable. The makeup had made a tremendous difference. My eyes were really pretty and looked very much like Wendy's eyes. My red lips looked eminently kissable. I couldn't help posing in various ways in front of the mirror. I looked and felt very sexy. "Wendy," I said. "I really do look like a woman. I just hope that I will be able to pass as a woman tonight." "I'm sure that the ladies at the beauty parlor will even do a better job tomorrow, but for a quick makeover, I think that you look great," she remarked." "If you transition, you might need some facial surgery, as I did, on your nose and chin, along with breast augmentation, but nothing too major unless you decide to go all the way." "Wendy, the more I look at myself, the more I wish that my breasts weren't just glued on and that any changes I need were already finished. I love looking like a woman and right now I feel like one." "That's wonderful, Joanna," she remarked happily. "Now, I think that it is time to go to the restaurant. We have a reservation for about a half hour from now and I am getting hungry." "How can I ever thank you, Wendy, for all that you are doing for me," I asked. "Without your help, none of this would be possible. I wish that I had a way of repaying you." "Don't worry, sweetie," she answered "when we get back tonight, I'll think of something." Since this was my first time to go outside in feminine clothing, it was also my first time to ride in a car as a woman. Just getting into the front seat was quite an adventure, first with the stilettos and then with my dress pulling up almost to my hips. "Joanna, turn and sit in the seat backwards, then pull your legs in after you. I think that you will find it much easier that way and certainly a lot more ladylike," said Wendy. I got out of the car and tried it again as she had suggested and it was indeed much easier that way. "Now, when we get to the restaurant, just do it in reverse," she said as she started the engine. We arrived at the restaurant without any problems, and Wendy turned into the valet parking area. She explained "parking here will save you the trouble of walking a longer distance in your heels." The attendant came over to our car and opened the side door so that I could get out. I turned my knees outward as Wendy has suggested and although my dress rode up so that a garter could be seen by the attendant, at least it wasn't obscene. The attendant took my hand and helped me out of the car. I noticed that he was staring straight at my breasts as he did so. The attendant then went to driver's side to help Wendy. She had already gotten out of the driver's seat and held her car keys out to the attendant. As Wendy and I walked the short distance to the front door of the restaurant, I felt something that I had never felt before. It was a breezy evening, and I could feel the air blowing under my dress and between my legs. Between that and the delightful friction of my nylons rubbing against each other, not to mention the butt plug, it was quite erotic. Since both Wendy and I are quite tall, especially in our heels, I imagine that we were very noticeable as we entered the restaurant. I was aware of people at several tables turning to stare at us as we stood waiting to be seated. "Don't be concerned, Joanna," Wendy advised me. "They are staring at two lovely, tall, desirable women. I assure you they have no idea who you really are." I relaxed a bit when we were seated and given menus. "By the way," said Wendy, "I forgot to remind you that you will have to go to the women's restroom this evening, not the men's restroom. Don't worry. If you have to go, just let me know and I will accompany you. There are no urinals in there so just select one of the stalls and be sure to sit down to pee. After you are finished, just wait until I knock on your door. I'll take you over to the mirrors and let you repair your makeup, if you need to. After dinner, I usually freshen my lipstick." I looked around the room and saw a few men looking our way, and one or two women as well. It was disconcerting to be ogled like that, but it was also something that I would have to get used to, especially if I were to continue to wear revealing clothes. I also realized that it was so much more comfortable wearing a dress with a lower neckline, than a shirt, tie and jacket. It had always bothered me to feel so many layers of cloth around my neck. Perhaps now, I wouldn't have to put up with that any more. Instead of watching others, I concentrated on my own feelings. Here I was in a crowded, fashionable restaurant, totally dressed in women's clothes, with makeup, perfume, long fingernails and jewelry. I was somewhat uncomfortable with real or imagined stares from others, but I was mainly thrilled to be in this position. I had never done anything like this before, and if it wasn't for Wendy's urging, it wouldn't have happened now. Whenever I moved slightly, I could feel various items of clothing move in such delicious ways. Looking downward, I could see the swell of my breasts. I actually felt desirable, to men as well as to women. I began to wonder if after tonight, I could ever go back to my male existence. Our waiter took our dinner order, glancing at Wendy's cleavage as he did so. I actually felt a pang of jealousy that he seemed be more enchanted by my friend's charms than my own. I glanced downward, and could actually see a noticeable bulge in his trousers. I don't know what came over me, but my hand actually started moving towards it before I stopped myself. Once our food was delivered, I found that my longer fingernails made it more difficult to handle my silverware comfortably. Just one of many new things to get used to, I thought to myself, like stilettos, gaffs and a hairless body below my neck. Once we completed our meal, Wendy rose and said "come on Joanna. It is time for your first trip to the ladies room." A feeling of panic swept over me for a few seconds. But then, I realized that if I were to transition, this would be a normal, everyday place that I would be visiting. I pushed my chair back, rose, wobbling slightly on my high heels and followed Wendy to my new, totally feminine environment. I quickly realized that the ladies room wasn't much different in structure than the men's room. It had more stalls and no urinals, but it had the same types of sinks, mirrors and hand dryers. The major differences were in the smells and sounds. Men's rooms always have an offensive odor inside, no matter how many times a day they are cleaned. The odor in the ladies room was quite different, possible mitigated by the perfume and lack of body odor of the women using it. Also, women peeing while sitting down, have much less chance of peeing on the floor, than men do with urinals. The women seemed to talk to each other more in the ladies room. High pitched giggles and the sounds of long hair being brushed were so much different than the silence usually heard across the hallway. Men strive to leave the men's room as quickly as possible, whereas women seemed to be using it as a meeting place. I followed Wendy's advice and I was waiting for her to knock on the door to my stall. When I heard her, I stood up, pulled up my gaff as quickly as possible, flushed the toilet and exited, smoothing my dress as I did so. We went over to the sinks, where Wendy fished a lipstick out of her purse. It was then that I realized that I had left my purse on the table. "Wendy, I screwed up and left my purse on the table. Can I use your lipstick?" "Sure," she answered. "I gave you a tube of the same shade. Just remember, a woman's purse goes with her wherever she goes." After our repairs, we returned to the table. As our waiter passed by, Wendy asked for the check. "Tonight's dinner is on me, Joanna, as is the rest of the weekend. I don't want you to worry about anything. Just enjoy the experience of being a woman." "Thank you so much Wendy, for dinner and for everything else," I answered. "I've learned so much already and I'm looking forward to the next two days. I wish that I had met you years ago." The waiter came back with the check. Wendy grabbed his wrist and asked him to give it to her. I couldn't help but hear his breathing quicken as she touched him and then when he realized the double entendre. When he returned for the payment, he carefully leaned over my right shoulder without touching me to pick up the check and Wendy's credit card from the table. As he did so, I glanced up and saw that his eyes were looking straight down the front of my dress. I felt quite emboldened, so I reached up with my right hand and pulled the scooped neckline of my dress a little more to the side so that the waiter could see more of my breast and a little bit of my bra. As I did this, the waiter picked up the bill and credit card, straightened up suddenly and coughed. Wendy couldn't help herself from laughing. As the waiter left hurriedly, she said "that was great, Joanna. What you did could be a part of the tip that I leave for him. Do you see now how much fun it is to be a woman? Men can be so predictable. It is easy to make them appear to be blithering idiots. They will do just about anything to see an extra inch of breast, or leg." We decided that we had enough fun with the waiter, so when he brought our credit card and receipt back, we just thanked him and got up to leave. As we walked away, I could literally feel his eyes boring into our behinds as we wiggled away on our high heels. On the way home, Wendy asked, "well what did you think of the evening, Joanna. Did you enjoy your first time in public as a woman?" "Absolutely," I replied. I was really nervous before we went, but you did such a good job at making me appear womanly, that I really lost my fear of being found out after awhile. I really liked the feeling of men ogling my body. It made me feel so desirable and sexy. To tell you the truth, I am more sure than ever that I want to begin my transition as quickly as possible." "I'm glad to hear that I was helpful," answered Wendy. "If you are really sure about beginning your transition, then you will have to decide when you will be coming out at your workplace. You really can't start some of the procedures until then." "Well, earlier today, I thought that I'd like to postpone that as long as possible," I said. "However, now that I am sure I want to begin my transition immediately, I want to get my inevitable work announcement over right away. This coming week would probably be best, so I could get it over with. If I do that, when could I start on the first procedures?" "The first steps that I would suggest," answered Wendy, "would be the facial hair removal we discussed earlier and getting started on female hormones. Both of those take a long time and the sooner you get started on them the better. Breast augmentation wouldn't take as long. It is just a matter of getting an initial appointment with the surgeon, making your decisions about size and shape and then waiting for the surgeon to have an opening. However, once you have that procedure completed, you can't go back to work, or anywhere else as a man, especially with the breast size you seem to like. As far as your office is concerned, you could probably get by with having your ears pierced tomorrow and having a pedicure. You already have fingernail extensions in place that can last the weekend. The stylist can paint them for you to match your lipstick. I can take off your extensions on Sunday, before you go home. You could wear studs in your ears when you go back to work that are suitable for men, or make up another excuse for the piercings. Your toes will be hidden in your socks and shoes and I can take off your fingernail extensions on Sunday. I'll ask the stylist at the beauty parlor what she can do with your hair for the weekend that would allow you to go out as a woman, but give you the ability to comb it back into a man's style or pony tail for the workweek." "How soon could I start on the hormones and hair removal" I asked? "I would have to make appointments for both of them for you," she answered. I mentioned earlier that I know a relatively inexpensive hair removal expert that could probably start you this coming week. The thing is, once she starts on your face, you will be quite blotchy for a few days after each visit. I can also make an appointment with my endocrinologist for you. She should be able to examine you and start you on hormones within a week or two." "How soon will I be able to see the results of the hormones?" "That will probably take several months until your breasts start to come in and your body fat starts to redistribute itself to your hips and butt. But you skin will start feeling smoother and your hair will become more lustrous within a few weeks. Of course, your breasts will probably never get as big as your breast forms are now by just taking hormones . If you want breasts the size of the forms you are wearing you will have to get implants. The other things, like additional facial surgery, can wait awhile and of course you have to live as a woman full time for at least a full year before you can get sexual reassignment surgery." "Wendy, I think that I'd like to get the ear piercing done tomorrow. "I'd love to wear long, dangly earrings the next time we go out. I think that they would feel so feminine on me. I could also get the pedicure, the fingernail painting and the hair styling that you mentioned. I would also appreciate it if you could get an appointment for me with both the endocrinologist and the hair removal person as soon as possible. I'd like to get started on them both. To tell you the truth, I would love to have the breast implants tomorrow as well. I would just love to feel my real nipples rub against my bra, or to have someone sucking them. But I guess that can wait awhile, until we can get an appointment with the surgeon. I would really like to use the same one that you used. You have the most beautiful breasts that I have ever seen." "By the way, sweetie, is your butt plug still in place," she asked? "Yes it is," I answered. "To tell you the truth, it hasn't really bothered me at all. In fact, when I was eating dinner, I was moving my butt back and forth on the chair because I could feel it move inside me. It was quite exciting. How long do you want me to wear it?" "Just until we get home," said Wendy. "After that, you won't need it any more. I think that you have been opened up enough to take something a little bit larger. I want to make love to you tonight, and let you know what it really feels like to be a woman. Is that alright with you Joanna?" "Of course it is, Wendy. I am as ready as I will ever be. In fact, I am overjoyed that you find me attractive enough to make love to, even though I have a long way to go before I could really be called a woman." As soon as we entered the house, Wendy took me in her arms and kissed me. Our boobs pressed against each other, as our tongues intertwined. We went straight to the bedroom, each of us discarding clothes along the way. "Take everything off ," said Wendy, and pull out the butt plug. I have something to put in there that I think will feel a lot better to you." After our clothes were all off and my butt plug was removed, Wendy had me get on the bed on my hands and knees. My head was pressed against the pillow. My securely fastened breast forms were hanging straight down. She spread my ass cheeks and put a liberal dose of lubricant on a finger and worked it into my behind. She also spread lubricant on her penis, which by now was quite engorged. "Alright Joanna. Are you ready to be deflowered, she asked? "Just be gentle," I implored. "Remember this is my first time." Wendy got on the bed behind me on her knees and started to press her cock into my tight hole. "This might hurt a little, but bear with it. Soon it will feel just wonderful." I could feel the head of her cock starting to enter me, opening me for what lie ahead. Wendy continued to press slowly and the crown popped into me. I felt a bit of pain, as if my skin was being stretched too much, but when the crown finally penetrated me fully, the pain lessened to a great extent. "How does that feel," Wendy asked. "Do you want to wait awhile before I go further, or can I continue now? You feel really tight to me." "It hurts a little bit," I answered, "but nothing I can't tolerate. Let me have more, but go slowly." Wendy pushed again a couple of times and I figured that I had taken about half of her cock. I felt completely filled, bursting at the seams, but the pain had lessened even more. I was totally shocked when she said "congratulations, Joanna, you have taken my entire cock inside you, up to my balls. Are you OK so far?" "Oh yes, Wendy. I feel so full and vulnerable. It is a wonderful feeling. I want more. I want you to fuck me. Please do me. Make me a woman." She started moving slowly and deliberately, inside of me. I could feel the friction, especially against my prostate. This was so different than when I had my cock inside of a woman. This was the exact opposite. Now I was the one being fucked. I was the submissive one and Wendy was the dominant partner. The pain soon subsided totally and was replaced by quite a wonderful feeling of excitement. I could feel Wendy inside of me and I was loving it. Being fucked like a woman was even more exciting than any love making I had done previously as a man. "Oh, Wendy," I cried. "This is wonderful. Please don't stop. Keep fucking me. I love this. I need this so much." I found myself pushing myself backwards to get Wendy's cock into me as deeply as possible. "Harder, Wendy, push harder darling. I think that I feel you all the way up to my throat. That's it. Faster, harder. I want to feel you cum inside me." By this time, Wendy was thrusting into me like a jackhammer, and I could hear her grunts and squeals. I suddenly went over the edge and my rigid cock spurted all over the bed. I had cum without my cock even being touched. Wendy didn't miss a beat, pumping faster and faster until I could hear her groan and she flooded my bowels with her sweet nectar. It was a moment of sheer ecstasy. I think that I passed out for a few seconds, only to awake feeling Wendy's limp body on top of me, her lips softly kissing my neck. Later, after cleaning up, Wendy gave me a blue, satiny nightgown to sleep in. It felt so smooth and delicious on my skin. After remaking the bed, we cuddled together before falling into a contented sleep. It had been a day that I would never forget and my first day as a woman. I awoke on Saturday morning and immediately noticed the rise and fall of my breasts in my nightgown. I cupped them, wishing again that they were mine rather than silicone boobs pasted to my skin. I rose and since Wendy was still asleep, I went into the bathroom. After using the enema bag, I showered, shaved my face as closely as possible and reentered the bedroom to find Wendy awake and putting out an outfit for me to wear. "Are you alright, Joanna," she asked? "I hope that I didn't get too rough with you last night. You seemed to be enjoying it so much that it was hard for me to control myself. I hope that I didn't hurt you." "You didn't hurt me at all, Wendy," I answered. "Oh, a little bit at the very beginning, but that disappeared right away. From then on I thought that I had died and gone to heaven. I have never felt anything that compared to it, certainly nothing that I have ever done as a male. It makes me think even more that I want to become a woman as fully and as quickly as possible. I admit that my butt is smarting a bit this morning, but it is a small price to pay for what you gave me last night." "I'm so glad, Joanna. I want you to enjoy this weekend fully and completely. I hope that you enjoy today and tomorrow just as much as last evening. But now, it is time to get dressed and eat breakfast. Don't forget that you have your first appointment at the beauty parlor in an hour or so." "I'm looking forward to it, Wendy and I meant what I said last night. I want to get my ears pierced, get my hair styled, and get a manicure and pedicure. I also want you to set up appointments for me as soon as possible with those people you mentioned who can start removing my facial hair and start me on female hormones. I even want to see if we can get an appointment with your implant surgeon. I will still be wearing male clothes to go to work on Monday, but I have de