The Office Boy

 The Office Boy

My name was Mike Grant, and I say was, because it’s different now. I have two years of college and I’m taking classes at night to finish with a degree in Business. In order to support my school expenses and have some spending money, I found a job working in an office as sort of a glorified office boy. I’m 5′ 7″ tall with soft brown hair and blue eyes and I have never weighed more than 140 in my entire life. Valerie Hooper, the woman I report to is in charge of the office, and also prepares parties for Christmas and so on. Valerie is about 50, married, with two sons and a husband. For Halloween she wanted everyone to come to work in costume, fully expecting a lot of monsters or ghosts. When I told her I wanted to do something different but had no idea of what, or who, to come as, she smiled and told me that I could easily come as Diane Benson, the actress, when she was my age! “You have the same facial structure she does, and with the right makeup you could be her twin Mike. Think about it and let me know. That night I told my mother what Valerie had suggested, and to my surprise she agreed! “I can help you if you like Mike. Your sister still has a lot of her clothes here so that would not be a problem. Besides, it could be a lot of fun!” I told her that I would think about it.


For years I was lonely, depressed, angry at myself, the world, and the gods that made me this way. I knew I was smart and had a good job, but at age 20, I was still driven by urges I never had any control over, no matter how hard I tried. I often felt the urge to dress as a girl, but each time I did, and then looked in the mirror, I saw a clown instead of the woman I wanted to be. Including my makeup, I was merely a parody of the woman in my dreams. My frustration at my inability to achieve any semblance of the woman I felt I wanted to become had driven me into silent secrecy when I did try to dress up. That night, in my robe, I munched snacks as the television played in a muted tone. The young women on the screen were a constant reminder of what I wanted to be able to look like, and equally, my inability to either conquer my desires, or forget it, or become the woman I had so many dreams about. In my heart I knew I was going to do it, because even though I had secretly tried on my sister’s clothes many times when I was growing up, and always felt like a clown, this time I would have my mother to help me. My mother’s tacit approval lifted the veil of frustration and I felt as if I was soaring. I knew, in my heart, that this time, I would look good. Since Claire was just a year older than I was, most of her clothes fit me pretty well, and I was sure that with some help, I could look pretty nice. My biggest concern was how everyone in the office would react to me dressed as a girl. The next morning, when I told mom about my concerns, she told me that in her mind, the best way, if I was going to do it, would for me to be perfect. Since I didn’t want to come off as a clown or one of those freak of the week people, I agreed. “I’ll get a few things today and we can see how you do tomorrow. If you like it then you can stay dressed as a girl until Monday.”


Someone once said that tears are merely a reflection of the soul, whether its fear, joy, or sadness. All those years of hiding, frustration, fear, and secrecy came to a head all at once, and I started to cry. Why are you crying Michael? This is what you want isn’t it? To live and work as a female?” My head popped up, and out came, “What!” “I’m sure its true Michael, based on the number of times you wore Claire’s clothes!” Shocked that mother knew about my dressing up as a girl, and afraid of what I might blurt out, I kept my mouth shut. “I said I would help you if you let me Michael, and I think that you should practice dressing every day after work, and each weekend from now until the day when you go to work.” I started to say something, but mom held her hand up and said, “You did say that you wanted to be perfect didn’t you?” “YesÉ” “Well this will give you a few weeks of practice before the party!” I could find nothing more to say about it, swallowed my pride, nodded my head yes, and quietly went to my room. That night I decided that mom was right. I would do the best I could or not at all, and if she already knew about me dressing up and wanted to help me then no matter how I thought I looked it wouldn’t matter.


 

 

officeboy-p2.jpgOn Saturday morning right after breakfast mom told me to go to my room. I have everything you’ll need. I’ll just show you how to use it and you can take it from there.” As far as my mother was concerned it was a done deal, and that combined with my natural desires made it easy for me to stay silent in my agreement. Mom gave me the stuff, which I recognized as a popular hair removal cream. As soon as she left the room I stripped and quickly had a coat of the cream all over me, from the eyebrows down. After a shower and a close shave I stepped out and patted myself dry. I had never yet shaved my body or used hair removal cream before, and I was surprised at just how smooth my skin felt. My beard, while not what you would call light, was a light color and only moderate in growth, and after I shaved I had nice soft skin. With the towel wrapped around me I went into Claire’s bedroom and closed the door, hesitating for just a moment because I was pretty sure that as soon as I was dressed and stepped out of the room I was not going to want to quit. Ignoring that thought I forged ahead, opened her dresser and selected a pair of lavender colored cotton panties and slipped them on. When Claire was younger she had a shape like a pencil and used a padded pantybrief and some breastforms to give her some shape. I had found them while I was in her room dressing once, and made sure I left them right where I found them. I slipped on the pantybrief, adjusting the pads to suit me. The pantyhose went on easily, but the nylon against my now naked skin was like an electric shock as I slid them on. I went to the vanity and sat down facing the huge mirror.


Makeup was the only thing I had managed to almost master simply because that was all I could do on so many occasions. I applied the foundation using a powder to set it, brushing away the excess as soon as it dried, leaving my skin looking soft and smooth. On my eyes I used a mint green with copper and gray highlights with deep black eyeliner both over and under my eyes. A bit of rose blusher on my cheekbones and black mascara on my lashes. My naturally curly hair was thick, and as it was drying the ends started to curl, so with a brush I was able to create a modest if messy pageboy that framed my face. The curly ends added just the right touch to the style. I didn’t even need a curling iron. I heard mom knock on the door, and when she came in the room and saw me, she told me that my makeup was fine. “Let me help you with your nails.” I opened the small drawer and pulled out the box of fake nails. Using the glue in the box mom attached one to each of my nails and filed them into an oval shape with rounded tips. The polish I selected was one shade up from pink. It took a while for the polish to dry, and while I waited I stood in front of the closet and tried to select what I was going to wear for my first public debut.


As soon as my nails were dry I slipped my arms into the lavender bra and settled it in front after I fastened the single front hook. The breastforms were flesh colored, filled with silicone to a small ‘B’ cup, which was perfect on my frame. The waist nipper was beige with eleven hooks and a zipper, and once I had it on it made my waist a trim 25 inches. Unable to decide on what to wear, mom picked out a light blue floral summer dress for me to wear. She said it would ‘go with’ my bra and panties. I wore off white sandals and a matching blue jacket. Mom redid my hair a bit and it seemed to flow around my face. I looked in the mirror and was floored! The reflection in the mirror I saw that I did look like Diane Benson in a way and I stood before the mirror in a dream like state looking at the girl standing there. I loved the image I was seeing. The girl that I had only dreamed of stood in front of me, not perfect of course, but I did not feel like a clown this time. The image I saw in the mirror burst all of the illusions I had about my maleness! Inside, in that private place we all have, I knew that I would never again be happy again unless I was able to become this young woman more than once in a while.


 

 

The girl, me, was looking back from the mirror, and like my sister, she is stunning. Her large blue eyes with their long lashes look deeply into me. She has wide, pouty lips highlighted by sensual reddish pink lipstick. Her soft brown hair falls a few inches above her shoulders, styled with bangs, gently brushed without a single hair out of place. White button earrings and a thin white necklace merely enhance the simple blue dress. The simplicity of the dress draws my eyes to my face. Without any fanfare at all I turned to face my mother, and when she looked up I heard her gasp. “Damn!” Mom stood up and had me turn around for her. “If I did not know it was you I never would have guessed that there was a boy under that dress!” “Thank you mother.” I sat down facing her, my knees firmly locked together and my hands in my lap. “I can see that you know how to do makeup and get dressed, but how are you in public?” “I’ve never been out of the house mother.” “Then it’s time that you experience things all women enjoyÉ like shopping, having your nails done and your hair styled.” “Like this!” “Of course dear! How else?” “ButÉbutÉ” I started to sound like a car that needed a tune up, but mother had made up her mind! “Michael, you and I both know that you want to go out and make people think that you are really a girl, don’t we? Lets stop pretending that you are so attached to your macho self and admit that you love being a girl.” Why did she always know? Are all mothers able to read their children’s mind like this? Without waiting for an answer she said, “Get a purse and put your wallet and some lipstick in it and I’ll get cleaned up a bit before we go.”


As I waited for her to get ready I knew that mother was right. I no longer had any reason to use excuses or delaying tactics. The time had come; I had to step outside wearing women’s clothes. I had to, and wanted to, act enough like a real girl to convince everyone that would see me that I really was a girl. I had to act in a way that everyone who saw me would believe I was a female. The very thought of being a convincing girl made me feel weak and vulnerable, yet fear was attacking every nerve in my body, and the longer I waited the more my fear grew. Mother finally showed up, but before we left the house she asked me what my girl name was. “I never picked one mother!” “Then why don’t we use the name of the actress you look so much like?” I agreed, and from that moment on she called me Diane.


The first thing that I became aware of was how the breezy air felt on my nylon covered legs. That same slight breeze also kept teasing its way up and under the hem of my dress. It was a new sensation, but I have to admit that I loved it. I found that wearing high heels made my hips sway, and I had to walk with a better posture just to help me to maintain my balance. It wasn’t long before I began to hold my arms up at my sides bent at the elbow instead of putting them in my pockets like I normally did. Mother saw the way I was reacting to the clothes, but instead of saying anything she just smiled at me warmly, with approval written on her face. I wondered about that, and finally I asked her about it as we drove to the mall.


 

 

“You would have done this sooner or later anyway Diane. If I help guide you then you’ll have an easier time of it and I get to have another daughter who is a lady to her core.” She glanced at me and saw the worry on my face. “Diane, you are a boy, that’s true. But only on the outside I think. Inside, where it counts the most I think you’re a girl. That wasn’t clear to me until I saw you for the first time this morning, then it was obvious, to both of us I think. Am I right?” It was my moment of truth, and without even thinking about it I nodded my head yes. “I don’t think that you feel you’re much different from any other girl at this moment Diane. I know that you want people to think you’re a girl, and you want them to treat you like a girl, so we’ll have to make them think you’re a girl, won’t we?” Again, I nodded my head yes, but this time I knew I had a smile on my face. “You’ll need panties and bras of your own Diane, so why don’t we start there.” It was a statement of course. We both knew I would do whatever she wanted.

I walked right beside my mother, keeping step with her, noticing how she held her hands and like her shadow, I began doing the same things. In the lingerie department we bought a dozen panties and three new bras before we moved to the junior department where I tried on several skirts and dresses which we bought along with two suits. In the shoe department I tried on shoes and found that Claire and I wore the same size, so I only bought a pair of beige flats. “Let’s put the packages in the car Diane, and then we can have some lunch before your appointment at the salon.” “My appointment?” “While you were in trying on that nice pink suit I asked the girl to call ahead and get you an appointment. You do want to look your best on Monday don’t you?” “But I thought I was going to do this on the weekends for three weeks before I went to work as a girl!” Mom was pushing me to see how far I would go, so in a fit of bravery, I one upped her to see what she would do. “Of course! Maybe I’ll get my hair colored and a nice perm at the same time.” “That’s probably best if you’re going to work as a woman. Maybe they can pierce your ears at the same time.” Mother was not about to be one upped by me, and had even raised the stakes a bit higher. Unfortunately I had nothing else to offer and my bravery made it firm. I could only smile in my acceptance. I had walked up to the cliff and stepped right off so to speak.


After lunch we walked to the salon in the mall and a woman named Betty took me to a chair. “This is Debbie, she’ll be your stylist.” I looked at her and smiled. After some discussion about what I wanted, Debbie concluded that I didn’t have a clue, and she simply told me that she would do a ‘modest’ amount of work on my hair before she started on me. I simply let her do her work with a minimum of chatter. When I had to move to the dryer another girl came over and started in on my nails, removing the ones I had put on that morning then made them slightly longer and used a light red polish on them. While she was doing my nails another girl pierced my ears and added small gold hoops! When Debbie was done and I looked in the mirror I was stunned at just how much a simple hairstyle can make a person change. My once soft brown hair was now blond, done in soft waves on top that terminated in sharp curls behind my head. My hair was just below my ears, brushed out to frame my face with bangs that were swept to one side. In my ears sat small gold hoops. I looked so different that it was hard not to keep looking in the mirror!


 

 

Mom and I drove home and at mom’s urging I moved into Claire’s bedroom. I put the clothes away and started to move things from my old room to the new one, moving some of Claire’s things, like underwear, to my old room. Later that night I went on line and found a site I had visited before. They sold things to help make men look like women, even if they were naked. I had visited this site many times in the past but had not yet bought anything. I saw that they had improved everything, so I used the on line ordering system to buy a few things I knew that I would need. I did not tell my mother. That night we watched television, mom in her flannels, me in a nightgown and robe set that was not much more than a diaphanous swirl of light blue


The next morning I got up, brushed my hair, did my makeup and dressed in a skirt and blouse before I went to the kitchen and started the coffee. Mom came in shortly, and as we had our breakfast, she asked me what I had in mind for the day. “I have a few things I want to do on the computer, but I would like a picture of me first.” “I’ll get the camera!” Mom snapped the picture as I stood in front of a blank wall, handing it to me when it popped out of the camera. I took the picture and in my room I scanned it into the computer so I could clean it up a little. Then I scanned in my college ID, drivers license, and work ID. With the software it was easy to cut my old picture and paste the new one in its place. Changing the name was harder because I had to match the font, which was different on all of the items. When I was done, I printed out one of each on my printer, in full color, and other than the picture and name, I had exact copies of each piece of my ID. My name on each was Diane Michelle Grant. My dad had used a laminating machine quite often, and it was still in his office, so I went in and laminated each one.


I was so elated at being able to dress as a woman that almost could not stand it. I fixed up a wallet that I had found in Claire’s room with all of my new ID, moved my pictures, credit cards, and money to the new wallet and put it in the purse. My image in the mirror kept my attention, which was narcissistic I suppose, but I loved the way I looked and did not want to give up being a girl any sooner than I had to. At three that afternoon the things I had ordered arrived. Their ad was correct! Next day delivery! Mom signed for them, and as soon as I saw her she gave them to me. “What is this?” “I’ll show you in a little while mother. Right now I have to examine them to make sure everything arrived undamaged.”


Of course nothing was damaged. It’s hard to damage latex just by shipping it. I eagerly opened the package, and right on top was the panty with the artificial vagina. I set it aside and pulled out the box containing the breastforms. Each of the breasts was made so real looking that it was scary! I eagerly stripped my blouse and bra off, read the instruction sheet carefully, and using the enclosed adhesive, attached them to my chest. As soon as I smoothed out the seams they seemed to become one with me as only the almost invisible seam remained. The vaginal panty was harder to put on, but again, following the instruction sheet, I managed to slip it on, removing all traces of my manhood. Naked, I looked in the mirror and saw a young girl from head to toe. In my reverie I failed to hear the door open; when my mother gasped I turned to see her ashen face.


 

 

Without a word she walked up to me and touched the breastforms, assuring herself they were fake I guess. She knew for a fact the vagina was a fake. “I see that you have become a girl after all! Do you have to take that off toÉ” “No mother, but I have to sit just like any other female.” “Well, since you’re so much a girl now why don’t we go out tonight?” Without waiting for an answer she told me to wear the same blue dress and walked out of the room. After shopping, and a trip to the salon I knew that I was not a clown at all. I was now able to present myself as a female and make people believe it, but mom had posed a challenge of a sort, so smiling I went into the bath and after washing the old makeup off, I shaved as close as possible.


I was not yet able to make myself over into the various ‘types’ girls, but I knew what I wanted to look like. I wanted silky soft skin, full, sexy lips framing a radiant smile, a gorgeous outfit, and perfect hair. I did not want to be a girl with a sweet childlike look, but instead I wanted to look pretty, like the proverbial girl next door grown up into a sexy woman. I went to the dresser and pulled out a corsolet and tossed it on the bed, then added black panties to the pile. I was going to wear black, not the same dress I wore earlier in the day. I found one I liked better. This one was also a sheath dress, but it had a plunging back with a low cut front and was a very hot mini dress. I had seen Claire wear it exactly once, for a dance she had gone to, and spectacular does not describe how she looked in it. I hoped I would look half as good!


Sitting at the vanity I did my makeup, and with the new cut, my hair seemed to fall in place with a minimum of fuss. I no longer needed the padded pantybrief and slipped the black panties on. The corsolet was a lot harder to get on than I imagined. It had eleven hooks up the front with a zipper over that, and laces up the back. I was unable to tighten the laces on my own so mom came in and did it for me. Once I was all cinched in, my ‘breasts’ sat in the cups, the nipples barely held in. I pulled on the pantyhose and reached for the dress.


The dress had a single strap that went around the back of my neck attached to the sweetheart neckline, fitted bodice and hip hugging skirt. I slipped it over my head and mom zipped it up for me. The hem of the dress was a good three inches above my knees while the bodice defined my now trim waist and my breasts were clearly displayed. Smiling I went to the jewelry box as mom left for her room. I found the black and gold chandelier earrings and attached them, then fastened the matching choker style necklace around my neck. On my left wrist I wore a thin gold bracelet, which was all the jewelry I wore that night. I did my lips in a deep red and spritzed myself with perfume. Looking in the mirror I knew without a doubt that this is what I wanted. I could not simply give her up now that I had been allowed to find her, and I made up my mind right then. Diane was going to stay no matter what.


 

 

officeboy-p7.jpgMom said nothing when she saw me, but I saw her smiling as she turned to get her purse, and I knew I had made a good impression on her. Dinner was at a new place by the river, and as we dined mom and I talked about the transformation that had come over me in just a few days. It was my turn to tell her the truth. “Mom, I’ve always felt this way, I just never had the chance or the nerve to tell you about it. When Valerie suggested it I was afraid to tell you. When I did, I was sure that you would be angry at me. But now I know that I have to dress this way, all of the time, even at work. I have to become Diane all of the time or I think I will bust!” Mom reached out and took my hand in hers, and told me she knew that the first time she saw me. “If that’s what you want, then I’ll support you of course, but you have a lot of catching up to do if you want to be a real lady. Starting now, I’ll teach you all you have to know to become a woman.”


I spent all day Sunday getting ready for my debut at work, which made mom just shake her head. “You don’t have to do anything special Diane, you look very nice right now!” But my concern manifested itself in an obsession to be better than just okay. I used the hair cream again then shaved every inch of my body that I could reach until my skin was as silky smooth as any woman. I washed and cleaned the vaginal panty and breastforms before I put them back on. This time, rather than rely on pressure to hold the panty in place, I used glue to secure the seams in the crack of my butt. The breastforms were pert with no sag, and made me feel very feminine once I had them secured to my chest. Somehow they felt natural, like I should have had them all along, and I could not, or did not, want to visualize myself without them. Mom had given me an aloe based skin lotion, which I rubbed in all over, making my skin softer to the touch and smelling of flowers. I slipped on some panties and a bra then some shorts and a tee top and began to select my wardrobe for the next day.


In my heart I knew that the only thing I was going to wear was the new pink suit mom and I had bought on my very first outing as a girl. It had a straight skirt that was above the knee a little, and a fitted jacket with no lapels. Both were lined, which meant that I didn’t need to wear a slip with it. For a blouse I selected a thin gray pullover blouse that had a single button at the neck, in the back. The blouse was mom’s but because of the vagaries of women’s sizes it fit me perfectly, and I wore a size 12 to her 10. Claire had a pair of gray shoes that I borrowed, size 8 by the way, and in my mothers jewelry box I found pearl earrings and necklace set. I already had a gold watch and two rings. Once I had everything ready, I relaxed and made a late lunch.


With the vaginal panty it looked as if I had rounded hips and a natural taper in the front, just like all women did. Mom even commented on it once. “You might want to call Valerie and tell her how you’ll be dressed in the morning Diane. I’m sure she won’t mind, and at least she’ll be prepared when she sees just how pretty you are.” That made sense, and right after lunch I called Val and told her that I would be dressed as a woman when I showed up for work. Her only comment was that she would look forward to it!


 

 

I spent the night in curlers, getting up early to do my hair and makeup. As I slipped the panties on and saw the cleft in the front a feeling of calmness came over me and I relaxed and got dressed. A soft, lace trimmed demicup bra in white, nude pantyhose, and a white waist nipper. I pulled the skirt on, then the blouse, stepped into the shoes and pushed the earrings into the small holes in my ears. I pulled the jacket on and used a soft reddish pink lipstick to outline my mouth, added perfume, the necklace, watch, rings, and bracelet. Looking in the mirror I could see no trace of the man I was just a few days ago. Once unleashed, Diane had taken over and consumed me, and now, I was Diane Michelle Grant, inside and out. My purse was filled with my wallet, lipstick, tissue, and car keys. Drawing in a breath I left the house for the biggest event in my life. Whatever happened today, a spectacular success or a colossal flop, everyone would know that I wanted to dress and work as a woman, and there would be no going back. Strangely, the fear that had consumed me before did not cross my mind as I drove into the parking lot.


I locked the car and walked to the door, showed Walter, the guard my phony ID and walked in. It was no longer a maybe, and I walked into the office and straight to my desk, and the first thing I saw was the nameplate. ‘Diane M. Grant’ etched in white on a blue background sitting on my desk! I stashed my purse in my desk and went to get a coffee, returning just as Valerie walked in. She took one look at me and broke out in a huge smile. “I was right! You look spectacular Diane!” She went to get a coffee, returning to my desk quickly. “I’ll introduce you around today Diane. The way you look, nobody will believe it if we told them who you really are, so I’ll let them assume you are a new hire and we can go from there okay?” It really was the best way, so I agreed.


As I was introduced around the office I saw a lot of different looks that I had never seen before. From the men it was mostly an evaluating look and each time I felt as if I had been mentally stripped. From the women it ran from indifference, (from the pretty ones), to envy (from the older ladies). Valerie motioned me to join her in her office, and as soon as I was seated she asked me for my ID. I gave her the one I had made up, and after a quick look made arrangements for me to have a new one made. “You’ll have the same duties Diane and the same rate of pay of course.” Then she explained the looks I got from everyone. “All men are on the make all of the time Diane, and to them, you’re fresh meat so to speak. Ignore them and they’ll relax after a few days. The older women are jealous of the way you look while some of the younger girls see you as competition. You can ignore them as well, or play it as you see it.” Then she had me go and have my picture taken for my ID card, assigned a new computer sign on, and I went back to work, doing the same exact job as before.


During the morning I settled in and finally relaxed as I discovered that everyone accepted me for what I appeared to be; a woman, about 20 years old or so. At lunch Kelly and Beth asked me to join them, and we sat together at one table. I got an earful as they discussed the single men that worked in the office, in graphic terms, and some of the older women who they thought were ready for the retirement farm. It was a very educational lunch!


 

 

officeboy-p9.jpgFor my part I paid close attention to what the other girls wore and so on. My new ID card arrived at two, just as I had my first phone call. In person mom and Valerie both told me that I looked like the actress I had taken my name from, but I sounded like Kathleen Turner. On the phone I had no idea how I would sound, so I was relieved when the male caller addressed me as a woman. That night I collapsed on the couch from the stress mom said. After that it got easier each day, and at the end of a month it was as if I was a natural born female. I hated shaving close every day because my face became sore and very tender. That’s when I saw an ad in the paper, showed mom, and she agreed. I made an appointment by phone, and that Saturday morning at eight I was at the clinic.


I was shown in to see the doctor, and was surprised to see it was a woman. I had to tell her my true status of course, which was hard because by now I did not look like a male in any way. She sat there quietly while I told her all about myself and the dilemma I found myself in. When I was done I fully expected her to toss me out, but all she did was ask me some medical questions, my medical history and so on. Then she asked me if I would like to have my own breasts! “Of course, but I’m not taking any hormones, so that seems out of the question right now.” “Maybe not Diane.” When she told me how she could do it, that day, I was all smiles and agreed to it right then.


I was out for the entire procedure, but essentially, she used a laser to remove my entire beard, then Liposuction to draw fat from my waist and used it to make breasts, the same size as my fake ones. When I awoke I was sore, but not bad, and I had a few small stitches. But I also had a 23 inch waist and two perfectly formed, completely natural breasts. I was in heaven as I got dressed and then drove home. Mom knew I was going to have my beard removed, and when she saw my slightly swollen face she started clucking like a mother hen and immediately wanted me in bed. I was just too sore to argue with her and let her help me get undressed. When I removed my bra and she saw me, a common occurrence in our house, she saw my brand new boobs and narrow waist for the first time. “Those are real!” “Yes, they are! Aren’t they nice?” Then I explained how the doctor did it. Mom helped me get a nightgown on and I went to bed, staying there until late the next morning. In the shower I felt my new breasts, washed the stitches in my navel carefully and wearing just panties I slipped on a top and a skirt, which fit a lot better now that I had a smaller waist.


 

 

During the next week I became used to having sensation in my breasts, and loved every minute of it. On Friday Valerie invited Kelly and I to her home for a barbecue on Saturday afternoon. She failed to mention that both of her sons would be there. I picked out a tan floral summer dress, and wore tan sandals with a thin, short sleeved jacket. My hair, now trimmed, flowed around my face like a halo. I had a small brown leather purse to complete the outfit. I examined myself in the mirror. My hair was longer now, cut and styled in a more business like way, but still casual. My shoulders, accented by the short sleeves of the jacket, were trimmed with brown piping. The top of the dress did not have a deep neckline, but it was low enough to allow a hint of my cleavage, and that was accented by delicate gold locket suspended from my neck. I wore a minimum of makeup, just a hint of eyeshadow, a soft red lipstick and my best perfume.


As soon as I arrived at Valerie’s her youngest son, Mike greeted me and showed me to the patio. Unlike Valerie, who was my size, Mike was huge! He stood at least 6’3″ tall! I had to look up to see his face! Kelly was already there, sitting with Douglas, Valerie’s other son. He was also quite tall. Both of her sons had dark hair, Mike with green eyes and Douglas with blue. Her husband was not as tall as his sons, but he had the same build. He was wide, with a barrel chest, and dark hair. It was immediately obvious that Valerie had arranged this little party so Kelly and I could meet her sons! While I had been living and working as a woman for almost four months now, I had never had a date nor had I ever looked at a man like a woman would. I had known that sooner or later some man would hit on me, and now, it seemed, was the time. Mike almost, but not quite, doted on me, and I often saw his gaze drift to the top of my dress; I knew he was not admiring the material my dress was made of!


When I looked up at him I could see that atypical look of male superiority on his face. I felt so feminine right then, and it was a wonderful new feeling. I now knew what my mother had told me about men was true. They had a magnetic appeal to women that simply could not be denied. I knew that there could be a lot of joy to be had in being so attractive to a man, and the thought of being Mike’s new girl friend ran through my mind. I was flattered that he thought I was pretty enough to make him come to me, yet in the back of my mind I wondered why I felt this way. Until I had started to dress as a woman I had never had a sexual thought about another male in my entire life! Now I was thinking about Mike in ways I had never dreamed of before. We sat at the table side by side eating, and even though I held up my end of the discussion, I was thinking about the way Mike had looked at me.


Thinking of Mike, as my boy friend did not turn me off at all, instead it had just the opposite effect. I was a girl and I had a real live male catering to me, like a boy friend would. Not only that, but I was flirting with him the way girls do to their guys. I began to feel hot inside as my thoughts drifted to more erotic places. That scared me momentarily, because up to that moment I had never had an erotic thought about a maleÉ ever! As our food was eaten and just the drinks were left, I felt his hand on my leg half way up on my thigh! Right then Valerie started to clear the table and Kelly and I jumped up to help her. It saved me from making a decision whether to let his hand stay there or ask him to remove it.


 

 

officeboy-p11.jpg“My sons seem to be taken with you girls.” That was obvious, but it was Kelly who stated it. “Like you didn’t arrange this Valerie! I’m certainly not complaining mind you, Douglas is very nice.” They both looked at me, and all I could do was smile. Nobody said anything else, and we filled several pitchers and rejoined the men. Mike asked me to take a walk with him, and took my hand in his as we walked along the waters edge. We rounded the point and as soon as we were out of sight he spun me around, held me close, and kissed me. He was gentle but urgent as his tongue probed against my mouth and I opened so his tongue could enter me. I was unable to pull away, not because he was so big, but because I didn’t want to. He asked me out for the next night, and I agreed. By the time I got home I had become like a young girl in my anticipation of this date. I know mom saw it, and when I told her about it all she did was remind me what good girls did, and did not do. Big help she was!


I had chosen to wear a skirt that flared slightly at the hips with square cut pleats in a dark green. A simple white blouse, and black two inch heels. I added jewelry and perfume. My makeup was for evening, darker eyeshadow and a dark red lipstick this time. I was nervous as I waited for him to arrive, but when he did I calmed right down. He took me to dinner, and later, he drove to a secluded spot by the lake. As soon as he kissed me all of my mothers admonitions went out the window, especially when his hand found my breast. Every nerve ending was on edge as he manipulated me like a musical instrument, making my body play his tune. When he took my hand and placed it on his member I felt myself shudder, not in revulsion, but in lust. I wanted this man to take me, love me, make me love him back, and he did. Unbidden my hand began to stroke him and I felt the buttons of my blouse come undone and his hand found my naked breast while I unzipped his pants.


He popped out all engorged and hard, throbbing in lust as my hand again found him. The skin was like velvet, yet hard like iron beneath my hand. I was stroking him when all at once he gushed, filling my hand with goo. “Sorry about that Diane.” He gave me a hanky and I cleaned up. “This isn’t the place for two people our age Diane, why don’t we go back to my apartment?” Common sense kicked in and I asked him to take me home, and like a gentleman he did.


 

 

Mike called me every day at work and each night at home. Valerie told me he was so in love he could hardly stand it. Kelly asked me if I had slept with him yet, and when I did not give her an answer she assumed that I had. On Friday night Mike and I had a date, and I knew in my heart that I was going to have sex with him, so I packed a small bag to take along. Mom could hardly miss it, but this time all she told me was to be careful. “That vaginal panty is very good Diane but this can lead to disaster if your not very careful.” “I’ll be careful mom, but this is the last hurtle isn’t it? I have to do this even if he finds out.” Later it turned out I was right, because right after dinner he drove us to his place. As soon as he had closed the door he was all over me, and I once again became like warm bread in his hands as he massaged my nipples with his fingers. I felt the zipper of the dress going down, and when it did I stepped out of it and tossed it aside. Mike watched as I removed my bra and tossed it aside as well. I reached out and began to unbutton his shirt, then his pants. He stepped out of his pants and just stood there. I ripped his briefs down in a single motion leaving him naked in front of me.


I sat on his couch and removed my pantyhose and shoes, leaving my panties on as he grabbed my hand and took me to his bed. He found every single spot that turned me on and some I didn’t know I had. I wanted him to be mine and pushed him on his back. His erection stood tall and proud as I went to my knees, bent over, and kissed his member. It was not unpleasant, and when my mouth opened I took all I could in a single motion. His hands held my head as I bobbed up and down, until I felt him starting to tense up. I straddled him, and helped him find the opening in the vaginal panty. He slid in and I began to rock back and forth, watching his face the whole time. His eyes closed and he was moving his head, but his hands remained firmly on my breasts as I pumped him. I was now in charge of this man and I loved it! Finally he released and filled my panty. Spent, he fell back as I went to the bath to clean up. He was still naked in the bed when I returned, also naked as his hand reached out and pulled me to him. I lay next to him, my hand on his manhood while he kissed my breasts, renewing my excitement.


He grew hard once again and once again my mouth found him. This time I wanted to taste him, and did not move as he swelled and released his seed into me. I spent the night with his arm around me firmly cupping a breast with his hand. I woke before he did, dressed in the skirt and blouse I had brought along, brushed my hair into a ponytail, and started the coffee. It was a very domestic scene for sure as he woke up and saw me. Naked, he went in and took a shower, returning in shorts and a tee.


I put both of my hands on the cheeks of his butt, and tried to keep him from moving to far away. I wasn’t surprised to find that he was rock hard once again. I genuinely hoped it would not be too long before he wanted to take me out on a date. Then Mike kissed me again. “Eat your breakfast Michael, you’ll need your strength for later.” I know it was coquettish of me to tease him, but I simply could not resist. After breakfast he helped me wash the dishes, and then his hands found my breasts again.


 

 

officeboy-p13.jpgHe had the stamina of a bull and it was another two hours before he took me home. Valerie was there talking to mother when he dropped me off. “By the look on your face I would say that Mike is a very happy man this morning!” “A polite woman never talks about her conquests Valerie, even if it is the bosses son!” “He’s going to ask you to marry him Diane, probably this week.” “Diane, I think it’s time that you told him about yourself, and made arrangements to make yourself into a woman, don’t you?” Mom was right, Mike deserved more than a lie. “Okay mom, but maybe you and Valerie could be here when I tell him.” They looked at each other and nodded their heads yes. “We’ll be by tomorrow Diane, around six.” The next day was hell as I wondered how I would tell Mike about myself, and Valerie was no help either. All she said was that Mike and I would have to find a way to overcome this minor obstacle.


After dinner mom and I did the dishes and I sat, waiting for Mike and Valerie to arrive. Promptly at six the doorbell rang and I admitted them into the house. “Mom says that you have something serious to tell me Diane, what is it? Valerie and mother had mysteriously disappeared, leaving me alone with Mike. Direct is usually the best approach, so I drew in a breath and told him. “Mike, I’m not a female, but I love you and want to be your girl, and hopefully, your wife.” “What do you mean your not a girl? You and I slept together, and I think I would know a girl when I saw one, especially when she is naked!” “I’m sure that’s true Mike, but none the less, I am not a female. I will be shortly, but not now, right this minute. I wear a special kind of panty that lets me have the look and feel of a woman Mike. These are my boobs of course, but the rest is all latex.” By the look on his face I was sure he was going to hurt me and started to back up. “I’m angry that you weren’t honest right up front Diane! You tricked me, and that is wrong!” “Yes I tricked you Michael! What would you have said if I told you, “hey fool, I’m a man just like you!” You would have dropped me like a hot rock and you know it! But it wasn’t deceit on my part so much as my desire to be your woman, or your lusting after me, panting every time you looked at me. No Michael, this goes both ways. I love you, I really do, and I will make you a fine wife if you let me. I just need time toÉ become that woman you want me to be!” By then I had tears running down my cheeks and ran out of the room straight into my mother’s arms.


“He hates me mother!” My tears ran down my cheeks because I was ashamed of what I had done. I was not a woman, I was a pile of latex trying to be what I was not. I tried to tear myself away but I felt Mike’s hand on my arm and in a rush of emotion I fell into his arms. “Oh Michael, what are we going to do?” he said nothing as he picked me up like I was a feather, and carried me to my room, slamming the door behind us. “We,” he said very forcefully, “are going to make love again and then we are going to talk about this problem we have.” Then he unbuttoned my blouse and began to undress me. I stood very still as he slowly ran his hands all over me, making me tremble in delight and lust. Then he stood there as I undressed him, ran my hands all over him until I reached his manhood when I began to stroke him. As he purred I slipped into bed and lay there, naked and smiling. He took me quickly but forcefully, and then later, slower and with a methodically slow tempo which drove me crazy. Unable to quiet his lust, I rolled over, got on my knees, put my head down and allowed him to take me. We were both panting when he completed and lay there for a moment. Then I got a warm washrag and cleaned him up so that I could use my talented tongue once again. He stayed in my room that night and we talked about the future. I told him how it all began and why, and in the end he asked me to marry him. “You have a year Diane, after that we get married!” The he went back to being forceful again, but I said yes and that night I slept like a baby.


Less than a year later I was a woman, and on our wedding night he found out just how much of a woman he had married.

Leave a Reply

Your email address will not be published. Required fields are marked *