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Boobs Janet L. Stickney [email protected] I have always liked the way the girls looked wearing those skimpy, tight orange shorts with their wonderful cleavage enhanced by a tight tee. I wanted to be able to wear one of those uniforms but, as a guy that was probably out. Still, I had bought a uniform that was very close to the one described and with each effort to wear it and look even remotely like one of those girls it seemed that I only got slightly better at it. Not good, just better, but I still looked like a boy with bad boobs and no butt and terrible makeup yet I was tantalized by the prospect that some day, maybe. "Leslie, you have a letter! From the HR department where you work!" I was very concerned as I opened it . "Upon receipt of this letter you are being notified that next year, on October 23, we will be hosting an event for the city wide party. The costume we have selected for you will be that of an OWL girl. You may use any available assistance you need. Since you have stated on your application that you are a singer, we would like you to try out as an OWLET singer. Please contact Janet in our office for further information." An OWLET? Me? My most fervent desire and my greatest failure at the same time. I simply could not understand how they selected me! I mean, we have many very attractive young ladies that could do it easily, and they might even like it, and they are certainly better equipped than I am! On Monday morning I called Janet and was invited to see her in her office. "How nice to see you Leslie! Your application says that your name is Leslie A. I had at first assumed you were a girl! I'm so sorry, but I guess you're wondering why I asked you here, right?" "Yes Ma'am, but... I mean, I'm a... we have girls that can do this, so.. I'm very confused Ma'am." "Yes, well, when your name came up, when we tried to decide what we'll do, the people on the committee, well, they saw your name and already think you are a girl, which I understand, and I hear that you sing like an angel. You put on your application that you sang in a quartette in school. I checked, and everyone said that you have a wonderful voice, which is when I found out that you're a boy! If you do not want to do this that will be fine, but all of the top managers look very favorably on the employees that participate in these events. I know that this is very presumptuous Leslie, but I can fix everything if you want you to do this. You can say no of course, but you should think about it first. Talk to your Mother before you decide. I am positive that you will look simply gorgeous, and since we have well over a year for everyone to get ready, I was thinking that with some proper help you can not only become a very attractive young lady, but I can arrange it so you can work as a girl. I can take care of the paperwork, You think about it. Let me know by tomorrow." "But why?!" "If we let it be known that one of our girl singers is really a boy and nobody can tell, and we don't say who it it, it will let everyone know that we value perfection in everything we do, including this!" "I suppose, it's a bit convoluted, but if I do this I'll need a lot of stuff, especially if you want me to dress like an OWLET! Like great boobs! And really round buns!" "Yes of course. If you tell me you'll do it, then, if you need me to, I will help you find out how to do the rest, okay?" "Okay, I guess I'll do it, but only if I look perfect!" "Deal!" "Deal." Back in my cubicle I went online to see about a boy becoming a girl and was shocked at what I found. There were a lot of boys like me turned into absolutely gorgeous girls complete with perfect boobs, hips and buns! All of them had always wanted to be girls while I only had a dream. I always wanted to be a girl, or to at least try it, but I was unsure if I could actually do it. I noted the websites and shut down to think about what Janet wanted me to do, and wondered if I could do it. While I had dreamed of being an OWLET, every one of those girls was beyond gorgeous while I am a boy with a dream. Out of curiosity I called the specialty shop I had found online. When I called, the owner Madelyn said that they wanted to know if it was just a costume, was I being forced, was it my idea, a family members idea, or did I really want to be a girl, and if it was all my idea, why did I want to be a girl. The reason the lady told me, was that after what they do, I would seem to be a natural born girl in every possible way except that I could not get pregnant. She was very insistent that I be truthful, and when I told her that I had always wanted to be a girl but did not know how to do it, or why I wanted to do it, then my age. I also told her about becoming an OWLET. She told me that I should bring my mom. She said that it would be much better for everyone. I did not know why and the lady did not say why. Since the lady told she wanted to meet me, I told mom she wanted to see her and I in person. Then I talked to Janet. I told Janet what I found, and asked if she would pay for whatever the lady said I needed, and if I let her do it, could I still work at my job. "Of course you can work here! Just let me know when you will start. Take a few days and let me know in advance when you are coming in." The minute I told mom she broke out into a huge smile. "Well it's about time Leslie! I mean you have been struggling with this for a very long time and you have almost worn out that skirt and blouse you have. Now you can find out what it's like to be a girl. Not be an equal at work, and learn about the way the guys treat women! You'll finally find out all about being a girl. What its really like. Tell me about this shop." I showed mom their website, then she and I went there the next day, and with mom insisting, I took my one skirt and only blouse in a small bag. It was a very interesting first hour or so as she questioned my resolve about doing this because, she said, it is a very big life altering change. For Madelyn it was not just about the money it was about lifestyle and self. She said that because of the efforts she makes towards her clients she has never ever had even one complaint, and so far, not one of her 'girls' have retreated to being a male again.! After talking to mom and learning that I had been playing dress up my entire life, she decided that I was worthy of her efforts and began. Eight hours later I had the body of a girl my age. Boobs, hips, buns, and even a twatsie! I wasn't expecting that. I wore the skirt and blouse home. I felt elated and scared at the same time. The unknown lay ahead of me, a wide avenue filled with fear and joy, learning and pain. Everything on my body was moving which felt very different, and I wondered if mom felt the same way. I know what girls wear, but not what and when. They had a lifetime to figure that out while I have a few days to begin my new adventure. That night I struggled with my new parts. My boobs seemed to get in the way when I walked down stairs because I could not look down, and in the bath, well that was an experience. In bed that night my fingers did the walking as I explored my new twatsie. It felt very real to me! The next morning mom and I left for her salon. I thought, just get a nice dress, some heels and great makeup and I would be set. Silly me. Mom popped that bubble when she took me to her salon the next day, which was full service, and threw me to the lions so to speak. "Hi! This is my daughter Leslie Ann, and she needs everything, top to bottom." "Seven hours I would think Madam, but Leslie will be a doll when we're done!" "She's all yours!" With absolutely only the barest idea of what they do, I let them do what they wanted. Once I was naked except for that that short gown, I was introduced to a sauna where they baked me until I was a nice red all over, then without warning, they doused me with cold water. "It closes the pores" the girl told me. It was true. I was positive that I could hear the pores on my skin slapping shut. Then came the waxing. Two full hours of rip and tear as my entire body was denuded and left with no trace of hair. The green facial felt good until it hardened and they ripped it off, which is when the lasers fired up and I could smell the hair on my face burning away. When that was done I got another soothing facial that lasted quite a long time as they added extensions and began styling my hair. I sat there as a sudden wave of femininity washed over me and I felt the excitement growing inside me. New nails, makeup, ears pierced twice, and a great hair style helped them create the beautiful young lady that I had always held inside. I was overwhelmed at the way I looked, which was nothing like the boy in a skirt that I had started out as. When mom picked me up she looked shocked, but I was smiling widely. Once we got home she had me take a few of the bags she had inside. "I bought a few things that you will definitely need. Lets see how they fit." Of course there was a bra and some panties which felt very nice but seemed skimpy compared to my briefs, then the pantyhose which felt very nice when I pulled them on, and a well fitting sheath dress that was all black with a red jacket. The shoes were low heels. Mom had me look in the tall mirror. The girl I saw looked faintly like me, but then, not at all. Bright red lips with great eye makeup and rosy cheeks, and a nice figure. I was surprised at the outcome of the salon and the clothes, but I was both scared and thrilled at the same time. While I had always thought about what it would be like to be a girl, and did buy that one skirt and blouse, I never once expected that I would have the chance to experience the feminine side of life. With the addition of the red jacket and a silver necklace, I looked every bit young lady. I spent the next day trying on all the clothes mom had bought, plus she and I added a few more. Then I went to work. I was wearing the black dress and red jacket with the shiny black heels. When I walked into Janets office she did not recognize me right away, but then... "Ohmygod! You look just delicious!" "My name is Leslie Ann, but I would prefer that you call me Ann." "I'll adjust your records." I settled into my usual work and it was not long before I felt very comfortable. I was immersed in my work when a few moments later I felt a presence, turned and saw it was my boss. "Hi. My name is Howard. I run this department. You are Ann?" "I am! Nice to meet you!" "I usually take our new employees out to dinner, a sort of meet and greet if you like. Maybe we could do dinner tomorrow night?" "I think not, but thank you anyway. My boyfriend would not like that." "A boyfriend. Well, nice to have you with us." Slimy bastard. I already knew that he hit on most of the girls working there even though he is married with two kids. At lunch I was accepted by the other girls working there and when I mention what happened they all agreed he is a bum. "I told him my boyfriend wouldn't like him hitting on me." "But you don't have a boyfriend, do you?" "Thats true, but he doesn't know that!" "Well," Megan said, "my fiance has a second cousin or something like that, and I hear he is simply a hunk and a half, and his girlfriend decided to leave him and he needs someone to take to all of the wedding parties we're having. Maybe he could fill in as your boyfriend! Its a few months away so you have plenty of time." "Well, I guess, but..." "Great! I'll set up a dinner date for Friday! You'll love him." With zero experience being around a guy as a young lady I was a bit scared but I also knew that with an entire year or more as a girl, a girl my age not having a boyfriend would look very strange, so I silently agreed. I nodded my head yes and Megan smiled. That night I told mom about it and she broke out in a huge smile! I had assumed that she would be totally against it! "This is wonderful honey! You finally have a chance to feel like a real woman! What is his name? How tall is he? What does he do for a living?...." "I cannot answer any of your questions mother! I'll find out on Friday." "Wear that cute red dress you have. It'll show some of that sexy leg you have and it fits you perfectly." My red dress is a sheath that is just above my knees on me, snug on my hips, displays my waist and enhances my breasts with a square cut neckline that also exposes some cleavage. I bought it without trying it on, but it fits me nicely, and I will admit that I like the way it looks. For my very first date such as it was, I went back to the salon and once again allowed them to turn me into a doll. By the time he came to pick me up I was ready, and mom said that I looked better than delicious, but she is biased. His name is Greg. He's about 6'2" tall with a very masculine if a bit husky build. He said that he is a plumber. Megan was right. He is very handsome, and for the first time in my life, I felt an attraction to another guy. But of course, by then I had been Leslie Ann for about a month. Mom said it was a normal feeling for a young girl like me. Greg picked me up, and when he saw me for the first time he started grinning, which was a very good sign. He took my hand and led me to the car. "You look wonderful Ann." "So do you! Megan said that you are a plumber?" "Yeah. Push in, turn to the right, everything runs downhill and they pay me on Friday." "I know it's not that easy! It's hard work." "It can be. Megs says that you're an Accountant?" "Not licensed yet, but yes. I work with a lady that does have a license and I am taking classes to get my own license." "You go on blind dates often?" "You're the first one, and only because Megan said that you weren't and axe murderer." "I might bite though...." "No biting, but maybe a small nibble would be okay." When we walked in Megan saw us and waved, took one look at my dress and smiled. Taking me by the hand... "Damn girl! I said to dress nice! You look like a sweet treat for some horny guy!" "You're the one that set me up, you said he was a hunk, which he is, and for me to dress nice. This isn't nice?" "You look like a treat for a starving man honey and you know it." "Mom said that if Greg doesn't like it he's dead." "He is definitely not dead Annie. I just hope you wore your chastity panties! The way he is looking at you, well, just be careful! But damn you look great!" The party was a great success and Greg was very attentive all evening, but in front of my house he took me into his arms and kissed me. With his tongue halfway down my throat I knew that he was turned on and wanted more, but that option was out, for now. I was panting hard as I went in, knowing in my heart that any thought of returning to being a boy was totally gone. The moment he kissed me and I let him do it, my destiny was fixed. The next morning at breakfast I told mom that I was going to get my own apartment, and while she did not say anything I knew that she was glad. I found a place the next day and began moving. Mom gave me some pots and pans plus a set of dishes. I bought a toaster and a coffee pot and once the bed and tv was set up I was ready to start my new life. Since I knew that my future was now fixed, that same week I also started taking the hormones to help me become a real woman I was destined to become. The four singers that had been chosen were called into a meeting. "We have been served with a restraining order that prohibits us from using any form of their outfits, name or brand in any way. So, we are open for any suggestions you may have." "I never liked those booty shorts! I don't like displaying my girl that way! How about sequined dresses? Maybe thigh high? We can get matching dresses and wigs. It'll be hot!" We all agreed that sequined dresses would be our uniforms and Carol said that she would find them. I was back in my office when Megan stopped by. "Greg was arrested this morning." "For what!?" "My mom told me that the cops have surrounded his house and are saying that he is the largest drug dealer in the state! She told me they found $380K in cash and 40 guns in the house plus three kilos of coke, two K's of heroin and 60 pounds of meth! She said that cops are saying that is enough meth to kill every person in the state! I don't know that for sure, but that sounds like a lot of drugs!" Later that day I got a visit from a detective and a patrolman. "You know Gregory. How well do you know him?" "I met him about a week ago, we had dinner and that's it." "Your number is in his phone, so we are concerned." "Wait a sec." I called Megan who came right in. "Tell them how I met Greg." "I set her up on a blind date! My boyfriend and I were with them, why? Annie didn't do anything wrong!" "We don't think she did, but we have to chase all possible leads, and the two of them being together is... interesting, which is why we are checking her out, but it seems that you're clean." They left Megan and I standing there wondering about Greg and the revelations we heard about him. Megan was shocked because he is connected to her fiance if only by a remote family connection. Then we saw on the news that night all the police around his house, the hazmat crews, the ATF and cops all over the place. Apparently he was a very big deal. Then it was announced that 33 of the 40 guns they found had been stolen. Probably traded for drugs. On TV he looked a mess, head down in handcuffs, messy clothes and under very close watch by the cops. Three days later the patrolman that first came to my office stopped by. "Hello again. My name is Daniel." "Can I help you?" "Yes. I'm very hungry, and need a dinner companion, and you were my first choice." "Me? Why me?" "Well, you are very cute, I already know that you're single like me, so why not?" "I agree" I said with a smile, "I am single and I like your directness!" "Six then? I'll pick you up." I gave him my address and he left smiling. I was smiling too. "Annie has an admirer and he's cute too!" "Stop it Megs! It's just dinner." "Maybe, but he has the look." Dinner was very nice as we talked about our families and ourselves. He is the second oldest boy in a family of four while I am an only child. I am two months older than he is. Dan is funny and very quick, plus he was holding my hand as often as he could. Without thinking about it I was enthralled with him, and knew in my heart that I would like to be with him some more, and since I was taking hormones to become a real girl, I was hoping I would blossom soon. I went out with Daniel several times before he managed to entice me to go much further than I thought I would ever go. After we spent several hours exploring each other with some spirited groping, I knew that he was for me. Then, the very next day they changed his shift. Seeing him was going to be hard, but might give me time to develop my own breasts, hips and so on. He and I talked every day and he continued making me feel very womanly. Then my boobs popped out. Mom told me that she went from tiny, like me, to a full B cup within a short time, and there is the possibility that I would too. She was right. I did blossom to a full B cup with my own rounded hips and smooth hairless skin, and it did not take long. What I wanted by then was for Daniel to find them acceptable. Our singing group sounded wonderful as we mostly did songs from the 50's and early 60's. Each of us took the lead on various songs and as we practiced we began to feel when it was perfect. All of us loved the Motown sound so we tended to do a lot of their songs, but also many others from the era. We each had four sequined dresses, red, blue, white, and black, we all wore the same wigs and heels. Janet said we had an impressive and sexy 'look'. For myself, I decided to wear pushup bras and tiny panties when we were singing. It was my challenge to myself to be more sexy. As each day went by I became more and more feminine in every movement, the way I moved and talked, and how I thought about people, especially Daniel. I have his picture on my computer and phone. Even though we talk almost every day on the phone I cannot wait to have him hold me again because I have a surprise for him. Megan and I were having lunch near work when Daniel and another officer appeared in front of us! "Daniel! What are you doing here?" "We heard there were two female desperadoes hanging around so we thought that we would apprehend them. Make our superiors happy." "Yes", the other officer said, "but the most desperate one of all needs to be searched for dangerous weapons. Stand up Ann. Daniel, please do the honors." He took me into his arms and kissed me, hard and with passion, all while fondling my backside. "I'm going to take this one for further questioning" Daniel said as he took me by the hand. "You do know that you're the girl for me, right?" "I know that!" "My mom is having a nice dinner on Sunday and she asked me to ask you to come." "I guess, what time?" He told me, then left. I began to wonder what to wear to meet his mom, but I had no idea so I called my mom. Turns out that mom and I had to go shopping to find the perfect dress. It is a shirtwaist style, sleeveless, and hugged my figure perfectly, allowing just a hint of my girls. Mom said that I once again looked delicious. Mom also told me that his mom obviously going to check me out. To make sure that I am good enough for her little boy. All six foot of him. On the day of the dinner my salon once again did their magic and I was beautiful again. Daniel was wearing a suit when he picked me up, driving to a country club on the outskirts of the city. I had assumed the dinner would be at his mothers home. "My mother has been a member here for a long time, and is a bit of a snob I'm afraid. You should have heard her when I joined the force. She was adamant that I go into the family business, but I'm not cut out for sitting at a desk counting money and managing stocks. So be careful what you tell her." His mother was dressed to the nines in a black sheath dress that fit her perfectly, her hair well done and her makeup tasteful. She was smiling when we met. "Hello dear, you're Ann?" "Yes ma'am." "I understand that you are an accountant?" "I'll get my license next year Ma'am. I am currently studying for the exams." "That's nice dear. Have you thought about having children?" "No. Because of an accident of birth I cannot have children." "But Daniel wants a family." "Good for him. I do too, but I'll have them another way. Adoption is the most probable way to have a family." "That's true, but they really aren't family are they? I mean, they aren't blood." "I'm adopted. At one day old. And I am just as much a member of my family as anyone else. My mothers name was added to my birth certificate virtually at my birth, so your assumption is just crap and you know it. You have a dog? Or a cat? One that you adopted? And is now a valuable member of your family, right?" "I see. We have already picked out a woman for Daniel... she is a real woman! She can have children." "So... being able to have babies is your criteria for being a woman? Can you have babies? Or Daniels Grandmother? You cannot have a baby, so does that mean that you're not a woman? That's a ridiculous argument and you know it. Why don't you have a nice day." Daniel must have seen the angry look on my face and rushed over. He took me by the hand as we walked outside. "I doubt if we gave a future Daniel. Your mother is very pushy and very provocative, asking me about our love life. I had to tell her to mind her own business, but politely. She told me that she had already picked out a woman for you. I am not going to play games with her. Please take me home Daniel." He was furious at his mother but took me home. He promised he would take care of it. I doubt that. And if his mother finds out the real reason I cannot have children it will hit the fan big time. That accident of birth was the fact that I was born a boy. By the time I was back home I was beyond furious and Dan knew it. I finally exploded. "Your mother essentially told me that I wasn't good enough for you! She said she had already picked out a woman for you! This is not Pakistan Danny! She also said that adopted kids are not really family. Well I'm adopted and she can kiss my ass if she thinks I'm going to take crap like that! You better go back to your mommy now." He was more than angry at his mother when he dropped me off, promising to give her hell. I can imagine that he will, and I can also imagine that it won't make a lick of difference. She is from that generation and from a country where the parents do the match making, but Dan was born here, went to school here, and grew up with our value system. Therein lies the struggle. I called Megan and told her what happened and we talked a while. Then my mom called and I unloaded on her and got the same response I got from Megan. None of us thought that women like his mom existed. Two days later a girl I did not know came to my office. "Hello. Are you Ann?" "Yes, who are you?" "My name is Jennifer. I'm Danny's sister. I'm here to tell you a little story. I am doing my internship as a neurosurgeon. I graduated from one of the best medical schools in the country and now I'm the leading candidate for a job at the prestigious neurology institute, but my mother signed a contract with the cousin of a friend of theirs to marry me off to their son. I was seven when they did that I think. I met him exactly once. Short, skinny, full beard, beady eyes, slightly dirty with a skull cap. There wasn't any way, none, zero chance that I would marry that guy. I checked him out and he's on the watch list from Interpol! Some kind of junior terrorist I guess. He had some idea that I would move to that shit hole third world country of his and live in his mud hut and cook his beans. My mother was a bit shocked at how he looked and acted of course, especially when he started to boss her around. He only stopped doing that because Danny and my Dad stepped in and had a word with him. I don't think he liked the word he got. But, regardless of what he did, she told me that I had no choice. She said that I had to marry him. Except I was born here, raised here, went to school here and I am about to achieve my dream. I told her the only way I would go anywhere with that guy would be for them to kill me first and drag my dead body. His father threatened to sue me and I told him to go ahead. I did not sign the contract my parents did. Well, my parents got sued for breach of contract but the courts threw it out because arranging marriages that take US citizens out of the country by force is illegal, especially one that tries to force me to marry a possible terrorist, and since I was born here and I did not sign that contract it was never going to happen. My mother was beyond angry at me but after a lot of arguing she finally realized that I wasn't going to give up my career as a surgeon to marry a terrorist and live in a mud hut, so she quit harping about it. That's when she saw her chance with Danny. The girl they wanted him to marry is related to the the guy they wanted me to marry. She lost that one too. She and my father are in an arranged marriage and it worked out for them, so she simply cannot see why it won't work for everyone else. Now my mother is angry at both of us. Danny gave her hell for talking to you like that and she tried to justify it and started up again, which is when my father finally stopped her. I never saw her quit talking that fast. It was like my father stuffed a ball in her mouth! My father, besides being the CEO of the family company, is a professor of Advanced Mathematics, usually a quiet man, he lets my mother run the house, so when he is sharp with her she knows he is very angry, which he was. He tore into her like I had never seen and she had no choice but to take it. I seriously doubt that she would dare bring up your situation ever again, because between me, Danny, and my father, she has no chance of forcing us to do anything, especially marrying into that half ass family. I will not apologize for her, I'm just trying to explain that Danny was innocent in all this. I think he loves you and would never hurt you, but this thing with our mother scares him. He glares at her every time he sees her. He won't even have dinner with her. Give it some time Ann. Danny will eventually come see you, then you two will have to work it out." As Jennifer left I just sat there mulling over what she told me, but there is no way that I can ever get chummy with their mother, and she would never ever try to get close to me. If it does come to be that Dan and I get married, that woman will never be around my children. She will not touch them, hug them, get close to them. Nothing. I would have to tell Dan that, and I did not look forward to it. But having children is at least three years away. She might get hit by a bus, but I knew that any future with Dan was out because his mother would always be there, and always be a problem for us. Sadly, I called him and broke it off, telling him why. Then our quartet started singing and we became a big hit. Someone put our stuff on the net and before long we started getting fan mail! We started to do a wider variety of songs, just the four of us girls although on one song we needed a baritone so Carols brother Ethan filled in on that song. He is very handsome and well built. I liked him but did not think about him very much. But he was at every one of our performances and practices. After the second time he showed up Carol finally told me that he wanted to talk to me but was afraid. For the third time since I started living as a girl I have a guy interested in me. I was thrilled and shocked at the same time. But this time I am almost a complete girl, so I broke the ice and said hello to him. We talked a few times, then, a week later I had my scheduled surgery. Only Megan, Janet and my mom were there when I was in the recovery room. I did not feel any different, but everyone was smiling After a month of healing time I was back with the group singing, and sure enough, Ethan was there, tall strong and handsome, and he was staring at me. Carol nudged me and I moved a bit closer. As a complete woman I could be the girl he wanted, and frankly, I wanted to have someone too. As time went on Ethan and I began dating, and two years later he and I got married, We now have a boy and a girl, Jeff and Claire, both adopted, and both doted on by the grandparents. A long road, yet one filled with learning and joy, pain and sorrow, ending in a dream. © 2023 The above work is copyrighted material. Anyone wishing to copy, archive, or re-post this story must contact the author for permission.