Babydoll free porn video

I had been working for the Robinson family for about 4 years, before the incident had occurred. They were a friendly family, Don, the father was in his early forties, Mike, his son, had been off to college for a few years at 20, and Vicki, the daughter, was only 9. Their mother had sadly passed away 8 years ago, shortly after Vicki had been born. So that's where I came in. Don was a private surgeon, and a good one at that, but found himself oftentimes away from home, burying himself in it, and not necessarily having the time to take care of Vicki like he needed/wanted to. I didn't know who his clientele were, but he made bank working for them. So, that's why it probably seemed odd to anybody who found out that the Robinson family's babysitter/caretaker was a 19 year old male -- but none of the Robinson's found it strange at all. I had met Mike at a young age in AA, I was 15, and he was 16. Mike had gotten into drinking early as a way to deal with the passing of his mother, but also as a way to defy his father. I on the other hand had been a bit of a trouble maker growing up. I never knew my parents and often took out that frustration on others, picking fights with people much too big to fight. I was, after all a scrawny little white kid with blonde hair to my shoulders and a soft, punchable face. People tore me apart in a fight. I had been forced to go to AA after a drinking dare turned bad and I nearly killed someone while driving my buddies car. I had been trying to show off in some way or another, and the act nearly got me thrown in prison for a few years. Since then I had been proud to say I turned my life around, and was more than grateful that all I had been stuck with was a couple sessions of AA, and some community service at the old folks home. I grew to love taking care of people, and found joy in helping others out, something even I was shocked to discover. Over the course of several AA sessions Mike and I grew to be good acquaintances, and despite Dr. Robinson's protests at the time, I somehow ended up babysitting Vicki for an evening while the Robinson men got stuck at a gala for Don. Vicki and I for some reason or another just clicked, and despite her distaste for every babysitter she's ever had, seemed to genuinely like me. My guess was that growing up around men had for some reason made her uncomfortable around women, and at the age of 5, she was more tomboy than little princess. Needless to say I slowly babysat more, and as Mike moved off to college across the sea, I was hired full time at the Robinson's and grew to love my job. I even stayed at a little guest house connected to the main one, nothing big, but my own space, and it gave me quiet time whenever I needed to study for my night classes. After four years, the Robinson's kind of became like family to me, and despite Mike rarely being home, we stayed good friends, and Dr. Robinson was always a friendly man, if not a little demanding and pig headed, but that wasn't terrible for a guy whose wife had passed away. Vicki over the years however, slowly grew out of her tomboy phase, but never grew tired of me. I just found myself participating in more and more feminine activities as she grew up, to encourage however she felt. I had painted nails on occasion, or was forced to have my hair braided, but I took the embarrassment in stride, and eventually grew past it. She was always a bit stubborn, spoiled, and rarely ever didn't get her way, but she was just a kid, and a lot of fun. In truth, Vicki became a sister to me, and somebody I would do anything for... Which led to something I never expected... Month 1 I don't know how she got a hold of it, or who gave it to her, but some way or another, Vicki got a hold of a DVD for a movie called "Sucker Punch". She knew she didn't have permission to see it, so without my knowledge, she snuck into the living room one night and watched it... If I didn't know any better I would said it changed her life, but instead, it changed mine. Immediately, the next morning, it was all she could talk about, and she admitted her guilt to me, only because she wanted me to watch it with her. I put my foot down and told her it wasn't an age appropriate film for her, but she countered back that since she had already seen it, it didn't really matter anymore... I couldn't really argue with that logic, so I succumbed to her pleading, and watched it with her... I barely heard or watched the movie, as Vicki freely reenacted and warned me of every moment that came next in the film... I didn't have the heart to tell her that the film wasn't all that good, and I definitely wasn't going to tell her how attractive I thought the women in it were. I realized that all in all, she loved the movie because it seemed to combine two things she now loved, it was heroic and tomboyish, while still carrying the feminine quality she now loved. The woman in it were her heroes - badass and beautiful. We watched it every day for a week... I nearly had to kill myself... By week two I accepted my fate, and was at least grateful she was limiting the viewings to every other day, even if she didn't stop talking about it every second in between. I soon found myself getting my longish blonde hair styled by her to look somewhat like "Babydoll's" and reenacted scenes with her. At the end of the third week, she demanded to get her hair cut like "Rocket" who had become her favorite character. I eventually gave in to her demands, and found myself pleased with the resulting cut. After putting her to bed that evening, I stayed up for Don, to warn him about Vicki's new haircut, and to make sure he complimented her on it... And also to finally admit to letting her watch a movie she shouldn't probably shouldn't have been watching at her age... I prepared dinner for him and I - one of his favorite dishes as a plea bargain to hopefully ease the anger he might feel at his 9 year old watching a Pg-13 rated film. It wasn't until I set the table, and heard the door open at his arrival, that I noticed my reflection in the stove and smacked my head with my hands. I looked ridiculous. Vicki had forced me to wear a makeshift "Babydoll" outfit while she styled my hair and reenacted scenes. I was wearing a pair of my blue shorts, that we're slightly obscured by a blue towel around my waist -- making what I think she thought was a skirt. But the really embarrassing part was that I was wearing a blue sports bra she had dug up from the bowels of the house somewhere, and she had decided that was my "top." It didn't feel like much more than an undershirt so I hadn't taken notice. Finally, to top it all off, my hair was styled just like the actresses who played Babydoll, with a hairband, bangs, and two pigtails, that weren't that long but made it to the tops of my shoulders. I did have to give Vicki credit on that, she could completely make my hair look like hers, and it creeped me out a bit when I saw it. I just froze as Don drew nearer, accepting the oncoming embarrassment as he stepped into the room. There was a pause... He stared. He was a tall man, maybe 6 foot, with dark hair and the physique of someone who traveled a lot and didn't eat much. He said nothing as we stared at each other, but that was quickly followed by at least a minute of laughter... Don eventually forced himself into his seat and wiped his tears away. "Vicki being rough on ya huh?" he asked, still snorting. "I only blame myself," I shot back, shrugging my shoulders. I joined him at the table and began to eat. "What are you supposed to be?" he asked, trying to hide the smile. "Ever hear of a movie called 'Sucker Punch'?" I asked hesitantly. "Yeah, I think so." "Yeah, well one of Vicki's obviously troublemaking classmates gave her a copy of it, it's all she can talk about now." I sighed. "She watched it in secret, and instead of punishing her, I was an idiot and let her show it to me... Now I'm getting what I probably deserve. Sorry Don." Don just chuckled and smiled. "It's alright Jordan, it's nice to see her actively interested in something... And she seems quite interested in this?" I nodded and laughed. "Yeah, a bit too much. I think dress up isn't going to go away for a while." "I trust ya Jordan, if there's no harm being done, I have no reason to be upset. Hell, I accidentally let her watch the entirety of Raiders when she was 6, hasn't melted my face off yet. Glad you can be a good sport about it." "Haha," I pointed at my appearance, "no harm -- depends on how much harm this is doing to your eyes." Don just chuckled again. "I think I'll live. I've seen worse people dressed in drag. But I gotta tell ya, your outfit could use some work." "You should see her 'Rocket' costume," I laughed, "She cut up some garbage bags and piece mealed something together." "She's that into it huh?" he asked. "Oh yeah." I nodded earnestly. Don paused for a second, seemed to think for a bit, then shrugged, "Think I can make up for missing her birthday next week if I get her something that looks like the actual costume?" "I think you could probably miss every birthday for the next few years if you did that. But those aren't really costumes for kids." "I meant your costume. So she can dress you up." There was an awkward pause after he said this... Was he joking? After another second, Don broke and laughed loudly again. "Sorry! Sorry!" he teased. "The look on your face! I couldn't help it." I cracked up with him a bit, sighing slightly. "I'm not that mean," he reassured me. He wiped his eyes and returned to his dinner. I thought nothing of it. Month 2 But it turned out, Dr. Robinson was that mean. Once Vicki learned her father was going to miss another of her birthday's she threw a fit. In my opinion, understandable so. He had promised to take her on a trip, so she hadn't planned a party. Instead, she was now stuck at home, without a party, and without her father. I had hoped at this point she would move past sucker punch, but she hadn't at all, and had in fact stayed just as obsessed, and still had us reenacting scenes. The only shining light, was that with her father now out of town on her birthday, Sucker Punch was far from her mind, and it seemed like the catalyst to finally put a stopper on the odd obsession... Then the package arrived. It came to the door gift wrapped and addressed to Vicki, but also a smaller box with a small card addressed to me on it. I gave her the large package, and it seemed to pull her out of her gloom, but only just a little. Then I sat down and opened my card, which was from Don and read: "I hate myself for this, and I'm sorry Jordan. I'm sure we'll eventually look back at this and laugh. I hope when I get back in two weeks you'll forgive me, I promise I'll make the torture worthwhile. Also hope it fits..." My stomach sunk, and I nearly bolted for the package to grab it from her hands, but I was too late, the wrapping was long gone and the garment shaped box was already being opened. I heard her squeal with delight, and my stomach sunk further, but what she pulled out wasn't what I feared. It was a custom made Rocket costume, which appeared to have had all the sex appeal pulled out of it, and even came with pants. Vicki didn't even seem to notice that it basically just looked like a jumpsuit with a couple added trinkets, she was just ecstatic. I sighed with relief for just a second, but suddenly realized, her box was too big for just that. She set down the outfit and squealed again. She motioned me over and smiled up at me. In the box was a custom made Babydoll costume, with absolutely none of the sex appeal pulled out of it. It looked like it belonged in the film... And I wish it had stayed there. I turned to Vicki to set my foot down immediately and let her know this wasn't going to happen, but the look on her face was just so damn happy... I found myself saying nothing, just staring with my mouth open. Vicki sadly took this as me being in awe and nodded happily, "I know! It's beautiful! You'll look so pretty Jordan!" She squealed again and pulled out the costume: sexy skirt, sexy top, and even some heels that I didn't doubt would fit me... How was I gonna wear shorts under this? There was barely any material there in the first place! Vicki ran to my package I had left on the couch and was already opening it, I just let her, I was too shocked to do much at the moment. On one hand I hated Don for what he did, but on the other, I admired that he knew exactly what to do to make his daughter happy, I'm sure giving his male house-sitter an outfit like this was just as embarrassing to him as it was too me. I heard Vicki squeal again. Pulling out the contents of the box to show me. It was a bra and panty set, and stockings... Well, that answered how I was going to wear shorts under the skirt: I wasn't... "Oh my gosh! Oh my gosh! Oh my gosh! I love daddy, this is gonna be so fun dressing you up!" My understanding of Don's motives reversed, and I went back to being angry again. I was gonna give him a piece of my mind when he got back... In two weeks... Two weeks! Oh... Great... But then Vicki grabbed all of the Babydoll gear in her hands, and hurried up to me, smiling and sticking it out for me to take... I had never seen her so smiley... "Aren't you excited!!!??" she beamed. My anger melted away again... Well, if I was going to do this, I may as well make a little girl happy while doing it... I took the outfit and lingerie. "I'm super excited!" I answered back, sounding way more honest than I expected. "Okay, you go take a bath and get changed, and I'll wait while you do your hair and makeup Babydoll! But I wanna do your nails! I'm gonna go change too!" She ran off at top speed, leaving me holding a pile of clothing I would have loved to see a woman my age wearing... Not have me about to put on... I inhaled and exhaled slowly, then headed for my own bathroom, snagging the heels out of the box on the way. What was gonna happen was gonna happen. I was gonna be Babydoll for an evening. I ran myself a bath, and started by removing the fingernail polish from the day before, an activity I had gotten used to. Once that was done, I sat in the tub and just soaked for a bit, slowly easing myself into a relaxing mood so I wouldn't chicken out... The odd thing was, I wasn't too worried about it. I'd been playing dress up with Vicki for years, so my embarrassment had died years ago, but an odd part or me was kinda curious... The outfit was obviously designed to for me, nothing else I wore ever was, so I wondered what I would look like. There had been times dressing up with Vicki where I sometimes wished I looked better in the clothing, Vicki always seemed to make a deal of pointing out and wishing I fit into the outfits better, and was often sad I didn't look like a proper "mommy" as she uncomfortably called me on occasion. It kinda tore at my subconscious a little, and the more I looked better in the clothes, the happier she seemed, so it came as no surprise that in a way I was almost being trained like pavlov's dog to want to look better in female clothing, and also explained why I could wear it without taking notice, like the dinner with Don last week that had started this. So, I wasn't surprised at all when I picked up my razor, and instead of shaving what little facial hair ever grew on my face, I began to shave my legs... At first I cursed myself for succumbing to the desire, but as I continued on with the task and finished one leg, I was shocked, and pleasantly surprised at the result. I had always had a thin feminine body, and as I shaved more and more of myself, that become even more apparent. Soon is was smooth from my neck to my toes. After I rinsed off and stepped out of the tub, I couldn't help being a little turned on by reflection, but also by the feeling as my soft, now silky legs brushed up against one another... I heard a soft feminine moan echo in my bathroom as I rubbed my legs together, and I was shocked to realize I had made the sound. I shook it off and headed for the new clothing. I had thrown the lingerie back in the box it came in, so I opened it up again and slowly pulled out the contents, starting first with a little flyer that came from where it had been ordered. It said it was a lingerie set from Victoria's Secret, and the woman in the picture on the pamphlet looked amazing in it. Not only that, but this was a very, very sexy bra set. The pamphlet said it was from the Victoria's Secret's "Scandalous" collection. The tag line was even "There is only one thing this collection is made for..." I snorted at the cheesiness, but also felt a little uncomfortable. Hopefully this had just been ordered without any thought put into it... Because if there had been, this was weird... Well, weirder than it already was... I threw the pamphlet on the counter and pulled out the panties... They were dark blue, with silk and lace, and were "bikini" panties. Which I wagered would likely fit like the kind of underwear cheerleaders wore under their skirts... But not this sexy.... I slipped them on, and was shocked at how amazing they felt as they slide into place... They fit beautifully... Almost too beautifully... Like my backside should be wearing underwear designed to fit this way. My hips always had been a little big. I spun in the mirror and looked at my freshly shaven backside in the new panties... That was a woman's ass... There was no way that that wasn't... I stared in awe, mouth agape... From the back, I looked just like a woman. This wasn't shocking as much as it was fascinating to me... I finally snapped out of it when my still drying hair dropped some water on my shoulder... I spun back around and reached for the bra. It was even sexier, dark blue, with matching lace and satin running over it. A woman would be lucky to own a bra like this... For an odd second I felt flattered, Don hadn't skimped, that's for sure. Not every woman got such sexy lingerie from their boss... I hesitated... Had I just referred to myself as a woman? I ignored it and pressed on, reading the bra tag. Bombshell Bra 34B. Didn't know what it meant, but didn't matter to me... I slipped it on... And was just as pleased to do so as I had done with the panties. I adjusted the straps, and hooked it in the back after a few failed attempts. It was then I noticed that the bra was actually quite padded, so I readjusted what flesh I had on my chest, and fixed the placement of the bra. After I did so I stared again... There were no breasts there... But there was something. The bra definitely didn't make it look like there was nothing... I looked in the mirror again... From the neck down, I couldn't tell you that was a young man. Hell, maybe even from the face down, with my wet hair hanging, and my soft face, it wasn't easy. I hurried to slip on the rest of the lingerie, gently rolling and savoring the moment as the stockings slid over my skin, and planting my feet in the three inch, Babydoll style heels. I hurried to the full length mirror, finding it a little, but not too difficult to walk in heels... I stared... The heels made my legs and ass look amazing! I was perched beautifully. I had always wanted to see a sexy woman in lingerie in my bathroom... And here she was!!! I just never would have assumed I would be that woman. Sure I was far from perfect, but it was still shocking how I looked. I couldn't help posing a little... Cocking my hip to the side... Putting my hands on my hips... And then mocking the woman in the pamphlet, grabbing my hair with my hands and piling it up on my head a bit... Had my waist always been this tiny? My butt this big? I couldn't help feeling a little excited about putting the costume on to see the rest, but first I sat down in the "make up" chair. Vicki had been obsessed with makeup lately, and knowing she wasn't old enough to wear it yet, had no problem trying it out on me, which meant I knew exactly what to do. But this time, I tried a little harder... Usually I just threw the crap on, to please her, but I kinda wanted to see where this would go. So I took my time with the mascara and eye lash curler, and I took way too much time putting some light lipstick on. Then I grabbed the blow dryer and hair straightener... She had become obsessed with doing my hair since she was 7, and after forcing me to wear it like Babydoll's... It wasn't hard to replicate... Within minutes, I had my hair looking like hers, and finished the look with the little black hair band. I stood up, trying to ignore, for now, the very feminine face looking back at me in the mirror. I approached the costume and stared down at it... God, it was sexy. Sexy little pleated skirt, sexy top that would show of my stomach... What I wouldn't give to see a woman wear this for me... Well, I figured I was kinda about to. I picked up the skirt and slipped it on first. Laughing a little as I realized I was still wearing heels and hadn't noticed... As the material slowly slide up my stocking covered legs and over my panty covered booty, I couldn't help giving a little wiggle as I settled it into place. I buttoned it up, and wasn't shocked to find it was definitely made to my measurements. Don never skimped. The skirt stopped about half way down my thighs, just above my stockings... It looked great! I shook my hips a little, watching the pleats swirl a bit, and I got a little turned on by seeing the slit in the skirt reveal some of my sexy leg. I giggled. I stopped... I actually giggled? Well... I suppose what else was I supposed to do dressed like this? I grabbed the top and put it on next, sliding it over my head, careful to avoid my face and hair, and letting it settle around the makeshift boobs my bra created... I finished by buckling the belt just above my navel and flattening the neckerchief around my neck. I spun around and faced the mirror... I wasn't perfect. But I could have been a contender in any cosplay competition. "Wow." I said to the empty bathroom. I giggled again, this time at the somewhat manly voice that came from this image of the sexy school girl. I would have to work on that... If I saw myself in public, I know I would want to meet this girl. I pulled myself from the mirror and headed out, expecting Vicki to be upset at how long it was taking. I found her quickly, out in the living room, already in her simple costume. She was already pretending to beat up the couch. I approached a little nervously, finding myself subconsciously doing the act of flattening my skirt as I walked. Vicki a just beamed at me. "Oh wow!!! Hi Babydoll!!!" She punched the couch one more time, then twirled. "Do you like my costume!?" "I love it Vicki!" I encouraged her. "It's Rocket now!" She laughed and punched the couch some more. I waited... I don't know what I was expecting from her really... I was kinda throwing myself out there by wearing this, and I kind of wanted more acknowledgement of that from her. I stepped out from the couch to make sure she wasn't missing any part of my outfit and waited. She was still very happily fighting the couch and pillows on top... I finally just asked. "What do you think? Do you like how I look?" Vicki nodded, kind of half of ignoring me. "Yeah! You look great Babydoll! I wish it fit you better though! Like mine! Mine is perfect!" She punched again. I felt my heart sink a little? What? Come on, this was a big deal here, I didn't look that bad did I? "Oh, what do you mean?" I asked, reexamining how I looked. "You know," she said, her breath now a little labored as she grew tired of the couch fight. "I wish your body looked more like Babydoll. You still look like you!" She finally stopped fighting and was panting a bit. She seemed to notice my face fall a little... But why was my face falling in the first place? I was a dude after all, of course I looked a little funny like this... Vicki seemed to feel bad anyway. She rushed up to me and hugged me around the waist. "I think you look very pretty!" she said happily. "this is the best birthday ever! You wanna fight on the train?!" I got over what she said almost instantly and nodded, seeing her happy was all I needed anyway. We played for the rest of the day, before Vicki ran out of steam, and I tucked her into bed, still dressed in her outfit. As I kissed her on the head she asked, "Can you dress as Babydoll tomorrow too? I want to play!" "Of course!" I'm answered without processing. I patted her head, turned off the light and closed her door. Running around in heels for several hours was killing me, I painfully started heading towards my room across the house, wondering how women did it. Along the way, I passed Don's large room, which had both it's double doors open. I caught my reflection in a mirror as I passed. He had a little circular stand and circular mirror system set up by his walk in closet. He used it whenever he had suits made... I ignored my aching feet and walked towards the mirror, still curious. I stepped up on the platform and let the motion sensors turn on the lights... I was still attracted to the image, but I could see what Vicki was talking about. My waist was a little pudgy. My butt was a little flat... And my chest, well, I didn't really have one... I mean, that made sense after all... But on another level.... I was curious... What would I look like in this outfit if I had a butt? And a thin little waist? And even... Some breasts? The thought made me shutter a little... And it also made me look over towards the room connected to the mirrors... Don's wife's old bathroom... It had basically been untouched since she passed away. At least by anyone but Vicki, who had stolen make up, clothes, and the occasional jewelry item from there... I found myself walking in and turning the lights on without really thinking... I just looked around a bit at the counter tops, and opened the first cabinet I found... I didn't know what I was looking for until I saw them... Birth control pills... I picked up two full packets and looked at them... Was I really thinking about...? I slowly walked out of the room, carrying the pill packages in my hand, with my heart racing... What was I doing? And why was this so exciting to me? By the time I made it back to my room I felt like I was going to explode, and as soon as the door was locked, I had opened the pill packets. I looked in the full length mirror, holding two pills in my hand... Vicki was right, I still did look like me... But for how much longer? I watched as Babydoll lifted the pills up and put them into her mouth. I played with them on my tongue for a bit, then swallowed... The thrill I felt was overwhelming... I quickly threw the pill packets in a dresser drawer and crawled up onto my bed. I loved the feeling of the pleated skirt as it swayed around my hips and brushed my stocking covered thighs... I quickly grabbed a pillow and pulled it to me. I wasn't sure what I was doing until I had straddled the pillow and had pulled my panties down. In a very unladylike fashion, I then grinded and bounced my crotch on the pillow... Or maybe it was somewhat ladylike... I began to moan, and as I did, with each moan, I made my voice sound more and more feminine, until I was rocking up and down, and squealing like a woman about to reach orgasm... And that's what I did... I shuttered violently, and moaned one last time... Sinking back onto my bed... I was breathing heavily, and very femininely, and I couldn't help rubbing my hands up and down my smooth, and costume covered body. I had been a naughty girl, and I was very pleased with the result. Month 3 Two weeks passed quickly, and over that span of time, wearing the Babydoll outfit went from becoming a hassle, to becoming somewhat of my uniform. I woke up and put it on, and wasn't allowed to take it off until I had tucked Vicki into bed. She threw a tantrum when I forced her to wash her costume, so I didn't even want to deal with spending a day not wearing mine, out of my desire to avoid another freak out. Vicki demanded that in seven months, when Halloween arrived, we both knew exactly who we would go trick or treating as... And so, with that as something looming on the horizon... I found myself taking those pills every night... Knowing full well I shouldn't be taking them, but also knowing being seen in public dressed like this, was a good incentive to do it right... Maybe I was crazy, and a part of me thought I was, but I couldn't stop for some reason... I had to know what I would look like... The night Don arrived back home, I remained in costume... I wanted him to see what his handy work was doing to me. My anger at this point had passed, but I definitely was starting to feel other emotions more strongly. I blamed the pills. I set the table, a big meal for him, and a light salad for me. I was working on my figure. This time when Don entered, there was no laughter, he just stared, first in confusion, then after recognizing me, in awe... "Uh..." was all he managed. "Hi Don," I said happily. I sat in my chair, folding my little skirt under my butt as I did and crossing my stocking covered legs like a lady. "So..." he managed again. "Yeah, she's still obsessed with it," I answered, finding myself smiling. That seemed to break the tension. He sat down, but at least he was smiling awkwardly now. "You... You realize that was a joke right?" he stated, he was trying to keep from bursting out laughing now. "What?" I asked, curious. "That outfit was a joke, that's why it was in a separate box for you, I was just razzing you... The real gift was for Vicki." "They both came in the same box," I responded, still unsure what he meant. "Oh shit..." he stared. "Yeah, I was just teasing you... You didn't get that from the note? I thought you'd... Well I didn't think..." He snorted and tried not to laugh again. "I admire your commitment." "Didn't have much of a choice, once she saw it there was no turning back." He leaned over and inspected my handiwork... I oddly felt a little uncomfortable and became painfully aware of how little clothing I was actually wearing. The hell was I doing? How was I okay with this? Don probably thought I was insane. "Where'd you get the stockings?" he asked curiously. "What do you mean? They came with the rest?" There was a pause as Don tried to figure that out. Then he snorted again. "Oh shit... Jordan are you... Wearing it?" I just nodded. "I'm so sorry, that was supposed to arrive before I left... It was a gift for... Well for someone else... But it didn't work out anyway..." I felt my stomach sink. Of course it was. Why the hell would he buy that shit for me? I felt silly as all hell. I opened my mouth, but said nothing... What was there to say? "Look," Don said, finally stopping the smile. "All jokes aside, I'm impressed man. Not everybody would dress up like that to make a 9 year old happy. You're a good kid Jordan. And I appreciate you." "Thanks Don... I just... Well feel kinda stupid now... I should have known it was a joke." "Don't worry about it!" He laughed. "Honestly, you don't look half bad at all. It took me a full 10 seconds to register who you were." "Really?" I asked, not quite capable of hiding my excitement. "Yeah." Don nodded, then looked my up and down again. This time he paused a little too long on my legs... And my stomach... The stares actually gave me butterflies... But why? I excused my self and picked up my empty plate. As I walked towards the sink I could feel his eyes on my backside as I sashayed to the kitchen. Month 5 Two months went by... And I began to change... As I lost weight I gained it in other places, and I watched in anticipation almost as everyday, my hips became wider, my butt bigger, and my breasts... Well I had breasts now. Not huge, but definitely breasts. The Babydoll outfit became my uniform. I didn't go a day without wearing it, as Vicki demanded. And her passion for the film and dress up only grew stronger as she seemed to notice the changes in my body. She was the only one who seemed to notice actually. Seeing as they were slow and gradual, Don made no mention of them. He in fact offered to step in and stop the dress up for me, telling me I didn't have to do it. I finally admitted I enjoyed doing it for Vicki, and it didn't bother me... When in reality, I was kind of just doing it for me now. At first I thought Don was going to refuse and tell us to knock it off. But after Vicki finally forced him to watch the film, he actually did something even worse, depending on perspective... I found two new packages one day in my room. One was slightly smaller and garment shaped, and the other was quite a bit bigger, and heavier. I opened the smaller one to discover Babydoll's second outfit from the movie. A similar style and shape, but white, and adorned with cute little jewels. I actually clapped my hands together giddily when I saw it. Now I could rotate the costume and not have to wash everyday! That was why I was clapping right? Not that I was excited to see myself in it? I opened the other box curiously, I gasped. Not only was there a sexy white bra, panty, and stocking set to match with the new outfit, but it looked like Don had purchased half of Victoria's Secret... I had mentioned the week before how irritating it was to wash the clothing every day, and I cracked a joke about getting tired of wearing the same ole "sexy underwear." We had had a good laugh, but Don seemed to pick up on my actual irritation with the situation. I stared down at the box is awe... This was too much, he had to have spent a fortune... There was like 30 bras of varying colors, and matching panties... All incredibly sexy! Not only that, but also several corsets, nighties, and slips... All of which would be useless under my costume... Unless I wore them outside of it... Would be a shame for that lingerie to go to waste... I quickly snatched up a deep red colored corset and matching panty. I was already wearing stockings, so that was no worry. I wrapped the corset around me, latched up the front hooks, and began to pull the laces. I was shocked to see my waist become so tiny as the corset shrunk fit to my body, and was even more surprised when the cups of the corset filled out with my developing breasts, pushing up to form some decent cleavage as the corset grasped me tighter. I tied off the laces with a smile on my face, then slipped into the panties and hooked the stockings to the corset garters. I looked in the full length mirror. My hair was a mess, and my makeup was wearing off over the course of the day, but I looked pretty damn sexy despite that. My new curves were really developing!!! My ass looked great in panties, my little breasts were perky but full, and my waist was so devilishly thin!!! What was missing were heels to make my legs look thinner and sexier. And they needed to be red to match! I remembered the Don's ex wife had a closet full of untouched clothing and heels... Dare I? I definitely would dare... But first, some touch up. I quickly sat in my hair and makeup chair. I applied a new coat of makeup, and added a little darker color to help match with the dark red lingerie, then I attacked my hair. I had been playing with my hair for years with Vicki, so it wasn't hard for me. It was actually more fun, seeing as it was longer now. I took a curling iron and made my hair into little ringlets, then, I took a bunch of Bobby pins and stacked my hair on my head. After about 30 mins I looked like I had an almost wedding style up-do, but much messier. I giggled as I imagined this was probably what a bride's hair looked like after the honeymoon. Pleased with the result, I stood up and headed for Don's bedroom, he had already had dinner and was likely watching tv in his own room. My heart was racing as I approached the door frame. I took a deep breath then slunk around the corner, leaning sexily against the frame. It took Don a second to become aware of my presence, and then another full second to recognize me... And several second for his eyes to take it all in... He sat up in bed and cleared his throat. "Oh... Hey... uh Jordan... Need anything?" "Just wanted to say thanks for the new clothes! That'll help a lot." I smiled at him. He just continued to stare. I could see he was liking what he was seeing, even if he was trying to hide it. "Yeah... Yeah, no problem," he whispered. "Just wanted to ask a favor, can I possibly borrow a pair of heels?" "Uh? Heels? Oh, yeah. Yeah, they aren't any use to me." I smiled and headed for the old back room, making sure to swing my hips more than normal. I found the heels quickly and slipped them on. An almost perfect fit! I entered Don's room again and strutted across the room towards the door. I could feel his eyes on my body. I stopped at the door and waved coyly. "Thanks Don." I winked He just muttered, "Yes." I giggled the whole way back to my room, and once I was there, I threw out all my old underwear and put my new lingerie in instead. I went to bed wearing the lingerie and heels, and was excited to see where this went. Month 6 I waited a full month before putting the new outfit into rotation. By that point I had perky, B cup sized breasts, and my hair was all the way down to my bra strap. The first time I put on the new Babydoll outfit, Vicki nearly died! She complimented me on fitting into it better, and gave me a big hug. And of course, she told me I had to learn how to dance, just like Babydoll. So I began to take lessons privately in my room. The first time Don saw me in it, he choked on his morning breakfast. I wasn't hiding my breasts anymore, and the new outfit definitely didn't hide my cleavage. Don showed some major restraint and didn't ask, but being a surgeon, I knew he knew what I had likely been doing to myself. But other than glancing at my new breasts quite often as I moved about the kitchen, he asked nothing about my new body shape, and just ate his breakfast. So I decided to tease him into talking about it. I planted my booty on a bar stool and crossed my legs, making sure to also sit up straight and push my chest out. He had no choice but to see my body if I sat there. I was eating a small yogurt and was happily sucking and slurping on the spoon as I started a conversation. "Hey Don?" I asked innocently, licking the spoon. He turned to me and forced himself to stare only into my eyes. I batted my eyelashes at him. "Can I ask a favor?" I asked. "Of course," he said quietly. "Do you think you might be able to get me a sports bra? And maybe some yoga pants? Been taking dancing lessons and it's been hard to do it naked." Don visibly swallowed then answered. "Yeah... Yeah sure, I can do that." "Oh thanks so much!" I set my yogurt down and gently lifted up my breasts to draw attention to them. "So I'm a 34B up here. I was thinking maybe a cute little push up sports bra? Pink? Or whatever you think is sexy, you have good taste." Don just whispered, "Okay..." And stared at my breasts as I held them. I slid off the stool and turned around, I leaned over and set my elbows on the stool, my plump little ass in the air as I curved my back. "And maybe a medium yoga pant? Haven't gotten them before but I think that'll fit? Do you?" I looked over my shoulder and wiggled a little, I loved the feeling of my short little skirt swaying over my ass as I did. Don stared, with his fork halfway to his mouth with no food on it. "Yeah... That sounds right..." "Awesome! Thanks Don!" I stood up quickly and walked over to him, quickly planting a kiss on his cheek, then I headed for the living room to play with Vicki. I was so evil... One night, a week later, while dressed in the sexy white outfit, and after finishing the dishes, I joined Don and Vicki in the living room, where they were of course watching the film. They were on the smaller couch together, and Don was trying to hide his obvious boredom from watching the film a third time. He should be so lucky to have only had to watch it three times... "Come join us Babydoll!" Vicki exclaimed. I was no longer Jordan to her, in or out of costume I was Babydoll, and I wasn't out of costume often. "Sorry sweetie," I said. "There's no room on the couch for me!" "Sure there is! Come on, just sit in Daddy's lap!" She shifted out of her father's lap and patted it, then curled up on her side of the small couch. I hesitated, and Don was trying to avoid eye contact. "Come on!" Vicki exclaimed. "Sweetie, I don't think daddy -" I started. "Come on! Sit down, or we'll have to start the movie over." Vicki pouted. This caught Don's attention, and he just nodded at me. "Let's not start the movie over!" he said in what sounded like fear. I smiled and walked over... I stopped in front of Don, my back to him... I wasn't sure what to do next, or if I even wanted to, sure I'd been teasing him lately... but thankfully Don acted instead. He grabbed me by my skirt covered hips and pulled me down into his lap. I quickly smoothed out my skirt as he did so my panty covered ass wasn't just planted on his crotch. I felt so small in his lap, as he could easily look just over my head. I kind of just froze, and so did he as we both realized how awkward this was. But it appeased Vicki, who started the movie back up. For about five minutes neither of us moved at all. Basically frozen in terror, but I finally had to shift as my leg began to fall asleep. I wiggled a little, rubbing my skirted bottom over his lap, he shifted, making me realize he still had his hands on my hips. "Sorry," he said, "you uncomfortable?" "Not really. But, here." I slid back further, until my back was against his chest, and my plump bottom was pressed further against his crotch. Then I curled my legs up and underneath me. He had no choice but to wrap his arms around me, where they found their way into my own lap, but actually rested on my smooth thighs, just above the stockings and just below the hem of the skirt. I couldn't tell you who started it first, but 10 minutes later, he was gently stroking those thighs, and fingering the hem of my skirt, and I was gently grinding into his crotch, feeling the bulge as his erection began to form. I shifted, and he froze, seeming to realize what was happening, but I was only making my self more comfortable, leaning back and nuzzling my head into his shoulder. There was a pause, and I think we both had to process what was happening. Here Don was, with his 19 year old male employee, curled up in his lap, wearing something incredibly sexy and revealing, and willingly turning him on. Here I was, a 19 year old male, who now looked and was for some reason happy with appearing as a sexy 19 year old woman, edging him on... We both seemed to reach the same conclusion at once. I grinded into his lap a little more, and he went back to running his hands over my thighs. An hour later the movie was over, and Vicki went off to bed, blissfully unaware of what was happening between me and her father. As soon as the door was closed, I heard Don try to cover his tracks. "Jordan, I'm so sorry! I don't know what has gotten--" I just put my finger to his lips and said, "Shhhhhh..." He fell silent. I slowly crawled off his lap, and then leaned over, letting him stare at my cleavage before I leaned in a kissed him on the lips. Babydoll was in charge now. I slowly backed away, and approached the stereo, making sure to keep him entranced as I swayed my hips back and forth. I put on a song, slow and rhythmic, then turned around. I had been practicing for a couple weeks now. I smiled seductively at him, then began to dance. Swaying my hips, bending over, tossing me hair. A little of everything. Eventually I made my way toward him and his shocked face, and I planted my booty onto his erect crotch. I pinned my knees against his hips and put my hands in my hair, piling it on top of my head, as I grinded against him. He slowly reached out towards my hips. I quickly grabbed them, and planted his palms on my waist. He grabbed tightly. I smiled and guided his hands along my body, first down to my thighs, where he tugged at the stockings, then up under my skirt to my ass, where he rubbed the satiny material of my panties. I squealed most femininely as he did so, which only seemed to make him more excited. He ran his hands over my skirt covered hips, across my smooth stomach, and up to my perky breasts, where he massaged them through the white, satiny material. I began to moan, and bounced more, letting him fondle me with passion. "Oh god... Oh god..." I whispered, half moaning and half seductively. I had never felt like this before. My new feminine hormones were screaming in pure joy. My nipples were at full attention. "Oh god Babydoll..." I heard Don whisper, as he leaned in and began kissing my neck. "Fuck me, oh god fuck me!" I whispered in his ear. "Make me a woman Don." He suddenly stood up, taking me by surprise but not letting go. I wrapped my stocking clad legs around him and let him fumble with his pants as he continued to kiss my neck. He eventually dropped them and kicked them away, letting his erection brush up into my skirt, and rub against my panty covered ass. He gently lowered me onto the couch on my back, where I looked up at him, biting my lip and squirming a little, trying to tease as much as possible. He kissed me from my lips to my belly button, then grabbed my hips, and gently spun me around. I got on my hands and knees, pushing my hands against the couch arm rest for support. Don slipped in behind me, putting his knees on either side of me. I was still moaning as he put his hands up my skirt and lowered my panties. He stared at my backside in awe as I looked over my shoulder and winked at him. "Spank me sweetie," I told him. "I've been a bad girl." "Oh yes you have Babydoll!" He responded. He slapped me on the ass, and I was shocked to feel a sexual flutter throughout me, I moaned loudly. Don couldn't take it anymore. He pressed himself up against me, and I arched my back as I felt his stiff erection find it's way. I moaned in ecstasy as he entered me. It was a little painful, but I was so overwhelmed right now, it was hardly a feeling. There was a slight pause, and then he began to pump. I matched his rhythm, happily swaying back and forth with him as he pounded me. I loved the feeling of my swinging breasts underneath me. My hair flying everywhere, and especially my little skirt flipping back and forth with each thrust. "Oh God!" I squealed. "Fuck me Don! Make me a woman! A sexy woman!" "You are a sexy woman Babydoll!" He moaned back. "A hot sexy little woman!" He grabbed a hold of my hips and thrusted hard one last time, I squealed with delight and we both reached orgasm. Don slumped back, panting heavily. I sat up and pulled my panties back up, then fell backward onto his chest, into his open arms. We both just breathed heavily for a while, laying on the couch. "I just... Wow..." was all Don could say... I just giggled, then nuzzled into his chest more. "I was... Not expecting that." He continued on. I sat up slowly and straddled him, putting my knees on either side of his hips, and my booty on his crotch again. He just stared up at me, in both confusion and lust. I just wanted lust, so I reached up and pulled my top off, revealing my breasts and sexy white bra. I put his hands against them and let him fondle them as I ever so slowly grinded on him, trying to get him erect again. He was back to just plain lust again. As he fondled my breasts, I slowly unbuttoned his shirt, revealing a physique that most 40 year old men didn't have. He was well built, and I loved that in comparison, my body looked so small and feminine. I gently ran my hands over his muscles, running my manicured nails over his chest. "Jordan... I..." he began, but stopped and enjoyed my touch. "I shouldn't be doing this..." he whispered. "Why not?" I whispered back. "Aren't you lonely? Haven't you been lonely for a while?" He just stared up at me. I knew the answer. I knew he could never get a relationship to work with all his travel and also having a kid. "Don't you like how I look?" I pressed, hoping to guilt him. "Of course!" he answered quickly. "I mean... I'm shocked at how... How this happened... You... You look gorgeous." I leaned down and kissed his neck, then up to his ear where I whispered., "I feel gorgeous." I nibbled on his earlobe and felt him shudder. "I never expected to be so turned on by..." he started again... "By what?" I pressed. "Knowing what you are... I... Knowing what you have in your... Your panties... And yet seeing you so hot and sexy like this..." "I know!" I agreed. "Isn't it fun! I never saw this coming either but I love being sexy like this. Sexy for you." I winked, he smiled. "I can't wait to get my body as feminine as possible." I sat back up and began rubbing on his crotch some more. He began to become a erect again. "Yeah... Me too..." He fondled my breasts some more. "You think these will grow any more?" I shook my head. "Probably not... They kind of slowed down..." I put on what I hoped was a pouty face. He smiled devilishly. "You want a little help?" I smiled. "Oh? Offering your services?" He laughed. "Maybe... Nothing too big, but I could help you get a C- cup?" "I would love that," I smiled. "But I need something in return." Don chuckled. "You need something in return? I thought they were for you?" "More for you than me Don," I winked. "I like my B cups." He laughed again. "Okay, what do you want?" I smiled and kissed him on the lips. "To be your girlfriend." He smiled but then thought about it. I knew he was thinking about what that entailed. I answered before he thought too hard. "All that means is we stay as we are. I take care of Vicki. You do what you do..." I leaned in and nibbled his ear again. "But I want to sleep in your bed." He shuddered again and smiled. He pushed me back up. "Deal," he stated. I giggled and grinded harder. I felt my boyfriends penis become erect again. Month 7 In no time at all I had moved out of the guest house and moved into Don's bedroom. I could tell he was still having mixed feelings about the whole situation, but I made sure he never saw me as old Jordan to help sell the illusion. To be honest, old Jordan was pretty much gone, my new body had taken over. It didn't take long for Vicki to catch on that something had changed, but thankfully she seemed very pleased with it, and often reminded me that she always knew I could be a good mommy. After a couple weeks had passed, Don started to accept the situation, and for the first time in a while, started to be happier, and began to treat me like his actual girlfriend. He began buying me new little gifts, like clothes or lingerie, and even jewelry. He even began making dinner for me on occasion. I enjoyed it immensely. I had never been in a real relationship before, especially not in the role of the woman, so I really liked the attention... And we both liked the sex... One of the gifts I made Don get "me" was a stripper pole in the bedroom. I had really been getting into dancing and liked to tease him every night. When the installer came to put in the pole, I made sure I was dressed appropriately. Don had gotten my a very sexy pencil skirt suit, but that didn't mean I couldn't show a little bit of cleavage. The contractor who installed it was nervous the entire time, but did the job and politely referred to me as ma'am. There was no question he thought I was a woman... I loved it. As it turned out the contractor actually knew Don from an old circle of friends, and it didn't take long for the rumor mill to piece together what they thought was the truth: Don Robinson had finally fired his odd house sitter, and was now dating a woman half his age. Oddly enough, Don was only congratulated on this, as everyone in his circle of acquaintances was just happy to hear he was finally dating again. Month 9 I squirmed in my chair. Feeling the tight satin of my dress slide on the leather of the restaurant chair. A lot had happened in the last two months. For one, I had C-cups now, and I loved them. They were currently filling up the bra cups of my new dress, and doing a damn fine job of it. In the meantime, the new hormones I was taking had filled in the rest of my body, and there was no denying the hour glass shape I know had. I had even gotten a little work done on my nose, adding to the feminization. All thanks to Don. I spotted a couple a few tables down from me. I could see the young man in the relationship looking at me while his girlfriend talked over the wine list to the waiter. I smiled at him, and could see his eyes nervously dart up and down my body. I had bought a new little black dress for the special occasion this evening, and it was currently hugging every curve of my body. The dress length didn't come mid thigh, but was more just "ass length" and covered up only what it needed to to be appropriate. It was a light satiny material that clung to me tightly, so at least it wasn't going anywhere... For now. I ignored the couple and watched as my dinner mate entered the restaurant. He exchanged words with the maitre'd, who pointed out my table to him. After a moment of confusion, he thanked the maitre'd and headed for me. I sat up straight as he approached, pushing my breasts out a little and smiling. Mike Robinson stopped at the chair in front of me. He had changed a lot since I'd last seem him. Taller somehow, and already showing a little grey in his hair at only 21. He looked a lot like his father. He nervously stuck out his hand. "Hi, I'm Mike. You must be Jordyn?" You could tell the wheels in his head were clicking a little, but he hadn't connected the dots yet... He would in time. "Hi Mike," I said, smiling up at him. He gently shook my hand, then took his seat. He cleared his throat, somewhat uncomfortable with the situation. I couldn't blame him, it was probably a shock meeting his dad's girlfriend and realizing how much younger she was than he was probably expecting... But he'd be more shocked soon. "I would order some wine, but I know we both don't drink." I offered. "How about an appetizer?" "Sounds good," he answered quickly. The next hour or so of the dinner passed quickly, I simply kept Mike busy by having him fill me in on everything he'd done in the last year, and he was more than willing to talk to fill any awkward silence. I was happy to hear things were going well for him, I was still his friend after all. Then he dropped the question that I knew was inevitable. "So, how'd you meet my dad?" he asked inquisitively, pushing his finished plate away. I smiled at him, dabbed my mouth with a napkin and sighed. "Through work," I offered. "What do you do?" "I housesit... Or babysit... Wasn't what I always intended, but pays the bills until I get my degree in IT... Though, to be honest, that doesn't seem as interesting to me anymore." There was a very long pause, in which Mike just stared. Then scanned me from my face, to my chest, to my legs, and back again. I let him figure it out on his own. "Oh my god... Jordan..." "Hi Mike," I answered sheepishly. He just stared, then grabbed the elbow of a passing waiter. "Can I get a double scotch on the rocks?" he asked the waiter quickly. "What brand sir?" "I really couldn't care less," he stated simply. "Make that two!" I called after the waiter as he nodded and walked off. Mike didn't say anything else until he had two drinks in him. He didn't try to ignore me, or seem upset, he just kept looking at me and opening his mouth as if to say something, then stopping. Finally he shoved his empty glass away and asked, "It's just weird... Ya know? Well not weird, but... Well... I'm just surprised." "Yeah, we were too." "Yeah..." He stared some more. "You look good though. I mean, if I'm allowed to say that." "You are. And thank you." I smiled. "I just didn't think my dad was... Or you were... Ya know..." I shrugged. "Neither did we." "So you're... You know down there..." He motioned towards my nether regions. "Oh, no, that's still there." Mike nodded slowly. "Right... Okay... And how is Vicki taking all this? Your new relationship?" "She loves it... She's happy to have a new mommy soon." "Soon?" I raised my hand, showing Mike the cute engagement ring around my finger. "So... You're gonna be..." "Your step mom." "Right... Gotta say... Didn't see that coming first time we met in AA." There was a pause, then we both burst out laughing. Which upset the tables next to us, but we didn't care. The laughter seemed to erase most the tension across the table. Mike nodded at the waiter to bring another round. We had a couple more drinks, and chatted some more, eventually breaking away the tension, and talking like old friends do. The night went much better than expected, and when we got up to leave Mike offered his arm, as the drinks had had more of an affect on me than him. He drove home and dropped me off, letting me know that as weird as it was, at least his dad and I seemed happy. He had no idea. I entered the bedroom all smiles, Don watched me enter, a look of worry already on his face. "How did it go?" he asked nervously. "Fine." I smiled at him. The worry vanished instantly. "Good. I didn't know what to expect." I bent over and slipped my heels off. Don stared at me lustfully. I sat down at the edge of the bed next to him and raised my hair off my back. "Unzip me?" I asked innocently. Don rubbed my back for a bit, then answered. "There's no zipper." "Oh? There isn't?" I teased. "Guess you're just going to have to pull it off." I winked at him over my shoulder. He grabbed my hips and drug me towards him. I laughed gleefully. Month 10 I stared into the mirror. I hadn't worn the Babydoll outfit in a couple months. Even though it didn't seem possible, Vicki had lost interest in the film over time, and stopped expecting me to dress in it everyday. So I was pleased to see how I looked when I put it back on again. I had wondered what I would look like in this costume with an ass, womanly curves, and breasts. And the answer was sexy. Sexy as hell. There was gonna be a lot of trick or treaters out there that were going to have to use their candy bags to hide something I gave them... "You ready Babydoll?" Vicki asked from the door, wearing an "Elsa" from Frozen costume. "Definitely sweetie!" I answered. "Let's go! It's already getting dark! I don't want to miss any candy!" Vicki rushed off. I looked into the mirror one last time and blew myself a kiss, before heading for the door to introduce Babydoll to the world.