Becoming Miss Cooper Ch. 01

This is a transformation story. There is masturbation in this story but it is not the main focus.

Thank you so much to my editors for all your help.

Chapter 1

My name is Jared Cooper. I am 4'11" and I weigh maybe 85 pounds. I am Chinese with slightly yellow-tan skin, but get mistaken for Korean or Thai all the time. I have light brown almost golden eyes. I have jet-black hair but I only seem to be able to grow it on top of my head and in a very small patch around my very small penis. I would say I look like a girl, but since I have no breasts, so if I look like a girl, I look like a tomboy.

I'm 22 years old but get carded to buy R-rated movies and over-the-counter medications because I look so young. I have an associate's degree in business and I am working on my bachelor's in Architecture. I love to draw and thought my life was pretty good. When my mom passed away everything changed.

My birth Dad left my mom when I was six and my mother remarried when I was eight. My new dad's name was Timothy Cooper. He was 26, six feet tall, and maybe 200 pounds. He is African American with bronze-colored skin, a shaved head, and a short well-trimmed beard. I can honestly say I didn't like him at first. I had never had a stepdad but I had seen all the movies with an evil stepmother so I was very worried. Tim took it slow with me, felt that showing me he was a good guy was better than just telling me. He treated my mom like a queen and me like his real son. By the time I was ten, I had no trouble calling him, just Dad. He was the best Dad a kid could hope for, so when he called and told me my mother was very ill, I rushed home from school.

He had not wanted to bother me with my mom's failing health. I told him I would have preferred that he'd told me sooner, but understood why he had waited, he was trying to protect me, like always. Mom's passing came quickly but the effect of her illness had huge collateral damage to Dad, their home, and their finances. I asked for a leave of absence from school, and they said no problem and wished me the best. My job said if I didn't come back, I was fired so, I quit.

Dad worked for a warehouse supply company loading trucks with things like water, soda, and sports drinks. He worked 7 am to 4 pm, then came home after a quick stop at a local bar, Bill's, for one beer and to decompress from the day. Needless to say, after loading trucks all day he was pretty tired and was not really in the mood to do a ton of housework. I told him I was taking the semester off and that I would move back in to help.

They had left my room exactly how it was when I moved out, which was both comforting and slightly creepy. My mom had a good life insurance policy and had kept good records even in the last few months as she fell ill. I also knew all of her passwords as they all had to do with me or Dad. It took me a month to set all of her accounts right and pay all the bills. Even with Dad being gone from work for almost a month, in the end, we were doing OK.

The chore that got me into the most trouble was laundry. I knew how to do laundry, I had been doing it since I was twelve, it's what was in the laundry that proved to be my undoing. Like all the rest of the housework, Dad had let the laundry go. I was doing so many other things at first, I only had time to do a load or two a day which meant I was able to keep up with our day-to-day needs but only start to make a small dent in the backlog. Naturally, I knew where to put Dad's clothes but I need to figure out what to do with mom's old clothes.

My first thought was to throw them all in a box or a bag in the laundry room. Then let them collect until I didn't find any more and then take them to the local Goodwill. I didn't want to make a bunch of trips to the drop-off site, I just wanted to make one. Oh, how my life would have been different if I had just gone with that plan.

Clothes were the one thing that my mom never skimped on. My mother had great taste. I mean she wore stuff that any young woman would like. She mixed new designs with classic ones. She loved Asian-styled or influenced dresses. I considered taking them to one of those clothes exchange places, as many of them came from there, but they usually only gave you a few dollars for the clothes. Then I thought about selling them online but thought that would be a huge undertaking and I was not sure if anyone would buy the clothes of someone who had just passed away.

With nowhere else to put them I simply started to hang her dress up in her closet and put other things back in her dresser. I am not sure why I did it, probably because it was easier. Maybe it was because they still smelled of her perfume. Maybe it was just curiosity, but one day I was putting away some of her clothes and came across a casual short sleeve qipao dress hanging in her closet.

It was off-white and covered with waterlilies, a mandarin collar, and a little green toggle to keep it closed. My mouth went dry, hands began to shake a little as I touched it. The material was muslin and so soft. It was as if it was calling to me. I felt like Gollum from The Lord of the Rings. I stepped back and shut the door so I was not tempted to try it on.

The thing started to settle down. I found out I could take a number of my classes online but they would not start for a few months. I had cleaned every inch of the house. Every piece of clothing in the house had been washed or we were wearing them. Therefore, with nothing else to do, I went online and watched porn.

I sort of just wandered around looking at this and that. Then I found a video of a large man with chocolate brown skin having sex with a small Asian woman. I got seriously hard and kept watching. Imagine my surprise when in the middle of the video the man took the woman's skirt off and you could see that she had a small bulge in her panties, a little later her panties came off, and you got to see her very small dick waving limply in the breeze.

The ladyboy had been wearing a jean skirt, fishnet stockings, and a hot pink tube top. I started thinking how much hotter she would look wearing the dress in mom's closet. I also thought about how much she looked like me. I mean I would need to grow my hair out and I would never wear such garish or copious amounts of makeup. I know this was for a porn movie but come on, she almost looked like a clown. Other than that, our basic body composition was the same right down to our small dicks. Mine is only three inches long even with me as horny as I was.

I passed the next few days doing my chores and then spending a lot of time online looking at Ladyboys, T-girls, and transexuals. I also found myself straying to a site with mature African American male pictures too. I found a ton of videos on everything from applying makeup to stuffing. Every day just before starting my evening duties I would go into mom's closet and look at her clothes. I was growing bolder by the day. I hadn't put any of her clothes on, yet, but I did hold a couple up to myself and imagined them on me.

Dad couldn't believe how nice the house was now. Dad had always been a hugger but now it seemed like we were embracing and cuddling more and more. I have to say I didn't mind it at all. It was nice to be held by his big strong arms. I felt completely safe. He said it was because he was going to miss me when I left for college again. The truth, I think was more that he missed mom but I understood and was enjoying the physical contact either way.

I told him he didn't need to worry about me leaving as I was not going back to school. He got a little upset but I settled him down by explaining that I could take a number of my class online for now and transfer to the local university down the road if needs be. I told him he needed me. He said he didn't but then he looked around and agreed he did. He joked, "You are going to make someone a very good wife someday."

"Only if I can be your wife Dad," I replied. He was silent. I don't know why I said it. Obviously, my heart and brain agreed or it wouldn't have gotten to my lips. Later I would wonder if this was the moment, I planted the seed for events that would happen later.

I had gotten my clothing addiction under control. I was only going to look at mom's clothes once or twice a day now. OK, three times but who was counting? One of the things that helped a lot was I started wearing my mom's panties. I took most but not all of them out of her dresser and hid them in mine, under my boxers. Then I spread her remaining panties, stockings, and bras out in her drawer so no one would notice their absence.

I started by wearing mom's panties for only a few hours a day. The time it took to change back and forth between hers and mine became tedious and besides, they felt so nice. I know it sounds weird but I rationalized wearing her panties by telling myself that I wouldn't have to look at her other clothes as much because I was wearing some of them. It's amazing what you can tell yourself to excuse an addiction.

Then one day the ancestors, God, Buddha, or I personally think my mom intervened. I was 'organizing' mom's closet for the thousandth time. When I found a box of treasures. My mom had known about her cancer and had planned for the future. In the box, I found a synthetic hair wig fashioned in a bob haircut with air bangs, the style she always wore. I also found a mastectomy bra with breast inserts that ranged from size A to C.

I carried the box back to my room and hid it under my bed. I felt like I was a teenage boy hiding my porn stash. I left it alone for almost an hour before I nervously went back to my room. I started with the wig as I figured that if Dad came home, it would be a lot easier to explain me wearing a wig than me having fake boobs. I watched a quick video on how to put on a wig correctly and then went into my bathroom.

The video said that head size was very important to get a good fit and look. Well, my head must be the same size as mom's because it fit me almost perfectly. I had to tighten a little Velcro strip but not too much. I tried to brush it like real hair and it didn't move. I found this nice gel band in the box and decided to try that quickly. I was just as secure but didn't make me feel like I was wearing a wig. I looked in the mirror and saw my mom, much younger, looking back.

Figuring I had pushed my luck as much as I dared. I put the wig and gel band back in the box. And watched several videos on wig care. I knew that my hair was already pretty long but I wanted at least 3 to 5 more inches. If the lady online was right this wig would just about get me halfway there. There seemed to be a debate as to how long a wig would last. I figured with light use it should last me at least 3 or 4 months.

The Next day was busy. I paid bills and ordered groceries for online pickup. I had other non-grocery shopping to do as well and some grout to clean. It turned out that after an hour the grout was going to be easier to strip and replace than clean, so that is what I planned to do in the coming weeks. Long story short I didn't have time to get back to the mom's clothes.

To reward myself for not looking at mom's clothes all day, I decided to figure out the mastectomy bra and then try on that dress. I was already wearing a pair of black panties that matched the bra. Figuring bigger was better I pulled out the biggest size fake breast and put them in. I looked in the mirror. The insert sagged every time I moved and then fell out completely. Back to good old YouTube.

I had put the breast inserts upside down and not in the little pockets designed for them. I decided to reverse my path and choose the smallest inserts. The good news was I got the inserts in the pockets and the right way up. The bad news was they were uneven. I played with them a little and got them a lot more in line. Then I found an article that said they don't have to be even as many real women do not have perfectly even breasts and I felt better.

I looked at myself in the mirror with the bra and panties and was amazed at how much of a difference it made. I mean I still looked like a boy but now I was a boy with breasts. I moved up to the B-size inserts. I liked the way they looked and they felt right. I put a regular t-shirt over the bra and I could defiantly tell they were fake but at a glance, they kind of looked real.

I ran to my mother's closet and grabbed the short sleeve Qipao dress I had been admiring for a month. I scooped the wig out from under the bed and went to my bathroom. I put the band around my head at my hairline. My hands were shaking so badly that I had to do it twice. I put the dress on and then mom's wig. I straightened a few stray hairs and looked in the mirror.

I was shocked. I was not an unattractive man but I was a pretty girl. And I say girl because dressed like this I didn't look 22. I looked like a girl on the verge of womanhood, just barely 18 at most. I wondered how much younger or older I would look with make-up.

The dress was supposed to fit the wearer tightly and it was tighter than anything else I owned but not as tight as it was on the girl on Amazon. It was also supposed to cut off halfway to my knee but because I'm so short it went 2/3 of the way to my knee. The slit in the side came up to my lower thigh but not high enough that my panties were showing, bonus. My fake breasts seemed to magically know where to go and the tightness helped hold them in place. I was liking this dress style and this dress, in particular, a lot.

I pondered wearing shorts under the skirt for extra protection. Then I smiled at the idea of not wearing panties at all. I thought that nylons or very high thigh highs would work best with this dress and made a note to see if mom had any or if I would need to get some on my next shopping trip. I did remove my panties and it felt so freeing.

The image of the porn I had watched over a month ago flashed into my memory. I bent over the sink in my bathroom. I took the place of the girl in the clip. The African American man just pushed my skirt up and started fucking my ass. I, in reality, started to play with my little dick. "That's it, Daddy." I said to the empty bathroom, "Fuck me. Fuck your little girl."

Then my brain turned the guy into Dad. Instead of playing with my dick, I started fingering my ass hole. I didn't get my finger in very far before it started to hurt. I found some KY jelly I normally use for jacking off and put some on my finger. I straightened up so I could get more of my finger up my ass. "That's it, Daddy. Fill your little slut." I cooed again to the thin air.

My cock was at its full erection. I knew it was wrong to dream of Dad being the man that was pleasuring me. Hoping that Dad would take my virginity was out of the question. Dad had never said or done anything that even hinted at him being gay or bisexual. Why was I setting my sights so high or so dirty depending on how you thought about it?

I didn't have any toys but if today was any sign of what life was going to be like I was going to need to get one or two. The thought of having a dildo handy for times like this was keeping me hard. I thought of a butt plug being up my ass while I stroked my cock. Then I thought of having a butt plug up my ass while wearing the dress. I began to grunt and breathe heavily. The image of Dad went through my mind again and a little squirt of cum shot from my pencil dick.

I looked down in horror. I was so wrapped up thinking about dildos, toys, and Dad, I had just cum all over the inside of mom's dress. I was frantic. What should I do first? Take off the dress? But the cleaning supplies were in the house. What if someone saw me and told Dad? It took me several minutes to get my thoughts in order. I removed the wig and the jell headband. Then I removed the dress and hung it in the shower. I took the bra off, put it back in the box, and placed the wig lovingly on top. I made a mental note to see if I could find a manikin head or something to put the wig on to keep it nice.

I ran to get club soda and a wet cloth. I checked the tag and it said the dress was machine washable but I didn't want to risk it. I dabbed at the spot with the club soda and other than a wet spot it looked fine. I hung the dress back up in mom's closet and realized it was nearly 4:30. I had been playing dress up for hours. I needed to make sure that didn't happen again.

I still couldn't get focused on my chores. I went through mom's makeup and found most of what I needed but not all. I made a list which took another hour so we had sandwiches and chips for dinner. If Dad noticed anything he didn't say anything. "Hey, Dad. I have some errands to run tomorrow. I may be a little late. Can you grab dinner at Bill's?" I asked.

Please don't ask me where I'm going. Please don't ask me where I'm going. I said to myself.

Dad laughed. "No problem. In fact, it works out nice I can stay and watch the game." He took a bite of his sandwich. "I'm a little relieved to see you're going somewhere other than the store." He said with an exaggerated breath, "I was starting to think you were becoming one of those, stuck-at-home people, agoraphobics." He popped a chip in his mouth. "You need any money?"

I wanted to say to him, I do the household books, but just said "I've got cash."

Chapter 2

Dad left the next morning at 6:30 am and I had promised myself I would wait. I mean to wait till noon but only made it to 7:25 am. I felt bad about not telling Dad the whole truth about where I was going today but I didn't exactly lie. I did have errands and I was running them. I just didn't tell him I was running them in a town 45 minutes away.

I arrived in Centerville at about 10 o'clock. I spent an hour at Walmart buying make-up, thigh-highs, and three pairs of really cute Mary Janes in black, dark green, and brown with pink flowers. I got the car's oil changed too as the little sticker said it was three months and 600 miles overdue.

Next, I stopped at a cosmetic supply store to try and find a make-up head to practice with and to use as a wig stand. I couldn't believe that there were 20 different heads for people of European descent but only one if you were African American or Asian. And it wasn't cheap. The sales clerk, who was also Asian agreed with me and so knocked 50% off of it.

My last stop was the one I feared the most, Adam's Adult boutique. It was also why I had planned to leave at noon and not be at the store by noon. I figured showing up at an adult supply store in the middle of the day would mean it would be deserted and judging by the parking lot I was right. I had thought about ordering toys online but was worried about what would I do if the package came after Dad got home.

I walked through the door and an electronic bell chimed. "Hey," came the voice of a very nice-looking man who had just come through a beaded curtain. He was fortyish, six feet tall, and had a dad body. His skin was mocha-colored, with brown eyes and long black hair that he kept in a ponytail. "I'm Sal." He introduced himself, "I own the place. I have some stock I'm working with back here. Take a look around and hit the bell if you need anything, OK?" He walked back through the curtain and then stuck his head back out. "Cute guys like you always get 10% off everything."

I was not sure if it was just a sale pitch or if he was serious but it made me blush and my dick started to tingle. As I suspected the place was empty. There were some cool statues, one of a dragon, "Wow Dad would love this for his birthday." I thought out loud to the empty store. Then I saw the price and very carefully put the statue back.

I looked around the store for probably half an hour. I found a pack of three butt plugs that I had seen online and had been recommended for beginners. I also saw an anal toy that was also a vibrator that had pretty good reviews. Even with the promised discount I could not afford both so I was trying to decide which one I wanted more. I became aware of how long I had been standing there and so figured I should wander around looking at other things while I pondered which toy, I wanted more. I then found myself pulled towards the club wear and Cosplay section.