7 comments/ 35090 views/ 30 favorites Dena and Annie Pt. 01 By: daisyboi_sissy This story is a complete work of fiction and is only to be taken that way. If Transgender sexual ideas offend you then do not read. If you are not above age 18 then you should not be here anyhow. ***** Dad and I were left alone when mom decided to walk away from both of us. She said she did not care about the house or money but had to leave. She had withstood Dad's work alcoholic lifestyle and just being a housewife was not what she wanted her life to be like forever. My Dad's name is Ray Owens and I am Daniel - his only child. This all happened 4 years ago and today we live in the High Port community near the coast. Dad and are the original co-occupants of this big house he calls "Casa De High Port!" I have an entirely separate section of the house to myself for whatever I want to do all day. I cannot be blamed for being fortunate enough to be born to a filthy rich Dad. I have managed to live my life well under his radar and I have an allowance that would make anybody happy. I have never asked for a lot and what I wanted I could get for myself. At "Casa De High Port my Dad has some really ritzy parties and spends a lot of money putting them together. I know when they are happening and I always prepare for it so I will not be around. In my little world I can tune out all their noise and drinking. I have peeked from my window before during some of his pool parties. And I have seen some partiers end up without clothes. I have seen three of dad's best friends in their birthday suits before. A few of the ladies have lost clothing before too but none were ever naked. The pool house got a lot of visitors on those nights also. Folks coming out trying to act as if they weren't just frigging like rabbits. Only after the crowd leaves do I get to hear Dad and Annie pounding the headboard. Then they crash hard to sleep until lunch the next day. "Annie" is Dad's new wife and she is one of the prettiest and smartest women I have ever known. If she is wearing jeans and a tee shirt most women coo to be like her. A miniskirt, heels and a little Annie, that woman could stop a train. She works out hard in our gym and has a very good diet. It is really hard to find a flaw in this woman sometimes. She first made a slight friend with me when we met because she took dance lessons at the same place I took advanced dance glasses. Through my school I was given a scholarship to study there four hours a day and all my other classes were done online. In the fact that I am never at school is a huge plus for me physically and emotionally. Since middle school I have been the target of excessive bullying at school. Dad wanted once to have me attend private school but I talked him out of it just in time. I have only had one real friend in years from school. Dena Lee was in the very first dance class I ever took. We became friends that year because my mom then would take us home from the lessons. Dena's dad had his own company and was probably the richest black man in our community and damn sure the best looking. He has a voice like a machine and is very nice. Our neighborhood consists of only about 30-40 homes set on a golf course. All 5000-6000 square feet houses are manicured like your mommy's nails. When Dad and Annie married I got a makeover in the deal. Dad spent a bunch of money remodeling my wing of the house. He even added a large garage of my own. Annie has been responsible for the decorating and she is fantastic at it too. My dad met "Annie" when his company purchased the property where the dance studio was housed in the Becker Mall. It was on a recommend-ation from Annie that Dad bought the property. He says it was one of his best buys to this day. The owner was a lady I still see at dad's pool parties with her husband. Mr. Dean is one of the ones I have seen "au natural." One a scale of one to ten Mr. Dean rates a stiff 9.5. I have seen it open for the world to see one night. Everyday I leave the dance studio I get to walk by the Victoria's Secret store every weekday and on Saturday. I did walk inside one day to look for some leg warmers to use in my dance class. The Saleslady was very nice and knew I danced nearby. She remarked to me how cute and happy I seemed to her. Her name was Eve and was pretty to look at as she chatted with me as I looked around. Then she spoke telling me "The leg warmers are expensive enough that it qualifies for five of these panties for free if you will tell me your size." She was pointing at some tiny bikini panties in stripes and polka dots. I whispered a size 4 before I could catch myself. As the lady selected five items and most of them were pink. I smiled and brushed it off and made my way to the checkout. "Will there be anything else I can help you with today Honey" she said. I wanted to say "Hell Yea could you please show me some white garters and thigh high stockings Ma'am!" Three women in the store looked over at me and smiled as I turned a couple of shades of red. I grabbed my credit card from a small bag I carried to pay for my stuff. "I put you an extra pair in there too sweetie. Enjoy them! Smiling to each other the lady and I parted ways. The new panties would be pretty with the new leggings I bought from Macy's and a white top. The remodeling of the house, Dad marrying Annie, all ran right up to my 18th birthday. Dad bought me first class tickets and hotel stay to go see Lady Gaga in concert at $2000 per ticket. A friend of Annie's picked me up at the airport and got me to my hotel and I took a cab to the concert. It was the trip of a lifetime for me to go and dress just as I wished too for two days. I wore a really sweet black mini dress I purchased online from Victoria's Secret. I wore black tights and 3" ankle boots. With my small frame I need a little help in the rear occasionally. I spent $400 on a shape wear piece to enhance the ass in a dress. A little bit of lip gloss, something to darken my eyelashes, added a slight hint of foundation, toss my studded earrings for some cute chandelier ones and three sprays from my new Estee Lauder perfume. I stood in front of the huge mirrors to pause and see if I looked silly or good enough to kiss. Opting for the kiss as I snapped a few pics of my new look. I even snapped five or six sexy selfies for good luck. I had never stepped out of my house dressed anything like this before. The mini dress was made from my five foot two frame as a mold. I had no trouble remembering to shake my ass a little when I walked as this dress restricted most movements. Men will never understand the power that is in the female form. I desire the feeling and something tells me I can become that person. The concert was greatly orchestrated and I had a wonderful time being there. Lady Gaga sang with a piano and a couple of dancers but very pleasant to the eye. She has a beautiful voice that we don't usually hear. The event was handled as semi formal attire some very handsome men were there. Realizing I presented myself as something slightly older, men have very subtle ways to get your attention. And some can keep it! I was exhausted when I made it back to the hotel. I opened the door and saw there were two bottles of wine on ice in the room for some reason. I saw a note with the gift and I opened it to read. "Sweetie I sure hope you had a blast at the concert. I hear you looked great! Hurry Home! We've got a surprise for you sweetie." "How did she know how I looked and what's the surprise? Damn!" I yelled out. Her friend must have seen me when I left the hotel. I decided to have some wine as I got undressed. The wine was red just like I like it and Annie knew this from catching me taking two from a party once. She swore she wouldn't tell Dad and I assured her I was not an alcoholic. Once a week I do it to loosen up and relax I told Annie. "Careful that stuff will make you lose your underwear sweetie" she said laughing. As I undressed I filled the huge tub in the master bath of the suite I was staying in with steamy hot water. Relaxing and stretching in the huge tub I put away four glasses of that red wine. Reaching into my bag I retrieved a 6" plastic cock and some lube. The dildo attached nicely to the tub and I leg split over it and fucked myself silly with the toy. I almost screamed when I came because it was so good. I slipped on a sheer pink chemise and matching panties to head for bed. "I hear you looked great! Hurry Home! We've got a surprise for you sweetie." What in the world could all be in that message? Night Night!! I arrived home Monday afternoon from my birthday trip in a cab from the airport. I caught an earlier flight and didn't tell anyone I was coming in early. When I got home Dad and Annie were there talking in front of the house. They both yelled I was early and how good I looked after the trip. We all hugged and both gave me a kiss. I was surprised Annie kissed me since she had never done that before now. Dad never shows any emotion so he catches a call on his cell phone as we chatted - work I am sure of it. "Well tell me about your trip sweetie and how it went in Chicago. I am sure you had a good time since we didn't hear from you the whole time" Annie had my attention fully as Dad was just occupying space on the steps. "How and what did you mean in your note with the gift in my room Annie" I asked. Immediately she got Dad's attention and said "Let's go see the surprise present Honey!" We all walked around to my garage and Dad opened the door with his cell phone. There was sitting a bright red BMW 650i with a red bow on it. "Dad!" I yelled out and covered my mouth. "I cannot believe it Dad!" I almost screamed. I ran to it and sat down inside to look around. It was like the biggest thing I had ever received. "In a couple of years you can sell it and put a down payment on a house if you wish" Dad said to me. I could only laugh and almost cried a little since I had no idea my surprise was anything like this. Annie walked over to the car door and leaned down to me and spoke. "Yea my friend in Chicago saw you when you left the hotel for the concert. She also sent me pictures from the hotel's cameras of you looking really sweet in that black mini dress sweetie. If you wish we can fix it where you won't have to wear fakes to get the look you want on that cute little backside you have. You must have gotten your Mom's hips or from so much dancing. Like I said sweetie I can help you a lot if you wish to be that pretty little girl you want to be!" I answered her by saying "I have always wondered why it is that you never call me by my name, but sweetie? I like it but I just have wondered about that quite often Annie. "I like you a lot and I know you are good for Dad. You know I would love to be more like you than anything right now. I think you are remarkable and I know I never told you that before and I am so damn embarrassed" I say all that laughing like I was drunk or high. "Sweetie I have been able to read people all my life. Your Dad even takes me to some meetings to help with evaluations about clients. Since I laid eyes on you months ago I never saw a Daniel inside of you. I want to be your friend and maybe even your best friend. We can spend some time together next week because your Dad is going to Boston first thing Monday morning. I hope you don't mind me being nosy but, when I helped redecorate awhile ago I looked through your things. She just kept talking and I listened to her like a student to a teacher. (I kept two boxes under my bed. Each one is half the size of a king bed and they are nearly full of my "Stripper Goodies." Dad never checks my credit card bill if it doesn't get above $500 and I am a smart spender. Plus I have my debit card and a checkbook) "There are several envelopes waiting for you on the dining table when you go inside. I am guessing u have a couple thousand dollars in gift cards and cash. Your Dad's partner, Thomas Dean gave you a $500 gift certificate to the mall I know for sure. You can buy anything you want this weekend from the mall online. If we can go to the studio early, by the time we finish your stuff will be ready then sweetie. Macy's, Limited, GAP, Estee Lauder, Victoria's Secret all can be picked up if your order early enough" Annie spoke again like my guide. "I would love to have you for a best friend Annie. You know more about me already in less than a year than Dad has figured out all of my life. Dad did mention he was going to be not here for a while but did not say how long. I am really looking forward to Monday now Annie given what you just said. But I have just one more question for you Annie. If you see me so differently than what my real name is, what would you have my name be instead." I said. "As pretty as that cute little face looks and the sweet voice you have, I have often seen of you to be an Dena. Dena Owens! That's pretty! And I am going to help create Miss Dena Owens. Do you think we can do it Dena? "You and I" best friends" Annie says with a really pretty smile on here face. "Yes Ma'am I think we can do just that!" I say as I start my new car to back out of my garage. I wave to Dad and Annie as I go off down the long driveway. "Dena?" I like it! By 6 am I had showered and dressed to meet Dad and Annie for breakfast. Dad was behind his newspaper talking to us about his trip. I wore a pair of black yoga pants with pink stripes on each side. I slipped on a really pretty pair of pink French cut panties. I had taken them from Annie's panty drawer a week ago. They were very nice and my skinned feel in love with them the first time I put them on. An oversized black shirt that fell off my shoulders revealing what could have been mistaken for a sports bra. The night before I had thoroughly washed and conditioned my hair to look good. I put it up behind my head in a red scrunch and pulled it tight. Being pulled back like that still almost hung to my neck. Annie smiled at me as I walked into the kitchen and I could see something in her eyes that meant something was very different. Puckering her lips, she blew me a small kiss since no one was looking. After I hugged Dad "Good Morning" I smiled and took a seat across from Annie. My favorite Step Mom in the whole world was dressed in a very pretty white lace top and black stretch pants with four inch heels. This woman looked like a million bucks at six in the morning. She was showing off just enough cleavage and just enough brains to make any man desire her. Even her eyes, lips and face could cover a magazine. I looked down and saw a plate of fruit and a small bowl of cereal. A banana cut into two pieces with lots of strawberries, apple slices, cantaloupe and peaches. "Sweetie I hope you like what I prepared for you this morning. My dietician said all those things are good for energy you need before hitting the gym. I am glad we are going together this morning and we have a whole day to just us sweetie!" Annie said. Dad didn't close his newspaper the whole time we ate breakfast. A knock on the front door let us know that Dad's ride to the airport had arrived. We all hugged and said our goodbyes on the front steps and the car pulled away. ----------------------------------- "Well Dena, you ready to see how much fun we can have today? Do you prefer to go workout or let's just have an Annie and Dena Day? "I was hoping we could talk this morning Annie. I have no idea what to expect from today or this week we are about to have together. You obviously know more about me than anybody and I am not sure if that is good Annie. Your aspirations for me seem to be way ahead of who I am right now. You spied on me and found out things that until now were secret. "My secret" I say as we are walking up the steps and into the house. "Do you like the name Dena, Sweetie?" Annie asks me. Trying not to answer wrongly I hesitate to answer a few seconds. "Yes I do like the sound of it when you speak to me Annie. But I am not sure how it might sound elsewhere, or from somebody I know" I reply. By this time we have made it back to the breakfast table to take a seat. "Dena! And yes I do love the sound of that name. I just want to talk to you and become closer friends Dena. Since you don't allow anyone your own age to get close to you sweetie, I figured you might like an older friend. If we can get to know each other better and I am sure we are going to find things that we like to do together, places we like to go or just enjoy hanging out together. Dena I see something very pretty, beautiful, you're smart and so much more that I know you are keeping secret. You are way more to be found out than I think even you realize Dena." I listen as she speaks in a way that sounds like a teacher or speaker. All on time and right on the spot, with nothing wasted. "Dena I am not being brash or conceited when I say that most men find me attractive. I am totally dedicated to your Dad Dena but I know men very well. You on the other hand do not seem to find me to be something even remotely desirable. Men are not nearly as complex as they think they are sweetie. They have needs that we are able to exploit and use to our... pleasure, for lack of a better word" Annie spoke and finished touching the side of my face. I felt for the very first time in my life like a young girl who was being given the birds and bees talk to by her mother. If Annie's intentions were to make me feel like she was talking to a young girl then she was successful. I had never gotten this feeling without having my little rear end filled by plastic, but I wasn't telling her that just yet. I picked up the half banana and put it to my mouth without noticing how I looked before putting it to my mouth. Annie has my attention so good I put the banana to my lips and catch myself suddenly. I wrapped my lips on that banana like I was accepting a gift of COCK! My eyes opened a little and Annie was looking right at me. I burst out laughing but, she kept her composure a lot better than I did. "Don't laugh at me!" I yell. Turning my face away from Annie as I regained my composure, I laughed even more. "Should I add more bananas to the grocery list Dena? You seemed to enjoy that one a whole bunch. I can also check to see if we have any cucumbers that are fresh if you are looking forward to lunch sweetie. I thought we would head to the mall to pick up our orders. You did do some shopping last night didn't you Dena?" Annie asks. "Yes I did order some stuff last night with the money I received for my birthday. Mr. Dean did give me the $500 you mentioned and that was the one I used. He also left a picture and his business card in the envelope. Which I thought was kind of odd." I told her. Annie told me that she also did some shopping for me too. Saying she bought me some stuff that I probably would not buy for myself. That caused my brain to begin asking all sorts of questions. I am also expecting a couple of UPS orders here today for you too sweetie. We both were finished at the table, so we grabbed our plates and walked to the kitchen. I had never been so giddy around an adult as I was with Annie this morning. In the kitchen we put our plates and silverware in the dishwasher. I leaned back against the counter as we chatted. Annie stood next to me and popped a huge question. She stood closely in front of me to talk. "To get a little nosy Dena may I ask you something? Why don't we dress you a little differently today since it is going to be an all girl's day? We can skip working out and see how much fun we can have. Let me see what I can do with that pretty head of hair you have and test the waters a little for Miss Dena!" Annie says. "But I am not sure if I am ready to test the waters Annie. It is a world of difference in having fun in Chicago and right here at home. If people see you and a girl what are they going to think? They know you don't have a daughter and I would die if I was found out!" I reply. Dena and Annie Pt. 01 "Dena you keep seeing what could happen that is bad and I prefer to see what awesome thing might happen for you. I want to be your enabler and encourager for what it is you would like to do Dena. It is going to be more fun that I think either one of us can imagine. I will be here with you throughout this sweetie and please trust me that I won't let you down." Annie speaks again and it feels like she is reading my face for the questions I have. "All of these ideas sound like a good idea Annie and you know you have my attention. I will try to see things more like you do and see how I like it. And I am also hoping your taste in clothes rubs off on me Annie!" I say to her smiling. I exhale like I have just passed a kidney stone. The look on my face probably still shows some concern. Annie looks at me from head to toe slowly. It is like she is trying to figure out where to start. She point to my feet and makes her way up to the top, "Heels, Skinny jeans - low cut black skinny jeans, something cute underneath, white top fitted nicely, white lace bra A+ cup, jewelry for the neck and ears, trip to Estee Lauder Studio and I will surely have to call Gia to work on your hair sweetie." She says. The second Annie finished talking, the doorbell rang. "Your A+ cups are here sweetie!" she says walking to the door. I hear an exchange and Annie comes back to the kitchen with three boxes. "Is Dena ready to have the time of her young life? It is going to be a whole lot of fun and I can't wait! Let's go upstairs and pretty up my favorite little girl in the whole world. And when we are done we are going to show her off to everybody!' Annie says as she grabs my hand to lead me upstairs. We walked into Dad and Annie's bedroom, as she still has boxes in her other hand. Annie had a large area in the room where she dressed and it held her huge wardrobe. She told me to have a seat as she gets some stuff together- which I was not sure what she was getting. "Dena do you have a problem with me seeing you naked?" Annie says as she walks back to where I am. "No I guess I had better not be afraid to with the pep talk you have given me. Should I undress Annie now or what? I ask. "Please if you will slip off your yoga pants and top please. I have the outfit I want you to wear today ready but, I would also like to see what we are dealing with here." She says. I slipped off my shoes, yoga pants and my top. No one has ever seen me in this much skin since I was a small child. I fixed my panties as Annie began to laugh at me. "I knew you must have been where a pair of my new Bali panties disappeared too." Annie says. I can only reply with a giggle laugh. "I do admit that the panties seem to be working for you sweetie. They look almost as cute as do you Dena. Have you moistened those this morning with all the girl talk we have been having?" Annie asks. She moves up to my side and puts her arm over my shoulder. I feel her hand on my side as she slides it down to my hip. Just like on cue I can feel Annie's warm breath on my shoulder and I love it too. I flinched a little as she does that and her fingers touch my tiny bulge. "Sweetie I want to see if it is as pretty in person as it is in a selfies on your laptop!" Annie tells me. Her finger goes to my lips to stop me from speaking. I comply and keep my sound to a slight moan to the feel of her touch. My panties open and my tiny cocklet pop out in front of me. "Sweetie it is beautiful!" Annie exclaims. "I absolutely love the look of it on you. You sexy little nymph you!" I hear. Her fingers tease me as it sticks straight out like a tiny pencil. "No wonder I don't ever see a bulge under your dance outfits. You can tuck that it in and no one will ever be the wiser" Annie says to me. Her hand massages my tiny balls while holding me close to her body. I feel her press it into me and looks to see how easily it is hidden. Her hand covers my crotch and it appears to vanish completely. My head fell back to Annie's shoulders as I was melting in her hands. Annie's voice goes to a whisper and I cannot believe what she says next. "Do you wish you were being held by your Biology teacher right now Dena? Do you imagine him doing this to you in your dreams when you sleep sweetie? I am sure he would not let you off as easy as I am about too!" Annie speaks as I absorb everything she says. Her hands rise up to my chest and she finds my tiny nipples under my top. "You didn't answer me Dena and I want to know!" I turn my face to Annie and is really slow to speak. "How do you know that I... I mean no one knows about...:I murmur, still panting like I have been whipped. "Honey, of all my talents I am a whiz at hacking people's computers. I have read the captions you put on those pictures hidden on your laptop. There is nothing at all wrong with wanting a man to find you desirable Dena. I had a crush on my high school teacher too. The next thing to do is make him want you like you have wanted him! Maybe before long you can pay Mr. Lee a visit to see if the feeling is mutual Dena. We will do our best to make sure that he will want you as his little teacher's pet. "Yes I do have a crush on Mr. Lee! You read it for yourself if you hacked my computer. It's not fair that you know all of this, but I guess it isn't an issue now. As for me getting a chance to see him other than at school, I know that is crazy. That at best would be something that may never even happen." I tell Annie. We are really close, face to face standing in the bedroom. "Dena when you speak about it your tone changes and your breath gets deep. You must really want this man pretty bad honey! I have to meet this Mr. Lee to make sure he is good enough for you. If he is your knight in shining armor, he better get ready for my scrutiny or approval. We need to get you ready for your special day today Dena. I have a very special gift for you today, that is going to change so many things for you sweetie. Hurry and go clean yourself really good and use some of my new perfume so we can get ready. I tiptoe off to Annie's bathroom and used a warm cloth to freshen up. I added a few sprays of perfume and headed back to my sweet lady Annie. Annie had been preparing my outfit and was laughing as I entered the room. "Hello there sweet thing! Slip on this sweet patch thong to cover that little button you call a clitty and these jeans." Annie instructs me. I do as I am told and I have to maneuver my ass to get the jeans all the way up. And that mean I love them already. I look to Annie and she has in her hands what I have been wanting for a long time. I could tell when I saw them that they were very close to the color of my own skin. Annie had purchased me a set of magnificent breast forms for this day. My mouth fell open as Annie looked at me to see my surprise, with the new gift. "They were made especially for you sweetie. I sorted through numbers of them to find these for you Dena. They should match your skin color which is a huge plus and the size should also be perfect to match your frame. Let me attach these for you and then you can put on your bra." Annie continues to instruct me. I look to the bed and there is a very pretty white lace bra that matches the thong. The added weight to my chest felt strange but I looked down at my new tits as Annie reached for the bra. I smiled really big as I touched my new addition and wiggled them a little. Annie held up the bra and I put my arms through the straps and she hooked it behind me. The fit of the bra to my breasts was a little bit snug so we adjusted the bra. Annie reached and grabbed them and smiled as she told me that this alone would make 50% of all women jealous as hell. "One of the biggest surprises you are going to have honey is exactly how powerful a sweet set of tits can be Dena. Men may notice you from a distance because of your clothes Dena, but when you are closer, a sweet set of firm puppies will keep their attention. That attention is what you are going to enjoy a lot and you will learn how to use it to get what you want from a man, And Annie also let me know this wasn't even close to what all she had in store for me. Next I put on a very pretty red top that left a bit of my belly showing. I slipped on a new pair of 2 inch black Versace heels as the last item. Annie mentioned my plain toenails and fingernails but said a trip to the salon was going to take care of that. At that point I reached up and hugged Annie's neck. I was so happy that my eyes watered up and I shed a few tears. "Thank you Annie for everything you have done for me. I am sooo... happy" I tell her as I keep hugging. "Look at me Dena! I am doing this because I know it is something you want so badly. We are going to make you into the pretty girl you want to be sweetie. When we are through there won't be a man in this town that won't empty his wallet if you ask him too. I'll be here for you every step of the way Dena, but I hope we get to decide where all those steps take you. Today you won't have to worry much about anyone in High Port seeing you Dena. We are going shopping two hours away and we won't be back until tomorrow if then." Annie grabbed my hand and led me to her vanity for "Special instructions in makeup application" as she called it. Lip liner and eyeliner advice was given since I had never used either one. She added some eye shadow, but said she didn't want to make me look like a street walker she said. With a soft sponge she added some color to my cheeks but not enough to be easily noticeable. I was anticipating the lipstick and was not disappointed as Annie had me pucker my lips. The feel of lipstick is a sacred rite for those who choose to wear it - Girl or Gurl! I looked to Annie before I looked in the mirror and I had to hold back the tears to keep from crying. I knew who I was looking at because I had wanted to see her for such a long time. "You are so pretty Dena. I am here to help guide you but, you will ultimately decide how far we go with this change. Right now you are happy as you may ever be sweetie. You have to let me know everything you feel, think and "ANY" question you have honey!" Annie says. It sounded a little like she had just gotten choked up similar to me. She then instructed me to let down my hair and let her brush it for me. I did as she said and we talked as she also curled under the back of my hair with an iron. "Since we know that a trip to the salon is inevitable, I think hair extensions would be a really good idea Dena. We may even add some highlights to this sweet head of hair too!" Annie says smiling slightly. Adding some hair gel and running her fingers through it Annie said she was done for the moment. We both stood up and faced each other once again like girls do I guess. Annie placed a kiss on my cheek and again told me how pretty I looked. There was one more box on the bed and Annie handed it to me. A very nice black leather purse was in the box. She handed me some lipstick, and other makeup to put in my new purse I closed it and put it on my shoulder. Annie picked up her cell phone and snapped a picture of me in front of the mirror. "Alright Dena I want you to give me a catwalk strut to see how all of our work is going to look when we walk into the mall to pick up our stuff. Always remember somebody may be watching you when you walk Dena. I want to see that tight little backside of yours twitching like your trying to catch a big fish! Annie says laughing as loud as I have ever heard her laugh. "I know I could easily be called "Silly" but you seem to act the part well Mrs. Owens!" I say smiling at Annie. We are walking through the house going to the living room. I feel so good playing with my favorite female in the whole world like this. "Annie I want to tell you something that you may like a lot, My "Mother" left me and Dad a long time ago, yet will always be that to me. Do you mind if I call you Mom instead of Annie? It would mean a lot to me if I could." I stop in my tracks to ask her. "That is the nicest thing you could possibly say to me Dena. I would love it if you would call me Mom, especially since you are my daughter. My sincerest hope is that my daughter will become all that she can be. I hope she follows her dreams whatever they may be. And her Dad and I will love her no matter what happens or whatever decisions she makes." Annie tells me. Annie's phone rings and I can barely hear a woman's voice on the other end. "Thanks Eve and we will be there shortly to pick them up!" Annie says to the caller. She clicks her phone off and says it was the lady letting her know that she has two large orders to pick-up at the mall. We are going to have all the clothes we need for a trip sweetie and I packed a makeup bag and another for our necessities. Annie hands me a really pretty pair of white shades as we head out the door. I could hear the clicking of our heels on the floor of the garage and it actually sounded rather cool. Instructions to keep my shoulders back, never frown and smile very chance you get Annie tells me. I do have to pull up my jeans a little as I feel them creeping down my hips. The drive to the mall is not very far from our house, so we make it pretty quickly. As the SUV stops Annie puts it in park and turns it off, "Let's go see Eve for a minute so we can hit the road Dena!" and she opens her door. "I thought...uh...I say as I open my door too. "C'mon silly the mall isn't even open yet. No one will see you but us Dena!" Annie says laughing as she walked away from the SUV. Taking short steps I try to catch her before she gets to the door. We walk to an employees' entrance to the mall. As we do Eve greets us with a cart loaded with boxes from different stores. "How are you doing Annie? It is so good to see you today!" Eve says as we meet. Then she takes a look to me and you can see her face change quickly. Her mouth doesn't fall open but it does show her confusion. "Eve I would like for you to meet my wonderful daughter Dena! We are going out of town to have some girl fun while Ray is out of town on business. We each have orders here but we can sort them out later." Annie tells her. Eve's eyes are still stuck on me like she cannot believe what she is seeing. "Dena you sure are one pretty young lady and it is really good to see you... again. You certainly do have a pretty young thing here Annie and you had better keep an eye on her. We wouldn't want too many hearts to get broken by this girl!" Eve says as she looks at me amazed but I know she recognizes me. "Thank you very much Eve and thanks for the free pair of panties the other day in the store!" I say smiling back to her. "Anytime sweetie and I do hope to see you in the store again sometime soon. I will be sure to show you around and help with anything you may need Dena." Eve replies. Eve then remarks to Annie again about how pretty I am and we start to put the boxes in the SUV. "Thanks again Eve and we are headed out of town for the day! Dena and I have a big day ahead of us and I cannot wait!" Annie says smiling really big again. Driving away from the mall she asks me about how that went for me to meet Eve. I replied that it was fun and I am glad that Eve is such a sweet person. Annie replied that yes she is very nice. Dena and Annie Pt. 02 This story is a complete work of fiction and is only to be taken that way. If Transgender sexual ideas offend you then do not read. If you are not above age 18 then you should not be here anyhow. ***** On the interstate I grabbed us a drink from a cooler Annie had prepared for our ride. She made remarks about how perfect the outfit was for me. Also how she could not wait to see what else she could dress me in later. "So tell me about this Mr. Lee that seems to be the object of your affection sweetie. And tell me what makes him so special" Annie asks. I tell her that he is a first year teacher and fresh out of college. He is tall but not too tall that makes him dorky. He has a dark complexion and dark hair that is always in place. He has made remarks in class about how he is a trust fund baby and teaches because he likes it. He says his family lives in California and he seems so different than other teachers. He is very polite and has always been nice to me when other teachers just think I am weird. Mr. Lee remembered my birthday the other day and sent me a sweet email too. I catch myself talking like I am a girl who has found her first boyfriend. When I look to Annie she is smiling and I have this deer in the headlights look. "What? Did I do something wrong? Why are you looking at me like that Annie?" I say out loud. She says "It is going to be so much fun watching you mature just like a little girl who kisses her first boy or has her first date with a man. You are so giddy just talking about your Mr. Lee. I cannot imagine how many times he has made your little panties wet thinking about him as you lie in bed honey!" "Enough about him and I will make sure I introduce myself to him before too long. He still has to pass my test before I give him thumbs up to let him see what I see right now. We need to take care of some essential things right now anyhow. How do you like the idea of being Blonde Dena? I forwarded your picture from the house to a very special friend of mine in Charlotte. She loved the pics and said she would work on some ideas for our appointment at 11:30." Annie tells me. I find out where we are going when she stops in front of a very nice looking white building. In the parking lot are Mercedes', BMW's, two limousines and Jaguars. An attendant opened my door and I stepped out as he held my hand up like I was being escorted in a wedding. My doorman was a very good looking twenty something black man. He was bald and built like an athlete. I thanked him as Annie walked over being led by another hottie and both were in suits. The door was opened and we went inside the salon. "Good day ladies we are so glad to see you decided to visit Vision's Salon. May I get you girls something to drink or may I take you to your appointment. I know Gia is waiting on you as we speak" a very pretty blonde lady asks us. "Thank you Lindsey and yes we will share a bottle of your best red wine. Gia is such a sweetheart and I haven't seen her in a long time. Please do tell her we are here Lindsey! Annie says to her. Looking around the money just comes right out of the walls. Everything is so perfect and in place. A large wall has water flowing over it and the lighting makes it look like I imagine a palace looking. "Annie you look as beautiful as ever honey! I am so glad to see you again and how have you been?" a dark haired lady come over to greet us. They hugged as I watch two old friends reunite. "Now who do we have here and why haven't I ever met her before now Annie? She definitely got her look from her Mom and I am sure she is going to be a man killer in no time just like you Annie" Gia says and I thank her for the compliment. "This is my daughter Dena and I am sure she will love you Gia, just like I do. We just want you to work some of that Gia magic and make both of us feel like a million bucks. You have us for four hours and we are out of here for a day of girl fun" Annie speaks to Gia. Gia walked a little closer to me and began to look me over. Her hand grasped mine softly and held it over my head. She remarked she knew I was a dancer and I should twirl underneath so she could se more of me. I spun around as she wished and stopped when she let go of my hand. "You are a Doll baby and we are going to have lots of fun today. I have girls ready to do both of your manicures and pedicures. I have facials lined up and a new hairstyle for our little girl here and her Mom is getting highlights. Young lady have you ever considered going blonde? And I don't mean bleach blonde but light enough so guys will make jokes about you being one" Gia says to us. I smile really big at Gia and tell her I would love to do anything she thought might be pretty. Then we are taken back to Gia's room to begin our pampering. We were given very pretty pink pajama like outfits to wear during our visit. Annie remarked that these were to use so we wouldn't stain our own clothes. They were identical and felt good to my skin. I had a little concern that my extra equipment would become exposed in the skimpy outfit but so far so good. I did not have anything this pretty to wear to bed like them and wanted to keep them for myself. Annie asked one of the assistants to snap a pic of us in the cute outfits with her phone. We hugged and smiled really big as the girl took our picture. We then sat down to have our nails done in a reclining chair with our personal manicurists. It felt good as they massaged and played with our feet. I smiled at Annie and thanked her for everything she had done. She reached over and took my hand in hers to hold. "Girls everything today is going to have a pink theme so if you will please give us your prettiest pink toes a girl could ever want. I watched as my feet turned from sore dancer's feet to pretty girl feet with new polish. I had only ever done this once and I did not do a very good job either. I felt like I was walking on air as we stood to go over for our manicure. The girl doing my nails was not but four or so years older than me and her name was Emma. "Sweetie I am going to add some short extensions to your nails and use the same polish as I put on your toes" she said as if to ask and glanced at us for approval. I told her that I loved that idea and thanked her. Another worker in the salon brought in a large ice bucket with the bottle of wine Annie had ordered for us earlier. I sipped my first taste of the wine and it was so smooth, I sipped it again. The girls asked us about what was the occasion for our visit. Annie told them that it was my birthday and we were celebrating for a whole week. Both of them said "Happy Birthday Sweetie" and did not ask how old I just became. My nails were drying as I began to daydream a little. I imagined Mr. Lee taking my pretty hand in his to kiss as he told me how pretty I was. He was holding it as if to help me to stand up from my chair. I saw myself standing up to face him closely as he wrapped his strong arms around my waist. He held me closer as we stared to each other's eyes. As his hand goes to my tiny rear he leans down to give me my very first kiss. And we then!" "Dena!" "Wakeup honey and quit daydreaming!" Annie says bringing me back to reality. "Sorry I was way out there I guess. Maybe I was already blonde." I laugh and almost giggle as I say it. I looked to Annie still smiling at her as Gia calls me over to her chair. She leaned me back to the sink to start washing my hair. Her fingers massaging my scalp and the hot water felt good. I was finally being treated like a pretty girl and not a dysfunctional kid with awkward dreams. From a package Gia showed me the hair extensions she was going to add to my hair's length. I watched Gia slowly work the extensions into my hair. In the mirror I could see the difference between my old length and the new. She turned me away from the mirrors as she used her scissors to begin the new haircut. "Honey you will love this new haircut and I will show you how to do the styling so you can keep the look for some time to come." I finished my first glass of wine and politely declined to be poured another. Color treatment takes awhile and Gia told me all about herself as she worked. I told her I had trained young in ballet and now I am hoping do study modern dance in college. I look to Gia trying to see her reaction if any at all. "Honey there are dancers in this town are my best customers. All have six digit incomes with most of it in the bank because they have friends who take care of all their bills. A few of them began their careers just like you Dena. And I don't mean 18 and blonde sweetie, they were young and sweet just like you are. But they didn't have an Annie to help them along like you do. The thing that is different about you is what will drive men crazy in this town. Give you a stripper pole and some music and they would be begging at your door Dena. I am sure with a little time and effort a large bank account would be right around the corner. By the time you are in your thirties, you would be set for life. I don't know any men who can retire at that age. They are beautiful ladies who still have their life to live as they please. I do so envy them sometimes" Gia tells me. After the color treatment, I sat under the dryer to let my new color set in. Gia worked on Annie's haircut and style and they talked without stopping. The problem was that I could not hear a word of it because of the dryer. For some reason I thought about my friend's dad, Mr. Lee. Like I mentioned he is a very handsome black man. He attended some of the parties Dad gave and he had been caught on occasion coming out of the pool house with a couple of ladies. He seemed to have a soft spot for blondes also. Maybe that is why I thought of him right now. I had never until now pondered the idea of a black man. I am sure that would go over like a September hurricane in High Port. I smiled at the thought of Mr. Lee seeing me as a cute young blonde. One of the salon assistants came in carrying some boxes from the SUV. She was instructed to put them in the dressing area and walked out of the room. When the hair dryer turned off Gia called me back to her chair and Annie disappeared into another room. Gia wished me a happy birthday as I sat back down to have her style my hair. Slowly I watched in the mirrors as Dena was made into an entirely new "Gurl." -At times I did not like that word but my daydreams about Mr. Lee made me appreciate it. Gia removed all the strips to see the new color and how well it may have taken to my own color. As it dried and revealed the real color Gia's face lit up like a Christmas tree. "Honey we have hit the jackpot and the color is fabulous!" Gia tells me. She curled and cut and teased my new hairdo. Reading the excitement in her face made me so damn anxious to see how it looked. Gia called Annie's name and told her to come take a look. I had to look at both of them before Gia would let me turn to the mirrors. They spun me around to see how it looked and I was speechless. My hair hung to my shoulders very easily and was beyond what I thought was possible. "Dena if I didn't know better I would swear my chair was filled by a pageant contestant. You have all the looks to make any girl jealous as hell. You can't create in a salon what you have behind those eyes sweetie" Gia says to me. I looked to Annie and cannot believe that she is actually speechless. "Baby she is not just being nice. You are so pretty that any mom would be proud to call you her own" Annie says. Only in a dream could I have imagined this moment. "I really don't know what to say. I love it Gia! Thank you both for everything! Every thing I could have imagined in a mirror looking back at me has come true today. What I see looks and feel better than I could have imagined it might. This is what I want to be Annie, and Gia. I love it!" I spoke wondering what they are thinking. I stood silent for a moment. "Dena you are looking at two people who would love nothing more than to see you this happy everyday. We know we are seeing the beginning of something very beautiful. Gia and I know you are something very special. The hair and nails and color just help bring out the real beauty of which you are Dena. And besides we only have an hour and a half to finish and we still have to get you dressed, do your makeup and get that skin a pretty light bronze color. Gia has told the girls to get the tanning booth ready for you" Annie says. After hugs and kisses Gia led me down the hallway to the tanning booth. She closed the door behind me and said "Sweetie we need to get you out of that outfit to do this. When I don't move immediately Gia looks to me and says "Dena don't worry about taking your clothes off sweetie I am not gonna bite you. I know exactly what you have under there and you will learn to love yourself naked as well as clothed. That pretty little body of yours is gonna love being a deep dark brown." Gia reached forward and starts to undo the top of my outfit. "I know these are not real Dena - as she brushed my filled bra. Is it also your dream to have a permanent set sweetie? I am sure Annie will help you get a superb set of tits Dena if you want them bad enough. Ten thousand dollars and a few doctor's appointments will get you a sweet set of C cups" She says to me as she brushes my top off my shoulders. Stepping around behind me she undoes my pretty bra and helps me remove the breast forms. The room has a large mirrored wall and I can see her standing behind me. I feel her hands on each side of me as they slip down to my panties. "This is a pretty little package you have here Dena. I am surprised it has not shown itself to us before now. I slip off my short bottom to reveal the panties I am wearing. She tells me to slip them off as she hands me a patch thong panty. "Yes I would love to have a set of C cups one day Gia! But like you said they are not free" I say. Gia goes on to tell me that - I am at the age now where if I want anything bad enough, I could get it. A girl as pretty as me will have no problem getting what she wants. She said she understands how things for me will be a little different but she is sure it would amaze me to know how many men desire someone just like me. Gia says that a lot of very wealthy men actually hire "Friends" like me as highly paid employees. I ponder everything she says as we prepare for the tanning booth. She hands me a bottle of oil to cover myself with to help the process. She tells me that I am going to sweat a little but not to be concerned about my new hairdo. She helped me some with the oil before I entered the booth. The lights were hot and I could feel the tingle on my skin. I spent 15 minutes before a timer sounded and the lights went off. I stepped out of the booth and Gia hands me a towel and a robe to follow her. She has me shower off my skin and ready to get dressed. When I see Annie the next time she has already dressed and looks great in a new black outfit. "Come on over sweetie so we can finish and go get some lunch." Annie says. I see my new outfit on a hangar in the dressing room and smiles really big. She hands me a pair of black satin and lace panties to put on first. I sit on a chair to slip on a very nice feeling black thigh high hose. I take a moment to admire how well they fit my legs. "Those legs don't have a blemish on them Annie. How would you love to have that going for you? And they are as smooth as everything else is too. I don't even see a need for a bikini wax around the little sexpot's play parts. I cannot believe that she hasn't gotten a rise while we have been doing all of this either!" Gia says. "Slip this over your hose Dena to see if we need a smaller size or not" Annie says when she hands me a garter. With her help it is set above my panties and she says they are perfect. Annie shows me how to fasten the garter to the tops of my hose. With that done I position my breast forms and then puts another new black bra on my shoulders. The black cocktail dress on the hangar looks pretty enough to be worn by an actress on the red carpet of an awards show in LA. I stepped into the dress as Annie zips up the back I flip my new found hair out of the way. I glance into the mirror and so dreams of being that girl in the centerfold of a magazine. Annie and Gia keep up their babbling and seeming to egg me into saying something. "Gia you just haven't hit the right buttons with Dena yet. Ask her about the big crush she has on a Mr. Lee." Annie tells her. I just smiled and Gia was standing close enough to touch my crotch under the dress when Annie wasn't looking. I twitch a little as her fingertips tease my little equipment, but it feels good. Gia smiled and winked, knowing she startled me real good. "Is that all it takes to get your little clitty to spring up sweetie? Don't worry honey there will be many Mr. Lee's in your life but you will call them Sugar Daddy" Gia says smiling at me. "I really don't know whether to take anything seriously that you two say. Yes I do have a crush on a very nice looking man. Is that so wrong that I should be ashamed? Annie, you said to tell you everything I feel. Right now I feel like the girl I was meant to be and I love it too." I say to them with my hands on my hips looking to a huge mirror "That's exactly what I wanted to hear you say Dena. We have done and talked a lot today but all of this is so you can be the person you desire to be honey. We are going to head to downtown Charlotte to have us some lunch and talk about what is next. Gia thanks for everything and we will surely be back soon. If you would be so nice as to take a few pictures for me, we will be on our way" Annie says encouraging me with a soft kiss on the cheek. Gia snaps the pics for us and hands the Ipad back to Annie. She quickly shows me the pics and we are now at the front desk. The receptionist gives Annie a credit card receipt to sign and with a big smile says "Thank You Mrs. Owens and Dena!" I guess Annie left a huge tip for them. Valets escort us to the SUV and we drive away. Annie begins asking all sorts of questions about how I feel and once again building me up. She has me cross my legs and telling me how to sit as we drive. She says you never know who you might meet while in your car. "Dena we are going to a totally private place for lunch today. I want to have a really nice meal and maybe we will meet someone there to talk too. The more people you are around the more comfortable you will feel with your new look. It is a place where you can meet some of the wealthiest and most powerful people around. There are lawyers, doctors, politicians, and other rich business men. It is a very quiet place where everyone is so nice and respectful of each other. And of course it is expensive too. That's how they keep it private. Your Dad and I come here when we are in town" Annie says to me. Maybe it was the look on my face after Annie said that which caused her to grasp my hand. "Dena I am here like I said every step of the way. You just have to trust me and let things take their natural course. You have all the assets you need and I am just going to make sure that you have the opportunities you want. If anyone asks you about yourself just tell them that you are about to begin classes here in Charlotte and you will be living here soon. It will be that easy sweetie" Annie says. The place had no sign out front but as soon as you enter there was a sign that read Jennings'. We were greeted by a man in a black and white suit. He greeted Annie by calling her Mrs. Owens. The host led us into the place and I was amazed by how nice the place looked. From outside you have no idea this place even exists. Everything was very private and when you sat down no one else was in your sight. Annie and I were seated and the host held our chairs. I began by saying how shocked I was this place even existed. Dena and Annie Pt. 02 "Wow this is the kind of place that you want to be taken to by a date I guess huh Annie?" I asked. She could see the giddy look on my face and smiled as I went on. She replied "Honey if a date brings you here then he better have the wallet to pay for it. Only members can come in here and the membership is what keeps most people out. Your dad and I have been members for two years." Annie says. A waiter appeared and Annie ordered us a bottle of wine and an appetizer. She instructed him to make sure the wine was chilled on ice for me. The waiter never asked my age or even blinked when Annie ordered. "So tell me Dena how are you feeling right now? Was Chicago this much fun? You sure do seem to be carrying your new addition really well, I wanted to tell you. You have really good posture and it makes them look very natural sweetie" Annie says to me. "Annie I feel great and I appreciate everything you have done for me today. You and Gia were great at the salon today. I love my hair, my nails, my new tan and all of the clothes you bought for me. This black dress was made for me and I love it. No, Chicago was no where near this much fun. As for these - I nod down to my chest - I can feel every move I make with them. But then again they are what they are - artificial. And I do realize they are only temporary." I say. But I still have my smile on and very happy to be living my dream day out with Annie. She begins to tell me that if I would that this is how I want things to be then some things can be made permanent. We are interrupted by the waiter bringing us the bottle of wine and pouring each of us a glass. He asked if we needed anything else while we were waiting on our appetizer. Annie smiled and told him we were fine and would wait. "Dena if today is how you want to live your life, there are plans to be made and it would only be a matter of time. We would need to schedule appointments with a plastic surgeon and a medical doctor to assist you with Hormone Replacement Therapy sweetie. You are a very special person Dena and you will be a beautiful lady. A lady with something very sexy and desirable about her already" Annie speaks and I am astounded by her response. A shocked look must have been on my face when a man came to our table. "Hello Jennings! You look great today as always!" Annie says greeting the man. And then says "I'd like to introduce you to my daughter Dena. She may be living in Charlotte very soon and we just visited Gia before coming over." I held out my hand and his hand grasped it in his large hand and kissed it softly. "I am very pleased to meet you Dena Owens. You are a very pretty young lady and I hope we will see you around here again if you decide to call Charlotte home. I will be sure to warn the men around here who you are and that they had better stay away until your Mom gives the okay. If I can do anything to assist you Dena please do not hesitate to give me a call." He says to me and I am taken aback how deep his voice is how damn good looking he is. My hand was about to melt in his as he held it as he spoke to me. He finished speaking and then placed one of his cards on the table for me. My hand was let go, I still looked at him and that very expensive suit he had on. He speaks to Annie about something as I am not hearing anything but remembering his voice in my head. I snap back to reality and smiles really big. Jennings leaves the table and as he walks away Annie looks right at me and speaks. "Dena when your feet touch back down on the ground look at that card Jennings just gave you. I think you have just met your next best friend!" Thomas Jennings MD Jennings Medical Group Jennings Medical Park I told her that I see he is a doctor, but asked why he would be my next best friend. "Dena, Jennings owns the doctors contracts that would be the doctors you will be seeing to get that new set of $10,000 puppies and all the hormone therapy you would need that Gia mentioned earlier. My guess is that if you were nice to him, you could get those B cups and doctor's visits for free. Jennings is also one of the men that Gia mentioned who would hire you to be their friends. If you met more of the members here you would find a few others too. For a six figure salary and unlimited credit cards I am sure you would entertain Jennings a few days a week and some weekends. Wouldn't you Honey?" I am holding his card in my hand and I can still smell his cologne. "I don't see why a man like that would want to spend time with me when he has women who would give anything to be with him. I wouldn't fool myself into thinking that men like him would give me the time of day Annie" I say. And with that the waiter brought our appetizer. I take two good sips of my wine and check my lipstick in a compact I had in my purse. Then I pick up the glass and finishes off the wine. Annie laughs and pours us another glass before she speaks. "Dena the hardest thing right now for you to believe is that you are beautiful. You are about to become somewhat irresistible to every warm blooded male in this city. Men who frequent here would love to have a notch on their belt with Dena Owens' name. You have played around with your little plastic toys enough to know what feels good. But you have no idea what a man like Jennings would do for some discrete time with that little behind of yours. Add to him a lawyer or two and you are about to triple your salary and benefits. Use your money the right way and you could retire in Florida before the age of 30." I sat there and thought about what Annie said. She mentioned my attraction to the small collection of toys she found during the remodeling of our house. All of what we have talked about and done to this point have been to fulfill my desire to have a man make me his play toy. I thought if I can finally get to the point where I feel pretty enough for a man to want that from me. Well then that is okay with me. The wine was very cold and I took another sip. "This trip seems a lot like it is turning into setting me up in a career. I am only two written exams away from graduating from high school and I feel like my career is about to start. A career as a trophy piece of ass for older men that will pay me for my time." I say looking at my wine glass to Annie. "If the idea of being a man's play toy is what you want, I want to make sure you have every thing at your disposal Dena. You can go into this with some class and enjoy the ride to where you want to be. You have the benefit of money to begin the ride. And also you have the benefit of access to the best of care to make the transition. We left Daniel in High Port and now Charlotte gets to see Dena become all she can be. You can have your Mr. Lee, but here he is likely going to be filthy rich." Annie says as she tastes the shrimp appetizer. "Well I am all for beginning the process of leaving High Port behind Annie. I am going to trust your advice and see how it works. You seem to be working ahead of me so far with the shopping, the salon trip and coming here today to meet Jennings. But Annie I am not sure if you have forgotten or what about one important matter. I have never as much as been held or even touched by a man" I say. "I guess that little supply of plastic toys and lube you have hidden at home are for something completely different. The fact that you wet your panties, when I put the lipstick on you this morning makes me curious. Dismissing how your ass twitches in a pair of shorts or that black mini dress, I don't know. No, you have got the desire already to have a man teach you how to please him. I am just going to help you get the best start possible sweetie" Annie says lowering her voice a little. I didn't really have a reaction for that one and began eating the shrimp. Annie's phone buzzes a few times while we ate and I saw her sending some text messages. Our conversation eased up and we finished eating. "We should be on our way Dena to our next stop" Annie says as she grabs her things. I ask if we should wait on the bill and she says they will just charge her for the meal and tip on her credit card. We make it to the SUV and head out into traffic from the restaurant. Annie asks me what I thought about Jennings and I said he is a very good looking man. She asks me about whether I wanted a tattoo or not. I nod and say yes but no time soon. Annie mentioned getting my belly button pierced and maybe another in my ear. That brought a smile and I touched my belly button. Annie said that the color my hair turned out matched my face and skin tone really good. I flipped down the vanity mirror to look at my hair. Looking to see that the length was a little below my shoulders. I could not wait to put it up in a ponytail or pigtails. When we passed the mall she mentioned that we would go shopping there and shortly she turned into a nice development and turned in the driveway of a lightly colored brick home. It is nowhere nearly as big as Casa De High Port but a really nice look to it. Annie pulls a garage door remote from the console and one of two huge doors open and she pulls inside. To the left of us in the garage is my new red BMW. I look to Annie and she says that she had it moved today by two of my Dad's workers. "Let's go see how you like your new place Dena. If you like you can live here as long as you need to sweetie. Your Dad and I bought this place together a few months ago. I think you will love it, since I decorated it with you in mind" Annie says as if she is trying to sell me on the idea. I am certainly sold on the idea of having my own house in Charlotte. We begin getting the boxes and bags from the SUV. Both of us have to make another trip to get everything. The house on the inside is very wide open and bright. Each room is decorated and completely setup to move right in to live. The kitchen is huge, so is the living room, a dining room and a large pool table in another room. The master bedroom of the house is on the first floor. Double doors open up and the bedroom is as big as an apartment. Annie used a lot of white and in a few places has bright colors to add her touch. . "Well how do you like it Dena? Like I said you can do it or you can do it in style. You can have everything you need right here in Charlotte. No need to worry about High Port and anyone there. Let's get your stuff put away and see what we can do the rest of the day" Annie say smiling really big. I am walking around taking all of it in. My bathroom has double doors leading to it with a vanity and dressing area. Going through all the stuff I bought with my birthday money was pretty cool. Yoga pants, pink and red tops, lots of panties, a pair of pink and white running shoes and two really pretty satin chemise sets. Estee Lauder had a makeup console that was filled with everything imaginable and in every color or shade. It was the most expensive girl thing I had ever bought myself. I set it up in my vanity area and returned to the bedroom Annie is putting stuff away in the closet on hangars. I cannot believe how many outfits and dresses she pulls from her shopping. The smile on my face was huge as she filled a section of the closet with my first wardrobe. I could wear something different every day for a few weeks and not wear the same thing twice. She laughed when she emptied a couple of boxes that were sitting in the closet I hadn't seen. "You will love some of these Dena" she says and pulled costume outfits from the boxes. She had cheerleader, princess, nurse, Little Bo Peep, Lady cop outfits among others. Very tiny mini dresses and stocking and boots to go with them. "I know how much you love to play when you're alone so I thought you might enjoy those sweeties. "You can try them on later to see which ones you like best. What do you want to wear this evening Dena? I think we ought to pick you out something to show off that little behind of yours" Annie says to tell me and looks like she is trying to read my mind. I tell her that I love everything she bought and walked over to the closet. As I thumbed through the hangars I picked out a short black and pink mini dress and hold it up to look. "If you leave on the garter and hose it will really be sweet to look at Dena. You put it on and I am going to see if the wine is in the fridge. We need a glass right now to celebrate honey. And also leave on the heels too, because I want to see how good you can make that look in case Jennings or Mr. Lee saw you in it" Annie says as she walks out of the room laughing. I admired the mini dress a little before I slipped out of my clothes. The way the bottom was flared was pretty but I knew it was very short. Before I put on the new dress I adjusted my hose and garter to make sure they were in the right place. The mid section of the dress fits snugly so it made my new found breasts appear bigger. It also gives me a look of having a girlish shape like I should. The skirt itself was wide at the bottom it did not cover nearly as much as I had hoped. The tops of my stockings are showing and I can feel air under the back of it. A huge mirror gave me a good reflection of how I looked. I thought of how the next few days should only get better and I am having the time of my life. The outfit is so pretty and I tell myself the person wearing it is very pretty too. Going into the bathroom I freshen up with some lipstick that is nearly as pink as the color of my skirt. In a Macy's box on the counter was a pair of pink hoop earrings I ordered. I swapped those out and loved them instantly. When I walked into the bright open kitchen of my new place, Annie was putting a bottle of wine in an ice bucket. She looked up and yelled "Damn Dena all you need is a stripper pole and some music to start a party. I am sure the Cheetah Club would hire you right now to parade the stage. We need to get some pictures of this beautiful girl." Annie reached into her large bag she carries with her and got a new camera I hadn't seen before. I was told to pose for some reveal pics as she called them. "Dena I am sure that you are going to make you a Facebook page. Gia got some pictures at the salon, but I want pictures every time you change. You look so pretty sweetie and you are going to have so many admirers coming your way honey." Annie says seeming even happier than before and it makes me feel good too. I pose around the dinner table and chair for her, before she guides me to the living room. My white sofa is huge with lots of soft pillows and Annie had me pose on it for her camera. She took some close-ups of my face and asked for my biggest smile. Hearing the camera click so many times made me think of being a model, which is every young girl's dream. Annie finally relented and we went into the kitchen for some wine. I sat on a bar stool and crossed my legs with a deep exhale. I tell Annie thanks again like I have all day long. She showed me the pictures from the camera and they did look good I thought. I gave the credit to the camera and she laughs. She said the camera could download directly to our Ipads and she plugged it into hers. "I absolutely cannot wait to see you in that school girl outfit Dena. Please try it on tomorrow because I know you will rock it girl" and Annie's face lights up. I agreed to do the school girl outfit for her the next day We toasted each other and talked about our day. The wine was very good and cold. Our conversation turned to the sexual side of Dena maybe a little quicker than I had hoped. Since I knew my toys were not a secret to Annie it made it a little easier when she mentioned them. "I am guessing that you may want to do a little playing tonight huh sweetie? If you aren't in the mood after the day you have had, we need to get you a hormone shot earlier than I thought. I am not sure how much you take care of hygiene sweetie, but your bathroom is stocked with everything you need under the counter. And I left you a sweet new toy in the drawer too." Annie says. "I may do a little playing tonight before bed and I may even put on that school girl skirt for effect. And we can do those hormone shots as soon as possible. I am already looking forward to my first doctor appointment. And I hope we see Jennings again too! ...Smiling... As far as my hygiene, I don't have a problem there. Fresh and clean is good and I keep it that way in case you are wondering Annie. Smooth and pretty, just like a girl should be at all times. Though I do appreciate the fact that you picked that up for me, I will put it to good use. Soon!" I tell Annie. She hands me the camera and slips a small black plastic thing with a button on it. Then Annie explains to me that it is a remote for the camera. "Please snap us some pictures if you put on that outfit Dena. I would love to see it on you and I am sure Mr. Lee would too" I hear. We smiled and chatted some more about some of the stuff from the mall we hadn't opened yet. Annie tells me that we should be able to get an appointment by two o'clock with the doctor. I hugged Annie after finishing the second glass of wine and told her again thanks for everything she did to make my day special. She suggested I take another glass with me to make sure I slept well. I bounced off to my room with a glass of wine and camera in hand. Maybe it was the anticipation of a new toy or the wine but I was feeling really horny. I suddenly could feel the satin in the cute panties on my almost pink clitty. I lifted the dress over my head and tossed it on the bed. Reaching down I touched myself like I wanted to all day long. Black thigh highs with a garter attached, black satin panties and a lace bra seemingly full of perky tits on a slim tanned 18yr old pretty boi should be picture worthy. I grabbed my glass along with the camera and headed for the bathroom. Annie had put everything right where she said it was and I took what I needed to prepare. I sipped my wine as I performed a good cleanse as dirty as that sounds. Using feminine wipes I freshened up the outside too. That always has the feeling you know you are about to have your pussy played with. I think women still have it worse and I will take my fate. "I really beat myself up whether to come in here or not Dena! I sure do hope it is okay with you sweetie. Look at you all sexed up and it is written all over your pretty face how hot you are right now. Those pretty ass cheeks sure do look good in that garter too honey. Magazine quality looks I am sure many would agree. And I brought the wine bucket with me too if you want another glass." Annie says halfway smiling and waiting for me to reply. She was dressed in a very pretty black teddy and almost begging me to let her stay. If she wanted to be here I did not intend on making her leave after everything she had done. "Yes Annie I would love for you to join me. You are my inspiration and you know me like no one else does. The spy in you will love to see what I had planned to do before you came in here." I reply. She sat down the bucket on the way over to face me up close. Her hand reaches down and teases my little boiclit and balls with her nails. "Still no rise yet Dena? I figured it would be a stiff little pencil by now honey. Also I can tell you used your cleaning supplies. The lavender smell is so you right now sweetie" Annie teases me as she speaks and backs away. Annie poured us another glass of wine and by now I am doing good to walk in the high heels without stumbling a little. We toast again and smile really big. Annie asks me if I mind if she takes some more pictures and I tell her to snap away. I didn't tell her how fun I thought that was earlier in the living room. "Well I need to put on some panties before we start this little photo shoot. I cannot start out showing off the jewels, can I?" I say laughing from the wine and excitement. Opening my dresser she hands me a pretty black thong panty. I stepped into those and tightened them up on my tiny hips. The lights in the bathroom brighten to almost daylight. All of the mirrors give you about a 360 degree look from anywhere you stand. I liked being able to see myself completely as I stood there. Dena and Annie Pt. 02 ***** Please be nice and give a Sissyboi FIVE stars for this story. Dena and Annie Pt. 03 This story is a complete work of fiction and is only to be taken that way. If Transgender sexual ideas offend you then do not read. If you are not above age 18 then you should not be here anyhow. ***** "Come on sexy let's see what Dena has for the camera! Make some man want to rush over and ravish that little body of yours. I begin posing around the bathroom playing to the mirror at the sink. The smile on my face only reveals a little bit of how happy all of this makes me. Annie is loving it too telling me to strike different poses against the white vanity top. "Put your knee up on the counter sweetie" Annie says moving around behind me with the camera. When I do this I can see her over my shoulder and hearing the quick clicks going off. "Place your hands over your crotch sweetie as if you are trying to cover up for the camera. And if you feel brave enough you can let me see more when you are ready. Give those men something to make their mouths water. May be I can put some of these in a graduation invitation to Mr. Lee and Jennings." Annie laughs to me. I pose standing for her and pretending to keep my boi package hidden. It felt cute and like I was pretending to be a young girl for the camera. I stop what I am doing and I take a seat on the huge counter. Crossing my legs I wonder what to do next. "What am I supposed to do here Annie? Are these pictures just for me or what? You bought me a new toy and I had hoped to play with it tonight" I say laughing to Annie. I grab my wine glass sitting there and she walks over to the drawer. I see her grab a white tube and a small bottle from the drawer. Then I saw a curved realistic flesh colored dildo in Annie's hand. "Dena meets her next best friend! That's what we can call these pictures if you like. Don't you think it is nice Dena? This is what girls use when they put off a man to make him wait for sex. These don't ask you for anything in return. That's why they are called toys!" Annie says. In her hand I see how it fits and it looked very nice. She then handed me the toy cock to hold in my hand. I liked the feel of the plastic cock in my hand. She snapped a picture of me holding it and I burst out laughing. A glass of wine in one hand and a cock in the other, as we both laughed. I acted like an air head and said "Hey look at Dena folks! She has her two favorite things tonight to play with." I say acting silly as hell. Annie snaps the pics as I give her and the camera a dumb blonde act. I sip my wine and smiles really big for her. "Now taste the other thing in your hand sweetie to see if it is to your liking." Annie says trying to convince me to taste the cock. I look to my right and the plastic cock is eye level with me. "If you want to kiss it sweetie go ahead. Pucker those lips up and give it a big wet kiss. Your lips are still wet with lipstick and that will be pretty to see. Let the playtime start right now sexy Dena!" Annie gives a very good argument. I finish my wine in one sip and sit the glass on the counter. The toy was long enough that my right hand only covered about half of its length. I looked up to the cock with my hand against the fake balls. My lips touched the cock and electricity went through my young body. The curves and cuts of the cockhead were surrounded by my red lips. My eyes closed savoring the moment and illusions of it being a real live man's cock. Jennings in the dark suit came to mind when I began to suck on the toy. I dreamed up him unzipping his slacks and showing me a beautiful semi hard cock to play with. My hand pushes more of the cock for me to hide in my young mouth. The veins and texture of the cock felt so good as I was taking all of this in as I sucked it in and out. My eyes opened to see Annie with the camera pointed right to my face. Then I realize she is videoing me as I suck on the toy. My eyes go wide open and I stop what I am doing quickly. The dildo is wet with my mouth juices and I still have it near my mouth. "You were having so much fun with that toy Dena. Why did you stop sucking it honey? You will need to learn to pace yourself and enjoy doing that more. A real one is going to need lots more attention if you want to please it the right way. Sometimes a good blowjob will keep you from having to give up anything else." She says. The way I am sitting on the counter, my knees are up to my chest. I didn't realize how wet my panties had become and that Annie had a clear view of them. Annie's hand goes down to my crotch and she looks at me to ask if I mind if she... I figured she was going to touch me and I said "Go ahead." Her fingers tugged open my panties and my little boiclit and balls came into sight. "You wet your panties princess and you should never wear dirty panties. Let me slip them off of you sweetie" Annie says and nudges me to raise my hips, to slip off my black panties. I try to keep myself covered as I lean on my right side on the counter. With the mirror right behind me Annie comments "I can see your honey hole in the mirror sweetie. Wow it is pretty and pink like you said!" She went to a small closet and grabbed two large white towels. The counter is long with a sink on each end. Annie instructed me to lie down on my belly on a towel. The other one she handed me so I could put under my elbows. I stretched out on the counter with my little ass up in the air. I had no idea what was next as Annie picked up the bottle of lube. Standing at my side she slapped my ass cheek with her hand. I rose up and laughed asking her why she did that. Her hand rubbed my soft ass cheek and she slapped it again hard enough to leave a print. "I want to you to loosen up a little sweetie so you will really enjoy yourself. Sex is fun as hell and you will need to learn to enjoy it as much as possible. It is going to be your ticket to anything you want honey" Annie says as her hand softly rubs my cheek. Picking up the lube bottle she opens it and puts a small amount right in the crack of my ass. I jump and say how cold it is. Another squirt of the bottle and Annie massages my cheeks together to spread it out. I felt two fingers between my cheeks making sure the lube was in the right place. I moaned and wiggled a little at the feel of her fingers. I loved the way that felt, slick and smooth. Annie picked up the toy with her free hand and that scared me a little. Turning to the right I see she has the toy near my backside. My ass cheeks felt it when Annie slapped my ass cheeks with the toy. Annie rubbed the dildo back and forth over my boipussy. I loved the feel of the bulb tip teasing my pussy and then the length rubbing over it to the balls. I raised my little ass up to meet the toy, wanting to squeeze it tight inside of me. "This is supposed to be your fun night Dena and I want you to use this like you want too. Do you want me to mount it somewhere for you or should I help you myself sweetie. Something tells me that you really want this toy cock inside your little money maker. Reaching back to spread my cheeks a little, I moaned for Annie to help me out. In the mirror I saw her with the lube bottle pointed down to my backside again and the dildo ready to fill me up. "You can never have too much lube sweetie and don't ever forget that!" she says. The new lube began to run and Annie used it to lube up the shaft of the dildo more. With her left hand Annie guided me to raise my little ass up in the air. I felt the tip of the toy teasing my really slick rosebud. "This is going to be a little like you're giving up your pussy from behind Dena and I know you will enjoy this sweetie" Annie says as she begins. The bulb head of the cock opened me as I felt a push to slide the head past my sphincter. Annie did not waste anytime to ease it deep inside my cunt at all. Sissy cunt Dena was finally getting something hard inside her. My hips and ass were already moving to the feel of the plastic cock. The wine surely helped loosen me up and I was just so damn happy. I rose up on my hands and knees to meet the dildo easier. Annie laughed as I reacted to the toy in my pussy. The dildo slid back and forth with Annie's hand several times. Occasionally the head left me and was pushed back in to the bend in the toy dick. "Do you want it all in there sweetie? I am sure you have plenty of room for it! Tell me how much you want Dena!" Annie instructs me. She uses the bend of the toy as it grinds downwards against the walls of my boicunt. "Give it all to me Annie. I want it all inside of my Pussy! Please don't stop Annie!" ***** If you like this please encourage me to go farther. Please give me 5 stars also if you will be so nice.