Date: Thu, 14 Jun 2012 18:58:10 -0700 (PDT) From: Derek Alexander Subject: Miss Richards: The Enigma / TG / Highschool For the 10th part I wanted to write a little bit longer story as well as the one with the biggest twists so far. I'm sorry if this one takes a little longer than the others recently. Thank you for reading and I appreciate any readers that write to me and let me know what they think. Disclaimer: I am over 18, but if you are under 18 then stop reading right now. If you offended by sexual acts between teenage males and adult transsexuals then stop reading right now. If you are above 18 and like these kinds of stories then by all means continue. This is a work of fiction. Miss Richards: The Enigma I can remember every detail of the days that followed my night nestled in the arms of my new mother. It feels so strange to call her mother sometimes. Simply standing on the corner waiting for the bus and I couldn't be more lost. The funeral played again and again as every detail filled every space of my mind. Despite the pain that filled me there were simply no tears to be shed anymore. I knew that my mind had snapped. That my mind had shut down to prevent further pain and suffering. My psychology teacher last year had taught me that the brain could only stand so much before it would take measures to protect itself. The brain would compartmentalize the bad things and tuck them away and that many life changing things would develop within this person. The effects could happen overnight or come forth forty years from now. Do crazy people know that they are crazy or do they accept their actions as sane? "This should be fun." As the bus rolled to the curb all I could do was hold my head low. I couldn't face anyone on my bus or even at my school. I regretted coming back but Miss Richards insisted that I needed to get back into society and learn to overcome this problem. She would always be available if I needed to get away, she had talked to the staff and they knew to let me be. I wasn't sure if it comforted me knowing that every teacher felt so much pity for me that I could leave whenever and not get in trouble. I don't know if I'm comfortable with them treating me like a wounded puppy. "Hey Alex!" A familiar voice, a voice from the person I was most scared to face. A voice that shouldn't be on this bus. Sandy Dee was my girlfriend but for some reason she was the last person I wanted near me. Despite the pain it caused I went with the expected and sat next to her while still keeping my head low. "Alex, are you okay? Miss Richards told me what happened, but she wouldn't let me see you." "I'm, I really don't know what I am right now, but I'm not okay, no." "Oh, I'm sorry do you wanna talk about it?" "-sigh- Sandy, my parents are dead. I haven't felt like myself since the accident. I'm lost and nothing seems normal to me anymore. I need some time to get my head straight." "Are you breaking up with me?" "Please Sandy, don't get upset, I'm not doing anything right now except finding myself again. I just need some time to find ground again." After a few sniffles she composed herself rather quickly. "I can understand that Alex, just don't forget about me, okay? Oh, and if you wanna go to the Halloween party next week let me know." "What party?" "Justine Collins holds one at her house every Halloween because her parents leave and let her throw a big bash at their place while they go to New York and party." Justine Collins was one of the rich girls on the cheerleading squad. She had tried to get me to go out with her on more than one occasion, but I just wasn't interested. Justine Collins was the kind of person that got what they wanted and not getting me was one of the many drama filled events of the high school last year. "I don't know if I can go to her place, she and I had history last year, but I'll think about it." "Well it's Halloween, and costumes do wonders at hiding yourself. You don't have to, just let me know if you wanna go together, ok?" "Yeah, I'll let you know Sandy, thanks for being cool about this. Regardless, you're a really cool chick." "The best one you'll ever know silly." __________ "How was the first day back Alex?" "It wasn't bad, coach acted like nothing happened and that helped. All the kids rushing to say they were sorry got a little frustrating, but other than that I had some time to think about things." "Oh, wanna talk about what's on your mind?" Miss Richards was more radiant than ever today. She was wearing a tight white pencil skirt with black pinstripes. With a matching suit jacket that cut off at her navel. Her undershirt was a tight cotton black dress shirt that was accented by the whitest of silk ties. She wore another pair of 3 inch heels with shiny white leather on top and black bottom. Now that the day was finished her raven black hair had been let down to drape her shoulders further accenting the ensemble she had on. "I was invited to a Halloween party by Sandy on our way to school." "Uh huh, and you wanna go to this party? Are you sure you're ready for that?" "I think so and I think I want your help with my costume." "Do you wanna head over to Party Town? We can go get a costume now before the good ones are all gone?" "No, I was actually considering going as something quite different this year." "What do you wanna be?" "You. I wanna go as you Miss Richards." The car came to complete halt as she pulled over to the curb causing the car behind us to honk and speed past with obvious aggression. "You're not just talking about for Halloween are you?" "No, I've had a lot of time to think about what I want ever since the accident and I've never been more lost in my life and when Sandy mentioned the party everything seemed clear for the first time in over a week now. I know that you and Sandy grew up knowing what you wanted to be from the moment you were born, but after my parents died I might as well have been re-born when you stepped into my life. I don't feel like me anymore. What I was before was lost with them. You are my mom now and I wanna be like you. Will you help me?" "I would love to sweetie. There are some things you need to know though first. You have to know that if you go all the way with this that it won't be easy, that you will have some of the hardest times ahead of you and that you will need to learn to be someone entirely new. You will no longer be Derek Alexander, but you will now be a new person. If you are fine with this I will more than be happy to accept my new daughter into the family." "Yes, call me Alexandria Richards." "My darling Alexandria." __________ The rest of the drive was eerily silent. Miss Richards was lost in a world of thought occasionally saying things to herself as if checking off a mental list. Luckily it was a short drive back home and we pulled into the driveway within minutes. "Go inside and find my Nair, take the Nair and apply it all over the hairy parts of your body. Let it sit for about 10 minutes and shower off. Go find my razor and shaving cream and shave any remaining hairs you can find. Go slow and take your time going over it all, you don't want razor bumps. I have to run to the store and buy some supplies and I'll be right back in about an hour. If you finish early go into my closet and find some heels, practice walking around until I get back." Without a word, as I closed the door, she took off in the car. We had moved into her house now and when I walked through the door I was still taken back by the warmth that filled me when I stepped through the rooms. As I found my way to through her bedroom and the bathroom I started a search through the drawers and cabinets. Her cabinets were filled with feminine accessories and at first I was a bit taken aback by how much work Miss Richards put into maintaining her image of beauty. Within a couple minutes I had found the Nair and the shaving utensils. As I stepped into the shower I felt a twinge of fear for the upcoming change. The Nair spread over my skin with a slight tingle and my heart began to race with each passing second. My hips were more pronounced from the weight loss. As time passed I could feel the tingle turn into a slight burn and I felt that it was time to wash it all off. As the magnificent shower that Miss Richards owned buzzed to life I could see the hair fall in wet masses around me from my now smooth flesh. There wasn't much hair to begin with, but the new feeling of smooth skin filled me with such a rush of excitement. I took this additional time to wash and lather my skin. As I rubbed all over myself I could feel the newly smooth skin and I couldn't help but to rub more and more. As I reached my ass I felt the need to clean myself both outside and in and I slipped a soaped up finger inside my hole and tried not to moan despite being alone. I kept pushing deeper trying to reach as deep as Miss Richards had, but it was impossible. The thought of her brought me back to reality and I finished my wash. Not wanting to stray too far from the task set for me I grabbed the can of shaving cream, lavender scented, and spread the sweet smelling foam over my legs. I never really grew that much facial hair, but from the times I did shave I knew to go with the grain and use slow strokes taking the time to shave away every tiny centimeter. Miss Richards's razor was expensive looking; the entire structure was made of heavy cold metal. The blades looked sharp and keen. As I pressed the blades against my skin and went down the length of my leg it felt as though my leg was even smoother with each passing stroke. The motion was methodical and relaxing. I was filled with a sense of calm from this and I knew then that I had made the right choice. "I remember making that same face the first time my parents let me shave. You truly enjoy this don't you sweetie?" "You scared me, haha, yeah it just feels right." "So I see, you look fantastic by the way. Your frame is perfect and even you face in time could turn very feminine. I have to ask though, are you still ready to go through with this?" "Yes ma'am, I'm ready to be a woman like you." "Well just so you know this is going to take a while to become a full transition and you have to be patient before you can come out as a woman without heavy costume and make-up. If we get on it now maybe next year we can enroll you as my daughter?" "I would like that mom, so what's in the bags?" "Oh these? These are just some new clothes to wear, some make-up, wigs, some accessories, and a few other small things." "This is all so exciting, so what are we gonna do first?" "Well after you shower off I'd figure we would try on some wigs and underwear to see which ones fit and look best. Then after that we can have some fun and we can go over the schedule of your doctor visits and pill rotations." "Fun?" "Of course, you really think I can stand seeing you like this and not bend over that sweet ass at least once?" It was true, as we spoke I could see the front of her skirt start to bulge in front of me. The sight of her tenting skirt sent a tingle through my system and my own member started to come to life. The embarrassing rise to attention didn't go unnoticed much to my own dismay. "I'm sorry mom, I can't help it, you're just so pretty." "It's okay sweetie, let mommy take care of you. We don't need this to pop back up when you are trying on your new panties." Then she proceeded to take off her suit jacket and tie. As she unbuttoned her blouse the sight of her cleavage aroused me even further. The sight of her perfect alabaster breasts waiting to be released from the black lace bra underneath her shirt. Her huge breasts seemed so much bigger on her tiny frame and for once it truly seemed unnatural in the best of ways. "Do you like mommy's big tits Alexandria?" "Yes ma'am." "Come fuck your mom's breasts." It wasn't a request. She reached over without looking and spread some kind of soap between her chest which was now sheen and slick. As I stepped forward I felt the warmth of her chest envelop around my length. "That's it baby girl fuck your mom's tits. Fuck them harder, pump your cock in my tits." "Your breasts feel so good momma." "Yes Alexandria, you're such a big girl. You're getting your mother all nice and hard. I'm gonna fuck your cute little ass so hard later that you'll be begging me to stop." I was thrusting as fast as my hips would let me and the entire time Miss Richards kept up with me and kept my dick wrapped inside her flesh. The feeling was sensational as I pumped as hard as I could into her chest. "Mom I'm gonna cum!" Again, as if knowing exactly when I was going to cum, before the words could escape my lips she took me from her chest and replaced it with her mouth and I felt her tongue run over her my head as the cum erupted from me. Wave after wave of pleasure crashed over me with each pulse of cum left from within me. "That was delicious Alexandria, thank you for the treat baby girl." "Thank you momma. That was amazing" __________ After the shower Miss Richards went into the bedroom to change and left me to finish showering, dry off and apply lotion over my entire body. That was a new routine that I was told to do at any moment available. Not only would it keep my skin soft but also promote a feminine smell. When I was done I was told to come to the living room naked. There was Miss Richards sitting on the couch in her relaxed attire. Miss Richards was now Maria again and was wearing a pair of pajama pants with Hello Kitty faces all over the entire length of fabric. She wore a tight pink tank-top which showed just a little of her belly button. She had handed me a tiny wad of fabric when I entered the room. "Okay Alexandria, try on this pair. We need to figure out which cut of panties look best on you." The panties were small and black and were cotton with a little heart on the right front hip. The slid on and I felt tight and bunched up but the fabric was soft against my package. "Those are a standard bikini cut panties with a poly-cotton blend." She had pulled me over to her and was now making minor tweaks to the fabric around my ass and I couldn't help but to make tiny little moans as her soft hands ran over my skin. "See this bulge? You need to practice tucking yourself. There are many ways you can do this, just be careful if you need to use tape and be sure to keep yourself clean. You can find different ways online, but the basic way I was taught was to push your balls up into the place inside and then wrap the sac around your penis and pull and tuck underneath. You might not have that problem with your size, and if you walk neat and proper and your panties are nice and tight it should stay in place. If not you may have to experiment around with different techniques." I did as she said and it wasn't really comfortable pushing my balls up inside and neither was the tucking part. I didn't need to wrap any excess skin, and after I had it all tucked I had to admit that it looked pretty convincing. "How does that feel? It will feel different at first but you will get used to it after a while. I can't really tuck much without it being seen and so I wear skirts and pantyhose a lot." "It feels alright, it's a little hard to walk with my legs close together, but I think I can get used to this. What other panties do you have for me?" "Aren't you the eager one? Well I have hipsters and boyshorts for when you go in public, and I also have some tanga and thong panties for some private fun if you are interested?" "Which ones do you like?" "Well my personal favorites are these lace boyshorts. They hug tight to the body and cover most bulges comfortably and the lace feels wonderful as well. As for me they show just enough ass to tease and just enough thigh to not come off as a slut." "Well then I shall try those next then." As I slipped out of the bikini bottom I waved my freshly cleaned ass in her face. I could hear her breath catch as her face bumped against me when she reached for the boyshorts inside the bag on the floor. As I let my rear linger with the undies entwined in my thumps I felt her hands grasp my rear and her tongue tease me hole. She was now licking my little hole and breathing in deep the aroma in front of her. My once tucked penis was now dropped and rising quickly as she worked her tongue deeper inside of me. "You cleaned inside yourself as well didn't you? You little slut, I bet you enjoyed it too, fingering your little hole. Did it feel like this?" As she spoke she started to push her long slender finger into my wanting hole. Her finger twirled around mixing with her spit as she reached deeper than I had before. As she thrust her finger harder into me I was fighting back moans. That was until she shoved her second finger into me and I couldn't hold back anymore and moaned out loud. "That's momma's little slut, let it out, let momma know how much of a slut her little girl is." I soon lost myself in my own little world of euphoria as she fingered away at my hole, but was soon snapped back as I felt her hands pull me down to her lap and was met swiftly with the massive head of her cock. "Sit slut! Sit on mommy's cock, let mommy see how much you want her inside of you." My hands were braced on the couch around her thighs as I lowered myself onto her monstrous member. Despite having been fucked by her before her size was still astonishing. It was like willingly lowering yourself onto a baseball bat and even as I tried to fight it I couldn't help but to wince in pain as every passing centimeter of flesh pierced my bowels. "You're almost there sweetie, the head is almost in. Just keep going and then mommy will take real good care of you." When my hisses of pain broke through I felt her tender hands stroke my back and neck and her voice had softened to a soothing coo. I could feel the thickest part of the head approaching and knew that this was the most painful moment. "Mom, please help me, I can't do it without your help." Maria knew just how to help and she pushed up just slightly and the head popped in with a swift painful thrust. "There you go sweetie, now let bring your feet up and let momma take care of you." So I brought the middle of my feet to rest on the edge of the couch cushion and brought my hands back to the rear of the couch and as soon as I was supported Maria grabbed onto my hips and started to slowly thrust into me. She moved slowly and rhythmically in and out of me. There were no thrusts, just slow sawing grinds and I felt the same building pressure build as my erection rose without a single touch. As every inch ground its way into me my moans became louder and louder and I knew it wouldn't be long until the pressure became too much and I would release. "Mom...Momma, fuck me, please fuck me like the little slut I am." Without warning I felt my legs pushed from the edge of the couch and the remaining girthy inches crashed into me and I felt the dam break and I started coming directly up. The first shot arched high into the air and crashed down on my chest, the second was forced out with even more force and hit me on the cheek, the following shots weren't as powerful but the feeling of coming without a single touch was too much. Despite the immense pleasure she was far from being done and continued to abuse my now sore aching hole. She had her hands on my hips and she was lifting me along with her own hips and using my body like her own little fuck doll again. I had asked for her to fuck me and Maria was no longer the kind, sweet, Hello Kitty loving, and motherly woman who was helping her son become her daughter. She was now a hungry beast needing to fuck and cum. "You dirty little slut cumming on my cock like a little tramp. You like when I use your hole like this? When I fuck the cum right out of you? When I abuse your ass with my big cock like this? Answer me slut!" "Yes Mistress, I love it when you fuck me like the little whore I am!" "Lay on the ground slut, on your stomach. I'm gonna pound your little ass into the ground with my cock." "Yes Mistress." I did as I was told and as I laid down I felt how much I loved being her little slut as my newly renewed erection ground painfully into the carpet. Without hesitation I felt Miss Richards on top of me and her entire length was soon once again pounding into me as hard as she could muster. She was thrusting so hard that with each aggravated shove a grunt was forced from my lungs. Without a single touch I once again came. There was hardly anything to cum, but I knew I would catch hell for doing it into the carpet. "You little cock-slut! How dare you cum all over my carpet like that. Come here!" I could feel her dragging me back as she pulled me into her hips still maintaining her thrusts. "Lick up that mess you made, I want to see you clean it all. Yes that's a good little slut doing what she's told." I didn't hesitate, I knew what she wanted of me and I was there to please her. I started to tighten my ass on each thrust and it wasn't long before I knew she would cum. "You want your Mistress's cum that bad? Why you aren't just a little cock-slut, but you are a certified little cum-slut. Well you want it so bad, here! Ugh, I'm cumming so hard!" I felt her pull out of me with a fast pop and she started to spray on the carpet around me. "Lick up every drop you little slut!" I was entranced to do as I was told and I went to work to feverishly find every drop and clean it from the carpet. She could produce so much and I felt like I would be licking the floor forever. As she finished she collapsed back onto the floor and I continued to lick every spot I could find until it was all gone. Once I was done I went to nestle with my mom. I decided to pull up her pajamas and I rested my head against her soft chest which was covered with the now sweat dabbed shirt. "Thank you momma." "Thank you Alexandria. Let momma rest and I'll fix some dinner and we can talk about what else you'll need. Go get washed and dressed and come down for supper in thirty minutes." I left with a kiss and went to go wash, content with the pulsing throb coming from my abused hole. After my shower in my own bathroom upstairs I did my routine of lotioning up my skin. As I reached my new bedroom to grab some clothes I realized that I would now have to go back to being Alex once again. The thought depressed me and with each article of clothing I put on I felt my heart pang with grief. Instead of rejoicing in my new life I spent this time to grieve about the one I still had to live. __________ "Alex, sweetie, dinner is ready." "Coming." I had choked out my response for my throat was thick from tears and sadness. I had to wipe my eyes quickly, but I knew it would be no use. She would know, that was the true beauty of Miss Richards. Despite our short time together she knew me. She knew how to read me and knew how to react to me. As I sat down I waited for her response, and instead of the "Aww baby" response I expected I was met with a completely different one. "I remember the first time I cried over the life I could have had. I was in high-school, and one of the girls I was thinking of dating asked me why I didn't want to be a guy. We went back and forth over the subject and eventually she said she could never date me because her parents wouldn't understand her daughter dating a girl let alone a freak like me. I spent the rest of that night crying myself to sleep wondering if I had made the right choice with my life. The thing is, I had known for so long and knew it in my heart, but when someone makes you feel bad over who you know you are you will always question who you are. I know why you don't want to be Alex anymore and I am so sorry that I can't take away that part of your life, but I will do everything in my power to help you to be Alexandria so you never have to question who you are again. Just stick with it and give it time and soon you can leave it all behind sweetie." "Thank you momma. Truly. Thank you. So what's for dinner? I asked with true happiness. Her words had helped and to be honest whatever had been cooked smelled amazing. Not only did she understand me and knew what to say, but Miss Richards could cook. "It's my own recipe for pan seared chicken, mashed potatoes, leafy spinach with butter, and some dinner rolls." "You can make this in thirty minutes all by yourself?" "I learned from my aunt. She was a really good cook who taught me my way around a kitchen. A skill every growing girl should know." She said this with a wink and we dug in. The food was amazing, the chicken perfectly juicy with a little kick of spice, the potatoes and spinach were perfectly seasoned, and the rolls were an excellent addition to sop up the chicken juices. "That was amazing mom, wow!" "Glad you like it, okay now that we're done eating it's time to talk about what you're gonna need medically." "Okay, what all am I gonna need?" "Well first you'll need an appointment with the "family" doctor to get you started on hormone therapy. Usually there is a psych process to go through, but he has been my doctor since I was little and I'll get you through. After that you'll need to take additional vitamins for your skin, hair, and nails. Your hair is already a little moppy and so just continue to grow it out and when the school year is done we will cut it and style it how we can. Until then you'll have to make do with wigs when Alexandria is out to play so to say. For your body and facial hair we'll start you on electrolysis and laser treatments in unison to stop your hair growth and you won't have to shave anymore. Then to shape you feminine body we can start doing workouts together out back in the gym." "Wow, that's a whole lot of stuff. Do you think I would ever need surgery?" "I don't believe so, you have a light feminine face already. It just needs to be accented with the rest of you to pull it off. Your hips are pretty wide as it is for a guy and your shoulders are slender but powerful. The hormones will soften up your features and put a smoothness on you. Your face will round and become a little less sharp. You're gonna look fabulous Alexandria!" "Thanks mom." "Then the final thing is your voice. You can either practice and with hormones soften the voice and raise it, or you could get surgery done and with speech therapy go from there. The choice is yours, modern CTA, which stands for Cricothyroid Approximation, is actually very safe and from what I've seen it works wonderfully. It wasn't as advanced when I became the woman I am, but I didn't need much since I grew up talking like this." "And you sound lovely mom, I think I might look into the surgery one, it might be easier for me? Is it safe?" "There are rare cases of things going bad, but trust me, with the doctors I can afford, nothing will go wrong sweetie." "Alright mom, I trust you. Just tell me what I need to do and when I need to do it and I'll be there." "Okay sweetie, now let's go practice your walks, your voice, as well as try on some wigs that we missed out on for the party." __________ -Knock knock knock- "Hello, may I help you?" "Hey Sandy, are you ready for the party?" Sandy was dressed in a slutty nurse outfit. Her normally auburn hair was now dyed light strawberry blonde and was tied up in a bun with a little nurse hat clipped to the front. Her white and pink outfit was entirely made of latex it seemed. She was wearing white fishnet stockings and tall white leathery heels. Her small breasts were barely covered and I could almost see the edge of her areolas. The skirt that came with the outfit was riding dangerously high and I could tell that if she bent over her secret would be in danger of being revealed. "Uh, yeah, who are you?" Miss Richards was a miracle worker and had made me into a woman in three days time. She insisted that no one would understand me going as "Miss Richards" and so she suggested that I go as a sexy librarian instead. She had picked out a nice lengthy pitch black wig which she helped me do up in one of those stereotype librarian buns held together with a pencil. She also showed me how to put on all my makeup which was applied heavily for the "outfit's" sake. My lips were shined with glossy deep red lipstick and my eyes were dark and seductive with heavy liner, mascara, and shadow. The mineral foundation added the needed softness to my face without appearing overdone. I was also wearing a pair of thick black framed glasses so I could do the whole glasses removal trick. She made me wear a prosthetic bra to make me a medium A-cup which was shown proudly in a tight frilled black dress shirt with a power half suit jacket. The jacket stopped right above my bottom ribs and was wide shouldered and pinched tight at the bottom button making the appearance of a true hourglass figure. The skirt was a tight pencil skirt which came right above the knee with a slit that lead past my upper inner thigh allowing a view of the black mesh pantyhose underneath. I wore a pair of simple 2 inch black heels and was holding a few freshly taken out library books to finish it off. No one knew how to dress someone up like Miss Richards. I was a picture of pure seductive beauty and I could see it in Sandy's eyes as she eyed me up and down on her front porch. "I'm your date silly. Don't you recognize your own date?" "My date?" "It's me Alexandria, you invited me to Justine Collin's party on the bus, remember?" Her face was instantly drawn back in wonder. Her pretty lips pursed in surprise as the realization of who was standing in front of her. She stepped out and yelled her goodbye to the house and shut the door behind her. "No fucking way! Alex!? Is that you? Holy shit Alex, what is this? You look amazing, oh my god!" "Thank you, I know right? And it's not Alex tonight, tonight I am Alexandria Richards and I'm a sexy librarian." "Damn right you are! Shit Alexandria, you are so sexy, you got me excited just from seeing you in the doorway." "Thanks Sandy, if this night doesn't go well I just might need a nice big shot of whatever medicine you can give me Nurse Dee." "Oh don't you worry babe, no matter how this night goes I'll be sure to give you all the medicine you want. You ready to walk over?" "Yeah, I'm all set, let's go." As we walked I felt her hand slip into mine and I could tell she was taking the extra time to feel the new smoothness on my skin. Her fingers felt nice as they traced over my wrist and I felt close to Sandy once again and it felt nice to feel that way in my head again. To know that things could go back to normal except for a tiny little change. There was no girl I could date that could understand me more than Sandy and that calmed me as we stepped closer to the moment of truth. I would have to pretend to be the daughter of Miss Richards who would be going to school next year with all these people. My heart raced and with a grip of Sandy's hand I relaxed for once as we stepped up to the doorway. "You ready babe? Don't fret, you look amazing." My fingers trembled as I reached for the door handle. Here I go, fingers crossed. That concludes part 10. Was going to write more, but I have too much in mind for the party. I appreciate any ideas or suggestions or critiques you have to offer. Please feel free to reach me at das4200@yahoo and I will respond as soon as I can. Please also thank and donate to the fine people at nifty if you have the means. Without them these stories wouldn't be able to be shared.