Natalie's Story

My first attempt at writing a story so hope people enjoy and if successful will do others. My stories will be about my own personal experiences, some true and others fictional and I will note fiction vs. non-fiction.

First a little about myself I guess. I am currently 31 years old, Japanese-American and a transgender female. My first story is non-fiction and takes place when I was eighteen years old and how I lost my virginity. Besides my own name I have changed the names of the other people in the story. Hope people enjoy it.

My given name was Nathan but I use Natalie now, yes not a very Japanese name, but I was adopted by a white couple when I was seven months old and grew up in the U.S. and raised as a white American in Charleston, South Carolina. Being raised in South Carolina I don't have a Japanese accent but the subtle southern drawl common to the Low Country of coastal South Carolina and Georgia. Other than my looks you could not tell I was Asian at all. It was always funny to me when I met someone new and I spoke the look on their face when they expected me to have an Asian accent.

By the time I was eighteen I knew I was transgender and attracted to boys, hell I knew I was attracted to boys when I hit puberty, but I was still living my public life as a boy and while I had not started any hormone treatments or any type of transition into a female I was living my private life as a girl. I suppose you would call me a twink, gay, femboy, or crossdresser even though I identified to myself as a girl, to other people I was a twink, gay, sissy male with a crossdresser fetish (not that many people knew I was a crossdresser in private). I had been crossdressing as a girl for sometime now with only my best friend Renee knowing about it and then more openly in the privacy of my home with my mother knowing about it when I told her I felt I was transgender.

When I was five my father, who was a Marine Corps A-10 Thunderbolt (Warthog) Pilot, died in a training accident when his plane crashed so growing up it was just mother and I. My mother was fully supportive of me being transgender and by the time I was eighteen I had already completed a lot of the nonphysical steps of transition; such as seeing a Gender Therapist. My mother and I decided to wait until I graduated high school before I started the hormone treatment and by the time I would start college I would be a female. At home I lived as a girl. One reason we decided to wait until after high school was that I went to a private school in Charleston and like most private schools in the South it was religion founded and my mother and I were pretty confident they would not take to having a transgender student.

Physically I was always feminine looking and acting and even my voice sounded much more feminine than masculine even after puberty. Looks wise...well trying not to sound conceded, but honestly I was pretty almost to the point of beautiful in a feminine manner. I was never described as a handsome young boy but always a pretty young boy in a girly way. Even without makeup I was prettier than a lot of girls at school and when I put on makeup well frankly I was very passable and very pretty; I did not classify myself as "hot" because I lacked the curve of boobs, other than that I had...still have...a very girlish figure even if I was skinny.

Only thing I did not like about my looks whether dressed as a girl or not was that at age eighteen I looked much younger. Looking much younger for my age I would come to appreciate as I got older. I had a very small penis, four and half inches to about five inches at best and very thin, but I never cared about that. I liked having a small penis; made me feel much more like a girl.

At eighteen I stood only five six, weighed only about one twenty and had a very feminine figure without the breasts and zero male muscle tone and had a very cute feminine butt, skinny but just so cute. I wore my hair a little longer than most boys I knew so when I got home from school I could style it in a cute feminine short haircut and put girly hair clips in it. The only hair I had on my body was on my head, I had been using hair removal cream and or shaving the rest of my body for years now. My complexion was alabaster skin tone that would burn quite easily if I stayed in the sun to long without a high SPF sunscreen.

Naturally I had Asian features and almond shaped eyes but my eyes were wide that really complimented my heart shaped face and natural pouty lips. I have black eyes, but not a dull lifeless black but eyes that gleam like polished opals. I have always been rather prissy as well and very much a girly girl.

My mannerisms where also very feminine which I could think my mother for. My mother was a true southern lady and by the time I was eight she had me in etiquette classes and cotillions to learn how to be a proper southern gentleman and as I got older I focused my attention on what the instructor was telling the girls. My mother and I also watched old movies together and I modeled my feminine actions after movie stars such as Vivian Leigh, Audrey Hepburn, and others. They had so much class and feminine wiles compared to most actresses in today's movies.

It was a Wednesday afternoon in late March, a little after four o'clock and I was in my bedroom on my bed wearing a sexy school girl uniform with Charles "Chuck" Whitlock's on top of me making out. Everyone at school and his friends called him Chuck but I preferred Charles.

Charles was stripped down to only his underwear. My legs were wrapped around his body and we were grinding our pelvis against one another as we kissed and had each other's tongues in each other's mouths as I gave little whimpers of pleasure. My short plaid skirt was hiked up and I could feel his larger erect penis under his briefs rubbing against my own small erection though my white cotton bikini cut panties. Charles had my arms pinned above my head with one of his hands and the other was under me caressing my butt as I gave girlish whimpers of pleasure into his mouth. This situation with Charles was about standard once, sometimes twice a week.

Charles was far from my boyfriend and as a matter of fact had a girlfriend. I was just his little secret, his dirty little secret you could say, for a while now. Like me, he was eighteen and a senior at our school. Charles was a very cute boy who played linebacker for the school's football team and played third base on the baseball team and had a baseball scholarship to a Division 1 college. Why he started fooling around with me I never knew, maybe he had an Asian girl fetish or maybe he was secretly bi-sexual, I never knew and I never asked.

Charles was very cute, much taller than me but almost every boy my age or even a couple of years younger were taller than me. I had known Charles since middle school and had been his little secret for quite some time now. His girlfriend was popular, very pretty but prudish and did not perform oral sex on him. I also enjoyed how he "took control" of me when we had our fun get togethers. I had been and always was a submissive lover and enjoyed being such.

Charles was the only person besides my mother and my best friend Renee who knew I crossdressed and I knew he was not going to say anything.

"I want to fuck you." Charles said as lifted his head and upper body off of mine and let my hands go.

I ran my hands over his bare chest, "Charles, you know I am not ready for that."

While I had given him many blow jobs since we started fooling around as well as two other boys he did not know about. The two other boys were also 'straight" and masculine (I was not attracted to feminine type boys at all) but I never dressed as a girl for them and all I did with them was give them oral sex on occasion and they never kissed me or did the things Charles and I did. Thing was; I was still a virgin. I wanted to have sex with him or sex with someone, but I was scared of anal sex. When I masturbated I would use a finger inside me on occasion but that was it.

"You are never ready." Charles replied and I could tell he was getting a little frustrated, but I knew how to handle that.

I smiled up at him and brushed the purple strands of my wig away from my face, I preferred my natural hair but today Charles wanted me to wear my purple wig that had long hair. I had several wigs I wore on occasion and liked to style my makeup to match what ever look I was going for with wigs and outfits.

I leaned up and started kissing his bare chest and running my tongue over it and then his nipples causing him to give a masculine moan of pleasure.

"But I do things Jennifer does not do for you." I said as I flicked my tongue over his nipple and ran my right hand down to his crotch, slipped my hand under his briefs, and started gently stroking his erect penis.

"Fuck...that feels good." Charles moaned out, "Ok...but before you suck it I want to watch you do it."

I gave Charles a charming smile, "Do you want to help? I like it when you help me."

I knew what he wanted when he said "I want to watch you." Charles liked to watch me cum and of course I did not mind in the least.

Charles grinned, "Ok."

Charles moved off of me and kneeled between my spread legs and pulled my panties down to my knees as I unbuttoned my white shirt to expose my lacy white bra. I had no boobs but I liked wearing a bra; made me feel very girlish. Plus it made it easier to play with my nipples and I loved my nipples played with. I then pulled my bra up a little to expose my brown nipples.

Charles reached to the side of the bed and pulled out the lubricant that I kept there for just such occasions and also when I masturbated. I flinched and giggled when he dribbled the cold liquid over my small erect penis and then gasped out in pleasure as his hand wrapped around my shaft and he started stoking me slowly. I propped myself up on my elbows so I could watch. Charles's hand completely swallowed my penis.

"Feel good?" He asked me.

"Y...y...ohhhh God, yes." I moaned out.

"I still can't get over how small your dick is." Charles commented as he stroked me faster.

I did not bother answering and lay back on the bed and started playing with my nipples. I started out just rubbing them and then started pinching them harder; I liked my nipples played with roughly. I was making these girlish squeals and whimpers of pleasure as Charles masturbated me. It took me all of three minutes and I gave loud cries of these whimpering squeals of pleasure as I orgasmed. The warm thick fluid shot up and sprayed all over my bare chest.

Another thing I hated about myself and was very embarrassed by was how fats I always came. I never lasted more than four or five minutes even when I masturbated myself and with someone doing it for me like Charles was I came even faster.

Charles grinned down at me as I blushed at how fast I came and covered my face with my hands.

"I...I am sorry."

Charles chuckled, "I told you before I like that you cum so fast." He let go of my penis, which was still erect. "Are you going to eat it? I like when you eat your own cum."

I giggled and ran my right hand over my body to scoop up my sex fluid. "Yeah, but you like when I swallow yours more."

Charles laughed.

I placed my hand to my mouth and ate my own cum and licked my fingers and even scooped up some I missed and ate that also. I really did enjoy eating and swallowing cum; my own and even more so someone else's. I loved the taste of it, the texture of it, the smell of it, and when a boy came in my mouth it was just such an awesome feeling to have it shoot all in my mouth and down my throat.

Charles moved to sit on the edge of the bed, "Speaking of you swallowing my cum."

I grinned and he did not have to elaborate at all. I pulled up my panties and got off the bed and on my knees between his legs and pulled down his white briefs. His pretty penis sprang up and I started stroking it slowly and kissing it at the same time. I really loved giving blow jobs a great deal and I was rather good at it I had been told. Course truth be known I had a lot of practice with giving oral sex many times to Charles and the other two boys and there had been others also I no longer am "involved with". At eighteen I was already pretty much a closeted oral sex slut.

I started out slow and was teasing Charles with my hands and mouth and tongue; taking just the head of his seven inch penis in my mouth and running my tongue over it while my right hand slowly ran up and down his shaft as I enjoyed his masculine moans of pleasure. Charles had a very nice penis.

"Fuck, Natalie, that feels good but I don't have a lot of time today so make me cum."

Besides myself, my mother, and my friend Renee, Charles was the only other person that used Natalie as my name and not Nathan. I liked it.

I took my mouth off his penis and giggled and just kept teasing him. After about a minute of teasing him, Charles decided he had enough and he grabbed the back of my head and forced me to take him deeper into my mouth and down my throat. I knew how to deep throat him but the suddenness of it made me gag some and he held my head down so I choked a little on his penis.

"Slut, I told you I don't have much time. Now suck it good and make me cum, you fucking whore."

I liked being talked to like that; verbal humiliation turned me on. Charles let go of my head and I started sucking his cock harder and faster. My own saliva started to run out of my mouth and down my chin and over his shaft making it slick so my hand easily ran up and down his penis. Charles was moaning and I was making girly whimpers. He lasted several more minutes and put his hand back on my head, his body tightened, and he thrust into my mouth and down my throat as he came.

I loved the way his cum shot into my mouth and down my throat and swallowed as his penis jerked and shot his load into my mouth. He came a lot and I swallowed every drop of it. After Charles orgasmed I used my hand to milk every drop of his delicious cum out of his penis and licked and sucked him clean.

"That's enough." Charles chuckled as he pulled away from me and I looked up and at him and pouted. "Fuck you sure know how to suck dick."

Charles stood up and started getting dressed as I kneeled on the floor and wiped my chin and around my mouth with my hand.

"I like sucking yours." I told said and gave him an innocent look. I knew how to play the innocent girl next door very well and my natural physical looks made me appear as such.

Charles pulled his Izod shirt over his head, "You just like sucking dick in general cause you are a cocksucking whore." He said and grinned down at me.

"Am not." I gave him another pout. "I was a good girl before you made me start doing this."

Charles sat back on my bed to put on his shoes and I stood up and adjusted my bra and buttoned my shirt. "If I remember right it was your idea."

"Was not!" I said in mock indignation and stuck my tongue out at him.

Truth was, it was my idea. I had known Charles ever since we were eleven and as we got older we naturally did not hang out in the same social clique at school but he was always nice to me. It was very obvious by the way I acted and looked I was gay and that never bothered him. Then one day at school we were paired up to work on a project for our history class and it required out of school work together and I kept noticing how he looked at my ass and he made a comment about me being so girly looking and even said I was prettier than most girls at school.

I then confessed to him about being transgender and one thing lead to another and we were soon kissing and then I lied and told him I had never done anything sexual and wanted to try giving a blow job and he was all for it and the rest is history as they say. I always suspected after that Charles was secretly bi-sexual.

"Do you want to come over again tomorrow?" I said hopefully. "I can wear my cheerleader outfit. I know you like that." I said hopefully. "My mom works again tomorrow night."

"I can't. I have plans with Jennifer." Jennifer was his girlfriend.

I gave him another pout but was not at all jealous. I liked Charles but I had no romantic feelings for him at all. Once we were both dressed he kissed my forehead, he never kissed me on the lips after I gave him a blow job and swallowed his cum. He had this hang up about that. He then left and I was horny again so I masturbated once more and then changed into my Power Puff Girls Pajama set, did I mention I was also a huge nerd, and did my homework; fixed dinner, watched a little television, and went to bed before my mother got home from work around One A.M. Before I went to sleep I did get myself off one more time and fingered my own butt imagining Charles fucking me.

What I did not know at the time but was to find out the next day was that Charles and I were not alone in the apartment my mother and I lived in and I was seen being dressed as a girl and giving him a blow job.