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The Story Of A Kat

"Some background information, setting the story background, a first kiss, and agreeing to give a handjob."

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I recently got dumped by a thirty-nine-year-old black man, Marcus, who I had been dating for several months. Being heartbroken and that I have wanted to write a story to post on Lush for some time now, I decided to write about our relationship with the hope it will help me get over him. God knows I have tried so many other ways including random hookups with several men I met online and once with two men I met online who fucked me in a three-way. Meeting men online was nothing new to me.

I had been doing it for a while in between my relationships. I am a member of a particular online dating, fetish website. I joined the site when I was nineteen to meet men to hook up with. I live in a small city in South Georgia that borders the Okefenokee National Wildlife Refuge; we locals just call it The Swamp. Waycross only has a population of about fourteen thousand so it’s hard to meet men where I live that are willing to enjoy the company of a transgender girl.

It’s not impossible to meet local men or boys; I have had either one-time hookups with locals or have been the dirty little secret to some older men in discreet relationships. I was twenty-three when I started dating Marcus and before him, I had never dated a man or boy in an open relationship.

Marcus was not the first black man I had been with; the racial diversity in Waycross, Georgia is about thirty-five percent white and sixty-five percent black, and small percentages of other races. So yes, I have had relationships with black men and black boys also.

When I use the term relationship I am not only using it to refer to being in a boyfriend/girlfriend type relationship. I use it to include one-time hookups, meeting men online, or being the discreet dirty little secret to a man.

One of my Daddies I met online that I was a dirty little secret for I would meet in a dirty cheap motel room two, sometimes three, times a month. He was fifty-four years old, married and a Southern Baptist preacher from another close by city. That lasted about eight or nine months.

He took Viagra every time we met, not because he particularly needed it; but so he could fuck me, use me, and degrade me more times throughout the night than he could have without it. He used to enjoy doing a lot of non-Christian things to me and he got particularly turned on when I wore costumes for him.

I admit that I am a slut. I also have severe Daddy Issues so I tend to have relationships with older men, but I have been with guys my age as well. The men I met online have all been older, sometimes two older men, and once I hooked up with three older men I went to meet in a hotel room in Brunswick, Georgia.

The website I meet the majority of the men from is a fetish website. It’s a free site that caters to people with various fetish lifestyles whether you are straight, gay, bisexual, or transgender. It has a group section that people can create and or join groups in your area to post or reply to personal ads for what you are looking for. You can post photos and videos on your profile so that everyone can see whether they are a paying member or not, and you can exchange messages with other members for free.

It’s easy for me to meet men to hook up with online. Not because I think I am all that and think all men want me; being a transgender I know that certainly is not true. What makes it easy is that I have low standards for the type of men I seek out.

I don’t care about their physical appearance or their race. What I look for when I hook up with men I meet online is their age, at least fifteen years older than me, and that they are masculine, dominant, and willing to be my Daddy Dom and abuse and degrade me. I don’t care if they don’t want to get me off or if they don’t suck my tranny cock, when they are willing to do that, I consider it a bonus. I put my partner’s or partners’ sexual needs and satisfaction over my own.

I certainly do not care about penis size. As long as the man’s penis can become erect even with the help of EDD medication, yes been with a few older men who may not have needed it but took it so they could enjoy my skinny body as much as they wanted. While I have had a few men who were well endowed to just damn huge fuck me, I don’t care about penis size.

An example of how I want to be treated was with the three black men I met in a hotel room in Brunswick. The men were in their forties, clean-cut professional black men, and from Jacksonville, Florida. None of the three were particularly attractive and one must have been at least fifty pounds overweight. I made arrangements to meet them halfway in a motel off I-95 in Brunswick. Being a submissive, bottom, sissy, tranny slut; I consented to allow the three older men to dominate me.

They had me do a strip tease dance until I was wearing nothing but my panties, bra, and thigh-high stockings. One man used a red sharpie marker to write crude things on my body and then put a collar and leash around my neck. He made me get on all fours and paraded me around the room while his friends mocked and taunted me with various verbal insults. I was then led to the other two men and forced to suck all three of the men’s cocks until they came in my mouth and I swallowed.

They then proceeded to have more degrading fun with me. They took turns whipping my butt with a belt and took many photos of me. I sucked their cocks often, they tied me up, used anal toys on me, put my penis in a cock cage, and fucked me relentlessly for several hours. They did all that without letting me orgasm. When they were done with me, one man unlocked my chastity device and they left me in the hotel room. I was exhausted, sore, and horny. I jerked myself off three times before I was satisfied. I then fell asleep with cum over my body, on my face, in my hair, in my tummy, and in my ass.

The difficult part about meeting the men on that site is weeding out the men who are not serious about meeting and who just want me to chat with them, video chat with them, or send them other pics of me, etc.

Not that I mind having my photo taken or a video made of me. That turns me on and I take photos and make videos of myself to send a man I am either currently in a relationship with or ones that I have been talking to I met online and we are making arrangements to meet. I like for them to see what they are getting. I don’t get into just the erotic photo exchange with men. I have plenty of photos on my profiles for guys to look at.

I enjoy dressing in fetish outfits or costumes for the men I meet or I am in a relationship with. I like when they tell me what to wear when we hook up and will dress and play out whatever role they want me to. I enjoy it when they take photos or make videos of me when I am in a costume or a fetish outfit or lingerie. I like when they have me play with myself for them before they fuck me. Using an anal toy on myself, fucking myself with a dildo, or masturbating while they take photos or video it and watch me turns me on. Being an obedient, nasty slut for my Daddy is a huge turn-on for me.

By the time I met Marcus ten months ago in October; I had had sex with many men and boys. As I said, I am a slut. Unwisely I don’t always practice safe sex when I hook up with men, I know it is not smart but I prefer bareback so much. I do get tested for STDs after those encounters and so far I have never tested positive for any. Keeping my fingers crossed. I have read many articles about safe and healthy anal sex so I practice impeccable personal hygiene and keep my tranny pussy clean for men and my toys.

As I was thinking about how to start my story about Marcus, I decided to start at the beginning of when I first became sexually active at sixteen. I won’t go into detail about all the men and boys I had sex with, which would take too long. I will limit it to just a few and end with Marcus. I won’t go into much detail about how and when I started transitioning either, but I do think a few things need to be explained.

I would like to point out that I am not an LBGTQ activist; I am not some transgender who wants to be a role model or poster girl for others who may be questioning their gender identity. I don’t force my transgenderism on people, I don’t protest or march in LGBTQ parades, and I don't do all that Woke crap.

I don’t get my panties in a bundle when people refer to me as a tranny or a shemale, I often refer to myself that way. I don’t believe in forcing people to use proper pronouns and I believe that school systems should not play a role in a young person’s gender identity. I know who I am and just want to live my life as normal as I can.

I won’t describe my looks or voice, which can be seen in my story images, profile photos, and heard in my videos. I will write that I have always been feminine acting and looking for as long as I can remember. I do consider myself attractive and cute and I have been told I am pretty. I have been told that many times by people even before I started my transition. I was never called a handsome boy or teen or young man, but a pretty boy or teen and a femboy, twink type.

While I am thin, I do think I have a sexy body and a very cute ass. I have not had breast implants, something I am currently considering, and my breasts are very small, natural, not even an A cup, and developed from hormones. I do have a penis and it works and works very well. My cum has been affected by the hormones; it’s not as thick or abundant as it was before I started hormones and sometimes very little comes out, but the blissful feeling when I orgasm is the same. I do miss the days when I would ejaculate thick, creamy, sticky cum.

I am very outgoing and flirty and love to socialize and meet new people. I was not always like that, when I was in my teens I was shy and introverted. I came out of my shell around age nineteen.

I won’t say that being called a femboy or twink or other names I was called or overheard someone saying never bothered me. It did. Sometimes I would get home from school and cry in my room. Now, however, I have learned not to let it get to me.

I can be quite prissy and a girly girl and emotional. Not a drama queen by any means, but I do cry when I get my feelings hurt badly, from heartbreak, at sad and happy moments in movies or books, and my daddy has made me cry countless times.

I am attracted to dominant masculine men who are straight but like to have a pretty tranny girl as a plaything. Being a man’s first transgender fuck is a huge turn-on for me. I don’t have sex with other transgender, gay men, sissy femboy types, or girls. I am not attracted to those types. I don’t penetrate men. Besides a man’s mouth when on the rare occasion I hook up with a man who likes sucking my cock, I have never penetrated anyone and don’t intend to.

I have met some men online who have told me they don’t bottom and when I meet them they try to get me to fuck them. I tell them no because I find the idea of me fucking someone revolting and it just can’t do it. I mean that I physically can’t. I am so turned off by it that I can’t get an erection. If they want I will stick my tongue or finger up their ass, but that’s it. I don’t even like using anal toys on a man. I do like rimming a man’s asshole.

I am a submissive girl both in my sexual life and no-sexual life. I do believe a girl should be subservient to a man she is in a relationship with both sexually and non-sexually. Don’t mistake my being submissive to men as me being a doormat or that I allow all men to walk all over me. Men I am not in a relationship with, hooking up with, or having a one-night stand with cannot just treat me like crap. I don’t allow that and can be quite sassy and I do stick up for myself.

Sexually I can be rather freaky and kinky and do about anything to a man that he wants me to and allow him to do about anything to me he wants. Yes, there are things I won’t do but that list is pretty short.

My largest fetish is being with an older man who is my Daddy Dom. I do believe that my “Daddy” should discipline me for my misbehavior. I believe he has a right to fuck me anytime he wants, for me to suck his cock anytime he tells me, to keep my cock in chastity, and not allow me to orgasm unless he desires it. I believe that I am his property for him to use as he sees fit. That includes if he wants other men to fuck me as well.

My sex life is not just about being dominated. I am a very affectionate person and like to show it and have it shown toward me. I do like romance and intimacy and making love and kissing. I love kissing! I like to cuddle, be held, caressed, get flowers, and do all the silly things boyfriends and girlfriends do.

I do believe in love and I have been in love a few times with men or boys I have been in a relationship with, they just did not love me back like I thought they did. I do tend to fall in love quickly and confuse a man’s feelings for me and that has left me heartbroken at times. I deal with heartbreak in an unhealthy way.

When I am heartbroken, I aggressively seek out men, mostly online, to hook up with and go from one man to the next or sometimes two men at a time until I meet a man I believe cares for me. I always take a vow to myself I won’t fall in love so quickly and when I do get my heart broken I won’t do what I typically do, but I always end up in the same pattern.

I have been in five long-term relationships and in three of the four, I misinterpreted their feelings for me and ended up heartbroken.

The first was with a boy when I was sixteen and he was the same age, the next two were with older men including my recent relationship with Marcus. The other two long-term relationships were with older men, who include the Baptist preacher; I knew what I was to them.

I would like to add one more thing before I finally move the story along; I was never abused or molested in any way growing up. Because of what I enjoy sexually and how I like to be a nasty, tranny slut at times, and my deep-rooted Daddy issues I have been asked that. I wanted to clarify I never was and my Daddy issues come from another reason my story will make clear.

So that’s basically who I am and hopefully, I did not bore the readers too much. Now to how I became who I am today.

My mother and father got divorced when I was eleven. Daddy moved to a city south of Atlanta and left me and my older brother by three years and my mother. My daddy did not cheat on my mother that I know of and he was never abusive to her or his kids; it was just one of those things when parents can’t live together anymore. They did argue almost constantly for about a year before they were divorced.

My mother seemed much happier when they got divorced, my brother said it did not bother him but I could tell it did since he and daddy are close, but I took it the hardest. I don’t know why I took it so hard. I certainly was not my daddy’s favorite. It was like I did not even exist to him or was just some stranger in the house he had to acknowledge was there on occasion.

I do know why he never liked me. It was because I was a sissy, fem gay boy. I was not like my brother, who is masculine and tall and tough. I did not enjoy going camping or canoeing in The Swamp as my brother did. I did not like going hunting or playing sports or going to sporting events, all of which my brother enjoyed and excelled at. I was prissy and effeminate in every way including my looks and my father hated me for that. He didn’t call me a sissy or other derogatory names about my effeminate ways. That would have meant he would have had to acknowledge I was his child and that I existed.

I craved his attention, however; I needed it and would have done anything to get him to pat me on the back and say, 'I am proud of you,' or just say, 'good job.' One example of just many of my failed attempts for my daddy to love me or at least acknowledge me was when I was ten. He and my brother were planning a camping trip in The Swamp and I told him I wanted to go with them. He said no but my mother made him take me. It was a disaster.

I hated it! We canoed to the campsite and by the time we set up our tents, I was crying and wanted to go home. I was hot, tired, smelling like bug spray, and dirty. I hated sleeping in the tent and every sound I heard from the local wildlife scared me and the alligators terrified me. I could not sleep because I imagined an alligator crawling into my tent, pulling me out with his huge mouth, dragging me into the swamp, and eating me. The next morning, my father told me to get in the canoe. He did not say a word to me as he paddled us through the swamp. When he was able to get a cell phone signal, he called my mother and told her to meet us at the park’s welcome center to pick me up.

My mother told me to stop seeking his approval. She and I have always been close. But I never did stop seeking my daddy’s approval. Even after the divorce, my brother and I would go visit him for a month or so in the summertime. He never wanted me to visit but my mother used the divorce court order regarding visitation rights against him. Told him if he did not want me to visit then my brother would not visit either.

My mother did that not because she wanted me to go, she always tried to talk me out of it and tell me just she and I could have quality time together while my brother was away. She did it because I wanted to go, hoping my daddy would one day love me. When I came out as transgender, my daddy wanted nothing to do with me and I had not seen him since I was fourteen.

One would think I would have just given up or realized he was never going to love me and accept me, but I never did. Every time I went to visit, I would hope he would change. Even though I have not seen him since I was fourteen, I still have this fantasy he will show up at the restaurant where I work as a waitress and tell me he loves me and for me to forgive him for being the way he is. I still send him a text every now and then to say hello, but he never replies.

We grew up in a middle-class neighborhood and after the divorce, my mother kept the house. It was nothing fancy, just a standard three bedroom, two bath house. The neighborhood did not have many kids living there, it was mostly a place where young couples bought starter homes and after having a kid or two, they would move.

When I came out to my mother at age fourteen that I was transgender and she took it very well. We sat down and told my brother and he just laughed and told me that was not surprising. I have always been close to my brother and he took it upon himself to protect me. I never did have to come out that I was gay, that was a given. What would have shocked people was if I had come out as straight.

My mother took me to all the doctors, both the physical and the mental, for counseling and advice on medical procedures and drugs. It was not to try and get me to change my mind but was the best and safest route to take because it’s not just a simple thing to one day say, I am a girl, not a boy, or vice versa. I decided, with my mother’s approval, not to start the hormone treatment until I was eighteen. There could be some serious side effects when taking them as young as I was at the time. I did start seeing a therapist who specialized in gender reassignment. I was surprised there was one in Waycross. I still see her once a week.

Even though I was not going to start hormones until I was eighteen, I wanted to start part of my transition at fourteen. My therapist warned me of the negative reactions I would get from people, which I knew there would be a lot of, but said it would be a good idea. I decided to start dressing and acting like a teenage girl and to let other people know I was transgender. That was the scariest thing for me.

I started slowly. I did start shaving what few hairs I had on my body and by age sixteen, it progressed to getting waxed at a salon, including my private area. I did not start wearing skirts and dresses to school but did wear girl jeans and tops and panties and even a bra, although I didn’t have any breasts. My mannerisms were already feminine so that was easy and my voice was already girly-sounding. I started to let people know I identified as a girl and not a boy when I started high school. My mother met with the school principal to make him away. I was expecting the bullying and the name calling and even maybe getting beat up at school.

Surprisingly, most of that never happened. Yes, I was called names and even heard the whispers as I walked the halls of the school, but no one physically touched me. It was like they expected it of me or they just didn’t care. Also, they were afraid of my brother and didn’t want him to kick their asses.

My brother had a well-earned reputation of being one mean son of a bitch. He was tall, masculine, strong, muscular, and mean. Well not to me, to me he was a big teddy bear. To others, he was not. He was not a bully at all, but he did like to fight and got into a lot of fights. He never started them but he did have a quick temper and if anyone wanted to fight him he was all for it.

My brother saw fighting as a competition and even got some type of strange pleasure out of it. He didn’t always win but the rare times he lost, the person he fought didn’t want to ever fight him again because even when he was losing, he didn’t quit. I hated when he got into fights and they scared me.

My brother also had a sort of honor or chivalry to him. He liked to protect the weak, people who got bullied, and girls. The worse I ever saw him beat another boy was when my brother saw this black boy at school hit his girlfriend. My brother didn’t even know the girl but just another student in the school. He got suspended for a week for that one.

I always imagined my brother as a knight of King Arthur’s Round Table. Yes they, like my brother, were flawed, but they were chivalrous and protected the weak. When I was twenty and he was twenty-three, he joined the army and became a Ranger. He is still an Army Ranger and excels in his career.

By the time I was sixteen and started my junior year of high school, I was wearing skirts and dresses to school and everyone knew I was transgender. My brother’s girlfriend, Denise, taught me how to put on makeup and do my hair, which was then just touching my shoulders. I liked Denise. She was a sweet girl and on my birthday and Christmas would buy me makeup kits and take me shopping for girl clothes. She and my brother are no longer dating but I still talk to her often.

I was still pretty much left alone and not harassed too much. Yes, I still heard the names and the whispers, but at age sixteen, I no longer went home crying over it. What did bother me was that I didn’t have any friends, not really. I had yet to meet my best friend, Melissa. I was lonely for friendship.

The only kid my age in our neighborhood was a boy named Kevin. We went to the same school and I had known him since I was about eight or nine when his family moved into the neighborhood. We used to play together until we got older and got at the age where kids start noticing the difference between girls and boys more. He noticed I was different than other boys and we stopped hanging out. He was still nice to me and said hello when we were not at school. At school and around his friends he ignored me.

In the late spring when we were both sixteen, he started to come over to my house and hang out. It was not to be my friend but to use my brother’s video game systems and play my brother’s video games when my brother was not home. My brother had a great gaming system but at nineteen, he didn’t play much anymore. He was working and going to the local community college, taking the occasional class and trying to figure out what he wanted to do with his life.

Kevin was not an attractive or even a cute boy. I would not even call him average-looking. I hate to use the word ugly so I won’t. He was just not an attractive boy. He was tall for sixteen, I guess. I didn’t know because I was only five-six at the time and would never grow past five-seven so most boys my age were taller than me. Kevin was maybe five-eleven or even six feet tall. He was not fat but was slightly pudgy.

His bottom teeth were crooked and he needed braces to fix them and he had a bad break out of blackheads on his forehead just below his hairline. I badly wanted to give him a facial and teach him how to wash his face to improve his complexion.

I knew he was not very good with the girls and that was not just because of his looks. The boy did not have much in the way of social skills. He could be crude and vulgar at times with stuff he said and cursed a lot. But he was nice to me. I knew he came over just so he could play my brother’s gaming system but I didn’t care. I was glad for the company.

I would hang out with Kevin in my brother’s room while he played the games and even played a few with him. He was into first-person shooter wargames and I was into RPG fantasy games so we didn’t have the game selection in common. I tried to enjoy the games he liked and played them just so I could pretend he and I were friends.

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Kevin was really into gaming and would sometimes play with other people online and I would watch and listen to what he was telling people he played with. I would make him snacks while he played and made sure I was a good hostess and get him stuff he wanted. I didn’t have a crush on Kevin, I was just that starved for friendship and I felt it was a girl’s responsibility to be a good hostess and take care of her guest.

One day during the early summer after school was out, Kevin came over to play the newest releases of a wargame he bought. He wanted to play it on my brother’s system. I happily let him in just to have company. Plus when he took breaks from gaming and ate the snacks I fixed for him, he talked to me as a friend would. I guess he was more comfortable around me than with other girls because he might still have seen me as the young boy who he used to play with and not a girl.

Kevin normally sent me a text to let me ask if he could come over, but that day he didn’t. It was a little after eleven in the morning and I had yet to take a shower and get dressed. The tee shirt I wore was the same one I had slept in for the past week and had not washed and had food stains on it. I am not the neatest person in the world and hated cleaning my room.

I let him in and when he went to my brother’s room, which was not something my brother would have liked, I quickly went into the bathroom I shared with my mother. My mother and I, being the girls in the house, shared a bathroom, and the other bathroom we left to my brother.

I smelled my armpits, wrinkled my nose at the smell, and put on some deodorant. I then brushed my hair and washed my face because I had strawberry goo from the pop tart I ate for breakfast in the corner of my mouth. I brushed my teeth and then put on a little makeup. I put on just some mascara and eyeshadow and lipstick. It was nothing too drastic since I was not trying to impress Kevin, I just didn’t want any boy to see me like I just got out of bed. I went into my room and put on some clean panties, a padded bra, and a clean tee shirt. I know I didn’t need a bra but I liked wearing one. I then put on a pair of tight, short, purposely faded jean cutoffs. I grabbed a fashion magazine and went to my brother’s room.

When I walked into my brother’s room, Kevin was already playing the game and wearing a headset and playing with other people. I watched for a while and then started looking at my fashion magazine. I liked watching him but did get bored after a while. It was just nice to have someone around besides my mother and brother. Yes, I was that lonely.

After about an hour of playing, Kevin cursed into the headset, took them off, and threw them on the floor. I winced. They were my brother’s and I hoped they were not broken.

“Fucking sorry ass newbs!” Kevin shouted. “Don’t know what the fuck they are doing!” I giggled at his nerd rage. “God damn fuckers. I hate playing with these fucking…” He then used the F word which was a slang term for homosexuals.

Kevin looked at me. “Oh fuck, Steve, I am sorry,” he used the name I was born with. “I didn’t mean it like…”

“It’s ok, Kevin,” I interrupted his apology. “I’m not that. I’m a girl who liked boys so I’m not gay, but you shouldn’t use that word.” I smiled at him. “And it’s Katherine or Kat.”

When I turned sixteen, my mother signed the form to allow me to legally change my name to Katherine and most people who used my new name called me Kat. Katherine was my maternal grandmother’s name. She died when I was eight but I remember how much she loved me and spoiled me.

“I forget sometimes,” he told me. I knew he was not talking about he should not use that word. He sounded uncomfortable. “It’s, well, it’s just that… fuck I don’t know what I am trying to say. I just get confused sometimes about it.”

“You think you’re confused,” I said giggling.

Kevin chuckled. “I didn’t mean that. I mean it’s confusing because, well, umm, fuck, I don’t know what to say or how to explain it.” The poor boy looked frustrated.

“Just say it,” I told him. “That’s the best way.” I braced myself for him to call me a freak or sissy boy or use one of the other words some kids at school called me.

Kevin took a deep breath. “I know you want to be a girl.”

“No I am a girl,” I corrected him. “Inside I am a girl but outside I have a boy’s body.”

“Damnit, this is not fucking coming out right. That’s what I meant. I know you are a girl. You look like a girl and act like one and sound like one, but you have a dick and no tits and… Fuck, I don’t know what I am trying to say.”

I found his frustration amusing but I didn’t let him off the hook because another part of me wanted him to pay for using the vulgar slang term for a homosexual. I was also waiting to see if he would use it again or refer to me and people like me by other derogatory terms.

“And you are so fucking pretty,” Kevin blurted out so fast that I barely understood him.

“Oh,” I said and my eyes opened wide and my mouth hung open. I was not expecting that.

“I’m not a fa… not gay,“ the boy tried to explain. “But you are pretty. If I have not known you since we were kids I would never know you are a… well, have a boy’s body under your clothes.”

“Thanks, I guess.” It was my turn to be confused.

“God damn it!” Kevin exclaimed loudly in frustration. “I am trying to explain and you are making fun of me.” He sounded like he was getting angry.

“I am not making fun of you. I just don’t know what to say or what you mean,” I assured him.

Kevin sighed, “Ok let’s say that if I just met you or any boy we know just met you. Like if you just started our school and no one there knew you from years ago and they saw you for the first time they would think you are a pretty, skinny, flat-chested girl.” Kevin looked at his feet. “You should hear what some of the boys at school who have known you since freshman year or even the ones we went to school with in middle school and elementary school say about you.”

I rolled my eyes, “I can imagine. I hear what they say about me sometimes and what they call me.”

Kevin chuckled and looked at me. “Not that stuff, but other things.”

“Like what?” I asked. I was curious.

“Well, the things like you think they do say. Stuff like call you a sissy, a twink, a freak, and use that word you don’t like, but some guys say other stuff.”

“Go on,” I pried.

“Well, just, that… ok this is what they say, not what I say,” Kevin was flustered. “Some guys say that even if you are, well, those things, they call you that you are decent enough looking as a girl and would have you suck their dicks and some say they would turn you over and fuck your skinny ass as long as they didn’t have to see your cock.”

“Why don’t you say those things,” I teased Kevin.

I did not tease him to flirt with him but to try and show that I didn’t care what other people said about me. I did care and it did hurt my feelings but also excited and flattered me a little that boys thought of me that way. I thought of some of the good-looking boys in school that way and even a couple of the male teachers and some of the other kids’ good-looking fathers. I was sixteen after all and I got aroused and thought about boys as other girls do.

But what the hell did decent enough mean? My assessment of my looks was that I thought I was cute but too skinny to be pretty and I didn’t have boobs to be pretty. Even if I had developed boobs naturally, they would be small because I was so thin. I did think I had a cute butt though. Yes, it was small and skinny, but I thought it was sexy. I definitely thought I was better than decent looking!

I thought if I had been born with a girl’s body that I was attractive enough to have had a boyfriend by age sixteen. Something I desired badly. Not for sex but to have a boy I could kiss, talk to, go on dates with, hang out with other kids and couples with, and hold hands in the hallways at school like other girls. Yes, I thought about sex and masturbated a lot, but having sex scared me.

Kevin shrugged, “I guess because we used to be friends. It’s not that I don’t think you are pretty, because I do.”

“Do you want a snack or something to drink?” I blurted out.

I changed the subject because I was getting an uncomfortable feeling, had butterflies in my stomach, and also getting aroused. My five-inch cock was hard. I was aroused by what Kevin told me about other boys saying they would allow me to suck their cocks and even fuck me. Yes, I know they did not say it in a way that would show any type of affection for me or even like me, but just use me for their lusts. Still, it excited me and I was picturing in my mind which boys I knew at school said those things.

My penis was also hard because Kevin told me I was pretty. That was something I could not understand because I was not attracted to him.

“Sure. How about those pizza rolls you make? The pepperoni ones,” he sounded relieved I didn’t press the subject.

I giggled again, “I don’t make them, just pop them in the microwave.”

After I put the pizza rolls in the microwave, I set up a TV tray for Kevin in front of the sofa in the living room. I did not allow him to eat his snacks in my brother’s bedroom. When they were done I set the plate and a soda can on the tray and went to get Kevin.

I found Kevin standing over my brother’s bed looking at a magazine and some other magazines were stacked on the bed. He turned and looked at me when I walked into the room.

“What are you doing?” I asked in a fearful voice.

“I found your brother’s porn stash,” Kevin told me, grinning.

I walked to the bed and saw the magazines and blushed. I blushed so deep that I could feel my face flush. I did not know my brother had a porn stash, but then again I didn’t go snooping around his room either.

“Put those back. If my brother knows we have been in his room he will yell at me, but he will do worse to you,” I warned Kevin. My brother would never raise a finger to me but he would not be hesitant to kick Kevin’s ass.

Unlike me, my brother was not a slob and kept his room neat and clean and knew where everything was placed. My room was a mess.

“You never looked at them?” Kevin asked me as he held up the magazine he was holding for me to look at. It was open to a page where a blonde girl was exposing herself shamelessly.

“No that’s gross!”

I did think a girl’s pussy was gross. I was not attracted to girls and the thought of their pussies revolted me. I had no idea what I was going to do when I got older and if I decided to do a full gender reassignment surgery. I don’t think I could stand looking at a pussy on myself for the rest of my life.

“You don’t look at porn?” Kevin asked me and started to put the magazines away.

“No,” I lied.

Yes, I watched porn and I masturbated to it. I did not watch gay porn, but I did watch transsexual porn. My favorite was older men fucking younger transsexuals. Even though having sex frightened me I did fantasize about it when I masturbated. I didn’t always think of older men, but most of the time I did.

Even though I never touched another man’s penis, I thought of myself sucking their cocks. Even though I never tasted cum, not even my own, I thought of them cumming in my mouth. Even though I never had a man’s penis in my butt or anything in my butt and did not know what it felt like, I thought of them fucking me. At sixteen, I was unaware of my Daddy Issues. I discovered that a year later but I don’t want to get ahead of myself. That part of my story comes later.

We left my brother’s room and went to the living room. I sat on the opposite side of the sofa with Kevin on the other side. I was sitting propped up with my back to the arm of the sofa and my knees up to my chest and my bare feet flat on the seat of the sofa. I had the TV remote in my hand and pretended to watch TV. I was watching Kevin, however.

I watched the boy as he scarfed down the pizza rolls, slurped soda out of the can, and even belched once. Kevin was very lacking in manners. As I watched him, I started to think he was not that bad looking.

At sixteen, he already had a masculine appearance and I was attracted to the masculine older-looking boys in school and the masculine men I saw. He already had whiskers on his face and should start shaving. When he wore a V-cut tee shirt I could see he already had black chest hair. When I watched, I much preferred the men with hairy chests and who didn’t shave their pubic hair. I had seen him in shorts and his legs were covered with black hairs that were much thicker than a lot of other boys his age. I got butterflies in my stomach again as I studied him.

Maybe he was not so ugly after all. I could show him how he should get his thick, black hair cut and styled. I could give him a facial and teach him how to clean his face to get rid of the blackheads. I could teach him manners. I blushed when I thought maybe if Kevin was my boyfriend, I could change him.

I squirmed a little because my cock was hard again as I looked at the boy. I was glad my jean shorts were thick enough to hide my erection. I don’t know why I suddenly had these thoughts about Kevin. Maybe because he said I was pretty? Yes, he said he was not gay, but I was not another boy so him thinking I was pretty did not mean he was gay. I was a girl, after all, not another boy.

“Do you watch a lot of porn?” I suddenly asked as Kevin shoved the last pizza roll in his mouth.

Kevin started coughing as he choked on the roll and took a drink of his soda.

“What made you ask that?” he asked me after he stopped choking.

“I don’t know, just curious if guys watch a lot of porn.”

“Yeah, we do. I do,” he admitted. “It’s good to watch it for the knowledge.”

I laughed and I laughed hard. “The knowledge? I don’t think people have sex like how they do it in porn videos.”

Kevin shrugged, “They seem like they are enjoying it,”

“Of course the men are, but the women do it for the money I’m sure,” I told him, still giggling at his comment about porn being knowledgeable.

“How do you know? Have you ever done it? Had sex?” he asked. I could tell he was getting a little mad. I don’t think he liked being corrected.

“Maybe I have.”

“Yeah right, with whom?”

“I can say, it’s a secret and he would get mad if I told anyone,” I lied.

It was Kevin’s turn to laugh. “Oh, is this some boy that lives in Canada and you met at summer camp?”

“Shut up!” I extended my legs and kicked his thigh. “I’ve never been to summer camp. I bet you never had sex either. I bet you never have even kissed a girl.”

“I never said I did,” he admitted. “Have you? Kissed a boy? I know you are lying about having sex, but what about kissing.”

“No,” I admitted. “But I bet I know how to better than you.”

Kevin laughed at me again, “Just because you know how to make out with your pillow does not mean you know how to kiss a boy.”

“That’s not funny!” I went to kick him again and he caught my foot in his hand.

“Stop kicking me with your nasty feet.”

I wiggled and squirmed and tried to break my foot free. “They’re not nasty!” I told him.

I was not angry as I pretended to be. I was enjoying the fact that this is the first time since we were young kids that Kevin seemed relaxed around me and paying attention to me and not the stupid video game.

“Yes, they are. They are dirty and stink,” he teased me.

“They are not!” I screamed but was laughing.

Kevin did not let go of my foot but instead ran his hand up my calf. I stopped laughing and looked at him. It felt nice. The butterflies in my stomach were going crazy.

“I bet I am a better kisser than you,” my voice had a husky sound to it. I was turned on.

Kevin looked me in the eyes for a few seconds and then let go of my leg as if it was a snake that bit him.

“Since neither of us has ever kissed anyone I don’t see how you can win that bet. It’s not like we can ask anyone to compare and even if we did you would not kiss the same people I would since I would kiss a girl and you a boy.”

“You can kiss me to find out,” I suggested in a whispering voice.

Kevin’s eyes focused on the TV for several seconds and I started to regret suggesting he kiss me. I had ruined everything. He was starting to be my friend again and I just blew that. Now he would leave and never come back and I would be lonely again. Maybe he would even tell his friends that the freak tranny girl tried to kiss him and everyone would laugh at me.

I started twisting my fingers in my hair, something I did when nervous, and Kevin looked at me.

“You can’t tell anyone,” he said.

I smiled and nodded, “I won’t, I promise.”

“I am serious, Kat, if you fucking tell anyone and it gets out I kissed you, I will kick your ass. I don’t care if your brother beats the shit out of me after.”

I swallowed hard at his threat but nodded. I was not going to tell anyone even if he had not threatened me. His threatening to beat up a girl did not even occur to me that he may have been that type of person. I figured he just said it to me because he knew me as a boy when we were younger. I did not know at that day Kevin could be mean at times. Something I found out later; he was not abusive, but mean in a way I discovered I enjoyed.

As Kevin moved toward me, I spread my legs and lowered myself on the sofa to lie on my back. He moved on top of me and we nervously kissed. It was just our lips touching at first but I soon parted my lips and he did the same and our tongues went into each other’s mouths. His breath smelled and his mouth tasted like tomato sauce and pepperoni from the pizza rolls, but I didn’t care. I kissed him harder and wrapped my arms around his back.

I didn’t know if Kevin was a good kisser or not, but I sure was enjoying it. Kevin and I kissed for a long while and I was whimpering and moaning and running my hands up and down his back. When he started kissing my neck I let out a loud moan and thrust my hips up. Kevin started moving his hips and soon we were dry humping each other. The friction on my cock felt great and I hoped he could feel me rubbing against his cock. He moved his hands to the bottom of my shirt and lifted it.

I grabbed Kevin’s face and moved his head back up to my face and started kissing him again. Kevin moved his hands up my stomach, to my chest, and he lifted my bra. I made a whimpering moan into his mouth when his fingers started playing with my nipples. I played with my nipples when I masturbated, but having someone else do it was much more pleasurable. Kevin started kissing my neck again and then down to my chest and then he started to lick and suck my hard nipples.

“Ohhh, God! Ohhh, Kevin! That feels so good!” I cried out as I placed my hand on the back of his head.

As Kevin aggressively attacked my nipples with his mouth and fingers, even pinching them hard, I started to grind myself into him harder and faster. Kevin responded by grinding his crotch into mine just as forcefully.

“Kevin, stop! Please stop!” I cried out after a while of him sucking and playing with my nipples. “It’s too much! Ohhh, God, please stop it’s too much!”

Kevin didn’t stop. He started sucking my nipples and grinding against me with more intensity. He then moved his mouth to my neck while his fingers toyed with my hard nipples.

“I want to fuck you,” the boy whispered in my ear.

“Uhhh, please no! Please stop, uhhhh, Kevin! I’m going to…uhhhh God! Uhhhh! Uhhhh, God!” I moaned and cried out as I had an orgasm.

I orgasmed with only Kevin playing with my nipples, kissing my neck, whispering he wanted to fuck me, and us grinding against each other fiercely. My body made a series of uncontrollable jerking motions, I was moaning out loud whimpers of ecstasy, and my fingers dug into Kevin’s back. He knew what was happening to me and just kept kissing my neck, whispering over and over how he wanted to fuck me, pinching my nipples hard and painfully, and grinding his cock into my crotch. The pain of him pinching my nipples seemed to only intensify my orgasm. I had never cum that much or that long and it never felt so good when I masturbated.

“Please, get off of me,” I told Kevin between my panting after my orgasm ended. I was so embarrassed I almost started to cry.

Kevin didn’t get off of me and I struggled to push him away. He was just much larger than me and much stronger and he wouldn’t move.

“I can’t believe you came,” he told me. “That was fucking awesome. The way you sounded and your body moved and the way your face looked was fucking sexy as hell.”

I did start to cry from embarrassment at his description of my orgasm. I didn’t sob or wail or anything dramatic, but tears ran out of my eyes. I continued to struggle and beg him to get off of me so I could run to my room and hide and cry without him seeing me. Kevin moved a little to his side and grabbed both my small wrists in his hands. He then pinned one arm above my head and guided my other hand down to his crotch.

“No, please, Kevin. I don’t want to,” I pleaded and tried to pull my hand away but he was just too strong.

“I want to fuck you, Kat,” he told me again. “I want to fuck that skinny, tranny ass. I bet that sissy pussy is so tight.” My hand reached his crotch. “My cock is so hard, you need to take care of it,” he told me.

The way he said it was like it was my responsibility to take care of his erection and to make him cum. Like it was some household chore or project that I was responsible for doing, he said it like I didn’t have a choice.

“No, Kevin, I am not ready for that. I don’t want to,” I begged again as he forced my hand on his cock.

I could feel his hard penis under the blue jeans he wore. Even though I was telling him no, I started rubbing his cock through his jeans. It was like my hand had a mind of its own and it would not obey my brain commanding it to stop.

My rubbing his cock made Kevin think he had my consent and he became more aggressive. He started kissing and sucking my nipples again and kept telling me he wanted to fuck me. He referred to my butthole as a sissy pussy or a tranny pussy. I liked that he did that. It made me feel more feminine and more like a girl than I already did.

When kids at school would call me a freak or sissy or other derogatory words to describe me it offended me, but for some reason with Kevin and me making out, him being so aggressive, me rubbing his cock, and overall what we were doing his words turned me on. My dick was hard again. I still was not ready to have sex, however.

Something strange happened. I started crying and begging Kevin not to fuck me. I thought he was going to force himself on me. But I was still aroused and rubbing his cock and didn’t want to stop. Kevin was sucking my nipples and pinching them and then he reached up and grabbed my hair and pulled my head back. It hurt and I cried out in pain but the feeling of it excited me. It was like a current of pleasure ran down my head to my penis. Kevin started to kiss my neck again as he pulled my hair. I made whimpering moans of pleasure and pain mixed as I still cried and begged him to stop.

“I have to fuck you, Kat,” he said in my ear. “I need to fuck your sissy pussy.”

His hand not pulling my hair started to unbutton my jean shorts. When he unzipped them, I suddenly found the strength to resist.

“No!” I cried out. “Stop, Kevin! I don’t want to do that!” I managed to turn my head and bit his arm hard and pushed him off of me.

Kevin moved to sit on the other end of the sofa and I sat up on my end and started crying. Kevin looked angry as he rubbed the spot on his arm that I bit.

“I told you I didn’t want to,” I said and sniffled as I cried.

“Jesus, fuck, Kat,” Kevin looked at me. “Stop being such a bitch and stop fucking crying, I was not going to make you.”

I sniffled again and wiped my eyes. “You… it… you wouldn’t stop. I’m not ready for that.”

He took a deep breath. “I got carried away, that’s all. You got me all worked up and you were letting me do things and you came and you were rubbing my cock. Were you just being a tease? ”

“I’m not a tease,” I muttered out. “I liked what we were doing and I didn’t mean to… to cum. It just happened.”

Kevin took another deep breath to calm down. “You didn’t have to bite me. That hurt. You left teeth marks,” he held up his arm to show me. He was smiling.

I giggled and wiped my eyes again. “I’m sorry.” The tension between us evaporated.

“You could give me a blowjob,” Kevin suggested with a grin on his face.

I started twisting my hair and looked at the TV. I thought for several seconds as Kevin remained silent. I did want to see his cock, I wanted to feel it in my hand, and I wanted to put it in my mouth. I turned my head to look at him. Kevin was staring at me as an alligator stares at his prey before he attacks.

“I… I can use my hand,” I suggested.

Kevin nodded, “I guess that’s better than nothing and better than me jerking myself off.”

I giggled at him again, “Ok, but let’s go to my room. I don’t want to do it in here.”

Kevin gave me a huge grin. He grinned like someone who just won a grand prize. “Ok.”

Published 
Written by Kittycat
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