This is the first chapter of my very first story so please forgive me if the writing is not up to par with what you are used to. This first story will be about me and my sexual experiences with a boy and going from a crossdresser to a transgender female. I am now twenty-three but my story starts when I was sixteen.
Before I start, a little about myself: I am Korean but born in the U.S. in Jonesboro, Georgia. Jonesboro is about twenty miles south of Atlanta. I am a third-generation Korean American so no I don’t speak Korean and the only accent I have is a southern accent, not a Korean one. I was born a male and two months premature. While I was not born with any birth defects, as I got older, I never fully developed as other boys my age did. At the age of sixteen, I was much shorter, thinner, and had a feminine body type. I was also born with Puberphonia; a voice defect where after puberty, my voice did not change and remained a falsetto tone. Basically, my voice will be a girly type of voice my entire life. I stood only five feet five inches and would only grow another inch. I always looked about two years younger than I actually was, had a very thin and girlish body with no muscle tone, and truthfully was always very pretty. Not handsome like nice-looking boys but pretty like a girl. I never had to come out as gay since it was very obvious by my feminine looks and mannerisms that I was gay. I was what one would call a twink, a femboy, and a sissy boy. I was named Michael by my parents.
I grew up as an only child and was just me and my mother, my father died when I was two. My mother dated men off and on but she never remarried. My grandparents and other family members still lived in California and I rarely saw them. Growing up, it was really just me and my mother. My mother worked two and even sometimes three jobs to make ends meet and I was a latchkey child. We lived in an apartment complex in a two-bedroom apartment. I lived on the second floor of a two-story apartment building that housed eight units per building. I went to public school and surprisingly, I was never bullied at all for being gay. Yes, there were the occasional crude and vulgar comments at times but never physically bullied and I did have a few friends. I was, and still am, into the fantasy genre such as video games, books, and movies. At sixteen, I was a virgin and had never even kissed a boy. All changed one afternoon in the summer and I kissed my first boy.
His name was David. David was my age and lived in the apartment below me with his grandparents. His mom and dad were divorced and neither wanted custody of him so they dumped him on his father’s parents. I had known David since we were both twelve and we were friends and he had no issue with me being gay and we hung out often. David was cute, other girls thought so as well, but they considered him odd. He was taller than me and had an average body type.
Like me, he was into the fantasy genre and he got me into playing Dungeons and Dragons. I always played a female character. I also knew one reason why he did not have a girlfriend was that David was really into porn. I would not say it was an addiction but he watched a lot of porn on his computer and had a lot of porn DVDs. That was why he never had a girlfriend. He thought girls liked to be treated like the women in the porn videos and all girls had sex as the porn actresses and enjoyed sexual acts as the women in porn videos did. David went out on a couple of dates in the past but after the girls found out he had no social graces at all and that he really did not treat girls with much respect, they never wanted a second date with him. Hell, he even took one of the dates to a softcore porn movie thinking she would like it and get turned on by it. He was not very much of a lady’s man, could be crude, and had very little social skills. I liked him anyway and even had a slight crush on him.
My first kiss happened on a rainy weekday in June. David wanted to start an impromptu D&D game. I was all for it and we planned it in my apartment since my mother was at work and our group would not be interrupted. Since it was not a planned D&D for us no one showed up. David and I waited for about an hour and decided to give up hope so we ended up sitting on the sofa watching television.
“I wish Tracy would have at least shown up,” David said out of the blue.
“Oh, you got an itch for her?” I teased.
“Duh, who doesn’t? Well, I mean you don’t but every other guy does.”
Tracy was our age and she was absolutely beautiful. It was a big shock to us she liked playing D&D. She was pretty and popular at school but she really enjoyed the game and got into it. Tracy was one of those girls everyone liked. She was not just pretty; she was nice and sweet and kind and unlike her older sister; Tracy was a good girl. Her seventeen-year-old sister Melanie had a reputation for being a slut. They lived in the same complex we did.
“Yeah, Tracy is sweet and pretty but not my type,” I giggled and David chuckled.
“Mike, have you ever kissed anyone?” David asked me.
I blushed, “No. Not many guys I know want to kiss me. In case you have not noticed there are not any gay or at least guys who admit it around for me to kiss.”
“Well, you would be surprised. I know a few guys at school who have said if you were a girl, they would want to fuck you.” He laughed. “They talk about it in the locker room at the gym. I know some even said they would let you suck their cocks. I think it’s the Asian fetish thing.” David laughed. There were very few Asians in our high school. Heck, the entire city of Jonesboro only had about a one percent Asian population.
“Oh, please tell me who, cause I really want to kiss someone,” I teased.
I knew there was this homoerotic talk in the boys’ locker room even if I never took part. I did not like gym class and did everything I could to always get out of it but it was a required school class. I did dress out or I would get a failing grade for the day but I never really participated. I was not very athletic and always the last picked for a team. Since I never worked up a sweat, I never needed to take a shower after gym ended and changed back into my clothes. I usually left the locker room as quickly as I could. Yes, I did check out some of the other boys’ bodies as they changed and got turned on but I kept that hidden from them. I did not feel like getting my ass kicked for looking at some other boy’s body.
“Have you ever kissed a girl? You went out with Stephanie and Melissa.”
David sighed, “No, they did not want to kiss me.” David turned his body to face me better. “You know we can try it. I mean if you don’t tell anyone… if you did, I would kick your ass. I am not gay but if you want we could kiss. You look and even sound like a girl anyway.”
I blushed again. I know he did not mean it as an insult when he said I looked like a girl. Everyone thought so anyway and I was used to it. I was into my kind of emo look. I was not the full emo type but I wore my black hair longer than my peers and it was styled with an emo flair to it that made me look even more feminine. My fashion consisted of mostly skinny jeans and tee shirts or shorts and tee shirts. That day, I was wearing a pair of white shorts and a black tee-shirt with an obscure rock band logo on it.
“I… we can and I won’t tell anyone… I promise.” I was excited and really wanted to kiss him.
David leaned toward me and I leaned toward him and we met halfway and we kissed. It was clumsy at first but then we relaxed. I parted my lips slightly and felt his tongue trying to go into my mouth and I parted my lips even more and soon we were French kissing.
David put his arms around my waist and pulled me closer to him and when my body pressed into his, I let out a moan as I wrapped my arms around his neck. It was not long before David had me on my back and was on top of me and we were making out with passion. David started moving his hips and kissing my neck and I moved my hands down to his butt and I was making very girlish whimpers and moans. It was great and my own penis was rock hard and I could feel his was as well. We kissed and made out for a long time and when David took my hand and moved it to his crotch I did nothing to stop him and even started rubbing my hand over his jeans to feel his hard cock. I liked the feeling and fondled him for several moments.
“David…please…ohh, God that feels so good…please, David stop,” I moaned out and jerked my hand away from his crotch.
“Why? You like it, don’t you?” he whispered in my ear. He tried to put my hand back on his crotch but I resisted.
“Yes, but please stop. It’s…we are going too fast.” I pushed him off of me and we both sat up.
“What’s wrong,” he asked and I could tell he was a little angry.
“Nothing. I just…it was going too fast and…and I just needed to stop.”
“I was not going to try and fuck you,” David told me and I again I could tell he was angry or frustrated or both, “I just thought maybe you could suck my cock or at least jerk me off. I mean you are gay.”
“I…I never did anything like that and I am not ready to, I think.” While I was a virgin, I was not naïve about sex or even gay sex. My mother gave me the sex talk and also gave me pamphlets about male on male sex. I was not very much into porn but I had seen gay porn. My favorite was masculine men and twink-type boys or Masculine men and Transgender females. And naturally, being a sixteen-year-old boy, I masturbated a lot and even a few times put my own finger in my butt when I did so, but I was not ready to go further and I was also more than a little scared about it.
“Can’t we just kiss some more? I liked that,” I suggested.
“Yeah, I liked it also. We can.” We started kissing again.
David and I started playing a game that I liked to call husband and wife and I was always the wife. Over about the next three weeks, we played our game as much as we could and also went about our normal activities as well. I really liked the game we played and I knew David was not my boyfriend even if, at times, I liked to think he was. He often reminded me of him not being my boyfriend by telling me if I told anyone of our game, he would kick my ass. During our make-out sessions, I often had to get him to stop when things got carried away. Sometimes, he got mad at me for it but he always stopped when I asked and I felt bad but I was just not ready to go further than kissing. During those three weeks, I discovered my desire to be a girl for him, not just act like one when we played the game but to look like one as well. It was easy for me to act like one; that came naturally, but dressing like a girl and wearing makeup was more difficult.
I had a natural feminine mannerism and ever since David and I started our kissing and making out I did my best to act even more feminine. My mother liked to watch old movies from the forties and fifties and I enjoyed watching them with her and as we watched them, I paid close attention to the way the actresses moved, sat, flirted, and basically presented themselves. To me, the actress in the older movies had much more class and style than the ones in the present movies. I would practice being like them when alone. Makeup was a different story.
I never knew makeup could be so hard to put on. Lipstick and mascara were easy but when it came to the eye shadow and base makeup and concealer, it was much more difficult especially if you were going for a specific look such as smoky eyes or something more gothic. I watched a great number of YouTube tutorials. The dressing was not too hard since I had my mother’s clothes.
My mother had me when she was nineteen. So, by the time I was sixteen, she was in her thirties and she was also a very attractive woman. Like me, she is petite, even being about an inch shorter than me, and she still dated when she had the time. She had two long-term boyfriends since my father died; one was a white man and the other a black man. I also knew she was sexually active because the walls between our bedrooms were not very thick.
When she was not dating and when I was old enough she felt I could stay alone, she sometimes would go to Atlanta with her work friends. Sometimes, she would not get home until the next day and I thought she may have hooked up with someone. It was when I went through her underwear drawer I found out she had some sexy lingerie, panties, bras, and thigh high stockings. I tried on some of her dresses and they also fit me pretty well and I would dress up in them when she was not home. Wearing my mother’s clothes made me feel so feminine and also much more natural than wearing my own boy clothes. I think that was when I started to realize I was not just gay but also transgender because I felt more myself when I dressed and acted like a girl.
I also started shaving my body. I was not very hairy and did not even have chest hair but what little hair I had I shaved and also used hair removal cream on my arms and legs. I did make the mistake of putting it on my crotch and learned the hard way that was not a good idea; it burned like crazy.
I never told David I was practicing being a girl for him; I wanted it to be a surprise. It took about two weeks for me to get my makeup well enough and to my liking and the courage to show myself to him as a girl. We had just finished playing our D&D game in my apartment, my mother was at work and would not be home until after midnight, and when everyone left, David suggested we play our husband and wife game. I agreed enthusiastically but told him to come back in about an hour because I had a surprise for him.
When David left, I hurried to my mother’s bathroom and put on makeup, which I had gotten pretty good at. I put on mascara and dark eye makeup, some concealer and blush, and then red lipstick. I could have styled my hair into something more feminine but I recently had brought a cheap wig at Party City that was brunette and styled in a page boy cut. I put on a wig cap and attached the wig with bobby pins to hold it in place After I was satisfied with my makeup and the wig, I thought I looked very pretty. I went into my mother’s room and put on an outfit I had previously decided I would wear. I put on a pair of lacey black bikini cut satin panties, the matching bra even though I had no boobs, black thigh highs that had a seam running up the back legs. I selected a black pleated skirt that came about four inches above my knees, and a white button-up blouse that was made not to be tucked in. I admired myself in my mother’s full-length mirror and was really surprised by how hot I looked. I looked just like a very pretty girl; actually, I looked younger but I was super cute.
I waited for about twenty minutes before David knocked on my door, he was ten minutes late. I was very nervous as I waited and even flinched when I heard him knock on the door and started to think I made a mistake. I answered the door and fidgeted as David got his first look at me dressed as a girl. He stared at me for several seconds with his mouth actually open.
“Fuck, you look hot,” he finally said and walked into the apartment.
His comment made me smile and I closed the door behind him. When I turned around he was still staring at me and I blushed.
“Do…do you like it? I…I thought I could play the girl much better this way.”
“Oh, fuck yeah, I like it. You look sexy, Michael. Fuck, you are so pretty.”
I giggled, “It’s Mia, not Michael.”
David smiled and sat on the couch and I sat next to him. He immediately put his arms around me and we kissed for a moment and I pulled back and playfully slapped his shoulder.
“I am not that type of girl,” I teased. “Let’s watch some TV.”
David chuckled and put his arm around me willing to play the game, “Ok.”
Well, we did not watch much television and soon were making out on the couch and then soon I was on my back and he was on top of me. I spread my legs apart for him and put my arms around his neck as we kissed with passion. David seemed even more into our kissing than he had before and was soon thrusting his hips into me and I was moving mine up to meet him. It was not long before I thought we needed to take a break before things got carried away and I pushed him off of me and sat back up on the sofa.
“God this is fun.” My breathing was heavy and my cock was hard and pushing against my panties.
“Yeah, and you look so damn hot, Mike…Mia. Fuck, you are so pretty and sexy.”
“Better than Tracy,” I teased.
“Yeah, you are in a way. Different, I guess.”
I smiled at that and leaned over and kissed his cheek. I thought he was lying but it was nice to hear. I was glad I decided to be a girl for him and I also felt so very sexy and even more comfortable dressed this way. I really liked being a girl, not just for him but for myself.
“I think we should do something else,” David said.
“Oh, like what?” I had an idea what he wanted to do but I still did not think I was ready for that. I had been researching anal sex online and the dos and don’ts and how it should be done and how a person can prepare for it. I knew eventually I wanted to try it with David but not that day.
“We can watch each other jerk off if you want to,” David suggested.
“I…if we did can we go to the bedroom?”
“But that’s all right? I mean nothing else. Just kiss and we can watch each other?” I asked nervously but excited about seeing David’s cock and seeing him jerk off and cum.
I agreed and we went to my bedroom. Once in my room, we lay on the bed and started kissing again and once more David got on top of me as I spread my legs apart as a girl would. As we kissed and thrust into each other, David moved my skirt up higher and then cupped my butt with his hand as I made moaning whimpers into his mouth. I was not expecting us to make out again but I was not complaining because it felt great. I loved kissing him and being dressed as a girl made it more exciting and my penis was erect and the sensation of David grinding into me making my penis rub against the satin panties felt wonderful.
My fingers pressed into David’s back as he started kissing my neck and my moans sounded very feminine. “Da…David…ohhh, God, baby, ohhh, that feels so good…I…I thought we were going to do the, ohhh, God, David, I thought we were going to do the other thing,” I managed to moan out. I found it difficult to talk. I was much more aroused than I had ever been since the two of us started playing the husband and wife game.
“We will. I just like kissing you dressed like that. You are so fucking hot and sexy.”
I really liked that he thought I was pretty and sexy. I felt David’s hand move under my panties and his hand was grabbing my bare ass but I did not stop him nor did I stop him when his other hand grabbed the back of my upper thigh and he lifted my right leg higher. I really did feel like a girl making out with her boyfriend and I enjoyed the feeling. I was taking such pleasure in it so much that I did not even notice David’s fingers run up my butt crack until it was too late and I gasped out as his finger entered my tight hole. There was a little pain because his finger was not wet but other than that it felt very good. I had often fingered my own ass when I masturbated so the sensation was not new but for some reason, it felt even better. I suspected it was because someone else was doing it and I gave a loud girlish moan of pleasure as his finger went deeper into me. I never put my own finger that deep inside myself and it felt so good but I got scared.
“Please…ohhh, David, please don’t… you promised,” I pleaded with him.
“Shhh…you know you like it. I can tell. I am going to finger that tight little pussy and then watch your jerk off.” David pushed his finger even deeper and my fingers dug into his back.
It did feel very good and when he called my butthole a pussy I felt excited and lifted and spread my legs apart to allow him to finger fuck my asshole. As he used his finger to fuck my tight hole, David started kissing my lips again and grinding his hips faster into me as I whimpered and moaned in pleasure. I really felt so much like a girl but then something else happened.
“Ohhh please…please stop…David you have to stop…please…I…ohhh, God please…I…uhhhh…uhhhhh…ohhh, God!” I begged and moaned and made a series of loud, feminine squealing whimpers as I orgasmed.
You see I had a problem. Well, I called it a problem or an issue, and later as I got older, I still had the same issue but I discovered men seemed to like it. My issue was I orgasmed very quickly, even when I masturbated. By quickly I mean it would only take me three to four minutes before I would orgasm. I knew it was not normal to cum that fast and it only bothered me only a little up until that moment with David. With David, it bothered me a great deal. I orgasmed just by him fingering my butt and my penis rubbing against the satin of the panties and I was very embarrassed by it.
“Did you cum?” David asked as he pulled his finger out of my butt. He was kneeling in front of me between my spread legs.
I covered my face with my hands, “Yes…I am sorry…I…I could not help it.” I felt like crying I was so humiliated. I could feel how wet my panties were from my own cum.
“Wow, that’s hot. I want to see it.” David did not wait for me to answer and pulled my panties down before I could resist. “Fuck, you came a lot,” he chuckled, “your panties are soaked.”
“Please…stop, David,” I begged and moved my hands down to cover myself but David grabbed my hands. I pleaded with him and squirmed my body trying to get away but he held my wrists with one of his hands, used his body weight to hold me down, and then ran his free hand down between my legs. I was wiggling and squealing for him to let me go but he just laughed and told me to be quiet. His fingers then ran over my thighs and my panties and David bought them to my mouth.
“Lick them,” he told me and his voice was commanding.
“No…please, David…you promised we would only watch each other,” I begged him. I was not opposed to eating my own cum; I have done that before when I masturbated and liked the taste but this was different. I did not want him to see me do it.
“Do it,” he told me again. His tone was much more forceful. David grabbed my jaw and gripped it so tight it hurt as he forced my mouth open. I whimpered from the slight pain and even felt like crying, but for some odd reason, it also turned me on.
I opened my mouth and stuck out my tongue and started to lick his fingers and then he put them in my mouth and I sucked them clean. I did enjoy it and started to suck them more enthusiastically.
“I knew you would like it. You are such a cum-hungry little slut, aren’t you?”
I did not bother answering and just kept sucking his fingers. David laughed at me and pulled his fingers out of my mouth and let go of my jaw. He then straddled my chest and used his knees to pin my arms to my side. I watched as he unbuttoned his jeans, pulled them down a little, then pulled down his underwear, and his hard cock sprang free. David started stroking his cock slowly.
“David, please let me up…please,” again, I begged and squirmed.
“Hold still, you little bitch. You said you would watch me jerk off.”
“I…not like this.”
“You like it, you sissy whore. Now, look at it.”
He really did not have to tell me to look at his cock. I was already looking at it and could not take my eyes off of it. It was average length like mine was and I thought it was nicely shaped and very sexy. He was right. I did like watching him stroke his cock. It took me only a matter of seconds to stop squirming and watch him. I also found out that I enjoyed him pinning me down and taking control over me like he was and even him calling me a sissy whore seemed to arouse me and I felt my own penis start to get erect again.
David leaned forward a little more and touched his cock to my face and it touched my lips. I don’t know what came over me, well that’s a lie I did know; I wanted him in my mouth badly. I parted my lips, leaned forward, and took the head of his erect cock into my mouth.
“Oh fuck…that’s it…suck it, you little slut,” David moaned out.
I pulled my head back, “I will…I want to but…but can I do with you lying down?” I asked.
David grinned, “Sure.” He got off of me and lay down next to me. I moved down between his legs, took his penis in my hand, and once more took him in my mouth and ran my tongue over the tip to taste his precum. I then proceeded to give my first blowjob.
Naturally, it was not the best blowjob I was to give. It was really terrible. I gagged and choked, felt David flinch when my teeth accidentally grazed his hard cock, and had to take my mouth off of him several times to catch my breath. Even though I was doing an awful job, I still loved it and David did not complain. I loved sucking his cock; I loved how it filled my mouth, I loved the taste of it, I loved the smell of it, and I loved his masculine moans of pleasure. There was so much about it I enjoyed; I enjoyed how my saliva made his shaft slick and shiny, I enjoyed stroking his wet shaft as I sucked his cock, I enjoyed his hand on the back of my head, I actually enjoyed him calling me a “cocksucking sissy whore”, but most of all I enjoyed how feminine it made me feel.
“Ohhh fuck, Mia…uhhhh, God damn, I am going to cum,” David moaned out. I liked how he called me Mia.
I could have taken my mouth off his cock and jerked him off until he orgasmed but I did not want to. I wanted him to cum in my mouth. I wanted to taste his cum and swallow it badly. He did. I felt his body tighten and heard a series of grunting moans as his cock exploded in my mouth. It was amazing! The feeling of his warm sticky fluid shooting out of his cock and into my mouth, hitting the back of my throat, the taste and texture of it was just wonderful. I kept sucking and jerking his cock trying to milk every bit of his cum I could from him. I did my best to swallow it all but I was not experienced and some leaked out of my mouth but I kept going until he pushed my head off of him. I sat up, wiped my lips and chin, licked my fingers, and smiled at him.
“Did…did I do ok?” I asked.
“Fuck yes…that was great,” he told me.
I grinned and lay next to him. My own penis was erect and I wanted to cum again. “Can…can I jerk off?” I asked.
David looked at me, “I don’t care. I have to go now so you can do it after I leave.”
“Leave? My mom won’t be home until late and…and…I thought we could hang out and…and I can do it again…suck you again if you want.” I felt sad and even used. I wanted him to stay. I wanted him to cuddle with me, to kiss me again, to play husband and wife some more, and to suck his cock again. I wanted to suck his cock forever.
“I have to go. It’s almost time for dinner and my grandma is going to want me home.”
“Oh.” I felt so disheartened.
“You can come down for dinner if you want. I mean after you change and clean up,” David chuckled, “I don’t think my grandma and grandpa would like it if you came for dinner dressed like that.”
I giggled and felt better, “No I don’t think so.” His grandparents often invited me to dinner. I really liked them. They were very nice to me and watched over me when my mother was at work.
“Cool and then after we can come back up here and play some video games or something.”
I giggled again, “Or something? Can…can I be Mia again?”
David smiled, “Yes, I like Mia. Mia is hot.”
Our friendship changed after that day. For about the next two and a half to three weeks, I gave David many blowjobs and I got very good at it. Most of the time, I did it dressed as Mia but not always. There were times when I did not have the chance to dress up for him and he wanted his cock sucked or I wanted to suck it. Like one time on a Saturday afternoon, we were hanging out in my apartment and my mother was home. She went to the grocery store and I suggested giving him a blowjob while she was gone and of course, he agreed. Another time, we were outside hanging out with other kids in the complex and when it got late and getting dark David and I walked back to our building and he led me to a secluded area between some woods and one of the apartment buildings, kissed me, and told me he wanted me to suck his cock so I got on my knees and gave him a blowjob. The best, however, was when I was able to be Mia for him and for myself.
I started buying my own makeup and even some cheap female costumes at Party City or nicer female clothes and underwear at Walmart or Target. I had money saved up from birthdays and Christmas, money my grandparents in California sent me, so I bought some sexy costumes, sexy skirts and tops, and sexy bras and panties, thigh high stockings of pantyhose, and even a sexy lingerie set David really liked. I spent all my saved up money on female clothes.
David never touched my penis unless it was a mistake and he never gave me a blowjob but I did not care. He did like to see me cum and would watch me masturbate and orgasm and then watch me eat my own cum. David would also finger my tight asshole as he kissed me and I would sometimes cum from just that sensation. I did buy some lubricant for that purpose and I liked how he called my little hole a pussy. Other times, he would lie between my spread legs and finger fuck my butt, sometimes using two or three fingers, while I jerked off. I liked it when he would finger fuck me. I liked how he took control and how dominant he could be and even liked when he called me degrading names at times.
One time, he teased me about being such a naughty slut and a bad girl and I needed a spanking. I played along, thinking he was just teasing me, but he wasn’t. I was squealing and squirming as he put me over his knees, pulled down my panties, and spanked my ass hard. By the time he was finished, my butt cheeks were burning with pain and I was crying and telling him how mean he was. David just laughed at me, called me a whore, and started fingering my asshole for several moments with three fingers. He then made me get on my knees and he fucked my mouth hard. I was gagging and choking and my saliva was pouring out of my mouth as I cried, but he did not relent. When he orgasmed, David pulled out of my mouth and came all over my face. After he came, he would not let me clean my face but made me jerk off in front of him and finger my own ass. I came in about three minutes. The entire ordeal was humiliating and the spanking was painful, but, God, did it arouse me so much for him to treat me that way.
David, of course, wanted more, he wanted to fuck me and I wanted him to but I was scared. It was about three weeks since I gave him that first blowjob when I found myself ready to have him fuck me and I was going to make it sexy for us both or at least try.