#Mature #Teen #Trans #Virgin
By TransTwinkBoi
When I turned 14, my Uncle Matt gave me some extra responsibilities during my summer stays with him on the ranch.
Every summer, I usually stayed with a family friend out of town. He had a huge ranch and my parents always seemed so happy to get rid of me for the summer. When they were home they hardly ever talked to me, or even noticed me at all aside from my mom feeding me sometimes. All I wanted was for someone to tell me they were proud of me, to just fucking be there. That’s where the family friend, who I called Uncle Matt, came in. He was so much different than my parents. He complimented me all the time, hugged me, carried me, even as I got older. My favorite thing to do was watch Gunsmoke while I laid my head on his leg. He’d stroke my hair and sometimes make a comment about the show, or ask me what I wanted to do the next day, or what I was thinking about. He showed so much care for me that I never even questioned the other things he did to me. The first time he touched my private area I was 10. That was a little after I kept telling my parents I’m a boy. They ignored me mostly aside from telling me to accept that I was a girl. After I told Uncle Matt, he tried to say it was a phase and that it would pass. While we were watching Gunsmoke like usual one night, he asked me why I thought I was a boy, and if I understood what makes a person a boy or girl. I told him not really. I just wanted to have short hair and do “boy things” like I saw my cousins do. I wanted to be treated like they were and I wanted to be strong. So he asked if I wanted to learn what really makes boys and girls different. I said yes. He asked me if I trusted him. I said yes. Then he told me we should shower and get ready for bed. I said ok and got up to go to the bathroom. Instead of staying on the couch, he followed me. I got into the bathroom and he followed me in. I asked why, and he asked if I was sure I was ready to learn what’s the difference. I said yes, I really want to know! So he said we would both get naked. I felt a little weird, but I didn’t feel bad, so I just started undressing. Uncle Matt did too, and I finally saw the difference. He told me to get in the shower and he would teach me more about body parts than what I learned in school. I did what he said. As we stood under the hot water, I couldn’t stop staring at his body. I was tall for my age, but Uncle Matt was really tall too. I came up to about his elbow height. He asked what I thought was different. Our privates, duh, I said. I laughed. His parts were funny looking and kinda jiggly. He smiled at me and explained the names of each part. I never knew privates had special names for each part until then, but I was happy to learn. Uncle Matt seemed happy to teach me. He asked if I wanted to touch his, and I didn’t say anything. I just grabbed his dick and squeezed it like a hotdog. He let me play with it a bit and it started getting hard and bigger and eventually pointed straight out toward me. When I asked why that happened he said that’s just what happens when something feels good. It made me happy to make my uncle feel good, since he always made me feel good when he petted my hair when we watched tv. So I kept playing with it and finally we were done showering. He asked if I still wanted to be a boy. I said yes, because I wanted my body to look like his when I grew up, not my mom’s. I didn’t want boobs or a big butt. I didn’t want long hair either. He asked if I wanted him to cut my hair. Yes! I loved my Uncle Matt a lot because he always listened to me and made me feel special. So he put a towel around my shoulders and cut my hair just like how he did my cousin’s when they came over. It was a regular side part and I felt so good about myself when I finally saw in the mirror. He said there’s just one more thing we have to try before I get to be a boy. I asked how would I become a boy and what we were going to try. He told me to go sit on the couch naked and close my eyes, and to wait. So I did. He sat next to me and was still naked too. Then he told me to lay back, and he pushed me down and spread my legs. I got a little nervous because I didn’t know what was happening, but then he put his mouth on my pussy and was licking and sucking it. It felt so good I didn’t want him to stop. I think he could see that I liked it, so he asked me again if I still wanted to be a boy. I said maybe only half boy, because I really liked having a pussy now. It felt so good when he used his mouth like that on me. Soon, my body started shaking and I had my first orgasm. I realized after I opened my eyes that I had been gripping Uncle Matt’s hair with both my hands. He told me it was ok, and called me a good boy. When he called me that I felt my heart jump and I couldn’t stop smiling. Then we got our pajamas on and he showed me a bunch of videos on the computer about people that are transgender. Some of it was porn too and he asked if I liked it. I did like it and he said it’s ok that I liked it, I just had to keep it a secret. I didn’t really care and it’s not like my parents would ask anyway, so I never told anyone about it. I just saw it as another thing that was special about my summers at the ranch. A couple years later, I had just turned 13 and it was summer again, time for me to stay with Uncle Matt. By then puberty had just barely started. I was glad that I was a late bloomer because the thought of growing into a woman made me sick. Still, I couldn’t shake the yucky feeling in my stomach, even though I looked like a boy still, and everyone treated me like one, I had to admit that my chest started developing. My nipples hurt sometimes and I could tell they were trying to turn into breasts. Uncle Matt liked to play with my nipples sometimes and he would let me suck on his too. He finally let me suck his cock that summer and even bought me a vibrator. Although I was still quite slim, I was afraid I would start to grow curves soon, and the scariest thing of all, a period would happen sooner or later. All of these fears I told my Uncle Matt as soon as arrived. He promised to talk to my parents about puberty blockers. They didn’t like it but when they picked me up after summer was over, I was allowed to go on blockers, then they even let me start low dose hormone therapy since I was so sure about what I wanted and also my therapist agreed I was mature enough to decide for myself.
The summer after that, I was 14. That’s when everything changed and I realized why I had been born with a pussy but felt like a boy on the inside and wanted to look like one on the outside. It was early morning time, and I was in the kitchen drinking a big glass of orange juice and devouring a pack of lunch meat. Ever since I started hormone therapy, testosterone, I was even hungrier. I was already hungry all the time, but now I was hungry AND horny. So as I sat in the kitchen eating, I also had my hand in my pants, playing with myself. I was never embarrassed about it, because Uncle Matt was very open about sex and sexuality and he taught me to be the same way when it was just me and him alone together. I couldn’t sleep, so I was hoping Uncle Matt would wake up soon to play with me. I wanted to suck his cock and wanted him to suck my clit, which had gotten a lot bigger since I started hormone therapy. Finally, I heard his footsteps approaching the kitchen. He stopped in the doorway when he saw what I was doing. My cheeks pouched out like a chipmunk’s, but instead of nuts I had a mouth full of baloney. I wish his cock was in my mouth instead.
“I couldn’t sleep. I’m really horny.” I said, a pice of food flying out and plopping on the table.
He shook his head and smiled. I took my hand out of my pants and gulped down some orange juice.
Uncle Matt slowly walked over to me and rubbed a hand gently down my back. I shivered. My body had been trained on his touch, and I knew what to expect as soon as he’d touch me like that. At least, that’s what I thought. This time, he had a different look in his eye. Dangerous. Threatening, almost.
My stomach dropped. Was I in trouble?
“Uncle Matt?” I asked quietly. I examined his expression. I couldn’t tell what he was thinking at all.
He ran his big, warm hand through my messy hair. I closed my eyes and leaned in. He had started off so many of our sessions just like this. My body was already responding in kind, my stomach filling with heat and butterflies.
Despite us having messed around every summer for the past few years, we had never done anything more than oral and hand jobs. I thought it was always going to stay like that. That’s what my body was anticipating. That’s what I was expecting and looking forward to.
Suddenly, Uncle Matt’s hands were gripping my shoulders tightly. He pulled me up to stand and leaned down, kissing me deeply on the mouth. His tongue pushed in, and I felt my legs get weak. His mouth was so warm and slick. I was already horny, but now my body was on fire. He let go of the kiss and my shoulders and placed a hand on the back of my neck. He guided me like a dog by the scruff to his bed and shoved me down hard. He’d never treated me so roughly before, but my heart pounded and I couldn’t even speak because of how much I wanted to please him. Before I knew it, my pants had been ripped away, and without a word he was sucking my clit and shoving his tongue deeper than ever into me. I almost came immediately, but he stopped and pulled away before I could. I whimpered and he slapped my cheek.
“Did I do something wrong?” I asked, my eyes watering from the sting.
“No, you’re a good puppy boy, I just had to show you how it will feel if you try to resist me. We’re going to do something different today.” He said.
I rubbed my cheek and blinked away any tears. I’m tough, I thought. I can handle anything. He won’t hit me again either because I’m going to be good.
That’s when he yanked my hips forward. I realized what he was about to do when he started rubbing his cock against my pussy. I thought about asking him to stop, but the pain on my cheek still lingered and I didn’t want that to happen again. I couldn’t move. I was frozen. Could he really fit his whole cock inside me?
Just a second later I found out, yes, he could, but it hurt like hell.
I gasped and was about to let out a scream but his hand clamped over my mouth and muffled it. His cock was buried fully inside my tight young pussy. I could feel him throbbing inside me. It felt so big I thought I was going to be torn in half. He leaned down over me and held me in his arms, groaning into my ear and he held his cock deep inside. I couldn’t believe how much it hurt, but as he held it there, throbbing and so warm, I felt my body begin to relax. The stretching feeling actually didn’t hurt so bad anymore. Then he started to pull out and the pain came right back. I moaned into his hand and my eyes were streaming with tears at this point. He looked at me and petted my hair to calm me.
“Ssshhh, it’s alright baby, I got you. I’m being gentle right now so you can get used to it. I won’t be able to control myself much longer though so you be good for me, ok?”
He finally released his hand from my mouth and I had to take a few big breaths to stop myself from crying. He began to thrust slowly, at first just pulling out a little bit and thrusting back in a little at a time. Each time he moved I couldn’t help but moan a little. I just felt my body making noises that I couldn’t control. It felt like forever that he was pumping his cock slowly in and out of my virgin pussy. Eventually, I don’t know exactly when but I could see the sun was finally above the tree line, it started to feel kind of good as he fucked me. It was a mix of pleasure and pain, and when he sucked on my nipple it started to feel really good. Now I wasn’t moaning because it hurt, I was moaning because it felt good. It made me feel different, more naughty and sexy than I’d ever felt before. Before now I always just felt good physically when he played with me. This time everything was different, I felt good in my body but also in my tummy and my brain. I felt like I wanted to tell Uncle Matt the same dirty things he would whisper in my ear sometimes. I just didn’t know what to say, so I just tried anyway.
“Uncle Matt, you’re making me feel so good! I like what you’re doing, it feels different. I feel good in my brain not just my body. I don’t know what to say, but I like it so much!”
He stopped thrusting and pulled out. “Oh you like that? You like having my cock inside your tight little pussy?”
I stared at him wide eyed, not believing this naughty feeling that had taken over my mind. I was almost shaking with how horny and excited I was about these new feelings. It seems like his very words were causing me to feel pleasure.
“Yes, yes! I like it when you talk to me too as you did it.”
He smiled and pulled me close again, rolling so I was on top of him. I sat on his hips, my dripping wet pussy resting on his rock hard cock. My hips bucked on their own to find some stimulation.
“Fuck, you’re such a naughty little tranny boy. Show me how much you like my cock in you.”
I looked at him questioningly. But sat up and kneeled over his lap anyway. He wasted no time in showing me what he meant. I understood as soon as he rammed his cock back into my pussy. His fingers dug into my waist as he lifted me up and slammed me back down on his cock a few times. I began to flex my thighs and knees in time with his thrusts, just like I did when I galloped on Clementine, the mare that I usually rode here at the ranch.
“Mmm, Uh- uncle m-Matt that feels-” I stuttered. I couldn’t even think anymore. I’d become a little cock hungry slut at this point.
“Say fuck, just say fuck if you like it.” Uncle Matt growled.
“Fuck!” I said. I never said a bad word before, but now it felt like honey, not poison in my mouth. “Fuck, fuck, FUCK!” I repeated as my uncle’s rock hard cock smashed into my guts over and over. I started feeling something like an orgasm build, but not in my clit like usual. My clit was tingling too, but now I had some kind of buzzing, some kind of heat radiating from my pussy and all the way to my toes. Uncle Matt was moaning now too as I bounced on his cock. I was breathing so hard and fell forward, bracing myself on his strong chest.
My legs were strong from growing up riding, but the way his cock kept stretching my pussy and pushing into my belly deeper each time he slammed in made them weak and soon I couldn’t move at all. The way I moaned was starting to change as that hot pressure built in my stomach. I was moaning from my chest now, not my mouth. Uncle Matt was breathing heavy too, and suddenly we both opened our eyes at the same time. He was locked in to my eyes, looking at me as he fucked me. I felt my already blushing cheeks get redder and the heat spread to my neck and chest. He was staring into my soul as he fucked me. Then he rolled us over again and once more I was under him, his weight pressing me down into the mattress. His thrusting became more frantic and fast. My head was spinning now and I threw my head back, squeezing my eyes shut. He grabbed the back of my head, yanking my hair so that I was looking at him again. I never realized before how he had brown spots in his blueish greenish eyes. Now that I was staring into them, feeling every inch of his cock sliding in and out, massaging the inside of my pussy, I couldn’t look away. The bed sheets had become a tangled mess now, and he was practically fucking me off the bed. He leaned down and sucked my mouth into a sloppy kiss, moaning into my mouth and I couldn’t help but moan back. He pulled away and whispered the naughtiest thing into my ear I had ever heard before.
“Tell me you love daddy’s cock pounding your tight little pussy.” He growled.
I panted in his ear, willing my voice to work but no sound would come out.
“Speak.” He demanded, slapping me again. It shocked me back into reality and I heard his command this time.
“Look at me, boy. Tell daddy you love taking his cock deep in your little tranny boy pussy.”
My heart was pounding in my ears and suddenly I realized my pussy was aching from how hard he’d been fucking me.
“Say it!” He growled once more.
I tried my hardest to obey, but all that came out was garbled squeaks and stutters as his cock kept abusing my tight little hole.
“Uh- I- da- da- ddy” I managed to mumble.
Even though I couldn’t speak, that seemed to satisfy him because he started thrusting so hard and fast that I let out a yelp of surprise. For the first time I showed a hint of resistance. I made the mistake of pressing my hand against his hip, trying to slow his thrusting. He instantly grabbed my wrist hard, and flipped me around while still impaled on his cock so I was on my tummy. He pulled me back onto the bed all the way because I was almost falling off by now. As soon as he had pulled me back, he began thrusting again hard and fast. His cock felt even more massive in this position and screamed. I was at my limit and couldn’t take anymore!
“Uncle Matt!” I finally found the strength to speak. “Please- slow- slow down, p-please! Ow! It hur- hurts!” I mumbled as he kept ripping into my body.
“Shut the fuck up, slut and take it like a good boy! Or are you a wimpy little princess girl who needs to be handled gently?” He growled and slapped my ass. I bit back another cry and held back tears. This time there seemed to be some malice in his voice. Looking back, I understand that he was just using my trans-ness against me to make me compliant. I should have known back then too but in my childish mind, I just wanted to be seen as a boy.
Even though I was back to reality, I couldn’t ignore that the good feeling was coming back again. My pussy got used to his size and this angle again, and somehow it felt even better than before. This position- doggy, was quickly becoming my new favorite. The conflicting emotions in me were soon gone again and I was back to being a moaning little whore. I had some idea of what he wanted me to say now, and the dirty little voice in my head told me to indulge him as well as myself. I reach a hand between my legs and rubbed my clit. I’m sure he knew what I was doing, but I don’t think he expected me to say anything in that moment.
“Fuuuck daddyyy, fuck me harder! I like it when your cock stretches me so much it hurts, it feels so good after that. Fuck me harder please daddy.”
I felt his hands begin to shake as he pawed at my ass cheeks and thrusted. He wasn’t moaning anymore but let out a series of grunts and stopped thrusting. He pulled me back hard and just held me there. His arms were wrapped around my shoulders and chest now, and my back arched hard as I came. His cock stiffened even more and I could feel it throbbing as my pussy started to clamp down on it. We came together for what felt like an hour. I’m sure it was only a little while but I didn’t want it to end. I was dizzy with lust and these new dirty feelings.
We collapsed on the bed, his weight almost crushing me except his elbows keeping the last of his weight off me. I turned to look back at him, and he caught my lips with his in a kiss. It wasn’t a deep kiss. We were both too out of breath for that. Instead he just kept kissing me softly over and over as we tried to catch our breath.
“Fuck.” I said, trying to use my new bad word.
“Fuck, yea.” He replied with a grin.
That was the first and only time he fucked me. The next day he went to go run a few errands and some drunk driver hit his car head on. He died and before anyone could help him.
I miss him every day.
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By TransTwinkBoi
#Mature #Teen #Trans #Virgin
