First Experiences [mt, trans, oral]

I always knew I was different.

I don’t mean that in the way people always do. Everyone was unique in some fashion. I just always knew that I never fit in. That something inside of me was off. That as I developed, I was unhappy with the changes that were occurring, because it was taking me away from what I wish I was. I thought it was just a phase, but as the years passed, I just got more depressed. Other boys were rough, rugged, always playing sports and chasing the girls. And I was none of that. At first, I thought something was wrong with me. I didn’t enjoy the things other guys did. I didn’t have any friends, and was terrible at talking with girls. How could I explain to them that I was jealous of the bodies they had, the things they got to do. Deep down inside, I knew I wanted to be a girl, but I hid from this side of myself. I was afraid. They’d call me a creep, I just knew it. And so I turned to the one place where I could go to be what I wanted. In chat rooms and on forums, I was a girl. It was the only bright spot in my life. I could talk to people without fear, without feeling scared for being different. It was a lie, but it was a lie I enjoyed.

Online, that’s where I learned there were others like me. That’s where I learned that I wasn’t all that different, that there was nothing wrong with me. That’s where I learned the word for what I was. Trans. Finally, the way I had felt all my life was rationalized. I was trans. And there were plenty of others who were like me. I loved getting online and chatting with people who understood what I was going through, they made me feel accepted and normal. I loved seeing these people who looked like me, and after a couple years, had transformed into beautiful beings that reflected what they felt on the inside. I too vowed that I would transform.

It started before I graduated from high school my senior year. College loomed ahead and it gave me a chance to become the new person that I wanted to be. I grew out my hair and started working out. I learned how to put on makeup, even though I wouldn’t wear it out in public. I started talking to people a bit. My new look was giving me confidence. Even though I had to dress like a boy, I started to dress a little more feminine, wearing tighter shirts and pants. I even started hanging around with a couple girls. I guess they thought I was gay, but I enjoyed being around them and listening to them talk about girly things.

A month after I graduated, I started HRT. I knew that this was what I wanted, and being able to do so before college was important to me. I decided to take a year off so I could work so the changes to my body could really develop. I was afraid of starting college still manly and a year later looking like a girl. I took a job as a waiter, and cried when people stopped calling me mister and sir, and started calling me miss. My hair was long and thick, my breasts were budding, my hips were wider. The estrogen was working a miracle on my body. All except for a gender reassignment surgery, I looked and felt like a girl.

After my year off, I went to college. It was surreal. I had completely transformed myself into the woman I always wanted to be. I got put in a girl’s dorm and was meeting plenty of people, all who only knew me as a girl. It felt right, like the complete opposite of growing up. I had finally found my niche, and I settled in for college life, the only thing keeping hidden was the fact I still had a penis.

You know those days, where you wake up and think nothing about it being special, but it turns out to be a day your remember for the rest of your life. That was this day. I came back to my dorm after class to find that my roommate had tied a ribbon on the doorknob, her signal for telling me to stay away from the room because her and her boyfriend were screwing. I didn’t mind, we’d only been living together a couple weeks and this wasn’t too often, most of the time they were in his dorm.

I decided to take a walk in the bluffs behind our dorm. It was nice to go up there, the couple times I went up there wasn’t anyone around, and I could just be alone with my thoughts. After about twenty minutes, I decided to take a rest. I stepped off the beaten path and went down and around a rocky outcrop so I could sit in the shade. September wasn’t terribly hot, but hiking in the sun did make me want to cool off a bit.

Resting my back against the rocks, I leaned back and took a breath. My mind drifted towards thoughts of my roommate. She was back at the dorm, probably getting her brains drilled out for the second or third time today. Probably getting pumped by her boyfriend’s dick. Probably moaning so loud the people walking by the door outside could hear them. I had heard them before. She sounded like she was in ecstasy. Even though I felt embarrassed, I had gotten a little erect back then. It had been a while since I masturbated; I was always so scared to do it for fear of her walking in on me. She didn’t know I was pre-op; no one did. This was my chance to reinvent myself, be the person the HRT pills had helped me to become.

Still, I had needs. I might not like my penis, but I still enjoyed the pleasure it could give me. Just thinking about my roommate getting plowed had already stiffened me up a bit. I reached into my pocket and pulled out my smartphone. Yes, still had some service. I closed my eyes and held my breath. One second passed, then another, then another. I heard nothing, no one on the trail. Finally, a little privacy. Passed my phone to my off hand and reached into my pants with good one. I started to fondle myself, using my phone to take me to my favourite porn site. I turned all the sound down, so if anyone came walking along the gravel path about fifty feet away, I could hear them and cover myself. The only students I’d seen come this way were the stoners, loud and looking for a secluded place so they could smoke. I’d have no problem hiding myself if a group came this way.

I picked a video of some blonde with implants getting drilled and unzipped my pants. I took solace in the fact that the HRT had done great work for me. My breasts had recently gotten to a B-cup. They weren’t as big as the girls’ were in the video I was watching, but compared to my old self it was an improvement. I pulled out my member, letting it all air out. Who knew how much longer I might have a penis, so I might as well enjoy it while I do. I slowly started to work my hand up and down, up and down, slowly at first. I started getting harder, stiffer, and small waves of pleasure were drifting down every time I changed direction. It had been nearly a month since I had last gotten myself off, and the pent up sexual frustration started making itself felt.

In the video, the girl was being worked on a bed, her legs wide open, eyes closed. She looked like she was enjoying it immensely. I hoped that when I got the surgery, I would feel like that. I had never even so much as kissed someone else; the only pleasure I ever received was from my own hand. I was starting to rub a little faster, holding a little tighter. I could feel myself shuddering as a little pre-cum started to come out. I stopped myself, and reached into my backpack, grabbing a couple Kleenex. I don’t know what I would say if I went back to the dorm with cum stains on my clothes, I didn’t want to be thought of as a slut. I turned my attention back to the video, watching the guys’ cock go in and out of this blonde. I timed my own strokes to match those in the video, pushing a little more pre-cum out with every stroke. I could feel the big finish building slowly. I wiped the pre cum off with the Kleenex and went back at it. Up, down, up, down, up, down. It was starting to feel really good, I was as erect as I usually got. Leaning back harder against the rock, I closed my eyes, steadily stroking myself, feeling the tension build up as I got closer to blowing, hearing my breathing getting heavier, hearing the wind blowing through the trees, hearing “Well that’s something you don’t see every day.”

Wait, what?

My eyes shot wide open. I froze, my blood turning to ice. Slowly I turned my head to the right, where the voice had spoken from, and I saw him, my worst fear of being caught in mortal form. Short brown hair, athletic build, eyes half hidden by his cheeks that were pushed upwards by his smile. It wasn’t a big smile, he wasn’t showing teeth; it was more of a content smile, a kind smile, the ends of his lips turned upwards. He was my worst nightmare, my secret was discovered, so why was he smiling. In my mind, I always imagined that someone would be disgusted, but there he stood, just smiling and looking into my eyes.

He started walking towards me. In my imagination, people who found out were always running away from me, shocked and horrified. But here he came, silently, still with that smile and looking me in the eye. I was still frozen, staring straight at him, my hand around my now flaccid penis. My brain was sending all sorts of signals to all facets of my body. Run, it told my legs. Hide your dick, it told my arm. Bludgeon him with a rock so he gets amnesia, it told my other arm. But the only thing I could do was to lower my phone down to the ground, to try to hide the porn I was watching as if it was the most shocking thing he was seeing.

He came up to my right side, and sat down beside me, leaning back against the rock. The smile had disappeared; he only displayed a solemn face. My mouth was open, slightly agape as I reminded myself to breath.

“Are you trans?” he asked me.

My words caught in my throat, bottlenecking. I was trying to say everything, such as “Where the fuck did you come from?” and “What are you doing?” and “Please don’t tell anyone.” I must’ve looked a fool, eyes wide with terror, mouth open, and unable to talk. I nodded my head.

“You don’t meet many trans out here.”

Again, I could only nod my head, but at least I was able to close my mouth and look a little less like an idiot.

He took his hand, putting it over mine and removing it from my feeble attempt to try to hide my cock. He looked down at my penis, and my eyes followed his. I felt like I could die. He was inspecting me, I just knew it. He would soon go back and tell everyone at the school that I had a penis, and everything would be ruined. I’d get kicked out of the dorm; people would make fun of me and never want to speak to me again. I’d have to transfer to another college, in another state, but only after I got the surgery. If my legs didn’t feel like lead, I would’ve run.

I looked back at his face. His eyes had drifted up and were looking at my breasts. I felt so ashamed. After staring at my chest for a few seconds, he blinked, and when his eyes opened they were trained back on mine again.

“If you don’t mind me asking, are those real or do you stuff them?”

I should’ve been offended. That’s not the kind of question you ask someone, but I was sitting in the middle of the forest, looking entirely like a girl except for my penis that felt to me like it was a lighthouse on a dark day, drawing all attention, something you can’t turn your eyes away from no matter how hard you try. Weakly, I was finally able to get words out of my mouth, and “Real” was my response to him in a murmured tone, my voice hushed and straining to break.

He just smiled again, not with teeth, but with the corners of his mouth curving upwards. I stared deep into his eyes, thoughts still drifting in my head of finding something to hit him in the head with, hoping that he would forget this whole ordeal. Again, his eyes turned back towards my penis, and then I felt something. It was a strange feeling, as if I had a third hand that was just feeling something for the first time. My eyes turned back down to my embarrassment, and I saw it. He was holding my penis in his hand, slowly rubbing his thumb below my second head. My body started to react, and my erection started coming back. He noticed the Kleenex near my bag, and grabbed one, wiping away the old pre-cum that had accumulated from before I was aware of him. As he wiped my head, I could start to feel pleasure again, though it was miniscule compared to the level of fear I still had.

I still didn’t comprehend what was happening. Why was he here? Why was he still here? Had I gotten so into the moment that I didn’t hear him coming up the path? By this point, I was erect again, this strange feeling of having someone else touching me sexually spreading throughout my body, replacing the frozen tension I was stuck in. His hand was going up and down my shaft tenderly. A shudder went through my spine; I was gradually realizing that this was feeling good, but my mistrust of this stranger was still prevalent. He was still focused on my member, stroking it a little quicker now as I stared at his head, still wondering who he was and why he was doing this.

However, after about thirty seconds of this, I was beginning to feel the pleasure that was emanating from my loins. My body relaxed, and I leaned back against the rock again, still alert but less stiff everywhere but by cock, which was at the most erect it had ever been in my life. He had moved his other hand under my stiffness and started to fondle my testicles, gently rolling them in his hand. As he did so, my body shuddered, and I relaxed fully, leaning back against the rock and closing my eyes. My mouth had opened up just a bit again, and I could hear myself breathing heavily again, my breath shaking with every change in direction his hand made.

My mind turned to reflect upon my enjoyment of the experience. This was the first thing I had ever done sexually with another person, and it was so unexpected and unfamiliar that I was having a hard time processing it. This was my first hand job, the first time someone else had ever jerked me, and I didn’t even know who this person was.

“I hope you’re relaxed. I want you to enjoy this.” I heard him say, his words faintly penetrating my ears. The only response I could muster up was a slight moan followed up by my breath pushing out my mouth involuntarily from the feeling of the hand job. “Just let me know when you’re going to finish.” I opened my eyes to see him looking at me with his little smile on his face. Looking into his eyes, I felt like the things he was saying were genuine, even though I still harbored feelings of mistrust of this sexual stranger. He had a kindly face when he smiled, his voice oddly calming.

My eyes looked down looked back down at his hand, watching him rhythmically going about my meat. My pre-cum was now overflowing, glossed over my entire head and running down towards the base of my member. I could hear a slight squishing noise as it worked as a lubricant for his hand, smearing down the length of my shaft. How long had we been here, maybe five minutes, maybe twenty? I was so distracted by the experience, and by now whatever doubts I still had in my mind of his intentions were replaced by my enjoyment of my first time. I worried that his hand was getting sticky, and out of experience, I reached for the Kleenex again to wipe my pre-cum away, hopefully giving me a little time to try to sort out my thoughts and not blow my load soon. I was enjoying every stroke now and didn’t want it to end, as I just knew he would let slip back at the university that I was not what I seemed. I picked up the tissues, but as I moved my hand to clean myself, he took his hand off and grabbed my wrist. I froze again, feeling my warm fluid pressed between his hand and my arm. Was this his game? Was he just teasing me? I was sure he was going to pin me down and have me answer all the questions that I didn’t want to answer. His eyes turned back towards my difference, and all I heard was silence save for my breathing. This was it, he was going to take his other hand off my balls, grab my other arm, and pin me. I was terrified, but the thought of him holding me down worked to arouse me subconsciously, and my muscles twitched, my sticky erection standing tall and hard as the trees surrounding us. With is hand still gripping my wrist, he leaned towards me, then down, and put myself into his mouth and started bobbing his head.

For the first few seconds I was stunned. Then, shivers shot throughout my entire body. I had never felt anything even half as good as his mouth in my entire life. It was warm, moist; his lips creating a suction that made my whole body tingle as he worked. He was fitting half of my mast into his mouth, his tongue swirling around and below my head. My body slumped against the rock again and I closed my eyes; rolling my head back and to the side as the stress in my shoulders and neck vanished. All tension in my body had disappeared, very much in the same way my penis had disappeared inside his mouth. I dropped the tissues and reached out my arm, resting my hand on the top of his head. His hair wasn’t long, but I was still able to nestle my fingers into its smooth flow and enjoy the feel of it. My mouth was open again, my breath unable to be retained to my nose. I felt at his mercy, trying to keep my moans hushed as I felt his lips and tongue making the journey back and forth from the tip down.

“Oh god” I muttered, his hand starting to play with my testes again, rolling them around and rubbing them. Everything was just too good to be true. My discovery had just moments ago felt like the worst experience of my life, but this warm cavity that I had entered now felt like the best. “Oh god” I repeated, trying to get a firmer grasp of his hair as it kept dropping down and springing up as he sucked. If this was what blowjobs felt like, I understood why the boys in my high school were always bragging about getting them. “Oh god.” My muscles were tensing up, my legs started to shift. This unworldly feeling was radiating stronger, my entire body was quaking slightly. And still, up and down, up and down, I felt his mouth moving, my tip pressing against the back of his mouth, his tongue rubbing the underside of my penis, his lips giving me more joy that my hands had ever given me. Suddenly, I realized what was happening. I opened my eyes and looked down on him as my loins started to tighten. “Oh god, I’m cumming.”

The feeling was heavenly. My entire body quivered with delight as the floodgates opened and my cum spilled out into his mouth. My knees were vibrating, my abdomen twitching with each blast. My breath rushed out of my lungs and I moaned loud enough that if anyone was hiking the path, they would’ve heard me. My eyes rolled into the back of my head with my joy, my fingers clenching his soft hair. He never stopped bobbing his head up and down, he kept the same pace and kept his lips tightly locked around my shaft and he gripped my testes firmly, as if he was trying to squeeze out every last drop of my cum.

My mind was blank after that. For about ten seconds I had no thoughts, I was just a slave to the wave of pleasure that was slowly fading. I opened my eyes and saw myself staring into the sky, gazing up at the clouds. I rolled my head down so I could look at the person who I owed this great feeling to. His head was still down, and he had stopped his vertical motion. Spasms afflicted my entire body still, but I could feel his lips, still in a tight suction just under the head. His grip on my sack had lightened up, and with his other, sticky hand he wrapped his thumb and index finger around my cock, still erect but slowly starting to grow limp. He gripped at the base and slowly worked his hand up to his lips, jumping bit by bit, working the cum from out of my shaft, pumping me dry. I could feel my cum, sloshing around my head as his tongue worked my tip as the last drops were pushed up and released into his mouth.

He lifted his head, keeping his lips tight so none of my seed would fall out. I felt the moistness of his mouth leave and he picked his head up and sat up straight, exposing my wet dick to the cool air. He removed his hands from me, grabbing the Kleenex as he turned his head and spit my cum against the rock. He turned his head towards me, cleaning his saliva and my cum from my shaft with the tissues as he looked at me again, and I stared into his eyes.

“Sorry I spit.”

I didn’t know what to say. What was I supposed to say? What was anyone supposed to say in this situation? My mind and mouth fumbled for anything so I wouldn’t seem like such an idiot.

“That’s okay.” I heard myself reply. I guess it was better than saying nothing at all.

He smiled that gentle smile again, and I started to blush. My hands fumbling, I tucked myself back into my pants and zipped them up. He turned towards his backpack and took out a water bottle, squirting water into his mouth and spitting it out again, rinsing his mouth out I assumed. Finished, he tossed the bottle back into his bag, and turned towards me again. I was just sitting there, dumbfounded at what had happened. My body was returning to its normal state and I felt like I was in control of my legs again. Run, my subconscious told me, run and forget this ever happened and hopefully he will too.

He leaned towards me and reached over my side, picking up my phone that I had dropped. The porn was still playing on it, and I felt ashamed for having been caught watching it. He looked at the screen, laughed, and paused the video. Tapping on the screen, I saw him go to the main menu.

“Are you at the university?” he asked me.

This was it, this was my chance. I could run now and not answer any questions. Maybe he would forget what he looked like. He didn’t even know I was a student. I didn’t even know if he was a student. For a second I considered it, until I realized that he had my phone, looking at the screen and tapping away on it.

I remained silent. If I could get out of this situation without revealing anything about myself such as my name or dorm, maybe this would get swept under the rug. I even started to think, I have some leverage here. What was he going to do, go and tell his friends that he blew some girl out on the bluffs? This could be our little secret, and hopefully I’d never see him or hear about this situation again. It would just be my own little memory, a personal dear penthouse story that I could look back on. I turned away to look out at the scenery. It really was quite nice here, a lot more lovely than any bedroom or back of a car where I expected some of my first experiences to happen.

We sat in silence for a minute before he handed me my phone back. It was on the main menu. What did he do? I checked my message history really quick and saw he hadn’t sent anything to anyone. Was my name somewhere on my phone? Was that was he was looking for, so he could blackmail me? My name was, but it was in my contacts with my number, with no distinguishable characteristics that would make a stranger realize that it was my name.

“I didn’t do anything to your phone.” He assured me, gazing at my face as I searched my phone. “I just put my number in there.” He grinned again. “You’ll recognize it when you see it. I’d love to hear from you, and hopefully I’ll see you around.”

He leaned in and kissed me. I was taken off guard, but once I realized what was happening, I leaned into it and closed my eyes. His lips met mine, forceful yet caressing as he took my lips between his. My first real kiss. My chest fluttered as we were locked there, lips intertwined. His lips were rugged, wrinkly, and a bit dry, but I didn’t want to let go. I pulled back a bit, opened my mouth slightly, and went back in. He took the cue and his tongue penetrated into my mouth. Mine own was there to greet his, and they danced inside our mouths passionately. I knew if I hadn’t just cum a little while before, I would’ve been rock hard again.

Finally, he pulled back, his eyes half hidden by his smile. His eyes gazed deep into mine, and I smiled. For a few seconds, the world was calm. Then he turned from me, stood up, grabbed his backpack, and started walking around the rocks. I watched him go conflicted, not wanting him to go but also wishing that he would just disappear. When he was almost out of sight, he turned back towards me, his face expressionless again.

“You’re extremely pretty.”

And then he was gone, hidden by the rocks. I could hear his footsteps walking away, each step he took shifting the pebbles underfoot. They faded the next minute, and all I could hear were the birds chirping in the nearby trees. A part of me wanted to chase after him to explain to him all that I had been through and why I am the way I am, but I didn’t want to see him again. Not immediately at least. I wanted to be alone right then and reflect on how close I had come to becoming an outcast again, someone different who wasn’t understood. My worst nightmare had come true, and it had turned into something my wildest dreams couldn’t compete with. I took a moment to reflect on my emotions. They were all swimming around inside my head: fear, joy, surprise, pleasure, shock. I just needed a little while to sort them all out. I hoped that he wouldn’t tell anyone, that this was our little secret. If not, I don’t know what I would do. But maybe, I thought to myself, maybe he’s a decent guy, and I won’t have to worry about him.

Him. Oh god, I thought as I came upon the realization, I had never even learned his name. All I had to go on was the memory of what he looked like, and that would probably be fuzzy in an hour or two. I’d be at least nice to know his name. Then I remembered that he had put his number into my phone. What did he say about it, that I would recognize it? I grabbed my phone and went into my contacts. I scrolled down quickly. I didn’t know his name, I don’t know what he put in, I was just looking for anything different. Reaching the bottom of my list and not noticing anything, I scrolled back up, in reverse, reading each contact and recognizing who they were. There was nothing unfamiliar. I kept scrolling, looking at each name. It wasn’t until I was nearly at the top and I had almost given all hope that I noticed something different. I was in the B section, and there it was, normal to anyone else but clear as day to me. I smiled, because it was clever. “BJ” it read, and I’ve never known anyone who went by BJ. I touched his name to check to see if he really had left his number. It was there, ten digits with the local area code. I knew it had to be him, because underneath he had written a little message to me.

“Don’t worry, your secret is safe. Text me :)”.

Seeing the smile in text form reminded me of his gentle smile, the one he had on his face when he walked up to me while I was frozen with fear. Just thinking about its soft curves and tender nature helped me to trust that he would stick to his word. I took a breath, and smiled down at my phone. Tomorrow, he would get that text he asked for.

Source: reddit.com/r/sexystories/comments/2ca8om/first_experiences_mt_trans_oral