It began with me wanting to be a woman, and preparing myself for the change. And my best friends dad was going to very much test my mind and body.
I was always a smaller than normal boy growing up. I got picked on being called pee wee, and girly boy. And I really wondered since I was young if I would have been better off born a girl. I had a few sexual moments with boys in the past. One time was a attempt at anal sex. But neither of us could get big enough and/or hard enough to have penetration. But just the feeling of a boy climbing onto my back and trying to mount me, with his penis trying to find and penetrate my anus was extremely sexually arousing. It was a single memory that burned deeply into my young and developing brain. Even though I was very attracted to women, I also couldn't stop the curiosity of being a woman. I had turned eighteen a few months earlier, living in a small town in New Hampshire. It was the week of thanksgiving and my parents where going to Massachusetts to visit family. My older sister was planing on having a party at the house, while our parents where gone. I didn't want to be around her and her friends. I talked to my best friend Ricky who was also leaving town with his girlfriend. He told me that I could stay at his house for the week. His dad (Big Mike)was a over the road truck driver and was also leaving out for work. My parents didn't like me hanging out with Ricky. A lot of people didn't like his dad big Mike. He was a old biker guy, who was always up to trouble in his younger days. So for years I always lied about hanging out with Ricky. But we got along so good. And big Mike always treated me good, when he was around.
I was excited about just being alone for the week. I took some extra days off just to not do anything, after all I had just graduated high school too. Ricky gave me the key to his house on Monday morning and said his dad was leaving out Tuesday morning. So Wednesday morning I headed over to Ricky's with bags of food and a little weed to smoke. I walk down the long driveway looking for big Mike's truck, just in case he hadn't rolled out yet. He was gone, I unlocked the door and walked in. It was the cleanest I've seen in years. I found a note Ricky left saying he had cleaned up for me. I thought it was funny he cleaned the house. Since big Mikes divorce, and Ricky's mom and sister moving out years ago it was pretty messy since. I got comfortable and just watched tv and smoking a little pot.
I end up passing out on the couch. I wake up early Thursday (thanksgiving) morning. I smoke some more, and I wonder around the house. I remember that big Mike had a little stash of porn in his bedroom. Flipping through I find a video of a thin guy wearing girls clothes and a buff guy with a big cock on the cover. I bring it back to the living room and pop it into the vhs playing. The buff guys fucks the shit out of the guy dressed up as a girl. I was feeling horny, that's when my curiosity ran wild. I wondered what it would take for me to really be a girl. These day's with the internet to learn from, and the fact that one's sexual preference is more accepted. But in 1990 things where very different, there was no way to really research and learn about anything considered a taboo lifestyle.
I wonder into Ricky's sisters room to see if anything was left behind. I was shocked, it was like she never moved out. The door has always been closed, and I just never thought much about it since she moved out. I quickly find a sexy pink sundress in her closet that I loved at first sight. I started looking through a stack of magazines about looking sexy. I looked for any woman that kinda looked like myself, to see what would make me look and feel like a real girl. But that wasn't it, I really tried to think of what really made a girls personality. I thought about how I had to leave the strong dominant male attitude behind. And started to think about how I needed to have submissive female attitude, with a eagerness to please a man. As I went through her clothes I didn't only think about how they would make me look feminine. But how they would make me feel. Did the pink sundress make me look and feel truly feminine. Would a guy walk down the street with me holding my hand. Did I feel truly sexy, would a boy be want and need me sexually. I roamed around her room for hours looking and thinking. The more I dug around her stuff I found a shoe box with directions how to perform a coconut oil enema. She had the oil and the bag to flush out with. She must have been pretty into anal sex. I knew this would be a must for me. Obviously oral and anal is all I would have to offer to a boy.
I followed the directions. I ran hot water to mix with the coconut oil and hooked the pieces together. I inserted the small butt plug end into my anus, and squeezed the bag. It felt so sexy to flood my insides. I kept inside me for as long as I could before exploding into the toilet. I did it a few more times, I thought I would want my ass to be clean like a girls vagina. I did it probably more than needed, since I wasn't going to be having sex. But I was enjoying the feeling. I then ran a hot bath, and shaved off all my body hair and my legs. When I got out I rubbed lotion all over to make sure I was silky smooth. I had long hair because I liked metal music. So I just fixed my hair to look more womanly. Then moved into a putting on a little makeup. I followed simple but sexy technique from a magazine. The red lipstick I was putting on seemed to be brighter than what the magazine was recommending. I spray a little of her perfume on. Then I had grabbed a pink lace g-string that she had. It felt weird as I started to step into this tiny little thing. I was afraid of ripping it in half, I thought about how a guy could rip this thing off with little effort. As it reaches it's final position, the string slides into the crack of my ass. I instantly started to get hard, it felt so sexy. As I looked at myself in the mirror. I closed my eye's and moved my hands around feeling my ass and following the g-string into my ass crack. I was pretending it was another boys hands exploring me.
I then slide the sundress over my head. It fit tight in the upper body to show body curves, and loose on the lower end. It was short, a good wind it would easily blow up revealing my ass cheeks. I turn and look at myself in her full body mirror. I didn't even recognize myself at first, I was amazed just how good I looked as a girl. Being young and petite surly helps to give a good feminine look. I started to smoke a joint, and working on walking through the house in a sexy posture. The magazine got into how to walk to make your ass look it's best. I put on sunglasses and was walking around the house like I was in the bar trying to turn guys on. I noticed something out the corner on my eye, but being high it didn't dawn on me at first. Then I turned and almost walked right into big Mike standing in the door way watching me. I almost died, I didn't even know if I was seeing things. When he said 'Hi', I was like oh fuck. I quickly apologized, as I removed the sunglasses. He looked me up and down, and my eyes looked down over myself. Then I just stared at the floor, while apologizing again. I knew all hours of effort that I had put into everything was very obvious. I couldn't just say I was just trying on a sundress. I tried to think of anything that would take away from how I looked. I told him Ricky said I could stay at the house. He tells me I don't need to apologize for anything, and that he knew I was staying in the house. And that his truck broke down a few towns away, that's the only reason for coming home early. He thought he was going to have another crap week like many others.
He hadn't said anything about how I looked at first. I told him that I was going to go and change. As he again looked me all over. Big Mike was a huge intimidating man. He was very tall, short beard, big muscles, beer belly and a very hairy body. He always has a very very serious facial expressions, rarely ever smiled. He tells me not to change just because he's home. And that I look amazingly beautiful and a sight for sore eyes. I was hesitant, but I was also young and naive and figured I would stay in the dress a little bit longer. After all I had put a lot of work into it. He grabbed a beer from the kitchen and came back into the living room and sat on the couch. I was still standing oddly around, trying to think about what to do. He told me to come sit with him. I sat down next to him on the couch, I hadn't sat down yet in the dress. It raised up almost showing my cock in a g-string. I notice him looking at my smooth legs and thighs. He then asked 'your eighteen now aren't you?' I told him ya I was, as I look at him with a little smile on his face. I think it was the first time in a long time I've seen him smile. It didn't dawn on me at the moment why he was asking that. He asked me if I really wanted to be a woman or just experimenting. I told him I do want to be a girl, I have always thought about it. He said "well your eighteen now, and your life choice to make. He tells me that I need to be very careful dressing the way that I am, not everyone will agree with my choice. I told him that I know it doesn’t fit in the normal. He tells me being a woman is a lot different than a guy. I told him that I know, and that I played with a few boys. He chuckled and said “your not just messing with little boys anymore hun, your eighteen years old now".
He tells me that I have to really like the idea of dealing with hairy, fat, sweaty, and horny men having their way with my body. And that I will never really know what I'm getting into. That a man might only fuck for a few minutes, or it may go on all night long. Aggressive behavior can be pretty normal when a man is aroused. That some men might be small, or are going to be very well hung and could very much hurt if they are being rough. I acted naive and cocky saying I know. I told him that I was aware of all of it, even though I wasn’t. I didn’t think of what I would do in a situation of like a older out of shape man wanting to have sex with me. Just like the current situation of my best friends dad sizing me up. Again young and naive I was, but I was also very cocky. I didn’t really care, I just wanted to experience everything in life. He asked me to get him another beer, so I strutted my little ass toward the kitchen. I look a little over my shoulder to see if he was watching, and his eye's where glued to my ass. I came back with his beer to give it to him, I step in between his legs to be close. As he leaned forward to get it, I turned so my ass was just inches from his face. I look toward the tv and I see the porn video I grabbed from his bedroom. I shook my ass a little and walked away. I shook my ass by the tv as I set up the Atari video game system and try to hide the porn. He asked me if I liked the video. I turned beat red as I turned the tv on. I said I was sorry, I shouldn't have gone into his room. He said 'you'll become a woman in that bedroom'. I looked back as he had a smile, I smiled back. So I laid down on the floor on my stomach in front of the tv, and my back toward him. I knew he will have a perfect little peek up my skirt. I would do some wiggling as I played, to give an added effect. I was being such a cock tease.
After a bit it I noticed he was like rubbing his thigh over his sweat pants. He asked me to get him a beer from the kitchen. I jumped up and strutted my ass a little more for him. When I came back and handed him his beer. I noticed a pretty big bulge running down along his inner thigh. I was thinking he looked pretty big. He winked at me and I gave a big smile back, and went back to my game on the floor. He tells me how good I look and that I did a really good job putting myself together. I thanked him, and told him it was a lot of work. I said I hadn't done a lot of it before. He asked like what. I told him I never shaved my whole body at one time, or give myself a coconut oil enama. He asked “you gave yourself an enama, that's so Hot”. I realized maybe it was a bit too much information, I said Yeah. He said “Well, that’s good. It’s best to be cleaned out, you’ll make a good woman. Are you sure you did a good job, maybe I should check”. I told him you can check if you want I know I did a good job, I did it a bunch of times. I heard him moving around as I played my game. He had straddled my legs. I felt his hands land on my legs by my knees. His fingers on the outside of my legs, while his thumbs where on the back of my legs. He asked if I has sure if I wanted him, I thought he meant about checking my cleaning. I said sure, go ahead.
His hands slowly moved up my legs. They go under my dress, his big thumbs gently move over the curves of my ass cheeks. His hands stop when they are just above the top of my g-string. I realize it was to move the back of my dress out of the way. His hands start sliding back down to my ass cheeks. Then his hands start massaging my ass cheeks. I could feel what I thought at first was his big thumbs spreading my ass cheeks apart. But after a minute, his thumbs move to the point of almost touching my little anus. His face moved in so close I could feel him breathing on my ass. I get a little self-conscious when I realize that he is staring right at my anus. Then one of his thumbs hooks my g-string and pulls it all the way over the cheek of my ass. My anus is now fully exposed, as his hands move to my hips. I hear and feel what seemed to be him now sniffing at my anus. I become very self-conscious over his inspection of my anus. My mind was racing, hoping that I would meet his approval. It seemed to be the longest pause of nothing happening, I began to think I didn’t meet his requirements. I then could feel the roughness of face lightly making contact with my ass cheeks. As his face pushes lightly between my ass cheeks, he pauses again. I thought he might be checking me out again, I wasn't sure if he was liking it or not. His hands on my hips begin to hold on even tighter. Then his tongue makes contact with my anus. After a few licks of his tongue I let out a moan, as I had never felt such a feeling before. His continued licking at my little hole drove me crazy in a way I couldn't ever imagine would happen.
The stubble of his facial hair felt like sand paper on my ass cheeks. His hands on my hips start to pull my lower body off the floor. With my ass now high in the air, I start to raise my chest off the floor. A hand firmly pushed on my upper back to push my chest back to the floor. He was in full control of how he wanted me. Then his tongue then started desperately trying to penetrate my little hole. The feeling of his tongue trying worm it’s way in side me, was driving me even crazier. As I moan loudly, I find myself pushing my ass harder into his face. He realizes my liking of this. His hands slide down from my hips to my ass cheeks. His thumbs again began to work at spreading my anus to allow his tongue more access. I tried as hard as I could to loosen my little hole, not really knowing how to do so. I was dying to feel his tongue penetrate me. I got so carried away by everything happening, I began to become exhausted. My legs begin to weaken, I was putting a lot of my body weight onto his face just to keep my position. This was just the thing that needed to happen. Like the whole world came to a stop, as I began to feel his tongue slowly and fully enter me. I yelled out ‘Oh my fucking god, don’t stop please’. He let out a moan also, as I’m sure he was proud to have successfully entered me. He began to drool a lot, I could feel his saliva running down the back of one of my legs. I put all my energy to not move in anyway to jeopardize all the enjoyable feelings. I let out the weirdest moan ever heard as he licked the inside rim of my anus. It was such an amazing feeling, I never wanted it to stop. But after a minute his tongue began to tire. I whimper as I feel his tongue slowly start to slide out of me. I desperately wiggle and move in anyway I could to try to stop it’s exit from inside me. I almost cried as I lost his tongue totally and he pulled his face away from my ass.
His hands began rubbing my ass cheeks as he realized my disappointment. I felt a finger begin to rub my now saliva soaked little anus. The tip of his big finger presses firmly against my anus and begins to penetrate me. I yet out a moan as his finger slowly disappeared inside me. He moved his finger in and out in a finger fucking action. Then pull his finger out and his hands spread my ass cheeks apart, and he starts spitting onto my anus. As I thought this was a rude, he shoves his big finger all the way back inside me. He begins finger fucking my hole again, and my body started to move with acceptance. He stopped moving his finger and just watched me fucking his finger. He tells me ‘that a girl! You have such a sweet little ass, with nice womanly hips’. He then slides me around, and leans my back against the couch. As his face comes closer and closer to mine, I notice the manly roughness of his face close up. He lands his lips slowly onto mine. I feel his mouth start to open. I start to open my mouth to receive his tongue. But his tongue doesn’t wait to fully open. His tongue forces its way though my lips and quickly finds my tongue. His tongue works at my tongue aggressively, as we made out passionately. He pulls away from our kiss, with my mouth still open from the kiss. He raises up, and I notice his pants and underwear are gone. As he pulls his shirt off, I stare at a long really thick cock. I could tell he was only semi hard, and he was at least eight inches already. I noticed a lot precum starting to leak out of his huge cock. My eyes travel up his hairy body to see the look of sensual passion on his face. Slowly he reposition his body to move his manhood closer to my face. His man hood moves to just a couple inches from my face. He asked if I was ready to receive my first taste of his manhood. I nervously shook my head yes.
I reach out and wrap my little hand around his cock. I raise it up, it was sweaty, big and heavy. I could feel the blood pounding into it making grow in my little hand. I stroked it lightly, I was amazed by it's size. My hand couldn't make it all the way around his shaft it was so thick. I started to open my mouth and move to receive him. My lips meet his huge cock head. His precum runs onto my lower lip, I use my tongue to lick it away. I get my first taste of his sweet tasting precum. He then pushes forward, causing his cock head to force my lips far apart. My lips feel his huge cock head fully enter my mouth. I realize just how thick he is, as my lips are fully open and tightly wrapped around the thickness of his shaft. I could feel his cock grow bigger and bigger in my mouth. He began to move his hips. I began to think I wasn’t doing a good job, so I removed my hand. His hips moved his cock in a fucking motion inside my mouth. He began to moan as he continued his face fucking. One of his hands moved to the back of my head. His moans became louder as he began to shove his cock into the back of my throat. He then pushed really hard into the back of my throat. I started to choke as his cock started to stretch my throat. He yelled out “oh fuck yeah”. He then pulled my head back, enough to let me breathe. I was no where near being able to take it all. I just wanted to please him. He pulls himself from my mouth, telling me that I'm so hot.
He asked if I was really ready for him to make me a woman. I shook my head yes. He tells me that it's going to hurt, his manhood is going to stretch my little body. After adjusting to taking all of his manhood inside my body. He's going fuck my brains out, so I forget that I'm a boy. After tearing down my mind and body, he'll give my sore insides a full deep breeding. So if that's what I want, follow him to his bed. There's no turning back once in his bed, so I should think hard about my choice. He got up and walked his already sweaty body to his bedroom. I started to get up off the floor, I wasn't about to stop now. I thought I should think about it, I seemed to be beyond thinking. I walked down to his bedroom. He was standing next to his bed, as I nervously walked over to him. He reached down and grabbed the bottom of my sundress and pulled it up and over my head. Then reached down and pulled downward on my g-string. My g-string fell to my ankles. His big hand landed on my lower back and started to push me toward the bed. I stepped out of my g-string and started to climb onto the bed. He quickly followed me onto the bed and pushed me down onto my stomach. He straddled my legs. I feel him pouring a little oil into the crack of my ass. I was excited, but also nervous about how big he really is. I was really starting to think he's way too big. His cock was the size of my forearm.
He starts rubbing his huge cock head around in the oil on my ass crack. Then his cock starts to spread my ass cheeks apart as he pushes inward. His head pushes hard against my little anus. I whimper as it starts to stretch my anus open. I start to push back, he quickly tells me to not to fight it. I still pushed back till I began to tire. I all sudden lost the fight, my anus sucked his huge cock head in quickly. I cried out as I was painfully stretched and now tightly wrapped around his thick shaft. He moaned out with the his success of his penetration. He say's 'Damn your little ass looks so fucking hot with my big cock in it'. He start to lean forward, he rested his hand on the bed by my head. As he leaded forward his cock slowly started to push more into me. I struggled as his huge cock started to push deeper into me. He moved from his hand down to his elbows, his big hairy belly started resting onto my smooth lower back. He starts thrusting with his hips forcing his cock deeper. All the sudden it felt like he was starting to penetrate me all over again. He had started to push into my inner ring of my rectal folds. I whimpered loudly and yelled out too big. He responded with 'Oh fuck yeah your so tight. It's going in, your going to be a woman tonight hun'. He stopped with the thrusting, but kept a full inward push. I felt his throbbing cock slowly keep pushing deeper and deeper. I felt his pubic hair start to tickle my over stretched anus as he hits full penetration.
I cry out a little as I painfully start to cramp up under my left ribs. I could feel his heart pounding through his huge cock into my body. My insides where so sensitive. I seemed to tighten as my body desperately tried to to reject and push out the penetrating cock. He yelled out 'oh fuck, your desperately trying to milk my cock of it's seed. But your not getting off that easily hun.' He started to slowly fuck me. His sweat started to drip onto my upper back as he works me. I started to struggle as his speed started to pick up. His body started to then raise up off my body, so he could put his whole body into the fucking action. The now full painfully hard slamming into my body is causing my to slide across the bed. My head starts to hit his headboard. I had to use my hands to push myself back so my head would stop hitting. He loved me pushing back against him. I started to loose my sight and focus, I realized my eyes where rolling back in my head. I started to see stars as my mind drifted away. I started to think this must be the feeling of getting your brains fucked out really means. Then a moment of clarity came over me. I could hear his grunting as he fucked me. I could hear the bed moving from the fucking action. I could hear a sloppy wet sucking sound coming from loosening anus. And a wet slapping sound of my sweaty ass cheeks getting pounded hard filled the room.
The smell of sweat filled the room. It all seemed like it went on forever, I lost any sense of time. I struggle to focus on his alarm clock, I realized it had been a few hours of him pounding me. He started to slow, so I knew he was getting tired. He started to lay down on top of me. His weight seemed to push out the air in my lungs. He started to suck on my neck as he continued to slowly fuck me. He continued to fuck me like that for another hour. Then he raised up off me, as I tried to catch my breath. He started to aggressively fuck me again. I was thinking it was never going to end. And then he slowed to short thrusting inward only trying to make sure he was as deep as he could go. I knew he was as deep as he could go, my cramping under my left rib cage again started to return. He yelled out 'your about to be full woman'. We where totally still, I had a death grip on the sheets. Then I felt his cock start to twitch inside me, he grunted loudly like he was in pain. I felt his first explosive shot of his thick cum blasting out of his cock. Then he started to flood my insides with his thick baby making seed. He then moved to get more comfortable top of me, while keeping his cock still inside to prevent his cum from leaking out of me. He sweated so much on me, the sheets under me where soaking wet. I couldn't move as his body kept me pinned underneath him. A short time later he seemed to fall asleep on top of me. My struggle to breathe eventually caused me to pass out also.
After a little while he rolled off of my body. His cock seemed to pop, as it exited my anus. I suddenly felt so empty and hollow, and was already missing the full feeling of his big cock being inside me. Sore and exhausted I rolled onto my side. I felt a small amount of his cum leak out and run down my ass cheek. I didn't know if it was curiosity or my new role to clean myself. But I reach back to feel my sore and cum soaked anus. My fingers explore and find my poor little anus, I find a large gaping hole. With a couple fingers, I scoop up the cum off my ass cheek. With out thinking I bring it to my toward my face, I look at it briefly. Then stick my fingers into my mouth and suck his cum off my fingers and I swallow it. His thick and stringy seaman was hard to swallow. It seemed to travel very slowly down to my belly. I knew this night was going to change my life in so many ways.