The Day My Best Friends Dad Made Me A Woman by BreePhillips

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.