The Making of a Sissy (Part 5: Boys Will Be Girls)
Eyl 6, 2021 // By:analsex // No Comment
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The Making of a Sissy (Part 5: Boys Will Be Girls)Struggling to keep my eyes open, I stirred my spoon around in my cereal slowly as if I were hesitating to get on with the day. In a way I was procrastinating. My mom had just woken me up to remind me that it was Friday, and this was the weekend I was supposed to go stay with my dad. Since their divorce, I only saw him for one weekend out of every month, which for me was more than enough. Don’t get me wrong, it wasn’t that I didn’t like my father, I just struggled to keep myself entertained when I went to visit. As I sat on the stool in the kitchen, my aching sissy hole reminded me of how fast the week had flown by. It had only been a week since I had met Sam, the man who had changed me in so many ways. Each night I would lay in my bed wearing nothing but my panties and stockings, with my ass up ready and waiting for him. He would come in late, after he had finished with my mom, and he would feed me his big black dick. I had become totally addicted to him in every way. I craved his manly touch, and I couldn’t keep my mind off of his long throbbing cock. It really saddened me that I wouldn’t be getting to experience it during the upcoming weekend. In a way I didn’t want to go, just because I didn’t want to miss out on the amazing sex we had been having. My mom’s cheerful smile made me even more envious as I could tell she was looking forward to her upcoming weekend with Sam. As I drove to my dad’s place, I thought about how he might react if he knew what had been going during on the past week. I dreaded the notion of him finding out about me, but nonetheless I had still packed a few pairs of panties for my trip. He only lived about 45 minutes away from us, further into town. I had pretty much grown up there, and I still had a few friends in the area. Once I made it to his apartment complex I parked and unloaded my bags from the car. I headed upstairs into his empty apartment, and laid my things in my bedroom. He was still at work, which was were he spent about 75% of his whole life. I wandered down to the pool to hang out and get some sun while I killed some time. On my way to the gate, I noticed a friend of mine who was walking around the pool. Her name was Heather, and we had gone to high school together. She was a year older than me, and she had just finished her first year of college. As she noticed me, she approached me. The sun was beaming off of her fair porcelain white skin, her long auburn colored hair flowed with the wind, and her beautiful soft blue eyes made contact with mine. Her D cupped breasts hugged each other in her bathing suit, and her curvy hips moved so smoothly as she came closer. She was a gorgeous young lady, but I had never really considered myself attracted to her.”Hey there Brian!” she shouted with a smile.”What’s up Heather.” I smiled back.”Another weekend at your dad’s place, huh?” she asked with sympathy. I simply nodded.She knew how little I looked forward to visiting, but she always made me feel better. Heather knew a lot about me, and she was extremely open about herself as well. Whether I wanted to or not, I knew a lot about her. In school she had been one of the most promiscuous chicks I knew. She had slept with so many guys I couldn’t even count, and she would always inquire about my sex life. I had dated a girl in high school, and she always wanted to know every detail about what we were doing in the bedroom. I considered her a pretty close friend, and since she lived in the same apartment complex as my dad I was always glad to see her when I came.”So what’s been new with you?” she asked as her eyes glanced up and down at me.”Oh, nothing.” I responded, trying not to blush.The gestures on her face began to change as she could tell something was not right. It looked like she was pondering deeply about my answer. “No, something is different about you.” she added as she kept observing me.We were walking to the lounge chairs to sit down, and as we walked she kept looking around me from front to back.”I can tell by the way you’re walking, something is different. şişli escort Have you been getting laid?” she giggled curiously. My face was turning red by this point.”No!” I exclaimed. As we sat down, she smiled and continued to pry.”So…who is she?” she inquired. “Do I know her? How did you meet?”Frustrated with all of the questions, I shook me head vigorously. “It’s not a girl!” I yelled. I couldn’t catch my breath as I looked around nervously to see who all had heard me. Heather’s jaw dropped open, then she began to giggle.”So it’s a guy?” she asked even more curiously. I closed me eyes and shook my head.”I’m not going to say” I responded.She wouldn’t leave the question alone and kept digging for more information. “Well…what are you saying then Brian” she nagged. I could tell she was getting frustrated.I slid my shorts down a little, exposing my pink and black thong, and I glanced up at her. Her face lit up with shock.”What the…who?” she was almost speechless. While we laid there under the sun, I tried to explain everything to her. Who Sam was and how he was changing me. Heather, being the very open minded person she was, had truly understood me. It felt great to get everything off my chest, and share it with someone else. She asked me how long I thought I could keep it from my mom. Honestly, I hadn’t even thought about it until then, and I was lucky she hadn’t caught me yet. Heather opened my eyes to a lot of things, and I was so happy that I could talk to her girl to girl. “You know, I could help you” she said.”Help me?” I asked as I blushed.”You know, with your transformation.” she added.I wasn’t sure what she had in mind, but I liked where she was going. She told me there were a lot of things I needed to work on if I wanted to look like a girl, and she began pointing them all out to me in detail. After the pool, we went up to her apartment where she began my sissy makeover. One of the first things she pointed out to me is that I needed to have a completely smooth body. I wasn’t a particularly hairy guy, but even so, all the body hair had to go. She drew a bath for me, and as I laid in the tub I lathered up one of my legs and used one of her razors to shave. As I felt the smooth blade swing up my long legs, I felt so natural. I managed to get everything below my waist completely smooth, and then I worked on my arms and everything up top. Once I came out of the bathroom, she gave me a lesson on how to use makeup. We spent hours together going over everything, and she even let me have some of her kits and accessories. Before going back to my dad’s place, I hid everything she had donated to me in my car. Heather and I had made plans to spend time together the next day. That night I stayed with my dad, mostly in awkward silence. My smooth body felt so different underneath my clothes. It was almost impossible for me to fall asleep that night as I thought about Sam. This was the first night I had not had him inside me since we met. I thought about all of the things he might have been doing with my mom, and suddenly my hips started sliding back and forth. My cock rubbed against my panties as I laid in the bed underneath the sheets. Before I knew it I was humping the mattress as my cock stiffened up. I rolled over on my back and slid one hand down my panties. My fingers went right past my sissy clit and down to my hole. I started massaging around my hole until one finger made its way inside. My pussy was still very tight, and I started stroking my semi hard cock with my other hand. I thought about how Sam would take me in this position with my legs wrapped around him, pumping his cock into me until my clit squirted onto my tummy. He would fill me up with his seed as we both climaxed together. Just the thought of that sent my cock oozing, as tiny spurts of cum leaked out underneath my panties. I wiped my mess up with my fingers and slid them into my mouth, sucking all of the cum off, only wishing it was his instead. After that I dozed off, dreaming about the big black cock that I was craving.The next morning mecidiyeköy escort I got ready, and I told my dad that I was going out with Heather. He seemed to think she was my girlfriend. I giggled to myself, and told him it wasn’t like that. Once we met up she put her hands on my arms and said. “I know what we need! Manis and pedis!” She was so excited to share these moments with me. She took me to her regular nail salon, and the Vietnamese women went to town on our hands and feet. It felt so good sitting in the fancy chair, getting pampered. Now I knew what the big deal was for women and why they paid so much for this. Heather had recommended a french manicure, so that’s what we got on both our fingers and toes. After we were finished she took me shopping for clothes. She picked out a few cute outfits for me, and of course we increased my collection of panties with her recommendations. Once our day came closer to an end we went back to her place. “I appreciate all of this more than you can imagine.” I said smiling.”Don’t mention it.” she smiled back. “I’m glad you let me help you. It really means a lot to me.”We enjoyed our last evening together, sharing stories and talking about the big cock that was waiting for me back home. Heather had taken her share of black cocks as well, so she knew why my obsession was so huge. She was also very familiar with anal sex, so she tried to give me some tips on how to handle it and what positions worked best. She was such a sex guru. That night was no different than the one before, as I tried to get to bed while my mind raced and thought about Sam.The next morning, Heather and I met up again mostly hung out in her apartment. The whole weekend was flying by, and I hadn’t hardly spent any time with my dad. He didn’t seem to mind however, because he thought Heather and I were dating. Instead of leaving early, I stayed with her until it got pretty late that night. I called my mom and told her I would be coming home late and that she shouldn’t wait up for me. I wanted to be dressed and made up for Sam when I got home that night. Heather helped me with my makeup, and helped me choose which outfit I would wear. Our similar skin tones gave me a huge advantage with her inventory of makeup. We used a little bit of eye shadow and blush, as well as a thin layer of eyeliner. She recommended a light pink lip gloss that would make my lips sparkle irresistibly. Before she sent me on my way she said she had one more thing for me. She handed me slim package.”What’s this?” I asked.”Those are my birth control pills.” she said. “You should take them. The hormones in them will improve your feminine looks.”As I opened the package, I saw the calendar of pills she had been taking. This package was only about a third of the way empty, and there was another full package behind it.”Each time you come to visit, I’ll keep you stocked up.” she winked.I popped one of the pills out of the package and swallowed it, and I thanked Heather for everything and for being so supportive. She kissed me on the cheek and sent me on my way. During my ride home all I could think about was Sam. I had hoped he would like the way I looked now, all dolled up for him. I was overcome with anxiety as I got closer and closer to home. Once I arrived, I quietly tried to sneak into the house. All of the lights were turned off, and I couldn’t hear anything. I slipped downstairs, hoping to see him, but to my surprise the room was empty. I was a bit disappointed that he had not been waiting on me to get home. I walked back up and unloaded all of the bags from my car. All of the new things I had acquired needed a hiding place so that my secret wouldn’t come out. I dug in my closet finding the best place to store all of the makeup and clothing I had brought home. When I closed the closet door shut, I was alarmed by a voice.”Damn you look sexy.” It was Sam! I turned around and looked at him, smiling. I had on a pair of short white shorts that came up to my ass cheeks, a light pink tank top that came down just to my belly button. şişli escort bayan My smooth long legs ended in a pair of sandals, with my freshly painted toenails. My little clit was trying to get excited underneath my panties as I bit my lip and walked toward him.”I missed you so much!” I moaned.I put my arms around his neck, and he grabbed me and pulled me closer. He kissed my irresistible lips, and his hands ran underneath my shirt and then down my shorts and around my ass. He squeezed my ass with both hands and pulled me into his throbbing cock. I could feel his bulge growing against mine as he pulled me close and made out with me. Sucking on his lips and his tongue we both let out moans of pleasure as we couldn’t get our clothes off fast enough. One of my smooth arms reached down and unzipped his pants as I dropped to my knees. I pulled his pants down around his hips as his massive semi erect cock popped out of his boxers. My sparkly glossed lips wrapped around his huge head, pushing my mouth further onto him. His cock got harder as it went deeper into my warm mouth. He smiled as I looked up into his eyes with his cock feeding me. I was his girl, and I had shown him that that’s exactly what I wanted to be. His hands wrapped around my head and he pulled me into his cock further, pushing it deep into my throat. As he kept fucking my mouth harder and harder, tears were welling up in my eyes as I gagged. He pulled his cock out of my mouth and slapped my face with it. Sucking on his balls, he rested his long cock across my face. I stroked it with one of my soft hands, while my mouth slurped around his huge balls. Then he pushed his cock back into my mouth, fucking my throat once again. My mascara was starting to run down my cheeks as he pumped his huge cock into me. Then he pulled me up off of the floor and turned me around. One of his hands grabbed the back of my neck and pushed me down onto my bed. His hands wrapped around me as he unbuttoned my shorts and slid them down to my feet. He pulled my panties down to my knees and started rubbing his cock between my ass. I arched my back as he spread my ass open, pushing his cock against my hole. His head penetrated my tight boy pussy as my hole loosened up to accept him. His hands rubbed my smooth hips and around my smooth body. He pushed his cock further inside me while I was bent over against the bed. I felt the wet pre-cum leaking out of my semi hard clit while he went deeper into me. I was letting out girlish moans of pleasure while I thought about how much I had missed his cock. He leaned down and turned my head to the side and kissed me while he continued to thrust his cock in and out of my sissy hole. He pulled his throbbing hard cock out of my ass and turned me over and laid me down on my back. My legs were spread open for him, and he guided his cock back inside me. One of my smooth arms reached down and my soft manicured hand grabbed his cock and helped guide him into my hole. Once his cock penetrated me again, my semi soft clit oozed out with a spurt of sissy cum, leaking onto my smooth tummy. He grabbed my hips and fucked me harder, pushing that big black dick deeper inside me, filling me up completely. His hands caressed my body, rubbing around my chest and fingering my nipples. Then he put one hand around my neck, choking me while he pounded my ass harder and harder. One of his fingers slipped in between my lips, and I sucked on it, rubbing my tongue around it while he kept fucking me. I felt his cock go further into me as he pushed it balls deep inside me. His pelvis was pushed against my ass cheeks, making me take the full length of his big black cock, and he just held it there. His throbbing dick started twitching as he climaxed, releasing his cum deep into my sissy womb. He flooded my pussy once again with his warm load. He let out a loud moan, and pushed his cock deeper a few more times, releasing the last spurts of his cum inside me. My little cock was leaking the entire time, and as he pulled his long hard dick out of my hole, he rested it against me. His massive, heavy cock laid on top of mine, covering it, and extending upward to my tummy. I was convulsing as his long shaft rested on top of me, and a few more squirts of cum leaked out of my cock onto my tummy. He leaned down and kissed me deeply and then whispered into my ear.”I missed you too Brianna.”TO BE CONTINUED
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