Losing My Cherry
There were times, until Linda left for university, that I was sure she was going to spill the beans about who I really was but every time, she kept quiet and assured me every night that she was well into keeping our little secret. Until she left, she gave me a crash course on being a girl every chance she got. She showed me how to walk, talk and hold my hands without looking like I was some effeminate gay. She also told me not to wax my legs until I moved in with her the following year. It’s funny, looking back, I was about to do the waxing and never thought that when I was in the shower room after gym class, I would be more than obvious to the other guys. Shaving around my cock was not that big a deal since the jocks did it anyway so that their dicks looked bigger. Throughout the last year of high school, I worked hard on my grades, worked harder on my feminine side and worked even harder not to reveal my little secret to my parents. In her wisdom, Linda took the bra set she had given me with her and assured me it would be there every time I visited her. I visited Linda once a month and our parents were so happy that we had such a natural brother and sister relationship and that we wanted to spend time together. It makes us smile even today!
It was in that last year of high school that I also had my first sexual experience with a man. One day, my chemistry teacher asked me to stay after class to talk. I knew I could not be in trouble since my test scores were almost always perfect in chemistry and all of the other maths. He told me that one of the boys on the football team needed to get his grades up and suggested I tutor him and I agreed. I knew Steve to see him and always thought he was hot but he was always surrounded by the girls as most typical football players are. Anyway, we made arrangements to meet twice a week and for three weeks it was all business. Steve was not stupid, just distracted by his “jock” life and he picked up the basics of chemistry pretty fast. My parents were going to be going away one weekend and I suggested Steve come over if he had the time and we could spend all day Saturday working on it rather than an hour here or there. He quickly agreed and it wasn’t until later that I realized why. As agreed, he showed up just before my parents left and met my dad and stepmother. “No parties!” my dad ordered. “Oh no sir,” Steve countered, “it will just be the two of us and we will be studying hard.” My parents left and as we always did, Steve and I got down to studying. Two hours later we needed a break and we went into the family room just to kick back and talk. I had no grand dillusions that Steve saw anything in me othe than his tutor. After all, he was a jock and had his pick of any babe in school but something deep inside me wished that I had become that girl before I started my last year. But I did not let on that I wanted him.
We were joking around on the sofa and having a laugh when suddenly, he leaned over to me and kissed my cheek. “What the hell?” I asked seriously.
He could see the horror in my eyes and said, “Sorry man, I thought you were gay! I have been watching you for a long time and I thought that you liked me - you know!”
“Steve,” I probed, “Are you telling me that you are gay?” My biggest concern was that he was not gay but only trying to rack up a good story for his football buddies. Steve nodded slowly! “But all of those chicks,” I countered.
“Well, I have to put on the show right? I prefer boys and although I have fucked a couple of babes, I have never really had a guy before because I have been a chicken shit. But you are different. I like you a lot and I have seen you in the shower room and I like what I see.”
I was more than a bit skeptical and as much as I wanted to jump on his body, I was also very worried that this might be a trap and I told him so. Without saying a word, Steve stood up and began stripping until he stood in front of me completely naked. It was the first time that I had seen a hard cock other than mine and it was definitely hard. Nature took over and my body seemed to lean closer to him until he could feel my warm breath cascading over the pulsating head of his cock. “Oh that feels so good,” he said. I did not need any more encouragement. I leaned ever closer and my lips made contact with his hard cock and I naturally began to start licking it and examining this hard beast like I had always dreamed. He placed his hands on my head and gently pulled me towards his hard dick; my mouth opened and as my fingers now danced along his shaft, I began to administer my very first blowjob to the sounds of his deep passionate moans. “Can we go to your bedroom?” he asked. Without a pause, I released my lips from his cock and led him upstairs to my room where I quickly turned down the bed, removed my own clothes to expose my cock that was harder than I had ever known. When we climbed onto my bed, I was still hungry to taste his cock and more importantly, his jizz and I immediately went down on him to resume my virgin cock sucking. As I cradled and massaged his balls in my hand, I could feel them begin to rise and knew I was about to receive the white foamy cum and sucked and lapped at his dick even more furiously. He moaned long and loud and suddenly, I felt him explode in my mouth until the cum trickled down my chin. He had blown his load and now he wanted to have mine. He lay back on the bed and spread his legs, lifting them above his head. Instinctively, I knew what to do. I wiped the cum that I had not swallowed over his tight little ass hole and got it wet. When my finger slid into him without resistance, I aimed my hard cock and began my first expedition into fucking a hot guy. As much as I wanted to blow my load, I needed a cock in my ass. I knew that would feel right and before I came, I pulled out of his tight sphincter, knelt face down on my bed and panted, “I need you to fuck me real hard Steve!” He mounted me in a heart beat. The searing pain was meaningless as he rammed his cock deep inside my ass and humped me like a rabbit in heat until he came once again. While he fucked my ass, he reached around and grabbed my cock and with every push of his cock, he rubbed on my cock until we both exploded together. Steve was as hungry for sex as I was that first day as we both lost our virginity. After I had blown my load all over my sheets and Steve’s softening cock slipped out of my ass, he knelt over my cum load and he ate it telling me he wanted to taste me like I had tasted him.
For the balance of the day, Steve and I fucked in every room of the house including in Linda’s bed. We talked a bit and I told Steve about my desire to be a shemale which really turned him on. He said that if I looked like a girl, we could date all of the time and no one would know he was fucking another guy or that he was gay. I told him I could not do it yet but maybe by the summer. In the meantime, we could study more than chemistry whenever we were alone and he quickly agreed. The following afternoon, after I finished tutoring him, he undid my pants, slipped them down and gave me another blowjob saing that he needed to drink me one more time before going home.
Linda was thrilled that I had finally lost my cherry and as she had promised to do, by the end of the school year, she had me to the point where I could almost greet the world as a woman. When I moved in with her a month later, the metamorphosis would be complete.
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