Learning to be a Shemale Woman
It was the weekend before my eighteenth birthday when I really started to learn how to be a woman. My father and his wife had gone away for the weekend leaving me and my stepsister to fend for ourselves. Now you have to realize that Linda was beautiful by anyone’s standards and the two of us had always gotten along great. From a sex standpoint, I had no interest in her but I did have an interest in her body which, to me, was the kind of body I wanted with the exception of course, she did not have a cock.
Anyway, on that weekend with my parents out of town, Linda had planned on going out with her boyfriend. Linda, a year older than me, was off to university in three weeks and would be a four-hour drive away. The only good thing was that I planned on going to the same university the following year and that would make a huge difference in my life. I had no plans for the night since I did not tend to date and when you are a boy in high school who is more interested in men than women, you do not tend to date guys for fear of the fallout. Linda kissed me on the cheek as she left and I curled up in the family room watching a movie. Halfway through the show, I felt the need to get dressed in Linda’s bra and panties and so I went upstairs. I stripped naked in her room and pulled the bra and thong she had discarded in her hamper and put the on. God I loved the way I looked. I pranced around her room and then picked up her perfume bottle and dabbed a bit on my neck just like I had seen her doing it. I felt electrified and I was also starting to feel horny. Rather than getting her in trouble again, I slipped the thong off and my cock stood hard in my hand. I watched in the mirror as I jacked off in my bra that perfectly squeezed my little tits and forced them into a pretty awesome cleavage for a guy trying to be a girl. I was coming along pretty good when I heard the door downstairs open and then slam shut. I quickly pulled off the bra and slipped them back into the hamper and then, after picking up my clothes off her bed, raced to my room with my hard cock swaying from side to side as my little bum quickly wiggled through the hallway. I was not expecting Linda until well after midnight so her return was a surprise.
She knocked softly on my bedroom door as my t-shirt cascaded over my slender shoulders and I invited her in. Linda was obviously upset. She told me she dumped her boyfriend because all he wanted was sex before she left for university. Linda was a smart girl and she knew there was no future with the jerk even though she was horny as hell she told me. She sat on the edge of my bed and cried; then she suddenly stopped and looked at me with a look that I had never seen before. “What’s wrong?” I asked.
“Do you ever have sex David?” she asked.
I could see the reflection of my discomfort in her eyes as I tried to explain to her that I was a virgin. I don’t know why I kept talking though. I felt the need to finally tell someone about my feelings and since I trusted Linda and really loved her as a sister, I began to tell her about my desire to be like her physically causing her brows to furrow in disbelief. “Are you saying you are gay?” she asked but without an judgment.
“I don’t know, I have never had sex with anyone. I just know that I like to wear your underwear.” Oh shit! I let the cat out of the bag but Linda was not surprised at all. “I thought someone was putting on my undies,” she said with a smile. “Come with me,” she said inviting me to her room.
Linda did not close the door when we entered. She simply told me to strip. When I stood naked in front of her she went to her dresser and pulled out a satin bra and a matching thong. When asked if I had tried these on I told her no and she wathed as I put them on. All the while her eyes were glued to my cock which, although it wasn’t hard, was still big and she told me so. When I had her undies on, she came over to me and reached into the thong and pushed my cock between my legs and aranged my tits in the bra so they looked great. As her hands pushed and prodded me, I got hard and she knew it. “Look at yourself in the mirror,” she said and as I did, she took off her own clothes down to her undies. “You would make a beautiful girl,” she said with such a supportive tone I hugged her. The feeling of her body pressed against mine, and mine hers, got my cock a little hard and I could tel that she enjoyed it too. Then, Linda led me to the bed and said, “Let’s talk like girlfriends,” and she put her feet up and I joined her. I could see why her boyfriend wanted to fuck her so badly. She was really hot. As we lay on the bed just talking and her giving me suggestions as to how to be a better woman she suddenly asked if I had ever tried having sex with a girl. When I told her I had not, she slipped off her thong and her bra and then she took off mine. It as the first time in my life that a hand other than mine was on my cock and it did respond quickly. Linda quickly sank to my hard cock and began to lick the shaft and head while I eagerly rubbed my hands over her round firm tits that, to be honest, I wanted to have as my own. As she sucked my cock, I examined her nipples as the got hard and watched as she sucked like a woman and wanted to try. That night, was the first and last time I have ever fucked a woman although after that night, Linda and I would often sleep naked together but it was always like two girls sharing a sleepover. The next morning when we got up, Linda began to help me become a woman. She shaved my legs and most of the hair around my cock. She even began to show me how to put makeup on but suggested that I be careful with that around mom and dad and certainly around school until I had it refined. She told me to come up to her once a month and she would continue the lessons until I moved in with her the following year at university. Somehow, Linda seemed almost more excited about me becoming a shemale than I was. I would be the girlfriend she always wanted. Until she actually left for university, Linda taught me how to act and walk and talk like a girl every chance she had when my parents weren’t around.
On my birthday after Linda knew my secret, she gave me a secret present late that night when the folks were asleep. She crept into my bedroom, slid into my bed and said, “Open this one sweetie.” She had bought me my very own satin bra and thong set from Adorably You where she bought all of her sexy things. I kissed her and held her tight as the tears welled up in my eyes. I felt her hand touch my cock but it was not for sex. She knew it made me happy when she touched me.
Stay tuned for the next instalment of The Shemale Diaries.
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March 20th, 2010 at 10:30 am
Nice site, look forward to reading more of your posts in the future, keep up the good work!