My name is Kalynn; I have been living as woman for the past four year. It all started when I wore my first pair of panties at the age of 14. I am 5 foot 6 inches, 145 pounds brown hair, brown eye’s, a nice smooth round ass, just right for a pumping. When I put those panties there was no turning back. My mother and I lived in a small house, out in the country, there were a few neighbors around us, mostly older couples, except for one man, James Walker, he was about 50 years old, salt and pepper hair he was a substitute teacher. He would come over at night a few times a week and have coffee with mom and I. Mom had discovered my little secret, the first few weeks into it. She didn’t mind it, as long as I stayed out of her panty drawer, she even went as far as to buy me my own panties, red, black, green, pink, orange, gold. She even went as far as to buy me panty hose, slips,. It seemed to me that she was encouraging me to go beyond just panties. She finally told me that the reason for this was that , she had always wanted a daughter, and seeing that she wouldn’t have any more kids, I would fit the bill. How much I didn’t know and how I was going to learn.
This had gone on for quite some time. Mom had taken me out of school, and Mr. Walker was home schooling me. Which I was all for, but Mom had insisted that in order for me to do this I would have to dress and act like a girl all the time. It was fine with me, but I didn’t know what to do about Mr. Walker. Mom told that she had told him, and that he was alright with it. My first day of school I was a nervous wreck, I had worn a knee high blue satin skirt, a white blouse, had done my make-up, and hair, and at exactly nine o’clock Mr. Walker arrived. An hour into my first lesson, he had me at ease. He didn’t look at me funny, make any remarks, it was all teacher student. I did find him a few times standing beside me, looking down at my work and smiling. His only comment was “nice work Kalynn”. I was stunned at first, that he knew my girl name that mom had given me, but the work went on. Mom had been giving me vitamins she said , but I later found they were hormones, she even had me use cream, it smelled of lavender, on my breasts, they had begun to form little nubs, my bra size went from training bra to a 32c in about a year. My little cock was just that, little even when I got a hard on.
Anyway with all this going on, I was required by law to attend school, and Mr. Walker fulfilled that requirement. I had never had any sexual thoughts about being with another man. When I would masturbate, it was the wearing of women’s clothing that excited me the most. One day Mr. Walker announced to me that dance class would begin. I didn’t know what to say, after all he was the teacher, but he went on further to explain, that I would need to learn how to follow, instead of lead, if was going to continue to be a girl. So I did as he said. He took me in his arms, grabbed my right hand, placed his left hand on my hip, I placed my left on his should, and he told to follow his footsteps. Which I did I was clumsy at first, but he told that as time progressed I would get better.
That night I didn’t tell mom about the dance class, I told everything else. As I lay in my bed, I couldn’t help but think how Mr. Walker smelled, how he held me with confidence, how he looked in my eyes. I soon found my little cock, and was stroking it, thinking about the dance. I came hard that night. The next day it was the same old thing, teacher talk, student listen. No more dance class, I was a little disappointed about that. That I read some real good articles on how to flirt, I wanted another dance lesson. The next day, I worn a pink midi shirt, with a white satin top, dark panty hose, and white 2 inch heels, I wanted him to notice me, and he did. After his normal two hours of teaching he stopped, and slipped on CD with slow music. “Kalynn, come here, time for another lesson”, he said. I got up and walked over to him. He grabbed me, this time he held me close, so close that I could feel the bulge in his pants. He began to lead me, in slow rhythmic dance, all the time I could feel the bulge grow in his pants. He looked down at me, and kissed me. I had never kissed anyone before. I just let it happen. I felt the heat building up in me. Oh my, is all I could think. We ended up on the couch, our make out session lasted for a good hour. He wouldn’t let me take out his cock, but he did let me rub him through his pants. This had gone for a week every night I lay in my bed think about how his cock must be, I would masturbate, two or three times a night, with the only though of taking Mr. Walkers cock in my hands.
Thursday after noon, mom came early from work, and announced to me and Mr. Walker that she would be out of town until Monday after noon, her job was going to send her on sales contact she had won. After a she had packed, Mr. Walker and I helped take her bags to her car. Mom turned and smiled at me and gave a peck on the cheek. She looks at Mr. Walker and said with a wink take care of Kalynn now. Mom drove off. I walked through the fort door, Mr. Walker followed. He closed the door. “Kalynn, come here”, he said as he pulled me to him, and started kissing me. He pulled back, and said, “Your mom told me to take care of you, and that’s what I’m going to do now”, He took me by the hand and lead to my bedroom. He laid back on my bed. “Take my pants off Kalynn, I know you want to see my cock”, he said. I was so nervous, I got on my knees and took his shoes and socks off, I reached up and undid his belt, and his pants and I pulled his pants and shorts off. I stared in disbelief. There was his cock, oh my god, he must of be at least eight inches, the head looked so big and purple. “Touch it Kalynn, do now!” he said. I reached for it, my hands went around his shaft. It felt so hot. “Stroke me Kalynn” he said. It was so hypnotized by it, I followed his order. “Umm good, baby, come on up here next to me”, Mr. Walker said.
I crawled up next him, “Kiss me”, He said. “Umm good Kalynn, make me feel good”, he said after our kiss broke.
“Kiss it Kalynn, kiss the head of my cock”, he said.
I didn’t say a word; I just lowered my head to his big beautiful cock, and started kissing the head. I flicked my tongue out and tasted the ooze that was coming out, “ummm” I said. Mr. Walker had pulled me around so that my ass was facing him. I felt his hand slip up my skirt, and pull my panty hose and panties down. I felt a wet finger slip into my ass, it hurt a bit at first, but he took his time, telling me to relax, all good girls need a good finger fucking he said. I gave in, and he was sliding his finger in and out my tight virgin ass, he had soon slipped two fingers in, and he had begun to rub my little balls and cock, it felt so good I had to stop licking the head his cock, I couldn’t concentrate. He pulled away, and slides up behind me. I knew what he going to do, my hear traced. I felt the head of cock push against my young tender virgin ass. “Relax now”, he said and then spit on his cock, and began to rub against my ass. I jumped when the head entered me, it hurt, but he keep sliding in, nice and easy, and then pulling back, the pain slowly went away. He was soon fucking me so good.
“Kalynn, you’re so tight”, he said as he pumped. I soon found myself, meeting his every thrust. Oh my god it felt so good, I started to get a tingling sensation in my ass and balls. “Oh baby fuck me”, is all I could say. This drove him on. I reached up between my legs, and I started to message his big balls. “Ummm good”, he said. His breathing got heavier, his pace got faster. “Kalynn, Kalynn, I’m going to cum”, He said with grunt. I felt his him stiffen up, and his cock pulsed, and filled my ass with his sweet cum. With each squirt, it felt better and better. I came in my panties, I was thrilled my first anal orgasm.
He filled my ass so full when pulled out his cock; his juices ran out of my ass and on to my panty hose and panties. I collapsed. If being a girl is feeling like this. This is all I want then. I rolled over on my back, smiled at him, all the time his cum dripping out of de-flowered ass. “We need to clean up Kalynn, and get dinner”, he said. All I could do was smile, that nigh he fucked me again, this time I was on my back legs wide apart, black garter belt matching nylons, panties and bra. I was his ass slut for the nigh.

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This is not porn, if you came for porn, you may as well leave. This is a story designed to educate people about the hardships of gender dysphoria. This story is the story of a very good friend of mine; she wrote it herself and wishes to remain anonymous for reasons that should become apparent as the story progresses. There will likely be follow up stories dealing with other issues of gender dysphoria as her own story continues to unfold.