Young and old meet to build lifetime memories
A light breeze blew as I sat out on my back porch looking out across at the woods behind my grandparents’ rural homestead. It was late evening and a time when the deer moved out to forage for food. I watched as they came out to feed. My thoughts took me back to an early time in my life. A time that I had realized who I really wanted to be. I grew up in a one parent family. It was just my mother and I and an older sister who moved out once she turned seventeen to live with our father in another state. Nancy, my sister, was three years older than me. My mother often let me spend my summers at my grandparents. I loved playing in the woods and fishing in the stream nearby. One day I found a magazine on the path leading to my favorite fishing spot. I picked it up and started looking at the pictures. They were young boys dressing as girls. And they were kissing and having sex. My little cock got hard in no time. I looked around to see if anyone was looking then I pulled my cock out and played with it while I looked at the pictures. I put the magazine inside my pants behind my belt and took it to my room and hid it. That Summer I found three more magazines and three books about cross dressing and took them home with me.
One day after school had started they let school out at noon because of some electrical problems. Mother wouldn’t get home from work until six so that gave me a lot of time to snoop around. I found where Mother had stored the clothes my sister left behind and curiosity got the best of me and I tried on some of her panties and slips. I immediately fell in love with the feeling. I especially loved the petticoats. So after that I began to dress. The next summer came and I visited my old fishing spot. It wasn’t until the fourth time that I went there that I found a new magazine entitled “Transgender U.S.A.”. I loved the pictures and found myself kissing those gorgeous cocks. I didn’t know who was leaving them for me or if it was meant for me. But I loved it. Two days later there were two books. One was titled “A Boys Dream Comes True.” I really loved this book because it could almost fit me since I discovered my sister’s things.
One Monday morning I decided to go fishing early and as I settled in I heard a noise and saw a handsome older man coming down the path.
“Good morning!” The older man said. “Have you caught anything?”
“Good morning! No, I just started to fish.” I said, smiling at him.
He sat down and we talked about a lot of things like what my home life was like, how many girl friends I had, if I played any sports, how old I was and what grade I was in, and also about my parents. He told me that his name was Seth Samuels and that he lived nearby. He was pretty for a man his age and had a slender build. He also had long blonde hair like myself. He talked softly and smiled a lot. And his eyes took in every inch of me which made me tingle inside. It was something that I never experienced before and I loved it. We must have talked for two hours and before he left, he invited me to his home.
“Well gosh Davy, I better be going. It was so nice getting to know you and I do hope you will stop by for a visit. I hope you catch more fish. Bye!”
As we were sitting close to each other, he did something that I hadn’t expected. He reached over and kissed me on my cheek close to my mouth. I didn’t react in a negative way but simply ducked my head and giggled. I looked him in the eye and said,
“Seth it was so nice meeting you and yes I’d like to come and visit. I think we could become very good friends.”
“Good, my house is a blue house with the white trim. See you very soon!” He said almost in a girlish form and blew me a kiss.
I watched him walk off thinking that I wanted to know more about him. He seemed so nice and he was so pretty and my insides were burning with a new and unknown desire. One that I never felt before. It was strong and it sent thousands of bolts of lighting soaring through me. My cock was stiff with desire. Two days later I got up early and walked over to Seth’s house. I knocked on the door and he let me in. He had on a robe and it looked like I had gotten him up.
“Did I get you out of bed? I’m sorry I didn’t mean to disturb you.” I told him.
“No, no, you didn’t disturb me. I had already been up for coffee and was sitting up on the bed thinking.” Seth said. Would you like something to drink while I drink my coffee? I have orange juice and chocolate milk!”
“Ooooh chocolate milk, my favorite!” I caught myself saying it in a girlish way.
We sat close to each other and from time to time he would touch my arm and each time a wave of electricity soared through me. Then I saw the magazine and I asked him if it was him that left the magazines and books. He took my hand and looking deep into my eyes and said,
“Yes it was me. I had been watching you whenever you came to visit your grandparents. I just knew by watching you that you would like to dress as a girl. And so to help you along I started to leave you some ideas. I was praying that I wasn’t wrong. I like to dress also and I hope I wasn’t wrong.”
“Gosh no, you weren’t wrong. I always liked how the girls looked so pretty in their skirts and dresses. I loved how their petticoats spread out the skirts and dresses. The first time I saw the pictures of the gorgeous dicks it made me feel funny inside and so I started to dress in my sister’s things. I like putting on her things, it makes my dick hard.” I told him.
Still holding my hand he asked me if I wanted to dress up? He told me that he had some things that would fit me and it excited me. He led me to a bedroom where I could look in the closet for something to wear and in the chest of drawers I would find panties and bras. Walking out to meet him, I saw a beautiful blonde goddess. She was lovely and dressed in a pink with white lace trimming summer dress. The dress hugged her body and my dick stirred. I stood in front of her and twirled around, my petticoats flared out showing my girly legs. She reached out to me and taking my hand brought me close to her
.she patted her lap and I sat down. With one hand holding me, he turned my head with the other. He brought my face close to his and whispered to me to open my mouth a little. Then with my mouth open he placed his lips over mine. What a wonderful feeling it was, her tongue swirled around my mouth leading me to new heights of ecstasy. I never felt so alive as she held me and explored my hot mouth. I soon joined in the exploration of our mouths and letting our tongues dance with each other to the music of lust. My arms went around her neck, holding her fast to my ios. I felt her hand as it slipped under my dress and to my panty covered hardened dick. I let out a big sigh as her hand laid over it. We stopped kissing to catch our breath. She was smiling and looking at me. Then she sweetly said,
“Ooooh sweetheart! You’re a natural born kisser. I think I am going to love having you dress so pretty and sexy. Have you thought up a name for yourself? I want to be called Sabrina.”
“Mmmmmm that was so wonderful and so exciting. I want more of it. And no I haven’t thought of a name. Mmmmmm and your hand on my dick is so wonderful. Can we do more love making? I want it so much.”
“Sure baby girl and I think you should call yourself Diana after the sex goddess Diana. And because you are such a pretty little thing and so sexy. Mmmmm yes the goddess Diana.”
“Ooooh god yes, I could be Diana. I am so on fire that I want all that I can get and learn to do!”
“Mmmmmmm honey, whoa! Let’s not get in a rush and miss out on something. We have lots of time to do and learn. Right now I want to taste your precious virgin seed, why don’t you lay back on the sofa and let Miss Sabrina love you. Gawd you’re so fucking sexy!
As I settled back Sabrina raised my dress and petticoats. I raised my little ass to let her slide my panties off. Sabrina started to kiss my leg as she worked her way to my hardened dick. His tongue worked magic on my cock as I started to call it but Sabrina told me that it was my clitty from now on and that my ass was my pussy. Sabrina’s mouth felt so marvelous as it slid over my clitty. I was rock hard and pushing up to meet her. I nearly lost consciousness when Sabrina placed my ball sack in her mouth and played with it. I was moaning and breathing hard as she worked on my clitty. She turned me over and had me get on my knees. I nearly died as I felt her tongue slide across the crack of my pussy. I groaned in absolute ecstasy as she worked on my pussy. Her tongue searched as far as it could into my pussy. She turned me back over and finished me off by taking in all of my seed.
We snuggled closely for a while then I moved to get between Sabrina’s legs. I followed her pattern and pushed up her dress while kissing her legs as I did. I reached her clitty and laid my cheek on it. I took in her aroma and felt a hot chill run through me. I tugged on her panties and she raised up to let me pull them off. Her clitty was gorgeous, long and slender. And her nut sack hung so magnificently. I reached out to hold her clitty then lowered my head to kiss the head. I devoured his precum and began to love on the gorgeous love pole. I rubbed it against my cheek giving it kisses and licks as I worked my way to her nut sack. I was so excited about what I was doing and it all came so naturally to me, so easy for me to do. I closed my eyes as I encircled her nut sack with my mouth and like her I played with it with my tongue. I love feeling her clitty sliding in and out of my mouth. It was a new experience and so enlightening. I felt like a new girl and I fell in love with all of it. I sucked and jerked on her clitty. I was sucking when she tensed up and shot her first burst into my hot mouth. It took me by surprise and I lost most of it as it seeped out of my mouth but the other three burst I did better. I cleaned her up like she did me and then I slid up to nuzzle her. Sabrina lifted my head and turned it towards her. She kissed me lightly on the lips and said,
“Ooooh Diana what a wonderful find I have in you! You’re so magnificently talented. It seems as though all of this is coming naturally to you. I am so excited to find out how much more love making comes easy for you. I have never met anyone like you before. Mmmmmmm you’re so special. Let’s stay dressed for the rest of the day and be girls.”
Sabrina was out of breath as she held me tightly. I too pulled her tightly wanting her to know that I was okay with all that had taken place. I wanted to become her girl. Night came and I ventured in for the night. The next morning I got a cup of coffee and went out to sit on the back porch. Soon my thoughts went back to Seth’s and my time together. Along the way I lost my grandparents and I had inherited the homestead. Seth and I enjoyed a lot of fun times and I especially liked going to Taos, New Mexico. One day Seth asked me what I thought about attending a swinger party for people like us. It would be for couples who were young and old. It had to be an older man with a young man. I thought about it and asked a lot of questions then decided that it might be fun. I had turned twenty one and didn’t need anyone’s permission to go. I packed the most sexy dresses that I had. We arrived at Taos and registered and went to our room for the night. Sabrina and I made sensual love that night. The next day was filled with signing up for different events. During the signing, I noticed a man that stirred something inside me. I was drawn to him. It turned out that we were signed up for the same things. That evening at the grand opening. I had chosen to wear a tight fitting red with white lace trimming summer dress. Sabrina had on a light blue with dark blue lace trimming dress that hugged her body. The man that stirred me saw me and made his way to sit next to me. We exchanged names and soon I felt his hand on my leg. I turned and smiled at him. After a few announcements the music started with a slow number. The man asked me for a dance and I accepted.
Out on the dance floor he held me close enough for me to feel his hard cock. He told me that he was called Rick and I told him that I was Diana. He massaged the cheeks of my pussy as we danced. I looked up at him and softly said,
“Mmmmmm you horny old man, if this evening doesn’t hurry and end, I think that I may just get raped right here on the dance floor.”
He smiled and laughed and that night he made passionate love to me. I had three other men that week but none like the first one. On the ride home I told Seth that next year if we were invited that I would like to go again. We did it three times before he died of heart failure. He left me a small monetary amount and with that and what my grandparents left me, I am set for life.
🔞 Candy.AI 🔥 AI Sex Chat – Roleplay, Erotic Stories, Try for Free 🕹️