Growing up very poor and youngest of five and being only boy and no father. We lived in a very small town. Most definitely all my clothes and shoes were hand me down from them including panties and heels and dresses and stockings and bra’s ect. Honestly the only hair on my entire body was my eyebrows and eyelashes and long hair on my head and my sister’s where the same way even thru puberty.
We were home schooled by my mom who was a teacher by trade she was not very easy on us major subjects and they were even hardest could get and we had to read speak write Latin and dutch. Well soon my sister’s moved out and away since they were older than me youngest sister 9 years older. By the time they moved out I had my ears pierced twice and wearing makeup and lipstick and mini dresses and corsets and g-strings and bra’s and thongs set and high heels and stockings my eyebrows done thin and arched feminine and nails done and painted and toes painted. Mom always said that she only had girls.
I just turned 14 when she told me that a man who she knew was coming over to stay with while she was going out of town for a couple of weeks about a new job and lots of money. Well honestly she barely knew this old man. She said that he knew all about me. The next morning he showed up and she left. He was very nice and after she left he started to do work around the house fixing stuff and even painting. Well I knew how to cook so I made lunch and dinner and did the cleaning and stuff ladies do. After a couple of days he started to rub my hand or stocking covered legs and my ass . I just didn’t think nothing about it.
One night after dinner I was doing the dishes and I didn’t realize that he had came up behind me and put his arms around me and started to kiss my neck. I was shocked at first but it felt so amazing an was making me turned on. Then I must have let out a little moan. Because he whispered in my ear and asked if I liked it and I said that I did. I turned around and in his arms facing him. He put my arms around his neck and kissed my lipstick lips passionately as we kissed he unzipped the back of my mini dress. I didn’t even hesitate to stop him as he slipped it off my arms and pushed it down my body to the floor. I was just in my pink full corset and silicone breast that my sister’s sent me and thigh high stockings, g-string and high heels.
He picked me up an carried me to my bedroom and laid me down on the bed an kissed me passionately again and said that he would be back in a few minutes. I heard the shower going then stop . I had removed my g-string and was playing with my gurly-boi-pussi when he came back in the room naked seeing me playing with my gurly-boi-pussi virgin hole. He looked at me and said that he would take care of that for me . He came over to the bed and his cock was getting hard as he stood there by my head. I learned up and kissed and licking his cock. He asked me if I wanted to suck it for a few minutes. I said yes he sat down on the bed and I immediately wrap my lipstick lips around it and started to give him a BJ as he rubbed my gurly-boi-pussi and fingered it. He said that I was such a natural at sucking him. He couldn’t believe that I was deep throating him an not gagging. It felt an tasted so good in my mouth. Then he asked me to keep sucking him till cums. I sucked him for about 15 minutes then he said that he was going to cum and he shot his hot thick creamy load in my throat and mouth and I swallowed every single drop of it. I loved the taste and an way it felt when he came in my mouth.
He kissed me passionately after I was done kissing my neck and lipstick lips. He asked me if I liked sucking his cock I told him that I loved it. He said that when my mom asked him if would stay with me and told him about me he had his doubts about seeing me. But when he did he couldn’t wait to get be alone with me. Then I said when you started kissing my neck I could not believe how wonderful it felt. We talked an made out for a while and then he was completely over top of me kissing me.
I open my legs and wrapped them around his waist as we kissed very passionately he had lubed up his cock and my gurly-boi-pussi hole . He keeps his mouth on my mouth as his cock slowly stretched open my virgin hole. It hurt a bit as he was stretching my gurly-boi-pussi open he was going slow and gently soon he had all his thick 8 inches completely in me. He stopped when he was for a minute then he slowly started fucking me. For the next 45 minutes I was in seventh heaven and I completely in pleasure. Just before he shot his seed deep into my gurly-boi-pussi he got faster I was already moaning in pleasure and when he shot his load I screamed in pleasure. We laid there kissing after kissing and cuddling with his cock still in me till his cock slipped out of me. We fell asleep in my bed.
The next day by noon he had fucked me a couple of times. I was doing some homework and housework when my mom called. We talked for a few minutes then she asked me if I was cooking for him and making sure he was completely satisfied. I said yes I was. So after a while more talking she said so you don’t mind laying an sleeping in a wet spot. I said nope not realizing that I just told her that I was having sex with him. She then said that she was going to be gone for longer than she thought about a extra month. She said that I was way ahead in school and that I should be a good woman and really take very very good care of him and never refuse to give him sex anytime. After a few more minutes she hung up.
The day she came home she brought new clothes and shoes lingerie and everything else for me. She asked him if I took very good care of him he said yes I did as he put his arms around me. I was very surprised when he said that I was always ready an willing.
#Gay #Teen #Trans
I would have liked to have more build up of how you felt as they first started to dress you up in girl clothes. That could have been a whole chapter