How my Sex life came about part 1

How my Sex Life came about part 1

My name is John but I go by Jenny now most of the time. I am a 64-year-old bi crossdresser. I am non-passable but play dressed with others when having sex. I have a pair of 40EE silicone fake tits that I love to wear while dressed.

This story is about how all that came about. This a true story, not fiction. Some will not believe it while others might be able to relate to certain phases of my life.

My life was full of events that I had no control of and fate was in control. In other events, I was in total control. However, I did not always make the right decisions.

Do I regret my chooses in life? Did fate deal me a bad hand in the game of life? I will let you the reader decide that. I am not sure one way or the other. I hope you enjoy it and perhaps you can relate to my life.

I came from a well-off family my father owned an engine repair/built restoration shop. He owned a classic car collection and people from miles around would bring him cars for him to restore.

My mother and father very well knew in our small town. We lived in a huge house on 35 acres of land most of that being woods behind our house. We had an in-ground swimming pool with a diving board. There was even an outside kitchen/bbq area.

I started at a young age having fun in our neighborhood. It started when we all were playing hide and seek. The girl who lived next door to me was hiding with me in the woods. Her name was Patty and she was 1 year older than me.

As we were hiding she said she had to pee. She stood up dropped her pants and squatted. I stood there watching pee gush from between her legs. It was amazing as I had never seen a girl peeing.

I didn’t know much about sex or girls at this time as I was young. However apparently my cock liked what I was watching. It was tingling and had grown hard.

Patty pissed for a long time smiling at me as she did. Patty was a ginger, a redhead. She even was starting to get red hair around her puffy pussy. She had a lot more than I did. Her tits were just starting to form. They were puffy with big nipples already.

I had discovered the great feeling one gets when you rub your cock when it starts to tingle. I learned that in the bathtub. I played with my dick every time I took a bath.

My cock was tingling and hard in my pants. I started to rub my cock through my pants watching her pee. Patty smiled telling me to show her my dick. I pulled my pants and underwear down exposing my hard dick to her.

Patty looked at it as she asked, “You want to rub butts?”

Patty stood up and showed me her ass and had me place my butt against hers. We rubbed butts together as we both rubbed our private parts. We heard others coming through the woods so we stopped and pulled our pants up before they saw us.

Patty and I would go into the woods daily after that. We would strip and rub butts. We did finally figure out she could rub my dick while I rubbed her pussy while also rubbing butts. Patty had me suck on her little tits as she seemed to like that.

We played anytime we could. To use it wasn’t sex it was just having fun. I don’t think we ever had an orgasm but it sure felt good. I was heartbroken when Patty and her family moved to end our fun. However, we would meet again later in life.

That summer my cousin from Florida came to spend the summer with us. We always visited his parents and him each summer. His name was Scott, he was my father’s sister’s son. My mother was against him spending the summer as she thought he was a bad influence on me.

My father told her it was just because she didn’t like his sister. That we were just boys being boys. If it didn’t work out it would never happen again.

Scott and I spend the summer swimming, riding my dirt bikes, and playing in the woods. When swimming my mother would often be laying out on the patio. Scott was always checking her out if she was out with us.

My mother was 34 years old 5’5” blonde hair, deep blue eyes, and in shape as she ran and worked out regularly. My mother had 40DD tits with very shapely legs and an ass to die for.

While we were visiting at his house he had told me she was a MILF, Mother I’d Like to Fuck. At the time I didn’t even know what fuck was. He would look at her then but now he was staring at her all the time.

It was worst when she had her two-piece swimsuit on. Her big tits and that lovely butt were hardly covered by it. He was always waiting for her to bend over so he could see her tits or ass.

One day while swimming my mom came outside to layout on the swim deck. We were standing in waist-deep water as she walked to the deck. Her big breasts swaying and bouncing as she walked there.

Scott had his eyes following every step. His eyes grew large when she bent over to lay her towel down on the deck. Her tits were damn near hanging out her top. When she stood back up and turned around her hungry ass had sucked her bottoms up between her butt cheeks.

I whispered to Scott not to stare as mom would spank him if she caught him. He whispered back I wish she would spank my dick. He then swam to the other end of the pool.

Once there we hung onto the edge of the pool. Scott asked me if I had ever seen her naked or fucking my father. I told him no and asked what was fucking. Scott told me what it was and how our parents did the nasty. He told me all about watching his mom sucking and fucking his father.

He told me he often watches them fuck and his mother sucking dick. He told me his mom even took his father’s cum in her mouth. That his mom was a screamer in the bed.

I told him I have heard that from my mother. However, they keep the door shut so I didn’t know what they were doing. Scoot told me damn I was hoping we could watch them together.

Scott looked back at my mother. I saw him rubbing at the front of his trunks underwater. I looked back at my mother.