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. Her tits were all shiny with her lotion on them. You could see the sides of her big tits as her top was a little small.

I was soon rubbing my cock through my trunks. I was looking at her tits too. I was thinking about when I used to play with Patty in the woods. I was wishing I could see my mother pissing.

My mother had sunglasses on and she lowered them a bit down her nose. She told me to be a dear and go fix her a drink. I often fixed both my parent’s drinks.

I started to swim toward her to get out but then turned back to the other edge of the pool. I didn’t want her to see the boner I had in my pants. I told Scott I would be back or he could come with me.

Scott joined me and we wiped off as we walked into the house I noticed he had a boner in his trunks. Once Inside I got a glass and put some ice in it. I make her a screwdriver her favorite drink.

“Here let me stir it,” Scott said smiling.

I handed him the glass. He told me to hold it. Scott pulled his dick from his trunks. It was still hard but was only 4 or five inches and not as thick as mine.

Scott used his dick to stir mom’s drink. My dick got hard again seeing his cock. He stirred it a few times in her drink. Then took the glass from me.

“You stir it too,” Scott said.

I took my dick out and shoved it into the glass. My cock was 6 inches, thick and still growing. Scott told me I had a nice cock as I used it in my mother’s drink. At least our dicks had lost their boner with sticking them in her iced filled drink.

We went back to mom and I handed her the drink. She sat up and her tits bounced. Her nipples were hard poking from her top. She took the glass and sniffed it.

I thought we were busted. She looked at us both then handed the glass back to me. She told me I could have a small sip. I told a sip and gave it back to my mother.

“Thanks, mom your the greatest,” I said smiling.

“You want a sip?” Mom asked Scott.

He shook his head no. Mom took a big drink then placed it beside her. She rolled over to lie on her back.

When she did most of her ass was showing as her swim bottoms were buried in her ass crack. Her butt cheeks were so lovely. I wondered if she rubbed butts with my father.

“You boys go ride motorbikes or something so your not staring at my ass,” mom said smiling at me.

Scott and I went back to my room to change into motorbike clothes. In my room all Scott could talk about was my mother’s ass. When he removed his trunks he was rock hard.

“How did my dick taste,” Scott asked laughing.

I laughed as I replied,” Like a screwdriver.”

“I thought you said your mom would spank us if she caught us looking,” Scott asked.

“She normally yells at me that it is not polite to stare then I would get spanked later, “ I replied.

“Does she spank you or did his uncle?” Scott asked.

“Mom always did with her bare hand on my bare butt as I laid across her lap,” I replied.

He asked me how did she do it. I told him she rubbed my ass then smacked me. She would rub again then spank. She kept doing it that way till she told me I had learned a lesson.

Those are love taps, my father uses the belt on me when I am in trouble Scott told me. He asked if I ever popped a boner in her lap. I told him, no but it would feel all tingly down there.

“You got me all tingly down there,” Scott said showing me his throbbing dick laughing.

I told him I had some other things to tell him once dressed and in the woods. We put on motorbike riding gear and grabbed two helmets. We went to the backyard bike barn and got the bikes

Scott wanted to ride past mom but I told him we were going the other way. We rode around for about a half-hour then I told him to follow me. I took him to the spot Patty and I played. I told Scott about Patty and what we did in the woods.

I told him about watching her pee. About the red hair on her private part. How her tits were just coming in but they puffy and had big nipples on them. I told him about rubbing butts and that Patty was always grabbing my cock.

Scott reached over and grabbed my boner in my pants.

“Like this?” Scott asked grabbing my dick.

“Yes but we were naked,” I replied.

“Then let’s get naked no one is going to see us out here,” Scott said.

We took all our clothes off until we both were buck naked. Scott asked me if I had ever jacked off. I shook my head no. I only knew to rub my cock with my palm.

Scott told me to watch him. I watched him as he wrapped his hand around his hard cock. He started to move his hand back and forth on his hard cock.

I wrapped my hand around my cock. I did what he was doing. It felt so much better than just using the palm of my hand. As we played I couldn’t take my eyes off his cock.

I noticed this clear fluid as it formed at his pee hole. Scott took his finger wiped at it then licked it from his finger. In a few minutes mine was oozing the same fluid.

I tasted it and I thought it tasted good. We both kept pulling on our cocks. We told each other how wonderful it felt.

I suddenly felt weak in my knees. I slipped and fell toward Scott. My dick went against his. We started to rub our dicks together. Scott took both our dicks in his hand they were sort of on top of each other and he jacked them off together.

Scott removed his hand from our dicks. He told me he wanted to show what his mom loved doing to his father. Scott got on his knees in from of me. He reached up and took my cock into his hand.

“I do this with boys back home all the time, we suck each other I think you will enjoy it,” Scott said.

Scott started to pump and squeeze my cock lightly with his hand wrapped around it. He told me he had learned watching his mom suck his father.

Scott pumped my cock until that clear fluid oozed from my pee-hole. He moved his mouth to my cock. He kissed my pee-hole like mom kissed my cheek good night.

He then opened his mouth taking my dick inside of his mouth. He started to move his mouth up and down my cock. He only would take about half of it into his mouth before running it back up to the head of my dick.

Scott worked into a steady rhythm on my dick. While doing so he was sucking it on the upstroke. I moaned softly as this felt better than my palm or jacking my cock off as he had shown me.

Scott did this for about ten minutes. I got that weak feeling in my legs. I never felt anything like this. Suddenly I felt my cock throb and it seemed to grow bigger.

I moaned loudly as Scott sucked hard on it. My eyes closed as I got the feeling I was going to pee. About a minute later Scott removed his mouth from my dick.

My dick was wet and still throbbing. Scott stood up and brought his face to mine he opened his mouth wide and I saw a small pool of that clear stuff inside his mouth.

Scott put his arms around me closing his mouth. He kissed my lips with his. He slipped his tongue between my lips. His tongue slipped into my mouth and they rubbed in our mouth. I could taste that fluid from my cock as he did. He broke his kiss and unwrapped his arms from around me.

“Well, what did you think?” Scott asked smiling.

“That felt fucking great much better than anything I ever felt,” I replied.

Scott told me that kissing at the end he added himself. He had seen his parents doing that after his mom sucked his dad. He told me he found me very attractive and had wanted to kiss me.

“My turn,” I yelled dropping to my knees in front of him.

I played with his cock pumping and squeezing it as he did. The only difference was his cock was leaking vast amounts of that clear fluid. I skipped kissing his dickhead. I took his cock into my mouth.

I took all of it in my mouth. I start to run my mouth up and down it while sucking on it. Scott was moaning in less than a few minutes.

“Ahhhh John going to cum,” Scott yelled.

I just kept moving my mouth up and down over his cock. I felt my mouth filling with fluid. I started to gag and removed my mouth. That clear fluid ran from my mouth. It ran down my chin dripping from it.

“Damn I had never shot off like that before,” Scott said.

I wiped my wet lips off with my hand as I stood back up. Scott licked my chin then kissed me like before. He danced his tongue in my mouth as he did.

I had my first cum that day. My first kiss and I had also sucked my first dick. The only thing that would have made it better was if Scott didn’t cum so quickly. We sucked each other again and I lasted for 15 or 20 minutes. The second time Scott blew his cum in less than 2 minutes.

He told me I sucked too good and he couldn’t hold it. He told me that he had been wanting to do these games with me for a long time. However, he was unsure if I would play.

We played for the next few hours. We even rubbed butts while jacking each other off. Scott had me pee on his cock and all over him as well.

We played all the time from morning till night. I even sucked him in my bedroom as we slept in there together. I always made sure my bedroom door was locked so we wouldn’t be caught.

It seemed our cocks got bigger as we played through Summer. Scot was really into kissing me. I was really into sucking him and tasting his cum. By the middle of July. We had tried a new game.

Scott told me he had watched his father fuck his mom up her ass with his cock. He told me we needed some Vaseline to make our cocks slippery. I found some in our bathroom.

I let him do me first. He had told me to get on my hands and knees like a dog. He told me that was how his parents did it. He lubed up his dick and shoved it in. It hurt at first as he slipped the head of his dick up my asshole.

Scott grabbed my hips and butt fucked me for maybe 5 minutes before he moaned telling me he was going to cum. I could even feel his cock pumping that clear fluid up into me.

I did him next. My cock being larger took some time to put up his ass. It also took longer for him to get used to it. I butt fucked him for at least 20 minutes before I blew up his asshole.

In time Scott was able to last longer and I liked his cock up my asshole. It didn’t even hurt any longer. Plus he would blast that fluid up my ass. He shot twice as much as I would. However, he was quick on the draw as they say. We even told each other that we loved the other. Just like our parents told each other.

We also would still swim and check my mother out. But not as much as we enjoyed being with each other. Mom even seemed mad about us not being around her.

More than a few times she would see us leaving on our dirt bikes. She would wave us over to herself. She would tell us it is too hot to be in those riding outfits and that we should join her at the pool instead.

Most of the time we told her we were fine. Mom would lower her sunglasses giving us that look. She even asked us more than a few times if we were up to no good while riding those bikes.

“No mom just having fun riding, that is all,” I would reply.

One day we got up and got dressed to ride. We looked for mom in the house and figured she was at the pool. But when we looked there she wasn’t so I figured she went to town.

We dressed in our gear and went to the bike barn. Mom was inside we both stopped dead in our tracks. Mom was standing next to the bikes in the barn. She was dressed in motor cross gear except for the chest plates we had on. Instead, she had this tank top covering her breasts.

We both stared at her as you could see the tops of her huge breasts. Her nipples were hard and poking out of her tank top. Those motor cross pants were tight on that hot ass of hers. I almost blew in my pants when she bent over in front of us.

“l hope you boys don’t mind me tagging alone today I felt like a ride this morning,” my mother said smiling at us.

I couldn’t tell her no you can’t as we wouldn’t be able to have sex. So I told her it was fine. Mom put her helmet over her long blonde hair. She kick-started her bike. Her tits bounced as she did. Mom revved up her bike then told us to catch her if we could.

“If you catch and touch me I will give you a surprise, I call it moto tag ” mom said before racing off.

Now my mother could ride her bike as well as my father. He had taught her well. Her tits would be bouncing and swaying. She would allow us to get close enough to see that before speeding off from us.

We must have chased her for two hours. Never getting close enough to touch her. Just close enough to those tits or her hot ass in those tight pants. She would even stop and wait till we were in reach before speeding off. Both Scott and I crashed our bikes regularly trying to catch her and touch her.

Mom finally drove her bike to the bike barn. We followed her. As she parked her bike we both flopped our bikes and ran to her and touched her.

“We caught you where is our surprise,” Scott and I yelled together.

Mom laughed telling us the game was over before we touched her. We told her that was unfair. Mom removed her helmet and fluffed her long hair.

“Well, you boys were good sports so,” mom said smiling.

Mom tossed her helmet to the ground. Now you boys don’t tell anyone about this. Mom’s hand went to her tank top. She lifted it over her head taking it off. My mom stood there in front of us with her breasts hanging out for us to see.

She shook them as we stared at them. Her nipples were twice as hard as when poking through her shirt. She only stayed like that for a couple of minutes. But it had our cocks trying to bust out of our motor cross pants.

Mom put her tank top back on. She told us to remember not a word about this to anyone. We promised we wouldn’t tell. Mom came to me and rubbed her hand on my face then kissed me on my cheek.

“I am off to shower and you boys put the bikes away,” mom said walking away.

I watched her shaking that hot ass in those tight motocross pants. Her cheeks seemed to bounce individually as she walked. She even looked at me winking.

I watched her walk into the house. I turned around to find Scott pulling down his motocross pants. He fished his cock out and was jacking it. I went to him and dropped to my knees.

I sucked him till he blew in my mouth. Scott kissed me as I stood up. He told me my mom was hot but I was hotter as I swapped his cum with him.

That made me feel good. It also made me feel that I was gay. Something that I wasn’t sure of till then. It also confused me a bit. However, it didn’t linger in my mind and I pushed it from my mind. After all, all I had to do was hide my being gay from everyone especially my parents.

That night while my father was cooking steaks outside he asked us what we had done today. We told him we had played moto tag with mom. He sort of looked to mom giving her the eye. Apparently, he knew what it was.

“Don’t worry dear they didn’t catch me,” mom said laughing.

“You boys missed out on a hell of a prize,” my father told us laughing.

For the rest of the summer, Scott and I played. Mom would join us from time to time but fully dressed in her gear if we played motocross tag. She told us she would give us the big prize if we caught her. We never got that prize or ever came close.

My body changed quickly during that summer. My dick had grown as well. We had measured them one day mine was 7 and 3/4 inches veiny and fat. Scott was about 6 inches and still thin. He had told me many times how lovely I was during this time which only made me love him more.

By the time Summer was coming to an end. I was pretty sure I was gay and in love with Scott my cousin. Our last night together was the best and the worst day of my life up till then. That night Scott and I played all night long.

We sucked and fucked all night long. In the early morning, we were still having sex. I was sucking his cock as he laid in my bed. He was jacking mine. By now I had told Scott that I loved him many times and he had told me he loved me.

I could also tell when Scott was going to cum. He had become a little better at controlling his quick cum as well. As I sucked him I sensed he was going to cum. I removed my mouth from his and pulled on his cock with my hand.

We both blew a nut together. It was flying over us both. We kissed as we told each other we love the other.

“What the hell are you boys doing,” my mother screamed.

We both told her nothing as we got dressed quickly. My mother told us bull shit she had seen everything. I had forgotten to lock the door. She told Scott to get his ass to the guest bedroom.

As Scott left my mother came to me. She slapped me hard across my face. She screamed and yelled at me. She told me I had ruined my life and hers as well. That I was was grounded for life.

“How dare you be gay,” my mother screamed crying. “You just wait till your father gets home.” She added.

My father was away on business and would be home tomorrow night. I was confined to my room. When Scott’s parents arrived I heard my mom yelling about this all being Scott’s fault. That he was never welcomed here again.

I also knew Scott would get beat with the belt from his father. Scott and his parents left before my father got home. My mom had told them she couldn’t stand the sight of him and to get him the hell out of here.

They all left and I would never see him again. When my father came home I got beat with his belt as well. It was the first and last time he would ever use it on me. Please leave your comments

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