Uncles Sissy Bitch Part 1 by Juicy Lucy 1

Incest story: Uncles Sissy Bitch Part 1 by Juicy Lucy 1. David is a troubled boy who needs some fatherly guidance. His mom thinks his uncle can give him what he needs. She’s right! All characters are completely fictional and over 18

Genres: Fiction, Boy, Gay, Incest, Male Domination, Spanking, Toys, Transsexual, Young

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Incest story: Uncles Sissy Bitch Part 1 – Chapter 1 – 2

by Juicy Lucy 1

My name is David. I am 18 years old and just finishing high school. I live with my mom in a small apartment. We struggle a bit as my mom has had problems in the past and my dad’s not around and never has been. I don’t know anything about him my dad and I don’t want to.

Mom works really hard, holding down two jobs to make ends meet. She works in a local store during the day and a late night diner most evenings. It means that I fend for myself most of the time which is fine. Sometimes I have friends round but most of the time I’m on my own. I have no problem with that. I enjoy my own company and spend quite a bit of time online.

My mom really wants me to go to college nest year and it breaks my heart to see mom work so hard in an effort to get me there but it doesn’t look as if I’ll be able to attend next year.

We live at the end of a quiet street, our next door neighbours are Martyn and Diane and they have twin boys, Kevin and Robert who are two years older than me and both at college. We used to play together when we were young and age differences didn’t matter but as they started high school we drifted apart. They were total jocks too and both played in the football team and fucked their fair share of cheerleaders if you believed what you heard.

I’m a slightly built boy and quite small, I’m only 5ft 8” and weigh 125 lb soaking wet. I am however fit. I’m a good middle distance runner and workout to keep my body athletic.

I’m told I’m a good looking boy; cute is the word most often used to describe me by the other sex. I’ve had plenty of girlfriends although I’m still a virgin. I am attracted to girls and watch my fair share of online porn and jerk off the same as any 18 year old boy, all the time in other words.

I do however differ from the mainstream 18 year old male type though. I increasingly became aware that when I was watching porn I was imaging what it felt like to the girls I was watching. They all looked so sexy as they were penetrated. I found that I was imagining myself in their position when I fantasized. It wasn’t long before I was pushing, first a finger and then the handle of my hairbrush into my ass as I masturbated. I liked how it felt and my orgasms grew in intensity as I experimented in anal play.

Things gradually developed from there and one day when my mom was working I went through her closets and underwear. What I found shocked me a little. Buried at the bottom of her drawers was quite a selection of lingerie. She owned corsets and stockings and many different sexy thongs and panties with matching bras. I picked them up individually, feeling the softness and the silkiness and the texture of the lace. I found myself getting an erection and then I came across something that made me gasp.

Buried at the very bottom of this drawer was a rubber dildo! It was a good 8” long and heavy and had a suction cup at the base. I pulled it out and stared at it, my hard on throbbing in my pants.

I suddenly made my mind up and grabbed the lingerie and the dildo and rushed to my bedroom.

I had about two hours before my mom was due home and I quickly undressed and put my laptop on and went to my favourite porn site.

I stood naked and looked at the lingerie spread out on my bed. My mom was a petite woman, my friends told me she was hot, a milf even. She was only about an inch shorter then me and I thought that the underwear would probably fit.

I started simple and pulled on a white lacy thong. My 7” dick was so hard that it wouldn’t be contained by small triangle of material and so I just let it stick out of the top. I looked at myself in the mirror, turning slowly. I loved how my ass looked and decided to go for the matching hold up stockings and bra. I padded the bra out with tissue paper and admired myself in the mirror. I liked what I saw and my dick was throbbing, I pulled off the panties as I was scared I’d get precum on them and I tugged my cock and found that I was really close to cumming already. I wanted to try something sluttier so I pulled off the bra and stockings and held up red corset and fishnets. I struggled with the clasps on the corset and even more with the suspenders but eventually I saw a slutty fem boi looking back from the mirror.

I climbed onto my bed and assumed various positions, looking back over my shoulder as I got on all fours and pushed my ass up into the air. I loved how sexy, dirty and horny I felt. I grabbed the dildo and some moisturizer cream and lay back on the bed and watched some porn. I immediately imagined that it was me who was being fucked as I rubbed cream into my ass and over the dildo.

The rubber cock was considerably bigger than anything that had been in my ass and I pushed a finger into myself then added another as I tugged my dick. Suddenly an orgasm took me completely by surprise and I shuddered and groaned as I sprayed cum harder and further than I ever had before, splashing over my mom’s red corset.

When my orgasm subsided I quickly undressed and cleaned myself, my mom’s corset and the unused dildo and put it all back, carefully placing it all back exactly as I’d found it. The corset was still damp but I felt pretty safe that my mom wouldn’t be putting it on after a shift at the diner.

Things progressed quickly from there. As soon as my mom left for work I’d race for her lingerie drawer and climb into one her sexiest outfits. I fucked myself with her dildo which started as a an even mix of pleasure and pain but turned into pure ecstasy, especially when I stuck it to the leg of my bed or the bathroom wall so I could fuck myself doggy style. Once happy in lingerie I decided to go further and dressed in mom’s skirts and dresses. Her shoes were one size too small for me but I squeezed them on and tottered around painfully in her heels until eventually I could walk around quite well, albeit still painfully. I found cross dressing websites and studied how to apply makeup, learning how make myself quite pretty. I wanted to shave my body smooth too but I was afraid. I wasn’t very hairy anyway but how would I explain the lack of hair on my legs and under my arms if someone should notice?

It didn’t take long before I discovered sissy boi porn and hypnosis. Now whenever my mom was working in the evenings I would put on some lingerie and heels and watch hypnosis. I changed from a boy, cross-dressing and masturbating, to a filthy, cock crazed sissy slut. I took selfies of myself in lingerie and filmed myself fucking my pussy with the dildo. I craved cock and found myself looking at guys in a completely different way. I’d stare at crotches and imagine what size dicks men had. My friends noticed a change in me and because I always wanted to be alone when my mom was out I’d became a loner for the last few months of school.

I had never considered myself gay or even bi before but now I wanted to be fucked by a real man with a big hard cock. Unfortunately I was shy even with girls and had no idea how I’d approach a guy or even how to tell which guys would be interested. There were some obviously gay boys at school but they were all effeminate and I wanted a real man, butch and big to take control of me.

Soon that would all be taken out of my hands.

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Incest story: Uncles Sissy Bitch Part 1 – Chapter 2

by Juicy Lucy 1

One day I returned from school and found mom crying at the dining room table.

“Mom, what’s up?” I said, running to her and putting my arm around her.

“Oh, baby I’m so sorry.” She sobbed.

“Why, what’s the matter? What’s happened?” I asked.

“Baby, I can’t afford for you to go college and I’m so sorry your father wasn’t around.”

“Jeez Mom, don’t worry. It’ll be okay and screw dad, it’s his loss not mine.”

“I know Davy but you haven’t ever had any male role models and now no college….” She sobbed.

I calmed her down and dried her eyes, this was unusual for my mom, she was a strong woman and we’d already discussed the fact that I probably wouldn’t be able to attend college. I wondered what had brought this on.

“David. I’ve had an idea and called your uncle Bob. He’s going to help us.” Mom said, looking into my eyes.

Uncle Bob. That was my mom’s brother and we hardly ever saw him. He had been in prison and now worked construction. He lived about an hour away and I hadn’t seen him for years. My mom had told me that he was a shady character with some even shadier friends.

“Your uncle said that he can get you some work at weekends until school finishes and through summer too. Maybe you can earn some decent money and although you won’t make college this year, with your uncle’s help it’s a real possibility for next year.” She smiled at me with a trace of sadness.

How could I not agree when I saw she was so sad? I was to go and work construction with my uncle Bob. He’d pick me up every Friday night and return me home on Sunday evenings. I’d stay with him every weekend for the foreseeable future. I wondered what was in store for me and since tomorrow was Friday, I didn’t have long to wait.

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Also in this series:

• Uncles Sissy Bitch Part 1 - Chapter 3 - 4
• Uncles Sissy Bitch Part 1 - Chapter 5 - 6
• Uncles Sissy Bitch Part 1 - Chapter 7 - 8
• Uncles Sissy Bitch Part 1 - Chapter 9 - 10