Incest gay story: Uncles Sissy Bitch. 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.
Incest gay story: Uncles Sissy Bitch – Chap 1
by Juicy Lucy 1
Genres: Fiction, Boy, Gay, Incest, Male Domination, Spanking, Toys, Transsexual, Young
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.
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.
When I was waiting for Uncle Bob to turn up the next day I was pretty nervous. We hadn’t seen each other for years and I really didn’t know him at all. I wondered what on earth I could do in construction. I saw a big red truck pull up outside and a large guy get out and walk toward our apartment. I answered the door when he knocked and was confronted by a big muscly guy. He was about 6ft 2” and barrel chested; his arms were the size of my legs and covered in tattoos. He peered down at me and held out his shovel sized hand.
“You must be David. Good to see you again.” He boomed.
My small hand disappeared as he closed his around it and shook it hard.
“You got your gear ready?” He asked and I nodded. “Go throw it in the truck and wait for me; I’ve just got to talk to your mom.
Mom appeared behind me and I gave her a quick hug, said goodbye and made my way to the truck throwing my bag in the back and climbing into the passenger seat.
I watched as mom and Bob talked on the doorstep, occasionally glancing back at me where I sat in Bob’s truck. Eventually he turned away and marched back to me and Mom waved sadly as we drove away.
As soon as we were out of sight Bob reached over and patted my leg.
“Your moms pretty worried about you kid.” He said, his hand lingering on my leg.
“She thinks you need to be around some strong male role models to straighten you out and I was the best she could do.” He laughed and squeezed my thigh gently. “Of course this has the added bonus of earning you some money for your college fund and if you perform well your uncle Bob will put in some extra too.”
I stared straight ahead and wondered why mom was suddenly worried about me. Surely she didn’t know about my secret. I was sure she would talk to me about it.
“Don’t worry kid, I’m not here to judge you in anyway, or change you if you don’t wanna be changed. You can work for me in one way or another; we’ll find out for sure what you are and maybe have some fun along the way. How does that sound?”
“Err, okay?” I said quietly, wondering what on earth Uncle Bob was talking about.
For the rest of the journey Uncle Bob quizzed me about my life in general, just general chit chat about my friends, my classes, my interests. He seemed very interested in whether I had a girlfriend or not.
When we arrived at his place I was pleasantly surprised. He had a little house at the end of a track with some land too. The house was a single storey cabin type affair with a porch all around it. There were a couple of outbuildings and I could see a car and a couple of motorcycles in various states of repair.
“Well, this is me. Let me show you around kid.” Uncle Bob said as he grabbed my bag and led me up the steps and pushed open the door.
Inside was a large open plan living room and kitchen. It was reasonably tidy but obvious that no woman lived here.
I was led down a corridor and shown my room which had a closet, single bed and chest of drawers.
Next to my room was Bobs and at the end of the corridor was the bathroom.
“Why don’t you get settled in and I’ll make us something to eat? Help yourself to a shower.” Uncle Bob said.
I sat down on the edge of my bed and thought about everything that had been said on the journey here. What did uncle Bob mean ‘I’m not here to judge’? I shook the thoughts from my head, I was probably being paranoid.
I decided to take a shower. Uncle Bob had kindly left me a towel on my bed and I took that and my washbag to the bathroom.
There was a tub with a showerhead on the wall and a shower curtain that ran around the tub on a metal pole. I turned on the water and closing the door went to lock it. No lock! Shit! Well I guess a guy on his own didn’t need a lock on his bathroom.
Feeling the water was a good temperature I quickly unchanged and stepped into the tub, drawing the curtain behind me.
I enjoyed the sensation of the hot water coursing over my skin and felt all my worries disappear as I soaped myself up and then rinsed.
Turning the water off I stepped out of the tub and went to grab my towel. It wasn’t there! I looked around the bathroom, my clothes were gone too! I frantically looked around the bathroom. Everything was gone!
What? I was sure I’d left them right here on the floor. What was going on?
I had to get back to my bedroom. I opened the door a crack and peered out. I could hear uncle Bob preparing food in the kitchen and humming. I made a dash for it and made it my bedroom and closed the door and leant back against it, dripping wet, heart pounding. When I looked around my room I gasped in shock.
My bed was abundant in women’s clothing. The closet was open and I could see dresses and tops hanging. On the bed were mini-skirts, more tops and shorts. On the floor were several pairs of heels some sneakers and some boots too.
The drawers of my chest of drawers were pulled out and I walked over and looked into them one by one. The top one contained panties and bras. I pulled out the tiny pieces of cloth and saw that there was a wide selection of panties ranging from white cotton ones to thongs of lace and silk. The next drawer down contained stockings and knee length socks. The stockings, like the panties varied in colour and transparency and style. Fishnets, opaque, hold ups, lace topped etc.
The next drawer had corsets, Basques and bustiers, all silky and lace.
The bottom drawer contained nighties, babydolls and chemises.
I searched for my own clothes but couldn’t find them anywhere. I started to panic as I realised that Uncle Bob and my mom might know my secret.
“So what do you think?”
I spun around and uncle Bob was in the doorway, leaning and filling the space with his large frame.
“Where, where are my clothes?” I stammered crossing my legs and trying to cover my penis.
“YOUR clothes are right here” he said indicating to the room in general with a sweep of his hand. “Your OLD clothes are safe with me. You’ll get them back when I take you home.”
I stared at him dumbfounded, almost shaking with fear and embarrassment.
“Listen” he continued “your mom knows what you’ve been doing. She noticed her things were not where she left them and noticed a change in your behaviour. She waited until you left for school and quickly got to your laptop before it went to sleep and she needed your password. You really should be more careful “he admonished me. “She found your pictures and went through your browsing history.”
I felt my face redden and I looked at my feet.
“She called me up and told me that you needed a man in your life to straighten you out, she showed me your pics.” He paused “I thought you look damn hot.”
I looked up at him and he was smiling at me.
“I do think you need a man in your life but not how your mom thinks. I think you should be allowed to be whatever you want to be so here’s the deal. You can stay with me at weekends, I have lots to show you and you can be free to embrace your feminine side, I promise we’ll have a lot of fun. There are conditions though. You have to do whatever I say though and you’ll only dress as a girl when you’re with me. If you decide you don’t want this then you can have your old clothes back and I’ll take you home right now. “
I stared at him not knowing what to say. Luckily he broke the silence.
“Now I’m going to finish preparing dinner and you can decide what you want to do. If you stay I want you to head back to the bathroom and shave yourself completely smooth. The only hair on your body I want to see is on your head. You’ll then put on some of these clothes, you can choose, and join me for some food and drink. We’ll just hang out tonight and watch a movie.
If on the other hand you decide you want to go back home then you can come and tell me and I’ll give you your old clothes and take you straight home.”
With that he turned away.
“You have an hour until dinner” he called over his shoulder and walked away, humming again.
I sat down heavily on my bed. My head was spinning. I picked up a gorgeous white corset and stared at it, four suspender belts hung from the bottom. I felt my cock twitch and I couldn’t help imagine how I’d look in it. I wanted this didn’t I? I’d go home on Sunday and wouldn’t have to come back if I didn’t want to.
I thought of my mom and what she must be thinking. She’d been through so much. I didn’t want to hurt her.
I tossed the corset onto the bed and stood, my mind made up. I headed for the door.
When I walked in to Uncle Bob he looked up and grinned.
I felt amazing. My body was completely smooth and after trying on several items of clothing, I had selected the least slutty thing I could find which wasn’t easy. Everything I tried looked at was ridiculously revealing and slutty. A couple of the tops actually had ‘SLUT’ or ‘SISSY BITCH’ emblazoned on them. I was wearing a tight fitting white halter top, some white cotton panties and short, pink towelling shorts. I had pulled on some pink converse ankle boots over my white knee high socks. My clit was so hard that I had had to tuck it the elasticated waistband of my shorts.
“Very nice” Uncle Bob said “Very nice indeed. You’ve made the right decision.”
We sat around his table and enjoyed a dinner of pasta and some fish that he had caught. He opened some wine and told me that I needed to learn how to drink and I found that I liked wine.
I didn’t get a chance to finish my glass, as soon as it was half empty, Uncle Bob would top it up and by the time we’d finished eating I could feel the affect. I was definitely feeling looser and more comfortable.
“So, do you like your things?” He asked.
“Oh yes. Thank you Uncle Bob” I replied.
“Now we can’t have you call me uncle Bob. I’d like you to call me daddy okay?”
I couldn’t see any harm in that and so I agreed.
“Now what should I call you? Have you thought about a nice girls name before?”
I had thought about before. “You can call me Lucy if you like?” I said.
“Lucy? Well okay then. Lucy it is. I shall always call you that except in front of your mother. Tomorrow I’m going to go and pick up some more things for you. Now I know you’re staying I can finish shopping for you. As you can see I’ve spent a lot of money on you so I hope you’ll be worth it.”
“Thank you…..daddy.” Actually, calling him that felt right.
“That’s okay sweetie, I want you to look always look beautiful for your daddy.” He said pouring more wine into my glass.
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Also in this series:
- Uncles Sissy Bitch - Chap 2
- Uncles Sissy Bitch - Chap 3
- Uncles Sissy Bitch - Chap 4
- Uncles Sissy Bitch - Chap 5