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my uncles little sissy  

realkimmikane 53T
1 posts
8/5/2020 7:01 am
my uncles little sissy

My name is john. 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 .
Mom works really hard, holding down two jobs 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 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 go college nest year and it breaks my heart see mom work so hard in an effort get there but it doesn’t look as if I’ll be able 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 and both at college. We used 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 5 lb soaking wet. I am however fit. I’m a good middle distance runner and workout keep my body athletic.
I’m told I’m a good looking boy; cute is the word most often used to describe by the other sex. I’ve had plenty of girlfriends although I’m still a virgin. I am attracted girls and watch my fair share of online porn and jerk off the same as any 18 year old boy, 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 the girls I was watching. They 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 .
Things gradually developed from there and one day when my mom was working I went through her closets and underwear. What I found shocked 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 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.

Chapter 2

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.

“, baby I’m so sorry.” She sobbed.

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

“Baby, I can’t afford for you 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 attend college. I wondered what had brought this on.

“David. I’ve had an idea and called your uncle Bob. He’s going 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 that he was a shady character with some even shadier friends.

“Your uncle said that he ca“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 every Friday night and return home Sunday evenings. I’d stay with him every weekend for the foreseeable future. I wondered what was in store for and since tomorrow was Friday, I didn’t have long to wait.

Chapter 3

When I was waiting for Uncle Bob to turn 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 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<b> gear </font></b>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 k**.” 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 k**, 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 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 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 . Let show you around k**.” Uncle Bob said as he grabbed my bag and led 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 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 eat? Help yourself a shower.” Uncle Bob said.

I sat down the edge of my bed and thought about everything that had been said the journey here. What did uncle Bob mean ‘I’m not here judge’? I shook the thoughts from my head, I was probably being paranoid.
I decided take a shower. Uncle Bob had kindly left a towel my bed and I took that and my washbag to the bathroom.
There was a tub with a showerhead the wall and a shower curtain that ran around the tub a metal pole. I turned the water and closing the door went lock it. No lock! Shit! Well I guess a guy his own didn’t need a lock his bathroom.
Feeling the water was a good temperature I quickly unchanged and stepped into the tub, drawing the curtain behind .
I enjoyed the sensation of the hot water coursing over my skin and felt my worries disappear as I soaped myself and then rinsed.
Turning the water off I stepped out of the tub and went 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.

Chapter 4

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.


LacyLovedoll 54T
5 posts
9/29/2020 5:57 am

Very good, this deserves a sequel. Reminds me of my situation at that age and dressing up in my mom's lingerie. Unfortunately I didn't have an uncle to train me as his weekend sissy slut though.


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