Uncles Sissy Bitch Part 1 free porn video

Chapter 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.

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.

“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.


Chapter 3

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.


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.

“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.


Chapter 5

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.

“Now your job while you’re here is to look after me. That’s the last time I’m cooking and I won’t be doing laundry nor doing dishes. That’s your job all the time you’re here okay.”

“Yes daddy.”

“You have to keep house, keep yourself beautiful and follow my instructions for making you a real girl. How does that sound?”

It sounded great. “Sounds good daddy” I grinned happily.

“Okay, you tidy up here and do the dishes. I’m going to watch some TV; you come and join me when you’re finished.”

I could see Uncle Bob lounging on the couch from where I stood at the sink. He was actually a good looking guy, so big and strong. I wondered why he was doing this for me. He hadn’t made any move toward me yet and I couldn’t believe a big strong handsome man like him would want me anyway. Perhaps he just wanted someone to cook and clean for him at weekends and wanted to help me too.
I decided that whatever he wanted was fine with me.

When I’d finished I walked into the lounge and went to sit on the spare couch.

“Sit next to me please Lucy” Uncle Bob asked patting the seat beside him.

I sat next him and he handed me my glass of wine. He also picked up a large reefer from an ashtray.

“Joint?” he asked.

I’d smoked marijuana with friends before like most teens.

“Sure” I giggled. Amazed and excited to be smoking and drinking with an adult.

Uncle Bob took a long drag on the joint and exhaling, passed it to me. Soon I was high and grinning stupidly. I took off my shoes and curled my legs up beside me on the couch between Uncle Bob and me.

“Let’s watch a movie shall we?” Uncle Bob asked.

I looked over at him and he held my gaze for a moment before picking up the remote control and pressing some buttons.

“What are we watching?” I asked.

“Some chick flick” he replied. “Something suitable for a little girl like you.” He chuckled.

We watched the film and smoked and drank and I got more and more wasted until I was giggling stupidly. I started to feel really comfortable with Uncle Bob, he laughed with me and made good humoured fun of how wasted I became and we chatted. He told me that he’d being going out tomorrow to buy me some wigs and makeup and asked if there was anything else I wanted. I shook my head and told him how grateful I was for all of the lovely clothes and how nice he was being.

I woke with a start. I was still on the couch next to daddy who was watching something else on the TV. I straightened myself up and as I did I noticed that something felt odd in my crotch.

“Good nap?” Uncle Bob asked, pressing a button the remote to switch turn off the TV.

I was still groggy and shook my head clear to see him smiling at me strangely. My hand went to my crotch and I felt something hard.

“Take a look” Uncle Bob said having seen my puzzled expression.

I pulled open the waistband of my shorts and peered inside. There was my clitty locked away in a stainless steel chastity cage. My eyes widened and then I looked back to daddy where he was waving a tiny key in his hand and grinning.
“Firstly, let me say what a good job you’ve done making yourself smooth. In the future we may go for waxing or electrolysis but for the time being I always want you smooth and will not be happy if you are not. I put the cage on you while you were passed out. You must get used to it as you’ll be wearing it all week when you’re not here and a lot of the time when you are. I’ll decide when you can cum okay?”

I stared at him as I tried to take in what was happening.

“OKAY?” Uncle Bob asked again, a sternness entering his voice that I hadn’t heard before.

“Err, yes daddy. Okay.” I stammered.

“Good girl. You’ll get used to it and even learn to love it.”

“What am I going to do about school?” I asked.

“Don’t worry. From now on you shall pee sitting down like a girl. Be careful and it’ll be okay. Now its late so let’s turn in shall we?”

Standing, he reached down and took my hand to pull me to my feet. As I walked toward the bedrooms he patted my bottom and squeezed a cheek.

“Fuck Lucy. You do have a great ass.”

“Thanks” I shyly replied.

When I reached my room I still wasn’t sure what was going to happen. I turned around.

“Goodnight daddy, thank you so much for everything.”

“Goodnight Lucy” he replied and leant in to me offering me his cheek to kiss. I pecked him quickly on the cheek and felt myself redden again. I quickly turned and entered my room, closing the door behind me.

Once safely inside I pulled off my clothes and examined my chastity cage. My clit pretty much filled it already and as I examined it, it tried to stiffen and I watched as it filled the cage and pressed against the bars as it tried to grow.
There was a ring between my balls and my groin and it connected to the cock cage with a small padlock locking the device in place.

I selected a deep red silk baby-doll nightie for my nightwear and made my way the bathroom. Just as I got there Uncle Bob was coming out. When he saw me he grinned from ear to ear.

“Wow, you look gorgeous Lucy.” He said as he held the door open for me.

“Thanks daddy” I beamed, feeling fantastic.
So ended my first day with Uncle Bob and my first day as Lucy.


Chapter 6[/b]

I woke up still feeling a little groggy from the drink and smoke of the previous night. I reached down and fondled my cage. I needed the bathroom so I headed there and urinated sitting down, washing the cage and my clit in the sink afterward.
I put on a pot of coffee and began to find everything for daddy’s breakfast. Luckily my mom’s long hours had turned me into a half decent cook. As I began getting things ready I realised that I was happy. I like the idea of having nothing to do but make myself pretty and look after someone. Girls had it made.

I heard a cough and then the toilet flush and I felt a wave of excitement as I began cooking eggs. I felt him behind me and then his arms reached around me and he hugged me, kissing my neck.
I could feel a large bulge between my ass cheeks and then he broke away.

“Good morning Lucy” he said, sliding into a seat at the table. “You’ve made an excellent start.”

“Good morning daddy” I beamed. “Coffee?”

“Sure”

I slid a steaming mug of fresh coffee over to him and carried on with the eggs.

“I’d like you to pick something for you wear today”

“Sure”

“After breakfast I have some laundry for you to do and then you can shower and get ready. I’ll lay out you something to wear on your bed.”

We finished breakfast together and once I’d put the laundry on I took a shower and made sure I was smooth for daddy. I just loved how soft my skin felt without all the horrible hair. I hoped we could do something so I wouldn’t have to keep shaving myself.
When I went back to my bedroom I could see some clothes laid out for me. There were black seamed stockings, topped with lace with matching lacy panties and bra. A short black pencil dress hung on a hanger from the closet. It had beautiful lace detail on the shoulders and hem.
Some 5” black platform heels were on the floor.

When I emerged from my bedroom I felt amazing. My cock cage wouldn’t fit inside my panties very well but other than that everything fit beautifully. I felt a million dollars as I looked at myself in the full length mirror. I really needed a wig and makeup to complete the look and some hips wouldn’t go amiss.

“Daddy” I called.

“In here” he replied, his voice coming from his bedroom.

I walked to his room and pushed open the door. He was just pulling on a white thong.

“I’m sorry” I said, looking away and blushing furiously.

Uncle Bob laughed. “Don’t you worry baby. I don’t mind at all.”

He whistled. “Wow, you look amazing Lucy.”

“Thank you” I replied.

I wanted to tell him that he did too. He made himself comfortable by arranging his package into the small cotton pouch that barely contained him. I’d only caught the tiniest glimpse of his dick as he pulled up his thong but I could safely say he wasn’t small! His large thighs were hairless as was his groin area and chest which was big and chiselled. He looked like one of those wrestlers or ultimate fighters. I felt my clit stir in its cage and I got butterfly’s in my tummy.

“Daddy, there is something I’d like you to get for me if you can?”

“What is it?”

“I’d like something to pad out my bras. I use tissue paper which is okay but not ideal”

Uncle Bob looked at me and my chest thoughtfully for a moment.

“Hmn, okay. I’ll ask in the shop when I go today.”

“Oh thank you daddy!” I cried and flung my arms around him forgetting he was half naked.

“Woah” He replied, clearly a little shocked. His strong arms hugged me as I pecked leant up and pecked his cheek. “I’m not promising anything but I’ll ask. Now go do the laundry while I get changed.”

I skipped away to do the laundry excited at the prospect of some more new feminine things coming for me later.


When Uncle Bob came and found me I was running a vacuum cleaner around, tottering in my heels.

“Leave that Lucy, I’m going out now and I want to get you ready” he said.

“Get me ready?” I frowned quizzically.

“Follow me”

I followed Uncle Bob out of the back door and to one of the outbuildings. He unlocked a door and we went inside.
I was taken aback at how nicely the outbuilding was inside. It was very clean and painted and had blinds in the windows. The floor was tiled and it had bright fluorescent lighting.
In the middle of the floor was a single wrought iron framed bed with a mattress on it. It was cover in a white sheet and had a couple of pillows thrown on it. At the head of the bed was a table with laptop on it which was plugged into a mains socket. There were various cupboards and sets of drawers around the room and a large leather couch against one wall.

“I’m going to leave you here while I go out Lucy. Please climb onto the bed; you can leave your heels on.”

I remembered that I had to do as I was told and obediently climbed onto the bed.

“Please lie on your tummy.”

I did as I was told. Uncle Bob picked up the pillows and told me to lift myself up. He then pushed the pillows under my tummy and told me to lie down again. My butt was now pushed into the air, I felt very exposed and wondered if Uncle Bob was looking up my dress. He moved behind me and moved the pillows about so my caged clit rested against the edge of them. I then heard him open some drawers before he grabbed and ankle and put what felt like a bracelet around it. My leg was then pulled out before he applied the same treatment to the other spreading my legs. I looked around and realise that he’d fitted a leather cuff to each ankle which had some nylon rope attached and now each leg was tied to a bed post.

“Daddy, what are you doing?” I enquired nervously. I wasn’t frightened. Uncle Bob had done nothing to make me feel threatened; in fact he’d made me feel special and appreciated.

“Don’t worry honey, I promise you’ll like this.”

He appeared at my head and secured two more leather cuffs around my wrists and the tied my arms outstretched so I was spread like a starfish on the bed. There was still a little wriggle room but not much.
Next he switched on the laptop and suddenly the sprung to life with a sissy hypno clip much like the ones I had been watching myself. Cocks filled the screen and a hypnotic voice began informing me what a slut I was and how much I wanted a real man and big cocks.
I blushed furiously.
Uncle Bob disappeared from my view and then he pulled my skirt up over my ass and bunched it around my waist. I could hear him sigh deeply. He pulled my panties to one side and then I felt his big rough hands on my buttocks and I held my breath as he stroked and squeezed them. No-one had ever touched my ass before. My clit twitched in its cage. Without warning Uncle Bob tore off my panties, ripping them easily making me cry out in surprise.

“Don’t worry, I’ll buy you some more” he grumbled.

He moved away again and I heard him rummage through the drawer again. Standing at my side he put something on the bed between my legs.

“Owwwwwwww!” I squealed as Uncle Bob brought the palm of his hand down on my buttock, spanking me. It was probably only a playful one but it still stung deliciously.

“Spanking will be a regular part of your training” he said spanking the other buttock making me cry out again.

Uncle Bob alternately spanked and caressed my butt before stopping and picking up whatever it was between my legs.

I jumped as something very cold was drizzled over my asshole and I guessed it was lube. My tummy did somersaults as I imagined what was coming next. Was uncle Bob going to fuck me?
Something hard rubbed the lube around my hole and then pushed. I felt my pussy open up as the object was slowly pushed into me.

“Ooh” I quietly groaned.

Suddenly my pussy lips closed around the object and I could feel the base between my ass cheeks.

“This is a beginners butt plug darling. We’ll gradually work our way up until you can take the biggest we can find. I’m going out to shop for you now. Stay here, watch the sissy porn and enjoy yourself. I shouldn’t be too long.”

With that, he slapped my ass again and left, locking the door behind him and I was left watching the sissy hypno, my pussy working the plug inside me.


When I heard the door unlock about three hours later I was as horny as I’d ever been. One sissy clip on the laptop had been replaced with another and then another. I stared at the screen as my clit pressed painfully against its chastity cage and I began to lust to suck and be fucked by a real man with a real cock.

“So, how are you doing?” Uncle Bob asked walking up to me.

I looked over to him and he must have seen something in my eyes as he chuckled.

“Ah, I see the hypno is working.”

He moved to me next my ass and he pulled gently at the plug opening up my pussy until the widest part of the plug was stretching my fuck hole. He held it there as I groaned. Suddenly his other hand came down sharply on my ass cheek making me squeal.

“You want cock don’t you?” he asked.

“Yes” I breathed.

“Say it” he demanded.

“I want cock” I repeated. I really meant it too. I badly wanted Uncle Bob to fuck me.

He let go of my plug and my body sucked it back into my body. Again he spanked me.

“What do you want to do with cock?” He pulled on the plug again.

“Oh fuck.” I moaned. “I want to suck cock, I want cum.”

“Do you want to be fucked?”

“Yes, yesssssssss.” I hissed. “I want to be fucked.”

The spanking continued with Uncle Bob asking me questions until he seemed satisfied and finally pulled on the plug until it slid all the way out.
Uncle Bob moved away and I really hoped he was undressing to climb onto the bed and fuck me. However, when he returned he drizzled more lube onto my pussy and I felt the familiar feeling of a butt plug being pushed into me. I grimaced as it stretched me more than the last one.

“Ow” I whimpered quietly as Uncle Bob pushed gently then pulled back and then pushed again, gently working it inside me.

Eventually I moaned as my pussy lips closed around the stem of the plug. It felt even better than the last one. This one seemed to fill my pussy and I could feel it touching spots the other just couldn’t reach.

“Good girl” Uncle Bob sighed and I felt my buttocks jiggle as he slapped my ass again. “I’m going to prepare some lunch. I’ll come and see how you’re getting on soon.”

With that he left again. Locking the door behind him.


An hour later he returned and I was going a little crazy. The sissy porn was taking its toll and I was wriggling and squirming on the bed as I moved the butt plug around inside me. I had mastered the technique of using my pussy muscle to push the plug out a little before relaxing and allowing it back into me and my clit was leaking precum at such a rate that it felt wet and slimy in its cage.

I looked up at him pleadingly when he came in.

“Daddy, I need cock, please.”

“Very good Lucy, you’re a natural slut aren’t you?” he laughed as he stood at my side.

Uncle Bob repeated a process I was going to come to know very well. He tugged on the plug and held it stretching me out as I moaned. He spanked me and allowed my body to suck it back in as I squealed and told him what a sissy slut I was and how much I wanted to be fucked.

When he stopped he asked if I was hungry. “I’ve got some food prepared if you’d like to stop?”

Food was the last thing on my mind and although it must have been after lunch I didn’t feel remotely hungry. I shook my head.

“Okay then Lucy. I am very impressed.” Uncle Bob said. “I think we’ll try the largest plug that I have.”

“Please fuck me daddy” I begged.

“All in good time sweetie, all in good time.”

The plug he pushed into me this time had a 6” circumference. (As I found out later) It wasn’t huge by any stretch of the imagination but to my untrained pussy it felt it.
I groaned as he worked it inside me. “Oh my god!” I moaned when my cunt finally took it all in and closed around it.

“How’s that?” He asked.

“Oh Jeez it feels so good.” I panted “So fucking good”

Again I was left.

By the time Uncle Bob returned I was a cock hungry mess. I had never felt so horny in all my life and I was actually dizzy with lust. I was writhing on the bed and there was a puddle of precum on the bed beneath me. As soon as he walked into the room I began begging and pleading for him to give me his cock, to let me suck him, to fuck me. Chuckling he moved to my side and began the process that I now knew quite well, spanking me and tugging on my plug as I squealed and moaned like a whore, all the time telling him how much I wanted cock, cum and how much I wanted to be fucked.

“So Lucy, have you had enough now?” Uncle Bob asked as he allowed my pussy to suck the butt plug back inside. “If you want more I can leave you again? Or maybe you’ve had enough now?”

“Please fuck me daddy, I need to be fucked soooooooo bad” I pleaded.

“No Lucy. I’ve got you right where I want you and you need to learn it’s not about your pleasure anymore. You have two choices. I can leave you a little longer to enjoy this plug or you can be released to have your lunch.”

Uncle Bob would later reveal to me that not giving in to my wishes at this time was the hardest thing he’d ever done.
I had no intention of eating lunch at this stage. I could think of only one thing, cock.

“Longer” I blurted.

“Oh my god Lucy. You are amazing. Let me show you what else we have in the drawer for your future amusement.”

Disappearing from sight again he reappeared with a box which he placed next to the laptop. The first thing he pulled out of it was a dildo almost identical to my mom’s.

“There, now you have one of your own”

Placing the dildo on the table he pulled out some anal beads and placed them next to the dildo. Two more dildos came out of the box they were longer than the first and seemed to have a hole in the bottom.

“These go with a toy you’re gonna love” Uncle Bob told me “but that’s for another day.”

The last thing to come out of box was an enormous black dildo. It was about 10” long and the girth was frightening, it looked to be a good 8” in circumference.

Right then I was so worked up I’d have been happy for him to use any or all of the toys on me, even the scary one, but slowly he put them all back in the box and put them away.

“Right, I’ll be back in an hour but then you have to stop okay? You have to eat. You can always get back on after that. Don’t forget I’ve been shopping for you and have some things you’re gonna love.”

I’d completely forgotten that he’d been out to get things for me. As he locked the door behind him I stared at the laptop once more and began moving my hips and using my pussy muscles to move the butt plug around inside me.


[b]Chapter 7

After Uncle Bob had released me from my wonderful torture I made one more futile attempt to entice him to give me his cock. I dropped to my knees in front of him and rubbed his crotch and tried to undo his pants. I couldn’t believe the change in me. I was so desperate and horny.
Uncle Bob laughed and brushed me away but not before I got to feel the large dick he was hiding behind that denim making me want him even more.

I was instructed to shower and wash my cage properly as it was dripping with precum. I was still plugged and he told to remove that one and wash it too.
I felt like I was a little out of mind, high almost. I didn’t know if it was the hypno or being kept at a peak of sexual excitement for so long but I felt strange and different. I was ready to do anything for cock now. I felt like I WAS the sissy slut I’d watched in all the video clips.

When I got out of the shower I had managed to calm down slightly and I realised how hungry I was. Dressed only in a robe I ate a quick lunch before Uncle Bob placed several large bags in front of me.
I grinned at him and tore into the first bag. Wigs! He had clearly spent lots of money again as there were 4 real hair wigs in the bag. Two were long; the hair would reach almost to the middle of my back. One was blonde and the other brunet. The other two were shorter. There was a platinum blonde one cut in a short bob and a jet black one, shoulder length. I loved them and began thanking him when he cut me off and signalled for me to open the other bags. He’d bought me lots of makeup and false eyelashes and nails.
There were also some breast forms! I tore open the packaging and felt the silicon in my hands. They were heavier than I expected. Uncle Bob had decided that a 34D was a suitable breast size for me.
They were amazing, they uses double sided tape to stick to me and had the most realistic nipples! I couldn’t wait to try them.
Uncle Bob told me to go and get changed and apply makeup as if we were going out to a nightclub.

A couple of hours later I appeared.

When Uncle Bob stared and then whistled at me I could have cried I was so happy. It had taken me a long time to get my makeup right and now I felt it was worth it.
I was wearing the blonde wig cut in a bob and an electric pink, tight fitting stretchy dress that finished halfway down my thighs. I decided to go bare legged and had painted my toenails and put on a pair of white strappy 4” heels. I had on a white thong that was only just big enough to hold my caged clit.
I was so pleased with my fake tits. The dress bulged beautifully in all the right places. The makeup, false nails and eyelashes really finished off my look perfectly and I really felt I looked like a slutty girl rather than a boy in drag.

“You look fucking hot babe” Uncle Bob said. “Let’s go out. First I need to do something.”

He took my hand and led me to the kitchen table. He gently bent me over it and pulled my dress up around my waist. Using his knee he parted my legs and then I felt him pull my panties to one side. His finger sought out my pussy and cold lube was rubbed around my hole. For one wonderful moment I thought he was going to fuck me but then I felt something cold and hard pressing at my cunt.

“This is a nice glass plug that I want you to wear when we go out sweetie” He told me as he pressed harder, stretching me open.
I groaned but it felt nice as it slid into me, opening me up. With a little effort, finally my cunt lips closed around the stem of the plug. Uncle Bob repositioned my panties and pulled down my dress.

“How does that feel?” he asked.

“Nice” I panted, as the very familiar feelings of lust resurfaced.

Walking with the plug in me felt amazing and made me walk with a feminine wiggle. I was grinning from ear to ear as he led me to his truck and starting the engine we drove away from the house.

“Where are we going daddy?” I asked

“Wait and see baby” he replied winking at me.

As we drove, the plug in my pussy kept me excited and I learned to love the bumps in the road. I closed my eyes and shuddered when Uncle Bob hit a pot hole in the road and I bounced in the seat next to him. When I opened my eyes he was grinning at me and he made sure to hit every bump and hole in the road after that.

I kept glancing at his crotch and I was just plucking up the courage to put my hand on his thigh when we pulled up outside a large supermarket and Uncle Bob killed the engine.

“Okay Lucy. You’re gonna do a little shopping for me okay?” He said, handing me list with about a dozen items on it.

“I want you to flirt with ALL the men in that store. I’ll reward you for getting results. If you can get asked out on a date or asked for your phone number that’ll be good. If you can get groped or touched, that’s even better. If you can get a guy out here to blow it’ll mean a huge reward.”

I stared at Uncle Bob.

“I’ll follow you in to see how you do.”

Oh my god! I was terrified. I wanted to please Uncle Bob. He’d been so nice to me and god knows how much money he’d spent on me already. My mind was full of dicks and cum from the hypno and ultimately I was so horny from my mornings training I wanted to try. Fuck it. No one knows me around here anyway and Uncle Bob wouldn’t let anything bad happen right?

I climbed out of the truck and straightened my dress, and then I walked across the lot toward the supermarket. I noticed people staring at me immediately. It was early afternoon and I was dressed like a hooker and walking oddly. A couple of middle aged women shot me filthy looks and tutted before turning away to bad mouth me. The guys however were another matter. They stared and I loved it. I began to walk with a bit more of a swagger, swinging what hips I had from side to side as I strutted, the plug causing wonderful sensations that made my knees weak.

The man parking the shopping carts headed in my direction pulling one behind him. “Cart ma’am?” He asked smiling widely.

He called me ‘Ma’am’! I beamed back at him and accepted the cart. As I thanked him I noticed him checking me out. His eyes moved up and down my body and he told me to find him if I needed any further help. He was probably in his early thirties, black, with a stubbly beard and tattoos and a pot belly. I immediately wondered how big his cock was and I made sure to give some extra wiggle as I walked away.

I wandered around the store, familiarizing myself with the layout and occasionally placing an item in my cart. There weren’t too many men in the store but I was pleased to notice that the ones that were, were definitely checking me out. I saw Uncle Bob every now and then, keeping an eye on me from a safe distance. After 30 mins or so I grew braver and when my little dress rode up my thighs, as it did as I walked and bent over, I stopped pulling it back down. Soon it was only just covering my ass and I knew if I bent over it would ride up further displaying a good quantity of cheek.

It wasn’t long before I noticed an older gentleman following me about the store and I decided to flash him. I made my way to the back of the store and waited for him to arrive. Sure enough his cart rattled into view and I bent down low keeping my legs straight to reach something from the bottom shelf. I felt my dress ride up my ass and I paused to make sure he got a good look before I straightened. My dress stayed up and I pretended to just notice and I turned to him, tugging my dress down a bit.

“Oopsy” I giggled looking at him.

The guy stared at me open mouthed as I smiled at him and turned away. I wondered if I could more out of this guy. He was older than I’d have liked. He was retired probably but not ancient.
I pretended to want something on the top shelf and the struggled to reach it. Suddenly I felt hot breath on my neck and the man’s body pressed against mine as he reached up around me.

“Let me help you with that my dear” he breathed.

I could feel his hard on bumping between my ass cheeks and he pressed it against me. He dropped the item into my cart and then his hands were on me. They slowly ran down my body from under my arms to ass.

“You are such a naughty little tease” he whispered.

Lifting my dress around my waist he squeezed and kneaded my ass. My eyes darted around as I looked around the store, my heart hammering in my chest but we were well hidden and I closed my eyes and moaned quietly.
I was scared he’d reach around and find my caged clit but he seemed satisfied with groping my ass. Suddenly he pulled away.

“Thank you dear. I’m going to go home and surprise my wife now.”

I turned around breathless and excited and pulled my dress down again. The man was walking away. Oh my god. Had I really just done that? Could I go further? I found that I was ridiculously horny and turned on. I was behaving completely out of character and I didn’t care.
I looked around and satisfied that we hadn’t been spotted continued with my shopping. I tried the same thing a couple more times and although I got plenty of stares and smiles but no-one else made a move on me.
Uncle Bob finally stopped me.

“Very good Lucy, finish getting the things on the list and meet me back in the truck” he whispered as he walked past me.

I did as instructed, quickly gathering the rest of my shopping, smiling sweetly at the check-out girl as she bagged my groceries and shot me dirty looks. As I was leaving the store the cart guy approached me.

“Hey baby. I’ve been checking you out. Why don’t ya give me your cell number so we can get together sometime?”

Without hesitating I gave him my cell number and grinned as he scrambled to get it into his phone before he forgot it. Laughing, I made my way back to the truck.

Climbing into the truck I couldn’t wait to tell Uncle Bob how I’d done.

“Did you see daddy?!” I said excitedly as I climbed in.

“I saw baby “he replied “you did very well for a first time” I saw you getting groped by that old man. Did you have fun?”

“Yes daddy, all the men stared at me and I felt so pretty and sexy”

I could barely get the words out fast enough as I told daddy about the cart guy.

“That’s great Lucy. I want you to get him to send you a picture of his cock.”

As if on cue my phone chimed. I took it out of my purse and saw I had a message from a new number.
Hey pretty girl, this is Rufus from the store. When can we meet?

I read it to Uncle Bob as he pulled away. He smiled and told me not to reply until later as I had to learn not to be too keen. Like a girl.

Uncle Bob was clearly very happy with me. He told me that I’d be shopping there regularly and wanted me to dress inappropriately every time. He rubbed his crotch and I could see a large bulge. I wanted him so badly, like I’d never wanted anything this much.
I reached over tentatively and placed my hand on his thigh. He didn’t move it so I slid it up and down and when he didn’t protest again I placed it on his crotch. I could feel he was hard and as I squeezed I felt it throb. Slowly I moved my hand about, massaging his dick and then I felt for his zipper and tugged it down before locating the button and pulling open his fly. Uncle Bob shifted in his seat and pulled open his pants some more, giving me the green light. With both hands I reached over tugged his cock out of his pants. I stared.

His cock was beautiful, I hadn’t a chance to look at it properly but now I could admire it in all its glory. There are ugly cocks and there are pretty cocks and this one definitely fell into the second category. It was a little over 8” long and thick. It curved beautifully up toward Uncle Bob’s stomach and I could see the circumcised head glistened with precum. Without realising it I licked my lips.

“Oh daddy, you’re sooooo fucking big” I murmured.

Uncle Bob chuckled. “You can stroke it little girl. This is your reward for a job well done in the store.”

I was a little disappointed that I wasn’t allowed to suck it but at least I was going to get to touch another man’s cock at long last, and what a cock!

I reached over and gently closed my hand around the shaft. My fingers couldn’t meet and although I did have small hands it was still a girthy dick. I felt the velvet skin move over the rock hard core as I gently stroked and I jumped when it bobbed in my hand making Uncle Bob laugh.
I began jerking him off slowly and then I used my finger tips on the glans, remembering what felt good to me. I alternated between gripping him firmly and pulling down hard and being gentle and tender, working out what gave him most pleasure and I soon realised he liked to be handled firmly.
I pumped his cock hard.

“Does that feel nice Daddy?” I asked

Uncle Bob grunted the affirmative. His head went back against the headrest of the truck and I knew he’d close his eyes if he could. His cock throbbed and twitched in my hand and then twitched and suddenly he quickly pushed my hand away.

“Fuck” he laughed “I almost came then baby. That’s enough for now. We’re nearly home.”

I smiled happily unable to take my eyes off his dick as it slowly softened. My own however remained hard, as it had been all day, pushing hard against its cage. I continued to wiggle on the plug which felt almost part of me now, bumping delightfully at my insides.


Chapter 8

Once inside the house Uncle Bob took my phone and had me lift up my dress and pose for a few sexy pics and then suggested I got changed into something comfortable when we got inside. When I undressed I saw my panties were a mess. I’d leaked so much precum that my cage required a good clean. I told Uncle Bob and he unlocked me so I could clean the cage properly under strict instruction NOT to touch myself. It was such sweet relief to be uncaged and I could see marks all over my clitty where the bars had been pressing.
When he saw my clit he said that it would be a good idea to spend a little time unlocked and unplugged.
I pulled some tiny pink flannel shorts and a tight white t shirt over my fake titties. I just loved having some shape to my body and knew for sure that I wanted real implants now.

I made Uncle Bob’s dinner as he drank a couple of beers and made some phone calls and then disappeared to one of the outbuildings for a while. I felt so at home and happy here and was dreading having to go back home to mom the next day.

After we’d eaten and I’d washed the dishes and tidied up Uncle Bob told me we’d watch a film tonight and gestured for me to join him on the couch.

Teens love huge cocks the title on the screen said and I smiled as I realised we were going to watch porn.
Pretty quickly the action started and a young girl who said she was 18 was introduced to a guy who immediately began licking her pussy.
My cock, which had gone limp, grew very hard again and the tiny flannel shorts were useless at covering it. I shifted in my seat and used my hands to cover my hard on.

We watched the film in silence for a while. The guy in the film stood up and the girl knelt before him she pulled down his pants and an enormous cock sprung free. It was really huge and thick, easily 10 inches long. The girl put her forearm up to it as a comparison and it was the same.

“Woah. That it is one big dick huh?” Uncle Bob said.

Suddenly his hand was on my thigh and he moved it over my skin.

“Mnmmmm, lovely and smooth. “ He murmured and pulled at my leg spreading them a little.

“I bet you’d love to be her wouldn’t you?” He said running his hand up and down my inner thigh.

The girl was doing her best to take the massive cock into her mouth. My clit throbbed.

I looked at Uncle Bob and he grinned back at me suddenly moving his hand and pushing mine out of the way as he placed his on my crotch and squeezing.

I couldn’t help a small moan escaping as my clit twitched in my shorts.

His hand took mine. “Come here” he commanded and pulled me toward him until I was right next to him. He took one of my legs and pulled it over his so mine were effectively spread. I made a feeble attempt to cover my hard-on with my hands.

We carried on watching the film, the girl was on all fours and moaning about big the cock that was sliding slowly into her pussy.

I was so horny and I squeezed my clit through my shorts.

“Looks so good doesn’t it?” Uncle Bob asked, referring to the action on the TV.

“Fuck yeah” I replied.

“You’d like to feel that cock stretching your pussy wouldn’t you Lucy?”

“Yes daddy” I panted.

“Take off your shorts”

I peeled off my little flannel shorts and kicked them off to reveal little white cotton panties.

“Panties too”

I attempted to cover my hard clit as I removed my underwear and sat back down next to Uncle Bob but it was no use.

Uncle Bob pulled my leg over his again his left hand stroked my thigh as his right hand rubbed his crotch.

“Stroke your clit for daddy” he said “slowly. If you cum I’ll be cross”

I did as asked, slowly masturbating as I watched the porn on the TV. My clit felt so hard and was big, purple and angry looking.
Uncle Bob’s hand moved along the underneath of my thigh and I shuddered at his light touch. I wanted him to fuck me like I’d never wanted anything before.
Suddenly Uncle Bob slipped of the couch and knelt in front of me. He grabbed me and pulled me to the edge of the couch and pushed me back. He pushed my legs back so I was lying on my back.

“Hold your legs” he commanded.

My pussy was exposed to him and he kissed the underside of my legs and licked along them before flicking his tongue against my cunt.
Soon he was lapping at me hard and pushing his tongue inside me and then I felt his finger probing and pushing as I hugged my legs open for him.

“Ohhhhhhh daddy” I moaned as he pushed a finger inside me.

I watched the girl on the screen being fucked as Uncle Bob finger fucked me, occasionally pulling his finger out to lick me some more.

“Oh my god” I groaned as he added another finger and slowly fucked me with two.

“Does that feel good baby?” he asked me.

“Oooh daddy. It feels sooooo nice.”

My clit was leaking so much precum it was pooling on my tummy. I wanted him to fuck me so badly.

Suddenly the fingers were withdrawn.

“That’s enough for now. You ever sucked cock before Lucy?”

I shook my head.

“Well, I think it’s time you started” Uncle Bob chuckled as he pulled himself up.

I released my legs and sat myself up as Uncle Bob stood in front of me.

“Don’t rush now. Be seductive.”

I crawled from the couch and knelt in front of him. I reached up and rubbed the bulge in his crotch, moving my hand along the outline of his cock, my eyes staring up at him all the time. Undoing his pants I pulled them open and reached inside. I grasped his shaft and pulled out his dick letting it go once it was free of its confines and allowing it to spring free.
Once again I stared at the big cock swinging in front of me. It was hard and it bobbed as blood was pumped into it.
I gingerly reached out and held it at the base and moved my head toward it. I’d never had a cock in my mouth but I’d watched enough film of it and had practised on my dildo. I knew what I was going to do.

Sticking out my tongue I licked slowly up the underside of his shaft and back down to his balls a few times. It didn’t taste of anything until I got to his glans and then there was the slight salty taste of his precum. I took the tip of his dick into my mouth and massaged the underside with my tongue and then stretching my mouth open wide pushed my head forwards to take him into my mouth. Our eyes never left each other as I took him to the back of my throat and then pulled back before pushing forwards again.
I took my hands away and held them behind my back and began bobbing my head, fucking his cock with my mouth. I just loved how it felt