Incest gay story: Uncles Sissy Bitch – Chap 3
by Juicy Lucy 1
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.
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.
—————-
Parent Post: Uncles Sissy Bitch. by Juicy Lucy 1
- Uncles Sissy Bitch - Chap 2
- Uncles Sissy Bitch - Chap 3
- Uncles Sissy Bitch - Chap 4
- Uncles Sissy Bitch - Chap 5