Katie's Sissy Adventures Ch. 04

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The continuing adventures of a chastised sissy bottom.
1.6k words
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Part 4 of the 7 part series

Updated 06/11/2023
Created 09/01/2022
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I took a day to rest my well used pussy and deciding I couldn't wait for my new plug to come in. I went to an adult store after work to try and find one big enough to stay put.

Looking around the store, which was busier than I had hoped, I couldn't see anything displayed that would work. I noticed some larger ones on the shelf behind the counter and after pacing around a bit I worked up the courage to ask the older chubby brunette girl at the till if I could see them.

The store wasn't very big and I noticed a few people look my way but I just stayed focused and with her help managed to find a plug that was 3" and flared down to 1.75" with a wide bottom so it couldn't go too deep. I also bought 2 huge pump top bottles of lube and a cute brunette with purple highlights wig so by the time I confidently walked out of there, looking the other patrons in the eye with a mischievous grin, everyone knew what I was into and it turned me on like crazy.

As soon as I got home I got smooth again and got ready for my new plug. After a little lube I worked it slowly into my still tender sissy pussy and watched some bbc hypno till I woke up to my alarm the next morning still plugged and my panties sticky with sissy cum.

I wore my plug almost constantly that week. I messaged Dale hoping he would come by but he had a guest for a few days so I had to wait till they left before we could play. My pussy felt healed after a few days, no more discomfort but it did seem bigger, my panties felt like they didn't cover it anymore when my plug was out and I loved how easily my plug went in and out after a few days.

That friday as I left work I messaged Dale and he said he couldn't be free till the next morning. I arrived at home to find my fuck machine at my front door and my other butt plugs. Having been caged almost uninterrupted for almost 5 weeks I barely noticed it anymore. I only touched it to wash or tuck it into my panties but still loved seeing it dangling there dribbling cum while I rode my toys or took a fat cock.

I set up my fuck machine to fuck me in missionary on my bed. I set up a towel and attached my 13" 3" thick BBC dildo. I rode my smaller BBC dildo first for 10 min before lying back and positioning myself on that huge dong so it was buried in me at the max depth of my machine. I grabbed the controller and turned it on low, feeling it slide slowly out about 6" then back it slowly till it pushed against my p-spot. I slowly increased the speed and when I got to around half way it was hitting just right.

I put down the controller and pulled my legs into my chest to allow it even deeper inside me. I layed there for over half an hour being rhythmically pounded by my robot lover. I had a puddle of cum in my belly button when I shut it off. After removing myself from my new favourite dildo I popped in my plug, which now felt small but held in place. I attempted to get to sleep but ended up posting another ad on Craigslist.

I dressed in a full body stocking without my breast forms and my new brunette wig. I slipped on a new pink tight t-shirt with Cumdump written on it in purple. I decided not to have my plug in so as not to scare a possibly timid top and then posted some pics.

I got several replies pretty quickly, there was an older sikh guy with a turban and a long grey beard that struck my interest. He had a powerful looking stocky body and seemed nice but dominant in his messages he didn't say how big his cock was but it looked fairly thick and was dark like my BBC toys. I invited him and also messaged a 28 year old guy that I wasn't entirely sure was real. He was a skinny red head with a cock that looked so big on his frame it appeared photo shopped.

My sikh daddy got back to me right away and told me he'd be about an hour. I didn't hear back from the ginger so I assumed he wasn't real or just a pic collector. I waited patiently and he was right on time. I greeted him at the door confidently and rubbed his cock through his pants as he came in. It was bigger than I'd hoped and already rock hard.

I dropped to my knees and started sucking his as soon as he dropped his pants. He fucked my face and talked dirty to me in Sikh I guess. It was a major turn on and he kept pulling out so he didn't cum too quick before plugging it right back in. He was a solid 8" and thicker than Dale. He finally got undressed as I greedily sucked on his cock. He pulled me up and I led him to the bedroom.

He threw me down on the bed face first and I arched my back up into doggy. He pushed his thumb easily into me and I purred my approval. He worked in two, then three fingers and after a minute or two I felt his cock head rubbing against my sissy pussy lips. He entered me slowly but easily, his big brown hands gripped my hips hard and pulled himself into me forcefully with each deep slow stroke. It felt amazing but I wished he would fuck me faster. He pulled out and ate my pussy for a few minutes, his beard tickled my smooth ass and when he noticed my caged clit he squeezed my balls and slapped them with his rock hard brown cock. It was so hot looking back through my legs and seeing his big cock hanging there behind my pathetic little locked up cocklette.

He flipped me over onto my back and I pulled my lega to my chest. He pushed his cock back into me and again slowly pounded me, each time grinding as deep as possible. He was now rubbing my p-spot though and each thrust made my body feel warmer and my muscles feel weaker and my mind more fuzzy and cock drunk. My clit spurted a huge spurt of cum all over my stomach and he then pulled right after out and shot several big shots of cum into my face and mouth. He was super into my caged clit and asked if we could play again soon. I of course gave him my number and my schedule and he showered and left.

I checked craigslist and found a reply from the ginger top. He'd sent several more pictures and they were much more convincing than the first. He lived in rhe neighborhood and said he was obsessed with caged sissy sluts and couldn't believe I was real and nearby. I messaged him back and he was at my door 20 min later.

His cock was 10" and as thick as his skinny forearm. The head was massive and had a huge foreskin over it that slid right back when he got rock hard. I drooled all over and did my best to deep throat him, accomplishing it breifly a few times. He talked really dirts and was super into me being a caged submissive. He loved that I didn't even have my keys and agreed that it should never be allowed to cum. He came in my mouth without warning, his cock suddenly swelled and I almost choked on the massive load of cum. I licked him clean and he had me suck him again till he was rock hard.

He couldn't wait to fuck me and got me on my back with a pillow under my ass on the edge of the bed. He slammed his cock in hard and kept telling me how perfect and slutty I was. I begged him to fuck me harder and loved all of the praise. He got me into a spoon position and he pulled my face to his and forced his tongue down my throat as he jammed his cock back inside me.

I'd been fucked by several guys now but never kissed one, I'm not sure I liked it but I liked the sounds he made as he fucked me and made out with me. He pulled out and shot a jet of cum onto my swollen little balls before plugging back into my pussy and finishing off. I felt him dripping from me as he pulled out. I sucked him clean and he asked me if I had a butt plug. I found my new 3.5" plug and he worked it into me slowly. He marveled over how wide my pussy stretched and I let out a little yelp as it finally popped in keeping whatever cum was left inside me.

He showered and I gave him my number and then sucked his cock for a few minutes before he said he had to go. It was now 4am and I had Dale coming at 10 am. I set an alarm for 8:30 and passed out plugged and satisfied.

Thanks for reading

Katie

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