Katie's Sissy Adventures Ch. 06

That next week at work I wore panties every day. After a couple days rest my sissy pussy had recovered and I was wearing my jeweled plug again during the day and then coming home and shaving and cleaning before putting in a larger plug.

I decided that I needed to get out more and try to not just obsess over playing the sissy role all the time so I took a coworker up on his invitation to go to a baseball game that friday. Dale had plans with friends that evening so we planned to meet later if I was up to it, or the next day if it didn't work.

I wore my 3" plug and of course my clit was caged as always, all tucked into some pink panties and my boy underwear on top.

I guess I didn't think about the grandstands being just wooden benches so I spent the whole game grinding on my butt plug whether I wanted to or not. During the seventh inning stretch the whole place was shaking as the fans did a choreographed cheer and I came so hard I had to excuse myself to go wipe the cum out of my panties, some soaked through anyway so I bought a couple beers on my way back and "accidentally" spilled some to cover it.

As my friend dropped me off I noticed Dale standing on his deck when we drove by. My clit stirred in it's prison as I thought about what he would do to me in about 45 min. I almost forgot to say goodbye or thank you as I got out of the car, my mind already planning my outfit and makeup. I messaged Dale before I even got to the door to my building. I noticed messages from my sikh daddy and my ginger daddy as well.

He was ready and waiting so I asked for 30min to get ready and quickly douched and got dressed. He was right on time and I buzzed him right up. Messaging my other two daddies while he made his way up the stairs. After getting out and doing something "normal" albeit while plugged and caged, I was ready to be a slut for the rest of the weekend.

Dale came in and we went straight to the bedroom. I had picked out a tiny short skirt and no panties and was wearing my pink Sissy shirt stretched over my breastforms and my new sissy collar with my blonde wig. I tried to suck his cock but he wanted to be in my pussy immediately and pushed me down on the bed roughly and told me to pull my knees to my chest.

I obeyed and he pulled out my plug, I begged him to fist my wide open hole but he instead slipped his cock in and waited for my gape to settle around him before starting to thrust in and out slowly. He squeezed my balls hard as he fucked me and teased me about tossing my keys in the river, the torment made my clit so hard that I spurted onto his hand and he made me lick it off. He fucked me on my back for almost an hour before he decided he was thirsty so I ran to get a drink of water and checked my phone.

My ginger daddy had gotten back to me and wanted to play, my sikh daddy wasn't free anymore but wanted to see me the next day.

I went back to the bedroom and I sucked Dales cock while he had some water. He layed on the bed after and I got ontop in cowgirl. As I rode him I decided to ask if he wanted to dp me again with Tom. At first I was nervous because he seemed a little put off but he began to fuck me harder and told me he needed to breed me first that night. He grabbed my hips hard as he fucked me hard and fast till he unloaded inside me. His load dribbled out on his stomach as I climbed off of him so I licked it up and cleaned his cock with my tongue before putting my massive plug back in.

I messaged Tom and he said he would head right over. Dale got me to get on my bed in doggy and told me he was going to have my pussy plump and juicy for he and Tom to play with. He pulled out my plug and replaced it with his lubed up fist. I was a little embarrassed by how easily I took his balled fist already but the way he marveled over my cunt lips and dipped his raging hard cock in every now and then kept me just buzzing with arousal.

Tom arrived and Dale had me go answer the door. My pussy was so open I could feel either side of what felt like a slit with lips rubbing against each other as I walked. Tom felt up my cage and slightly prolapsed pussy lips as he came in. He dropped his pants right there and slammed his already raging cock into me against my open door.

I managed to lead us inside and close my door and we made our way to the bedroom with me leading him and his cock buried in my sissy cunt. We shuffled into the room and Tom and Dale greeted each other with giant grins. I endured another slut shaming while Tom got me leaning over the bed so I could suck Dales cock while Tom pounded away on my sloppy wet pussy.

Dale encouraged Tom to altenate between his fist and his cock while he fucked me and I moaned my approval around Dales cock. Tom started to fuck me hard in short fast bursts then pull out and push his fist into me before replacing it with his cock and rubbing it around my spacious hole, moaning and cooing the sexiest sounds as he did.

He lasted about 20 min before dumping his load inside me and resting in me till he went soft. Dales cock didn't leave my throat the whole time. After Tom went limp I pulled off Dale and cleaned Toms cock. We swapped positions and I sucked Tom hard again while Dale mostly just rested inside me grinding against my pspot and making my clit drool in big long sticky strings.

Once Tom was hard it was time for the main event. I got up on him in reverse cowgirl and he grabbed me by my breast forms and rested my back against his chest. Dale slipped some fingers in beside Dales cock and basically used them as a shoe horn to slide his cock in ontop of Toms, keeping his fingers in me as well till he had almost buried himself to the hilt and my swollen sissy sack was pressing against his stomach.

They took turns as to who was thrusting while the other held me down on they're cocks. I was lost in the look of lust in Dales eyes as he held me by the hips and kept my tiny balls pressed against his thick patch of pubic hair. It turned me on so much to know I was giving them both so much pleasure and I started to wimper as Tom pushed himself in balls deep and Dale began to take his turn. It hurt so good everytime he slammed against my sack and I soon again shot an involuntary shot of cum on my self. Dale finger fed it to me and they both congratulated me on being such a good sissy.

They carried on for quite a while, I was flipped into doggy and Tom jammed his tongue down my throat again and made love to me while Dale pounded away on my sloppy sounding hole. I was actually a little put out by the kissing but when Tom came again and he bit my lower lip gently as he groaned and shuddered it was incredibly hot.

Dale wasn't quite done yet and kept fucking me as Tom slipped out. He picked up the pace and after 5-10 minutes he also pumped his load into me again.

I worked up the strength to pull myself up and clean both they're cocks, Tom got hard again as I carefully licked under his foreskin so when I was done we got in a spoon position so he could be inside me while we rested. Dale showered and left and after a couple hours of resting/grinding on Tom I rode him in cowgirl again till he came and then asked I him to leave, not wanting to cross the line from fucking to dating or anything like that. He seemed a little put out but I knew that half of what I loved about being a sissy was the feeling that it was somewhat shameful and dirty.

I got cleaned up before bed and set an outfit on my dresser for the next day. I planned to see my sikh daddy again and Dale was free all day as well. I was the sissy fag slut I'd fantasized about and it was better than I'd imagined. I'd now been caged for close to 3 months straight and my asshole definitely resembled a well used pussy now. I had the taste of cum in my mouth still as I got into bed. I decided not to plug myself to let my pussy hopefully tighten back up a bit before it was destroyed again the next day and the way it swallowed the string from my panties made me feel like such a whore. I noticed I was laying with my back arched so as to allow access to my sissy pussy and was so happy with myself for being such a natural bottom slut. I popped on some sissy faggot hypno audio and drifted off to sleep with thoughts of cock on the mind, in a state of sissy bliss.

Thanks for reading

Katie