Katie's Sissy Adventures Ch. 02

The day after my loosing my sissy virginity to Dale I was walking around in a daze. I got myself all cleaned up and aside from my chastity cage put Katie's things away in the closet.

The next week or so I was pretty caught up in work and even though I think I would have liked it I was glad Dale hadn't texted me. He told me before he left my apartment that he would let me decide when I needed a good fucking and that I should text him first before sending pics.

I had gotten very accustomed to my chastity cage and decided if I was going to wear it permanently I should get one sized better and easier to clean myself in, I'd been using q-tips to try and keep it clean and unlocking once a week to make sure I didn't have any problems.

I decided on a black custom apoxy 1" long with an anti pull out and 2 locks and 35mm ring, very tiny. While fanstasizing about my new cage I decided I should probably have a keyholder if I want to be permanently locked so I messaged Dale to see if he wanted to come over that coming weekend to play with Katie. He got back to me a few hours later to say he was out of town working and wouldn't be back for a few weeks. I was disappointed but figured I could wait for him to get back, I didn't really have trouble staying locked... it was more a mental control thing I was craving.

Work slowed down again and I started to really get into the sissy hypnos and playing with my dildos again. I managed to squirt a little bit riding my toys but the sissygasm I had with my first real cock was not to be found. I ordered a fuck machine and a few more larger dildos, the largest over 3.5" wide flaring to 5" and a jeweled large pink plug for my pussy.

One Saturday a week before Dale was to be back and before my new toys had arrived I found myself riding my dildos and frustrated and posted another ad to craigslist. Slutty caged sissy bottom in need of long hard pounding, I posted it with some pretty explicit pics of my gaping hole with my bbc dildo deep inside and my caged up clit dangling uselessly in my schoolgirl outfit. One of the pics you could almost make out my face but it was too hot not to post.

I got myself all smooth and did my makeup like a whore and then checked my replies to find several older guys that fit the description. One guy really stood out, he looked fairly old... like grey pubes and chest hair but he had an absolute python between his legs. He was married though and said he couldn't sneak out that late so I made a date with him for the next morning and messaged the next guy that caught my eye.

He was early 50's tall and handsome with a thick beard and a 7" nice looking uncut cock.

He said he was available anytime so I sent him my address and he messaged back saying he would be about 45min. I rode my smaller dildo as I waited for him, before I knew my buzzer was going off and he was at my door. I was definitely not a nervous as the first time when I opened the door, he looked me up and down and half grunted half spoke his approval as he came in and immediately started taking his shirt and pants off. I took his clothes and put them on the couch then helped him out of his underwear and then started to devour his already rock hard cock, it actually seemed a little smaller that I expected from the pics but still made mine look like pathetic and was furiously pumping my eager throat so I was right back in sissy heaven.

He suddenly tensed and began pumping ropes of cum down my throat and I gagged and spit it up in him, he told me to lick it off and I gratefully licked every drop off his still raging hard cock. I thought he was going to get dressed and leave but he instead bent me over the edge of the couch and pushed his raw cock into me hard without any lube or spit or anything, luckily my pussy is well trained and it only took a second for him to be slamming away, it sounded sloppy and wet just like a cunt and the angle was making my caged clit drool like a leaky faucet.

He lasted for almost 30 min, sometimes slowing down briefly to pull his cock out and finger my gaping hole before pounding away on me again with reckless abandon. Finally I felt him grab my right shoulder and my left hip so hard it almost hurt and drive his cock as deep as it would go as he loudly moaned and pumped his load into my needy sissy fuckhole.

I cleaned his cock and he had a quick shower before leaving. It was an awesome fuck but I was still horny as hell. I fell asleep that night still dressed with makeup smeared all over my face and my bbc dildo inside me.

The next morning I awoke with the first really uncomfortable erection attempt my clitty had since starting with the holy trainer. I only had about an hour till my next cock arrived so I tried to ignore it while I got shaved and cleaned and pretty for the monster on its way over.

I went back to my first time outfit and wore the maids skirt and leggings and panties with my sissy shirt over my breast forms. I was almost frighteningly comfortable with what I was about to do. A few weeks ago I was still just fantasizing about porn but now I was minutes away from opening the door to a much older very well hung daddy that was coming to breed me and this was the third guy in as many weeks.

He was about 20 min late but he'd messaged to confirm and so I waited patiently till the buzzer went and let him up. When I answered the door I was a little surprised at how large he was... at least 6'6" tall with huge hands and I would think size 18 shoes. Also he was older than I thought... like 75 or so but seemed to be in good shape and well groomed.

He was gentle, not forceful at all. I undressed him and he sat on the couch. As I pulled down his underwear I was actually astonished at what I saw, it was at least 8" soft and thick like a pop can. My clit was absolutely ready to burst by this point and I excitedly started to massage his balls and lick his cock, it took longer to get hard than Dales did but as it did I could eventually not get my mouth around the head anymore and it grew to about 11" long. I stroked and licked his cock while he moaned and called me sweetheart and baby and told me I sucked cock better than his wife even though I couldn't actually get the monster past my throat.

Finally I couldnt take it anymore and straddled him right there on the couch. I tried to get him in without lube but it wasnt working and he went slightly soft so I sucked him rock hard again and generously lubed his big cock before guiding him into my desperate cunt. I worked down till I felt him against my inner hole then pushed out till he popped past the second ring. He grunted his approval and was amazed when I settled down taking the rest of his huge cock balls deep.

I rested on top of him for a minute then started riding him so he almost popped free and then back down to the hilt. His huge hands squeezed my ass and rubbed my back, he grabbed my hips and started pushing me down onto him even deeper.

I grinded my prostate against his cock as he viciously assaulted my hole and felt that feeling coming back where my body was warm and my legs were weak and I felt like everything was fluttering. I felt my caged clit getting wet and slippery as it rubbed against his stomach and he kept fucking me like nothing had happened. A few minutes after I came he pulled me down hard and grinded against my ass as he unloaded way up in my pussy.

He quickly went soft and I licked his cock clean before he dressed and left, he didn't say much and seemed embarrassed but I had just ridden a monster cock like a pro so I was on Sissy cloud 9. I watched him walk to his car from my window and felt his cum start to run down my thighs.

I messaged Dale and told him to let me know when he's back. Those other cocks were great but I thought Dale would be a better keyholder and more reliable fuck. He messaged me back almost immediately with a pic of his cock and his hairy chest. Can't wait slut, maybe I'll have to share you next time.

I spent the rest of the day watching sissy hypno and day dreaming about being gangbanged. I ordered a few more outfits and a sissy collar. Hopefully everything comes in by the time daddy's back I thought.

But that's another story

Thanks for reading

Katie