Katie's Sissy Adventures Ch. 01

Hi I'm Katie, or sometimes im Katie. I'm a 31 year old closeted crossdresser that loves to play the very submissive role with dominant older men from time to time.

This is the story of my first time indulging my sissy urges.

I had recently broken up with my first long term girlfriend and had spent the last couple weeks getting moved and set up in my own apartment. I'd been obsessed with trans porn for several years at this point and had secretly collected a variety of dildos and a cb-6000s chastity cage in pink, I loved to fantasize about being the bottom in the videos I was watching but had never actually acted on those urges.

I've always thought I was too big to be a bottom, I'm thin but at 6'2" tall I was worried that no matter what I'd be too masculine to play the role I fantasized playing. I am however fairly naturally hairless and my cock is a pathetic 4" rock hard and not much thicker than my thumb so I've never felt comfortable playing the alpha role either.

Finally moved in and fully broken with the ex I had settled into a routine of locking myself up in my chastity cage every morning and then coming hone from work and watching porn and riding my dildos till I couldn't take it anymore and unlocked to jerk my little cock off before passing out and doing it again the next day.

That is until the day I couldn't find my key when I went to unlock and jerk off. At first I panicked but not wanting to break my cage without a replacement I attempted to sleep with it on hoping I'd find the key the next day and everything would be fine.

After a very restless night I again failed to find my key and went to work in a frustrated uncomfortable state. That night when I got home I turned the place upside down and still couldn't find the key, by now it was feeling a little more comfortable so I decided to get online and order another cage, in the suggestions for other products I noticed a set of breast forms and backless panties and before I knew it I'd ordered a Holy Trainer nano in clear, A new 12" 2.5" thick black dildo, a set of breast forms, a schoolgirl outfit, a maid outfit, a blonde wig, a makeup kit and a tight fitting white T-shirt that said Sissy on it in big pink letters. I spent the rest of the night pounding my ass with my toys and went to bed dreaming of my new gear arriving in a few days. Still had a pretty rough sleep as my little cock kept waking up in its cage but with no key I just tried to ignore it.

The next day after work I stopped at the drug store and got some nair and lady razors and shaving cream, I couldn't stop thinking about being dressed and looking slutty, not sure if I would actually want to dress for someone or just me at that point but I wanted to feel as feminine as I could.

After shaving and using the hair removal I felt so smooth and soft that I couldn't even focus on the porn, I abused my ass for hours that night. Rubbing my hands all over myself and just raging in my cage, it was dribbling but no relief was to be had.

A few more frustrating days later and my package was waiting for me when I got home from work. After cleaning and shaving again I gleefully opened everything and started trying on my outfits, loving everything and how well my breast forms fit me and my wig I practised for hours that night on my makeup. Leaning over the sink with my new dildo stuck to the wall behind me, stretching my ass while I watched youtube tutorials and made myself look like a total whore. I never got around to taking off my old cage... it was starting to feel like it was part of me I guess.

I slept in my maid outfit and breast forms that night, slept like a baby.

The next day I decided to break my old cb-6000s off and try my new holy trainer cage out. After carefully removing the old one I resisted the urge to stroke my somehow even smaller looking dicklette and locked it up in the new cage. It was much more snug I loved how it fully contained my tiny little member even when soft and prevented even a little growth when I got excited. After my toys that night I again slept through the night without much trouble and after a few days I was thinking about my cock less and less everyday. I started to add sissy hypno and chastity hypno into my porn watching and soon most of my evenings were consumed with sissy training. I went 30 days in chastity without really planning on it and then when I went to jerk off upon release it felt so unnecessary that I just ended up locking up again 2 min later.

As the weeks went by I started to become obsessed with the idea of being used by a big fat cock. I would type up ads on craiglist then not post them, then I started posting them but with no pics and wouldn't reply to the few resposes I got. Then one friday after about 2 hours on my bbc dildo I took some pics of my locked up clit and my wet lubed up smooth hole and my thin hairless body in my maid outfit, careful not to post my face and put up an ad looking for a dominant older guy with a big cock that wanted to take my sissy cherry.

I was amazed at how many responses I got, most were guys that loved my pics but couldn't or wouldn't meet but from the few guys that fit the bill i narrowed it down to a 55 year old guy named Dale, he was about 6" shorter than me but fairly stocky and had a 7.5" thick cock with a nice curve and huge veins that made my mouth water when I looked at it. He was very eager and as it turned out lived just a block away in another apartment building. I had wanted to host but he insisted on hosting so after setting a time I shaved smooth, applied some vanilla body lotion and picked out my maid outfit skirt and panties with my tight sissy t-shirt stretched over my breast forms. I packed my makeup and wig and slipped a pair of sweats and a hoodie over my outfit and made my way down the street to his apartment building. I was so horny that my clit felt like it might break the cage but also so nervous that I almost turned back a couple times.

After what seemed like way too short of a time I was at the entryway to his building, taking a deep breath I rang his number and waited for him to answer. He called me my gurl name when he answered me and it was the first time anyone had called me Katie out loud, it was incredibly hot... all my nervousness started to fade as I made my way up the two flights of stairs to his apartment. I knocked and he answered the door wearing white briefs and a T-shirt I could see the outline of his soft cock in his underwear, it was so much bigger than mine. He pointed in the direction of the bathroom and squeezed my ass as I slipped past him and mumbled hello in my most feminine tone. I had planned to go all out with makeup but ended up just doing coverup and eyeliner and lipstick with a bit of blush, didn't want to keep him waiting too long. I quickly fingered my ass to make sure I was spotless and swished some mouthwash before making my way to his bedroom down the hall, clit straining and head swimming with excitement.

I knocked on his door and it swung open, he was laying on his bed naked with his soft cock resting against his leg. He made some remarks about how sexy I looked and asked me to spin for him and flash him my ass and my locked up cock. When I raised the front of my skirt he leaned forward and grabbed my swollen balls and gave them a squeeze and said "you sure know your role dont you slut".

I answered yes and asked if I could call him daddy, he said "of course slut daddy is going to take good care of his toy". He told me to get on my knees then stood up and got right in front of me and told me to get him hard.

I started massaging his balls and stuck my tongue out to lick the tip of his cock. It started to grow as I worked him into my mouth and before long I could feel his thick veins and bulbous head running over my tongue and into my throat, making me gag a little but I managed to deep throat him without making too much of a mess. He would use my throat till he was close to cumming then pull out and smack my face with his big cock and smear my makeup all while calling me whore and slut and faggot and whatever degrading thing that popped into his head, I was absolutely cock drunk and loving every second of it. I started begging him to take my cherry and he asked me if my pussy was ready to be fucked... I loved that he called it my pussy... I said yes daddy please fuck my pussy. He made me repeat it several times louder each time till I'm sure his neighbors could hear me but I didn't care. I was so horny and desperate to get fucked I would have let him take me in the middle of the street.

He pulled me up off my knees and pushed me onto the bed, lifted my skirt and started to finger me. He questioned my virginity because I wasn't as tight as he expected I guess, but I had already told him I rode my dildos almost nightly and then seemed happy to not have to prepare me to get fucked. He walked away behind me and I heard a condom package open and lube getting applied. Face down ass up I waited till I felt him rubbing his thick cock head against my hole and gently moaned as he pushed till the head popped in and gave me a second to adjust to it before sliding himself all the way in till his balls rested against my taint. He made such masculine noises as he started to pound away slowly all the way out till just the head was in me and back in, every time he bottomed out I made a girly squeal and pushed back making sure to take every inch. His pace quickened and before long he was slamming into me and my pussy was so wet it was making the hottest sex sounds. Every grunt from him made my clit squeeze against its prison and his hands firmly grabbing my hips to control me made me him feel so powerful and manly I knew in that moment I was exactly where I needed to be.

He turned me over and I pulled my legs up so he could enter me again, his cock was slightly limp so I sat up and pulled off the condom so I could suck his cock again. He fucked my throat till he was rock hard again and I layed back for him to enter me, he went to reach for a condom and went against my better judgement and begged him to breed my sissy pussy make me his. He smiled real big and called me his cumdump as he came and slid his cock back into me. His raw cock felt better than it had before and somehow harder, I could feel the giant vein on the top of his cock as he pounded away on me and I started begging him for his load.

Please daddy please fill me with your cum, make me your cum dump daddy breed my slutty pussy daddy. He started to really pound away on me and I could tell he was close, I tried to squeeze around his cock with my pussy but I was so open by that point it probably didn't help. His body tensed up and he drove himself balls deep and he moaned and grunted the most satisfied sounds I'd ever made a sexual partner make. I couldn't feel his cum inside me but I could feel his cock pulsing as he unloaded his balls deep inside me. He layed ontop of me till he started going soft then pulled out and let me clean his cock, I savoured the little drops of salty cum left over and could feel his load dripping down my inner thigh as I made my way down the hall to the bathroom and he layed back down on his bed.

I was still so horny but now in the aftermath I also kind of ashamed and wanted to escape back to my place. I slipped my boy clothes back over my outfit and half ass removed my make up before letting myself out without even saying goodbye. I felt bad but the urge to run was strong. When I got home I messaged him with an apology and he said he didn't care and understood, told me when I was ready for round 2 to give him a call and sent me his cell number so I didn't to go through craigslist.

I had a shower when I got home and finger fucked myself trying to taste his cum from inside me, pretty sure most of it was now dried on my stockings, I made a mental note to get a butt plug. After I got out of the shower I was still horny so I played with my dildos for a bit then decided that I was ready for round 2 right then.

I put on my schoolgirl outfit and did all my makeup super slutty before sending him a pic over text and asking if he had another load wanted to pump into me. He texted me back in about 1 min with a pic of his rock hard cock. This time he came to me. He came in the door and I sucked him right in the entrance way before he bent me over my kitchen counter and fucked me till my microwave fell off the other end of the counter and smashed. We moved into the bedroom and he layed on the bed so I could ride him. I got ontop with my hands behind me and he guided his cock into me. I could feel his cock head against my prostate every time I slammed down onto him and the feeling was building like when I'd been close to cumming while riding my toys.

As I got closer to an orgasm my body always tightens up and I end up frustrated but this time as I got tense he took over and kept pounding me till waves of pleasure were running through me and my body was quivering uncontrollably. I didn't feel it but when I had regained my composure I had squirted cum all over his stomach and chest. He got me to lick him clean then turned me over and fucked me into the bed till he unloaded inside me again. I cleaned him up and he used my shower before getting dressed and going home.

I had finally lived out my deepest fantasies and I'd loved every second of it. I slept that night with his cum inside me and my face all covered in smeared makeup.

That was my first time playing the Sissy role but as it turns out not anywhere near the last.

Thanks for reading

Katie