Sissy Plug Stories

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A Missy Affair Pt. 03

by Stillherer on Jul 20, 2020
BDSM

When I finally found the place I sat in my car by the gate for a long time watching the property nervously. Eventually I ran out of excuses in my head and slowly drove up to house. All was quiet and there didn't appear to be anyone around even though I could see their vehicles through the open garage door. Hesitantly I got out of my car and started shuffling...

Sissy Instructions

by FrostShard on Sep 13, 2017
BDSM

Dear sissy, I trust you are preparing yourself well for our session next week. This session will be your final plunge into the realm of sissyhood. Thus far, you have simply dabbled in it, all the while essentially staying a man. All that will change starting from this session. Starting now, from the moment you finish reading this letter, one thing will cha...

Sissy Hotel Play

by elliotsconfessed on Dec 24, 2018
Fetish

It was a Friday afternoon and I was feeling a little bored and some what curious... I had spent the last hour or so watching porn, but not just the usual straight type of porn I'd usually watch... For some reason I had an urge to watch men fuck other men and have guys dress up as girls and fuck themselves with toys! I was so turned on and a little confus...

A Missy Affair Pt. 02

by Stillherer on Jul 15, 2020
Fetish

I tried to carry on like my life was still the normal, everyday existence it had been. Beneath this facade of normality seethed the memories of Mrs Smith's parting words, "When the call comes for you Missy, you had best not displease us." I fluctuated between being terrified that the Smith's would out me and a seemingly incomprehensible desire for more of t...

Sissy Shopping with Princess T

by Subboi23 on Apr 1, 2020
Fetish

I excitedly pull my tight red lacy panties up over my small, limp penis. They feel so nice. Tight, but soft, containing the perfect amount of room to hold my little package. My penis does not attempt to get hard despite the pleasure, if anything it seems to shrink a bit in order to fit more comfortably. This was my first time seeing Princess T without her in...

Das Leben als süßer Sissy Sklave

by Captain Simpel on Oct 30, 2020
Miscellaneous

Justus war ein durchschnittlicher Junge mit etwas längeren schwarzen Harren, der gerade zu übers Wochenende zu Marie wollte. Die beiden waren schon seit der fünften beste Freunde und unzertrennlich. Etwas beneidete er sie für den Reichtum ihrer Eltern, die ihr mit 18 ein Leben in einer eigenen Wohnung ermöglichten, obwohl sie im Moment nie viel verdiente. Al...

Familie mal anders

by Herrtobi27 on Aug 2, 2020
BDSM

"Hi, mein Name ist Tobias Schneider und bin 19 Jahre alt. Ich bin ein Einzelgänger, besser gesagt mache ich mir nicht sehr viel aus anderen Menschen. In meiner Freizeit gehe ich gern in den Park Joggen oder schraube an so manchen Dingen in der Garage. Körperlich bin ich sehr Fit und würde fast schon sagen Muskulös. Um ehrlich zu sein Sexuelle Erfahrunge...

Sissy Stretching for Princess T

by Subboi23 on Apr 15, 2020
Fetish

I balance my phone up against my dresser, take a deep breath and wait patiently for further instructions. I had already received orders to be dressed in my pink negligee with no panties (or underwear of any kind) on and my butt plug inserted by 7 pm. I was in position 10 minutes early and was attempting to clear my mind and focus solely on obeying whatever o...

Sissy Stretching for Princess T Pt. 02

by Subboi23 on May 12, 2020
Fetish

Once I get home, I practically run to my room. Sitting in the car has pressed my plug deep into my ass and now my running causes it to wiggle around while still deep inside me. "Home Princess," I text as soon as I close and lock the door to my room. I quickly peel all my clothes off except for my panties and get on my knees. My toy is retrieved from a draw...

Cyber Sissy Ch. 04

by missvicky53 on Sep 25, 2017
Fetish

Megan rested for a moment, still recovering from her climax. After a bit, she stood and while making sure the butt plug was still deep inside me, closed the zipper in my panties. I was once again trapped in the silken caress of the purple panties, with my "pussy" filled. Megan kissed me gently on the lips while stroking my cheek. "Sleep well my pet, for tomo...