Sissy Butt Plug Stories

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The Jewelers

by mollycactus on Sep 16, 2017
BDSM

Author's note: my BDSM stories are mainly D/s in nature – there is no Literotica category for these, so if you do not like D/s, you can skip this story. ***** Molly had taken on a new submissive male, who had what seemed to her to be, a strange need. Kneeling before her, Robyn explained his desires. "Please, Miss. Cage my cock so you'll be completely in c...

Mistress Patty Ch. 02

by timeagain93 on Sep 17, 2017
BDSM

Mistress Patty was brushing her teeth in the motel bathroom; she paused to spit and continued talking. "Y'should see what my sister does to her husband! You're getting off light, believe me!" I could only nod. I was blindfolded, butt plug in my mouth, hands cuffed behind my back on the toilet. She uncuffed me and removed the plug. When the motel door slamm...

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...

Don Takes Over Ch. 01

by chas19839 on Sep 12, 2017
Fetish

The giant butt plug made me squirm and moan in discomfort as I knelt by the door. Don had been training me well from a distance; having me wear bigger and bigger plugs each week. The one lodged in my ass as I knelt patiently felt like a giant log. It had taken me months to convince Steph that we should have Don visit us. But now that she had finally agreed...

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...

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...

A Sissy's Life

by Queen_Diana on Jan 27, 2020
Fetish

A Sissy’s Life by Queen Diana Slutty pink lip gloss? Check. Ass cheeks practically hanging out of a scandalously short pink skirt? Check. Pink tube top, butt plug, and thigh high stockings? Check. “Check, check, and check! That’s everything!” I giggle. Looking over at the body length mirror. Writhing with satisfaction, as I realize, what a pretty little sis...

Sissy's sister

by acepmn on Nov 21, 2015
Bisexual

Anna had always seemed like a good girl. Our parents weren't suspecting anything bad about her, just like they didn't suspect I was spending a lot of nights dressed as a girl in my room. I had skirts, cute tops, slutty dresses, panties and sexy thongs, butt plugs, dildos, cockrings, vibrators... A whole panel of varied toys to play with while dressing up. I...

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 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...