Sissy Caged Sex Stories

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Sissification 101: Ch. 05

by silkstockingslover on Aug 31, 2020
Interracial Love

Sissification 101 Ch 05 Summary: Erica practices taking BBC in both of her sissy holes. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught by a very supportive girlfriend in pantyho...

Anklet Adventure Pt. 02

by dometoo on Oct 29, 2018
Interracial Love

Day two of our cruise started with the sun shining through the open balcony slider and a slight, warm breeze dancing over our naked bodies. The rhythmic sound of waves breaking against the hull was memorizing, almost hypnotic. My beautiful wife of 20 years and I lay exhausted on the cum stained sheets she and her bull made without me last night. We were both...

A Cuckold's Journey Pt. 03

by yukonnights on Nov 26, 2018
Fetish

The big day had finally arrived. In fact, for me it arrived so fast that I was on pins and needles all day until Sarah came home a little early from work. I had the house work done and was just sitting in the living room waiting when she walked in. "Hi babe," I said as I got up to give her a hug. "How was your day?" "It was good. We weren't too busy today s...

Sailing Away Ch. 23

by Jasmyn_White on Jun 1, 2020
Fetish

Lacy, done with her recollection of the trio of BBC, asks, "what do you think?" "I think it went spectacularly well, and I'm glad you enjoyed so much." "Oh, I surely did my bitchboi. And I've got just the way to reward you. In a sense." I knew you had something afoot. "Let me see your cock, sweetie, I want to unlock you so you can shower." Doing as told...

My New Life

by gbr2004 on Jun 1, 2020
Fetish

This story is totally fictional and involves forced fem, discipline, interracial sex, among other kinks. Kind of a long story with probably too much dialogue and not enough sex but I hope you enjoy it. *** I'm not going to take any more shit from this asshole. I'm talking about my stepfather. Sure, he's nice when Mom is around but when she isn't here, he t...

Sorry Sissy You Lose Pt. 02

by LittleDickSissy on Jan 22, 2019
Fetish

Mistress enjoyed watching herself primp in the mirror. Music playing in the background, a glass of alcohol to sip from, and the knowledge she was going out on a date with George - the older gentleman she had been fantasizing about. As she slid her smooth legs into a pair of crotchless hose purchased by her sissy slave she looked at her trimmed bush. The si...

The Sexy Cuckold Couple Pt. 16

by cuckcpl4play on Sep 26, 2017
Fetish

PART 16: REST / EVENING EVENTS Showered with mixed feelings, I thought about the day's events thus far and looked at my beautiful wife. She gazed back at me and it was such a strange sensation as I could literally feel the love and energy between us despite all of the events that had transpired. My mind brought me back to the moment; we were absolutely exh...

The Sexy Cuckold Couple Pt. 15

by cuckcpl4play on Sep 26, 2017
Fetish

PART 15 POOL 2 As we walked outside, I noticed that our private area was more populated than expected. There were a few more additional males but more than a handful of additional and very attractive females. Sir Jeremy approached my wife quickly and I watched as the other women gawked at her and then began laughing at her as several of them even engaged in...

Abuse my Sissy bitch

by Red10Dog on Mar 3, 2020
Fetish

This is a story from the sissy's wife. Telling you a story that happen a few weeks ago and it was orgasmic! So late one Saturday night I put my sissy bitch in a teddy, nylons, cock cage and a jeweled anal plug under his pants and shirt and headed out to the casino. I am not ready dress him out in public yet, but I am getting close. I decide to slut mysel...

A Sissy Girl Bitch, 'BEST IN SHOW'

by keptsissy on Mar 3, 2020
Fetish

** Author's note: All characters depicted in this story are fictional, well beyond age-of-consent, and are consenting adults. ********************************* He made a point of showing me off, displaying me. That was obviously his thing from the start. Many men at the clubs he'd take me to were allowed to not only look but touch me too. I never thought a...