Sissy Jail Stories

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Orientation
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Infinite Scroll

Paying Rent Ch. 03

by JailBird Dreamer on Sep 16, 2017
Transsexuals & Crossdressers

I woke up in the morning, still on my mattress on the floor. My boy pussy was on fire and my panties were soaked with lube and cum. I went to our cell's toilet and let out a stream of my new master's cum. I couldn't believe I still had that much in me! I looked around for Jermane, but he wasn't in the cell. I figured he must have gone to his job in the kitch...

Cinderella - a BDSM Retelling

by MistressMoira on Sep 25, 2017
BDSM

Once upon a time there lived a kinky girl, a very kinky girl indeed, named, well never mind her real name, her chosen nick for play was "Cinderella", for reasons which will become apparent later. Cinderella lived in a polyamorous family with an assortment of bdsm proclivities with her "Daddy" (a switch - top to Cinderella and bottom to his Domme to whom he...

Riley's Bar Ch. 06

by Just Plain Bob on Sep 15, 2017
Loving Wives

I almost smiled as the cell door clanged shut behind me. The decision on how to handle my Friday the 23rd problem had been taken out of my hands by some judge. I would be a guest of the county on Friday. In fact, being me it was almost certain that I would be a guest of the county for a while. The "failure to appear" had to be over the divorce and the paper...

Second Amendment Gun Rights are Wrong

by SusanJillParker on Sep 13, 2017
Reviews & Essays

Lay down your weapons and pick up your water guns. Ready? Aim. Fire. Under the second Amendment, the right to bear arms, one of the reasons given for owning a gun is because it's in our constitution. Yet, as if that's the limit to our constitution, I dare say that the 2nd amendment, for all the wrong reasons, is the one amendment most quoted behind the firs...

Sheila and Penny

by Sheila_TSSub on Sep 19, 2017
Transsexuals & Crossdressers

Part 1 I had been upstairs that morning doing my chores. I was dressed in a cute little yellow summer dress and leather heels with 4" wedge heels. When I came downstairs I found Mistress Tina (my wife) and Princess Gina (our daughter) in the den. There was a man there that was unknown to me. "Come here." Tina commanded. I went in and knelt beside her cha...

Two Hot Blondes Get Burgled Ch. 07

by scatwoman on Jun 15, 2020
Interracial Love

Chapter 7: "Repercussions" "SMACK!" "RRGH!!" "SMACK!" "MRRGLFM!" "SMACK!" "CRFFT!" "Heh, whatsa matter whiteboy?" Donk chuckled as he stood behind Todd and alternated slapping the left and right side of the bound quarterback's face with his flaccid 20-inch dick, "doncha like big black dick as much as yo girl over there?! I thought ALL white bitches lo...

Anthony/Toni

by orvette1 on Sep 16, 2017
Transsexuals & Crossdressers

When I was 15 I was hanging out with some bad guys. We robbed a store, I got caught and went to jail for five years. Anthony, my brother, was only ten when this happened. When I got out of prison my parents told me to not come back to the house. So I moved out of town. Five years after getting out of prison things weren't going well for me. When you are an...

Afro Stress Relief Ch. 10

by llts1970 on Mar 30, 2020
Transgender & Crossdressers

I woke up on the Saturday, not believing what I'd got up to in the Beer Bust and not sure what to do, now everybody knew what I was, a little white sissy bitch that worshipped black dick! How would everyone treat me on Monday at work, Elizabeth had said not to worry as 'what happens at the Beer Bust stays at the Beer Bust', however how could I tell my black...

Kate's Mom Comes To Visit Ch. 05

by Catytheghost on Sep 16, 2017
Transsexuals & Crossdressers

Part 5 A wedding to plan Carmen OK, dinner was a total surprise for me, that's for sure: Ally and Kate getting married, and Mary putting the fear of the Gods into Maggie. Now that really was a shocker, as Mary gets along with everyone. I even asked her about Lady Jenna using me for her pleasure, and she said, "Honey, you just please her and all will be goo...

Letter From Tacoma

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: When my husband, who is owner and ringmaster of the Epic Circus, comes into our hotel room (We, thankfully, don't have to live in the circus trailers) I'm ready for him. He lays the whip down, and then it's my turn... "Strip it all off Apollo, my love! Now you'll get a nice thrashing....it's MY turn to use the whip!" Sometimes after th...