Tiffany Can’t Pay Her Rent.

It was a sunny winter afternoon, and Tiffany was dressed in her cosplay best, all set to go to the role play gathering in the park. Today she was a warrior princess, complete with golden crown and ceremonial dagger. The nerdy guys get horny whenever they see her and she loves the attention. She often dances at these get togethers and usually picks up some spare cash.

Just as she was about to leave, the doorbell rang, and on the doorstep stood her landlord and Mistress J. Tiffany was trapped and startled. You see, Tiffany was a naughty girl and had been spending her rent money on slutty outfits and makeup. She had been dodging the landlord, hoping he’d forget she was behind on rent since he has a nasty temper. Apparently, he was at his wit’s end trying to reach Tiffany and got Mistress J involved, as Tiffany always obeys her mistress.

The following conversation took place and it was just like a scene out of an old melodrama.

Landlord: “You must pay the rent!”

Tiffany: “I can’t pay the rent!”

Landlord: “You must pay the rent!”

Tiffany: “I CAN’T pay the rent!”

Landlord: “You MUST pay the rent!”

Mistress JI’ll pay the rent!”

They both stopped arguing and looked at Mistress J in disbelief. SHE, Mistress J was going to pay Tiffany’s rent? 

“Oh Hell no!” Mistress J said. “I’d never do that. I want that bitch beholden to me.”

Mistress told the mean and nasty landlord that Tiffany would work off her debt any way he wanted. He paused and a little grin appeared at the corner of his mouth. 

“I have a few ideas,” he said. “I need my dick sucked and I want to see you get pounded and take it like a slut by Mistress J.”

Tiffany had never been banged by two people and was very scared about this. She simply didn’t feel up to the task and tried to talk her way out of it. Mistress J was adamant. Afterall, she was trying to help the careless slut keep her apartment, and the least she could do was show some gratitude and get down on her hands and knees for the both of them. 

Mistress J stuck a plug in Tiffany’s ass (pussy) as warmup. Unsure of her cock sucking skills, Tiffany gave them show by practicing on a few rubber cocks. She really wanted the landlord to enjoy his BJ. Landlord stood nearby and closely watched what she was doing, offering praise or pointers depending. As her throat and pussy warmed up simultaneously, she started moaning and grinding on the stool as she sloppily and loudly sucked the cocks. She even chocked a few times from deep throating, poor girl.

Turned on, landlord dropped his pants. He was free balling and his big cock jumped out angry and red. “Suck it.” he said and Tiffany greedily sucked the giant member. Slowly taking the whole thing in, then sliding back up to the tip and swirling it around. This went on a bit and Mistress J got bored and grabbed Tiffany’s head, and pushed it deep down on landlord’s cock. She gagged and tears rolled out of the corner of her eyes as Mistress forced her small mouth down to the thick base of landlord’s thick juicy cock.

Finally, Mistress allowed her to get up and Tiffany got on all fours. Mistress played with her pussy

Riding Miss J’s cock and sucking another!

as landlord demanded more cock attention. Tiffany alternated between her hands and mouth and the landlord enjoyed her techniques, saying she was a sweet and talented dirty whore. Tiffany surprised him by sucking on his balls, and landlord liked it so much he almost shot his load right then. But he backed off and Mistress J decided the girl needed to be fucked into submission.

Mistress J strapped on a cock and told that bitch to straddle it backwards. As the slut mounted it reverse cowgirl, Mistress told her to suck off the landlord and not stop until she was told to.

Pounding that pussy.

Tiffany had never been treated like such a piece of meat before. Her holes were being filled and she loved every second of it. The landlord yanked his dick out of her mouth and slapped her face with it. Tiffany squealed as  the pre-cum landed on her cheeks. Mistress J slapped her ass as the little whore rode her cock moaning with delight. Mistress stroked Tiffany’s dripping wet clit and the girl squirted into a towel. But was she allowed to stop sucking dick? No. The bitch had to keep going until the landlord was satisfied.

Things were getting pretty intense as Tiffany experienced full on submission as a plaything. She was forced to suck and tug until the landlord finally grunted and shot his load deep into her throat, intensely thrusting until not a drop remained. The bitch had to swallow it all too.

Grateful to be able to keep her apartment, she kissed his feet and he slapped her ass as he walked out of his building. Mistress J said to Tiffany that she expected gratitude for this and Tiffany needed to show her appreciation in some way, otherwise, she would not help her again.

What do you folks think? Did Tiffany do a good job of working off her debt?

The complete set of the Tiffany Tales are here:

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My email is  I am in San Jose, California.  I look forward to hearing from you.

31 thoughts on “Tiffany Can’t Pay Her Rent.

  1. What a naughty little girl. Happy to hear she was properly punished for her late rent. For good measure I would have also made her ware a sign around her neck in the yard that said she is a sissy slut after she took her load from her landlord.

    Spankings could also have been good, one for each day she was late.

    • Would love to see Tiffany work off her rent back in the park where she did yoga. Tie a collar to a tree and she can work to earn some cash and get some fresh air.

      Love the blog post and love the suggestion here. I love the look of heal resistants to keep a sub on her toes!

      • I was recently at that park, and of course thought about Tiffany. She’s a nasty thing. I’d love to pound her down by the creek bed.

  2. You let this bad girl off easy! I would expect that she be forced to take the dildo and cock ATM. Next time she is late make her do a workout to get her tired before you continue the punishment.

  3. Very fitting punishment. I would love to know if the landlord felt that he got him money out of her dirty holes.

    I would have left the bad girl in the house with a tight corset and deep anal plug forced to walk in high heals for the rest of day. Maybe make her cut the grass in the outfit.

    • Landlord
      I did feel like I got my moneys worth for now. We’ll have to see when rent is due again. Maybe we go to the gloryholes to get some money back. Have to watch the blog to see what happens next

  4. Tiffany is a total slut and took all she could get. Maybe you should have her pay YOUR rent mistress, sounds like she liked it very much. Can’t wait to see what is next.

  5. Hello readers. I wanted to publicly thank my Mistress J for helping me pay back my late rent. I owe her a lot of thanks and I will continue to do everything she asks me to do.

    My landlord was a great Dom and I was proud that I was able to be a good sissy SLUT who was able to pleasure his alpha cock.

    I look forward to my next session with you MJ!

  6. I think the point system is a fun way to work off a debt for the sub. Pull together a list of activities and give each a value. Example is one spanking with a paddle is 5pt, spanking with hand is 1pt. BJs could be 10pt.

    This lets the sub get a feel for what is to come based on the amount of debt given. Have fun and make the list your own.

  7. Sounds like the perfect transition for Tiffany to become a sissy house maid. Put her in that tight corset, plug her hole and make her tour the house in high heals cleaning and dusting the furniture. The more uncomfortable the heals are the better!

    • If she looks and works good enough you could sell her “cleaning services” to some lucky friends. I would love to have this Gurl over to clean my high shelving and my guesthouse

      • I absolutely love this idea. That slut has it way too easy. Are you local to SJ? She could start with your house, after she does mine of course.

  8. How I envy Tiffany for this unique chance to repay the rent money! It’s too long since Mistress J strapped on a cock and told me to straddle it backwards. Mistress J is fantastic and I am saving all my rent money to book a session.

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