Cuffed and Stuffed

By Kendra Holliday | August 3, 2014

I had another wild-n-crazy roleplay date with my friends Capn Marrrk and Bianca. They always do such a good job of creating an elaborate scenario and are so clever with costumes and props! For example, there was the time we pretended to be two sisters disciplined by a military instructor…

This time, I was playing the prisoner, Bianca was playing “Mama” the police officer, and Capn was the mean Prison Warden.

They kicked it off with a letter that announced I was up for a parole hearing:

Parole hearing notice

Parole hearing notice

I showed up with my orange prison costume on hand so I could change when I got there. Truth be told, I had a terrible day and was stressed and overwhelmed. I didn’t feel like an elaborate roleplay scene. I felt like vegging on the couch and whining and being coddled.

But when I got there, I discovered they were already dressed up and in character! She was wearing a tight, sexy blue police uniform, and he was wearing a brown suit and police sunglasses. Both had their arms crossed and looked STERN. They meant business!

Right away they addressed me as Prisoner #23049 and escorted me upstairs to change. OK, here we go!

As soon as I was in my jumpsuit, they cuffed me and led me to the chair for interrogation.



The Warden asked me all kinds of probing questions and grilled me. He made me state why I should be allowed early release, my plans on the outside, etc.

He informed me that if I wanted to get out of prison, I had to do whatever they say, including being their sex slave! They both were very serious and weren’t going to let me off easy.

He told me I had to start by paying “Mama.” She straddled my lap and her amazing cleavage was right in my face! Right then and there, I forgot about my stupid, stressful day, poof!

Her creamy breasts looked like they were going to burst out of that tight uniform. She kissed me – it had been a while since I kissed a woman, and it was so sweet and soft and sensual! Such a treat, like eating a cream puff after a bunch of potato chips.

After we made out for a bit, they stripped me down and marched me to the bed. I pretended to be horrified by everything they were making me do, but I secretly loved being forced to have lesbian sex! Oh my god, who wouldn’t?!

I'm their prisoner!

I’m their prisoner!

I melted into the sexytime with her – we went down on each other. I got lost in the lust as the Warden looked on. Stockholm Syndrome!

Finally, he was ready for a turn.

He barked, “Prisoner #23049 – can I kiss you?”

I stopped and stared at him. He wasn’t supposed to ask – he was supposed to prison rape me! But of course he is sex-positive and a firm believer in consent and didn’t want to take liberties, even in a roleplay situation. We hadn’t negotiated the scene ahead of time. A lot of guys would’ve used it as an excuse to be entitled and aggressive, so I appreciated his consideration.

That said, I whispered, “You’re not supposed to ask – you’re supposed to have your way with me!”

With that green light, he jumped in and made me suck his dick and fucked me hard, wearing nothing but a condom and police sunglasses. I squealed and begged, “Please no! I haven’t had a dick in five years!” and cried and had a blast. I loved all the attention!

Once they both had their fill of me, they surprised me with something rude and scary – they violated me with a fake gun! They thoughtfully put a condom on it for my protection πŸ™‚

Fucked with a gun!!!

Fucked with a gun!!!

I knew it was pretend, but it was still edgy and scary for me because I HATE GUNS EEEEK.

It turned out to be a wildly sexy, fun evening. It really took my mind off the daily grind and gave me excitement and release.

After we were done playing, I gave my partner a call to check in. I was all happy and sex drunk.

He knew I had a date with them, but somehow I neglected to tell him the nature of the date until after the fact. He was NOT pleased to find out that way. OH NO! My bad. πŸ™ We had been having such a frantic, busy week. I had been updating him on all kinds of random bullshit over the phone, and thought for sure that had been one of the topics we covered.

When it comes to being with other people, we both like knowing what to expect, especially if it’s something beyond vanilla sex (such as, you know, prison rape roleplay with handcuffs and guns). I pride myself in my good communication, so I was really disappointed with myself for this oversight. We talked it over and I apologized and we worked it out and I learned a lesson – I won’t be dropping the ball next time.

Still, if he wants to punish me, I’m ready…


CapnMarrrrk 2014-08-03 22:39:22

Honestly out just popped out of my mouth.It’s not what I was thinking,I wasn’t thinking! Fuck if I know.

Thank you for the article. I loved reliving it.


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My name is Kendra, and I'm a beardoholic.


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