Day Two Arrives

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Tag: chastity

Ruby Ryder shares black and white photo of a captive cock in chastity cage - day two!
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Day Two Arrives

Masturbation Month 2022 #8 (Link to Part One) The arrival of day two couldn’t come soon enough. Tossing and turning that first night was no fun. Frank woke up many times with his cock attempting to have spontaneous erections, and

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The First Night Concludes

Masturbation Month 2022 #7 (Link to Part One) The first night was a total success in Cynthia’s mind. She went down the hall and stepped directly into the shower. That was fucking hot! Of course this was only the first

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Ruby Ryder shares chrome chastity cage to be worn during pegging
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Doing the Dishes and More

Masturbation Month 2022 #4 (Link to Part One) Doing the dishes felt the same as eating dinner; something he just needed to get through to finally get to the main event. So as Frank cleaned out in the shower, he

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Ruby Ryder shares stainless steel chastity cage for tease and denial during pegging
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The First Night

Masturbation Month 2022 #3 (Link to Part One) Somehow, Frank got through that day, sitting at his desk with the weight of the cage between his legs. He kept redirecting his thoughts back to work. Not an easy job when

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Ruby Ryder shares steel chastity cage in story of Frank as kitchen maid for a week
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At First it Felt Good

Masturbation Month 2022 #2 (Link to Part One) The cage felt good. That was a surprise. He sat there eating lunch at his desk and marveled at the sensation. Nice. Frank was beside himself with thoughts that had nothing to

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Ruby Ryder shares stainless steel chastity cage with lock for chastity play
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Seven Days as a Kitchen Maid

Masturbation Month 2022 #1 “Cynthia, where is the key?” Frank’s voice had an urgency to it that I’d never heard before. But after 5 days of his cock in prison, I understood his urgency. Frank was a very highly sexual

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Ruby Ryder shares long legged woman in red latex stockings and red strap-on with dildo
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Lend an Ear to Podcast #288

For your listening pleasure – it is indeed time to… Lend an Ear to Podcast #288! She offers more info re: chastity, cuckolding & humiliation questions He noticed men’s clothing ads in the US don’t show asses – WTF? Podcast

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Jacob’s Unusual Homecoming

by Ruby Ryder Erica said she’d be there to pick me up at the airport. I could hardly wait to see her. After a week away, I was seriously out of sorts. I missed serving her and cooking for her. I

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Ruby Ryder shares woman wearing black boots, fishnet bodysuit and strap-on with black dildo
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Pegging Paradise Podcast #269

Pegging Paradise Podcast #269 He writes back with more thoughts about cum eating A Taste Tester shares his journey He takes it to the level of pre-cum in a shot glass! His story about coming to terms with his love

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Distance Chastity Play That’s SAFE!

Cellmate Catastrophe With the news about the Cellmate that came out recently, that anyone can hack into the device and lock up a cock permanently, I suspect there are many of you out there still searching for some kind of

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