Day Two Arrives

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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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No Way Out

Masturbation Month 2022 #6 (Link to Part One) There truly was no way out of this adventure at this point. From the moment Cynthia thrust that purple cock into his ass, Frank’s legs began to tremble. His craving for this

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Ruby Ryder shares small purple dildo by Fuze used in a strap-on for pegging
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Happily Bent Over the Sink

Masturbation Month 2022 #5 (Link to Part One) Eager to be bent over the sink, Frank couldn’t get to the bedroom fast enough. He returned with the leather harness and thick purple cock, offering them to Cynthia. “No, we’re going

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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 man face down over couch receiving pegging from woman behind him wearing strap-on
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Podcast #282 – Have Issues, Want Advice

Pegging Paradise Podcast #282 Want advice – When he asks for what he wants, she shuts him down She struggles with self-confidence and the learning curve He speaks eloquently about opening up and submission She understands her husband more after

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Ruby Ryder shares Woman wearing strap-on pegging man with his hand on his penis
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The Shyness of Being Seen

Part Six – The Shyness of Being Seen Being seen on a deep level is unsettling for you. Now that I’ve flipped you over, you see my intentions, and I can almost feel you internally letting go, the better to

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Ruby Ryder shares gif of tattooed man face down being pegged by woman with strap-on
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Two Weeks of Fond Memories

Part Five – Two Weeks of Fond Memories Oh, Lordy, while we are on that subject, I have never met a man who enjoys being fucked as much as you do! We moved in together after we’d been dating for

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Ruby Ryder shares man face down on bed getting pegged by woman wearing strap-on
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A Sound Fucking Commences

Part Four – A Sound Fucking Commences You’ve passed my test, given me a lovely collection of words, and made me laugh. You have certainly earned a sound fucking, and I have every intention of giving it to you. After

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