“I Love Seeing You Like This” – Podcast #302

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Tag: crossdressing

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“I Love Seeing You Like This” – Podcast #302

“I love seeing you like this.” My interviewee, Steve, has heard these words many times while receiving pegging from his partner. We hear Steve’s story about how he began walking down the path of pegging and how his experience has

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Ruby Ryder shares black ribbed butt plug with remote to tease the fuck out of a partner
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Operation Tease the Fuck Out of Frank

Masturbation Month 2022 #10 (Link to Part One) Cynthia’s goal was to torture Frank with pleasure. To tease the fuck out of him. She began touching him everywhere that excited him, in exactly the ways he loved the most. She was

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A New Apron

Masturbation Month 2022 #9 (Link to Part One) Frank and Cynthia chatted while they ate, as if it were perfectly normal for Frank to be naked, sitting at the table with his cock locked in a cage during dinner. It was

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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 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 woman wearing military cap, black latex stockings and strap-on for pegging
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Podcast #289 is in the Room!

Listen to Pegging Paradise Podcast #289 No butts in the USA He discovers about real trust with pegging New to pegging but not solo play, he has size questions He lets go of the shame and guilt, and talks to

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Great News! It’s Podcast #274!

Pegging Paradise Podcast #274 He shares his crossdressing journey! He and his wife had a go at prostate massage. Fireworks! He wonders about women who peg and don’t judge. He asks if there are women who will teach guys pegging

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Ruby Ryder shares brunette woman with bangs wearing a black strapon and bra
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Podcast #259

Listen to Pegging Paradise Podcast #259 Patron/Donation update He wonders – is it okay to ask a Mistress if she orgasms while pegging? He wants to listen to the first podcasts – where to find? Post webinar – He’s feeling

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