Pegging Paradise Podcast #299 She used to peg him but not anymore. Advice? He wonders if pushing the cock and balls back behind the legs has a point? He wants to find the right formula to increase her enthusiasm and pleasure Pegging Celebration Time! He has Equipment questions after their first 3 times He comments on my article and tells a story Seven words and a grammar lesson Shout out and a question Sub seeks prostate orgasm and wants more pleasure for his mistress He's post-op prostate cancer, seeking advice about a strap-on for him He's a virgin looking for a dominant partner, advice? She said no, he made a Funky Rocker! Articles/Information Review of Strap On Me Multi Orgasm Bendable Review of [...]

(Link to Part One) Frank’s fifth day was full of reminders of his punishment the night before. From the moment he got up, even sitting on the edge of the bed, his butt smarted. He checked his cheeks out in the bathroom mirror before his shower. Yep, a few marks, as he’d expected. They stung a bit with the hot water. There was nothing like a good beating. It forced him to be in the moment so powerfully. Nothing else existed but his butt and whatever Cynthia used to deliver his ‘punishment’. He’d slept surprisingly well and suspected that was also a benefit. Once again, he thought about asking for nightly spankings when this week was over. Cynthia was still in bed when [...]

Sportsheets Saffron Cuffs Masturbation Month 2023 May 22nd - (Link to Part One) They laid in silence for a bit. Quiet but for the heavy breathing. “Do you like your new toy, Ma’am?” “Mmm… I do.” Cynthia’s words were slow and deep. “Can I see the toy, Ma’am?” Frank petitioned again, despite his better judgement. He really wanted to know what was buried in his ass, and what just sent Cynthia to orgasm land in record time. “No, Frank!” She sounded slightly annoyed. “You’ll see it soon enough. Right now, you just lay there while I fuck you. That’s all I need you to do.” Yum. She was playing into his desire to be treated like a thing. They’d talked about this before. “Yes, [...]

Masturbation Month 2023 May 22nd - (Link to Part One) “Deep breath.” Cynthia commanded Frank, and slowly withdrew the plug from Frank’s ass. Along with it went the delightful feeling of fullness. His caged cock felt heavy, hanging down past the end of the cushion. His ass was hungry for more and for something bigger. That wish was about to come true, unbeknownst to Frank. Last night was all about him, Cynthia thought, but tonight was for her. Not only did she expect to come while fucking Frank, but she hoped to come more than once. That had never happened while using a strap-on. And if she could, this toy was the one that might get her there. Her brief trial run earlier had [...]

Masturbation Month 2023 May 22nd - (Link to Part One) The new toy looked impressive; Cynthia had to admit. Frank knew nothing about her latest acquisition. She’d kept it hidden ever since it arrived in the mail. There weren't many dishes, and Frank didn't linger in the kitchen. He wiped down the table This was a different kind of toy, one that she’d never tried before. It had two ends, one that fit inside her and the other that would go inside Frank. The main reason she wanted to try it was because it had a special clit stimulator. The name of the toy included the words ‘multi orgasm’, which certainly sounded promising. Cynthia had already given it a test run before Frank got [...]

I regularly receive messages with the general theme of wanting something for nothing. Here is an example. I used to have this awesome pegging thing with my partner. I broke up with them. I can't afford a pro. Where can I find another person to peg me so that I can get my needs met? Not looking for a relationship, just the pegging. As a woman who loves pegging, and as a professional, this always ticks me off. I'm going to tell you why. First off, I am acutely aware of how much effort it takes to be the giver of pegging. A lot. When I first started seriously exploring pegging, I had some fun. I welcomed a bevy of beautiful young men [...]

The punishment he deserved. Masturbation Month 2023 May 22nd - (Link to Part One) There weren't many dishes, and Frank didn't linger in the kitchen. He wiped down the table and counters one more time, took a deep breath, and headed to the bedroom. His fear of what was waiting for him equaled his anticipation. He was familiar with this push-pull thing. He wanted the beating; he'd asked for the punishment. But he feared it, too. Mixing pleasure with pain was a challenge. A delicious challenge that had offered some profoundly thrilling rewards in the past. That was why he asked for it occasionally. Frank didn’t think he could handle getting beaten every night for any length of time, like he was getting fucked; [...]

Hump day arrives, and Frank receives another new apron! Masturbation Month 2023 May 10th - (Link to Part One) Frank awoke with a smile on his face. Last night with Cynthia had been a revelation. So that’s what a prostate orgasm felt like! He chuckled to himself to see her side of the bed empty. Off running, no doubt; her sneakers were missing from their spot in the closet. There was a yummy scent in the air that he couldn’t place, too. Interesting. Frank showered and dressed for work. Impulsively, he chose a silky blue pair of Cynthia’s panties and slipped them on. This would be a nice addition to the day! And a soothing feel against his balls. His cage was not horribly [...]

13th birthday of pegging paradise - Ruby Ryder A few thoughts about pegging from your truly on the 13th birthday of my pride and joy, Pegging Paradise! That's a long time to be talking, thinking, teaching, and let's not forget, (still) learning about the act of pegging. As I am fond of saying, I went down the rabbit hole and I'm still there! (I know my use of the word 'hole' begs for a bad pun, but I'm gonna pass.) More than anything I am happy to look back and see what I have created. A wealth of knowledge about a very misunderstood sexual activity. An activity that during these 13 years, is slowly but inexorably coming into its own. According to Clips4Sale [...]

Master Series Incarcerated Masturbation Month 2023 May 10th - (Link to Part One) Frank lay there on the massage table, so in love with Cynthia at that moment. He was completely smitten. She was a fucking goddess; of that he had no doubt whatsoever. Seems that chastity play did have a few surprises after all. If he'd known something like this could happen, he would have locked up his cock a long time ago! To be sure, that was a toe-curling, eyes rolling back in his head kind of intensity. Jesus. Frank opened his eyes again and turned to his back, smiling shyly at Cynthia. Talk about vulnerable! When your partner gives you so much pleasure that you are basically a trembling pile of [...]