May 04

Day 4, Orgasm 3


Porn is an interesting thing. There are three factors that when included in a porn clip, will turn me on more than any other. Reality/enthusiasm, one or both of the people making noise, and anal penetration.

Found a gay clip recently where the top is so clearly into the bottom's ass, playing with it, biting his cheeks, slipping fingers inside. He already sounded worked up by the time penetration happened. Never heard a peep out of the bottom, although his hard cock and balls were in a cock ring and pulled back between his legs to be visible.

The top was so vocal when he came, quite loud and authentic. He was all over that ass!

So fucking hot.

Definitely sent me over the edge, laying there in my bed with my phone and earphones connected...watching porn.


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May 03

Day 3 Orgasm 2

A Bondage of Fake Pearls


Jesus Christ! Who was this woman?!

Randy just wanted a quick, uncomplicated hookup that night and Harvey's seemed the logical place to score. He'd had good luck there before. He headed down to the pub and tried to discreetly scan the possibilities right after walking in the door. Halfway through his visual sweep and halfway to the bar, there she was. The reddest of lips and a mischievous, amused look on her face. Miranda stared boldly at him with an expression that told him he'd been caught checking out all the women. Her smile said there was nothing wrong with that, though. That's what Harvey's had a reputation for. Looking to get laid? Come on down.

She crooked a finger at him and patted the bar stool next to her. She was alone. He sat down next to her and halfway into the second drink it felt inevitable that they would end up in bed together. And they did. But before they left the bar, Miranda had a strange request.

"Just don't fucking talk to me, okay? I am so damn tired of all the talk. Just pretend I speak a different language - one you don't know. Okay? Do that for me and I'll happily take you back to my house for some fun."

Well that was certainly different. That was the moment when Randy started talking to Jesus and wondering what Miranda's deal was. But he didn't let that stop him.

Her house. A sumptuous canopy bed surrounded by flowing white curtains. In his buzzed state, it felt like a dream to Randy. Miranda took off Randy's clothes and made out with him for a while in that cocoon of cozy passion. Then she pushed him back on the pillows, stripped down to her fake string of pearls, slipped a condom on him (that she seemed to pull out of nowhere), climbed right up onto his cock, and rode him! Randy loved aggressive women.

Ride him she did.There was a moment when he was close to coming. Miranda could tell from his breathing and his muscles starting to tighten. She stopped moving on top of him and wagged her finger at him while shaking her head, wordlessly. Randy nodded in understanding. He had decent control. He could do this. She continued riding him until she came, trembling and moaning. He was still hard. She smiled her appreciation.

Miranda rolled off of him and pulled his face into her pussy, forcing him to taste her juices, tainted by a slight condom flavor. He didn't mind. He loved eating women out. But she didn't give him long before she pushed him onto his back again. She hopped off the bed and pulled a harness and dildo out of her dresser drawer, and cinched it down on her hips while she gave him a one-sided smile.

This wasn't Randy's first rodeo, but pegging and one night stands usually didn't go together. He hadn't exactly prepared for this. He held his finger up in the universal one moment please sign and scampered off to the bathroom. Five minutes later he returned, cleaned out, cock soft, no condom, and bearing a towel, which he laid down underneath himself, resuming his position on his back.

Miranda smiled and nodded her thanks. She took some lube and started to play with Randy's cock, which quickly responded. Then she did an odd thing. She took off her fake pearls and put them around the head of Randy's cock, almost like mini reins.

Randy wouldn't think it was odd later, as Miranda fucked him with his legs in the air. He would think it was fucking brilliant as Miranda slid her sparkly purple cock into him over and over as she tightened those pearls around the head of his cock little by little until he wasn't sure which sensation was going to overwhelm him first, the pleasure of his fucking or the pain of his cock in bondage. A bondage of fake pearls.


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May 02

Day 2 Orgasm 1

Good Boy


You arrive exactly on time.

You're here...for me. To do whatever pleases me. Whatever brings me the comfort or release or satisfaction that I need. It's different each time. Your instructions are printed out and ready for you on the kitchen counter.

First, all your clothes come off. I always want you naked.

I have everything you need to make us a simple dinner. The recipe is there for you to follow. I sit and sip wine, feet up, reading a book, while you cook. We are both quiet. Soft music plays in the background.

Per my directions, right there in the recipe, you periodically come over to me, rub my shoulders and run your fingers through my hair. Then you resume cooking, glancing back at me with a smile.

  • Combine all ingredients in a large bowl.
  • Mix well until vegetables are well coated with oil and seasoning
  • Go rub Ruby's shoulders and run your fingers through her hair
  • Place vegetables in a 11" x 14" baking pan

Dinner is minimal but tasty and nourishing. It will sustain us into the evening. While we eat, you occasionally get up and rub my shoulders and neck. That's in the recipe as well.

  • Bake in 400 degree oven for 25 minutes
  • Drizzle balsamic reduction over vegetables and serve
  • While you eat, occasionally get up and rub Ruby's shoulders, and run your fingers through her hair
  • Offer her more wine when her glass is low

Mmmm. I'm being fed a meal that I didn't have to prepare. I'm being attended to and pampered. I'm smiling.

Comforted? Check.

Dishes are abandoned. Who cares about dishes when my needs are being met? Not me! We move to the play room because I'm ready to play.

You are on the massage table. I have you tightly restrained. I start off with a flogger, warming you up. Though I occasionally hit your back, your ass is what I am most interested in, naturally.

I methodically work through my collection of floggers, paddles, and straps, finally ending with my crop. I don't rush you, because my intention this night is to release some of my stress. It's been a tough week. We have done this dance before and it's one we both love.

After a while, your ass is covered with marks you will be proud to show me the remnants of three days hence, and my forehead shines with sweat. I pull on a harness with a medium sized dildo, climb on top of you and fuck you with little ceremony.

You are face down on the table, unable to move. I lay my body down over yours and push into your ass, knowing your cheeks are still sore. The sheer physicality of beating and fucking you is a workout for me, and offers me the release I seek. Your moans become louder and louder. I stop just shy of your release, intentionally. You whimper. After a bit, I resume fucking you, and again stop just before your orgasm. This is a delicate line to walk but I've gotten quite good at it.

The fourth time I stop, you let out a kind of growl, which surprises and delights me. I pull out, take off the harness and release your bonds. I tell you to get off the table. Your cock stands at attention as you slide to the floor. I grab it and you groan. I smile.

Release? Check. For me, at least.

I slip onto the massage table, turning on the heated pad underneath. I feel my body sink into the warmth. You massage my back, with a slow, confident touch that works out the knots in my shoulders and nearly puts me to sleep.

You ask me to turn over and I do so languorously. My smile is a natural part of my face, now, instead of a reaction to your ministrations. Your hands continue to caress me, only occasionally touching areas that arouse.

That was in the instructions as well. After I turn over, your touch must constantly have these two qualities: teasing and gentle.

You really are quite adept at following instructions. I take care to use specificity when I write instructions for your visits. I know that whatever details I describe will come to life. You are willing to do whatever pleases me. It's a heady feeling, that level of control.

Your fingers circle my nipples and tease my clit ever so gently. Perfect. Leaves me reaching for more. Exactly where I love to be. Finally, two fingers are inside me, pleasing my G-spot with strokes that feel just right, and you are kissing me, holding me while I tremble, and tears slide down my cheeks.

The intimacy of it all is temporarily overwhelming, and you immediately get that. Your arms encircle me and your lips against my ear, whisper, "I'm right here, babe. For as long as you need me to be."

Laying there on that massage table, I am feeling grateful. That I have a man who will cater to my needs the way that you do. That you know exactly what I need when I get emotional - holding, tenderness, acceptance. And that you follow my instructions to the fucking letter, setting aside your own needs, for mine.

Satisfaction? Check. Mine, at least.

We crawl into bed together and you spoon me. No, you will not be allowed to come tonight, but you will not complain. You know better. Your full cock finds a natural home between my thighs, and I nestle back against you. Sleep finds me quickly. You work hard not to fidget, your heavy balls a reminder of your need.

The next morning you wake with a hard and dripping cock. But you dress, clean the dishes, and take the linens off the massage table to put them in the laundry. You return to the bedroom to find me still dozing. You run your fingers through my hair for a bit and kiss me goodbye. As you leave, I murmur my appreciation with two simple words.

Good boy.

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May 01

Day 1 Orgasm 1


She pushed him against the wall, sliding the dildo deep into his ass.

"I know how much you love this, baby..." She whispered the words into his ear even as she drove her cock deeper.

"Ohh! Ohh! Ohh!" Every thrust brought the same whimpering sound out of him, without his consent.

He didn't know which way was up, and he didn't care. All he cared about was the amazing sensation of that toy caressing this insides, creating a buzz of excitement that began to spread over his whole body. Her breasts against his back, her hands on his hips, the scent of her; all of it came together in a level of arousal he almost couldn't handle.

"Let's see how long you can last this time, baby." She began to count. Whenever she counted, it sent him over the edge. He had no idea why. She'd found out it worked completely by accident. But work it did.

"One. Two. Three. Four. Five..."

This time, five was the magic number. Five was when his mouth opened in shock at the thrills shooting through every part of his body. She helped hold him up, burying her toy deep inside him and thrusting softly against him as he rode the peaks of intense pleasure that left him speechless.

He'd tried to say no, that afternoon. She came out of the bathroom wearing the harness and he shook his head, trying to avoid what he knew would be an experience of vulnerability so complete it scared him. That's the way it was every time. But she wouldn't take no for an answer. She pulled his jeans down around his ankles, pushed him against the wall and fucked him.


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Apr 30

Masturbation Month 2016!!!

Well here we are again...the merry month of May is upon us! May brings a lot of merry in my world, and I love to share that merriness with you all!

If you'd like to know the story behind how Masturbation Month orginated, Click Here. (Thank you, Joycelyn Elders!)

There is a time-honored tradition here at Pegging Paradise, one so sexy that you might want to check out my archives for the months of May in previous years. For the entire month of May, I post every single day. I share what turns me on, what titillates me, what sends me over the edge when my fingers or toys are bringing me to peaks of pleasure. Guaranteed to spice up your May. Sometimes I find a picture that tells a story and write that story. Sometimes it's a tried but true fantasy that never fails to get me off. And once in a while it's a fantasy I've never tried but long to. I combine all this sexiness with my usual curated collection of photos. It's such a win win win win...LOL

So...for May of 2016....

I invite you to take my Pegging Paradise Masturbation Month Challenge!

Pleasure yourself every day  for a minimum of 15 minutes

I have recently discovered the joys of edging, so I'm not going to insist you have an orgasm every day, though you certainly can if you like. I just want you to pleasure yourself, in some manner that makes you and your sexy bits happy, for at least 15 minutes every day. Feel free to write in and let me know how things are going. And if you don't get to it for a day or two, jump right back on the sexy wagon and start again. Perfection is neither expected nor required. I just want us all to have bigger smiles on our faces at the end of the month....K?

Who's in?


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Apr 29

Podcast #131 – Crossdressing!


Pegging Paradise Podcast #131 Crossdressing

❤ His Aunt Linda trained him from the start!
❤ It started with a dream and now he wears panties and pantyhose every day!
❤ Joanne's crossdressing is an "all or nothing" experience - and she has her own room!
❤ He looks forward to combining pegging and crossdressing, and wants a spanking first!
❤ Fransesca was introduced by a part-time domme
❤ He's on the DL and is a very horny crossdresser
❤ This alpha male likes to pretend to be a woman every once in a while.
❤ It all started with panties!



Podcast #112 - For the Ladies

Zion Pic!!

May 15th Classes in Long Beach

Ruby on Comedy Central!


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Apr 26

Hey Guys – Unsure about Exploring Your Ass? Listen to What This Guy Has to Say…

Zachary Zane

Zachary Zane

"It perplexes me how men who seem to value sexual satisfaction above everything else refuse to let anything enter their rear. If they just dropped their heteromasculine facade, they could start having real pleasure. Real intimacy. Real connections. Real empathy. There’s no reason why only gay and bisexual men should get to experience all the good stuff."

The above is a quote from an article titled "Why I Believe Every Man Should Experience Being Penetrated" by Zachary Zane, the handsome man above.

Do yourself a favor and go read the entire article!

I can talk all day long about how much pleasure can be experienced with prostate play, but sometimes it's different hearing it from someone who actually has a prostate.


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Apr 20

I’m BACK!!

Zion National Park

Zion National Park

Refreshed and relaxed, ready to kick some ass and take some names. Wait, what was I thinking! That's fuck some ass until he is calling my name! Right? There's nothing quite like getting out in nature, especially nature as beautiful as this. Sitting by the campfire, under the stars, breathing fresh air...being outside for days at a time. It's good for my soul. I hope you all regularly take time out for yourselves in the way that most nourishes you!

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Apr 14

Headed to the Mountains…


Taking a break from all the exciting stuff that's been going on!

Time to clean out my brain and the best place for that, in my world, is the mountains.

Back Thursday the 20th, so you have until then to get me your crossdressing stories for the next podcast!!



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Apr 11

Comedy Central Talks About Pegging!!

Ruby's TV Debut - spreading the word about Pegging!

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