May 24

Day 24, Orgasm 14

voyageintotheheartofdarkness

voyageintotheheartofdarkness.tumblr.com/

So the 15 minutes each day of giving myself pleasure? That was a little bit of a challenge during DomCon, but the massage was good for one day (Saturday) and a bath was good for another (Thursday)...and as I mentioned, Friday was certainly taken care of. (Sunday night was the two orgasm replay of Friday night memories. Last night was another bath, and paying with the ducky again.)

At DomCon, I felt sexy, alive and turned on, wherever I went. Hips swinging a bit more and a big smile on my face.

The other hotel guests tended to look askance at the DomCon people in our wild fetish wear and sexy outfits. I watched as women pulled their men to them possessively as if to say - don't look.

Coming back from Saturday night's party, which was way too crowded (good thing the fire marshal wasn't there...), my service submissive and I were in the elevator with a clearly not-kinky younger couple. Awkward silence. I was wearing over-the-knee boots, patterned hose, a leather miniskirt and a corset. Quite sexy, but somewhere in the middle in the range of wildness that presents itself amongst the attendees of DomCon, especially at the play parties. This couple in the elevator, though, they couldn't have known that.

I looked over at my service man in his suit and watched him pull the key card out of his pocket just as we reached our floor. We departed the elevator and the couple continued to a higher floor.

"You know what the assumption was there, don't you?" I smiled because he was so into service mode that I could tell he hadn't noticed.

"What do you mean...?"

"That couple on the elevator. To them, you were clearly the wealthy businessman and I was the hooker."

We laughed raucously in the hall at the misconception. My corset was loosened, boots removed and my feet massaged. I remember thinking, I could get used to this. And then I self-corrected, though still not out loud and thought to myself, I will get used to this, because this is the kind of man I am looking for.

2016-05-22_00.35.07[1]

 

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May 24

Pegging Article!

Written by Life On the Swingset's own Kat Stark!

Kat is a sex-positive, geeky, Canadian, pansexual pervert who came to the non-monogamous lifestyle 21-years into her relationship with her husband. After a quick toe-dip to test the waters (and hours of obsessive reading and podcast consumption), they dove in and she almost can't imagine they lived any other way. She isn't sure whether they fit the traditional definitions of swingers or poly, probably landing somewhere in between, but surely, redefining traditional concepts is what the lifestyle is all about. @WetcoastKat on Twitter.

I have to say that him straddling me and panting and sweating while fucking himself on my cock is the hottest visual.

Read the entire article here!

 

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May 23

Day 23, Orgasm 13

sensualpegging.tumblr.com

sensualpegging.tumblr.com

Well, well.

DomCon was quite an experience-filled weekend. All good.

Thursday night I was running late packing everything up and leaving the house for 4 days, so I missed the Mistresses dinner. Decided not to stress about it, and even found someone who was looking for a ticket to the sold-out dinner, which worked out well.

Friday I lounged around the hotel in casual clothes, not yet ready to put on any constricting fetish-wear.

Friday afternoon/early evening I had a visitor. Quite a big, strong, and fit visitor, actually.  His G-Spot skills were remarkable; I squirted twice. And I fucked him soundly for a long luxurious time. 😉 We enjoyed intensely hot hotel sex for 4 hours, before he had to leave. That really set the tone for my DomCon adventure. I walked around in a well-fucked kind of mood all weekend. So did he. 🙂

My lovely service submissive (which I found by putting an ad up in the DomCon group on FetLife.com) arrived late that evening to begin his service and escort me to the Friday night play party. He loves serving and I had an extra VIP pass plus a hotel room. So though the chemistry wasn't right for me to engage him sexually, he served me practically flawlessly all weekend.

I had coffee fetched and brought to me each morning at the time I specified. I enjoyed doors opened for me, food brought to me, arms held out to steady me when I was in heels, and foot massages. Dressed smartly in a suit, he escorted me to play parties  both Friday and Saturday nights, and he fetched me my drinks all evening. I had his assistance dressing/undressing with corsets and boots (he even took a corset lacing class there at DomCon). I led him through giving me a back, shoulder and neck massage on my massage table, which considering he'd never given a massage before, he did quite well at. He was also fine with absenting himself from the room when I wanted time to myself.

I was very happy with my choice to allow him to serve me.

On Sunday, I taught 2 classes, and his support before, during and after was indispensable. Luggage carried to and loaded in my car. All with a smile and such earnest willingness.

It's Monday now and I really missed having my coffee brought to me this morning...

My right shoulder is still a bit sore from the beating I gave my Friday visitor, and my pussy is just a bit sore from the fucking he gave me. When I got home I replayed the sweet spots we shared in my mind and enjoyed not just one but two orgasms. Yum.

I love my life.

 

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May 22

Day 22, Orgasm?

domina-et-servus.tumblr.com

domina-et-servus.tumblr.com

 

Continued...

I remove his butt plug and throw it down on my skirt, to be handled later.

Chicago Man is so ready, in such an intense state of need.

I spank him, gently at first. I love to fuck a red, sensitive ass and I will not be denied it, no matter how intense his need is.

When the redness begins to appear, I place the head of my cock against his ass and push just the head in. It's not much larger than the plug and he takes it easily. But I pull out again and continue his spanking. He whimpers. Music to my ears.

Next penetration about an inch further, and then out again for more spanking. The sound that comes out of him is tortured and incomprehensible. Excellent. Back and forth 3 more times until finally, with loud moans from him, my cock sinks all the way into his ass.

I grab his wrists and use them for leverage as I begin to fuck him, hard and deep like he's wanted me to since I was eating my chocolate mousse at the restaurant. I turn on the vibe in my harness and just use him for my pleasure, fuck him over and over until juices run down my legs and trembling, I come hard and long against him.

I pull Chicago Man up from the couch, push him down on his knees and then onto his back, laying on the carpet. His pants are still around his ankles and his shoes are still on. He is effectively hobbled, with wrists still restrained behind his back.

His cock is hard and dripping. I climb onto him and slide it deep inside my hot wetness, swooning. Chicago Man has a nice cock. The sheer pleasure of my hot, slick pussy astonishes him and his eyes lock with mine as his mouth opens. I begin to ride him with purpose, fucking him relentlessly. Finally I place my hands around his throat and begin to squeeze. The power of the roars that come out of him seem to match the strength of his spasms, the spasms that shoot come so hot inside me, I can feel it.

It was a good idea to have that dessert.

 

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May 21

Day 21, Orgasm?

peggingwithasmile.tumblr.com

peggingwithasmile.tumblr.com

Continued...

I drive home and play with the remote all the way. It's a 15 minute drive from the restaurant. He is no longer quiet now that we are alone. His moans are loud and occasionally high pitched when I turn the plug up to the strongest setting. He reaches his hand down to his swollen cock reflexively and squeezes it.

"Don't...touch." My tone leaves no room for anything but obedience. Immediate he lets his cock go and clasps his hands together, needing a place to put them.

"Yes, Ma'am! Oh! Please."

"I know. You were such a good boy during dinner. You'll get your reward." I smile at his discomfiture. He loves this. The waiting. The erotic torture. My control.

Immediately after walking in the door, I lead him over to the couch. I stand behind him and reach around to unfasten his pants while I gently bite the back of his neck. Pants to the ground and I push him over the back of the couch. I retrieve lube and wrist restraints from my purse. I planned this evening so well.

Wrist restraints go on Chicago Man and are fastened behind his back.

I slip out of my skirt to reveal what I've been wearing all during dinner, a harness and pretty blue cock that I'd tucked between my legs and kept there with a tight pair of panties. Off go the panties. On goes the lube, all over my cock.

One more press of the remote and a squeal comes out of Chicago Man that delights me.

He's been waiting so long for his reward...

 

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May 20

Day 20, Orgasm ?

pariscowboy.tumblr.com

pariscowboy.tumblr.com

Reliving hot experiences with awesome men...yes. That has definitely provided masturbatory fodder. In fact I more often masturbate to thoughts of specific men as opposed to nameless fantasy men.

This time it's about Chicago Man, because he occupies a lot of space in my erotic treasure chest these days.

We are out to dinner. He has a vibrating butt plug in and of course I have the remote. In fact it sits right there on the table next to my plate. True, those in the know would recognize it. Even if they did, they would just smile and have a whispered conversation with their companions...and share in our erotic energy there in the dining room.

I play with that remote mercilessly during dinner. I hold it in my hand with my thumb on the button and just...hold it, having a relaxed conversation with him about nothing sexual. He squirms a little, and then more, every time I turn it on. I play with the patterns of vibrations, and the strength.

I order dessert, much to his chagrin, and coffee to accompany it. He squirms.

Finally he puts his hand over mine and looks at me with pleading brown eyes.

"Please."

I see the fire. I see the need. I press the button again, and wave at our waiter.

"Check, please!"

 

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May 19

Day 19, Orgasm?

pariscowboy105

One of my favorite fantasies goes way into the 'fantasy' territory.

I am Queen of a kingdom. I get the hottest men together in my castle to play once in a while. With me, and with each other. I match them up in pairs - at my whim. They are required to fuck each other while I watch. Who fucks whom is determined by a coin toss. They have all been trained to be considerate, skilled tops and receptive bottoms. This is for my viewing pleasure, but for their pleasure as well.

The scene around me is unbearably erotic as I watch what basically amounts to live gay porn all around me.

I look over and see a large muscle-bound man fucking a small, slim bottom without regard for his enjoyment. He's getting too aggressive and the bottom looks to be in pain. I order them to stop, and decide to punish the large man. All the other men stop their fucking and help to tie him down to a spanking bench. His legs are wide apart and he is very exposed.

I whip him and use paddles and leather straps on him until he is crying out with every stroke. As I beat him I lecture him on the proper way to fuck an ass. I am livid. All the other men stand around and watch the spectacle. Finally I strap on a cock just a little too large and give him a taste of what he was doing to the smaller man. He will sit carefully for the next few days.

I leave him tied to the bench, in tears, and go back to my throne, ordering the men to continue fucking each other. The smaller man I invite to kneel at my feet and push his head between my legs as I watch all the fucking resume.

It is good to be the Queen.

 

Note: Please know that I never condone causing pain through anal sex. The fantasy can be hot, though!

 

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May 19

Podcast #133

newryder9

Pegging Paradise Podcast #133

❤ Pegging mentioned in Cosmopolitan online
❤ She wants the biggest double out there!
❤ Ethical Non-Monogamy
❤ He found a pegging partner but now she wants him to be with a man. Help!
❤ He says Kegel exercises calm down his hemorrhoids
❤ Kegel exercises can do much more, including improving your sex life!
❤ "Waking up the Prostate" information
❤ She's naturally dominant and finally found a partner who loves that about her!
❤ He's single and wants it bad. Where can he get these cravings met? How to handle dating?
❤ He’s getting divorced 🙁 Where to find women who like pegging?

 

Linkorama
Cosmopolitan - "I'm a Straight Guy Who Loves Pegging"
Article - Navigating towards Non-Monogamy
Article - What I Love About Pegging
Where can I find a woman to peg me? - Collection of articles

Kegel Exercisers
Private Gym for Men
Minna kGoal for Women

Self-Play Toys
Aneros Helix Syn - Waking up the Prostate
Njoy Purewand
Suction Cup Dildos!
Hugo Prostate Massager
Loki Prostate Massager
Loki Wave Prostate Massager

Patreon - Support my work!

 

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May 19

Off to DomCon I Go!

bendoverboyfriend.tumblr.com

bendoverboyfriend.tumblr.com

Later this afternoon I will be headed down to DomCon. No telling what awaits me!

Plans change in a flash and it is the tail end of Mercury Retrograde, after all.

The big strong guy who was going to join me there and serve me, was beset by illness and regretfully cancelled. So I'm interested to discover what the Universe will bring me this weekend instead!

Angel_Bojangles

 

 

Two years ago this man came into my classroom, dressed pretty much exactly like this picture...that's the amazing thing about DomCon, this kind of dress is allowed. And by the way, that's a thong he is wearing. I asked him to come up and be my model to demonstrate good pegging positions. Best model ever.

We ended up have so much fun, at parties and back at my hotel room. (And yes, I have permission to use his picture.)

See why I trust in the Universe? 🙂

 

 

 

 

So meanwhile...I don't foresee that I will have the time to manage daily Masturbation Month posts in addition to having ALL THE FUN. So I'm going to bank a few for you all, so you get your daily fix of eroticism.

You'll notice that my orgasm count will be a question mark over the weekend. I will fill you in on what exactly ALL THE FUN entailed (pun intended) when I return, and update my number of orgasms!

Have a great weekend!

♥Ruby

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May 18

Day 18, Orgasm 11

peggingwithasmile.tumblr.com

peggingwithasmile.tumblr.com

 

"It's pink," she said, matter-of-factly.

"Seriously?" He sounded disbelieving.

""Seriously!" She laughed. Too bad if he didn't like it, he'd refused to shop with her for the equipment. Such a push-pull with this man. He wanted to get fucked but didn't want to actually admit that he wanted to get fucked, say it out loud, get eager about it.

She knew he wanted it, though. That night when his tongue had been loosened by tequila she'd discovered his secret. He denied wanting it when she asked the next morning, then sent her an email with links to equipment. He wouldn't get online with her and make the purchase, but he put money in her account to cover the cost.

Tomorrow was the night. She'd explained that to him several times. He couldn't even respond to her when she talked to him about it. His cheeks just turned red and he wouldn't meet her eyes.

So, fine. She'd put a gag in his mouth and have her way with his ass, preparing him for the new toy. That way he wouldn't have to be embarrassed that he couldn't speak, he could blame it all on the gag.

And then slowly, inch by inch, she'd sink that bright pink cock in his ass. Just like he said he wanted that night he'd done 6 shots of Patron. And then she'd see if he'd talk.

 

 

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