Tag Archives: anal sex

Early morning erotic musings

Sleep is something that seems to elude me lately.

Sleeping with a broken jaw is turning out to be difficult – or perhaps more accurately – turning while sleeping with a broken jaw is difficult…  I keep turning over onto the side with the break while I’m sleeping and waking myself up.  It is just ever-so-slightly maddening.

But it does give me lots of time to think.

I have a new submissive trainee.  She is wonderful.

I want her to burn for me, and I told her that I would leave her be until today while she saves herself for me, but after today, all bets were off.

I planned to share this story with her, but I know she’ll see if it is here, and I thought perhaps the rest of my readers might benefit as well.

Plus – who doesn’t like a little voyeurism into the life of their favorite online Dom?

While slightly embellished, this is a story based on reality and the names of the parties involved have been changed to mask the identity of the guilty, but if you happen to be reading this and know who you are – I’ll gladly remove the story at your request.

I have a fetish that I have never fully satisfied.   I’ve had a pretty varied sex life to date, and I’ve actively sought out every fetish that I have been able to identify so far, including this one, but I haven’t quite managed to hit the right combination of factors yet… the short version is that I have a desire to have sex with a fully unconscious woman.  Consensual, of course – pre-negotiated, adhering to limit terms even while unconscious, etc.  But, as you can imagine, this is a tricky thing to negotiate.  It requires a seriously intense amount of trust.

My new trainee is willing to satisfy this for me, at least in theory, and for that I owe her much, including this story.

As I said, this is a fetish that I have not yet been able to fulfill, but I do have something of a confession to make.  While it is true that I have not fulfilled the entire fantasy of mine, I have, sort-of, possibly, had sexual intercourse with an unconscious woman before, but she didn’t start out that way, and I didn’t drug her or anything nefarious like that.. in fact, I’m pretty sure that the experience was pretty profound for her, but I’ll relate it now in full.


I would like to preface this story with the fact that this happened several years ago, and at the time I was a very different creature, emotionally, than I am today.  I was a more callous, hurt, and dangerous person, but I don’t want to sugar-coat my past.


This all happened several years ago.  I was freshly broken up again, which seems to be a recurring theme in my life, but that’s not the point.

During the course of my relationship, which was mostly polyamorous, my girlfriend told me that I could have sex with anyone I wanted to with the exception of three people, two of which were her friends and the other .. is not important.

One of these friends and I had some serious sexual tension from the time we first met.  Within moments of meeting, we were locked in a kiss and my girlfriend had to separate us and ask us not to pursue each other because it was going to induce Ratatosk-sized brain squirrels for her if we were to continue, so – since we both loved her – we stopped and let it drop from that point forward.

Let’s fast forward a bit to where I was broken up with.  This friend was one of the few who remained friendly with me in the aftermath.  I know that her motives were not entirely selfless, but then again, neither were mine.  The sexual tension had never completely dissipated.

In my sorrow at being emotionally wrecked yet again, I was out drinking at a strip club and I received a text from this woman – let’s call her Ruby.

Ruby texted me, letting me know that her date turned out to be a dud and that she was home alone, waiting for her girlfriend to get back from the kink event that she was volunteering at..

Home alone safely now. Date was a total bust. The guy was at least four inches shorter than he claimed and he was about as Dominant as the gum under my shoe.  Now I’m just sitting around and waiting for Ariel to get done at the Citadel.  What are you up to?

Interesting, I thought to myself.   It was about 10:00pm and the event that was going on was going to go until 1:00am at the earliest.

She was sitting at home, looking at three hours of doldrums ahead after having had her fires stoked for a bit by a guy who turned out to be a total schlep.   I was already horny, a little bit drunk, and not looking forward to the prospect of bringing home another stripper for meaningless and somewhat risky sex.

Besides, Ruby was hot and I wanted her more than any of the girls who were hanging off of me because I’m respectful, good looking, and came with lots of cash…  How can I work this to my advantage?

I’m just sitting here watching London climb the pole topless and waiting for her to finish her stage show so that I can try to talk her into blowing me in the back room.

Leave out lots of information… make the pieces that you do reveal tantalizing… tilt the direction towards the thing you want… it’s okay, she wants it too…

Oh really?  Who is London?  Where are you?

Bingo. Gotcha.

Absolutely.  She’s a rather attractive young girl who would really like my money.  I’m at the Hanky Panky, drinking way too much and trying to forget why it’s a bad idea to offer London money to suck my cock.

Damn, I’m horrible… I might as well be hanging out a sign saying, “I want sex and my inhibitions are down.”  The real question is whether or not she’s really been hooked and will let me reel her in now, or if I’ll have spooked her.  Even with the pre-existing tension, trying to reel her in with only a couple of text messages is pretty bold.

You mean that horrible dive bar/strip bar in Redwood City?

That’s the one.

Yuck.  Isn’t that place gross?

Now I know that I have her.  She’s making disparaging remarks towards the competition and seeking to elevate her place in my eyes.

Meh.  It’s not so bad… once you’re six or seven drinks in, anyway.. and London is very cute.  Much too young for me, but that never seems to be much of a problem.

Now I’ve reinforced my claim that I’m dis-inhibited (nevermind the fact that this is true, at the time, I was rather full of myself) and I’ve let her know that her competition actually has my attention, I should become irresistible…

You really should stop robbing the cradle, Rant.  I would think that you’d have learned to appreciate the experience that comes with a few more years by now.

* evil grin *

You’re not suggesting that you would be a more suitable tribute than young London here now, are you?  Besides which, you’re still several years younger than me.

Three years is not several.

I have to admit, at this point, I’m pretty excited.  I’ve wanted to nail Ruby for well over a year at this point and I’ve been denying every impulse.

I can’t drive at this point, but if you’d like to come get me, I might be persuaded to leave now.

I’ll be there in ten.

Holy shit! Did that just happen?!

At this point, I have to actually get rid of London, because she really is sitting on the stool next to me with her hand in between my legs and asking me if I’d like to go back and have that ‘private dance’ with her now.

I politely tell her that I’m not feeling well and that I need to close out and leave, but I give her a $20 for sitting with me for the couple of minutes that I was arranging for what would turn out to be rather extraordinary.

I closed out my tab at the bar and walked outside, to wait for Ruby to show up to pick me up.  One of the other dancers was outside and took the opportunity to chat me up and handed me a slip of paper.  It happened to have a name, phone number, and email address on it.  I figured I’d keep it for later, so I put it into my pocket, but I ended up losing it – sorry, Cheyenne…

Moments later, Ruby pulled up to the street next to where I was standing and rolled down the window of the passenger side door, on the curb next to me.  She leaned over to look at me through the open window, “Hello, Sir.  I’m ready to take you home now.”

“Thank you, Ruby,” I said as I opened the door and sat beside her in the passenger side.

“I’m not sure this is a good idea,” she said as we pulled away.

“It almost certainly is not,” I replied. “But I’m not altogether certain that I care.”

“I agree,” she said, and then not another word all the way back to her place, which was not far.

“I suppose I should have asked if you wanted me to take you home, shouldn’t I?” she asked demurely once we’d pulled into her parking spot.

“Don’t be foolish,” I said, “this has been over a year in the making.  Show me upstairs.”  I already knew the way to her apartment, having been there several times in the past, but I wanted her to lead me.

She led the way to her apartment and I followed.

Once inside the door, I closed it behind me and then turned around to find her only inches away from me, looking up at me, directly into my eyes.

“You don’t smell good, Sir,” she said, without the slightest hint of guile.

“Does that matter?” I asked, knowing that I was in the throes of grief and had not been taking care of myself for several days, not to mention the fact that I had recently been drinking heavily and even smoking a bit – which I am somewhat ashamed to admit that I occasionally do when I’ve been drinking.

“No. I suppose not,” she said, in the most demure voice I’d ever heard. “I want you,” she said afterwards, while looking me directly in the eyes with the most innocent eyes she could manage.

“I am here, Ruby.” I said, with all the gravitas I could summon, and shockingly, it worked! She dropped to her knees in front of me, wrapped her arms around the back of my thighs and looked up into my eyes.

“May I suck your cock, Sir?  I’ve been waiting ever so long to do so.”

“You may, Ruby.”

She undid my belt, slowly, with purpose.  Then she undid the button at the top of my jeans, then the next one down in the fly, then the next, and finally the last one.

As she started to pull on my pants to bring them around my ankles, I held onto my belt, pulling it free as my pants fell.

Then she brought her hands to the front of my boxer briefs and stroked the bottom of my cock, from balls to head, through the fabric of my boxer briefs.

She looked up again into my eyes, pleading for me to give her permission to pull my boxer briefs down, even though the permission was already implicit in my affirmation that she could suck my cock.

I put my hand under her chin as she lifted her head, and tilted it back.

With the other hand, which was holding my belt now, I quickly looped it around her neck and pulled it taught, dragging her upright on her knees.

Then I pushed my boxer briefs down and pulled my rigid cock free, letting go with my hand to allow the belt to settle around her neck and come to rest between her breasts, still covered by her clothing.

I grabbed the back of her neck with my free hand and guided her mouth around my cock.

I thrust slowly in and and out a few times, deeper than was comfortable for her, but not enough to cause serious discomfort.

Then I grabbed the belt again, and pulled her off of my cock, and up to her feet.

I stepped out of my pants and my boxer briefs and I walked her back, forcing her to back up several steps until she was abutted against her ottoman.

Then I let go of the belt and I leveled my sharpest gaze directly at her soul and I said in my Command Voice, “Remove your clothing and lie on this ottoman on your back.  I want to eat your pussy until you scream.”

Before thoughts were registering in her mind, I think, she had removed her top and was halfway through removing her bra.

“Wait – can I put a towel down?  This is new furniture….”

“Yes, of course, but if you make me wait any longer I’m going to hurt you.”

“Yes Sir!” and with that she quickly removed her remaining clothes, ran to put a towel on the ottoman, and laid down upon it, on her back, spread legs in front of me.

Cunnilingus is my favorite sex act… it allows me an awful lot of control over my partner’s orgasm, and I really like that kind of control.

I dropped to my knees and closed in on her gorgeous pussy.

I thrust my tongue deep within her and then drew it up through her inner labia to her clitoris, and as I did so, she let out an audible moan.

I focused my attention on my tongue and her clitoris for some time after that, bringing her to a state of near frenzy and backing off to deny her orgasm several times.

Eventually her frustration was staring to climb and she called out in an exasperated tone, “Sir! Are you ever going to let me cum?!”

“Why should I?”  I asked in the calmest, clearest tone that I could.

“I thought you said that you weren’t a Sadist?!!?”

“I said I’m not a physical Sadist.”

“This feels pretty fucking physical to me!”

“You’re right, Ruby,” I said and then immediately put my right forefinger and middle finger into my mouth to wet them, and then thrust them with nothing held back deep into her pussy.

She exploded with her first orgasm, shaking and moaning.

I began to feather my fingers inside of her, hitting her g-spot as I put my face back between her legs and started circling her clitoris with my tongue again.

“Ugnghshg!”  – She can be pretty eloquent when she’s cumming.

“ARGH!” she screamed out as every muscle in her abdomen contracted at once and she came extremely strongly, pushing my fingers out of her with the force.

“That was almost a word,” I said, sarcastically.

“ARGH!” she replied, so I stuck a finger into her asshole.

“UGHAASHUEDUDSAVJ!” she squirted all over me and pushed my fingers out of her vagina again, but the one in her asshole remained, so I curled it on her.

“HOLY FUCKNUTS!” she screamed, which I took as an invitation, so I put my fingers back inside her and attacked her clitoris with my tongue again.

“AGISDGDH! What?! WHo?! How?!?”

I straightened up so that I could look her in the face, because reactions like these really need to be seen to be understood.

I pulled my thumb up to start pushing on her clitoris.. not moving around, just steady and increasing pressure.  I was kneeling above her now, so I could see the fact that she was holding her breath.  She was starting to turn purple, but I didn’t want to stop what I was doing, so I pulled my finger out of her ass and stuck the tip of my cock in instead.

“AHDFGSHDSAJD!”

I began to push with my hips while I was continuing to kneed at her g-spot with my fingers and push on her clit with my thumb.

By the time I had half of the shaft of my cock in her ass she had squirted again, her eyes rolled back into her head, and her body went completely limp.  Her arms flopped back behind her, and the action pulled her tits up and forward and that made me even harder, if you can believe it.

Now balls deep inside her ass with my cock, two fingers into her pussy, and putting increasing pressure on her clit with my thumb, it was clear that she had passed out.  She was still breathing though, and making noises that were somewhere between a moan and a ‘coo,’ so I just kept fucking her ass.

A few moments later, I came in her ass, pulled out, pulled her body against mine and held her while she tried to catch her breath.

Eventually she came back around and she looked up at me and smiled and said, “Thank you, Sir,” before dropping her head onto my shoulder and trying to steady her breathing.

I helped her to clean herself up, and clean up the mess we’d left behind.  I put on my clothes and then I walked home.

It was a pretty intense night.  Some of the details I’ve glossed over and left behind.  Some of the details I’ve embellished upon, but the core of the story remains true, and my desire for the real thing is unabated.

I hope you enjoyed my story.

I know that bunny is going to enjoy the reality much, much more.

  • Rant.