A Random Encounter [MF]

I’m a married man who travels … a lot … and fools around. A lot. Most of my flings are rather unremarkable one-night stands. Most of the stories I post here, however, revolve around my occasional slave, the Night Owl. This is not one of those stories…

You see, I’m not usually into that kind of sex.

I met Sherry over drinks after a long day at a conference. I’m 40, she was just short of 50. We’re both married, we both are away from home substantially from work. I have a free pass – as long as I’m on the road, and as long as I share all the gritty details if asked – but Sherry does not. I haven’t gone up to my room from the conference yet, so I’m still in the requisite suit and tie. She leans back, with a little saucy attitude, wearing a slinky black dress that barely containers her enormous breasts.

The waitress, a sultry redhead I mentally note to ask after on another night, delivers our drinks and saunters off with an almost joyful bounce to her step. Sherry seems to look after her just as longingly as I do, but ultimately brings her attention back to me. I’m barely lifting my drink to my lips when she gets down to brass tacks.

The time my slave disappointed me Pt 2 [MF] [Mdom] [Fsub] [oral]

I’m a married man who travels … a lot … and fools around. A lot. Most of my flings are rather unremarkable one-night stands. I have one rather submissive friend, however, who I make sure to get together with whenever I’m in town. While work doesn’t take me her direction very often, when it does, an amazing night of nonstop, marathon fucking is sure to follow.

What follows might detail an actual encounter between us, a fantasy we’ve shared with one another, or maybe even my plans for our next visit…

A while later, once again I find myself sitting on the couch regarding my slave as I sip my drink and stroke my cock. As we lock eyes, I see in her that mischievous look that tells me I might have been played a bit earlier. Her cheeks are flushed red, she looks almost chipper. She struggles to keep a smirk off her face. She hadn’t forgotten her role at all; she’d wanted to be brutalized, and she knew that’s what would happen if she broke the rules.

Well. Two can play this game.

The time my slave disappointed me Pt 1 [MF] [Mdom] [Fsub] [anal]

I’m a married man who travels … a lot … and fools around. A lot. Most of my flings are rather unremarkable one-night stands. I have one rather submissive friend, however, who I make sure to get together with whenever I’m in town. While work doesn’t take me her direction very often, when it does, an amazing night of nonstop, marathon fucking is sure to follow.
What follows might detail an actual encounter between us, a fantasy we’ve shared with one another, or maybe even my plans for our next visit…

I arrived in town late last night and have had to be at work early this morning. Thinking about my slave left me distracted through most of the day. My last meeting finally winds down and I head back to the hotel.

As always, I’ve told her only how to greet me. I always aim for something a little different, but usually I have her waiting for me, presenting herself for me to use her as I please. Tonight, I decided on something a little more active on her part.

A night with my slave [MF] [Fsub] [Mdom]

I’m a married man who travels … a lot … and fools around. A lot. Most of my flings are rather unremarkable one-night stands. I have one rather submissive friend, however, who I make sure to get together with whenever I’m in town. While work doesn’t take me her direction very often, when it does, an amazing night of nonstop, marathon fucking is sure to follow.

What follows might detail an actual encounter between us, a fantasy we’ve shared with one another, or maybe even my plans for our next visit…

My slave is dutifully waiting for me. As always, she has checked into the hotel ahead of me, has prepared herself, and is awaiting my arrival. My flight was long, and the sight of her there on her hands and knees, waiting for me, is enough to perk me up considerably.

Tonight’s sight is a bit different: the usual lingerie and bonds are gone. She waits for me completely naked, her crop balanced across her back. I grunt a slight approval, but otherwise ignore her, shucking my backpack and luggage into a corner, before I pour myself a drink from the minibar. I pull up a chair off to the side, take off my shoes, and kick my feet up onto her ass. I’m not sure why this never occurred to me before, but she makes the most amazing footstool…