What Does That Look Like to You? Ch. 01

Literotic asexstories – What Does That Look Like to You? Ch. 01 by siblah01,siblah01
It all started so simply. I’ve had an on and off interest in S&M and femdom dynamics that goes back to my youth. I won’t bother trying to psychoanalyze why, it’s always been with me. I’m older now and have had many experiences with professional dommes. In my youth I was lucky enough to have had some personal relationships with either women interested in D/s dynamics and in one case a pro domme my age who became a lover.

I’ll leave that story for another day. Like so many other encounters with pro dommes, I met her by way of one of the websites dedicated to escorts, mistresses and other providers. Young, pretty in an unconventional way and a favorite of mine: plenty of tattoos. Blue hair in some of her photos, I couldn’t resist reaching out. Even my friends know my type (but not my proclivities) going back to my teen years and she was it.

It had been a while since the last time I saw a pro domme in truth. I’d say the urge has come and gone over the years. I’m more often quite vanilla in my desires so I bounce between straight sex and my little obsession.

This is a true story so I’ll leave out her name or a reference to her specialty embedded in her moniker which might give away her identity. Bottom line she likes ass play and strap-on. I say likes because her obsession extends beyond the professional realm as I’ve come to find out over the last three years of seeing her professionally and personally at our many dinners out.

Have you ever tried to see an independent domme or provider? Care must be taken. Follow her instructions carefully. The person you’re contacting is screening for undesirables. Anyway, I got past the screening and scheduled our first session for an hour. She gave me an address in Ridgewood Queens.

First meetings can be so awkward but this was different from the usual. At the time I didn’t realize I was going to a S&M rental dungeon. Without giving away too much this was the first of three or four spaces we’ve played in, run by another domme who rents out the space and has since moved it twice. More if you include my home once…let’s call that part 10 or something…

After emailing that I’d arrived I buzz outside an industrial door down the street from some auto body shops and wait to meet her. Finally the door opens and standing before me is the woman pictured on the website, sort of….

“Hi, Sam?” (Not my real name) She said. I’m a bit taken, she is not all dolled up in domme gear and is instead in sweat pants and a hoodie that says UMASS…so sexy. “Um..hi, yes, sorry I didn’t expect the outfit.” “Right, it’s cold so I put something warm on to getcha”, she said with a cute smile, “c’mon up”.

Although we had exchanged interests we sat and discussed how the sesh would play out and some limits (no one has no limits, saying so is another way to get your potential pro domme to turn you away). “Let me step out and get changed, when I came back you should be naked, eyes closed standing here” under some leather wrist manacles hanging from the ceiling.

When I was allowed to open my eyes I saw her dressed in a black camisole that was under her sweaties, so thin and lithe, with small breasts she took me over. My wrists secured over my head. “Open your mouth” and the sweetest taste came to me in the form of her spit and then the even sweeter smell of her underarm. We’ve sessioned many times since but these tastes and smells are still addicting to me and I never shower after our sessions so the smell of her remains as long as possible.

“You said lite pain, right? lets test that…” and she grabbed me hard by the balls. “Light enough?” her lips just inches from mine. Speechless. If I write more about our sessions and how they’ve evolved the one thing we’ve never done is kiss. Kissing is so intimate and I’ve begged for this more times than I can count. She has a boyfriend now and knowing her I wonder how long it lasts but she even admitted to me that it was months before she allowed their lips to touch despite having sex. Their relationship although not D/s is far from conventional. Ass play is more than a profession for her and she’s further confessed this makes finding a boyfriend difficult. Also, she’s clearly the one in charge.

She lets me go and moves around the room with grace and speed and returns with a small butt plug. “You’ll need this if you’re my sub”. Condom, boy butter and some spanking and in it went. “Good job you deserve a reward I suppose.” More tasty spit a string of it hanging between our lips. God, never enough of that sweet taste.

“Let’s warm up that ass”, “Oh wait” and she walked away and then returned with some clothes pins for my nipples. Sweet pain. “Not to bad, right?” She said. Well it was too much in fact and yet I felt the desire, even in our first session, to take it. I’m basically hard enough to knock something over with my cock at this point.. If I keep writing I’ll explain how far we’ve gone exploring pain. When your loving obsession is as strong as mine and the level of trust is so high “anything you want” becomes real and limits fall away to trust in how far your domme can take you.

Now came the crop over and over across my ass. At this point pain was still easy to elicit from me so after every few strokes some spit or some smell of her. Or just the intimacy of her touch close to my face. “Hi, how are you?”, I blubbered out something affirming but she just laughed at my spaced out state. She’s so amazing at combining pain with the intimate pleasure of her touch and breath. As we’ve gotten to know each other well that dance has become wonderfully intuitive.

For those of you who have seen a pro domme you probably know when the session is going well (or poorly). Go to a house in NYC and you’ll see what I mean. It’s not even a 50/50 proposition. But when it’s good it can take you away. This was that, even in this first session I could feel the chemistry.

After a good cropping and spanking with several adjustments to that butt plug and the clothes pins she said “I think you’ve had enough of that for today…except for my favorite part.” Off came the clothes pins which is more painful than wearing them and then…”let’s give those nipples a squeeze” wow…there’s some real pain…and further laughter from my future obsession..

She removed me from my manacles and let me decompress for a couple minutes and then asked for help getting out a pink floor mat you’d see in a high school gym. “Let’s relax a bit, you took pain pretty well and you deserve a reward, you said foot worship, right?” ” leave the plug..”

How we end our sessions is often the same but not always. Keep in mind we had just met. Us on the pad on the floor. Giggling over my pain, sucking on those lovely toes. Making love to her feet really. I love feet. Particularly her toe with the little circle tattoo. Me touching myself and then her feet on me and then me all over her feet. “Clean.” Just one lick this time and then laughter from us both. But I said relax and went and grabbed some paper towels and cleaned the rest of me off her feet.

“That was awesome” I said like an idiot at a loss for words after an intense session.

Then all business. We chatted as I dressed, promised to see each other again. Money. A quick hug and out the door I went in a pretty good mood. Little did I know then how much more intense our sessions would become and with them my desire for her to love me the way I love her.

I will say it’s evolved into an odd relationship. Some combination of transactional professional engagement, strongly shared friendship, two way therapy and advice, lovely foodie dinners at amazing restaurants. It’s not as two way as I’d like but we are both busy people. I usually reach out first but we’ve become so much more intertwined that it’s more of a two way relationship.

If you’re wondering about the title. Now three years on in our relationship it’s the words I least like to hear from her lips. What does she say when I express my strong feelings of love (yes love) and hope that she might love me back despite our existing relationships and differences in age, “what does that look like to you?” Ow..

Thanks for reading my first story.