A Date with a Mistress I Met Online

Introduction

Who I am? My neighbors/colleagues would say something like this: Your average guy, early forties, tall. In good shape but not overtly muscled. Flat stomach (very proud of that). Well-groomed but not overdoing it. Physically active, that is clear. Got an eye for the ladies, but no pervert. Fast thinker. Probably high sexual energy (not sure if they'd say that out loud). A good cook, good with his hands. Sense of humor. A good job, a nice car, a nice house. I trust easily, as you'll find out.

However, they got the pervert bit wrong. Very wrong. I am obsessed by BDSM and kink. And sex. All the kink.com stuff and derivatives, I devoured them. Have an anonymous account on several kinky dating websites. And one day I came across Her profile online. That is what this story is about.

The Date.

Finally, the five minutes are up.

As instructed, I push the front door of the unknown house open.

The hall is quite large, about 15 square meters I think and mostly empty.

Black stone floor, white walls, pleasant soft light. No windows.

There is a black door across the front door, without a doorhandle.

Handcuffs, a blindfold and a collar hang on a hook on the wall.

A small opening in the wall on the left at about hip height.

In the middle stands a black leather footstool. She told me about it.

I close the front door behind me. The lock clicks and I notice -- too late? -- there is no doorhandle on the inside of the front door.

The point of no return again got closer. I am nervous as hell.

As instructed, I undress and put my clothes through the small hatch in the left wall. Shoes underneath.

I listen whether I hear my clothes fall to the floor in the adjacent room.

I don't hear any thud; my clothes are really gone. I notice that I can't reach into the small hatch anyway.

My horniness is getting again the better of me, as it has been doing quite a while now to bring me to this point, this situation.

Again, my horniness takes over and I take the collar, the blindfold and the handcuffs.

The cuffs look to be of an electronic type, I don't see keyholes.

I put on the collar, making a tight fit around my neck with the strap.

My shaking hands make it difficult to find the clasp.

The blindfold follows, and then finally my horniness forces me to lock my wrists behind my back.

There I am, equal parts crazy and horny.

Naked, helpless, horny, shaking with nervousness. I slept poorly for weeks.

What drove me to do this? Some pictures of a beautiful Dominant Lady and many, many exchanged messages. On mail. Whatsapp. Fetlife. For weeks on end. It started to affect my work performance, my social life. This exchange completely filled my mind -- day and night.

The issue with fantasy and reality is that there is no in-between. It is either or.

There is only fantasy. Or there is reality.

And I knew, If I don't do it, I'll regret it forever.

It will mess up my life.

So that's where I stand now.

In a house with no nameplate, living room window curtains closed, not much people on the street as I walked towards it.

Naked, blindfolded, helplessly cuffed. Very clearly aroused with a raging hard-on.

And now at the mercy of what is to come.

I prepared as instructed. Freshly showered, freshly shaved, cleaned out my rectum. She had strong opinions on preparations.

"You can keep your eyelashes and you can keep your leg hair. In between those, I want ZERO hair."

Luckily my torso is not hairy at all. During my preparations I decided for a very thorough shaving followed by gentle chemical dehairing. I was as smooth as I could be.

We agreed again on the sublist that I completed and emailed long ago.

It seems like an eternity now.

She had given me an address, about one hour drive from my location.

So far everything is going as agreed.

I rang the bell at the agreed time.

Immediately, a small digital counter next to the door counted down 5 minutes.

At 0:00, the front unlocked automatically and I went inside.

"Here is the address. Be there on Saturday morning 10 am sharp. After ringing the doorbell, the door will be unlocked after the countdown, slave.

You go inside. You close the door behind you.

Undress, throw your clothes through the hatch on the left, put your shoes underneath and put on the blindfold, collar and handcuffs. Hands behind your back!

We discussed the footstool on Whatsapp. You know what to do."

I have no choice now. Keeping my balance, I lower myself to my knees and crawl in the direction where I've seen the footstool.

"When you get there, search for the little surprise with your mouth, my horny slutboy":

I lower my upper body so my mouth finds the black leather. I explore the surface of the footstool with my tongue and find an artificial cock protruding towards the ceiling.

That wasn't there a minute ago. The last message of Mistress looked like this:

"As you are well aware, there are tons of guys that want to submit to dominant women. Tons of them. And unfortunately, I wasted my time on several of them. Which has made me appreciate the value of first impressions, my little slutboy. If you don't want to be remembered as a time waster, give me a show. A good one. For which you get one chance. If you hear the front door unlock behind you, it means you're out.

If you encounter vibration, you're on the right path. Don't expect a full session, I want to see what you have to offer that I can work with. That is the best you can get out of this appointment, and consider it high praise from Me. Men always want more, but have to learn their place."

With that in mind, I go to work with my mouth, lips and tongue on the dildo that apparently is a realistic imitation. I feel the veins, I feel the foreskin that is softer than the rest, I feel the tip that even has a little pisshole. I try to get it as far in my mouth as I can, I try to make it as wet as I can. In real life, I have no experience with this. In order not to be a time waster I am worshipping the cock like my life depends on it. For size, I think I am slightly larger myself.

Suddenly there is an ejaculation of lubricant coming from the pisshole. And one more.

It seems the artificial cock has remote control.

Somewhere in the hall there must be a camera that I missed.

It has great view on how I express my perversions of my own free will.

I'm ashamed, very ashamed. I am aroused, very aroused.

At the same time, I am also grateful to the Mistress for the lubricant and spread it over the cock with my tongue. My mouth and chin are dripping with lube and it's on my cheeks too.

Yet another load comes out and then the cock starts to vibrate gently. The sign. I am not a time waster.

I get upright again, facing the black door, move forward on my knees with the footstool between them and try to find the cock with my ass.

That's not that easy when you're blind and handcuffed, but then I feel the vibration with my hole and slowly lower myself onto it, until my ass touches the leather of the footstool.

The cock starts to go up and down with varying intensities of vibration, speed and penetration depth.

My erection is almost painful and my horniness is through the roof.

Time passes by, it's hard to tell how much. I am now super horny, up for anything, totally raw and worn out from behind, totally raw from the front because of the strongest and longest lasting erection I have ever had. And it has yet to really start.

Then I hear a lock click in front of me. The black door...

I try to hear through the door with all my senses, but it seems to stay quiet.

The intensity of the cock is increasing, both in fucking and vibrating.

Then all motions stop when the cock is all the way in.

The door opens, I feel a draft that brings a beautiful perfume with it.

Then I hear heels clicking on the stone floor.

There are goosebumps running all over my body.

All senses, all nerve pathways have to deal with an overload. I almost seem to be in a trance, almost to be hallucinating.

I'm taken out of my thoughts by the feeling of my nose being clenched.

As a reflex I open my mouth and I feel two fingers are put in. Fingers with long nails.

Cautiously, and sensually -- at least I hope it is -- I to lick and suck them.

The fingers wipe the excess of lubricant from my cheeks, my chin and are offered to me to be licked clean, over and over again.

I hardly noticed that the dildo started pumping up and down again. With a slow rhythm, all the way in, almost all the way out. Then the fingers disappear and my nose is released again. The hand cups my chin firmly and tilts my head back a bit. I feel nails digging in my skin. If it wasn't for the blindfold I'd be looking into Her eyes.

More perfume. Spicy and sweet.

It all makes sense now. The nakedness, the perversion, the sleepless nights, the giving up of control. It is what She wants. I am in Her presence now. She has time for me. She takes care of me. I feel comforted and secure.

Then I feel something is being attached to my collar.

"Get up slave!" and I am pulled up by my collar.

So, I am leashed now.

I barely keep my balance when I respond to the jerk. Phew.

Also, the artificial cock is out of my ass now.

I am being pulled along with stiff legs -- and not only legs -- and manage not to stumble too much.

The heels of Mistress on the stone floor are the best drumbeat I ever heard.

It seems like we move through the black door.

It's slight warmer there than in the hall, that's all my senses can tell.

"Stop"

Her voice is beautiful, commanding, feminine, soft, persuasive, sensual. Her perfume is all around me now, it is very erotic.

I feel her hands on me, everywhere, with a light touch. There is caressing, gentle scraping with her nails, some squeezing.

"Not bad, slut, not bad"

"Hold still, now. And don't move."

"Yes, Mistress"

My hands are released from the cuffs, but I know better than to remove them from behind my back.

"Hands behind your head slave, fingers intertwined. Legs wide. Back straight up and butt back."

"Yes, Mistress."

I do what I'm told.

"This is called Stand, slave. Count to 10."

10 strokes of a whip hit my ass. I think it's a riding crop. I almost forgot to count, but I manage to catch up halfway through the first and second stroke.

"Grab your ankles slave, keep your knees straight. Keep your back straight."

Again, I do as I am told.

"This is called Bend Over slave. Just count to 10."

The 10 strokes on my ass again, harder this time. I count to 10 again.

"Now on your knees, slut, elbows on the ground, palms on the ground, forehead on the ground."

I quickly assume the position.

"This is called Down, slave"

The 10 strokes again, harder again, counting to 10 again

"Now Stand."

I take the position again and feel how I am being touched by Her hands again, over my buttocks, my crotch, my torso, my face, my thighs.

"Stay still, slave, and don't squeak"

I hear something metallic rattling and without notice nipple clamps are applied.

My sack is next, is, it gets several clamps on the left and several clamps on the right.

I'm breaking out in a sweat, but at the same time it's also very hot.

Then it feels like a condom is placed over my still very erect penis and unrolled.

Next, it seems something warm is rolled around it. Still blindfolded, I can't see.

"I will make a cast of your erection slave, that will become your personal anal plug.

I know men, they want to stick their thing in everything.

This will help you understand what that feels like."

"Now I will plug you with a plug from the store, but certainly not smaller. I am in a good mood; you will get lube on it"

My ass had barely recovered from the artificial cock when the plug is pushed in, and then I feel myself clinch the thin part.

A tug on the leash follows, and the Mistress orders me to follow her.

A door opens after 10 steps, a right turn, and after about another 15 steps we stop.

"You are a slave in the kitchen, in the cupboards you will find glasses and bowls.

In the refrigerator you will find white wine and grapes.

Pour me a glass of wine and prepare a bowl of grapes. I'm going now

back to the room, when I call you, take off the blindfold and start.

Then you will bring me everything, slave."

When I take off my blindfold, I notice that I am in a very beautifully designed kitchen.

Wasting no time, I collect the things She requested, put them on a tray and start back towards the living room.

The Mistress sits on the couch, beautifully made up and breathtakingly strict in a shiny tight-fitting long latex dress with a long slit at the front and behind.

Combined with the shiny latex riding boots, she is simply perfect.

I can't help to judge looks and figure, as all men do all the time. She seems slightly older than me, in between blonde and brunette, straight hair to her shoulders. She has that perfect shape that mature women can have that is a beautiful balance between slender and curvy. And those beautiful eyes are Her most amazing feature! Her make-up is subtle and perfect. She is one of those women that don't need a lot of make-up.

She is reading a book and doesn't look up or back at me.

"Put it on the table next to the couch. Sit on your hands and knees front of me." I feel that her boots are placed on my back and that I become a side table for her.

She drinks and eats for a couple of minutes, and I notice that the clamps on my nips and sack start to really hurt.

"Suck it, bitch!"

I lift my gaze slightly and see that from the front slit of the dress a strap-on cock sticks out. I execute the command with dedication and give the second blowjob I ever gave. This one is bigger than the one on the footstool earlier. Again, as if my life depends on it.

"Ok. Ok. Stop it, I know you're a slut now."

"Stand."

I get up and assume the position.

Mistress gets behind me and grabs something.

"Open your mouth".

I feel a ballgag entering my mouth and the strap is pulled tight around my head.

This is my first experience with a ballgag and I find it definitely uncomfortable.

The leash is unclipped from my collar.

"Hands behind your back".

She puts on the handcuffs again.

"Don't squeak"

And before I know it, she unclips the nipple clamps.

Fuck, that hurts. That really hurts. I try to hold my posture, and let out a large moan through the ballgag.

"Don't whine"

And she gives a sharp pull on the clamps that are still on my sack.

And then suddenly, she is all over me. She pushes her body against me hard. I feel her curves, I feel the latex dress against my oversensitive skin. I feel her body warmth through the dress. One of her hands pushes the plug in deeper.

"Whose ass is this, slut!?"

"It is yours, Mistress." I try to say through the ballgag.

The other hand is on my cock, on my balls, on my gland. She alternates between squeezing, digging in her nails, pulling, twisting. It is a beautiful mixture of pleasure and pain. I drown in the attention She is giving me.

"And to whom do these cock and balls belong, slut?!"

"They are yours, Mistress." I try to say through the ballgag again.

Then She lets go of the plug and slaps my face, hard. While still having my balls in a death grip with her nails digging in. Again, a slap on my face. Again, now on the other cheek.

"And to whom does your mouth and tongue belong, slut!?"

I try to answer, but I get slapped again, even harder.

"And to whom does your mind belong, my little slut?! To me, my little slut!?" The deathgrip increases. She squeezes my chin with her hand and nails. I nod.

"You're a bit crazy, huh!? Coming to a stranger's house, undressing, putting handcuffs on. So strong is your urge to submit to Me!" I nod.

"Good, slut. Then we will find out how useful you can be as a sextoy."

"Starting now!"

"Move to the dinner table and bend over it."

I do as I am told and the Mistress quickly and efficiently ties my ankles and locks my collar to a clip on the table surface. She has me fully immobilized before I know it.

Then I feel the butt plug being pulled out of my ass.

She places her hands on my hips and I feel something larger pressing against my ass.

Slowly but surely, I feel the strapon enter me and the Mistress starts fucking me.

She reaches around and grabs my dick with her nails, squeezes the tip of my dick with her nails, all the while keeping the fucking going.

After a while, she takes away her hand, she seems to reposition herself and I hear the Mistress breathing more and more heavily.

Is she fingering herself under the strapon, while still fucking me?

Wow, this date has become amazing.

"You're not a waste of time, slut. You have a lot to learn, but there is enough to work with!"

Then she comes, which I can feel from the hard thrusts in my ass and her moaning.

After some time, the strapon is removed from my ass and -- while I am still tied over the table - the blindfold is put back on.

Then my feet are freed from the ropes, the leash is clipped back on and I am being led back to the hall, I think from the direction we're walking.

"Sit on the footstool again, slave"

The Mistress puts me back on the cock machine! she forces me to sit down and I feel the cock against my ass again.

This time the cock is even bigger than the strapon. Someone replaced it?!

"For a straight boy, you are VERY cockhungry, slut. We are going to have a lot of fun."

She says, and puts her weight on my shoulders to impale me.

"The condom is still on your cock, slut, to keep things from getting messy, but first I'll put the machine on a heavy program for you."

It feels more like I'm riding a rodeo bull than a dildo, my ass abused by that thing!

Meanwhile, the Mistress is jerking me off until I scream and cum, and I almost pass out from the extremely intensive orgasm.

Then the clamps are removed from my sack, again that hurts like hell, especially after orgasm. I scream and complain into my ballgag.

Then the Mistress says:

"When the handcuffs come off, you can get dressed and go home go, slave.

Your clothes are on the floor behind you.

In any case, keep the condom on until you get back into your car. What you do with it is up to you."

"Check your inbox when you are home. You may call me Mistress Stephanie from now on."

And I hear her heels clicking on the stone floor and the black door closes.

After a few minutes the handcuffs automatically click open.

Apparently also remote controlled.

I get up from the cock, take off the blindfold and ballgag and see that my clothes are on the floor behind me, near the front door, which stands slightly ajar.

As I put them on, I notice there is a generous dash of Her perfume on them, so that I will smell it all day long.

Back home, after a shower, I open my Inbox.

"It was a good decision to take the risk today, my little slut. I enjoyed your dedication to the purpose of your visit. I took the liberty to tell two good girlfriends about today's date and they are very interested to inspect you as well. I expect you Saturday morning 10 am. Same place, same preparations. Please confirm, my little slut. Mistress Stephanie."

"P.S. They don't have a lot of time, and again, don't expect a long session."

Even as it's less than an hour after the unbelievable orgasm, I feel my dick start to rise again. Quickly I confirm the appointment and I fear another week of sleepless nights.