Meeting a Mistress

As I was walking up to her hotel door my mind was replaying our entire relationship. Well maybe relationship is the wrong word, I was actually meeting her in person for the first time in just a few minutes. Let me go back to the beginning.

I am a man with some submissive tendencies. Basically, the thought of being restrained and helpless while being teased or forced to cum has been haunting me for years. The Internet has been my friend, for in it I have found stories and pictures and videos of ever more extreme situations. These have been the fuel for my imagination leading me into the world I'm about to enter.

I have played with self-bondage, but being a man has hindered me. Tying myself up definitely arouses me, but then with no stimulation I'm quickly bored. Leaving one hand free allows me to stimulate myself, but doesn't truly leave me feeling helpless or controlled. Either way I don't really experience the fear of being helpless at someone's mercy. This is a common theme that races through my favorite stories.

Having gone as far as I could go on my own I decided that I needed to find a Mistress to go to the next level. Not knowing where to find one, I turned to the Internet yet again. That is where I met her.

I'm not even sure I remember how I found her site, but when I found it I inhaled every word. I lingered over every page, reading it multiple times. I studied every image until my imagination was using her likeness to restrain and tease me. She was actually a fetish model, so I searched the Internet to find even more images. I even found a few videos. Then about a month ago I took the plunge and filled out her application.

We traded a few emails back and forth until we setup today's meeting. I had almost cancelled a few times, and once had even written a polite email explaining why I was backing out. I deleted that email unsent, and now I was nervously knocking on her door.

She opened the door and invited me in, closing and locking it behind me. She was wearing a black skintight lycra top that accented and highlighted every delicious curve. On top of this she had a black silky corset that both highlighted and exaggerated her figure. It disappeared into a black skirt, with black stockings sensuously covering her legs down to her black heels. Her black satin gloves went up to within an inch of the short sleeves on her top. In short she looked every bit the fetish model that she was, and seeing her in person took my breath away.

She greeted me with a big hug, wrapping me up in all the satiny smooth textures she was wearing. Her strong, athletic body left no doubt as to who was in charge as she pulled me into her grasp. It ended all too soon for me, but that only reinforced the thought that she was the one in charge.

She was warm and friendly as we sat down at a small table to chat. She really put me at ease, making me want to open up to her as we talked. She referred to our emails on an iPad, and she took some notes as well. After a few minutes she was ready to begin.

"I thought we would do some role play today. Are you ready?"

"I guess. What setting are we using?"

"Stand up and just go with it. You'll figure it out." she said as she stood and tied a small white lace apron on top of her skirt. Adding a cute little white tiara turned her into a classic fetish maid. She turned away from me and walked over to the dresser to pick up a feather duster. She bent at the waist with her legs straight to reach down and dust the bottom edge of the stand. I had to adjust my pants before I could get to my feet.

She stood up, turned towards me, and gasped as she said "Wer bist du! Wie bist du hier reingekommen?"

I was a little shocked, but I tried to play along. "Umm... I don't know... I don't understand."

She set down her duster and started speaking English in a heavy German accent, pretending to struggle with the language. "English then. Why you are here?"

"I was invited."

"You lie. No guests today. Tell truth now or we make tell truth." she said as she removed her apron and skirt. Her top turned out to be a bodysuit, and her stockings were actually pantyhose that went all the way up under the lycra.

"What, are you going to call security? I already checked, no guards." I was starting to get nervous... but I was enjoying the feeling.

"We are security." she said. Then she attacked me. She shoved me backwards onto the bed. Jumping on the bed after me, she rolled me onto my stomach and straddled the small of my back. She pulled my left arm down and I heard the distinctive metallic ratchet of handcuffs as she closed the bracelet around my wrist. A moment later my right wrist joined the fun.

Flipping me over onto my back (and arms) she pulled my shirt up over my head, effectively blindfolding me. While she went to work pulling off my shoes I checked the cuffs and found that they weren't real. They were play bondage cuffs with a safety release. While she yanked off my pants and underwear (Ouch! My dick was not in position for that!) I uncuffed myself and pulled off my shirt.

"So, you think you are the slippery one!" she said as she jumped back on top of me. I struggled, but I really enjoyed the way she was man-handling me. My swollen and hard dick showed just how much I was enjoying it!

We struggled a bit, but with her already on top (not to mention her natural athleticism) the outcome was a forgone conclusion. After a couple minutes she had me pinned. She was straddling my chest with her silky nylon-wrapped legs. My upper arms were held to my sides by her knees, while my forearms were trapped on both sides between her calves and thighs.

"Now Mr no invited, we make truth. Why you are here?" she said while squeezing me with her legs.

Instead of answering, I struggled harder to get out from under her. She squeezed harder and laughed. "What you do now? You do nothing! Olga have you now, you stuck."

I tried again to buck her off when she reached over to the night stand for something. I almost got an arm out, but she quickly had me pinned again.

"Bad boy, you must behave for Olga!" She reached back and buckled padded leather restraints on my wrists one at a time. I honestly fought against it with everything I had, but I failed. She got off me to shift position, and for a minute I thought I might get free. Then her legs clamped down on me.

Now I was stuck again. She had her legs around my head and both arms, pinning my elbows to my ears! She must have hooked her ankles together because when she squeezed those thighs I thought my nose was going to break. My hands flopped around by the head of the bed for a minute, then I heard three small clicks. When I realized what I heard (and felt) my member got bigger and harder. The first two clicks must have been locking the cuffs on, because after the third one my hands were linked! Another moment and they were secured by some rope that had been waiting for me.

"That make it easy for Olga to get truth." she said as she released me and sat on my chest again. I felt around with my hands, locating the three locks and feeling the rope. The rope had been looped between the cuffs and tied out of reach. I was now truly stuck without assistance. That thought made me even more aroused than I already was.

"Maybe Olga forget reason and just keep you to play." she said. She reached down and gently stroked my cheek and chin. Reaching back she took off her heels, tossing them to the floor one at a time.

"You fun to play." Unseen, she started gently stroking my cock with her feet while she caressed my face. I relaxed, enjoying both the view and the treatment. Un-noticed, her other hand slid down and squeezed a nipple.

"aaaAAAAAAHHHHH!!!!" I screamed. She released my nipple.

"But Olga have job. Why are you here?"

"I was inviiiiaaaaAAAAAAAAARHG!" She twisted both nipples.

"You lie, tell truth now."

Thinking fast, I struggled to make up something in character. "I'm here to see you."

She started stroking with her feet again. "Ooo little boy, that not so hard was it? Well, this seems plenty hard!" She stopped moving her feet and slapped me in the face.

"Now, why little boy come to see Olga?"

Thinking fast, I blurted out the first thing that came to mind. "You are gorgeous. I wanted to see you for myself."

SMACK! She slapped me in the face. Not the half gentile slap from a moment ago. This one snapped my head to the side.

"Lie. Little boy think I fall for... how you say... pretty words? Why little boy come to see Olga."

"No... it's true! I heard there was a beautiful maid that was also effective security. I wanted to find out for myself."

She started stroking with her feet again while she spoke. "MMmmm. You wrong, but Olga believe you speak truth. Olga not maid. Olga is security, maid is only cover." She began gently and delicately circling my nipples. It felt good, but it made me nervous. After a moment, she proved me right by pinching and twisting them, making me scream.

"Little boy should no have lied to Olga." She climbed off the bed and then pulled me down by my ankles. This had the effect of pulling my arms very tight. I didn't even struggle as she produced more cuffs for my ankles, and pulled them tight with ropes to the bottom corners of the bed. I was now strung out in an inverted Y, and everything was pulled tight. "You are now Olga's sex toy. Enjoy!"

She went to a drawer and pulled out some pantyhose. "These have run, Olga find better use." Producing some scissors she cut one of the legs off. She then used the leg to tie up my cock and balls. Tying up my genitals made me really uncomfortable, but it also increased my hardness.

She started playing with my cock and balls. I was so turned on I was ready to shoot in under a minute, but she stopped me by grabbing my nipples and twisting. After waiting a moment she continued and brought me to the edge again. Again she stopped me. Over and over again I was brought to the edge and stopped by twisting my nipples, or viciously slapping my dick, or my face. She proved to be a genius about knowing when I'm about to cum, and also about preventing it. She never ignored me, but she kept me balanced on the edge of orgasm against my will.

If I tried to ignore her, she teased and stroked me relentlessly; not allowing my interest to flag... and when I tried to cum she wouldn't let me. She was also an expert at applying just enough pain to stop my oncoming explosion without being cruel. Of course, I couldn't exactly prevent her from touching me, cuddling, kissing me, or using any part of her body to excite me. I also could not stop her as she toyed with me for her pleasure, but she never allowed me to cum.

The best I could do was to return an occasional kiss, or sometimes lick and nibble her a little when she put something close enough to my mouth. I did get to suck her fingers a little, she seemed to enjoy that. She also seemed to enjoy having me lick and suck on her toes. I actually did quite a bit of that. Never got to taste any pussy though...

Anyways, this seemed to go on forever! Finally when I felt that I would go insane with lust if I couldn't cum she relented. She squeezed me with one hand while she was gently stroking my balls with her other hand. It was enough to push me off that cliff. Then she continued pushing me, working my shaft and balls while avoiding the head of my dick. She milked me for all I was worth, giving me the longest orgasm and one of the greatest cums I think have ever had.

"Did little boy enjoy that? It look like he did. Now Olga have some fun." Now that lust was no longer making me an idiot I realized I was helpless with a complete stranger. A cold shaft of fear went through my gut. She began to tickle me, playing with the head of my cock. What felt so very good a moment ago is now pure sweet torture. The pleasure is simply too much for me to handle as I screamed, bucked, squirmed, yanked, and did everything possible in an adrenalin-fueled panic to break free and make it stop by brute force. It was an epic failure. In the next few minutes I spent an eternity in heaven and hell at the same time.

While I was screaming to make it stop I suddenly realized that I'm quickly approaching that cliff again. Slowly as lust starts to take over my brain I notice that my hips have started bucking into that sensation instead of trying to pull away. My screams changed their note as well, and they are now an expression of my mounting pleasure. That's when I felt her spreading lube into my bum hole. I clenched and squirmed to stop it, but a single finger pushed up my ass and reached inside to tickle my prostate. The prostate massage was the last straw as I immediately began blowing my load again.

After the second cum I was just numb and I quickly became soft. She finally dropped the accent as she released me, handing me a warm damp washcloth to clean up. Looking at the clock I was amazed that an hour had gone by so quickly.

As I was walking to my car I was already making plans for my second appointment. I realized that even though the time had flown by, I didn't know if I could handle anything longer. On the other hand that devious little voice inside my head was saying that it didn't matter how long our next appointment was. Once we set it up and got started it wouldn't be possible to back out mid session. I wonder just how badly two hours would fry my brain...