Blind Date

It had been a long day of meetings, and I was finally returning to my hotel. Business trips were always long and tedious. With the economy as bad as it is, your day was packed with meeting after meeting in order to justify the cost of the trip. I was a little on edge, and needed something to relax, so instead of heading up to my room, I went right to the hotel bar. The bar was dimly lit, reds and dark colors created a brooding but trendy atmosphere. It wasn't too crowded since my hotel wasn't in the middle of the business district, so it really didn't get a lot of walking traffic.

I walked up to the bar, and took a stool. The bar keeper wasn't busy, and he took my order for a vodka tonic. I sat sipping the drink, just decompressing for a moment, feeling the tension of the day begin to fade. There were a couple small groups adn couples in the bar, each spread out providing each with a certain level of intimacy. I took another sip of my drink, and I had resolved that I would just finish my drink, and head upstairs since it didn't look like I was going to get lucky tonight, not that I ever did. One of these business trips, I was determined to get lucky, but I had no idea how to make that happen. Even when I spotted a single woman, I never had the nerve to approach her. Groups of women were out of the question. If I couldn't approach a lone woman, I knew I could never face a group risking getting shot down in front of the group.

As I was finishing my drink, I noticed that in the corner of the bar, in a booth sat a lone woman. I hadn't seen her before. Probably because she had on dark clothing, and had long dark hair. In this lighting, it was easy to miss her. She looked like she was looking at me. I self-consciously looked the other way to see if there was another person behind me that was really the target of her stare. No one was there. I looked back again, peering over my drink, trying not to look like I was looking. The waitress was at her table now, blocking my view of her. When the waitress left, she had leaned back in the booth, and I could hardly see her again. No wonder I had missed her.

I took the last swig of my drink, pushed it toward the bartender, and I was about to reach into my wallet to pay when the bartender held up his hand.

"Its taken care of sir. In fact, there's another one waiting for you, but I've been told that you will have to go and get it," he said, pointing at the booth where the lone woman sat in the dimly lit corner.

My heart immediately began to beat faster. Careful what you wish for, I told myself. I wanted to get lucky, but I honestly really didn't know what I would do if luck came my way. I took a deep breath, and decided the worst thing that could happen is that I ended up in my room alone again. There was always pay-per-view.

I got out of my stool, dropped a couple dollars tip on the bar for the bartender, and walked to the booth. I tried to look confident and masculine, but I felt scared and weak really. My throat was suddenly dry, and I felt like a teenage boy again.

The drink was on the table, sitting next to this mysterious woman. She was sitting in the back of the booth. It was a round table with a circular booth surrounding it except for a narrow opening allowing you to slide in and out. She looked up at me, confident and smiled. It wasn't a beaming hi-how-are-you smile, but a sexy measured smile that said 'want some candy little boy?' Her long black hair shimmered in the dim light. She wore a low cut dress that left all but her breasts exposed. Her hands were folded neatly in front of her on the table, her nails painted some dark color, maybe even black. Her eyes sparkled from within dark eye shadow that made her look even more mysterious in the dimly lit room.

"Sit," she said, gesturing with a nod to the space next to her.

"Thanks," I managed in a hoarse voice, and I slid into the booth with her. "My name is--"

"Shhh...it doesn't matter what your name is," she cooed. "It only matters if you are willing to stay."

"Umm sure, yes," I responded, not really sure what else to say. She was a younger than me. Maybe a decade, maybe more. I certainly didn't mind being with a younger woman, what man does? She had a striking face. I couldn't see much of her in the darkness, but I could tell by her facial structure that she was a petite, hot woman.

"Good. Now drink your drink," she said, raising her own glass of wine in a toast.

We clinked glasses, and I took another swallow. Typical of my company, they kept us long, but didn't feed us well. What they called dinner had consisted of a couple tiny finger sandwiches 3 hours ago. Already, I could feel the alcohol seeping into my system. The social lubrication was welcome as it was probably the only thing that kept me from fleeing the scene. Why not let this play out?

"So, have you done this before?" she asked me. My heart skipped a beat again. She could tell how nervous I was.

"No, not really. But as you said, I'm willing to stay if you are willing to let me," I offered.

"Good. Then finish your drink and, we can go upstairs," she purred, and I felt her hand on my thigh.

By now my mind was racing, and I could feel myself getting hard. This was far too easy, but I was not going to complain. Maybe this is why they call it getting lucky? I took a long swallow, and finished the drink. The vodka burned a little, but it was a welcome burn. I tried to look relaxed, and not overly excited, but I'm sure that I hid nothing from this woman.

She reached over and took my hand. Her hand was warm, and she gripped my hand gently, but firmly and pulled me out of the booth. When I got back on my feet, I could feel the alcohol in my system already, as my balance was off just a tad. She let go of my hand to take straighten her dress. She was wearing what could best be described as a little black dress and strappy heels. Very simple, but it showed off her sexy figure. Her waist was tiny, and it showed off the swell of her hips. She was facing away from me, turned to look over her should at me, and then simply said, "Come."

She began to walk out of the bar, weaving through the mostly empty tables. I followed her, watching her ass and admiring the view. As we were nearing the doorway, I almost didn't see another gentleman, and we bumped into each other.

"Oh, sorry, I didn't see you," I apologized.

"No problem, I was looking for someone, and I didn't see you either," he said. Oddly, he looked as nervous as I felt. Didn't matter, I was nervous, but I was getting lucky. I turned back to see the mystery woman was halfway across the lobby now, headed for the elevators.

I caught up to her as the elevator doors opened. She stepped inside, and I followed her. She pressed the '9' button, and the elevator doors shut and began its climb to the 9th floor. She stood next to me, looking me over in the better lit elevator, clearly sizing me up. I was doing the same. She had a tattoo on her neck, but I couldn't see it well because of her long hair. I could also smell her perfume now that we were in an enclosed space. It was light, vaguely flowery, definitely feminine and sexy.

I followed her out of the elevator down the hall to the end. A room card appeared in her hand from out of nowhere, and she unlocked the door. She walked in, and I followed. The door almost closed on me as she didn't hold it for me, but who was I to complain?

The room already had a lamp on. It was identical to my room in the hotel except that it had her scent. I don't know how long she had been in the room, but her scent had clearly made its mark. It was intoxicating, and I felt my cock getting hard with anticipation.

She turned to face me as we stood at the foot of the king sized bed. I didn't know what to do or say, so I just looked at her and tried to look like I knew what I was doing.

"You are a nervous one, aren't you? Don't worry, I won't bite...too hard," she said playfully, as she reached for my tie. She began removing my tie and unbuttoning my shirt. I watched her undress me, and at the same time, looked around the room. A laptop sat on the desk, the screensaver drawing random lines on the screen. Besides the small lamp in the opposite corner by the armoire, it provided the only other light in the room. When my shirt was unbuttoned, she rotated me, slipped my suit coat off of my shoulders, then my shirt. She reached around my waist, and started working on my belt.

I was now facing the mirror over the dresser, and I could watch her undoing my belt, then my pants. She wrapped her arms around my chest, and put her lips to my ear, whispering, "Take off your shoes." I looked down, and saw my pants in a heap at my ankles, my socks pulled up my calves. My cock was forming a tent in my boxers.

I knelt, untied my shoes, stepped out of them, and stepped out of my pants. I pulled off my socks, and was now bent over wearing nothing but my boxers. I could see her standing in her strappy heels right behind me.

"Stay there, on your knees now," she said. Her voice had taken on a bit of a harder edge to it. I didn't argue with her. I got onto my knees. I could just see my face in the mirror, and her standing behind me. I watched her in the mirror as she reached behind herself, and unzipped her dress. She shrugged it off of her shoulders, and it spilled to the floor around her feet. She stepped out of it, and using her foot to pick it up, took it and walked to the closet, and hung it up carefully. I noticed my clothes were strewn about on the floor. She returned to the spot behind me, still in her heels and only a lacy black thong and matching bra. She had more tattoos on the rest of her sexy body. One of them disappeared below the top of her thong. Knowing that she had exposed herself to the tattoo artist to get it was oddly exciting.

She looked down at me in the mirror, and smiled. She reached over me, and took something off of the dresser right in front of me. I realized what it was just as she was pulling it over my eyes. I didn't say anything, but I was about to.

"Shhh....this is what you want, isn't it?" she asked. I didn't know how to answer that question, so I just nodded. "Stand up for me now," she said, again with more edge to it. She wasn't asking me so much as telling me. I stood. I felt her hands brush my sides, then pull down on my boxers. I was nude now, blindfolded in a hotel room with a woman who I didn't know. My cock was fully erect, and I thought to myself that it just doesn't get any better than this.

She turned me around with her hands. I knew I was facing the bed now. She pushed me toward the bed, and I took a small step, reaching forward until I felt the edge of the bed.

"Stand there at the foot of the bed while I get you ready," she said. I didn't know what that meant, but I was too excited to care. I was getting lucky, and I wasn't about to rock the boat. I heard her moving about the room. She was behind me again, and I felt her pushing my ankles with her feet. "Spread your legs wide," she ordered. I complied. She ran her finger nails down my back and across my ass. Her touch was electrifying. Then I felt her grab my ankle, and squeeze it. I heard the clink of metal, but I couldn't fathom what the sound was. She released her grip, and I realized there was still something wrapped around my ankle. Then she grabbed the other ankle, and before I knew it, both ankles were encased in something soft, but unyielding. I tried to move one of my feet, and the realization struck me. She had somehow locked my ankles so they couldn't move. A panic started in my mind.

She pushed me forward, and unable to move my feet, I fell onto the bed. She grabbed one arm, and in moments, it too was secured. At this stage my panic bubbled up, and I started to struggle. I reached for my bound wrist with my free hand to try and release myself. I knew if I lost my hands, I was not going to be able to escape.

I felt a thick cuff wrapped around my wrist. My fingers closed around metal fixtures that I could feel had rope tied to them. I kept feeling for some sort of clasp to release myself and then a sharp pain shot through me. My ass was alive with pain. Then again along with a loud slap. I cried out in pain, and instinctively, I reached for my ass. As soon as I did, I realized my mistake as she grabbed my arm, and pulled it behind me, bending my elbow and pulling my wrist toward my opposite shoulder blade. She had me pinned by her own body weight, my free arm twisted behind me. It didn't hurt, but I knew she could hurt me. I stopped moving.

"Now, hold still, don't struggle or this will only be worse for you. If you scream, then I'm going to have to gag you," she hissed. There was power in her voice. She secured the the cuff on my wrist, and I could feel her pulling the rope through the metal rings. With a quick pull of the rope, my hand was pulled securely in front of me.

I was bend at the waist, legs spread, ass in the air, chest on the bed. My hands stretched out in front of me, and I was totally immobilized.

"What are you going to do to me? If its my money you want, just take it from my wallet!" I said, fear clearly in my voice.

"Did I say you could speak?" she asked, and another slap echoed through the room, and my ass was again stinging.

I stopped talking, and I listened. Hoping she would explain herself. Moments ticked by, then I heard her moving about the room again. More noises, more fear crept into me. Then she was behind me. Her hands gently caressing my ass cheeks where she had hit them. She swept her hands between my legs, and took my cock and balls into her hands, stroking me. Despite my fear, my cock responded to the touch, and I was hard once again.

She continued to stoke me for a few seconds longer. I was totally confused now. Was I being sexually assaulted? If I was, why did it feel so good?

Something cold touched my ass. Then I felt her fingers rubbing my asshole. It wasn't so much cold as wet. The I felt her push her finger against my ass. I clenched my ass, trying to stop her from violating my asshole. Another slap, and I clenched even hard in reaction which resulted in another slap, this one even harder.

"Relax, or this will only get harder on you!" she warned me.

I took a deep breath, and I tried to understand what I should be doing. I felt her finger again pushing against my asshole, and before I could tighten my ass, I felt it slide inside me. She worked her finger in and out of me, adding more lube. Then she added another finger and more lube. Her other hand was stroking my cock again. I could no longer tell if it was the alcohol, my confusion, or what, but I realized I was deeply aroused. No one had ever done this to my ass before. Another finger was added, and I could feel myself being stretched. An involuntary moan came from me. Between my ass and the stroking of my cock, I was now totally aroused.

She removed her fingers from my ass. Then I felt something pushing against my sphincter. It was cold and large. She pushed it, and I could feel it sliding into my ass. I was much larger than her fingers, and I yelped as it stretched me to my limit. She backed off, and started fucking me with it. She kept stroking my cock at the same time, and soon, I felt her push it hard again, this time, I felt myself getting stretched again, but it didn't hurt as much. Soon, I again reached my limit, and I let out a yelp of pain. This continued for sometime until finally whatever she was fucking me with pushed into me completely. I felt it push past my asshole with a popping sensation, and then it was seated deeply in my ass. She let go, and it stayed put.

"Good boy," she cooed. Then I felt her climb on the bed. She sat above my head, and she began to run her fingers through my hair. "Now, be a good boy, and pleasure your Mistress," she said. Between my heighten aroused state, and the fact that I was tied up and totally vulnerable, I did not want to argue with her.

"Yes, whatever you want," I said.

"Yes, what?"

"Yes...um...yes Mistress?"

"That's better."

I felt her moving around on the bed, then she had my head in both hands, and she was lifting my head up off the bed. I felt her warmth on my face, and I could smell her now. I realized she was sliding her pelvis beneath my face. When she let go of my head, my mouth came to rest on her. Her warm body enveloped my face.

"Now, lick me, slut, and you better make me cum," she ordered.

I opened my mouth, and began to kiss and suck on whatever was in front of me. It didn't take long for her to position herself so that my mouth was square on her pussy lips. I licked her as best I could, my nose rubbing her clit. Her scent was intoxicatingly feminine. Her taste was sweet and heady. She was already wet. I licked like my life depended on it, and for all I knew, it might have been. After what must have been 15 minutes she shifted herself so that her clit was now in my mouth. I sucked on it, licking it with my tongue, and sucking it in and out of my mouth like a little cock. I could hear her breathing was getting faster. Her hands were on my head, holding me to her pussy, directing me.

"Ooohh god, ooooh, yes, that's it, you are going to make me cum...oooh yes, I'm cummmmmming," she groaned in ecstasy. She pressed my face into her with her hands, and I licked and sucked with everything I had. Her orgasm peaked, and I could feel her shudder and convulse, then she stopped moving, stopped breathing, just for second, then exhaled, and her body slumped beneath my face. Her hands relaxed. She breathed fast and deep, coming down from her orgasm.

She slipped out from beneath my face. Leaving me lying on the bed as before. I caught my own breath, and was now reminded again that my ass was stuffed full. She was moving about the room again, then I felt her pulling on whatever was in my ass. It came free, and I felt empty but only for a moment. Something cold and hard pushed against me again. This time, it slid into me rather easily. This was longer. I could feel it sliding in me, deep.

Her hands were on my hips, and I felt this new intruder in my ass begin to pump in and out of me. With each stroke, it pushed deeper inside of me until I felt her pushing against my ass. She was fucking me with a strap on. It didn't take long for her to create a steady rhythm. She pulled almost all the way out of me, then slammed it back into me. Each thrust of her strap on pressed against my insides. A new sensation began to build inside me. It was a feeling of fullness, but more than that. It was pleasure. Indescribable, but my entire core was pulsing with warmth and pleasure with each thrust of her hips.

I couldn't help it, but soon, I was groaning in time with the thrusts like porn star. I could hear her as well, equally aroused by her thrusting. My mind had lost all sense of time, and was singularly focused on the sensations that were rippling through me from my ass and deep within me. I started to feel like I was going to cum. My balls were boiling with desire. She hadn't even touched my cock since the before.

I heard her moans, and I knew she was close too. Then I felt her hand reach between my legs, and begin to play with my balls. I groaned louder, knowing that I was closer now. Her thrusting was relentless. Her hand grabbed my shaft, and she began to jack me in time with her thrusts. That was too much, and my orgasm ripped through me. My entire body shuddered as waves of pleasure moved from my ass to my cock and throughout my body. My cum shot from my cock in hot thick gushes. She kept jacking me and fucking me until I couldn't take it any longer.

She let off then. The strap on pulled out of me, and I was left gasping for breath on the bed. I was in a daze, but I knew that she was releasing me from my bonds. The blindfold came off, and she was standing by me in her strappy heels, her bra still on, a strap on with an 8 inch dildo swaying in front of her. She had the afterglow of a woman satisfied.