After my ordeal in her hotel room, I had left it a couple of weeks before I had plucked up the courage to call her. I had tried to put off our meeting, but money was becoming a bit tight, and the contract we had verbally agreed on was still not signed, and was waiting for me to collect.
She had given me directions to her house and instructed me to be there at 10 o´clock SHARP OR ELSE!! Her tone had sounded stern, so I didn´t want to upset her, and dutily turned up as I had been told.
I tentatively rang the doorbell of her villa, and it seemed an age before the door slowly opened, and I pushed through the small opening. As I got my body inside, the door was slammed shut and I turned around to see her standing in the hallway. Seeing her again bought back memories of our first meeting, when she had left me in her hotel room tied to the bed with a butt plug inserted in my ass. I was only released the following morning when the maid came in and untied me, but not until after she had stripped off and abused my vulnerable position for her own sexual gratification first. Now here I was again, putting myself in her hands, just for the sake of money.
She looked fantastic, as beautiful as I remembered!! She was wearing a very tight white blouse with a very low cut cleavage and a very very tight black skirt which actually accentuated her curvaceous legs and thighs, she also had on a pair of the sexiest black high heeled boots I had ever seen, they were patent with high spiked heels and long spiked toes.
I was so nervous that I just stood there staring and without speaking. She immediately grabbed me and started to kiss me so passionately that I was even further taken aback, although it seemed to break the tension. She then slid her hand down to my crotch and started to slowly rub my cock through my trousers, and at the same time pushing her tongue deep into my mouth. Suddenly she pulled away, her manner changed and in a forceful tone said,
"Go upstairs into the bedroom on your right, and take off all of your clothes. I will be along shortly, you’re in for a bit of a surprise today.
“What kind of a surprise?” I asked innocently.
“You’ll get your answer to that soon enough,” she said, smiling at me.
I meekly did as I was told, went up the stairs and entered the bedroom. I was looking around the room, trying to take in my new surroundings when I heard her footsteps coming up the stairs. Without hesitation, and not considering why I was agreeing to her demands, I found myself stripping as fast as I possibly could. I had just finished when she entered the room.
I suddenly felt very embarrassed, as she looked me up and down and said,
"Now you are ready, you can follow me," to which we left the room and entered the door opposite.
“Ready for exactly what?” I asked insistently, hoping to get some kind of explanation.
"You´ll see" she said, and after giving me a dirty look, gave me a little shove to speed me along.
The first thing that I noticed was situated in the middle of the room, and was a metal frame in the shape of a pentacle. It was just over six feet in diameter, and was mounted on a low platform, about six inches high. Who was this woman, and what was happening to me?
Without speaking to me, she indicated that I should stand on the platform close to the pentacle. When I was in position, she ordered me to lift my wrists to the horizontal points of the star and snapped some steel rings around them. Then she fastened my ankles to the lower points. I was now secured with my feet flat on the floor but unable to bend down at all.
It was as though I was in a trance and couldn´t stop myself obeying her!!
"Today I am going to challenge you a bit........to test your constitution, so to speak. For our time together today, you will address me as ma´am, and will only speak when I give you permission, nod if you understand".
To which I did. Now that I was secured, I suddenly found myself not wanting to be here, and pulled at my restraints. The memories of our first meeting flooding back. She found this funny and a slight smile appeared on her face as she continued,
"I am very experienced at this, and you cannot escape no matter how hard you try, and I am anxious to see how well you do. I have great confidence in you, and I’m sure you will make me happy enough to sign that contract that you badly want. Just how badly you want it though remains to be seen."
I´m sure she only bought the subject of the contract up just to put me in my place, and remind me to do as I was told, as she was holding all the aces.
I had guessed that this was not her first time doing this, as a metal frame isn´t your normal bedroom furniture. I didn´t have any choice now anyway, I was hers..........and she knew it.
She then stepped very close in front of me, almost touching, and grasped my balls in one hand. As she looked at me, she squeezed my balls. “What do you think of me?” she enquired.
“Ma´am, I think you are a very beautiful woman, but I don’t know you that well at all, so I have no basis for an opinion other than that,” I said, in what I hoped was a suitably subservient tone.
She squeezed my balls tighter until a jolt of pain shot through my groin, making me moan.
“Flattery and bull shit will get you nowhere, you asshole,” she snarled, turning really nasty. “Before I’m done with you, you will give me a better answer than that! You will tell me exactly what you thought of me before this session started and exactly what you think of me at the end!”
She walked across the room to a cabinet, opened a draw and took something out.
“I think that you like pain. We’re going to find out whether you really do. Do you like pain? Does pain excite that puny male organ of yours?”
As she asked these rhetorical questions, she pinched my nipples and attached clamps to them. “Uuuggghhh…uuuggghhh,” I moaned as each clamp closed tight on my tender flesh. I had very sensitive nipples and normally liked a woman to suck and massage them during foreplay, but I wasn´t enjoying this one bit. Hanging from each clamp was a lead weight about the size of the end of my thumb. When she was satisfied that the clamps were not going to slip off, she flicked them back and forth with her fingers. As they swung, they increased in the intensity of the pain sensations in the pinched tissue. I tried to remain silent, so has not to let her know how painful it was, but I could not help making a few low sounds. “mmgghh…mmgghh.”
“Does that hurt?” she asked sarcastically.
“A little,” I lied.
“WHAT DID YOU SAY?” she shouted, again turning scarily nasty.
“I said "a little,"
“I didn’t hear you address me properly when you said it. You sniveling worm, you will address me respectfully every time you speak to me! Do you understand that?” she snarled.
“Yes, ma am,” I replied in as respectful a tone as I could muster.
“Fine! Now, lets see if we can find something that hurts more than ‘a little’,” she said as she returned to the cabinet, which slightly worried me. She returned, this time with a riding crop. Immediately she smacked me across the butt with it. WWHHHAAACK.
“AAAHHH,” I shouted as I lunged forward against the bars that formed the pentacle.
She hit my ass another blow. WWHHHAAACK.
“AAAHHH,” I shouted again, pressing hard against the metal bars.
She continued beating my butt.
My head shot back and my pelvis thrust forward through the pentagon formed at the centre of the star. I could not regain my balance after one blow before she delivered another. Surprisingly, my cock began to stiffen and bounced with each time the crop struck my ass.
When my penis was fully erect, she stopped and walked around in front of me. She tapped my erection from below with her crop and, smiling said,
“Ah yes, just as I suspected, you do like pain.” Then, letting the crop hang from her wrist, she removed the nipple clamps and pressed hard on my nipples with her thumbs. It felt like a jolt of electricity shooting through them. I grimaced and moaned.
“Tender, aren’t they?” she taunted me. Then she looked up at my face and said, menacingly, “Now, answer my question again, and answer it honestly, unless you’re anxious for more pain from this crop. What did you think of me before this session?”
“I thought you were a lovely, sexy woman, ma´am.”
She smacked one of my tender nipples with her crop. “Is that all?”
“Uugghh,” I moaned from the pain. “No, ma´am. I thought you were hot and I wanted to fuck you,” I couldn´t beleive I had spurted this out, but hoped that it would calm her down.
“You want to fuck me, do you," she smacked the other nipple..
She laughed mirthlessly. “So do you want to taste my pussy. Is that right?”
“And what did you think would happen, if you really tasted my pussy…sucked on it…stuck your tongue in it?”
“I didn’t know, ma´am, I thought you might be offended if I told you.”
“Easily offended, am I? Well, I’ll show you how ‘easily offended’ I am! What offends me is a wimpy man, who is so easily intimidated he can’t please a woman.
Then she proceeded to unfasten my feet, lower the bar, and release my hands. I sighed and thought that my ordeal was over, but she had other ideas.
As soon as I was standing unrestrained, she smacked my hard cock lightly with her crop and said,
“Let’s see if you can use that thing.”
She slipped out of the little thong she was wearing, bent forward over a padded table and hoisted her skirt up, presenting her bare butt to me, and said, “Stick it in my ass.”
“What, ma´am?” I said, slightly startled by this request, and a little apprehensive.
“You heard me! Stick that cock in my ass. I want an ass-fucking and I want it NOW!”
I hesitated for a moment, not believing what she was asking.
“Yes, ma´am,” and I nervously stepped up to her lovely little butt.
I gently spread her cheeks, but before I could press my cock against her tight little sphincter she held out a tube of lubricating jelly.
"HERE, you´ll need this" she shouted.
“Thank you ma´am,” I mumbled to her as I squirted some on my cock, and some on the puckered flesh in front of it. I put a generous amount on, as hurting her didn´t seem like a good idea. I placed the head of my prick against the target and pressed forward with my hips.
As her tight little asshole yielded to the pressure, she moaned slightly, “aaahhh, aaahhh.”
I stopped pressing forward, worried about any repercussions me hurting her might bring me.
“What are you stopping for, wimp?” she demanded. “Stick it in there…FUCK MY ASS!”
“Yes, ma´am,” I replied. I pressed forward harder. As I pushed my cock into her, she pushed back against me. My shaft quickly disappeared completely between the cheeks of her ass.
“Aaahhh…mmmm…aaahhh,” she moaned. When my cock was completely buried in her, she said, “That’s better, now fuck it, show me you know how to use that prick of yours for something other than to pee through it!”
I didn’t reply. I just started to withdraw and thrust, slowly at first, still wary of hurting her, then faster. I had never felt a hole as tight, the sensation was incredible. She was now moaning softly and pressing back against each thrust. I was quickly approaching a climax. I again thought of her leaving me in her hotel room and thrusted harder as though it was some sort of revenge over her.
Suddenly, she pushed back hard against me, causing me to lose my balance and fall backward. My cock was ripped out of her ass as I fell to the floor on mine. She turned quickly and, looking down at me growled,
“That’s enough of that, you horny slut! You’re enjoying it too much. Now it’s your turn! She pointed towards a bench in the corner and said,
"Get on your stomach on that bench over there,” She smacked me on my head with her crop.
“Yes, ma’am.” I scrambled to the spanking bench and lay face down on it, without a second thought. Normal service had been resumed, SHE WAS BACK IN CHARGE!!
She quickly secured me to the bench, and went over to the cabinet and got something from it. I still couldn´t believe that I was doing everything that she told me to, but I had gone too far now to back out. Besides, I needed that contract.
A few moments later I felt fingers spreading my ass cheeks and applying lubricant to my asshole. No sooner was this done than a pair of hands were spreading my ass. I felt my legs start to tremble as she proceeded to press something against my asshole, just as I had done to her. I felt a sudden thrust as my ass was penetrated by a strap-on cock.
“AAAHHHH,” I cried out from pain. My ass felt like it was on fire.
She ignored my moans and cries to stop, and immediately began to pump the cock in and out of me. Withdraw…thrust…withdraw…thrust. At first each thrust was very painful, but as my asshole began to adapt to being stretched the pain seemed to diminish. After a while the thrusts no longer hurt. In fact it quickly became a very exhilarating sensation. As she had done before me, I began to moan softly and found myself try to press back to receive each thrust.
As she continued fucking my ass with her strap-on, I heard her say,
“You really are quite a slut, you´re really enjoying this,” and the truth was......she was right, although there was still a slight bit of pain every now and again, I REALLY WAS ENJOYING IT!!
She was now pushing deep inside me then withdrawing in a steady rhythm. Occasionally, she would smack my butt just before another thrust. I was pushing back against her each time she thrust the cock home. Her rhythm became faster and faster. She was gripping my hips and ramming hers against my butt. I knew the strap between her legs that held the dildo in place must be massaging her clit, because she was moaning softly with each penetration. I had no doubt she was nearing a climax. Suddenly, as she penetrated deep in me, she screamed out, “AAAAHHHH.”
She thrust hard into me, paused for a moment, then withdrew and penetrated hard again. “AAAHHH,” she screamed a second time. I could feel her nails dig deep into my hips as she thrust again. “AAAHHH,” and again, “AAAHHH.” Finally, she stopped and collapsed on my back, the strap-on cock still deep in my ass. She was sweating and breathing hard.
I plucked up the courage and asked her, “Did you enjoy that, ma´am?”
After a brief pause she replied “Very much, I’ll have to do that again sometime.”
“Whenever you wish, ma´am…I’m at your service,” I found myself replying, still hoping to keep her happy, at least until the contract was signed.
She kissed me softly on the shoulder and slid slowly off my back. The dildo slid out of my ass as she did so. No sooner had her weight lifted off my back and the cock slid out than I was startled by a sharp whack across my ass. WHAACCKK.
“AAAHHH!” I shouted.
Several more blows rained down on me. WHAACCKK.
She was beating me furiously with the crop. “It’s good you pleased me…” WHAACCKK.
“…but you were enjoying it too much.” she snarled. WHAACCKK.
“I´m not here for your enjoyment!” WHAACCKK.
I´m here to see how you respond to pain!”WHAACCKK.
“Does pain excite you?” WHAACCKK.
“AAAHHH! Yes, ma’am.”
“Are you excited now?” WHAACCKK.
“AAAHHH! YES, MA’AM.” I cried out through gritted teeth, trying to ignore the pain.
“Is your cock hard?” WHAACCKK.
“AAAHHH! Yes, ma’am!”
“Do you want to CUM?” WHAACCKK.
“AAAHHH! Oh yes please, ma’am!” I said, although I would have agreed to anything at that point just to make her stop.
She did stop beating me, and released me from the bench, and returned me to the pentacle. I was in too much pain to resist and my ass was now stinging, and tears were streaming from my eyes.
“I want to see this hard cock that wants to cum.”
Very shortly I was again spread-eagled on the star. My cock was rigid and throbbing, and my ass still felt like it was on fire.
She stood close in front of me, still holding her crop . Looking up at me, she demanded, “Now what do you think of me? Do you still think I am easily offended?”
“No, ma’am. I now know that you aren’t,” I responded.
She grabbed my stiff prick and jerked downward hard.
“UUUGGGHHH.” I thought she was trying to rip it off.
“DON’T TELL ME WHAT YOU THINK I AM NOT!” she screamed. “TELL ME WHAT YOU THINK OF ME!”
I did not know what to say that wouldn’t get me in more trouble with her. While it is true that the pain had turned me on, I had been beaten enough for one day. I tried to placate her by answering,
“I think you are a very stern, demanding and beautiful woman ma’am.”
“STILL MORE FLATTERY AND BULL SHIT,” she shouted and immediately whacked my balls with her crop.
“AAAGGGHHH,” I screamed as I lurched backward..
“TELL ME THE TRUTH! WHAT DO YOU THINK OF ME?”
I had no idea how much more abuse I was going to receive, and I could think of nothing else to say that I thought would stop it. So as flattery hadn´t worked, in the end I just blurted out, “I THINK YOU’RE A SADISTIC TWISTED BITCH, AND I’M FRIGHTENED AS HELL OF YOU!”
She stepped back and began to laugh.
“Finally, the truth comes out! I scare the hell out of you and make you hot to cum at the same time. I love it!”
She laughed, and added. “I’m quite pleased with you.” So pleased that I think you´ve earned some relief?”
This was music to my ears. My ordeal was nearing its end.
She approached me and gently caressed my sides and hips with her soft hands. She leaned forward and gently kissed each of my nipples. Then she knelt down and slowly took my cock into her mouth. As she began to suck my cock, I felt her cool hands gently caress the cheeks of my butt. It was still on fire from the beating she had given me, but her gentle touch was soothing it delightfully. Because of that and the incredible sensations her soft mouth and flicking tongue were creating on my rigid cock, the pain from the beating was diminished rapidly. I gripped the bar to which my wrists were shackled and, in response to light pressure from her hands, I began to thrust my hips forward each time she slid her hot mouth down my shaft. It was amazing how much she could take.
With each thrust I felt her nose press against my belly. It was not long before my eyes were closed, my head was flexed back, and I was moaning softly. She was in no hurry. She knew exactly how to keep me at the brink of excitement without pushing me over the edge and making me cum. I wanted release, and, at the same time, I wanted these incredible sensations to continue forever. She had me in a state of both agony and ecstasy. I had lost all awareness of my surroundings and the previous events as I stood, eyes closed, head back, legs spread, clutching the bar overhead.
She kept me on the brink longer than I would have thought possible, but after what seemed like an eternity, she released me from her mouth and quickly stepped behind me. She reached around me with one hand and grasped my wet rod. I heard her soft voice whisper in my ear, “Cum for me.” She stroked my throbbing cock two or three quick strokes and I exploded. Every muscle in my pelvis contracted violently, and from the end of my prick erupted a great stream of white, sticky fluid. It flew at least six feet before curving downward and landing in a gleaming mass on the tiled floor. “AAAGGGHHH,” I shouted.
She stroked me again as she whispered, “Cum again, shoot that load.”
A second stream of hot, white fluid was expelled violently from my cock. “AAAGGGHHH.” My hips thrust forward and my knees buckled. I hung from the bar above my head.
She kept her arms around me tightly and continued to grasp my cock. As she stroked it another time, she encouraged me, “That’s it, empty that load. Cum some more for me.”
“AAAGGGHHH,” I cried out again as my pelvic muscles continued to spasm in response to her expert touch. More semen spurted, this time only a few inches.
Even then she did not give up. “Get it all out, give me all you have,” she said, as she stroked some more.
My muscles continued to spasm with each of her strokes and my body responded with small convulsions, but my load was spent. Only a small drop of cum was produced with each new stroke. I moaned softly as she made sure she had milked me dry. When she finally stopped, I hung exhausted from the bar, sweating and breathing hard. My cock went limp.
She then reached up and freed my wrists. I bent down and released my ankles and was instructed to get dressed and be downstairs in five minutes. As I was dressing, I glanced in the mirror and saw the red marks all across my ass, which seemed to bring the pain quickly back. I did as I was told, and was greeted at the foot of the stairs with a open door. All I got from her at the door was an abrupt goodbye, and it was firmly slammed shut behind me. I stood on her doorstep for a while, in shock at my quick exit before walking gingerly back to my car, because of my stinging ass. I drove off in a daze, and was a few miles down the road before realising that I hadn´t even mentioned the work contract.........the real reason for my visit.
"OH SHIT," I shouted, I had left her again with it still remaining unsigned.
Then despite the burning pain still coming from my ass, I couldn´t stop a huge smile come across my face, as I realised that it would mean that I would have to return to see her once again...........................................
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with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/reluctance/the-business-dealpart-2.aspx">The Business Deal........part 2</a>