Online Dating, Gone Awry…

Online Dating, Gone Awry…

I awoke very groggy and not recognizing my surroundings. The last thing I could remember was the blonde silhouette entering the room. I couldn’t move. I was secured to some kind of table completely nude. All of my limbs tied down. The room was totally silent. I was still unable to move with any real strength. I must have been drugged, but why?

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Let me give a short description of myself and some background. I’m a white male in my late twenties. I stand just over six feet and weigh just over two hundred pounds. I have a slightly less than athletic build due to my job in construction and weekends consisting of beer and late nights.

On the way home from work one day, a guy on the radio was talking about his success with online dating. He mentioned that nine out of ten dates, with older women, ended with sexual escapades. This greatly intrigued me. Being a single guy, getting laid is a high priority.

I sped home and jumped on the net. After searching several sites I found one that caught my attention, focusing on women in their thirties and forties. I signed up, paid the fee and typed up a profile. I spent several hours browsing the site and sending out a few emails.

The next day at work seemed to drag on forever. The anticipation was killing me. I couldn’t wait to see if I had any responses. Finally three o’clock came and I rushed home eager to check my email. Sure enough I had three replies. I returned the emails with immense excitement.

After a few emails back and forth with each person I asked them out, each on different nights.

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It’s been a couple months and I’ve been on about fifty dates, each with a different woman. All but two of those ended with us either in my or her bedroom.

Let me say that the rumors about older women, teaching you techniques in the sac, are most definitely true. I’ve learned more in the last three months than I ever thought possible.

Most of the women were either still married or recently divorced. On a rare occasion one would come with no strings attached. A large majority of them were wealthy and all had a high sexual appetite. Some were independently wealthy and successful; others acquired their wealth through their divorce.

Today I received an email from a very beautiful brunette woman in her late thirties. Of course, I replied and we chatted off and on for a few days. Her name was Sydney. I asked her out and she agreed to Friday night. She decided that I would pick her up at her place. I thought this was kind of odd for online dating, most want to meet in a public place, but who was I to argue.

Finally Friday came and while driving through the neighborhood couldn’t help but notice that I’ve been in that neighborhood before. I pulled up to the house, walked up to the door and knocked. After a few seconds the door opened and I was in shock. She was more beautiful than her profile led me to believe.

Sydney stood at five eleven and had long flowing brown hair. She had emerald green eyes that sparkled in the night light. She weighed around one fifty, which for her height was perfect. Not too skinny with wide hips and a natural thirty eight double D bust. Dressed in a sexy business suit to, top it off.

Sydney invited me in and we made small talk for a few minutes. I hadn’t been this nervous on any of my previous encounters; however this was an unusual situation. I have never met a date at her house. Something just felt too forward, but that wasn’t going to stop me.

We continued to chat and Sydney offered to make us a couple drinks. I agreed and sat dumbfounded while watching Sydney’s ass sway side to side as she walked to the kitchen. Still unable to get over how well this was going and how comfortable she was inviting me into her home.

Sydney returned with our drinks and we continued to chat. I learned she was the CEO of an up and coming shipping company that she had been working with for the past eight years. This explained the large house in a very nice neighborhood. Sydney had never been married or any children. She admitted that her career was to demanding to share any time with another and that she has been online dating for years.

We put down a couple drinks and I couldn’t help but notice my drinks kept getting stronger. I was about half way into my third drink when my vision started to get blurry. I figured it was the alcohol and shrugged it off. Then I tried to take a drink and realized it was a struggle to lift my arm. Sydney noticed this as well and an evil grin donned her face.

Just then Sydney made a hand gesture and a tall blonde silhouette entered the room. I couldn’t move or focus my vision on anything. Sydney and the other figure were talking but I couldn’t make out the conversation.

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As I looked around the room, at what little I could see, it appeared to be a cross between an exam room and a dungeon. The walls, ceiling, and counters were white; I couldn’t see the floor in my current position. There were a few contraptions that I couldn’t even begin to describe. The walls were littered with chains, straps, paddles, whips, and many other tools that didn’t look pleasant.

I began to panic a little. I tried to free myself from the table’s restraints but could barely move my arms and legs. The silence was broken when a door, on the far side of the room, opened. Two figures approached. One of the figures was Sydney. The other I recognized almost instantly once I saw her face, it was Katy.

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I had met Katy on the same website and went out with her. We had a great time and ended the date with a long, hot, fuck session. She was very attractive. Katy stood at five nine and weighed in at one twenty five. She was a little too skinny for my taste but I wasn’t going to kick her out for that. She had long dirty blonde hair, blue eyes and full lips. Katy had a perfect set of legs that rose up as far as the eye could see and a pair of natural tits that measured in at thirty four D. She was a perfect example of a blonde bombshell.

After our date she continued to attempt to contact me. As beautiful as she was I could not bring myself to set up another date. I had never done it before and I wasn’t going to start now, so I ignored her advances. My system worked just fine and I had already had the next weekend lined up with two other women.

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As they approached I became weary of what they had in store for me. Neither of them said a word to me nor me to them. I could only assume that Katy wanted some kind of revenge and that she and Sydney had set this up like some kind of sting operation. Sydney walked around to my head and proceeded to put a rubber ball gag in my mouth and attach the strap around my head, securing it in position. Next she placed a blindfold over my eyes which also had a strap that went around the back of my head, as to not be easily removed.

It was quiet for the next few minutes. I could hear one of them moving around near the counter I had seen earlier.

The next thing I felt startled me. The other of the two started running her nails very lightly all over my body. Normally this is something that would cause me to spring an erection in a heart beat but the fear running through my veins slowed that from being instantaneous.

She ran her nails across my shoulders and around my chest before doing little circles around my nipples. This caused my hard on to become more apparent. She then went down my sides and across my stomach. Next she proceeded down the outsides of my thighs; I could feel her warm breath on my cock.

She continued down my legs and then to my feet. She moved both hands to my right foot and tickled around the top and bottom at the same time. Then she moved to my left foot making the same movements.

By this time my dick was standing at full attention, along with every hair on my body.

I heard Katy tell Syd that I was ready and Syd said she was ready as well.

I heard Syd approach the table on the opposite side as Katy. Syd set something down on the table and I felt something very warm, almost hot, being spread on my chest. I was running many scenarios through my mind trying to imagine what it was. Then I felt something being pushed on the warm gooey substance. Syd asked Katy if she would like to go first. Katy agreed excitedly.

In the instant before it happened I realized what it was, but there was nothing I could do to stop it.

Just then a strip of hair was ripped from my chest. This was unlike any pain I have ever experienced. I screamed as loud as I could but it was muffled by the ball gag in my mouth.

I am not a very hairy person to begin with but that didn’t stop them from removing all the hair from my chest, stomach, and arms. Katy and Syd seemed to be enjoying themselves immensely. I tried with all my might to block out the pain but it was just too much.

I heard Syd say she needed more wax and left the table. Katy began running her hands all over my smooth chest, marveling at their work. She then started teasing my skin with her nails again, focusing on my feet, legs, and groin. My dick was flying proud once again from the stimulation I was getting from Katy’s nails.

Katy was moving closer and closer to my cock. She started running her nails up and down the shaft, teasing the head of my prick. Her nails were sharp on the sensitive skin but the pain and pleasure mixed brilliantly.

I could feel her hot breath on my cock. Katy’s fingers moved toward the base and I felt the head of my dick slip into the warm confines of her mouth. Katy was sliding my cock in and out of her mouth. Running her tongue around the head of my prick before dropping her head all the way down, taking my cock into her throat.

I was so caught up in what Katy was doing to my cock that I didn’t hear Sydney return to her side of the table.

I was on the brink of orgasm when I felt a chunk of hair being pulled out of my groin, right above my dick.

Katy never broke pace, continuing her oral manipulation of my cock. While Syd carried on removing every hair from my groin. All the while Katy kept me on the verge of orgasm.

Once Syd was done with my groin they both took turns removing the hair from my legs.

When they finished and were pleased with my hairless body they left the room. I still had an enormous hard on. As I lay there trying to come up with a reason these two extremely sexy women would be doing this I suddenly became very tired.

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I must have dozed off. I am in a different position now.

My head and arms were secured in what I can only describe as a sixteenth century stock or pillory. The kind criminals were put in for humiliation, in the center of town. It had some sort of soft padding lining the neck and wrist holes. The mast of the stock was adjustable, as was the tilt, and set with my head about waist high and reclined back slightly.

My legs were bent and my knees were strapped into some sort of stirrups that came up out of the floor, also adjustable for height. They kept my knees spread apart fairly wide. A second set of stirrups came up out of the floor and secured my feet.

I felt extremely vulnerable in my new position. The blindfold had been removed but the ball gag was still in place.

Syd and Katy entered the room and mockingly asked how I was feeling, knowing I couldn’t respond due to the gag.

Katy returned to her position by my side and started the light tickling over my back and the backs of my legs. Presumably this means Syd is heating up more wax.

My prick began to harden again and Katy was quick to notice. Her left hand tracing lines up and down my spine. While her right hand made its way under me and got a firm grasp on my cock. She squeezed my cock rhythmically, simulating a pulse.

Just as I had suspected, Sydney joined Katy and they began removing any and all hair from my back, the backs of my legs, and my ass. I was completely hairless from the neck down.

After they had cleaned up and I had a chance to take in everything that has happened, Syd came over by my head and set some kind of protein shake on a cart in front of me with a straw sticking out. Syd looked down at me and informed me that the room we were in was completely sound proof and that she was going to remove my gag, in order to drink the shake, so making any screams for help was futile.

Syd turned a crank on the side of the stock which rotated my head from a tilted back position to a tilted forward position so I could reach the straw. She then removed the gag and left the room before I could ask why they were doing this to me.

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After what I can only assume was several hours, they returned to the room.

Syd approached my head and cranked the wheel which caused the stock to return to its reclined position and pulled the cart, holding the empty glass, away. Syd pulled out a collar of some sort and began to explain to me that it was a shock collar. She continued to inform me that the collar carried enough juice to knock me out, cold.

Katy came around and said that if I tried to escape not only would I be violently electrocuted but when I awoke I would be severely punished.

I found it hard to believe that a collar of that size could do any real harm. I was no electrician but it looked like a shock collar for a dog. I was calling their bluff, in my head of course.

Syd then began to prepare something at the counter while Katy walked around behind me and started lightly caressing my ass. Katy put a very small drop of lube on my asshole. It was very cold and caused me to clinch my asshole. Katy then started slowly rubbing the lube into my asshole, gradually increasing pressure until the tip of her finger was in my anus. I had never had anything in my ass before and this made me very uneasy.

Syd said she was ready and Katy left my side to assist Syd. Katy wheeled over what looked like a metal coat rack on wheels, something you would see an I.V. bag hanging from. Syd then came over and hung a large clear plastic bag from the metal stand, which was full of a clear liquid that was steaming. Katy then handed Syd a long clear plastic hose that had some sort of bubble in one end and a plastic valve in the other.

Syd attached the side of the hose that had the valve to the bag while Katy took the other end and smeared a small amount of lube on the bubble.

I felt Katy’s finger on my asshole again, smearing a little more lube on my anus. Katy removed her finger and began inserting the clear plastic tube in my ass. She slid about three inches in before it got to the bubble. I felt extreme pain as Katy tried to force this two inch wide bubble in my ass. I squirmed around trying to get the tube out of my ass.

Katy and Syd said that this was my warning and if I continued I would be punished. I paid no attention to them and continued to struggle trying to get this intruder out of my ass.

Syd had had enough. She yanked the tube out of my ass and walked over to a wall, I couldn’t see, and returned with some kind of paddles in her hands. Syd handed one paddle to Katy and they took turns swatting my ass with the paddles until my ass was bright red and burning. Each swat shot a stinging pain through my body.

After about fifteen swats from each of the women, they decided I’d had enough of the paddles. Syd took the paddles and set them on the counter. Katy reached under me and grabbed my flaccid cock. Syd returned with a large rubber band. Katy folded my soft prick in half and Syd wrapped the rubber band around my dick, forcing it to remain doubled over.

Syd returned to the side of the stock and cranked it so I was leaning forward again.

Sydney then grabbed a chair and placed it in front of me. The chair was a metal frame with pads on the seat and back. It was set in a reclined position with stirrups on either side and a wheel on each leg. She then stripped all of her clothes. This was the first time I’d seen Sydney’s nude body. She was mare perfect than I could have imagined.

I could feel blood rushing to my bound cock.

Syd sat in the chair in front of me and, a now nude, Katy came over, nude as well and just as perfect as I remember, and adjusted the stock so my head was aligned with Syd’s cunt. It was apparent to me that they also used the wax on themselves. I could not see a single hair on either of them.

Syd grabbed my head from her seated position and used it as leverage to pull her chair, and pussy, into my face.

My cock was now straining to free itself from its confined status.

Syd ordered me, in a very stern voice; to eat her pussy or I would get the paddles again. She continued to inform me that my cock would be released when I brought her to orgasm.

I began lapping at Syd’s pussy while she held my head firmly in place. Just as I found Syd’s clit I felt a tongue on my balls. Katy had knelt behind me and was alternating between teasing my sac with the tip of her tongue and sucking one testis into her mouth then the other. My cock was pulling against its restraints, desperate to free itself.

Katy’s menstruations on my balls had distracted me from Syd’s cunt and Sydney had grown angry with the pause. Syd grabbed two handfuls of hair and fiercely shoved my head back into her pussy.

The pain brought me back to my task and I continued sucking on Syd’s very wet, bald pussy. Trying especially hard to ignore what Katy was doing to my sac. My cock was on fire and I wanted nothing more than for Syd to cum and release my throbbing dick.

Katy added the light touching of her nails to the head of my cock without skipping a beat with her tongue.

Had my prick not been tied up I would have shot my load all over the floor ages ago.

This torture was too much to handle. I focused on Syd’s clit, sucking and rolling it with my tongue, praying she would cum soon or the rubber band would break.

Syd was moaning louder and forcing my head harder into her cunt.

It seemed the louder Syd got, the more Katy did to distract me.

Syd was panting. Her body started to convulse. I took her clit in my mouth and sucked as hard as I could and nibbled on it, finally bringing her to orgasm. When Syd came she flooded my mouth with her cum, so much that I couldn’t swallow it all fast enough and nearly choked.

Syd sat back in the chair for a few moments trying to regain her composure. However, Katy had not stopped teasing my cock.

Finally, Syd pushed the chair back and got up to join Katy. They both admired my dark red and purple cock held in place by the rubber band. Syd grabbed a knife from the counter and ran the cold steel over the head of my dick before using it to cut the rubber band.

My cock sprung free, but with out a little more touching there was no way I was going to find release.

I started rocking back and forth trying to bounce my cock off my stomach hoping it would be enough to bring me to orgasm, but it wasn’t. Syd and Katy stood back laughing at me trying to get myself off and then left the room.

I hung in my restraints, extremely frustrated, for about thirty minutes without any sign of Syd or Katy.

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When they returned Katy came over and said it was her turn in the chair. Syd helped Katy get adjusted and in position and then Sydney disappeared. Katy grabbed hold of my head and told me the start eating. I did as I was told and dove in. Katy was not nearly as rough as Syd was and I realized that they must do this, set-up and abduct men to torture, quite often. Syd was obviously the brains of the operation and Katy acted as the bait.

As soon as Katy started moaning I felt Syd around behind me. Syd was reapplying some lube to my asshole and I knew what was coming. I felt the tube being shoved in my ass.

Syd was not going to put up with any shit from me, no pun intended.

I tried to focus on eating Katy’s pussy and ignore what Syd was doing, but Syd was definitely making her presence known.

When Syd got to the bubble she added a little extra lube and shoved it in without warning. It felt like my asshole had been ripped open, but only for a quick second. When the bubble was all the way in the pain subsided and I continued my work on Katy’s cunt.

Syd slowly started turning the valve on the other end of the hose that was attached to the bag. Suddenly I felt near boiling hot water rushing into my anal cavity. I could feel my insides expanding as the, near two gallon, bag emptied itself into my bowels.

When it was apparent that I was full, Syd shut the valve and yanked the bubble out, which was more painful than when it went in; quickly filling its place with a butt plug of the same diameter. Syd then told me that I would be able to relieve myself after I brought Katy to orgasm.

As hard as I tried to focus on Katy the immense pressure in my lower abdomen was drawing my attention. Katy grew irritated with my subtle advances and forced my head into her cunt.

I decided I needed to get this over with as quickly as possible. I located Katy’s clit and began to suck and nibble, causing her to moan loudly. It took a few minutes but Katy finally started to quiver and unloaded her love juices all over my face and in my mouth.

Syd pulled Katy’s chair back so Katy could recoup and started unlocking the stock. As Syd was doing this she reminded me about the shock collar, which I still thought would be too weak to do what she said, and told me not to remove the plug until the last minute or I would be cleaning up the mess.

Syd also informed me that I was not to move until they were out of the room and that they would be watching me via several cameras mounted in the room.

I counted the seconds as the exited the room. Once the door shut I leapt up and tried to run to the toilet. I nearly crashed to the ground, due to my muscles not wanting to move, because I was locked in that position for so long.

Once I hit the toilet I grabbed hold of the plug and began to pull. The pain was too much though. I couldn’t bring myself to pull it out. However, the pain was still building in my stomach. Finally I grabbed it and yanked the plug out. Almost instantly the water and excrement came rushing out. I sat there for nearly fifteen minutes until all the water had left my system.

When I was finished I headed for the door. I was about three steps away when the collar zapped me. I fell to the ground, seizing, and blacked out.

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I awoke in total darkness. The gag was secured in place. There was something new. I could feel a wide leather belt that was around my stomach just above my hips. It was adjusted so that it could not slide down past my hips.

I also felt four small chains, two on my front and two on my back. The chains attached to the belt near my hips, forming a V shape in front and back. All four chains ended in the same spot, my asshole. They were attached to, I’m assuming, a dildo that has been placed in my ass. The chains were holding the dildo firmly in place; I tried several times to push it out with no success.

There was a sudden burst of light and then it was gone. I heard Syd and Katy approaching my head.

The lights in the room were flicked on and there was Syd and Katy standing right in front of me. They were completely nude except from a harness on the waist. Each of their harnesses had a large rubber dildo standing out, pointed at my face.

Syd’s was thicker and slightly longer than Katy’s, both were black.

Syd began removing my gag as Katy walked around behind me. I felt movement on the dildo in my ass. The four chains were released.

Syd had my gag off and shoved her cock in my face. I was ordered to suck her cock.

I took the rubber dick in my mouth and felt Katy grab hold of the dildo in my ass and start pumping it slowly.

Katy pulled the cock out of my ass and I felt my asshole holding its position. I could only imagine what my hairless, gaping asshole must look like in this position.

Syd continued thrusting her cock into my mouth.

Katy had a bottle of lube and squirted into my gaping asshole. Katy then stood and thrust her cock into my ass. Katy’s cock was a little larger than the dildo that was removed.

Surprisingly this was not as painful as I expected. To my amazement, my cock was twitching.

Katy had hold of my hips and Syd had hold on my head, both thrusting into me in a timed rhythm.

Syd pulled her cock out of my mouth and lifted it up, exposing her pussy. She stepped forward, grabbed my head with her other hand and shoved it into her pussy.

Katy was picking up speed and thrusting harder into my ass.

I began to enjoy the sensation of Katy’s dick deep in my ass.

I was now moaning into Syd’s pussy.

Syd dropped my head and walked around to my side. She reached under me and gave each nipple a hard pinch. She released my nipples and headed for my dick. Syd grabbed my now throbbing cock and squeezed it hard.

Syd then stood and told Katy it was her turn. Katy pulled her cock out of my ass, walked to my head, and shoved her wet cock into my mouth.

Syd stepped up as soon as Katy was out of the way and shoved her, much larger, cock into my ass. I felt like I was going to be split in half. My asshole was being stretched to its limit.

Katy was now forcing her cock into my throat. I was gagging around her cock as she continued thrusting her cock down my throat.

Syd was now pumping my ass hard and fast. To my surprise my dick was rock hard. I could not believe I was enjoying this.

Katy pulled out of my mouth and moved around and under me. I could feel Katy’s hot breath on my cock before she took my dick in her mouth.

Syd was now pulling her dick completely out of my ass, admiring my gaping hole, and thrusting her cock back into my asshole.

Katy was bobbing her head quickly.

I couldn’t believe I was finally going to get to cum.

The sensations, between Syd’s dick in my ass and Katy’s hot mouth on my cock, were too much to handle. I exploded into Katy’s mouth.

Katy took my load in her mouth and moved out from under me. She approached my head, leaned down and kissed me deeply, forcing my own cum into my mouth.

I had never tasted cum before. It was warm, thick, and salty. Katy held her mouth to mine until I swallowed my own load.

I felt Syd in my ass still. There was some odd side to side movement and I felt Syd’s body move away from me but her cock was still in my ass.

Katy moved around behind me and they attached the chains of my belt to the dildo in my ass, holding it in place.

Another shake was placed on the cart and wheeled in front of me. The stock was adjusted so I could reach and the women left the room.

To be continued…

again this is the first story i have posted on this site. i am looking for some consrtuctive criticism. please leave a comment or an idea or fantasy of where you would like to see it go.

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