Jack was sitting in his office alone and it was rather late. No worries as he had all keys necessary to lock up his room as well as get in and out of the building and back to his car. Everyone else was gone. Well there may have been a cleaning person a few halls over, but no one was around to disturb him, so he was safe to be sitting at his desk and surfing porn.

Now some people would assume Jack was a fool to be surfing porn in his office and not the privacy of his own home, but Jack had already looked into how the University monitored internet usage and true to the school’s nature their methods were…antiquated. Jack wasn’t an IT specialist but when he made some inquiries about the internet access at the school, which was only installed last year, he soon realized he knew more about the field than anyone else on staff.

The reality was they didn’t monitor it at all. They had a company come in and set it up, but there was no system in place and no one responsible for overseeing how it was used. Jack also had a little back up, in that if questions were ever raised he could claim it was research, either for one of his classes or a paper he was writing. As a professor of archeology and the ability to think on his feet, he was sure he could explain away any sites. ‘Notice the differences in the cultural approach to sex for pleasure vs procreation’.

So safe in the knowledge that no one would ever know and that even if the impossible occurred and someone did discover his actions, he was prepared to brush them away as a necessary component of his work and not the prurient interest one might assume, he sat at his desk prepared to find some late night satisfaction.

He was always searching for something new; perhaps that went hand-in-hand with his dedication to research. He was also looking for something dirty and nasty. He had found himself drawn to a lot of fetish sites and images, whips and chains, bondage, mistresses in thigh-high leather boots, and the dungeon atmosphere.

In fact, he noticed many dungeon settings and bondage sites were using old equipment such as old iron bars and cages from old prison sites, or at least based upon some historical references. He was happy when he could identify a certain piece being used and could compare its original use to the use he could witness on the screen.

So various old-world tortures were often translated into new-world kinks, and he was perfectly okay with that. Sometimes the accessories would be as simple as manacles of a time long passed, and other times it would be strange contraptions that had been used in the treatment of mental cases when medicine was a bit more of a guessing game, practiced by corrupt people.

All these dark devices and images would stir Jack and get his heart beating faster. Tonight he had already begun his quest at a bondage dungeon site he had come across last time. It quickly linked him to another where the focus was quite intentionally on historic porn. People were dressed of the day and men and women were held in stocks while they received their punishment.

This was all good and Jack had already taken his cock in hand; his pants unzipped and open as he sat at his desk. His eyes caressed the bare bodies on the screen and he could feel the soft flesh in his hand. He also grew excited seeing the faces of fear and pain. He was enjoying this site quite a lot and was looking for the best content available.

He checked a few links but most while leading to similar scenes took him further away from this history of bondage. Then in a few link hops he noticed one that was adding a dark supernatural element. It mentioned witches but went on to mention succubi and the risks to one’s very soul.

Well there were leather boots and whips which oozed the sexiness he was looking for, and the addition of fake horns or red painted skin was something different and new which was also a hook. So he followed a few links down this path, some promising but then having little to show, and he felt he may have to give up and go back to the stockades and prison site that had been working for him. Then he found the Hellfire Dungeon.

It was a site much like any other, though they certainly were playing up the flames and devils aspect. There were lots of fire-flickering torches and smoldering banners. The site was set up to show the dungeon was filled with devils and demons all waiting to grant your desires, but at a cost. It was well played and they hadn’t skimped when they put the site together.

The dungeon was also divided into categories and levels. So if one simply was looking for bondage in a cell or slaves being lead around on a leash, you could find those on the first floor. Simple whippings and spankings were also found here and on the second floor. A quick look and it was clear the severity was the difference in where the images and video clips were placed. Simple spankings with just a red bottom would be on the first floor, but on the second floor you could find more serious canings with a lot of blood and bruising.

Bondage appeared to be everywhere but again, the more severe was located lower in the dungeon. So as the positioning of victims became more cruel or water torture was added, the activities were supposedly taking place deeper within the setting. Likewise, the use of fire became more prevalent in the lower levels.

This was quite serious and as he went looking deeper into the dungeon, he realized that the actors involved had to be much more experienced to endure these scenes. I mean, the average person just couldn’t twist their body that way, or had the strength to hold themselves up to keep from being choked, or could endure that level of pain without passing out.

And all of that knowledge, those sights, those sounds, it was all building a burning fire within Jack. He was sure he could come from what he was looking over now, but he had already planned for a marathon masturbation session. He had all night if he wanted, so whenever he found himself close, he backed off. He had become something of an expert in edging himself and could go on for hours before he finally blew his load.

So while he had been getting a lot of enjoyment already, he was still consuming mass quantities of fetish filth to feed his insatiable hunger. He would scour a floor of the dungeon, experiencing all the pain and lust it had to offer and then he would sink lower and continue his search.

As he made his way through the dungeon site, he would occasionally come across various warnings. Warnings of the graphic nature of what lie beyond and that such activities weren’t for everyone. Of course Jack flew past the warnings. He read them, but mostly just to have a better idea of what was coming next.

The site, as mentioned, was well put together and for some of these doorways, to keep the dream alive, he would have to submit in some way. For example there was a whipping room run by a Mistress Violencia and to gain access one had to first kiss the tip of her boot with the cursor and then kiss her whip, and finally you had to type ‘whip me without mercy’ into a box before you were allowed beyond.

It was interesting and he had to slow down a little to read and discover what it took to go further. That wasn’t so bad as it was also like a small puzzle he was having to solve and each one unlocked a new treasure of sexual gold. Did we mention that the mistresses just got sexier and sexier?

Jack would have rated most of the women at a ten when he was still on the first floor. But as he went deeper into the site, he was convinced that the world was unaware of some elevens wandering about. It would have been difficult to pinpoint just how they were better but the eyes didn’t lie. A mistress was a solid ten and then compared to another, she simply fell a bit short.

This was already one of the best masturbation sessions Jack could remember and he knew he would be reliving many of those images for days and weeks to come. But he still wanted more. He still was going deeper into the site.

He had already seen a lot and while he wasn’t new to the game, some of what he came across was stuff he had never seen before. Some worked for him better than others and he was finding some images a little scary to be contemplated for real life. But still he went further.

Then he came to a portal. According to the site he had reached the Demon Portal and this was serious stuff. Jack briefly considered if some of what lay beyond might be illegal, as the warnings were quite dire. He had to be willing to give up his rights; all rights, if he dared to enter the portal. He was promised pain and pleasure awaited him on the other side.

And there was a cost. Of course there was. He tried not to be deflated as he prepared for the description of credit card payments and how he would be billed. But that isn’t what he found. Instead the portal said that cost would be determined based upon services received and there were many payment plans in use; however, he would have to offer his soul as collateral.

Well that was different. Maybe they were taking this devil thing just a tad too far. Jack stared at the screen as minutes passed. He just wasn’t sure what sort of price they may be expecting, even though he hadn’t given any payment information and at this point had no intention to. He was also concerned about just what it was he might see beyond the portal. And though it was just marketing, the whole ‘soul as collateral’ was a bit creepy.

Finally, his cock having taken a break as he sat at the portal, he decided to go through. He hit the button stating he wanted to go through the portal. And then another step came up. It wasn’t another button but rather a phrase he had to type in. And the phrase read as follows: I hereby relinquish my soul, being of sound mind and body, to be held as collateral for services rendered beyond the Demon Portal.

They didn’t play around, whoever put this site together. Jack sat for a moment and then slowly began to type. He reached the end and his finger hovered over the ‘enter’ key. And as he pressed the button the bulb blew out in the overhead light. Maybe it was a split second before or after but it startled him nonetheless.

Jack took a moment to catch his breath and then chuckled at himself for acting a fool. It was an old building with old fixtures and he couldn’t remember the last time he had changed the bulb. It was bound to happen at some point; though it was funny that it happened when he entered the Demon Portal. He took a moment to laugh and relax and give himself a good stretch, before he returned to the glow of his computer screen to reap the benefits of passing beyond the portal.

A woman appeared in a dark corner and she was walking forward to meet him. The woman in question was in full body makeup, as she was practically nude, but her skin was red and there was a pair of convincing horns poking through the hair on her head. She also had some sort of tail, but Jack could only see it briefly and from the front. Her dress, what little it was, was black leather or PVC and looked to be very expensive. He would also have to rate this woman as one of the elusive elevens he had encountered this evening.

“Well hello, Jack. So nice to see you on this side. What would you like to see first?”

He was pleasantly surprised. He figured he had given his name somewhere along the line with all the steps he had taken, but they had inserted it flawlessly. This was definitely high quality that he had found. The devil woman looked on expectantly and he realized he had to make a choice. He didn’t have anything specific he was looking for but rather expected to scour through all that was available beyond the portal until he was forced to stop in some way.

“Show me whippings.”

“Indeed. Whippings are always a pleaser. Let’s start with this.”

There was a heat wave effect on the screen and then appeared a naked woman strapped to an angled wooden frame. She was standing with legs and arms spread, facing forward and her back rested on the reclined wooden frame. She was already showing marks of a whipping and the tears were just beginning to well at the corners of her eyes.

The devil woman turned around and took a swing of her whip to the poor victim. As the whip moved through the air, the end split into three and the ends ignited in flame before it landed across the bare skin, biting into breast and torso. The flames, if indeed there really were any, went out after contact. But they returned when she lashed out at the slave again.

The camera drew in and focused on the naked form, now crying out, her tears no longer in check. Jack noticed something familiar about her. Could he have seen her in an earlier image that evening? He didn’t think so. It felt more like she reminded him of someone he knew in real life, not some porn actor on the internet. Try as he might, he couldn’t place the resemblance.

A few more strokes and the girl was sobbing uncontrollably, and the fresh marks on her skin looked profoundly painful. Blood dripped from her breast and stomach. This was no amateur whipping. And then the devil woman stepped closer to inspect her work.

The camera again pulled in tight and the devil woman stroked the slave’s cheek; her hand in a fingerless glove, and her long black nails each coming to a piercing point. She shushed the girl and told her she had what she needed. Then the devil reached behind the frame and scooped something into her hand. When she brought her hand forward, she began rubbing it over the girl’s tortured skin and immediately brought new screams from the bound slave.

As best Jack could determine, the devil was applying something like alcohol or salt or some combination to the girl’s wounds and the pain was clearly intense. The slavegirl shook her head furiously and if he had to guess, Jack would say at that moment she would have preferred the whip.

The devil looked back at Jack and asked if he was enjoying what he was witness to. Jack had to admit the devil was, well, sexy as hell. And the slavegirl, whom he still couldn’t place, was attractive and taking her punishment like a pro. But while part of him enjoyed it, he also wasn’t quite onboard.

“Let’s leave the girl alone and try whipping a man.”

“Ooh another good choice. Let’s see what we have to offer.”

Another heat wave effect and the girl disappeared along with the whipping frame she was attached to. A second shimmer and Jack was now looking at the back of a naked man, his toes barely reaching the ground as he was strung up in a box frame, his wrists in black leather cuffs attached to lengths of chain.

Unlike the girl, the man showed no signs of previous whipping. And while his face was hidden, Jack felt the man was rather surprised to find himself in such a situation. At the first bite of the lash he howled like a wounded animal. He then asked the devil why she was doing this and she replied that this is what he had asked for.

Before he had a chance to protest, he was lashed again and this time it was more of a curdling scream which escaped him. He was panting and shaking in his chains. He had a feeling that this man might be new to the more serious whippings which took place here. But that only made it sweeter. After what he had witnessed with the slavegirl, he knew this man was in a lot of trouble.

He began begging as soon as he caught his breath, but the devil was having none of it. She whipped him again with an even stronger stroke and followed that up with another. His screams filled the room and he tried begging once more.

“This one is a little loud. I think I’ll muzzle him.”

And so the devil approached the whimpering man and from somewhere she pulled out a gag and fastened it over his head. He fought a little, but there was really nothing he could do. Once she cinched it in place, she stepped back to take another look at her human canvas.

She made a few more passes over his flesh and the gag was working. Not that it blocked all sound from him, it was still clear he was screaming and yelping, but it didn’t overshadow the sounds of the whip and better fit as background noise.

“Not bad, but I’d like to try something a little different.”

There was another heat shimmer and now the man’s head and hands were in something of a stockade or yoke which hung from the ceiling. This was a flawless production. Then the stockade was lowered such that the man was bent over, though not fully at a 90-degree bend at the waist, but rather something in between which left his torso in a slanted position that was likely awkward and uncomfortable for him.

But then that discomfort was nothing compared to the whippings which resumed. The devil brought down the lash again and again. Jack became aware of his hand on his cock and he was now stroking in time with the devil. He was both afraid and delighted that he wasn’t going to be able to last much longer.

“Now I think we’re getting somewhere.”

The devil then began a slow walk around the victim and the camera followed. As it moved around to the other side, Jack could see the man was in tears, his head hanging in the stockade. The devil approached and grabbed a fistful of hair to yank his head up, and slap his face. And Jack had yet another surprise. The man looked a lot like him. In fact, he looked a lot like him.

He questioned whether this was all coincidence or if somehow they had captured an image of him and done a masterful overlay. But he couldn’t concentrate on those thoughts because now rather than just watching the man take his punishment, he could now imagine himself in the room with this hellish vixen and her hands on him and the flaming scourge coming down across his back and buttocks.

She held his head up and put her face next to his, such that they both faced the camera. The difference was stark as she showed no signs of exertion and the man already appeared exhausted and broken. She was clearly in control and he had no choice but to suffer at her hand.

“Shall we continue?”

Jack croaked out a yes response as his fist worked his cock. He was surprised he hadn’t already come as he knew there was a limit to how much he could hold back. But he pumped away knowing it would only be a few moments before he made a mess of himself. This night might just be worth his soul after all.

“I’ll send someone over.”

She said that and then blew a kiss at the screen. What? Surely, she was to continue with the whipping. Jack was so close. And then the screen went black. The power failed and he was dropped into a pitch-black room. Nooooo! Not now! This was so unfair. He tried to recall the last images of the devil and her whip to get him over the top but for some reason, it wasn’t enough.

He sat in the dark ready to cry tears of frustration. It wasn’t fair. He was so close and it had become so much more than he could have hoped for, and now all seemed lost. Plus he was going to have to carefully find his way out without tripping over stacks of books or banging into furniture. He just sat in the dark to let his eyes adjust as much as they could before he made any big movements.

He noticed two red lights across the room, but he couldn’t place the source. In fact, the more he considered those lights the more he was sure there was nothing electronic over there that should be producing any light. It was just bookshelves which met in the corner. Again, it was an old school and there were little electronics beside the laptop he brought into the office.

Then the two lights moved toward him and as they did a woman was revealed to him. Not a woman; a devil. She looked similar to the one on the screen but she was completely naked. And she wasn’t on the screen. She was in this very room!

“Hello Jack. Ready to have some real fun now?”

THE END