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Worst BDSM Erotica Ever

Jenelle Watson

I did not write this! This manuscript was written by a friend who knows I’m an erotica writer. She wanted to give it to me, which was very kind, even though it is so badly written.

When she asked for my opinion, I carefully told her how much potential it had, then how bad it was in execution. We both ended up laughing. I suggested we present it as is. Since she has a good imagination, you may find this story as amusing as I did in its own right. Enjoy!

My Friend’s Attempt At an Erotic BDSM Story

It has been over a year since Jenny wrote her last paper in law school. She had not earned enough to pay off her old college debt. Due to some unusual complications having to due with debt and the State of California, she needed $5,000 in order to be admitted to the bar.

The law profession was not her passion. Jenny’s real drive was to be a professional model. This has been what she has been practicing, and she loved her job. She also liked to have one-night stands and is very much into sex. but she never tried BDSM.

Jenny did try things related to modeling, such as performing in video arcade peep shows.

One of her friends, Victoria, had seen her in one of the booths and that freaked Jenny out. So, she simply stopped performing. Besides, Victoria had offered to introduce her to a cousin, Bobby who had his own company. She thought he might be in need of some informal legal advice. Perhaps by helping him, Jenny could get the money she needed. Jenny agreed to see Bobby.

Jenny would never have found his place, if not for the detailed description her friend had given her. After driving for a long time in the country, Jenny came to Bobby’s security gate with a speaker and camera next to the passenger side of her car. She pushed the button on the speaker and introduced herself. Without a word, the gate swung open.

She drove up the long, curving driveway. When the mansion appeared, she was so fascinated that she almost hit a fountain. It was a huge, exquisitely appointed palace, with statues, marble arches and gargoyles, all of which were overly elaborate and ornate. She pulled up in front of the main door, and parked her Toyota. As she gathered up her purse, opened the door, and got out, she almost bumped into a stout, older woman, who seemed to appear from nowhere.

The older woman quietly escorted her into the foyer, and she stood there gawking at the two staircases that curved up each side of the enormous hall, punctuated with a huge crystal chandelier hanging in the middle. Still staring at the grandeur of the place, she was guided into a smaller, but well-appointed room, just off the main entrance.

The woman motioned for her to take a seat on the far side of the room and she did so. Jenny was getting quite nervous. The woman’s silence spooked her. She sat down, knees together, clutching her purse and looking around. The room had floor to ceiling cherry wood bookcases filled with what she surmised were first editions of many classics. Situated about fifteen feet in front of her was a massage table, with a few odd additions.

The table had large leather straps hanging from it, but what really caught her attention was the large object at the far end of the table. It was covered with blue cloth. This was all just a bit too weird for her. She had a hard time slowing her breathing, and began to panic. She was seriously considering making a run for the door, when perhaps the most handsome man she had ever seen walked into the room wearing a thick white robe.

“I hope Tola has made you comfortable. She is dedicated, but not much of a conversationist,” he said with a chuckle and charming smile.

The pictures Jenny had seen of Bobby didn’t do him justice. He was stunning, with long black hair, perfect teeth, the face of a Greek god, and the physique to match. She gasped at his passionate masculinity. ‘This is the wild sexual lion that exists in my naughtiest fantasies. I really want him to bang me,’ she thought.

She hadn’t noticed before, but Bobby was wearing tightly fitted trousers and the shape of his cock and balls crouched below. She couldn’t take her eyes off his cock, and he noticed.

“I realize you studied law, but am not in need of a lawyer at the moment. I am interested in having you as my sex toy for five days while I pay you all the money you need for it. You are the most erotic lady I have ever seen,” he said softly.

One thing Jenny hated about being a redhead was how easily she blushed. His words made her flush crimson head to toe. However, to her surprise, she did calm down. Opening her mouth, she agreed, not because of the money, but because she was so attracted to him, and simply wanted to have sex with him. They shared a glass of wine, then she went home.

The next day was a hot sunny afternoon. Bobby picked up Jenny and took her to his place. At his place, Bobby chumed her into a playful girl with his charming gestures, body language, and remarkable masculinity. It was easy for him to seduce her with his powerful combination of touch and sexual whispers. She gasped as Bobby took her in his lap, rubbed the back of her skull softly with his fingers while enjoying her lips. He also pressed her calves while fumbling her nipples through her blouse before undressing himself. As he undressed himself, he climbed face down on the massage table. He was completely naked and his cock was soft but sizable, one of those corncob cocks you see in porn flicks. She hadn’t noticed before, but there was a large hole in the massage table at crotch level, so that his huge cock and balls comfortably hung below the table.

“I realize this all must seem more than a bit strange, but just relax as you give me some hot sex. I will expose you to some wild fantasies you have not experienced before. Your figure is the most erotic one I have ever seen,” he whispered.

He had her give him a brief massage, which she enjoyed, simply to be touching such a man. Then, he instructed her to undress, as he sat up on the massage table, and simply stared. She was self-conscious, yet it also made her even more horny.

Hopping off the table, he then instructed Jenny to take his place. He bound her ankles and wrists with the leather straps. While she pondered what she had gotten herself into, he opened a closet and rolled out a heavy table, topped with some sort of bulky equipment. She was wondering if it was a pump. It had a wheel bigger around than a dinner plate, and a long pipe sticking out. He locked the heavy table’s wheels into place.

Jenny had a longing for something in her vagina. His penis would be a good choice.

She wouldn’t be empty for long, as he positioned his machine on the table. Once he installed a dildo on the end of the pipe, she had a pretty good idea what the machine did. It was fucking equipment. Before turning it on, he set it up precisely so that the dildo was just touching her vagina. Turning the dial on the machine, the dildo started insistently pressing against her pussy lips, then backing away, over and over again. He pushed it closer, but the machine would not enter her. It was becoming slightly painful, but still highly erotic. She started feeling that feeling one gets when one is starting to juice up. Suddenly, on an out-stroke, the machine stretched her open, and the dildo popped in a couple of inches for a moment. Boy, did that feel great! Pretty soon, the thing was pushing the dildo into her deep, then backing almost all the way out. fucking her hard.

Bobby grabbed a smaller dildo, lubed it, and touched it against her asshole. First, he was very gentle. The contrast between the insistent, powerful machine and his gentle pressure was exquisite. Then, like the machine, he started pressing harder, and in time, he had penetrated her ass, backed out, then pushed in again.

In and out, the fucking machine and toy in her ass taking turns sliding in and out. He moved around, stretching himself to reach everything, and stuck his hard cock in her mouth. There she was – her ass, pussy, and mouth full of cock. She orgasmed hard at how dirty it was to be fucked so hard by three cocks all at once. He slowly pulled the toy from her ass, moved around behind her and asked her not to cum again until he told her to. He took his dick, wet with saliva, and pushed into her ass. feeling the dick from the fucking machine rubbing against his cock through her, both of them deep inside her. He turned up the pace on the fucking machine while also hammering her ass while hearing her moan, and feeling her cum over and over making the bed sopping wet.

Jenny enjoyed this hot and steamy sex. It was the best she had in her life. Her lust and pleasure were only growing.

Bobby was not happy that she had cum that early. He had always fantasized about a higher level of passion. Jenny would have taken him to the peak of his ejaculation. It was when he was enjoying the hot steamy sex that she had cum. To him, any lady that cums before him should not go unpunished.

Bobby planned a punishment for when next came. He would pull out of her ass, turn up the fucking machine a little more, and pound her so hard using a bigger sex machine. This would be her punishment and it should subdue her more. He was excited thinking about seeing her stretch her pussy using his big pink machine, and at another time seeing her fuck a Redbull can. He would rub some of her cum on his dick, and then turn the pace down low on the fucking machine. She would stretch around the dildo from the fucking amchine and his hard cock – both of them inside her would stretch her out. He would turn off the machine, replace the rubber dildo with a vibrating wand, then turn the pace up on the machine, while slowly raising the vibrations on the wand. In and out both the vibrating tip on the fucking machine and he went. Harder and harder, stretching her, making her cum over and over. He would increase the pace, and the pace on the machine. By now she would be cumming again, and he wouldn’t hold it any longer. He would pull out, and quickly shove his dick in her mouth, filling her mouth with his cum while the fucking machine continued to pound her. When she was fully drained, he would turn off the machine, untie her, unzip the hood, pull it down, and roll her over. She would would be spent, totally exhausted. He would kiss her deep, tasting his cum off her. “I’ve had this fantasy for a while,” he said to himself. “She will fall asleep in my arms from exhaustion.”

Jenny returned to the mansion, which she thought of as a castle for three more nights, excitedly and happily enduring similar treatments.

The fifth and last night was a flurry of activity. Jenny spent hours changing her mind about what to wear the next day. She finally settled on a short black skirt, white low cut blouse, six inch heels, black nylons, and hot pink panties. She decided to go without a bra, as her tits are small, and she liked the freedom. Tossing and turning, she tried to imagine what it was going to be like. She finally got a bit of sleep, when her alarm went off. After showering, she applied makeup, taking extra time to get it just right. Normally, she didn’t bother with eyeliner, but today, seh applied it to set off her green eyes. She brushed her long red hair, and got dressed.

Jenny entered the room behind Bobby. He quickly used the straps to buckle her in securely. He watched her the entire time. She managed a weak smile as he stripped her naked. Bobby uncovered the device behind him. Her eyes went wide, as she realized that it was a bigger fucking machine with ropes and flogger hanging from it! The pipe protruding from the powerful looking motor had a lengthy and thick dildo attached to it much larger than the ones he had used previously.

He lubed the big black dildo, lubricated her butthole, and gently slipped about half of the 12 inches into Jenny’s ass. She found it terribly uncomfortable at first, but when her body got used to the extreme stretch, she actually craved more.

She never took her eyes off him whole time. He started whipping her with the sex flogger and while doing that, turned up the sex machine that fucked her pussy with a dildo. He also massaged her breasts. Bobby picked up a remote control for the machine and sat in a chair behind the table. She could see his head. He was looking at her. She became flustered, not sure what to do in such an unusual situation. To calm herself, she took an extremely long breath, and focused on the experience. The fucking machine rammed the dildo into Jenny’s love canal so deep it was pushing her cervix aside and bumping against the far wall. After she got use to that, it was a spectacular sensation like none she had experienced before. She moaned in time with the pumping.

After a few more inhales and exhales, she figured out that Bobby was timing the dildo thrusts to her breathing. She began taking even deeper breaths, holding them a long time. She didn’t say a word, but grunted heavily with each stroke. Bobby’s cock stood out like a flagpole beneath the table, rock hard. She was becoming so horny, and a bit light-headed from the treatment. Without thinking about it, her left hand moved between her legs and began rubbing her clit. She continued moaning softly, as she took another breath, exhaling through her nose.

By this time, Jenny and Bobby were in perfect rhythm. She was taking it in the cunt full speed now, the motor was whining with the effort, while he equaled the machines efforts with the dildo he was jamming in her ass. She was rubbing her clit furiously. They watched each other, without the least hint of shame. She strained against the strap holding her, as her pussy and ass took a brutal concurrent pounding. His eyes glazed over in pleasure.

Without warning, Jenny made for under the table, firmly gripping Bobby’s cock. She began stroking him hard, and he moaned loudly in response. She milked him as the fucking machine roared, and his eyes grew wide. As her head came back down she saw him cum, shooting long wads of cum on the floor. Her fingers fanned her clit until she came too, squirting streams, leaving a pool on the hardwood floor.

The room echoed with the sounds of both of them cumming, their eyes locked on each other. Finally, Jenny released him, and the fucking machine fell silent. The only sound in the room was the two of them still panting heavily. Their eyes were closed and they both looked spent.

“I am… gasp… sorry for the mess,” she said, stammering.

“You were perfect, darling,” he said in his rich baritone voice. He steadied her and led her out of the room before handing her a brown envelope and walked her to the car. She thanked him, got in, and drove off. Once past the security gate, she couldn’t contain her curiosity any longer. She stopped the car and ripped open the envelope. As she expected, there was a check in it. However, instead of $5,000, the check was made out for $10,000.

She squealed with joy, knowing that Bobby had been happy with her performance. However, she quickly felt ashamed of what she had just done. Then, she thought, ‘fuck it! If one of the richest men in the world wants to get off making me his sex toy, and pay extremely well for the privilege, then what’s wrong with that?’ Besides, she had a series of wonderful orgasms too. She smiled and drove home.

Before Bobby slept, a text came from Jenny, thanking him and asking him to continue their relationship. He agreed, this time around without the payment, because instead he proposed to her.

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