Jennifer’s Twisted Fate by Tobey Phillips

Jennifer’s Twisted Fate by Tobey Phillips

This story was written strictly for pleasure only. I own the character’s and they are of my own creation. This is a work of fiction and any resemblance the character’s have to real life people are strictly coincidental. , Jennifer had the most intense and bizarre sexual experience happen to her when her husband was away on business. He was a salesman for a fast-paced software company which meant that he often traveled to go to trade shows or meet potential customers and investors.

It was very late at night and she had just finished a personal session with her favorite vibrator when she swore she heard footsteps in the hallway outside of the bedroom. “Jeff? Is that you?” She called out, frowning. Her husband normally told her when he was returning from an engagement early and the last text she got was over an hour ago saying good night. It couldn’t possibly be him, right?

Jennifer was naturally scantily clad in a silk nightgown that barely went down past her thighs. She would later curse herself for her attire that night, though it was her favorite nightgown that she owned to date.

She moved toward the door and screamed with shock as a large man wearing a black ski mask appeared in front of her. He pushed her backward and she stumbled and fell back, landing on her ass on the floor. She recovered quickly and scrambled onto the bed, unfortunately having no means of protection like a gun or knife in the room. Another decision she would later regret.

Four more men appeared beside the other man. They were dressed head to toe in black. Black pants, black long-sleeved shirts, black ski-masks, and black boots. They were of average build and every one of them was tall muscular. Their eyes didn’t look familiar at all to her and she didn’t recognize any of them whatsoever.

Jennifer was so scared that she was shaking, and she barely recognized her own voice as she spoke. “What do you want? Is it money? I can take you to the safe with all the jewelry and money we keep in the house!”

The one that had pushed her into the room spoke up and his voice was deep and gravelly. “Money, among other things.”

Jennifer paled as she saw the man lick his lips as he spoke. She noticed then that they were all staring at her with a lusty look in their eyes and she gasped audibly as she saw the one that spoke to her was hard and aching in his jeans. She could see the large bulge that had formed under his pants and the sight frightened her.

“Oh, no. Please. Anything but that! I’ll give you anything. Just not that. I have a husband, he’s going to be home any moment! He’ll call the cops on you and arrest you all! He is a very powerful man.” Jennifer thought that maybe her lies would be convincing enough to get them to leave. No one wants to go to jail, right?

“Honey, we don’t care about any of that. You’ll take us to the safe.” He paused for dramatic effect. “After we’ve had our fill of you.”

Jennifer was more scared than ever. “Please, no, please. You can’t!” But she knew it was useless. There were five of them and one of her. And they looked to be extremely strong, capable men. She had no idea what was in store, but she didn’t want to resign herself to her fate just yet.

The first man, we will call him Sean, moved so fast that she barely had time to scream before he was upon her. The others, Jim, Gary, Josh, and Chris, were helping Sean out by holding her still as she struggled uselessly.

It wasn’t long before her nightgown was raised high above her tits and she let out a gasp of shock as Gary and Chris began to suck on her nipples and breasts, biting, nipping, lapping, as her back arched and she continued to struggle against their advances.

Her nipples were always a sensitive subject for her during foreplay so having the two men’s rough lips manipulating them in such harsh ways was unwillingly turning her on. “No, please, no! Oh, God.” She was so embarrassed and ashamed, as her nipples got steely hard from the men stimulating them. Seeing her react like that, just caused them to further their efforts, and she moaned and groaned as they both kept relentlessly sucking and slurping on her hard nips, occasionally giving them a sharp nibble that made her gasp loudly.

“Fuck, this bitch is loving this,” Chris said, with a throaty growl.

“I am not! Don’t put words in my mouth! Bastards!” She shouted, attempting to push Chris’s head away from her breast. He angrily grabbed her hand and trapped it behind her on the bed, effectively pinning it as he went back to happily suckling and feasting on her tit flesh.

“Oh, God. Please, stop, please!” She begged. She could feel her pussy absolutely throbbing from all the sensations these men were giving her tits. It was so much pleasure that her brain went to overload and she knew if they kept this up, she could cum just from having her breasts sucked on.

They did stop, just for a moment, but it was a brief reprieve as they easily removed her nightgown. She tried to struggle to stop them from getting it off, but they were too strong for her.

“Holy fuck, this bitch is so wet!” Said Sean, amazed at how dripping she was between the legs. He could clearly see the fluid there, and the sight aroused him more than anything.

Jennifer was blushing as the men ogled her pussy, which, to her shame, was indeed slick and hot. She was too modest to admit to them that she had masturbated before they showed up, knowing they would just get off even more if she said that.

“Please, I beg of you, don’t do this, please,” she pleaded, trying to scoot back on the bed to curl up into a defensive ball.

Of course they immediately grabbed at her and she squealed as she felt herself being held down while Sean inspected her pussy more closely than she wanted him to. She could feel his fingers probing her most sensitive place, and she bit her lip as his middle finger easily slid into her and began to wriggle around. He was soon fucking her with the long, thick digit. Not long after his thumb began to lightly stroke her clit in small circles, and she saw stars as her world exploded and she had an involuntary orgasm on his thick finger.

“Oh, Goooooood,” she moaned out, rolling her hips as the sudden release took her by force.

“Holy shit! What a fucking slut! She’s cumming all over my finger!” Sean exclaimed, and all of the other guys laughed with delight as they saw her hips gyrating to the movement of Sean’s soaked digit.

As she was calming down she found herself flipped over so she was on all fours, with her ass vulnerable and exposed to the aroused men. Jim and Josh who hadn’t had much of the action were now squeezing and groping her sensitive tit flesh, pinching and rolling the nipples between their fingers to get her juices flowing again as she prepared for what was next.

Her eyes shot wide open as she felt Sean spreading her juices over her puckered star of her anus. “What are you doing?! Not there, please, not there! I’ve never been fucked in the ass!”

This just made all of the cruel men in the room laugh harder. She hated the fact that she was an anal virgin and how that naturally got them even more hyped up for what was to come.

“Oh, that just makes this even that more satisfying, baby,” said Sean, with that confident and seductive tone in his voice.

She squealed as his middle finger that was just in her cunt began to push on her puckered star. With all the pussy juice it didn’t’ take long for him to get a finger inside of her. Just that tiny penetration hurt but it was soon replaced with something else she was unfamiliar with, a slight tingling as his digit frigged her ass.

He soon had two fingers inside of her and was stretching her, preparing her for what was to come. His fingers weren’t hurting her, but she knew the moment his cock penetrated her, she was going to be in for a world of hurt.

“Please, stop, please!” She begged, unbelieving that this was actually happening. She felt so powerless and defenseless, for there was nothing she could do to stop these men from using her for their pleasure. And sadly they knew it from the beginning.

“I don’t think so, bitch. It’s going to hurt at first, but you’ll soon be begging all of us to have a turn at your tight ass,” Sean bragged, again so cocky and confident. She had to wonder if this is what they did for a living, breaking into random houses and fucking housewives wherever and however they pleased. She shuddered at the thought and quickly pushed it out of her mind. At this point she was just preparing for the inevitable.

Once Sean felt she was stretched enough, he thoroughly lubricated his cock with her juices and placed his large member against her ass. She screamed into the bed as the fat, purple head began to penetrate her poor virgin anus. The pain was intense and as the head finally popped in, she screamed some more and begged for him to take it out.

But Sean ignored her pleas and wails of pain. In fact, they seemed to excite him and the men watching even more, if anything. Her tight little hole clenched around his protruding rod as he forced more and more of his length into her, stretching her tight little hole. Despite her resistance, his manhood found its way through her defenses, forcing its way through her squeezing hole inch by painful inch until he was soon buried balls deep in her stretched ass.

Jennifer begged for him to take it out as her assaulted sphincter contracted and sent constant pain throughout her body. She felt him withdraw until just the tip was inside and then slam forward with a strong push, causing her to screams to grow in strength as the cruel man behind her began to fuck her tight, squeezing ass.

“Oh, fuck, she is so fucking tight!” Sean exclaimed, giving Jennifer’s ass cheek a nice hard slap as he banged into her overstuffed, abused chute.

The burning friction was almost unbearable and she screamed and cried as Sean continued his assault on her raw bum. All of this just seemed to excite the other men more. They now had all removed their pants and she could see their thick, throbbing erections dripping precum as they jerked them at the sight of the erotic scene before them.