The Punishment of Jim ~ Strap-On Erotica

By Josephine, on December 1st, 2009

She then penetrates him, with the huge black strap-on dildo ripping his ass open. As if he were watching a movie, he sees himself screaming in the mirror.

Jim worked out and took care of himself. He would often spend thirty minutes in front of the mirror just admiring himself. He flirted with women and was considered a male chauvinist. In fact, the ladies in the office talked behind his back about what an asshole he was. They could have easily reported him for sexual harassment but knew that ultimately they could lose their jobs, and with the economy and job market in the state it was many couldn’t take the risk. To save on money the company hired temps during heavy workloads. Jim was especially flirtatious with part-time temps because he knew he’d probably never see them again.

Then there was Josephine. A sexy, well-dressed young woman in her early 30’s. There was something “different” about her. She was like the girl next door with an edge. She walked confidently across the room in a skirt that was considered too short for a professional office. Her long blonde hair hanging freely down her back. She wore black four-inch pencil-thin stilettos. One of the secretaries pointed out the dress code to her the first day of her temp work but she laughed and said, “Fire me. I’m not buying new clothes for this job.”
After a few sexual innuendos and no response, Jim pushed his crotch against Josephine’s ass as she bent over to get water from the water cooler. He pretended to be squeezing by but had plenty of room. Calming herself, Josephine stood up, turned, stared him right in the eyes and said, “No problem, you should have stayed.” Her beautiful blue eyes had a cold stare, and when she smiled it was almost dangerous. Of course Jim accepted this as an invitation for additional advances. Stupid man.
“Josephine, would you like to have a drink after work?,” he asked her.
“Actually, I would love that, Jim. I’ll meet you downstairs and we can take my jeep,” replied Josephine.
At 5 sharp Jim was downstairs waiting for Josephine. Josephine watched out the window to make sure everyone left first and didn’t see her leave with Jim. Once the parking lot was clear she went downstairs to meet Jim.
“I think its best no one from work knows we’re meeting after work. I wouldn’t want you to lose your job, Jim,” Josephine tells him as they get into her Jeep.
“I’m not losing my job, Josephine. I’ve dated lots of girls from the office and they know better than to kiss and tell. If anyone loses their job it will be them,” Jim laughed condescendingly.
They drove across town to an intimate pub where they sat and drank martinis. Josephine smiled and listened as Jim talked about himself and his achievements. What he didn’t know was Josephine wasn’t at all interested in him. In fact, she despised him and thought he was a jerk. She was just waiting for the right moment to make him pay for it. Jim excused himself to the men’s room. While he was in there, Josephine slipped something into his drink.
Jim woke up barely able to move. Once he became fully conscious he realized that he was on his stomach legs spread open, forced apart and tied down. His legs hung from chains and a spreader-bar, his chin rested on the edge of the table leaving only his torso and arms securely strapped to a small table. He felt something on his legs, ass and crotch … pantyhose. He began to scream.
“Shut up, fool. No one can hear you down here.” Suddenly Josephine came into his view wearing a mistress corset and thigh-high leather boots. She is carrying a long riding crop.
“I bet you think you’re a big man, don’t you? I bet you actually think all the women want you when in fact, Jim, they can’t stand you,” Josephine laughs. “And I bet you thought you were going to get lucky, didn’t you? That maybe you’d get a chance to fuck me?,” she continues to laugh.
“Get me out of this thing. This isn’t funny anymore,” He commands.
“I’ll let you out after I’m done making you pay for what you did. You can tell anyone you want. No way anyone is going to believe you. And when I’m done with you I doubt you’ll ever want to admit this to anyone,” she replies as her laugh now becomes wicked.

She walked behind him, pulled down the ass of the pantyhose, and shoved a five-inch inflatable butt-plug into his ass.

She walked behind him, pulled down the ass of the pantyhose, and shoved a five-inch inflatable butt-plug into his ass. Jim screams. Attached to the end of the butt-plug is a long rubber tube and pump. With the riding crop in one hand and the pump in the other, Josephine sits on a stool in front of Jim’s face. She moves her crotch into his face. “Lick it, bitch!,” she commands. She then reaches over and smacks him with the riding crop. He opens his mouth and begins licking her sweet pussy. Her pussy is slippery-wet as though it’s been excited for hours. Suddenly he hears her squeezing the pump and the sound of air pushing through the pump. The butt-plug begins to grow inside of him. Jim tries to move. Josephine brings the riding crop down across his ass even harder. “Lick that pussy, sissy bitch!,” she shouts.
Jim licked her warm, moist cunt until her body shook with a satisfying orgasm. Josephine bent over, looked Jim straight in the eyes and said, “Don’t worry, Jim, I’m not done with you.”
Josephine walked away but returns rolling in a full-size dressing mirror. She places it in front of Jim’s face. He can now see the contraption she has him in, with his legs suspended, spread open and available. He can now see Josephine behind him. She walks over to the stool she previously sat on and begins placing several sizes of dildos on it in front of him.
“I am going to fuck you with every single one of those,” she informs him.
Jim looks at the seat and becomes terrified at the size of the dildos. Surely she will rip him apart with them. His heart races and he finds it difficult to breathe. Josephine now stands in front of him with a huge black cock strapped inside of a leather harness. She shoves it deeply into his mouth. “Suck it whore!” Jim has no choice then to suck the large, black tool. She then walks behind him, getting close to his rear, and begins sliding the massive cock up and down the crack of his ass. He watches her in the mirror that is in front of him. He watches the look on her face as she sees his face in the mirror. She then penetrates him, with the huge black strap-on dildo ripping his ass open. As if he were watching a movie, he sees himself screaming in the mirror.
“Shut up, Jim! I want you to watch me as I fuck that man-pussy. I want to see the look on your face as I violate you.” She increases her pace driving the cock into him deeper and deeper, faster and faster. Helpless, his legs dangle and he is unable to escape her as she fucks him. For the next hour she takes him with every dildo she placed in front of him. She carefully picks each one up, shows it to him, straps it in her harness, forces him to suck it and then fucks him as he screams.
Jim’s screams eventually turned to moans as his ass became hungry to be full again. Each time she pulls out he begs her to stuff his ass again.
As she concludes the session with the last dildo, she pulls the cock out, walks over to his face, squeezes the balls, and white fluid squirts out all over his face. She chortles with satisfaction, “Looks like you’re MY bitch now!”
Josephine drove the now-unresisting Jim back to the office. Excited, yet utterly embarrassed at what had just happened, he climbs into his car hoping no one will ever find out what happened.

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