Jake's Daydream & Nightmare Pt. 01

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A virgin overachiever, meets his daydream and nightmare.
1k words
4.19
16.6k
10

Part 1 of the 2 part series

Updated 06/10/2023
Created 08/25/2021
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Jake, a 20 year old, was an academic overachiever in the first year his college. Straight As, math and science gold medals, special recommendations, he had it all. He sucked at sports and wasn't the most physically well-built but he was never bullied as he actively helped the jocks with their tests and homework so they were glad to call him their friend.

However, there was one area where he was a total loser, and that was when it came to girls. He just couldn't talk to girls. Anytime he tried to talk to one he would freeze up. He wanted desperately to get laid but he just couldn't do it. Moreover, his college was extremely liberal when it come to boys and girl staying together and allowed both of them to come and go or stay in each other dorm rooms. He often saw boys on his dorm have girls over, wishing desperately to be one of them but all throughout first year that opportunity never came.

The second year would have been the same for him had it not been for Chrissy, a 19 year old freshman. Chrissy was a tanned, 5.1 feet tall, college freshman. She was exceptionally hot. The moment the boys saw her on her first day, they were instantly attracted to her. They all eagerly waited to see where she would go sit. To all their surprise, she went and sat next to Jake. Jake was shocked for a second but then thought she had picked him at random. That's when Chrissy spoke.

"Hello Jake, I've heard a lot about you."

Jake almost went into shock. He could not believe what he was hearing. He could utter a single word in response.

"Oh I'm the younger sister of one of your older sister's sorority sisters, nice to finally meet you."

Jake was quite surprised by this revelation as his sister went to college literally thousands of miles away so it was quite the coincidence that someone connected to her had turned up here.

"let's have lunch after this seminar together, "she giggled.

Jake was overjoyed and scared. He was about to go on a date with the hottest girl he had ever met but was scared that he would mess it up by being a loser who can't talk to girls. Nevertheless, he reached the café excited.

Chrissy arrived 30 minutes late, she was wearing a cropped-tank top that wasn't hiding much and hot pants. Just looking at her turned Jake on.

"Hi!" Said Chrissy.

Jake tried to say Hi back but words didn't come out of his mouth so he just waved like a moron.

"Sooooooooo, I have heard a lot about you, you are an overachiever, you excel all academic stuff and you even good money by taking side projects in your free time! A total winner."

Jake turned red and a big smile covered his face. He finally managed to say two words, "Thank you."

Then Chrissy face changed into a wicked smile "I also know you are an A grade loser who can't even talk to girls."

Jake's smile vanished. He couldn't believe his ears. He just sat back, looking dumfounded.

Chrissy continued " So I have an offer for you. I have dealt with guys like you before, what you need is strong dominating woman to tell you what to do because otherwise you will never be able to interact with a girl."

"I can be that dominating girl for you. I will make you my pet. I will control everything you do and in return, you will do all the college work for me and I get 70% of what you earn through your projects."

Jake was stunned at what he had heard. He tried to say " no" but before he could he realized that he was feeling extremely turned on. More turned on than he has ever been before. So instead, he just nodded in agreement.

"Perfect!" exclaimed Chrissy " Now just one thing to make sure you can't change your mind. Take this bag, go to the washroom, find a stall and figure out what needs to be done and then click picture and send them to me.

She handed take a black bag and Jake hurriedly went to the washroom and found a stall, locked it and opened the bag.

Each item was more shocking that the last. Their was a thong and bikini top, both in pink, followed by something shook Jake to his core. It was a chastity cage. A metal one at that. "For Long term wear, Unbreakable" was written on it's cover.

Jake just sat their looking at the contents of the bag. This was the moment. It was now or never for him.

It look him 20 mins to figure out how put on the chastity cage and another 10 to actually put it on as his tiny boner was interfering with him. Once he did manage to it on, for some reason it felt natural to him.

He put on the thong and the bikini and then clicked pictures as instructed. The cage was pressed hard suppressing his boner but he didn't feel much discomfort. In fact, he felt like a huge load had been taken off his chest.

She replied with laughing emojis and a single line message reading "You're mine Now, loser!"

He got dressed and came out to find out she had already left. He was slightly annoyed at this but he paid the bill and went back his room. That is when the gravity of the situation hit him and he had a mini freak out. But he calmed down soon enough.

It was the first day of his sophomore year in college and he had had more female interaction today than ever before. He was locked in chastity cage and a girl he had just met had pictures of him that could end him. He felt both terrified and excited at the rest of the year held for him.

To be continued in part 2


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AnonymousAnonymousover 1 year ago

These stories are all the same. It would take alot more to get a kid that smart, to go along with blackmail that would jeopardize his standing. Lazy writing.

AnonymousAnonymousover 2 years ago

Awesome story.

Looking forward the next chapter.

AnonymousAnonymousover 2 years ago

Great, but much to short.

AnonymousAnonymousover 2 years ago

Good start!

CornixCornixover 2 years ago

looking forward to the next chapter and seeing where this goes. Thank you.

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