Blackmail is only enjoyable when you’re on the giving end of it.   

It’s even better when that blackmail is deserved.  It was my first year of college and I was always broke.  I had two jobs but as everyone knows, college is expensive and I struggled to make ends meet.  I was dating a really nice guy named Jeff whose parents were wealthy and he was able to breeze through college life without any financial issues.  Lucky guy.  I didn’t like going to his parents’ house because they looked down on me and spoke to me in a very condescending way.

“So… how are you able to afford college?” His father, Bruce, asked me one day.  “Financial aid for low income families or something like that?’

I smiled sweetly.  “No, Bruce.  I am actually working two jobs to pay for college. No free ride for me.”  I said, sounding more defensive than I planned.

“Oh.  Grades not good enough for a scholarship then?”  He said, snottily.

I wanted to slap his face but I shook my head.  “We can’t all be as brilliant as Jeff.”  I said, putting my arm around Jeff.  “What’s in your fridge, Jeff? I’m starving and I’m going to eat a lot of your food today.”   I said, much to Bruce’s disgust, I’m sure.  

“I’m sorry about my dad.”  Jeff whispered in the kitchen.  “He’s a dick.  Nobody likes him.  Not even the dog.”  

One month, I was really struggling and became so desperate that I decided to answer a Craigslist ad.  It requested a young, college age girl for some casual and discreet fun with a successful and generous businessman.  I texted with him and we agreed to meet at a hotel in the next town and the “donation” was $500 for one hour.

When I knocked on the hotel room door, I was met with a huge surprise.  Standing there, wearing only boxers, was Bruce himself.  He actually gasped when he saw me.

“Sabrina?  What are you doing here?” He asked, incredulously.  

“I answered your ad, Bruce.”  I walked into the room and he quickly shut the door behind me.  “You should do a better job of screening your potential hook ups.”  I sat on the bed and smiled at him.  “I take it your wife has no idea that you placed that ad?”  

His face turned red and he dropped to the floor on his knees.  “Please.  Please.  Whatever you do… she can’t know.  She’ll destroy me. Oh god.  My life would be ruined.”  

“Now, now, Bruce.” I reached out and patted his head.  “Nobody has to know.  You have the money, right?”

“The money?”  He looked at me blankly.  

“The fucking $500, Bruce.”  I raised my voice.  “The so called donation.  Where is it?”

He jumped to his feet and grabbed an envelope.  “It’s all there.  You can count it.”

I counted it and slipped the envelope into my bag.  “Get dressed, Bruce.  We’re driving to your bank and you are going to withdraw a couple of thousand dollars for me.  I’m short on rent, I need a new couch and I’m tired of eating Ramen and your shitty leftovers.  Let’s move.  Come on.”  I snapped my fingers at him.

“You’re going to blackmail me?” It was more of a statement of resignation than a question.

“Yes, Bruce.  I’m going to blackmail you.  You’ve been nothing but an asshole to me since I met you and blackmail is the kindest thing I can do to you right now.  Would you rather I visit your wife than blackmail you?”

He shook his head slowly.  He looked like a beaten man.  Blackmail is certainly a hard pill to swallow.

“As long as you keep me comfortable with my blackmail fee every month, your wife will never know.  I promise.  But don’t fuck with me, Bruce.  I’m a man eating bitch.”  

After coming home with almost $3,000 in cash, I called Jeff.    Rather than tell him about his dad and the blackmail, I told him I got a fantastic tip at the restaurant I worked in and told him dinner was on me that night.  As far as Jeff knew, the next year was a great year for tips for me!

Blackmail role playing with Steamy Sabrina! 1-888-437-0012

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