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When I was in 15 years old and in high school I went out with a girl from a different school called Lily and she was an angel when I was with her. She often sent me pictures of herself wearing only her lingerie and even naked sometimes. But she had expensive tastes and I found myself having to buy her all kinds of stuff and that was hard for a teen like me.
But as they say ‘Love is blind’ and to be able to afford all the presents she liked I had to do loads of things to make some extra money. The worst was cheating on tests to get “reward money”. I also began to steal other peoples cell phones, jewellry, ipods, and anything I could get my hands on to get money to buy her things. I also stole money from my parents and from school to help pay for the goodies.
My reward was sexy images emailed to me and I would jerk off for hours to them.
But the day came when we had a huge fight and I broke up with her because I knew she was just using me. Keeping me on leash with her pictures so I would spoil her rotten. But the problem was she knew about all the things I did to support her and to my surprise she blackmailed me, threatening to tell the teachers and my parents all about my light fingers.
I couldn’t even imagine what the consequences would be if they knew. I could end up in a juvenile prison because I had literally stolen thousands of dollars over the time I was dating Lily. So I asked her, “What do you want?” and she told me to come by her house the next day and she would tell me.
I arrived at her home about 4pm and I knocked on the door and she answered smirking at me. “Hi Lily!” is all I said and she put her hand on my chest and pushed me into the front yard closing the door behind her.
Finally she said, “I wondered if you’d have the nerve to show up!”
I shrugged, “You didn’t give me any option did you!”
She smiled again making me feel so frustrated I confess I had the growing urge to grab and punch the shit out of her. Don’t get me wrong I am not usually a guy who hits women but something about her attitude towards me right now just made me feel angry. But I resisted even though I had my fists clenched.
“OK Lily so let’s get to it. What do you want to keep your mouth shut about all that stuff?” I asked.
“I just want fairness, that’s all,” she replied tilting her a bit and smiling while looking up at me. Something that always melted my heart in the past but I was over that now. I knew it was just one of her poses she used to manipulate me.
“What do you mean fairness? You gained a lot from going out with me, I bought you so much stuff worth lots of money and now you want “fairness”? That sounds ridiculous!” I crossed my arms and glared down at her.
“I never asked you to steal for me so don’t go blaming me for your crimes. If you couldn’t afford it then you should have been a man and owned up. Instead you went and stole it all? You’re the ridiculous one!” she shot back.
“Alright have it your own way. So what’s the deal do you want money to keep silent about it?” I asked.
“Before I say what I want come inside and meet my girlfriends!” she said evenly.
“Meet your girlfriends? What is this shit?” I said throwing my arms in the air in anger.
“Fine then I will just call the cops and tell them how I just found out my ex-boyfriend is a thief!” this time she crossed her arms in anger and stared at me.
“Fuck! OK I will meet your girlfriends then,” I said sarcastically.
So I entered Lily’s house following her through the front door and found four of them were sitting on the sofa waiting for us. They were all the same age as Lily around 15-16 years old and they were I had to admit all gorgeous. This was typical of Lily as she was what you would call a looker too and so her friends were the same. No ugly fat chick friends in Lily’s world that’s for sure.
They all looked at my with a smirk so I could feel something bad was going on and I had to admit I felt a bit scared. I mean I felt like a someone being circled by sharks just waiting ever so painfully for the first bite.
Lily walked over and sat herself right in the middle of her friends on the couch so the five of them squeezed in all looking at me with evil grins.
Finally Lily said “All I want was fairness Todd. You seen me naked and now I want to see you naked!”
I lost my shit, “Naked? This is what this is all about? So I suppose your posse all have to see it too do they? This is such bullshit Lily!”
Lily turned to the blond girl to her right and said, “Belle, hand me your phone!”
The girl did so and I could see her begin dialling a number which I assumed was the cops.
“Alright! Alright! You win you fuckin bitch!” I yelled and she put the phone down on her lap and looked up at me expectantly.
So I tool off all my clothes in front of them wondering why all these pretty girls would need to blackmail a guy into doing this anyway. I mean hey most guys would do this for nothing. I stopped at my boxers but one of the girls said, “Come on Todd, the cops are only a phone call away!”
I gulped and lowered my boxers to my knees and naturally they all burst into raucous laughter.
“OMG, that’s all you’ve got? My 8-year-old younger brother has a bigger dick than you!” the blond girl named Belle said loudly.
“Are you even a boy with that? I can see why Lily dumped you now!” another said.
I must have blushed one hundred different shades of pink and red while they paid out on my cock. But that stung the most becuase in all truth I was the one that broke up with Lily, not the other way round.
“Does it even work? I mean maybe he has like a disability or something?” a red head said looking a little concerned.
“It’s not really a dick it’s more a like a clit,” Belle said sending the girls into gales of laughter. Just when I thought the torture was going to stop Lily told me again, “Fairness is what I want Todd and I didn’t get that!”
“What do you mean?” I said looking at her confused.
“You seen me naked sure but you also seen me in my underwear” she said.
“Well you seen me in my boxers just now. That’s fair?” I said confused not really understanding what she was up to.
“You have my pictures wearing LINGERIE, Todd. Now I want you to put on these pink panties so I can see you in lingerie. I bet they will fit you perfectly too with your little dick there!” she said throwing them at me.
I had tears in my eyes I admit. I had never felt so humiliated in all my life and Lily and her friends all sat their smirking and giggling as I suffered so terribly.
As I put the panties on the final blow came when she said, “Those panties really fit you well Todd! Just as if you were a girl!”
Suddenly phones were out and the girls were taking pictures of me. They made me pull them down again and took pictures of my cock as well. I never really thought of myself as small until that day. I knew I wasn’t the biggest tool in the shed but I didn’t think I was that bad. But the girls were right the panties did fit me well and it just made me feel that it was like I had no cock at all.
I was a small dick guy and now Lily had me back in her grasp once again. This time she wont need sexy pictures to manipulate me into buying her shit and giving her money. This time she really had me by the balls, my somewhat very small balls.