From Misery

From her, Misery.

‘Do you want me to pick your sister up from school? D*** Secondary right?’, the stern tone of the man’s voice woke me up from my afternoon nap, sending me right into confusion as I tried to recognise the number. ‘Hello? Lenny? Are you there?’, whoever that person was, he called my name, and even knew where my sister studied. I couldn’t wait for him to spill any more details and hit him with question number one, ‘who are you?

Background noises came from the speakers and his voice got even clearer, as if switching to a earpiece to talk to me. ‘I am the person you cheated two hundred dollars from’, the words came loud and clear to me, as I recalled the one time I posted a Craigslist ad to sell my used underwear, except that I didn’t turn up. The money went into my friend’s account and everything went quiet.

I replied with a trembling tone throughout the conversation, listening to my address as well as the companies my parents worked for. I couldn’t understand how he managed to get all those details from. Not even my social accounts held those information.

‘So, what do you want?’, the most important question had to be asked, and he began rambling about how he wanted to complete the deal – with extras. I couldn’t reject even if I wanted to. Going to the police would only complicate things. One person suffering is better than my whole family right? His first question was what kept me thinking about my sister’s safety.

Panic got the better of me and I finally gave in to my despair, sobbing softly into the phone. His tone changed to a better one, but it was still as bad when he said, ‘I want to meet you now’. I knew I could excuse myself from everything just to see him then, it was just what I should wear or do that bothered me the most.

We arranged a time and location near my house, set by his knowledge of my whereabouts. Finally, the man showed up at the designated void deck, fit and in his late twenties or early thirties until what I imagined.

‘Lenny?’, he mumbled those words while loitering near me looking at his phone. ‘Yeah. Sit down?’, I sounded impatient in my hopes to get things over and done with. What could be the worst thing to happen? Sex? A square, plastic box caught my eyes and he looked at where my eyes glanced.

‘Actually, I am not sure what is happening. My dad just clipped this camera on me and asked me to wait here for a girl’, my heart immediately deflated upon learning of his ‘task’, feeling way better than if his dad met me. God, I could only imagine. ‘9XXXXXXX: Make him happy, and I will not bother your family. If you try to take advantage of him, I will destroy you completely. Don’t even think of turning the camera away.’

So, his dad will review the video and see if I served his son well? What a twisted idea coming from an old man. I had felt better after seeing the younger dude and actually didn’t mind if it was him. Following him to a closed community centre, I had no idea he was a volunteer entrusted with an activity room.

‘Wow, what do you guys do here?’, I couldn’t help but asked after seeing computers lined in front of the windows, and a few tables decorated the centre of the room. ‘A group of us give tuition to kids from needy families, and help people get jobs’, his shyness faded as we found a corner to sit, in front of his camera set up on a table.

‘What did you do to my father?’, the concerned expression really made me want to tell him, but it was for the better if he not know about my scam. Turning his focus away from my plight, I invited him to take off my clothes. He carefully unzipped my skater dress and held it at my knees for me to get out off. Unsure if he was really kind or a monster yet to show itself, I watched quietly while he undid his jeans.

We sat awkwardly together and I had to initiate, leaning over to his dick and bringing it to life. ‘Can I touch you?’, he popped the cutest question out of my unfortunate situation and I brought his hand to my groin, where he introduced his knowledgeable fingers to my clit. I did not hold back from moaning and he promptly joined me, taking multiple shallow breaths as I rubbed his cock.

His comment on my wetness got me to compliment on his size, slightly boosting his confidence with me. ‘Let’s go to the table!’, he pulled my arms eagerly and I was placed on top of the two conjoined desks, hair adjusted over my chest to prevent the edges from clipping them. Seriously? Was he going to make me enjoy the blackmail?

He aligned the camera in our direction and held my knees ninety degrees up, calves hanging freely. It came as a shock when I felt his tongue licking my pussy, sending me into a frenzy of squeals as he tickled my clit in rapid strokes. My mind went blank from his oral skills, causing an orgasm to make him work even harder. ‘Stop stop.. ‘, I barely got those words out of my mouth before he stopped, and stood motionless under my raised legs.

‘I don’t have a condom’, the lost look almost turned the whole tryst into a comedy, but I wasn’t going to get into trouble by not pleasing the man’s son. Taking a deep breath, I told him exactly what to do next, ‘just don’t cum inside me. K?’ He flashed a smile at me and placed his chest under my thighs, pushing his way into my hole in loud gasps.

‘Shittt. You’re so tight! I.. I don’t think I can last long’, his voice got more desperate the longer he stayed inside me. That six inches of pleasure, was throbbing so hard I could understand how confused he was. One thrust, two thrust, and the third marked the end of his day as he yanked his cock out suddenly, spreading my legs and got ready to cum.

Before I could let him ruin my redemption just like that, I caught hold of his dick and stroked it, singing moans to intensify his ejaculation. I only saw a bit of his load when he came, shutting my eyes to the shot flying into my face. The moment his warm cum landed on my chest (instead), I opened my eyes one by one to see him thrusting wildly into my palm.

‘Sorry’, he kept repeating it as he fell on his hands, panting for his life over my belly. ‘It’s okay.. it’s okay. You enjoyed yourself right?’, the lousiest consolation did nothing to ease his guilt and he cleaned me up with his wet tissues. I got off the table and pushed his butt against the edge of the table, purposely standing close to him so he would put in a good word for me.

‘You’re making me weak.. please stop.. ‘, he begged me as I fondled his shrinking cock, turning me on with his pitiful response. Making a grown man moan like a woman actually made me felt powerful, and I finally stopped after he fell to the ground. He set the pace to wear our clothes back (which was fast), in case anyone returned. The walk back to the block we met was pretty much quiet, except for the messages his dad sent regarding his son.

Well, I didn’t want to say much since he would be ‘seeing’ my action on cam. Jason, the well-mannered guy hugged me before walking away, and I made my way home without any questions from my family.

9XXXXXXXX: We don’t actually live far from each other. See him tomorrow at 9pm, same place.

What seemed like blackmail turned into a matchmake for me, but I wasn’t going to take any of that lightly either. There is no going back if I screwed up. I took a long shower after confirming my attendance and went to bed. Somehow, I didn’t feel compromised, even though penetration did took place. Tomorrow.. I’ll see how.

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