All characters are 18+
I made one mistake in my life. I let Billy finger me in the back of his car. I couldn't help it, I was young and a virgin and he was so beautiful. I was only doing what teenagers were supposed to, exploring. I remember the heat of him pressed against me, his lips against mine, the weight of his body on top of me in the back seat of his car. It was hot. I knew I should have stopped him when I felt his hands sliding up my legs. I definitely should have stopped him when I felt him rubbing my pussy over my panties. It had gone too far when I felt his fingers slip inside my soaked pussy. Truth is, I knew I should have stopped him but I was young and horny and I wanted it just as much as he did. His fingers felt good inside me, I had to stop kissing him to moan. The heavenly pleasure was cut short though as my phone started to ring and I knew it would be my father wondering where I was. It was getting late and Billy knew how strict my father could be so he drove me home and made sure I was through the door before curfew.
That night I lay in bed, drunk on the hazy memory of our all to brief encounter. I wanted more. I wanted more of him and I brought myself to several orgasms in bed fantasising about Billy stripping me naked and having his way with me. My parents were going out of town for a big election rally at the weekend. I would have the place to myself. I decided to invite Billy over and let my fantasies become real. I just had to get through friday.
Friday morning at school was uneventful. Billy was busy with football practice so I didn't get to talk to him much, but he texted me saying he would drive me home. At lunch I told my girls I would meet them in the canteen, I just had to use the bathroom.
I was stood at the mirror checking my makeup when the bathroom door opened. I turned and saw Rebecca walk in. Rebecca was a girl I was aware of but had never spoken to. She was short, big and formless. The exact opposite of me and the stark difference between our bodies was highlighted as she also came to stand in front of the mirror next to me. At first I thought that maybe she needed to wash her hands but she just stood there staring at me.
'Hello?' I said, wondering what the strange girl could possibly want.
'Hello Sarah. I have something to show you.' she replied, an eerie smile spread across her plain face.
'To show me?' I replied, confused but a little curious.
I watched her reach into her jacket pocket and pull out three polaroid pictures. She laid the pictures out on the counter and my stomach flipped when I saw what they were pictures of. All three pictures featured me very prominently loving the feeling of brads fingers inside of me. My face and pussy were both clearly visible. I stared at Rebecca with a dumb look on my face, my mouth hanging open in shock.
'You're dad is running for local government right?' She asked me, clearly already knowing the answer.
I just nodded.
'So if these pictures ever got out, it would probably not only ruin your life, but his as well.'
Again, all I could do was nod.
'Well luckily I don't plan on showing anyone. Don't make any plans tonight princess, I'll be at your house at seven and we can talk about what you're going to do for me.'
I watched her turn and leave the room.
A million thoughts and fears ran through my head for the rest of the day. I couldn't concentrate on anything else. Rebecca had said she wouldn't show anyone but I had no idea what she could possibly want from me. In the space of 24 hours I had gone from being on the verge of losing my virginity to my handsome boyfriend to probably being blackmailed by the short dumpy strange girl at school. This wasn't supposed to happen to girls like me. I was beautiful. I was a cheerleader. My family was wealthy. I was supposed to live a blessed life, not end up having my own nudes used against me. All I knew for sure was that I couldn't let those pictures get out. I would just have to do what she wanted and make sure I got those pictures back and destroyed so I could forget any of this had ever happened.
I floated home in a daze. My parents had already left for the rally when I got home so it was just me and my thoughts. I was so worried I could barely eat so I nibbled at a slice of toast before showering and changing into some comfortable pyjamas. I knew Rebecca was coming but I just needed to find any level of comfort I could and my pyjamas had always offered security. At exactly seven there was a knock on my door. I took a deep breath before opening it and sure enough, there was Rebecca in a gross stained t-shirt and a backpack stood on my doorstep. Before I even had a chance to say anything at all to her she shoved past me and into my house.
'Wow princess, your house is even nicer on the inside huh.' She said, walking through into the dining room and putting her backpack on my table. I followed her into the room, suddenly feeling very vulnerable in my short pyjama shorts and loose fitting vest top. She looked me up and down like I was a piece of meat. I decided to just cut to the chase with her and get this over with.
'Rebecca, I need you to destroy those pictures. I don't know why you took them and I don't care. If you destroy those pictures right now, I'll forget any of this even happened.'
A moment of silence passed where I foolishly started to believe that maybe she would do what I would say.
'Okay. Here's my alternative deal, you do what I want for one evening and I will destroy the pictures.'
'You will?' I asked, hesitant to trust how easy this had been.
'Sure. I will destroy them and never talk about them ever again. You just have to go along with what I say for one evening.'
One evening didn't sound too bad but I had no idea what it was she had in mind and the way she looked at me made me fear the worst. I think she must have been able to tell what I was thinking as she then quickly added 'I'm not a lesbian. I know people at school think that but I'm not. I don't want to do anything sexual with you. Actually I just want your help with two things.'
'You want my help?'
'Sure. It's no secret that I don't have any friends. I know how I look and I know that me being poor means no one wants to hang out with me. I'm used to it. I only live with my dad and he's hardly ever around. It's kind of embarrassing but I don't know how to be pretty like you. No one ever showed me how.'
She blushed as she said it. Like she was aware of how pitiful what she had just confessed was. But I didn't pity her. Actually I found it endearing. It felt like for the first time Rebecca had gone from being a strange cartoon character to be laughed at and mocked at school to being a real person. I saw her, I respected her vulnerability and I even liked her a little bit.
'You're the prettiest girl in school. I was hoping that if you could show me how to do makeup and get dressed up all nice, then maybe the other kids wouldn't laugh at me so much.'
'And what was the other thing you wanted help with?' I asked. Rebecca got quiet then and looked at the ground.
'Well, like I said. It's just me and my dad at home. He hunts a lot and isn't home all that much. I kind of figured that if I could get good at hunting, then maybe he would take me along and we could actually get along. Look, I know what I'm doing is wrong but you don't understand what my life is like. I have no one and I have nothing. This is the only way someone like you would ever even look at me let alone talk to me.'
She was right, I realised. If she didn't have power over me I would never have given her the time of day. I was mad at her for what she had done but I understood why she had done it.
'Okay' I said, 'I'll help you.'
I took her upstairs. I could only imagine the dump she must have lived in with the way she was staring in wonder at every little detail of my house. It was honestly like she had never seen a chandelier before. She followed me into my bedroom and I told her to sit on my bed while I sat down at my dressing table. I talked her through what everything was, what it did and how to apply it. I showed her my favourite shades and how the colours can complement each other. She watched with rapt attention as I applied a smokey eye and a red lipstick. We even started to laugh and joke along as we went. She asked great questions and learned relatively quickly.
When my makeup and hair were done she very sheepishly asked me to show her how to choose and style clothes and by that point the dynamic honestly just felt like friends at a sleepover so I felt happy to help her out. She politely turned away while I chose some underwear and put them on. I wanted her to see how clothes could help accentuate a body or hide undesirable bits so I chose a nice pushup bra to highlight my perfect tits and a thong to frame my cute little ass. When she turned back around she couldn't believe what she saw.