“Yeah,” She informed me. “It’s kinda weird, but knowing I lost this… bet to a man who has no issues using my body however he wants… well, it rapidly puts into perspective. I mean, I am glad he was at least considerate enough to let me give my virginity to a man of my choice, but in exchange he basically raped my ass hard. I wasn’t ready and it didn’t feel good… Okay, it hurt for a while, but in the end I orgasmed… I was so ashamed of it.” She snuggled up to me, curled up and obviously feeling small. “I realized there are men that will do anything to a woman, no matter how much it hurts her, and well… I started googling. I’d never even heard of some of the stuff some women will do. And I realized that like it or not, I was probably going to end up doing it for this asshole.” Then she looked up at me, “So I figured why not try to get as many enjoyable experiences as possible before this asshole ruins things that could be fun for me and my man. It’s amazing how many things, even revolting things, become less revolting when it is a matter of when and who, not if.”
She snuggled right up to my chest. “I think I picked a good one.”
I felt like the biggest scumbag ever. I had manipulated and abused this poor girl and in a cruel twist of fate she was now surrendering to me completely, both willingly and unwillingly. She simultaneously thought I was the best guy in the world and the scum of humanity. I deserved the scum of humanity title, but was nowhere near the best guy ever.
She must have picked up on my guilt, because she propped herself up, tits swinging tantalizing between us. “Hey, none of that. You aren’t allowed to feel guilty about this.”
“But we’re only having sex because some asshole has leverage on you, it’s basically rape.” I admitted.
“Nope. You stop that right now.” She told me, “I am not going to let the man who has given me more orgasms and pleasure in the last two days than I’ve had my entire life talk about himself that way!” She poked my chest hard, “I’ve felt more love from you, a boy I only had classes with and ignored for two years, than I have from my own father my entire life.”
“I’m not dumb enough to think that the random guy I picked to fuck me, because I wanted to control who broke my hymen, is going to marry me. But I am smart enough to know you’ve made the last two days of my life heaven, and while I’ll never tell the asshole who I lost the bet to, losing that bet has been one of the best things that happened to me.”
“It brought you into my life and between my legs and I’ll be damned if I’m not going to enjoy every second I get to have sex with you.” She was really heating up. “And hell, it beats being pushed to marry some rich old bastard for my dad’s ambitions.”
She snuggled up to me again. “I don’t want to end up like my mom. Married for money and security to a man I only have sex with so he doesn’t leave me penny-less. I know dad made mom sign a prenup. And infrequent sex was listed as a legitimate reason for separation. She told me when she was trying to get me to do yoga and gymnastics because she didn’t think I was smart enough to go to college or support myself. It was the first time she talked about getting me breast augmentation. She told me I had to start doing beauty pageants so I would make a better trophy wife and could marry a richer dude. She even had a few options picked out. Not one of them was under 50 years old and I was 17 at the time.”
“Compared to that, you are a superstar.” She breathed, “and if I have to fuck a guy I don’t love a hundred, five hundred, times to get the love and satisfaction I have with you…. lube my ass and pussy, and I’ll do it gladly. Though I wish it were you fucking me, not him, it’s worth it. Plus you’re going to help me catch up in school.”
I looked at her, unsure how to feel, “I’ve been meaning to ask you about that. You have some of the best grades in our classes, and you said you’d already turned in the assignment yesterday, but when we were working on it, you didn’t seem to understand any of it. What’s up with that?”
She hung her head. “Promise to keep a secret?”
I nodded.
She held out a pinky like a kid. I laughed and held the pinky.
“It’s not funny.” She muttered. “Well, here goes…. I’m cheating.”
I was caught aback. Was she really telling me this?
“I haven’t gotten honest grades since middle school.” She admitted. “My mom saw my grades and started using my father’s money to get test keys and completed assignments for me to turn in. She taught me how to find people who could get me answers and how to find what was expected on the open answer questions. I thought I could get through college and get a degree like I got through high school. Then I’d get my trust fund and could just live off that.”
I was processing, so it wasn’t tuition money she’d be out if the blackmail information got out and she got expelled, it was her trust fund.
“I won’t tell anyone, but what would happen if anyone found out.” I asked horsley.
She readily replied, “My life would be over. Daddy would take my trust fund away. Mom would do her best to get me married as a gold-digger, but even with all the plastic surgery, fake tits and ass, she warned me if it blows up and becomes public knowledge I got expelled for cheating, even most the old fat horny rich guys who usually marry dumb bimbos wouldn’t want me. There is no shortage of ditz with more boobs and ass than brains who will fuck them for their money, so why settle for one with public baggage? Especially one that has no sex experience.”
Holy shit! My blackmail had accidentally been much bigger than I thought.
“How much money is in your trust fund?” I asked legitimately curious.
“Oh, I hardly pay attention, it’s like a hundred or a hundred and fifty million or something.” She tossed out flippantly.
I just about choked.
“Yeah,” she said, “I know. Not too much, but enough to live on.”
I looked at her to see if she was teasing me, but thought she might be serious.
“That’s actually what this whole thing is about.” She confessed. “It wasn’t a bet. It’s blackmail. The asshole found out I’m cheating and said he’d go to the administration if I didn’t do everything he said. I’m just so glad he let me give my virginity to you. This has been the best.”
My head was spinning.
“So what are you gonna do?” I asked.
“Well, I get fucked until I figure out how to get him.” She grumbled. “At this point he has probably a hundred nudes of me too, because that was the first thing he started asking for.”
154. I thought, thinking of the external hard drive full of those nudes. It was locked in my desk, password protected.
“I’ll have to show you the highlights, I mean,” she looked over her naked form, “I’m nothing special.”
“Lies and slander!” I gasped.
Courtney laughed, a cute happy laugh. “Oh, come on. I barely have boobs, and my ass is too small.”
“Oh, let’s see.” I leaned down and sucked her left nipple into my mouth, pulling as much boob as I could into my mouth, eliciting a gasp of surprise from Courtney. “Yep, and…” I gave her other breast the same treatment. “… yep. Enough boob to fill my mouth and my hands. Anything bigger is just a waste that makes your back hurt.” My ex-girlfriend in high school had always been complaining about how much her tits made her back hurt.
“Not enough to give you a decent titty-fuck.” She told me.