“So if another virgin offered to let you deflower her, would you?” Courtney asked curiously, looking up at me.
“Doubt it’ll happen. But while we’re together, no.” I told her, squeezing her tight. “I’m happy with what I’ve got here.”
“But the only way you’d fuck another girl is if she’s a virgin?” Courtney pressed, still curious.
“I guess other circumstances might exist. I would be willing to try a relationship with a girl who has had maybe one other partner, and got cheated on, or he died. But most girls, once they give up their virginity if they leave their relationship, nowadays, they just turn into sluts. And most of them are walking STD hives as far as I’m concerned.”
“Hmmmm.” Courtney mused.
“I hope that doesn’t come off as entitled or snobbish. I’m just not going through that again.” I explained.
“I know some girls would say it’s entitled. Mostly because they want a gentleman when they’re done being the party cum dump.” Courtney agreed, “But I see where you’re coming from. I was kinda desperate when I asked you to fuck me. I really hoped your reputation was right, that you were the ‘boring nerd’s who didn’t go to parties and sleep around. Pretty much for the same reasons. I’m sorry Nikki did that to you, but her loss is my gain.”
She lifted her head a bit, “But that does mean since most of the girls I hung out with were the virgins who hated party sluts, I need to be careful introducing you to my friends. They might decide they want to try the dick good enough that I gave up my cherry to it.”
Courtney was getting nervous. “Usually he responds after something like this.”
We had sent the technically still mandated picture of Courtney’s fucked pussy to her blackmailer. Then, since he hadn’t replied, Courtney took the time to take me up on my offer of a dinner date.
“Let’s just enjoy the time together and we’ll see what he says when he replies.” I told her.
We ended up going to a local sushi place, since it turned out we both loved sushi. It was a nicer place, a little pricey, but Courtney insisted and she was paying (despite my objections).
Courtney was looking good in a tight top that showed of her tits and a tight leather skirt that just made her ass beg to be fucked. The one time she bent over it pulled the skirt tight enough I could see the strings of her thong pressed onto the leather and it gave me an erection that would last until we got home.
“I’ll try, but I wish I knew what he was up to.” Courtney accepted glumly.
The conversation turned to books, and it turned out we were both fantasy lovers.
“The Eragon movie was a crime against literature.” Courtney declared, “Almost as bad as the Avatar: The Last Airbender movie.”
“Right! Hollywood needs to either learn that a beloved book is beloved for a reason and ‘Artistic Licenses’ just pisses people off, or they need to stop doing film adaptations of books and start actually making films of original concepts.” I started.
“Yea, verily. ” Courtney announced piously.
We chatted about books we liked. I was a little more into action fantasy, and she was a little more into the romance aspect, but I liked some romance with my action and she liked action with her romance.
“Have you ever tried Dungeons and Dragons?” I asked.
“No. The one time I tried, I went to a local game store and the Dungeon Master was a creep and tried to hit on me. I was sixteen. He was like thirty.” She recalled with a shudder.
“We’ll have to play sometime.” I told her, “Though I’m a little old school. I personally like the third edition. Fourth edition was garbage, almost anyone will tell you that. Fifth edition is better. But in my opinion: third edition was an eight, good but with room for improvement; fourth edition was a two, it could get worse but not by much; and fifth edition is a 6, better than fourth edition, but why play it when third edition is better?”
Courtney laughs, “Sounds like I have a lot to learn, and not just about Computer Science.”
We were both computer science majors. Iit turns out Courtney had decided if she was actually going to work, instead of living off her trust fund. She was going to go into either web design or game development.
“The nice thing for me is I could open my own gaming studio.” She explained, “My team and I could work on anything we wanted. And a breakout game would put us on the board and make us millions.”
Her mother had disapproved of her gaming, since it wasn’t ladylike, until her late teens. “I’m so behind on games,” she bemoaned, “and the worst part is going back and playing games that were revolutionary in their time just doesn’t do it for me. Like the first Legend of Zelda game I played was Skyward Sword, and everyone says Ocarina of Time was game changing, but I don’t get it because I started after it. Twilight Princess felt more revolutionary to me, but that’s just because it was the biggest jump I saw in the series, but going back to the older animation with only less freedom just didn’t do it for me.”
We both had liked anime growing up but had too much to do recently to really keep up on the new stuff. Once again, I was a little more into action than romance, with the reverse being true for her, but both appreciated the other aspect in our anime.
We finished up our sushi, Courtney paid, tipping generously, “Never anger your sushi chef.” She declared overly dramatically. “You never want a mad sushi chef.”
We had taken an Uber to dinner and ordered another to take us home. We were both sober, but neither of us had a car.
I didn’t drink alcohol. My dad had been an alcoholic until I was twelve. After one too many drunken incidents, my mother had begged him to stop, and he had started going to Alcoholics Anonymous. I had never wanted to touch the stuff. It helps that the “fun” parties with alcohol either reminded me of when Nikki had stabbed me in the back, or the number of STDs the drunk sluts getting passed around, mostly passed out, probably had. There had been a big stink at my high school when a girl drank too much at a party and died of an alcohol overdose. Any appeal alcohol had ever had was dead for me.
Courtney didn’t drink either but for different reasons. “Mom loves her wines, champagnes and cocktails. She once told me that I needed to hold up my tolerance so I could win a rich man and keep him happy by sleeping with him after parties. I’d already decided I wanted to be nothing like her, so I swore off alcohol. Then I saw my girlfriends in high school mess around with alcohol, then weed, then drugs. It’s sad how many rich kids do drugs. Some of them ruined their lives, some got pregnant, and only a few have managed to stay okay. That’s why I don’t drink. My drug of choice is video games.”
Courtney went to the bathroom while we waited for a ride, and I typed up the next message from her blackmailer, but didn’t send it yet. I really wanted something to light a fire under us for figuring out how to get Courtney free of this blackmailer. I didn’t enjoy the duality of being her lover and blackmailer nearly enough to keep up pretenses. And I’d rather know if Courtney was just going to dump me when she was free of it, or if what we were developing was something real. When Courtney got back, the Uber was just pulling up.
Halfway back to her place, while chatting with the driver, I hit send on the message I’d typed up. Courtney saw it, and almost seemed relieved. “He sent me a message, I’ll read it when we get to my place.” She whispered to me.
We got in the door and she flopped on the couch. “Let’s see,” she muttered, pulling up the message and reading aloud, “You can stop with the pictures. Honestly, fucking you was a disappointment. I should never have let you have another man fuck you. I don’t want some other guy’s sloppy seconds. I wanted a virgin. I didn’t get it.” I was laying it on think in the message, but I needed to give her a reason her blackmailer wasn’t insisting on continually fucking her, like I had planned at there start of this thing.
I was pretty sure at this point I was falling in love with her. I was glad she was so happy with me. I wanted her to be healthy, physically, mentally and sexually, and that wasn’t going to happen if she kept having to fuck her blackmailer.
But it would have been too suspicious if I just stopped. I’d had to find something else to ask her for, and she’d actually given me the idea.
“So here’s what I want. Everyone knows the bitches ‘too good’ to have sex with college dudes know each other and hang out. I want them. Your virgin friends. You’ll start by getting me pictures of them. Naked. All those pictures you gave me of your naked body, I want something similar of theirs. Then you’ll convince them to let me fuck them, blindfolded like you were. But they won’t be giving your boyfriend their virginities first, and after I’m done, your boyfriend will step in, fuck them and pretend like it was him the whole time. That way, they’ll give themselves willingly and happily to me. Not crying and complaining, like you, bitch. If you wanted me to be gentle you should have just accepted it and cooperated. This time it’ll be your boyfriend getting my sloppy seconds, and they’ll think they know who fucked them. Once that’s done, they’ll be useless to me. Deflowered then contaminated. I don’t care what you decide to do with them after that. And once you run out of virgin friends, I expect you to find me virgin freshmen to fuck. Understood?”
Courtney finished reading aloud, then stared at the message.
“Are you okay?” I asked.
Courtney didn’t speak for several minutes and when she did, her voice was shaky. “… yeah, actually.” She stammered, staring at her phone, “I think he thinks this is worse for me… but actually this works out.”
“What do you mean?” I asked.
“Well, first off, if he’s not making me fuck him anymore, I can do this.” And she lowered her phone, “Tom, will you be my boyfriend? I promise not to have sex with anyone but you and satisfy all your sexual needs. I have loved our time together and never want it to stop!”
I smiled, holding back a laugh at her sincere and innocent declaration, “I’d be honored! I promise to meet all your needs and be the best boyfriend I can. I’d promise not to fuck anyone else, but…” and I glanced at her phone. “We could fight him on this! We can take our time getting him his first virgin and make him back off! Then I could promise you that.”
“Actually, I’m okay with this.” Courtney confessed.
I gaped at her in confusion. This was not where I expected this to go.
“Let me explain.” Courtney started, “I told one of my girlfriends that we were seeing each other, and she’s been dying to meet you. She is absolutely certain you took my virginity and wants to meet ‘the man of the year, worthy of your pussy’, her words, not mine, but not wrong.” Courtney laughed, “She hasn’t stayed a virgin because she’s trying to wait for her husband on their wedding night, like I was, every guy she’s met she’s tested and found to be an asshole she’s certain would pop her cherry and dump her.”