Courtney was pretty done after her throat fucking, and I dressed then went home. This ranked as one of my best nights in the longest time. I wasn’t even home when Courtney sent her blackmailer the photo proof of our activities of the night. God, it was hot. I now had the photos of me absolutely fucking the shit out of the hottest “untouchable” girl in my department at college, sent willingly to her lover and sent begrudgingly to her blackmailer. Though she only sent the 12 most smug “I got fucked” photos to her blackmailer. Courtney texted me a few hours later telling me that while all three of her holes were incredibly sore, she had really enjoyed the evening and hoped I was okay doing it again. I replied that I would happily have repeat sex with her whenever she wanted. She sent me a smirking emoji and said she was glad.
My roommate asked me what was with the shit-eating grin. I didn’t even care what he thought I just told him it had been a good day.
“Oh, you ace a test or something.” He asked.
“Or something…” I laughed.
“Whatever dude, you’re fucking weird.” He laughed.
The following morning, I was sitting in my Operating Systems class when Courtney came over and sat as non-gingerly as she could.
“Sore still.” I asked softly, as class was about to start.
“A little.” Courtney confessed, equally quiet. “So I called and talked to daddy last night, and he just wanted to confirm, do you have over a 3. 75 GPA?”
“3. 97 last I checked.” I informed her.
“Perfect.” She glowed. “If you can get me a transcript to prove it, he’ll hire you as my Private Tutor. He said if you had a 3. 75 he’d be willing to pay you a thousand dollars a week to help me keep my grades up. With a 3. 97, he might up that to encourage you to stick to it.”
I gaped at her.
“Think you can work with that?” She asked. “You may want to close your mouth, or you’ll attract flies.”
I closed my mouth and swallowed, “You have yourself a private tutor.”
She smugly sat back in her chair. “I will beat this.”
And class started…
Between classes, I was able to get a transcript of my school record and Courtney was able to send it to her father to prove my academic record. A few minutes later my phone rang with a number I didn’t recognize from outside our area.
“You should probably answer that.” Courtney told me, “I gave Daddy your number, he probably has one of his secretaries calling so you can get paid.”
True to her word, it was one of her father’s secretaries, and they collected various information from me, including my name, and bank account info.
“Alright, with that you should be set up. Your first payment should be in your account momentarily.” The secretary informed me, “I don’t know what Mr. May is hiring you for, but your payments will be made each monday morning. You will receive your tax statements in January. Take them to H&R block and tell them who you work for and they should take care of your tax statements, then please reach out to this number and as part of the agreement Mr. May will take care of your owed tax burden. Have a wonderful day.”
I hung up and checked my bank account and there it was. A $1000 payment. I now had the largest balance in my bank account that I had ever had, except for like the two days between my scholarship funding and having to spend it all on books, tuition got taken out before it even hit my account.
“So, now you can quit your campus job.” Courtney beamed.
“I’m doing it right now.” I told her and called my boss. He was pissed I was dropping him with no notice, mid semester, but when I told them what kind of pay he’d have to compete with to keep me, he got the picture.
When our last class for the day finished at 1 pm, Courtney took my hand and whispered in my ear, “I know it’s early in the day but my vagina is aching for some attention.”
We were at her house in record time. As soon as the door was locked, Courtney was shedding her close fast. Her dress flew over her head, and bra and thong hit the floor at what must have been record speed. I could only get my pants off before she pushed me on the couch, pulled my boxers off, licked my dick to make sure I was fully erect (unnecessarily), and lowered herself on my dick skewering her womanhood on my raging hardon.
“Fuck,” She breathed, starting to bounce up and down.. “I used to say that girls who couldn’t wait for sex were sluts, but damn, once you’ve had a dick in you everything changes.”
I took one hand and started rubbing her clit and shamelessly groped her tits with my other.
“OhhhHHHHhhhhhhhhhHHHHHHHhhhhh!” She moaned with closed eyes. Twitching as her orgasm hit her. Her twitching cunt seemed to milk my cock, unsurprisingly making me explode in her hot, tight pussy. “Fuck!” She gasped her eyes widening as she felt me pulsing and squirting in her. She lay forward on me, nestling my face between her tits. “That feels so good.”
She rolled off me, and lay naked on the couch next to me with her legs spread.
Tired from our quickie, but still excited. I grabbed my phone and snapped a shot of her with my sperm dribbling out of her cunt. In response, she grabbed her ankles and raised them up by her shoulders, forcing a glob of cum out, which was promptly photographed.
“Oh shit,” She yipped, jumping up. “I can’t get any on the couch. Daddy might hear from the cleaners.” She explained and ran to the bathroom.
I quietly pulled up the college messenger app. As her mystery blackmailer, I messaged her.
“What the fuck! I told you that you could only fuck one guy! You’ve had your fuck last night, now you’re fucking another guy! One penis and suddenly you’re acting like a cheap whore!” I sent her.
Her phone bussed from her purse.
I jumped and realized. Shit, I need to turn notifications off on my phone for this account or she would hear my phone go off when she messaged her blackmailer back.
“Can you get my phone for me? I heard it go off.” Then Courtney happily giggled, “There is so much sperm dripping out of me right now. You were horny!”
I turned my notifications off for my blackmailing account, then grabbed her phone and walked to her bathroom. “Well, I was watching your cute butt practically run home so you could fuck me, why wouldn’t that make me horny?”
I handed her her phone and watched the blood drain from her face, making her post-sex blush even more prominent.
“Everything okay?” I asked.
“It’s the guy that I lost the bet too…. Somehow he guessed we’re fucking and he’s not pleased I am taking a second round.” She muttered, typing out her response.
I saw the notification of her message, pulled down the top of my screen and read her response.
“You never said I could only have sex once. You said I could only have sex with one guy. I am holding you to that. Same guy, two days.” Her message read.
“Well, I will let you finish up in here.” I told her. Stepping out into the hall.
I stepped into the hall and then replied. “Fine. I did say that. But I want your pussy tight for me. You can do what you want with him, but he can’t fuck your pussy anymore until I get to fuck it. If you want to have sex with him, you’ll have to deal with his dick in your ass or mouth.” I messaged her as her blackmailer.
“Tom can you send me the pictures you took after you just fucked me?” Courtney asked, straining on the toilet.
“Sure!” I told her and sent them.
“Well, you didn’t say that fast enough. He just fucked my pussy before you said not to let him do that. I’ll stick to having him fuck my ass and mouth in the future.” She sent along with the pictures of her with her legs spread and sperm leaking.
Fuck, this was hot. Here she was bragging that she just fucked me, too me, and I was quietly calling the shots behind the scenes.
“Ugh.” I sent her. “Fine, but I want a picture to prove which hole he is fucking each time he’s over there. Each time his dick goes in you, I want you to prove it isn’t in your pussy, and if I figure out you are skimping on me, I will ruin you.”
Courtney was smirking, “Well, the guy I lost the bet to found out we’re having sex.”
“How?” I asked, “Is he, like, psychic or something?”
Courtney sat down, “I had to send him some of the photos you took of me last night. And I guess he saw us running off like newlyweds after class and put two and two together.” She shivered. “I wouldn’t put it past him to be watching the house though.”
“Well, what does he want?” I pressed.
“He realized you are over here fucking me again and says you can’t fuck my pussy anymore.” she informed me, “At least, not until he gets a shot at it. He wants it tight for his tiny dick.” She laughed, “It’s okay, I wanted you to start almost exclusively fucking my ass and throat anyway.” She flipped her hair, making her tits jiggle. “Our romp on the couch proved to me my vagina can handle anything his tiny dick can deal out.”
She rubbed her butthole and winced. “This is still a little sore, but I want you to keep fucking it so it can get used to it. My personal trainer always says that if you are sore, stretching and working out is important to maximize your gains….” She gave me a lust filled glance, “And I want your dick as deep in my ass as I can get it.”
“Holy fuck,” I breathed, “How did I get so lucky?”