Authors Note: Not the most well-developed story, but I challenged myself to go from idea to finished story in 24 hours and this is what I came up with. Apologies for the lack of polish in advance as I am still without an editor at the moment. Anyways, hope you enjoy.
"Mmmmmmm Yes! That's the stuff my little stud, give your Chastity her little deposit!" The petite brunette said riding Dale's painfully hard double condom covered cock as he, to his dismay, felt his body comply. Though, how he heard anything through the athletic thighs wrapped around his head, that belonged to her younger sister, Charity, he had no idea. Not to be forgotten, said younger sister ground her dripping slit into his face to remind him his tongue had gone idle, he sped up his tongue work and soon was rewarded with her high-pitched scream and a gush of liquid before she collapsed back onto his chest, her own chest heaving from her orgasm. He felt Chastity dismount him, and pull the condoms off, "oh yes, your swimmers are developing nicely, my dear slave. Soon they'll be more than ready for my eggs, if you don't keep my grades up, that is."
He mentally groaned in his head wondering just how exactly he had fallen into the clutches of the Klein sisters and their sexual desires. They were cute, he thought to himself, admiring their glistening bodies, well their lower halves anyway, they were too prudish to show their chests off to him, as they dressed and perfectly restyled their brown hair. After all the precious daughters of a minister could not be seen looking like the sluts they were deep down. Actually, he knew exactly how this happened, he loved his sister, so he had made a deal with the devil that looked like an angel to everyone else. His little sister Julie was having a tough time fitting in at her new high school, in fact she was being bullied by the other girls in her grade so he asked the ministers daughter, who he had been lab partners with the previous year, if she could help. Chastity agreed to get help for Julie, for a price. It started out as tutoring, then he found himself doing Chastity's work for her to save time, because cute and likable as the girl was, she was as dumb as a post. Once they were eighteen, Chastity started using him to experiment with the forbidden, it seemed ministers daughters had desires too. At first he was glad to be getting something for all the help he was giving Chastity, besides Julie's happiness and popularity, Charity having taken Julie into her circle. He was a horny teen too, and Chastity was an attractive girl. Her hard-core religious background meant she refused to service him though, and very soon the novelty of fooling around wore off as it became clear she viewed him as nothing more than a sex toy to use for her own pleasure.
He tried to cut things off, but she reminded him Julie owed her whole high school friend circle to Charity and demanded he lie down. She then buckled him to the bed and sat on his face until he ate her to three orgasms. This is how it went for the remainder of the school year, him doing her work where possible and having his face sat on at least once a day. Eventually he no longer needed to be buckled, and his tongue work got so good the sessions only lasted as long as he wanted them to.
Senior year was more of the same, though he began getting lustful looks from Charity, that told him her sister had shared the price of Julie's social status, thankfully at 17 Dale knew she would not act on her lust for another year.
When it came time to go to college, low and behold Chastity had scraped the grades to follow him, he had hoped he would be free of her at college, but alas no. In fact, without her father there to limit their time together, Chastity got worse. Now eighteen and away at school, she began to ride him after the face sitting, even with the condoms he was usually raw after she used him. When his penis stopped responding to her, she somehow got blue pills for him that made him painfully hard against his will so she could use him at her leisure for hours. Like today every time she got off him she would look at his semen and remark on how potent it was looking due to all the sex. He knew that her eventual plan was to get him to knock her up and have her dad force him to marry her, but she still wanted to make her parents proud by passing college if she could. If not motherhood and a good husband would satisfy their wishes fine. So, if he kept her grades up, the baby plans would be on hold. The new wrinkle this year was weekend visits by the newly 18 Charity, who had taken her sister's place as the one sitting on his face. Every time both sisters mounted him Chastity would state he had the 'honor of being inside both Minister Klein's angels at the same time.' He never felt that honored as his cock was being rubbed raw on one end and he was fighting to breath between the cheer captain's thighs on the other. Charity as head cheerleader, had been able to make Julie's high school experience, which had once been a nightmare, into a dream. So, Dale figured this was a small price to pay so long as no one ended up pregnant and things became more permanent.
A knock on the door sent everyone into a flurry. Dale, still naked, ran for the bathroom leaving his clothes behind, Charity flung herself on the couch as Chastity opened the door.
"Tessa, so nice to see you, did I miss something in class today?" Tessa was a TA for Professor Franklin, a no-nonsense teacher who taught the only class Dale and Chastity shared.
"No, I was looking for Dale actually, you two usually have your study session now, so I was hoping to catch him here."
"Well, my sister is in town, so I canceled, sorry." Then after a pause, "That's a nasty bruise you have there Tessa, did you take a tumble?"
"Something like that," Tessa said before adding, "well if you see Dale, have him come by my office."
With that Tessa was quickly ushered out of the apartment. Once she was gone, Dale quickly dressed and left the Klein sisters to their afternoon.
He decided to stop by Tessa's office after a quick lunch, no sense delaying the homework, he'd have to do two sets.
"Ah, Dale, I wondered how quick little miss priss would send you over here. Word to the wise, if you're going to screw that twit in exchange for doing her work, use protection. She's the type to have daddy take out the shotgun and trap you for the rest of your life, and with her little sister there too. That family is messed up, too repressed I suppose. I digress, anyways if you want to keep covering for that ditz so you can keep screwing her, at least vary your wording a bit. Professor Franklin is busy, but she's not stupid, and nor am I."
"That bruise on your face says otherwise," Dale said without thinking unable to take his eyes off what really was quite the mark on her otherwise beautiful face.
"Excuse me?" Tessa said standing up and Dale took the rest of her in even under the loose clothes she wore, Tessa was prettier not trying than the Klein sisters were with their best polish look, why a woman as smart and pretty as she was would ever be with someone that hit her, he had no idea.
"You heard me, you think I'm playing with fire with Chastity, fair enough, though you have some details off, but you're in a relationship with some rich boy who hits you enough for it to show. Makes me wonder where else you have bruises."
"That's none of your business, and tell me Mr. Stud, what have I got wrong about Chastity besides she's an airhead who is using you to pass this, and probably all her classes? Don't try to deny you weren't screwing her this afternoon, your clothes were on the floor behind her, and she and that place reeked of fresh sex. I was pleased to see the condom wrapper on the floor, which means you're not completely irresponsible and stupid."
Dale shrugged and perhaps born out of his frustration with being labeled the player when he was being raped he said, "Prove that asshat hasn't given you any other bruises and I'll tell you about how wrong you are about the Kleins."
Tessa stared at him calculating, then said, "how do I know this isn't some trick to get Chastity a free pass by blackmailing me?"
"Because not all men are slimy dickwads like that jerk you're dating. I know your whole story Tessa, I asked around, word is you lost your scholarship, and went to the dillweed for help. You owe him and his family big, or else you wouldn't stand for the drunken assholes behavior. I don't care how much he's done; you don't deserve to be hit."
"Fine, but the flipside is true for Chastity Klein, and I'm super curious to see what it is you see in her. So let's do this." Tessa then proceeded to strip down to her underwear. Dale admired every inch of her, surprisingly, bruised-free body. She was smoking hot under those loose clothes she wore, from her black hair in a tight bun to her cute toes, she was curvy in all the right places and Dale felt himself getting painfully hard again.
"I see you see something you like," she chuckled, "and look, no bruises." She even gave him a quick twirl to finish her point. Whether it was her sexy form, the drug lingering in his system or both, his erection found another level it seemed. He had found Chastity so repulsive for so long his erections with her were due to the amount of drugs she pumped into him. When faced with an attractive woman he liked, and he had admired Tessa for some time now, it was all he could do not to tear his pants off. He also began to freak out he was about to be one of those guys that had to call the hospital for an erection.
His pain must have shown on his face because Tessa looked at him concerned. "Dale, are you ok? Does getting turned on for a guy really hurt that much?
He looked at her and decided she had earned the truth and honestly it was probably for the best anyways given he was facing the hospital.
"No, it's not," he said, "though my pants aren't helping."
Tessa smirked, "well that's easily fixed, take them off, only fair given I'm not wearing mine right now either." Dale didn't have to be asked twice he dropped his pants and boxer briefs letting his cock spring free. Tessa stared at it, "whoa soldier I didn't mean the undies too, though wow Dale, very impressive." Dale could not help noticing the wet spot that was suddenly present on Tessa's panties that certainly had not been there moments before. It appeared he was not the only one that liked what they saw.
"To answer your question, I don't use those twits for sex, it's the other way around, hence the mega boner here. Funnily enough getting ridden daily against your will by a dumb church girl loses its luster after a while, so Chastity has been drugging me. Charity has thus far thankfully only used my mouth, but she's getting bolder by the visit. I suspect if the older one ever stops putting the condoms on and gets the baby she's threatening to make me shoot into her, she'll let Charity have a ride too."
Despite his admission Tessa's eyes never left his still titanium hard rod. She smiled, "well that's a lot to unpack, thank you for sharing that with me, I know rape is hard to talk about, especially for men. I'm sorry Dale, I misjudged you. That said, given you probably have a valid reason for letting two women half your size use you like that, I suspect we should take care of that thing before we must take you to the hospital and avoid having you having to tell that again." With that to his utter shock Tessa got on her knees and looking up at him said, "sorry, manners, do you mind if I um, help you out here? Given how you got this, I don't want to assume consent." Dale in shock nodded and Tessa wasted no time taking his hard shaft in her mouth. What followed almost made the pain he was in worth it. Tessa clearly knew what she was doing and even though Dale had just cum less than an hour before, he found himself exploding into her throat in no time flat, Tessa swallowed, then cleaned him up a bit before getting off her knees and asking, "better?"
Dale nodded stupidly and felt the pressure releasing in his cock. "Thanks."
"No problem," she said walking around her desk, and opening a drawer she pulled out a fresh pair of panties before with surprisingly little hesitation she dropped hers.
