The next day, back at work at Holy Cross School, Jacob Smith, the headmaster, was priding himself on resisting his would be temptress when in walked Cassie Parks again, this time with the nun who monitored the dorms and Cassie’s roommate, Jill Pierce. If Cassie was on one end of the spectrum, Jill was on the other. Fully aware of her sexuality and how to use it to get what she wanted. Jill was basically a slut. She snuck off campus, offered blow jobs to male teachers for better grades and had already been kicked out of another co-ed boarding school for having sex with an entire basketball team. The girls came in and the teacher told Jill and Cassie to explain what she caught them doing. Cassie started in about her rubbing herself as he had told her to do when Jill came back from class and interrupted her. Jill, taking advantage of Cassie naiveté had convinced her to “teach” Jill how to do it to and Cassie had taken to rubbing Jill’s clit for her. She was trying to convince her to use her tongue when the teacher interrupted them. Jacob swallowed hard with the visual. Jill began offering to demonstrate for Jacob what they were doing; the nun was clearly uncomfortable so Jacob dismissed her from the room.
“Jill", Jacob chastised her, “you know better. What you are doing is immoral and leading Cassie into temptation for your own pleasure.”
Jill batted her eyelids feigning ignorance. She walked up to Jacob, turned around and bent over placing her hands on the floor. “How many paddles are you going to give me Mr. Smith? I’ve been a bad girl”. Looking suggestively back at Jacob, she spread her cheeks and lifted her skirt revealing her tights were actually thigh high stocking secured with a black lacy garter belt. Her back arched more showing her lack of panties. Jacob stared down at her exposed asshole and pink swollen lips. He grabbed the paddle and gave her 10 whacks across the backside, large welts formed on her smooth skin. Each time he smacked her, she cried out with a “yes” and encouraged him with the instruction to hit her harder.
Jacob lost himself in the moment, forgetting Cassie was sitting on the coach waiting her turn. Jacob smacked Jill hard across the face. To his surprise, this only seemed to turn her on more. Jill stood up and acknowledging his bulging package grabbed his cock over his pants. She whispered in his ear, “I want to help you teach Cassie; maybe we can do a little hands on instruction for her?”
Jacob looked over at Cassie and smiled at her confused expression. She was clearly aroused by what she had seen. She had taken to rubbing her breast with one hand and was writhing around trying to release her from the mounting pressure building in her on the arm of the couch.
Jill looked over. She asked Jacob, “I would love to show Cassie what’s in your pants Mr. Smith.” Cassie looked down, noticing his arousal for the first time. Jacob swelled harder trying to find the words when Jill skillfully unbuckled his belt and unzipped his pants freeing his hard member from the prison it was in. Her skilled hand caused Jacob to fall back onto his desk. With still one hand clutching his cock, she motioned for Cassie to come over to get a closer look. “See Cassie”, she said sliding her hand up and down on the shaft. “This is what men have.” “See how big Mr. Smith’s is, that’s because he is so turned on by us Catholic girl sluts. He wants you to put his cock in your mouth. Do you want me to show you how to do it?” Cassie nodded. “OK, take your panties off and lift your skirt up so Mr. Smith can get a good look at you.” Jill continued with her instructions, “Sit over there on the couch and spread your legs. While I suck on Mr. Smith’s cock, you show him how I taught you to rub yourself. Make sure you get your fingers nice and wet and stick them in your pussy, like I showed you. Mr. Smith really wants to see what you have learned.”
Cassie followed Jill’s instructions. Jill knelt down and began licking Jacob’s cock. She was clearly very experienced as she slid her hands in a tight rhythm stroking him to the same motion that Cassie was now fingering herself to. The visual of her tight pussy dripping with wetness as her fingers slid in and out combined with the moist and determined sucking of Jill’s mouth and Jacob could not hold back. He blew his load deep into Jill’s mouth, releasing her head that he had pressed forcefully against his crotch. She seductively licked up the remaining cum, licking the sensitive head until it was clean.
Cassie was overwhelmed by what she was seeing; Jill asked her if she liked what she saw. Cassie nodded emphatically. Jill crawled over to Cassie and knelt before her. “Now I want to show you what it’s like to have your pussy licked. Do you want me to do it first or should we let Mr. Smith lick it for you?” Jill whispered in Cassie’s ear, “ I bet he would like to taste your virgin pussy juices.” Cassie pointed to Jill and without hesitating she went to work.
Jacob was treated to the most beautiful display of images. Cassie getting eaten out by Jill while seeing the garter straps dig into Jill’s thighs and ass which was still red from his previous spanking. Jacob found himself getting aroused again. He grabbed and began stroking himself.
Cassie was getting close to orgasm and Jacob looked at Jill with jealous contempt, he had to be the first to taste her. He pushed Jill away from her. He told her, he would take over and dived deeply into Cassie mound. Licking and slurping up her squirting juices. Jacob felt her hot pussy grind on his face and she was moaning in her pending ecstasy. Jill was now freeing Cassie breasts and squeezing her hard erect nipples pushing her ever closer to orgasm. Suddenly Cassie cried out and Jacob felt the hard thrusting of her hips as she came on his face.
“While Cassie recovers”, Jill started, "why don’t you show her how you liked to be fucked Mr. Smith. You can use me as the demonstration. Tell me how you like it and I will make sure she is ready to take your cock in her first." Jill proceeded to fill her well rehersed seductress role, " I just need to know if you like your girls to fuck you hard or do you like to be in charge?" Jacob was taken back by her explicit offer, " I can ride your cock like a whore if you want or do you like to be on top, take your time teasing me with it until I am begging for it."
“My God Jill”, Jacob sputtered, “How did you learn to talk like that?”
Jill undressed slowly revealing her matching bra for her garter belt, her bra only covered the lower half of her small perky breasts, her erect nipples standing out at attention. “Fuck me, Mr. Smith” she cooed pinching her own nipples and bending over slightly so he could get a full view of her perfect mouth size tits, “let’s show little Cassie how you get off by slutty little school girls who like to suck your cock and swallow your cum.”
Jacob was at a loss; he wanted to fuck both these girls but didn’t know what to do.
“Okay, Jill”, he relented sitting in the chair with his pants around his ankles, cock in hand. “Why don’t you get your hot ass over here and sit on my lap”.
Jill leapt at the chance to fulfill her long time fantasy of fucking Mr. Smith. She had dreamed about him since her first meeting with him at Holy Cross and knew Cassie was her way in. The way he got a hard on whenever she was around, Jill knew he wanted her bad and she could deliver the stupid bitch to him like a dog in heat. She had been secretly arousing Cassie for weeks, doing strip teases in their room, grinding on her when they danced, making sure she caught her pleasuring herself at night. Earlier when Jill pulled Jacob’s cock out of his pants, she knew she had to have her chance to ride him. His cock was bigger than she thought it would be, thick and hard as steel. She could barely relax her throat enough to take him fully into her mouth. He had to be a full ten inches, and despite her ample experience with high school boys, Jill was very happy to have a full man to fill her pussy who would know what to do to her.
She straddled Jacob facing away from him guiding his cock into her dripping pussy with one motion. He bent her over and pulled her deep onto his rock hard staff. He thrust up hard into her, taking her breath away and reached up and grabbed her hips pulling her down on him as he jabbed deep into her. She looked up a Cassie while Mr. Smith pounded her and pitied her. She clearly was aching for some cock for herself and Jill temporarily thought about sharing but his was too good to stop.
Jacob also looked over at Cassie and told her to watch Jill to see how she moved her hips grinding into his cock. He told Cassie to come over to Jill and let Jill suck on her nipples while he showed her how he liked to fuck. Cassie hesitated briefly but quickly stood in front of both of them, removed her bra and top letting her tits fall in Jill’s face. “That’s good”, Jacob told her, “Now let this dirty whore suck your big titties while I fuck her.”
Jill quickly reached up and took Cassie heaving breast into her mouth. She ran her tongue around Cassie’s big nipples and massaged her breast in the other hand. Jacob was close to exploding but again he wanted Cassie so much and didn’t want to miss his shot at finally fucking her by cumming inside Jill. He grabbed Jill’s hips and slowed down her frantic pace. He could feel how close Jill was to climax and with a few deep slow thrust he sent her over the edge until she cried out in elation. He thanked Jill and asked Cassie if she thought she was ready for her first time.
Cassie, aroused from watching Jill and from having her nipples licked and sucked, was dying to experience what Jill had just done. She took her fingers between her pussy lips and slid them over her clit as Jill had taught her. She pulled her fingers out and placed them on Jacob’s mouth and leaned over to whisper in his ear letting her breast fall in his face. “I am a little scared it will hurt but I am really wet for you”.
Jacob smiled at her and licked her juices off her fingers. He told her not to worry, we would be gentle. He asked Jill to help Cassie mount his cock. Jill seemed eager to be included so she held on to Cassie and helped ease her down onto the enormous rod. Cassie cried out, “relax sweetie, it will feel good if you relax”, Jacob whispered stroking her breasts. Jill reassured her as well. Telling her how good Mr. Smith’s cock is going to make her feel.
Cassie’s virgin pussy put up some resistance to the hard object penetrating her but
slowly Jill and Jacob raised and lowered her letting Jacob slide inch by inch inside. When the last inch was met Jacob had to stop to prevent himself from cumming right then. She was so tight, like a vice grip on his cock, he wasn’t sure she could handle his full member.
“How’s that feel?” Jill asked her. “Mr. Smith, reach around and rub her little clit”. Jacob followed her instructions and Cassie instantly began to rise and lower herself on his cock at the moment of his touch.
“Good girl” Jacob whispered to Cassie. “You’re such a hot piece of ass, I am so lucky you are going to let me be the first man to pop your cherry”. Surprised by his dirty talk, Cassie grew flushed. She found that she liked it and it awakened her pushing her to move up and down faster. “oh yeah” Jacob cried out. “You’re pussy feels so good!”
Cassie tried to imitate Jill’s movements but found that taking him too deep was painful. She asked Jill what to do. Jill suggested that Cassie lay on the desk and let Mr. Smith fuck her while standing. She pulled Cassie off Jacob and helped her lay on his desk.
Jacob stood up and pulled her to the edge of his desk with her ass hanging off. “Come here”, let me get my cock inside you again”. He entered her with force this time, plunging deep inside her and furiously pumped his way until he fully entered her without resistance with each stroke. Cassie cried out with a loud moan.
Jill climbed on to the desk and straddled Cassie’s face. “Lick me while you’re being fucked you little slut”, she commanded. Cassie’s inexperience was not evident as she let her tongue explore Jill’s clit playfully licking and sucking it. Jill was riding Cassie’s face blocking Jacob view of her as he continued to thrust powerfully into her. He could see only Jill’s tight ass raise and lower on Cassie’s face. He began to feel overwhelmed by the sensation of the small cunt against his engorged rod. He took a few last pumps before filling Cassie with his cum. His climax timed perfectly with the strong contractions of Cassie’s biggest O yet. He could feel her muscles start to contract while she was still completely engrossed in eating out her roommate. Jill was moaning and moving frantically over Cassie’s face. Jacob moved over to get a better view of Cassie eating Jill out. He reached out and grabbed Jill’s tits, helping to suck her nipples to get her over the edge. It did the trick and soon Jill was at yet another climax.
All three of them collapsed on the desk in exhaustion and contentment. Jacob, still giddy from the encounter did not want to move. His body covered by two beautiful half naked girls. He looked over at Cassie, grabbed her ass and asked her if she enjoyed herself. Cassie nodded, covering up her naked body replacing her school girl uniform top. Jill asked Jacob, if he had ever done a student before. Jacob replied that he hadn’t; they were his first. Jill smiled at this, satisfied she had successfully seduced yet another school official. She looked over at him and asked when they could fuck again. Jacob told her he didn’t think there could be another time, what he had done was bad enough.
Rejected, Jill got up and got dressed and left the office leaving Jacob alone with Cassie at last. Cassie still lying half naked on his desk with cum dripping out of her replied, “But we have to be able to fuck again, I have so much to learn”.
Jacob felt himself growing hard again, “That’s true, and I suppose that it’s my job to teach you.”
