Story Details

Chaz gets disciplined

Crave121212 on Sissy Stories

Chaz had never been the best student. He wasn't the smartest and he didn't put in the most hours studying... but he maintained decent grades and made sure to get everything done on time. He surprised himself when he was accepted into a sociology grad school program. Chaz thought undergrad had been difficult, but man was grad school a whole different level. He was constantly struggling and barely maintaining passing grades. He finally got to the point that he did something he had never done before... he cheated. He had 2 days left to finish a paper he hadn't started so he browsed the internet and found a paper on a similar topic to submit as his own (with a few tweaks of course). Chaz told himself he would never do it again and would make sure to stay on top of his work better. A week after the paper was submitted he was pretty certain he was gonna get away with it... until he got an email from Dr. Rowen requesting he come to her office.

Dr Sasha Rowen was not what you would expect for a grad school sociology professor. Thirty nine years old, long blonde hair, big blue eyes, slim waist, and an hourglass figure. Her breasts looked closer to a D cup than a C cup and had the appearance of being fake but who knew for sure. She tended to wear a short skirt and revealing top much to the excitement of her male and some female students.

To be honest Chaz was kind of scared and excited at the same time as he entered Dr Rowen's office. Sure he might get expelled, but at least he got some one on one time with one of the most attractive women he had ever seen. He knocked on her door and waited. "Come in" Dr Rowen softly replied. "Hey Dr Rowen, you wanted to see me?". "Yes Chaz, please sit down. I was grading the papers from last week and was a little concerned with yours". Chaz felt a twisting in his gut... well this is the end of my grad school career. "I noticed that it looks very similar to another paper I found online... you didn't happen to copy it did you?". Chaz knew the gig was up, no point lying "yes... I'm sorry. I just didn't have time to do it. Please don't kick me out". "Well Chaz this is a very serious offense and you will be expelled if I report this to the Dean. However, this isn't the first time this has occurred with my students and I like to try and give my students a second chance... if they earn it...". "Yes! Please, what can I do" replied Chaz. "Well first things first, can you walk around to this side of my desk and open this drawer?". Chaz got up and walked over to the drawer she was pointing at. He opened it up... and his eyes went wide... Inside was the largest dildo he had ever seen. 12 inches long, at least 3 inches thick, with bulging veins and a strap lying next to it.

Chaz was in a state of shock. what the hell was going on??? he didn't say anything he just stared with his mouth open. She can't be serious he thought. "Chaz you look concerned, have you never been around one of these before?". "no dr dr dr rowen" he stuttered. Chaz had to admit, he had stumbled across strap on porn before and masturbated to it, but the thought of actually having someone use a strap on him was crazy, especially a monster strap on like this one. Against his will... Chaz felt his cock starting to get stiff. "Dr Rowen... are you uh... are you like saying you want to use this on me???". "No, no, no Chaz. Although I do see a slight bulge growing in your pants, I do not plan on using this strap-on on you". Chaz wasn't sure if he was relieved or kind of disappointed, but just then he heard a knock on Dr Rowen's door. "Oh shit someones coming" chaz yelped and slammed the drawer shut and tried to cover his growing erection. "Don't worry Chaz, I'm expecting someone... Come in!".

The door opened and Dr Rowen's teachers assistant Samantha came in. Samantha was in Chaz's class and had always been the smartest student in class. He hadn't really spoken to her much because she was smart and beautiful and therefore intimidating. She had brown hair, dark skin, large breasts and somehow a bigger ass than Dr Rowen. She also was into crossfit so every part of her body was toned and her thighs were thick as tree trunks. "Hi Chaz" Samantha said casually. "Uh Hi" Chaz mumbled hoping she didnt notice his hands over his cock. "Samantha here has assists me with disciplinary measures with students". "Uh okay.. I don't really know what you mean though" said Chaz, confusion evident on his face. "Chaz will you open that drawer again for me please?". "You want her to see whats in there?!" Chaz whispered. Dr Rowen slowly nodded so Chaz opened the drawer expecting Samantha to be as shocked and confused as him.

Samantha just stood there with a smile on her face. "Chaz, I know we don't really know each other that well... But I am about to fucking destroy your boy pussy. Your asshole is going to be stretched to its limits and then you'll be begging for more." Chaz's jaw dropped for the second time in the last 5 minutes. "you're... you're kidding right? This is just a big joke to scare me because I cheated huh?". "Sorry Chaz, but this is no joke. You submit to our will... or you get expelled... your choice. And don't even think of trying to report us to anyone... who would be more believable, a teacher and her assistant, or a guy who just submitted a plagiarized paper..". "Fuck me... " said Chaz, "Yes. thats exactly what we intend to do" said Dr Rowen. "Samantha why don't you get strapped up while I show Chaz one more surprise." Samantha grabbed the monster dildo and the strap and began to strip down as if she'd done this many times before. Chaz couldn't help but stare at her amazing body. The thick muscles that rippled under her soft flesh, her large breasts and perky nipples. He looked at her arms and realized that her biceps may actually be bigger than his... he also realized that despite his fear of that huge dildo his cock was harder than it had ever been. "Enjoying the show?" asked Samantha as she hitched the strap up her thick legs. "Your cock seems to be awfully hard with the idea of getting pounded by my monster cock. If I didn't know better I would say your asshole is pretty excited about being stuffed. Are you a little sissy faggot Chaz?". "What! No!" yelped Chaz slightly embarrassed. "You and Dr Rowen are amazingly hot thats why I have a boner, Im not into this kinda thing at all but I clearly don't have a choice if Im going get expelled."

"Calm down Chaz" Dr Rowen said. "Come sit over here with me." Chaz shifted his focus from Samantha's amazing body to Dr Rowen as he remembered that she said she had a surprise for him; although he doubted anything could be a bigger surprise than what has just occurred over the last few minutes. "Chaz do you like my tits?". Chaz thought his dick was about to explode. "Yes. Very much so". "Do you want to unbutton my shirt?". "Sure thing" Chaz was starting to like where this was headed even though the threat of the monster dildo in his virgin ass loomed in the back of his mind. Chaz unbuttoned Dr Rowen's shirt and starred at her very large (and clearly fake) breasts in all their glory. "those are amazing". "Yes and they cost a pretty penny" Dr Rowen said. Dr Rowen stood up, "would you like to unbutton my skirt now?". Holy shit thought Chaz, am I going to get to fuck Dr Rowen also?. "Dr Rowen... are we going to have sex while Samantha fucks me with her strap on?" Chaz asked with an excited tone. "In a manner of speaking, Yes" replied Dr Rowen. Maybe this wasn't going to be as bad as it sounded, thought Chaz.

Chaz unbuttoned Dr Rowen's skirt and pulled it down. Looking back at him was the largest real cock he had ever seen in his entire life. It was almost the size of the strap on dildo Samantha had equipped. "Are you fucking serious?!" yelped Chaz. 11 inches of thick shemale dick nodded back at him as Dr Rowen thrust her hips a little. "You're a Tranny?!" chaz asked. He was immediately slapped across the face by Dr Rowen's hefty piece of ladyboy meat. "Now that wasn't a very polite thing to say Chaz" said Dr Rowen with a wicked grin on her face. "You thought that the monster dildo was going to be bad, just wait until I ram my huge cock down your throat. If you're lucky I will pull out and cum on your face but Im likely gonna make you choke on my dick and fill your stomach with my seed." Chaz didn't know what to do. He was beginning to think it might be a better idea to just get expelled. "Alright Chaz, before we destroy your ass, why don't you wrap those sweet lips around by thick cock." Chaz couldn't deny the fact that his cock was still rock hard... "Okay... fine" mumbled Chaz. He had never had gay fantasies but this cock looked much more inviting since it was attached to a smoking hot woman. He got down on his knees and starred at the monster cock in his face. He leaned forward and opened his mouth wide. "thats a good little faggot". He wrapped his mouth around Dr Rowens huge dick and began to bob his head back and forth on the tip of her dick. "come on you sissy bitch I know you can fit more than that down your throat." Dr Rowen put her hands behind Chaz's head and pulled it towards her. Chaz's eyes bulged. He couldn't breath, his eyes began to water. 11 inches of meat slid down his throat as he choked on dick. "much better Chaz" groaned Dr Rowen. "You're turning out to be a good little sissy Chaz" said Samantha as she admired Dr Rowen's large cock pumping in and out of Chaz's mouth. Unable to reply, Chaz just gurgled on cock and nodded. As difficult as is was to breath with this monster pumping his throat, he couldn't deny that he was still more turned on than ever. He looked up at Dr Rowen's beautiful face and she smiled back. "Aw Chaz you really do love this you little faggot. You're realizing you're a slave for my luscious cock. I wish I could say you're gonna enjoy Samantha joining in as much as you enjoy this... but its probably gonna be pretty painful for you at first." Chaz didn't care any more. He was in a state of sexual ecstasy and was ready for anything. "Samantha, please fuck my boy pussy" chaz exclaimed. "Wow, that really didn't take much coaxing" said Samantha. Samantha got behind him and got some lube out. "Alright I hope you're ready for this, drop your pants."

Chaz was painfully aware that his dick was about the third the size of the two women in the room with him. He bent over with his hands on Dr Rowen's desk. He couldn't help but clench his asshole as he felt Samantha hovering behind him. Dr rowen rested her huge cock on Chaz's forehead, "here little sissy, maybe this will help you relax". Chaz grimaced as he felt a pressure against his tight hole. Oh god here it comes he thought. "Ahhhh Fuck" Chaz exclaimed as he felt Samantha enter his ass. It was painful, but not quite as bad as Chaz had been expecting. "Chaz" Samantha whispered in his ear. "Yeah" he grunted. "That was just a few of my fingers lubing your ass up. Here comes the real deal" and she rammed the monster dildo right into his asshole. "AAAHHHHHH FUUUUCKKKKK!!!!!!" screamed Chaz as he felt all 12 inches of fake dick rip into his insides. "Shhhh its okay little faggot" said Samantha as she held tight onto Chaz's hips and waited for him to accept the huge cock that was inside of him. Chaz struggled to get off the cock but Samantha's biceps were bulging and she had a grip of steel, there was no escaping her. Chaz did his best to stop the tears that were flowing from his eyes as the pain in his ass subsided. Gradually the pain turned into excitement. Samantha began to pull her massive cock out of him and then slammed it back in. Chaz felt the fake balls slap his balls from behind as she buried her fake dick inside of him. "Thats it you sissy bitch" screamed Samantha as she continued to pound his ass. She pulled all the way out for a minute and admired the gaping hole in front of her. Chaz couldn't believe how empty he felt without cock inside of him. "Please put it back in Samantha" Chaz whimpered. "Chaz, what about me" said Dr Rowen. Chaz grabbed her dick with one hand and pulled it back towards him and guided it into his mouth. Chaz wiggled his butt towards samantha and she didn't waste any time ramming her strap on back into him. Chaz couldn't believe how amazing it felt to be filled with huge cock in both ends. He violently thrusted back and forward to get as much cock in his ass and down his throat as he could. "Wow I don't think any student has turned into this much of a cock whore this quickly" said Dr Rowen as she enjoyed her blowjob.

Chaz took his hand and reached between Dr Rowen's legs looking for her asshole. He found it and slid two fingers in. "Woahhhh" exclaimed Dr Rowen, "If I didn't know better I would say you are trying to make me cum". Chaz couldn't deny that he had been doing whatever he could to pleasure Dr Rowen but he didn't want her to cum yet. As if reading his mind Dr Rowen replied "Don't worry Chaz, if I cum right now I will be hard again in minutes and can continue to fuck your face and maybe even your ass." In that case.... thought chaz. He used his other hand to rub Dr Rowen's balls as he fingered her ass and choked on her dick. Samantha continued to slam his ass from behind but all he could think about was getting Dr Rowen to release a load inside of him. "Oh fuck here it comes" exclaimed Dr Rowen, Chaz could feel her dick swelling in his throat, her asshole clenching his finger, her balls lifting up towards her body. "Ahhhhhhhh" screamed Dr Rowen. Chaz's eyes went wide as he felt hot fluid surging down his throat into his stomach. Dr Rowen pulled her massive cock out of his throat and continued to spew cum all over Chaz's face. Chaz enjoyed the feel of sticky semen leaking out of his mouth and hanging from his forehead over his eyes. "Chaz you're a natural cumslut" said Dr Rowen catching her breath. "I've fucked a lot of bad students but none of them worked as hard as you did to make me cum". Chaz didn't know what to say. He was slightly embarrassed and confused about his emotions but couldn't deny that he just had the most intensely erotic experience of his life. "I.. I... I am a cumslut, and I never knew it... Thank you for helping me realize that." whispered Chaz softly. "You know what Chaz, I think you deserve to keep exploring this new identity you've discovered. Samantha, can you go grab Tammy and Sophie from their offices?". Samantha quickly got dressed again but left the dildo on and slipped out the door.

Chaz felt his dick twitch in excitement. This experience wasn't over. Dr Rowen's throbbing half hard dick began to start growing again. Chaz crawled on his hands and knees over to Dr Rowen's chair and began to lick her balls and up to the tip of her dick. "Oh Chaz, I do enjoy your mouth, but I think its time I tried that asshole". Chaz crawled up onto her desk and laid on his back with his legs up in the air and his hands spread his ass checks apart. "What a good sissy slut, your body already knows the best positions to be fucked even though you've never done this". Chaz already felt so empty without a cock inside of his ass. Dr Rowen's monster member hovered over his slightly gaping no-longer virgin asshole. "Ohhhhhhh" Chaz moaned as he felt her dick slowly slide inside of him, stretching his asshole every bit as much as samanthas huge dildo. Dr Rowen began to thrust faster and faster, "Chaz you really like getting your boy pussy pounded, huh?". "I love it so much" gasped chaz between grunts as Dr rowen's balls slapped his back repeatedly. "Now that you made me cum once already I should be able to fuck your ass for a long time before unleashing another load inside of you" said Dr Rowen as she continued thrusting deep inside of Chaz. Chaz was completely lost in sexual oblivion. How had he never understood the pleasures of being a slave to cock. Sure he loved sex and when he normally orgasmed he couldn't imagine anything better... but this... this was better. He wanted nothing more than to make other people cum inside of him. All he could thing about was giant penis now, especially giant penis attached to women with giant tits. Chaz was so engulfed by this assfucking experience that he didn't hear Samantha come back in the office with company. He just felt the soft velvety flesh rubbing against his forehead that he quickly came to realize were the tips of two big cocks. He opened his eyes with a huge grin on his face and saw the throbbing rock hard members floating above him, he then saw the beautiful grinning faces of the two ladies they were attached to.

Dr Rowen didn't stop pounding his ass for a second as she introduced the newcomers. "Chaz I know this is a surprise to you but to be honest, about half of the professors in the Sociology dept are transgender. I want you to meet my two best friends, Tammy and Sophie. Both of them are familiar with how I discipline my students but even they are going to be surprised by what a special treat you are. The most passionate cum slut I've ever had." Tammy and Sophie giggled as Dr Rowen introduced them then grabbed Chaz by head, bent it backwards so it was hanging over the desk and Tammy slammed her huge cock down his throat while Sophie moved over to the side and made Chaz start jerking her off his free hand. Chaz was in ecstasy. He could barely breath with Tammys dick so deep in his throat but he didn't care, he just wanted to make these women cum no matter what it took. He looked like a pig getting spit roasted with Dr Rowen and Tammys dick penetrating him at both ends. He was vigorously masturbating Sophie at the same time and pulled her closer to him. He let go of her dick and reached between her legs and slid his fingers in her asshole. "Oh my" Sophie said, this little slut really does know how to get a girls juices flowing. Dr Rowen pulled out of Chaz's ass; his hole was gaping open about 3 inches wide. Chaz started whimpering with Tammys cock still pounding his throat. "here sophie slide in here quick I think his boy pussy is aching now that its empty of cock". It was true, Chaz thought. His asshole, well really his stomach, felt an intense desire to be filled. He missed the throbbing sensation inside of him that these giant cocks provided. Sophie didn't hesitate, she slammed her dick inside of Chaz so hard that her balls made a loud smacking sound against his ass cheeks. Chaz's eyes rolled back in his head with pure delight. Both his holes got fucked a few minutes longer while Dr Rowen stroked her meat and watched. "all right ladies, are you gals about ready to give Chaz a sticky creamy treat?" said Dr Rowen. "Samantha, why don't you come over here and fill Chaz's asshole with that dildo so he doesn't start whimpering again." Sophie and Tammy pulled their dicks out of Chaz and they joined Dr Rowen over on the side of the desk where chaz's head was hanging off. Samantha slid her monster dildo into Chaz's ass and began pumping even more furiously than anyone before her. Chaz stared at the three thick veiny cocks above his head and the 3 pairs of huge tits hanging over them and couldn't think of anything in the whole world that looked more enticing. He knew what was coming. And he was desperate for it. "please cover me with your cum". The three beautiful shemales gave wry smiles and jerked their lady meat a little faster.

In perfect unison, as if they were one person; Tammy, Sophie, and Dr Rowen unleashed a torrent of semen right at Chaz's face. Three thick ropes of cum splattered all over his face and down onto his chest. They kept pumping and cum kept flying. There was so much cum that for a moment you couldn't even see Chaz's face, it was just a white blob of sticky cream. Chaz was moaning in ecstasy and cum was leaking into his mouth with strands sticking between his parted lips. Samantha pulled her dildo out of his ass and the 4 women took a step back to observe their handiwork. "Well Chaz, I do think you look like the most used up cum slut we have ever seen" said Dr Rowen. "Its time for you to sit up and put your clothes back on". Chaz's head was spinning and warm from all the hot jizz covering him. He sat up and cum dripped from his chin all over his body. "Um Dr Rowen... Do you have a towel or anything I can use to clean up". Dr Rowen put her hands on her hips, "Chaz cum sluts have to wear their cum as a badge of honor. It really is part of your punishment but its clear at this point that this is no punishment for you. You love it. And I don't care if everyone sees you with a cum covered face. Just don't tell them it was me or you will be expelled... and you won't get to experience this again. Now get out of my office until I telll you to come back." "Yes Dr Rowen. Thank you all for fucking me. Please fuck me again soon." Chaz said in a subdued tone. Chaz put his clothes on, walked to the door, opened it, and ran full speed down the hallway hoping he could make it home before too many people noticed that he was completely covered in cum.



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