Note: This story was dynamically reformatted for online reading convenience. ï>¿Naive Teacher in Winston -" Side Story - Chloe by potatoHead42 Winston Stories: New uniform tryout with Bill and guests. Day 11 -- Thursday Morning -- School Chloe Chase knocks on the imposing door of the principal's office. "Come in!" - says a voice on the other side. The blonde opens the door and is surprised to see Principal Bill sitting on the couch with a couple of oversized shopping bags. "Hello, Mr. Bill?" - she says unsure. "Chloe! Thanks for agreeing to do this. Also, as I told you before, please call me Uncle Bill." - the old man says with a wide grin. He gets up to greet her. Bill is as tall as his nephew Andrew, at 6'3, and she can see that he was once a very attractive man, even if he was old and slightly overweight now. "Oh, sorry, Uncle Bill. It always feels weird calling you that at school." - she explains. "Nonsense, we are family. Now come give me a hug!" - he orders. She approaches him and they embrace intimately, with him taking a big whiff of her scent. He then puckers his lips, expecting a kiss. With reluctance, she stands on her tippy toes and gives him a quick peck, the loud smacking sound echoing across the room. "Thanks, darling." - he says, breaking the embrace and sitting back down. "Hopefully, Andrew is taking good care of you." - he mentions, emphasizing the words. "He is, Drew is a great boyfriend." - the cheery students answers. "I know he's great, but I meant it in a sexual way. Is he making you orgasm often enough?" - he asks nonchalantly. Chloe sighs, she was already used to the lecherous behavior of the men in Winstonstead. "You know we are both virgins, Uncle Bill. Andrew thinks it's more appropriate for us to wait until we are out of school and can get married." - she says. "Beh! That 'saintly' mother of his putting nonsense in the boy's mind." - he shakes his head disapprovingly. "Nevertheless, have you been doing other stuff, like..." - he says, making a jerking motion with his hand. "Rarely. You know how Drew is focused and serious about his future." - she answers. "Certainly, a young sexual thing like you must want it?" - he says with a knowing smirk. "Erm... of course, Uncle, but Drew is my boyfriend, so I have to respect him." - the young lady admits. "Well, if you need, I can teach you a few things." - he guffaws. "Hmm, thanks but... no need... Miss Lana has been teaching us enough." - the blonde says. "Ah, so I heard. That is very good." - he looks at her seriously, his demeanor changing. "Still, you need practice with a real cock if you are going to be able to please my nephew and have his babies. It's expected from all the women of the Winston-Phillips family." - he says, with a reprimanding voice. "Yes, Uncle Bill." - Chloe answers with a sigh. ***** Lil' Backstory Chloe + Andrew Chloe Chase was 13 when she met Andrew Winston-Phillips. Well, "met" might not be the right word. Introduced, perhaps. You see, the Chase family has always been a part of Winstonstead's history, so when Andrew's parents needed to arrange a future wife to become engaged to their eldest son, the Chases were one of the first names on the list. Their first "date" was extremely awkward. It was a dinner party at the Chase's house, with the sole purpose of introducing the two lovebirds. Chloe was dreading the event, but when she and Andrew excused themselves to have some time alone, the blonde girl was surprised by how different he was and how much they hit it off. They have been dating ever since. Of course, dating a Winston-Phillips came with a lot of expectations. Chloe had to attend numerous parties, have perfect manners and always be on her best behavior. She was always required to stay quiet and talk as little as possible, mostly serving as a trophy girlfriend for the young boy. Possibly that was the reason she was so cheery, peppy and crass outside of the 'fancy scene'. She started to develop an almost hatred of the prim and proper version of herself. Naturally, she was still devoted to Drew, so he had to tolerate this and act the part when they were with his family. A good aspect is that everyone in the family was very respectful of her and treated her as their own. She was pampered and cared for, as if she was an official Winston-Phillips. That even extended to her parents. If they kept dating, she was set for life. Chloe and Drew had a good relationship, but it was not without any issues. They were teens after all. She started to get curious about sexual things and opening up with her boyfriend about it. Even though Andrew loved the cheery blonde deeply, he had been groomed to be serious, distinct and decorous, so he always pushed any sexual desires or explorations aside, much to the chagrin of the girl. As they grew and developed together, Andrew started to become more accepting of Chloe's openness about sex, but still, he refused to go any further than kissing, light touching and masturbation. They saw each other naked on occasion, but it was rare. She thought Andrew had a decently sized penis, but at that point, she had little to no real-life experience to compare. Secretly, Chloe became slightly pervy, interested in everything related to sex. She read books and erotic stories online, looked up videos, masturbated and fooled around with some of her friends, mainly Jen, her bestie and neighbor. She developed strong sexual feelings towards both men and women, and while she had many opportunities to betray her boyfriend, she refused any man that even remotely tried to get close. Her best friend Jen was always frustrated that Chloe "cock-blocked" her, but she understood that Andrew was probably the biggest catch in their age-range. She knew her friend was ultimately doing the best thing for their future. Needless to say, Chloe was extremely frustrated and horny all the time. ***** Eighteen Everything was going great until Chloe turned 18. You see, in Winston, it was customary to leave young people in the dark until they became of age, when it was then encouraged to share with them the deepest secrets and depravities of the town. In the first week, nothing changed. Nobody dared get near to the future wife of one of the heirs to the Winston-Phillips name. Chloe knew she was lucky, and other girls and women wouldn't share the same fate as her, being at the mercy of every person in town. But then, a big family gathering was held. Andrew sat down with her and reluctantly explained what could happen during the event, since they both were adults now. He didn't like any of it at all, but there was nothing he could do, since it was "tradition". He asked Chloe to grin and bear through it. Everyone considered this just part of her 'initiation' into the family. That night, the blonde was touched, groped, squeezed, prodded and spanked. Every adult from the family kissed her in the mouth, some with tongue, much to the anger of Andrew. Of course, he was very frustrated by the events, but acted like nothing had happened. They continued going to a few more parties, and things kept escalating. Some men made Chloe sneakily touch their naked members, while others openly twisted her nipples in front of everyone. Principal Bill was one of those men, being known as a notorious lecher in town. This was the time that Chloe realized that her boyfriend, and future husband, wasn't very well endowed, with most of his family having bigger and thicker penises than him. Chloe secretly started to develop a 'size queen' / 'big dick' fetish, which soon became her most searched and viewed porn term. Sometimes she would masturbate 5 or 6 times in a row to videos of teen blondes being fucked by monster penises. After this, Chloe started to get some more attention around town, as the 'word' started to spread that the couple didn't mind the groping and that it was safe to do so, as long as their limits were respected. The last event was held about a month before the school year started. That was the night where Chloe was fingered by a man for the first time. In front of Andrew. Drew's grandfather, Dick, made her sit on his lap and started groping her in front of Andrew and some of his cousins. He called it a test of some sort. The old man soon started touching her under her skirt and finding no resistance from the couple, went a step further, touching her virgin cooch directly. In a span of a minute, he was fully fingering her young pussy in front of his grandsons. They could all see the thick digit sliding in and out of her pink wet snatch. Andrew was mortified. Nobody else had touched her twat before, besides Jen, and now she was letting Dick, Drew's grandpa, do it in front of him and his family. Chloe was trying to not enjoy it, but it was impossible. She felt lewd and horny. She couldn't avoid the massive orgasm that was building, and soon she came and convulsed all over the old man's index finger. Andrew was extremely upset with his grandpa, swearing to abdicate from parties for the foreseeable future. That was only a month ago, but so far, he kept his promise, and they haven't attended anything since. None of this quenched the blonde's horniness, it was just fuel to the fire burning inside her wanton and demanding pussy. She needed more, she wanted more. ***** Start of School Chloe was elated when Lana Cox was introduced to the class. She found the busty educator extremely attractive and the more time she spent with her, the more she liked her. Besides being sexually drawn to Lana, she also valued that the teacher was loyal to her fiancee, even if she had plenty of studs throwing themselves at her or even if she constantly got into naughty situations, showing her slutty body or stroking cocks. That was one of the reasons she disliked Mary Hunter, as the vulgar teacher always cheated on her husband. In Chloe's eyes, it didn't matter if Lucius Hunter did the same, it was still not right. She would never betray Drew. Chloe's commitment to Andrew was iron-clad. At least, that was what she thought until she saw Lukas Hunter at school again. He had grown a lot and had developed into a handsome, young man with piercing blue eyes. Yes, she hated Lukas, but wanted to fuck his brains out at the same time. She always got wet just by provoking him and yelling obscenities at him. She secretly enjoyed seeing Andrew all jealous and bothered by their naughty interactions. Chloe also loved to see Miss Lana in lewd situations, it excited her tremendously, to play around with her and see others messing with her. She never wanted to be mean to her teacher, as she cared for her, but sometimes her sexual side won over. Her most prized possession was the photo of her and Lana flashing her boobs in the Gym shower. This selfie was something she had not shared with anyone and used at least twice a week for her daily masturbation sessions. ***** With everything that had happened lately, Chloe knew that she wasn't going to remain a virgin much longer, even if Andrew was not up to the task. The pot was boiling and would spill over if this train of events kept going. ***** Back to Present 1 on 1 Sesh "Glad we are on the same page, Chloe." - Bill says, pleased. "So, what am I doing here today exactly?" - she asks, changing subjects. "Right. So, you know that we are planning some new uniforms for this year?" - he says, and she nods. "It's a delicate subject with students since we never had anything of the sorts, besides dress codes and color requirements." "Don't need to tell me twice. You remember that the student council voted last year, and we all agreed to the new uniforms, we think it will add more structure to the students." - the young class-rep says. "Indeed. Still, might be a tough sell, that is why I asked Andrew to convince you to try them out and be the 'image' of the new uniforms." - he explains. "I see, that is why he was so adamant about it. You know I can never refuse him, Uncle Bill. So, what do you need?" - she says with resignation. "We have a few different pieces to try on. Then I will order them and when they come, I was hoping you would pose for a few posters wearing the outfits, to get everyone on board." - he explains. "Okay, but I was also under the impression that this was also related to Miss Lana?" - Chloe asks, confused. "Yes, well observed. Lana tends to dress too conservatively. It's out of place with our customs for such a pretty, youthful lady to wear such outfits." - he elaborates. "Uhum, I can see that. Her sense of fashion is very outdated, she dresses like my granny." - giggles Chloe. "Exactly! So, I am going to give her some of the best pieces from today, as a 'provisional uniform' until the real things arrive later this semester." - he says. "Mary will also join us later." "Why is she coming here?" - asks Chloe, who disliked Mrs. Hunter. "It would be good to try the clothes out with different bodies, to make sure it fits Lana properly." - he explains. She sighs. Chloe approaches the bags and looks through them quickly. She notices that all the pieces are in shades of Red, White and Gray, the school's colors. "Oh, they are cute! Yeah, she will look so much better with shorter skirts and sleeveless blouses. She needs to showcase her top curves and thick ass more." - the blonde says cheery. "Precisely. I can see why Andrew loves you, you are not just a hot body with perky tits, you are a very smart young lady." - he compliments her. She blushes. She is normally not shy at all, so she wonders where this sudden timidness is coming from. The principal rummages through the bags and separates the outfits into a few sets. He hands her the first one. "Here. Change." - the old man orders with a salacious smile. "Where should I change?" - she questions, dubious of his intentions. "Right here is fine, just strip down to your underwear." - Bill says nonchalantly. "I shouldn't do that; Drew is not going to like it." - she says. "Nonsense, he asked you to help me. Besides, I talked to him." - he explains. "But..." - she starts to say. "Don't make me lose my patience, Chloe. It is for the good of the school and the town. I'm sure your parents will be glad you are contributing so much to our future." - the principal says with a stern face. "Okay, but don't laugh at my underwear..." - she warns, slightly embarrassed. Chloe starts to strip down. She first removes her sweater, leaving her in a pink cotton bra. Bill can't help but admire her figure. Chloe is fit and sexy, with big breasts for her frame and a small tight ass. What he wouldn't give to have a piece of that virgin pussy. Maybe one day, he thinks. She finishes removing her skirt and blushes deeply. She is wearing a pink striped thong underwear with the words 'Thursday' on it. It doesn't suit her adult body, looking more like something a young girl would wear. "Sorry about this, I wasn't planning on anyone seeing it." - she says, flushing. "No worries, looks dandy on you. An interesting contrast with your fit body." - he says with a lecherous smile. ***** Kenny Sesh They hear a knock on the door. "Come in!" - says the principal loudly. The door opens and in comes Kenny, the school's janitor. Having been caught by surprise, Chloe shrieks and covers herself with her hand. "Oh, shit! Didn't wanna interrupt, I'll come back later." - says the janitor. "Nonsense, Kenny, stay. Chloe doesn't mind, right?" - he tells her. She nods, still covering herself. "Ahm, okay. If you both say so." - Kenny shrugs indifferently. "We do. Now, Chloe, don't make young Kenny here feel uncomfortable. Remove your hands. You are making it seem like something inappropriate is going on." - Bill orders. "Yes, Uncle Bill." - says the blonde student. She removes her hands and tries to stand at attention. She closes her eyes with shame. Far from Kenny to complain about the situation, as he is practically drooling over the sexy volleyball captain's body. He knew how forbidden it was to get involved with someone from the Winston-Phillips family, and this blonde tart here was the next best thing. ï Chloe is feeling so embarrassed, she can feel the janitor's eyes burning a hole through her already small underwear. Andrew would hate it if he knew that she was practically naked in front of the custodian. "So, Kenny, what can I help you with?" - asks the old man with a cheeky smile. "Well, you see Mr. Principal William..." - Kenny starts to say, and dives into a small list of issues that he needs authorization to fix. The janitor's eyes are glued onto the scantily clad girl the whole time. She can't help but notice a huge bulge growing in Kenny's pants. It looks enormous. Her eyes widen and she starts to feel horny. "(...) and that's it." - the man finishes explaining. "Okay, you have my authorization. Tell that to Stella. Also, if I recall correctly, you are an ass-man, right?" - the principal asks. "Thas right, Mr. Principal William." - the janitor admits. "Call me Principal." - he says impatiently. "And you are in luck then. Chloe, please turn around and bend over, to give Kenny here a good look." - Bill says nonchalantly. "He has been doing a great job, so he deserves it." Chloe's mouth falls open. She is initially conflicted, but her naughty side quickly wins the argument. Turning fifty shades of red, the blonde athlete turns around and bends over, presenting her small tight ass to the custodian. She can feel her wanton pussy pulsating under her 'Thursday' panties. "Wow, fucking hot. Thanks Mr. Principal!" - Kenny says, adjusting his massive bulge. "Go ahead and give her a couple spanks." - Bill says, adjusting his own member in his pants. Chloe looks at the old man to complain, but upon seeing them both sporting big erections, she decides against it. She arches her back, offering her tush to the pale janitor. Without hesitation, Kenny approaches her and slaps her right ass cheek with gusto. *smack* The sound echoes lewdly in the room. "Ouch!" - the blonde yelps. It felt good. She arches her back again, asking for more. The janitor once again slaps her ass, this time aiming more towards the middle of her butt. *smack* The peppy student squeals, a mix of pleasure in her voice. "One more for good measure." - instructs the principal. Kenny aims between her cheeks and lets his hand fly. *smack* "Ahhhhh...." - the naughty class-rep moans, having been slapped right on her aching cooch. "Very good, nicely done, young man. Now rub where you just hit her, we don't want her to be sore tomorrow." - Bill commands. "Yes sir, Mr. Principal." - the janitor says. Foregoing any demeanor, Kenny places his palm on her mounds and starts to touch it. He blatantly rubs her pussy above her panties, smirking at how damp they are. Chloe moans loudly with lust. She was feeling horny and aching for more. "More..." - she whispers to Kenny, her sultry voice filled with desire. The janitor starts to pull his pants down to free his raging boner. The principal realizes that he needs to put a stop to the situation before the young tarts gets fucked by the custodian in his office. That would be a scandal indeed. "*Caham*! Thanks Kenny, that will be all." - orders the principal. The tall pale man scrambles to get his pants back up and moves away from the student. "Yes, Mr. Principal. Thanks for the authorizations." - he says with a slight bow. "And thank you, Miss Chase, it was hot. Seeya around!" - he says with a dumb smile. "You're welcome, young man. Keep up the good work. Chloe, what do you say?" - asks Bill expectantly. "Thanks for the spanks, Kenny. My ass appreciates it." - she says shyly. The janitor nods and leaves, closing the door behind him. ***** Outercourse Training "Well done, Chloe, you behaved perfectly." - the principal compliments her. "Yeah, but that almost got out of hand, it was a little scary." - the blonde admits, although she was still feeling frustratingly horny. "Don't worry, Kenny is a decent guy, he just needs to be ordered around, or else he can turn into a wild animal." - the old man laughs. "Really?" - she asks, images flashing on her twisted mind. "Oh, yeah. He was pulling his pants down, if I hadn't stepped in, he would have fucked you senseless." - the principal says. "Wow... ahm... thanks for looking out for me, Uncle Bill." - Chloe says. "You're welcome. Now let's continue where we left off." - he says. She starts to put on the first outfit. She is quite enjoying showing off to Drew's uncle, it feels somewhat taboo. She finishes getting dressed and then poses for him. "Hmmm, it doesn't work." - he says adamantly. "What doesn't work? I think it looks pretty cute." - she says looking in the mirror. "Right, but I think your underwear is in the way. Take it all off and try again." - he instructs. "Is it necessary? I think we can have a good idea." - she asks. "Yes, it is. But don't worry, I have seen you wearing less." - he reminds her. "And I have touched you all over, as have the rest of the family." - he winks. "Please don't tell Drew, he wouldn't like it." - the blonde pleads. "Of course, but don't forget I saw your beautiful tits and pretty snatch already and he accepted it." - Bill says. "Well, he doesn't particularly enjoy it..." - she explains. "Ah, he'll get used to it, it's expected from the family. And I sense that you don't mind it much, you are way naughtier than I judged. I approve." - he says. "No! I also mind it! I'm not entirely comfortable with being naked in front of you." - she admits. "Ah! I see the problem now..." - he exclaims. Principal Bill starts to quickly disrobe. Chloe is taken aback by his sudden behavior. She interrupts him when he is wearing just his loose boxers. "Uncle Bill! What are you doing?" - she says, slightly covering her eyes. "Getting naked with you. This way you'll feel more at ease, since you're not the only one." - he explains nonchalantly. He starts to remove his underwear. "That is not what I me...." - the blonde starts to protest. Chloe trails off when his huge penis comes out. She just stands there staring at it. His member is thick and long, and his swollen balls hang low, covered in white pubic hair. It looks like the old man is sporting a baseball bat with a couple baseballs between his legs. Chloe's big dick fetish seems to take over her mind and will, now she has only one thing in her head. "Wow..." - she says quietly. "Do you like it? It gets a bit bigger when hard. I never heard complaints." - he brags. "How big does it get?" - the blonde student asks bashfully. "Around 9 inches I believe, but it's been a while since I measured it!" - he boasts. "Almost twice as big as Drew..." - she says absent-mindedly, eyes fixated on his cock. He smiles, this was going better than he hoped for, the girl was in dire need of a real dicking. "See, I told you. I knew you would be more comfortable if you weren't the only naked." - he says with a sly grin. "Now let's fix this." He approaches her and deftly unclasps her bra. She can see his dick growing as it rubs against her bare skin. "Finish removing your bra and I'll take care of those precious panties." - he orders. She feels her nipples ache as she removes her bra, letting her bare tits out. Chloe has decently sized breasts, extremely perky, with small dark red areolas and tiny pointy nipples. The principal smiles and sits back down. He pulls down her panties and exclaims pleasantly when he sees that she is fully shaved. He can tell she is sopping wet as a trail of her juices dribble down from her dark red slit into her panties. "Beautiful, that is how Winston-Phillips's women should be, bare." - he praises. "Thanks, I prefer it. Feels cleaner this way." - she explains. "Me too, and she smells great." - he says, taking a deep whiff. "Erm, thanks, Uncle Bill." - she says bashfully. "Now it's your turn to undress me." - he says with a grin. "Hm? You're already naked." - she says, ogling his old cock. "Well...." - he says and points down at his socks. She lets out a surprised exclamation, she knew what was going to happen. Bill opens his legs wide, and she kneels between them, extremely close to his masculine penis, who seems to be growing harder by the second. "I noticed your pussy is wet, did Kenny get you excited?" - he asks. "Be honest." She starts to remove his left sock. Her face is inches away from his almost fully erect cock. "Yes, I enjoyed the spanking. And seeing your big dick. I wish Drew would let me play with his wiener more." - she admits. "Well, I am family, so he will certainly not mind if we fool around a bit." - Bill explains. "Are you sure? I don't want to upset my boyfriend." - she asks, removing his right sock. She glances at his dick, who is now at maximum attention. It was the biggest she had ever seen, even larger than Lukas's. It was so thick and meaty, and she wondered if it would hurt if it slid inside her. "Of course! I am his great uncle, and we come from a long line of Winston-Phillips's men. It's important that you are well trained for him." - he says nonchalantly. She is staring intently at his large member. He moves forward a bit and starts to rub it against her face. "You know I am devoted to Drew, that's why I can't cheat on him." - she says, practically salivating over it. Her pussy juices were dripping on the floor, obscenely. "This would not be cheating. Think of it as practice." - he informs. "Okay. Just a little bit then. What should we do?" - she asks as her twat twitches. "I would love to have you suck on it, but I don't want to end this too quickly." - he says, and she looks somewhat disappointed. "How about you come up and sit on my lap, so I can show you some moves." - he says lecherously. "Okay, but no sex, I am a virgin. My pussy is off limits." - she reminds him. He nods. She stands, letting his prick rub all over her face and chest. When his massive dick contacts her tits, she lets out a loud groan. She straddles him, pinning his cock between their bodies. She is in ecstasy. "We call this outercourse." - he says. "Doing it like this, allows you to rub your slobbering cunt along the shaft of the penis without the risk of it going inside." - he explains to her. He holds her by the waist and starts moving her up and down, her virginal cooch sliding along his big member. They keep grinding for a bit. Chloe is moaning deeply, extremely close to coming. "Of course, you can't go too high, or it can accidentally penetrate your snatch. Like this..." - he says. He lifts her up until the head of his dong is aligned with her vaginal opening. He pokes at it and puts a quarter of his cockhead inside. She cries with pleasure, almost climaxing. He then immediately puts her back down, sliding her cunt along the length of his erection. "Ah...." - she lets out a frustrated sound, not hiding her disappointment. He repeats the move another time and again she lets out an upset guttural noise. "Maybe another time." - he winks at her. "However, if the guy is too small, this might be risky. How big is Andrew again?" "Hmm... probably a bit more than half your size, but way thinner." - she admits, panting. "Yeah, that won't do. I guess I need to show you another position." - he says. "Yes, please... yesssss... teach me, Uncle Bill." - she nods enthusiastically. He holds her waist and pushes her away from his cock. He then slides the head of his penis across her whole slit, letting it come out at the bottom, momentarily poking her asshole on the way. She moans, her orgasm imminent. He positions her back on top of his shaft, letting it part her pussy lips lewdly. He then starts to slide his hog back and forth on her slit, coating it in her dripping juices. She groans lewdly. "Do you like this one?" - he asks. "Oooooh.... I do... fuuuuuck... so I need to do this with Drew... feels good..." - she moans. "Yes, and if he doesn't want it, come here and I'll help." - he says. "Now, are you ready to come, little slut?" - he asks. "Yes... Yes... please..." - she pleads. "Where do you want to come? All over my dick? Ask me like the good tramp that you are." - he orders. "Mmm... all over your big fat cock... ngg... yes... let me squirt on it, like the slut I am... fuckkkk... slide your cock all over my wet pussy... yeeeesss... I'm a pervert... letting Drew's uncle slide his big cock on my virgin cunt... fuuuuuuck... nnnng.... Yesssss..." - she cries, climaxing hard onto the principal's prick. She shakes uncontrollably on top of him, having had the most intense orgasm of her young life. Principal Bill gives her some time to recover, his steel hard member ready for a climax of his own. "Well done. Andrew will be pleased with your progress." - he states. "Now it's my turn..." A knock on the door brings him back to reality. "Tsk..." - he says. "Give me a second!" - he yells at the person behind the door. He lifts Chloe and plops her on the couch, as if she didn't weigh anything. He gets up, opens a closet and takes out a big fluffy robe, putting it on and tying it tightly. "Come on in!" - he says with blue balls for not having ejaculated. Chloe finally realizes what is happening and she panics, but it's too late. ***** Prof. Henry Sesh The door opens and an elderly scrawny man comes in. He seems to be a bit younger than Bill, but not by much. He has a mousey look and feel to him, being short, small and white-haired. The senior man stops dead on his track when he sees the naked blonde student, unsuccessfully trying to cover her bits. "Oh, s-sorry, d-didn't mean to i-interrupt." - he stammers. "Nonsense, Henry, join us. Chloe, you know Prof. Henry, right? He is the music and tech teacher." - the principal says. "Erm... yes... hi Prof. Henry. Can I get dressed, Uncle Bill?" - the sexy class-rep asks flushed. Henry is so hypnotized by the young tart that he doesn't notice that the principal is in a robe. "I don't see a reason for it, we'll resume as soon as I talk to Henry, so stay put." - he orders. "What can I help you with, Henry?" "Oh... erm... well... you see... I was wondering if we can get a couple of new instruments for the class." - the professor stammers, not breaking eye contact with the nude girl. "Of course, you have my approval. Stella will arrange anything you need." - Bill says. "T-thanks, Bill." - the skinny man says, not moving an inch. "Anything else? We need to keep going here." - the principal says hastily. "What w-were you two doing?" - the scrawny teacher asks. "Ah, just trying some new uniforms for the students." - Bill answers. "C-can I s-stay and w-watch?" - asks Henry with a lustful look. "I don't see why not. Are you okay with that Chloe?" - he asks rhetorically. "No!" - the principal stares at her. "Ah...I guess so." - she says reluctantly. "Very good, you made the right choice. It's what is expected of a woman with the Winston-Phillips name." - Bill nods approvingly. "Erm... do I have to be naked the entire time? It's embarrassing." - Chloe protests. "Of course, dear. You didn't complain much until now." - the principal reasons. "It's because you are my uncle, and you gave me no choice!" - the blonde argues. "Well, nothing changed in my view." - says Bill, pointing Henry towards an empty couch. The elder teacher sits down with a lecherous grin. "Professor Henry is here now! Drew is not going to like me being naked in front of him. Can I at least put on my underwear?" - she asks in a desperate attempt. "No, you will stay like that. I am Andrew's uncle, so he'll have to get over it." - the old principal says sternly. Chloe sighs deeply, she was already expecting his answer, there was no way to reason with a male from Winston. Especially the ones from the family. She was feeling mortified. The only men who saw her fully naked before were Andrew and Bill. Yes, some family members saw it, but only glimpses when they were molesting her. Nevertheless, parading totally bare in front of a random teacher was too much for her. "You can go ahead and start trying on the uniforms!" - Bill ays nonchalantly. Chloe starts to try on and go through different outfits. Both men express their approvals and their dislikes. In total, the blonde volleyball captain was naked for over ten minutes in front of the old man. Her pussy was completely damp again, thoroughly enjoying the unwanted attention and slobbering everywhere. The class-rep was worried, she was starting to relish these situations too much, even if she was slightly betraying her boyfriend. Maybe that's why Mary did it. She wasn't expecting to see eye to eye with Mrs. Hunter on this day. Both men were fully hard after the shameful exhibition by the young temptress, as is evident by Henry's pants bulge and the principal's massive tent on his robe. "Well done." - the principal claps. "I think we have a few winners." - he says. He puts a few winning outfits to the side, for Lana to wear in the future. "Thanks for letting me watch it Ms. Chase, this made my year." - admits Prof. Henry, not nervous anymore. "I didn't have a choice, but you're welcome." - she says defeated. "Thanks for the input, Henry bud. Before you go, want to request anything from Chloe?" - Bill asks. "Anything?" - the scrawny elderly asks lustily, adjusting his boner. The blonde turns red, imagining all the ways the professor could ravage her. "Sure, she's also in training today, so it would be good for her future." - the principal assures him. "In that case... since she has been flaunting that tight body of hers, I need to try it. Can I give her fresh cunt a lick? I could smell her pheromones the whole time." - Henry asks, any hint of shyness gone. The blonde athlete gasps. Nobody had done that before. "Hahaha!" - guffaws Bill. "Of course, of course. Chloe, be a dear and sit down on the couch and spread your legs for Henry here." - he says nonchalantly. "I don't think I should. Andrew has not done it yet." - she admits timidly. "Well, it's just another 'first' that my nephew will miss. No worries." - Bill says. "Just one lick, please. I haven't had a tight young twat in my mouth in years." - the teacher pleads. "Go ahead Henry, she doesn't mind." - the principal says. Knowing it was useless to debate, Chloe reluctantly sits down fully naked on the couch and spreads her legs wide, giving them a perfect view of her bare dripping dark-red snatch. "It's perfect..." - says the scraggy professor in awe. "Go ahead Henry, we don't have all day." - his boss hurries him. Not wasting time, he kneels in front of her and dives forward, licking from the bottom of her wet slit, all the way to the top, where her pubic would have been. Chloe moans intensely. The sensation was like nothing she has ever experienced. Instead of stopping at one lick, the boney old teacher starts to lap at her pussy, eagerly. "That's enough, Henry. You had your fun, now get out." - Bill orders. "Ah...." - the turned-on girl groans, not wanting this to end. The senior man dislodges from her virginal sex, stands up and lick his lips lewdly. "Thanks, Ms. Chase, exquisite taste. I'll see you again." - he winks. "Thanks, Bill, for the instruments." - he says, walking away hunched over, trying to hide his erection. Still on the couch with her legs spread, Bill approaches her and opens his robes, freeing his huge hard-on. Fearing that he was going to fuck her, Chloe recoils a bit. "Don't worry. I won't do anything. I just wanted to request something." - he explains. "What is it, Uncle Bill?" - she asks innocently. He kneels a bit and starts to hit her wet snatch with his dick, slapping it obscenely. She moans loudly with each cock-smack. "So, I was thinking. From now on, how about you wear skimpier outfits? Maybe skip the bras entirely since your tits are so perky anyway." - he proposes, midst dick-slap. "Ah... mmm... uh... I suppose... I could do that..." - she agrees between moans. "You can even forego your panties sometimes. Only until we get the new uniforms." - he says. "Ahh... I'll do it... hmm... I'll feel so slutty all day... Drew will be upset... ahhh." - she moans. "He'll get over it." - Bill says. "You like this, you little slut?" - he asks, smacking her with his cock even harder. "Ahhh... yessss... I love it... hit my cunt with your big fucking cock... ah... more..." - she pleads. He suddenly gets up and ties his robe back. He knew it was not yet the time to take things any further. "What... no..." - she complains softly. She was so close. "I have an appointment soon; we need to finish this." - he says sternly. Disappointment was stamped all over the pervy blonde's face. She wanted more, but she was not going to get it this time. She was frustrated again. Suddenly, there is another knock on the door. "Come in!" - says the principal merrily. ***** Hunter Sesh In comes Mary Hunter, dressed in a nice tight pencil skirt and an opened button-up blouse, emphasizing her cleavage. Her breasts were made more pronounced due to her fake boobs. "Oh, great of you to finally join us." - exclaims Bill, pleased. She glances between him and the wet naked slut on his couch and giggles. "Erm... this is not what it seems..." - Chloe stammers. "Of course, it isn't." - Mary says giggling. "You were just trying the new uniforms, right?" "Right... that is what we did... that is why I'm naked..." - the blonde excuses. "And dripping pussy juice. Suuuuuure. Shame on you, Bill." - Mary winks playfully. He laughs at the naughty teacher's acting. "Don't make her feel bad, dear. We didn't go too far, today." - the old man says. "Oh, so you didn't cheat on Andrew?" - Mary asks the horny teen. "No, I am not like you..." - she retorts softly. "Oh, I see. Well, don't worry, you seem to be more and more like me by the second." - she smiles. "I am also obsessed with huge pricks." "I don't love large dicks... Uncle Bill is just helping me practice..." - Chloe says. Mary giggles, impressed by the blonde's conviction. "As you can see, she's still resistant to some things. Give her time." - Bill acknowledges. "Good, that means I still can still have your big cock?" - Mrs. Hunter asks nonchalantly. Chloe gasps at the teacher's attitude. Mary could be very forward sometimes. "You can, I haven't gotten relief yet, this little tramp left me hanging." - Bill says with disdain. "No... I didn't... I mean..." - the class-rep stammers. She was abnormally nervous in the presence of Mrs. Hunter, who was a legendary figure in town. "Don't be nervous my little hussy. It's okay." - the teacher assured her. Mary comes closer and gives Chloe a kiss on the lips, who moans with delight. The two blondes quickly start to make out. Mary notices that the young student is in dire need of relief, so wanting to be a good role model, she slides her hand until she reaches Chloe's pussy. The athlete whimpers at the touch. "Please... let me come..." - she pleads softly. Mrs. Hunter starts to rub the needy wet twat. With one hand she rubs across the blonde's clit and slit, and with the other hand she slides a finger inside the student's tight vagina, fingering it sloppily. The naked girl just moans, completely lost in pleasure. In a matter of seconds, Chloe is coming. Once again, an earth-shattering orgasm rips through her young tight body. "Ahhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh...." - she screams in ecstasy. Mary kisses her forehead and holds her hands in place until the student's orgasm has subsided. The teacher turns around and smiles at the principal, who has taken his robe off and is stroking his large cock, mesmerized by the naughty lesbian display in front of him. "I guess it's your turn now." - Mary says sultrily. He grunts. The blonde bimbo kneels in front of the old man and starts to slowly give him a handjob. "Hmm... I don't want to dirty my makeup or clothes." - the teacher says. "Fuck that, Mary. I have been playing with this slut for the past couple hours, I need this." - Bill says. "I know, I know." - Mary replies. "Chloe, get your ass over here." - she orders. Obediently and still recovering, the class-rep gets up and wobbles to where the couple is. She pauses when she notices that Mrs. Hunter is just nonchalantly jerking off the principal's massive dong. "Erm... what should I do?" - Chloe asks nervously. "Just kneel down in front of the cock." - the teacher says impatiently. She does as was ordered, lust still controlling her every move. Mary spits on the principal's prick and uses her saliva to jerk it off. Even though she just climaxed, Chloe's pussy and brain ache for more. Her only thoughts were of lust and sex. "Are you ready to shoot, big-boy? Ready to spurt your old cum all over this little hussy's tits and face?" - Mary asks the principal. "Yesss... ung... Imma come on this little whore..." - he agrees. "Do it, she needs some cum on her flawless skin. Do it, squirt all over her!" - she eggs him on. Meanwhile, Chloe is moaning, absent-minded caressing her throbbing sex. "Nnnnnngggg... coming..." - Bill announces. His cock spurts rope after rope of white thick cum all over the blonde student. Mary aims his pulsating dick at the tart's chest and then at her face, covering it in white goop. Chloe squeals in delight. The teacher expertly milks all the cum out of the penis, painting her student with it, not letting a single drop go to waste. She grabs a handful of cum and feeds it to the naked blonde, who accepts it eagerly. She gets up and walks towards a close, leaving the two nude people panting, lost in desire. "Fuck that was good." - exclaims the principal. "Thanks, Mary, it has been a while." "I can see that." - the teacher giggles, glancing at Chloe, drenched in thick semen. Mary starts rummaging through the drawers. "Chloe, sorry about all the cum." - says the principal, feeling slightly bad. Mary always had a way with him, any man really. He always got carried away when she was around. He wasn't planning on going this far with the young blondie, but alas, too late now. "Ah... no problem... Uncle Bill..." - she says, breathing hard, completely covered in sticky cum. The principal hands her a box of tissues and they both clean themselves up. Mary is still fiddling around with the drawers in the background. "I know we got carried away, but we achieved great progress today." - Bill tells her. "Yeah, it was 'enlightening'." - the cheery student giggles. She starts to put her regular clothes back and he ties his robe back around him. "Glad you agreed to wear skimpier clothes and not wear a bra." - the old man says. "Hum, right. Almost forgot about that." - she admits turning red. "Make sure to also forget your panties sometimes" -- he winks. "Andrew would certainly enjoy seeing you parading around for the whole school." "Are you sure? He's very jealous." - she asks dubiously. "I am, he needs to learn." - the principal emphasizes. "If you say so." - she agrees. "Thanks for helping with the uniforms, I'll talk to Stella to order them. And I separated the best ones to give it to Lana on Friday." - he informs her. "I am looking forward to seeing Miss Lana wearing them." - the class-rep beams. The bell rings, signaling the end of the morning. "You should go now; we don't want you late for any other classes." - he grins at the cute student. Mary comes over and hands him a small blue pill without saying anything. "Ah, Mrs. Hunter!" - exclaims Chloe, shocked. You see, Mary was completely naked, her fake tits on full display as well as her freshly shaved pussy. "No need to be shocked, dear. Run along now, I have something to take care of." - the teacher says dismissively. Mary drops to her knees and fishes out the principal's old flaccid cock from inside the robes. The principal shrugs at his students, mouthing 'what can I do'. Chloe turns around and walks off, stealing a glance inside the office before closing the door. "Ready for round 2, old man? My cunt needs your big fat cock." - says Mrs. Hunter sultrily, licking her lips. That is all she hears before she leaves to go meet Andrew for lunch. She was smelling of cum, but hopefully he wouldn't notice that.