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Highland College - Season 1 Part 4	By : TheChemist Category: Celebrities - Misc > AU - Alternate Universe Views: 3129 -:- Recommendations : 0 -:- Currently Reading : 0
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Chapter List
- 1-Part 1
- 2-Part 2
- 3-Part 3
- 4-Part 4
- 2
- 3
- 4
While Megan was busy picking up her crew, Amanda was on route to the last place on her list. First she picked up Olivia Wilde, who was the sexiest Santa’s helper she’d ever seen. Hopefully good old Saint Nick didn’t have help like that or else adultery would be taking up most of his time.
Next on Amanda’s route was Ashley. The team captain had sent her a text once she had pulled up outside her house and Ashley came walking out immediately. The sexy brunette went as a naught french maid, and by the look of her, both Amanda and Olivia doubted that any cleaning would actually get done with her as a maid. In fact they were certain it would only lead to more dirty sheets.
“Anyone else find it curious Sarah invited Kristen,” Olivia asked her two other teammates.
“Yeah I was pretty surprised,” Ashley admitted. “I mean this is to sort out the crap going on between the players.”
“Okay, last stop,” Amanda said as she pulled up the curb in front of Kristen’s place. “I’m sure Sarah has her reasons.”
The sexy sophomore with auburn hair emerged from her doorway after giving her boyfriend a kiss goodbye. Kristen was dressed in a nurse’s outfit, but put a twist on the typical slutty costume. Instead of going with a modern version, the slim beauty was inspired by World War II by wearing an olive skirt, light yellow blouse, and high heels. To really give the 1940s feel, Kristen wore her hair in an old-fashioned bun topped with an old army burette.
“You look awesome Stew,” Ashley told her best friend as she got into the back seat of the car.
“Yeah Kristen, love the classy but sexy costume,” Olivia added.
“Aw, thanks girls,” Kristen blushed.
The girls chatted the whole drive about a variety of issues, each one more trivial than the last but they were having a great time. It didn’t take long until Amanda’s GPS was telling them that they had arrived at their destination.
“Fancy meeting you guys here,” Megan said to them.
“How long have you guys been here,” Olivia asked her teammate.
“We were like 10 seconds ahead of you so it was great timing,” Nina answered.
“Perfect. Well we shouldn’t keep Sarah waiting,” Amanda suggested.
The pack of 10 sexily clad girls in costume walked up the main door of the very fancy condo. They talked to the doorman who immediately sent them up to the penthouse floor as the blonde coach had already given him instruction.
“Who knew college volleyball coaching paid so well,” Hayden said in the elevator ride up.
“She married a fairly successful movie producer or something like that. She makes good money but probably not enough to support this place,” Vanessa relieved.
They arrived at the top floor and poured out of the metal carrier. Finding the right door, one of them rang the doorbell. Within seconds they heard steps approaching before the door opened. Carrie Underwood was standing in front of them in a super small flannel shirt, the shortest pair of lean shorts imaginable and a pair of cowboy boots and hat to round out the western-themed outfit.
“Welcome y'all,” Carrie greeted in her most Southern accent.
“Love the pigtails,” Taylor Swift complemented. It was the first words the Tennessee native had spoken since the lobby of the dorm.
“Thanks Swift. Come on in though,” Carrie offered.
“Hey everyone! Glad you all could make it,” Sarah said to her team. “You all look fantastic! So everyone takes a seat around the table while Carrie, Scarlett and myself bring out your drinks.”
“Hope you girls like martinis,” Scarlett’s voice could be heard from somewhere in the back of the kitchen.
“You’re home is amazing,” Kristen complimented the host.
“Thanks Stewart. Follow me and I’ll give everyone a tour,” Sarah offered. “And in case you were wondering, I'm a vampire for Halloween.”
The team followed their coach as she took them around her home. She had a massive living room with lots of floor space around a leather couch, love seat, chair and ottoman set. In the middle of that room was the coffee table but was covered with a black sheet.
“This is the spare bedroom,” Sarah described. “Just ignore the guillotine in the corner, it’s for a haunted house that my husband and I are helping to set up for tomorrow night.”
“It’s either for the haunted house or Coach S is really kinky,” Vanessa commented in a low enough voice that Sarah couldn’t hear her.
“My bedroom is in here. Just your standard stuff in here, nothing special. Washroom is at the end of the hall for whoever needs it and for the purposes of tonight I’ve transformed the dining room into a bar and poker area,” Sarah explained.
“Poker? But I don’t know how to play,” Nina complained.
“I didn’t bring any money to bet,” Olivia added.
“Yeah me neither,” a few more chimed in.
“You won’t need it,” Carrie interrupted. “And it’s to your advantage if you don’t know how to play but I’ll get to that later.”
“Everyone sit and have your drink. Don’t tell anyone we’re giving you alcohol, especially you minors,” Scarlett told them as she emerged from the back with a tray of drinks.
The entire team felt their jaws drop as they saw the busty administrator. Scarlett must have been a comic book fan as she was dressed like Catwoman, wearing a skin-tight leather suit, black mask that encircled her eyes and knee-high boots.
“It’s impolite to stare, ladies, not to mention drool,” Sarah told them, snapping them out of their lust-fueled daze.
The girls did as they were told and each one sat around the large wooden table while Sarah, Carrie and Scarlett passed out apple-flavored martinis. The only other thing on the table was playing cards but no poker chips, much to the curiosity of some.
“Where’s the chips Coach,” Megan asked.
“This is part of the team-building exercise for tonight,” Sarah answered.
“I don’t understand,” Hayden spoke up.
“You’re wearing your betting chips. Tonight we are playing strip poker. Anyone unfamiliar with the rules, they are quite simple. When you want to play a hand you must put in clothing. At any time you can choose to go all-in but you must remove everything,” Scarlett educated them.
“This is mandatory too. Anyone who doesn’t play is off the team,” Carrie added.
“So you plan on making us get along better by forcing us to strip,” Momsen asked sarcastically.
“Have faith naughty schoolgirl. Any other questions?” Sarah asked.
“What do we do once you’re eliminated,” Nina inquired.
“That’s when the real fun and bonding begins,” Carrie answered with a wicked smile. “But we’ll get to that in good time. And remember, anyone who fails to take part in the mandatory team-based activities is kicked off the team.”
“Oh and every time you fold your cards, you take a shot,” Scarlett added.
“You are trying to get us drunk,” Hayden accused playfully.
“Why would we want to get a bunch of gorgeous college girls drunk? That just seems ridiculous,” Carrie replied with a wink.
With all the questions seemingly out of the way, the three hosts took their seats. Sarah took the cards, shuffled them up and dealt each person two cards. Most of the girls had played Texas Hold’em poker before so they knew what to do, but there were a few who were new to the game.
“So you get two cards, take a look and if you like your cards you have to put one piece of clothing in the middle of the table. Anyone who doesn’t know what a good hand is, here is a list,” Sarah handed out a few copies of the playing rules.
“Next I’ll flip over 3 cards. If you like your chances then make another bet. You can fold at any time but you don’t get back your clothing. After all the bets are done, I flip over a fourth card. Another round of betting, a fifth and final card is flipped over. Last chance to bet then the girl with the best hand collects the clothes and can use them to bet for the rest of the game,” Sarah finished.
“And the best way to learn is by doing,” Carrie added. “I’m first to bet and since I like my hand I’ll throw my hat in.”
“Thank God I wore a thong tonight or else I’d just have my hockey jersey and shoes,” Nina commented. “I’ll fold.”
Each girl proceeded to either fold or bet conservatively for the rest of the hand until it was only Sarah and Megan left by the time the fifth card was flipped over. Sarah had the better hand so was left collecting a small pile of clothes while the black-haired player was left without shoes and her red cape.
The next few hands had a similar trend with modest betting and Sarah winning two of the rounds and Kristen also winning a hand. No major clothing had been lost yet, everyone short mostly footwear. The alcohol was flowing at a near constant rate though, and soon the girls were feeling the effects.
“That’s it. Someone has to get this party started and it might as well be me,” Scarlett announced. “I’m all-in.”
With that said, the busty blonde got up on her feet and kicked the chair back to have some room. With all eyes on her, Scarlett reached for the zipper of her leather outfit and slowly pulled it down until it reached its stop around her crotch. She pulled her arms free and exposed her massive tits for the party to see before stepping out of her costume, completely naked.
“Fuck you’re beautiful,” Megan gushed.
“Keep the mask,” Sarah told the blonde. “Makes you look so sexy.”
“Whatever you want Gellar,” Scarlett replied.
The next few girls were scared off of the large wager and folded. They poured themselves a shot and chugged it down until finally it was Sarah’s turn to do something.
“I’ll go all-in with you Scarlett,” Sarah announced.
“Shit,” Carrie commented. “I fold then.”
Everyone else folded too rather than go up against Sarah. Both the coach and Scarlett flipped over their hands and the naked administrator had the advantage with a pair of kings over Sarah’s queen and two. The three cards the dealer flipped up helped Sarah by giving her another queen but the fourth card was useless to her.
“How does it feel to have all your winnings from the last few hands ripped away from you,” Scarlett gloated.
“Even the blind squirrel finds the occasional nut,” Sarah muttered.
“No!” Scarlett shouted, as the final card was flipped over and revealed a third queen for the volleyball coach.
“Looks like my queens beat your kings,” Sarah rubbed in. “Thanks for playing but I think everyone here would agree that you look better naked so go have a seat in the living room and show the loser what awaits their exit from the game.”
“Alright,” Scarlett muttered.
Scarlett got up from the poker table and took a seat on the leather loveseat in the nearby living room. The seat was facing the game so that the naked blonde could watch how the game unfolded.
“Why don’t you show the girls what’s under the black blanket,” Carrie asked of the eliminated player.
“Gladly,” Scarlett replied. She reached over and pulled the sheet away from the small table to show the party the largest collection of sexy toys any of the students could have imagined.
“Holy crap,” Ashley gasped.
“How can one person own this many toys,” Momsen asked her coach.
“They aren’t all mine. Some are Carrie’s, some are Scarlett’s. Either way, they are for all of our enjoyment tonight,” Sarah replied.
“This little guy is my favorite,” Scarlett told them, showing off a large vibrator. “We’ve had some good times in the past.”
“Then why don’t you get busy with it,” Carrie recommended.
Scarlett threw one of her legs over the arm of the chair and pushed her ass further to the edge of the seat. With better excess to her pussy, the busty blonde lowered the vibrator to her clitoris, drawing a long and loud moan out of herself.
“Oh yes I’ve missed you,” Scarlett cooed, referring to the toy in her hand.
“So as you can see, the fun doesn’t end once you finish the card game,” Sarah told the rest of the group. “On the table is everything from didlos to anal beads and everything in between.”
“Will hurry up and deal the damn cards,” Megan ordered at once.
The pace of the game had sped up since Scarlett had started to pleasure herself. None of the players could deny that getting eliminated from the poker game wouldn’t be the worst thing in the world. The speed at which the ladies were playing nearly matched the increased tempo of Scarlett’s moans.
“I could really use one of you to shove that big dildo in my pussy,” Scarlett seduced while continuing to work herself over with the vibrator.
“Screw it, I’m in,” Megan said.
The dark-haired beauty rose up from the table and started to remove her superhero get-up. Having only wagered her cape so far in the competition, she was to take off her tight Superman tee-shirt, red booty shorts and matching boots.
“No underwear,” Hayden questioned.
“The costume was too tight to fit with them on. Plus I didn’t know I would be getting naked at this party,” Megan replied.
“When was the last time we didn’t all get naked at a team function?” Olivia asked, making the group laugh.
“I’ll call you all-in with one myself,” sexy cowgirl Carrie said to the now naked Megan.
“Then get those clothes off, assistant coach,” Sarah told her.
“Gladly,” Carrie said as she quickly removed her clothes and exposed her bare body. Megan’s body was a little longer with more curves than Carrie’s but the blonde was extremely tight with bouncy tits, smoking ass and lean legs.
“You two are thinking with your damn pussies rather than your brains so I’ll gladly take those clothes off your hands,” the coach told them.
Sarah was bang on about Megan and Carrie. Carrie had a weak hand of an eight and a two while the dark-haired co-ed had a pair of fours. The coach only had an ace high with a 10, but she flopped another 10 and easily won the pot. Sarah and Carrie seemed happier to lose and be kicked out of playing cards than if either of them was to actually have won the hand.
The card game was put on hold for a little while as the rest of the team watched as the team’s assistant coach and Megan sprinted over to Scarlett. Both girls took one of the busty blonde’s massive tits in their hands then targeted the nipple with their mouths.
“Oh yeah,” Scarlett moaned as she continued pleasuring herself. “It’s about time.”
“We lost as quick as we could baby,” Carrie told the blonde before swirling her tongue back around Scarlett’s sensitive nipples.
The Southern blonde moved upwards from Scarlett’s boobs and started passionately kissing her while Megan now had both oversized tits to play with. While using her tongue to coat Scarlett’s chest in saliva, the sexy dark-haired girl reached a hand down between the blonde’s legs and stuck two fingers into her soaking wet hole.
“Ahh,” Scarlett moaned into Carrie’s mouth as Megan used her fingers to thrust into her pussy.
As if perfectly in sync with each other, Megan and Carrie swapped positions so that now the leggy college student was hungrily making out with the head recruiter while Carrie went back down to entertaining Scarlett’s breasts. The tight blonde didn’t stay long as she licked her way down the curvy woman’s body until finding herself on her knees between Scarlett’s creamy white thighs.
“This one seems like you’d like it,” Carrie told the blonde. “Long and fat.”
The southern beauty grabbed the dildo from the table and inserted it into Scarlett’s pussy. The fake penis slid easily into her lubricated folds, causing Scarlett to scream out in pleasure.
“Ohhhh,” Scarlett moaned into Megan’s mouth.
As the tiny blonde continued to ram the dildo into the curvy administrator, the threesome was unaware that they had every set of eyes in the room on them.
“Can two more join?” Olivia asked.
“We promise to make up for our tardiness,” Amanda added.
“Get your naked asses over here,” Megan demeaned.
Amanda and Olivia had quickly lost all their clothing on the last hand. Despite having played poker quite a bit, both females rushed in to bet all their clothes on hands they knew they couldn’t win.
The threesome momentarily was paused as the pair made their way from the card table into the living room. The differences between the two girls were quite evident as they strutted into the soon-to-be orgy. Amanda was a somewhat short blonde with amazing curves, meaty ass and large bouncy tits. Olivia on the other hand was tall with black hair with a model’s body; slim, perky tits and a small ass that luckily still had some meat on it.
“Seems only fair that you guys make up for being late. You get on your knees and make it up to us,” Carrie suggested.
“Well we’d hate to disobey a superior’s orders,” Olivia replied with a wide grin.
“Since that small loveseat will be pretty tight with all three of you on it, why don’t you get comfortable elsewhere,” Amanda recommended.
As if in a synchronized orgy competition, Scarlett, Carrie and Megan got onto their knees and bent over the front of the sofa so that their asses were hanging up in the air.
Olivia and Amanda were both lesbians, even though the dark-haired girl would satisfy an itch with cock every now and then. The sight of 3 of the hottest girls giving them a view of their naked bodies was mouthwatering to the two college seniors.
The two latecomers took different strategies to give their new lovers pleasure. Amanda was going to go at them with her skilled and nimble tongue. She had much practice with it and was very interested in savoring each of their unique tastes. Olivia on the other hand was stepping into a harness of a lengthy strap-on dildo.
“Oh that’s good,” Megan complimented as Amanda wasted little time sinking her tongue deep into her teammate’s folds.
While Amanda took turns sampling each of the three women, Olivia was using her strap-on dildo to give them a different sensation. Shortly after the blonde went down Megan, Olivia stepped behind her and guided the long plastic cock into her slick pussy.
“Fits like a glove,” Megan cooed as Olivia reamed the first 5 inches into her.
Olivia continued to build momentum by slipping another inch into her lovely teammate. It didn’t take long until Olivia was gliding all 8-inches into her snatch, with each thrust causing Megan’s meaty ass to ripple due to the force.
“I love having a lesbian lick me out,” Carrie commented with a wide grin on her pretty face as Amanda sloppily went down on the assistant coach.
“She’s really good,” Megan answered while her body was being pushed about by Olivia’s thrusts.
“Come here,” Carrie told her before planting a deep wet kiss on Megan’s lips.
As Carrie and Megan wrestled each other’s tongues in their mouths, their teammates were continuing to pleasure them. Olivia had now worked up a sweat after 10 long minutes of hammering Megan’s once-tight pussy. Amanda’s jaw was starting to get tired as well, but the tastiness of Carrie’s folds kept her motivated for the task at hand.
“You’re going to make me cum soon,” Megan warned her dark-haired teammate. Megan’s mouth was now free to scream out in ecstasy as Carrie was now moaning into Scarlett’s mouth as the two were engaging in a long make-out session.
“Be loud for me bitch,” Olivia demanded as Megan’s breathing became quite labored.
After several more minutes of Megan’s moans getting progressively louder, her pink pussy started to spasm before the dark-haired girl cum violently.
“Uggghhhhh,” Megan groaned at a near deafening volume as came for the first time that night.
As Megan’s warm pussy juice flooded out of her hole and down Olivia’s dildo, Carrie’s own orgasm was approaching quickly. Amanda’s tongue was still buried deep in her folds as the co-ed explored every nook and cranny of her assistant coach’s insides.
“Oh yes! Keep eating my pussy. I’m going to cum soon,” Carrie encouraged while holding Amanda’s head firm against her backside.
“Mmmpph,” Amanda mumbled as she seemed to re-double her efforts of getting the thin blonde off.
“Aahhhh,” Carrie grunted as a wave of her juices smacked Amanda in the face. The lesbian did her best not to spill a drop as she greedily collected as much of the sweet fluid that she could.
“Wow that was hot…now bring that tongue over here,” Scarlett demanded, having been masturbating for the whole time that Amanda and Olivia were pleasuring Carrie and Megan.
“I had a better thought in mind,” Olivia told the busty blonde.
Amanda was in tune with her thoughts and allowed Olivia to slip the dildo into Scarlett’s wet folds. The fake cock was bigger than the fingers she was using to fuck herself with, but her pussy easily stretched to accommodate the added girth.
“Damn that feels nice,” Scarlett groaned as Olivia started to really slam into her.
“Feel free to jump in Seyfried,” Olivia encouraged her teammate.
“How could I pass up a second go at this sweet treat,” Amanda said as she licked her lips in anticipation while crawling over to Scarlett.
“Second time?” Olivia asked as she molested the blonde’s massive tits while continuing to ram her fake cock into her.
“We kind of hooked up in the sauna recently,” Amanda admitted while maneuvering herself under both Olivia and Scarlett.
“OHHH,” Scarlett exclaimed once Amanda’s skilled mouth latched onto her sensitive clit.
“You like getting licked and fucked with a big dildo at the same time,” Olivia asked.
“Of course,” Scarlett cooed. “But I’d love your tongue back into my pussy,” she said to Amanda.
“That can be arranged,” Amanda replied after exchanging a quick look with Olivia.
“Ooohhhh! That’s what I wanted,” Scarlett moaned as Olivia was replaced with Amanda’s warm mouth.
“This should be wet enough but you might want to bite the pillow just in case,” Olivia told the busty blonde.
The dark-haired girl pulled apart Scarlett’s shapely ass, placed the tip of the thick dildo against her impossibly tight rosebud and applied pressure until the tip of the fake cock entered into her.
“Uugggghhhhh,” Scarlett groaned as the pain of her anus being forcibly penetrated was omnipresent.
Amanda really stepped up her efforts of eating out the attractive administrator in order to get her mind off the pain of being sodomized. To her credit, Olivia was very slowly easing in the head of the dildo.
“Is this too much or does it feel okay,” Olivia asked.
“This isn’t my first anal little girl. Just give me another minute then you can really fuck my ass like you want,” Scarlett told her.
True to her word, Scarlett started to push back against Olivia and take more of the fake cock into her expanding asshole. It wasn’t long until the whole thing had disappeared into the blonde’s anus and the real pounding began.
“Mmmm that feels so good,” Scarlett moaned as Olivia and Amanda pleasured each of her holes. “Don’t stop.”
“You taste so good,” Amanda told the slightly older woman.
“I know. Just make sure you share my cum once you get it,” Scarlett replied.
“Speaking of sharing, why don’t you have a lick Amanda,” Olivia told her teammate while removing the dildo from Scarlett’s gaped asshole.
The dark-haired girl placed the cock against Amanda’s lips and waited for the blonde to accept it into her mouth.
Amanda was a little apprehensive about sucking on a dildo that came straight from another girl’s ass, but she figured why not do it. Swallowing her pride, Amanda parted her lips and took the tool along her tongue and savored the taste. It was much different than the flavor of her pussy, but the blonde had to admit she liked it.
“Alright ATM slut. Give that dildo back so I can have another go with it,” Scarlett told the girl.
“Beg for it,” Olivia demanded.
“Please stick that cock back in my ass and fuck me hard like the whore I am,” Scarlett pleaded, looking the skinny girl in the eye.
The two teammates resumed their original positions as Olivia slammed the dildo back into Scarlett’s loose asshole at the time that Amanda squirmed her mouth back around her sensitive pussy.
With the dual sensation going on behind her, it wasn’t long until Scarlett felt an orgasm build and brim to the surface.
“I’m going to fucking cum for you two soon,” Scarlett screamed out.
“This is so hot,” Vanessa commented from the poker table, the game being temporarily suspended.
Olivia stopped pumping into her once she felt Scarlett’s legs give out. Amanda did her best to collect all of the busty blonde’s cum in her mouth as the orgasm that she so desired rocked her curvy body.
“Don’t hog all the good stuff,” Olivia told her teammate.
The pair engaged in a long kiss as Amanda pushed much of the cum into Olivia’s mouth. They continued to swap the sweet juices between them until most of the fluid was lost either to swallowing or some flowing out of their mouths and dripping on their hot bodies.
“Hottest. Sex. Ever,” Taylor Swift stated, feeling wet between the legs after their amazing display.
***
After the quick exits of Scarlett, Megan, Carrie, Olivia and Amanda so they could start up an orgy in the living room, the game had slowed to a crawl. This was partly due to the girls at the table being somewhat good poker players, but also because they found it hard not to watch the scene unfolding on the couches.
Ashley Greene had started off well but she had taken a beating over the last few hands and was now almost completely naked. Her French maid outfit was spread around the table, leaving her only with a black bra and a short silk skirt. She decided now was the time to make her last move and stripped off the remainder of her costume, but it was all for not as she was eliminated.
“Going to jump into the orgy,” Kristen asked her friend after knocking her out of the game.
“I’ll just stop at the washroom then yeah I will,” Ashley responded excitedly.
Ashley walked down the hall and did her business, thinking the whole time of how hot being in her first all-girl fuckfest would be. On her way back to the living room however, she paused when she looked through the doorway to the guest room. She stepped inside and examined the object of her curiosity then donned a wide grin as a perfect idea formulated in her head.
“That will teach her,” Ashley commented to herself. The brunette wasn’t a mean or violent person, but a young dog could definitely learn some new tricks.
Ashley went back outside to the card table and observed the game. Kristen and Sarah had the lead with the Coach looking like she had a bit more clothing in front of her than anyone else. Momsen was struggling though, with her panties being owned by Hayden now, her socks and shoes belonging to Kristen and Nina having her schoolgirl tie.
“You look like absolutely perfect jailbait right now Taylor,” Ashley complimented the freshman.
“Ha ha. Thanks Ash. It’s kinda what I was going for,” the newly modest girl replied. “Glad you like it.”
“I’m really liking the new you. Maybe once you’re done here we can grab a room together,” Ashley asked the blonde.
“Yeah sure. That would be really nice,” Momsen said while starting to blush.
“Be right back,” Ashley stated before running into the living room. The girls were in the middle of a hand so weren’t watching as the brunette grabbed a few items from the sex toy collection then deposited them in the spare room before returning promptly.
Taylor didn’t last much longer. She beat the rest of her costume with a crappy hand and wasn’t surprised when Ashley’s friend, Kristen Stewart, knocked her out of the card game. Momsen could have cared less however as she followed Ashley to the guest room that the brunette had found earlier.
Even though Taylor was mostly into guys, she had to admit she found that playing with the sexiest group of girls for the past few months had given her a new appreciation for the female body. She had wanted to try some lesbian sex for a while now, and it seemed like tonight it was finally going to happen.
“This way,” Ashley said while offering her hand to the now naked blonde.
Taylor accepted her invitation and was led away from the dining room, down the hallway and into the guest room. The young blonde didn’t notice the toys Ashley had grabbed earlier, nor did she realize the brunette’s true intentions.
“That guillotine is so weird, don’t you think,” Ashley asked Taylor.
“Yeah for sure. Being bound in a wooden trap waiting for a blade to chop your head off must have been frightening,” Momsen replied as she felt Ashley’s hands roam over her slim body from behind her.
“You’re so sexy Taylor,” Ashley told her before kissing along the length of her sensitive neck.
“Thank you Ash. I think you’re so hot,” Momsen answered honestly as the kissing was making her wet between the legs.
“Before we get into the good stuff, can you satisfy a fantasy for me,” Ashley asked the blonde.
“Sure. Just name it,” Taylor said while turning around and giving the shorter girl a kiss. “I’m game for whatever you want.”
“I know it’s a little weird but can you just get set-up in the guillotine? It would make me so horny seeing you restrained like that,” Ashley asked of the girl.
Not wanting to upset the girl she wanted desperately to have sex with, Taylor complied with her wishes. Lifting up the top piece, the younger girl placed her hands in the arm holes and her neck in the head groove. Once settled, Ashley helped lower the top so that Taylor was trapped naked in the Halloween prop.
“Seeing your naked ass bent over like this is seriously hot,” Ashley told the confined girl. Much to Taylor’s surprise, she heard a metallic click then was unable to lift the wooden top piece off of her.
“Alright Ashley, very funny. You’ve got me in a guillotine. Good prank. Now let me out please,” Momsen asked politely.
“I don’t think I’m going to do that actually,” Ashley replied.
“Why not,” Taylor replied.
“You’ve been such a bitch with all your comments over these last few months. For some reason you can act all sweet for a night and everyone else accepts the new you, but not me. So I’m holding you responsible for all the shit you’ve said over the past little while,” Ashley informed her.
“I’ll scream,” Taylor warned.
“Weren’t you paying attention to the coach when she gave the tour? This will eventually be a music room for her husband so they sound proofed this place. No sounds leave this room bitch,” Ashley explained.
“What do you want from me,” Taylor asked.
“A night of fucking the living hell out of your rail-thin body,” Ashley stated blatantly. “If you copororate then I’ll go easier on you, but if you aren’t a submissive cunt then I’ll beat you until you are,” Ashley told her.
“I’ll tell everyone what you’ve done,” Taylor threatened.
“I’ll tell them you’re into kinky sex and can produce some of your conquests that can back me up. Any other threats,” Ashley laughed.
Momsen was quiet. She was screwed and she knew it. Ashley had her at her mercy and she was along for the ride.
“Fine, I’ll play along,” Taylor conceded.
WHACK WHACK WHACK
“Holy hell,” Taylor screamed after being whipped 3 times with the riding crop.
“I didn’t like how it took you so long to give in,” Ashley told her. “Look how red your tight little ass is already.”
“Okay okay I’m yours all night just please no more of that,” Momsen begged.
“We’ll see. Now I’m going to release one hand for you,” Ashley explained as she did so. “I’m going to squirt some lube on your asshole now I want you to finger yourself.”
“Go to hell,” Momsen shot back.
WHACK WHACK WHACK
“AHHH,” Taylor screamed.
“I said finger your ass. I won’t ask again. And be grateful I gave you oil to use,” Ashley ordered while yanking on her long blonde hair.
“Fine I’ll do it,” Momsen replied.
Reaching her skinny hand behind her back, Taylor gathered the lube that Ashley had left as a dollop in her ass crack. Pushing it further down onto her tight rosebud, Momsen rubbed it around before dipping a finger inside.
“Ugh,” Taylor grunted as her virgin asshole was penetrated for the first time.
“First timer I see,” Ashley smiled sadistically. “That’s it, increase the tempo blondie.”
Despite some pain for having entered her ass for the first time ever, after a while the pain subsided and it started to feel good. The emo girl was now pushing her entire finger up her backside with ease and was no longer grunting.
“Now a second finger,” Ashley ordered.
Taylor didn’t resist this time and did what her master ordered. She didn’t do it this willingly because the brunette told her so, but rather because she thought it would feel good. She was pleased to find that after her sphincter adjusted to the larger intrusion that she was back to receive pleasure from it.
Ashley let the skinny blonde drill into herself for a few minutes. For some reason she was really getting off on watching the bitchy teenager degrade herself.
“If you’re into ass all of a sudden, why don’t we broaden your horizons,” Ashley told her slave.
Before Taylor could ask what she meant, Ashley was in front of her face. The brunette grinned then turned around, bent over and backed her sweet ass into Taylor’s face. Momsen didn’t have to have a doctorate degree to know what Ashley intended for her to do. While still fingering her own asshole, the tall blonde stuck her tongue out and started licking the brunette’s rosebud.
“Don’t be shy, bitch, get right in there,” Ashley encouraged.
Curious as to the taste, Momsen did as her master told her. Sticking her tongue straight out, she wiggled it past Ashley’s sphincter and into her anus. Taylor was pleasantly surprised to find it tasted nothing like she had imagined and eagerly went about lapping Ashley’s inner walls.
With Taylor licking inside her ass and her own fingers thrusting in her pussy, Ashley was building a pretty big orgasm. It helped that the blonde was still penetrating herself as her moans caused her tongue to vibrate while in her hole. Finally Ashley pushed herself over the edge when thinking about how disgraced the normally tough talking Momsen was currently.
“OH BABY,” Ashley screamed while hitting her climax.
She felt her hand become soaked in her own juices as she came violently. Ashley brought her fingers up to her mouth but then decided it would be better to share with her slave.
“Open up,” Ashley ordered as she pushed her three fingers into Taylor’s mouth. “Suck them dry.”
“Please don’t do that,” Taylor begged once she finished sucking Ashley’s fingers off and the brunette threw her wrist back in the restraints. “I was so close.”
“You’re such an anal whore already!” Ashley mocked. “You almost came just by plowing your own asshole. Wow. Total slut.”
“Fuck you Ashley,” Taylor shot back.
“You dumb whore. Will you never learn,” Ashley provoked before smacking the crop down hard on the blonde’s extremely red ass.
Ashley disappeared out of the door for a minute before returning with a few more toys. Taylor did her best to crane her neck and see what was in store for her but the restraints were too much.
“I’ll behave from now on just more whipping,” Momsen pleaded.
“That all depends on you and your horrible attitude,” Ashley reasoned. “Now back to the fun.”
“What now,” Taylor asked.
“This is an anal plug. It’s pretty big but I think you can take it,” Ashley revealed.
“How big,” Momsen asked with a mixture of fear and wonder.
Ashley walked over to her head and showed the blonde the latest toy. It would only go about 6 inches up her rear but it was widest at the end, measuring easily 3 inches in diameter. Before Taylor could protest, the brunette shoved the tip on the plug into her mouth, preventing her complaints. Ashley kept pushing but no matter how much force she added, the restrained blonde couldn’t fit the massive girth between her lips.
“Now we don’t have to use lube with all the spit you put on this,” Ashley noted. “I’ll start slow with you baby. After all, this is a marathon, not a sprint.”
“No please! It’s way too big!” Taylor shrieked.
“Don’t worry Taylor. I have faith in you,” Ashley smirked. “And I grabbed this because I have a feeling your voice will really start to annoy me.”
Ashley picked up the ball gag she grabbed from her last visit to the toy table and placed it in the skinny girl’s mouth. She wrapped the strap around the back of her head so that no matter how hard she tried, the blonde wouldn’t be able to spit out the device.
With the butt plug glistening in spit, Ashley walked back around and placed the tip against Taylor’s rosebud. Giving it some force, the brunette forced the first 2 inches of the cone-shaped toy into the freshman’s tight asshole. Ashley felt the blonde’s hole clasp tighter at the point, which was at the same time Taylor whimpered.
“I won’t force it cutie. We have all night,” Ashley told her.
The brunette withdrew most of the toy before re-inserting it back into her anus to the same point. Momsen whimpered again but Ashley ignored it and continued to work the 2 inches into her ass while constantly increasing the pace. After each pass, the blonde’s hole would expand to the same point before not allowing the plastic toy to gain any further access.
“Look how big your asshole is now Taylor! I wish you could see it. No guy will ever want to fuck you back here because it’ll be just too loose. And have fun sitting for the next week,” Ashley continued to taunt the younger girl.
“Mmmph mmmmh,” Taylor grunted, the gag preventing her rage-fueled rant from being heard.
“That should loosen you up a bit,” Ashley said once her arm began to tire from the constant thrusting. “I’ll take the gag out now, but any yelling or swearing and I’ll turn your ass perma-red with wilts. Understand?”
Taylor took a minute to compose her emotions before nodding once in response to the older girl’s question. Ashley reached down and undid the device, allowing the lanky blonde to suck in some deep breaths after nearly 30 minutes of only having short inhalations.
“You know I’ve never used one of these but I’m pretty excited,” Ashley told the younger girl. “I imagine I just step into the harness then tighten the straps.”
“If you’re excited then you can imagine how happy I am for you,” Momsen commented.
“Was that sarcasm,” Ashley asked her while reaching for the whip.
“No no. Not at all,” Momsen backtracked.
“That’s what I thought. Now tell me you want this big fake cock in your ass,” Ashley told her.
“It’s too big,” Momsen reasoned. “It’ll rip me in half.”
“Oh don’t be so dramatic. It’ll be fun. $20 bucks says you’ll get off,” Ashley told the frightened girl. “I’ll use loads of lube and take it slow…at first.”
The blonde held firmly in the wooden guillotine took a big gulp as she saw Ashley disappear behind her. She heard the brunette squeeze out some liquid onto the tip of the dildo then felt the oily head rub around her rosebud. Her backdoor wasn’t nearly as tight as it was prior to tonight but she still doubted she could take much of the new toy Ashley was going to use.
“Just relax,” Ashley told her. “Breathe in…now out.”
“Ugh,” Taylor grunted once again as another plastic object was thrust into her bowels.
Much to the blonde-haired girl’s surprise, Ashley did as she promised and took it slow. Momsen had loosened up after the sadistic brunette attempted to ram her asshole with a massive butt plug, but Ashley was still going at a low tempo so Taylor didn’t feel excessive pain.
Ashley decided to work the fake cock in an inch at a time and give the taller girl a chance to adjust. After a few minutes though, Taylor was now taking the entire 9-inch dildo into her backdoor without a fuss. Pleased with the progress, the older girl increased the pace so now she was stroking the whole shaft in and out of her anus at a high speed.
“Ooh, ooh, aww,” Taylor moaned in pleasure.
“I fucking knew that you were an anal whore,” Ashley gloated when she noticed the freshman was getting off by anal sex.
“Please don’t stop this time,” Taylor begged. “This orgasm has been building for an hour now.”
“And what will you do for me,” Ashley asked while slowing down, letting Taylor know that she could stop at any moment.
“I’ll eat you out for the rest of the night and make you cum time and time again,” Momsen bargained.
“Deal. You can climax now,” Ashley told the girl before slamming the dildo back into her to the hilt.
“OH YES,” Taylor screamed in pleasure as her asshole was plowed into. “Rub my clit please.”
Ashley loved how Taylor used proper manners to ask for her to do something. The brunette complied with the lanky girl’s wish and used her one hand to get her off while the other hand grasped her hip and pulled back on to increase the force of the thrusts.
“I’m cumming,” Taylor wailed in bliss as she had her long awaited orgasm.
“Now the fun begins. Hope you had coffee tonight because it’s going to be a real long night blondie,” Ashley told the exhausted girl.
“Payback’s a bitch,” Taylor told herself. Those 3 words would be the only reason she makes it through the night but she promised herself she’d make Ashley Greene pay for this.
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Highland College - Season 1 Part 4