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Sexual Adventures in Beacon Hills	By : TheChemist Category: S through Z > Teen Wolf Views: 18746 -:- Recommendations : 1 -:- Currently Reading : 2
Disclaimer: I make no money from this. I don't own or have anything to do with Teen Wolf, especially the characters. See chapters for more detailed disclaimers

Chapter List
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Title: Sexual Adventures in Beacon Hills Part 4
Show: Teen Wolf
Author: The Chemist
Pairing: Allison/Lydia, Allison/Scott
Codes: MF, FF, Anal, Oral, Toys
Disclaimer: I make no money from this. I don't own or have anything to do with Teen Wolf, especially the characters Lydia Martin, Scott McCall, Stiles, Coach Finstock, Jackson, Derek Hale and Allison Argent
Summary: Allison really likes Scott, plus he’s coming over to study. Allison goes to Lydia for advice, who recommends giving the boy something special - her anal cherry. Allison has Lydia teach her about butt toys before showing her how some work

“Tell me you are free tonight,” Lydia Martin practically begged her best friend. “Because if you’re not, I’m stuck watching Hoosiers.”
“Ouch. Sorry but I have a study date,” Allison Argent smiled like only a teenager smitten with a boy could.
“Mmm so Scott’s coming over then,” the redhead stated, throwing a wink at the end.
“It’s just studying,” Allison argued.
“Studying with a boyfriend…alone in a house…is never just studying,” Lydia said. “Trust me. It’s like getting into a hot tub with a couple guys. You know you're getting DP’d and you have to accept that.”
“DP’d? What?”
“Double penetrated. One in the pink, one in the stink?” Lydia described, shocked her friend didn’t clue in. “When one of the guys puts his penis in your pussy while his friend shoves his up your butthole.”
“Oh my God, Lydia!” Allison shrieked in surprise. After all, the redhead was talking about the sluttiest sex act she’d ever heard about brazenly in the school’s busiest hallway. “You’ve done that?!”
“Well yeah. And so will you. Eventually,” the redhead stated with certainty. “I mean, you had your first group sex experience last week so you’re getting closer.”
“I don’t know about that,” Allison grimaced. “I haven't even, you know…” Allison started to say before leaning in close to the busty redhead and whispering in her ear. “...lost my anal virginity.”
“You haven’t taken a stiff one up the bum yet?” Lydia asked rather loudly, defeating the purpose of Allison’s whisper. “Well Scott is in for some leg work before getting into your backdoor.”
“What are you saying?”
“Come on Allison. You saw how excited Scott was seeing Jackson sodomize me last weekend. We both know he’s going to want to experience it for himself,” Lydia explained.
“Anal sex after one date?” Allison asked, still in shock.
“One date that ended in a freaking fourway!” Lydia retorted. “Don’t be a prude now. He’s a good guy. Give him the butt.”
“How do I…where do I…” Allison stammered, not knowing where to even start with asking for advice.
“You have lunch now, right?” Lydia asked, knowing the answer. “Good. Let’s go on a little field trip to my house.”
She was going to work on her genealogy assignment over lunch, but Lydia had the twinkle in her eye. The type that Allison had learnt meant that the redhead was not to be deterred. Rather than fight the current, the leggy brunette went with it. 10 minutes later, Lydia’s SUV pulled up in front of her empty house and the two teenagers made right for her bedroom
“Here. Come check these out,” Lydia offered.
Allison walked over to the drawer where the redhead was sorting through the contents and gasped in shock as she looked within.
“Oh my God, Lydia!”
“What? You haven’t seen sex toys before?” Lydia retorted in an unbothered tone.
“Yes. I mean, I know of…” Allison started to say before dropping her voice as if it was taboo. “...vibrators and um, dildos. But, these…wow!”
“Prude, much,” the redhead stated, though did so with a smile. “Okay so you know about the classic stuff. But how about stuff that will help with tonight…”
“If I go along with this crazy suggestion,” Allison reminded her friend.
“Please! You are here listening to me explain various butt toys and how to use them. You are clearly giving up that anal cherry to Scotty boy tonight. Unless you want Jackson to walk you through the endeavor. I can attest that he is a magnificent sodomizer. Or maybe I’m just great at taking it up the ass?” Lydia pondered.
“You are…” Allison looked through all the words she was thinking before arriving on the right one. “Special. But I think I’ll pass on the Jackson taking my anal virginity option. Now, when would you use something like this?”
Lydia watched as her friend lifted up a string that was a loop on one end and had round spheres spaced 2 inches apart. Each ball was roughly an inch and a half wide and perfectly smooth. The whole rope and spheres were made out of some type of flexible material, either latex or plastic or something along those lines.
“Mmmm…my favorite. The anal beads,” Lydia gushed, her pussy dampening at the sight. “Beside it is a vibrating egg. Feels really fun. Of course, we have various flavors of lube along the back of the drawer. And, of course, butt plugs of all material and size.”
“This collection is so insane,” Allison gawked. “But I wouldn’t even know where to begin. In fact, this may have been a mistake.”
“That’s it. Pants off,” Lydia ordered as she shrugged out of her jacket. Looking over and only finding Allison standing in the same position with a shocked look on her face, Lydia issued another order. “I said get your pants off. As your best friend, it falls to me to introduce you to the world of anal pleasure.”
“Pleasure? From…back there?” Allison asked, her eyes darting down to her own booty.
“Oh yeah! Sure, it may sting at times, but the pleasure you can experience from some backdoor loving is Earth shaking,” Lydia disclosed. “The orgasms you can have are seriously next level. But to find that out…clothing off.”
Allison didn’t move for another few seconds, but both girls knew that the leggy girl was going to do it. With a final grimace, Allison made up her mind and did as she was told, first removing her leather bomber jacket. After giving an apprehensive look over at the redhead, who replied with a gesture telling Allison to get on with it, the leggy brunette grabbed the bottom of her tee and pulled it over her head. Rather than remove her B-cup bra and expose her perfectly perky tits, Allison undid her tight pants before pulling them down her long, model-esque legs.
“Oh my God! Why are you setting up a camcorder?!” Allison shrieked, noting as Lydia took great care to make sure the lens was focused on the center of her large bed.
“Recording this for Jackson, silly. He’d hate to miss out on the live action but a recording will be good enough,” Lydia answered as if it was the most obvious thing in the world.
“No! Absolutely not,” Allison replied, immediately looking for the clothing she’d already removed.
“Well don’t be shy now,” Lydia retorted, growing serious. “After all, you’ve already fucked my boyfriend so why wouldn’t you let him watch this little display. I’ll make sure he doesn’t keep it. In fact, I’ll destroy it afterwards. Now, do you want my help or are you going to risk having anal sex for the first time with no preparation?”
Once more, Allison deliberated over the decision for several seconds, but the answer was never in doubt. With a massive sigh, Allison reached back behind herself and unhooked her bra, releasing her incredible pert set of breasts. Even though she saw them during their foursome last week with each other’s boyfriends, Lydia was still impressed. After all, Allison had the figure of a runaway model, lean and slender, and yet had a bubbly ass and medium sized tits. Quite the package, indeed!
After stepping out of her yellow panties, Allison stood completely exposed for her best friend to look her up and down, which she did but with surprising reserve. Lydia still gawked, but it was tamer then she expected of the horny bi-sexual. The redhead was looking her over completely though, observing Allison's amazing body from mere feet away, noting her completely shaven pussy, tight slender waist, and pokey pink nipples at the peak of each of her perfectly rounded and sagless tits.
"Great, now get comfortable," Lydia ordered, pointing to the bed.
Allison listened and sat back on her bed, in a position that portrayed that the very naked 16 year old was not comfortable. Lydia fixed her with a glare and within seconds, Allison began to melt away her icy attitude by settling her head in the pillows and laying on her back, legs pressed tightly together as to not flash her friend her pinkness.
"Ok so what now," Allison asked, awkwardly trying her best to not use her arms to cover her pokey nipples situated atop her medium-sized boobs.
"You should throw your feet on the bed and spread those long legs while I get the first of our little friends ready," the other girl replied.
“I can’t believe I’m doing this,” Allison muttered, and yet made no movement to leave.
“First, you need to relax a little bit,” Lydia said, returning from her drawer of anal toys.
The ginger princess sat at the edge of the mattress, within arm’s reach so she could take Allison’s chin between her thumb and finger. With being both firm and gentle at the same time, Lydia guided her face towards her own. Allison gave her lips a lick to wet them before the redhead pressed her mouth to hers as they kissed for the first time. They both allowed themselves to relax into the kiss, their passions building as their tongues danced in the interspace between their lips.
Breaking the kiss, Allison fixed her friend with a long stare as Lydia’s hand went between the brunette’s legs but instead of rubbing her snatch, Lydia went even lower until the pad of her middle finger could reach out and rub her crinkled starfish. To Allison’s credit, she didn’t flinch at all as Lydia began making small circles around her asshole, just holding her stare the entire time.
“That’s a good girl. Just relax and let momma take care of you,” Lydia teased and tempted.
“I…it’s just that…my butt’s so tiny,” Allison retorted, still apprehensive.
“You trust me, right? And you know I’ll be gentle. And I won’t go too crazy. Look, how about just a finger? Look how small it is,” Lydia said as she showed Allison her thumb.
After a bit of thinking and a whole lot of teasing circles around the rim of her anus, Allison finally answered, “Okay but just a finger.”
“Just a finger,” Lydia nodded, her piercing green eyes having an almost hypnotic quality.
Despite her relenting, the redhead could tell that Allison was concerned, but how could Lydia still not be excited that her leggy friend had finally said yes? Needing to make sure she kept things moving along before Allison got too nervous about the arrangement, Lydia got her quickly set up on hands and knees with the ginger directly behind her plump, rounded ass.
Allison could hear the ginger wet her thumb, but Lydia had to be sure to transfer as much spit onto the digit as possible. The brunette couldn’t help but jump a little bit when she felt her palm contact the top of her ass. Lydia slowed down and just rested her hand there until noticing that the leggy girl had calmed herself. Slowly lowering her thumb downward, Lydia stopped when it was pressed against Allison’s tightly clamped butthole.
“Just be gentle,” she pleaded softly, looking back over her shoulder with her dark brown eyes.
Nodding in agreement, Lydia started to apply pressure. The redhead knew her friend was still rather tense, but the combination of her urges and her not backing out made the ginger press on until Lydia saw that the hole was starting to gradually expand. Keeping her interia going, Lydia continued until finally the first part of her thumb disappeared inside the brunette’s backdoor altogether.
“Ugghhh…awww,” Allison moaned as her friend’s thumb slowly was worked into her virgin hole.
“See. I told you it wasn’t that bad,” Lydia said to her after a few more moments of pushing the thick digit into her rear and getting very positive groans as a result. “In fact, I knew you’d like it.”
“Mmm…yeah…I…I like it,” she admitted honestly with lust in her eyes as she looked back at Lydia. More than her confirming words and sexy look, it was her wide smile that was so telling.
“How much do you like it,” Lydia asked, burying her thumb all the way into her asshole.
“A lot…ahhh,” she groaned.
“Enough to let me try something…similar,” Lydia proposed.
Lydia, of course, knew what the answer would be and thus was prepared. When she was over at the drawer last time, she’d returned with one of the objects Allison had originally asked about. Grabbing them from the corner of the bed, Lydia held up the red string of beads so that the leggy 16 year old could get a good look at them, then Lydia placed her thumb next to it as a size comparison. It was true that the beads were slightly larger, but not by a lot.
“Lydia! Beads already,” she continued to exclaim. “You want me to put these in her ass? Isn’t that, you know, rather advanced?”
“Who’s the expert here?” Lydia asked rhetorically.
Lydia wanted to put her friend more at ease so she actually handed her the toy that consisted of 4 spheres all connected by a string running through the center of each. Lydia wanted her to hold them and see how non-threatening they were, while also serving a purpose. While it was true Lydia really wanted to see them buried in her friend’s tight little ass, it would also loosen up her bowels for when Scott tried putting his larger dick in her later tonight.
“What should I do with them,” Allison asked after sizing them up.
“Just put them in your mouth, it’s really no bigger than her thumb,” Lydia retorted.
Even as Lydia was saying the words, she was grabbing the end Allison wasn’t holding and bringing it up to her face. Like the submissive girl she was, the leggy girl parted her lips and let the ginger place the ball onto her tongue before closing up again. Seeing the little grin on her mouth as she spat it out, Lydia asked if her friend could fit more than one inside.
Allison may not have been an anal-craving slut, but she was competitive and very playful. Seeing it as a fun little challenge, she took back control of the toy and surprised the ginger by fitting a ball on the inside of each cheek and a third on her tongue before closing her mouth. She decided to have some fun and slowly pulled them free, going slowly so Lydia and Jackson (when he was shown the video) could see her plump lips sexily slide over the surface of all three.
“See. It’s no big deal.” Lydia stated with confidence.
“Yeah well my mouth is a whole lot bigger than my butt,” Allison replied, slapping her ass to make her point. “You felt how tiny it was.”
“But the elasticity…”
“Just use lots of lube,” Allison cut her off, feeling good enough to try the beads out.
Lydia loved that the brunette was getting more confident as she rose from the bed and grabbed one of the many bottles of lube she owned. There were quite a few options but Lydia decided that her friend would appreciate something cherry flavored. Returning to the bed, the redhead saw that Allison was now laying on her side, legs pressed together and ass towards the camera. The sight of her naked toned booty and cute dimples on her low back were enough to make the ginger excited, but what made her jaw drop was the red string dangling on one cheek and the rest of the anal beads obviously hidden behind her sealed tight sphincter.
“Thought you wanted lube,” Lydia smirked at her.
“Once I tried, I found they went in surprisingly easy. Still can’t believe I’m doing this,” the fit 16 year old commented
Lydia didn’t put the bottle of lube away, instead she kept it close for the next stage. With both hands free, Lydia grabbed the string that was dangling out of her and held it firmly as her green eyes never left Allison’s ass…more specifically the brunette’s insanely tight asshole. How she managed to get all 4 balls in before Lydia got back was a mystery.
“Just go nice and slow,” Allison told the ginger.
“I’ll be gentle. You just pull your cheek apart,” Lydia urged.
Having taken more objects (toys, fingers, cocks, etc) up her ass then she could count, Lydia wasn’t surprised at how much effort it was taking to overcome Allison’s muscular ring especially with how slowly Lydia was going. Maintaining steady pressure backwards, Lydia switched her gaze between Allison’s asshole and face before the redhead saw her efforts rewarded. Allison’s face started to contort with her brows furrowing and her mouth gaping as her asshole did likewise and the faintest hint of a red ball could be seen inside her.
“Yes, yes baby. Almost out. Just relax now,” Lydia ordered.
Still pulling in a smooth motion, Lydia kept going and watched as her asshole continued to expand and more red came into view. The redhead noted the veins on the back of Allison’s hand stand out even more as the leggy girl pulled with greater force on her butt cheek, looking for any advantage in helping ease the strain on her anal ring. It helped as Allison’s sphincter opened to its new limit as a red sphere came popping out from her backdoor.
“Hhhh….ahhh,” Allison moaned as the first bead left her ass.
“That’s one,” Lydia celebrated, taking a break from pulling. “Ready for the next part?”
“Wow. Okay, not horrible. Yeah…ughhh…yeah,” she groaned as the next part was slowly withdrawn from inside her rectum.
Lydia hadn’t waited more than a heartbeat after Allison said yes and had pulled the second ball loose with less effort than the first while still being sure to be gentle. But as it came free of her backdoor, Lydia couldn’t help but smile in surprise since the leggy girl was clearly liking it as much as the redhead was.
“Here we go again,” Lydia warned before slowly starting to rear back on the string.
“You like that? You like watching it come back out of my ass you dirty, dirty girl,” Allison dirty-talked. “Awhhh…oh her God…ahhhh!”
This time Lydia went even slower, but only once the busty redhead saw the third red ball start to open her asshole. As she slowly expanded, Lydia practically crawled to a stop so that Allison could really feel the ginger opening her tightest of balls with the toy then held it steady as it reached its apex, gaping her more than an inch before pulling it out and watching her seal back up but less quickly this time.
“Last one,” Lydia said as she resumed pulling.
This time both girls were aware of what Lydia was playing at so as the busty ginger nearly stopped with the ball holding her anal ring as far open as it could go, Allison pulled back hard on her ass cheeks. The 4th and final sphere slipped out of her loosened sphincter and fell to the bed below.
Wanting to show Allison what she had just accomplished and to be proud of it, Lydia lifted the string of 4 anal beads up towards her face. Lydia was once more shocked by the model-esque new girl as she clutched her wrist and kept guiding her hand towards her face until she was close enough to take the first bead in her mouth. Like before, she ended up with 3 between her lips…3 anal beads…fresh from asshole…seconds before hand!
“I know you have more cool toys in your naughty drawer,” Allison remarked after spitting out the beads that had just been down her dirt road.
As a matter of fact, Lydia did spy a toy that would be perfect for the model-esque new girl before graduating her to Scott’s cock later tonight. Leaving the bed for only a moment, the busty girl returned and revealed a bubbly black dildo for Allison to see. It was roughly 6 inches long with each inch bigger than the first with it beginning the size of her thumb and bubbling larger as it went back until it was the size of an egg.
“Holy crap! That’s so big,” the brunette gawked, grabbing hold of it. “And heavy! You really think I can fit this?”
The fact that she asked the question instead of refusing like earlier was the only encouragement Lydia needed to hear. Lydia nodded and smiled wide as she went about comparing the anal beads to the dildo, the first rung of the toy being roughly the size of a sphere before getting larger and larger.
“See, about the same size,” Lydia added.
“Are you blind?” Allison was right of course, as even the first bubble of the dildo was bigger than the bead…which was bigger than her thumb.
“Don’t worry. I’ll use loads of lube,” Lydia suggested, already smearing the toy before rubbing a healthy dollop over her friend’s backdoor. “And you try with the dildo. You have complete control.”
“Well I guess I could try at least,” Allison said. “But there is no way I can fit all that in this ass.”
“Only one way to find out,” the busty ginger said.
Allison was already set back up on her hands and knees with her impressive chest resting on the bed and her booty way up in the air. Lydia loved the fact that her asshole glistened as the sunlight hit the copious amounts of lube on its surface.
“Okay…okay,” she said as she placed the rounded tip against the crinkled surface. “Just gonna go nice and slow.”
Allison started pushing as Lydia could see her forearm tense before transfixing back on her ass. Sure enough, the anal beads had loosened her up as it was only after seconds before her hole spread and the first bubble of the dildo disappeared inside her ass. To her shock, she didn’t just hold it in but instead slowly fucked her own ass with the initial tip of the toy.
“Ahhh….ohhhh…” Allison cooed.
“Keep going,” Lydia encouraged.
Allison was a smart girl and understood that momentum meant a lot so she kept the toy sawing slowly in and out. Lydia was so wet and found her hand between her juicy thighs, rubbing her own pussy as Allison’s asshole constantly widened and shrank until she got to the tapered end of the first bubble. Without breaking stride, the brunette tensed her forearm again and pushed until the second part disappeared in her ass as well.
“God! Uhhhh,” Allison screamed as she had over 2 inches of a thick toy buried in her virgin asshole.
“You’re doing amazing,” Lydia said as her free hand closed over the dildo. “Let me take it from here.”
The model-esque new girl had no issue giving up control as she released the toy into her stead and Lydia immediately continued her good work. Pushing with steady force, Lydia didn’t relent until a third bubble pushed into her friend’s behind, which was met with louder cries, but none were of pain. But as soon as it was in, she reached back and took control, apparently only needing the ginger to get over that last bump.
Lydia didn’t mind as she watched while Allison fucked herself with the new thicker inch in her ass. The leggy girl was nothing short of a sexual dynamo and Lydia couldn’t have been more pleased at this development. With a firm grip, Allison pulled the third bubble out, then the second before completely removing the toy and Lydia saw her asshole seal as tight as if nothing had ever been permitted inside.
“Is my bum still pretty,” the model-esque girl asked with a cheeky smile.
“Oh yes,” Lydia replied as she thrust the toy back in, easier than ever.
First one bubble then a second went inside without issue before backing out the toy completely once more. Apparently with new found anal confidence, Allison fucked herself with the first two bubbles before building speed and thrusting the third level inside next. Lydia was pleased as she watched the new girl in town fuck herself faster and faster while her hand rubbed her own dick with increasing speed.
“Oh my God,” Allison screamed as she pulled the dildo from her ass. “How far down did I go?”
“Right here,” Lydia said, pointing to the spot.
Allison’s face was of pure elation as her thumb moved along the groove of the third and fourth bubble. Without hesitation, the proud leggy girl stuck out her tongue and licked the portion of the toy that had been wedged in her own ass, starting at the third bubble and going to the top. At this point, Allison opened up wide and sucked clean the first portion of the toy for a few bobs before lowering herself further and doing the same to the dirty second and third parts as well.
“I’ve created a monster! Or at least another Beacon Hills butt slut, like myself,” Lydia beamed with pride. “Now, I don’t want to do too much today and risk making you sore.”
“You think I’m ready for tonight then?” Allison asked, some worry creeping back into her voice.
“Absolutely,” Lydia comforted her with the honest truth. “Now, I’m going to leave the biggest butt plug I have in your ass for the rest of the day. After all, I’ve seen Scott’s monster cock! Take it out right before you do the deed,” Lydia gave final explanations. “Other than that, you should be great. Good luck tonight, sweetie!”
“Can I, um, shower first before putting them in,” Allison asked sheepishly.
“Oh. Right. Of course. Right through there,” Lydia gave her friend a comforting smile.
* * *
“Well you made good time here,” Allison said as she parked her car in the driveway.
“I took a shortcut,” Scott replied as he leaned his bike against the wall of Allison’s house.
Scott felt awkward lying to his girlfriend, but his awkwardness could not compare with Allison’s right now. While Scott’s was all mental, Allison’s was for a different reason altogether. With each step she took, Allison could feel the butt plug that was roughly 2 inches deep in her rectum. It didn’t hurt, but it’s presence was noticeable, especially as the pair climbed the long staircase of her house.
“Upstairs?” Scott asked as they started to climb.
“Don’t worry. No one will be home for hours,” Allison replied, unable to hide a knowing smirk.
The pair didn’t quite sprint up the stairs and into her room, but it was a near thing. Scott hoped he wasn’t being too presumptuous when he closed the bedroom door behind him, but he was sure he’d find out soon enough. Allison was placing her textbooks down on her desk beside her laptop so Scott removed his jacket, placing both it and his backpack on the far side of the bed.
“So I was thinking we’d start with…”
Scott didn’t finish that sentence. After all, it was hard to speak when your girlfriend was pressing her lips against yours moments before her tongue invaded his mouth. After she got rid of the books in her arms, Allison had pulled off her fitted leather jacket before spinning her muscular boy around and attacking him with her mouth. The kiss continued for several more seconds until Scott pulled her down with him to the bed, having her slender body land on top of his muscular form.
“I like your idea better,” the teen wolf quipped.
“I always knew you were smart,” Allison grinned down at him.
Allison gave him a wide smile before going back in for round two. They're lips pressed against one another and the brunette brought her hands up to the sides of his head in order to run her fingers through his hair. They found their rhythm of kissing one another pretty quickly, as they both wanted each other so much. It took no time at all for them to transition from lip pressing to tongues sliding on and against each other as they battled for supremacy. Both of them were clearly into each other as they hungrily ate one another's face with little regard for how sloppy their kissing was getting. All that mattered to them was how badly they wanted to show the other how horny they were and sexy they found one another.
“Could kiss you all day,” Scott moaned, his hands roaming Allison’s slender body.
“And I’d let you,” the girl replied, noting how his hands had transferred down from rubbing her back to kneading her ass. “But what if I had more on my mind than just kissing?”
Scott had seen that look before in her large, mischievous eyes and knew that the brunette already had her mind made up. Not that Scott was going to talk her out of it, so instead he just smiled back at her and went back in for more kissing. Their mouths parted the instant their lips smacked together and they went at it with each other with a renewed ferocity.
Wrapping one of his arms around her back, Scott rolled her onto her back atop her plush bed. Though Allison wanted him to find the little present she had waiting in her asshole for him, she decided she could wait a little longer. Now fully horizontal, the werewolf slid his hand from around her back and over her medium-sized boobs, giving each of the perky set a firm squeeze. Allison was intrigued why his groping didn't last longer but she received her answer when his hand kept travelling further south until his fingers clutched the hem of her dress. He peeled it back slowly at first so that his hand dragged over her wet panties in front of her sex then hastened his pace to bring it over her chest and expose her boobs.
"Never tire at the sight of these," Scott commented.
Bringing his lips down he kissed her milky white skin above her flat stomach and slowly migrated up her lean body. The girl was a perfect mix of skinny with meat on her bones, clearly keeping herself in shape despite the demands of high school and a move less than a month ago. He didn't waste much time until his mouth had kissed it's way up her perky tits and was now hovering over her small erect nipple. Descending on it he took the bright pink cap into his mouth and sucked on it all while flicking it with his tongue.
"Mmmm....yes," Allison moaned loudly.
As Scott kissed down the side of her tit before ascending the next and sucking on her other nipple, Allison lifted her shoulders and head off the bed and finished removing her dress from her body. As he continued his adoration of her breasts, Allison deftly unhooked her bra before pulling it from her torso as well. Now, all the brunette had left on her tight body was a skimpy thong that she doubted would remain on her for much longer. Allison allowed herself to get lost in Scott's kissing and touching but as his hand started down her smooth stomach she was reminded of the purpose of tonight's activities.
"Your turn to lose some clothing," the topless girl said to him.
With his help, Allison flipped him over onto his back with his head in the middle of the bed and his knees dangling off. While looking him dead in the eye she made short work of his shirt buttons to expose his abs. Ripped muscles layer upon even more muscle had Allison get wetter between her legs and made her unable to suppress the urge to kiss his stomach. Before starting on his pants, Allison decided to reveal her surprise to him.
Scott figured that his girlfriend was going to remove his pants next, given the trajectory of their undressing thus far. However, she surprised him by turning around before backing herself onto the bed, kneeling on either side of his body so her bubbly ass was over his crotch. Allison could feel his fully erect cock grinding against her pussy through her thong and his jeans. She bent over and arched her back, rocking back and forth, causing her pussy to grind on his cock.
"Absolutely adore the view," Scott commented before adding in a little, playful spanking to each of her cheeks.
"Does this make it better?"
Now was the time for the reveal. As she stopped her dry humping on his crotch, Allison reached behind herself and pulled the thong out from the crack of her ass. Now, the jewel-encrusted butt plug finally made its appearance. The silver edge of the handle of the plug that nestled between her cheeks had a blue crystal-like rock in the center, which instantly drew his eye. Having seen enough porn, Scott could instantly identify what Allison had inside her ass, and the purpose it served.
“Whoa! Allison!” Scott gasped, his heart thundering in his chest.
Allison felt the boy grow excited beneath her as almost every muscle tensed. His excitement only grew as the dark-haired beauty did a seductive look back over her shoulder, a smile plastered on her beautiful face. The look on her face also encouraged him to explore, so he took up the invitation. Stretching out his fingers, he ran his tip tentatively around the circular base of the anal toy. Noting how her face still had the sexy smirk on it, Scott made a pinch grip with thumb and forefinger so he could lightly and carefully spin the toy. As the werewolf slowly spun the anal toy, the leggy girl couldn’t help but note how her rectum could feel the lubed up butt plug rotating painlessly inside her.
“Mmm,” Allison cooed.
When Allison opened her mouth in a small moan, Scott gained more confidence and moved the toy in and out. It was only by fraction of inches so only the stem of the butt plug was moving between her anal ring, but he tested the waters a little more by pulling back a little harder, testing out her sphincter's resistance. He didn’t push too hard, but the werewolf did notice a slight widening around her sphincter, and more of the silvery toy beneath.
“Well don’t be a tease,” Allison with a playful tone as he continued twirling and lightly pulling. "Go ahead and pull it out."
“You’re sure?” Scott asked, making sure she was comfortable.
“Well it would be hard to fuck my ass with a butt plug already occupying it,” Allison quipped with a naughty grin on her face.
It was only as Scott's fingers closed tightly around the jeweled base and began pulling it out of her ass that Allison felt the swell of discomfort return. Luckily for Lydia’s work early, Allison knew to expect this and knew it would pass. The butt plug was only an inch wide at its widest portion but it was having a tough time being wanked free from her. However, the werewolf was determined, not to mention had supernatural strength. After another few seconds, the plug exited her asshole faster and without any more pain.
“Plllppp,” the metallic toy being pulled from the wet confines of the slender beauty’s ass.
“This is the sexiest thing I’ve ever seen,” Scott commented as he used the butt plug to push in and out of her rectum in short bursts.
“Do me a favor and push it back in me,” Allison asked. “I want to keep it as loose as possible as I get you prepped.”
Scott couldn’t argue with that request at all. Once the tapered end of the toy was clear of her backdoor, he put it right back up against it. The werewolf smiled in appreciation as she pushed her backside back towards him to help the butt plug back into her ass. It was a little bit of a struggle but it went in with half the effort as the first time she performed the feat.
"Uhmm...mmhff," Allison groaned as the widest portion stretched her muscular ring before entering her rear.
Moving quickly like only teenagers can, Allison swung herself around and planted a kiss on Scott’s lips before pushing off him and the bed altogether. She stood for mere seconds, just long enough to push her last remaining article of clothing, her thong, off her body to render herself naked. Dropping to the ground, she knelt at the foot of her bed as she pulled his pants down. Not the first time seeing his monster cock, the brunette grabbed a hold of his lengthy 10-inch manhood in her fist and gave it a long lick up it's main vein on the underside all the way up to the tip. She used her tongue to give his small slit a few quick licks before popping his bulbous head into her mouth.
"Oh God," he moaned in response to her warm mouth.
Allison stuck to just bobbing her head on his purple-colored tip for a while to get them both warmed up before exhibiting more of her talents. Opening her jaw wider and using her lips to cover her teeth she ran them down his cock until he hit the back of her head, at which point she dragged back along his length to his tip again. The brunette worked this maneuver over and over again, gaining more speed and making more slurping noises each time until she was a blur between his legs.
"Oh yes, Allison! Suck my cock," Scott grunted.
Tucking the loose strands of her long brown hair behind her ears, Allison sank down lower onto her knees. While stroking his spit-covered dick with her fist, she angled his manhood upwards to give her better access to his sack. Opening her mouth wide again she popped the first testicle into her mouth and worked it around inside with her tongue. Satisfied with the job she did on thoroughly polishing his first nut, she swapped it out with his next one.
"God I love cock. Love how it feels on my tongue, how it tastes, when it jerks and pulses," Allison admitted honestly, using her hand to stroke the spit on his shaft.
Allison seemed to have thought her effort sucking his nuts was complete so after finishing applying a touch more suction she freed her mouth from his sack. Of course she wasn't going to just rest on her laurels and instead parted her lips again to take his tip back inside her wet oral cavity.
Scott stopped focusing on how close the talented cocksucker was pushing him to his climax and just tried to enjoy the situation. Reaching down, Scott bundled up her loose hair and held it on top of her head as she continuously bobbed into his lap. After producing some gurgling noises as she built up a relentless head of steam, Allison found her stride and slowed things down again so as to not push his endurance too far too soon.
"You have a gift," Scott commented.
Scott knew he was going to be having sex with Allison Argent, the prettiest girl in school. Not only did he know this, but it was going to be anal sex, taking her last of her virginities. Therefore, in his mind, the least he could do was deliver to her a great orgasm. She didn’t know much about anal sex, but he felt pretty certain that a 16 year old anal virgin wasn’t going to climax her first time, or ever from sodomy. Therefore, he wanted to take care of her first.
Lifting himself off of the bed, he got his feet back on the floor and helped the much smaller girl up off the ground. Instead of pulling her up on the bed to join him, Scott clutched her rounded hips and spun her around so her perfectly curved ass was facing him. Marching her forward a couple of steps they came to rest with Allison's thighs pressed against the wooden desk against the far wall. Instead of doing a big dramatic swipe of her arm to scatter the paper and books, Allison simply pushed them to the edge of the desk, allowing her tits and stomach to lay flat on the wooden surface.
The brunette felt her mound gush another wave of fluid when the werewolf pushed her down. Instead of his rock hard manhood, Scott surprised her by licking the length of her clean shaven pussy that sent a shiver up her spine. Once reaching her puffy sex he extended his tongue as deep inside her pussy that he could and elicited a loud moan of pleasure from the sexy leggy girl.
"Oh Scott," she screamed out.
Scott didn’t know how to work the butt plug into his oral feast, so instead he mostly ignored it. Instead, he focused on his tongue work, making sure to stimulate and get to know every part of her pussy. From her adorable little lips to her tight opening to the little nub at the top of snatch, Scott pleasured it all.
Scott felt like hardly any time had eclipse when he heard Allison’s moan increasing. Figuring her was on to something with what he was doing, he continued in the same vain. Using the fingers of one hand to splay open her pink lips, his tongue dug hungrily within her snatch. All the while, his free hand was flicking out at her exposed clit, which was rock hard under his fingertip.
“Close! Gonna cum soon,” Allison announced between moans. “Play with the plug.”
Never one to argue with her, Scott did as she instructed. His hand went from massaging her clit to clutching the base of the butt plug once more. Remembering what she liked the first time around, Scott did a combination of spinning and lightly pulling it out before letting it slam back into her anal cavity. Her hand had replaced his on her clit, so between her own fingers, the anal toy and the tongue deep in her pussy, the triple sensation proved too much of her in a short period.
"God, Scott...I'm cumming! UUGGHHH...AAWWHHH....YEESSS," the beautiful girl yelled. into her fortunately empty house.
Scott continued to orally please his girlfriend, though he slowly backed off. First, he stopped twirling the plug that was buried inches deep in her colon, keeping her anal ring stretched out. Next, he stopped burrowing his tongue so deep in her pussy, despite the extra sweet taste she produced when she came. Lastly, he pulled his mouth from her sex altogether, allowing Allison to straighten up.
“So…did you maybe want to…maybe, if you’re willing, to put it in my ass," Allison asked, pretty sure she knew what his answer would be.
“Would love nothing more,” Scott replied, beyond excited. After all, the boy had only lost his own virginity to Allison last week before they proceeded to have a freaking foursome with Lydia and Jackson. And now, a week later, he was about to take Allison’s anal cherry!
"After that massive orgasm I just got from you, I'm as relaxed as I'll ever be so now's the time," she said with a slight nervousness in her voice.
Allison had spent the rest of her free time between her lunch-time anal practice session with Lydia to research sodomy. Specifically, the new girl in town looked up how to perform safe practices and ways to make it easier on the woman. A lot of it was about the proper positioning, which apparently was doggy style, hence why Allison crawled onto the bed and remained on all fours. Reaching over to her nightstand, she pulled from the drawer a bottle of lubricant, a gift from Lydia, which was also a big must before being sodomized. Passing the bottle back to him, Scott knew what to do. First, he smeared a generous amount of the slippery liquid on his own cock, making it shimmer in the sunlight coming in from the window. Next was to remove the butt plug from Allison’s ass before placing it down carefully on the edge of the bed, at which time he squirted a healthy amount of the slippery fluid directly into her asshole, which had remained with a decent-sized gape in it.
"You’re sure about this?" Scott asked, clearly hoping she hadn’t changed her mind, but nice enough to re-confirm her desires.
"Just be gentle Scott," Allison ordered. "It's my first time. But I’m happy I get to give you something so special."
"I’m happy to share this with you too," Scott assured her.
Allison was nervous, but she wasn't going to let herself back out at this point. Remembering all the advice she read or gained from the self-described butt slut Lydia Martin, the leggy girl took a deep, steadying breath before reaching behind her. With one of her bubbly cheeks in each of her dainty hands, the leggy girl pulled them apart to make the crack wider than ever. The position forced her to rest her upper body on the mattress with her head tilted to the side. It gave her the chance to look back at Scott who was staring at her ass with a sense of wonderment. She felt a wealth of emotion in her perfectly toned body, but the prevailing one was fear of the pain she had heard rumors that were associated with anal sex. She also felt very exposed in this position as her never-before-touched or seen asshole was now out in the open. However, that fear was soon banished from her brain as she remembered that this was Scott, and that he would never let any harm come to her...ever.
Seeing his beautiful girlfriend with her hands on her ass pulling her cheeks apart for him was causing his brain to work at a mile a minute.
"I’m ready, Scott. I want you to take my anal virginity," Allison instructed, breaking him out of his thoughts.
"How can I turn that down," Scott asked rhetorically.
Scott straightened back up on his knees behind the lovely leggy girl so that he once again towered over her. He grabbed his thick base in his hand and this time placed his tip at the entrance to her relaxed and lubricated anal ring. Allison still held her ass cheeks open for him which helped not only show him his target but gaped it as well. Scott placed his free hand on the small of her back to steady the brunette before pushing forward. Although she was tight as all hell, Scott managed to fit his head inside her rectum before her hole clinched down right at his crown.
"It's in," Scott told her, calming any anxiety or remaining fears she may have.
"Wow. That wasn't bad at all," Allison admitted then felt him start pushing more in slowly. "Just be gentle at first," she groaned as he continued making short thrusts into her ass.
Scott did what she had asked and stopped his forward progress. Even though he didn’t have any experience with sodomy, Scott understood that anal sex was a delicate act requiring patience and a deft touch. Continuing to do slow albeit steady thrusts since those were non-threatening for her, and soon he felt a shift in his girlfriend.
Allowing herself another couple of seconds to adjust to his mammoth size, Allison took one last deep breath. The brunette took her hands away from pulling her cheeks apart so that she could dig them into the bed and push her little body backwards. Slowly she could feel Scott's cock passing into her rectum until she stopped, looked over her shoulder and gave the werewolf a confirming nod. Scott knew exactly what it meant so he grabbed her hips for stability and gently rocked his hips into her.
"This bastard better understand how much I love him," Allison thought as his thick cock inched into her bowels.
It was a slow and uncomfortable process but they gradually made progress. Scott felt like he had pumped into Allison's ass about a hundred times, which was probably an understatement, yet had only pushed maybe an inch or two into her. The brunette's asshole was like a clamp and as best as she tried to relax Allison was having trouble pushing the mild pain out of her consciousness.
"Holy shit! This is the tightest thing I've ever felt," Scott grunted with the first third of his cock inside her asshole.
"Yup...feels tight on my end too," Allison groaned in response.
Scott was ecstatic with getting the opportunity to sodomize the hottest girl he'd ever known, but he didn’t like the fact that she was still struggling a little bit. Therefore, Scott pulled a hand down from her hips and placed it in her wet folds. He extended his middle finger and began rubbing her clit and immediately he could feel the leggy girl start to calm herself.
"That's much better," Scott thought then gave her ass a light spank in celebration.
"Oh...oh shit...just like that," Allison confirmed via a scream, loving the feel of her clit played with.
Allison realized that with the pleasurable effect of her clit being stimulated that her asshole had seemed to finally relax. The next time Scott did one of his baby thrusts they found that a whole inch passed anew into her rectum with ease. The werewolf was so excited that he pulled back out so only his tip remained inside her hole then pressed into her. This time 5 inches cleared her sphincter before it reflexively tightened. Both parties were excited by the recent development as Scott was now able to stroke almost his entire length past her anal ring while the pain and discomfort vanished for Allison. In fact, it was getting to the point where it was actually feeling good to have him stretching out her tightest of holes.
"Oh Scott! Yes! Fuck me," Allison cooed lightly.
"Whadda say," Scott asked, certain that he didn't hear what he actually thought he did.
"Fuck my ass Scott! It feels so good having you pump that fat cock in my butthole," the horny brunette stated loudly.
Scott could only smile wider than ever before in his life. With that knowledge in tow, Scott seemed to double his efforts in sawing into the leggy girl's asshole. As he did so, Allison was aware that she was getting fucked with his entire length as she looked over her shoulder and between her heart-shaped booty. It was a surreal feeling, the naughtiness of being ass fucked when she was a good girl catapulting the feeling of arousal to a new level.
It did hurt a little bit, more than vaginal sex but it also had a more visceral, more intense pleasure derived from the dirty act as well. She could only describe the discomfort as the pain someone felt while working out. You knew it was necessary which made it feel like a good pain, not a damaging soreness.
"Awh! That's so deep...in my asshole," Allison moaned, completely surprised by how good it was feeling.
"You love it, don't you," he asked knowingly, feeling his balls tapping her very wet pussy with each thrust.
Allison could only nod her head and giving him her best pleading eyes, truly portraying how much of an anal whore she had become in such a short amount of time. The combination of Lydia’s expertise, the anal toys preparing her and the huge orgasm she had right before getting sodomized all added up. They both didn't know she had it in her, to take such a hard ass-fucking on her first attempt all while moaning and smiling.
"Oh my gosh...oh my gosh...fuck," she squealed as he began fucking her at his top speed.
At a pace that surprised both of them, the boy was flying into her hole with such speed that he knew he couldn't keep up for long. However, Scott knew his orgasm was coming too fast, faster than he could stop even if he wanted to. Therefore, he pushed the fatiguing muscles out of his mind and concentrated solely on savoring the last few moments of occupying Allison Argent’s rectum.
"Need...to...cum," Scott grunted while still plowing his entire length past her anal ring. "Where?"
"Inside me. Cum in my ass, big boy," Allison replied, close to her own orgasm as well.
Scott didn't know if it was Allison demanding him to shoot his load in her ass or if it was her spectacularly shaped ass slapping him in his stomach for the first time since entering her bowels, but it was the catalyst for his orgasm. Rearing back his hips one last time, Scott sprang forward and buried his entire length in the girl's asshole. The brunette was impaled fully by his dick one last time before she felt him begin to palpably spasm against her inner walls. Him rubbing her clit with his finger in combination with the sensation of his warm cum spewing out into her surprisingly receptive colon triggered her second orgasm of the night.
Both of their grunts and screams filled the room as they came simultaneously. Allison felt three thick blasts of cum coat her anal walls while Scott nearly had a second orgasm when her anal ring clamped down mercilessly against his throbbing cock. When both their orgasms subsided in a few seconds both sets of their muscles gave out and they collapsed down onto the mattress with Allison sandwiched between the bed and Scott, who still was impaled fully in her ass. After a minute she felt his member begin to soften which triggered Scott to roll off of the smaller girl and back onto his feet.
"Allison...wow," was all Scott could think to say.
"You were pretty wow yourself," she responded with her irresistible smile donning her face.
"Did I actually make you cum while I gave it to you in the ass," Scott asked.
"Big time," she replied, equally as astonished as he was.
Before they could say anything else, Allison heard her front door open up before a conversation between her dad and aunt could just be heard.
“Shit,” the young couple said at the same time.
“You need to hide!” Allison added as they quickly tracked down all their clothing.
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Sexual Adventures in Beacon Hills