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Mandy's Sorority Initiation	By : TheChemist Category: G through L > Last Man Standing Views: 4772 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: I am not associated with the show Last Man Standing. I do not own the show or any of the characters including Mandy Baxter and Kyle. I make no money from this fictional story

Chapter List
- 1-Mandy/Kyle
- 1
"I can't believe I'm actually doing this," Mandy thought to herself.
Mandy had just started college only a few weeks ago and already she was faced with the hardest decision of her short life. Despite knowing the limitations of entering college with a boyfriend, the slutty brunette threw caution to the wind and enrolled with a serious partner, that being Kyle.
However, after only that short time frame, Mandy found herself in a pickle. Her time was being stretched thin between friends, Kyle, coursework and then pledging the biggest sorority on campus. It was originally her mother's idea, but she thought little of it until the popular group approached her, begging her to pledge.
Mandy, always wanting to be needed, not to mention craving to be on top of the social hierarchy, quickly consented. However, due to her love for Kyle, she refused to scorn him in order to enter the sisterhood of coeds so they had to accept her as is. She knew the sorority wouldn't be happy about it since they liked their members single in order to better mix with the group, but it was non-negotiable for the brunette.
After getting accepted to the sorority, Mnady found herself walking around campus between classes. As per usual she was hit on, this time by a junior who was a pretty big deal on the football team. Mandy flirted with him, even giving him a kiss on the cheek but it didn't go further than that before they parted. As she turned around, Mandy nearly ran right into the head of the sorority, who so happened to be looking for the middle Baxter child.
"Just the girl I was looking for," Jenna, the leader of the Sigma Pi Pi.
"Oh hey girl," Mandy said as they leaned in and kissed each other on the side. "What's up?"
"It's about your initiation. It's tonight," the bubbly blonde informed her pledge.
"Okay. Not much notice. I have a date with Kyle but I can cancel," Mandy replied.
"Negative. Okay here's what's going down. Bring that handsome man-child back to your room in the sorority house. I'll have cameras set up. Those techie nerds from the IV club will do it, any excuse to get into our house is good enough for them," Jenna told her.
"Easy enough," Mandy replied before shifting to a more concerned tone. "So go out on our date then bring him back and what, do it for the cameras? I've always wanted a sex tape."
"You're not getting off that easy. Oh, before I forget, I also want you to get a Brazilian wax. Bald...I like to see a nice hairless pussy when you're getting what's left of your brains humped out."
"Right, because a landing strip is so grotesque," she mused.
"And I already scored you a tiny Bluetooth from the IV club. Make sure it's in your ear the entire day and night," Jenna informed, passing the small device to the big-breasted girl.
"Any chance I can know my hazing," Mandy asked. "Keeping in mind I have a serious boyfriend in my life."
"Easy Mandy. I'm cruel but not sadistic. I'm gonna tell you things to do all night. Provided you follow my instructions to the letter then I'll only instruct you to do the dirty deeds with that hunk of meat you're seeing," the thin blonde explained.
"Deal. I'll get in touch with Kyle and make sure we are still good and be ready by later today. Say 2 hours with the salon appointment included," Mandy responded.
"Great. Call when you're ready. Where are you two going by the way?"
"Yes. A dinner date just at the Italian place near campus," Mandy answered.
With that Jenna grinned widely, a sight that made Mandy nervous. She had been friends with the short blonde since she first started college so she knew that the blonde had some dirty thoughts in mind when she smiled like that.
Without saying another word, Jenna left and allowed Mandy to finish her walk about campus, killing the hour before class. The curvy coed didn't know what to expect tonight but she had a great guess that a lot of sex would be on the cards.
* * *
Jenna had gone back to the sorority house to think of all types of devious things to do to her friend for her Sigma Pi Pi initiation. So wrapped up in her thoughts was she that Jenna didn't realized that she'd been planning for well over an hour. The only thing that snapped her out of her thoughts was the vibration of her phone.
"All done getting done everything you requested Master," the sweet voice in Jenna's earpiece spoke.
"Master? I like it. Let's keep that going," Jenna laughed. "Great. When's the boy getting you?"
"20 minutes. We're walking to the restaurant. He thought that we should take advantage of the lovely evening weather," Mandy told.
"Okay perfect. Make sure it's set for two-way transmission so that I can hear everything being said," the blonde dictated.
"It is, no worries," Mandy retorted.
"Then enjoy the date and stand by for my instructions slut," Jenna replied, setting the phone down for the mean time.
* * *
So far Jenna hadn't ordered Mandy Baxter to do anything yet. The small device in her ear, hidden nicely by her shiny brown locks did wonders to conceal it so that her boyfriend Kyle couldn't see it. They were already at the restaurant and were just finishing their meals when the blonde's voice was heard in her ear.
"Okay showtime Mandy. Reach down and unbuckle his pants. Don't take no for an answer," Jenna ordered.
"Mandy?! What are you doing," Kyle asked in surprised as her hand squirmed into his pants.
"Jerking you off sweetie," she replied as if it was the most normal thing in the world.
Mandy didn't know if he would be up for some public, albeit hidden sexual favors, as the long red-and-white tablecloth extended down the table and brushed the floor. However, his hand never pulled her arm away and she instantly felt him harden around her fingers.
Kyle had to concentrate as best he could while his girlfriend gave him a surprise handjob under the table at the popular restaurant. He didn't want his contorted face to give away anything sexual going on, even as Mandy slowly but firmly stroked him off.
"How's that arm feel? Getting pretty tired I bet since you can only stroke a few inches in his tight pants. Bet you it's burning and it's only been like 5 minutes," Jenna commented.
"Mmhmm," the middle Baxter daughter replied.
The slender blonde was 100% correct about her assessment of the situation. Since Mandy couldn't glide all the way down his shaft in long smooth motions, her handjob was jerky with short strides. This made it extremely taxing on her forearm muscles, though Kyle didn't seem to mind.
"Are you all done," the pretty waitress asked as she startled the pair.
"Not yet," Kyle replied in a rushed tone.
The waitress smiled at the handsome employee of Outdoor Man then walked away, leaving the couple to resume their hidden activities.
"Haha that was awesome. So exhilarating. It actually gave me a better idea too," Jenna said before explaining to Mandy what was to be done.
Mandy heard the directions spoken into her ear and couldn't believe what she was being asked to do. Demanded to do actually, and she was going to do it but it would require timing. She slowed her masturbation of her boyfriend to slow wrist motions, keeping him hard and pushing towards his orgasm just slower. As she was doing this she was thoroughly yet slyly looking around the smaller dining hall until finally her moment came.
Without warning to Kyle, Mandy quickly slid off her chair and onto the floor below. As if in one motion she was under the safety of the long tablecloth and out of view to everyone around. She knew for sure none of the waitresses saw her duck underneath and she was hoping that if any of the patrons saw then they would keep quiet about it.
"Mandy...what the hell," Kyle almost silently asked, directing his words under the table.
"Just sit and relax," Mandy said, pushing the tablecloth over his lap.
Now with freedom to his crotch, the horny sorority pledge moved his pants down to around his knees and slipped his meaty cock out through the hole in the boxers he wore. Being sure to keep her noises to a low, she opened her mouth and began to blow her boyfriend like she had done hundreds of times before, albeit this time as he sat in the middle of the crowded restaurant.
"Oh my God," Kyle groaned, trying to be as quiet as he could.
"You big whore. Sucking your boyfriend off in public like that," Jenna joked into Mandy's ear piece as she bobbed her beautiful face on his dick.
"Shut up Jenna," Mandy said, keeping her voice low.
"Oh shut up. You know this excites you to no end," the blonde retorted. "Plus Kyle will literally do anything for you after this little stunt."
As Mandy continued to push her lips up and down his thick shaft, she couldn't help but think that Jenna was right. She had given her caring boyfriend hundreds of blowjobs in the brief couple of months they had been dating for, but this one was definitely special.
"Your girlfriend didn't run out on you did she," the waitress asked in a flirty tone.
"Ha no she didn't. She just had some better place to be," Kyle answered.
"Yeah, that place being on her knees sucking some big fat cock," Jenna laughed into Mandy's ear.
"She's taking an awful risk leaving so a handsome guy alone like this," the woman said, stroking his shoulder.
Despite being out of view, Mandy could still hear everything being said on the other side of the tablecloth. Hearing another woman flirt with her man made her enraged, and Kyle was the one who was benefiting. It fueled Mandy to put all her energy and focus into her blowjob, making her bob quicker down onto his tool with his tip routinely hitting the back of her throat.
"I'm not certain on that. In fact I think she'll be around any moment now," Kyle said, straining to keep his face normal.
"I think that was a hint that he's gonna cum soon. Be a peach and swallow it like a proper lady," Jenna informed. "After all, that's what all Sigma Pi Pi girls do."
Mandy ignored her friend's constant commenting in her ear and focused back on the task at hand, chiefly doing her utmost to milk his cock. She was truly talented with her mouth, but when she combined her head bobbing with her hand, stroking the remainder of his tool not filling her mouth then she was damn near flawless. After another few moments of her relentless assault of his crotch, she could tell he was ready.
The fashion student slowed right down with her bobbing and held her head and neck in place so that only the head of his cock was on her tongue. In case he still needed some extra encouragement to give her his seed she used her hand to now stroke the entirety of his tool, a lengthy endeavor at that.
Her skill paid off and she felt the first squirt of cum land on her tongue, soaking into her taste buds. For the next handful of seconds he filled her waiting mouth with his hot, large load of baby batter. Given Jenna's earlier instructions, not to mention no place to spit it out, Mandy swallowed down his spunk in one big gulp, an action she always did after draining her boyfriend into her mouth anyway.
It was the first time in Kyle's life that he had cum and had to keep quiet, and it was proving to be a real challenge. As his balls started to drain into the waiting mouth of Mandy, he bit the inside of his lip to steel his expression. However he couldn't stop himself from slightly lifting up off his chair to push his cock a little deeper into his boss's daughter's mouth as she took his gooey treat.
"Anyway, are you all done with your plates," the waitress asked.
"Completely spent," he said with a dreamy expression.
The lady smiled oddly at him before she reached down and gathered up the place settings of both he and Mandy's. Once she had walked away, Kyle looked around the restaurant and waited until the bartender's gaze was taken up by checking the sport's scores behind him.
"Okay all clear," he said to beneath the table, tapping her on the head in case she couldn't hear.
With the agility of a mongoose, Mandy was off the floor and back onto her seat like nothing had happened. She took a sip of her pop to get the last lingering aftertaste of Kyle's salty spunk from her tongue before finally looking over at him with a wide grin.
"You are something else," he smiled in return.
"Let's go back to my place big boy," she said with a wink.
"But your parents in the room right next door...not that it has stopped us before," Kyle interjected.
"No silly, my room at the sorority," Mandy corrected.
Kyle called for the check then paid cash and left a tip before he and Mandy left the restaurant holding hands. It was only a short walk back to campus where Mandy had set up her room in the shared house to Jenna's specifics. However, right as they were walking into the residence building, Mandy heard Jenna's voice in her ear again.
"Now repeat after me," Jenna's voice said in the sexy coed's ear once again.
Mandy heard what her very blonde sorority supervisor said to her and her facial expression changed drastically. Kyle could also tell that his girlfriend of the last 6 months must be having a disturbed thought as her forehead creased noticeably around her eyebrows.
"I wan..."
"Everything okay," the caring man asked his date, not meaning to cut her off. "Sorry, go ahead."
Mandy took another moment to calm her tone before she mustered the courage to tell him what Jenna had instructed her. She hesitated still, her mouth opening and closing as she tripped over the words until she finally gained enough composure.
"I've been thinking a lot lately about a big cock," she said, flashing him a cheeky smile.
"Mine I'm presuming," he inserted a joke.
"Of course. And I really, really want it...in my ass," she blurted out.
"In your ass," Kyle repeated in a questioning tone, not believing his ears.
"That's right. I really want to get fucked by your huge prick," Mandy repeated.
"Are you kidding," he asked, more than a hint of excitement in his voice.
"No I'm 100% serious," the gorgeous Baxter girl said while staring him right in the eyes.
Mandy would be lying if she claimed not to be nervous about trying out anal sex for the first time in her life. She had many reservations, too many to list but one of her biggest concerns was the fact that, though she was curvy, she was still petite and Kyle's cock was so big. Even though she was very slim she still had quite a plump thick ass, but she was frightened to death that he'd still be too large that he wouldn't fit then would literally tear her apart.
What buoyed Mandy spirits, if only slightly, was the fact that Kyle was an extremely nice guy and very considerate, especially when it came to matters between the sheets. He was a great lover but never pushed her too far, always staying within her comfort zone, even though she had a rather large zone when it came to matters of sex.
Another positive that made the situation a little less scary was the fact that they had fooled around with ass play, albeit only to a small degree. Sometimes when they were having sex, Kyle would let a finger drift around back and rub her crinkled starfish, even slipping the digit inside to the first knuckle. This never hurt her, in fact it often facilitated a more intense orgasm when she eventually came.
They had just entered the building where she lived at with her fellow sorority girls and Kyle stopped in his stride. Mandy looked back at him, wondering what his answer would be. She had it moments later when he pulled her towards him, wrapping her petite frame in his large wingspan and kissed her passionately.
"Let's go to you room," he demanded.
The pair kissed as they clumsily made there way to the staircase, ascending the steps somehow. They didn't attract any attention since all the sisters knew to allow Mandy full roam of the house. The only break in their frenzied kissing was to allow Mandy to get her keys from her purse, unlock the door and enter her room.
The instant they were threw the door, Mandy pounced on her slightly older boyfriend, immediately pinning him to the wall. Mandy had to reach up with one of her arms in order to pull his head down towards her so that she could press her full lips against his and embrace him with a warm and passionate kiss again.
"Perfect, I have you on camera," Jenna told her watching the action on her computer.
As Mandy's tongue slipped back into his familiar warm mouth she could have cared less what her sorority sister was saying. Her eyes had misted over for her desire to be with her loving man and she wore an expression of lust across her face. She was ready and very willing to do anything with Kyle, including sodomy which Jenna had demanded.
"God you turn me on so much," she huffed, kissing his neck now.
"Would explain why you're so wet," Kyle told her as he snaked a hand under her dress and touched her naked and very wet folds. "Nice touch with the lack of panties."
"Well thank you," she grinned.
"I'll assume the thank you was directed at me," Jenna jested. "Make your way to the bed, ho."
"Turn around," the Outdoor Man employee instructed.
Mandy had to make a decision; listen to her sexual master or what her boyfriend wanted. The choice was made for her however, when she hesitated as the attractive man clutched her arms and gently spun her around so that her back was against his sturdy chest. Now behind the sexy girl with the wide bubble butt, Kyle bent forward just enough so that he could lightly kiss the side of Mandy's neck while he dipped a finger into her drenched twat.
"Mmmm," the coed moaned as shivers shot down her spine.
While still kissing her neck and fingering her sex with one hand, he slid his other large hand down over her chest. Of all her amazing physical features, her breasts were probably her best asset as they were large, perfectly rounded and without the merest suggestion of sagging. They were what got her the most attention since her body was relatively small, and she was constantly wearing shirts that showed off a healthy amount of ample cleavage.
He gave each of her firm boobs a hearty squeeze before his fingers traced behind her and found the zipper up under her flowing hair. first of her buttons on the front of her blazer. He made short work of undoing the zipper, taking it all the way down its track, which allowed for her light yellow dress to fall off her shoulders and down her arms.
"Alright it was sexy seeing him undress you but seriously go to the bed or I'll make you pay," Jenna condemned. "Like maybe you'll beg him to spank you...hard. Or maybe you'll feel inspired to take a fist inside you."
"The bed," she blurted out, almost panicked. "Let's go to my bed now.".
"Tell him to sit on the chair beside the bed."
Mandy continued to kiss her boyfriend, being cognitive of the fact that she needed to keep her long brown-colored hair over her ear to conceal the tiny device. They made their way to the bed but the middle Baxter girl stopped short of getting on the plush surface and instead turned to her right. Directing their bodies, Mandy backed Kyle up until he was close enough to the chair in the corner of her bedroom.
Mandy did as was instructed even when Kyle gave her a quizzical look. It was clear that the blowjob under the table at the restaurant was the warm-up and he didn't want to wait any longer to get to the main course. Mandy didn't leave him alone though, as she took a seat on his lap and kissed him while her busy hands undid his belt and pants for the second time in less than an hour.
"Masturbate for me...and him of course," Jenna demanded.
Kyle was going to ask what was up but Mandy brought her finger to his mouth to silence any inquiries. The fashion student backed up slowly while maintaining eye contact with him until she sat on the bed and dragged herself backwards until she was in the center.
Kyle didn't know what was going on but he wore a smile on his face the whole time. As Mandy got into position and settled herself, she spread her legs wide and gave her long-term boyfriend and Jenna via the cameras an unobstructed view of her bald pussy and bright pink lips.
"Like what you see," she asked him in a playful yet sexy tone.
"Mhmm," she heard in reply from both Kyle in front of her and the blonde in her ear.
"Good," she said before she brought two fingers into her mouth, sucking the digits then removing them to continue to talk. "Just sit and enjoy the show."
With the fingers now covered in her own spit, Mandy lowered her arm until her hand was directly in front of her beautiful snatch. Extending out her two fingers, the sexy coed dragged the digits through her pink folds from the bottom all the way to her sensitive clit, eliciting a loud moan from herself.
Mandy continued to rub herself and occasionally dug her two fingers deep within her twat. This move made the room fill with her moans but neither Kyle nor Jenna minded the extra noise. Finally she withdrew from her pussy and brought her fingers back into her mouth, simultaneously sucking her juices from the digits while adding more lubrication.
"Fuck you're really good at that," Kyle finally commented after another few minutes of watching his girlfriend play with herself.
"Practice makes perfect," Mandy moaned, eyes closed. "You have no idea how fun this is to play with."
"No but I know how hard it makes me to watch," he replied, eyes pointing to the large bulge in his undone pants.
"Rub your clit now," Jenna gasped, her own fingers pumping inside her own twat from only doors down.
Really putting on a show for both of them, Mandy listened to Jenna and used her free hand to reach down and rummage through her pink folds. She let out another loud groan as her fingers found her sensitive nub at the top of her slit, the feeling of electricity in the best way running through her whole body.
Kyle had no idea what had come over his girlfriend tonight, but he was thankful for the little show. She was currently pistoning two fingers into her clearly soaking wet twat, though the speed had decreased slightly once she found her clit and began frictioning over it.
"Let's up the ante again," Jenna breathed into her ear, giving Mandy the impression she was masturbating on her end of the radio as well.
Mandy paused briefly from her relentless assault of her clit to bring her other hand into the fray. Extending her middle and fourth finger and pressing them snugly together, the brunette wasted no time by inserting them as deep into her pussy as she could. Two fingers firmly in place, Mandy returned to Jenna's initial instructions by rubbing her sensitive nub once again.
"Gonna cum soon," Mandy shouted between moans. "Do you want me to cum?"
"Yes," both observed shouted back at her.
Mandy was grateful that Jenna had given her the go ahead because she was seconds away from cumming anyway. Now knowing that there wasn't going to be any consequences she could fully embrace her orgasm as it hit her like an ocean wave, washing over her entire body with a steady stream of endorphins flooding her brain.
The room was silent for the preceding moments after Mandy's extremely arousing solo show. Finally the fashion student began to stir from her supine position and propped herself up on her arms behind her as she faced her very turned-on boyfriend once again. Before she could speak though, Kyle beat her to it.
"So you still thinking about me filling up that tiny butt of yours," he asked.
"The first show went so well let's have you play with your other hole baby," Jenna told her pretty teammate.
Mandy smiled at Kyle and gave him a nod to answer his question. She moved before he could get up from his spot, giving him the impression she wasn't done performing for him. Lowering herself back onto the bed so she was firmly on her back, Mandy flexed her legs and widened them so that her knees were far apart and up towards her head.
"Great view," the tiny blonde told her.
"Wanna see me finger my ass," Mandy asked.
"Very much so," Kyle said, feeling his dick harden even more.
Mandy scooped both hands under her ass after sucking on several of her digits once again. She extended out her fingers as far as possible then gripped her round, plump ass to pull her cheeks apart, widening the gap while also slightly opening her extremely clenched backdoor.
"Do it," Jenna encouraged.
Mandy took a deep breath then brought her pointer finger to her arse. It was the first time she had ever touched her butthole like this and the sensation was weird. Even though the center was gaped somewhat the hole felt so crinkled like fingertips soaking in water.
Kyle watched on in anticipation as his girlfriend spread her cheeks and popped her finger into her own ass. She moaned in a tone that was almost surprise, which was accurate. Mandy was expecting the action to hurt but instead there was no pain and the sensation was interesting. She actually liked how her finger was getting so tightly squeezed by the smooth but powerful muscle of her sphincter.
Kyle saw her withdraw her finger fairly quickly after she had inserted it and figured she was done fingerblasting her own tush and so too was his chance of fucking the beautiful girl. However, she surprised him by rolling over to rummage into her drawer, withdraw a bottle of baby lotion and slather up her hands. This time she flipped onto all fours, spread her legs wide and her finger found it's way back into her lovely booty without hesitation.
"Holy shit Mandy, finger that ass," Jenna cheered.
"Awww...mhmmm....oohhh," Mandy moaned as her finger was worked in and out of her virgin hole.
"God that's sexy," Kyle said, practically drooling with a raging hard-on now.
Kyle continued to watch his girlfriend stick a finger in her amazing ass as he slowly started to undress. Mandy had helped him out already by undoing his pants so they slid off his legs and onto the ground fairly easily. He unbuttoned the top few buttons of his shirt then as quick as he could he lifted it over his head in order to miss as little of the show as possible.
"Oh my...it's so tight," Mandy cooed as a second finger was added, surprised by the lack of pain.
Finally Kyle couldn't wait any longer and needed to get in on the action. Already naked, he pounced up off of his seat and was behind her on the bed in the next instance. Her two fingers were already as deep into her caboose as they could physically go, but he withdrew slowly to leave her hole empty.
"So sexy," he groaned before leaning in.
Kyle bent at the waist and buried his face into her perfectly rounded, thick ass cheeks, the act tickling her due to his wispy facial hair. The whiskers no doubt scratched and tickled her sensitive skin but neither of them care, the only thing Kyle was focused on was sticking his tongue as far into her arse as he could.
"Well shit...go get some Kyley boy," the blonde commented, watching him expertly toss Mandy's salad. "Tell him this..."
"Oh shit baby...eat my ass," Mandy repeated.
Mandy didn't think the words sounded right coming from her mouth, but they seemed to encourage her man. She felt his grip on her thighs increase and it felt like his tongue was working even more force, driving into her taboo hole even deeper.
The fashion student never would have thought that getting your bum licked would be even remotely sexually fulfilling, but she was proven wrong. When Kyle's tongue pressed against the center of her hole and passed into her wettened passage with ease, she let out the loudest cry of pleasure that she had all night. Without even thinking, Mandy pushed away from the bed backwards to hump back against Kyle's invading tongue
Jenna was very much enjoying the show of Kyle with his hairy face buried between Mandy's perfectly smooth cheeks but she wanted to get to the main event. It was especially pleasing to see the asshole virgin actually pushing her thick booty back against him to get more tongue into her anal passage.
"Okay Mandy, I want you to repeat after me," Jenna started.
"Get that big fat cock in my tight virgin arsehole," the brunette demanded.
Mandy was disappointed when his tongue left her ass. To her surprise, she actually enjoyed someone's tongue being buried in her rectum and licking her inner walls. Hearing the bed creak snapped her out of her thought and made her realize why he had stopped eating out for butthole.
"You ready," he asked, standing behind her, his tip already brushing her rosebud.
When Mandy nodded, Kyle took a breath to steady himself. Never in his wildest dream did he ever think his date tonight would end with taking Mandy Baxter's anal virginity. Of course, ever since they first started dating, anything seemed possible, including going balls deep in the slutty girl's ass. In fact, he was surprised when he first found out that Mandy still had a virginity left, as it was well known around Denver how easy she was.
"Holy crap it's in," Mandy grunted as his head popped into her, realizing it wasn't so bad...yet.
"It feels so small," he groaned from above her.
"It's so fucking tight," she swore, as she was consumed in the pain that came with stretching her asshole around his giant cock as he got his entire tip inside.
"It'll get better, just relax," Kyle consoled.
"Ugghhh...awww," Mandy moaned as his tip slowly was worked into her virgin hole.
"See. I told you it wasn't that bad," Kyle said to her after a few minutes of pushing only his head into her rear and getting very positive groans as a result.
"Mmm...yeah...I like it," she admitted honestly with lust in her eyes as she looked back at him over her shoulder.
"How much do you like it," he asked, rubbing her folds slowly to help distract her.
"A lot...ahhh," she groaned. "Enough to let you go deeper in my bum."
"That's my girl you giant butt slut," Jenna laughed.
"Just go nice and slow," she told him. "And be sure to use loads of lube."
Listening to her instructions, the horny man took the bottle of oil that Mandy had used earlier, and poured a large dollop onto his shaft. As more of his cock was worked into her superior tush, the lube would be spread around the muscular ring and make it glide easier into her. Before tossing the bottle aside, he also dropped a good amount of the liquid into Mandy's ass crack and watched it drip over her asshole so that it too was greased.
Of course, he responded before gripping her lovely hips and pushing the next inch of his tool into her backside. It hurt a little bit but not nearly as much as Mandy had built it up in her head. It also helped greatly that Kyle seemed to be good at sodomy, a revelation that the UC Denver coed would be sure to probe him about later.
"Doing great Mandy," Kyle told her, frequently squirting more lube onto his cock and her ass, making it glisten.
Kyle kept a steady rhythm, never jabbing too much or going too fast. It was this constant pace that allowed him to keep pushing more of his shaft into her virgin booty without her complaining or yelping in pain. Within 5 minutes after the initial penetration into her bowels he was working over half his tool into her.
"Keep going...ugghhh...I want...ahhh....it all," Mandy begged.
"Your wish..."
"Oh my God," she shouted as she felt his hard abs against her bubbly butt, meaning she had taking his entire cock into her rectum. "I didn't think I could take the whole thing into my ass!"
"I had faith in you," Kyle told her.
"You actually like having a cock worked into your asshole," Jenna deduced. "You are such a little ho! You're gonna fit in great here...much like your boyfriend fits in great into her ass."
Delighted to hear that she was so into the anal sex, Kyle used his same tactic as before and pumped the length he already had in her for a while until she was really relaxed. Finally deciding now was the right time, he gave Mandy his entire tool by plowing forward until his hips slammed against her curvy ass cheeks.
"Oh shit," she groaned in a combination of pain and pleasure as he stayed balls deep in her tiny hole.
"You okay," he asked, concerned.
"Mhmm...I can take it," she answered with a sexy look back over her shoulder.
Kyle would have stopped if she wanted him to, but he was over the moon that she didn't ask that of him. Unhurriedly, the blonde-haired man pulled most of his shaft from her bowel before slowly working it back in. His hips touched her ass cheeks at a much lower speed then the last time he fully entered her ass, much to her liking.
"You like having a cock worked into your asshole," he asked, engaging her in dirty talk.
"Yeah I do. I'd like it more if you took the training wheels off and really gave me a proper fucking," she replied, catching him by surprise.
Pulling out almost completely, Kyle crashed his hips against her ass, causing it to ripple. It drew a sharp scream from her again, but when she looked back at him, her glance told him not to stop fucking her. Listening to her silent instructions, he did the same thing and smiled with glee as his dick disappeared within her asshole.
"Such a dirty slut. Only sluts take it in the bum," Jenna told her, demeaning her further.
"Then I guess I'm a filthy anal whore," she replied. "Now really fuck this big slut in her tight ass!"
Kyle was surprised by that commented as Mandy had gotten confused with who was talking to her, but he let it slide. The dirty talk promptly ended after that and the only noises filling the small room in the sorority house were moans and groans from the couple. Having cum earlier that night, Kyle was able to stroke hard and deep into his girlfriend's virgin ass without worry about cumming anytime soon, despite the overwhelming tightness.
"Help him out and fuck your own ass with his cock," Jenna said, the first time she spoke in her ear for a good 15 minutes.
Mandy had almost forgotten that she was wearing an earpiece with someone giving her instructions and video cameras recording her sodomy. Just like earlier when he was tossing her salad, Mandy dug her hands into the bedding on her mattress and straightened her arms. Gradually she pushed back against him in sync with his thrusting so that every time he pushed into her booty she was backing against him, taking him even deeper.
"Oh God that's so good," Kyle grunted.
"Sounds like someone is gonna cum again soon," Mandy noted the tell-tale tone in his last comment.
"Your fault," he groaned. "Such a tight ass."
And that's when Mandy realized something about herself; she too was growing closer to an orgasm. She had been so focused on Kyle, and Jenna that she was overlooking the feelings building up in her body. But now she was aware of her fueling orgasm, which surprised her. She was expecting the sodomy to hurt, or at best be neutral feeling, but never in a million years did she think she'd cum from it.
"Holy shit I think I'm cumming," Mandy shared via a screamed.
"You are such a massive anal slut, because only they can cum with a dick up their ass," Jenna chimed in.
"Cum for me baby. I'm not far behind either," Kyle expressed.
The pair continued to do what they were doing but with much greater urgency now that they knew the other was on the verge. Mandy dug her hands harder into the mattress as she continuously rocked back against Kyle's massive cock. To his credit, Kyle's thrusting became harder but still not too forceful, allowing Mandy to enjoy his drilling of her booty. which was aided by his fingers rubbing her clit, which had definitely sped up as well.
"Ughhhhh. I'm cummingggggg," she howled, as her super curvy body was rocked by an intense orgasm.
Kyle was happy she came when she did because he was in desperate need of release as well. He used every trick he had to delay his orgasm so that Mandy could ride her out for as long as she could, milking every last ounce of pleasure from her first time taking it in the ass.
"Fuck Mandy, I'm so close," Kyle groaned after fucking her booty for 30 straight minutes.
"Okay now I want you to say," Jenna's voice said into her ear, followed by a phrase that made Mandy blush. Hearing the pause Jenna spoke, "Say it Mandy. Night's almost over and you'll never have to do anything like this again."
Mandy snapped out of her post-cumming haze and resigned herself to the forgone conclusion and repeated Jenna's words. It was embarrassing and degrading and she only hoped that her boyfriend wouldn't look at her differently after the night was finally over.
"I want you to blow in my mouth," she said, repeating the first part. "I'm young, dumb and so thirsty for your cum!"
Jenna nearly laughed so hard she fell off her chair. She had thought of that line awhile back but never had a chance to use it at all. However, Mandy's initiation proved to be the perfect instant for that beauty of a line to be spoken.
Kyle didn't wait too long from exiting her booty after hearing the sluttiest line he could ever recall. He paused slightly to watch as her gaping hole slowly sealed back tight before walking around to get his dick towards her mouth. Mandy knew protesting wouldn't do her any good and her initiation was almost over so she parted her lips and accepted his cock which moments before had been in her asshole.
He couldn't believe that she was sucking the taste of her own asshole from his pole, but the act of degradation was really getting him aroused. Even more than that, she was surprised to find that she was actually missing the feeling of his dick filling up her rectum. But the surprises kept coming, as she found that she enjoyed the taste of her own ass, which made her ponder how fucked up she was.
"That's right, suck your own ass Mandy," Jenna cheered. "You're such a good butt slut."
Mandy's own thoughts and Jenna's running commentary were suddenly stopped as cum started to fill up her mouth. She no longer thought about how tasty her own ass was, instead she did her best to collect all his seed without spilling any. This load was smaller than earlier at the restaurant, but it was still a good mouthful that she was grateful to swallow down the hatch.
"Yum, yum yum," she said, licking her lips seductively.
"Oh my God," Kyle cursed, slumping back into the computer chair.
"Glad you enjoyed yourself big boy," she told him before sucking on his sensitive tip.
After a few minutes of them catching their breath, Kyle finally spoke. "So what did you think?"
"Let's see, I came like a freight train so I think I'm game to try it again," Mandy answered.
"Really," he said, trying to stroke his cock to life.
"Easy cowboy. I won't be able to walk right or sit down for a few days as it is, but in the near future we can revisit me being your butt-fucked girl," Mandy said with a grin.
"Ok good. Cumming twice so close together is going to put me out of commission for the night too," Kyle replied.
"Well how about we shower up and then maybe you tuck me in," Mandy asked in her sweetest tone.
"Of course my love," he answered.
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Mandy's Sorority Initiation