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The Man Who Has Everything	By : TheChemist Category: 1 through F > Community Views: 6768 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: I make no money from this story. I have no ownership or association with Community or any of the characters, especially Annie, Pierce, and Britta

Chapter List
- 1-Annie/Jeff
- 1
"Hey Annie," Britta Perry said as she entered the study room and found only one member of the Greendale 7 gang.
"Hi Britta," Annie Edison replied in a much less chipper voice than normal.
"What's wrong? I figured you'd be on cloud nine since your type A personality had been running wild planning your boyfriend's birthday party," the blonde commented.
"Normally yes, but I'm really having trouble thinking of a present to get Jeff," Annie replied, referring to the man she'd been dating for a few months now. "I mean, what do you get the man who has everything," Annie mused, slumping back in her seat defeated.
"An actual law degree," Britta joked, drawing a laugh from herself and a scowl from her friend.
"I'm serious Britta. I'm usually really, really good at gift giving but Jeff is..."
"He's Jeff. Enough said," Britta finished for her. "Listen, I've been reading for psychology class and they explained that gifts that are experienced-based are more well received than materialistic ones. So maybe there's something along those lines."
This wasn't exactly a new fact for Annie to comprehend. She had known about this for a few years, the only problem is that she had tried racking her brain for something fun that she and Jeff could do together. He was the man's man type, which meant that there wasn't a lot of boyfriend-girlfriend activities that he would enjoy doing.
After Annie shared this with Britta, the blonde sat back and tried to think. After a short time, the begins of an idea hit her, the only problem was that it was a very un-Annie solution. However, the brainy girl was desperate so she may just go for it. "How do you feel about sex?"
"I get that I'm younger than you and Jeff, but we've been having sex," Annie replied, though he showed some naivety by first looking around to make sure there was no eavesdroppers before saying the word sex.
"Okay good because this idea wouldn't work with a sexually immature girl, only for a woman who was..." Britta started before Annie cut her off. "Okay I'm in! Tell me! Tell me!"
Britta smiled, knowing that Annie was hooked now. In truth, the blonde was having trouble thinking of something to get Jeff for his birthday, but convincing Annie to follow through with her plan would solve both women's gift dilemma. And even better for Britta, the present wouldn't cost her a thing...
* * *
Roughly 24 hours later meant that it was now Saturday afternoon and no classes at Greendale Community College. It also meant that it was now Jeff's birthday, which was why Annie Edison was in her boyfriend's kitchen, lighting the candles on top of the small cake she had made for him. They had a few hours before Jeff's birthday party started in full with the usual gang, meaning Annie had him all to herself.
Annie walked somewhat awkwardly over towards the dining room table where Jeff sat with his phone in his hand, scrolling through as he read something. However, as his gorgeous and much younger girlfriend came into view he looked up and noticed the cake in her hand, and a gift bag hanging from her wrist.
"Happy birthday Jeff," Annie said, placing the single layer cake down in front of her boyfriend.
"Awwh, thanks Annie," the older man replied.
"Make a wish," Annie exclaimed excitedly.
Jeff knew better to argue with his girlfriend when she was in such a good mood, even if it meant he had to play along with her childish games. Pondering for a moment, the former lawyer tapped a finger to his chin in thought. Finally he came to a conclusion before bending down and blowing out the candles decorating the cake.
"Wanna know what I wished for?" Jeff asked.
"What?! No! You can't tell me or else it won't come true," Annie corrected him.
"Really? So you mean you don't want to know my deepest, most secretive desire," the tall, dark and handsome man questioned.
"Ugh! Of course I do. Okay, one clue," the younger girl allowed.
Jeff smiled up at her before gesturing for the gorgeous 20-year-old to come a little closer. As Annie bent down, Jeff was once more reminded about how much he loved that Annie loved wearing low-cut sundresses, like the one she was in now, as it meant that her wonderful cleavage was frequently displayed. As the brunette with the large tits bent towards him, Jeff ran his finger over the cake to gather icing before bringing his hand towards Annie face and smearing the white frosting on her tongue. As Jeff began pulling his finger from inside her mouth, Annie closed her lips around his digit and began lightly sucking, mimicking a blowjob.
"Why don't we go upstairs and spend some time with Jeff Jr before everyone gets here," Jeff suggested, leaning in and giving Annie a kiss right on the lips.
"Yeah? You want to have sex with me," Annie asked, immediately met with a nod and his hand coming up to squeeze her sizeable right breast. "One second, I have a present for you that I think you'll love."
Jeff released his grip on her chest reluctantly and watched as Annie scampered off into the kitchen once more, returning a moment later with a small gift bag in her possession. He noted once again how oddly the brunette was walking but banished the thought as the gift was handed to him.
Intrigued as to what Annie got him, Jeff took the bag and started to pull out the colored tissue paper until his hand found something solid...and phallic-shaped. Pulling it out, Jeff stared wide-eyed at an 8 inch pink colored dildo of about 1 or 1.5 inch in girth. He flashed his eyes up to Annie's, whose facial expression portrayed for him to keep going. Next was a somewhat fixed string of beads, starting off with ones that were tiny before the gradually increased in diameter, ending roughly 12 inches in length and about an inch in diameter.
"Annie...what? How...and what," Jeff asked, completely and utterly shocked.
"There not for you. Not in the traditional sense. They are more the physical manifestation of the gift. A means to an end, one could say," Annie explained, though judging by the look on Jeff's face he didn't follow her thought train. "See."
The gorgeous brunette spun around and bent over, this time pushing her slender hips and bubbly butt back at Jeff. Reaching back behind her, the gorgeous girl flipped the bottom of her floral dress up onto her back so that her boyfriend could stare at her bottom. Though he normally preferred a wider backside, Annie made up for a slimmer profile with a surprisingly bubbly ass with smooth, porcelain skin. However, he would have had to been blind to not notice the inch-wide blue-studded butt plug right where her asshole should have been.
"Get upstairs...immediately!" Jeff roared in pure excitement.
As Annie let loose a squeal, verbalising her own joy, she turned and practically bound up the stairs taking two at a time, Jeff on her heels with the toys in hand.
A few heartbeats later and the pair were standing in his bedroom. Jeff had caught up with Annie and before she jumped onto his bed and got comfortable he grabbed her by the arm and held her. After sharing a passionate kiss, Jeff ordered the girl over a decade his junior to strip out of her clothes. Obviously Annie was prepared for their day to end in the bedroom which was why she didn't bother with either a bra or panties, meaning that as soon as she pulled her short dress up over her head she was completely nude.
To say that Annie Edison was an absolute vision while naked wouldn't be doing her justice. First off, the girl had a beautiful face with pristine clear skin and big green eyes. As the gaze lowered, she went from strength to strength with a set of tits that inspired a pet monkey to be named after them. Annie's boobs were frankly flawless, both in terms of their large, rounded size and the fact that their wasn't even the hint of any sagging.
"God! I'll never get tired of this sight," Jeff mused as Annie climbed onto the bed.
Settling on her hands and knees with her little booty facing Jeff at the bottom of the bed, she asked. "Would you care for the honors?"
"Actually, I prefer a show," Jeff answered, grabbing a reading chair from the corner of the room and bringing it to the edge of the bed to sit on.
Despite how sexually adventurous Annie was seeming right now, Jeff knew that the younger coed was venturing into unknown waters so he knew he had to help. Instructing her what to do and allowing her liberal mind to run with the idea, when Jeff asked her to remove the butt plug currently lodged in her bowels, she did just that.
Annie was obviously familiar with it having wedged it up her own ass, she rested her chest and face down on the lush sheets so both hands were available. As the brunette coed began pulling the metallic toy out of her backdoor, she listened to Jeff and used her free hand to rub her snatch as she tested her sphincter by slowly pulling back on the toy.
"Mhmm...awhhh," Annie cooed. When asked if she liked how it felt, Annie pushed the plug back past her sphincter and into her butt. "Ahhh...I really, really do!"
"Ready for something bigger," Jeff asked after Annie resumed pushing the bulbous toy in and out of her ass every few seconds.
As Annie placed her first butt plug onto the bed, Jeff rose from his seat with a matching plug in hand, only this one was nearly twice the size. The former lawyer never would have thought that Annie could take something so wide into her virgin ass, but as he began pushing it into her rectum he realized that the brainy girl had done her homework once again. Knowing she could fit the plug inside her, Jeff let the widest part of the bulb sit and hold open her backdoor, stretching it out likely to it's limit before applying a final pressure to let it be enveloped inside Annie.
"Ahh...yes!" Annie cooed before asking "Does it look cute?"
"Adorable," Jeff answered, adding a playful slap to one cheek before adding another to the other side.
Jeff had his girlfriend restart rubbing her pussy as he prepared to remove the wide butt plug that was actually bigger than his sizeable cock. With Annie's hand once again finding her clit, Jeff began tugging the toy out, bouncing it against her sphincter several times without enough force so that it simply poked against her exit. Moaning as he did so, Jeff finally pulled with sustained pressure, going slowly so that as more of the silver plug came free, it kept her asshole yawning open before it winked shut as the toy was removed fully.
"What else do we have," Annie mused, reaching over to the bag before pulling out the firm string of beads.
"Shall we see how far we can get it into you?" Jeff asked, handing Annie back the large bulbous plug.
"I bet I can get at least half," Annie said, rolling a bead that was roughly an inch wide and 6 inches away from the tip of the toy. "But since it's your birthday I'll try for more."
After the gorgeous coed embraced her naughty side and lubricated the toy by running her tongue up and down the pink beads, Annie placed the first bead at her entrance. Since the bridges between each round bead was solid, the toy a mix of dildo and anal beads. Also, since the beads at the tip of the toy were less than half an inch wide, the first two balls disappeared up Annie's ass with no resistance, drawing a girlish giggle of surprise as the brunette felt the tip tickle her inner rectal walls.
"Mmhmm!" Annie moaned as she pushed the toy forward, causing another pair of beads to enter her virgin asshole.
"Yes. Keep going," Jeff instructed, stroking his cock after removing all his clothes.
As the muscular man watched one, lightly stroking his cock from the chair at the foot of the bed, Annie repositioned her hand and pushed again. This time the beads entered one at a time and slower, but another 2 went inside her. At this point she had reached the segment of the anal beads she was predicting to fit in her booty, but the brunette showed no signs of slowing. Sure enough Annie kept going and pushed a ball larger than an inch past her sphincter and into her ass, leaving only 3 progressively wider beads left.
The brainy girl didn't even hesitate, only grabbing a better grip of the pink anal toy and continuing to push it further into her. With a bit of the lip and tensing of her arm muscles, Annie Edison successfully added another bead into her asshole, albeit with more effort. She kept going and got half the next bead into her asshole before it spilled backwards, however Annie wasn't to be conquered today. She pushed again and this time the bead fell the right way, giving her 9 of the 10 beads in her very full rectum.
"Only one left. Do it! You can do it," Jeff encouraged, his fist beating his cock harder.
Annie didn't know where this was coming from but with pressure against the back of the last bead, which measured well over an inch and a half in diameter, she crammed the final one in. She giggled and moaned in victory, surprising herself with how nice it felt to have her bowels spread and feeling full.
"Now pull them out. Nice and slow for me," Jeff continued to dictate.
At this point Annie was full and truly along for the ride. Holding the ring at the end of the toy in her hand, she followed her boyfriend's instructions and slowly pulled. Jeff watched and stroked his member as the widest of the beads stretched Annie's asshole deliciously until it popped out. They started coming faster and faster, Annie forgetting what Jeff had asked and going with what felt good, and that was having her bowels empty and rubbed along the way.
As the last ball popped out, Jeff instructed again, his hand a blur on his cock. "To your mouth. Suck on them."
Once again Annie reverted to her training and didn't think, only reacted. As the pink toy came fresh from her rectum and across her face, Annie ran the beads along her tongue before capturing the free end in her mouth. If it had tasted gross she surely would have stopped herself, however it was fine so she closed her lips on the first several beads and slowly sucked on them, moaning all the while as her asshole actually stayed gaping open.
"Fuck! Open up," Jeff bellowed, becoming a giant blur of motion.
With cock in hand Jeff straddled her as he walked on his knees up the bed. Hovering over Annie's pillowy chest he gave his cock a couple final tugs to push over the edge, with her anal show getting him 99% of the way to the best orgasm of his life. Aiming for her face the first spurt hit her cheek and sent a sticky rope along her cheekbone almost to her ear. The second jet hit Annie just above her adorable chin and splattered all around her mouth. By the third spurt of jizz Jeff had pushed his cock into her open mouth to finish draining his balls.
"Mmm...so much cum," Annie cooed, still surprised at the suddenness of his orgasm.
Jeff took another moment to gather his strength as he stayed straddling Annie's impressive chest. He would have preferred to stretch out the afternoon for hours, knowing it would end in anal sex with the gorgeous and sexually naive Annie Edison, but seeing her take anal beads that moments before had been lodged firmly up her ass then take it straight into her mouth with a moan was simply too much for the man to handle.
"I'll grab you a tissue," the satisfied yet slightly disappointed man said.
By the time Jeff had gotten off the bed, walked to the side table to grab a box of facial wipes and returned, Annie was no longer on his mattress. Instead the brunette who had shoveled most of the cum on her face into her mouth to swallow down had sunk to her knees on the tiled floor, kneeling before the well muscled man. He was about to protest, knowing that he was no longer a teen who could fuck right after cumming, but as soon as her lips closed around his sensitive, slowly deflating cock the words caught in his throat.
"Ahhhh...fuck," Jeff swore, looking down to observe the kneeling girl sucking his dick.
And just like that his cock began to swell. It likely helped that he hadn't gone complete soft, in fact it was a bit of a perfect storm as enough time eclipsed so his bulbous head was too sensitive but was long enough that a reset button for a boner was hit. Getting hard right after fucking was something he did in college, being able to bang a few times a night, but since entering his 30s it was something that was rarely achieved.
Though she wasn't nearly as experienced as the older man, Annie knew what was need and wasted no time at all, bending low and extending her tongue before licking Jeff from his full sack to the top of his cock. She looked him in the eye the whole time she did so, feeling his member harden so that after her second lick along his length he had grown to his full size.
"I think someone wants to play again," Annie stated with a playful smile, stroking his heavy manhood in her small fist.
Jeff's reply was a grunt of pure pleasure because Annie took that moment to open her mouth and swallow the first several inches of his cock once more. This time, Annie wasn't going to surface after a few seconds, instead she repeatedly bobbed her head to the top a moment later before descending back down, twisting her head so the swirl of her tongue could cover more of his sensitive shaft.
Blowjobs were an area that Annie had improved upon massively since beginning to date Jeff. The former lawyer had gotten across to the coed that oral sex was an important facet of sex, and she was very receptive to his coaching, which transformed Annie into one excellent cocksucker. Just as she was taught months ago, Annie kept her gaze up into Jeff's eyes as she devoured his cock with her mouth and proceeded to show her enthusiastic skill. Everything about her blowjob was erotic. The way she was now inhaling half of his manhood with each bob of her head, the way her cheeks hollowed slightly as she applied suction, and especially the noise she made as his spit-covered dick entered her mouth fully, making a wet gurgling sound.
"Oh God, Annie," the former lawyer cooed. "Suck that dick."
Annie smiled with her eyes but her demeanor remained all business. Showing her newly gained experience, the younger college girl switched up her technique, going to shorter bobs so that her lips were now only running over his tip and next inch down. Her speed had increased as well, a stark contrast to the slow, deep strokes she was taking only moments before.
Much like before, as soon as Jeff was getting use to one technique, Annie zigged a different direction. After her lick-down of his cock, the horny girl took him back in her mouth, taking him all the way into the orifice until he poked her throat. She gurgled and spat extra saliva onto his dick before bobbing back up and starting the process again.
"Definitely a great birthday" Jeff groaned as he held some of her silky hair out of her face.
"Glllkkk...kkllkkk," Annie choked as she tried to deep-throat him, ultimately failing as her nose remained an inch from his pubes. "Main event still to come honey."
"I need to fuck you, now!" Jeff demanded, looking down to see Annie drool some extra saliva on his cock before straightening up.
Just like with everything in life, Annie had done her research for Jeff's birthday surprise. For one, she knew she needed to prep her asshole for its maiden voyage, hence why she already had a butt plug spreading her backdoor out. Next was learning what to do when it was time and the two big things were lube and positioning which she took care immediately. Rolling over to get the bottle of lube from the bedside table, Annie applied a healthy dollop onto her palm before rubbing it around Jeff's member before settling onto her hands and knees and using the remainder of the fluid to rub on her loosened up asshole.
Jeff watched as Annie went through her preparations, but he only had the burning desire to be inside her as soon as possible. Therefore as Annie began applying the lube over her sphincter, he moved right up behind her and planted half his length right into her vacant pink folds. Holding her hips, within two more thrusts he was stroking his entire shaft into Annie's twat, which she had freshly shaved bald for him just this morning.
"Oh my God Jeff! Yes! Mhmm," Annie practically screamed.
Normally Jeff would have worked his way in solely with Annie, allowing her to get used to his size, but not tonight. For one, his dick was lubed up well so that he effortlessly glided into her snatch without issue. And for two, he didn't worry about making himself cum too soon as he was essentially numb in that department. Scientifically he had learnt that men had a refractory period of roughly 15-20 minutes between orgasms, so try as he might Jeff could fuck as hard as he wanted and there was no risk of popping his load.
It was for these occasions that Jeff thanked his lucky stars he had a mirror serving as his headboard as it allowed him to see the look of glee on Annie's face as he sawed into her with reckless abandon. Even better was the fact the mirror afforded him the view of Annie's large, heavy tits swaying back and forth, threatening to give the poor girl two black eyes from the amount of rocking they were under.
"Keep fingering your asshole," Jeff grunted, his own hands being used on her curvy hips to hold her steady while Annie was still in the process of lubing up her rear entrance for him.
"I'm...mhmmm...ready...awhh...birthday boy," Annie cooed, Jeff knowing exactly what she was referring to.
Annie couldn't help but find everything going better than planned, which left her feeling very optimistic about losing the last of her virginities. Thus far, the toys used to loose her ass up had performed admirably with little to no real pain. A little discomfort but even that passed quickly. And now, as Jeff thrust into her pussy at neck breaking speeds while she had 2 of her own fingers wedged deep in her ass to smear the lube, it felt very pleasing.
"You ready," Jeff asked, having pulled out of her pussy while guiding her hand backwards so his tip was now brushing her rosebud.
"Just be nice to it," she pleaded, feeling a ripple of worry.
He nodded then took a breath to steady himself. Never in his wildest dreams did Jeff think that his 35th birthday would end with taking the beautiful Annie Edison's anal virginity. However, in his mind he believed he deserved it. After all, he was going to Greendale Community College as redemption so ass-fucking this gorgeous coed with big tits was his reward. Sure, he cheated his way to becoming a lawyer and was only at Greendale to get back his lofty, well paying job, but that was semantics.
"AAWWWHHH YEESSSSSS," Annie screamed as his head popped into her backdoor.
"It feels so small," Jeff groaned from above her, forgetting how tight an asshole felt as the last one he fucked was nearly a year ago.
"I can take it," the coed insisted, wanting to soldier through since it was Jeff's birthday gift. "Just keep going."
Not surprisingly, Annie was being rewarded for her preparation with the adsense of pain and even the discomfort being minimal and short-lived. They had done a thorough job stretching out her elastic hole so that even though it didn't feel great, it was rapidly responding stretched her asshole around Jeff's truly giant cock.
Jeff normally would have started a lot slower but just from reading her body language he knew the the busty coed was ready for more. Not stopping at the tip, Jeff slid more of his lubed-up cock until he sensed her tighten up. He sat still for a moment and looked down to find that more than half his length was in Annie's ass!
"Good girl...taking that cock so well," the former lawyer congratulated as he began pulling his hips back.
Now knowing where her limit was, the birthday boy stayed within her asshole, constantly pushing in and out only half his length, no more. Jeff didn't go very fast but now wasn't the time for speed, it was time for Annie to get comfortable with anal sex. Deciding she was ready for more with her muscles losing tone and her moans slowly returning, Jeff grabbed her wrist and placed it between her legs and let her instincts take over.
Like Jeff expected, his girlfriend began to rub her clit and the rest of her folds which allowed Jeff to start actually fucking her. Now that she was more relaxed, Jeff opted for pace rather than trying to cram inside deeper, and was rewarded for his decision. Even though it was only 5 inches in Annie's butt, he was plowing her just as fast as he had done to her pussy minutes earlier.
"Uhh...awhh...you like your birthday present?" Annie asked him.
"You fucking bet I do," Jeff answered. "And you're doing so good. I'm already halfway in."
"I can take more. Give it all to me Jeff," Annie demanded greedily. "Stuff your whole cock in my tight ass!"
Delighted to hear that she was so into the anal sex, Jeff slowed his pace again to about half speed which allowed him to probe deeper. After every inch or so Jeff would speed up and stay at that depth for awhile before plunging down again. Finally deciding now was the right time, he gave Annie what she wanted and pushed the rest of his shaft into her until hips slammed against her curvy ass cheeks.
"Oh God," she groaned in a combination of pain and pleasure as he stayed pressed against her, his balls resting against her rounded tushy.
"You okay Annie?" Jeff asked after hearing her sharp yelp.
"I'm good. I can take it," she told him confidently.
Jeff would have stopped if she wanted, but he was over the moon that she didn't ask that. Unhurriedly, the former lawyer pulled most of his shaft from her bowels 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 Annie's pleasure.
"You like having a cock worked into your asshole," Jeff asked, engaging her in the dirty talk, something they normally didn't do.
"Yeah I do. I'd like it more if you stopped treating me like a little girl and actually fucked me," Annie replied, catching Jeff by surprise. However, after a moment of being stunned he shook it off knowing that when Annie committed to a project she devoted herself completely.
Giving them both what they wanted Jeff pulled out almost completely with only the head remaining to hold open her sphincter before he crashed his hips against her ass, causing it to ripple. It drew a sharp scream from Annie again, but when she looked back at him, her glance told not to stop fucking her. Listening to the horny coed's silent pleading, Jeff did the same thing and smiled with glee as his dick disappeared within her asshole.
Jeff was truly finding his stride now, though enough time had elapsed so he was feeling his endurance ebbing away. That being said, the former lawyer just seemed to tune everything out, including the burning feeling in his balls as it just felt like he could sodomize this large chested 20-year old all day and night. Jeff ran on animal instincts, slapping her ass, first the left cheek then the right all while looking down and watching as his entire dick would disappear then reappear every second or less.
"Such a dirty girl...ughh...taking it in the bum with a big smile." Jeff groaned, delivering another quick slap and lingering for a hearty grope of her cheek.
"Then I guess I'm a filthy anal whore," Annie replied, upping the ante both in terms of language and by tensing her arm muscles so she could propel herself backwards. "Now really fuck this big slut in her tight ass!"
"It won't be this tight ever again, not after I'm done with it," Jeff told her while slamming into her asshole again at a quicker speed.
"Yes! That's it! Fuck that ass! You know I fucking love it," Annie continued her encouragement, diving into her role as an anal loving nymphomaniac.
Jeff felt like a man reborn. Not since he was in his 20s, fucking while high on cocaine did he feel as free and energetic as he did with Annie today. It was likely the combination of cumming not long ago which gave him the confidence and ability to thrust as hard as he wanted without fear of jizzing too soon. However, the knowledge that he had successfully sexually corrupted the pure and innocent Annie Edison, transforming her into an anal-craving fiend heightened the experience to new levels as well.
There was simply no plausible way that any man could keep up with this blistering pace for very long. Jeff had been lucky that he had already cum not long ago, as that was the only thing that allowed him to fuck this hard and this fast. However, even his refractory period had its limit and this insane pace was about to break it. Of course, Annie was helping matters by using both arms to throw herself backwards, increasing the speed and power of each of his thrusts into her once virgin ass.
"Lay on your back," Annie demanded, as if sensing his desperation.
"Annie...I don't have much left," Jeff warned, feeling a second orgasm on the horizon.
"Then lay down quickly," the nerdy girl once more pushed.
Though they had only been together for a few months, they had been friends for a few years so Jeff knew that when Annie was in this type of mood it was best to do as she said. Therefore the muscular lawyer pulled out of Annie's asshole, only able to appreciate the massive gaping hole that led to darkness for only a heartbeat before flipping over to lay on his back.
Annie was on his in a blink of an eye. Despite the intense fucking for the past hour, the 20 year old apparently had boundless energy as she swung one leg over Jeff to straddle his waist before reaching back to guide his cock towards her ass once more. It didn't just slip right in, but his dick's passage into her backdoor was much easier this time, aided by gravity on her side.
"Mmm...guy could get use to this," Jeff grunted as his cock was instantly given the tightest, most sensual massage by Annie's asshole.
In truth, Annie didn't know what had overcome her but she just needed to have him inside her butt once more but with her doing the fucking. Just like when they were having sex in doggy style, Annie rode her boyfriend with speed and power, thundering her curvy body down before shooting back to the top of his wide manhood.
"And these tits," Jeff added through gritted teeth, using both hands to knead the bouncing globes in front of him.
Annie smirked at his remark, happy in the knowledge that the muscular man was as big of a fan of her glorious boobs as she was of them. The thought didn't distract her from continuing to bounce her small body up and down his rock hard dick, skewering herself in the ass each time she descended on his tool.
Jeff couldn't believe how extraordinary this woman was. She had the face of an innocent angel yet she was taking his dick in her ass with ease and loving every minute of it, if her chorus of moans were anything to go by anyway. Over and over she rose up only to swiftly fall back down his veiny member, eliciting primal grunts from them both.
"Almost...ughh...real soon," Jeff grunted through gritted teeth, trying to hold out for as long as he could.
"Cum for me, birthday boy!" Annie cooed, seemingly to thrust herself down even harder on his erection.
Jeff was going to get another birthday gift in the form of cumming inside Annie without a condom to collect his spunk. Though Annie was on birth control, she was still not okay with Jeff creaming in her pussy just to be on the safe side. However, today was different and he planned on taking advantage of every opportunity ass-fucking the 20-year old coed presented.
Finally Jeff couldn't take anymore. His orgasm was coming and wasn't going to be delayed, but he wanted to putting the icing on the cake, so to speak. Begrudgingly he took his mitts from pawing Annie's massive boobs and onto her hips so that he could lift her up and roll her onto her side without his cock coming free from her backdoor.
"Woooah!" Annie shrieked in surprise and excitement as she found Jeff thrusting into her ass harder than anything before, which was saying a lot.
Not worried about cumming too soon or having to pull out, Jeff checked all reservations and simply opened the throttle fully. He was a blur of motion as she stroked hard and fast into his girlfriend's bubbly ass, hoping she could handle the intense fucking. Luckily, Annie was up for the challenge as her asshole was loose enough to withstand the bombardment as her large tits and cute tush bounced and rippled.
And just as suddenly as Jeff began fucking her at top speed, he slowed to a near crawl, only leaving the first 2 inches of cock in Annie's butthole as his muscles tensed. Jeff gritted is teeth as his orgasm washed through him, his cum making the journey from balls to blasting from his tip and painting Annie's bowels. It was far less spunk then the load that absolutely covered Annie's face earlier, but the adorable coed still felt several warm streaks splash her inner walls.
"Oh my God," Jeff finally groaned, feeling all his muscles relax at once, slumping forward but still managing to stay on his feet.
"That just about covers it," Annie agreed, still laying on his bed. "I'm gonna need a shower and a lengthy nap before tonight."
"I'll settle for a shower and scotch. Maybe an ice pack," the lawyer joked.
"I could use one of them as well," Annie giggled. "Something tells me I won't be sitting comfortable for awhile."
"Oh, and Annie...my birthday wish totally came true."
* * *
A shower, scotch and nap later, the first party guests were beginning to arrive. Jeff's party wasn't going to be a big affair, really just the study group. Troy and Abed came together naturally, gifting Jeff a box set of their favorite Science Fiction show, as well as an admission pass to the next Comic Convention. Shirley's gift was her baking while Pierce gifted him a box of Cuban cigars and a bottle of 25 year old scotch.
"No gift from you Britta? I know your not into the whole consumerism but not even a little something is heartbreaking," Jeff said as he approached Britta alone in the corner of his condo.
"Are you kidding?! I got you the best gift of all," the blonde replied. She saw the look of disbelief on the birthday boy's face so she continued. "Annie Edison's anal virginity. What, you thought that nerdy girl came up with such a sexually mature idea all on her own?"
"Britta...I'm speechless." Jeff replied, completely stunned.
"Your welcome," Britta smiled. "I guess I didn't Britta your birthday then."
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The Man Who Has Everything