It was now Jeff's...or as he would be known to his students as, Mr. Winger's second day of teaching. Even though Greendale was a rundown, fairly crappy joke of a community college, Jeff had to admit it had done a lot for him. Not only was he able to complete his bachelor's degree and able to actually become a lawyer, he had also gained a core group of friends that made him a much better person.
Greendale wasn't done with the tall, good-looking man just yet though. After a failed attempt at becoming a defense lawyer again, though this time for people that were innocent, he needed a job. The community college's dean was more than willing to come forth and make Jeff a professor, shaping young minds with the course "Fundamentals of Law."
However, things didn't get off on the right foot. He completely bombed his first class, in which he was utterly unprepared and the students recognized it right away. However, a talk with his new office-mate Mr. Hickey of the Criminology department gave him new confidence. He still didn't need to plan a course but simply bullshit his way through the class having the students do group work.
When Jeff sauntered into class this time he was 5 minutes late and texting on his phone, dressed in a fitted brown sweater and tight blue jeans. He wasn't prepared by the sight of his good friend and annoying bookworm Annie Edison to be in his class. Mr. Winger had just given the class their work for the day, essentially having the students teach each other the reading from the textbook while he sat back and did dick all. But Annie had other plans.
"Okay so read chapter 1 in small groups," he said without looking up to even realize that a familiar face was in his class. "Any questions?"
"Yeah...a few," Annie replied, hand still hanging up in the air.
"Well no questions. Just read chapter one."
The class went by painfully slow for Jeff. Annie constantly was asking him questions, making him actually have to teach the students. When the perky brunette realized that Mr. Winger was completely shutting her out, she took it upon herself to teach the class some of the harder content from the text. Finally the bell went to end the hour-long class.
"Okay homework for Friday. Read chapter 2 and be prepared to talk about it within your group," he instructed.
"And read the memorize the federal rules of civil procedure," Annie shouted out.
"Class dismissed," Jeff added, before trying to make a quick exit.
"Not so fast," she spoke to him.
Getting up from her seat, she rounded her desk in the front row and approached the handsome man. He looked back at her, already halfway towards the door but the stern look on her face was enough to make him spin back around and slump down in his somewhat comfortable chair.
Approaching the sulking teacher, Annie looked annoyed and disappointed with her friend. He had his arms crossed in front of his strong chest, head drooped and refused to make eye contact with the beautiful pupil. She also had her arms crossed in front of her, but it made her look like in authority, while her large, pixie eyes remained fixed on the older man.
"Do you know why I'm keeping you after class," she asked.
"Not really. The other students in the class got lots of stuff wrong too," he replied, finally looking her in the face.
"Yeah but you're a teacher Jeff. What I saw today...was embarrassing," she scolded. "You were late, you had no idea what tort reform meant and when I asked you to explain the 6th amendment, you plead the 5th."
"I know my rights," he answered.
"No, you don't! That's the problem," she shouted in frustration.
Turning away from him she went back to her desk and retrieved a stack of what had to be 5 textbooks. Using all the strength in her petite body, Annie hoisted the collection up onto Jeff's desk right in front of him.
"I collected some material for you. By Friday morning before class I need to verify that you know enough to teach," she told, then quickly followed up before he had a chance to argue. "Yes I'm going to quizzing you."
Jeff knew his friend well enough to know when she wouldn't back down from something. Even if he was on his A game, which he wasn't, he doubted that he could have talked himself out of her punishment. Knowing that the argument was lost, he decided to accept his fate so he moved onto something more pressing for him at this time.
"Can I ask you a question now," Jeff asked the stern-speaking student after her rant.
"I suppose," Annie said, finished her tirade. "Well what is it?"
"Why didn't you wear a belt with those dress pants," the handsome man asked.
Annie gave him a cute little smile only using the corner of her mouth. She leaned in close so that no prying ears could listen in then said to him in a low, husky voice: "Easier for you to get them off is why."
Jeff smiled as she pulled away from him. He felt his dick stiffen from within his pants, the combination of her words and her warm breath on his neck.
"Then why not wear a skirt," he asked, keeping his voice low.
"Because I have to make you work a little bit for it," she replied.
With those words spread she diverted her large eyes down towards Jeff's groin. Sure enough she could see the material bulging slightly as her words alone made him erect. Satisfied with her effect over him she gave him a knowing smile and kept eye contact with him as she turned around before walking back to her seat to gather her things.
Jeff had made some arrangements within his pants so that any students leaving the room wouldn't see his large erection currently tenting his tight pants. Standing up, he slowly walked to the front of his desk before rocking back on his heels and resting his ass on the corner of the wooden table.
Annie had finished gathering her books, placing them with exact precision into their specific location within her bag. Even though she couldn't see Jeff's face, she knew, or was willing to bet her apartment on it, that the older man was scoping out her well formed, rounded ass. Putting her arms through the straps of the back pack on at a time, she gave any leering eyes one final wiggle of her backside before turning around to walk out the room.
She didn't get very far though. As she walked only 3 steps from her middle seat in the front row towards the aisle, a strong hand closed in around her lean upper arm. The contact was firm so that she knew that he was in charge, but not so strong that it hurt. Jeff did a combination of pulling her gently yet firmly towards him while also leaning his tall frame towards her.
"See me after your last class Ms. Edison," his hot breath on her sensitive neck making her wish that he would just bend her over the desk right now and fuck the living hell out of her.
"I hope it's not for anything serious," the naive sounding girl asked, her expressive face showing concern.
"Very serious actually," Jeff replied, sounding stern.
"Well in that case I'll come quickly," making sure she lingered on her pronunciation of the word come.
This time Jeff did a sweep of the room to make sure no students were around. Satisfied that no one was around, he leaned in even closer so that his nose was now touching her hair right above her ear. The contact was minimal, probably not so much that anyone walking by the room likely wouldn't think anything inappropriate was happening, yet it still made the brunette flush with excitement.
"I'll make sure I don't cum too quickly though," he whispered in her ear.
As soon as the words were out of his mouth he released his grasp on her arm, freeing her. Annie took a moment to collect herself, trying to normalize herself even though her pussy was gushing like a hillside creek during spring thaw. After one last deep breath, in which she focused on puffing her stomach out while inhaling and drawing her naval in during the exhale, she continued walking until she passed the door and went out of sight.
* * *
Annie finished her Criminology class with her least favorite professor and looked at the watch. It read 6:55. It would take her 7 minutes, 5 if she really hustled to make it back across campus to the Law wing of the building. When Mr. Hickey had dismissed class she already had her bag packed and was the first out the door.
On her brisk walk-cum-run through the sparsely filled hallways, she couldn't help but think about what awaited her in the empty classroom. In fact, she had been thinking about it all through her last course. It was the first time in her academic career that she could remember being so distracted.
Finally she had arrived at her much-anticipated destination. A check of her wrist watch, a gift from her old friend Pierce Hawthorne who had since graduated from Greendale, revealed it took her just under 5 minutes.
"All time best," she thought to herself. "Must be excited about something."
Looking inside the dark room, made that way with only east facing windows, she didn't see the man she desired. For more than a year now Annie and Jeff had been seeing each other in private without anyone else knowing, much like he had done with Britta several years ago. Annie was excited about the arrangement as it meant she had a real grown-up relationship with a man she lusted over for 4 years, but without receiving any of the negative attention that people of Greendale would have given them over their age difference.
"What are you doing in here Ms. Edison," a stern sounding voice said to her.
"There are no students allowed in the classroom after hours," Jeff said, now coming into view from the rear of the class. "We keep important things in here. Like the answer sheet to exams. Is that what you were doing in here? Stealing?"
"What? Well...ummm," Annie stuttered. She realized Jeff was playing a game and she was very much willing to exchange with him. "Fine you caught me Mr. Winger, please don't think less of me."
"Think less of you? It doesn't matter what I think of you Ms. Edison, it'll only matter what Dean Pelton thinks when I bring you to his office and tell him you tried stealing the exam," he answered, moving closer to the heavy breathing girl.
Annie's expressive face went through a range of emotion, alternating seamlessly from confession to scared to hurt to fear then finally to thoughtfulness. That's when she brought her hands up to her hair and began to undo the clip that held her bangs in place in the center of her head. Jeff watched on as the studious brunette tied her hair into two symmetrical pigtails, each one starting somewhere behind her ears and flowing down over her large chest.
Jeff allowed her to fix her hair and to take a few moments to think over the scene he had created. One of the things he adored about the cute-yet-still-sexy co-ed was her imagination and dedication. Anything that the 4.0 GPA student did, she committed 100% and that was why he gave her the small grace period
"You don't need to take me to the Dean's office Mr. Winger, we can work out our own arrangement," she said, drawing close to him so that she could run a hand down his muscular chest and onto his chiseled abs through the sweater.
"Possibly," he said, wheels turning within his head. "But this goes down as I want it."
"Yes Mr. Winger, anything," she pleaded again.
"Take off your top. Bra too," Jeff instructed.
Annie looked like she was thinking about whether or not to do it, but he knew it was all an act from the studious girl. After about 30 seconds of thinking it over, hesitant hands were lifted to the top of her silk blouse. Her delicate fingers expertly undid each of the buttons of her light blue shirt until it hung open down the middle of her torso, a black bra and ample amounts of cleavage now in view.
She hesitated at this point, pretending to be modest despite the fact Jeff had seen her naked several hundred times in their relationship. So Jeff decided to give her some help. Still within an arm's reach, the lanky man stretched out and placed strong hands on her shoulder, fingers slipped inside the shirt to rest on skin. Steadily he pushed the smooth material back until it crested over the top then descended easily down her toned arms to settle on the floor behind her.
Now, keep going," he encouraged.
"How about we leave something to the imagination," she fake implored.
"Or I call campus security and have Dean Pelton throw bribing a teacher onto your list of offenses for tonight."
Annie rolled her eyes back into her head as an act of defiance, but there was only ever going to be one outcome at this point. Bringing both arms behind her back, the defeated brunette reached up and clasped the back of her bra with both hands. A second later Jeff saw the cups in the front slacken before they ultimately fell away, dropped to the floor.
Finally Annie's most impressive sexual asset came into view...her amazing tits. The globes were rather large, more than a handful for even Jeff, which was saying something. Located in the perfect center of the breasts were small pink nipples, currently poking out due to the excitement the short girl was feeling. Equal impressive was the fact that the heavy boobs hung flawlessly directly in front of her chest without even the hint of sag. Even after a year of seeing her naked body, Jeff still had a tough time believing that these huge magnificent tits belong to a girl that was so petite and that he had access to them at his leisure.
"Satisfied," she said after giving him some time to scope her out. She didn't know why but she accompanied the question with a light, almost playful one handed push to Jeff's chest, a move that caused her boobs to jiggle and sway in front of her.
"And now you are trying to assault me," he countered, clutching her wrist firmly.
He was obviously under no threat from the tiny girl, who measured in at approximately 5'2 and 115 pounds. However, the older man was looking for any excuse to bring his handcuffs into play in order to use on Annie. Reaching into her back left pocket of his pants, Jeff withdrew the shiny metal restraints, and dangled them right in the brunette's face.
"Why does a law professor have a pair of handcuffs," Annie asked.
"Because he knows of the filthy minded sluts in his class," Jeff replied to the horny co-ed. "And you never know when one of you will get too crazy and get aggressive with me."
"Don't you want me to get aggressive with you," she said sexily, her piercing blue eyes staring through the loop of the cuff to gaze him directly in his eyes.
"Yes...but on my terms," he replied then acted.
In a gesture that was shift enough to make Annie think he must have practiced the maneuver in private, Jeff snapped the first cuff onto the wrist he still held in his hand. Annie winced and let out a slight moan, more out of surprise than anything, as the cool metal snapped tightly around her flesh.
Annie let another gasp escape her plump lips when Jeff spun her around so that her back was to him. He wrenched, softly as to not cause the girl any actual pain, her cuffed around as well then easily found her free arm and brought it behind her topless back as well. Annie first heard then felt the restraint as it cinched around her right wrist, leaving her arms bound behind her.
"You know I own you now for the rest of the semester," Jeff whispered into the detained girl's ear. "Don't do as I say when I say and your perfect GPA is ruined."
"Oh but please Mr. Winger, I'll do anything for that not to happen," Annie played along, hamming up the mock innocence that Jeff had long ago taken from her.
"I still have half a mind to call the cops," Jeff mused.
"There's no need to call them, or the Dean," Annie said while spinning around to face him again, her large tits swaying as a result. "I was just...coming back because I thought I forgot a book."
"Don't bullshit me Ms. Edison. It was my job for a long time to make up that stuff so I'm pretty good at knowing when others are doing it," the ex-lawyer told her, his gaze never leaving her nipples.
Annie decided she'd take a new tactic. Rolling her shoulders back and standing up tall she pushed her amazing breasts out even more and stepped nice and close to the Law professor.
"I bet seeing all these horny and loose girls coming through the halls and in your class gets you all hot," she said in a sultry voice. Especially since they all flirt with you, you being all tall and handsome."
"Are you one of these girls," he asked.
"So horny. In fact you can touch my dripping wet pussy just to verify that I'm telling the truth. And by not reporting me, I'll let you do whatever that sick, dirty mind of yours can think up."
With that said, Annie slowly turned around again so that she was pressed tightly against the front of her Law teacher. Her short height and his long legs meant that her restrained hands were at a perfect level with his bulging crotch. Pinning his lengthy shaft against his inner thigh, the horny brunette was able to rub his pole through his jeans, causing Jeff to moan audibly.
He allowed her to stroke his hardened cock for a minute, getting him good and worked up. Using his power over the defenseless but willing participant, Mr. Winger pressed his palm between her shoulder blades. The brunette understood and began leaning down until her naked perky chest was resting against the unforgiving wooden table.
Jeff walked around the desk until he was standing in front of the gorgeous girl. Annie was committed to the role playing that they were doing so wore an expression of apprehension mixed with longing. Jeff was very much prepared to fulfill the fantasy for both she and him.
"Open your mouth," he barked all while pushing his pants down his leg and having his 8 inch penis come springing out
"Are you going to...put that in my mouth," she asked in more mock innocence, her large eyes flashing to his erect cock.
Jeff didn't bother responding with words. He simply looked down into her eyes with a stern look then waited until she parted her lips like he had ordered, sticking her tongue out as well for good measure. Jeff stepped closer so that he could reach down and clutch the pigtails that she was donning. With a good grip now he placed the tip of his dick between Annie's lips, resting it right on her tongue.
"Now suck," he ordered.
Without missing a beat the eager bookworm sealed her plump lips tightly around the crown of his member and applied suction. Jeff grunted loudly into the empty classroom as her moist mouth began to work. Knowing that she barely had any leverage, Jeff had to do all the work to get full pleasure from the blowjob.
He pushed his hips forward while holding Annie's head in place. Jeff watched as the first several inches of his cock disappeared inside her mouth. He held himself inside her, soaking in her saliva before withdrawing, feeling the underside of his dick gliding along her wet tongue and finally felt his tool sandwiched between her muscular lips.
"Fuck that's good," he exclaimed.
After the first pass into her mouth, Jeff seemed to lose his inhibition. This time when he thrust his hips forward he also dragged her head in the same direction. The result was the tip of his cock poking the back of her mouth, naturally stimulating her gag reflex. Annie had gotten a late start on sex, and even though she'd been getting plugged by Jeff regularly for the past year she still hadn't been able to deep throat.
This meant that as Jeff pulled his cock and her head away, thick strands of saliva connected his pole with her lips. Looking down at this, seeing spit covering his member, seemed to make his dick grow even harder somehow. He re-doubled his clutch on her pigtails and slammed her face and his dick into each other. This time she audibly gagged, turning Jeff on even more.
Over and over Jeff plunged his erect cock into her mouth to the beginning of her throat. Each time she sputtered and coughed, spewing more and more spit onto his rod while giving him the wettest and loudest blowjob of either of their lives. Jeff was very much wrapped up in the moment, but every now and then when he thought the treatment was getting too rough he glanced down at the beautiful girl. Sure enough, Annie was already looking back up at him with her eyes encouraging him to keep going.
Jeff couldn't take it any longer, he needed to be inside the gorgeous girl. Not wanted to enter her, but he felt like he physically needed to or else his entire being would begin unraveling. He pull back his hips one last time and took a step backwards as well, putting some distance between her mouth and his very hard cock.
"Did I do something wrong Mr. Winger," Annie played along, looking up at him with a scared look.
"No Ms. Edison," he replied, thinking to himself that she was doing too good of a job.
He walked around her, leaving her eye sight as he circled the desk. There seemed to be an urgency in his stride, Annie noticed and rightfully so. She had been extremely horny so she imagined that he was prior to her wrapping her talented lips around his manhood and blowing him for 15 minutes straight.
Jeff was now standing directly behind the plump-bottomed girl, one hand lightly stroking his dick and the other undoing her dress pants. Even with only half his focus and a solitary hand he was still easily able to have the pants bunched down at her ankles in no time at all. Jeff stopped touching himself long enough to give both of Annie's meaty butt cheeks a firm squeeze before hooking his long fingers in her panties and pulling them down her short but toned legs.
The law professor was milliseconds away from guiding himself into her dripping wet pussy when he looked down a got an idea.
"I can do whatever I want to you," he asked her.
"Whatever you want," she moaned in response.
Jeff smiled brightly then brought his right hand swooping down until his palm connected with her ass cheeks on the same side. This action caught Annie by surprise and made the nude girl shriek in surprise.
"Mhmm eeekkk," she screamed.
Before Jeff slapped her other cheek, making a bright red handprint on each of them, he used his talented fingers to rub her bald pussy. Sure enough, the brilliant co-ed wasn't lying when she said she was horny as his fingers were positively drenched in her fluids.
"Oh my God," Annie moaned in pleasure.
Jeff couldn't take it anymore. Placing on hand on the small of her back to hold her steady, he guided his erect tool into her pussy, entering it with ease until he was completely buried with her. This caused Annie she scream even louder but this was far from his end game. He soaked himself within her flowing juices for a long few seconds then pumped once in and out of her twat before withdrawing altogether.
The beauty with the type A personality was about to complain when she learnt of Jeff's true motivation. He had simply used her pussy juices as a natural lubrication for when his dick entered her asshole, which would be any second now. She felt his tip contact the sphincter that kept things out of her most taboo of holes, simply waiting there for her to relax. The second Jeff felt the younger girl's tone ease up, he made his move by pushing his hips further forward until he felt her anal ring squeeze the crown of his cock, the penetration confirmed by a wet slurping pop.
Then Annie did something she had only done once before...she came immediately
If her mind was able to think, which it wasn't do to the intense pleasure, she'd have known why it happened so fast. She had strong feelings for the man currently sodomizing her, mostly lust but possibly some of true love as well. That, coupled with him making her wait for sex all day made her ride a wave of horniness and longing for hours. Then he teased her with light rubbing, even fucking her pussy for the briefest of moments before giving her an actual penetration. The role playing and handcuffs further spiced things up.
Jeff noticed that her ass seemed to loosen up extremely quickly, especially compared to the few other times he had gotten luck enough to get Annie to agree to anal sex. He thrust into her asshole with slow short strokes to get her warmed up, but it seemed that with each passing moment she was able to take more. Riding his luck, Jeff continued to thrust deeper, slowly increasing the speed simultaneously until his entire dick was passing in and out of Annie Edison's asshole.
"Oh yeah! That's what I wanted," Jeff grunted as Annie made small, subconscious moans.
Jeff had been getting faster and faster at slamming his dick into her asshole so that it looked like a flesh-colored blur that repeated kept disappearing inside her. However, he'd been at it for the better part of 10 minutes and it was beginning to wear on his stamina. He needed a break so he pulled out of her rump, watching with a perverted smile as her once tight asshole stayed gaping open for a few seconds then it constricted back like nothing had ever been side her bowels.
Then a wicked idea struck Jeff. It would have been a first in their relationship but then again, role playing and bondage had also been new experiences that they shared tonight. He walked back around to the front of Annie, who remained bent over the desk, her plump ass still waving in the air on the other side now.
"Open up," he demanded, hands gripping her ponytails at the side of her head.
"Wait! What are you doing Jeff," Annie asked with genuine shock.
"First of all, it's Mr. Winger to you. I'm a teacher after all," Jeff told, staying in character. "And you my dear said that you'd do anything to not fail my class."
"But that was..."
"Correct, just in your perfect little asshole. I'm glad to see you're still paying attention Ms. Edison," Jeff responded. "Now do s I say and open that sharp-tongued mouth."
"Jeff please, not that," she begged, her eyes like a puppy dog.
"Okay how about this. You don't taste test your own butt then I'll go get the security and tell them I caught you trying to break in and steal the answer key for the exam. Not only is that a fail but you get expelled. Now...what will it be," he said, then broke his role. "From what I've heard it's not gross if you're clean, it only has a slight metallic taste. Please Annie, it'll be so fucking hot."
Annie's face looked like it was about to argue, even parting her lips. Then she stopped and had a thoughtful look flash across her. Finally, much to Jeff's excitement, she resigned her argument and did as her secret boyfriend and now current professor asked of her, she opened her mouth wide.
"You want me to clean it up," Annie said from her knees, mouth inched away from taking him inside. He was pleased she had dropped the defense and gotten back into character.
"Mhmm," Jeff replied, the anticipation killing him.
Annie would never have thought that she'd even think about degrading herself so much as to suck on someone's cock that had come straight out of her asshole. Yet there she was kneeling on the floor of a classroom, hands cuffed behind her back with a ass-covered dick less an inch from her face.
Unable to reach up with her hands given their pre-occupied situation, the pretty brunette took one last deep breath to steel her nerves. She was very concerned at how horrendously gross it would be to wrap her lips around something that had come straight out of her ass. Seeing no other way around it, and desperate wanting to please Jeff, she opened her mouth and lowered her head so she could take the tip into her mouth.
"Mmmm...yeah," Jeff grunted as he got an extra perverse thrill seeing a girl suck her ass off his member.
Even though she never thought in a million years she would take something that came directly from her asshole and put it in her mouth, it was too late for that now. With the tip already in her mouth, Annie blocked out how repulsive an act of such a nature was and focused on just giving him a good blowjob.
She had bobbed her head a few times on his member now, taking almost half of his rod into her mouth when Annie thought about how the taste of her anus didn't seem so horrible. It had a slight metallic taste, not nearly as strong as bl**d though, but other than that it wasn't too powerful of a sensation. This wasn't something she'd do all the time, but she would definitely be more open to trying it again to impress Jeff.
As Jeff's cock was engulfed in the warm, moist opening that was also known as Annie's mouth, he couldn't help but continue to groan loudly. The girl was talented enough with her mouth that she would have been able to elicit grunts from him on a normal day, but the fact his tool was fresh from her bowels made it even sexier. Looking down at the top of her brunette head starting to bob up and down into his groin, the ex-lawyer couldn't help himself by resting one hand on the top of her head, helping her get just a bit more of his flesh into her mouth.
"Oh yeah, such a dirty little slut," Jeff insulted while the bookworm tasted her own asshole from his dick. "Clean that dick."
Jeff kept peering down his long torso to watch the studious girl pleasure his cock with he mouth. Just visible beyond her head, the college teacher could see Annie's large tits jiggling in front of her each time she energetically bobbed up and down his shaft. This combined with her natural blowing skills to push him closer to cumming, which was something he didn't want to do yet.
"How'd your ass taste," Jeff asked, pulling his dick from her talented mouth.
"Really good," she replied with a smile as she got to her feet. "I liked it."
Jeff clutched the back of her head and brought her in for a kiss. His passion was seemingly burning hot in him and he needed to kiss her or else his chest would burst. He held her tightly for a few seconds before letting his hands roam her body once again. One palm found itself at one of Annie's extremely large tits, squeezing the globe for good measure while his other went down between her legs to rub her still-wet snatch.
"I got an idea," he said with wide eyes.
"Oh? What's that," Annie replied with a questioning look.
Rather than tell her, Jeff showed her. Using one of his long arms, he placed it on the desk before swiping across it. Instantly books and papers went clattering to the tiled floor below, making an absolute mess.
"I always wanted to do that," he said with a gleeful smile.
"You know I'm going to have to clean that up after, right," she told him.
Jeff simply shrugged his shoulders before climbing onto the de-cluttered desk. Despite still having her arms restrained behind her back, Annie was hot on he's heels and joined him up on the wooden structure. The recent professor had gone supine, laying his muscular back on the table in a position that would make the studious girl do all the work. Annie didn't mind though, her earlier orgasm fueling her sex drive even more than ever.
Annie had no trouble swinging her short leg over his torso so that her pelvis hung suspended over the older man's lap. Even though the hand cuffs were firmly in place, the brunette was able to reach down and clutch Jeff's wet and stiff cock. She had no hesitation steering it back towards her asshole once again, only stopping to rub his slick head around the crinkled orifice.
"Mhmmm," they moaned in unison as he entered her rump once again.
Annie didn't cum right away like she did last time, but it still felt amazing to have her secret boyfriend back inside her. She slide further down on his lap, impaling herself more and more with each stroke she did on him until she was finally gliding down all the way that the back of her thighs would touch the hair-covered skin of Jeff's quads.
"Fuck Annie you feel good," the lawyer grunted, reaching up to squeeze her impressively sized tits.
Annie moaned even louder as she rocked her ass on his lap with his shaft completely buried in her bowels while Jeff played with her breasts. The dual stimulation was driving the young co-ed crazy, but she wasn't the only one who was enjoying the sex.
From beneath the energetic girl, who had resumed bouncing up and down on his cock, Jeff was in a world where only pleasure was able to be experienced. Her asshole was tight, but not too tight to the point where it squeezed his dick painfully like a hungry boa constrictor. Plus from his angle he had a perfect view of her bouncing large tits, her shaven bright pink pussy plus could watch his fleshy pole disappear every other second into Annie's underrated rump.
Unfortunately the half hour of anal fucking his kind-of girlfriend was really starting to wear on his resistance. Jeff knew that at this point there was little good in changing position or slowing things down as he knew an orgasm was only a matter of time.
Annie knew that the man of her dreams was getting close, what with all the face grimacing and extra firmness in his groping. It also confirmed her suspicions when Jeff dropped a hand down from kneading her bouncing tits and moved it so that his index and middle fingers were rubbing her clit. Jeff could be selfish at times, but never when it came sex, despite what Britta had said about him. The ex-lawyer was on the verge of cumming himself but he wanted to make sure that his brunette nymph came with him.
"Almost there," he warned. "Cum with me."
Annie grunted her approval but was receiving too much pleasure to reply with words. She simply began to ride his dick harder in her asshole, springing to the top with all the power her toned legs could muster than allowed them to go limp so she could slam down his shaft with reckless abandon.
This was more than enough to get Jeff off, pushing him past the point of no return. It also proved too much for Annie Edison as well, especially in combination with his frantic clitoris rubbing.
Annie was quicker off the draw and beat Jeff to the climax. Her second orgasm of the night lost no intensity that the first one had, in fact may have been even stronger. The real kicker for the studious girl was the stimulation from so many different areas. The cock impaling itself in her ass, the fingers to the clit, the hand squeezing her tit and the mouth enclosed on her sensitive nipple made for one power-packed, scream provoking orgasm.
"AWWHHH MMHMMM UUGGHHHH," Annie screamed incoherently.
"Gonna...ugghh...cum," Jeff warned, face severely twisted.
No sooner had Annie cum had her asshole clamped down like a vice around his already cocked and loaded shaft. As the last word escaped his lips he felt the last wall of resistance break down and the warm liquid began bubbling up from his sack. Jeff had thought of really milking the master and slave game and cum on her face, but the thought of not having her snug pressure around his cock just felt so wrong.
Annie barely registered his last words due to her own orgasm, but she certainly felt the first squirt of hot jizz shoot deep into her bowels, coating them. The tall man continued to erratically thrust his hip upwards into her now still body as stream after stream of his thick fluid came flowing out, pouring into her anal canal.
Eventually the gorgeous and smart girl knew Jeff was completely spent. His facial expression relaxed into one of serenity, his iron-like grip on her various curvy body parts relented and his hip thrusting stopped altogether, replaced with the mere light twitching of his sensitive dick still invested in the comfortable clamp she called a rectum.
Having some energy return to her after her climax, she summoned the remains of strength in her tired legs one last time. The innocent-faced brunette lifted herself slowly and carefully off the cleared desk, squatting down to rest her ass on the table then ultimately got her feet back on the floor.
She was still handcuffed but Jeff snapped out of his daze quickly after noticing her clamp-like ass was no longer surrounding his dick. He rolled off the desk as well and located his pants before searching the front pockets. He withdrew a small metal object, and seconds later Annie was free from her bounds. The pair got dressed after that, Annie realizing the cum in her asshole was already dripping from the orifice, ruining one of her favorite pairs of panties.
"I think we can all agree that the classroom has more purposes than just learning," Jeff joked through exhaustion.
Annie took a moment to smile at his corny joke and get her breath back before speaking to him. "I still expect that assignment done by next class Mr. Winger." Annie left, unaware that Abed could see cum dripping down her legs as she walks past
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