Anal Academy

When she felt the warmth of her sister's tongue on her sphincter, Maddie jumped, "What are you doing? Are you licking my...ass?"

Heather didn't answer. She just giggled and stuck her tongue back inside her sister's ringed bud and licked up the remaining semen. After a lengthy slurp, Heather stood up. Maddie was confused as to why she quickly stood up and turned around.

With her mouth full, Heather tried to speak to Maddie in her mumbled language, "Ohen...uuu."

Maddie thought Heather was nuts and repeated what her sister instructed, "Open up? You mean my mouth? Are you nuts? I don't want you..."

Heather interrupted her rant by planting a huge kiss on her sister and spit the contents she was holding into Maddie's mouth. Before Maddie had a chance to react, Heather ordered, "Swallow it. It's good."

Maddie squinted her eyes and swallowed. She nodded her head in agreement with her sister, "You are right. It is not bad. It reminds me of orange sweet tarts."

They both laughed and the rest of the summer, whenever one of them would have anal sex, they would come home and allow her sister to sample the deposit. There were several days where they would both do it and come home and lick each other's gooey anus. It just became second nature.

As the summer was coming to an end and Maddie, Heather and her parents attended the late July orientation, Heather wondered over to Dr. Anderson's office while the rest of her family sat through the same presentation as they had done the previous year. The Dean was happy to see her and was elated when Heather told him that her younger sister was also going to join Anal Academy. They exchanged phone numbers and Dr. Anderson told her they would meet on that Sunday night before Monday's first class.

Finally that day arrived. The girls were rooming together and settled in by that Saturday. When Sunday rolled around, they drove to the apartment that Dr. Anderson had designated as Anal Academy Headquarters via a group text. Maddie and Heather walked in the nice place and the Dean greeted them before offering them to have a seat.

He introduced the other girls. In attendance was Michelle who was a tall thin leggy blonde who stood 5'10. A short 5'0, 95 pound cute Asian girl named Keiko and a 5'8 athletic muscular black girl named Aleesha with a large booty and huge boobs were also in attendance.

After they all sat down on the spacious couch, Dr. Anderson began explaining, "Thank you girls for committing yourself to this club. You are here because you love ass play and anal sex. We will have some challenges and plenty of, said, anal sex this year and then you can decide if you want to remain in the club or move on. But, there is one catch you may not know and that is you will be judged on a point system. After the last meeting of year, whoever has the most points, wins a full year's university costs completely paid. That includes tuition and room and board."

When everyone heard that, all of the girls just about jumped out of their seats. They talked over each other asking him if he was serious and eventually he had to quiet them all down to continue explaining the rules, "Hold on girls. Please get quiet so I can continue."

After their silence, he continued, "Yes I'm dead serious and you will receive a full year's scholarship from a secret account, so you are not to mention it. Upon winning, you will be given the pass code for its access."

He passed out a laminated sheet to each of the girls. It was bullet pointed and read as such...

●2 points = Every anal sex session to orgasm with a different guy/cock

●1 point = Every anal sex session to orgasm with a repeated guy/cock

●1 point = For an additional kinky act after any anal sex session. (Kinky acts are defined as...ass to mouth sucking, anal creampie eating, snowball kissing after anal creampie extraction, or anything pre-arranged with Dr. Anderson)

●3 points = Every anal sex session to orgasm with Dr. Anderson

●.5 points = Dressing slutty before each session

●5 points = Completing the challenge at the monthly meetings

●10 points = Winner of the final challenge at the May meeting

NOTES: 1-No condoms allowed

2-Every session must be proven with video tape

3-Upload videos to google shared document

4-Dr. Anderson's judgement is final and binding

Dean Anderson allowed the girls to read the instructions before he asked, "Are there any questions?"

Aleesha asked, "If we want a session with you, how do you want us to get in contact with you to arrange that?"

He responded, "That is a good question. You can either email my school address or text me 'academic meeting' then give the time. My wife has access to my phone so we have to be careful. All sessions with me will be here and will be first come first served."

There were a few more questions asked before he dismissed. Each girl was given a case of standard enemas so they wouldn't have to pay for them themselves with a promise to get more upon request. That was just the initial meeting and the monthly meeting wasn't scheduled until the end of August. Heather and Maddie stayed back until the other three girls had left. They purposely went to the bathroom to discuss everything.

While whispering, Heather asked Maddie, "Wow...can you believe it? That is a lot of money. You realize you have no chance to win if you don't have anal sex with more than just Colton? Look on the bright side, we might have to get slutty but we don't have to worry about getting pregnant. Are you going to stay in the club?"

Heather was half expecting her sister to say she was going to remain faithful to her boyfriend when Maddie surprised Heather with her answer, "I guess what he doesn't know won't hurt him."

They both giggled and discussed maybe staying back and doing Dean Anderson. Even with Heather's warning about his size, Maddie agreed. They returned to the main room and smiled at him.

Heather spoke for Maddie, "Dr. Anderson...does today count as day one? Maddie and I would like to get a head start and maybe have you do us. Do you have time?"

He smiled as he unbuckled his belt, "I do have some time. I think that is a wonderful idea."

When his pants hit the floor, Maddie blurted out, "Holy shit! Are you serious?"

Heather laughed while assuring her, "Don't worry about it. You can take it if you concentrate and I will be right here with you."

Both girls were on their knees sucking and playing with Dr. Anderson's huge dick while using his bunched up pants as their knee pads. They also alternated kissing and licking his balls. When his monster became engorged, Maddie sucked the best she could and jerked it with both hands even though she could barely fit it in her mouth.

He groaned, "Damn girls...you must be horny. Which one is going to take me first?"

Maddie stopped sucking to beat her sister to the response, "I will!"

While both girls were getting undressed, the Dean removed his pants, shoes and socks and while only his shirt, laid down on the floor on his back. He told Maddie where to get the lube in the bathroom and the nude teen returned carrying the bottle with a huge amount already in the palm of her hand. After greasing up his cock, Maddie was straddling and squatting overtop it while Heather was politely holding it straight upward to make it easier for Maddie.

Heather went into cheerleader mode while encouraging even though she really didn't believe Maddie could take it, "Come on...you can do it. Clench your ass then relax it. Do that a few times."

Slowly Maddie descended until that huge head pressed firmly against her anus. Dr. Anderson quickly redirected her, "Face the other way. I want to see that gorgeous ass of yours while we do it." She turned around then squatted back down. Heather continued holding his cock with one hand and held Maddie's hand with the other one for added support. Without much thought, Maddie began to sit down, shrieked loudly, then continued her journey until see was sitting completely impaled on that magnificent meat on the first try.

Heather had little time to move her hand out of the way from the sitting Maddie but was simply amazed how well Maddie took it without stopping or having to retry the entry like she had done. Maddie gasped, "Oh my God! I am so full right now! I have never experienced anything like it! I love it! I could stay like this all night."

Dr. Anderson also loved it. That young tight rectum clenching his meat like a warm oven mitt was making him anxious when he impatiently instructed the 18 year old redhead, "Ride it baby girl! Don't be shy...giddy up"

Maddie began to ride that dick like she was a cowgirl. She bounced up and down...up and down while moaning. Dr. Anderson put his hands on her hips but mostly to touch her soft skin. He allowed her to do the work and loved seeing her asshole stretch and accept his girth.

Heather continued holding her sister's hand for balance and support but knelt silently stunned how well her sister had developed her love for anal sex right before her eyes. Maddie was genuinely getting maximum pleasure without any pain. She was also using her middle finger to rub her own clit while she rode. When her orgasm overtook her, she stopped riding and sat down on the cock while grinding causing her to violently shake and squirt on the floor between his spread legs.

Dr. Anderson got that look on his face when Maddie started back up again. That tight warm asshole was just too much and he unleashed his load while it seemed as though Maddie was milking it with her insides. He groaned, "Oh Fuck! Ohohohoh! Aughhhhhh! Damn girl! Ohhhhhhh! You made me cum too quickly! Wow that was a good one!"

Even though he had finished spurting, Maddie didn't care and continued riding until she squealed in another explosive climax! Her entire body trembled and she squirted even further. When she got off him, cum dripped from her gaping hole. She stepped gingerly to her sister and bent over in her face, "What do you think? Is it stretched?"

Her gooey asshole was as wide as a full roll of tape. Heather dipped her face inside and licked the slime that had coagulated around the inner sphincter. It was that same delicious combination of salty and sweet. Dr. Anderson was so aroused while watching Heather consume Maddie's anal creampie. He jerked his meat and it stayed hard. He was quickly to his knees, and behind Heather in a flash.

Heather never lifted her face out of her sister's gaped anus while Dr. Anderson was trying to put his cock in hers. Finally, as it started stretching its way in, Heather tightly grabbed her sisters thighs trying to acclimate herself to the initial pain. He held onto Heather's hips just as firm as she had done with Maddie. He was pumping his huge rod into her doggie style.

He was talking extremely dirty, "Eat her ass you little slut! Get in there deeper and get all that cum out. I shot a huge fucking load and it needs cleaned out. I bet it tastes good!"

Hearing his filth, Heather began orgasming with her face buried in her sister's ass. Her screams were muffled like in a cave which technically she was in face deep. Even Maddie got into the action by twisting around and pulling Heather's face in deeper by the back of her head. Dr. Anderson was in ecstasy watching the younger sister forcing the older sister to eat out her sloppy ass.

He blurted, "I'm going cum again! Get ready for Daddy's second load!"

Maddie adamantly insisted, "Don't cum in her ass! I want it! Tell me when you are going to do it!"

Dr. Anderson continued feeding his dong into Heather's rectum, "Shlump! Shlump! Shlump! Shlump!" He was doing his best to hold out as long as he could to prolong the pleasure. He was shaking his head and even slowed down for a little while but eventually had to release.

"Here it comes! Hurry Baby Girl...get over here! Hurry!" He desperately warned.

Maddie jumped over and got down on her knees next to her sister. She leaned her face only inches from where the penetration was taking place. Suddenly, Dr. Anderson let out a roar and pulled his cock out while pinching it off to stop any semen flow. Once he placed the head in Maddie's mouth, he began to jerk it furiously!

He bellowed even louder, "Aughhhhh! Augghhhh! Aughhhhh! Take it! Take it all! Aughhhhh! Augghhhh! I'm still cumming! Aughhhhh!"

After his first and second shot, Maddie heaved like she was going to gag but quickly regained her composure to suck the cum out of Dr. Anderson's large dick. She was an absolute pro at taking his manhood ass to mouth. Maddie gladly accepted every drop without allowing any to spill down her chin. Dr. Anderson was cumming so hard he felt like his own asshole was turning inside out.

When it had stopped ejaculating, Maddie squeezed the base of the shaft and ran her hand upward to milk out the last remaining dollops before swallowing. She then gasped for air like she had held her breath throughout his orgasm, "That was great! That was a lot of cum. We need to do this again soon."

Dr. Anderson agreed with the two beautiful coeds and gave them their four points each and a kiss as they all dressed. When the girls got back to their dorm, they showered and discussed what had just happened. They both were hooked even more and not just a desire for anal sex for the club's competition.

School started and the first week was difficult. Neither Heather nor Maddie had much time to score any points while getting some anal pleasure. They were consumed with the rigors of the Harvard schedule and getting their academics in order. However, they concocted a great idea with the guys in their co-ed dorm hallway. There were twenty rooms and every other room was occupied by guy roommates which meant there were a total of 20 potential guys for a low key Saturday night sex party.

Throughout the week, either Heather or Maddie would knock on doors to invite them over for the fun. It was to begin at 8pm and the only stipulation was it had to be kept a secret. The girls purchased more lubrication and towels along with three large sheets to cover their futon couch and beds.

Around 5pm, the girls gave each other her enema and within the hour, each was cleaned out and had taken her shower. Feeling and smelling fresh, it was time to dress up really slutty to acquire that half a point. Heather wore a spandex skin tight black mini-skirt that barely reached past her butt cheeks and a spaghetti strapped half top with black four inch high heels. Maddie wore a teal sundress about two sizes too small and high heel mules that her feet slid into. Neither girl wore a bra or panties.

While applying her makeup, Heather told her sister, "Set up the camera. Put it up on the little thingy on your dresser."

The first knock on the door was Mickey and Lance who resided in the dorm directly across from their room. They had sneaked in alcohol. The girls blended some mixed drinks and shared them with everyone. Eventually other guys showed up either as a pair or solo. Not all the guys in the hall wanted to participate but when the final count was tallied, lucky thirteen had filled the room and the girls hadn't gotten to know any of them beforehand except Mickey and Lance.

Heather informed the crowd of guys, "OK boys, here are the rules. My sister and I want it in the ass. We are safe and clean so nobody will used a condom. We are only doing anal so do not put it in our front. Use lots of lube...there are bottles sitting right there. Be respectful and we all should have a lot of fun. So who is going first?"

With the short skirt and dress with no panties, all the girls had to do was pull them up to allow access for the guys, where by then, were mostly standing around the room anxiously awaiting their turn. Heather and Maddie both got on all fours on Maddie's bed with their high heel covered feet hanging over the edge.

Two unknown guys lined themselves up behind each girl. The tall skinny blonde haired guy had the lube in his hand and dropped his jeans and underwear to the floor before profusely smearing it all over his hard cock. He slid his 8 inches inside Maddie's ass causing her to give a small grimace as it penetrated. He was loving the smooth textured friction on his prick but needed to see it disappear inside her butt so he gently spread her cheeks with his fingers as he pumped. He watched it move in and out.

The muscular guy had his shorts barely pulled down and driving his 6 inches up Heather's ass. The girls held hands for moral support and with heads turned, smiled at each other while soaking up her own pleasure. The muscular guy was the first to announce, "This slut's tight asshole is going to make me cum!"

From against the wall, his roommate who was now rubbing his own cock through his pants yelled, "Do it Tommy! Give it to her! Bust inside it!"

Tommy growled, "Fuuuuck! I'm cummin, boys! Yeahhhhhhhhh! Augghhhhhhhhhh!"

While Tommy finished shooting his load inside Heather's rectum, the tall skinny guy kept pumping away inside Maddie, letting out an occasional moan. Tommy's orgasm was too quick to allow Heather to have one first. He backed away and shuffled his feet allowing another guy to take his place. Another stocky blonde haired guy fumbled with his belt, anxiously trying to take his turn. When his pants were down, he ignored the frothy cum that had formed a circle around her ringed anus and pushed his 7 inches in on top of it.

Maddie was so close to orgasm that she ordered Tommy, "Come around here and put your cock in my mouth."

She didn't care that it was slimy and had just came out of her sister's ass. Maddie wanted that oral sensation to go along with the anal sex she was receiving. Putting himself on his knees up on the bed, Tommy was happy to feed his spent penis inside her requested mouth. She gobbled it and could taste the gooey juice all over the shaft.

Maddie was now being spit roasted and her pussy began to first tingle, then build. With a mouth full of cock, she could scream but only let out a muffled yelp when she orgasmed. She trembled and twitched but never once stopped sucking Tommy even as she squirted on the bed.

The second guy that had taken Tommy's place behind Heather was pumping roughly and within a minute, also exploded, yelling out, "Fuck! Fuck! Ohhh! I'm cummin! Ohhhh!" His orgasm triggered Heather's. She clenched in ecstasy.

Finally the first tall skinny guy fucking Maddie let loose and ejaculated inside her ass. He removed his hands from her hips, leaned forward and held onto her shoulders as he individually thrusted every spurt inside her with such force that she had to be careful not to bite Tommy's dick that was lodged in her throat.

Tommy's cock had grown back into a full blown hard-on. He held onto Maddie's ears and fucked her mouth with equal force which made it more difficult for the next guy to put it in her ass. Maddie didn't mind that every third pump gagged her because she couldn't get enough.

Heather was now on her third guy. He put her legs together and stood with his apart as he fucked her sperm slickened asshole. When Tommy let loose for a second time, he pushed Maddie's head completely down on his spurting manhood. Even with her eyes watering and her throat stuffed, she took his seed directly down her esophagus. She began to orgasm forcefully again ejaculating two large squirts, but could not verbalize it for obvious reasons. When Tommy pulled out of her mouth, a string of cum snapped off and hung down her chin.

While still side by side, Heather smiled before leaning in and slurping the hanging string. She followed it up with her lips like a strand of spaghetti before latching onto her sister's lips for a long kiss. When they broke their lip lock, Maddie said, "Mmmm...that is so good. I want more."