Anal Academy

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May 18, 2021 // By:analsex // No Comment

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Heather and Madison were sisters and only 14 months separated them in age. Heather was the older one and at age 19 had finished her first year at Harvard University while Madison had just graduated from high school and had gotten accepted at the prestigious college so to follow in her sister’s footsteps. Madison or Maddie as she was called, looked up to her older sister and since they were so close in age, they were best friends as well. Even that year they spent separated while attending their respective schools, not a day went by where they didn’t chat online or communicate on their phones.

Both girls looked similar and sometimes were mistaken for twins. With their middle-of-the-back length dark auburn red hair and greenish eyes, they both were drop dead gorgeous who had boy after boy chasing them. Heather stood 5’5, with hazel eyes and was a toned 125 pounds from playing Women’s Lacrosse for the Crimson. Her natural D breasts slowed her down on the field but her thin waist and round butt gave her good leverage and agility. She received a half paid academic scholarship and earned a 4.0 GPA her first year to keep it, while studying Pre-Med.

Maddie was not as athletic but equally beautiful and intelligent. She was slightly smaller in stature at 5’3, 115 pounds with perky 34C breasts and had actually performed two shoots as a retail clothing model in a prominent magazine when she was 15. Both girls were sweet and even though Maddie wasn’t as outgoing, they both were on the correct path to becoming something special.

With all their similarities, there was one characteristic that made them different and that was sexual prowess. Heather loved guys and was very promiscuous from an early age. Even though she had many outside interests, there was nothing she loved more than feeling a nice hard cock sliding in and out of her pussy. She had no trouble getting it from college guys and she took every advantage of it. Even as a late teen, she could have powerful orgasms which only fueled her sexual appetite.

Maddie had a boyfriend named Colton that she had dated since her freshman year in high school. They were serious and once she turned 18, she had given up her virginity to him mainly because of his multiple requests. She liked it but didn’t want their relationship based on sex and feared a life goal-hindering pregnancy, so they rarely did it. In spite of her young age, she was more the romantic type and he was always required to wear a condom.

Heather thought her powerful orgasms could not get any better until she tried something different. Towards the end of the university school year, she hooked up with a senior athlete who was on the rowing team. He talked her into trying anal sex and at first she was squeamish but once they got going, she absolutely loved it. She had no idea how good it was going to feel, judging from many of her girlfriends’ opinions who had told her about the pain, but soon discovered it was amazing. She felt none of the discomfort and had the best orgasms of her life.

After that day, she preferred anal sex to vaginal and most guys had no problem with her desire. One such incident that led her into trouble was also the same incident that opened up a new sexual world for her. It happened to be the next to the last day before summer break and many of the students either had one more final exam or had finished. Heather had one last test and was inside the university library studying for it.

A third year Pre-Med student named Bradley whom she knew from a couple of study groups, came up to her table to chat. They hit it off and they both felt the other was attractive. When the conversation turned more into flirtatious sexual innuendos, they moved it to another floor in a rarely used aisle of books. The kissing started and soon Heather had her pants off with one foot up on a bookshelf while Bradley’s pants were around his ankles, pounding his seven inches into her ass like he was angry with it.

She was trying to keep her voice down, as she quietly moaned in a whisper, “Oh God! I love it in my ass! Keep going…I’m close!”

He was also whispering while huffing, “Take it baby! You like this big dick in your asshole, don’t ya?”

The entire bookcase was rocking and even a couple of books fell. Heather’s moans got a little louder when she began to orgasm. That big meat was jarring it out of her and soon after, Bradley let out a loud grunt, “Yeahhhhhhh! Auuughhhhhhh!”

Just as his cock released its last spurt into her rectum, a security guard cleared his throat, “Huh…ummm!”

Both their heads snapped around and were horrified. They were busted and after pulling up their pants, they were escorted to a holding room where their names were taken down in spite of their pleas.

“If you let us go, we promise never to do it again. I swear,” the desperate Heather begged.

Bradley was just as worried, “We are so sorry! Please let this one go. We made a big mistake.”

The security guard listened bahis firmaları to the pleading coeds but knew if the Dean of the school found out he had just let them go, he might be fired. He had a family and needed his job but was sympathetic to young college students and their crazy antics. He decided not to call the police but called Dean Anderson to decide their fate.

Within the hour, the Dean had both students into his office. After a stern lecture and a requirement to sign a letter of apology, he told them that if they performed a community service project the following school year, then they would have served their punishment and no expulsion sanctions would be handed down. Bradley couldn’t get out of there fast enough while Heather stayed back and continuously thanked Dr. Anderson.

She showed her gratitude, “Thank you Dr. Anderson. Whatever you have in store for me, is fine. I just appreciate you not expelling us.”

The Dean became brave and boldly asked, “Anything? I would like to ask you a personal question. Mr. Bell our security guard happened to mention that you and that young man were engaging in anal sex when he caught you. Is that something you practice all the time?”

Thinking it was none of his business but she didn’t want to upset him, so Heather uncomfortably responded, “Uh…I think at this stage in my life, I enjoy it. What does that have to do with anything?”

He continued, “Well perhaps we may have found your project. I am starting a club with a few girls next year. So far we have only three members but I hope to increase that number before fall registration. I call it Anal Academy and it is for girls who love anal sex.”

Heather questioned it further only to have Dr. Anderson answer all her questions. The more he spoke, the more intrigued she became. There were going to be a series of challenges throughout the school year only to end in a huge anal gangbang party. Because of their conversational content, she began to see him in a different light. He was more of a man rather than an administrative official.

She found him attractive. Dr. Anderson was only 38 years old and the youngest dean in Harvard history. He was 5’10 with dark hair and weighed 190 pounds. He had a rugged scholastic look which meant he was a hot manly nerd. Heather’s demeanor began to change from a scared student awaiting her discipline to the gorgeous young coed she knew that she was.

Her thoughts drifted for a moment when Dean Anderson asked, “So what do you say? Do you want to be a part of this club as your service fulfilment?”

“If I agree, will that be the end of it and I can go on like before?” She asked.

Dr. Anderson agreed, “Sure. You have my word. If you know anyone else that might want to join, we need more girls.”

Heather immediately thought of her sister Maddie and was going to use the summer to approach and possibly recruit her. The Dean once again interrupted her thoughts, “Before you do this, I need to find out if you are serious about your love for anal sex or are you just telling me that to prevent disciplinary action. We probably should do something right now for proof.”

She was taken back by his brash request. Was he blackmailing her? When he asked her again, she began to reason with herself, “Well, if I will be doing these things during my Anal Academy initiation, then would it hurt do to it now?” She hadn’t orgasmed when she was caught by the security guard and Bradley had shot his load into her so she was still unsatisfied and reasoned with herself, “Maybe it would be a great release to do the Dean?”

She agreed, “OK but where do you want to do it? Right here in your office?”

He nodded and then locked the door. For the second time in less than an hour, Heather was removing her pants while still on campus. She draped them over a chair and stood in her shirt and panties which by that time were wet in the back. She almost felt she was disrobing for a doctor but this doctor happened to be a PhD. Holding onto the back of that same chair, she slid her panties off and she could see the creamy wet spot in the back where Bradley’s semen had oozed out.

She couldn’t help herself so she licked the slime off the silky material before sitting them down. Tasting the salty goo fueled her fire and increased her desire for more. When she turned around, the Dean was standing before her, naked from the waist down.

Her eyes widened like she had seen a ghost when she saw his massive hard-on pointing skyward. She commented in amazement, “Oh…my…God! Are you for real? That thing is huge!”

Dr. Anderson laughed and tapped it a couple of times causing it to sway side to side while responding, “Nine and three quarters inches long and four inches in diameter. It is a blessing and a curse. I love the thought of having anal sex with someone but I have never had a woman brave enough to take it. I was hoping you would be my first.”

With a large uncertain sigh, Heather replied, “I love kaçak iddaa anal sex and have powerful orgasms with it but I don’t know about that thing. You might tear me up with it.”

He gave his idea, “How about we try it and see if you can take it and if you can’t, we will stop?”

Giving it some serious consideration, she asked, “Do you have lubrication because there is no way I’m trying that without it even with cum already in my booty?”

He smiled, opened his desk drawer and pulled out a bottle of Penchant Premium lubrication while explaining, “I just happened to have some. I had one of the other girls you will meet during Anal Academy in here prepared to do the same thing but when she saw my size, she said she would need more time.”

Even though she was apprehensive, Heather also was intrigued. She knew that the full feeling she received from anal sex created the perfect vibration in her vagina which in turn gave her amazing orgasms. She gave strict instructions, “Let me control it going in. Go very slow and if I say stop, then stop.”

After deciding on the most optimal way of trying to take it, Heather chose to put her knees on the big leather chair while holding onto the back rest. She spread her legs as far as they would go, arched her back and gave the OK, “Lube it really good, then come here and put the head up against my hole.”

Dr. Anderson coated his entire cock with the lubrication two times over. It was so slippery, it looked wet under the light. He stood behind her and placed the large mushroom up against her previously used sphincter. It had given Heather a little relief knowing it had just been stretched and inseminated by Bradley or she might have changed her mind.

He warned, “Get ready hon…you better take a deep breath.”

Heather took two small breaths before a sizeable inhale, “OK…put it in.”

Dr. Anderson took hold of her thin waist and began to slowly push. The head stretched its way through until Heather yelped, “Ouch! Ouch! Ouch! Take it out!”

The Dean pulled it out to give Heather her much needed relief. He dejectedly said, “Damn! At least you tried to take it. I thank you for that even if it didn’t work out.”

With her knees on the edge of the chair, she was holding her asshole in pain and looking between her legs, “Hold on! Who said it didn’t work out? I just need to rest a second and we are doing it again and we will keep doing it until we get it in.”

Dr. Anderson perked up with surprise and gratitude. The second time he managed to get it in a little further before being ordered to pull it out. The third time was a charm and he was able to get his beefy hog all the way up her ass.

She was panting and ordered, “Hold it right there! Let me get used to it and then you can start.”

He thought her snug rectum wrapped around his huge penis felt amazing. The tight warmth gripped it like it was the most perfect sensation in the world and he was so grateful that he was able to finally experience it. Just when he thought it couldn’t get any better, he moved his hips. It was like velvet!

She cried out, “Ohhh! That feels fucking wonderful! Ohhhh! Ohhhh! Ohhhh!”

The Dean was finally getting to drill his big cock into a tight, round bubble butt of a stunningly gorgeous redheaded 19 year old girl and the most amazing part was she also loved it. He thought he had died and went to heaven. Apparently he couldn’t hurt her with it so he fucked her with reckless abandon.

That pressure was building Heather up to an earth shattering orgasm. Her breathing became shallow and irregular. She exhaled and then her entire body began quaking. Her legs were contracted and she squealed into the head-rest leather! She thought she might pass out it felt so amazing!

He was working up a sweat and was getting close himself, “This is great! Your ass is so tight! I can’t believe how you are taking me! I’m going to cum inside your gorgeous ass! There we go! There we go! Augghhhh! I’m cumming! Augghhh! Uhhhhhhhhhhh!”

When he released his spunk, Heather let out another yelp while climaxing even harder than her first one. Involuntarily, she collapsed to her side on the chair, causing his dong to slip out, leaving a gooey gaping reddened hole. She continued to shiver in pleasure even after the fucking had ceased.

Both she and Dr. Anderson had the best orgasm of their lives. Neither knew what to say but no words were necessary. Finally, after a minute of a quivering recovery, the Dean sighed, “Whew! That was amazing! I have never exploded like that. Thank you Dear for that gorgeous ass of yours.”

She agreed with him and after dressing, headed back to her dorm. It was tough to study for her last final exam with Dean Anderson’s semen running out of her butt. The next morning, Heather took her final, finished packing up her things in her car and headed home for the summer.

Upon arrival, she was happy to see her family. She and Maddie had fun chatting and catching kaçak bahis up because they hadn’t seen each other since Christmas break. The entire family went out to eat and had a great time. While at dinner, Heather whispered to her sister, “I got something to discuss with you when we get home.”

Once they arrived home and settled in, Maddie wanted to know what Heather wanted to tell her but Heather wanted to wait until their parents were in bed. Finally around midnight, the girls ended up in Heather’s room sitting on her bed. Maddie was wearing a long Goo Goo Dolls t-shirt with white cotton panties and white socks scrunched down around her ankles while Heather was barefoot and wearing silky pajama pants with a comfortable white spaghetti-strap camisole top.

With her legs crossed Indian style, Heather kept her voice down to make sure their parents could not hear, “Have you and Colton ever done anal?”

Shaking her head, Maddie responded, “No. We have never even thought about it. It seems like it would be too painful.”

Heather became a shade louder with excitement, “Sis…sis…sis! That isn’t true! Oh my God, it feels so amazing! Ever since I started doing it, I don’t want to do anything else. Keep this to yourself but…I did it with the Dean of the school!”

Maddie’s eyes widened in curiosity, “What?! Are you serious?! How did that happen?”

Heather giggled then began to reveal everything from switching over her preference to anal sex to the library incident to fucking the Dean in his office. Maddie listened with her mouth hanging open. Heather then told her about Anal Academy and how Dr. Anderson wanted her to also join. Maddie was unsure about that and needed more than just being asked to be persuaded.

Heather got off the bed and reached into one of her suitcases. She pulled out a six inch thin dildo much to her sister’s surprise. Heather suggested, “I think we should try it on you. You will see, once you try it, you won’t want to go back.”

After a little persuasion, Maddie agreed to try it. Heather greased up the dildo with a glob of Astroglide. While on all fours, Heather pulled up Maddie’s long shirt to her waist, slid her panties to the side and slowly twisted it at the entrance. As she slid it in her sister’s virgin asshole, she assumed that Maddie would stop her. She didn’t and once it was buried, Maddie sighed, “That didn’t hurt at all. That actually feels great. Fuck me with it.”

Heather had Maddie turn sideways so that she could sit down on the bed while she did it. Once again, Heather was sitting comfortably with her legs crossed behind her sister. She started moving the dildo slowly, fully expecting Maddie to wince or tell her to be careful but once again Heather was shocked when Maddie instructed, “Do it faster and harder.”

As Heather picked up the pace, Maddie enjoyed it more and more. The smooth rhythmic friction that rubber cock was creating in her booty was so pleasurable, she approached orgasm within minutes. She never really had orgasms with her boyfriend but that was vaginal intercourse. She was in heaven and suddenly spasmed, “Ohhhhhh! What the…Ohhhhhhhhh!”

When she began to climax, a stream of lady juice squirted onto Heather’s bed. It startled Heather and she stopped pumping much to her sister’s plea, “Don’t stop! Keep going! This feels insane!”

Heather obeyed her sister and kept thrusting the dildo into Maddie’s rectum. Every minute or so, Maddie would squeal and ejaculate onto the bed. She was like a timed geyser. Finally, Maddie pulled away and fell into the puddle, a quivering mess. It was the most incredible feeling of her young existence.

Heather was excited for her sister because she had introduced her to anal sex but was concerned for her bed. She quickly had Maddie get up so she could gather all the bed covering for the wash. The girls had to flip the mattress over to allow it to dry. They giggled and discussed anal sex further. Maddie wanted to know more about Heather’s exploits with the Dean and other guys on campus.

From that evening forward, Maddie was hooked. The very next day, she and her boyfriend had anal sex in the back of his car. She squealed and climaxed several times before he shot his load inside her ass. When she got home that night, she couldn’t wait to tell her big sister.

This time, they were in Maddie’s room when Heather asked, “Did you like it?”

Maddie responded, “Oh my God! I loved it. I can’t believe I haven’t been doing it all this time. Thank you for showing it to me.”

Heather was beaming and she asked, “Let me see it? Let me see your asshole?”

Maddie pulled her jeans off and when her panties followed, Heather used her thumbs to spread Maddie’s ass cheeks apart. Maddie was standing and bent over her dresser while her older sister inspected her anus. Heather relayed, “Yep, it is gaped a little. There is still so much cum running out. Can you feel it?”

After Maddie giggled her affirmation, Heather found that gooey stretched hole just too tempting. Keeping it spread open, she leaned in and sampled just a small speck of sperm with her tongue. It was still warm and tasted a perfect blend between sweet and salty.

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