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Teen in the Castle -4- Anal in the Morning

Adjusting to her new life style, Alyssa keeps practicing every day.
The last few days have been pretty hectic for Alyssa. The teen has been exploring new functions for her body, she had never imagined possible. Getting taught by Clover, Damien and Martin is certainly a great way to practice for her marriage. Although she has to keep her virginity until then, she now has a larger knowledge about men and how to please them. Alyssa had been such unknowing and innocent teenage girl, but since her first lessons with Martin one week ago, that all changed.


As it was still early in the morning, Alyssa found it a good time to raid the kitchen cellars. The teens weren’t always allowed to eat what they want, but Damien and Martin had showed her when to sneak in and get the goodies. As she was searching through some jars with cookies, looking for her favorites, Alyssa heard someone enter the room. She turned around. Oh thank god it’s Damien. If it had been Elory she would’ve gotten in trouble.”Good morning.” She called out to him.

“Hey.” By the way he walked up to her, Alyssa knew what time it was.
Damien was bigger than Martin even thou they were the same age . And he was a lot stronger too. As the other teenager confidently approached, the girl prepared her body for what was about to come.

“You’re taking cookies are you?” He snapped in an arrogant tone. The grin on his face revealed that he wasn’t actually angry, but was merely feigning his dander.
He took her by the waist, turned her around and firmly pushed her against the wall.
Not resisting anything, Alyssa tried to relax. She did find him a bit rough compared to Martin, but Damien could be nice as well.
“I’ll be taking your chocolate cookie first.”

He bent through his knees to reach to bottom of her dress. With one swift movement he pulled it up to her shoulders. To prevent it from falling down, he pressed his torso into Alyssa’s back. Trapping the young girl against the wall, preventing her movement.
His hands went down again. This time they grabbed her underwear. Damien pulled it down slightly, just far enough to reveal her buttocks.

She sensed him reaching into his pockets in search of something. When the boy found his handkerchief, he unwrapped some butter from it. By the time Alyssa realized what was happening, Damien’s finger was already covering her tight anus with the slippery paste. After he had smeared the outside of her anal ring, his finger pulled back. Alyssa readied herself for what was to come.

Damien made sure to fully cover the rest of his finger with the butter, after which he launched it into her tiny hole. The girl gasped for air. Trying to coat as much as possible of Alyssa’s insides, the finger wriggled around in her butt. Spreading as much of the ointment as he could.

Startled by the surprise invasion, her anus didn’t want to co-operate. Alyssa had lost full control over her contracting muscles, as her sphincter desperately tried to push the intruder out off her body. It didn’t work however, as the more she convulsed around his finger, the more eager Damien seemed to become to get in. Poking harder and deeper, until the finger fully entered her body, his knuckles pressing on Alyssa’s arse.

Damien used his other hand to open Alyssa’s left hand, giving her some new butter. He seemed to have butter stored in each of his pockets. Alyssa knew what it was for, Martin had taught her well. With his finger still inside of her tight butthole, Damien used his other hand to unbuckle his trousers and dropped them to his ankles. With the ample freedom she was given to move, Alyssa brought her hand behind her back and started to rub the butter around his throbbing cock. She knew that the better she lubricated it, the less pain the thing would bring as it entered her.

Alyssa had done her best to cover as much of the restless cock as she could, but Damien didn’t give her a lot of time. Eager to penetrate her ass, he removed his finger from her lubricated hole and pushed away Alyssa’s hand that was rubbing his cock. As she let go of it, his dick swung up, slamming in between Alyssa’s buttcheeks. The tip of his cock was touching the lower onset of her vagina. But Alyssa knew she didn’t need to fear for her virginity. Damien wasn’t aiming for her pussy.

The top of his cockhead had received the largest share of grease. Damien pointed it to the entrance of Alyssa’s backdoor. Automatically Alyssa spread her cheeks to give him easier passage. Without warning, unlike Martin, he violently started to push his cock up her hole. Alyssa had gotten used to letting her ass get stretched like that, but the speed at which Damien was entering her was unmatched by any previous session. A silent squeal escaped from her mouth as he worked his way up her teen body.

Once his entire cock had entered, she could feel his balls at her lips. The slapping of his sack again her naked pussy helped ease the pain as Damien pushed her harder against the wall. With each thrust, Alyssa felt her teen breasts squash into the cold stone. She tried to push herself away from the wall, but failed, he was to strong. For a moment she thought about asking him to stop, but Alyssa knew she had to practice. For when she got married.

Damien just kept pumping. He seemed to not notice how uncomfortable Alyssa was, the girl kept a stiff upper lip. The only thing he did know was, that she felt blissful around his cock. Her muscles tightening around him as he pounded, drove him mad with passion. As he took her waist, to lift her from the floor, he made sure to keep her pressed against the side of the room. Moving his legs and feet even closer to back her up, resulted in Alyssa being pinned up against the wall. Desperately she wiggled her feet around as she felt herself being thrust up in the air. With Damien being so much more powerful, the girl’s struggle didn’t have any effect. She was afloat, held up by the cock in her ass.

As the boy started to breathe heavily into the back of her neck, she remembered what Clover had said the other night. With the power she had left, Alyssa started contracting her sphincter even harder. After she had squeezed his hard cock for a while, she changed to pushing. It felt like a giant turd not wanting to come out, but in. Her firm convulsions were enough to take him over the edge. With one last thrust Damien made sure to bury his cock as deep as possible into the girl’s ass. His ball pressed against her lips.

As she heard Damien grunt, Alyssa felt his cock exploding in her rear body. The hot cream was as much of a relief to Alyssa as it was to him. The juices softened the firm cramp she had endured in her anal ring. Damien’s cum flowed through her bowels as he kept filling her up.

When he had fully unloaded into her, he pulled out. Alyssa landed on her feet, but fell to the ground as her legs had no energy left to carry her weight.

“You two give quite a show.”
It was Clover. Alyssa never heard her enter the room and didn’t know if she had been there for long. Looking up to her friend from the floor, Alyssa felt embarrassed. It seemed like the other girl always knew when she was messing around with one of the guys. Clover had caught her again.

“Maester Naelan wants to see you, Alyssa. You’d better hurry he’s not a patient man.”
The blonde explained as she looked down to Alyssa.

Damien and Alyssa didn’t say a thing as they fixed their clothes.
“You remember where he stays?” Clover added, not sure if Alyssa could find the way on her own.

“Ye.” She mumbled, still affected by the fuck she had gone through.
With her butt still filled with cum, Alyssa found the strength to stand up and set off.


“Open your mouth, stick out your tongue and say ‘a’.”
A small spatula pushed down her tongue as the master peered into her mouth. The maester was a peculiar old man, with a long beard and arms as thin as Alyssa’s. He looked more fragile than some of the vases her father used to merchant. Alyssa wondered if the big glasses he was wearing, weighed more than the man himself.

“Very, well. You’re as healthy as your old man ever was.”
Naelan was his name. Her dad had told her about him. They had known each other from before Alyssa had even been born. It was partially the maester’s doing that she was allowed to stay here in the castle.

“You can get off the table now, dear.” The Naelan continued as he kept examining her.
“I want to listen to your lungs, you can put your dress over there.” He ordained. Pointing at a wooden chair.

Alyssa pulled the dress over her head. She felt a bit uncomfortable in just her panties. But the maester was a friend of her dad, he just wanted to make sure she was healthy. As she hopped back onto the table, she could feel her guts rumble. Damien’s cum was trying to find a way out. Alyssa tightly pressed her butt together. The topless teen waited in silence for what Naelan was going to do next.

A cold metal thingy was pressed beneath her right breast. It was connected to the maester’s ears with some tubes. “Cough please.” Requested the old man. Alyssa coughed. The sudden jolt caused her butt to relax and she felt a drop of cum drip into her underwear. For some reason she couldn’t control her lungs and her butthole at the same time.
“Cough again please.” He had moved to the upper side of her breast. The mouse of his hand gently brushed her nipple as he moved the stethoscope. Alyssa coughed again. Her lower body grumbled loudly when she squeezed her butt together. No cum seemed to have flown out this time, at least none that she felt.
“Seems like your belly is a bit upset. Are you feeling well?” Naelan sounded honestly concerned about her well-being.

“Yeah, I’m fine. Just ate something wrong I think.”

“Ok, just had to ask. Your dad told me to make sure you were healthy.” Said the man as he put the stethoscope away. Alyssa was eager to get up and put on her dress again, but the old man stopped her.

“Your dad has also asked me for something else. I heard you’re getting married soon.” He paused and looked into her face. “Your father asked me to regularly check your hymen. We don’t want to risk finding a husband for you, just to find out you are not fit. Do we? You are still a virgin yes?”

“Yes.” Said Alyssa in a low voice.
Doesn’t my dad trust me? Or does he just want to make sure?

“Can you take of your panties?” The maester requested. Since Alyssa wasn’t showing any indications that she was going to.

“Uh, yes.” The girl stumbled.
Fuck. She went to sit a bit further onto the table, so he wouldn’t have vision of her butt. Alyssa guessed he would only have to see the front. Slowly she pulled of her underwear hiding the inside from his view. The girl wasn’t sure that there were cum stains in it, but she didn’t want to take the risk of looking. Maybe he would see them too.

The maester pushed her knees apart. Her naked pussy was now revealed to him. Clover had taught her how to shave down there. Everything was now so bare, so visible…
“Pull up your legs a bit.” Said the man, as he put his hands under her knees and already started pushing them up himself. Alyssa couldn’t remember ever feeling so exposed to someone like this before. With her legs spread like that, she had no control of her asshole. As the maester’s boney fingers started to investigate the inside of her genitals, Alyssa felt the cum slowly dripping out of her anus. Oh please, don’t see it. She was already planning to wipe the cum from the table with her panties, in one quick motion she should be able to jump off a clean table.

The old man stepped back. If he had seen the liquid, he surely kept a straight face about it. It seemed like he hadn’t noticed.
“Very well. Everything is how it should be.” It sounded almost like a compliment, the way he said it.

Alyssa closed her legs.
Took her panties.
Jumped off the table and turned around to clean up. Just like she had intended.
Or almost…

After the jump, as she was sliding her panties over the table, her guts rumbled again. Louder then both previous times together. She felt something escape her body. A trail of cum formed from her asshole, over her thigh, to the inside of her kneecap.

The old maester was right behind her. He had to be both blind and deaf to not notice something had happened. The naked girl didn’t dare to turn around. Some seconds passed, the man didn’t say anything. Maybe he hadn’t seen it?
Then Alyssa heard the old man speak in a low curious voice.
“What was that?”
She felt two boney hands grab her buttcheeks to pull them apart.

His face must have been close to her butt. He was inspecting her. But she couldn’t help it. As the old man spread her ass like that, there was nothing to hold back the cum. A loud fart sounded as Alyssa felt the white cream stream out of her body and splatter onto the stone floor.

To be continued…


Thanks for reading.

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For the people who’ve read my series ‘Vacation with Teens’, I’m currently deciding which one I’m going to continue. If you have a preference for either ‘Vacation with Teens’ or ‘Teen in the Castle’ Please let me know through PM. (Or comment)

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