Entrapment

Three days had passed since Fluttershy had walked home topless. She was settling into her new life rather comfortably. She had done everything Malak had asked her, and he had been fair in his treatment of her. She was a little upset that he was the only one being pleasured, but his response to her had always been positive. She was happy that he was happy. That is, until today. Today, she wanted something from him.

As of this morning, she was allowed to freely walk around his house. She found him in the living room, writing something in a notebook. It was time to employ her primary tactic: asking politely. She walked up to him, kneeled down between his knees, and looked up at him. "Master Malak?"

Malak set aside his notebook. His letter to his mother could wait. "Something you needed, Fluttershy? If it's a companion, Nightshade will soon come by."

"Well, I was just wondering... I've been good, right?"

Malak smiled and patted her head. "You're a well-behaved and lovely mare. From the tips of your toes to the ends of your hair."

Fluttershy smiled. "When you first brought me home, you told me that if I was good, I would be allowed to see Applejack. If it's not too much trouble, I'd like to do that. You know, if it's not too much to ask."

Malak nodded. "I did say I'd reward you as such. And as your training goes, you've grown very much. This evening, I'm headed to see Jax at Kayson's request. I'll ask him then if he thinks that is best."

Fluttershy placed her cheek against Malak's thigh. "Thank you so much, Master. I really appreciate it."

"Now, Jax may not be in agreement," Malak warned. "When it comes to slave training, he's very vehement. He may ask you for a show of your skill, and though I do not doubt your sheer force of will, he may demand to take your behind, a task that you haven't yet performed, you may find."

The smile drained from Fluttershy's face. "So, he'll try to force himself up my butt?" Malak nodded in response. Fluttershy shivered. Malak had told her that she would need to learn this skill. She hadn't been looking forward to it at all. She didn't feel ready for this yet. "Master Malak, will it hurt?"

"You're not trained enough to take it in stride. But I can't help you once he's slipped inside. All I can offer is to train you for Jax. The yoga you've been doing will help you relax."

"How so?"

Malak pulled off his pants and grabbed a bottle of strawberry lubricant from a drawer in his desk. Escorting Fluttershy to the couch, he commanded her to strip. She did so, having spent all of yesterday walking around the house completely nude. She was growing bolder under his tutelage. He sat down, and she began to lick his shaft. She was becoming more familiar with his genitals, and knew exactly what to do when they were presented to her. When he was fully erect, he took her by the hand and lifted her up. He spun her around so that she was facing away from her, and brought her down so that she was sitting on his lap.

It was a new experience for her, seeing his dick poke up from between her thighs. Even when they slept, it was placed against her back. Reaching around her waist, he applied a bit of lubrication to his tip, then brought her hands down to it. She was familiar with the concept of a hand job, though all of her training thus far had been focused on her mouth. Still, she had no problem gliding across his skin, as the lube was very slick.

When he was completely covered, he leaned her forward, giving him access to her hind end. Despite her nervous whines, his fingers slipped inside of her easily, lubricating her insides. She squirmed and wiggled, but allowed him to continue anyway. It was only two fingers, after all.

Soon, he was done, and she relaxed. This didn't last long, though, as he lifted up her hips, and she remembered why he had been fingering her arsehole. He pushed her legs apart as wide as they would go, and gently lowered her down until the tip of his cock was resting gently against the entry to her colon.

"Relax and breathe deep, think a peaceful thought." Malak gently pulled apart her pucker with his thumbs. "That should make it easier as I enter this slot." With a soft, slow push, Malak's hard cock crept inside of her anus. Fluttershy gasped and whined at the feeling of being entered in such a way. It wasn't as painful as she had imagined, but it certainly wasn't pleasant. She had a lot of trouble breathing deeply, as her body wanted her to hyperventilate, and to push out the offending foreign object. Despite everything going through her head, she tried her best. When she finally came to a stop, she could feel his medial ring. She was halfway down.

Malak would give her a moment to rest. While he intended to have her take his entire length, he wasn't sure she could handle the whole thing in one go. Two steps seemed a more reasonable pace, as she hadn't even trained against his fingers very much. Still, she was doing well for her first time.

After a minute of respite, he began pushing into her again. As the two grew ever closer, Fluttershy's sphincter stretched ever wider. She didn't stop until she could feel his testicles gently pressed against her vulva. She took a very deep breath as she tried to relax. He had been right about the yoga.

Neither of them moved for several minutes. Malak wasn't wanting to strain her too much, and Fluttershy was scared of being in any more pain. She wasn't badly hurt, but this feeling of fullness was very unpleasant. Slowly, Malak brought his hand up to her chest, pressing her back to his chest as he leaned her into a reclined position. It helped a little, as she no longer had to devote any effort to balancing herself and could focus more on relaxing.

"Anyone home?" called a voice from the entryway. Nightshade had arrived.

"We're in here," called Fluttershy, unable to hide the whimpering in her voice. Nightshade entered to see their position, smiling as she approached.

"Master Malak, would you like some assistance?" she asked, licking her lips.

"No," responded Malak, gently spreading Fluttershy's labia with his fingers. "For now, you lick her. She's doing quite well, and a reward she deserves."

Fluttershy let out a loud moan as Nightshade began to eat her out. She'd never had this happen to her before. As the writhing mass of muscle bombarded her sensitive folds, she was overcome with pleasure, in stark contrast to the pain she was feeling in her arse. Before long, she squirted her own liquid all over Nightshade's face and Malak's hands. Neither of them stopped however, rubbing and licking at her unused vagina. She was so enraptured by it, she didn't even notice as Malak began to slowly gyrate his hips.

Before long, he was gently thrusting up into her, and she was loving every moment of it. She was starting to associate the feeling of having her arsehole stretched with the pleasure of cunnilingus. As she came for the third time, she could feel Malak shooting his load deep inside of her. He slid out with an audible pop, and gently picked her up as he stood. She was out of breath, and very much in need of a rest. He carried her to the bedroom, gingerly tucking her in. She managed a soft thanks as he exited the room, giving her the opportunity to recover while he was out.