Trained by a Succubus Ch. 02

Day 93

It'd been nearly three months since Jack had summoned Emily to his world, and two months since she had locked his dick in a little cage. The key, of course, was attached to a necklace so that it always hung between her large perfect breasts. Every time he saw them, he was reminded that she had complete control over him, despite being named master in their contract.

"Good boy," Emily cooed, "I'm almost there."

Jack found himself frequently dozing off in class since then. His mind always going back to the night before with Emily. Her smug face smirking down at him. The way her cock stretched his "boy pussy" as she called it. She even forced him to wear panties since she claimed he wasn't big enough to need boxers.

"I've got a big reward for you."

Even though Jack's grades were dropping, Emily kept him awake for hours each night to continue "training" him. And she'd cum so much that his ass or stomach was always full. He had to bring extra panties with him to change between classes since they'd get too wet from her cum dribbling out throughout the day. And when he got back to his apartment, she'd just fill him up again.

Splurt. Splurt.

Forgetting where he was for a moment, the memory of her warm cum filling his ass made him moan. The whole class went silent. Jack looked up to find all eyes on him. He cleared his throat, trying to ignore them, though he noticed the girls he knew had dicks were staring at him with lustful eyes. A few even had visible erections.

One of the other girls, Blair, looked concerned. She was a childhood friend of his, and one of the few girls in the school without a dick. Jack had a huge crush on her, but Emily was always so rough that he was too exhausted at interact with her as much. Ironically, he had summoned Emily so that when he would eventually ask Blair out, he'd have enough experience to satisfy her. Despite his size.

When class ended, three of the girls who had an erection earlier surrounded him. In fact, he could clearly see they still had impressive bulges down their pant legs.

"Hey, little guy." One of them said. "Want to come over to my place to study?"

"Yeah," said another, "All three of us are going."

"And we'd love it if a cute guy like you would join."

Ever since he met Emily, he noticed a change in how his classmates treated him. The guys started to distance themselves and the girls seemed strangely interested in him.

"Sorry, but I really must be- "

He was cut off as the first girl's arm slipped around his chest and pulled him close. Her breasts were large enough that they forced his head downwards.

"Come on." She whispered in a sultry voice that made his knees weak. Her free hand slid down to caress the front of his pants. "I promise we'll make you feel really good."

"If you're a good boy, that is." Said the second. She and the third girl slowly surrounded him. They were so close that all he could see was the immense cleavage from their low-cut shirts and their smug faces grinning down at him.

Jack gulped, knowing they wouldn't take "no" for an answer. Before he could respond though, he felt someone grab his wrist and pull him free. "Sorry, but we actually have plans."

To his surprise, it was Blair. The three women glared at her as she led Jack into the hall. He could hear them talking angrily to each other. Calling him a tease and Blair a flat bitch. Jack felt his ears turn red with rage from the second comment but stayed with Blair instead. Once out of view, she pulled him into a secluded closet. It was cramped, but still better than somewhere those girls could find him.

"Thanks, I owe you one." He sighed. "You really saved my ass back there. Literally."

Blair smiled up at him. Which was something Jack wasn't used to since most girls were incredibly tall. But Blair was someone close to his height, just a bit shorter.

"No problem." She pulled at her ponytail draped over a shoulder. A cute habit of hers. "I actually wanted to talk to you."

"Sure, I've always got time for you."

"That's actually what I wanted to talk to you about. I haven't really seen you the past couple of months, and when I do, you seem distant. Always quick to leave class. Taking days to respond to texts." Blair looked away and pulled at her ponytail more aggressively. "I thought we were close... or maybe something more than close?"

Jack didn't realize how close she physically was until now. The closet was small enough that the tips of their shoes were nearly touching. And with his slight height advantage, he could see down the front of her shirt.

"Well, I..." Jack stammered, not sure what to say. He liked her and wanted to be more than friends, but how could he explain Emily to her? "I've just been so busy with... uh... homework. And it's just left me exhausted, you know?"

Blair looked uncertain. As if she wanted something more from him.

"And well..." It was now or never. "I know I've been distant, but I do see you as a close friend...and maybe more if you wanted. I've been wanting to ask you about that, but wasn't sure how to- "

Blair placed a hand on his chest and kissed him. Softly at first, but it quickly became more passionate. As if a deep desire of hers had taken over. She forced her tongue into his mouth and pushed him against the wall. Caught in the heat of it, Jack went along. His hands awkwardly grabbed her waist. Then one of them moved down to grab her ass while the other moved up to cup a breast.

Her breasts were smaller than he was used to with Emily, but he didn't care. They were hers and that was enough. To Jack, she was perfect. As soon as he thought that though, a desire formed in the back of his mind. After all the time he spent with Emily, he had the urge to get on his knees and suck Blair's dick. Something she didn't have.

He didn't have long to ponder that new desire because he felt Blair's hand boldly slide between his legs. Jack's heart fluttered and his knees nearly gave out. The girl of his dreams was taking this far. And Jack desperately wanted her to, but as much as it pained him, he couldn't let her.

Jack immediately pulled back and gently pushed her away. If they went any farther, she'd easily notice he was wearing both a pair of panties and a cage. And he didn't know which one would be more awkward to explain.

"Sorry, that was unfair of me. I-" Blair turned and grabbed the door handle. "I should go."

Jack placed his hand on the door, breathing heavily, and gave her a quick kiss. "No, I'm sorry. I... do feel that way for you, I really do. But right now isn't a good time."

"So, you're saying we can do this another time?" Blair smiled hopefully.

"Definitely!" He said a bit too excitedly. Now he just needed to figure out how to explain all this to Emily. Despite how... intense she could be, he couldn't deny the fact that he liked her. And he'd miss her when their contract eventually ended. "I have a lot of homework this week, but you can come by any time after that."

Blair kissed him and playfully rubbed his crotch. "I can't wait."

Day 99

Emily forced Jack to his knees. Her massive cock dangled in front of him as she swayed her hips from side to side. Jack had to fight the urge to immediately start sucking it. He wanted to so badly, but knew he'd be punished if he did. The succubus smirked down between her breasts at him, waiting to see if he'd disobey.

"Good boy," she cooed. "Now, go ahead. Just like we practiced."

Instead of getting right to it, Jack placed his hands on Emily's hips and started kissing. Not her cock, but around it. Her toned stomach and down her thighs. Soft and gentle.

"Good, good. Just like that." Her cock twitched in excitement. "Remember to take your time and make her feel good. Girls love a slow buildup to get them in the mood."

Jack continued taking his time kissing and caressing until her cock started growing stiff. Then, he started kissing it from base to tip. Her cock was so big that by the time he reached the tip, she was fully erect. Jack gave the skin under the head a quick flick with his tongue, earning a grin from Emily.

"I almost thought you'd forget again." She teased. "The skin there is sensitive, so that tongue flick is sure to make a girl moan. Or maybe even cum if they're as small as you."

Next was the part Jack loved the most, but always had to hold back. He spat in his hands to lube them up, wrapped them around her cock, and then slipped her tip into his mouth. His hands stroked her length while his tongue lapped around her tip.

"Mmm, good boy." She hummed. Her pointed tail flicked back and forth happily. "You might not have any experience using a dick, but you've gotten damn good at sucking them."

Jack took her deeper, slurping and sucking loudly. He felt a spike of satisfaction as Emily ran her fingers through his hair and moaned softly. That was always the best compliment she could give him. It might not have been the most vocal of compliments, but to Jack, it was a sign that he was able to please her.

Emily's cock was big enough that even with both hands wrapped around it, there was enough of it for Jack to choke on. He was getting better at suppressing his gag reflex, but she was just too thick and went so deep that he couldn't help it. He gagged hard, causing it to twitch in his throat.

"Don't be ashamed." Emily stroked his cheek soothingly. "Gagging is just a way of complimenting a girl's size."

Jack leaned into her hand and gurgled happily. With renewed vigor, he took her in deep again. He gagged over and over until he could force her down his throat far enough that his lips could reach the first hand wrapped around her length. The first goal. He released that hand and placed it on her hip for support.

"Almost there, master. Just a few more inches." Emily cooed. Her thumb gently stroked his cheek. "If you can finish without messing up this time, I'll return the favor."

When she started training his oral skills, Jack didn't realize how difficult it was to force a cock that large down his throat. It was one thing when Emily would fuck his throat since she'd force it down him. But it was different when he had to choke on it himself.

Jack gagged and slurped her deeper. Each bob of his head made his spit dribble down his chin and lubricate her cock. Emily gently swayed her hips back and forth, clearly trying not to ram it in herself. Part of him wished she would. Something about being used that way made him excited. But he also wanted to prove that he could give her a proper blowjob.

After a few more attempts, Jack managed to reach his other hand wrapped around her. He let go and instead used that hand to fondle her balls, which were large and heavy. Filled with the cum he wanted so badly.

Emily moaned softly in appreciation. It wasn't something she said was required, but it was extra points. He looked up between her breasts to see her reaction, but they were so big that they blocked most of her face. One of her hands fondled a breast and all he could see were her eyes filled with lust and pride.

Jack took her deeper as tears ran down his cheeks. Each inch he took was more difficult than the last. And the closer he got, the more he could feel her throbbing. Until finally, unable to breathe, he felt his lips reach the base of her cock. His nose poked her firm stomach.

"Wait, not yet." She placed a hand on the back of his head to stop him from backing off. "Don't you want to savor the moment? Feel the accomplishment of giving a perfect blowjob?"

Jack tried not to struggle, but he desperately needed air. She held him there with a firm hand as the edges of his vision started going dark.

"Mmm, I just love the way you look with your lips around my cock." She was breathing heavily. "But you aren't done yet. I still haven't cum."

Emily gave him enough room to back off and take a deep breath, and then rammed her cock back down. Now that he had proven himself, she didn't care anymore. She fucked his throat, balls slapping his face, until she blew her load. After which, Jack continued to softly suckle her tip to make sure he got every drop.

"Open." She placed a hand on his cheek. Jack opened his mouth and Emily slipped her thumb in to move his tongue around. Once confirmed he swallowed her load, she rubbed her thumb along his lower lip. "Good boy. Good little cocksucker."

Jack's head began to swim as it usually did after she fucked him. Her hot cum in his stomach made him feel warm inside, but also made his dick twitch painfully in its cage. It begged for some sort of relief.

"Since you did so well, I guess I can give you your reward."

Emily picked him up from under his arms and tossed him on the bed. He landed face down but didn't move. His body had a hard time moving properly in his state. Instead, he let Emily lift his ass and spread his legs while his face stayed snug against the sheets. Jack expected her to slip her cock in as his reward, but she surprised him.

With cheeks in both hands, Emily spread his twitching hole and jammed her tongue in. Since the day she first fucked him in the ass, she made sure he kept everything clean. And she really meant everything.

Emily giggled as her tongue made him squirm. Jack had almost forgotten that succubi tongues are unnaturally long. Even longer than his dick. She'd also hummed happily as she worked, which made her tongue vibrate in his ass. Jack couldn't hold back anymore. His little dick started dribbling all over.

"You know," Emily slipped her tongue out and inserted her middle finger, making Jack moan into the sheets. "Sometimes I don't think you want to fuck me."

She gently slid her finger in and out. Her pointed tail wrapped around his upper thigh to occasionally fondle his balls.

"Except for your blowjob, you haven't made any progress with your training. Your little dick hasn't been touched in two months, I fuck your ass for hours every week, yet we still haven't gotten any closer to fulfilling our contract."

She started thrusting faster, making sure to rub his prostate every time. Jack squirmed and moaned. It felt so good, but it wasn't enough.

"I guess it's understandable," she laughed. "If you like my cock that much, you'd rather be fucked by it instead. But don't you even want to get your dick wet? To know what a pussy feels like?"

Emily slipped in another finger. Which felt amazing on its own, but his ass exploded in pleasure when she spread her fingers apart—stretching his ass.

"I mean, I don't want to give up this ass, and it'd be almost impossible for someone like you to find a girl who'd enjoy a dick this small."

In the back of his mind, that made Jack remember Blair. He wanted to say he did have someone, but Emily increased her speed. Thrusting her fingers fast and deep, aggressively rubbing his prostate. As fast as he remembered Blair, he forgot about her.

"Guess it can't be helped," she said nonchalantly. "Men are just little toys for women with proper cocks to play with, after all."

Satisfied with her work, Emily slipped her fingers out and stood up. Jack felt her cock slide between his cheeks. It rubbed back and forth, reminding him of its size. Then, her tip pressed against his hole.

"Speaking of which, it's time for me to play with mine."

Day 100

Classes were over for the week, and today was the day Jack would finally tell Emily. He was still upset he didn't tell her the night before. Despite his feelings for her and the way her cock made him feel, Blair was more important. Emily would be gone after their contract, but Blair would always be there for him.

Jack entered his apartment, and the scent of Emily's cum immediately made his dick excited. It throbbed and struggled painfully in its cage. Though after the past couple of months, he no longer had the itch to stroke it anymore. Instead, his asshole twitched for something to pound it.

Strangely, Emily didn't greet him. She usually pounced on him at the door to begin his training, but today she wasn't even in the room. Down the hall, Jack could hear her talking. As far as he knew, no one should be able to see or hear her. He quietly made his way down the hall and noticed the door to his bedroom was cracked open.

"Mmm, yeah." Emily moaned. "I'm almost there."

Jack slowly pushed the door open to find Emily standing in the middle of the room, facing away from him. With legs apart, one hand on her hip, and the other moving furiously in front of her crotch.

For a moment, Jack thought she was jerking off but then noticed someone on their knees in front of her. He couldn't tell who it was, but they were clearly sucking Emily's cock.

"Emily?" Jack asked.

"Hmm? Oh, just a second." Even from behind, Jack could tell she was getting ready to cum. The girl gagged as Emily filled her stomach. She tried to pull back but did so a moment before Emily finished. The succubus' final load splattered across the girl's hidden face and small breasts. Wait...

Emily sighed in relief and stepped over the girl to sit on the edge of his bed. Her legs spread and her impressive cock still hard. "Need something?"

Jack couldn't believe what he saw. On her knees, covered in Emily's thick cum, was a shorter girl with small breasts and a ponytail.

"Blair?"

"Hey... Jack..." She said between gasps. Drool and cum ran down her chin and breasts, and tears down her cheeks. A position Jack knew all too well. "Surprise......"

"I don't understand," Jack said quietly. He wasn't sure how to feel. "Why are you- "

"Why?" Emily interrupted. "To have sex with you, obviously. She came by looking for you, and I couldn't turn away a pretty girl like her. Not when she has an ass like that."

Blair nodded quietly. "I thought if you were having that hard of a time studying, I'd come over to help and... thought we could do a little more."

"She can see you?" Jack asked surprised. He was touched that she came over because she was worried about him, and wanted to sleep with him, but there was too much happening.

"It'd be hard to suck my dick if she couldn't." Emily shrugged. "And you're lucky you came back when you did. I was planning on fucking her pussy next."

Jack blushed at the thought of that. "I thought only I could see you."

"You were," Emily grinned, "until you took my cock in the ass like a bitch. That brought me closer to your world. Now anyone you're romantically interested in can see and feel me. Like Blair, who introduced herself as your girlfriend."

"I'm sorry." Blair looked away ashamed. "I tried to say no, but when she pulled her cock out... I just couldn't say no."

Seeing the look on her face was like a stab in the heart. Jack rushed over to her and wrapped his arms around her. It hurt to see Blair with someone else, but he couldn't blame her. He knew exactly how hard it was to deny Emily's cock. The sight of it would get anyone on their knees.

"Shh." He whispered. "It's okay."

Blair hugged him back, trying not to think about the fact that this was the first time he saw her naked, but also relieved that he understood. They held each other until Emily stood up and pulled them apart.

"How cute." Emily tossed Blair onto his bed and then forcefully stripped Jack down to his panties. Blair's eyes went wide in surprise and her face turned bright red, but she didn't say anything. Then Emily tossed him on the bed next to her, "But right now, Blair and I have a contract to fulfill."

"A contract?" Jack asked confused. "You can have more than one?"

"Of course." Emily made a show of removing his panties as if showing Blair how far he'd fallen. Then, she took the chastity key off her necklace and reached between his legs. "As long as they're someone who can see me, that is."

She played with his balls for a moment and then unlocked his dick for the first time in months. The fresh air felt amazing. Jack half expected his dick to get hard now that it was free, but it didn't. Even when Emily gave it a few strokes, nothing happened.