Day 1

Jack finished drawing a chalk rune on the ground. If this book was right, he’d summon a succubus. He was already in school but hadn’t been able to lose his virginity. For a man, his dick was pretty average. A little above average if anything. But since Matrovirans had enormous cocks, it was hard to get laid.

He figured that if there was one sure way to lose it, it’d be from a creature specifically bred to take men’s virginity. Like any sane man would do. Jack grabbed a garnet off his shelf and placed it in the middle of the rune. It began to glow a deep crimson and the floor began to warp.

It opened a hole to show a dark endless abyss. And in that darkness, a figure emerged. It was a woman. A tall woman. She had to be nearly seven feet tall. Once he got over the height, his cheeks flushed at the rest of her. She was slim with killer hips and larger breasts.

The hole snapped shut and the woman landed on the floor. She looked him up and down, like she was trying to judge his worth. “You’re the one wanting a contract?”

“Contract?” He asked confused. The book hadn’t mentioned that.

“A contract.” She raised an eyebrow. “When I’m summoned, I make a deal with my summoner, who will be my temporary master. I will do something they want as long as they do something I want.”

“Oh, that’s easy. I want you to take my virginity. Any way you want. In return, I’ll do whatever you want.”

“That’s it?”

He nodded. “That’s about it. I just don’t want to be a virgin anymore.”

The succubus grinned at him and licked her lips seductively. She pulled out a paper and pen. “This states, according to what you’ve said, that I will take your virginity any way I want. And likewise, you’ll do anything I want. Sign your name and this deal will be unbreakable.”

Jack felt a bit unsettled having to sign an actual contract, but it was worth it. He took the pen and signed his name. The contract vanished immediately.

“All right then.” She clapped her hands together. “Let’s get rid of that pesky virginity of yours.”

She pulled him close. Their differences in height were so great that her bare breasts loomed over him. Noting the problem, the succubus picked him up with ease and set him on the table. Then, she kissed him passionately. Her tongue forced its way into his mouth. She tasted sweet. And he could feel something…

The succubus undid his pants and his dick sprung out. It was already hard. She pulled his pants and underwear off completely and flung them across the room. After that, his shirt went too. Now he was naked in front of a very attractive woman who wanted to bang him.

She was topless, but not naked. Below her waist, was a pair of tight mini-shorts and thigh-high stockings. Instead of taking those off as he expected, she got on her knees.

“You know, the saliva of a succubus acts as a strong aphrodisiac.” She smiled. “One taste and you’re as hard as you can possibly be. So don’t feel ashamed for getting so hard from your first kiss.”

A lone finger trailed up and down the short length of his dick. “How big is this little guy? Three inches? Four? Well, I guess you are a man after all, so I shouldn’t expect too much.”

She moved down and licked his dick, her tongue circling the tip before wrapping her lips around it. Her mouth was warm and wet and made him feel amazing. He’d never felt anything like it before. As the succubus sucked on it, her tongue teased the sensitive skin at the tip, causing him to suddenly cum.

“Already? I barely even touched it.” She didn’t seem disappointed though. If anything, she looked excited. “Men on this planet are such quick-shots.”

Jack’s dick went limp. It at all times needed some time to calm down before he could get hard again, but that didn’t stop the succubus from trying. She spat in her hand and stroked it. “W-wait. It’s too sensitive down there to keep going.”

“Hm?” She looked unconvinced. “But it’s already hard again, see? All I had to do was stroke it and play with your cute little balls. I guess I know another way to get you off without touching it since you’re so worried.”

“What do you…” Jack’s eyes widened as she pushed him back and flipped him over onto his hands and knees.

Her pointed tongue prodded against his inexperienced asshole until it forced its way inside. Jack clenched his fists. She’d stopped jerking his dick, but she still firmly held it and used a thumb to gently rub behind the tip.

“Feels good, doesn’t it?” Somehow, the succubus was able to talk while using her tongue. Her voice made it vibrate in his ass. “This is where men are the most sensitive, after all.”

Jack didn’t say it, but he had to admit to himself that it felt surprisingly good. This wasn’t how he planned things to go. He wondered she’d bounce on his lap until he came in her. Instead, he found himself cumming on the table from her tongue up his ass.

“Good boy,” she cooed. “Just a few more rounds and you’ll be ready.”

Jack panted, trying to get his thoughts together as the succubus looked down at him with an insatiable hunger. “I can’t keep doing this. It’s too much.”

“Fine, fine.” She waved dismissively. “I guess since you’re a virgin, you don’t have enough stamina yet. We’ll pick this up tomorrow then.”

“T-tomorrow?”

The succubus nodded innocently. “Of course. You haven’t lost your virginity yet, so the contract hasn’t been fulfilled. I’ll need to stay here until it is.”

Day 7

The succubus, Emily was apparently her name, couldn’t be seen by other people. Only Jack. She spent the next few days following him around campus. It was hard to focus on classes when a topless woman was at all times in sight. Sometimes she’d tease him by rubbing the front of his pants or sucking on his neck. The most distracting thing she’d do was sit on the desk in front of him and play with her breasts.

When asked about when she’d take his virginity, she’d simply say he wasn’t ready yet. Instead of fucking him, she’d use other methods to get him off. Hands, tits, mouth, anything except her pussy or even her ass. It made him feel more like her toy than her master.

Jack sat at his desk, trying to focus on his homework. His zipper was down, and his little dick was out as Emily licked it like it was a piece of candy. Occasionally she bounced it side to side with her tongue. That was long enough that it could wrap around his dick and stroke it.

Her devilish tail flicked back and forth contentedly. She like to make it tease him when she toyed with his dick. It’d dart out to flick at his nipples, or if he was laying down, prod at his asshole. Like every time she played with him, he came too soon.

“Jeez, master.” She complained with a smile. “It’s already been a week and you haven’t improved at all. If I’m gonna take your virginity, you need to be able to fuck me properly.”

“I-I’m trying.”

“I know, little guy. I know. If only you were a little bigger down there, I’d fuck you right now. But since you’re so small, you need to make up for it with endurance.”

She got out from under the desk and stood behind him. Her arms draped around his neck. “Look at it this way. Not only will I have a good time at the end, but you’ll also be able to please other women once I’m gone. It’s a win-win.”

Emily kissed him deeply, her saliva making his dick hard again. Her hands rubbed at his nipples until they hardened too. Then she rolled them between her fingers. In a swift motion, she slipped his pants and underwear off so her tail could tease his little hole.

Jack didn’t know how long he’d last with this much input. The succubus didn’t even need to stroke his dick or anything. Once she licked his ear, it was too much. He came again.

She sighed, sucking on his neck. “That one was even faster, master. We can’t stop till I’m satisfied with you.”

Day 14

“Come on, master,” Emily said while stroking his dick. Her pointed tail prodded at his ass, threatening to push in at any moment. “Just a little bit longer. You’re so close to breaking your record!”

Jack breathed heavily, desperate for release. After the past two weeks, he’d figured out that he can not break his record. She wouldn’t let him. When he was close, she would just slip her tail inside his ass. No matter how hard he tried, he couldn’t last a minute, let alone the five Emily had set as the first benchmark. The record be damned, he needed to cum now. He moaned, trying to form the words.

“Or could it be that you want to cum instead?” She teased. Jack mumbled incoherently at her. “I can’t just let you cum, master. You need to convince me. Beg for it.”

“I-I wanc…um.”

“What was that?” She grinned. “I couldn’t understand you. Are you begging me to let you cum? Would you be my little bitch for such a tiny bit of relief?”

“Please!” He moaned. “I want to cum!”

“I guess I can let you cum, bitch.” She sucked on his neck as her tail hovered closer. “Though it’s kind of pathetic that your little dicklet can’t last any longer. It’ll take quite a while till I’d consider letting you fuck me at this rate.”

Her tail moved away from his ass and was replaced by her fingers instead, she used his precum to lube them before ramming them up his ass. One hand stroked him while the other fucked him. She expertly massaged his prostate.

“Do my little fingers feel good?” She said. “I’m starting to think you like it up the ass. It always makes you cum faster.”

Just like she said, his hips twitched against her fingers as he came. His measly load spurted across his stomach. To be honest, she was right. Every time he came, he wouldn’t feel relief unless she teased his ass. He’d still cum from her stroking his dick, but he’d be restless and frustrated.

“I think I’ll start touching down there even more. Since you’re my little bitch now.”

Day 23

“Uh, Emily?” Jack asked. “What’s this?”

Between his legs, Emily had put his dick in some sort of cage made of metal. It was locked so he couldn’t take it off. Emily grinned at him with red cheeks as she fiddled with the key that hung between her breasts.

“It’s a chastity cage, obviously.” She said excitedly. “You haven’t made any progress in over a week. If constantly making you hard isn’t working, then maybe preventing you from getting hard will work instead.”

Emily slid her finger up and down his cage, though he couldn’t feel it of course. He wasn’t quite sure how to feel about it. Losing his virginity seemed to be getting farther away from happening.

“So now what?” He asked. “You’re just going to hang around till it’s time to unlock me?”

“No,” she said as she climbed onto his lap, her pussy pressing against his cage. That was the closest he’d ever come to fucking her. “That’d be boring. I plan to keep things interesting for the next week.”

“A week?”

Emily kissed him. He could feel his dick try to get hard, but the cage was so small that it strained helplessly against it. She slipped her tongue in deep and probed around. The longer she kissed him, the more his dick struggled in its confines.

“Don’t worry.” She said, pulling back. A trail of saliva hung between them. “That doesn’t mean we can’t keep having fun. Plus, I’ll give you a big reward if you can make it.”

“I guess I can accept that.” He said defeatedly.

“Now,” she reached to the side and grabbed an unmarked box. “Time for today’s session.”

“But you just put this cage on me. You can’t really do anything with it now.”

Emily opened the box to reveal a pink dildo. Not a big one, it was actually pretty close to his size. In fact… “Is that a copy of my dick?”

She grinned sadistically. “It is! I had it made the other day for this occasion.” Her hands fiddled with his cage as she attached the dildo it and gave it a few strokes. “Now it’s like your dick is free!”

“How is that supposed to help me? I can’t actually feel that.”

“True,” her grin widened. At the bottom of her shorts was a zipper he hadn’t noticed before. Emily unzipped it, which opened a hole big enough for her pussy to be seen. “But now I can do this.”

The succubus lowered herself onto the recreation of his dick. She bounced on it, holding onto his shoulders for support. Her large breasts bounced hypnotically in front of his face.

“Look!” She stopped bouncing to give him a quick kiss so his dick could keep struggling. “It’s almost like you’re fucking me!”

Jack desperately wished that was his actual dick. He had a hot girl riding him, yet he still didn’t know how it felt to be inside her. What a pussy would feel like around his dick.

“P-please.” Jack whimpered. His dick hurt from the cage preventing his erection. “Let me use my actual dick.”

“Sorry, little guy.” She shoved him down on the bed. Jack’s eyes widened as her crotch hovered over his face. “Your little dick would cum the moment it went in, and where’s the fun in that?”

Her enticing ass sat on his face. The wet pussy on his mouth and the asshole on his nose. Jack expected a foul smell, but instead, she smelled…like lavender?

The pussy grinded against his face while the succubus’s fingers probed at his exposed asshole. “Feels like your little hole is pretty sensitive now. I just have to poke it and it starts twitching for me.”

Jack licked at her pussy. It wasn’t only the first time he’d seen a real one, but also the first time he’d touched one. Her juices were sweeter than expected and made his dick struggle even more. If her saliva was an aphrodisiac, he guessed these fluids were more potent.

“You sure you’re a virgin?” She asked as her finger nonchalantly slid in and out of his hole. “Cause gods, you really know how to use that tongue.”

Emily’s legs suddenly clamped around his head. He couldn’t move and her pussy smothered him. Jack squirmed, trying to breathe, but she wouldn’t let up. He started thrusting his tongue inside of her, hoping that she’d let him go if he got her off.

The succubus gently blew on his exposed hole which made him tighten around her fingers. Jack started to feel dizzy from the lack of air. He tried to discover her clit. That should be her weak point, but as he moved his tongue up, it just poked at something thick. He couldn’t tell what that was. Whatever it was did the trick as it made her squirt all over his face.

“Ah.” She sighed. Her legs released him and Jack gasped for air. “Thanks, after teasing you the last couple of weeks, I really needed that.”

“You sure you won’t take it off?”

Emily slipped her fingers out of his twitching hole and rubbed his swollen balls. “I could, but then you wouldn’t get your reward.”

Day 30

Emily was out of the house and Jack couldn’t take it anymore. It’d been a week of Emily constantly teasing him and fucking herself on the dildo he wore, and he needed to cum. His balls ached for relief. Jack found the dildo copy of his dick and knew he had no choice. Because of Emily’s teasing, His ass was so sensitive now that it should help his problem.

He laid down on his bed, not quite confident in how to do it. Emily had at all times been the one to poke around down there. Jack spat on the phallic object and prodded his hole with it. By instinct, his ass twitched for more.

Fighting back a pitiful moan, Jack slid the dildo in. It felt good rubbing against his prostate, but it wasn’t the same as when Emily did it. Either because he didn’t have her saliva to turn him on or because he simply lacked the skill down there.

Jack’s hand started moving on its own. In and out, in and out. He sped up, feeling the pleasure gradually create up. It made him feel warm inside. He needed Emily’s touch for a better orgasm, but this would still help.

He was on the edge, about to cum any second when his door flew open. Emily waltzed in with a smug look on her face. Jack froze. The dildo still firmly up his ass.

“What a naughty boy.” Emily cooed as she approached. “Trying to get himself after I had said he wasn’t allowed.”

She didn’t pull the dildo out or knock his hand away. Instead, she used both hands to grab his balls. Her thumbs massaged them carefully.

“Well, the good news is you didn’t cum. And It’s been a week.” Emily climbed onto the bed between his legs. “So, I guess I can give you your reward.”

Jack eyed the key that dangled between her breasts. He hoped she meant it was finally time to lose his virginity. Emily brushed his hand to the side and slowly pulled the copy of his dick out of him. Then, his eyes widened as her fingers slipped into her shorts and began to slide them off.

“If you’re gonna stick something up your ass to cum, why use something that tiny? It can’t possibly get someone off.” Jack froze again when her shorts revealed something unexpected. A enormous cock fell out and plopped against his caged dick. “You need something this size to do it right.”

Laying against his inferior dick, Emily’s cock had to be at least twice his size. And it wasn’t even hard yet. The succubus used her stimulating saliva to lubricate her cock. She stroked it all the way from tip to base. Slowly, and smugly.

Jack gulped, feeling small by comparison, as her cock got bigger and bigger in her hands. When it stood fully erect, it wasn’t twice his size anymore. It had to be closer to four or five times his size. A minimum of over a foot long, but he guessed it was longer. And it was thick too.

“Don’t be scared.” She murmured into his ear as she caressed his cheek. The large tip of her cock pressed against his little hole. “I’m finally taking your virginity like you wanted. You’re anal virginity.”

“N-no, I didn’t mean- “

The tip forced itself inside, stretching him so much that he swore it’d tear something. He moaned loudly despite how it made his ass burn with pain.

“Sorry, I didn’t quite catch that over your girly moan.” She said with a sadistic grin. “Could you say it again?”

Jack was powerless against her. His ass craved for more and her saliva made his head swim. Emily’s hands rubbed at his nipples, teasing them between her relentless fingers.

“It’s too big.” Jack gasped. His mind tried to fight against his body. “It won’t fit.”

“Hm?” She placed her hands on his waist and dribbled more spit onto her cock. “Your ass is tight, but I’m sure it can handle more. I’m gonna push a bit deeper, so bear with me.”

Jack’s back arched as the cock not only went deeper, but it also crushed his prostate when it slowly pushed past it. It made him feel weird as it forced him to cum. His dick couldn’t get hard, so instead, it dribbled onto the larger cock under it.

“Already?” Emily laughed. “I’m not even all the way in yet.”

“I-I don’t want anymore.” He lied. “Pull it out, it’s too big to fit down there.”

The succubus stroked his waist comfortingly. “Are you sure you’re not just afraid I’ll make you cum again when I’m balls deep?”

“N-no, it just doesn’t feel good.” He lied again.

“Mmm, I don’t buy that.” She said. “The way you’re gripping my cock says otherwise. I’ll even prove it to you.”

Without giving him a moment to brace, she shoved the rest of her cock inside with one strong thrust. Her large balls slapped against him. Jack could feel her deep inside as if she’d just rearranged his insides. He dribbled another small load all over her cock.

“Good boy. I knew you’d like it.” Emily sat back and pulled him into her lap. She was so much taller that his head was squished between her breasts. “Now the real fun begins.”

She started thrusting, bouncing him into the air so his weight would slam him back down on her cock. Jack was too weak from the pleasure to withstand. He couldn’t stop moaning as his hole glided up and down her length.

Emily’s fingers started rubbing at his nipples as he bounced. There were too many sensations that his little dick dribbled another load. This time between their stomachs. It was such a strange, yet satisfying way to cum. Better than her tits, hands, or even mouth.

He came a couple more times before she grinned down at him as her cock twitched deep inside of him. Warmth flooded his insides as she blew a enormous load. Her saliva and pussy fluids were already potent aphrodisiacs, but her cum was far stronger. Jack felt his brain shut off completely and was replaced with only pleasure. He went limp against her, unable to control his body anymore.