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Thirteen days after Aldyn’s initial encounter with the rival thieves’ guild, he approached their hideout once more at night, this time voluntarily. He’d been unable to stop thinking about the rough fucking and punishment he’d received on his first visit. He’d cried a lot, but he’d also come harder than he could ever remember coming before, and even the lingering soreness after the encounter had been pleasant. He’d masturbated several times while savouring the ache of his bruised backside, remembering what had happened and fantasizing about further possibilities. The leader of the guild had made it clear that he was welcome to return, so he finally was giving in to the temptation, now that his ass was no longer black and blue.
He quietly slipped through the front door and looked around. To his surprise, most of the eight people that had been there for his previous encounter were not present. Only one was, the tiefling named Demerian who had fucked Aldyn’s ass while he was riding the guild’s leader, Gaskus. Aldyn hadn’t really gotten a good long look at him before, but he was tall and handsome, with wavy black shoulder length hair that contrasted with his red skin, two large horns that curled away from his forehead, and dark grey eyes. Aldyn stood, silent, letting the door fall closed behind him. Demerian looked up from the desk in the corner with a smirk. “Why, hello, bluejay. Coming back for more, are you?”
Aldyn merely nodded, blushing hotly.
“I’m afraid the others are all out on a job. I stayed behind to do some paperwork, but it’s almost done, so I could certainly entertain you if you like.”
Aldyn managed to stammer out a reply. “Y-yeah.”
The tiefling stood up, grinning. “You look a little disappointed, though. I bet you were hoping to get both holes stuffed again, weren’t you? Don’t worry. I’m a magic user, and there are plenty of ways I can make up for the lack of another partner. You’ll be more than satisfied.” He approached Aldyn, stroking the smaller man’s cheek and tousling his hair. “Think you might be able to go for two rounds tonight?”
Aldyn gulped and nodded, still blushing furiously.
“Good. We’ll have some fun. Well, come on, get undressed. Time to warm you up.”
Aldyn took off his jacket and boots first, then slipped out of his pants, unbuttoning his shirt and unlacing the binder he wore underneath it. He cast them aside, face getting even redder, and finally slipped out of his boxers. He was slim and petite, with smooth light brown skin, small breasts and a surprisingly plump, curvy little ass. His pubic hair was bluish-purple, just like the hair on his head. Demerian chuckled, reaching out and stroking between Aldyn’s legs gently. “Don’t see natural purple hair very often. You’re a special one, aren’t you? Okay, to the desk with you.”
He picked Aldyn up effortlessly, tossing him over one shoulder, and deposited him on the desk, face up. With one practiced movement he lifted Aldyn’s legs into the air, holding his knees towards his chest with one arm as the other hand rubbed his backside firmly. The hand strayed between Aldyn’s legs, pressing firmly against his crotch, and he whimpered with need. “You want me to smack your little ass until you’re dripping wet and crying, Aldyn?” Aldyn nodded, biting his lip. The hand between his legs applied more pressure. “Want me to smack you here too?” Aldyn nodded again, eagerly. That had been one of the most memorable parts of his earlier encounter. Demerian grinned. “Good boy.”
The tiefling began smacking Aldyn’s exposed backside firmly, pausing every five smacks or so to land a couple of blows between his legs as well. His hand wasn’t as large as the half orc Gaskus’ was, but he was still much bigger and more muscular than Aldyn, easily able to quickly warm his bottom. After smacking the smaller man for a couple of minutes, he roughly thrust two fingers inside him, provoking a whimper. “So wet already. What an eager boy.” He kept the fingers inside Aldyn, crooking them and rubbing them against a sensitive spot inside him until he squirmed and whined. “You’re sweet. You just can’t wait to get fucked, can you? Greedy little brat.” He pulled his fingers out and smacked Aldyn hard, right over his slit, and the half-elf gasped, hips jerking. “Don’t worry. When I’m done with you you’ll be so worn out you won’t even be able to think about getting pounded again without whimpering.” He continued to punish Aldyn’s backside, still stopping every few moments to focus between his legs as well, until his hand came away slick with fluids and the younger man was starting to choke back sobs. He stopped then and licked his hand, letting go of Aldyn’s legs and smirking down at him as he relaxed against the desk, breathing heavily.
“You taste almost as sweet as you look. Well, I got to fuck your tight little ass last time. This time can I fuck you in front?”
Still sniffling, Aldyn nodded.
“Great. Well, get up and pick up the cushion from the chair back there. Might as well try to make you comfortable.” Aldyn got up, his legs shaky, and picked up the cushion from the chair, standing to face Demerian while holding it, a questioning expression on his face as he wondered where to put it. The tiefling took it from him and placed it on top of the desk, then casually picked up Aldyn with both hands at his waist and deposited him on top of the cushion before pushing his own trousers to his knees and leaning over the younger man with a grin. “Put your legs around my waist.” Aldyn obeyed, biting his lower lip as Demerian slowly sank into him. He wasn’t quite as large as the half-orc had been, but he was certainly large enough, and being on his back with his legs wrapped around the other man’s waist made Aldyn feel vulnerable and overpowered, which was exciting. The tiefling's cock was also covered in ridges, bulging even thicker near the base, and unusually firm inside him. Demerian tangled his hands in Aldyn’s hair and leaned forward, licking and then gently biting his left nipple. “You like that?” Aldyn nodded, blushing hotly. “Good. You’ve got such a cute little body, it’d be a shame to ignore any of it.”
He started rocking his hips, thrusting into Aldyn slowly while smirking. “You’re soaking wet, but still plenty tight enough. Feels good. I only fucked you with the first few inches before, but you're going to take it all now.” He lifted his head from Aldyn’s chest and leaned further over him, pounding him relentlessly for a good couple of minutes until Aldyn was whimpering and panting. He rubbed Aldyn's lower belly gently with one hand, slowing the thrusts, then grinned down at him and held the smaller man by his hips, slowly pulling him up until the base of his cock was fully inserted. Aldyn looked up with wide eyes, his muscles spasming around the bulge as he gasped. "It... it feels so much bigger now, it barely fits..." Demerian laughed. "Thanks for the compliment, but you've taken bigger than me. But getting the widest part into your other hole would have been a challenge, that much is true." Then he stood up straight and began to withdraw, leaving Aldyn confused and spreadeagled on the desk. Demerian grinned at Aldyn and ruffled his hair, then strolled around to the chair behind the desk, sitting down. “Come over here and bend over the desk. Fold your arms and lean on them.”
Aldyn obeyed, standing on shaky legs and arranging himself as requested, blushing again to think how he must look with his legs spread and his dripping sex exposed. Demerian gave him a stinging smack on the ass and pulled his chair close. “Just lean forward and let the desk support your weight. I’ll hold your legs up.” Aldyn gasped and his hips twitched as Demerian lifted his legs up towards his sides and slid his rigid cock inside him from behind. The older man moaned quietly, placing his hands on Aldyn’s hips and pulling him closer. “That’s better. Now I get to grind against your cute little ass. And I can give you more of this.” He smacked Aldyn’s left buttock sharply and began to rock his hips, pulling Aldyn tightly against him with each forward motion. Being fucked from behind ended up stimulating a spot inside the younger man that hadn’t been reached in the other position, and the ridges along the shaft of Demerian's cock built up a pleasant friction against his inner walls and slick opening. Aldyn began to whine and squirm in pleasure as Demerian’s motions sped up, several more firm smacks landing on his stinging backside. The tiefling reached around and began to rub Aldyn’s throbbing clit as he fucked him, thrusting more shallowly and rapidly as the half-elf's sensitive opening pulsed and rippled around the thick base of his dick. Aldyn gasped and eventually choked back a sob, his legs trembling. He could barely recognize his own voice as he cried out, begging. “Please… harder… keep fucking me harder, faster, please…”
Demerian groaned and dug the fingers of his right hand into Aldyn’s hips as he fulfilled Aldyn's demands, fucking him even faster. His left continued to rub his clit in quick, urgent circles. Aldyn nearly shouted as his legs stiffened and trembled and he came, panting against his folded arms, his insides spasming rapidly around the tiefling’s cock. Demerian stopped rubbing Aldyn’s clit and gave his ass another slap, then used both hands to pull the panting, whimpering boy’s soft, well-spanked backside tightly against his hips as he rocked against him a few more times and reached his own orgasm. With a smirk, he leaned back in his chair, not pulling out right away, and kneaded the flesh of Aldyn’s plump bottom with both hands. “Damn, bluejay, for a little thing you’ve got a hell of an ass on you.” Aldyn slumped against the desk, breathing hard, but managed a little giggle in response. A mixture of cum and his own fluids was already starting to drip down his thighs, and when Demerian withdrew from him he could hear more of it splashing onto the floor. He felt hands on his waist and looked up, startled, as the older man flipped him onto his back and leaned down, licking gently between Aldyn’s legs. Aldyn remained in stunned silence as the tiefling licked him clean and finished with a gentle kiss just above his clit. Demerian smirked. “What, has no one ever done that for you before? You taste nice. And licking up some of my own cum is hardly the most adventurous thing I’ve done. Want to have a little rest? The others aren’t due back for hours yet, so we have plenty of time.” Aldyn sat up, nodding weakly. “Come here, then.”
Demerian buckled his trousers back up and patted his knee, and Aldyn shyly took a seat. The tiefling picked up his coat from nearby and wrapped it around Aldyn’s naked body and held him close, leaning back in his chair. He stroked the younger man’s hair tenderly and murmured in his ear. “Go to sleep, sweetheart. You’ll need the rest before the evening I have planned for you.” Aldyn relaxed, exhausted, and drifted away within minutes.
Aldyn slept for over an hour, and awoke to find Demerian gently stroking his hair still. “Ready for round two?” Aldyn yawned, then nodded, blushing. Demerian pinched his backside, then lifted him up and set him on his feet. “Okay. I have something in mind, but I guess I should ask… are you afraid of tentacles?”
Aldyn blinked and stared. “Um… well… no, I suppose not.” He had seen some mages use spells that caused tentacles to materialize, and he assumed that was what Demerian was speaking of. “I can’t cast any spells like that myself just yet.”
“Well, after this perhaps you’ll be motivated to learn.” Demerian stood behind Aldyn and raised both hands, moving them carefully while murmuring an incantation. A pool of purple liquid appeared on the ground, and suddenly a mass of slippery, shining tentacles spilled forth from it. “Purple, to match your hair.” Aldyn laughed nervously. “Okay, bluejay. Get down on the ground on all fours with your ass facing them.”
Aldyn swallowed hard and obeyed, getting onto his hands and knees and presenting his well-spanked backside to the tangle of tentacles. He cried out in surprise as they seethed forward, wrapping around his arms and legs. “Don’t panic. They’re just going to lift you up. They’re very strong; you won’t fall. This is going to feel good, I promise.”
Despite the reassurances, Aldyn couldn’t help but whimper as the tentacles lifted his body. One was wrapped around his hips, holding him so his ass was the highest point. Others coiled around his knees, keeping them spread. More supported his arms. Aldyn cried out as a heavy, firm and moist appendage slapped against his bottom, leaving behind a film of slick fluid. He then went still as he felt it probe between his legs for a moment before sliding into his cunt.
It was thick and could get further into him than Demerian's cock, but entered easily thanks to the fluid dripping from it. It rippled and flexed inside him and felt pleasantly warm, warmer than Aldyn’s own flesh. It wasn’t long before Aldyn’s initial shock and surprise turned to pleasure, and he moaned quietly. He heard Demerian speaking.
“The fluid has aphrodisiac qualities. It should feel very nice.” He walked around to face Aldyn, smiling. “How is it? Are you ready for both of your holes to be stuffed full?”
Aldyn’s face was burning, but he nodded shyly. Within seconds he felt another tentacle probe between his buttocks and begin to slide into his ass. His hips were lifted even higher, and the two tentacles inside him began moving in tandem. As the one in front slid in, the other slid out, and they moved faster and faster. They remained extremely slick, and Aldyn could feel fluid dripping down his thighs. His legs were spread even further apart, and the two tentacles continued to thrust into him urgently, never quite pulling out entirely, filling him completely as he whined and squirmed. The piston-like motions with which they thrust into him made him feel like part of some perverse machine. Demerian stepped forward and reached underneath Aldyn, finding his clit and rubbing it insistently while pinching his right nipple with his other hand, and the younger man almost sobbed in relief as he reached his first orgasm. But the tentacles remained inside, moving a bit slower now. Demerian stood back a little, tousling Aldyn’s hair gently.
Aldyn felt very warm and sated and his mind was hazy, focused entirely on the sensations of being penetrated. Suddenly he was aware of the tentacle in his cunt swelling, stretching him, but it wasn’t painful. He just felt pleasantly full. He whimpered and moaned as the bulge inside him began to vibrate and grow even warmer. He was also being pulled into a different position, sitting almost upright now but still being held aloft. “What… what’s happening…”
The tiefling just grinned at him. “Just enjoy it, Aldyn. It’s okay. I won’t hurt you.”
Aldyn cried out as the vibrating stopped and the swelling sensation intensified. There was a slight pop, and realization dawned on Aldyn’s face.
“It’s… putting eggs inside me?!”
Demerian grinned. “Don’t worry, they’re not going to hatch. They’ll fall out later. But just wait.” Aldyn whimpered, looking down at his belly as the vibrating sensation began again. He couldn’t see anything different about his body after the first egg entered him, but after the third, his stomach was protruding a little. Aldyn traced his fingers through the film of purplish fluid coating his skin, feeling the thrumming bulge inside him with awe. Then the tentacle in his ass began to throb, and the process was repeated until he was filled with five eggs, three in front, two in back. The tentacles inside him slithered out slowly, giving Aldyn’s stretched holes time to contract, holding the eggs inside, though large amounts of liquid seeped out. He cried out in surprise as the eggs inside him began to grow warm, even warmer than the tentacles had been, vibrating more intensely now. His legs, still held up by more tentacles, trembled. “Demerian… I can’t… are they going to fall out?” His expression turned sulky, his cheeks puffing out in frustration. "I don't want them to fall out yet... they feel nice."
Demerian chuckled and stepped forward, pushing his trousers down his hips. “They won't. Not yet. I’ll help.” Aldyn gulped, stunned, as the tiefling plunged his cock inside him again. Aldyn was amazed that the man was even able to enter him with the eggs inside, but to his surprise it wasn't painful. Strong hands cupped his bottom as the larger man began to thrust. The eggs continued to pulse and throb. Aldyn had never felt so full, not even when Demerian and Gaskus had both fucked him at the same time. Demerian leaned over him, moaning quietly. “Fuck, the way those eggs are moving inside you… feels amazing…and it’s so warm.” He kept his hands on Aldyn’s buttocks, keeping them pressed together so the eggs in his ass couldn’t escape, and thrust into him again and again. Before long Aldyn was sobbing desperately and shaking all over, overwhelmed by the heat, the throbbing vibrations of the eggs, the effects of the aphrodisiac, and Demerian’s large cock pounding into his sore, overheated opening. “Touch me again, please…”
With a smirk, Demerian began to rub Aldyn’s clit again, his thumb slick with the fluid which made everything feel more intense. Aldyn’s third orgasm of the evening was the most intense yet, both of his stretched and aching entrances throbbing and spasming around the eggs and cock inside them. Demerian continued to thrust roughly into Aldyn’s fatigued body a little longer before coming as well, carefully pulling out. The tentacles continued to hold Aldyn up as Demerian rubbed his belly soothingly. “Okay, little one, just relax.” He continued to rub gently over the bulges formed by the eggs, and Aldyn felt the first egg stretch his opening and fall, sighing in relief. The next two soon followed, and he was left only with the ones in his ass. Demerian smiled and patted his cheek. “Those two will take a little more effort from you. Just push them out.” The tentacles around his knees lifted them up slightly, and Aldyn blushed and began to push the first egg from his ass, moaning shakily as the small opening stretched and a large egg slowly made its way out, followed by a gush of purple liquid.
“Good boy. Just one more.” The last egg continued to vibrate inside him as Aldyn whimpered and pushed, and it too slid forth and dropped to the ground. Looking down, Aldyn could see the fragments of the eggs slowly turning back into glimmering fluid, being re-absorbed into the puddle. The tentacles pulled him upright, setting him down on shaky legs, and Demerian took him into his arms, chuckling, as the tentacles began to retreat and dissolve into the pool, which itself began to shrink and eventually disappear.
“You look a little stunned, bluejay. Gonna be okay?”
Aldyn nodded weakly with a whimper, nuzzling against the older man’s chest, still breathing hard with tears streaming down his flushed face. Demerian laughed again and picked him up, returning to his chair behind the desk and settling the exhausted boy on his lap, holding him close and stroking his hair. “Okay, I’ll hold you until you’ve calmed down a bit. Maybe I can take you to the inn and give you a bath before I send you on your way… would just be cruel to send you home dripping purple slime, wouldn’t it? Does that sound alright?”
Aldyn nodded, still sniffling a bit. It would take him ten minutes to stop shaking, but as he lay weary and sated in Demerian’s arms, he didn’t regret his visit for a moment.