Captain Alessa's Company Gangbang

Alessa looked up, and gave him a knowing smile, as she felt his hard-on press into her cheek. She slowly moved her head up to the waist of his pants, took it in her mouth, and pulled down. She felt dirty, pulling down a man's pants with only her mouth, and she loved it. Eventually she pulled his pants down far enough for his cock to spring free.

Alessa looked over his erection for a second, and licked her lips. Despite her father's best efforts, this wasn't the first cock she'd seen, but it was the first she'd seen in quite some time. She wanted to take it in her mouth, and use every trick she had practiced or read to give him an experience he wouldn't soon forget. However, when she looked up at his expectant face, she got a better idea.

Alessa brought her gaze down towards the cock in front of her face. Leaning forward she planted a kiss right on the the head. Slowly she took the head into her mouth, stopping her lips when they passed the glans. She began to suck on it and ran her tongue around the head once, enjoying the small shudder that ran through his body. Then, she released the pressure with an audible pop. She stuck her tongue out, and ran it down his length, taking his balls into her mouth briefly, before making her way back up the shaft.

"Think you're funny, don't you?" Lethodolus said just as Alessa was positioned to kiss his member again, "I can show you how to give a proper blowjob."

Alessa felt Lethodolus get a firm grip on the back of her head, and start to push against her mouth. However she kept her mouth firmly shut, preventing him from entering. She wondered what he was going to do next; force her mouth open, or just hold her nose closed until she didn't have any other choice but to open up for him. A sudden cold chill hit her bare ass, and she realized that her dress had been pulled over her ass and now just hung from her waist.

She looked up towards Lethodolus to confirm her suspicion. She saw him give a nod to the man standing behind her, Thadrian. She barely had time to relax her throat before she felt him enter. He pushed his entire length inside her in one thrust, it might've hurt if she hadn't been so wet. Finally, after years of waiting she had a hard cock filling her pussy.

"Fuck, this slut is tight." Thadrian grunted as soon as he had pushed all the way in.

She opened her mouth to let out a moan, but it never escaped her lips. Before it could, Lethodolus took advantage of the opportunity to shove his cock down her throat. She had prepared as best she could, and while it wasn't enough to stop her from initially gagging from the sudden intrusion, that's all she did, and she stopped soon afterwards.

Thadrian began to pull out, leaving a noticeable emptiness behind, only to slam back in. He entered her roughly enough to push her forward. Thadrian took ahold of Alessa's bound wrists, pulling them back as he pushed forward again, the rope biting into Alessa's flesh.

Lethodolus looked down at the submissive woman below him, her face awash with pleasure, he knew from one look that she enjoyed the rough treatment. He had a hand at either end of her head, as he thrust into her mouth over and over. He timed his thrusts with Thadrian so that he could get as deep into her throat as possible.

Alessa found her mind assaulted by a onslaught of pleasure. Her conscious mind quickly drowned, as she just enjoyed the experience. Without thinking she began to push back into Thadrian's thrusts. Soon she felt her first orgasm of the night hit its peak. Alessa felt herself tighten around Thadrian as she came. Just as she felt the waves of her orgasm start to ebb, Thadrian buried his cock deep inside her and shot out his cum. She felt Thadrian pull out, and shoot a couple more strands on her back and ass.

Lethodolus followed suit, pulling his cock out of her mouth and jerking it off in front of Alessa's face. Alessa closed her eyes and opened her mouth. In just a few moments she was rewarded. Warm cum splashed onto her face, one strand hitting her closed eye, a couple landing in her hair, and few more going into her open mouth, or landing on her tongue. The rest was scattered across her cheeks, nose, and forehead. She opened her eyes, and made eye contact with Lethodolus as she closed her mouth and swallowed his cum.

"Delicious," she said, licking her lips.

Lethodolus smiled, as he looked down at her. "You know what, I like you, you remind me of someone I know." He said, "Come find me next month, and I'll have something special for you." He made a gesture towards Thadrian, and they both left, disappearing into the crowd.

"I hope you're not done after just one round." Terrowin asked from behind Alessa, suddenly bringing her back to the moment.

"Not even close." She responded.

"Good, because this is going to be a long night for you."

Suddenly, Alessa felt a pressure building at her asshole. Her breath caught in her throat. She had never had anal before, and despite having gone through rigorous training in pain resistance, it was still something she wasn't eager to try dry. Terrowin could feel her apprehension and chuckled to himself.

"You want me to use this?" He asked pulling a small glass vial from his belt and dangling it in front of her face.

"Yes, please."

"Well, I don't know if I should, this is supposed to be your punishment, after all," he said pulling the vial out of her sight. "Maybe if you did something for me in return."

"Anything." She responded, biting her lower lip.

"Alright, now this may sound a bit weird, but I want you to role-play as our Captain, Alessa Saisset."

Alessa's heart skipped a beat. She wondered if Terrowin had actually figured her out, and was teasing her with the knowledge. Either way it was safest to play along, and assume it was just a coincidence.

"I've never met her, so I don't think I can."

Terrowin leaned forward, reached around her, and started to fondle her breasts, somewhat sore from the pressure put on by the ropes. "Oh, don't worry, it's an easy role. Just act like you're in control, while being a cock hungry slut." He let go of her breasts, and straightened up, uncorking the vial. "It looks like you already have the second part down."

Alessa took a deep breath, and closed her eyes. "I know I said you could have any reward you wanted when you saved me from that orc warlock, but this wasn't what I had in mind."

"Stop pretending like you don't want it," he said, as he began to pour the slick liquid on her asshole.

Alessa flinched instinctively as she felt the oil hit her skin, "You could at least untie the ropes."

"Alright, I will, if you can honestly tell me that you want them untied." He paused, and Alessa squirmed a little, she noticed that the ropes felt like they hadn't loosened up at all. "Well?"

"Whatever, let's just get this over wi- Ahn."

She was cut off, as she felt him push his index finger inside her asshole. He wormed his finger, spreading the lube around inside her. Alessa closed her eyes as she adjusted to this new feeling, it felt strange and a little painful, but she could also feel a building pleasure. Eventually he pulled his finger out, and positioned his cock behind her.

"Ready?" He asked as he started to gently push forward, his arm grabbing her bound wrists to keep her place.

Alessa could feel her tight entrance start to give, as the tip of his cock started to push its way inside her. Her breathing became heavier the deeper it reached inside her. After the head made it through, it started to pass a little faster. She could distinctly feel each inch as it entered her.

"No, it's too big, I can't take anymore." She cried, as she squirmed a little harder under him.

"Shh," Terrowin cooed, as he reached around her, and pinched her clit, "You're doing so well, my little anal slut."

Alessa moaned, and she suddenly felt the rest of his cock slip inside her. She let out a yelp, her ass felt like it was completely full. It wasn't nearly as painful as she expected, but she couldn't help and wonder how some women enjoyed this. She closed her eyes and tried to adjust herself to this new feeling. After a couple moments she realized that he was staying still.

"Why aren't you thrusting?" She asked, in between heavy breaths.

"I'm waiting for you."

"Thank you." She said closing her eyes, "I think I'm ready now."

"Good," he said, but he didn't start moving. "Beg for it."

"I'm sorry?" She said craning her head to look at him, "I'm your commanding officer, I'm not going to 'beg' like a bitch in heat."

His gaze turned ice cold for a second, before he began to chuckle. "I'm surprised you have any dignity left. I mean, here you are tied up, bent over, one of your subordinate's cocks in your ass, acting all high and mighty. You might be a Captain out there, but that's not what you are right now, right now you're my little anal slut." He paused for a second, as he looked over the face of the whore below him, "Now beg for me to fuck your ass."

"P-please, sir, please fuck my ass." Alessa began, "use my tight hole for your pleasure. I want to feel your big, hard cock sliding in and out of me. No, I need it."

"Good girl." Terrowin said as he began to pull his cock out, "Now for your reward."

Terrowin started out slow, but it didn't take long for him to start to speed up. Alessa felt like he would consistently speed up just as she was getting used to last speed. It didn't take long for him to get a good pace going.

Alessa bit her lip, as she got her first taste of anal. The discomfort and pain quickly faded away, as the pleasure started to build. She realized how it was different to normal sex, this way she felt like she could feel every slight bulge in his cock. Despite what she thought earlier, she could see herself getting addicted to this.

Terrowin's thrusting got faster and faster, and Alessa could tell he was getting close to orgasm. Her own pleasure, was building faster, and she felt like she would reach her second orgasm of the night before he reached his first. Terrowin could see she was getting close as well, and he gave her ass a hard slap.

"Are you going to cum for me?"

"Yes, sir. Your anal slut is going to cum from your cock pounding her tight ass."

"I don't remember giving you permission to cum."

"Please, let me cum, sir."

Terrowin looked over her, as he continued to fuck her. He could tell she was really close, probably on the edge of orgasm. He thrust into her a couple more times, before speaking up again.

"Alright, slut, cum for me."

"Thank you, thank you so much." She practically screamed as her legs shook, and the pleasure building in her was finally released. Terrowin pulled out of her just as he was about to cum, and shot out his cum all over her back and ass. He let go of her wrists, and she fell onto her knees unable to hold her own weight anymore.

"You're pretty good at roleplaying." Terrowin, said tucking his cock back into his pants, as he stood over her.

"Thank you." Alessa breathed, as she felt the waves of her orgasm still move through her. She saw him make his way back towards the crowd, "Hey, can you remove these ropes, they're starting to become a little uncomfortable."

"That's not up to me," he said turning back to face her. "Now that I'm done with you, it their turn."

"Who's turn?"

"Their's." Terrowin, responded simply, gesturing to the crowd of people that had been watching since Lethodolus started to fuck her. The crowd that was now starting to close in on her. She realized that her night was far from over, and a smile crept across her face.

~~~

A couple hours later, Annabell made her way back towards the dorms. The building reeked of sex, as it always did after these sessions. She made her way inside to see soldiers passed out everywhere, at least most made it to their beds. The whores who were still there were gathering whatever items of their clothing they could find scattered around the room. In the center of the room was Alessa, lying on the floor, covered in dried cum.

Annabell walked over to her sleeping friend, and prodded her awake with her foot. Alessa slowly awoke, a dreamy expression on her face. She tried to stand but seemed to lack the strength. Annabel offered her hand, and pulled Alessa to her feet. Alessa threw her arm around Annabell's shoulder for support, as the two made their way back towards Alessa's quarters.

"So, I take it you enjoyed yourself?"

"It was great, I can't wait for next month."

"Yeah, well let's see if you're still saying that in the morning when you're sore all over, and need to take fifty baths to clean off the stench of semen."

"It'll still be worth it."

"Whatever, you slut."

Alessa giggled to herself, leaned into her friend, and closed her eyes. "Thank you, Anna."