The Regiment Ch. 07: Op Tour Bonus

Thwack.

"Shit! Shit! Shit!" She cried when the cord struck her between her shoulder blades. She could feel the welt start to rise almost immediately. Before the first rush of pain had subsided, she heard the cord slicing through the air again.

Thwack.

"Fuck! Fuck! Fuck!"

Thwack.

"Ngh! Ngh! Ngh!"

Thwack. Thwack. Thwack.

Jen did not even make a sound under the final barrage. Instead she gritted her teeth and leant against the bed. It is a funny thing about pain. Once you are immersed in it, you realise that it is never as bad as it felt at the start; much like getting into cold water. When it was clear that he had stopped, she hissed out a breath, but the pain simply felt hot on her skin.

Alexei launched the cord into the corner of the room and stepped behind her, running his hands over her tortured skin, then round to her front to massage her breasts. 'He must get through a fucking pile of phones every month if this was how he got his kicks.' She thought to herself. While the flogging was not exactly doing it for her, she did admit that it had an odd effect on her senses. In comparison, his hands circling her nipples seemed impossibly gentle, but not tickly as it sometimes did when men felt her up. The pain had turned all of her nerves on at once, but filled her with adrenaline and serotonin.

His hands traced lower, fluttering over her smooth tummy and settling on her jeans. As she felt the buttons come undone, his lips pressed against her neck leaving little kisses from her shoulder to just behind her ear. She let out a breath, despite herself, then drew it back in as he slid her jeans to the floor, kneeling down as he did so. She stepped clear of her trousers and pushed them sideways a bit, feeling her phone still in one pocket. Alexei's hands then held her by the hips and stopped her motion. They remained like that for a long moment before he looped a finger through the gusset of her light blue thong and pulled it to the side.

She could feel his breath on her bare pussy lips as he inspected her from point-blank range. Then she felt his lips, again placing soft kisses, this time on her inner thigh. Well that did something for her at least. She arched her back and stuck her bum out a bit more and was rewarded by the lightest kiss on her labia. Alexei then trailed his tongue upwards until it was circling her arsehole. That definitely did something for her and she wriggled a little bit, trying to find the best angle to present herself. It was a cruelly short experience though as he stood up and walked to the bedside drawer, in her eyeline. She watched as he removed a tube of lube and then a stainless-steel butt-plug. 'Bugger' thought Jen, prophetically.

Jen had been late to the realisation that playing with her butt could be pleasurable, but was now convinced that a well lubed finger or Lauren's tongue could really add something to sex if carefully used back there. But she had never been penetrated with more than that. She had seen similar devices to the one in Alexei's hand on Tumblr and knew that they were called 'princess plugs' because of the jewel on the flat end. This was not a big one, in fact it might be the smallest one she had seen, but it was still bigger than a finger and that was her only measuring stick at the moment. He looked at her as he dripped lube onto the pointed end and then walked back behind her.

She took and deep breath and held it, but he scolded her. "Breathe normally or it will hurt more." She tried to take his advice but her breath still caught when she felt the cold, slippery metal nestle into her most private area. Clearly not shy, he pushed firmly and she felt herself stretch to accommodate it. Just as it felt like it was about to hurt, the widest part slipped inside her and the sensation went away. She wiggled her butt in celebration.

"Pride comes before the fall." He scolded again. He pulled her belt from the loops on her jeans and stood up behind and to the side of her. Jen was pretty sure she could guess what was coming next - and it wasn't her.

With unerring accuracy, Alexei brought the belt round in a wide arc until it connected with the soft skin of her buttocks. She tensed everything as the pain hit and was intimately aware of the invader still lodged in her anus. He struck her again and again. The sensation, very different from the flex, was still causing her skin to burn. He swung irregularly, making her wait for the next blow. She jinked left and right, straining her wrists against the rope, but it helped her none; he never missed a stroke. Her cries were louder each time, but also felt curiously liberating.

She had been the recipient of a spanking or two in her life, but this one was marked as different by the presence of the plug. Sometimes the path of the belt was across the top of the jewel. This actually provided some relief as the metal transferred very little of the impact into her butt, and took away some of the punishment from her cheeks. Other times, the leather cracked across the tender flesh where her buttocks ended and her legs began. When this happened, she could not help tensing her whole pelvis. Doing so pulled the plug in tighter until she relaxed. This continual 'pulsing' of her muscles and the plug was starting to bring a strong warmth to her face and chest in a way that made her slightly ashamed of herself.

Eventually Alexei stopped, and while his composure was still firmly in place, at least he was breathing hard now. He turned her around again, forcing her tip-toes to pirouette as she faced him. He then kissed her on the mouth with surprising passion. Jen surprised herself by moaning softly as he did so. It wasn't that she was desperate to kiss the man, but more a continuation of the rough treatment heightening the pleasure of softer sensations.

Jen realised that she was in for a bigger treat as he quickly dropped to his knees and tugged her thong all the way down. Alexei nuzzled into the crease at the top of her thighs and then gently parted her lips with his tongue. He slowly circled her clit with a slow, steady pressure and she gasped in response. He kept up his slow movements for several minutes, and when he started slipping a finger into her wet pussy, Jen felt the pressure built inside her. Abruptly, he stopped again and left her dangling by the soft, silk ropes.

The idea that she was being worked over by the Russian version of Christian Grey re-surfaced as he knelt and pulled something large from under the bed. It was another thing that she had only seen on the internet. It was like a low, leather footstool with a curved top. At its highest point was a strip of pink latex with a small, raised area near the front and a modestly dimensioned dildo near the back. A sybian. This guy had his own, fucking sybian. Weren't those things meant to be a thousand bucks? Alexei obviously took his perversions seriously. He saw her eyes watching his actions and smiled.

"Ah, my pretty, little one. I am not a man who believes in doing things in half-measures. If I want to achieve a goal, I use everything in my power to do it." Jen would not have doubted him five minutes ago when he was beating her up with a part of a telephone, but now he had unveiled the Rolls-Royce of wanking machines, she was certain. Alexei was a singularly committed man.

Reaching up above her head, Alexei released her hands; her fingers tingling as blood flowed back into them. He guided her by the shoulders to the side of the bed and then gently pushed her down towards the floor. She had an idea of how these things worked so she did not need much direction. She straddled the sybian, he knees resting on the carpet either side of it and her pussy hovering just above the fake cock. He pushed on her shoulders again so she wriggled her hips until the dildo was correctly lined up before sinking lower, penetrating herself. It was a pleasant, but somewhat unsatisfying sensation considering how worked up she was.

Alexei then knelt next to her, holding two black nylon straps with metal attachment points. He looped them around her thighs and then clipped them somewhere on the base of the machine. Jen could feel herself being pulled towards the ground as he tightened the straps until she was unable to lift herself upwards by more than an inch. Alexei's love of control, and Jen's lack of it was once again obvious to her.

"Try to have fun, my dear." Alexei said patronisingly as he picked up the control unit for the sybian. Jen was about to make a smart-arsed reply, she could never help herself, when he clicked the machine into life. Instead, all she managed was a shy exclamation.

"Eeek!" Which she then followed with a more considered "Ooh!" as the intense vibrations spread through her groin. Immediately she knew this was different from her vibrator at home. Her trusty rabbit was nothing but light tickles compared to this. Because her whole weight sat her pelvis down onto the top of the machine, and the protruding dildo and existing plug filled her up nicely, there was a whole-body feeling to this stimulation. "Wow, this is actually pretty... ah ... good." Jen managed to whisper, wiggling her hips to better position her clit over the buzzing pad.

"Tell me, darling," Alexei said lightly, "On a scale of one to ten, how good is it?"

"Uh, oof, maybe a six or seven?" Jen responded, her voice going high at the end as she really started to enjoy the sensations. Alexei did not reply. He simply smiled and turned the control unit towards her so that she could see it was set at one out of ten. Jen's heart lurched with the realisation. Still smiling, he moved the dial up by one click. Immediately the buzzing noise in the room grew louder and another squeak escaped her lips. Regardless of her mission, Jen was now officially thinking with her clitoris. She focussed all of her attention between her legs and chased the orgasm that was just out of reach.

Alexei gave her the helping hand she needed by ramping the power up a few more clicks. This time, the increased buzzing was easily drowned out by Jen's increased moaning. She squeezed her internal muscles and closed her eyes, her breathing becoming shallower. The straps stopped her from rising and falling like she would if she was on top of a man. However, she found that if she rocked forwards and backwards, the pulsing, intermittent stimulation of her clit on the sybian and her asshole around the plug gave her what she needed. The pleasure rushed up from her core and escaped from her mouth as she gasped out her orgasm. From start to finish it had taken hardly any time at all to arrive. With her eyes still closed, but her breathing much deeper, Jen did the maths to decide whether she could afford to buy one of these things when she got home.

When Jen opened her eyes, Alexei was stood to her side, watching her. He had obviously enjoyed the show, as proved by the large erection obvious in his suit trousers, though other than that, he still looked ice-cool. He had also dialled the sybian back down to its lowest setting but even at this slow speed, its rumbling was keeping Jen's pussy juicing away. When he was sure she was watching him, he slowly undid the buttons on his crisp white shirt, slid it off his muscled shoulders and carefully laid it on the bed. Next, he removed his shoes, which were also placed neatly away. Finally, he dropped his trousers and startlingly white boxers, folded them onto the back of a chair and turned to face her, holding the sybian control.

Alexei towered over her and she was again reminded of the straps holding her in position. His bouncing cock was at her eye level and it arched aggressively towards the ceiling. He reached his hand towards her face and encouraged her to open her mouth before slowly feeding his rigid cock between her lips. Despite herself, Jen enjoyed the feel of him; so hard for her, so male. But knew immediately that Alexei, like always, wanted to be in control of this. She slowly closed her mouth around his shaft and applied some suction to his head. Alexei gripped a handful of her hair and, keeping his hips still, started to move her head back and forth along his length.

Concentrating on applying even suction along his shaft, Jen surrendered control of her head to his hands. He clearly appreciated this as he muttered several things in Russian while closing his eyes. When he opened them again, Jen made sure she was staring up into his face, wide-eyed. She was rewarded with a smile and the head of his cock being withdrawn to the front of her mouth so she could rub its sensitive underside with her tongue. They continued like this for some time, Alexei showing impressive control. He then changed the game.

'Click, click, click.' Jen heard and then felt the sybian being powered up. She let out an exclamation around the dick that was wedged in her mouth. 'Click, click, click.' He ramped it up again. "Mmmppphhh!" Jen managed to say. He was still stood totally still, using her hair to bob her lips up and down his cock, but now he applied more pressure on the downward stroke, testing the back of her throat with his steely dick. Jen mashed her wet, slippery lips onto the sybian and the vibrations she received in return made her toes tingle. It was difficult to concentrate on pleasuring Alexei with her mouth as the pressure built inside her.

Kindly, Alexei seemed to understand this problem, so gripped her hair even tighter and pulled her face towards him. Jen gagged, loudly and struggled against the invasion, but in no time at all, her nose was buried in his black pubic hair and her throat was spasming around his shaft. Her juicing pussy was forgotten while the need to breath was at the top of her priorities. She made eye contact again and he winked at her before releasing his grip on her hair. She sprang back off his cock and gasped for air, but even as she fought to get oxygen into her lungs, the sensations from the sybian roared back into her consciousness. It was like all of the sensations had been stored up and now were released at once. Jen barely had a moment to enjoy it before he gripped her hair again and pulled her mouth over the head of his cock and rammed himself down her throat again. Alexei grunted with pleasure as Jen gagged again, her pleasure forgotten once more. He fucked her face slowly but firmly, running her along his entire length. Tears ran from her eyes, her lungs burned, thick saliva dripped from her chin.

But then he released her again and as the air filled her lungs, the heat filled her pussy. Her clit felt it was on fire, her cunt rocked back and forth on the dildo and her arsehole grasped at the plug. She moaned loudly just before he went back to fucking her face. The pattern repeated itself as he treated her roughly with his cock then let her wallow in the intense sensations in her pussy. The moments of pleasure were so short lived that they were never quite long enough to get he to her peak. Eventually she knew Alexei's stamina was not going to give out, and she needed her climax.

She should have been worried that this selfish act was going to incur some future punishment, but all she could think about was the throbbing pressure inside her that had to be released. As he lined up her face for yet another throat-fucking, she stopped him for the first time. "Wait, please, wait. I need this..." she gasped, holding his thighs. She rested her forehead on his spit-slick balls and ground herself down on the furiously buzzing sybian. Using him to support her weight she tensed every muscle in her pussy and ass, heightening her pleasure as much as possible. Finally, she was there.

What started as a low groan, became a long shriek as her orgasm finally crashed around her. "Fuuuuuck! Shitfuckshit!" She screamed into his lap. She could feel the wet base of his penis rubbing in her hair as it towered above her, but she didn't care at all. Her thighs slipped on the smooth sides of the sybian as her moisture flowed out of her. Waves of pleasure flowed out from her centre, only to re-double in intensity when Alexei turned the control all the way up to its highest setting. Within seconds she was scrabbling to try to lift herself off the vibrating pad as the sensations overwhelmed her. "Enough! Stop! Please!" She begged, but Alexei made her wait a long moment before the assault on her clit relented. As the machine turned off, Jen slumped back down on it, then fell forward onto her hands as Alexei stepped away - removing her pillar of support.

"I am glad you experienced that, Jen" Alexei said, smugly from somewhere behind her. Jen didn't respond as she was still gasping for breath, her face a mess of ruined makeup and her own drool. She could feel her own hot sweat running down her face and breasts as her body fought to keep up with what was being done to it.

"I get great enjoyment from the extremes of your experience, my little pet." He continued. "Your greatest pleasure and your greatest agonies are what interest me the most. It is when you feel the most intense stimulation that I can see what a beautiful person you are." Jen didn't feel very beautiful at that moment, but she didn't say anything. "And that is why I must torture you more."

Wait, what?

She felt his fingers grip the end of the plug in her ass and then suddenly her eyes were bulging as it was ripped from inside her. She barely had time to scream before his weight squatted down behind her, pushing her forward. He gripped a handful of hair to keep her in position, while his other hand aligned his rock-hard cock and her arsehole.

"Wait!" she squealed. But it was too late. He pushed forward aggressively, shoving his way past her resistance. This time she did have time to scream. "Ahhhggh! Ah! Arrgghhh!" The pain was intense and did not abate as he continued pressing forward until he was completely sunk into her butt. Once there he stopped and she could feel him flexing his steely shaft inside her. He pulled her head up closer to his by her hair.

"Good girl, good girl. Take it for me." He whispered in her ear. "Endure this and show me I was right to think you were different."

'Click'

Jen felt the sybian rumble into life beneath her, vibrating her clit. It did nothing to reduce the pain she was feeling, but her body still immediately embraced the pleasure. Between the dick in her arse and the dildo in her pussy, she had never felt so full. And with the constant friction on her clit, she had never been so stimulated. It wasn't exactly a nice feeling, she couldn't imagine doing this everyday, but even with the pain, it wasn't entirely unpleasant.

Alexei started a very slow rhythm, slipping backwards until only his helmet was still inside her, then pushing forward until he was buried to the hilt again. Each movement caused reactions in her pussy or on her clit, until she felt like she was having sex with three people at once. Despite her intention to stay quiet, she squeaked like a chew-toy every time he bottomed out in her. Jen wondered again at his stamina and self-discipline as he continued to ream her slowly, making her feel every inch of him while never losing control of himself.

'Click'

Gradually his speed increased, along with the force of his thrusts; each one pushing her harder onto the sybian. At the same time, he was gradually increasing the power of the vibrations underneath her until she saw stars behind her eyelids.

As her body adapted to his invasion, the pain lessened dramatically, while the increasing power of the vibrations pushed her higher up the ladder of pleasure until she faced a shocking realisation. She was going to come while he was fucking her arse. She had spoken to friends a lot about anal, some of them loved it, some of them hated it. But none of them could say they came the first time they tried it. In the back of her mind she once again did the sums to decide whether her Operational Tour Bonus money could stretch to buying her a sybian of her own.