Imprisonment Ch. 04

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Justin was slightly surprised to see his boss, the warden, arrive at his door around four in the afternoon Friday instead of the usual time of five. Blinking up at him from his desk, he hesitantly asked “Something wrong, sir?”

“Nothing’s wrong. Is there anything you’re working on that can’t wait until Monday?”

Justin considered for a moment. “No, I suppose not.”

“Good. Come along with me, then.”

Justin stood and reluctantly walked over to Fairfax’s side. The older man put an arm around his shoulders and led him down the hallway. “We’re just going to take a few minutes to get you ready this time.”

“Get me…ready?” This was the third Friday in a row that Justin would be punished for his embezzlement of funds by putting him in a room with the prisoners whose families he’d stolen from, but it was the first time Fairfax had said anything about getting him ready.

“That’s right. Remember last week, one of the blokes said you’d look nice in a dress? And he suggested you should shave…”

“…what?! Oh, sir, please, don’t make me do that…” he remembered all too well the man reaching between his legs, yanking out several of his pubic hairs while commenting that he’d look better without them.

“Oh, really, it won’t be so bad. What’s putting on a dress and shaving compared to all the other things they do to you?”

Justin sighed. The man had a point. In comparison to the beatings and forcible sex, skirts and the removal of a little hair didn’t seem like such a big deal.

Fairfax led him to the infirmary, where once again a room had been left vacant for them. Steam rose from hot water in a large bathtub. “Go ahead and undress, Justin.”

“Um…do you have to be here for this, sir?”

Fairfax smiled. “I suppose I don’t have to, but I was planning on shaving you myself.”

Justin blushed hotly. “Why?! I can do it…”

“I’m sure you can, but it’s a difficult area to reach and see. I’ll be able to do a more thorough job. Go on, get undressed and soak for a little bit.”

Justin disrobed slowly, still blushing and keeping his eyes lowered. He placed his neatly folded clothes on a chair before stepping into the tub, lowering himself shakily into the water. It did feel nice, at least. He sank in until his shoulders were nearly covered, sighing. He kept his hair pulled back and out of the water.

Fairfax approached the tub with a smile, holding a washcloth, soap and a razor. “We’ll let you soak a little while, makes the hair come off easier.” He gave Justin a little pat on the cheek. “Cheer up, it’s not so bad.”

Justin huffed a little. “Easy for you to say.”

Fairfax chuckled. “I know it hurts. But after tonight, it’ll be more than half over.” He was silent for a moment, then asked Justin, “Have you tried stretching yourself a little? Maybe make it hurt a bit less?”

Justin grimaced. “Most of the time I’m just too sore. And I don’t like touching myself there. Just…reminds me.”

Fairfax nodded. “I can see that. But you know…some people actually enjoy being touched back there.”

Justin scoffed. “I don’t see why.”

“I understand that what the prisoners do to you is no fun. But it can be very different.” Justin still looked skeptical. Suddenly Fairfax reached into the water, then soaped up his hands. He reached in again with one hand, and began to move it between Justin’s legs. The younger man scooted back against the side of the tub, startled. “S-sir…what casino siteleri are you doing…”

“Just relax and let me show you.”

“But…sir, please…”

“Come on, Justin. I took care of you last week, didn’t I? Didn’t it feel good?”

Justin could only blush at the recollection of being held close and stroked to orgasm by his boss, and fell silent as the man’s fingers slipped between his cheeks. He bit his lip as a slick finger began to push at his entrance. It wasn’t very sore any longer, but the feeling of anything back there was still unwelcome. The finger continued to press further inside him, prodding insistently, until it rubbed over a place that made Justin gasp and grip the edges of the tub in surprise. “A-aah, what…”

Fairfax smirked, his face near Justin’s own. “Doesn’t feel so bad now, does it?”

Justin didn’t reply, only panted and leaned his head back as Fairfax began sliding another finger into him. He began rubbing against that spot inside him with both fingertips now, continually back and forth, until Justin began to whimper and shake. His cock, soft just minutes before, was now stubbornly erect and throbbing against his belly. “Ah…God…” his eyes were closed, but suddenly he felt a soft kiss on his cheek, then his neck, as the gentle prodding continued.

Desperate for release, Justin reached down to wrap his hand around his erection, stroking himself quickly as his legs began to stiffen and tremble. Fairfax kissed his face again, and with a final shudder of his slim frame Justin reached his peak, adding his own fluids to the water. He then leaned back weakly against the side of the tub and opened his eyes as Fairfax chuckled and withdrew his fingers. The older man caressed his chest briefly with his damp hand, then dried his hands on a towel with a grin. “You didn’t seem to think that was so terrible.”

Justin blinked up at him, flushed. “W-well…it was very…different…”

Fairfax nodded. “Certainly. I don’t have any particular interest in hurting you myself. I just wanted you to know that it isn’t always awful. If someone were to go slowly, and if you weren’t already sore from being beaten, being fucked could actually be very pleasurable for you.” Justin listened, looking embarrassed but not saying anything.

“Well, let’s get you shaved. It’d probably be easiest if you stood up.” Justin stood, closing his eyes in self-consciousness again as Fairfax lifted his cock and began to gently soap and shave his groin and scrotum. He didn’t open them again until Fairfax said “Okay, now turn around and bend over a little with your legs spread a bit.”

“W-what? Why?”

“So I can get the last of the hair. It wouldn’t make sense to shave you in front and not in back, after all.”

Blushing, Justin turned and bent slightly at the waist, placing his hands on his knees. He felt the razor slide smoothly between his cheeks as Fairfax shaved him with careful strokes. “Okay, all done – you can rinse off now.” Justin eagerly sank back into the water, wiping the soap residue from his skin. Fairfax smiled. “You really do have a cute backside. I’m a bit jealous of these men.” Justin looked up at him incredulously, but couldn’t think of a response. What was one supposed to say to such a thing? He finally spoke as he stood up and began drying off. “Don’t you like women, sir?”

Fairfax looked thoughtful for a moment. “I don’t dislike them. But I’ve never really felt anything for one. My family slot oyna pressured me into getting engaged a couple of years ago – she was a nice girl, but I couldn’t see spending the rest of my life with her. Luckily for me she ended up falling for my younger brother instead.” He grinned. “And what about you? You’re sort of a catch – got a good job, easy enough on the eyes. Why aren’t you married yet?”

Justin shrugged as he toweled himself off, really having to think about the question. “I guess…I’m the same as you. I’ve been around girls, but never really met one I wanted to be with all the time.” He looked up to see Fairfax lifting a big box tied with string onto the counter and opening it up. First he pulled out a rather skimpy pair of white, lacy panties, which he handed to Justin with a grin. Justin took them with a grimace.

“Ugh. These don’t look very comfortable.”

“I wouldn’t worry too much about that, they won’t stay on for long.” Justin winced even more at that thought as he stepped into the underwear, pulling them up carefully, tucking his genitals into the small slip of fabric. Fairfax stood grinning at him like a Cheshire cat. “Cute. Now pull this on.” He handed him a ridiculously frilly dress of pink and white checkered fabric, liberally trimmed with white lace. Justin sighed heavily and pulled the dress over his head, smoothing it down as the skirt fell down over his hips. To his surprise, it was tailored to fit his shape exactly, clinging to his flat chest and narrow waist until the skirt flared out. “Did you, uh, have this made, sir?”

“Yep. Brand new, just for you.”

Justin blushed furiously, bewildered as to why the man would have paid for a brand new dress just for this occasion. And that wasn’t all – next Fairfax presented him with a garter belt and white stockings, also trimmed with lace, and finally a pair of shiny black patent leather mary jane shoes. Once he was all dressed up, Fairfax tied a pink ribbon around the younger man’s long red hair and beamed his approval. “Oh, you look lovely. They’ll be delighted.”

Justin just sighed again as his boss put an arm around his waist and led him to the usual room, where he was greeted with catcalls and laughter. As usual the table of implements was present, this time holding a large wooden-backed hairbrush, a riding crop and a leather martinet along with the tub of petroleum jelly and lengths of rope. Justin was somewhat relieved, however, to see that there were no objects evidently designed to be shoved up his backside.

After Fairfax’s typical introduction, Justin was once again subject to the whims of four prisoners, all of whom were taller and more muscular than himself. The tallest of the men approached him first, walking in a circle around him with a predatory grin.

“What a pretty little slut. What do you say, boys, should we tie her up and take turns?” After the others approved, Justin found himself forced to bend over the back of a chair, and his ankles roughly tied to the legs. Another prisoner happily tied his wrists to the front legs of the chair. Justin trembled in apprehension, already uncomfortable in his restraints. Someone lifted the skirt of his dress up over his back, and he blushed hotly as the men whistled and laughed at his frilly undergarments. Someone smacked his scarcely protected bottom with a hand, and he flinched.

“Well, we can’t do as we like with these things on. Sorry, darling, maybe daddy’ll buy you new ones.” Justin winced canlı casino siteleri as the underwear were yanked on and torn, leaving his bottom only covered in a small area near his waist by the garter belt. Everything between his legs was now exposed, and groping hands felt the smoothness of his skin. “So soft, just like a pretty young girl. We’ll have a good time with you.” Justin heard steps retreating, and then a firm hand was placed on his waist. “But naughty little girls like you get punished until they’re sorry.”

Justin yelped in pain as a hairbrush smacked his backside hard. The man wielded it with ferocity, quickly bringing redness to the young man’s bottom, then harder blows that would surely result in bruises. He only stopped when Justin began to sob uncontrollably, his slim body shaking over the chair. Before he could gather himself at all, slick fingers were shoved inside him, and then the man was fucking him, hard and relentless, pounding his pelvis against Justin’s throbbing little beaten backside.

It only got worse. The next prisoner didn’t hit him first, but his cock was improbably large and his ruthless thrusts made Justin shriek helplessly in pain. He felt as if he were going to be ripped apart. The lashes of the martinet that came afterward were almost a relief in comparison. Then he was fucked again, and though this man wasn’t so large he was certainly energetic, slamming against Justin’s enflamed and scarlet bottom.

The riding crop came next, sharp, quick slashes that felt almost like cuts, and another round of vigorous penetration, leaving him as usual a sobbing, limp wreck at the end of the hour. He could scarcely breathe from crying so hard, and felt as if he’d pass out as Fairfax untied his limbs. He barely registered the man’s touch as he massaged the skin where the ropes had scraped against it. As he was drawn into Fairfax’s arms, he unconsciously curled against him for comfort, weeping pitifully.

“Shh, shh. It’s all over now. You’re a good boy. Good boy.” Justin vaguely thought that at least his boss was referring to him in the male gender. He’d grown tired of being feminized by the prisoners, who’d called him things like “dirty girl” and “filthy little bitch.” He lay limply in Fairfax’s arms as he was carried to the infirmary, whimpering needily as he was laid down on the cot – though he’d never admit it, the man’s embrace had been soothing. But Fairfax was soon touching him again, cleaning him gently as always, undressing then redressing him in his ordinary clothes, untying his hair and brushing his fingers through it. Justin didn’t manage to speak, even once they were in the carriage. He lay with his head in Fairfax’s lap, secretly thankful for the man’s warmth and his gentle touch as he continued to stroke his hair. When the carriage stopped and Fairfax carried him out, he blinked in confusion. “Sir…where are we?”

“You seem more upset than usual. I want to make sure you’ll be okay, so I’m bringing you to my flat. You can go home tomorrow if you feel like it.” Justin looked up at his boss, his expression a mixture of gratitude and embarrassment, as he was carried up two flights of stairs and into Fairfax’s home, which was dignified and comfortable. Not unlike the man himself, Justin hazily thought. He was deposited on a cozy sofa as Fairfax lit a fire, and then helped to a large, comfortable bed. Fairfax helped him undress to his underpants and vest, and eased him into the bed. “I’ve only got the one bed, but it’s big enough.” Too exhausted and sore to protest, Justin lay silent as the older man joined him, wrapping an arm comfortingly over his chest as he lay down beside him. “It’s okay, Justin. Get some rest.”

So he did.

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