Riding Bone
Chapter 5
Paul blinked quickly in the afternoon light, momentarily blinded. In the bright haze, he could tell that he was on a busy street. Someone jostled him and he felt their hand up against the bare skin of his waist.
“Watch where you’re going there, sweetcheeks,” a deep, amused voice said. He squinted but couldn’t see where the person who had said it went. The haze started to clear, and from the rainbow flags on the businesses and the large phallic columns on the street corner, he could see that he was in Boystown. It looked to be late afternoon. Several people were bumping into him on the way to their destinations, murmuring apologies or outright obscene statements.
Paul looked down and realized why they were making the remarks. He was wearing nothing but a pair of extremely short leather shorts that bunched up in front to give his crotch a very rounded look. A chain descended from each of his nipples, meeting around his navel and disappearing into the leather shorts. And he was wearing some sort of leather vest that barely reached his sides, leaving the front of his body almost fully exposed. He searched around quickly for his bike, but couldn’t see it anywhere. He fumbled around the shorts, feeling for a pocket for his wallet or keys, but couldn’t find them anywhere either, and he didn’t have any of his gym bags. He was stranded almost 10 miles from home without money or transportation! And in this get-up, there was a distinct possibility he may never get home.
The worst part was, he had no idea how he’d gotten here or what was going on. His nipples throbbed from the two nipple rings, but he couldn’t remember getting a piercing. He could feel something constricting against the base of his cock and balls, keeping him semi-erect, and he deduced that it must be another ring from the chain attached, but he had no idea how they’d gotten there. He looked like some sort of gay rent-boy or something, and in the gay area of town. He started to panic, trying to think of how to get out of the situation.
The first thing he thought of was to get out of the busy street. The stares he was getting were making him uncomfortable. He started walking quickly, and just as quickly slowed down significantly as the chain tugged on his very sore nipples with each step. He hunched over slightly to give the chain more play, and sighed in relief at the ease of the tension in the wire.
The walking, though, brought the clear understanding that he had something lodged deep up his ass.
With each step he took, he felt it squirm around inside him. He instinctively put a hand to his ass and felt around his asshole; there was a noticeable bulge of something there. He had no way to get it out here in the middle of the street, though, and the only businesses around him seemed to be gay bars and porn shops. He couldn’t get it out in either of those places; he’d be jumped the moment he got in!
Paul resigned himself to having to continue on with the plug buried inside him. This was like some sort of strange, erotic nightmare, only he knew he was awake. Had he been drugged and raped? Had some sort of psychotic episode? As he slowly walked, the plug bringing him involuntarily to a full erection as the bright afternoon sun beat down on him, he tried to think back to how this had all happened. He was drawing a total blank.
In shock, he stumbled down the street, putting one foot automatically in front of the next, trying to pretend he was anywhere but where he was, in the clothes he was in. He could feel the eyes on him anyway, staring. His head was down so far that he walked right in to a fleshy wall. He actually bounced off of the man in front of him before he could stop himself.
The man, a shirtless behemoth, had to have been 250 pounds of muscle, making Paul feel small by comparison. His close-cropped grey hair and clean-shaven face showed him to be a man in his fifties, and he was looking down at Paul with a sardonic grin. He reached out a hand to steady Paul but held him at arms length, openly checking him out. Paul stumbled out an apology.
“None needed, son,” the man breathed. “None needed at all.” He slid his hand down to Paul’s elbow and squeezed. “Now what could a boy like you be doing in a hurry on a day like this?” Paul felt himself flush all over.
“I…uh…”, he stammered, unable to think of a plausible excuse for a straight man to be out dressed like this. He felt intensely uncomfortable in the middle of the sidewalk with this man holding on to him. He tried politely to shrug the guy off, but his hand stayed there like it was welded to him. The man smiled.
“Oh, come now, it’s a beautiful day. No need to be in such a rush,” he said, and he pulled Paul closer to him. He smelled of cologne and sweat. Paul’s arm brushed against the man’s chest as he pulled Paul beside him and placed his hand on the small of Paul’s back. He grabbed Paul’s other hand and shook it vigorously, sarcastically introducing himself. “Name’s Darrell, boy. What’s yours?”
“I don’t think…” Paul began, and the hand tightened on his own until Paul winced. “Paul,” he muttered. The man’s eyes narrowed, but he maintained his smile. “Well, now, Paul,” he said as he slid his hand down Paul’s buttocks until they rested against the base of the plug up his ass, “It’s so great to run into you today.” He pushed on it, once, hard, driving it deeply into Paul’s ass, hitting something deep inside that made Paul see stars. He could feel his cock immediately grow to a full erection – in fact, he almost came right there in front of the street. He gasped and pushed his groin out, trying to evade the hand. The man just followed Paul’s ass as it bucked forward until Paul felt like he would lose his balance.
The man leaned in close to Paul’s side and spoke lowly into his ear. “Now a boy like you doesn’t dress up like that unless he wants some tail, or wants someone to take his. And given your little friend,” he pushed on the plug again, “I think I know which you want more.” Paul tried to protest, but the man spoke right over him as if he weren’t talking. “Now it just so happens that I have a room here in this little club that would do us both some good, if you want to follow me in here. I’m going to head on in. If you want what I think you want, you tell them you want room 35. They’ll show you the way.” He removed his hand from Paul’s ass and pointed at a nondescript door in a storefront. A simple sign hung over the front, reading “Open for Business.”
The man moved away from Paul, letting him go, waved at him as if to an old friend, and turned around and headed inside. Paul noticed despite himself that his back was thickly muscled, and he had a tight, large ass framed well by the black denim jeans he was wearing.
Paul felt relief at first that the man had gone away, and started trying to trudge on back north, toward his home. Every step, though, now caused him more and more arousal. He involuntarily thought back to the older man, and a twinge of lust started in his groin and spread to his abdomen. He couldn’t believe he was feeling sexual arousal from a man, but he knew it for what he was. His steps began to slow, and as he reached an intersection, he stopped altogether.
What could it hurt, he thought? The man wanted him, he was horny as hell, and the whole situation was so ridiculous. He’d never seen the man before and would likely never see him again. Where would be the harm? Something had conspired to put him in this place, in this outfit and condition, and left him free to do as he saw fit. Excitement pulsed through him. He could do this. Nobody need ever know.
As he stood there contemplating his options, shocked inwardly that he was even considering it, something clicked in his brain. Of course he wanted this. He was a young, virile man, and could get his rocks off however he wanted. So what if it was another guy? He could experiment if he wanted to… He straightened up, ignoring the pain from his nipples as they protested the strain from the chains attached to his nipple rings, and started striding back to the door. He opened it and stepped through.
His first reaction was surprise. A long hallway spread before him with velvet carpeting, dark red colored walls, and lighting tented red as well. The feeling was almost oppressive, except for the prints beside each door in the hallway depicting men in various states of arousal. A deep techno beat was thumping somewhere down that hall. A bored-looking attendant looked at him and held his hand out. “$20 per room per hour,” he said mechanically.
“Um… I’m here to see someone who already has a room. They said you’d let me through? Room 35.”
The man took another look at him and grunted. “Oh yeah, you want Big D. Well, go on then.” His face took on an almost pitying look as he gestured Paul through.
Paul walked down the hallway, glancing at the prints on the wall. The further down he walked, the more sexual the photos became. By the time he reached the door marked “35”, the prints were of men openly fucking, some in groups. Paul looked more closely at the one in the room he was about to enter. He was so close to turning around and running out the door, but he couldn’t get Darrell’s amazing body out of his mind. He steeled himself and extended his hand to the doorknob, and turned it.
When he opened the door, two arms quickly pulled him in and the door slammed shut behind him. The room was pitch black; he couldn’t see a thing. He felt Darrell’s physical presence more than saw it, though aside from the initial grab, the man hadn’t touched him. He stood still, not daring to move or speak, as the seconds ticked by. All he could hear was the sound of his own heavy breathing.
A hand scraped across his chest roughly, rubbing against his sore nipples and eliciting a gasp, then disappeared again. More seconds passed. Now the hand was on the inside of his front upper thigh, barely scraping against the leather shorts. It angled upwards and cupped his crotch momentarily, causing Paul to groan, and then went away again. Barely a minute had passed, but it felt like he’d been standing there for an hour. His eyes still hadn’t adjusted in the dark.
Now two hands latched on to his vest, pulling backwards, and he allowed the vest to slide off his upper body, the movement of his shoulders backwards tightening the chain between his nipples and causing him to groan again in a mixture of pain and pleasure. He now stood with nothing but the shorts and a butt plug in the dark, and Darrell had still not said a word.
More moments passed. Paul felt the arousal in the room like it was third soul, pressing in on him, making him strain against the tight confines of his leather shorts. A hand reappeared, snaking down his hip-bone to the open sides of his shorts. With a yank, it untied the knot on the shorts, and slowly, slowly pulled the lace out of each hole until the shorts gaped open on one side. Paul felt his aching cock and balls spring free from their confinement, balls sweaty from the walking and the imprisonment in the shiny leather. The hand disappeared.
“What…” Paul finally ventured to say between gasps of lust, and a rough hand quickly covered his mouth. He felt Darrell’s presence behind him and then Darrell was enfolding him in his arms, forcing him back against the unyielding muscle. They fit together like two pieces of a puzzle, the ridges of Paul’s back sinking into Darrell’s abdomen and chest. Darrell cooed softly in Paul’s ear, saying nothing, just murmuring calming noises, as he reached around and grabbed Paul’s twitching, dripping cock. His thumb made smooth circling noises over the glans of Paul’s penis, causing him to breathe harder through the hand gagging him. Darrell’s hand moved from Paul’s mouth and reached between the two embracing men, finding the now-uncovered butt-plug. He pulled it halfway out and shoved it back in again, causing Paul to see bright stars in his field of vision through the blackness. He would have come then and there, but Darrell’s fingers clamped down on the underside of his cock preventing the orgasm from completing. Paul bucked against the hand as his dry orgasm pulsed through him and sagged into Darrell’s arms silently. The experience was so mind-blowing. No woman had ever taken control of him like this, had focused their every effort on making him experience higher and higher levels of sexual arousal. And the age of this man was its own turn-on, with the experience he could clearly offer. Darrell’s mouth clamped on to Paul’s lobe and began sucking, discovering another erogenous zone Paul had never known he had. As he squirmed in Darrell’s arms, he opened his legs wider to give Darrell more access, which Darrell took advantage of by removing the butt-plug entirely with a loud squelching noise. Left with a feeling of intense emptiness, Paul could only groan in protest. “Please…” he whispered.
“Please what?” Darrell whispered into his ear.
“Please put … put it back in!” Paul whispered back, high-pitched, simultaneously embarrassed and aroused. He’d never talked like this before with any woman.
“I can do better than that,” said Darrell, and Paul felt himself being gently pushed forward until his knees hit a solid yet soft object. He allowed himself to be bent over it and realized from the sheets that it was a bed. The dark was still complete and he couldn’t see it, but it had a soft quality and smelled of dried, old sex. Every time he inhaled brought the scents of sex and cum to his nostrils, which drove him even more insane with lust. He heard Darrell behind him making squelching noises near his waist, and realized he was spreading lube on his cock.
Darrell positioned himself behind Paul and Paul felt the head of a warm, pulsing foreign object enter him without fanfare. The pain was both sharp and intense, and deeply erotic. He let out a low, deep moan and tried to scootch back on it, but Darrell held him fast, one hand on his abdomen and the other pushing down on the small of his back. “Just relax, son, and let me drive,” the man said, and slowly, ever so slowly, he relentlessly drove inch after inch – Paul had no idea how much but it seemed to go on forever – into Paul’s ass. The shorts hung off his side on one half, giving access to his asshole but not falling off. His cock ground against the bed, dripping and hard. For what seemed like minutes, Darrell pushed himself into the smaller man until the base of his groin met Paul’s ass, and then he held himself in there, flexing his penis but not moving.
“How does it feel in there, boy?” he demanded roughly, and Paul let out a loud groan. “God, it feels like I have a Peterbilt up my ass,” Paul moaned, and the man laughed. “Yeah, I guess I might could have loosened you up a bit more, but you took it like a pro, and the buttplug helped loosen you up too” Darrell said between his own pants. The older man began pistoning slowly in and out in small jerks and maintained his hand on Paul’s raging hard-on, gripping it tightly.
“I’ve never done this before,” Paul said, and Darrell grunted in surprise. “I mean it, I’m straight,” Paul said, and Darrell laughed outright. “Boy, nobody in your get-up is straight. Nobody moaning like a bitch in heat under my cock is entirely straight, though I am flattered,” as he pulled out and pushed in deeply, causing Paul to moan loudly. Paul ruminated on this as he was slowly fucked from behind. Was he bisexual? Prior to today, he would never have given another man a thought – or would he? Between pants and moans, he tried to think about whether he’d ever done anything like this before, but he came up blank. He could remember a string of women that had been mediocre lays, though they’d had excellent emotional connections. Darrell seemed to sense that Paul’s mind was wandering, so he reached up with his free hand and gently tugged on the chain connecting Paul’s nipple rings to his cock ring. The pain was immediate and Paul cried out, all other thought forced from his head by the searing pain,, but it was almost immediately replaced by a slow burn, not at all unpleasant. His entire body felt hot, and he felt completely filled by the huge man behind him.
Paul reached around behind him and tried to touch Darrell, but could only manage a few swipes at the man’s abdomen. “Let me face you,” he whispered between grunts, and Darrell obliged by expertly flipping Paul over on the bed with his cock still driven deep inside him. Paul’s legs were now spread wide, and Darrell was able to drive further into him than before. Paul found his eyes had adjusted to the dark as well, and he could see Darrell’s silhouetted shape above him, like a dark shadow grinding away above him and deeply into him. Paul spread his legs as widely as he could to give as much access as possible, nearly doing the splits, and he reached his arms up and enveloped Darrell in a bear hug, using the man’s broad shoulders as if they were pull-up bars, meeting Darrell’s own strokes now. The two men pumped against each other quietly, allowing only grunts and moans to break the silence, and suddenly Darrell went stiff and groaned loudly. Paul felt the man’s cock pulse deep within him, and then a feeling of warmth spread from deep within his bowels, seeming to coat him all the way down. Darrell stood stock still for a moment, and then a long, long sigh escaped him. “Oh god, lad, that was amazing.”
Paul was too busy to listen, though, as his own orgasm had begun. It seemed to last forever, from the moment he had felt the first spurt of semen coat his bowels, he had erupted himself, coating his chest with long ropes of cum. He couldn’t keep quiet and started weeping from the ecstasy, gritting his teeth to try to prevent the sobs of joy from escaping. After what seemed an eternity, the pleasure subsided and his suddenly weak arms gave way. He fell back onto the bed with Darrell still buried inside him.
He heard Darrell say something, but he had no idea what it was, as Darrell physically picked him up and scotched him further up on the bed. He felt a soft towel being wiped across his chest, and then a tongue was licking around his sore nipples, bringing relief and more sexual pleasure. He cried out, saying “Too much, too much!” and tried halfheartedly to escape, but Darrell continued his tongue assault. He had a smaller orgasm within seconds of the big one, and Darrell planted his mouth on Paul’s as he started weeping again, twining his own tongue about Paul’s. He lifted his head up after a moment. Paul could see his eyes gleaming in the near total darkness. “You are one hot fuck, son.”
“You were amazing yourself,” Paul said, and he lifted his hands to his face to dry his eyes. Darrell pulled out of him, leaving Paul with just the memory of his ass being filled to the brim, and he could hear the man getting dressed in the darkness. Paul fumbled with the undone lace of his own shorts on the bed until he got them done up again, leaving the buttplug behind. “Will I see you again?” he asked hopefully.
Darrell said nothing. “I’d love to get your number,” Paul begged. “I don’t think so,” Darrell said. He seemed to have lost interest. Paul couldn’t understand. Had he done something wrong? As Darrell left the room without a goodbye, he lay back on the bed trying to understand what had just happened. He wasn’t confused about the sex – that had been amazing – but he was very confused about his feelings regarding the anonymity of it. He’d never had sex without attachment before, and yet this had clearly been exactly that. After some thought, he decided he’d liked it. It had added an air of danger to the entire experience.
He got up off the bed and fumbled around the room for a light, finally finding it near the door. It blinded him for a moment, and when he was able to see he saw that the room was filled almost entirely with a bed, with just a nightstand on the side with some towels and lube on top. His vest was on the floor, and he grabbed it and shrugged back into it, then looked around the room. He could feel cum trickling out of his ass, collecting between his legs. His cock was still half-hard from the cockring, but he felt completely spent. Still, he felt like something had changed within him, as if Darrell’s breach of his sphincter had breached something else within him. He knew he would do this again.
He left the room and walked back down the hallway, past the smirking attendant, and back into the blinding light of the late afternoon. He couldn’t have spent more than a few minutes in the dark chamber of the sex hotel, but it had felt like hours. Of Darrell there was no sign. What to do now? He thought, and determined that one way or the other he would have to get back home. How he would get inside without keys he had no idea.
He began walking up Halsted, no longer trudging, but with his head held high, basking in the erotic stares he was getting from the gay boys on the street. He knew he looked amazing, and he puffed himself up a bit to give a better view. He openly checked out the other men now, often liking what he saw very much. Thin men, muscular men, even some slightly overweight men, he could find something in each that he admired or appreciated. The tilt of a nose, or the width of a jaw, or a particularly large mound in the jeans; he almost felt like he’d been granted a new lease on sex, and one that came far more readily than the few encounters he’d had with women. He knew he was being checked out in his own skimpy gear. He began to consider his own preferences – he liked the way the older men looked, or the muscular college frat boys, but the excessively young look turned him off. Definitely he liked the muscled more than the ultra-thin or the overweight. If they showed more skin, he found it a huge turn-on. And here in Boystown, everyone liked to show skin.
Several minutes of walking later, he reached the edge of Boystown and was in Uptown, the seedier area of the city. Black and Hispanic men walked past him, most staring straight ahead but a few giving him admiring looks out of the corner of his eyes. One or two muttered “fag” as he walked past, which caused him to blush furiously, but nobody accosted him. After about a half-hour of walking and a couple of miles, he was in Andersonville and felt less conspicuous, with its quirky shops and own gay scene. The men here were older, which suited him fine, and they definitely seemed to be interested in him. He struck up a conversation with two men in their 60’s who were clearly a couple, walking hand-in-hand down the street, and allowed them to run their hands up and down his body as they chatted with him, while men and women walked past them in the street. It was so liberating to be this sexual in plain sight, and he could feel his cock respond to the attention.
A car honked at him while he was talking to the men, and it slowed down as it approached. “Paul!” a voice shouted, and Paul turned to look at the man and the car. The car was a black convertible with a white interior, the hood down. The man inside was wearing a white suit over a strong frame, and Paul felt a small sense of recognition but could not place the man’s name. He said a confused “hey,” and was about to turn back to the men when the man in the car addressed him again. “I’m headed back to your place to look at your rhododendrons. Want a ride?” and Paul suddenly felt the world drop away from him. Without saying goodbye to the gay couple, he stepped away from them and hopped into the car without opening the door, settling into the passenger’s seat. The man grinned at him and waved to the gay couple, and sped off.
Paul sat in the car quietly as the man drove. “I can tell you’ve had quite a day,” he said in a soft tenor voice over the hum of the engine, “and I gather it’s been quite educational. The best part about it is how you did it without being under this time. I’ve managed to completely strip away your morals, your inhibitions.” He reached over and untied Paul’s shorts while he drove, unlacing first one side and then the other. Paul just sat in the car, allowing him to do what he wanted. When the shorts were completely unlaced, the man yanked on them, leaving Paul completely naked from the waist down. The cock ring gleamed in the evening light, and his erection was visibly jutting out from his legs, slapping against his navel whenever the car hit a bump. “Why don’t you jerk yourself off while we chat,” the man said amiably, and Paul obliged.
“I knew the day I met you in the office two months ago that I had to have you,” the man said conversationally as Paul yanked on himself. “It wouldn’t be enough to just have you once, though. I wanted to completely change your outlook. I have some expertise in the subject,” he grinned, and yanked Paul’s legs wider. Paul slid down a little in the seat, but had easier access to his cock, and continued to pump away at it. At a stop light, a young man looked over and gaped open-mouthed at the situation. “and you looked like a good candidate. Nobody spends that much time on their body without a little narcissism, and that meant you had at least a few homosexual urges. All I had to do was break down your inhibitions. Why don’t you take off that vest, you look hot.” Paul yanked off the vest himself, letting it slide to the floor of the convertible, and sat in the passenger seat in nothing but his golden chain, nipple rings, and cock ring. He continued to pump away at his now-dripping erection while staring straight ahead.
“You won’t need to go under for much longer. There’s just a few more things I need to do to you, and then you’ll be as free of me as you’ll ever be. Though,” he grinned, “you might ask to be put under for some games every now and again.” Paul said nothing, but suddenly gobs of come sprayed out from his dick, and he yelped like a puppy. He continued to stroke his still-hard cock long past the erection, writhing on the seat from the pressure on his now-ultra-sensitive cockhead, using the come as a lubricant. The man reached a hand over and rubbed the cum that had splattered on his chest into him, rubbing patterns into his trimmed chest hair as they rode.
“I’m going to give you your keys and your wallet. Your bike is back home, safe and sound. Your old clothes have been thrown away. I’ve left you an assortment of niceties. Nikol will be by on Monday evening to deliver the suits I have made for you. I think you’ll find them provocative. I know your officemates will. You won’t be seeing me again, Paul. I have some clientele I will be sending your way, though. I am sure they’ll find you quite accommodating. He smiled almost viciously at Paul.
“You won’t remember this ride, or me. If we pass each other on the street, you will not recognize me. You will simply go about your life as if nothing has changed. Your old self, though, is gone forever. I think you will be intrigued by the changes you will be going through in the coming months. You won’t know it, but I’ll be watching.”
“It has been a real pleasure coaching you, Paul,” he said as they drove into Paul’s condo parking lot. Paul opened the door and climbed out, naked, collecting his shorts and vest. Mac Avery shoved Paul’s wallet and keys into his hand, then grabbed Paul’s neck and gave him a rough, possessive kiss. He backed into reverse as Paul stood back up blankly, blissfully unawares of his obscene nudity, as Mac drove off literally into the sunset.
Paul stood for a moment watching Mac leave, then, still pumping his cock, walked up the three flights of his stairs to his apartment, opened the door, set his wallet and keys on the kitchen countertop, carefully laid out his leather vest and shorts on the dining room table, walked into his room, laid on his back on his own bed, and fell asleep, still jacking off. He came for a fourth time in the day right as the first dreams began.