The Rise of Alec Caldwell is a serial read. To start at the beginning please go to the archive to the left of the page and you’ll find the first section hiding under May 2011.
Alec listened as Chloe reeled off the latest conquest in her ‘fuck every man in a fifty mile radius’ life goal. Josh, apparently, was thirty-two and married but his wife didn’t like sex now she’d had their first child. Poor Josh had to make do with once a month – if, he was lucky. That sounded more than lucky from Alec’s corner. The words floated through his brain initiating auto response as his mind focused on the curve of Rick Hamilton’s ass where he was leaning over Sophie’s shoulder, at the desk behind Chloe. Alec’s eye slowly traced the line over the hip and shoulder to – fuck… Hamilton was looking at him. Alec flushed at the smile playing over Hamilton’s lips and concentrated on Chloe, concentrated so hard, that when Hamilton touched his shoulder, he jumped almost a foot in the air.
“I’d like to see you in my office, Alec.”
“Yes, sir. Now?”
“I think so, yes.”
Damn and blast. Alec tidied a few things on his desk and made his way to Hamilton’s office. He blushed as he closed the door and stood before the desk. Alec tried to fill his mind with mundane things – the sky looked grey for the time of the afternoon, maybe it would rain. The cherry colour of Hamilton’s office furniture was the same as that of the toilet cubicle where Alec…not such a good train of thought. Alec coughed lightly, trying to shake the idea of wanking to the image of Hamilton’s face out of his mind.
“No need to stand on ceremony. Take a seat.”
“Thank you, sir.”
“How long have you been here, Alec?”
“Two years, sir. Ten months on your team.”
“Do you like it here?”
“Very much.”
“And why is that?”
Was it a trick question? Was he expecting Alec to own up to the fact it was because he liked staring at Hamilton’s butt? “The salary is good, the people are friendly and I enjoy my work.”
“I may have something else for you.”
Fuck, no. Hamilton was going to transfer him out of the department. Alec's shoulders slumped and his hands gripped the arms of the leather chair as he shuffled uncomfortably in his seat. Get rid of the embarrassing co-worker with a crush. What else would it be?
“You’ll continue with your present workload. This will be along the lines of additional duties. Do you think you would be interested?”
No transfer. “Absolutely, sir. I’m very keen to increase my experience within the company.”
“Hmm. Stand up, Alec and come here.” Hamilton gestured to the space directly in front of him.
Alec did as he was told, trying not to swoon as he met Hamilton’s gaze. Looking down into Hamilton’s face definitely made Alec feel giddy. If only he had the courage to reach out and touch.
“You’re a sweet boy, Alec. Something tells me you haven’t quite understood what I’m offering you.”
“A chance for additional duties, reporting directly to you, sir?” Maybe, I think. No, Alec didn’t have a clue. What other possibilities were there?
Hamilton stood up and walked behind Alec. Alec could feel his breath so close to his neck, his cock started to swell. Think of something else. Think of anything else.
“It would mean late nights, working over your lunch hour and reporting to me personally every day.” The hot breath curled into Alec's brain. “Will that be a problem?”
“Not at all, sir.” Not in a million fucking years would spending more time with you be a problem.
Hamilton moved back around to his desk and picked up a piece of paper. “There will, of course, be a pay increase to reflect the extra duties. Will this be sufficient?” He handed Alec the paper.
Fucking hells bells. An extra fifteen thousand a year. Fifteen… fucking… grand.
“More than sufficient, sir. Thank you.” Alec placed the paper back on the desk.
Hamilton moved back behind him and leaned his chin on Alec’s shoulder. “But you don’t know what the duties involve. How do you know if it’s enough?”
“Oh, well, um…” Nope. Alec couldn’t get the words out with the man so close. If he were to turn his head, his lips would brush Hamilton’s cheek. Rock hard cock. Fuck, fuck, fuck.
“You look uncomfortable. Let me take your jacket.” Hamilton’s arms slipped around Alec’s waist and opened the button. He slipped the suit coat off Alec’s shoulders. Nothing left to hide the erection straining against his trousers now. Hamilton folded Alec’s jacket over the desk and stood in front of him. “You seem to have a problem,” he smiled, tracing light fingers over Alec's cock. Alec’s shuddered. He’d blow any second. How more pathetic could he be?
“I’m so sorry, Mr Hamilton.” Alec closed his eyes and looked at the floor. Just shoot me already.
“Nothing to be ashamed of, Alec. I like that you find me attractive.”
“I do. I mean, you do?”
Hamilton chuckled, still stroking the line of Alec’s cock. “Oh, yes. It will help tremendously. It will ensure your new duties are much more pleasant.”
“It will?”
Hamilton sat back in his chair and studied Alec again with those damn sexy eyes. Alec missed the man’s touch. How fucking stupid was that? Shouldn’t he be thinking of sexual harassment? The man had touched him up. But what did Alec expect when he was the one always making eyes at Hamilton?
“Let me help you out with that.” Hamilton wheeled forward in his chair and reached out to unbuckle Alec’s belt. You have got to be kidding me? Hamilton unhooked Alec’s trousers, pulled the zipper and let the trousers drop to the floor. Alec could only stare, open mouthed as Hamilton kneaded his cock through his undewear. Hamilton winked at him as he pulled at the waistband and slipped his hands into Alec’s shorts, pulling them free of his erection and sliding them down to meet his trousers. Holy, fucking, moly. “Everything okay so far?” Hamilton said.
“Oh, absolutely, Mr Hamilton, sir.”
“Good. Then we understand each other.”
I don’t understand a fucking thing but I am not complaining – oh no, not me.
Hamilton watched Alec’s face as he leaned forward and licked a drop of pre-come from the head of Alec’s cock. Alec groaned loudly and Hamilton chuckled before taking the whole head into his mouth and sucking.
“Oh. Sweet, lord. I’ll come in about five seconds."
Hamilton pulled back, letting Alec’s cock slip from his lips and took up a steady stroking motion with his hand as he watched Alec’s face.
“I’ll make a mess,” Alec said, squirming on the spot but not wanting it to stop.
“Yes, it does tend to do that.” Hamilton let go and sat back. “Do you suck cock, Alec?”
“Do I, uh…no, sir. I never have before.”
“But you’d like to, you like men?”
“Yes, sir. I’m happy to have a go. For you I mean. I’m willing to learn.”
“You are a strange one.” Hamilton picked up his phone and appeared to send a text. He put it back on the desk and looked at Alec. “Take off your shoes and trousers and bend over the desk.”
Fuck. This was it. Hamilton was going to pop his cherry. Alec couldn’t believe his body was complying with the instructions without his mind engaging. It had always been the other way around. Alec would be desperate to follow through but his body wouldn’t move. Now, here he was in an office where anyone could walk in, half-naked so his boss could play with him and everything seemed to be working. Was the risk of being caught the key all along, or was it the authority in Hamilton’s voice that pushed Alec into motion? Alec realised he couldn’t care less, he was just glad it was happening. It brought a whole new meaning to the phrase ‘being caught with your trousers down’.
“Good boy,” Hamilton said, as Alec bent over and held the edge of the desk. The words went straight to Alec’s cock and it jumped obediently. Alec watched through his legs as Hamilton wheeled his chair around behind him. Soft hands kneaded Alec’s butt cheeks before prying them open. A tongue lapped over his hole and he jerked. “Everything okay?” Hamilton asked.
“Yes, I just wasn’t expecting it.” Why would I think my boss was going to lick my ass? For fucks sake.
“Do you prefer to be prepared with lube?”
Damn. He was going to lose the opportunity of his life and all because he was a useless waste of a space virgin. He should lie. Just say yes and let the man get on with it.
“Are you sure you’re okay with this, Alec?” Hamilton’s hand smoothing over his back was the last straw.
“I’m so sorry, Mr Hamilton.” Alec was close to tears. Desperately trying to hold on to a last scrap of dignity seemed silly in his current position, but he really didn’t want to cry. “I’ve never. It’s just that…I don’t know what to do.”
“You’ve never been taken before?”
“No, sir.”
“That’s okay, how do you prepare your boyfriends?”
Alec felt completely stupid. There was no point lying, he was rubbish at keeping up pretence. Better to just tell the truth and get it over with. “If you want to replace me, sir, I understand. I’m sorry I’m not suitable.”
“You’ve never had anal sex?”
“I’ve never had any kind of sex full stop, sir.”
“I’m sorry, Alec, are you telling me you’re a virgin? As in, a God’s honest truth, pure as the driven snow, kind of virgin?”
Alec couldn’t hold the pose anymore; he fell to his knees in front of Hamilton and reached for his hand. “Please, Mr Hamilton. I want to do this with you, for you. I want you to fuck me. I know I’m stupid and pathetic, but I fancy you like crazy and you’re the first person to suck my cock, so it makes sense for you to be the first to fuck me. I –“
“Stop.” Hamilton seemed to be thinking. He stroked Alec’s hair and face and Alec moved into the touch. It felt so natural. “I won’t fuck you.” Alec dropped his forehead on to Hamilton’s knee. Now he wanted to cry but the tears were stuck. “Not today anyway.” Alec looked up at him. Was that a glimmer of hope? “You’re first time should be special, Alec, not over the desk at work.”
“But you will?”
“Yes, of course. I’m honoured, really. Beautiful thing like you falling at my feet and pleading, how could I refuse?” Alec gasped lightly at Hamilton’s smile. “So sweet,” Hamilton said and reached forward to touch Alec’s lips with his. Alec curled a hand around Hamilton’s neck and pulled him into a full kiss. This at least he knew how to do. He groaned as Hamilton’s tongue slipped into his mouth and he returned his own, searching out the man’s taste. Incredible. Everything he’d thought it would be. Alec’s cock bounced back to attention and he stroked it while deepening the kiss.
Hamilton pulled back, his eyes sparkling. “Wow, well you seem to have mastered that very well.” He noticed Alec's hand and slapped it away. “You don’t touch unless you’re given permission.”
“Sorry, sir. I don’t know the rules. Will you teach me? Make me what you need me to be.”
“Bend over the desk again. I’ll start to open you up a little.”
Alec was more confident this time. Hamilton knew the truth and still wanted this, still wanted him. That had to count for something. Hamilton spread his cheeks and licked and kissed his pucker.
“You must tell me if I do anything you don’t like or if I hurt you.”
“Yes sir, all good, so far.” The sound was throaty. Hamilton was already licking and sucking over his hole again and then fucking hallelujah, his tongue pushed straight inside Alec’s ass. Alec’s knees buckled and Hamilton let out a short laugh, propping up Alec’s hips but still fucking him with his tongue. Alec rocked gently back against him, imagining a cock there instead.
He’d always wanted to shove something up his ass when he’d been wanking but never had the courage. He’d always wanted to watch gay porn but was too afraid the police would come knocking on his door, even though it seemed everyone watched endless porn online these days. But now… now, Alec was being personally inducted into the sex club. It was such a weight off his mind knowing he wouldn’t die a virgin because of his indecision. Hamilton didn’t love him but he obviously fancied him and that was more than enough. Hamilton also seemed to know exactly what he wanted and that made Alec’s job easy. He just had to do whatever he was told to do. The thought sent a sudden, unexpected rush to his cock. “I’m going to come,” he mumbled. Hamilton stopped. “No, don’t stop. Please.” But the moment passed and Alec’s breathing started to settle.
“First lesson, Alec, you don’t come until I tell you.”
“I’ll try not to but –“
“No but’s. If you come before I say, you will be punished. Do you understand?”
Punished? What the fuck? Alec tried to gather a few thoughts together.
“Alec, do you want to learn the rules or not?
Rules. Rules were good. Alec could follow rules. Rules kept him safe. Rules were his life. “Yes. I’m not to come, until you say.”
Hamilton stroked a hand over Alec’s back. “Good boy.” Pre-come seeped from the tip of his cock at those words. “I’m going to fuck you with my fingers. Just relax and try not to clench.” Hamilton rummaged in his desk draw. A moment later, a slick finger slipped through Alec's pucker into his ass. Not uncomfortable but an odd sensation. Was that all there was to being fucked? What an earth was the fuss about? A steady rhythm started and again Alec rocked into the motion. “Good boy,” Hamilton purred. “You’re a natural. Just stay nice and relaxed.”
Oh, fuck. Alec’s knees buckled again as Hamilton hit something.
“Say hello to your prostate, Alec. The reason even straight men are known to like a finger fuck.”
“I can see why. Oh, shit, I’m going to come. I won’t be able to stop it.”
Hamilton stood quickly and Alec jumped as Hamilton slapped hard over his ass. Another blow, surprisingly painful, made Alec flinch. “Do I need to continue?”
“No, sir. I’m sorry. I’ll try harder.” Fucking hard was the right word. His cock was bordering on painful, but that stung, and wasn’t fun. Not really. Maybe a little. But he had other things to concentrate on right now.
Hamilton resumed his position and continued to fuck him, this time with two fingers. Good, it felt very good. Alec was trying to think of random things, willing away his erection when the door opened and closed softly. Alec heard it lock. Fucking hell. Hamilton didn’t stop and Alec kept his head down.
“Mr Hamilton, sir.” Holy hell, it was Michael from the second floor. Despite the fact a colleague was witnessing him being finger fucked by his line-manager, Alec couldn’t stop the gentle rocking motion his body was caught in.
Hamilton smoothed over Alec’s back in that reassuring way he was starting to like. “Good boy, Alec. This is Michael. Strip, Michael. He’s another one of my boys, Alec.”
Not just Alec then. No wonder all this seemed so normal to Hamilton. Did Alec care? Fuck, no. He watched through his legs as Hamilton’s fingers disappeared inside him. It was the hottest thing he’d ever seen. He saw a naked Michael, with an impressive semi hard cock, kneel at Hamilton’s feet and lean forward to kiss his shoe. Alec was too close and desperately fighting his orgasm to have thoughts about it. The relentless rhythm was threatening to carry him away.
“Suck Alec’s cock, Michael. We want this to be a day he remembers for a very long time.”
Michael crawled underneath Alec and sucked in his entire length. Alec whimpered. “Please, I can’t, oh god, please.”
Hamilton thrust faster with his fingers, stroking Alec’s back steadily. Michael was doing clever things with his tongue that ate away at Alec’s brain, eroding his composure. His whole body trembled with the strain of not coming. Don’t come, don’t come, don’t come. “Please, Mr Hamilton, please. I want to be a good boy but it’s so hard. I’m so close. I want to be good. Fuck, fuck, fuck.” Hamilton thrust deeper and faster, rubbing over that spot as Michael sucked harder.
“Come for me, Alec.”
“Oh, fuck yes.” Alec sprayed into Michael’s throat. On and on it came, his body clenching around Hamilton’s fingers. He rested his head on his arm and panted. His shirt stuck to his back, sticky with sweat. Michael licked over the head of Alec’s cock one more time then took up his position at Hamilton’s feet.
“Very well done, Alec. You came on command first time. I’m very pleased with you.”
“Thank you, sir.”
“Now take off your shirt and come here. Michael is going to teach you how to suck cock.”
Interesting on the job training, Alec thought as he stripped off the sweaty shirt and rubbed the come into his belly. He took up a position on his knees next to Michael. Hamilton stroked Alec’s cheek and sat back in his chair. Every second of attention from Hamilton did things to Alec’s insides. He had the strange urge to climb on to the man’s lap and curl against his chest. No time to think about that now.
The lesson began. Michael took out Hamilton’s cock. He demonstrated teasing the tip with his tongue and then sat back. Alec looked at Hamilton who motioned him forward. Alec took hold of Hamilton’s cock with a small contented sigh and stroked it. Magnificent. His daydreams had never taken him this far. Hamilton’s cock, waiting for Alec’s attention, did it get any better than this? He leaned in to kiss the tip, tasting salty pre-come on his lips, and he licked them slowly before copying the tease Michael had showed him. He kissed the head again and for good measure, and because he could, he sucked the end into his mouth. It tasted amazing. His tongue swirled around the head and he groaned softly, sucking once more before he let it go and sat back. No good, he couldn’t leave it alone. He reached forward once more to kiss it again.
“Are you sure you need me?” Michael chuckled. Alec blushed and Hamilton took hold of his chin and pulled him up for a kiss. Alec threw himself into that kiss letting his hands wander and stroke Hamilton’s cock.
“I can’t believe it,” Alec said, when Hamilton broke away. “I can’t believe I get to touch you, and kiss you.” Alec dipped his head for another quick kiss and suck of Hamilton’s cock before sitting back to await instruction.
“You are the most incredibly, beautiful thing,” Hamilton said, stroking Alec’s cheek again. “My beautiful boy.” Alec smiled. He liked that a lot. Hamilton’s beautiful boy.
The lesson continued. He didn’t do too badly and he certainly enjoyed himself. He sat back and watched as Michael finished the job and swallowed Hamilton’s come. When Michael came up for air there was a small drop on his lip. Alec wanted to taste it. He wiped it away with his thumb and licked it off.
“Do you like it?” Hamilton asked, with a broad smile.
“Very much,” Alec grinned. “Is there anymore?”
Hamilton roared with laughter. “You are remarkable and hard again, I see.” Alec went to stroke his cock but remembered he wasn’t allowed to touch and dropped his hand. “Good boy. I think you deserve a little something special.”
More special than the orgasm of a lifetime and getting to suck Hamilton’s cock? Maybe Hamilton was going to fuck him after all. Alec certainly felt like he needed something up his ass right now.
“Michael, present yourself for our boy.” Michael spun around on his knees and leaned forward placing his chest and shoulders against the floor. He opened his legs slightly and spread his ass cheeks. Fucking hells, bells that was hot. Alec’s cock was as eager to get to work as he was.
“You’re going to fuck him for me, Alec.”
“I don’t know how.”
“I’ll guide you.” Hamilton grabbed the lube and a condom. “Kneel between his legs.” Alec followed the instruction. His cock bounced along Michael’s crack and the pucker spasmed. Hamilton knelt behind Alec and wrapped his arms around his waist. He leaned his chin on one shoulder and rolled a condom over Alec’s cock, spreading lube all over it. “Hold out two fingers.” Hamilton poured a small amount of lube on Alec’s fingers. “Now push them slowly inside, like I did with you.” Alec rubbed over Michael’s pucker a few times and pushed past the tight ring all the way in and back out. He repeated the process and Michael started to moan. “Good boy, Alec,” Hamilton whispered in his ear. “Very good. Do you like to be a good boy?”
“Yes. I like being your good boy, sir.” Alec turned to capture Hamilton’s lips whilst still finger fucking Michael, so erotic. He was certainly making up for lost time and being told what to do made everything easy. No stress, no mistakes to make. He was free to enjoy the process.
Hamilton kissed over his cheek as Alec looked back to see his fingers disappearing into Michael. Incredible. Why had he thought this would be so difficult?
“That’s enough.” Hamilton placed a hand around Alec’s cock and lined it up with Michael’s hole, leaning against him from behind a little to move his hips. “I’m going to fuck Michael using your cock, Alec. Is that okay?”
“Use me as you see fit, sir”
“God, you are so fucking hot,” Hamilton said, biting down on Alec shoulder and pushing forward so that Alec’s cock pushed past the ring and into Michael up to the hilt.
“Fuck,” Alec gasped. “It's so tight. I can’t, oh…”
“Just rest there until it passes.” Hamilton kissed over his neck and shoulders. “You’re no longer a virgin, Alec,” he whispered. “And tomorrow I will take you home and make love to you all night long, until all thoughts of virginity are banished from your mind and all that’s left is me.”
“Oh, yes. I want you so much.” Alec started to move and Hamilton held his hips, rocking back and forth with him. Michael seemed to disappear and all that remained was Hamilton moving Alec’s body, Hamilton whispering sweet nothings, Hamilton kissing and stroking and pumping him faster and faster, stealing his mind and his thoughts and claiming his soul.
“Stand up, Alec.” Hamilton sat back in his chair and pulled Alec to him. Stripping away the condom, he took in Alec’s whole length and sucked. Michael knelt at Alec’s feet and Alec stroked his hair. He pulled him close, holding him around the shoulder as Hamilton worked over Alec’s cock stoking the heat pooling in his guts and driving him closer to the edge. Hamilton let the cock slip out of his mouth and smiled up at him. “Come for me, Alec.” he said and opened his mouth. Alec let go and erupted a fountain of come over Hamilton’s face and lips. Hamilton sucked him back in and swallowed the rest, licking and cleaning. He wiped over his face with a smile. “It’s very good for the skin. Now, I think Michael deserves a little something. Suck him until he comes, Alec and make sure you swallow it all.”
From virgin to two cocks in one sitting, Alec thought as he sucked Michael’s cock with the techniques he’d been shown. But this wasn’t really for Michael. This was for Hamilton. It may as well have been Hamilton’s cock and Alec was extremely pleased with himself as he felt the hot liquid spill over his tongue. He lost most of it as it dribbled over his chin, but he did swallow. Not a bad taste. Not as good as Hamilton’s.
“Oh, bravo,” Hamilton clapped, pulling Alec in for a kiss and sharing the come around his lips. “Definitely a natural. I am going to have so much fun with you.”
“I hope so, Mr Hamilton. It’s certainly been fun for me.” Hamilton slapped his ass playfully.
“Get dressed both of you and head back to work. Alec, I’ll see you first thing in the morning please.”
“Yes, sir, thank you.”
That evening Alec jerked off in the shower to the sound of Hamilton’s voice in his ear, to the feel of Hamilton’s hand stroking his back and the sensation of Hamilton’s fingers thrusting inside of him. Overall, Alec decided it was a very satisfactory promotion indeed.
