The Last One to Let You Down

by K. L. Hiers

  Heat flashed over Tom’s face. “Like… like a dog?”

  “Exactly so,” Cypress confirmed. “You don’t deserve to walk upright. Not yet.” He started toward the bedroom, snapping his fingers. “Come on. Wanna be a good boy, don’t you?”

  Dropping down on his knees, Tom felt ashamed. He was literally going to crawl on the floor like an animal. The twist of such humiliation made this even hotter, but he didn’t know why. The hardwood floors felt cool as he moved forward, making his way to the bedroom door.

  “Good boy,” Cypress praised, waiting for him by the bed. He patted his leg, urging him over. “Just a little closer.”

  Blushing furiously, Tom did as he was told. He stopped at Cypress’s feet and gazed up at him, asking, “Like this, sir?”

  “Very good.” Cypress sat down on the edge of the mattress, urging Tom into his lap. “Come on, bring that pretty ass up here for me.”

  Tom laid over Cypress’s thighs, his cock trapped between them as his legs dangled awkwardly. No one had ever spanked him like this, and he was so excited.

  Cypress rubbed his ass, not giving any warning before he swung back and spanked him hard.

  Tom grunted, breathing through the initial sting. Fuck, that hurt, but he already wanted more.

  Cypress spanked him again, even harder this time, and Tom’s back arched in protest.

  “Ah, fuck.” Tom gritted his teeth, trying to work through the pain as he grinded his hard dick into Cypress’s thigh. The next spank made his eyes water, and his whole cheek felt like it was on fire.

  “Just a few more,” Cypress soothed, licking over his fingers and sliding them down between Tom’s legs. He rubbed over his little asshole, stroking all around it but not yet pressing in.

  Moaning softly, Tom tried lifting his hips to chase Cypress’s taunting fingers. He got another hard smack in reply on his other cheek, causing him to cry out from the new flash of pain. Now, both of his cheeks were throbbing and hot, and he continued to grind his aching cock down to find some sort of relief.

  “You want me to fuck you, don’t you?” Cypress asked, ever so smug because he obviously knew the answer.

  “Yes, sir,” Tom pleaded. “Please. I’ll take all my spankings, I will, but please, fuck me first. I need something, anything.”

  “Not yet,” Cypress warned, giving him another sharp smack. “Reach back here and help me spread your plump little cheeks. I wanna look at you.”

  Tom was too far gone to be embarrassed, his hand joining Cypress’s on the opposite cheek to spread himself wide open. He had to reposition himself to keep from falling, wiggling his upper body up onto the bed and leaving his legs in Cypress’s lap, straddling his thighs.

  “Good boy, now come on,” Cypress said, urging Tom’s legs apart. “There we go… mmm. You look good enough to eat.”

  Tom could feel his heartbeat down in his cheeks, and his cock currently chafing on Cypress’s hip. He couldn’t imagine how lewd it looked to be spread out like this, weakly rocking his hips as he whispered, “Thank you, sir.”

  Cypress squeezed Tom’s ass, his other hand coming down and smacking right on top of his hole.

  Tom jerked in surprise, the pain reverberating down in his balls and up his spine. He couldn’t help how he clenched up, gasping when Cypress spanked him there again. “Oh, f-fuck!”

  Cypress stroked his long fingers up and down between Tom’s thighs, pausing to massage his tender hole and sighing happily. “Mm, I love watching you squirm like this… ready for more?”

  “Yes, sir, please. I need, I need something,” Tom begged. He was so hot and starting to sweat, whimpering when the tip of Cypress’s finger pushed inside of him.

  “Mmm, almost.” Cypress gently pushed Tom up the rest of the way onto the bed. “Go ahead and make yourself comfortable and get on the pillows. I’m going to tie you down now.”

  Clumsily, Tom rolled over and scooted up so he could rest his head on the pillows. His ass was still stinging, and even the smooth comforter beneath him felt too rough against his sensitive skin.

  Cypress brought out the cuffs, attaching them to the bed and securing Tom’s wrists. He kissed his forehead, checking the fit and asking, “Good?”

  “Yes, sir,” Tom replied.

  “Now, let’s see how flexible you are,” Cypress said with a sly wink, lifting Tom’s legs and pushing them back toward his chest.

  Tom had to spread his legs to accommodate the stretch, and he usually hated any position like this. It made his round belly fold up in a way he thought was very unflattering, but there was something about how Cypress was looking at him right now that made him not mind as much.

  There was so much adoration in those big brown eyes, and it stole Tom’s breath away. No one had ever looked at him with such heat or desire, and he felt so beautiful.

  “Stay like that for me,” Cypress commanded, reaching under the bed for something.

  Lust made Tom’s stomach flip when he saw what Cypress was now holding a slick black riding crop.

  “We’re going to start slow,” Cypress said, teasing the crop over his red ass. “Just a little taste to see if you like it.”

  “I’m ready, sir,” Tom said, tugging impatiently on the cuffs. “Please, give it to me.”

  Cypress cupped Tom’s balls, squeezing them tight as he cracked the crop over Tom’s ass.

  Tom flinched, groaning out loud without meaning to. Despite only striking a small area, the sting of the riding crop was much more intense, and the welt left in its wake burned white-hot. He could feel fresh tears in his eyes, and his brain focused right in on the path the crop had taken across his tender cheeks.

  The throb was incredibly deep, and Tom would have thought he’d actually been cut had he not known the source of this pain. “Oh, fuck, oh, oh, fuck me!”

  Cypress pressed his fingers back inside Tom’s hole, giving him teasing thrusts as he asked, “Do you like that? Do you want some more?”

  “Yes fuckin’ sir!”

  Cypress snapped the crop over Tom’s thighs, his fingers pushing deeper.

  The burn of his hole getting stretched and the crack of the crop made Tom moan from deep down in his chest. He could feel his legs starting to shake from holding himself in this position and the sweet adrenaline pumping through his body.

  The crop whipped across his thighs again, and Tom was ready to sob. He could feel each individual lick pulsing, and he pulled at the cuffs as hard as he could to create some sort of counter pressure.

  It was too much, too overwhelming, and he mumbled a prayer to whatever god was listening when Cypress eased his legs back down on the bed.

  “My good boy,” Cypress whispered, kissing Tom’s flushed face and stroking his cock lovingly. “You did so well. You were such a good boy for me.”

  “Thank you, sir,” Tom whispered back, worried his voice was going to crack. “Thank you so much.”

  “We’re almost done with your punishment,” Cypress said, petting Tom’s damp hair. “Just one more little thing, mmm?”

  “I’m ready, sir.” Tom watched as Cypress gently pinned his cock flat against his belly, and the hand holding the riding crop rose to strike.

  He didn’t know how much strength Cypress had actually used, but when the crop hit his cock, he thought he was going to pass out from the rush. There was a stinging sensation like none he’d ever felt before, but it was followed by a flood of pleasure that nearly made his vision white out.

  It almost felt like coming, but his whole body was trembling. He held onto the feeling for as long as he could, his hands going limp in the restraints, and he moaned loudly. “Ahh… oh, Cypress.”

  Cypress bowed his head down, planting a loving kiss on the shaft of Tom’s pounding cock. “Mmm, good boy.” He smiled up at him. “Feeling good?”

  “Yeah,” Tom wheezed out in reply, drawing in a shuddering breath. “Yes, sir, I mean. I’m good.”

  “Now that you’ve taken your punishment, are you ready for yo
ur reward?”

  “Fuck, yes, sir.”

  “Wait here for me,” Cypress said, sliding off the bed and heading to the bathroom.

  If Tom’s brain was fully functioning, he would have laughed. As it was, he was grateful he didn’t have to worry about breathing on his own as he continued to float on a blissful cloud. He felt sort of sleepy, and he couldn’t stop smiling.

  He heard the sink running for a few minutes, and then Cypress came back out with a small, black, zippered case.

  “These are for you,” Cypress said, sitting back down on the bed. He set the case down and grabbed a tube of lubricant from the bedside table. “If you don’t want to try it tonight, we don’t have to… but I can’t think of a better way to reward you.”

  “What is it?” Tom tried to lift his head to study the case, but he had no idea what it could be.

  “These are,” Cypress explained, pausing as he unzipped the case to show Tom the contents, “urethral sounds.”

  There were eight in total, four fitted on each side in their own special elastic loops to keep them in place. The sizes ranged from a diameter that reminded Tom of the ink cartridge inside a ballpoint pen to one nearly as thick as his fingers.

  “Oh, shit.”

  “Uh huh.” Cypress picked out the smallest sound and offered it out to Tom for his inspection. “These have all been sterilized since the last time I used them, my hands are washed, and I’ve got plenty of lube. I need to know if you really want me to do this?”

  “To… fuck my cock?” Tom blinked, unable to look away from the sound. It had seemed so small in the case, but it looked much bigger knowing it was potentially going inside him.

  “Yes.”

  “Will it hurt?”

  “It may be a little uncomfortable at first,” Cypress replied honestly. “There may be some burning as it’s going in. You have to be careful not to move or jerk around while it’s inside you because you could get seriously hurt.”

  Somehow, the risk made this more appealing, and Tom was already saying, “Yes. Please. I want… I want it.”

  “There’s my good boy.” Cypress seemed very pleased with Tom’s decision. He put the tiny sound away, picking up the one that was the next largest. “Now, we’re going to go nice and slow. You need to stay very still and don’t move.”

  “Yes, sir,” Tom agreed eagerly. “I’ll be so very good for you.”

  “I know you will be.” Cypress slicked up the head of Tom’s cock and the sound until they were both dripping. He got settled between Tom’s legs, stroking his cock until he was almost fully hard. “Take a few deep breaths for me.”

  Tom closed his eyes, excited and terrified and turned on all at the same time. Feeling himself shiver so hard that his nipples stiffened, he looked down at Cypress patiently waiting for him. “I’m ready.”

  “Good boy,” Cypress said, carefully inserting the tip of the sound.

  Wrinkling up his nose, Tom tried to quantify the new sensation. It burned as Cypress had warned, but the pressure felt good, too. He watched as Cypress worked the sound in, bit by bit, totally mesmerized by the shining steel vanishing inside his cock.

  It was an agonizingly slow process, but all the nerves the sound was hitting made Tom moan. He couldn’t believe there was something there, inside his dick, and waves of goosebumps were prickling his skin from the intense feeling.

  His nipples were still hard, and he let out another moan as Cypress drew the sound out and pushed it right back in. He had to fight the urge to draw his legs up and chase more of the sweet sensation, keeping his hips flat against the bed.

  “Almost there,” Cypress said as he advanced the sound even deeper. “Doing okay? Are you good?”

  Tom was afraid to speak, terrified what sound might escape his mouth right now.

  “Thumbs up for yes, thumbs down for no.”

  Tom immediately gave a thumb’s up.

  “Good boy. We’re almost there.”

  The sound was so deep that Tom would swear it was about to go right through him and hit the bed. His cock was so damn tight, and it still burned a little. As the discomfort faded with each gentle stroke, the wonderful pressure remained and magnified every little touch.

  “There.” Cypress was grinning, and he was holding the sound firmly in place.

  “It’s in?” Tom grunted.

  “Yes. Oh, Tom…” Cypress sighed. “You look so beautiful like this. Look how stuffed your cock is. You took all of it.”

  “F-fuck.” Tom stared at his cock, shining and slick from so much lube with the end of the sound sticking out like a glittering jewel.

  Cypress held the base of Tom’s cock, ducking his head down to kiss the head softly. He wrapped his lips around it, carefully taking the end of the sound in his mouth and hummed.

  The sound vibrated deep inside of Tom’s body, and he whimpered loudly. It was an impossible sensation, and it grew stronger as Cypress’s hum dropped into a low purr.

  Tom’s toes curled, and he panted and sobbed as he struggled not to move. It felt so good, weird and delightful, and fuck, he wanted to come so badly. He could feel the vibrations on his prostate and being able to experience anything there from this impossible angle was incredible.

  “Like that?” Cypress asked, licking his lips.

  “Yes,” Tom whispered, desperately willing the tremors in his legs to stop. “Yes, sir, I do.”

  Cypress gently wrapped his hand around Tom’s cock, and Tom swore he was going to come. His cock was a thousand times more sensitive now, and Cypress’s feathery strokes were almost too much.

  “Cypress, I… I’m so close…” Tom gasped in a deep breath, the wicked level of sensitivity now teetering between pain and pleasure. “Please. I need to come!”

  “Almost,” Cypress tutted as he continued to stroke him. “Almost there, baby boy.” He slid his other hand down behind Tom’s balls, his thumb pressing firmly against his taint.

  “Oh, f-fuck!” Tom moaned as Cypress’s skilled touch found the end of the sound through his skin, deep inside of him, and pushed it right against his prostate.

  Cypress rolled his thumb back and forth, jerking Tom off a little faster as he urged, “There you go, there you go, baby. Now come on, come for me.”

  It took all of Tom’s strength to keep his body grounded as he came, gritting his teeth to hold back a scream. He came so hard that he felt dizzy, his orgasm rocking him from head to toe from deep within his loins. He watched in awe as his come bubbled up around the sound, leaking out in quick little spurts as Cypress carefully pulled it out.

  “Christ.” Tom was shaking, unable to stop the symphony of blissful little shivers taking over his body. His cock felt weird, empty, and everything from the waist down was hot and overstimulated.

  Cypress was on his knees, opening up his pants and pulling out his hard cock. He started jerking himself off, crowding over top of Tom as he hissed, “Fuck, baby. I’m gonna come. I’m gonna fuckin’ come all over you.”

  “Yes, yes! Come on! I want it! Please, I want your fuckin’ come!” Tom tugged at the cuffs, opening his mouth and letting his tongue hang out. He didn’t know where he’d gotten this sudden urge, but now he wanted nothing more than to taste Cypress’s load.

  “Oh, fuck, baby,” Cypress growled, shifting his body upwards until he was straddling Tom’s chest and holding the headboard for support. He jerked himself off faster and faster, groaning low, “Here it comes, baby!”

  Tom easily caught the first pulse, closing his mouth to quickly swallow it down. The rest landed on his chin and his lips, and he opened his mouth again to catch the last splash. “Oh, Cypress… oh… fuck..”

  Cypress tilted his hips forward, pushing his cock into Tom’s mouth. “Go on, baby. Take it all.”

  Tom sucked hard, relishing in the hot taste of Cypress’s cock, running his tongue around the head as if he could work out another load.

  Cypress pulled back with a very satisfied groan. He used his thumb to wipe th
e come from Tom’s chin up into his mouth, smiling wide as it was promptly sucked clean.

  Tom let go with a loud pop, grinning up at Cypress. “Good?”

  “Perfect,” Cypress replied, moving off Tom to free him of the cuffs. He rubbed his hands and his wrists, pressing little kisses all over them. “You were absolutely incredible.”

  Tom flexed his fingers as Cypress massaged them, and he grinned dumbly up at him. “Me? Ha. You… you were… wow… amazing.”

  “How are you feeling?”

  “Sore,” Tom said a bit too quickly. He laughed and ducked his head down. “Yeah, definitely sore.”

  “From the riding crop?”

  “And the dick fucking.”

  Cypress chuckled. “Come on. You need to take a piss, and I’ll finish cleaning you up.”

  “I do?”

  “Flushes you out,” Cypress explained. “You know, after the dick fucking.”

  After Tom was finished using the bathroom, Cypress wiped him down and applied an aloe vera balm to all the welts he’d left behind.

  The whole time he was cleaning him up, Cypress was telling Tom how beautiful he was, what a good job he’d done, and how proud he’d made him. The praise added to the warm glow fogging Tom’s mind, and he stretched out in bed with a happy smile.

  Even though his ass and thighs were still singing their complaints, he was perfectly content if not also totally exhausted. He flopped face-first into the pillows, mumbling, “Mmm, I could sleep for a week.”

  “You can if you’d like,” Cypress reminded him. He had stripped down to a pair of shorts and started rubbing Tom’s back, sliding into bed next to him. “Off for a little bit, remember?”

  “I just might.” Tom turned his head, so he could see Cypress. “All of that… wow. It was so good.”

  “Everything okay?” Cypress asked. “You’re not hurting anywhere? All’s well down below?”

  “It did kinda burn when I peed,” Tom confessed, wrinkling his nose a little.

  “Totally normal after sounding. Especially for your first time.”

  “I liked it.” Tom grinned. “I liked it… a lot.”