Riding Buddies Ch. 03

"Aaaahhh! Damn! Oooohh!" Sidney grunted as stream after stream flew into my captured mouth.

He held me in place until he was satisfied, then eased up while slowly thrusting his spent tool in and out before relinquishing his usage of me. I fell backwards onto the carpet when he finally let go of me. I was up in an instant and stood to tower over him, uncertain if I should be angry. Sidney turned out to be a short, thin, geeky type tech nerd. He was still dressed much like Alan had been, except the glasses were thicker with black plastic frames and more functional than fashionable. His clothing hung awkwardly from him, as if he had no business wearing an outfit of that nature. His spent cock stuck out through his open zipper.

"Damn Alan, I wish I could have lasted longer the first time."

Alan was now standing behind me. I don't know what he thought I might do to the newcomer, but he seemed ready to intervene. I wasn't sure what to do either. I had more or less been forced to swallow him instead of finishing him manually like I had always done with Alan so far. Instead of waiting for my possible objections or outrage, Alan took the lead immediately and led me to the bed.

"Sorry about that Brad. Things kinda went a little fast and I forgot that Sidney doesn't always take his time or warn anybody about anything."

I saw Alan look directly at Sidney during that last observation. Sidney looked a little sheepish at the gentle admonishment, but the guest didn't give any sort of explanation or apology.

Alan had me on my hands and knees on the bed before my mind could catch up with everything. I didn't even hesitate to follow Alan's directions as he discarded his robe and slid into place at the head of the bed, guiding my head down towards his leaking cockhead. He stroked himself as he guided me into doing one of his favorite activities.

"Open up Brad. You know exactly what I like."

My head lowered with Alan's hand guiding me. Of course I knew what he liked. I had done this several times, all of them to his obvious satisfaction. I enjoyed Alan's cock and his seemingly endless patience due to my inexperience. My oral skills were growing, but there were things I knew he wanted that I had not been ready for yet. As I wrapped my lips around him once again, I heard the telltale sigh that he always expressed during my initial contact.

"That never gets old." he said.

I continued the task that I had started just a few minutes before. I felt the bed shift as Sidney moved around, but with my attention elsewhere I was unsure what he was doing. I was unsure for only a few moments though. The little tech guy came up from behind me, used his hands to spread my ass open, and ran his tongue right down the middle. I yelped in surprise and made muffled moans around Alan's tool filling my mouth. While I was doing what Alan enjoyed, Sidney had instantly found what I enjoyed. Enjoy was not really an accurate measurement though. Fireworks were going off in my head. My breath was coming in short gasps. I couldn't stop the sounds I was making. I had completely forgotten what I was doing, as I couldn't concentrate on anything but Sidney's efforts. Alan's hands started making my head resume its movements. I wasn't putting forth my best efforts, distracted as I was. I had experienced this once before from Alan and it had scrambled my brain then as well. Alan finally just sat back and waited as Sidney tongue fucked me into uselessness.

"Damn it Sid, you're messing him up." Alan joked over my loud moans. "I bet you could get him to bark like a dog by doing that."

Sidney didn't stop or slow. He drove his tongue deeper just to mess with Alan. I no longer had Alan's tool in my mouth, and indeed had completely forgotten about it at that moment.

"Oh fuck! YES!" I groaned, my forehead resting on the bed.

Alan got on his knees and lifted my head back up. He knelt in front of me and rubbed the head of his member across my lips. My eyes were squeezed tightly shut as Sidney's tongue continued rendering me powerless. Alan got me to open up for him and he started thrusting his hips, plunging his cock into my mouth. I guess he still wanted his oral gratification and he planned to get it regardless of who had to do the work to get him there. I let him use my mouth however he wanted as Sidney stayed behind me. Alan drove himself deeper and I still struggled with accommodating his last couple of inches. He seemed fine with working the length I could handle. I lost track of time as I enjoyed both guys on either end of me. In the back of my mind I could hear Alan getting close.

"Just keep him right there Sid. I only need another minute."

Sidney's tongue twirled around my opening and I moaned some more. Alan was thrusting quickly and erratically.

"Oh damn! I'm gonna cum."

I heard the words, but didn't want to disrupt Sidney's activity behind me. I stayed in my current position as Alan pulled himself halfway out of my mouth to stroke himself as was his preference. He noticed I wasn't moving away like I always had. With a final groan Alan unleashed his river of cum into my mouth, over my tongue and down my throat. I still stayed in place, quickly swallowing him down as I also had with Sidney.

"Fuck yeah! I've been waiting a long time for that." Alan groaned.

He released his grip from around his shaft and pushed his cock back into my mouth. He had flooded my available space and I was unable to contain it all. Some of his cum came out from between my lips that were still stretched around his member. Alan didn't seem to care, simply relishing in finally having me blow him to completion. His heavy breathing began to subside as Sidney kept me rooted to my spot with just his tongue.

"Okay Sid. I had mine. Now you can have yours."

Alan gave up his position in my mouth and got off the bed. He sat down heavily in a chair across the room which afforded him a good view of the bed. Sidney changed his position as well. He had removed his clothing and came around to take Alan's former place at the top of the bed, laying back on the pillows and putting his groin right in line for some oral attention as well. He didn't ask or tell or give any indication of what he wanted. His placement was enough for me to guess. My hand grasped his tool and gave him a slow handjob for a minute before my tongue joined in and started running up the underside of his shaft. I would engulf his entirety for a few moments before licking him like an ice cream cone again. Sidney allowed this for several minutes as he moaned in approval.

"You trained him pretty well. No wonder you wanted him to join us tonight." Sidney remarked.

His hands directed me lower until I was running my tongue over his smooth, heavy balls. I sucked each into my mouth one at a time and bathed his entire area until his hands pushed my head even lower. I was now lying flat on my stomach between his spread legs. He raised his hips up and shoved a folded pillow under him to keep him in the air. He directed my head farther down even more. He now wanted what he had done to me just minutes before. My tongue trailed down from his balls, gliding down his seam. He gasped at the sensation. I knew exactly how he felt. I was willing to do just about anything for that kind of attention again. I was afraid to actually say that though, as I wasn't sure what it would cost me. Once my tongue reached his puckered hole, he was writhing in place, tightly holding my head as I explored.

"Oh damn!! Right there. Keep licking me! That's it, keep that tongue moving." Sidney demanded.

I alternated between lightly brushing over him to tongue fucking him into oblivion. I traveled back and forth from taking his cock into my mouth for a few strokes to licking back down and making him moan and whine uncontrollably. Making him respond like that kept my own tool rock hard. Was that what I sounded like when that had been done to me?

"Ooohh fuck! Keep that up and I'll cum before I ever get a chance to make you my slut puppet."

Sidney let me continue for a few minutes before lowering his legs back down. He was breathing hard but since his position changed denying me the access I had before, I went back to sucking him instead. I knew he was enjoying my performance, but he had other ideas for what he wanted. He pushed my head away and rolled off the bed. I saw him grab a bottle that had been sitting on the nightstand before turning back towards me. I heard the bottle pop open and could smell the scent of vanilla, so I knew that to be Alan's bottle of lube. I looked over to see Alan lounging in his chair, still watching while slowly stroking himself. I hadn't ever met or talked to Alan's conference companion before today, and still hadn't even said a single word to him, but the bottle in his hand indicated what was coming next. Had I just become a sex doll which Alan could loan out to his friends on a whim? I glanced at Alan, and my expression was enough to make my riding buddy pause.

"Hold up Sid." Alan interrupted. "Brad, do you trust me? I think you know me well enough that I won't do anything you won't like. So you trust me and I trust Sid. That means you can trust Sid."

All three of us had stopped while that conversation took place, and remained that way as I mulled over Alan's words. I gave a short nod in agreement, but Sidney had now changed what he wanted.

"Off the bed." Sidney demanded.

I didn't question or argue, I simply moved off the bed. Sidney put me standing right up against the side of the bed and bent me over it.

"Spread your legs."

I spread my feet apart, but apparently not enough to his liking. He kicked my feet apart even more until my ass was at the height he wanted. The way he was behaving, arrogant and demanding, I really couldn't picture Sidney as a bottom. He was aggressive in tone and action. The bottle of lube was upended, pouring a generous amount into his hand. After slathering it over his pole, Sidney ran his fingers up and down my ass, getting them slick with the vanilla scented liquid. He jammed two fingers into me and I yelped in surprise and pain. He ignored that and fucked me hard with those fingers.

"Slow down." I suggested as I groaned. "Take it easy."

A swift slap against my ass let me know his opinion about my words.

"Fuck easy. You've already had it easy. You might normally be Alan's little bitch, but I'm the one who's gonna be doing the fucking now."

I still emitted sounds of discomfort as his fingers prepared me for his upcoming destination. He removed his hand as abruptly as he had began and started sliding his cock along my ass, skimming the surface of my skin as he humped me from behind. A little more lube was applied before Sidney pressed his tip firmly against my hole. He gripped his cock with one hand and spread my ass with the other. I suspected I might be in for a rough ride.

"Take it easy on him." I heard Alan caution.

Apparently it was different when Alan said it compared to when I said it, even though we said the same thing. I was suddenly grateful that Alan was sitting there watching. I could feel Sidney's intensity lessen somewhat. The tip of his member pressed harder against me as he leaned forward.

"Go ahead, try to keep me out." he whispered. "I like when you fight it."

His hips backed off slightly, but then pushed ahead until he was pressing a little harder against my natural resistance. He kept repeating that action and I could feel my ass weakening. One more push forward and the head slipped inside me. We both groaned in unison. I was thankful that he hadn't rammed himself fully into me with his first thrust like I half expected. If Alan hadn't been there, that's what he probably would've done. Of course, if Alan hadn't been there, neither would I be. Sidney pushed ahead slowly, burying himself inch by inch. The lube made it easier, but I still groaned and whimpered at his advance, not used to being penetrated.

"Yeah, take it! Take it like a bitch!" he muttered softly so that only I could hear him.

He would slowly sink almost all the way into me and then thrust hard the last little bit, slamming himself home. He was progressively getting faster and soon he abandoned all pretense of "taking it easy". Sidney started fucking me hard, fast, and with purpose. I was starting to moan more as well. Even though I wasn't going to say it to Sidney, he was hitting a spot that made me want more. My cock was hard beneath me and rubbing against the comforter as my body was jostled with each thrust. I could feel my orgasm building, and I was trying hard to stave it off. I didn't want to cum from Sidney fucking me. I didn't want him to know how he got me off. What I wanted seemed to be irrelevant though. I couldn't stop my inevitable march towards my finish.

"Just a little more...a little more. Oooohh, yes! I'm gonna cum!" Sidney groaned.

He thrust into me several more times before he reluctantly pulled out and jacked his cock as he stood behind me. His hand on my back kept me in my position laying face down on the bed. He let out a long growl and I felt his hot semen land in trails up my back. For a small, nerdy, tech type guy he had quite the load of cum in him. He leaned against me as he forced the last few drops up his shaft to drip onto my ass. I sighed in relief that he had cum, but my own orgasm had subsided. He sighed in relief from the aftermath of his climax. Just as I thought my interaction with Sidney was over, he slapped my ass to get my attention.

"Get on your back up on the bed." he demanded.

Was he going for round two? There was no way I could ever recover that fast, but maybe that was Sidney's super power. I heard the bottle pop open and could smell vanilla again. Sidney was into the lube once more, but I wasn't sure what he used it for. He climbed onto the bed and stood over me. He grabbed my legs and pushed my knees towards my chest. Then he squatted over me. I was completely exposed to his whim. I was surprised when he took ahold of my throbbing meat and lightly jacked me with his lube coated fingers. He guided himself over my cock and began lowering himself onto it. His slick hole opened up around my tool as he made my inches disappear. I groaned loudly, even more loudly than he did this time.

"Mmmmm! Oh fuck, you're big!" he exclaimed as he sank lower. He voice got quieter so that once again only I could hear. "Now I'm gonna make you shoot! You're not just gonna cum, I'm gonna TAKE your load from you, so you'll still be the bitch!"

So this was the versatility that Alan had mentioned. Even though his ass was being filled, he still wanted to be the one doing the fucking. He settled his weight fully onto me as his ass pressed tight against my groin. I moaned again as I felt my recently avoided orgasm start to creep back up. Sidney held my legs apart as he fucked himself on my tool. From my current position, I was unable to control the speed of his impalement. He was getting it how he wanted, but I realized the result would still be the same. His hole was contracting around my meat each time he lowered himself onto me. He was watching my reactions as he fucked himself on me. I couldn't hide the pleasure I was getting from him, and he had a pretentious smirk on his face from knowing. He leaned forward and grabbed my wrists, pinning me to the bed. In most other positions I could have gotten out with ease, but with my legs up over his shoulders I was going nowhere...not that I was trying to. With each stroke that his hole swallowed me, I was getting closer to exploding. I couldn't speed up or slow down. Sidney truly had control over my impending orgasm. I could see that he knew it, he could tell that I knew it, and he had that smirk on his face again. We both could tell I was close. My moaning was constant now. He was enjoying getting reamed, but was also enjoying the control he exerted.

"Uh huh...give it to me. Give it up. Come on bitch, give me what you've got!" he demanded.

I wanted to deny his victory so badly, but I lost that battle quickly. My eyes squeezed tightly shut as I could feel my climax start.

"Keep your eyes open!" Sidney ordered. "Look at me when you cum!"

My eyes flew open to find him staring as he loomed over me. He thrust himself onto me with short, quick strokes as I groaned. I lost my remaining control and I shot my load up into Sidney's waiting orifice.

"Oooh! Oooohh! Ooooohh FUCK!" I moaned breathily.

"Mmm hmmm. Just like that. Couldn't hold on could you? I told you I'd take it from you."

He sank all the way down to fully engulf my cock and watched me as I was drained until I had nothing left. He slowly lifted and sank a few more times to make sure he had gotten everything I had. He made sure I watched him all through my climax, as if he was trying to take possession of my soul.

"You're a pretty good fuck. I see why Alan keeps you around. Next time your ass is all mine. Trust me, I'll fuck you until your legs don't work, and I'll pump you so full of cum in you it'll leak out of your ears."

Sidney lifted himself off of me, letting my legs fall to the bed as I lay there out of breath and wondering if there were future plans I was unaware of. I saw Alan give a goodbye gesture to Sidney as the tech nerd gathered up his discarded clothes and went through a door which connected the two rooms. That was how he got in without me seeing. They had adjoining hotel rooms, and clearly Alan had left his side unlocked beforehand. After the door closed behind Sidney's departure, Alan finally got up from his chair and crossed the room to the bed.

"Yeah, Sidney's kind of a dick, but he can be fun in the sack. He's not usually that bad, but apparently he gets a power trip when he gets a little bit of control."

"Kind of?"

"Yeah...no argument there. But if I had known that was what it would take for you to swallow, I would have made sure to introduce you much sooner. Now...roll over. I'm about ready to burst from watching all that."

I weakly rolled onto my stomach and pushed myself up to my knees. Alan slid his own meat up and down my ass which was still slick from all the lube that Sidney had used. Without any warm up, Alan pierced my opening with the tip of his pole. I gasped hard and loudly. Sidney had fucked me thoroughly already, but Alan was considerably larger.

"Oh fuck! Take it easy!" I begged.

A slap to my ass was his initial response. "Sidney was right...fuck easy. Your boss needs to cum, and you're the little wage slave bitch that's gonna make it happen."

Alan fed more of his cock into me as I groaned against the bed. He did seem to take it a little slower, for which I was grateful. He pumped into me a little more each time, and it seemed like his cock went on forever. Once he pressed tight against me, he didn't pause. He went straight into long and deep strokes, intent on getting what he wanted, how he wanted. It was only a couple of minutes before he grabbed my shoulders and started hammering me from behind. I had opened up for him and he was taking full advantage of my willingness. The sounds of slapping flesh were loud as well as the constant moans.

"Yes, yes, yes, yes, oh yes, oh yes!!!" I was repeating as he pounded me over and over.

"Fuck yeah! I'm almost there. Almost...almost. Oh yeah. Here it comes. Cumming!"

Alan used the leverage from holding my shoulders to take one long, slow, final, drawn out stroke to bury himself as deep as he could. He held still as his hot cum shot into me. I felt his cock pulse with the release of each stream. I moaned in response, enjoying the feeling of him filling me.

"There's your bonus...direct deposit." he groaned as he slowly thrust a few more times into me for good measure.

I seemed reluctant to remove his tool from inside me, but as he softened somewhat he backed away. He moved off to the side and fell onto his back on the bed beside me. I slid my legs down until I lay flat on my stomach. I rested for a few minutes before I got up to go clean up and shower. Before I got out of the shower Alan stepped inside, crowding me out from the hot water coverage. I half heartedly dried off before climbing into the bed, finally getting under the covers. I didn't bother wearing anything. I was too tired to care about that. I was asleep before Alan emerged.