Riding Buddies

"Oh, I like this show." I announced.

"Eh." he responded noncommittally after a few seconds before continuing going through the channels.

Alan stopped flipping when he reached a rerun of The View. I was not impressed, not being a fan of it, but I watched as the cast argued over each other about the merits of their opinions on the topic at hand. After a few agonizing minutes of mind numbing debate on the screen, I decided to address an issue with my travel companion.

"How come we started talking on a hookup site, and you'll discuss that stuff over messages, but you've never mentioned it in person?"

Alan looked at me for a minute before answering. I began to wonder if he forgot the question. When he did speak, his answer was very deliberate.

"I figured I'd let you get used to me as just a normal person before we got into any of that. You said you're brand new to this, so I figured I'd give you time to decide if that's still the way you wanted to go. I wasn't gonna push anything you might not want or be ready for in favor of my own agenda. Also, I wanted to figure you out on my own, and I've come to some conclusions."

"Such as?"

"Well, I'm pretty sure you're not lying about being new to this. Some guys will lie about that just to get what they want. Also, you're not just a bottom as you already figured out. You're also more of a submissive."

"Really? How do you figure that?"

"Well, with few exceptions so far, you're always following. Just a minute ago you were watching a show I could tell you hated just because I chose it. Yeah, you're a little bit sub. Maybe more than a little."

"I think you're reading more into something than is actually there. I was being polite."

"Yeah? Well, we'll see." Alan got up and headed towards the bathroom. "I'm gonna take a shower. I smell like we've been riding all day."

Before he entered and closed the door behind him, he stopped and cranked up the heat. Once he relinquished the TV remote, I immediately changed the channel to something I would prefer to watch. When Alan came out wearing a towel around his waist, I went in and took my turn. Afterwards I wrapped a towel around my own waist and draped another around my shoulders. I emerged from the bathroom to find Alan still in his towel, once again sitting on the loveseat, and once again flipping through the channels on the TV. I sat at the other end as he finally settled on a channel. Without taking his eyes off the screen, Alan went ahead continuing our earlier conversation.

"Since you brought it up, it seems like you're a little disappointed that nothing has happened between us besides riding our bikes. Now that we've laid our cards on the table, feel free to ask me whatever you want."

"I think you've probably already answered everything in your messages that I would have asked in person." I acknowledged.

"Well then, since you're new to all of this, feel free to go at your own pace...for now."

Alan still sat at his end of the loveseat, seemingly engrossed in watching the TV. It seemed that he was fine whether something happened or not. I hesitated. This exact type of thing is what I had believed I wanted, but now that I was in the moment, I didn't move. I didn't know what to do or how to start. Watching videos, having written or spoken conversations, or even the mind's own fantasies were one thing. Real life was a little different.

Alan noticed my indecisiveness and made the move to start the ball rolling. He reached over, grabbed my wrist and placed my hand on his towel covered groin. Then he went back to his TV show. I froze, not making any progression, but not pulling away either. My hand rested on his groin directly over where the towel came together to cover his front. Alan didn't make any conscious movements himself, but his unconscious movements gave him away. I could feel his cock start to harden beneath the towel covering him. Even though my hand remained still otherwise, his growing phallus pushed through the opening of the towel around his waist. The more it grew, the more it emerged from beneath its covering. My gaze was focused on Alan's tool, surveying it as it reached its full potential. It was large and kind of scary. Maybe that assessment came from the simple fact that it was not my own. Even with that thought, my hand still started moving incrementally. I glided my hand along the shaft, the towel opening further as my hand disrupted its placement. I glanced at Alan's face to see him still watching TV and ignoring my actions. He was obviously aware, but did nothing to either encourage or dissuade me from what I was doing. I directed my hand slowly up and down the foreign tool, watching as it reacted to my light touch. I wrapped my fingers around the circumference of his cock as I continued to manipulate it.

"Mmmm..."

Apparently Alan wasn't able to totally ignore everything, or even make it seem like he was. My grip firmed and my stroking became a little faster. I looked over again and he wasn't even watching the TV. Alan's eyes were closed and his head was tilted back slightly as he simply sat there letting me explore on my own, but enjoying my efforts.

"So, how am I doing?" I asked.

My question sounded kinda sarcastic, but I was actually interested in his answer. The activity was not new to me, as I had done the same to myself for years, but it was new for me to do it to someone else. I didn't know if I was doing it right, or if I should continue.

"You're doing just fine."

Alan's towel had come undone by now, falling off to his sides. The more I jacked him, the more he shifted on his seat. His member was leaking heavily onto my hand, making my hand glide easier across his skin. Alan sighed heavily every few minutes during my experimentation. I realized how much time I had spent just fondling his unit. It was no wonder he was shifting, squirming, and unable to keep silent. I had wanted to take things slow, and didn't regret doing that, but had gotten a little lost in my infatuation with handling my buddy's organ. I was kind of impressed with Alan's self control. I probably would have either cum from the handjob or rushed my partner into the next stage of activity. I looked again to see Alan still in the same position. The TV was forgotten, he still sitting there mostly quietly, with his eyes closed as he just tolerantly enjoyed my achingly slow progress. Slow torture was not my goal, getting familiar and comfortable was. But if I stayed in my comfort zone, we wouldn't even be in this hotel room together and I would not be handling Alan's hard member. I leaned over so as not to disturb his peaceful concentration. His cockhead was right at my lips as I looked at the penis from a whole new and different perspective. Sparing another quick glance up to see him still unaware of my change in position, I opened my lips wide and took the first couple of inches into my mouth, sealing tight around the shaft.

"Whhhooooaaahhh!"

That got his immediate attention and his hands went straight to my head. He held me in a firm grasp, not pulling me down more or pushing away, but clearly in surprise at the sudden change in the situation. His hips involuntarily thrust forward a little momentarily until he regained control of his bodily instincts. He gasped a few times before he loosened his grip and let go of my head. I stayed still while leaning over his lap, his rod still only partially engulfed. Once he settled back again I resumed my oral exploration, my achingly slow descent keeping him hard and wanting more. I was appreciative that the target of my experimentation was letting me control the speed and intensity of the encounter. I took more and more of his length into my mouth. I fought my instincts and assorted reflexes as I took more inches with each downward movement. I was learning fast, figuring out what I could and could not do. I was bobbing up and down over the length I had already mastered, eager and learning to swallow more of him as I went. I felt Alan's hand rest on my head, still not guiding or pushing me, but seeming to offer encouragement in my activity.

"Mmm hmmm. Keep going." he whispered.

The prolonged position I was in was uncomfortable. I had ignored that for too long, but decided that it was time for a change. I removed Alan's member and tossed one of the loveseat's pillows onto the floor, moving off the furniture to kneel in front of my travel partner. Alan allowed me to do as I pleased and didn't hesitate to spread his legs wide open for my prying hands. I lowered my mouth back down to continue my education, quickly figuring out that I could go deeper than before in my new spot. Alan groaned some more as I made my discovery and nearly took his entire length. Try as I might, I was unable to fit his entirety into my mouth and throat. I did try, more than once, but my gag reflex was a little too strong, and I would back off, only to try again. Alan's hand was back on my head again. He had started to gently pull me downward ever so slightly each time I would take as much of him as I could manage. I mentally applauded him for his restraint. He kept his patience even as I unintentionally prolonged his path to relief. It seemed that his patience was nearing its end though. Both of his hands were now on the back of my head, doing a little more than encouraging this time. I was still moving up and down, but Alan's hands were now more encouraging of the downward stroke. Actually he was now doing more than encouraging, definitely more than guiding. He was becoming more insistent the longer I remained where I was. His hips had started moving forward as I descended upon him. He had now abandoned his lack of vocalization and was moaning and offering more openly spoken endorsement of my activities. My hand moved down to rub the exposed portion of his rod that would not fit into my mouth. Then it wandered down even further to rub his balls. Alan's new moan of apprehension accompanied my activity.

"Yeah, ooohh yeah. Keep doing it just like that Brad. Right there...keep going."

I was enjoying myself, enjoying what effect I was having on Alan, and enjoying the experience in general. All of his groaning just made me suck him harder and faster. He was holding my head tightly now, thrusting his cock into my mouth from below. Even though this was my first time sucking another guy, I instinctively knew he was close to his orgasm. His tool had been leaking precum while I was stroking him. It continued to the entire time it was in my mouth as well.

"I'm gonna cum!"

Alan's announcement made me hesitate. I wasn't sure I was ready for that. I'm sure it had taken great restraint on his part not to have finished already, but this was still my first time, so I wasn't exactly certain how I would handle that. I did want to experience the whole fantasy through to the end, but I was still uncertain. Alan's hands on my head pulled me towards him as he groaned and growled towards his well earned finish. He pulled his cock half out of my mouth and stroked himself hard and fast as he watched me remain in place. My mouth opened from around him and I stuck out my tongue, running it along the underside of his tool. He let out a long growl and aimed himself right into my opening.

My hand replaced his and took over stroking it for him. Just before he erupted I chickened out and aimed him in a different direction. His cock exploded, covering my neck and chest in hot, sticky ejaculate. He grunted as each spasm released another thick rope of cum to cover my skin. My hand milked his shaft, ensuring he had nothing left to shoot. I continued the slow up and down sliding of my hand around his member as Alan seemed to melt a little more into the cushions of the loveseat. I felt bad that I hadn't completed things as I had wanted, but this was my first time so I felt justified in my last moment decision. Alan was not complaining. He had still gotten off, regardless of how bad a job I had done on him.

"Maybe next time." he reasoned as he continued to breathe heavily from the results of my efforts.

It sounded like maybe I hadn't been so horrible after all, as it seemed like I had a future invitation to try this again. I took my towel from around my shoulders and wiped off Alan's deposit from my skin. I got off my knees and went back into the bathroom for a second quick shower to clean off the results of my oral lesson. By the time I came back out Alan was in his bed, under the covers, and softly snoring away. I guess his energy had drained away just as his balls had. It wasn't even dark out quite yet. I watched some more TV until my own eyelids started to droop. I went to my bed and quickly fell asleep, ignoring my own cock's requests for attention. It seemed rude to jack myself off a few feet from a sleeping roommate, even if I had orally pleased him just a short while ago.

I woke up in darkness. I couldn't see the alarm clock, as it was facing the wrong way from me. Light from the parking lot barely came in around the edges of the curtains. It was just enough light to make out vague shapes inside the room. My cock was hard and was being stroked, but not by me. I was on my back which is not the position I normally sleep in, so I wondered if I had been moved. I awakened enough to recall the events leading up to me being asleep in a hotel room along with my riding buddy. I assumed that the hand currently rubbing me belonged to Alan. There was no good way for me to be sure without asking, and I didn't want to interrupt his unsolicited attention. I just lay there, unsure if I should pretend to be asleep. Maybe he already knew I was awake. My tool was definitely enjoying his focus, and since I had already given him his relief earlier, I surely didn't mind his returning the favor.

"Ready for round two?" Alan asked.

Apparently it was a rhetorical question, as his hand increased its pace. I moaned loudly at his touch, unsure of how long he had been stroking me, but I was sure of how close I was to exploding all over his hand. I guess he could tell I was near my limit, as he slowed to keep me from a quick finish.

"Slow down there bud. Don't want things to be over so soon, do we?"

Alan continued his slow manipulation of my tool. I could barely make out his position in the dark room, but it seemed like he was laying next to me on his side. I saw his form lean down and my breath caught in my throat as his warm, wet mouth took me inside.

"Oh fuck!" I groaned.

It had been five years. Five years is a long time to go without any form of contact. My hands went to hold his head as he bobbed over my cock. I had long since forgotten how that felt. I had trouble catching my breath. I found myself unable to talk. He moved slowly, somehow knowing I wouldn't be able to hold back. He removed his mouth from my unit and continued to slowly jack me. I was gripping fistfuls of the covers, unable to do much more than hold on. Alan could sense my struggle as his hand was still holding me, but now barely moving. I was coming away from my edge, but it was slow.

"Fuck it." Alan said.

I guess my riding buddy decided on a change of plans. His grip tightened and he took me back into his mouth. I was moaning immediately. Each long, drawn out sound got louder and higher in pitch. It was embarrassing to my own ears, but I was unable to make it stop. Alan didn't stop or slow down this time. He moved his hand to my sack and fully took my member into his mouth and throat. I could no longer think and I was beyond stopping.

"Stop, stop, stop, stop, STOP!"

I finally was able to utter that one word over and over, although I didn't know why. I didn't want him to stop. It was too late to stop anyway. Maybe I was trying to warn him. If so, he paid no heed to what I said. I grabbed his bobbing head and pulled him all the way down to me, holding him tightly against my groin. I lost the fight of holding back and felt my cock release all of my pent up sexual energy into the waiting mouth of my hotelmate. I grunted with each spasm, and Alan never pulled away as he swallowed me down. I think I may have briefly blacked out from the force of my orgasm. I returned to awareness with my still hard cock being lightly milked by his hand.

"Damn, I guess it's been a while for you huh?" he said.

I was panting hard as if I had just completed a marathon. I couldn't bring myself to answer. I wasn't even sure if my voice would work.

"Now...roll over. Get on your knees." Alan suggested.

I could see him laying there waiting. I moved, but it was slow. I hadn't regained any of the energy that I had just lost, but now was supposed to change position at his direction. I finally rolled over and felt the bed shift as Alan moved as well. I was on my stomach but unable to get up. I needn't have worried, as Alan was there to assist. He grabbed my hips as he knelt behind me and pulled me up onto my knees. My chest was still on the bed, but apparently that was fine with what he wanted. I felt his hands spread my ass open.

"Guess we're moving on to round three." he said.

My inexperience was proving to be a hindrance to understanding some of the things he said or wanted. The position I was now in, and my previous habit of watching porn gave me a clue as to what Alan was thinking about next. In our messaging, Alan had been quite explicit about his love of fucking. My wants had been restricted to jacking and oral experimentation. Even though he had included fucking in the list of the basics of sex, I still always steered away from that, as I was still new and unsure about my wants and likes. It crossed my mind to say something to stop his progression. I was a little speechless at the moment though, still literally drained from our activities that had just completed.

I was quite surprised when after he had spread me open I felt his tongue wetly run along my crease. The moment he hit his target in the middle my eyes flew wide open and I gasped in shock and rapture. This was a feeling I had never experienced. I moaned loudly in encouragement as Alan continued running his tongue over the area. I was unable to tell him to stop. I was unable to tell him not to stop. I kept finding myself in unfamiliar territory. It wasn't unwanted attention I was receiving, but it was new to me. Unwanted was far from what I was experiencing. Alan reached between my legs and grabbed a hold of my hanging tool. His hand worked in concert with his tongue, leaving my mind a babbling mess. I was groaning and moaning uncontrollably. I couldn't think and I couldn't act. Alan kept up his activities, keeping me in that position, keeping me hooked with his attentions. When Alan pulled both his hand and tongue away, I shamefully whined in exasperation at his departure. He moved to stand between the two beds and rummaged around on the communal nightstand before retaking his place behind me. His hand remained on my back, keeping me in place with nothing more than his touch.

"Did you want some more?" he asked.

"Yeah." I quickly agreed.

"Don't agree just because I asked. Agree because that's what you want. And if you agree, that's the last time I'm gonna ask. So...do you still want more?"

"Yes!" I said almost before the question was out of his mouth.

Something flashed a warning in the back of my addled mind. It was the way he asked coupled with the qualifying comment. I hadn't hesitated to answer, and wouldn't have answered any other way in order to get him back to what he had been doing to me. Once answered, Alan did exactly what I had hoped. His hands spread me open and I felt his coarse facial hair brush against my skin in passing. His tongue found its mark...my mark. I gasped anew at the return of Alan's mind scrambling tongue work. I was moaning louder with each passing moment from his attentions. In the back of my mind I heard a popping sound and the scent of vanilla was noticable, but was unsure and really kind of uncaring about the source. Alan moved his head away, and I felt some liquid drip onto my spread apart and exposed area. His hand reached under me and grasped my engorged pole once more. Lightly stroking me, his other hand was spreading the liquid over my skin where his tongue had previously been exploring. I didn't question and just stayed in place enjoying it all. His fingers glided over my skin, but I felt them pressing against my hole each time they passed. He centered his movements and I felt him slide one slick finger inside me, followed quickly by a second one when he encountered no complaints or resistance from me. I groaned a little louder. It was a unique feeling. I wasn't sure what to think beyond staying in place and letting him do what he wanted. His grip around my cock and his fingers plunging into my hole left me little choice otherwise. Alan spent a couple minutes with his repetitive motions before he added a third finger. I grunted in discomfort and disapproval at that move. Alan stopped stroking my rod and reached up and smacked my ass. The sound was loud and broke with what had been happening up to that point.