A gay story: Riding Buddies It had been five years. Five years is a long time. Five years is a long time to go without sex. Five years is a long time to go without any kind of intimate contact. A quick kiss before I head out to work is NOT intimate contact. My wife and I were basically roommates sleeping in the same bed. I had adjusted to the new reality so much that once when she touched my shoulder to get my attention I had flinched, not knowing what her intention was. I now have a large bubble concerning my personal space. I don’t like to shake hands or fist bump. I’ve never been the touchy-feely type and I’m not a hugger. Obviously it’s different with my wife. Correction…it was different with my wife. But five years is a long time.
So in regards to my self care I watch porn, but obviously when she’s not home. Watching it while she was home would be rude. We work opposite schedules. She works the regular Monday through Friday like most regular people. I work Friday through Monday, ten hour days, and then usually cover at least one more day or more if needed due to call offs, vacations, extra work to fulfill the needs of the customer contract, and so on. So my wife and I do not often have days off at the same time except on major holidays. I know I get on her nerves at times, and vice versa, so our schedules work for us. It helps me relieve my frustrations with the help of porn in the living room instead of holing up in my office in a chair not made for that type of activity.
I must admit, over time the type of porn has changed. For a long time it was simply one guy, one girl type. Over time it started to change. I started watching hentai, femdom, two girls and a guy threesomes, cosplay, cartoon parody, bondage, and so on. I eventually went on a few apps and created “dating” profiles. It had nothing to do with dating. The problem with that was the guilt factor, so I never actually met any of those women. We would talk for a while, but that would fizzle out one by one when we ended up not hooking up. I would not host at my home. That was a “hell no” in my book. I did have a cover story in case it ever got that far. I ride my motorcycle. I’ll take day trips out of the city just to ride around. I have taken multi day trips to other states to ride through the scenery. But I had not physically cheated…yet. The longer I went without human contact, the more interested I was in letting it happen though.
On my day off while watching my dose of adult entertainment, an errant click put me firmly into the guys with guys category. Instead of instantly correcting my choice, I ended up watching the clip. Then I watched another…and another. Soon those were as much a part of my viewing repertoire as any other. At times even more so. I was horny as well as fascinated. With women I loved their entirety. It was their hair, lips, breasts, hips, legs, and pussy. It was their soft, smooth skin and general femininity. With guys it was simpler, as guys are in general. With guys it’s about their aggression and their cock. I have my own and yet now wanted to play with another.
As mentioned, I already had a few dating profiles. Well, let’s classify them as hookup profiles, as that’s really what they were. Not that they had been successful thus far. Now I made a couple of new profiles on a couple of different sites. The guilt factor didn’t seem like an issue to me. I wasn’t gonna to leave my wife to shack up with some other woman. I wanted to have some human interaction with another guy, and that was it.
You tend to learn new things when introduced to terms you thought you knew before, but mean something else entirely depending on the context. For example, she left her purse on top of the car, and the expiration date is on the bottom of the can. When filling out profile details, those words came up…top, bottom, or versatile. I actually had to look up the meaning of those terms in the new context. Then I had to actually determine how I fit into that spectrum. After a bit of self reflection and judging by the videos I now chose, I determined that I’m a bottom. I’m a bottom in terms of I want to be the one holding, rubbing and stroking another man’s hard cock. I’m interested in licking it like an ice cream cone, and seeing how that affects the person I’m doing it to. In the bedroom, I tend to be a people pleaser. My wife never complained. Looking at our sex life in those terms, we’re both bottoms. In looking at it like that, no wonder it’s been five years. There were other medical reasons with her, but both of us being bottoms didn’t help.
Once posted, I quickly got some interest. Requests for pics, crude comments about my profile, and offers of “right now” were prevalent. I wasn’t interested in any of that. I wasn’t looking for a one time thing. I wasn’t looking for some anonymous blow and go action. It sounds interesting for a moment, but once that moment is over, it would be back to square one. So I was looking for a FWB. That’s much more difficult to find than I expected. I guess the consensus is that blow and go encounters are much more of the mainstream ideals than what I was looking for. Another roadblock was that nobody seemed to be able to host. It looks like almost everyone is in the same boat as I was. Nobody had a place to play. It’s one thing to meet and talk in a coffee shop or bookstore, but patrons tend to frown on someone whipping out their johnson to play show and tell in public. They tend to place urgent calls to the authorities. People end up in jail or having to register as sex offenders for that kind of faux pas.
There were constant challenges in trying to meet the right person. Times available, a place to play, only wanting hookups…the list went on. I was getting as exasperated with the guys as I believe women do. I was at work checking the sites when I got a message from someone I had never talked to before. Checking his profile, he lived fifty miles away. Well, that was definitely not too close to home. As I wanted to remain married, discretion was important. So I never had any intention of messing around with my neighbors, or even people in the same part of the city. Fifty miles away was far, but not too far.
“I ride also.” his initial message stated. “What do you ride?”
He was addressing the part of my profile where I had mentioned that I ride motorcycles. I replied with my bike’s information and he provided his. We both rode big touring bikes. I found out his name was Alan, and he was kind of in the same situation as me. He was married but without sex except on special occasions like his birthday or Christmas. The short messages back and forth were sporadic, sometimes a few in a day, sometimes no replies for a couple of days. I didn’t mind this, as I was not rushing into a quick hookup. Eventually we got around to messaging information of a more sexual nature.
“So what is it you’re looking for on here?” he questioned.
“I’m not entirely sure. I’m pretty new to this. I guess I’m open to pretty much everything at the moment.” I replied.
“Maybe you think that, but you’re probably not. Some people are into some extreme stuff that I doubt you would even entertain. My suggestion would be to start with the basics and work your way up.”
“And what would you consider the basics to be?”
“If you’re new to it all, I would say touching. Just get to know what you like doing with that before moving a little further to oral. Then maybe eventually work your way to fucking. Since you say you’re a bottom you would be getting fucked. Maybe you’re more versatile and would enjoy giving as well as receiving.”
“That’s the basics? That sounds like everything.”
“Nope, that’s still just the basics. You could always try out stuff like bondage, group sex, exhibitionism, role play, webcamming, domination, fisting, furries…the list goes on.”
“I think I’ll stick with the basics to start.”
“Good idea.” he agreed.
Alan and I agreed to meet to ride our bikes around some back roads near where he lived. I was nervous, as this was further than I had ever taken things before, and was now second guessing my decisions. I had committed to the decision though and that means something to me, so even with my second thoughts and feelings about backing out, I went to meet him.
We were to meet at a gas station that he chose. I arrived early as I tend to do, and fueled up while waiting. When it hit fifteen minutes past our agreed time, I started to feel that he wasn’t gonna show. Maybe he got cold feet and reconsidered just as I had thought about doing. I mounted my Harley and was about to fire it up when I heard the rumble of an engine’s exhaust getting closer. It sounded similar to my own, so I waited. Sure enough, Alan’s own Harley pulled into the station and he parked it at the gas pump behind where I sat. He started filling his tank and then approached me where I still straddled my bike. He held his fist out for the greeting bump that had become a societal norm which I went ahead and exchanged. He looked just like the picture he had sent. His shaved head and goatee were in classic biker style. The tattoos that emerged past his short sleeves and ran midway down his arms reinforced the image even more. On this particular day his tattoos were not visible though, as he was clad in jeans, a long sleeve flannel shirt, and a black leather vest which completed that “biker” look. I was dressed much the same, but don’t really consider myself to be a “biker”. I’m just a guy who rides a bike.
“Sorry about that. This is the first time I’ve brought my bike out this year. I still think my tires are low, but I figured I’d check it once I got here rather than be even later.”
Without prompting I hopped off my bike and dug into my saddlebags for a tire pressure gauge and mini air compressor. I was the type who always liked to be prepared. The smallest issue could screw up an entire trip. The part where he mentioned not riding year round was foreign to me. It was only March, but whether it was 100 degrees or 30 degrees, I still rode. I would forgo the bike in favor of my truck if it was raining or extremely cold, but otherwise I rode all year long. To me, living in the south had its advantages for riding a motorcycle. The outside air temperature was already in the upper fifties and going up. It was supposed to be a nice day.
“We can check ’em and take care of it before we hit the road.” I assured.
Both of his tires were low and it took a few minutes to get them properly inflated. Once we were ready to go he took the lead, as this was his area, and he was the one who knew these roads. I was happy to follow and check out the scenery.
Riding a motorcycle is a solitary experience. Even riding in a group, unless you have Bluetooth in your helmet connecting you to other riders, or a passenger sitting right behind you, you’re by yourself in your own head with your own thoughts. I have neither a passenger nor do I wear a helmet, so my thoughts and the passing scenery are what occupied my mind. We rode for a couple of hours along back roads that I had never been on, and probably wouldn’t be able to purposely find on my own again.
We stopped for lunch at a small diner, discussing this and that…little things that moved the conversation along without any real substance. We finished up, refueled, and rode for another couple of hours before reaching the end of the looping route back at our original meeting spot. With agreements made to meet up again and another farewell fist bump, we went our separate ways. I’ll admit that I was disappointed that riding bikes was all we did. Even though I loved riding, our meeting held ulterior motives which had not been fulfilled.
The following day I got a message from Alan in order to set up another ride the following week. I readily agreed. Even if nothing happened, a Harley and the open road was always an enjoyable experience. Commuting to work and back just didn’t cut it.
We exchanged a few messages throughout the week leading up to the next ride. Whereas our conversation hadn’t even touched anything remotely sexual in person, in cyberspace it was different. Alan had much more experience than I, and he was open and candid about his likes, wants, and past encounters. His messages on those matters always left me hard and wanting.
The morning of our next ride we met at a different gas station midway between our homes. This ride was not as planned as the last, but more of a aimless wandering wherever it looked interesting type route. We followed much the same routine, filling up before heading out, and then it was the bike and the road. I was in the lead this time, and we ended up riding around a sizable lake before lunch. Lunch consisted of decent food and more small talk. After lunch was more riding and seeing the sights before calling it a day. I was once again a little disappointed that absolutely nothing happened or was even mentioned, but I still enjoyed Alan’s company and our discussions. As an introvert, I tended not to have much of either of those things outside of work or home. By the end of our fourth ride I had kind of adopted the attitude of “if it happens it happens”. Thus far it hadn’t.
Another week went by before Alan suggested another outing. This time he wanted to head south to an area known for being a popular motorcycle route. This wasn’t close to home, this was several hours away just to get there. The route once we got there was around three hours, and then there was the ride back home. This was definitely an all day thing. My wife had no problem with it, as she was used to my motorcycle trips. I had told her about Alan, in that I said that I met him out in the road, and we had ridden together a couple of times since. She was fine with all that. In fact, she seemed happy that I had expanded my social circle from zero to one. I’m an introvert, what can I say.
Alan and I had messaged leading up to the trip. We hammered out the details, the route, the fuel and pit stops along the way, and discussed the weather forecast. It was now well into May, and we expected it to be sunny and warm. We had postponed a couple of our previous rides due to poor weather conditions, but that didn’t look like it would be the case this time.
We decided not to take the highway south. Although that would have gotten us there quicker, riding is not about the destination, it’s more about the journey getting there. It was also decided that Alan would take the lead, which I was fine with. I actually had never been to that area before, whereas he had…twice. Both times he had been by himself and had taken different ways to get there. This was another different way as well, so he had been there before, but the route getting there would still be new. He also mentioned that it had been years since he was there last.
The date arrived and we met closer to his house, as our route began over his way. A gas station was always our meeting spot, as just getting out there would put a dent in my fuel available for the ride. I arrived a little early as usual and was filling up when Alan pulled up behind me to do the same. The familiar fist bump was exchanged and we soon were ready for the road. It was a long, leisurely, and thankfully uneventful trip south. That’s exactly what you want on a bike. We weren’t the only ones out and about either. We saw lots of other bikes on the road. It seems that our aversion for highway travel was shared by numerous others on two wheels.
We made a couple stops along the way for the requisite fuel and food, as well as just to stretch our legs and see the sights as we took a break. We got to the beginning of the popular looping route just after filling up the tanks again. When you can only go around two hundred miles before filling up again, you never pass up the opportunity to refill before it becomes absolutely necessary.
The route itself was everything I had heard it to be. In my opinion, the straightaways, twisties, hills, sweeping curves, and up close scenery can be appreciated from inside a car, but not nearly as much as from on a bike. We stopped at several points of interest and scenic overlooks that most cars would fail to notice or want to stop for. Once we finally completed the full route, I realized how late it was compared to the hours it would take to get back home. Even if we hit the highway immediately we would be out well past dark. We had already been in the saddle all day, and I wasn’t as used to the long distance as Alan seemed to be. My legs ached and as much as I love riding, getting back on the bike and heading home was not exactly a joyful prospect at that moment. We were at another gas station filling up when I broached the subject.
“It’s kinda late to be trying to head for home, isn’t it?”
Alan looked at his watch and looked at the sun in the sky. I saw him doing the calculations before answering.
“It is later then we planned, but what are our options?”
“Well, we can still head for home, but that’ll make it a really long day. We can get as far as we can before we just decide that it’s time to stop, and then look for a place to sleep. Or we can find a place close by here, relax, and get a fresh start in the morning.”
Alan thought about it for only a moment. “It’s dangerous to ride when you’re tired. It sounds like the best option is to find a place nearby. Also, we can do the loop in the opposite direction tomorrow morning before heading back. They say it feels like a different ride in each direction.”
“Sounds like a plan. Know of any hotels that are close?”
After briefly consulting the internet, Alan rattled off a list of names. None of them were the regular hotel chains I was familiar with. With no sense of quality besides their reviews, I simply let Alan decide. He chose and off we went. He picked a place that the price range fell right in the middle of the two extremes, but was really close to the start of the route for our ride out in the morning. On our arrival, Alan went inside to check in while I waited with the bikes. We had decided on one room with two beds in order to save on the unplanned expense. After a few minutes he returned and we rode to the far end of the lot. We were on the ground floor in the last room at the end. Alan opened the door while I gathered my stuff from my bike.
For those who don’t ride, when you’ve got a touring bike you’re always carrying certain things, even when just going down the street. You leave that stuff in your saddlebags so you have it if you need it. I have a toolkit, first aid kit, a small overnight bag of essentials, usually containing a spare set of clothing, coat, gloves, and assorted conveniences. Also, motorcycles are much less secure than cars, in that it takes very little effort to break into locked saddlebags on a bike. You can break a car’s window, but that’s noisy and obvious, and now most cars have alarms.
As I went in Alan grabbed his stuff which seemed similar to mine. Riders quickly find out what they do and don’t need to carry, and more often than not, it’s typically the same types of things. The room was pretty spacious, with two queen sized beds and a separate area with a loveseat and large TV. I guess I hadn’t been expecting much from a place I had never heard of, so I was pleasantly surprised. I was turning on the TV as Alan entered with his own stuff. He tossed his stuff on the bed farthest from the door and immediately took off his coat and boots.
I frowned slightly at his choosing without debate. I always prefer to be as far from the door as possible, but Alan hadn’t asked. To be fair either had I, and I had been in the room first so I had my chance. I shrugged it off and took the other bed.
“Taking off your boots already?” I asked. “What did we want to do about food?”
“Eh, we’ll order a pizza to be delivered.”
That sounded simple enough. I doffed my coat and boots as well. We sat on the loveseat and Alan grabbed the remote, flipping through the channels, stopping every once in a while to see if the program was worth watching. The screen lit up with a certain show.
“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.
“Quiet! You can take it. Just relax.”
I had instantly shut up as he stretched me further with the added finger that I had initially protested. All Alan’s previous attention had gotten me wound up mentally, but had also bodily relaxed me and inadvertently opened me up for what he was doing now. Alan was still slowly sawing his three fingers in and out of my ass, stretching me out more than before. I still was groaning in protest, although since he had been working his digits inside me, I had gotten more used to it then expected. My sounds of protest slowly changed to the familiar moans of enjoyment from being used as I was. Alan obviously noticed the change in my attitude regarding his actions.
“Round four…ding, ding!” Alan quipped.
Even though he had abandoned any and all attention on my now neglected member, I was still rock hard. I felt Alan place himself directly behind me. I heard the bottle top pop again on what I now realized was a bottle of lube. The smell of vanilla filled the space again and I heard Alan squeeze out some of it before the squishing sounds implied his use of it, presumably on himself.
“You’re liking that, aren’t you? Yeah, you do. You’re not complaining anymore. Your moans kinda give you away. You want more, don’t you? Just relax Brad. I’ll give you something more.”
I heard him, but didn’t quite grasp the meaning for a few moments. Alan used those moments constructively, slowly removing his fingers and placing the tip of his erection against my opening. I realized his intention just before he pressed into me, his thick head pushing past my slick outer barrier and overcoming my feeble resistance. I gasped hard and let slip a high pitched whine as he fed his pole into my ass.
“Oooohh fuck! Alan, please…”
I had intended to add a few more words of protest, but was cut off as his cock penetrated me even further. My pained groan did nothing to stop Alan’s aggressive advance. Another hard slap against my ass produced a very unmanly yelp from my throat, but effectively cut off my argument.
“Quiet!” he demanded. Then he moderated his tone to reassurance. “Juuuust relax. Juuuust take it.”
My potential argument ended before it even began as he fed another couple of inches into me. I groaned as he advanced, only quieting when he paused his efforts. Alan was gripping my waist, holding me in place as he took me how he wanted. I couldn’t gauge if it was seconds, minutes, or hours later, but finally his groin pressed against my ass, with him groaning as he pulled me back towards him. My experimentation had advanced far beyond what I had expected. We had not discussed anything like this involving me. My intention was to go slowly and find out what I liked, but now Alan had his tool buried all the way into me and I obviously hadn’t made a sufficient effort to stop him. I wasn’t sure I would have wanted him to stop. I wasn’t sure if he would have stopped regardless of any effort on my part.
“Damn Brad, you’re tight. I’ve never gotten to break in a virgin before. But I guess you’re not one anymore, are you? Is this what you wanted?”
I couldn’t tell if he was being genuine or sarcastic. He started languidly screwing me, holding me in position as he treated me as his personal fuck doll. I was no longer offering any form of protest, and I still made no effort to stop his activity. Once that was noted, Alan removed his hands from my waist. He briefly paused to reach under me, grabbing my tool in order to gauge my interest in his continuation. My erection had never subsided, even during my times of uncertainty and denial. He grunted approvingly and grabbed both of my shoulders, pulling himself deeply inside me, using the leverage to gain precious little more depth. He would pull away, then groan as he would fully bury his cock once more. He started moving faster, pulling me hard against him as he thrust forward. The harder and faster he fucked me, the more sounds I made in response. The sounds were once again not the sounds I normally made during sex. My low pitched voice could growl with the best of them, but now I didn’t recognize my own voice as Alan continued to sodomize me.
“Mmmmph…mmmph…ooh…ooohh. Oooh yes.”
I was shocked that I sounded more like a chick getting pounded in the myriad of pornos I enjoyed watching, rather than the authority figure I actually am. I tried to stifle the sounds coming from my mouth, but failed as Alan continued to take my ass. I heard him chuckle behind me as he thrust extra hard, making me yelp like a girl.
“That’s right. Just listen to yourself. Just like a little bitch. I told you that you’re more than a bottom. Just listen to how a submissive little slut takes a hard cock.”
Alan thrust hard into me once again, eliciting another higher pitched whine. I heard him chuckle again as he got the reaction he wanted. I couldn’t have cared less about his observations at that moment. I was already occupied by his large cock infiltrating my backside. Alan suddenly slowed his pace. He buried himself fully into me before rolling us both onto our sides on the bed. He now spooned me as he positioned himself to be able to effectively continue fucking me. He slid in and out of me several times before stopping briefly.
“Do you want to cum Brad? I doubt it would take much.”
Alan’s hand reached around in front of me to grasp my member. His light stroking produced more moans from me. He tightened his grip and moved his hand faster. As he did that, he resumed fucking me. I was quickly overwhelmed and unsure what I was supposed to be focusing on. Alan’s cock slid in and out as his stroking hand matched the speed of his thrusting. Between his attention at my front and his taking me from behind, Alan was right. It was not gonna take much to make me explode. Alan placed his mouth right next to my ear, making it easy to hear his whispered words.
“Do you want to cum Brad? I want you to cum. I want you to know that you’re cumming from being fucked. You’re gonna cum because I have my hard cock buried in your ass. That’s what being a bottom really is…it’s taking cock.”
I could barely hear him, even as close as he was. To say I was distracted was an understatement. My building pressure was offset by the feeling of Alan still fucking me from behind. My breathing became heavier as my cock was expertly handled.
“You’re almost there. I can hear it. I want to feel you shoot your load.” he encouraged.
His voice was almost hypnotic as I was edged closer. I was still moaning at the attentions from both front and back. Each thrust of his cock kept pushing a button in me and my own tool leaked constantly as Alan took me. I felt myself begin to climax as the hand around my tool now furiously jacked me off. Alan buried himself deeply in my ass and held still as he now focused on forcing me across the finish line. I would have done anything he asked at this point…anything he demanded.
“That’s it. Cum for me Brad. I want to feel your ass clamp down on my cock.”
“Oh God, right there! Oh God! Yes, yes, yes, Yes, YES, YES!!!” I heard myself say.
The power of my own orgasm surprised me as I shot across the bedspread. I groaned loudly as my organ spurted while Alan still stroked me. He groaned as well as my ass tightened around his buried phallus with each of my bodily spasms.
“Fuck yeah! Damn…that’s what I wanted. You don’t know how good that feels.” Alan said.
His hand jacked me until I had nothing left. I had been pushing back against him as he thrust into me, but now I lay in a useless heap. Alan began fucking me in earnest this time. I could hear his own heavy breathing echo mine. His thrusts were long and hard but no longer steady. He was about to cum. We both knew it. Whereas we hadn’t discussed going as far as we already had, we definitely hadn’t discussed what I wanted in this regard. However, what I wanted seemed secondary to what Alan wanted, and what Alan wanted apparently was exactly what Alan was going to do.
“Oh yeah! Here it comes.”
That was the only thing he said before he wrapped his arm across my chest and pulled me tight to him as he buried himself fully inside me. His cock seemed to grow even bigger inside my hole and I felt his climax. His tool pulsed with each shot as he filled me from behind. He grunted with each spasm, holding still until his cum stopped flowing. He was now the one trying to catch his breath, trying to recover from the fucking he had just delivered. I didn’t have the energy to move away, and he gave no indication of moving himself. We both remained where we lay,
My eyes opened. I must have fallen asleep…maybe passed out was a better term for it. I still had no idea what time it was, but it was still dark out. I was still on my side, but my body was lurching forward. I felt Alan behind me, and more importantly, I felt his hard cock still buried in me. My body lurching was the result of Alan taking another turn with me. I was surprised that he was ready for another go. Not just ready, but already in the process. I moaned as his cock slid into me more slowly and gently than before.
“Mmmmm. Stay still. Don’t go anywhere. I’m almost there.”
I’m not sure if he had been worried about waking me, but now that he knew I was awake, he thrust harder and faster. This felt like deja vu. It seemed like we had just gone through this very scenario. Alan held me still as he thrust harder into me from behind. His breathing became heavier…again. His thrusting became erratic…again.
“Ready? You’re about to get another load.” he growled.
Once again, there was no asking or debate. Alan said it as a simple fact. It was an inevitability. His hand grabbed my hip tightly as he buried himself in me as far as he could. He groaned and grunted and I felt his hot liquid squirt out of him just as he had done earlier. I moaned at the sensation.
“You like that huh?” Alan panted. “You like feeling my cum shoot deep inside you. Did I turn you into a cum slut in just one day?”
I wasn’t willing to answer that at the moment. I wasn’t sure I wanted to know the answer. My riding buddy stayed in place, just enjoying his current position behind and inside of me. Eventually I felt Alan shift behind me. His member had lost some of its rigidity, and he slipped out of my abused ass. He weakly rolled off the bed, and headed into the bathroom. While waiting for him to come out, I fell back to sleep.
It was daylight when I finally woke. I could see Alan sitting on the loveseat flipping through the channels on the TV from where I lay. He was wearing a towel around his waist again. Apparently he had already taken his shower and was clearly waiting for me to get up. I sat up on the side of my bed and got up, shuffling towards the bathroom. When I finally came out clean and refreshed, Alan was now on his own messy bed packing his things. He watched as I went and got my overnight bag and got dressed before packing up everything I previously had strewn around the room.
“Yeah, I can tell you’ve been fucked good. You’re walking differently.” he chuckled.
I was admittedly more than a little tender. Alan had not exactly taken it easy on me the night before…twice. Soon we were ready to load up everything on the bikes and hit the road. I was sitting on the end of my bed trying to get the zipper of my bag closed.
“Pop quiz. What’s being a bottom really about?” Alan suddenly asked.
I felt my face flush red as I pointedly looked at the floor. I saw him come to stand in front of me where I still sat on my bed.
“Taking cock.” I barely whispered.
“That’s right. You were paying attention.”
I heard the sound of a zipper and looked up enough to see Alan’s hand lower his zipper, pull his underwear out and down enough, and free his cock from the opening of his pants. His meat hung down but I could see it stirring slightly. Even though this was unexpected, I knew exactly what he wanted. I slid off the end off the bed and knelt in front of him. My hands went to his waist as my mouth opened and I came up from beneath to take his flaccid member into my mouth.
“Mmmm, yeah. I never get tired of that feeling.” he sighed.
His cock quickly grew to full size as my saliva made his skin shiny and wet. He stuffed his hands in his back pockets, ensuring everything that happened was all my own doing. I briefly looked up and saw that he was intently watching my latest performance, a satisfied smile on his face.
“Don’t worry Brad, I’m not gonna shoot down your throat this morning. I don’t think I have anything left at the moment. Besides, I want to save something for you for after lunch.”