A couple of nights in a hotel away from the wife and kids. That’s all I wanted. But I have to room with Toby instead.
This gay erotica story is about dealing with an unexpected roommate.
“I’m sorry, sir, I’m afraid the hotel is fully booked. The booking we have on our system from your office only has the one room. Though it is an American twin so it’s two double beds if that is any consolation.” The young lady standing at the check-in desk poured the customer service apology voice on thick, her smile broad and plastered on. I did my best to remain calm. This was a stupid inconvenience but it wasn’t her fault. The new office manager was already on strike two, only booking one room for the two executives who were attending this conference was strike three.
I signed the check-in form in front of me, took my credit card back and picked up the key cards. After thanking the check-in clerk for her efforts, I turned back to my colleague, waiting at the end of the desk.
“Guess what Kay fucked up this time?” I asked, holding up the single set of key cards.
“No way.” Toby realised immediately that we only had one room. “I’ll email HR when we get up there.”
“I already have. She’ll be gone within hours of our return, don’t worry about that.”
“It had better be a decent room.” Toby grabbed his suitcase and wheeled it alongside me as we walked to the elevator.
The lobby was busy; full of other business people checking in for the conference at the centre next door. I glanced around, keen to see if anyone I knew was around. I had a love/hate relationship with these conferences. For the most part, it was a hard grind of non-stop networking, putting on the business boss facade to connect with clients, pore over product manuals or sit with salespeople. That part was tiring. But there was also the chance to reconnect with former colleagues and enjoy the occasional productive conversation. But the real win was three nights in a hotel room, in a big comfy bed all to myself, with no kids knocking at the door asking for another bedtime story and no wife hogging the ensuite bathroom with their hour-long nightly skin care routine.
As I stepped into the lift with my colleague, I sighed to myself. The rare solo moments of relaxation that were the highlight of these trips had just been ripped away from me. Not only that, but the colleague who would be sleeping only a metre away from me was Toby. I had nothing against him personally, but if you had to ask me to share a room with anyone in our company’s C-suite, he’d probably be the last on the list.
“So do you think this fuck-up will help us convince Angela to include the mini-bar on the company card this year?” Toby joked as we stepped out of the elevator on the 15th floor.
“If we keep the drinking below the cost of the extra room it will. It’ll be the pluses and minuses that win that battle for us.” I turned to 1515 and pressed a card against the panel.
“I think I can manage that. It’s not like I’ll be bringing extra guests to the room this year.” Toby followed me through the door.
I huffed a short laugh, but his comment reminded me of one of the reasons he and I didn’t get along.
Toby had a reputation when travelling. Beyond the business connections he was obligated to make over these three days, he also spent just as much energy making personal connections. And he wasn’t shy about it either. Last year our separate rooms shared a wall and while I had my tablet open, enjoying a rare, uninterrupted solo session, I couldn’t help but hear the grunts and gasps from next door.
Don’t get me wrong, all power to him for getting the action and I definitely didn’t have a problem with the fact that it was the grunts of two men I could hear. I had lived in residence during my university year. I was no stranger to man-on-man action happening around me. But having to hear the session at 8pm and then the second session at midnight and then listen to the proud retelling of those events at the breakfast buffet the next day, didn’t really endear me to the guy. I also didn’t connect with him always putting his sexuality at the forefront of his personality. Call me old school, but I just think there are some things that should be kept to yourself.
At least a silver lining of sharing a room with him this year would be that he wouldn’t be up all night ‘entertaining’.
I swung my small suitcase onto the bed closest to the window, Toby already having claimed the bed closer to the door. I hung my suit bag into the small wardrobe and then turned to check out the view.
“At least we’ve got the good side of the hotel. Remember the year we had a view of the carpark?” I asked as I stepped over to the floor to ceiling windows.
Toby walked up beside me, he already had a beer in each hand. I took the one he offered, clinked the bottles together and took a long sip.
“The south side windows face the other hotel. Those years I can’t even open the blinds, if you catch my drift.”
I did catch Toby’s drift, and I rolled my eyes and shuddered a little at yet another implication of his promiscuity. Then I felt Toby’s head turn towards me.
“Sorry Bry, that TMI?”
Shortening my name from Bryan to Bry was another tick on the negative side of the ledger for Toby, as was his use of unnecessary abbreviations. Maybe that was a Gen Z thing and I was showing my age. The difference between 41 and 28 maybe?
“Maybe it’s just I’m not used to hearing about it. I just have never really talked openly about that stuff.” I tried to remain diplomatic and not give away how little I actually wanted to hear about his sexual exploits. That wasn’t specific to Toby, now that I thought about it. Even in my younger days, pre-marriage, I hadn’t wanted to hear about what my neighbours in the dorm had gotten up to. I hadn’t shared any of my stories with anyone either.
“I guess you older married guys have less to talk about.” Toby chuckled. “Is it true what they say that once there’s a ring on it, the ladies shut up shop?”
I shook my head and then opened my mouth to reply. I closed it again, not knowing what to say.
“You were probably looking forward to the solo room so you could beat off uninterrupted eh?” Toby laughed again, draining the last of his beer.
I blushed. Luckily, Toby had already turned away to return to the minibar.
“Well, if I’m lucky enough to find another room to spend a little time in tonight, I’ll let you know how long you’ve got the room to yourself alright Bry?”
“Thanks.” That was the only reply I could manage.
“Alright. One more beer while we unpack, then I’m going to change into something designed for style not comfort, then we hit the opening night social eh?” Toby thrust another bottle into my hand. I quickly downed the last of the one I already had and placed it in the bin before moving back to my suitcase.
The bar at the bottom of the hotel was packed and it was only 6:30. The opening night social was the unofficial start of the conference. The talks, the meetings and the conference floor didn’t start until tomorrow morning but 6pm on Tuesday night was where the first connections were made.
I stood with a glass of red wine in my hand, searching for a waiter with a tray of something that would help me line my stomach. Toby was already mingling. After completing my obligatory phone call home to wish the kids good night, I had arrived at the bar later than he had. It was hard to tell whether his conversations were personal or professional. He seemed to have the same gregarious approach to all situations.
I grabbed a couple of sausage rolls from a passing tray and hastily downed them before moving into where the action was. I talked with a couple of familiar faces, including a manager from one of our interstate offices. My glass was topped up regularly by the waiters and I made sure to grab food from any servers that passed by. After an hour and a half of mingling and chatting I was feeling the buzz of the wine and beginning to relax a little. The shared room was inconvenient but I was still determined to get as much as I could out of the time here.
Another half an hour later and the event seemed to be winding down a little. The crowd was thinning and I had already chatted to most of the people I wanted to see at this initial event. I picked Toby out in the diminishing crowd and found him sitting in a booth with another guy. There were empty glasses on the table and they sat close side by side. As much as I had struggled to discern his intent earlier, it seemed pretty clear that this wasn’t a professional conversation. His hand now rested on a thigh and Toby leaned in to speak into the other man’s ear. They both nodded before standing and sliding out of the booth.
I turned away quickly, not wanting Toby to know I’d spotted him. I faced the bar and asked for one last top-up of my glass. By the time it was poured, I sensed Toby walking up beside me.
“Bry. You got your wish. Florian is an intern at A.B. Glass. He’s keen to make a good impression. What do you think? He’s hot eh?” Toby winked and nudged my shoulder.
I opened my mouth to answer before I realised and stopped myself.
“Just kidding mate. It’s almost 9:00pm now. I reckon you’ve got the room until around 10. Is that enough time?”
I couldn’t help but blush a little. Toby was right, I absolutely wanted some time to relax with my own company in the hotel room. I just didn’t know how I felt about him knowing that. I didn’t come up with the words to reply quickly enough.
“I’ll take that as a yes. The room is yours mate. Do with it as you will, just have it done before 10 if you’re shy and don’t want me to see.” The grin on Toby’s face broadened before he turned back towards Florian and they headed to the lift lobby.
I grabbed my glass and took a slow sip. I didn’t need another drink and was suddenly keen to return to my room, but I wanted to make sure Toby was already headed up. Rushing to the lift lobby after the hints he had dropped would make me seem far too enthusiastic about the activity.
After another sip I left the bar, walking quickly to the elevators and tapping my card. Within a couple of minutes I was on floor 15 and entering the room. My dick was already beginning to grow in my trousers. This didn’t happen often and was a pretty clear indication that the action ahead was overdue. I only flicked the switch to turn on my bedside lamp before I walked further into the room.
I slipped my shoes off and undid my belt. After unbuttoning and removing my shirt I returned it to the hanger in the wardrobe. My pants slid from my legs and I tossed them over the chair by the bed due to a shortage of hangers. I stood for a moment and took a deep breath. I slid a hand over the bulge in my briefs, slowly reacquainting myself with the length. I tried to remember the last time I had been able to take my time with it, when I had been able to do more than just tug it hard and fast in my morning shower.
As I stood at the window, looking out on the city skyline, running my fingers slowly along the hardness beneath the thin fabric I sighed. I couldn’t remember anything like this between now and the last conference trip. My manhood twitched in response to the light squeeze I gave it and I felt the first leak wet my briefs. These chances were rare and at this year’s conference this might be my only chance.
I turned away from the window, stepping to my shoulder bag to retrieve my tablet. The opportunities for solo pleasure were few and far between, the chance to do so with visual stimuli were even rarer. I tossed the device onto the bed and then slid my underwear off. My hard dick caught in the waistband before flicking up and slapping against my body. It bounced and then stuck straight out, already rigid. I fell back onto the bed and settled in.
Picking up the tablet, I quickly unlocked it and opened a private tab on the browser. With one hand I tapped at the screen, hurrying to find a suitable video. I had my favourites and those came up early in the search results but I scrolled a little further, seeking something new for what might be the only session of the week.
My other hand toyed lazily with my erection, sliding over the hard length and then over my heavy balls, occasionally squeezing it and sending a shudder through my naked body.
I found a video I hadn’t seen before, with a porn star I had liked from her other work. I tapped on the screen, skipped through the ad and then set it to full screen. After turning off the lamp by the bed, I propped the tablet up beside me with a pillow. Now everything was set in the perfect position. I settled again into the mattress and wrapped the fingers of my right hand around myself.
The response from my body was immediate. Goosebumps broke out over my skin. A long sigh escaped my lips and I leaked over my fingers. I opened my legs slightly, sliding my left hand under my balls, feeling how heavy they were with overdue need.
My eyes moved from the screen to my erection. I watched the skin slide over my head, growing steadily more slick with my leaking. I paused for a moment and held my dick up from my body, admiring the length and the thickness. When we had first started dating, Samantha had been impressed by this. She almost couldn’t get enough. Now it felt like she only did it out of obligation.
I returned my eyes to the screen, to focus again on the action there and slid my left hand from my balls to join my right in gripping my shaft. I slowly worked myself over, watching the woman on the screen gasp and moan as she was bent over a kitchen bench and opened up by a thick piece of meat. Each of her hands wrapped around another dick in the group scene taking place in what was meant to be a commercial kitchen. I let out a soft moan as a ripple of pleasure ran through me.
I turned back to watch myself stroking. The skin slid back and exposed my head as my hands moved down my length. I squeezed, urging another drop of precum forth before moving my hands up to slide the wet skin over my sensitive glans. A grunt accompanied a spasm of need hitting me. I paused and let out a slow, deep breath. I couldn’t afford to release too quickly tonight. If this was the only time I was guaranteed to have this room to myself, I would push it to the limit. I glanced at the clock by the bed. 9:20pm. 9:55pm would be my time. That would leave me enough five minutes to walk to the bathroom and clean off before Toby returned. For a moment I wondered if Toby was also checking the time or if he was just freely enjoying bending that guy over. I pushed the thought from my mind and returned my attention to the group of guys taking turns on the girl on the screen.
I stroked steadily, maintaining a slow pace that allowed me to enjoy myself and the feeling of my dick filling my hands. The noises from my tablet speakers increased in volume and pitch as the next large cock hammered harder at the woman now lying on her back with her legs spread. I smiled to myself as she cried out about his length and his girth, remembering that it was these kinds of videos that helped me realise a lot about myself in my younger years. Her moans were suddenly muffled as one of the other guys pushed his dick into her open mouth.
I squeezed two hands around my shaft, feeling it pulse in response. I grunted with pleasure again, without caring if anyone on the other side of the wall could hear me. This was the stuff hotels were made for. I was determined to enjoy myself with what little time I had.
As I continued to slowly slide my hands over my hardness, I heard my phone buzz and I looked over to my trousers hanging on the chair. It was probably my wife with her nightly goodnight call. Another inescapable duty I had while travelling. I checked the clock. It was now 9:40pm. A little early for her to be going to bed. I decided that returning her call could wait the 20 minutes until I was done. Another surge of precum leaked from my slit and I knew I didn’t want any interruptions at this point.
A loud grunt came from the speakers of my tablet and I turned back to the screen in time to see the first stud firing over the woman’s face, her tongue sticking out and lapping at the seed shooting forth. An involuntary shudder passed through me and I halted my stroking, breathing deep to hold myself back from the edge. I paused my stroking as the other two men gripped their impressive cocks and fired hard, their loads flying from their dicks.
I removed my hands and leant forward, tapping the screen to move onto the next video. My phone buzzed again. She could wait 10 minutes.
The video started and I returned to my stroking. I checked the clock. 8 minutes now. I picked up the pace a little. I was pushing closer to climax but put in place all the tricks I knew to hold myself back. I opened and relaxed my legs. I breathed slowly, deep and steady. This new video didn’t waste any time. Any storyline was already skipped and my favourite porn star was on all fours on a bed, moaning and shaking as another big dick thrust into her, this time there was only one and the stud who owned it held her hips in place as he entered her.
I felt the first tingle in my toes, knowing just how close I was to hitting my climax. I slid a little further down the bed, laying my body out to prepare for my release. The cries of the woman in the video increased as she reached her own orgasm. The stud pulled out, tore off his condom and gripped himself, spraying his load over her back as she panted and he groaned. I watched the action intently before the screen went dark.
I decided against clicking the next video and just gripped myself tighter, increasing the pace again. I knew I no longer needed any other stimulation to reach my conclusion. Another tingle in my toes began to spread up my legs and I screwed my eyes shut. My head fell back on the pillow and I grunted, feeling my pleasure building to its final moments.
As my body shook and my dick pulsed in my hand I heard a gasp. I opened my eyes to shut off the autoplaying of the next video. But the screen was dark.
“Holy shit!”
My eyes turned to the sound to see Toby standing in the doorway.
“Fuck!” I yelled as I grabbed at the blankets beside me. They twisted in my hands. With my body laying on top of them and the tight hotel tuck they didn’t move and gave me no opportunity for coverage. I grabbed the pillow from behind the tablet and pressed it over my still-hard dick. The device fell to the floor but I made no move to save it.
“Sorry Bry. I uh, I texted you saying I was done and coming back. You didn’t see it?” Toby’s grin was wide. Thankfully he let the door close behind him but didn’t move into the room any further.
My heart slammed in my chest. I opened my mouth to speak but no words came out. My dick twitched under the pillow.
“Unless you wanted me to see it.” Toby took a step forward now. “I mean. From what I did see you got something that’s worth showing off that’s for sure.”
I blushed again. My dick wasn’t going down at all despite the embarrassment.
“I’m sure I’m not the only guy who’s seen it and been impressed right? You played sports in university didn’t you?” Toby took another step. I froze.
“You were meant to be back at 10.” I finally managed to get some words out, mostly in an effort to deflect Toby’s last question.
“I know. That’s why I texted. We were done quicker than we thought and then he started talking about work so I was keen to dip.” Toby sat on his bed, facing me. “But I don’t want to give you blue balls. Go ahead and finish. I’d love to see that big thing a little closer.”
My jaw dropped. Those words hit me with a flashback. Second year university. The guy in the room next door had walked in on me in the shower of our shared bathroom. Unlike Toby he had quickly apologised and darted out, but later that night, after a couple of beers he had said those exact words, “I’d love to see that big thing a little closer.”
“Bry. You with me?” Toby leant forward a little. “That pillow isn’t doing much at all to hide the fact that you’re still stiff as a board under it.”
I gulped.
“If you don’t take care of it there’s no chance you’ll be getting any sleep tonight.”
My dick twitched again and I moaned despite myself. I knew that Toby was right. I had been seconds away from a long overdue and long built up orgasm. If I didn’t release now I would spend the whole night tossing and turning in bed. I slid my legs off the side of the bed, realising too late that I had moved towards Toby. I held the pillow in place as I stood.
“I might just head to the bathroom to finish off.”
Toby reached out and placed a hand on my hip. I flinched but didn’t move away.
“You don’t have to.” He spoke more softly now. “The bed is more comfortable and I’m going to hear and know exactly what you’re doing in there. At least let me see how that big thing finishes.”
I sighed.
“And they say what happens on the conference stays on the conference.” Toby continued.
I looked down and my eyes locked with his. It had been years since anyone had shown genuine interest in my dick. Samantha had loved it early on, but had always struggled a little. My dorm neighbour had loved it too, and had struggled less with length and more with the volume of release. My body shook with pent-up desire and walled-off memories.
“I just wanna watch. I’ll keep my hands to myself.” Toby grinned and rubbed his crotch a little. “Unless you give me permission, that is.”
Another flashback hit me. My last scout camp. A group of curious boys, sneaking out at night to skinny dip. All eyes on me. My inability to stop the hardening. Then my inability to stop myself from taking their compliments and giving them the show they had requested. The stars that clouded my vision as I fired the hardest orgasm of my life so far.
Without thinking any further, I fell back onto the bed. Toby’s grin spread even wider across his face.
“Stay on your bed alright?” I chuckled a little as I slowly slid the pillow aside. My cock had hardly diminished in size or stiffness.
“Holy shit man. I thought I was gifted.” Toby licked his lips.
I slid a hand over myself again. “Thanks. I guess.”
“If Samantha isn’t getting on that, she’s missing out.”
A shudder of pleasure passed through me again and I relaxed into the sensation. “It’s been a while,” I admitted.
“Is that why you stayed so stiff even after your gay mate stormed in?” There was a glint in Toby’s eyes now and a cheeky edge to his tone.
“Yeah. It’s overdue.” I stroked a little, hoping the action would stop any further questions.
“How big is it Bry?”
“Call me Bryan please.” The words slipped out before I realised, the dynamic shift between us finally giving me the guts to correct him.
“Sorry Bryan. How big is it?” Toby’s eyes were locked onto my dick as I resumed sliding the skin over my wet head.
“About 9 and a half.”
“Thick too.”
“Yeah about 6 and a half around.” I grunted after I spoke, my dick twitching in my hand.
“You often use two hands?”
I smiled and added my other hand to my dick, remembering that was the scene Toby had walked in on.
“Holy shit Bry, sorry Bryan. That’s impressive.” Toby moved a hand back over his crotch and I noticed the bulge in his trousers. I couldn’t help but feel a sense of pride. This guy had cum not long ago, but was already hard again, because of me.
“I’m glad someone’s appreciating it again.” My confidence was growing with each stroke now, as Toby stared at my dick and rubbed himself.
“Say the word and I’ll appreciate it in any way you want.” Toby leant forward a little more, getting as close as he could without leaving his bed.
I stroked slowly for a moment. I was already back on the edge of cumming and knew that I could fire my long-awaited load at any moment. But I realised I was enjoying the attention and the admiration.
“Am I the first guy who’s seen this thing in action?” Toby asked, the arousal in his voice was obvious.
I paused, preparing myself to make the admission. “No,” I said softly.
Toby’s eyes darted back to my own. He raised an eyebrow. “Well. No wonder you don’t like hearing me spill, if you’ve been hiding these secrets.”
I laughed. “That’s part of it.”
“And the other part?”
“You just talk too much.”
Toby shifted off his bed, moving onto his knees beside mine. “There’s a line I always use when a prospect says that to me you know?”
“Yeah?” My dick was leaking steadily again, slicking up my foreskin and my fingers as my hands worked over my shaft.
“If you want me to shut up, why don’t you fill my mouth with something.” Toby looked back up at me, winked and grinned, edging right up against the mattress.
I shuddered and my dick pulsed. I looked Toby in the eyes. “What happens on conference stays on conference.” I said the words softly before letting my hands fall away from my dick.
Toby moved quickly, sliding his fingers beneath my stiffness before lifting it up again. He leant forward and immediately wrapped his lips around me and slid them steadily down until I felt my head push against the back of his throat.
“Oh fuck.” I cried out, at a volume that almost definitely would have reached the neighbours.
Toby huffed on my cock before working his throat muscles over me. I moaned and shook on the bed as he did so.
“Damn. Shit. Fuck.” I gasped out the only words that would come to me. My head fell back on the pillow as my legs stiffened.
Toby took a long deep breath. The vibrations passed over my cock. I felt his fingers wrap around the base of my shaft that hadn’t fit into his mouth. He moaned and I grunted. Then he began to move.
He slid his wet mouth over as much of my length as he could while his hand slipped my skin over the rest. The wetness of his mouth and steady stream of my precum worked to slick me up and the wet sounds quickly filled the room.
Toby’s body moved and I opened my eyes to see him shift onto the bed, kneeling between my legs. He picked up the pace and the new angle meant that each movement pushed my head into his open throat. The alternate sensations of wetness, movement and tightness were pushing me closer and closer to my climax. I moaned and gasped, unable to form words.
My legs stiffened. A shudder passed over my body. My cock throbbed.
“Fuck. I’m-” the words caught in my throat.
Toby grunted in response and I noticed the slightest nod of his head.
With permission granted I released. My eyes screwed shut, my head fell back and I fired. My cock pulsed and I felt shot after shot fire hard into Toby’s open mouth. He grunted as I climaxed, working to swallow the huge load I gave him.
“Holy shiiiiit.” I cried out as wave after wave of ecstasy tore through my body. My legs shook. My toes curled. My hips bucked. Toby worked through it all. Panting and huffing as he held his head in place to take it.
A long deep moan escaped me as the last of my orgasm poured out of me. One final, violent shudder hit me before my body relaxed and fell back into the softness of the mattress. I felt Toby’s tongue working over my shaft, his lips squeezing every drop of cum from me.
With one last, slow movement he lifted his head, licking at the slit of my dick before sliding off the mattress and resting on the floor between our beds.
“Damn Bryan. That was fucking epic.”
I kept my eyes closed, feeling my cock wilt over my thigh. Thoughts rushed through my head. A mixture of satisfaction and regret.
“You have an amazing cock. Thank you.”
I took a deep breath, trying to enjoy the post-orgasm bliss.
“I don’t want to say too much. But if you want that again, just ask.”
Every time Toby spoke it reminded me that it wasn’t my own hand that had caused my current bliss.
“Don’t feel guilty. What happens on conference stays on conference okay?”
I took another deep breath, my eyes still firmly closed. “Toby?”
“Yeah?” I felt Toby move and assumed he was now facing me.
“Shut up.”
“Yeah. Right. Sure.” For the first time ever I heard something other than confidence in Toby’s voice.
“Do me a favour?” I spoke softly and slowly, still coming down from my massive release. “Go down to the lobby and get some more beers.”
“Great idea.” Toby stood.
“Take your time. When you come back I’ll be watching baseball highlights and you will have just come back from fucking that other guy. Get it?”
Toby was quiet for a moment. I cracked an eye open to see him trying to work out what I meant. “I get it Bryan. No worries. Good with me.”
Toby turned and walked out of the room. After the door clicked shut, I opened my eyes fully. I walked into the bathroom and stepped under the hot water of the shower. My now flaccid dick hung between my legs. It was unappreciated these days. Toby had been there to appreciate it. That was it. Just like the neighbour in the dorm and the boys on scout camp. I had needs to release and something this big needed an admirer occasionally. That was it.
I turned off the water and stepped out. After drying myself, I walked into the room. I slipped a pair of boxer shorts on and my old university team t-shirt. I switched on the bedside lamps on and lay on the bed. With a couple of clicks of the remote, the baseball highlights filled the TV screen.
A minute later Toby walked through the door.
“Hey roomie.” He grinned as his eyes darted directly to my dick. “Thought I’d give you a little more time to yourself. That guy wanted a second round anyway. Brought more beers.”
I leant up on the bed to take the bottle Toby offered, deliberately opening my legs and watching his eyes lock onto the movement that created.
“Thanks Toby. Hope you had a good night.” I took a long sip of the cold beer.
“You too Bryan.”
“I did.” I tried to hide my grin from Toby as my eyes moved back to the TV and my dick twitched again in my boxers. This could become an interesting week.
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