Sharing with Jason

Anytime there is a manager's meeting or a conference, I always insist on a hotel room to myself and my area manager, Matt, is ok with that, even though it goes against company policy that we all share, cos he doesn't want to lose me. I also think he understands, as being in my early 50s, I'm a good deal older than the rest of the team. Saying that I might be older but I'm probably one of the fittest in the team and keep myself in good shape. What I don't tell him is that I like my own room in case I strike lucky with a barman or fellow guest, but that's another story.

This time it was the annual conference and the company had taken over an entire country house hotel, but I still managed to get my own room. The evening went well with a welcome reception, followed by dinner, then drinks and socialising. The conference proper started tomorrow 8.30 sharp, so I took it easy on the booze, unlike some of the younger guys. About 11 o'clock, I was thinking about calling it a night when I spotted Matt heading in my direction.

"Steve," he said, looking slightly uncomfortable, "I need a big favour."

"Ok" I said, wondering what was coming.

It turned out that Jason, one of the newer managers, who lived locallly, had driven here, with the intention of driving himself home, but thanks to some of the other guys slipping vodka in his diet Cokes , he was in no fit state to get behind the wheel. There were no taxis available for hours and no spare rooms, so I knew what was coming next.

To put Matt out of his misery, I said " Ok ok, he can share my room."

Matt looked relieved. "Thanks a million Steve. I know you don't like to share, but it's only for one night. I'll bring him over shall I ?"

I'd never met this Jason, so I watched Matt walk across the hall towards a tall, dark haired guy in his early 30s maybe and after a brief conversation, which resulted in Jason looking in my direction and shaking his head , they came over. Close up Jason was a handsome and fit looking guy, but a little the worse for wear.

After introducing us, Matt left me with him and I thought it was really great of him to leave me to babysit.

"Well I was just heading upstairs, but I can get another key card from reception if you want to stay a while."

He shook his head. " No, I've had enough of tonight. I'm quite happy to turn in."

So we took the lift up without much conversation but I could see he was a bit unsteady from the drinks he'd been slipped and I just hoped he wouldn't be a nuisance. Up in the room Jason eyed up the king size bed but didn't comment. He did apologise for being a pain and that he would be quiet and not disturb me. I felt sorry for him "What did Matt say to you exactly?"

"He told me you always have your own room and like your own space, so I wasn't to upset you."

I sighed " Look I'm sure we'll get on just fine. Anything else bothering you?"

He had another look at the bed. "Well I've no stuff with me for an overnighter and nothing to sleep in."

"Well if it's any help, there are complimentary toiletries in the bathroom, I'll give you my spare razor in the morning and I sleep naked anyway, so no pyjamas is ok with me. Now let's get settled down. It'll be a long day tomorrow."

Then I headed to the bathroom to go to the toilet and clean my teeth. When I came out, Jason had mostly undressed and was standing there in his briefs and socks, stilll looking pretty tasty and making a bad job of hanging up his suit.

"Bathroom's free." I said, taking the suit out of his hand to hang up properly." You'll need this to be smart for morning"

He headed for the bathroom with a thankyou and I hung up his suit, followed by my own and carried on undressing, listening to him clattering around next door. When Jason eventually reappeared, I was standing there in just my white pouch briefs, which I fill out quite nicely, if I say so myself.

Jason took one look and said "Wow, great body, you're really fit."

"You mean for an old guy."

He shook his head "No, that's not what I meant. I do think you're really fit"

"It's okay I'm only teasing you." and I gave him a grin, but I did notice that his focus appeared to be on the bulge in my briefs. Well if he was interested, he was about to get a good look.

"Come on, let's hit the sack." dropping my briefs and letting my cock flop out.

There was a big gasp of breath from Jason and he stood there, not able to take his eyes off my semi erect cock . Then he seemed to realise what he was doing. " Sorry I'm staring." he said but didn't move." I've just never been so close to a cock that big before ."

"Its fine. I get a lot of attention at the gym so it doesn't bother me"

Which was true, but having this handsome, semi naked guy standing a couple of feet away, giving my cock his full attention, was causing things to happen and I could see from Jason's face that he was loving it. He edged a bit closer cleared his throat and muttered "How big do you actually get?"

This was turning interesting, but I wasn't sure how far he would go.

" If you want to find out, help yourself."

Well he was on his knees almost before I got the words out, making a sloppy job of getting as much of my cock in his mouth as possible.

Boy, he could suck, which was pretty impressive as most guys struggled with my 11 incher, so I let him do what he wanted, till eventually he gagged and came up for air.

"Phew, just needed a breather. That's the biggest cock I've ever sucked."

I looked down at him kneeling there in front of me. "Ever been fucked by by one this big?

His eyes widened." No, but looks like tonight's the night. "

He pulled off his socks and underwear, revealing a hard 7 ins and as he turned towards the bed I got a first look at his rounded naked arse. Pushing him face down on the bed, I was straight in there with my tongue and as soon as I started probing his hole, he started to moan and his pucker twitched in anticipation. After getting him nice and wet, I spat into my hand, rubbing it over my cock head, then pushed against his hole. It obviously wasn't the first time he'd been fucked and he was pretty relaxed after the alcohol, so despite the size of my cock, before I knew it, I was three quarters of the way inside him. I took it slowly, not sure how much he could take, but he reached round and practically pulled me towards him and before I knew it, I was right up to the hilt. "That's better. Now ride me."

Well I didn't need any more encouragement, but started to build up a rhythm, pulling almost out then slamming back in again, which made Jason moan and grip the bed. I decided I wanted to see his face and cock, so picked him up and swivelled him round and dumped him back on the bed, then went back to fucking that lovely arse, my cock pumping into his hungry hole, while my balls slapped against his ass cheeks. He started wanking his own cock, all the time raising his head so he could see my massive thick weapon destroying his asshole , which turned me on even more. Every now and again, he looked up at me and whispered "Fuck me Daddy."

Reaching up a hand to caress my chest hair and play with my nipples, his other hand kept furiously pumping his rock hard cock, which was dripping precum. His gaze fixed on mine and we locked eyes. His breath was ragged "I'm getting close. I need to come so badly."

"Go for it, then. I'll be right behind you."

I watched as with a sharp intake of breath, his cock spewed out spurt after spurt of creamy white cum, shooting into the air, some of it hitting him in the face. That did it for me and I felt my cock swell as I filled his hole with my own cum, gushing out, wave after wave, till my balls were empty. I could tell that Jason felt it too, by the way he was looking at me.

"Fucking amazing, Steve."

I collapsed on top of him and we lay like that for a little while to catch our breath, then cleaned up and settled down. There was no shyness from him now about sharing a bed. He jumped in naked and lay next to me, fondling my cock as he drifted off. It took me a bit longer to get to sleep and the last thing I remember was wondering if Jason would regret this in the morning.

I'm not sure exactly what time I woke, but I was very aware of a warm mouth on my cock, coaxing me back to hardness. Lifting the covers, I saw Jason was enjoying himself, sucking on my balls then running his tongue up the underside of my cock and round the swollen head, before taking my length down his throat. I laughed. "Morning. Having fun?"

He mumbled something and nodded, as much as he could with his mouth otherwise occupied, but he came off me, only to squat across my stomach and reach behind, holding my cock as he lowered himself on to it, giving a sigh as his hole was penetrated by my thick, hard dick. He took it slower than last night and I was happy to stay still, enjoying being inside him and watching the expression on his face as, with his eyes closed, he moved up and down on my cock. I lay there with my hands behind my head, giving me a good view of my cock being ridden by this hot guy, who didn't seem to need any participation on my part, as long as he was getting some cock. I studied his leg muscles straining , as his own erection bounced in front of me and watched my dick slide in and out of his hole. Without opening his eyes, his hands found my nipples and he started rubbing and twisting them, just firmly enough to send a little tingle down to my cock and he started moving faster and faster as he rode my huge, throbbing knob, causing me to head quickly to almost losing control. Jason seemed to sense it and his eyes opened, locking on to mine.

"Come on, I want to feel that cock filling up my hole, Daddy."

He gave my nipples an extra hard squeeze and I let go with a roar, sending a flood of hot man juice shooting up inside Jason's arse, as he continued to rock slowly on top of me, tightening and relaxing to squeeze every last drop of cum from my cock. I lifted my knees to push him towards me, my cock staying embedded inside him, so I could get his erection in my mouth and it only took a few deep sucks till I felt him cum and hot salty semen flooded my mouth, which, although I swallowed, still dribbled down my chin. He leaned forward and licked it off, then kissed me , the taste mingling in our mouths. As we lay there for a bit of a rest, I was thinking this encounter had been pretty hot and wondered how it could be repeated.

Half an hour later, I was shaving in the bathroom, when I noticed in the mirror that Jason had come in and was standing, leaning against the door, watching me. "Steve, I've been thinking. I might get more out if this conference if I was staying in the hotel with the rest of the team. What do you think?"

I caught his eye in the mirror. "Yes you probably would, but I suppose that means you want to share my room for the week?"

He looked a bit crestfallen. "Well, only if you're ok with that, of course. "

"Well I might manage to put up with you a while longer. Let's talk to Matt at breakfast."

So, it was decided that Jason would stay in my room for the rest of the conference, just so he could get the full experience of bonding with the team, although a totally different kind of bonding would be going on in our room.

Later in the week, I had a chat with Matt, telling him, that as Jason was a nice quiet and respectful guy, I didn't mind sharing with him going forward and that would stop the others from thinking I was getting preferential treatment with my own room. Matt agreed, but I think he did have a very good idea about what was really going on, although I knew he would keep that to himself.

Meetings were going to be so much more interesting from now on.

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