Jack was the only gay guy I had ever talked to at any length. We both worked in the film biz, I was a carpenter, and Jack was a scenic artist/painter and was quite open about his homosexuality with the crew. I would build the scenery, and Jack would paint it. We were both part of a scenery crew sent to a small town just outside our home city to set up a stage set in a park for shooting the next week.
We all arrived as the weather started to threaten snow, and by the end of the day we were all wet and miserable. We had dinner in the restaurant attached to our motel and retired to our rooms. Production had arranged for us to stay overnight in this motel, which we filled completely, but Jack had only arrived that evening, driving through the storm, and was then told that there was no vacancy, all the rooms were now occupied, and as the roads were getting too treacherous to drive, Jack was stuck here.
Rebecca was the head painter of the small group of mostly female painters, and as I was the oldest carpenter and a grandfather, she figured that it was ok for Jack to stay with me. The younger carps would not want to share a room with gay Jack, but I could handle it since I was in my sixties and obviously my sex life was over anyway. Thanks, Rebecca.
Well, my sex life was definitely not over. I was horny quite often, and this was one of those times. I had just stepped into the shower and was soaping up my genitals and contemplating a relaxing jerk-off session when I heard the pounding on my door. I quickly wrapped myself in a towel and opened the door to see Rebecca and Jack standing in the hallway about to dump their problem in my lap. They both were somewhat embarrassed to see my half-naked sixty-year-old body. I had expected one of the carpenters, so I too was taken by surprise.
Rebecca started right in. "Please, Dave, Jack has nowhere else to stay. It’s just for tonight. It’s too late to make any other arrangement, and the guy at the front desk has gone home because of the storm and I don’t know what else to do.” She was obviously anxious, and I felt that I had to respond to her plea.
Now three things were going on in my head at this point. One, I knew I was pretty well obligated to let Jack stay with me, where else could he sleep? Two, I didn’t want Rebecca or anyone to know that I had the one room in the motel that had only one bed instead of the usual two, and three, the idea of spending the night with Jack in the same bed was strangely making my cock swell with anticipation.
“Alright, but keep this to yourself. I don’t want the guys to know about this.”
Rebecca rolled her eyes, but agreed. “Oh, you men! But thank you, Dave. I owe you one.”
I had been blocking the doorway so Rebecca wouldn’t see that my room only had one double bed. I don’t know what she would have thought if she knew Jack and I would be sleeping in the same bed.
Here I must confess to having had for most of my adult life various homosexual fantasies while masturbating, and Jack had played a role in some of them since he was openly gay. In fact, I had just made a teasing joke to him that very day when on the set I had just finished hanging a door on a closet in a room Jack was painting, and I quipped, “Hey Jack, look, I’m not in the closet anymore!” grinning at him.
Jack got this hurt look on his face and shot back, “Don’t tempt me, Dave. You don’t know what you’re missing.”
I had hoped Jack would have just laughed it off, but he caught me off guard and I was so embarrassed that my face turned red and I couldn’t look him in the eyes. I didn’t want Jack to think I was ‘gay-baiting’ him, so I apologized and reached out to him.
“Sorry Jack, I didn’t mean to make fun of you. I do value you as a friend, you know.“
“Don’t worry, I’m used to it.” He sighed, approaching me. “And yes, I think we can be friends, you’re not like most of the guys around here. I feel that you don’t judge me because I’m gay.” I think we sort of bonded at that moment.
And so he entered into the room with his small suitcase, and Rebecca thanked me again and left.
Jack was soaked with wet snow and said he felt chilled to the bone, so I took his jacket and told him to get in the shower and warm up, and I would have a nice glass of wine for him when he got out. Jack took both my hands and said, “Thank you so much for saving my ass, Dave. I can’t thank you enough. He looked me right in the eyes. I know this is awkward, you sharing a room with someone like me.”
Like gay, he meant.
“Not a problem, Jack. I’m happy to help. What are friends for?” Neither of us mentioned that there was only one bed. This fact hung in the atmosphere like a cloud, but I carried on, the concept of sex with Jack starting to work it’s way into my mind, until I realized that the idea was not just working but already fully developed.
“Give me your clothes. They’re soaking. I’ll hang them up to dry.” I wanted to get his clothes away from him so he would have to use a towel like me. This was another strategy to try in my now full-blown, yet strangely mostly subconscious plan to seduce Jack.
“Yeah, good idea. I’m freezing.” He headed to the bathroom.
I now took one of my Cialis pills that I had started using to augment my erections of late, bit it in half and chewed up and swallowed one half, and then ground up the other half with the base of a wine glass and dissolved it in the glass with the wine I had poured for Jack. We were both in middle age, and I knew I needed the Cialis to keep my cock hard for what I hoped would be... well, I did not know what, really, but I knew I was excited about it.
I ventured to the bathroom and knocked on the door timidly, opened it and said, “Can I get your clothes? I’ll hang them up to dry.”
What I saw next literally took my breath away. Jack was naked, bending over the tub, adjusting the faucets, and his cock was hanging down about four inches, a circumcised head, just like mine, truly a thing of beauty. Desire flooded through me. I could not look away. Jack looked over at me and he could see where my eyes were looking but didn’t flinch, he just smiled and let me stare. I gathered his clothes, and knees shaking, backed out of the doorway, my cock pushing against my towel.
Back in the room, I hung up the clothing with shaking hands and sat down in the only chair to catch my breath and try to figure things out. I opened the towel and took my fully erect member in my hand. I was hard before the Cialis could have had its effect so I knew that this was a special situation, not like my usual masturbation fantasies. This was for real and I was scared. But no way I was going to stop. I was shocked at my desire. I had not been with a man since my teenage years when I fooled around with my cousin and I really didn’t know how I should behave with an experienced homosexual. I did not want to make a fool of myself.
I checked Jack’s wine to make sure the Cialis was dissolved and took a sip of my own for courage.
When Jack emerged finally, I had calmed down a bit and immediately handed him the wine. “Looks like we’re having a toga party, eh?” I said with forced cheerfulness.
Jack laughed and said, “Yeah, this is cool. Thanks again for sharing your room. I’m feeling a lot better.”
We drank our wine and chatted about the weather, the job and the crew—Jack sitting on the bed, me on the one chair. Jack’s legs were stretched out, crossed at the ankles, and pointed at me. I found myself hoping I would be able to see up inside his towel and kept glancing at his legs. He seemed relaxed and at ease, but with a curious intensity of attention when he looked at me that made me self-conscious. I tried to pretend I also, was cool with the situation, but my face felt flushed and my hands were shaking, so finally I blurted out, "I guess we should talk about the elephant in the room.”
“Oh, you mean the one bed?” Jack blithely replied. “Don’t worry, I‘ll sleep on the floor if that makes you more comfortable.”
I panicked and too quickly said, “No, no. You can’t do that. Don’t be ridiculous . We have to share the bed. It’s only fair.”
After a pause, I blurted it out. “It’s just that I will probably be naked.”
I couldn’t believe I had just said that out loud, and in shock, I waited for Jack’s reaction.
“Well then, I should be too. I guess we should get used to it, don’t you think? There’s nothing wrong with being naked. We’re adults after all.” And just like that, Jack unwrapped his towel and tossed it aside, lying back against the headboard, in front of me, hands behind his head, as if daring me to look.
So I looked. Oh man, did I look.
Jack was shorter than me and thinner, but healthy-looking for a man in his fifties, and his cock and balls hung in a perfect triangle of pubic hair. I just stared for a moment until I realized I should do something, anything.
“Wow. You’re in much better shape than I am,” as I stood up and dropped my towel.
“Oh god, Dave, don’t worry, I’ve always considered you as something of a hunk.” Jack reassured me, flattered me actually.
My cock started to rise and I approached Jack almost automatically, as if my cock were leading me. Jack slid forward to the edge of the bed and stood up. I closed with him and jumped when our cocks touched, then suddenly our arms went around each other and Jack raised his face to be kissed. I had never kissed a man before, but his open mouth felt every bit as good as any woman I had known. His tongue made my cock throb to fully erect, and I ground my pelvis against him, feeling his shaft rolling against my leg. Another man pressing his naked flesh against me just felt so good, and all my fear and anxiety disappeared. I knew what to do next.
My desire took me over, and I gently pushed Jack towards the bed, forcing him to sit down. I fell to my knees between his legs and buried my face in his warm, soft genitals. His balls were loose, each testicle moving freely in his scrotum as I moved my nose back and forth, then I slid my face upward, my tongue caressing his sack and gliding higher onto his shaft until I reached his helmet. I licked the perimeter of the soft tissue, then took the cock into my mouth. I went as far down as I could without gagging, then tightened my lips and sucked as hard as I could on the way up. Then back down and up, several times.
As I took my own member in my right hand, I suddenly realized that this was it! I was sucking another man’s cock, my fantasy at last! I knew that I would go all the way; I would make Jack cum in my mouth and swallow his semen.
I was so turned on that I was afraid I might come too soon before tasting his juice, but Jack had other ideas and lifted me off him and said, “Let’s try something really gay, ok? Lie down on your back.”
He dashed to his suitcase and came back with a bottle, squeezed out some liquid rubbed it on my cock, then between his ass cheeks. He straddled me and rubbed the end of my cock against his anus. I could feel my cock entering Jack’s ass, then he sat back and I was deep inside the tightest, warmest hole a cock could ever ask for. It felt incredible!
Then Jack started moving up and down! I couldn’t believe it! “Oh! God! Jack, oh god!” were the sounds coming out of me. This must be what gay sex was all about and I was powerless to do anything but go with it. I knew I would ejaculate very soon, so I said, “I want you to come first, Jack. I want to suck you off while I am still this horny. Then I want to cum in your ass, if that’s alright.”
“Sounds good. Boy, I’ve got you hot, eh? I always knew you had some gay in you.”
I couldn’t disagree. Jack climbed off me and sat back against the headboard, spreading his legs and said, “I never expected to get a blow job from you, Dave, of all people. But go ahead, I am so ready.”
I climbed between his legs, took his balls in my left hand and the base of his shaft in my right and filled my mouth with male cock meat. I was in intense lust, grinding my cock against bed. The Cialis had kicked in by now and I suddenly felt that I didn’t want this raging desire to ever end. So I asked Jack to lie flat on his back and I straddled his face in sixty-nine position and asked him to lightly caress my scrotum and stroke my cock while I sucked him. I rocked my pelvis to simulate thrusting and help him with his stroking and to feel his fingertips sliding along my swinging ball sack. I hoped we could both come together, like had happened with my cousin forty years ago when I was a teenager. I had been fantasizing about this all that time, now it was real.
Meanwhile, my mouth was devouring his shaft, pulling hard on the upstroke, swirling my tongue around his frenulum and then taking him deep, feeling his head bump on the roof of my mouth. I wanted to make him cum so bad!
I was moaning and humming on his cock, hoping he could feel the vibrations. I measured how I was doing by Jack’s breathing and his vocalizing. It was getting deeper and louder, he was starting to thrust his hips and I knew my dream fantasy of sucking off another man was about to be fulfilled. I just bathed myself in this ‘wanting’. Jack stopped moving, stopped breathing, went silent, and I stopped too, and just held his cock in my mouth, knowing that this was it, here it comes!
And did it! Jack’s torso heaved, he almost shouted, and I felt a pulse in his shaft, then a stream of liquid hitting the back of my tongue and the unique taste and smell of warm sperm. Then another pulse and more cum pooling on my tongue, and I pulled back a bit to swirl the cum with my tongue to prepare to swallow, and then yet another gush of sex juice splashed out. I played the cum around my mouth, savouring the sensation, then easily swallowed most of it. I kept Jack in my mouth until he quieted down, then withdrew to gaze at this wonderful pleasure organ and swallowed the last bit. Then I squeezed out the last drop from his slit and licked it up greedily.
“Mmmmm, that was good!” I sat up and my balls brushed over Jack’s forehead and hair, an electric sensation, reminding me that I needed to cum. “Can I fuck you again, Jack? I don’t want to rush you.”
Jack laughed and said, "Don't worry, you certainly have earned it. Sit back and I will sit in your lap.“ I sat with my back to the headboard and Jack straddled my lap then moved up till his still swollen cock pressed against my abdomen. He took me in his hand and, leaning forward until our faces were touching, pressed my cock between his ass cheeks, found the spot and lowered himself onto my now throbbing pole. I involuntarily started thrusting into him, causing his softening member to flop against my stomach.
“Ohh, Dave, this is unbelievable. I can’t believe we’re doing this.“ I wasn’t listening. My orgasm was rising up from the depths of my body, carrying me with it and depositing me on a peak I had never experienced. I buried my face in Jack’s neck and roared as my cum shot into him, again and again.
“Aaahh, I can feel your shooting in me. Ohh, my god," gasped Jack. He was still in tune with what the two of us were engaged in. We were both on an amazing high. As our breathing quieted, we both felt amazed at the experience. We remained still, bathed in each other’s sweat and pheromones.
“I can still taste your cum in my mouth,” was all I could think of to say. Jack lifted his leg off my lap, causing a blob of my cum from his anus to drip on my thigh.
“I haven't tasted yours yet.” He scooped up a glob on his finger and popped it into his mouth.
“Jesus, Jack, that was just in your ass!”
“Don’t worry, Dave, I keep my ass super clean.” Then he said something that freaked me out. “You can taste it when you’re ready.”
I was speechless.
We climbed under the blankets.
I lay there thinking about the new world I had just entered. Images of eating my cum out of Jock’s asshole, or his cock entering my ass, and other until now unthinkable thoughts flitted through my mind. Although disgusting to the usual me, I wasn’t reacting to these things in the same way, and I wondered what waking up in the morning with a naked man in my bed would be like. The Cialis would last for thirty-six hours. As we spooned under the covers, I guessed I would just have to see what happens next.