Tom, Ryan and 1st time with Oliver

Tom, Ryan, Then 1st Time Oliver

This is part of an ongoing story over multiple Categories with common characters.

Ever suck a cock? For me, there's nothing so calming as the first time I slip a hard cock into my mouth. Not the very first time; I mean every time I take a cock into my mouth. As I wrap my mouth around it and slide down, I take a deep breath, breathe out and I'm relaxed. I can feel the calmness come over me and then I get into it. Up and down...you know the routine.

Anyway, I have a steady number of cocks to suck but you know, are there ever enough? That's why I'm still online, checking out what and who's out there. I live about 60 miles from the closest town so that makes it really good. I can meet guys over there and not have them meet my buddies over here. Sure, I don't get out there that much, maybe once or twice a month if I'm not too busy, but when I do I set it up really well.

I go across the river to one of the cheap casino hotels and usually book a couple of nights. That way I can get with more than one cock, usually three or four. Not always been that way of course, but now it works out that way as I've been doing it for a while and my guys enjoy it. So do I.

Online. That's how I met Oliver. He had contacted me first. I post my stuff on the sites and let them contact me. Same thing with women; works out well as you know if they're interested because they contact you. Oliver and I emailed back and forth, shot the breeze and I could tell he was interested but hadn't done anything yet. I remembered when I hadn't sucked a cock and would check out the websites and wonder. I gave him my phone and he texted me some. That led to talking on the phone and that is where we are now.

Had he been with a man? Not really. We had talked about it on the phone and he had said he had been with another guy and they had jacked off together over porn.

"How that'd work out for you Oliver?" I asked.

"It was hot man," Olive replied. "Haven't cum that hard in a long time. How about you? Ever been with a dude?"

"Oh yeah" I said. "Everything."

"Everything?"

"Yep, suck cock, been sucked, fuck an ass, been ass fucked. All good," I had decided Oliver was fun to talk to, but I wanted to step it up if I could.

"You still there man?" I asked.

"Oh yeah," he replied. "Just thinking about what you said."

"You okay? I mean I didn't mean to upset you," I said.

"No, no, you didn't. I mean we met online on a man to man, site, so well, you know."

"I remember when I first got started," I said. "I learned back then to take it slow. All the guys I've been with; we all took our time. I mean, I sucked a couple of guys off before they ever sucked me. Some I sucked, and they never sucked me."

"What? Really? You were good with that?"

"Oh, hell yeah Olivier. I love sucking cock," I replied. "Give me the chance and I'd suck yours...if you wanted. Or just jack off with you. You wouldn't even have to suck me off...unless you want to."

He got quiet. I wasn't sure if I had chased him off or if he was figuring out what to do next.

"You'd jack off with me?"

"Dude, I'll do whatever you want me to do, whenever you want me to do it."

We talked some more, and he said he'd get back to me. Yeah right, I figured not, so was surprised when he did three days later. He wanted to get together, I asked him what was best for him. He told me he had Wednesday and Thursday off, either day would work. I told him I'd be in town Wednesday afternoon and we could get together. He agreed.

I got online and booked a room for Wednesday and Thursday night. Like I said, I had a couple of "friends" up there so I was sure I would be using the room. 😊

************

I checked in around 230 Wednesday. While doing it I saw a guy looking at me with a quizzical look on his face. He looked familiar but... I smiled, he waved back. After I finished checking in, I went up to him.

"Ryan?" I asked.

"Tom?" he replied.

It came back to me. I had met him a while ago at the bookstore. A one off thing through a Gloryhole. It was Ryan.

"I remember you," I said.

"Me too. Bookstore, right?" he replied with a smile.

I nodded.

"What brings you to town?" he asked.

I smiled. "I like to get away, do some gambling and blow off some steam."

He laughed. "Blow off some steam. I like that. I was just leaving myself. Been here a couple of days and it's time I get going."

I nodded and said "Well, I just got here and was on my way to my room."

He flashed me a smile and asked, "You know, I have an hour or so before I really have to head back. Any chance of..."

"Hell yes," I replied. "Let's go."

We walked to the elevator and were in my room a few minutes later. I tossed my bag on the floor, turned around and said with a smile "Want your cock sucked?"

"After I suck yours, c'mon," he replied and headed to the bedroom.

That was unexpected. I mean I had sucked him off at the bookstore, then he left. I followed him into the bedroom, and we began to take our clothes off. I looked at his naked body, fuck, hot and hard, his dick like mine. He grabbed me by the arm and sat me on the edge of the bed. Spreading my legs apart he looked me in the eyes and said, "I been thinking about this since the bookstore." Down he went.

Ryan grabbed my hard, throbbing cock with one hand and bent forward. He rubbed the head of it across his closed lips, along his cheeks, and then dropped down to the bottom of my cock. Once there he placed his tongue on it, then slowly licked his way up to the head. Oh man, this was crazy good. Ryan was young, well-built and a handsome guy; and he was sucking my cock. Oh geez.

Once to the top he took the head of my cock into his mouth and started to swirl his tongue around the head. Slow, wet, he swirled while rubbing my balls. After a bit, his hand went up to his mouth, he wet it and slid it under his mouth, both wrapped tightly on my cock. As I watched him go down on me, I began to rub and pinch my hard nipples. Up and down, stopping halfway to swallow; Ryan was good at what he was doing, and I loved it. Down he went, sliding his hand away as he dropped lower, taking most of my hard cock into his hot mouth. Swallowing as he maxed out, he squeezed my balls then headed back up.

I was aching. My balls throbbed, my cock ached, and he continued to slowly go up my cock then down. Up then down, up then down, he picked up speed and settled into a routine. After a heaven filled five or so minutes, I wanted to cum, hell I would whether I wanted to or not; he was good.

"Oh dude," I said. "Fuck, I'm getting close to cumming."

He went back up and said quickly, "Cum in my mouth." Down back onto my cock he went, this time sucking a bit faster, squeezing my balls.

"Of fuck!" I yelled as I shot my load. Hot, long spurts of cum went into Ryan's hot mouth. He sped up the more I came until I began to dry fire. I pushed him away and took a deep breath. "Fuck that was good. Real good."

Ryan looked up at me and said "Yes it was. You able to suck me?"

I nodded. "Oh yeah, I'll suck it."

"Can I fuck your ass too?" he asked.

Whoa! That was unexpected. Hadn't expected that at all.

"Sure can," I replied. Well fuck, I mean I did hope I'd get my ass fucked sometime while I was up here. WTF, I went to my bag, pulled out some lube, condoms, and my dildo. Ryan smiled.

He walked over to the condoms and opened one. I grabbed his arm and said, "Not until I've sucked that sweet cock of yours."

He grinned and sat back on the edge of the bed. "Come get it Tom."

I dropped to my knees and grabbed his cock. I wet my hand and slowly went up and down, wetting it again when it went dry. "So, you want to fuck my ass?"

Ryan looked at me and smiled. "Yeah, I do."

I replied, "Good, cuz you'll like it. And by the size of this nice cock, so will I." Down I went.

Man, like I said earlier, I love taking a cock into my mouth and it felt great. I got the head wet, pulled it out and rubbed it against my face, looking into Ryan's eyes as I did so. I hoped he would appreciate it and the sharp intake of breath proved me right. I opened my mouth and slid my hot tongue onto his cock. I felt the bit of pre-cum as I ran my hand up his cock. I licked it then swirled my tongue around his cock head. Slowly, three times to the left, three times to the right, then I took it into my mouth.

Down I went, one, two, three inches down until I was halfway there. Did I mention he had a nice long cock. Once there I swallowed, and it was my turn to grab his balls. He took in a breath and further down I went. I couldn't get the whole cock into my mouth, but it wasn't from a lack of trying.

Up and down I went, up and down, him moaning as I did. After a bit he slid away, pushing me back. I smiled, handed him the condom and lube, and asked him "What way do you want me?"

Slipping on the condom and lubing up his cock he replied, "However you like it."

"I want to watch you when you cum," I said. I grabbed a pillow, laid on the bed, pillow under my ass and legs off the edge. He slid a lubed finger into my ass. I took it easily. He slid it in and out a couple of times then grabbing his hard cock he rubbed it against my asshole. Slowly he slid forward, first the head then more into my ass. I pushed back, I wanted it all...he gave all of it to me, his balls banging my ass.

It was thick, hard and I loved it as he slid back out slowly, not all the way out of course. He reached down, grabbed me by the ankles, spread me wide and slid in deep.

"Play with your cock Tom," he said. I reached down to my now half hard cock with a wet hand and started to stroke it. I wasn't sure how hard I could get it, but I didn't give a shit; he was fucking my ass and fucking it hard!

Bam! Bam! Bam! His long thick cock pounded my ass. I stroked my cock, it was hard now, and said "That's it Ryan, fuck me! Fuck me!"

He groaned and continued to pound me He was getting close, he was breathing faster, I couldn't wait... and I didn't have to.

"Oh shit! Oh shit!" he yelled. "I'm cumming Tom!"

I wished I could have felt his hot cum in my ass, but he was wearing a condom. Bang! Bang! Bang! Three deep pokes then he pulled out, sat back on a chair. I followed him, pulled off his condom and took his half hard cock into my mouth. He reached down to my shoulders but as I sucked it, his hot cum being swallowed, he didn't push. After I had sucked all the cum off his cock I pulled back.

"Next time we do this Ryan, you don't have to wear a condom. I'd like to feel your cum in me."

Ryan laughed and said "Deal. I wish I hadn't worn one, but I didn't want to take anything for granted."

"All good," I replied. "You have to leave tonight?"

"Yeah," he said as he nodded. "Have to head back to Vegas for my next appointment." He started to get up and get dressed.

Hmm, next appointment. Not really sure what he did for a living, tech I think, from the card he had given me. I got dressed too and we shot the shit.

Ryan went to the door and turned back to say goodbye. "We do this again?"

"Heck yeah, just call me."

"Now that I know you'll travel I'll let you know when I get back here or down there."

"Oh yeah, one more thing," I said with a smile. "Everything's on the table Ryan. Everything, just ask."

His eyes flashed, he smiled and went out the door.

************

Ding!

It was a text from Oliver. "Still on for 7?"

"Yep." I gave him my hotel info.

"Sweet. Can't wait." He replied.

"Me too." And I couldn't.

Oliver arrived at 7, right on time. I opened the door, and he came in.

"Want something to drink?" I asked. "Beer, wine, pop, even some whiskey."

Oliver smiled and replied "Wow, that's a lot of stuff. Sure, beer?"

"You got it," I replied. I pulled out one from the small refer, opened it, and handed it to him. "Still up for porn?"

"Yep," he replied.

"And jacking off with me?"

"Hell yeah," he said with a smile.

I had hooked my laptop up to the TV for a big picture and told him to pick a site he knew and liked. He did. I was familiar with it, course I had been using the "gay" and "tranny" sections. Maybe...

We sat back on the couch a bit away from each other. I made sure we were in arm's reach just in case. He started to pull his pants down, I took off my pants and shirt. He looked at me while I was undressing, not sure what he was thinking.

Anyway, he picked a nice vid, two guys spit roasting a girl, reminded me of Cyndee, Crystal, Debbie, hell, and a couple more of them. He wet his hand and grabbed his nice and hard cock.

It was a pretty sweet cock. Not huge, but thick and hard. I wished I could get it in my mouth, but first things first. I wet my hand and started to stroke. I'd look at him and he'd look at me.

"Ever spit roast a girl?" I asked.

"Uh, nope, can't say that I have," he replied. "You?"

I laughed. "Oh yeah, quite a few times."

"Really?"

"Yep, in fact if you're ever interested let me know. I have a couple of lovely ladies that love to do it."

"A couple?" he asked with a questioning look as he stroked. "You know more than one?"

I had to laugh again. "Yeah, three where I live and a couple in Vegas. Well, actually the ones in Vegas are trannies."

Oliver gave me a look that was a combination of disbelief, disgust, and interest. He kept stroking. "You've had sex with a tranny?"

"Yep, three or so" I replied as I slowly stroked my cock. "Trannies are hot. Looks like lady, tits, soft body, and a hard cock. Think about it, who knows how to suck cocks better than guys and trannies. Don't get me wrong. I have had my cock sucked by lots of girls, but..."

Oliver asked, "But trannies don't have pussies." He took his hand away from his cock.

"Yeah, but they have tight asses, and they love getting them filled." I looked at his cock then at him. "Did I offend you or something?"

He shook his head. "No, not at all. Was getting close, didn't want to cum yet."

We continued to play for a bit.

"Ever seen a guy suck a cock?" I asked. I waited a bit then continued, "I mean on porn?"

He shook his head and said that he hadn't. "Or trannies either."

"Well you are younger than me," I said. I figured he was at least 10 or so years younger. "Want to see some?"

"Sure," he said.

Cool, I went to my bookmarks and started with one of my favorite man on man vids. He started to stroke his cock again.

"So, you've had your cock sucked by a guy too, right?"

"Yes. I have. Been sucked and suck too. Ass fuck, trannies, hell, just about everything."

"How did that get started?" Oliver asked. I told him about Dave, the first time when he told me he wanted to suck my cock. Then I went on to tell him all of the rest, the spit roasting, being spit roasted, everything. He kept stroking, then would stop. I did the same.

"I can't imagine doing that stuff," he said.

"I know what you're talking about. I was the same way," I said and grabbed my cock again. He looked down at it while I continued. "It's all about trying things one at a time and only when you feel comfortable with it."

"Really? I guess that makes sense," he said.

"For example, I have a guy that I suck his cock and he hasn't sucked mine. I'm good with it and he's good with it. When he's ready, he can suck my cock. If he never does, it's all good."

Oliver gave me a quizzical look and asked, "You're good with that?"

"Hell, yeah, because most of the guys I've been with have started out like that and now...well everything's on the table with them."

"Everything?"

"Yep, I take them as far as they want to go."

"Even those that let you suck their cock but don't suck yours?" he asked.

"Man, I do not care. I love sucking their cocks, their hot, cum filled cocks and can swallow them," I replied smiling. "Unless you've sucked a cock, you don't know how good it feels."

He looked at me, got quiet and we sat and stroked a bit more. Then I said....

"I want to suck your cock."

Oliver looked at me, inhaled deeply and said "Fuck it. Suck me Tom."

I smiled, dropped to my knees, and said, "And you don't have to suck mine." I licked the head of his cock with my tongue, looked him in the eyes and said, "Unless you want to." Down I went; I stopped, smiled, and continued. "And one more thing, don't touch my head."

I grabbed his cock with my hand, my other on his balls, my tongue began a slow swirl around the head of his cock. Oliver took in a deep breath and moaned ever so slightly. Around the head to the left I went, slow and wet. Three times for taste then to the right. I caressed his balls as I took the hard, thick head of his cock into my mouth. Just at the start then deep down, way down. I felt that sense of calm and relaxation then began to come back up.

Oliver wasn't saying anything, but I think he was enjoying it and I could feel his thighs hardening, his waist slightly leaning up to my mouth. Halfway up I stopped and swallowed, once, twice his hot cock tasting great. Up I went to the top, to the head, keeping it inside, paused, then back down.

I wasn't in a rush and I like sucking it slow but of course, after a bit I wanted to close the deal. So, I squeezed his balls tighter, not too tight, and started to pick up speed.

Oliver breathed in slowly, deeply, his hands reaching down to my shoulders. Was he going to push me away? No one ever has so I thought not. Faster I went, now at a good speed, he started to moan, his cock wet, hot and I'm sure aching.

He exploded! He didn't start to cum, I mean he exploded. His first spurt was huge, memorable indeed and his second, third and fourth were large too. He started to scream "Fuck! Fuck!" and bounce up and down. I kept sucking, he started to dry fire, I didn't want to ever stop, but he pushed me away. As I moved back, he kept breathing hard and deep.

"You okay?" I asked.

He looked at me, nodded his head and replied "That was fucking great. I mean great."

I smiled. "Thanks, I loved it. Man, you came hard and a lot of it. Tastes great. I can do that any time you want."

He looked at me and said, "I want to suck your cock Tom."

I smiled and replied "I want you to, but not today. You see, once you cum, if someone shoots their load into your mouth it's hard to swallow it until you've done it quite a bit. I want your first time to be really good, so you want do it again."

He shook his head and said, "You have it all figured out Tom."

"I kind of do," I said. "You hungry?'

"Uh sure," he said.

"Cool, let's go downstairs, they have a great buffet here," I replied. "My treat." I started to get dressed and he said...

"You suck me off then buy me dinner? Can't get better than that," and he started to pull up his pants.

I looked him in the eyes, smiled, and said "Believe me, it can get better than that. Whenever you want it to. No worries, no rush."

He grinned, "I'll have to see, but I bet you're right."

We went down and had dinner. I'd love to say he came back up stairs and sucked my cock, but like I told him, everything in its time.