Tom Helps Oliver's 1st BJ and 3 Way

Tom, One Time Oliver & More

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

I had met Oliver a while back online and we had gotten together out in Laughlin, at a hotel, oh, maybe a little over a month ago. He was a young guy and had wanted to explore the guy on guy thing. Yeah, most guys have that question come up when they are young but only a few act on it. Well Oliver did, halfway. I had sucked him off and he said he had wanted to suck me too, but I told him not that night. I figured he'd go home and think he had had fun, or pretend it never happened.

Anyway, I hadn't heard back from him and that wasn't a surprise. I had been online meeting guys and while some worked out, lots of them I just sucked off once and never heard back. Don't get me wrong, I love sucking someone off. Anyway, I always let them decide if they want to get back to me. No pressure on them, especially when they are first timers.

So, when I got an email from Oliver, I was happy to hear for him.

Tom this is Oliver. We met in Laughlin a while ago and I thought we had hit it off pretty well. Sorry I haven't gotten back sooner but work and other things happened. I was wondering if we could meet again. Thanks, Oliver.

I sent him an email.

Hi Oliver, happy to hear back from you. Text me or call me when you have time, and we can make plans. Take care, Tom.

Later that day I got a text from him.

Ding!

Oliver: Tom, it's Oliver. This a good time?

Me: Sure is. Want to get together? What works best for you?

Him: Yes. This week any good for you? I'm free any night this week.

Me: Okay. That'll work. Need or want anything special?

No reply then...

Him: Not really. Last time was great. Maybe we can do something else too?

Me: Sounds good. I'll book a room.

Him: No, let me know what day and I'll book a room. You got it the last time. 😊

Me: Sound great. Take care.

Him: You too.

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

I was guessing Oliver might want to suck my cock this time. Maybe something more, I didn't know. But it would be good to have something in reserve in case he wanted to try other things.

Lori would be great but that might scare him off. Another guy, a three way. He could watch someone fuck my ass then maybe...okay so I might be wrong there, but it'd be fun to have a backup for me as well. I mean, what if he wanted me to suck him off then left? Besides, maybe I could hook up with some other guys while I was up there. Wonder if Ryan was around?

Bill would be fun to take up there, but he was still new. Aaron. I could trust him and well, he was always a good time. I texted him. He got back to me quickly.

Aaron: What's up?

Me: Have any free time to go up to Laughlin with me?

Him: Laughlin?

Me: Have a newbie.

Him: Sure. Thursday night, free all day Friday. Taking a three day weekend.

Me: I'll get back to you. Have plans tonight?

Him: Could. Would like to get my dick sucked and maybe more. Know anyone?

Me: My place at 7?

Him: Cool. Maybe a three way?

Me: I'll let you know ASAP.

Him: I'll bring some In/Out.

Me: And you'll get some. Later.

I texted Oliver and gave him the info about Thursday night. He was good with it. We'll see how much he'd be good with. Then I got on the phone, let's see who does Aaron know?

Ten minutes later I sent Aaron a text.

Me: Bring three In/Out.

Him: That sounds hot! Oh, wait, burgers. 😊

This was going to be fun.

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

7 o'clock and there was a knock at the door. Aaron always was on time and that was a good thing. I let him in, and we went to the kitchen. He unbagged the three orders of In/Out.

"Who we waiting on?" he asked.

"Frank," I replied as I took my food. Dave was my first cock, but Frank was close behind, maybe a week later. Him and Dave were my first three way, spit roast, we did it all. We didn't get together as much anymore, both of us having a lot of dicks to suck and fuck. I had to thank Frank as he hooked me up with Kelly the first time. There was a knock at the door.

I went to the front door and opened it up. Frank and Jason were there. That was a surprise!

"C'mon in," I said and headed to the kitchen. Frank and Jason followed, Aaron turned around, nodded at Frank with a grin, the extended a hand to Jason.

"I'm Aaron. Don't think I've met you before," he said. "But you look familiar."

They shook hands, and Jason replied, "I own Cup in Time coffee. Maybe you've seen me there?"

"Oh yeah, that's it," Aaron said. "I love that stuff."

"Thanks," Jason said. "I brought some food for myself, being a last minute thing."

"It's okay, right?" Frank asked.

"Jason and I go way back," I replied. "He's welcome here anytime."

Aaron said "A friend of yours is a friend of mine Frank."

The four of us sat down and shot the shit while we ate. We all knew the routine, having done this before many times, one way or the other. Grab a bite to eat, shoot the shit for about 30 minutes and after the food settled...well, everything was on the table. Frank was right on time.

"Anyone want their cock sucked or an ass to fuck?" he asked.

I laughed "Who doesn't want their cock sucked or an ass to fuck? But if you do, follow me."

I went to the bedroom and started taking off my clothes. They all followed suit as I opened the nightstand and pulled out lube and three dildos of various sizes. Aaron picked up the largest one and asked me if I had heard from Marcus.

"No, but I'll contact him and see how's he doing."

By now, Frank had dropped down between Jason's legs as he sat on the chair. I could see his head slowly moving up and down and the look on Jason's face said he was doing a good job of sucking.

"Say Aaron," Jason said. "How about you bringing your cock over here so I can suck it. Best way to get to know someone I think."

Aaron didn't hesitate and Jason reached out, grabbed the hard cock, and pulled it up against his lips. I watched the three of them going at it, my cock getting hard.

Well, Frank did ask if someone wanted an ass to fuck. I grabbed the lube, lubed up my cock and went behind him. I reached down and rubbed my wet finger on his asshole. He shifted a bit, ass more towards me and while he continued to suck Jason's cock, I rubbed, then slid my aching cock into his receptive ass. Deeper I went, slowly until I was balls deep.

"Fuck yeah," Frank said pulling his mouth away then back onto Jason's cock. I slid it back out, to the head then balls deep again.

The four of went at for a bit but I knew this wasn't the best way for all of us, so I grabbed Frank and pulled him away from Jason.

"Aaron, you'll love sucking Jason's cock," I said, and I knew he would. Aaron didn't waste any time, pulled away and dropped to his knees between Jason's legs.

"I want your cum Jason," he said. "I'll do whatever it takes as long as it takes to get some," and down he went.

I grabbed Frank and stood him up, facing the bed and pushed him on top of it. He got on his knees, bending away from me but presenting that fine ass. I was back inside it in a heartbeat.

"Fill me up Tom, fill by ass up buddy," Frank said.

Oh, I will I thought, I will. I started to bang him balls deep, slow, stopping every few inches while he clamped down on my cock.

I fucked Frank; Aaron sucked Jason. It was hot. I wondered who would cum first, me or Jason but as I picked up speed, I really didn't give a fuck. Frank sure did.

"Oh man that's it., Frank said. "Fuck me deep and hard buddy. I love it when your balls bang against me."

"Fuck! Fuck! I love it too," I said. "Want some cum Frank?"

"Fuck yeah, fill...me...up!"

Bang! Bang! Bam! I grabbed Frank's ass tight as I shot my load. I pumped faster and deeper, wanting to empty my cock of all my cum.

"That's it Tom! Oh fuck, it's hot," he said. "Fuck me, fuck me!"

"Oh shit!" I heard Jason yell and knew he was cumming. I fell away from Frank and sat on the bed, exhausted having cum so hard. I looked over at Jason and Aaron, but only for a bit as Frank had lubed his cock and it was at my asshole. Inside he slid, fast and deep.

"Yes! Fuck me," I yelled.

Frank grabbed my ankles and spread my legs wide, pumping his cock into me. I reached up and began to stroke and pinch his hard nipples.

"Oh yeah, Tom," he said loudly. "You're a good fuck." He slid in and out always keeping his cock head inside me, his balls banging my ass when he went deep.

Aaron popped up on the bed, knelt next to my head and rubbed his hard cock on my mouth. I grabbed it, opened wide and took it in. Cock up the ass and one in the mouth, doesn't get better than that.

As the two of them spit roasted me I heard Jason say, "Mind if I join in?" Jason was up on the bed a hot face cloth in his hand. He wiped my cock clean, kissed it and took it into his mouth. I wasn't hard but it felt great. And knowing Jason, I'd be getting hard soon enough.

By now, Frank was close, and I wanted to feel his hot cum in me.

Bang! Bang! Bang! Fast and deep into my hungry ass he went. "Here it comes Tom, here it comes," he yelled, and it did.

It was hot and a lot. He kept pumping cum into me and I ate it up. After too short of a time, he pulled away and backed up into the chair.

Actually, I'm guessing he fell into the chair as I couldn't see anything, but I sure could feel Aaron's thick, hard, dick in my mouth. I pushed him away and said, "On your back bro'" I wanted to do him right and when he was on his back, I was ready to...

Except Jason pushed me away and said, "Nah, Tom. I want this." Jason looked down at Aaron and asked "Dildo?"

Aaron smiled and replied, "Good guess. Use the big one."

Jason's eyes flashed as he lubed up the big black dildo. "We have something in common, Aaron," he said and dropped to his knees. Aaron smiled, looking at me, as the dildo, slowly slid in. Down Jason went, first licking the head of Aaron's cock then taking the head into his mouth. I watched as Jason's head went down Aaron's cock and the dildo slid in at the same time. When Jason had as much of Aaron's cock in his wet mouth, Aaron had as much of the dildo up his ass as he could take. Jason's mouth and the dildo were in sync and from the noise Aaron was making he loved it.

"Oh shit, man" Aaron said each time Jason's mouth and the dildo bottomed out. Jason picked up speed and watching them made my cock start to harden up. Frank saw it and pulled me up so I could watch Jason sucking Aaron.

Frank dropped to his knees and took my hardening cock into this hand, rubber it against his lips and licked it with his moist tongue.

Jason was on a roll now, mouth up and down, dildo in and out. Aaron was close, close then over the top. He pumped his hips up and screamed loudly as he came and came into Jason's wanting mouth.

"Bring it me Jason, kiss me," Aaron said as he came. Jason didn't need much coaching as he slid the dildo out then wrapped his mouth onto Aaron's. They swapped cum then continued to kiss. Or at least I think that's what's happening as Frank had my attention.

"Jason," Frank asked. "Cum fuck Tom in the ass."

Frank moved me next to Aaron on the bed and slid a pillow under my ass. As he knelt on the bed across form my waist, he took my cock into his mouth. By now it was really hard and aching not cum.

Oh shit! I felt Jason rub his lubed cock on then into my asshole. Oh, fuck yeah, he was balls deep. I guess with Frank's cum already inside me it was an easy thing to do.

Jason fucked me hard and deep. Frank was sucking my cock and squeezing my balls as he did. Frank sure knew how to suck cock and he was going a great job. He started slowly and went down an inch or two then stopped, swallowed, then down again. After reaching the bottom he'd do the same coming up. I knew this wouldn't last long and it didn't. Frank started a slow steady up and down on my cock while I rubbed my nipples.

Meanwhile, Jason was fucking me at a pretty good clip. Usually, it takes longer for someone to cum a second time after cumming, but Jason was good at it. He fucked me hard and fast, knowing he wanted to cum, and I wanted him to.

Oh fuck! I was getting close to cumming. Ass filled and Frank going really fast, it didn't get much better than that. I started to cum, Jason's cock preventing my ass from clamping down like you normally do when you cum.

"Oh shit!" I yelled and pumped a large amount of cum into Frank's mouth. Okay, fuck it, it felt like a lot and probably wasn't but Frank enjoyed it. And so, did I. Finally, I pushed Frank away having dry fired.

"I have some cum for you Tom!" Jason said loudly. "Want it?"

"Hell yes!" I replied, and he began to fire his hot, thick cum into my ass. Fuck I love the feeling of hot cum up the ass! Bang! Bang! Bang! He continued until he had to push himself away, spent.

We all sat, lay, around catching our breaths. After a bit Aaron went to the kitchen and came back with beers for everyone. We talked for a bit then paired off to fuck and suck some more. Not sure who was fucking who, but I know I got two more loads of cum. One in each end. Fuck, I love my life!

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

Aaron and I got into Laughlin Thursday afternoon. Oliver had set me up with a room and I was able to get another one for Aaron down the hall in case my three way idea fell through. Rooms are cheap during the week; food is great and cheap too.

I told Oliver to meet me at the buffet around six and he was on time. I paid and we got in line.

"Thanks for dinner Tom," Oliver said as he started to load his plate.

"Hey man, no problem."

We went to a quiet part of the dining room, got drinks from the waiter, and had dinner.

"So, Olivier, I was really glad to hear back from you," I said.

"I did a lot of thinking after we got together, and I thought I'd like to take it to the next level," he said looking around to see if anyone could hear. "I really want to suck your cock." He smiled when he said it. I shook my head and smiled.

'Man, as long as you're sure. You don't owe me anything," I said between bites. "I mean I would love to make this a regular thing with you, even if only I was doing the sucking."

"See, when you say that, I know sucking must be great."

"That's up to you to decide," I said. "Worse case, you do it once and decide it's not for you. Like I said, I'm into it as long as you are."

Now it was Oliver's turn to smile. "So, you said before that everything was on the table with you."

I nodded and kept eating.

"Trannies, spit roasting...is that how they say it? Three ways," he asked.

"Oh yeah, all that and more, "I replied. "If any of that interests you let me know."

"Really?"

"Oh yeah, I've done it all and was introduced to all of it. Easy to do."

He nodded and ate some more. Then he asked, "What would you recommend first?"

I love newbies.

"Sucking cock first," I replied.

"Yeah, I'm good with that. I'll do that tonight for sure. But what next?"

"Well, fucking someone in the ass is good, but not for everyone," I said with reflection. "I'd say sucking two dicks at the same time. A three way."

Oliver thought a bit then said, "I think I might like that."

First the bait. "Really? I know you'll suck me tonight but two dicks?"

He took the bait. He looked questioning at first then nodded. "Yeah, I could do that."

Got him. "Want to?"

"Sure," he replied. "When?"

Time to real him in. "Tonight."

He got quiet then said, "Tonight?"

I nodded my head and said "Yes, tonight. With that guy over there." I pointed at Aaron who was eating at a table a bit away from us.

Oliver looked and asked, "You know him?"

"Yep, we been doing it for a couple of years now. I trust him to keep things quiet and he's really, really, good at what he does. I brought him along just in case you might be interested."

Oliver looked at Aaron, then at me, got quiet for a bit then said "You can trust me too. Let's do it."

"Mind if he joins us at the table?"

"Oh, sure, sure."

I texted Aaron and he brought his food and drink over to our table. He introduced himself and we got more food, drink and the two got along pretty well. After a half hour or so we headed up to the room.

Once we got there we sat and relaxed for a bit. I told Oliver it would be best to let the food settle before we did anything.

After a half hour I asked Oliver "You good with getting naked? If not that's fine too."

He was kind of hesitant, so I said, "Tell you what, how about if we stay here?" I started to undo my pants as did Aaron. Once our pants and underwear dropped to our ankles, we sat down on the couch. Aaron and I started to stroke each other's hard cocks.

"Your choice," I said. Oliver smiled and walked over to me. He dropped down to his knees, grabbed my cock, hesitated then stuck it in his mouth. The first time is always the worse time in my experience. Usually all they want to do is the up, down, up down as fast as they can to get you to cum. Oliver was a bit different.

He swirled the head of my cock in his mouth, pulled it out then licked the head.

"That's it," I said encouragingly. "Take your time and enjoy it."

Aaron got up and knelt next to Oliver. "Can I show you a few tricks?" he asked.

Oliver pulled off my cock and said, "That'd be great."

"Okay, I'll talked you though it," Aaron said. He grabbed my cock with one hand and my balls with the other. "See, grab the balls, not tight, loose and as you suck squeeze them like this."

And he did, onto the head of my cock he went as his other hand squeezed my balls. Down slow, squeeze, then up slow.

"Here's a trick that'll make you popular. I use my tongue to lick right under the head of a cock. This is the sweet spot. Just do it a few times, not too much then swirl your tongue around the head." Aaron licked the sweet spot nice and slow, then swirled his tongue around the head of my cock, to the left three times, then right. He pulled away and said, "Now you do it."

Oliver switched places with Aaron, cupped my balls and licked under the sweet spot, then swirled.

"There you go, that's good, Aaron said encouragingly. Now wet your hand, grab his dick, and put your hand on your lips. Good. Now as you go down take your hand down. Go down as far as you can go, moving your hand off his cock if you need to."

Oliver wet his hand, grabbed my cock, and slid down, hand on his lips. He got quite a ways down then, stopped then went back up.

"That's it. Now speed it up, that's it, up, down, nice, and slow. Squeeze his balls," Aaron continued his tutoring.

I reached own onto Oliver's shoulders then let go. Aaron noticed and said, "If you want it's okay for them to grab your shoulders while you suck them, but not your head. When you suck cock, you're in control and it's best to let them know it. Tell him."

Oliver took my cock out f his mouth and said "Shoulders is fine Tom. Not the head though." Back on to my cock he went.

He was a natural, doing really well and Aaron coaching him just made it better. He started going faster then stopped, lifted his heads off me and told Aaron.

"Sit down, I want your cock now."

Aaron did and we looked at each other. With a smile. He was learning fast and knew what he wanted. He dropped down on Aaron and started to suck, showing the teacher what the pupil had learned.

I let him suck Aaron for a good few minutes then said, "Pull you pants down Oliver, I want to show you something."

Oliver pulled away with a frown but did as he was told. Aaron stood up next to him, both cocks hard and inches from each other. I dropped to my knees between them and grabbed each in a wet hand. I looked up at Oliver, then Aaron and slipped my tongue on Oliver's sweet spot. He let out a breath.

"Did you like sucking Tom's cock Oliver?" Aaron asked.