Hey there. My name is Samuel. But my friends call me Sam. I’m 36 years old and my job is to go to small businesses that are upgrading their technology infrastructure, or, if they’re old-fashioned, setting up their computer technology for the first time. This is my story, and it’s a helluva story so get ready for it.
On my latest business trip, I found myself in a medium-sized mid-western city where I was setting up a complex customer tracking system. It was my first day and, by the end of it, I was exhausted. All the management people in the business were NOT computer literate, so I had to spend a lot of time and energy teaching them what was going to happen while setting up their new system.
By the end of the day, I was exhausted. But I was also horny as hell. So, when I got back to my hotel I showered and relaxed for awhile, then checked out the local gay paper to see what kind of action was available in this city. Usually I don’t find much “entertainment” in these smaller places, so I wasn’t very hopeful. But, as luck would have it, I saw an ad for a gay bar just a few blocks from where I was staying.
So, I got dressed – nothing too fancy, just some casual jeans and shirt. Unfortunately, I had forgotten to pack my sneakers, so I had to wear the loafers I had brought.
I walked down to the bar. It was busy for a weeknight, and the music was loud and perfect for dancing up a storm. After a couple of drinks, I had loosened up enough to risk going out on the dance floor.
I was hot and sweaty, but it felt good to let loose a bit and enjoy the scenery. Most of the guys there were around my age or older and, I thought, just as horny as I was. But I wasn’t really interested in them. I like younger guys.
After getting a beer, a young guy came over to my seat. In this state the drinking age was still eighteen, so it didn’t surprise me that he was probably that age or perhaps just a little older.
“Hi,” he said. “May I join you?” I nodded, already mesmerized by his youthful look. He sat down across from me. “I’m Jonathan,” he said. “Samuel,” I said. “But my friends call me Sam.”
He smiled. “Does that mean I can call you Sam?” he said, a twinkle in his eye. “Only if you want to be my new friend,” I responded with a smile.
This kid was drop dead gorgeous. Tall, slender, an impish smile. Nicely styled blonde hair. “Okay, Sam. I guess we’re friends now!” he smiled.
“So,” I said. “This is a new city for me. Luckily, I found this bar so I could spend the evening enjoying myself.”
“Yeah,” Jonathan replied. “It’s kinda what they call a ‘one-horse’ town. Small, not much to do except for the bar scene.”
I already knew that I wanted him. I wanted to be in bed with him. I wanted to cuddle up close. I wanted, frankly, to fuck the hell out of him. “So, I take it you’ve lived here for a while?”
“Yeah. Grew up here. Just graduated from high school and turned eighteen, so I thought I’d enjoy my new-found freedom by hanging out in this bar.”
“Cool,” I replied. “Do you work here?”
“Nah, I just hang out here. My work is in a small electronic repair shop a few blocks away.”
“Sounds interesting,” I said.
“Well, I guess so. Actually, it’s kinda boring most of the time.”
“Are you planning on hanging around here, going to college, or what?”
“I’m not the scholarly type,” he smiled. “I had enough ‘academics’ in high school.”
“Interesting,” I smiled. “Sometimes it’s just nice to have completed school and then moving on. Tell me more about you, stud,” I said with a broad grin.
“I wouldn’t say I’m very studly,” he said shyly.
“Oh, I don’t think so.”
“Yeah. After graduating it’s been a little boring, actually. I miss the ‘action’ I had while in school.”
My ear perked up. “Action?” I asked, trying to be both sincere and interested. “Tell me about this.”
“Well, while in school I realized I was gay. I know it’s a small city, but it isn’t very homophobic. Had a lot of good friends while I was in school.”
“What do you mean, ‘good.’”
“Hanging around and stuff. Most of the guys in my class were athletes. Typical stuff. Butch. Girlfriends. Horny.”
I chuckled. “Yeah, I remember that part of high school. Did you spend time with these guys? Were they accepting of you?”
“Actually, yes. They always asked me a lot of questions about ‘What’s it like being gay?’ You know, curious.”
I nodded knowingly.
“Can I tell you something, Sam?” Jonathan asked.
“Sure, anything.”
“In school I became the go-to person for guys who wanted to talk about their girlfriends. It was kinda weird, though. Most of these jock-types were surprisingly unable to hook up with girls. This bothered them…a lot…so they always seemed to want to talk about it. I guess because they knew about my sexuality, they didn’t view me as a threat. You know, try to ‘steal’ their girls.”
“Ah yes,” I signed. “The old ‘you’re gay so you’re safe, do ya wanna listen to my story’ thing.”
“You’ve got it,” Jonathan smiled. What a smile he had! I felt myself growing hard and stared at him wondering where this was going. “So, what did you want to tell me?” I asked.
“Because they weren’t getting laid, they needed someone ‘safe’ to share their sexual frustrations with. At some point many of them realized ‘Hey, Jonathan’s gay. We can’t get any sex outta our girls. Maybe….’”
“Maybe they could spill their loads into you to keep them satisfied?” I said.
“But the thing is, they didn’t want to fuck me. That would be ‘gay’ in their mind.”
“And…?”
“They wanted to feel what it was like, so asked me to ‘help’ them.”
“You mean they wanted you to suck their dicks?”
“No.” Jonathan leaned over the table like he didn’t want anyone to hear.”
“They wanted me to fuck them.”
“What? Really?”
“Yeah. They wanted to know what it felt like, so they could do a better job with the girls who spread their legs for them.”
“Wow!” I said, genuinely surprised. “That’s…” I hesitated “…unusual.”
“I was down for the dick-sucking part,” he said. “But the fucking part…that was a surprise.”
“I bet it was!” I exclaimed, now more curious than anything. Why was he telling me this? What was he expecting?
“So, I did. I thought, ‘hell, at least I’m getting my rocks off, even it’s inside a boy’s hole.’ I didn’t expect this, but word got around and instead of guys thinking I was just a fag I garnered respect. Before I graduated, I was servicing a coupla dozen dudes.”
“You were topping them. You were the top and they bottomed for you?”
“Yup. I mean, at least I was able to get off regularly.”
“Okay. So, what happened next?”
“I realized that I was more attracted to topping rather than bottoming. They thought if they fucked me, it was ‘gay,’ but if I fucked them, it was just more ‘normal.’”
“I must be honest, Jonathan. That’s kind of creepy.”
He chuckled, “More than creepy. Kinda like a mix of creepy and sexy. The other thing is they always wanted me to cum inside them, not pull out and shoot my load all over them.”
“Hmm,” I responded, not really knowing what else to say.
“So, do you think that’s kinda weird? I mean, young gay guys like me seem to like bottoming and older gay guys like topping. At least that’s what I assume is true.”
“Well, yeah. I suppose you’re right. I’ve never met a younger guy who preferred topping me. They always wanted me to fuck them and cum all over them. So why are you telling me all of this? Not that I mind. It’s good for guys to share their stories sometime...and sexy.”
Jonathan smiled. “When I saw you walk in here tonight, I knew at once that I wanted to have sex with you. You’re so damned handsome. So, I wanted to share my story with you to gauge your interest in me.”
“Hell, yeah,” I said, a wide smile on my face.
“I thought so,” he replied. “But I wanted to know before I propositioned you that I’m strictly a bottom. If…I mean when…we have sex tonight I will fuck you.”
My mind was racing. Not only was this unusual, since older guys like to fuck younger guys, but it was a fascinating pick-up opportunity. I wasn’t at all adverse to bottoming for this stud. It was just, you know, a different situation than I’m usually expecting.
“Okay. Let’s get out of here and get to know each other better,” I said in a “very friendly” tone.
Jonathan extended hand to me. “Come on, let’s go.”
********************
We didn’t say much to each other as we walked back to my hotel. When we got to the lobby the male clerk looked at the two of us and gave us “the look.” He knew why we were together, but he had no idea that our roles would be reversed.
We walked into my room. I locked the door and when I turned around Jonathan grabbed me. “You’re so damn hot,” he whispered in my ear. I’m gonna make your night, old man.”
Old man! I decided not to respond to what could have been an insult. After all, I wasn’t that much older…well, twice as old since he was eighteen and I was thirty-six. But I told myself, age doesn’t really matter.
Jonathon pushed me backward onto the bed, then jumped on top of me, pinning my arms down. “You want it, don’t you?” he whispered. “Fuck yeah,” I whispered back. “Get inside of me.”
We quickly stripped naked and Jonathan did his thing. He kissed me, then began using his tongue to work his way down to my cock. I was hard as a rock and looking forward to him fucking me. It had been a long time since I was fucked. Usually, I seduced a younger guy and took him home so I could fuck him. This was definitely quite different than the usual.
Jonathan spread my legs and pulled them up. He then buried his face in my crotch, licking my balls and working his way down to my hole. I thought I was lucky to have showered before going to the club.
His tongue worked its magic on me, heightening my pleasure. It wasn’t long until I was completely relaxed and ready to receive his young dick inside of me.
“You ready to get fucked, Sam?” he asked, the saliva dripping from his mouth.
“Hell yes. Get inside of me. NOW!” I commanded.
Jonathan got on his knees and pushed up between my legs. He spat on his rock-hard dick and began to gently push inside me.
“Don’t be that gentle,” I told him. “Just shove it into me.”
He complied and quickly slid in. He clearly knew what he was doing and how to do it well. Pays to have all the experience fucking guys, I thought.
He raw-dogged me, almost brutally. Clearly, he was extremely horny and anxious to plant his load. I helped him by tightening my hole around his young dick. Hey obviously like this, because he began moaning loudly, picking up the in-and-out rhythm which would lead to an amazing orgasm.
“Holy shit,” he sighed. “You’re better than Roger.”
I assumed Roger was one of the horny high school boys that wanted to experience what a girl expected.
“God, Sam,” he moaned. “You’re gonna make me cum.” And I felt his jizz begin to flow into me. He kept slamming me as he ejaculated. I thought he’d never stop but soon felt his dick softening. As it slipped out of me, he collapsed on top of me. “Jeez. That’s the best orgasm I’ve ever had.”
“Better than you had with your high school studs?” I asked, factiously.
“Better. Ten times better.”
He snuggled up to me. We had been so anxious to get it on that I hadn’t taken the time to really check out his naked body. He was lithe and supple, with small brown nipples on his hairless chest. He had shaved his pubes, which made his appearance even more young-looking, but still had enough there that I could see it was bright blond, like his hair.
I rubbed my hand up and down his chest. “God, Jonathan. You’re so gorgeous…and I’m so lucky to have met you.”
“Shit, Sam. I’m the lucky one. You’re hella sexy.”
I propped myself up on my right elbow. “Jonathan,” I said quietly, “any interested in helping me orgasm?”
“I love sucking cock,” he whispered back. “Never got much of a chance to do that with my high school friends.”
I had been gently stroking my dick, which was hard and ready to go. “Go for it, stud,” I whispered. “Make me scream.”
Jonathan slowly moved down to my crotch, intent on giving me the best blowjob he could. I could tell he was not particularly experienced as he sucked me, but then again, he hadn’t had much experience doing that. I was happy to teach him how.
It didn’t take long for me to call out “Oh yeah. I’m cumming Jonathan. I’m cumming.” Then I began shooting my load into his eager throat. Wave after wave of hot semen flowed into his willing mouth, and, his lips still surrounding my ejaculating dick, I could feel him swallowing it.
Eventually, of course, I finished the job and began to soften. Jonathan pulled himself up to me and kissed me. I could feel some of his unswallowed jizz flow into my mouth. Funny. I had never really thought of what my jizz tasted like since I always sucked my partner-for-the-evening’s cum after fucking him. “Lucky boy,” I thought, “to have been on the “other side” of our pleasure together.
********************
We slept soundly together, both entwined in each other’s arms. I woke up first, and gently pulled away from Jonathan’s naked torso. Starving, I called the front desk and ordered breakfast to be delivered. After hanging up I crawled back into bed with him. He slowly awakened and whispered “The only guy that was even close to you having sex with me was Roger. Now I now how much better sex with an older guy is.
A few minutes later there was a knock on the door. “Room service,” I heard the voice say. I had almost forgotten that I had ordered breakfast. I got up and put on a bathrobe, then opened the door. A nice-looking young man was holding a tray filled with amazing food.
“Sorry it took so long,” he said as he walked inside. As this happened it reminded me that I had another guy in bed with me. The room service boy put the tray down on the small table that was next to the bed. “Well,” I thought, “So much for keeping things secret.”
As he turned, he caught sight of Jonathan. “Jonathan?” he asked in a voice that he had not expected.
“Roger?” Jonathan replied. “I…I…well, this is a surprise,” he said sheepishly. I then remembered Jonathan telling me that Roger was once a sexual partner to him.
Roger sat down on the edge of the bed. “Man, I didn’t expect to see you here,” he said. “This is kinda awkward,” he said nervously.
Jonathan propped himself up on his elbow. The bedding had been pulled down just far enough so that you could see the top of his smooth crotch. It didn’t seem to faze him, though.
“Roger,” he said. “Good to see you, man. Oh,” he said pointing to me. “This is my friend Sam. Sam, Roger. Roger, Sam.” Roger extended his hand to me and we shook.
“N…N…Nice to meet you, Roger,” I said, somewhere between mortified and turned on. Roger was almost a twin of Jonathan except that he had brown hair. I wondered what he looked like naked.
“So,” I finally said, “you two know each other, then?”
“Yeah,” Roger replied. “We went to high school together.”
Jonathan chimed in, “And after he graduated, he got this job at the hotel.” He leapt out of bed, not realizing he was naked, and shook hands with Roger, who was trying hard not to look at Jonathan’s body.
“Nice to “see” you,” Roger said a bit hesitantly. Clearly this was an awkward moment for him.
“You too, stud,” Jonathan replied as he grabbed a slice of toast from the breakfast tray. “Sam, Roger and I were best friends. I often helped him with his ‘little problem’ when he needed it.”
“Jonathan!” Roger exclaimed. “Don’t worry, Rog. Sam knows all about it. We met each other last night at the bar and told each other everything.”
“Everything?” Roger asked, then smiled. “Everything,” Jonathan replied. He patted his hand on the bed. “Sit down Roger. Let’s talk while we have breakfast.”
Jonathan’s nonchalant demeaner relaxed Roger and the two began sharing what had happened since they had graduated. “Don’t mean to embarrass you, Rog, but Sam and I were talking last night after…” he hesitated…” after ‘doing it’.”
Roger sighed, clearly relaxing after his entrance. “Yeah,” he said a little bit embarrassed,” Jonathan and I…well…let’s just say we were really good friends. He helped me a lot.”
“I don’t mean to be too forward, Roger. If you’re uncomfortable, I understand.”
“I’m not,” he said, “at least right now.”
He and Jonathan talked a bit about their former ‘arrangement.’ As they did, Roger clearly felt more comfortable. He reached over and put his hand on Jonathan’s knee.
“I miss those days,” he said, staring at Jonathan. It was clear he was excited by Jonthan’s state of undress.
“Me, too,” Jonathan replied. “So, are you on shift all day?”
“Nah,” Roger replied. “In fact, this is my last delivery then I’m done for the day.”
“Well then,” said Jonathan. “Would you be interested in reliving the ‘good-old’ days?”
Roger chuckled. “Well…”
“Don’t worry,” Jonathan said. “Sam here is my good friend now. I’m sure he would like to learn what our ‘good-old days’ were like. And,” he looked in my direction, “perhaps we could all get to know one another more intimately?”
“Jonathan,” I said. “Don’t you think Roger might be, shall we say, a bit unwilling to do this?”
Jonathan looked at Roger. “Well, would you?” he asked.
“Hell no,” Roger replied, standing up. His erection pushed the fabric of his trousers outward. “What shall we do?”
“Here’s an idea,” Jonathan replied impishly. “We can have a three-some. I’ve always wanted to try it.”
“Sure,” Roger said, “I’d like that.”
“Sam,” Jonathan turned toward me. “Sound interesting?”
I hesitated, then said “Oh, what the hell. Let’s do this.”
Jonathan became the director of this show and said, “Good. Now, Rog let’s have Sam fuck you while I fuck him. Maybe we can all get our rocks off at the same time!”
Roger stood up and began to get undressed. “Sounds good,” he smiled as he dropped his pants and unbuttoned his shirt. In just a few seconds he was completely naked with a nice erection jutting out from his crotch. Jonathan jumped up, dropping his robe. I stood up and dropped mine.
“OK,” Jonthan said, his tone very directorial. “After we all fondle each other a bit, let’s have Roger lie on his stomach while Sam lies on top of him and I lie on top of Sam. As I remember, Roger likes getting fucked. And Sam is certainly willing. And I am hella willing.”
By this time, we were all sporting erections and ready to engage. Like Jonathan, Roger had a hairless body except he had light brown pubes, while Jonathan’s were blond and shaved. The three of us began to stroke and suck each other, all of us moaning with the pleasure that brought.
When it was clear that things were getting hotter, we assumed our positions. Roger laid face-down, sticking his perky little ass up. I climbed on top of him and slowly slid my erection into his hole (which was nicely puckered, I might add). Finally, Jonathan climbed onto me. I felt like the meat in a sandwich between two sexy pieces of bread. But it was wonderful.
I felt Jonathan slide inside of me. The feeling of my dick inside of Roger at the same time as Jonathan had his dick inside of me was one of the hottest things I had ever experienced.
To say that the moaning and groaning was filling the room would be an understatement. Each of us was enjoying the pleasure the others brought. After a few thrilling minutes I whispered in Roger’s ear, “I’m almost ready to cum. Do you want me to cum in you?”
“Yes,” he sighed. “I want your load.”
“But what about you?” I asked. “You have no one to cum in since you’re lying on your belly.”
“Don’t worry,” Roger sighed. “My cock is laying between my belly and the sheet. I’ll fuck it and cum.”
The pace increased as each of us slipped into our blissful state of sexual ecstasy. Jonathan began to cum first. “Yesssss,” he moaned as he emptied his balls into me. That triggered me and I began emptying my balls into Roger. And that triggered Roger who began to wet down the sheet underneath him.
Even though it was one of the sexiest moments I had ever had, I couldn’t help but chuckle to myself. I was being cummed in while cumming in someone who was cumming beneath me. “Holy hell,” I thought as I began to pump into Roger’s tight ass, “this is fucking amazing!”
As usually, the mechanics of ejaculation subsided and we all collapsed on each other, Jonathan’s dick inside me and my dick inside Roger. I couldn’t tell if Roger liked being “assless,” but it seemed that he did.
After a few blissful moments, we untangled our spent bodies, and all rolled over on the bed. Roger’s dick was still dripping cum so because he didn’t have the wet enjoyment of his dick in someone, I took it into my mouth and gently sucked it. It must have been super sensitive because he moaned loudly and a bit more semen spilled into my hungry mouth.
“The only dick I’ve ever had inside me was Jonathan’s,” Roger finally said. “It was something else to have your dick in me, Sam.”
“Too bad we couldn’t have video-taped this,” Jonathan grinned.
“Yeah, YouTube would make a fortune from all the hits our video would get,” I laughed.
The uncoupling completed, we all jumped in the shower then got dressed. Breakfast was, of course, cold. But our “other breakfast” was warm…and delicious.
********************
After I left the city Jonathan and I stayed connected. The more we talked, the more we felt our attraction to each other. After a few weeks I convinced him to move to my city and live with me. Eventually, Jonathan convinced Roger to join us. The three of us became a sexual team, hardly ever apart. At my urging, Jonathan decided to go to community college to increase his skills, and Roger eventually enrolled also.
Oh, and Roger finally admitted he was gay and, instead of just getting fucked, began to fuck us as well. Way to go, Rog.
Oh, and Jonathan ended up being flexible, finding out he liked getting it as much as when he gave it. Way to go, too, Jonathan.
And me? I just enjoyed being inside both boys at both ends at all times. Way to go, me.
The end. Perhaps.
