To New Experiences

A strict top, fresh out of a messy two-year relationship, finds his day at the beach spiraling into a whirlwind of first-time experiences—thanks to his insatiable best friends and the elusive hottie from the quick mart.

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  • 19 Min Read

I was enjoying my day at the beach, the sun warm on my skin as I stretched out on the sand. My white Speedo clung to me, hugging my bulbous ass and somehow making it look even bigger. It wasn’t my favorite swimsuit—I always worried it gave the wrong idea to the sexually charged gays who flocked to this beach. And trust me, especially during school breaks, the place was full of them.  

As a top, I hadn’t exactly planned to wear this. But it was either the Speedo or my baggy shorts, and in the end, I’d chosen the lesser of two evils. At least the Speedo kept me cool, even if it came with unwanted attention.  

Slap! Slap! I felt the sting as I turned over, ready to tussle.  

“Hey, hey, calm down,it’s me,” Sam said, lifting his arms up, signaling he did not want to fight me.  

“Sam, you asshole,” I said as I play-punched him on the shoulder.  

Sam was a versatile top. He loved it any way he could get it, and honestly, why not? He was a mixed 28-year-old man who’d never worked out yet had a very defined body. His muscles were toned, and being 6’3” didn’t hurt either. His best feature by far was his green eyes,they were quite mesmerizing, shining against his golden-brown skin. Not quite black, not white, and not brown, his features were unique. If you asked him, he’d say his best feature was his thick, bulbous 7-inch cock.  

“How can you blame Sam? I mean, that looks delish,” Dave interrupted, giving my ass a hard squeeze. I slapped his hand away and helped them unpack our beach supplies.  

“What took so long?” I asked, pretending to be annoyed at them being late. Honestly, I wasn’t. I enjoyed my alone time, and after my breakup with John a few months ago, I was ready to get out there and just play the field a little.  

“Well, let me tell you,” Sam said excitedly. “Dave here had been after this 22-year-old cashier at the Quick Mart. What’s his name?” Sam mocked Dave with a smile as he pulled off his shorts, unleashing his chiseled body. I had to admit, his clean-shaven nuts and cock looked great, and he wasn’t shy about it. When it came to sexual partners, he loved younger guys with big asses,I guess that’s why he always paid so much attention to mine.  

“His name is Jack,” Dave replied with a smirk of annoyance.  

“Well, our boy Dave here couldn’t get the hot 22-year-old cashier and power bottom to give up his assets,” Sam emphasized as he took his balls and cock in his hands and gave them a good shake for us.  

To Dave’s dismay, Sam and I started laughing. “Sure, just take comfort in my pain,” Dave laughed with us as he started to undress.  

Now, Dave was something to look at too. He was a redheaded ex-high school/college wrestling champ. Everything about him was bulky and strong. He’d just turned 30 and was a top like the rest of us. He did bottom every so often,we’d poke fun at his adventures bottoming, and he’d say, “I’m a top, but things happen.” He was 6 feet tall and muscular, his pale white skin framing the red hair on his head just right. But unlike Sam, Dave had a full beard and a semi-hairy body that made him look like a catalog model for leather jocks… which he loved.  

“As I recall, you didn’t have any luck either, golden boy,” Dave fired back as he took his bright white balls and cock and shook them in our direction, sliding his black Speedo over his trimmed red bush.  

“What?! Both of you struck out?” I said, laughing at both of them. Soon, we were tussling on the beach towels we’d just set up on the sand.  

They loved taking their shots at who would grab my ass first, but it was all in play, and they knew I was a top.  

We settled down and lay there, soaking up the sun. We got the usual stares and glares from the guys, as we usually did, and talked about work and the coworkers we hated.  

“Well, shit, look at that,” Sam pointed to the edge of the beach. “That’s our boy toy and tease, Jack!”  

We sat up casually, but I could see what drove these two to pursue this kid. Jack was athletic with a strong frame, filling out his navy Speedos nicely front and back. He had a strong jaw and golden locks like a typical blond boy next door,effortlessly sexy and strong.  

“Well, damn, he’s fucking hot,” I said as Sam and Dave looked at each other and smirked.  

“I talked to him on our way here, but other than small talk, he’s a tough cookie,definitely not interested…. Power bottoms are choosy,” Dave said, smiling at Sam.  

“Yeah, that he is. Not like us at all. I know what I want,” Sam said, eyeing my ass. I, of course, pretended not to notice. I was used to it now,they couldn’t help themselves, which is why I rarely wore Speedos around them.  

“Well, let’s toast to that.” Dave passed around some wine-filled glasses, and we all took a sip.  

“To well-laid plans,” Dave said, smiling and clinking his glass with Sam’s.  

“To new beginnings and new experiences,” Sam followed, clicking his glass with mine. “Time to open yourself up to the possibilities, my friend.”  

They both knew how messy and toxic my last relationship was. “Yes, I’m ready for new,” I said, and they hugged me,then, as expected, rubbed my ass.  

I pulled away, and we all laughed again.  

“You know, Dean, talking about new beginnings,” Sam pondered, “I think you have a better shot than us old guys.” He looked out toward Jack.  

“Nah, if both of you struck out, I’m sure that kid is looking for someone his own age,” I said, eyeing the mouthwatering piece of ass frolicking with his friends at the beach.  

“No, really, I think you do. Shit, one of us should have him,” Sam said, glancing at Dave.  

“Both of us should have him,” Dave replied, giving my ass a good squeeze.  

I shifted the conversation. “How long ago did you meet him, Sam?” I asked.  

“I tried getting that boy four months ago, and after that didn’t work out, I told Dave all about him,” Sam said, walking over and rubbing Dave’s shoulders as he applied sunscreen. Dave lay flat on his beach towel.  

“How did it go for you?” I asked Dave.  

“Not good. He has his own interests in sex and knows what he wants. It bugged me, but after several dates, nothing came of it. He was just a tease,” Dave replied. “I did learn a few things about myself and what I’m willing to do for a guy,” he said, smiling.  

I noticed Sam now sitting in a mounting position over Dave’s ass as Sam lathered Dave’s back. Sam loved pushing his luck, but I knew better,Sam and Dave had grown as friends, and this was nothing.  

“But was it worth it in the end?” Sam said, pulling Dave’s red hair, forcing Dave’s head back.  

“Yes, it was worth it. Fucking amazing,” Dave paused.  

“There you go, Dean. We won’t hear anything of it. You’ll walk into that Quick Mart on Tuesday, make small talk, and see if this guy is your new start, new experiences,” Sam said as he brought out more wine, and we toasted several more times.  

The day trip to the beach felt short. We flirted and got a few numbers, but honestly, I didn’t feel ready for anything at the moment. Still, I did feel good flirting again,it made me feel wanted.  

Why not? I thought. I was 26 years old, in excellent shape. I worked out three times a week and watched my diet like a hawk. I had a well-toned, sculpted body. My 8-inch dick was nothing to laugh at,I had the ability to cum at least twice before going soft for a few minutes before I was ready again for round three. My face was framed by a strong, muscular jaw, and my brown eyes were piercing. My lower lip was round and full, and my partners over the years loved biting on it as we made out. My hair was black and cut short. I was semi-hairy but shaved everything off from my chest down, leaving only a trail from my belly button to my very trimmed pubic area.  

The day came to its end, and we’d had a blast. We joked, laughed, and just enjoyed ourselves between flirting and playing “who would you rather” with the unsuspecting public at the beach.  

We headed to our cars and promised to meet on Tuesday at the local bar down the street from the Quick Mart.  

“We’ll get you buzzed and confident so we can make our dreams come true,” Sam laughed as he play-punched Dave in the shoulder. We changed out of our Speedos and into loose shorts.  

“Fine, I’ll be there,” I said, trying not to sound too interested.  

“Excellent. We’ll get things ready. Be confident,you’ve got this, and you’ll enjoy it,” Dave said, taking my hand and shaking it gently. “Don’t be afraid of a new experience, of new beginnings,” he said in a comforting tone.  

We said our goodbyes and headed back to the real world.  

Monday was a heavy and emotional day. My ex sent his sister, Jackie, to pick up the last of his things. She and I had always been close in the two years I dated her brother, but now, there was an invisible wall between us. We spoke sparingly, and only when she was ready to leave did she say:  

“I’m really sorry things didn’t work out.” She looked at me with kind eyes. “I hope somewhere down the line, we can reconnect as friends.”  

I nodded and smiled as she walked down the stairs to her car, now filled with her brother’s stuff. She waved and then left.  

I’m glad she didn’t ask what went wrong,I doubt her brother told her the truth. He wanted an open relationship, to bring people home, to use dildos, cages, and bondage,and I wouldn’t budge. I should have tried, I told myself. I should have tried.  

I looked into the empty apartment. Damn, most of the things that made this place feel like a home were his. The apartment felt empty, but the smell of his favorite cologne still lingered faintly in the air.  I told myself that soon I would buy my own things and turn this place back to my place.

I showered and got my things ready for work and a second set of clothes for the bar later,a nice pair of 501 jeans, a white T-shirt, and black boots. Classic bar attire.  

Tuesday was just boring. Work kept me busy, but I always felt like Tuesdays were filler days that made no sense. As I got in my car to leave the office, I got a message from Dave:  

“Enjoy these from my vault.” In it were the pictures of Jack,two looked like profile pictures; the next one was Jack sitting on a dildo while wearing a harness top. My cock stirred.  

The next message had three more pictures in it. The first was Jack facing away from the camera; he was on his knees between a big guy with muscular legs and torso. It was only when I looked closely that I recognized it was Dave.  

Jack was sucking Dave’s cock, and you could clearly see the white skin and fiery pubes. Jack had his hand wrapped tightly around Dave’s hard cock. Damn, I thought! I was getting hard in my office parking lot. I adjusted again.  

The next picture was a little unexpected. It was Dave on his back on a bed with his arms tied and stretched to the bed frame. His eyes were closed, his mouth half open,clearly, he was enjoying himself. His legs were spread open like a split, and above him was Jack, holding on to his legs, his mouth gorging on Dave’s cock.  

Next to Dave’s sides were other things I hadn’t looked at yet: a blindfold, a small butt plug, handcuffs, and a cock cage.  

Damn, that was fucking hot. I can’t believe Dave never fucked Jack,clearly, Jack was having a great time too.  

Shit, I thought, I was hard now. I clicked on the third and final pic of the message. It was Dave shirtless, looking at the camera. His chiseled body was impressive; he was holding his red, glossy cock in his hand, as if teasing me with it. I had seen Dave naked before,I’d seen him hard,but I had never seen him like this.  

There was another message. It just said, “Sorry, just realized I got picture-happy and sent one of mine.”  

I replied quickly: “No problem, man. I can’t wait to ask this guy out,he’s fucking hot.”  

The next text from Dave was: “OK, see you at seven, man.”  

I rushed home, shaved, trimmed, and showered before starting a bath to relax and get rid of the Tuesday blues. I pulled out my phone and took a look at the pictures again. Damn, Jack was fucking hot. I zoomed in on his pretty mouth, opened wide, taking Dave into it. Dave’s balls were hanging, framed by the red of his pubic hair. I looked at the last picture he sent me, the one where Dave is sitting, cock in hand, smirking confidently at the camera. Now that was the picture. Damn, my friend was a stud, and I was proud of him.  

I met Sam and Dave; they were already seated at the bar. They liked coming here more than I did. I mean, I had a partner for two years; I had lost touch with the place.

A new bartender leaned in,he was jacked and strong, you could just tell. He reached out his hand and shook mine. “Nice to finally meet you, Dean. I’ve heard all about you,” he said, looking me up and down. It was normal,all guys size each other up. Why we do it, I don’t really know.  

“All lies,” I said jokingly, as I placed my card on the counter. “No need for that,your friends here,” he said, smirking. “Got you covered.”  

“Yeah, we got you covered,” Sam said, as he ordered some “liquid courage” for me.  

Whatever it was, it was heavy and strong. “Now, now,all of it,” Dave insisted, patting my head. “New experiences and new beginnings.” Our guy at the bar winked at me with a smile and was off to attend to other customers.  

After three of these drinks, I was confident and ready. Sam steadied me up, and Dave fixed my shirt and adjusted my belt, while giving my ass a nice squeeze. I just shook my head and slapped his hand away. We all laughed.  

“Dean, you are ready. Now walk out to that Quick Mart and ask that kid out,don’t take no for an answer,” Sam said, his mouth practically salivating.  

“Good luck, man,” the bartender said from behind the counter. “Name’s James, by the way. Nice meeting you.” He looked me up and down again.  

“Nice to meet you too, James,” I said, as Dave walked me out toward the street.  

“That kid is fucking hot,” Dave whispered in my ear. “What did you think of the pictures I sent you?”  

“Well, Jack is fucking hot. He looked like he was having a great time,and a mouthful,” I said, smiling. Dave pulled me in again and whispered, “Man, having my cock in his mouth felt so good. Most guys love when I push it deep. You’re gonna love this guy.” His lips pressed against my ear.  Sending my body mixed sensations.

“Now it’s all you, buddy,” he said, as I kept walking toward the Quick Mart. I was a little uneven, but I made it in and grabbed some water. Jack was stocking shelves before noticing me.  

“I’ll be right with you,” he said. His voice was deep,I had expected a more feminine quality to it, but nevertheless, he was hot, and it showed, even in his uniform. Let’s just say it hugged all the right places.  

“Did you find everything okay?” he asked. I took a moment to admire this fine piece of meat. “Sir?”  

I snapped back. “Oh, yes,sorry. I was drinking with my buddies and really needed some water. Can you throw in some mints, please?”  

Jack smiled and turned, giving me a great view of that muscular ass as he reached for the mints behind him. “Tuesday is such a bore. I’m glad you’re out grabbing a drink with friends. I haven’t seen you around here,” he said, his gaze wandering down to my shirt and pants.  

I looked away and adjusted to give him a better view. “Yeah, it’s boring and nothing to do. Well, nothing exciting,” I said with a smile.  

“There’s always exciting things to do,you just need to find them,” he said jokingly, peering deep into my eyes.  

“Excellent,” I said, smiling back. “Maybe you can show me where to find it,” I replied, stretching a little to make sure he could see my sculpted body.  

He gave me back my change and, with a naughty look, said, “I close at 8:30. Come back, and I’ll show you.” Damn, I thought, this was going to be a great Tuesday after all.  

I made my way back to the bar, only to find Dave and Sam had already left.   

“They had more shots than I could count, some game they were playing about whether you could come back empty-handed or not. They took it a little too far, if you ask me,” the bartender said, smiling.  

“They did pay for 2 more drinks for you.” He brought them out, and I chugged them down. They were strong, but I was nervous. After 2 years, I was gonna be with someone else, and I was feeling self-conscious.  

“Here you go,this one’s on the house,” he said. It was a shot, but it smelled deadly. “Thank you,” I half-said when he interrupted me, putting his hand over mine to keep the drink on the counter.  

“Take this just before you head out. It’ll take all your worries away,” he said, smiling but stern.  

I nodded, and just as I walked out, I took it. I stepped onto the street just as Jack got off his phone. “Yeah, if you can’t do it today, send it to me in Cash App,it’s the same thing,” he said before closing his phone and smiling at me.  

“Is everything okay?” I asked.  

“Yeah, just some friend who owes me gas money,” he replied, looking me up and down. “You ready?” he said, taking my arm as we walked a few blocks to his place.  

As soon as we walked in, he closed the door and forced himself onto me, pushing me down onto the couch and kissing me deeply. I responded in kind, using my superior strength to flip him over me.  

“Yeah,” he whispered as I kissed his neck and pulled his hair gently, tilting his head back as I bit softly into his ear.  

“Oooohhhhh,” he purred.  

“By the way, I’m Dean,” I said, pulling him close.  

“I’m Jack,” he replied.  

As I tugged at his shirt, he pulled away.  

“What’s wrong?” I asked. I was so horny.  

“I like things my way. So if tonight’s gonna happen… I don’t like anything serious until I feel safe with someone. Are you okay with that?” he said in a naughty tone.  

I was drunk,very drunk. I only nodded.  

“Good. Let’s go to the bedroom.”  

I walked in and recognized it from Dave’s pictures. There were a few things I hadn’t seen: a huge closet door, several skateboards, and even a bike rack.  

“Take it off,” he said, pointing to my clothes. I got naked really fast, my 8-inch dick flopping out.  

“Big boy,” he said with a smile. He got me into bed and added, “I like to be in control at first,at least till I feel I can trust you.”  

He pulled my arm, and I felt pads come over my wrists as he secured them, then moved to my legs and did the same. I was stretched wide,it was almost uncomfortable.  

But I was so drunk. I don’t think I’d ever been this drunk in my life; the world was blurry and slow.  

“Here, this’ll help,” he said, placing a tight blindfold over my eyes. “Let me get a pillow for my knees,” he added as I heard him open the bedroom door and then another door I thought. 

Next, I felt his glorious mouth on my dick. “Oooooo, yessss,” I purred as his warm lips gave me the most amazing blowjob I’d ever had. His free hands pinched my nipples,it hurt a little,but I moaned and thrust all 8 inches into his mouth.  

This kid was a pro; he was driving me crazy. I could hear the gargles as I pushed the head of my cock past his mouth and into his warm throat.  

Yes, fuck,I said, “This kid didn’t let up.” He pulled his hands down and began yanking my balls hard, his thick fingers torturing my sack with every tug. But I was too far in to care; my only goal was to cum.  

I felt him pull off, and I was sweating as he unlocked me then Quickly flipped me, he tied my hands behind my back. In a blur of quick movements I was face down, face buried in a pillow, my ass up in the air. Before I could complain, I felt the warm, moist swirl of Jack’s rough tongue licking my hole.  

I let out a deep grunt as I felt the kid go to work on my ass. I normally don’t allow anyone near my hole, but I was too drunk to complain.  

Jack's face buried between my muscular cheeks. He took turns spanking and biting my ass before diving deep into my crevice with his tongue. I could feel the warmth of his hands holding on to my balls, the other holding my cock tight, the stubble of his hair on his face as he moved his head between my cheeks…it was glorious.  

It was driving me mad,it felt so good. My cock was jumping and slapping my inner thigh as my legs shook involuntarily, then to my surprise Jack’s tongue slipped into my hole.  

“Oooooo shiiiit,” I whimpered as he began to tongue-fuck my ass. I love doing this to my own partners,it quickly opens them up for fucking,but I’d never experienced it myself.  

I was moaning and grunting as I gasped for air. This new sensation was amazing.

Jack’s arms reached under me, pinching my tits again. Every time he pushed his tongue in deep, he pinched me hard, and I’d squeeze my hole tightly around his invading tongue.  

I was leaking precum like crazy now, moaning as my ass was slapped hard. I was being used, and I was lost in the moment.  

Jack was amazing. As I started to break a sweat, he flipped me onto my back again, spread my legs wide, and tied them in place. Jack began to power-fuck his throat onto my cock, taking all 8 inches, gargling, then going back for more. I shook in place, knowing I couldn’t hold on much longer.  

“I’m getting close!” I yelled, but Jack wasn’t done yet. He yanked my balls hard to keep me from cumming.  

“Fuck, shit,yeah, ooooogh!” It was no use; I was gonna come.  

As I was about to announce it, Jack stuck two fingers deep into my mouth. He used his free hand to hold and jack me as he sucked feverishly. I gargled from the penetration of his fingers as I came.  

My whole body shook as I shot my first load into his mouth. The kid didn’t stop. He continued as I now feverishly accepted his fat fingers in my mouth and sucked on them hard for a second imagining it was Dave's hard cock in my mouth, before shaking that image away as The second shot made me yell out in joy.  

“Fuck!” I tried to yell, but the two fingers became three, and I shot my final load, my body shaking and writhing in a mix of pain and pleasure.  

I gasped as Jack pulled his fingers out and finally released my still hard cock only for it to slap hard on my abs. As I rushed to catch my breath Jack lifted my legs and  slipped his tongue back into my hole making moan loudly. After a few more thrusts, spanks and bites.

He silently walked out of the room, I heard some talking and then the shower start before he came back in the room. 

“Sorry,” he said, "I was grabbing a warm towel for you and talking to my supervisor. He wants me early tomorrow for my shift.

“ yeah no problem” I replied, I then heard some clicking as I was released, and he took the blindfold off.  I looked down to see my sweaty body, jack had really given me a workout. He had utterly worshiped my ass and to my surprise I had enjoyed it.

He was in a robe, his face nice and red but otherwise he looked fresh and ready for another round.

“Off to the shower” he said “I would play some more but I have an early shift” and as he picked up around the room I walked into the shower. 

I showered and felt great. This really was a new beginning—new experiences. I walked out and started drying myself, then curiosity got the better of me. I opened his bathroom sink cabinet and found three small butt plugs, two cock cages, and several popper bottles. *Well, damn*, I thought. This kid clearly had more experience with this kind of thing than I did.  

Two years in a relationship had either held me back or, more likely, I’d been unwilling to try new things. I’d never played with butt plugs, cock cages, or even poppers—always assuming they were for people who couldn’t get off like "normal" people.  

I got dressed, noticing my underwear were missing, but I paid no mind. On my way out, I said, “I hope we can do this again.” Jack smiled, bit his lip, and walked over to me. He came in close and whispered,  

“Come look for me at the Quick Mart on Friday. Maybe we can get together again for some fun.”  

“I’ll be there,” I said with a smile. 

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