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//NOTE: There will be a few more chapters to come!//
It was Friday night in Chicago and I decided to go downtown to Boystown—the gay district in Lake View East. I wanted to get my boyfriend a new dildo and look at some other toys, and it was the perfect time to do it, considering my 19-year-old sister had gone back to my parents’ house for the weekend. Boystown was only a twenty minute walk from my apartment, but that night I was feeling lazy so I took my car. I had thought about going to the popular Spin Nightclub on North Halsted Street that night, but my best friend and party buddy, Ryan, was spending the night in with his new guy.
When I got to Boystown I parked my car in front of Cupid’s Treasures, a sex shop I frequently went to. I went inside the store and greeted the cashier, a young Brazilian guy named Gary who I saw all the time.
“No clubbing tonight, James?” he teased.
“Naw, I’m all alone tonight. Ryan has a new boyfriend, so he stayed home,” I told him.
“Well, say hi to him for me,” Gary smiled.
“I will do that,” I said. Gary went back to whatever he was doing behind the counter, and I proceeded to walk to the back of the store where I knew the dildos were kept. When I got to the back, I stopped dead in my tracks as I laid my eyes upon the sexiest boy I had ever seen.
This boy looked about 18-years-old and was around 5’7″. He wore black skinny-jeans; a tight, white v-neck shirt; and cute glasses with black, square frames. His eyes were this gorgeous ocean-blue colour and he had long eyelashes and a lovely head of blond hair which was styled into a ‘faux hawk’. His lips were full, pink and beautiful… I just could not stop staring at him. He was the most perfect thing.
The boy was gazing up at the shelf of dildos with this cute, clueless expression on his face.
“Are you looking for something specific, babe?” I asked.
The boy turned to look at me and seemed somewhat embarrassed.
“Oh, um… I’m just browsing, really,” he said, smiling slightly as a soft, pink blush crept onto his cheeks.
Wow, even his voice is amazing… I thought, smiling back at him.
“Well, just in case you need a suggestion, I would recommend this one…” I took a packaged dildo off the shelf and showed it to the boy. “It’s a bit more slender, if that’s what you’re looking for, and it’s good quality silicone for a good price,” I explained.
“Wow, thank you…this actually looks perfect,” the boy said.
“No problem,” I said, handing it to him.
“Hey, um…this might be a stupid question, but what’s the difference between a dildo and a butt plug?” he asked, turning considerably red in the face. I couldn’t help but smile at his innocence.
“It’s not a stupid question. A butt plug is meant to stay in for a longer period of time to loosen up the hole, whereas dildos are meant for play,” I explained.
“Wow, that makes so much more sense now. Thanks,” the boy said.
“You’re welcome,” I smiled. He seemed so clueless about gay sex—it was cute. “Do you have any more questions?” I asked.
“Actually, I have a ton of questions, but I don’t wanna bother you with them all…” he said.
“It’s not a problem at all. I’ll answer any questions you have. Why don’t we take a walk?” I suggested.
“Um, sure…” the boy nodded hesitantly.
“Only if you want to, of course,” I added, seeing his hesitation. I didn’t want to make him feel like I was pressuring him. Plus, it was 10 o’ clock at night and he might not have felt comfortable walking with a total stranger at that hour.
“I do want to,” he assured me with a smile.
“Okay, let’s go,” I said. I wasn’t completely convinced that he was comfortable going with me, but at that point I was too turned on by him to pass up his company.
The boy paid for his dildo and then we left the store together.
“My name’s James, by the way,” I said as we walked side-by-side down North Halsted Street.
“That’s a great name.”
“Thanks,” he smiled.
“So, what are you doing down here alone so late?” I asked.
Tyler shrugged, “I just wanted to live. I’ve never been to Boystown and I just wanted to see what it’s like,” he told me.
I nodded, “How do you like it down here?”
“I think it’s great. I wanna get a place down here someday,” he said.
“Yeah, it’s a beautiful place to live,” I said.
“Do you live down here?” Tyler asked.
“About a twenty-minute walk away,” I replied.
“Wow, that’s pretty sweet,” he said.
I spotted a Starbucks about a block away. “Why don’t we sit down in Starbucks and I can answer those questions for you,” I suggested.
Tyler agreed and we walked to Starbucks. I held the door open for him when we got there and admired his perfect ass as he walked ahead of me and sat down at a table.
“Do you want anything?” I asked, nodding over to the counter where the baristas were serving drinks.
Tyler shook his head, “No, thanks,” he smiled.
God, his lips looked so good. I couldn’t help but imagine what it would be like to kiss casino oyna him… Tyler noticed my staring and blushed, looking down at the table for a second.
“Sorry,” I chuckled, “you just have the cutest smile.”
Tyler smiled even wider and even cuter, “You’re such a flirt,” he said.
“You like it, don’t you?” I teased.
Tyler blushed and laughed shyly. “Yeah, I kinda do…” he said, biting his lower lip.
I felt my cock twitch in my jeans as I watched Tyler. God, I was so into him.
“Have you ever flirted with an older guy?” I asked.
“No, this is a first, actually,” he replied, adjusting his glasses.
I nodded. “Anyway, you must have a lot of questions. Lay ’em on me, boy,” I smiled.
“This is so embarrassing…” Tyler laughed. I laughed with him—he was adorable.
“Don’t be embarrassed, I probably had the same questions when I was your age,” I assured him.
“Okay, well…what does anal sex feel like for the person who’s, like…on the bottom?” he asked.
“It’s pretty much this intense, amazing feeling deep inside you that you never want to end,” I explained, looking straight into his eyes.
“Wow, that sounds incredible…” Tyler smiled, looking right back at me. “Okay, next question. After a guy fucks you, does your asshole stay like…open for a while?” he asked.
“Depends on how thick the guy’s cock is and how long he’s inside you for. But, generally, yes your asshole will stretch to an extent, but it will return to its regular size in time,” I replied.
“Oh, okay,” he nodded. “What’s rimming?” he asked.
“That’s when someone licks your asshole,” I told him.
“Oh, that sounds gross!” Tyler laughed, wrinkling his nose.
“Trust me: If anyone ever gives you a rimjob, you won’t think it’s gross. It feels absolutely amazing,” I said.
Tyler raised an eyebrow and smirked. “Would you give me a rimjob?” he asked.
“I totally would if you wanted me to,” I smirked back. My heart rate sped up. I couldn’t believe this gorgeous boy had just asked me to pleasure his ass. I was ecstatic.
“Maybe some other time,” he smiled.
“You’re such a tease,” I chuckled. Tyler laughed and I watched him lick his lips subconsciously.
I wanted him so bad.
“I honestly don’t think I’ve ever been as horny as I am right now,” Tyler admitted.
I raised an eyebrow, surprised at his blatant comment. “I’m pretty horny myself…” I said.
“My parents think I’m at a friend’s house for the night,” he told me.
Okay, he was definitely insinuating something now. Tyler smiled and I smiled back and reached across the table, taking his hands in mine. “Well it’s getting late, maybe we can go to my place and I can answer some more of your questions…” I suggested.
“Only if you can drive me home in the morning,” he said.
“Of course, babe,” I said.
“Okay, let’s go,” Tyler said with excitement in his voice.
We both got up and walked back to my car, in front of Cupid’s Treasures. Once we got into the car, Tyler said something.
“What?” I replied, looking over at him.
“I said: Can you kiss me?” he asked, looking into my eyes.
I paused for a moment, pushing thoughts about Chase out of my mind. Then, without answering, I hungrily leaned in and pressed my lips against Tyler’s. It felt so good to taste him and I kissed and sucked his lips urgently, placing my hand on the back of his head, pulling him closer to me. After tasting Tyler’s sweet lips for a minute or two, I pulled away, panting from arousal.
“I want you so bad,” I breathed out, staring at him.
Tyler was breathing heavily and I looked down to see the growing bulge of his erection in his pants.
“I’m so horny,” he smiled.
“I can tell,” I smirked, staring at his bulging crotch.
“I wanna show it to you,” he said, rubbing his hand slowly over his erection. I grew more and more aroused as I watched him rub his cock. Suddenly, he took my hand and put it on his crotch. I could feel the outline of his hard cock through his jeans and it made me crazy. I started rubbing and gently squeezing his teenage cock, all the while looking into his eyes as he whimpered quietly.
“You’re so fucking sexy,” I said, kissing him.
“Ohh God, James…ohh yeah…” he moaned against my lips. By now my cock was so hard in my pants and I needed to get off.
“Are you gonna cum?” I asked.
“Yeah… I don’t wanna cum in my underwear though…” Tyler said.
I stopped rubbing his crotch at those words.
“Let’s head to my place to finish up then,” I said, starting the car.
“Yeah,” Tyler agreed.
“So, how old are you, by the way?” I asked as I drove.
“I’m eighteen,” Tyler replied.
I glanced over at him. “Really?” I asked, wanting to be sure.
“Yeah, really,” he replied.
“How old are you?” Tyler asked.
“Twenty-eight,” I replied.
“Wow…I thought you were like twenty-three…” he said.
“Too old for you?” I teased.
“No, I’m just surprised…” he said.
We got to my building soon and went up to my apartment. canlı casino I took Tyler’s hand and led him into my bedroom before shutting the door behind us. He stood awkwardly in the middle of the room while I emptied my pockets of my wallet, keys, cigarettes and lighter, and put them on my bedside table.
“Take your clothes off, babe,” I smiled gently at him.
Tyler smiled and blushed as he pulled his v-neck shirt off, exposing his gorgeous torso, complete with a budding 6-pack. I didn’t think my dick could get any harder than it already was, but when I saw Tyler’s naked body I felt it stiffen even more.
“Shit, you’ve got such a sexy body,” I said as he pulled down his jeans. I smiled when I laid eyes on his tight, hot-pink and black underwear, which showed the outline of his hard cock clearly. He was such a twink and I loved it.
“Do you want me to take my underwear off, too?” he asked.
“Not yet, just lie down,” I replied as I undressed myself.
“What are we gonna do?” Tyler asked, propping himself up against one of my pillows as he watched me undress.
I stripped down to my boxers and lay down next to him on the bed. “We’re gonna suck each other’s dicks. How does that sound?” I said, rubbing my palm gently over his nipples.
“Good,” he replied, leaning in to kiss me.
I slowly rubbed his dick through his underwear as we made out and was pleased to feel a wet spot where his pre-cum had soaked through the material.
“James…” Tyler breathed out.
“Hmm?” I replied.
“I don’t think I’m gonna last too long when you start sucking me…I’m already on the edge after what we did in the car…” he said.
“It’s okay, baby. Don’t worry about that,” I said before continuing to kiss him. “Take your underwear off now,” I said after a while of making out.
“Okay,” he said. Tyler lifted his bum so he could slide his underwear all the way down his hairless legs. I could not take my eyes off of his dick. It was perfect: It stood straight up, about 6 inches long, and thick with a nice pink head that was covered with clear pre-cum.
“Fuck…” I said under my breath as I took in the sight of this boy’s perfect cock. I wrapped my hand around the shaft and flicked my tongue over his swollen dick-head as he leaked fluid profusely.
“Oh shit, that’s so good… Oh my God…” Tyler moaned as he tightly grabbed fistfuls of the blanket.
I took the whole thing into my mouth after that and began bobbing my head up and down on his cock while he continued to moan and curse uncontrollably.
“I’m gonna come…” he warned me.
I sucked on him harder until I felt his muscles tighten and his warm liquid fill my mouth. I swallowed Tyler’s big load and then sat up next to him.
“Told you it was gonna be quick,” he smirked.
I chuckled, “Well, I guess it’s your turn now, hey?” I said.
“Yeah,” Tyler nodded.
I pulled my boxers off and Tyler’s eyes widened when he saw my 9-inch cock.
“Oh my God, you’re so big…” he grinned.
“Go ahead, babe,” I smiled.
Tyler lay down between my legs and began sucking the tip of my dick.
“Yeah, that’s it…” I moaned, placing my hand on the back of his head.
Tyler took more of my cock in his mouth and started sucking up and down my shaft, scraping it with his teeth every now and them.
“No teeth, please,” I said.
Tyler lifted off of my cock with a “pop” sound. “Sorry, it’s only my second time,” he smiled innocently before going back to giving me head.
“Geez, you’re so goddamn cute,” I said.
Tyler couldn’t fit my entire cock down his throat, so he wrapped his hand around the base and stroked it while he sucked on the upper part.
“Mmm, that’s good, baby,” I told him as he pleasured my cock.
To be honest, it was a pretty sloppy blowjob, but it was only his second time, so it didn’t really matter to me. I was just happy to have such a cute teenaged boy sucking my dick.
“I’m gonna cum in your mouth, Tyler…” I moaned as I got close. “Do you want my cum in your mouth? Do you?” I asked, breathing hard.
“Mmmhmm…” Tyler moaned, his lips still tight around my cock.
I felt my lower stomach tighten and a wave of intense pleasure go through me and I knew I was about to come.
“Swallow my load, babe, swallow it…” I moaned, grabbing a handful of Tyler’s hair, forcing him to swallow my cum.
As I squirted ropes of cum into Tyler’s mouth, he swallowed most of it, but some leaked out of the corners of his mouth, running down his chin.
“Mmm, that was good, James,” Tyler smiled, licking his lips as he looked up at me with those gorgeous blue eyes. I was in heaven, looking down at the beautiful boy between my legs, licking my cum off his lips.
“Come here, baby…come sit on me,” I said, patting my thighs.
Tyler sat up and sat facing me, straddling my legs. He put his arms over my shoulders and I kissed him, licking my own cum off his chin and bringing it back to his mouth with my tongue so he could taste it, too.
“You’re amazing,” he panted, licking his lips and looking kaçak casino straight into my eyes.
“No, you are,” I grinned. I held my middle finger up to his lips. “Suck on it,” I told him.
Tyler took my finger into his mouth and sucked on it gently, swirling his tongue around it.
“Get lots of spit on it,” I said.
Tyler did as I said and when I felt like my finger was wet enough, I took it out of his mouth and brought it down to his asshole, pushing at his tight entrance.
“James, no…” Tyler protested.
“Shh…just relax, babe,” I told him.
I got the tip of my finger inside him and he let out a whimper.
“It hurts…” he said.
I kissed him to try and shut him up, but he just pulled away and kept telling me to stop, so I did.
“You’re so tight,” I said, running my hands up and down his back.
“I’m sorry, I’m just not used to sticking things up there,” he smiled.
“After you try out your new dildo you’ll be more comfortable with things up there,” I said.
“Yeah,” he nodded. Tyler leaned in and kissed my lips gently—he was such an amazing kisser.
I kissed him back and we made out for a long time, just holding each other and getting even hornier.
“I wanna taste your cum again…” Tyler said against my lips.
“I’ll make sure of that,” I told him.
He laughed and pressed his forehead against mine. “I’m so glad I met you,” he smiled.
“I’m glad I met you, too,” I said back before pressing my lips against his once again.
A second later, I felt Tyler’s fingers wrap around my cock and start rubbing it. I smirked and looked over at him—he had this coy smile on his face and he was blushing like mad.
“You really want my cum badly, don’t you?” I said.
“Yeah,” he nodded, still smiling.
I leaned over to kiss Tyler hard on the lips. My cock was getting so hard beneath his touch and I was loving every minute of it, feeling his inexperienced hand squeezing and rubbing my cock. I pulled my lips away from his, breathing hard, and he whimpered longingly.
“Keep kissing me,” he begged, still rubbing my rock-hard cock. I felt my eyes glaze over with lust when I heard him beg for my lips on his, and I couldn’t get over how sexy and amazing he was.
“You bet I’ll keep kissing you. Get on your knees in front of me,” I told him.
Tyler did as I said and got on his hands and knees in front of me, with his ass in my face.
“Are you gonna rim me?” he asked.
I didn’t answer—I just spread his ass cheeks apart with my hands and let my tongue caress his tight, pink asshole. Tyler gasped and I felt his asshole contract and then release under my tongue. God, his ass was amazing. I slowly licked his hole all over, kissing and sucking it every now and then. He tasted so fresh and I loved it. I took in his boyish smell with every sweep of my tongue and I felt like I was in heaven.
“Ohh fuck, James… Shit, that’s good… I can’t believe how good it feels…” Tyler was moaning.
I took a break from working his hole and started kissing his ass cheeks, giving him bright red hickeys all over.
“My dick is leaking so much,” he said as I marked his ass.
“That’s good babe…that’s really good,” I said.
I reached between his legs and felt the tip of his cock. Sure enough, it was completely covered in sticky pre-cum. Once again, I spread Tyler’s ass open with my hands and went at his hole. I licked up and down his crack a few times before working my tongue right into his tight cherry.
“Ohh, wow, that’s amazing…” Tyler moaned as I moved my tongue in and out of him.
I spread his ass wider and tried to get more of my tongue inside him, but soon my jaw got too tired so I stopped. I kissed his asshole a few more times and then told him to lie down on his back.
Tyler lay down with his head at the foot of the bed and I started sucking his cock as I lay next to him. It wasn’t long before I felt his hand on the back of my head and his hips started to buck up, pushing his cock deeper down my throat.
“I’m gonna come…” he panted.
I felt his body go rigid and then his warm boy-cum poured into my mouth. I swallowed it all and then Tyler pretty much tackled me onto my back, got on top of me, and started kissing me.
“You are so fucking amazing,” he said
breathlessly as we made out.
I bit his bottom lip and he let out a sexy moan.
“Suck my cock,” I ordered him.
Tyler got off of me and I got up onto my knees, my cock pointing straight at him. He took it into his mouth eagerly, lapping up all the pre-cum from the head before sucking the whole thing. I took his head in my hands and held it steady as I began fucking his mouth. He choked a little when my cock hit the back of his throat the first time, but I kept going and eventually his throat opened up for me and I pushed my entire 9 inches into his mouth easily.
“Ohh, yeah, that’s it babe. Just keep going like that,” I told him as I continued to thrust my cock down his willing throat.
Tyler started moaning as he deep-throated my cock, which felt so good—I could feel the vibrations his throat made on my cock. I could tell he loved that I was fucking his throat; he was looking up at me with those innocent eyes that screamed, “Use me.”
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