Gay Sex

Part 5 of My Sizzling Collection of Attractive Brothers

Which brother does the twink first have sex with?

Spankmasters
Jun 1, 2024
16 min read
group sexgay haremtwinsvirgin assvirginanal sexhigh schoolMy Gay Harem of Hot Brothers Pt. 05first timeteenblowjob
My Gay Harem of Hot Brothers Pt. 05
My Gay Harem of Hot Brothers Pt. 05

Part 5 of My Sizzling Collection of Attractive Brothers

I apologize for the delay in posting. I don't like to post on holidays.

All characters are 18 years old or above.

Key to characters at the end.

--

I was sitting on Jordan's lap again. "How was your day?"

"It wasn't great," I honestly replied.

"Did you have any difficult customers at your job at Macy's?"

"No, that was fine."

"Oliver, you're usually chatty. What's going on?" He comfortingly ran his hands down my sides.

My eyes filled with tears. I didn't use to cry this much! Now that I had guys who would listen and support me, was I becoming more sensitive? Caleb told me it was better to let out my feelings instead of keeping them inside and feeling sad.

Jordan gently wiped my tears and waited patiently.

"A girl at school called me a slut."

Jordan stopped suddenly.

"And I feel like she's right."

"Oliver, don't call yourself that! You're not like that!" He tried to comfort me.

"But I'm Caleb's boyfriend at school, but I'm practically inseparable from Avery and Asher. I'm on Jordan's lap almost every day after school. I sleep in a different guy's bed every night... and... and I like it." I broke down sobbing now. "Am I a bad person?"

"No, you're the best person I know," Jordan hugged me tightly.

"Am I... promiscuous?"

"No, of course not. Sometimes attraction and feelings don't need to be difficult," Jordan continued to comfort me. "You shouldn't let someone's opinion shape you when they don't know the whole situation."

He was right. I should do what makes me happy and the guys happy. She didn't know the situation or the details.

"You never felt this way... before meeting us..." Jordan's voice sounded slightly different with that statement.

I wiped my tears and hugged him back. Crying left me feeling comfortable, but I hoped Jordan's legs hadn't fallen asleep or anything.

He kissed my forehead gently before getting up to start preparing dinner.

The next movie night, Reese showed up with just a pair of joggers on. His toned legs were completely visible, and his abdominal muscles were showcased by his thin, see-through white shirt.

No one said anything, and I couldn't take my eyes off his bulging groin.

One by one, the brothers left for bed. Jordan was the last to leave, looking like he wanted to say something to Reese. But Reese just ignored him.

Later, Reese muttered, "Fuck what Jordan said," and took off his shirt with one arm like I've seen jocks do. I didn't know what he was referring to, but he looked delectable.

I was now all alone with practically naked Reese.

The light coming from the TV shone on Reese's defined muscles, making them look even more delectable. His erect cock was clearly visible in his joggers.

"Can I suck you off?" I blurted out. I can't believe I said that!

"Have you ever given a blowjob?" He quirked an eyebrow curiously. I can't believe he's considering it!

"No, but aren't you experienced? You can teach me what you like. A blowjob is from a mouth." I hoped I sounded convincing without being too eager. I was so desperate to see him and touch him and taste him.

"Has anyone sucked you off before?"

"No, but..."

"Okay, I'll show you first, so pay attention."

What?!

He pushed me on my back and pulled my pants and underwear off at once. He pulled my shirt up, revealing most of my torso.

He completely ignored my erect penis, but just being naked in front of him caused it to harden even more.

Reese bent down and licked my nipples. He lathered them with spit. Then, he licked and sucked my nipples. I whined in pleasure.

He kissed down my chest until he stopped when he reached my hard dick. Was this the first dick he was going to suck? I jerked involuntarily.

He brought his head down and took me into his mouth. He went too deep too fast and immediately gagged. He used his hand to pull the bottom part of my dick away and focused on the upper part with his warm, wet mouth. It felt amazing! I barely held myself from blowing right away.

His hands reached up, caressing my sensitive nipples while bobbing his head up and down. His muscular, warm, and hot body between my legs... oh my...

Without warning, I came down his throat! He didn't mind, humming positive sounds while swallowing my entire load. Wow.

"It's amazing!" I gasped.

"Did you jot anything down?"

"Hmm... yeah?"

He chuckled. "I'll take that as a compliment." Reese stripped, sat on the edge of the sofa, and pushed me to my knees between his legs.

His cock was already stiff and pulsating. He must've enjoyed sucking me.

I couldn't help but stare at his stunning penis. Its slight left curve and size were perfect. His balls were brimming. I massaged them in my hand while my other stroked the length of his shaft.

"Lick me."

I glanced up at him as I gave him playful licks. He groaned. Then, I traced my tongue all over his gargantuan cock in a haphazard pattern. I relished the sense of his silky skin and feeling him contracting.

I wrapped my lips around his head, and his hips surged forward. He held my hair, forcing me down onto him. I provided him with sloppy, vehement head. I craved the heavy feeling of him on my tongue and rubbing against the sensitive insides of my mouth. I groped his balls and occasionally pulled on them like the twins had before. He appeared to appreciate that, too.

The chilly air on my erect penis as a result of him sucking me caused tremors.

Reese paused me periodically by pulling me by my hair to regain his footing when he appeared to be approaching orgasm, then resumed.

"Why are you holding me back? I want to taste your spunk." My request came across whiny.

He chuckled, holding my head firmly, and plunged his long penis deep into me. "I want - this - to - last."

My jaw ached, but I reveled in it. My left hand clung to his thigh for balance while my right continued to provide stimulation to his balls. I began to suffer from a different discomfort between my legs again. I used my right hand to snake my hand up and down my cock.

Reese halted. Before I could question his actions, he removed my shirt, leaving me completely naked, and then thrust back into my mouth.

"Stroke yourself until you release your seed again, baby."

At his words, a blazing fire ran down my body. I vigorously rubbed my penis with quick, firm movements as his massive cock slammed the back of my throat repeatedly.

Aaahhh! I adored Reese taking so much pleasure from me. I moaned around his thick cock. I recalled how great the vibrations felt when he'd hummed around my member. He increased his speed.

I came once more! My discharge on his leg elicited orgasmic reactions from him.

"Yes..." he hissed with pleasure as I sucked him through his climax and continued to lick him thoroughly afterwards. He hissed again when it became too much and pulled me up for a kiss. Our tongues intermingled.

We entwined our lips in a leisurely embrace until we hardened once more, and then he fucked my mouth, again.

It wasn't until the break of dawn when I awoke in his bed that I began to ponder what Reese was doing with me... He seemed inexperienced with gay sex but also adept at generally sexual activities. He definitely seemed to be drawn to me, but he claimed he was there to help me... Was that a ruse or was he simply unbothered with the physiological reactions of his body? Oohhh. It's so perplexing! I couldn't even inquire of one of the other brothers, as I didn't want to expose him or mislead him.

Rather than overthinking things, I ought to simply consider what else I desired to practice with him...

......

Another day after school when the other brothers were absent, I rushed to the office, thrilled for some time with Jordan. However, as soon as I entered and began to stroll towards the armchair, he suggested having a conversation about our days while he cooked supper.

Although that was fine, too, I was genuinely anticipating some hugs... and kisses... and embraces... I adjusted what I wore.

We still had a nice conversation, and Jordan made an extra delectable dinner with multiple courses.

That night, I slithered into bed with Caleb, clad just in a jock strap. I was positive he liked me in these.

However, rather than ravishing me when he detected what I was wearing, he became irate and stormed out, cursing about self control.

He never returned that night, so I slept alone. It hurt. He could have simply declined to sleep with me.

The twins were behaving oddly as well.

I was fearful they no longer wanted me. Were they weary of me? I would've given up, but I distinctly observed them gazing at me with desire when they assumed I couldn't see. Their penises were erect. I couldn't understand what was happening.

I blatantly sat between the twins and touched them more than was necessary at school and at home. They'd lean in, as though they were about to say or do something deviant, yet they'd retreat like they'd just remembered they had someplace to be.

......

One Friday night, Jordan shared at mealtime that everyone should keep their plans unplanned for the next day due to a household operation.

That family project turned out to be renovating my room! The room had dried out long ago, the pipes had been replaced, and drywall had been installed. Now, it merely needed paint, some finishing touches, and refurnishing.

Everybody woke up early the next day, much to Reese's frustration. We all had a big breakfast and started working on the house. It was lovely watching everyone pitch in, and the tension I'd been feeling for weeks began to fade away. The guys teased and joked with me as usual. Caleb hoisted me onto his shoulders to reach the high corners and paint them. The twins, by accident or intention, covered me in paint, even leaving some handprints on my backside. I'd missed their touch and playfulness.

Despite my insistence that gifts weren't necessary, they bought me new furniture. I paid part of the cost, and they took care of the rest. I saved the receipts, promising to repay them over my next few paychecks. Caleb said I was being silly for doing that but Jordan shook his head, silence falling over the room. I didn't want to be a burden.

Caleb, Asher, and Avery were tasked with picking out a new mattress and bed frame. They surprised me by buying a California King-sized bed - the biggest one I'd ever seen!

Reese's teasing was interrupted when Jordan reprimanded him. Reese responded with laughter and said he approved, earning him a slap on the back from Jordan.

We allowed the paint to air out for a few days before sleeping in my new room.

My first night on the new mattress was extremely comfortable. It was better than anything I'd slept on before. The pillows were filled with goose feathers or something, making me feel like I was sleeping on a cloud.

The first morning, I woke up with my body aroused and a wetness around my stiff penis.

"Uhhh, aahhh!"

I pulled the comforter up to find Reese watching me with a naughty smile on his face between my legs.

"Oohhh, Reese! Don't stop!"

I clawed at the sheets as his tongue pushed me closer to orgasm. His finger slipped behind my balls, across my perineum, and found my tightening anus. He slid his thick finger in, and I came. Then, Reese climbed on top of me and pushed his enormous cock into my mouth. A few forceful thrusts later, and he ejaculated, filling my throat with his salty reward.

We cuddled together after.

"How do you like your new bed?" he asked.

"I love it. And it feels even better when you wake me up in it."

"Let me know if you need help with unpacking your things later today."

"Okay."

He kissed me and left the room.

Despite the guys' continued kindness towards me, their behavior felt distant.

Even Reese was keeping his distance, looking at me sympathetically without saying anything.

What did I do wrong?

The guys were still nice to me, inviting me to join their activities, but...

I was horny! Maybe I really was a slut after all. I felt awful about it, but I'd grown used to their physical company, and now without any contact, I felt lonely and insecure.

I left the bathroom door unlocked while showering. Caleb accidentally walked in, his eyes scanning my naked body as the water ran over me. He grabbed the door, making it squeak open and shut.

Jordan started keeping the kitchen counter between us. We hadn't spent time in his office in weeks. He'd find excuses when I tried to get close to him while cooking.

The twins' labored breaths turned into shallow breathing since just looking at me made them flush.

The lack of Reese's presence in the house made me feel even more alone.

I loved my new room, but I asked if I could share Jordan's bed. I felt so lonely and thought Jordan might be the only one who wouldn't immediately leave the room if I came in.

Jordan seemed uncomfortable. He showered before going to bed, making sure he went in dressed in his pajamas.

When he came out, he got into bed as far away from me as possible.

"You can move closer," I said. "You're practically falling off the edge of the bed!"

He inched closer slightly.

"Good night, Oliver," he said with a cautious tone.

"What about my good night kiss?"

He turned towards me reluctantly.

One of his warm hands landed on my neck tenderly. He kissed me briefly. I deepened the kiss, pressing my tongue into his mouth until he responded. He grunted and pulled me against him.

I thought I'd surprise him by joining him in his shower, but he locked the door!

I decided to go to bed naked, pulling the covers up to my neck.

He came out, surrounded by steam and already dressed for bed.

He got into bed next to me, as far away as possible.

"Come a little closer," I suggested. "You look like you're about to fall off the bed."

He moved an inch or two closer.

"Good night, Oliver," he said, facing the opposite direction.

"How about that good night kiss?"

With an effort, he turned towards me, and I kissed him firmly.

His hand touched my neck carefully as he tried to avoid prolonging the kiss.

I snuggled up to him, and in response, he slowly moved closer.

"Good night, Oliver," he said, his hand lingering on my neck.

I fell asleep satisfied but feeling a little unsure about the situation.

He forced my tongue back into my mouth as his continued. His other hand reached my shoulder.

"Where's your shirt?" He asked in between kisses. "Aren't you cold?"

"Mhm, a little," I replied, sucking on his tongue.

He shivered and made a delightful sound that I savored. He pushed me against his body, encircling me in his arms. Ooh, my delicate nipples and naked d*ck rubbed harshly against his clothes.

His hand slid down my back and found my bare bum. He hesitated, then grabbed a handful of my ass cheek, desperate for it. He kissed up my jaw and down my neck.

"Where are your clothes?" His voice was harsh.

"Hmmm, I'm comfy like this. Oh!" He stroked the crevice between my cheeks. "The twins usually sleep naked- hmph!" He slammed his mouth against mine again, devouring me. I yanked on his hair, trying to get closer, even though we were almost joined at this point. His tongue f*cked my mouth. I moaned and hummed.

His hands seemed to be everywhere, leaving a trail of fire where they touched my skin. He briefly lifted one hand to tear his shirt off. He instantly pulled me snuggles against him again. Our chests rubbed together. Touching skin with Jordan was exquisite!

The next thing I knew, his pajama bottoms were off and our legs were entangled together. I was lost in his overpowering kisses. I couldn't remember if we were taking a breath at all. I didn't care.

"Jordie..." I moaned into his mouth. "You make me feel so good." I didn't recognize my own voice. It was sultry and greedy.

He flipped me over, crushing me into the mattress.

He lifted his hips and slipped a finger between us. He found and rubbed my hole exquisitely. He slipped a lubricated finger in. I'm not sure when he grabbed lube.

"Tell me to stop." His voice was gravelly. "I still might be able to if you..."

"More..." I kissed him urgently, running my hands through his soft hair. I pulled on it.

He groaned and added a second finger, stretching me.

"More!" I begged and looped my legs around his waist.

His thick fingers filled me so well. The stretch discomforted me, as no one had touched me in so long, but it soon turned into more pleasure.

Jordan's face hovered above mine, meticulously observing my reactions. His jaw was tense, and his pupils were dilated.

Three fingers entered and ground into me.

"Jordie!" I gasped. "M-moreee!"

He paused, then pushed more forcefully. A grunt escaped him. "Jordie!" I gasped.

He pulled his fingers out, and just when I thought I felt completely empty, his cocktip bumped against me. He pressed in gently, only enough for his cocktip to indent my hole.

My voice was barely audible. "More."

He practically howled, ratcheting up his pressure. His head slipped into me. "Oliver, you're perfect." He kissed me... reverently and tenderly and with a smooth seduction as his enormous cock sank further and further into me. "You're so tight," he groaned. "Aghhh!"

He was so big, I felt stretched to the brink. It was a tad painful, but I also finally felt full. Overly full.

Every now and then, he pulled back and thrust in again, each time going deeper. I was panting heavily, unable to keep up with his delicious kisses.

He finally seated all the way in, his balls pressed against my butt. He growled into my neck, grunting.

He ran his hands over my body, soothing me as he waited for me to adjust.

"You're so big, Jordie. I finally feel filled with you." I kissed him.

He grunted again. I enjoyed the deep noises he made! He took control of the kiss, forcing his lips against mine. "Oliver, you're perfect." He played with my nipples. Aaaah! And started slowly fucking into me. Each drag of his thick cock along my spasming walls caused me to shudder. The discomfort left, and I became a shivering mass of need and pleasure.

He wrapped his arms under my knees and nearly split me in half, pulling my legs to my shoulders.

He rolled his hips, culminating with a powerful thrust at the end of each thrust. Over and over, again.

All my nerve endings were overloaded. All I could sense, see, smell, and taste was Jordan. He was all man, all care, and all. "Aaahh, oh my god!! There! Right there!!" He'd shifted his hips and hit the perfect angle.

My head fell back. I arched my back into him as much as possible, savoring the feeling of the swollen head of his huge cock dragging against my prostate repeatedly.

"Jordie..."

I clawed his back. He really lost it in response to my reactions. His thrusts strengthened significantly, almost pounding me into the bed. I felt like a live wire on the verge of breaking. I adored it.

"JORDAN!!!"

Jordan's hand slid between us, rubbing my erection. Within seconds, I was reaching my peak. As he rammed his body into me, the tingling sensation in my canal increased. Then, I felt him release his own cum, which filled me.

"You're the most precious thing to me." Jordan gently raised his head and met my gaze. "I promise I'll always make you happy."

"You already make me smile," I said and managed to raise my hand to his face.

He leaned into the touch and kissed the palm of my hand.

That night, I had a peaceful sleep.

.................

Thinking about the moments when Jordan gazed at me with the same intensity as when he claimed my virginity made my cock hard again, leaving me feeling empty and burning with desire.

My hole was quite tender, so Jordan advised me to take it easy for a couple of days. But his caresses and longing looks were enough to send me over the edge.

Some of my brothers looked at us puzzled, and I was still confused about the situation.

.................

I was focused on my homework when I heard a commotion downstairs.

"This isn't a children's game!"

"I caught him first!"

I ventured out of my room to find the brothers in the living room, arguing.

"This isn't a contest!" Reese replied, turning to face Jordan with what looked like anger in his eyes.

Jordan attempted to say, "I'm sorry, we didn't mean to interrupt your home-" but got punched by Caleb in the face. Jordan's head moved violently to the side. Caleb was about to punch him again when Reese held him back.

"Calm down."

But Caleb continued, "How can I keep calm when..." It seemed like he was going to throw the third punch, when he paused, noticing the fear in my eyes.

"Hey, dude, I didn't mean to scare you." He took a step towards me, and I instinctively moved back. "Do you fear me?"

"N-no," I answered, feeling my face turning slightly red.

"You don't need to fear me." Caleb left and slammed the door.

The twins wrapped me in a blanket and held me in their arms. "We're going to ensure you're alright," Reese said, dragging Jordan away.

.........

Jordan's lip was bleeding.

"Jordie, are you alright?" I asked.

"Yes," he said weakly, wiping blood off his split lip.

"Did something happen?" I queried.

"It's fine," Avery said. "We'll take care of it." He led Jordan to the bathroom.

The twins held me in their arms once more, caressing my limbs to calm me down. I stopped shaking. Their soft whispers in my ear made my heart rate slow.

"What happened?" I asked.

"Did you think Jordan forced you into sleeping with him?"

Asher asked.

"No!" I cried, feeling my face turn red. "Jordan would never pressure me. He told me I could leave because someone else was about to show up before him," I continued, still feeling flustered.

"More like he lured you in to take him for himself!" Avery exclaimed.

Reese reentered the room, "Daniel, are you okay?" Jordan enquired.

"Yeah." I responded.

"I'm fine," Jordan said, rubbing his bloodied lip.

"Really?" I asked.

"I'm fine," he said confidently.

"What did happen?"

"Caleb got out of hand, which resulted in a family meeting after you cried that you were called a slut." Avery clarified.

"He told us all to give you space, but really, he wanted you to himself," Asher added.

"Really?" I shuddered.

"Yes, and we know," Avery said, giving me a comforting hug. "We did get jealous, but that doesn't mean we don't love you!" Asher added, also wrapping me in his arms.

"Okay," I smiled, feeling more reassured.

"Oh my gosh, did you see what happened? We came really close to a disaster."

"I think Jordan messed up first," I chimed in.

There was a brief pause as they both seemingly hesitated to speak. "Maybe," they uttered, "kind of," was their response.

"Let's stop being rational for now. We're still upset with him," Avery whispered in my ear, giving me a kiss on the forehead. "Wanna watch some TV? You can sleep here between us."

"That sounds like a great idea right now. Thank you," I curled up against them, drifting off to sleep from the weight of my emotions even before I realized what show they had turned on.

Characters:

Oliver (Ollie, Olive, Liv)

  • 18 years old
  • Gay, a bottom
  • Junior in high school, repeating a grade for personal issues
  • Nicknames: Ollie, Olive, Liv

Asher and Avery

  • Both 18 years old
  • Hair color: Red
  • Bisexual, prefer guys, share sexual partners
  • Juniors in high school
  • Started a grade behind to not be in the same class as older brother Caleb
  • Slightly mischievous, with Avery being more so
  • Avery calls Oliver Liv; Asher calls Oliver Olive
  • Asher's jersey number is 12, Avery's is 21 in Lacrosse

Caleb

  • 19 years old
  • Gay
  • Senior in high school
  • Summer birthday
  • Professional football player, jersey number 22
  • Caleb calls Oliver Ollie
  • Wants to take care of his brothers, but doesn't want them to feel like siblings
  • Previously dated a string of people, but has a soft spot for Oliver
  • Uses dirty talk

Reese

  • 22 years old
  • Used to be straight, is now attracted to Oliver (Oliver-sexual)
  • Studies accounting in college
  • Nickname: Little one
  • Enjoys boxing and crafting
  • Womanizer

Jordan

  • 25 years old
  • Gay
  • Lawyer
  • Called Oliver Oliver, Oliver calls him Jordie
  • Strict but can't say no to Oliver
  • Previously broke up with guys for being too clingy, while being very sweet to Oliver and wanting to take care of him, but doesn't see him as a brother
  • Gave Oliver his virginity

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