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Introduction:

Lena tries again with her older brother.

Hello again, Lovelies! I come with another chapter to Lena's story. This chapter follows the original version of chapter three, not the alt version. I hope you enjoy it! As always,
Xoxo, Cede <3

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Two weeks had passed, and I still couldn't look at my older brother. We both ignored the fact that he’d taken my virginity, and danced around the fact that it wasn't what it was supposed to be.

I started imagining sexual things when I was about ten years old, masturbating a few years later. I had made a promise to myself to lose my virginity by fifteen, and have tons of sex. But that had come and gone. I’d held onto my ’precious flower’ for three years longer than I’d planned, and was completely disappointed that actual sex wasn't what I expected.

Girls in romance novels became raging nymphomaniacs as soon as the guys throbbing cock busts through their steel-enforced hymens. So why hadn't it been like that for me?

Since Milo and I weren't really talking, he was back with Lucy. I swear he was doing everything possible to shove their loud, obnoxious sex in my face. I’m surprised Milo didn't FaceTime me while he was fucking her. The banging of the headboard against the wall was so loud, that when they finished and came downstairs, my mother had to awkwardly ask that they ’be safe, and try not to put nicks in the drywall.’

Mom was not so enthused when after breaking up again, Milo and Lucy got back together because she was pregnant. This did not stop them from having lots and lots of sex, though someone did accidentally leave up a yahoo answers search about having sex with your pregnant girlfriend and if your dick would hurt the baby.

I cried for a week straight after I found out. In the back of my mind, I always thought Milo and Lucy wouldn't last. I still wanted him. After much research, I decided I needed to try again. This time, with me controlling everything. I scraped my savings together, ordered a package called, ’first love’ that included a seven inch, hot pink dildo with veiny texture, strawberry flavored lube, and warming oil. I was all over that tracking number like ants on a lollipop, and practically gave myself an ulcer making sure no one else intercepted my package.

Who needs a man when you have three variable speeds and clit stimulation?

I may have made the mistake of forgetting to buy batteries, and having to borrow them from my tv remote. I wasn't planning on watching any tv anyways.

Things started out good. The lube tasted like strawberry candy, and things seemed to hum right along. The dildo wasn't intimidating, not like some that I had seen online, and with the lube, it slid in easy to home base.

It felt easier than my first time with Milo had, smoother. Maybe it was all the lube, I don't know, but it had me going, my hand shaking and my calves tensing.

And then it quit. “God dammit!” I cried out. I pulled the dildo out, and slapped the base against my palm. Nothing. I flipped the power switch back and forth. “Jesus fucking Christ!”

Milo burst into my room, a crazed look on his face. “Lena? I thought I heard something. Are you o-” His voice faded out as his eyes moved down to my exposed pussy, the pink dildo springing back to life in my hand.

My face turned beet red. He’d fucking seen me naked. For Christ’s sake, he’d fucked me. So why was him seeing me like this so anxiety inducing?

Both of us were frozen in place, his hand on the doorknob, mine holding a cartoonish pink penis in my hand.

“Get out!” I screamed, throwing the bottle of lube at him. It him him square in the eye.

“Ah!” The bottle tumbled to the beige carpet. Milo covered his eye like it was about to fall out of it’s socket. My embarrassment vanished, and I leapt up and rushed to my big brother.

“Oh my God, Milo! I’m sorry! I didn't’t mean to hit you in the face.” My left hand rested on his bicep and the other went to his face, fluttering like a hummingbird around him. “Here, let me look.”

“Holy fucking shit, Lena,” he swore lifting his hand from his eye. “What did you throw at me? It felt like a freaking brick.”

I bit my lip, avoiding his eyes. “Um, it was lube,” I mumbled. I touched the bright red mark right under his right eye. It felt warm and puffy.

“Ouch! Do poke at it!” He swatted my hands away. “What did you hit me with?” Milo glanced down and saw the bottle. “Is that-”

I shushed him. “Will you be quiet! I don't want the whole world knowing. Gosh!” Tentitavly, I looked down the hallway for anyone, but everything was quiet. I tugged Milo into my room, grabbed the bottle of flavored lube, and locked the door behind me

Milo looked at the vibrating dildo on my floor, flopping around like a dying fish, then back at me. A smug smile spread across his lips. “You’re wasting your time with that thing.”

Bending down, I swooped up the fake, pink cock, and turned it off. I shoved it under my bed, and fixed the ruffled bed skirt so my mother wouldn't notice. I flopped down on my bed, reaching under the covers for my undies. “And why is that, oh wise big brother?” I asked.

Milo advanced towards me, his hand snatching my underwear. “Because you have a living, breathing, cock ready for you right here.” He leaned down, and our faces were just inches apart. I could feel his body heat, and see the dark shadow of stubble along his jaw.

“I didn't realize your cock was a living breathing being,” I retorted.

“Yeah, so maybe Clark doesn't breathe on his own, but he sure needs a snug, warm house.” Milo gently pushed me down in the bed, and began to climb on top of me.

“Wait,” I said, pressing a hand to his chest to stop his approach, “you named you penis Clark? Why?”

The tip tops of Milo’s ears turned scarlet. “Clark Kent? Superman?” I giggled. “Don’t laugh. You’ll hurt poor, lonely Clark’s feelings!” He’d now maneuvered himself so that he was pinning me to the bed with his weight as he straddled my hips. I could feel his hardness throw the thin fabric of his boxers. He rocked against me, the friction on my outer lips torturous. “Clark misses his Lois,” he added, his voice barely louder than a whisper.

With that, he leaned in and began to kiss me, and I let him. I remembered my promise to take charge of what I wanted, and grabbed a hold of his head. I needed him closer, even though I knew it was physically impossible.

Our tongues danced, teasing each other. He did this thing where he sucked on my bottom lip, and my hips bucked against his groin. Milo’s erection was full on, and barely contained within the fabric. I let his hands roam under my shirt, over my breasts. He pushed them together, kneading them, and strummed my nipples with his thumbs.

“I want to be inside you,” he whispered, breaking our kiss.

I coudln’t say anything. It was if my voice had packed up and skipped town. My pussy pulsed, wanting him, needing him, but my mind was afraid. I didn't want it to be like last time.

“Lena?” He pressed, nibbling at my earlobe. His teeth scrapped against the tender skin of my neck, and sent chills down my spine.

“I- I-” my voice sounded small. Milo stopped his teasing, and sat up, looking me straight on.

“Lena?”

I squeezed my eyes shut, as if that could make everything okay, and blurted out, “I’m scared, Milo. It hurt before, and you didn't care...”

I felt his hand stroke my hair, tucking a stray curl behind my ear. “I’m sorry, Lena. I was so fucking turned on, my mind kind of went into auto mode. I didn't realize until afterwards when you locked yourself in here, and then you wouldn't open the door...”

What was I supposed to say? Forgive him? Tell him everything was a-okay? His fingers traced along my jaw line, and a worried look creased his brow. Here I was, my shirt up, bunch under my armpits, my older brother sitting on me, but still felt so far away.

I had a choice to make, and the look in Milo’s eyes made it simple. “Roll over,” I ordered. A dazzling smile lit up his face, and he scrambled off of me and out of his boxers. I crawled up between his legs, hoping I looked sexy. “Hands behind your head.” Milo complied, a big, cheesy grin on his face. I took his engorged boner in my hand, and gave it a squeeze. Pre-cum glistened at the slit, and I smeared it all over the head.

When I’d bought the dildo, I’d estimated it to be about the same size as Milo’s, but it fell short. Literally. Milo was wider and thicker, with the head of his cock more pronounced than the pink cock’s. Length wise, Milo made the dildo look like it belonged on a Ken doll.

And this is what made me nervous. I knew that was why things had been so horrible last time, but my research told me that the lube should help things goes smoother, no pun intended. Grabbing the bottle, Milo joked, “you’re not going to throw it at my other eye this time, right?”

“Ha ha. You’re so funny.” I rolled my eyes, and flipped the cap. The scent of strawberries reminded me vaguely of a baby doll I had as a child that was probably somewhere in the attic. I squirted a very generous dollop into the palm of my hand, the bottle making a loud farting noise. “Don’t even say it!” I warned Milo.

He chuckled, momentarily forgetting he was supposed to keep his hands behind his head. I reminded him.

“Sorry,” he replied, tucking them back, “I just-” he laughed again. “Are you sure you got enough lube or do you maybe need a little more.”

“Shut up!” I kicked him with the heels of my feet. “I read online that we should use lube to make things easier. It’s not like superman over here is as small as his action figure.”

“Oh, you sure now how to stroke a man’s ego, don’t you?”

“Whatever,” I muttered, rubbing the lube into my hands to warm it up. I grabbed his staff, covering it all over like I was icing up a cake. “There. That’s better.” I smiled, and squeezed Milo’s balls. I rolled them in my slick hand, momentarily entranced by their movement. Milo’s gruff moan snapped me back to reality.

It was now or never, I told myself. I had to take life by the balls. Grabbing my brother’s meaty cock, I hovered over him, trying to line us up. His hips bucked, and made me jump. He smiled sheepishly and apologized, “sorry.”

With agonizing slowness, I managed to center him up to my hole, and pushed the head in to me. His cock glided in, and after that, the rest of him slid easily into me.

I squealed, “I did it!” And Milo just groaned, his erection pulsing inside of me. Slowly, I began to move, just rocking at first then moved onto sliding up and down his pole. Our skin smacked against each other and made a wet, sucking sound.

“Lena, Lena, Lena,” he moaned, his eyes closed. “Just like that. Fuck, Lena.”

This encouraged me, and I upped my game moving quicker, harder. The head of his cock tapped against my cervix each time I took him the whole way inside of me. It felt like someone poking at a bruise, not quite painfully, but just enough to flood my mind with sensation.

With each downward stroke, a soft grunt escaped me. “Uh, uh, uh, uh.” Still I needed more. I began rub viciously at my clit, and my hips slowed to jerky rolling. My orgasm built quickly, a sensational pressure deep inside me. “Uh, uh, Milo!” My head flew back, and my spine arched as my pussy squeezed around Milo like a python’s vise.

It was just enough to send him over the edge, and he forgot to keep his hands behind his head. They flew up, grabbing my waist, and holding me down on him as he began to cum. I could feel his balls clenching beneath my bum.

Both of us collapsed, our skin slick with sweat and our hearts racing. We were silent, and I curled up into the nook of his arm.

We must have fallen asleep because the buzz of my phone vibrating on my nightstand startled me. With sleep clouded eyes, I tried to focus on the caller id. I couldn't make it out.

“Hello?” I asked, my voice hoarse.

“Oh my gosh! Lena! I didn't know if you’d pick up. Thank God you did!” Lucy’s voice was not what I had expected to hear in the middle of the night.

“Who is it, Lena?” Milo asked, raising his head up.

“Was that Milo?” Lucy asked. “Why the hell didn't he answer his phone? I’ve been calling all night!”

Fuck! “Um,” I mumbled, my brain was foggy and I couldn't think of an excuse. “We, um... Fell asleep watching a movie. He must have forgotten his phone upstairs.”

“Oh,” Lucy murmured. “Okay. Can you put him on, Lena? It’s very, very important that I speak with him.”

I held the phone out to Milo. “It’s Lucy,” I mouthed.

Milo took the phone. “Lucy? I’m sorry. I left my phone upstairs, and we fell asleep.” I could hear Lucy shouting on the other end of the line, but couldn't make out the words. “No, I promise I have not been avoiding your calls. God, okay?”

While they Lucy berated my brother, I slipped out of bed, and began to dress. The two of them went back and forth for a while, Milo’s voice getting increasingly louder, before she hung up on him.

“I forgot to call her and tell her goodnight,” Milo explained. He groaned and fell back onto the pillow with a huff. “If she wasn't’t pregnant, I wouldn't have to put up with this kind of shit.”

“Well, she is,” I said point blank. “And what are we going to do?” I asked. A ball of fear squeezed my insides. “She’s having your baby, Milo. You guys are supposed to be getting married after the baby comes. Are you guys going to be married and live in separate houses?”

“We’ll figure out,” he cajoled. I wasn't sure if he meant Lucy or me.

“We can't keep sleeping together when you’re with Lucy.” I sat on the edge of my bed. “It’s not fair.”

Milo’s jaw flexed as he clenched his teeth. “And what am I supposed to do? Huh, Lena? I want to be with you, but I’m stuck with Lucy.”

“Then we have to stop, Milo. We can’t continue this.”

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