The Losers Ch. 09

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A competition to determine Roscoe's next girlfriend.
1.8k words
4.69
7.7k
17

Part 9 of the 11 part series

Updated 06/11/2023
Created 12/19/2021
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Krosis
Krosis
767 Followers

To summarize: I'm June, and to keep my twin brother Roscoe from getting asked out by a 'barbie', I suggested that he start dating one of the girls in our club, The Losers: Sue, or Sulu, a cute, short Chinese gymnast with a flat chest; Bella, a very tall, pretty redhead; and Larissa, a Native American with huge boobs but an acne problem. Roscoe and I are brown-haired and somewhat average, though my ass and his chest have started to fill out. We're all 18, in case you were wondering.

In trying to convince Roscoe to choose one of them, the three girls, one at a time, did sexy stuff with him, finally resulting in all of them losing their virginities to him and also taking a load of his dangerous sperm inside their unprotected pussies. I saved the day, though, by giving each of them a birth control pill from my Mom's old stash. None of us really knew how birth control pills worked, so you can see the problem.

---

On Friday after school, all of us girls went to the thrift shop with our babysitting money to prepare for that night. My parents had gone out to another party, so we were free and clear for more illicit fun with my brother.

"Okay, bro, tonight you'll decide who your next girlfriend will be, but we're not going to make it easy. Swallow this, head downstairs, and we'll come down in a bit," I directed him.

Roscoe looked at the strange blue pill I had handed him. "What is it?"

Larissa spoke up, "It's from a drug trial my Dad's taking part in. You'll need it for later. Don't worry, it's harmless."

"Ooookay..." Roscoe swallowed the pill and went down to the rumpus room.

After a few minutes, I called down, "Now turn on the tape player." A few seconds later, I heard David Bowie's 'China Girl' playing on the boombox we had stored down there, and Sue headed down. We had tried to convince her to pick a different song, as it seemed a bit too 'on the nose', but she insisted. I watched from the top of the stairwell as she pranced down the steps and stepped out into the basement, revealing her short, fit form in a shimmery blue dress we had found that had a deeply dipped bodice showing off a strip of bare skin from her neck to her navel, with extra material gathered around it to hide her lack of breasts. I heard Roscoe call out, "Wow!"

David Bowie's crooning voice continued, talking about his little China girl and how she said that he should shut his mouth. "She says 'Ssh'..."

Sue took a bit of time to sashay about in her gorgeous outfit and, after a bit, the music abruptly stopped while she got the boombox to fast forward to the next song. We had created a mix tape, one song for each of us, but unlike CDs, you had to wait for the tape to advance if you wanted to skip ahead. Writable CDs were still a couple years away, so for now we were stuck with that delay.

Lionel Ritchie's 'Endless Love' came on, and I headed down. What? I love that song, and I loved my brother. Anyway, I had bought a likewise shimmery top, red and sleeveless, that hugged my boobs, and a pair of dark capris that were practically painted on that showed off my booty. I had a little trouble getting down the steps in the red heels I had borrowed from Mom's closet, but it was all worth it when Roscoe saw me.

"Damn!" His eyes went wide, and I flushed. I had never worn anything like this before, usually choosing t-shirts and jeans. I put my hand on my hip and thrust it out to the side, like some model I'd seen on TV, before striding around the basement to show off my outfit (and body).

Lionel Ritchie's voice filled the room, talking about two hearts beating as one. "Our lives have just begun..."

Satisfied, I strolled over to Roscoe.

"You're all going to show off your new outfits for me?" he asked.

"Yep, it's a fashion show," I said, and gave Sulu a look. She pressed fast forward again and we waited for the next song as I sat on the couch and crossed my legs.

Duran Duran's 'Hungry Like the Wolf' came on, and Larissa came down. She was wearing a yellow dress with a tight bodice that came down to just above her knees. The black Doc Martens she wore seemed out of place, but kinda fit her personality.

"Wow, Lariss," Roscoe commented, and she swayed her boobs from side to side as she showed off her outfit, boobs, booty, and legs while striding around the basement.

Simon Le Bon continued singing about strutting on lines, discord and rhyme, and being after whoever 'you' was. "And I'm hungry like the wolf..."

Finally, she headed over to join me on the couch.

Another fast forward, and ZZ Top's 'Legs' came on. We figured that Bella would win this contest, hands down, and we watched as she emerged from the stairwell.

"Wow," Roscoe repeated.

The tall girl had found a gorgeous slinky black dress that came down to below her knees, but with slits up the side that showed off her long, sexy legs in a pair of black pumps. She had splurged and purchased some panty hose, and we saw her gams glint in the light of the basement as she shimmied her hips, striking pose after pose.

"She's so fine, she's all mine,

Girl, you got it right..."

With a satisfied look, she strode forward to join the rest of us.

Then Sulu turned off the music, breaking the spell as the basement went silent. She joined us by parking her perky little ass on the arm of the couch.

Roscoe turned the La-z-boy toward us. "You all look amazing!"

"You're the judge," Larissa informed him. "Who wins?"

He looked stricken. "Oh...was this to determine who's my new girlfriend? But what if I said Sue?"

"Then I get '20 Minutes in Heaven' with you first, but then you'll have to pick Bella or Larissa," Sue responded.

"20 minutes what?"

Bella spoke up, "Up until now we've done all of our fun stuff with you as a group, other than the start of your first time with me." Her face reddened. "Whoever you pick first will have 20 minutes alone with you down here, and then number two, and so on."

He sat back, and we saw his erection tenting out his sweatpants. "But I can't choose just one of you; you all look so amazing." I noticed that his sweeping gaze included me as well.

Larissa turned to Sue. "Okay, if he won't pick, then we'll go off of his responses. Who got the best one, Sue?"

Sue looked uncomfortable. "Actually, it was June."

"What?!"

"Yeah, he gave all of us a 'wow', but June got a 'damn'."

"Damn."

"Yeah."

Larissa got up. "Okay, let's head up and give June her 'damn' 20 minutes."

Sue got up as well, but Bella just sat there, confused. "But they're related."

"So I guess they talk for 20 minutes...rules are rules," Larissa told her. "C'mon, Bella." Then she pulled the other girl to her feet and all three went back up the stairs.

"C'mere," Roscoe patted his lap.

I paused for a moment, but then got up and sat across his legs.

His arm went around my waist. It felt nice and warm. "You look beautiful, June." I flushed. He put his other arm across my legs.

"So what do you want to talk about?" I asked him.

"How about the fact that you're still my favorite?"

I gasped. He had whispered that in my ear as he fucked me in this very room a couple weeks past, but I had thought that he had made a mistake in the dark. "You...you knew it was me? Not Bella?"

He wrinkled his brow. "Bella? Oh...OH! You thought...but...that's why..."

I took his chin in my hand. "Use your words."

"Uhm...I thought that maybe I had gone too far and upset you, which is why you didn't mention it or show any interest afterward. If you thought I mistook you for Bella, then that explains it."

I hadn't noticed that he was pulling me closer until I felt his hard cock under my leg. Then the hand that had been pulling on my legs moved to one of my breasts. I gasped as he lightly squeezed it through my blouse. The top had been too tight for a bra, so I had left it off.

"Ros..."

His other arm pulled me all the way into his lap, and I felt his erection pressing up between my legs.

His eyes were intense. "I felt you cum when I was inside you...you liked it," he told me.

I had. I moved forward to kiss him, and his tongue slipped inside my mouth. This was my very first kiss, and it was with my twin brother! The boombox was no longer on, but I could swear I could still hear 'Endless Love' playing. As we kissed, I could feel him pulling my blouse up, and then his warm hands were on my bare breasts. I gasped into his mouth and pulled back.

He looked at me with a mixture of lust and fear. He must have thought that I was going to stop this. Hell no! I got to my feet and pulled my capris off, and Roscoe quickly pulled down his sweatpants. In a flash I was astride him, my knees on either side of his legs, and I reached down and quickly directed his hard cock inside me.

"Yesss..." I moaned as his thickness filled me. My blouse was still up around my neck, and he took one of my funnel-shaped nipples into his mouth. "Ohh!" I was desperate to get him all the way inside me, this time with the knowledge that he wanted ME, and I wiggled my hips until I made it happen. "U-hh..." I paused, feeling all of him deep inside, and he pulled his mouth from my nipple to look up at me with lust, and also love, I realized. I kissed him again as I moved upon him.

Time seemed to have no meaning, I was so lost in the moment, but soon I could feel my first orgasm building. Roscoe took my rounded butt in both hands, pulled my groin to his, and ground himself into me, which immediately set me off. I broke the kiss to cry out in pleasure, "AHH-HAHH! Ohh...huhhh..."

"Ohh shiiit!" Roscoe cried out, and I felt his cock throb inside me.

My eyes flew open as I felt my brother's cum penetrate my forbidden depths and my waning orgasm flipped on its head as I came hard. "Gaahhd! O-hhhh!" I felt throb after throb of Roscoe's cock as it inseminated my spasming pussy.

As I collapsed upon him, I heard clapping by the stairs. I whipped my head around to see the rest of The Losers there. Larissa was clapping, Sulu was looking on with interest, and Bella looked shocked.

"I KNEW IT!" Larissa gloated.

To be continued...

Krosis
Krosis
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AnonymousAnonymousover 1 year ago

I do like the story. I kinda wish there was more 'posse' stories with a risk element out there.

One thing I do find strange is where you use telling instead of showing. Some of the places you don't fill out which would have made a hot situation even hotter.

Still, that said, really good story.

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