Saturday Night Five Ch. 02

Story Info
The girls try to set Leo up, teasing him along the way.
11.1k words
4.7
26.2k
46

Part 2 of the 9 part series

Updated 11/23/2023
Created 04/11/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

The creaking floor of a quiet house hit my ears as I walked along the floorboards, en route to the bedroom,

Wearing nothing at, my cock stood to attention despite being depleted only what felt like moments before. It throbbed hard as I pushed the bedroom door open with my hand. As it opened up, I was treated to the sounds and view of an 18 year old brunette girl, rubbing furiously at her clit.

Legs stretched out wide, her fingers rubbed her bald pussy, nothing but her silky pink pyjama top on. Her matching shorts discarded by the bed, laying on the floor.

I walked inside the room to get a better look at her. Tayla opened her eyes as I stood next to the bed, she didn't stop fingering herself when I came into the room. Looking at her closely, I began to stroke myself again, I could easily cum right here on the spot.

"Just fuck me already."

Tayla's voice was direct and clear, pulling me down on top of her.

I didn't get a chance to realise I was about to lose my virginity before my eyes opened.

Sweating, I woke up on the couch in the dark lounge room. Everyone was asleep. Checking my phone, it was 5:11 am. I sighed, still high off that dream, also remembering what had happened with Tayla over night.

I drifted back off to sleep, having similar dreams.

The night at Tayla's house would continue to replay in my mind for weeks to come.

It would be a great source of jerking material. Every time I was alone and horny, I would think about each girl and how they appeared in front of me in their lack of clothing. My mind could never focus on one thing, it would always go from thinking about Rose's dancing to Katie's topless display and back to Tayla jerking me off.

She actually wanked me off... I still couldn't believe it.

I began to doubt it even happened considering she was pretending like it never did, acting normal around me. There was a lot of questions I had but I chose not to ask them since she didn't seem that willing to talk about it.

I never bothered to tell Michael what happened that night, he wouldn't have believed me even if I did tell him. To be honest, I wasn't exactly his favourite person right now anyway, with all the studying I was doing with the girls, I didn't have much time to hang out with him.

Yes, I'm aware I'm being a bad friend.

But I'd like to see you tell me that you'd do it any differently when the five hottest girls at school were at your disposal.

"Again? You've been in the library every night this week," he complained to me on Friday when I told him where I was headed.

"I'm sorry man," I apologised, "I was helping Katie and Milly yesterday for their geography assignment, now I have to help Rose tonight with her English essay."

He just looked at me still in disbelief that this was going on. Shaking his head, he was following me to the library on his way home.

"What are you even getting out of this? They're just using you!"

I didn't like to hear that one bit, as I stopped in front of the school library, "They're not like that, they're friends."

"You better be getting fucking something! Surely Rose goes down on you underneath the desk or something, the slut would do it if you asked her!"

The timing couldn't have been any worse for Michael who finished his sentence as soon as Rose had turned the corner and was now behind him. I just stared, looking at Rose with her arms crossed, raising an eyebrow. Michael's heart sunk when he turned around to see her standing there.

"Oh my... umm..."

"No, no, you're correct," she cut him off, taking a step closer to him, "I'm about to go down on him now in exchange for some more English notes."

Rose made a whole scene of licking her lips with her tongue very slowly, "I would have asked if you wanted to join us but... I don't think you've got too much down there to work with."

Michael was utterly stunned. Rose brushed past him as she grabbed me by the arm and pulled me inside the library.

That's the type of confidence the girl had. She could give it as well as she could take it... which was also true in sexual terms if all of the rumours were true. Rumours that included how she could suck off a guy better than any other 18 year old going around, rumours that her pussy was the definition of perfection.

I wanted to know for sure.

Rose led me to our usual table, "You've got to ditch that weirdo asap."

"Rose, I've known him since I was five, we're family friends..." I said, not wanting to pick a side here.

We sat down at the table with Rose still shaking her head, "I wasn't asking you."

The way she stared me down, I knew the girl wasn't messing around and she was a hard person to say no to. She didn't take that word well, not many guys had ever used it towards her. We weren't going to even be able to start working until I told her that I would ditch him.

"Rose, please, I'm sorry for what he said, it was super inappropriate but I can't..."

"Leo, do you realise where you sit right now?" she interrupted.

I shrugged.

Rose sighed and opened up her notebook. She flicked through the pages to find a blank one where she started to draw. The brunette was drawing up a social hierarchy chart. She wrote the girls at the top of the page and then went to the bottom of the page to write Michael.

"This is the social status of our school, this is where we are, that is where Michael is... you right now are here," she said, writing down Leo just underneath the girls names, "Good spot huh? You think you can stay there while being friends with..."

Rose was again pointing to Michael's name.

"The choice is simple, you can be friends with him, that's fine but we'll do these little study sessions and then we'll go our seperate ways... or you can leave that freak behind and we can study together but also hang together, all of us... I know what my decision would be."

I could see why people saw her as manipulative and a hard ass. But in reality, she was right, the decision was easy, I wasn't giving up what I had with these girls, not after what happened at Tayla's.

"Okay, I'll ditch him."

"You promise?" She asked, holding her pinky finger up at him.

I nodded as our pinkies connected, "Promise."

Her smile was back and so was her bright energy. Rose paid close attention for the next hour or so as we went through everything for her upcoming essay.

By the time we were done, the library was empty.

"Never thought I'd see the day that you'd be the last one leaving the library on a Friday evening," I told her as we walked out.

She laughed hearing that, "Trust me Leo, I didn't either. But you should take a picture because it won't happen again anytime soon, tonight's tough enough, still have to get to ready at Milly's before tonight."

I must have made a bit of a face as I tried to work out what was happening tonight, obviously something I wasn't invited to, Rose had picked up on it.

"Aw sorry, it's not another 'sleepover' if you were wondering."

I shook my head, "Oh no, I wasn't thinking that..."

"Bet you're waiting for the next time you get invited to one of those nights huh?"

Yes. The answer was yes.

"Umm yeah sure, I guess so," I replied.

I could see her glancing to her side so she could smirk at me while we walked. As much as I was trying to figure out these girls, she was doing the exact same with me.

Our houses weren't far away from each others, something she had just found out but something I had known for a long time, always seeing her around the neighbourhood when we were younger and of course during high school.

As we got to her place first, I was expecting her just to say a quick goodbye before she got ready but she stopped and turned to me, "I've got to know... why did you pick Annie the other night?"

Oh boy, under pressure with the tough questions again.

"Have you got a crush on her? Is that what it is?" she asked when I didn't reply straight away, the girl definitely wasn't holding back.

"No, no I don't have feelings for her," I lied.

"Do you have feelings for any others of us?"

"Uhh no, no."

"What about sexual feelings?"

I gulped, maybe I can get away with lying about the other ones but she would know it was bullshit if I said no here.

For whatever reason, I felt like it was extremely awkward to say yes so I just shrugged which her responding smirk taking it as a yes, "Do you think about fucking us?"

Fuck... all the time.

"Umm I don't know, I guess so."

She managed to stay so calm while she interrogated me, the girl had phenomenal powers over men. Especially virgins like myself who were still on a high from a late night handjob from another girl a week ago.

She said the next line so innocently, "You would fuck me right?"

I would have fucked her right on her front lawn in front of all her neighbours if she gave me the chance to. Instead I just calmly nodded, still not wanting to come across as over keen yet honest.

Rose smirked again, "Good to know... Have a good night Leo."

I watched her ass sway as she walked up the driveway to the house. God she made me horny, all that questioning just had me frustrated.

If only I had confidence, maybe then I'd stand a chance with somebody like her.

***

Later that night, I laid in bed alone. I had ignored the texts of Michael because of my conversation with Rose at the library. But it didn't seem fair, the girls were all still out and I was home alone.

The worse thing about it was social media. I couldn't put my phone down because I was checking every second minute to see if any of them had updated their Snapchat stories or put up a new post. Every-time I saw a new story of the girls out dancing at some club in the city, I felt my stomach sicken, real fear of missing out.

Wondering why I couldn't be there, why did I get invited to some things but not others.

And then the jealousy of knowing that these girls were more than likely certain to get with other guys at the club... that's what really killed me.

***

Saturday Night was almost an identical night for me.

Thankfully by Sunday, things were looking a little brighter thanks to an invite to the Miami Dolphins game from Milly. She had season tickets and was there at almost every home game. Usually she went with her father but with him being unwell, she asked if I would be interested.

I wouldn't say I'm the biggest NFL fan, my parents were originally from New York so I grew up a Jets fan which wasn't a much of an experience. It also didn't help that I wasn't a good athlete so my interest in sports didn't rival the likes of the popular guys at school. Checking my diary, this was probably the first time that I had ever spoken about a sporting league inside.

Video games and movies were always my preferred source of entertainment but if Milly would start inviting me frequently to the football then I was going to try and get into it.

The game started just after lunch but we were there way earlier than we need to. According to Milly, she would never risk missing the opening kick off, hence why we were there almost an hour early. But it didn't matter to me, I was just thrilled to be included, I also couldn't believe how good the blonde looked in an oversized light blue dolphins jersey, to go with her short shorts.

"You know, I never usually would bring along a Jets fan here so you should feel pretty honoured," she told me as we waited for the sides to come out.

"What about the girls? You didn't want to bring one of them?"

She shook her head while laughing, "Oh hell no... I mean, Katie's alright to take I guess, Tayla's a bandwagon Pats fan, no matter what she tries to tell you, Annie talks too much throughout the game and Rose doesn't know the first thing about football and even if I asked her, she wouldn't come anyway."

I chuckled as she went through the other girls, guess it did make sense why I was picked, "Well I'm glad you invited me along."

We continued to chat before the start of the match. I had to ask about how the last two nights out were, curious to hear what had happened.

Milly went into a ton of detail but not necessarily the most important bits of information. The blonde so easily got sidetracked. She would start explaining one thing but end up dragging the conversation elsewhere. I heard her mention that Katie wasn't there which had me curious.

"How come Katie wasn't there?" I asked before she went off course again.

Milly paused, "Oh... well... I guess she hasn't been too keen on going out lately, ever since the incident."

It made sense, what happened to her that night was soul destroying. At least for me, my beating was quick and I made friends with the five hottest girls at school from it but Katie had clearly been left scared. Pinned to the side of a car, being groped which may have only been the start of it if nobody came out to save her.

"That's terrible," I said softly.

She nodded, "I think everyone thinks we have easy lives but it's not true. Just look at me and Katie, how would you describe us in a couple of words."

Don't say it.

Don't say it.

Don't say it.

Milly knew by the pause that I wanted to say big boobs, "Yeah it's about our tits isn't it? You know that I know what the guys call me right? Milly milkers... I may happen to enjoy that sort of attention but Katie's not like that, she's quieter, she may come across as a snarky bitch at times but really she has a heart of gold that she never lets anyone really see. If she had it her way, she'd rather be invisible to the majority of the school."

That hit home.

Invisibility is how I felt my entire life at school but I had always dreamed of what it would be like to not be in the shadows. I guess it was a double edged sword.

"What about you? Do you ever feel that way?"

She stopped to think for a moment. Then I realised she wasn't thinking, she was just looking down on the field as the opposition, the Buffalo Bills came running out, "pfft... no snow to save them this time..."

Once she realised I asked her a question, she snapped back to reality, "Oh sorry... um, not really, maybe I'm just a bit of an attention whore but I love knowing the power these posses."

Her hands were pointed to her heavy chest with a big grin on her face. I believe I was just nodding along with her aimlessly as I began to appreciate the size of them once again.

We didn't have much time to chat about anything else once the Dolphins players were led out onto the field.

We had a really fun afternoon in the end. The Miami Dolphins caused a boil over in the warm conditions, holding on to win by three points over Buffalo. I had a great time, loving when Tua would score a touchdown or the Bills would turn over the ball, seeing just how excited Milly would get. Every time she'd be up on her feet, high fiving or hugging me.

Despite her boobs being covered by the Dolphins uniform, they felt fantastic every time they pressed up against my chest.

I left that game knowing a lot more about Milly and a little more about Katie.

***

"Don't know why you didn't ask me, you haven't invited me to a game in years," Tayla questioned Milly.

Sitting with the girls at lunch the following day, they were all interested in why Milly had chosen myself to go with her to the game.

Taking a bite of her apple, Milly shook her head at the brunette, "Because you were embarrassing me in front of our fans last time you cane, trying to tell Tom Brady how much you love him... even though you're a fake Pats fan!"

"Fake pats fan?? I am not!" she hit back, "I watch all the time."

Katie chipped in, "Oh yeah? Who's your new quarterback then?"

There was a silence at the table as Tayla tried to figure out when and where Tom Brady had gone.

"It's not Brady anymore??" she asked dumbfounded.

Everyone at the table laughed.

"You may be the smartest girl on this table but you sure don't know much about football," Milly told her, feeling like she had just won the argument.

After some minor conversations about the weekend, I began to panic when I saw Michael heading to the side of the table. There was an empty spot to my left and I knew what he was going to ask.

I hadn't told him anything after Rose told me to leave him behind. It wasn't an easy thing to do especially when the girls would still all go out on a Saturday night without me at times. But I was playing the long game here and that meant I had to be careful with my interactions with Michael.

"Mind if i take this seat?" he said straight up.

The girls looked at each other as if he had just told them that he had a gun on him. I didn't have a chance to turn him away as Rose answered first, "What? Think I might suck you off under the table if you sit here with us?... Beat it creep."

She had a right to be annoyed with Michael after overhearing the way he was speaking about her. But he was still my friend so I felt like I was in a really tough position here.

Michael looked at me, waiting to hear it from myself. I could barely look him in the eye, "Sorry Michael, table's full..."

It wasn't, there was definitely another room for one more. But he got the message, I'm sure he was giving me a dirty look as he left but I didn't look up at him, too embarrassed.

"Good boy," Rose commented.

I didn't feel good about it, like I was the girls' little lap dog or something.

"You'll be so much better off without him, trust me," Annie added, jumping on the bandwagon.

"Yeah definitely," Katie said, "Try having gym class with him, dumbass got hit in the head last week by a volley ball because he was too busy trying to perv on me... pathetic."

I sat quietly.

It wasn't long ago that I could have easily been that person who would be hit by a ball because I was trying to get a better look at Katie's boobs, the same boobs I had now seen in the flesh...

I would still take a volley ball to the head to get one more look at them.

"Just look at how much better you're doing without him," Rose then said, noticing I wasn't smiling, "Sitting with us five at lunch, going to Dinosaur games with Milly..."

"It's the Dolphins... the Miami Dolphins," the busty blonde corrected her, dumbfounded by what she had just called them.

"Yeah, yeah, whatever, the point is, you stick with us, we can really help you out."

"What about a girlfriend, we should be helping Leo find a girlfriend," Annie then suggested.

I appreciated the thought. But I would be lying if I said I didn't have growing feelings for the five girls right here, particularly Annie.

If I was to have a girlfriend, I wanted it to be one of the five that were sitting at the table. But the others loved the idea that Annie had brought up. Suddenly they all began to suggest ideas to help me, Tayla wanted me to get a specific new haircut while Annie wanted to take me out shopping to change my wardrobe, Milly wanted to take me to the gym and Rose wanted to help me learn the art of flirting.

The girls talked for the next ten minutes of ways they could help me.

"Let's start tomorrow night, I'll take you to get a haircut," Tayla said, "And Annie can take you clothes shopping after."

"Hang on," I said, "I thought I was meant to be helping Annie study tomorrow..."

"This is more important," the skinny blonde replied with a grin as the girls all began to get up.

So there you have it, they had made the decision for me. When school finished the following day, I jumped into the back of Tayla's light blue Honda sedan and we were off to the shops.

There was something oddly exciting about this. I had never had a makeover before, especially not from girls who had expertise in things like fashion and looks. We headed to the mall and Annie excused herself to go shopping for herself as Tayla brought me to a specific hairdresser joint, one that wasn't for the poor.