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.
“You’ll be in good hands,” she told me as I sat there waiting to be called on, “Selma’s an old friend of the family, she’ll look after you,”
Selma was in her 40’s but by the way she looked, late 20’s would be more accurate. Her skin was flawless, no signs of cracking yet, her hair amazing and in great physical shape. She also knew exactly what Tayla was after for me as my friend stood by us the whole time to chat and watch.
As she was almost finished, Tayla wanted to get involved more, “Selma, do you mind if I uh have a go with the clippers? Just for a little bit.”
“Sure sweetie, if your friend here is okay with it of course.”
I had a stunned look on my face.
What did Tayla know about cutting hair, she didn’t have a license to do it, if there even is a license for cutting peoples hair. She took over from Selma, as the woman went for a break, “Oh relax Leo, I’ve done this before.”
“Uhh when?”
“I practiced during lockdown a couple of years ago,” she explained, “My brother, my father, my sister as well until she told me that I had ruined her life because of the bald spot I accidentally gave her on her scalp.”
I wriggled in my chair, leaning forward so she couldn’t touch anything. But Tayla stood there chuckling, pulling me back into the chair, “I’m kidding, I’m kidding, I don’t even have a sister.”
Letting out a sigh of relief, I tried to calm myself down and just let her work. To my surprise, she definitley knew what she was doing. Tayla cut through my hair slowly, being cautious not to change too much since Selma had already done such a good job.
I watched in the mirror in front of me, the time and care that she was taking. I had to admit, I loved the feeling of her hands running through my trimmed hair, up against the top of my head. Naturally, I found myself thinking about where her hands were a couple of weeks ago.
We hadn’t spoken about the secret late night handjob on the couch. And all I wanted to do was talk about it but the timing never seemed right or I was just too much of a coward to ask. Maybe in a public venue, this wasn’t the right place either but if I didn’t bring it up now while none of the other girls were around, I may never bring it up and I would just live on, wondering if I imagined the whole thing.
“Tayla…”
“Yes Leo?”
“About the other night…”
I paused, noticing Tayla was now looking at me in the mirror and not looking at my hair. A sly smile crept up on her face as she helped me out, “Yeah, what about it?”
“Was that just a one time thing?
The brunette with the trimming scissors still in her hand had stopped cutting by now, she was looking at me, working out how to word this, “Look… the last thing I want to do is to lead you on, it wouldn’t be fair on you. What happened last Friday, happened. It wasn’t a mistake but I hope you didn’t think it meant anything more than what it was.”
Just like I had expected.
But I would be lying to say that I wasn’t disappointed.
“You’re a good kid, so innocent,” she continued, “I kind of figured you’ve never done that before… hope I didn’t take that moment away from you.”
“No, no, no, it was great,” I said right away, “I figured it was a rebound thing…”
She looked a little apologetic as I said that.
Tayla sighed, putting the clippers down the table, “The girls have probably told you about what happens with me and Declan every few months… I know I shouldn’t go back to him, he’s… he’s… I don’t know… but I always take him back, I’m not going to pretend it’s any different. So yeah, when things are rough between us, we take a break and I… I guess…”
Tayla looked around to make sure she was being quiet enough and nobody around us was listening.
“I guess I get a little slutty…” she whispered, “I was drunk and I was fucking horny… and then you came over and I could feel how hard you were so when I knew everyone else was asleep, I snuck up onto the couch and started to play with you.”
I gulped as she kept speaking, still looking at me in the mirror. My hard-on had returned and I was now trying to focus on getting rid of my boner inside the barber.
“Then after you came, I went upstairs…”
Again, she double checked her surroundings, aware that this still was a public venue. Sure that nobody was listening to us, she spun my chair around and now she was facing me, no mirrors involved.
“Then I fingered myself thinking about it…”
Oh my god, I was going to lose it. I knew she wasn’t going straight to sleep.
“I thought you were going to come up, I thought you would want more… but you never did.”
I had my mouth open, about to answer her, trying to excuse why I didn’t come up. Damn it! Why didn’t I? Is she admitting to me that she would have fucked me if I did, taken my virginity at last?
“But the next morning I understood,” she continued again, “You weren’t ready for more, that was a big step for you and I get that, it would be wrong for me to push you into anything more.”
She was treating me like a kid. Like I was too young or inexperienced to do anything more with her.
“No that’s not true, I’m ready!”
I realised I was speaking a little too loudly. Tayla spun my chair back around to face the mirror, after a customer near by glanced over at us.
“If you were ready, you would have come up to my bedroom, if you were ready, you would have been texting me the next night, telling me to come over,” she whispered, “It’s nothing to be embarrassed about, please don’t think I’m trying to embarrass you.”
I don’t know if I was embarrassed but it sure didn’t make me feel amazing.
But what did it really matter, I missed my chance because I was too inexperience to know that she was waiting for me to make the next move. This was going to bug me for a while, knowing exactly what I had missed out on.
Tayla let Selma finish the final touches of my haircut.
What could I say? They did a fantastic job, it wasn’t anything too flashy, but a 110% improvement from my last haircut. After listening to Tayla compliment it for the next five minutes, I was passed on to Annie who was going to take me shopping.
In one way, I felt like their own personal boy toy experiment.
Annie dragged me into a clothing store that I had never stepped foot in before. My wardrobe did need a complete update and she was going to be in control of picking what I bought.
“Here,” she said, pushing clothes into my hands, “And here… and this… and this.”
Jeans, shirts, jackets, I couldn’t keep track of it all. She led me to changing room area, “Start trying some of this on, I’ll keep looking to see what else there is.”
Annie was a woman on a mission. I entered the first changing room, shutting the curtain as I made my way inside. Awkwardly, I put the clothes down on the small stool. I stood there for another few seconds, mot having a clue on where to start.
Slipping my shoes off, I pulled down my shorts leaving me in my black briefs. There was a tiny wet spot on the material of my underwear. I must have leaked a bit of precum after Tayla had told me how she was fingering herself after getting me off the other night.
Looking for the new jeans Annie wanted me to try on, I was startled when the curtains reopened and closed. The blonde had come inside without warning, carrying a couple of more items of clothes.
“Oh shit,” I mumbled, trying to cover my crotch.
She giggled by the way I reacted, “Aw, somebody’s shy.”
“I just, I…”
“It’s fine Leo, you’re not the first boy I’ve seen in their underwear,” she told me, “Besides, fair’s fair, you got to see me in a thong!”
Annie then grabbed the jeans from me and told me to lift my right left. She crouched down and helped me into the jeans as if I was her child and she was helping me change. Obviously I could do this all by myself but I allowed her to take control.
She pulled them all the way up and even managed to do up the zipper and button up the jeans to complete the look. Her hands were so close to my cock that it brushed up against it while zipping me up.
I nervously stood there, trying hard non to pop another boner.
But she wasn’t done herself yet, Annie pulled my tshirt off without warning and helped me into a new buttoned up white shirt. She took her time to inspect my body. Because I didn’t work out, I didn’t have a great chest or big arms. But she looked at me with a look of potential.
“Oh my god, fantastic, you look so good!” she squealed, clapping her hands together.
I turned to look at the full sized mirror on the wall. Annie was behind me with a great big grin on her face, flashing those pearly whites.
I don’t know what it was about that smile but every time she gave me one, my heart started to melt.
“You have to wear this out Saturday!”
“Saturday?”
“Yeah, Saturday, Joshua’s birthday,” she repeated before realising it was another thing I hadn’t been invited to, “Oh don’t worry, I’ll make sure to get you on the list.”
Again, I appreciated her looking out for me. It would be interesting to head to a party now with the five girls well and truly in my corner. I didn’t want to look for a new girl if they pushed me in that direction, I’d much rather just hang out with the ‘Saturday Night Five’.
We trialled more clothes until Annie was 100% satisfied. My card got a nice little workout with what she made me buy but it didn’t matter what Annie told me to buy, I was going to do it, no questions asked.
***
The rest of the week flew by.
Milly took me to the gym to start working out with her, hoping to assist in helping me improve my physique. But for me it was just an opportunity to stare at Milly getting nice and sweaty in tight gym clothing.
Then I was invited around to Rose’s place on Saturday to go over a few things before the party that night.
The whole thing was a little daunting. I made friends with these girls through one moment of drunk courage but the idea of going out to a party to try and pick up with their assistance was daunting to say the least.
Getting to her house at 1pm, Rose welcomed me in, casually coming to the door in nothing but a pair of black panties and a white t-shirt. The shirt was baggy enough to cover her panties standing still but it was clear enough to see what was underneath when she moved.
Following her up the spiral staircase, I just stared at her ass. I wish those steps never ended.
“Mom’s out, taken my little sister to some concert,” she explained as we entered her bedroom.
Instantly I was trying to compare it to Tayla’s. The messiness was the first comparison I could think of, Rose didn’t pick up after herself, the carpet barely visible because of the amount of clothes that were left out.
Just watching the way she threw things out of Declan’s cupboard at his party, I could see why it was the same here. I took a good amount of time checking out some of her underwear and sets of bras that were sprawled out on the floor.
Her room however smelt amazing. I was taking in the scent of what I figured was her perfume.
Rose was quickly back up on her bed, sitting crossed legged in front of a little mirror stand that she had moved up there. In her hand was a pair of tweezers, she was taking care of her eyebrows.
“Come sit with me,” she said, seeing I was still standing there.
I tiptoed my way through her clothes, accidentally stepping on an orange coloured bra on my way to the bed.
“Just one second hun,” the brunette said, “A lot to be done before tonight.”
I waited patiently, just loving the fact that I was actually inside Rose Parker’s bedroom. It’s something I never thought possible, I had always wondered what it would look like from the inside, now I was here as her friend. A friend that wanted to give me advice on how to pick up girls…
Rose eventually finished up with her eyebrows, taking off the mirror from the bed, “Okay Leo, I’m glad you’ve come to the master for some advice.”
“Well, I didn’t really have much of a choice,” I replied.
She brushed that comment off, “It takes more than just a new set of clothes and a nice haircut to help you pick up. You’ve got to know how to flirt honey and from everything I know about you, that’s something you’re going to need help with.”
She knew me too well, that absolutely was not a strength of mine, not even close.
For the next hour or so, Rose gave him bits and pieces of advice on how to properly flirt with girls but she mainly spent that time sharing stories of the different ways she had teased and flirted with boys in the past.
As even as late as last weekend, Rose had a story.
“We ended up at some club in the city on Saturday,” she explained, still crossing her legs on the bed, “Katie bailed out earlier for whatever reason, I don’t know, she’s been weird lately. But the rest of all went out, of course we got in for free looking like this.”
Rose pointed to her own body in a very cocky way when she said that. She wasn’t wrong, killer body.
“Anyways, Tayla was in full slut mode, after ten minutes inside, she had found someone she wanted to fuck. Milly on the other hand, was off flirting with a couple of guys on the dance floor leaving me and Annie behind. Guys naturally flocked to us, there was one in particular that I fancied. He was handsome, ripped and oh was he a sweet talker, telling me how good looking I was and what he wanted to do with me.”
I listened in closely, wishing I was that type of guy.
“So I was super keen, trust me, I wanted to fuck him, I was going to give him a night he’d never forget… Anyways, some time passed, I left to get a drink and have a dance with Milly but by the time I was back, I saw him getting real close with Annie. He looked like he was playing both of us.”
I was even more interested to hear that Annie was involved with this. Rose continued to tell her story in detail as I sat with open ears.
“So when we had a chance, we compared notes. Just like I thought, he was playing both of us, literally telling each of us the same exactly thing about how we were the hottest girl in the room and what he wanted to do to us.”
Rose sighed as she continued, “Ugh, so disappointing, I haven’t fucked anyone in a month and I was sure I was going to break the drought that night. But I wasnt going down that rode with him after he tried to play us both. Instead, we came up with a bit of a plan to mess with him. Annie dragged him out to the girls bathroom, kissing his neck, teasing the outside of his jeans.”
I was conflicted. This was hard to listen to knowing Annie was again kissing and touching another dude again. But it was also making me horny, my shaft was growing in length as I covered my lap while Rose spoke.
She so knew I was hard, she didn’t miss a trick that girl.
“Annie took him into one of the stalls, he was so confident he was getting action in there. I waited for a couple of minutes and then pushed open their door, he was sitting on the top of the toilet seat with his pants and underwear down at his ankles, looked speechless to see me, figured he was in trouble.”
Rose shuffled positions on the bed, she leaned back to the side, I could very easily see her black panties underneath the shirt now.
“But we thought we’d mess with him a bit first,” she said, her hand moving down to her thigh, “We made him think we were keen on a three way, we let him sit there with a rock hard cock as we made out.”
Jesus… he wasn’t the only one rock hard. Rose looked down at my crotch as she said those words, her hand still running up her own thigh.
“We were pretty pissed too so we weren’t taking it easy, lord does Annie use a lot of tongue… He was loving every second of it, especially when Annie started to pull down my dress, I didn’t have a bra on underneath so she let my titties fall out in front of him. I had to admit, I was still pretty horny even though I wanted nothing to do with this guy anymore. He tried to get involved when my boobs came out, trying to reach forward and touch one of them… but Annie slapped his hand away.”
The more she spoke, the closer her hand got to the front of her own panties. Her pink painted fingernails were right in front of the black material.
I didn’t even realise it at first but I was doing the same, touching my boner from the outside of my shorts.
“Annie then bent down to put her lips against one of my nipples,” she continued, “Oooh baby… I’m surprised she hadn’t done this before because the girl knew how to tease a nipple. It was all meant to tease him but even I wanted to jump her bones. Anyways… after she sucked on my tit for a couple of minutes, we knew it was time to hit him where it hurt, his ego.”
Rose kept teasing the outside of her panties with her fingertips, staring at me the whole time with those pretty blue eyes. Her long brown hair down and to one side, giving her an incredible sexy look.
“We told him it was time, Annie kept him distracted by kissing his neck once more. It gave me time to pull his briefs and jeans off his ankles. He had nothing covering him now. I opened up the door wide, walking out with half his clothes. Annie stopped kissing him and followed me out. He yelled out for us to come back but we stood out there laughing, told him he shouldn’t play with fire.”
Wow they were crazy… crazy hot, I stayed hard the whole time listening.
“Pulled up my dress, we took his clothes and left him alone half naked in the girls bathroom of the club. We hid his clothes, waited to see if he would come out but he never did, probably had to wait until close to get out of there but I’m sure he learnt his lesson.”
Rose suddenly pulled her fingers away from her panties, knowing exactly what she was doing.
“God we’re evil! But he deserved it right?” she leaned forward.
It was the first time I had a chance to respond in quite a while, “Yeah he did… fuck, you really know how to get someone back.”
“Of course… what goes around, comes around, it’s Karma,” she stated.
I could see her looking at my crotch again. Being as bold as she was, Rose had no problem with moving my hands away to see the tent in my shorts, “Knew I could get you riled out with that story, come on, take it out, you need to get yourself off before tonight.”
“Wait what? What do you…”
She repeated it so naturally, “You need to jerk off before we go out, if we can get you lucky tonight, you can’t afford to be a one pump chump.”
The theory made sense.
If I did go out without doing anything about this now, I’d be in trouble tonight, if I somehow did manage to pull someone. I got up off the bed, “I’ll just use your bathroom then I guess…”
Rose grabbed my hand, stopping me from leaving, “Hang on. If I’m the reason you need to cum then I think I’ve got a right to see it happen.”
Hearing that, I gained a bit of confidence to ask something I would usually be afraid to ask.
“Well… did you want to do it yourself?”
A cheeky smirk curled up on her face, “Hmmm, been waiting for you to grow a pair and get direct with us.”
The brief excitement that Rose might wank me off like Tayla had done to me, vanished quickly, “But…” she continued, “I’m a bit of a petty bitch and I haven’t forgotten that you didn’t pick me after my sexy lap dance I gave you so that’s not happening today.”
I stood at the side of the bed, her hand still grasping mine.
“Alright, that’s fine,” I said, breaking away from her grasp.
There was a light purple blanket at the edge of the bed, I grabbed it and went behind her, leaning up against her pillows. Covered by the blanket, I quickly pulled off everything from below the waist so I was half naked like the guy from her weekend story.
Rose turned around to look at me, smirking even more so now.
My hand touched my cock which was already warm and hard. I could feel the precum already leaking from the head of my shaft. It was odd to be doing this in the current situation, I felt like I was doing something wrong.
But Rose sat there and watched the blanket move up and down as my hand bumped it while I stroked myself.
It was less than a minute of a quick handjob until the brunette had something to say. She bit down on her bottom lip, touching my leg from the outside of the blanket, “I’d still like to see, I’m not getting much of a view with that blanket in the way.”
I ignored her. If she didn’t want to help me out, I didn’t think it was necessary to show her anything.
“Come on now,” she teased, “You show… I show…”
I stopped stroking.
“What do you mean?”
“You heard me,” she repeated, “If you remove the blanket, I’ll show a little more skin to help you finish properly.”
My cock was twitching at the words of more skin. I would love to see this girl naked in her own bedroom more than anything. The brunette tease cocked her head, waiting for me to answer.
Rose grabbed the bottom of her shirt and lifted it up just a little bit, she moved it around with her hands in a teasing way, “How about we start with my shirt for your shirt.”
An easy deal.
I pulled up my t-shirt over my head and left it by my side on the bed. I shivered as it now sunk in that I was completely naked on her bed.
Like Annie had done earlier in the week, Rose glanced at my upper body, seeing what I had to work with. But she didn’t back out of her part of the deal, the brunette pulled her shirt up from the bottom slowly, all the way over her head. I was now seeing her in her bra and panties, both black, a similar but less expensive set to what she had on in her lap dance tease at Tayla’s place
Seeing so much more of her cleavage again with just her bra on, I picked up where I left off, stroking my cock. Trying to find the right pace, I didn’t want to cum too early if she was actually going to show me her tits tonight.
They looked amazing in that bra, sitting up proudly on her chest. I didn’t know what bra size she was, I also didn’t know much about bra sizes to begin with. But comparing their size to the other girls, she was comfortably in the middle. Milly and Katie had the biggest, then a drop off until Rose, closely followed by Annie and then Tayla with the smallest rack.
Rose grabbed her own boobs, squeezing them in her hands, “Alright hun, you want to get rid of this bra?”
She started to pull at the shoulder straps, slipping them off her shoulders but never removing them completely. Of course I wanted it off, I nodded enthusiastically with my hand on my cock, “What do you want for the bra?”
“I want the full Monty baby,” she told me directly, “Remove the blanket and let me see your dick… then I’ll remove my bra.”
Why I was so nervous to show her? I guess it was because I still did find her intimidating, it was hard not to. In the back of my mind, I was worried she would be embarrass me, laugh at the size of my dick, say it was nothing compared to all the others she had seen before.
“Go on then,” Rose repeated as she slipped one strap completely off her shoulder.
Fuck it. I had come this far already.
I didn’t waste time doing it slowly, I pulled the blanket to one side, revealing my nude self to her. The vulnerability I felt was overwhelming, there was nothing covering me now. She leant forward to pull my hand away so she had the complete view of my cock.
Rose bit down on her lip and slowly nodded. Maybe she did like she what she saw.
“Wow,” she mouthed, “You know… that is a really pretty cock.”
“Is that a good thing?” I asked, my legs wide open to her.
“Of course it is,” she explained, “And it’s the perfect length, not too big, not too small, we can definitely work with that.”
My length twitched in front of her eyes as she told me how much she liked the look of it. That was music to my ears and so was the sound of her bra strap unclipping from behind as she began to take it off. Rose held onto the cups of her bra as she wiggled her arms out of the straps, almost free from his confines now.
But the tease then let the bra drop, not removing her hands from her tits. This was part of her deal I guess, she was going to now tease me with them. I resumed stroking as she rolled her breasts around in the palm of her hands.
“Do you like my boobs?”
“Mhmm…” I muttered, jerking quicker.
Rose bounced them around in her hands, loving the way my mouth drooled and my right hand flew up and down my shaft.
“Are you almost about to cum?” she asked.
I nodded, “Can you move your hands?”
I wanted to see them in full. I wanted to see her nipples, I was hoping they were hard, I wanted this to be turning her on.
Rose giggled at first, acting dumb, “My hands?”
“Yes.”
“What do you want me to move my hands for?”
She wanted me to say it. She knew what she was doing to me right now.
“I want to see your tits…”
“My tits?”
“Yes!”
“Are you sure?” she continued her little game, “Can you handle them?”
“Oh god yes… please.”
I was getting closer, the way she showed more cleavage but continued to hide her nipples had me on the verge of blowing my load.
“But you didn’t even pick me the other night, I bet you’d rather see Annie’s tits.”
Again… I was getting sexually frustrated once more, “No, no! I want to see yours, I should have picked you, it was my mistake, please just show me your tits.”
I would have sounded like a pathetic desperate virgin but I didn’t care, I needed to see them before I came all over myself.
“You mean that?”
“Yes! I promise!”
“So you want to see my boobs?”
I nodded again, repeating the word yes in a now desperate tone.
“What? These ones?” she then said, dropping her hands.
My eyes widened and my hand went into speed mode as I jerked off to the sight of her now braless and handless bare breasts. She immediately began to shake her body, jiggling her tits in front of me.
Her pink nipples to my pure delight were a hard, solid size, they pointed out on top of her pink areolas. Those breasts had a nice drooping shape to them when not held up by her hands, again, the way she described my cock in size, the way I would describe her breasts, not too big, not too small, plenty to work with.
Rose knew exactly how to tease me with them, she put her hands underneath their weight and bumped them up repetitively. Seeing them bounce freely like that was the last straw for me, I had started to cum, shooting back in my direction.
I controlled it enough that only one drop didn’t land on my body. She watched with glee as my cock spasmed, letting out load after load of hot white jizz.
“Don’t you feel so much better now!” she cheered.
I was too out of it to speak with words, instead I nodded with a little smile, still looking at her bare tits. Rose got up from the bed, grabbed a box of tissues and threw them back to me. While I cleaned myself up, she headed for the door, “Good work today, I think we made plenty of progress, I’ll be back soon, taking a shower.”
I laid there, cleaning myself up, just in awe on how things had changed for me over the last month.
Then the thought of Tayla’s words from the other day struck me. How I was not ready to lose my virginity, how I didn’t come upstairs to see her.
Was it doing it again? Should I be following Rose to the bathroom?
I knew I would get it up again as soon as I had a look at her pussy. That drove me out of bed, walking out of her bedroom naked. I had never seen a girls pussy before and boy did I want to.
I walked down the quiet hallway, my footsteps making a creaking noise as I did so. Without know where the bathroom was, I followed the sound of running water. It led me to a closed door. Again, I had come this far already, what was the harm in pushing my luck.
I yanked the handle down and tried to surge forward. But I went nowhere, bumping into the door. I tried the handle again, fuck… the door was locked.
Awkwardly, I tiptoed back to her bedroom and changed back into some clothes, pretending I had never tried that.
***
Fresh and relieved, I was back at another party that night.
Again, I wasn’t invited, just an added plus one but who cares, I wasn’t the only one in that boat. This time, I felt a little more confident, I had my new friends behind me, the most popular girls at school. Socially I was better off from it and at least some other people actually knew who I was because of who I was hanging out with.
Without much experience at parties, I couldn’t tell if this was a fizzer or a great night. But the mood was a little dour for a party, nobody was really dancing, some of the more popular guys had left early. If the girls didn’t have their secret mission to get me laid or find me a girlfriend, they probably would have left as well.
But I just kept drinking.
And drinking.
And drinking.
When I realised I was speaking with Kyle O’Donnahoo for twenty minutes, the psychotic linebacker on the high school football team, I knew I was at least some what drunk.
Seeing where I had been for a while, Annie pulled me away from him, “I thought we agreed you were here to flirt with a girl, not a guy.”
She pulled me back to the girls group, “You need to get your head back in the game.”
“I was just chatting,” I said, as if I was about to be interrogated.
Rose, Milly and Tayla were here in the circle, looking out at the crowd of people, seeing who they could match me up with. With a boring party, I had suddenly become their only source of entertainment.
“How about we let him pick someone out?” Tayla asked.
Milly touched me on the arm, holding it as she looked out to a group of high school seniors, “Who tickles your fancy?”
The five of them did, that’s what I wanted to say.
I looked around and saw another attractive girl chatting with two other girls. Her name was Bella, she was another very popular high school student. She had a very similar body and complexion to Rose, instantly I was interested.
“I mean Bella’s pretty good looki…”
“Are you fucking serious? No.”
Rose looked at me with her arms crossing her chest, a stern look in her eyes. I figured the No was because she was too out of my league but I didn’t understand why suggesting her would make her so angry.
“Don’t you even think about Bella Thornton or any of her friends!” Rose said sternly.
I nodded quickly seeing how fired up she was to hear that name.
“Yeah… we don’t exactly get along with them…” Tayla confirmed.
The other two girls nodded as well.
“I’m guessing there’s a story there?” I asked.
They looked at each other before declining to give me any more details. They quickly began searching around the crowd again for someone else.
“What about Monique?” Tayla suggested, “That could work?”
Monique Cherry was way above my league, just like the other girls.
On looks alone, she could easily fit into the Saturday Night Five without anyone questioning it. Her light brown locks, petite figure with plenty of sex appeal. But her personality didn’t quite fit the popular girls group.
She wasn’t really a girly girl. Monique would hang with rough crowds. She smoked regularly, I had even seen her tonight out the back having a cigarette with a couple of older guys, dropouts from Templeton High.
I was reasonably drunk myself so I didn’t know it at the time but so was Monique, hence why they picked her, hence why they could convince her that I was a suitable person to hook up with tonight.
“Now,” Milly told me carefully, “She’s not the girlfriend type… but she’s pretty attractive, she’s not shy and if you don’t fuck it up, you’re a good chance to get your dick wet.”
The blonde was virtually escorting me up to Monique who she knew was out of it. Milly briefly introduced mine self to her which then led to some minor awkward conversation between just me and Monique.
Just because I was under the influence of alcohol, it didn’t mean I knew what I was doing when trying to flirt with a female. When conversation dried right up, there was an extremely awkward pause between us. I think I was staring at the grass when she finally opened up her mouth to break the silence, “So did you want to make out or something?”
Not exactly enthusiastic or anything but I’ll take it.
“Sure.”
We didn’t waste any time, out in the backyard, she put her hands on my body, bringing me in close as her lips went to work on mine. I could feel her tongue sliding in almost right away. The first thing I noticed was the piercing on her tongue and they say it felt every time it brushed up against my own tongue.
It was a little distracting at first but eventually I was looking for it every minute. Monique knew it as well, after what only felt like a couple of minutes but was much longer, she pulled my mouth away from hers, “If you like my tongue piercing, just wait until you see where else I have then.”
I gulped, I got a pretty good idea of what she was talking about.
“Down the hallway… second bedroom on the right, I’ll meet you there in five minutes…” she said as she walked back to the house.
Holy Jesus… was this it? Was this chick going to fuck me? Was I going to lose my virginity right here at a house party?
Maybe I wasn’t getting that lucky but I was at least getting something, no doubt about that after her little piercing comment. It had me sporting a nice big stiffy outside, thank god I listened to Rose’s advice at rubbed one out this afternoon otherwise this would be a very quick experience inside. Not wanting to look too over eager, I waited outside for a couple more minutes, I needed to control myself so I went to the side of the house, away from everyone to keep my thoughts in check.
“Oops sorry,” I muttered as I saw a girl around the corner sitting on her butt up against the bricks of the double story house.
I was about to hurry away when I stopped and realised exactly who was there. Katie, she was alone, crying softly, her head in her hands. My heart started to rip apart as I saw her there in obviously a very distressed moment.
“Katie, are you okay?”
Katie?”
She wasn’t responding, just hoping I would go away. This wasn’t exactly ideal timing, in a minute, I had to be inside to find where Monique’s other piercings were on her body.
But I couldn’t leave her alone like this, I slumped down against the wall so that was sitting right by her side. With her skirt and sleeveless top on, her body looked cold. She only moved her hands away from her face to see that I had joined her, “What are you doing Leo?”
“I… I just wanted to see how you were, is everything okay?”
She let out somewhat of an exhausted chuckle, “Oh I’m fine, I’m fantastic,” she said sarcastically.
“Is this about that night?”
Katie knew what I was talking about but she chose to ignore me again. In the back of my mind, I kept thinking about getting upstairs but my cock had to wait, this was more important to me.
We sat in a bit of silence, I was hoping she would eventually open up to me. Realising I wasn’t going anywhere, she turned her head to face me, “What are you still doing here?”
I cleared my throat, “You’re my friend Katie, I can’t leave you here like this.”
“I’m not your friend Leo…” she mumbled, “I haven’t done anything to deserve your friendship, you saved my ass and I barely gave you a thank you in return.”
She appeared to be annoyed with herself. But I was happy to see her at least talking now.
“You don’t need to thank me,”
She shook her head, “No I did need to but let’s face it, I’m not like the others, I can’t give you the puppy dog attention that they do.”
I had obviously noticed over the last few weeks that Katie certainly wasn’t as talkative as the other girls. She didn’t give me a whole lot, where as the others treated me almost like a new project, in some way.
Maybe I still hadn’t worked out if that was a good thing or a bad thing yet.
Remember my conversation with Milly about the way that guys saw them, I decided to use that new knowledge to try and make her feel that I understood what she deals with.
“Look, I know you have it a lot harder than what people think,” I said, “I mean to go through what you did a few weeks back and have guys just know you for your… you know… your…”
“Boobs?”
“Yeah, you’re boobs,” I said a little awkwardly, “I did it myself and I feel embarrassed about it now.”
“Leo, it’s fine,” she cut me off, “Yes you’re right, that gets old quickly but don’t put yourself in that category, there’s a difference between not being able to stop staring at my tits and using me for my body while not wanting to get to know me at all.”
We continued to talk a little more, until I couldn’t hear anymore sniffling. I just mainly listened, chipping in here and there when I could but after what she had been through, I had the feeling she mainly just wanted someone to listen to her.
“I don’t know, is it too much to ask for to have a normal date where a guy isn’t trying to feel me up in the cinemas or rushing us out of a restaurant to get me to his house so he can undress me…”
“Why don’t I take you on a date?”
“What?”
I couldn’t believe I had suggested it, “Yeah… you, me, movies and dinner, just something nice and then I drop you home, say goodnight and then go back home myself.
Katie was smiling now, chuckling at the idea of it. But I could see she wasn’t going to turn it down. Shrugging at first, she began to not, “What the hell, why not.”
“It’s a date then I guess,” I said, having not been on a proper one in years.
With her tears officially gone, we stood up ready to return to the party. She then realised what I was here for tonight, “I’m guessing the whole plan failed tonight then for you, if you’re sitting here with me.”
I shook my head, remembering what I had missed out on to stay outside with Katie.
“You got with someone??” she asked.
“Uhh sort of, Monique… we uh hooked up outside but um she wanted me to meet her in a bedroom inside but then I saw you here and I kind of forgot about it.”
She slapped my chest in a friendly way with a disappointed look on her face, “Why did you do that?? She would have so done whatever you wanted.”
I just shrugged, my cock was certainly thinking the same thing but my heart had said otherwise.
Katie leaned in and hugged me tightly, knowing what I had just done. If that wasn’t proof that I wouldn’t go against my word with our date then I don’t know how I could convince her.
“Maybe keep this all between us okay?” she whispered in my ear as we hugged, “It’s better that way.”
We shared a sweet moment.
It may have costed me the possibility of losing my virginity but instead… I had secured a date.
An actual date with one of the Saturday Night Five.