Fun with Step Sister's Friends Pt. 01

I am 19 and a freshman at a local university from my parents house so I could save money and stay home instead of renting an apartment on my crappy part time job. Which still leaves me living with my mom, step dad and younger step sister, Destiny, who is still in high school, albeit 18 and a senior gearing up to graduate. She and I are close, though we never thought about pursuing our relationship very far. We friendly towards each other and got along but we never spent much time together outside of living together or family functions.

We knew each other since we were 9 and 10, when our parents started dating and then got married a couple years later.

At the time of this event I was 5'10", 180 pounds, and short brown hair. while in high school I played sports, though not so much anymore. Destiny at this time was 120 pounds, also had brown hair, long, Down to past her shoulders. She had 38 B cup size and a pretty thin, curvy body due to her constantly working out as well.

During the week of spring break finally arrived, and I was grateful due to having a week to relax and not worry about classes. Destiny's spring break was the same week. I was especially happy due to this week our parents had scheduled a trip to celebrate their anniversary and they'd be gone all week as well, they decided on going on a cruise around Alaska. I didn't care that I didn't get to go. I was more excited that I could get a week without them was an added bonus.

As they were leaving that Friday evening to arrange for their plane ride they were giving us all the arbitrary threats and rules to what we could do or couldn't do while they were out. No parties, lock all the doors when we are gone, don't touch the A/C and all that jazz. We stood on the porch waving at them while they left. I was smiling all the way due to the idea of them leaving. Little did they know that I had a couple bottles of whiskey that I got from a college buddy that I planned on drinking through the week. We walked back in and closed the door.

Destiny sat on the couch and was scrolling through her phone after they left, replying to text messages.

"I'm glad they're finally gone. This is the first time they left us alone for any amount of time like this." I say as I sit in a recliner in the living room and flip on the tv to watch some Hulu.

Barely looking up from her phone, Destiny replies "oh I know. I'm glad they won't be breathing down our neck for once."

"Yeah, I just want to relax all week. I definitely need this, college has been pretty stressful lately. I'll mostly just play video fames and stay up way too late. You have anything planned?" I ask.

She looked over at me "you might as well know since you'll be here... I invited some friends over to spend a couple days here with me. I told them that our parents are so They're on the way now and should be arriving any minute. I know they told us to not have parties or anything. Please don't rat me out."

"Oh, well thanks for the heads up. And you think I'd care if you have friends over? Please, you think too much of me." I chuckle as I reply.

"Oh like that's even possible." She smirks.

"Hey now..." I say as I frown. "anyway it will be nice to have some of your friends around. So how many of your friends are coming?"

She sighs. "Three. Baylee, Jessica and Leah. Please don't bother them too much, my friends probably aren't looking to get hit on the whole time they're here."

I roll my eyes at her insinuation. "Oh yes mother. I'll be sure to brush my teeth and make my bed too."

"Just don't be weird, please?" She asks with an almost desperate tone in her voice.

"Sure, I'll play nice. Are you gonna tell your friends the same thing? Or am I the only one grounded on our vacation?"

She ignores my comment. After a few minutes we hear a couple car doors close. Destiny checks the door and her friends already arrived. She greets them and show

Them in.

Baylee is 5'5", blonde hair down right to her shoulders, 125 pounds and 34 C cup size. She is wearing a dress with flower patterns on it as she walks in.

Leah and Jessica are both a bit chubby, though has many differences between their body style and still attractive. Leah has raven colored hair. She has 36 D cup size breasts, and is rather curvy as well. She is wearing a black shirt and shorts when she comes in the house.

Whereas Jessica is slightly more heavy set of them all, though also has the biggest chest as well at 34 F breasts. She has brown hair that barely reaches her shoulders, and she wears glasses. She's wearing jeans and a green shirt.

All of them are also the same age as Destiny is. They all have bags, wherein Destiny shows them to her room to put their bags there and to talk for a while. I greet them all saying a simple hi as they walk by. Leah smiles and says hi back as they walk away down to the room. While in there they were chatting, wondering what to do. Destiny suggests we could all go for a swim in the pool that we have. Her friends all like that idea and change into their swim suits, then grab towels and walk out through the living room out to the back yard. I can't help but notice them all in their bathing suits. Leah turns to me and says "you just gonna sit there or come out to join us?"

"I'll be right out." I say as I don't even give it a second thought, I get up and change my clothes into my swim trunks as well. I get an idea and also grab my two bottles of whiskey I had stowed away. I bring them out with me as well as some solo cups to the pool area. By the time I got out they were all in the pool.

"Care For some fun, y'all?"

Jess and Baylee cheer a bit while they all get out of the pool. They grab some cups as I pop the lid. I pour us all some drinks and we have at it while we all go back in the pool. Some time passes and we are enjoying the water, playing chicken and the like. Destiny doesn't seem to mind me joining in, though the alcohol may be helping her hesitations. After a while I do need to use the bathroom. I head inside to do so.

While I'm inside they all talk.

"How about we all play the game?" Leah says.

"Which game you talking about?" Jess asks.

"You know which one I'm talking about. We all let oh big brother of Destiny in there to be the judge." Leah replied as she raises an eyebrow.

Destiny has a slight hesitation, though it's always a fun game as well. Plus it's not like she and I were related. They all agreed. I come back out after a couple minutes. The girls all get out of the pool and refill their glasses. Leah turns to me after taking a swig.

"So Brian, we were talking and we all decided we want to play a game. Though in order for us to play we need you to play as well."

"Oh? Sounds intriguing. What is this game?" I ask as curiosity gets to me.

Leah explains "well, your part will be more of a judge for us on four different categories. You rate us on these categories and tell us who wins in each."

"Oh yeah? Sounds simple enough. What would be the four categories y'all are competing in?" I ask.

"The categories are: who has the best boobs, who has the best ass, who is the best kisser, and who gives the best head." Leah states, she smiles as they all awaited my reaction to the categories. My eyes widen as I realize what I'm asked to do. I slap myself as to make sure I didn't pass out and this isn't some sort of buzzed dream. They all laugh as I then give my answer.

"Oh this does get better by the minute. I'm sure glad the yard has a privacy fence. So how would this start?"

They stand next to each other, from my left to right it's Leah, Baylee, Jessica and Destiny.

"The first couple of rounds will start now, we will begin." They all then reach behind themselves and take their bras off. I stand in amazement as they do so.

"Question, can I feel them in regards to determining who I think is best?"

"Sure!" Leah says.

I approach, Leah, with her and her now bare 36 D sized boobs are in front of me. I reach my left hand up and touch her chest. I begin massaging her boobs with my hand, feeling her nipples, watching them get more stuff as I do so.

"Thank you." I say as she smiles.

"Glad hou enjoyed them." She replies.

I slide over to the right. In front of me is Baylee now. She smiles as well. She pooches her chest out. "Like what you see? They feel better than they look." She says.

"Oh I doubt that, they do look amazing." Though I do reach out and feel her up as well. After a minute I pull away and nod to her as I smile.

"Come again!" She says.

I look over and slide to Jessica with her and her huge boobs she has, at 34 F size. I can't help but stare at them.

"My, you do sure have a nice pair." I say

"Why thanks, I grew them myself. Care to make sure they're real?" She says.

I reach out and massage her chest as well. Playing with them for a while. "They sure feel real enough. Like I'd complain either way." I chuckle.

I finish playing with hers and then slide over to Destiny. I give her a smirk "you mind if I do so?" I say as I open my hand and reach out slightly.

"Nope, go ahead. I'm sure this is something you've wanted to do for a while."

"Can't say I haven't thought about it." I reach out and feel her chest. her chest is the smallest though boobs are still nothing to complain about at all. I play with them both, then as I'm going back to in front of them I say "Thank you."

"Ok, so now that I've completed my mammary exam, I've come to my conclusion." I look at them all as I give my judgement. "Round one goes to..... Jessica."

"Yay first point to me!" She exclaims.

"Don't get too much of a big head yet." Baylee says.

"On to round two!" Leah says. "Off with the bottoms!"

They all grab their waistline of their bikini bottoms, bend down and take them off. They step Out of them and put them next to their tops.

I watch them do so, still not believing that I'm a part of this. Now seeing them all completely naked in front of me. They all turn around revealing their backsides to me. I approach and examine them all. They all look so good in their own way. After a couple of minutes I say

"Ok I've made my decision." They all turn to face me.

"This was a hard one as well, you all do indeed look beautiful, though in the end I went with my personal preference, and Baylee, you are the lucky winner of round two!"

She smiles in victory. "Yes I knew my ass was fire."

"Yeah yeah don't get a fat head for your big ass." Jessica jests and laughs. Leah and Destiny also laugh as well.

I ask "ok, so then round 3 is who's best at making out, right?"

"Yes indeed. We all get 30 seconds for these last two events. Who do you wish to test first?" Asks Leah.

"Might as well start with you again." I approach. "Are you ready?" I ask her.

"Ready when you are." She replies.

I smile, we lean in, slowly press our lips together and we begin to kiss. We open our mouths and slide our tongues together. I place my hands on her hips. She puts her hands on my shoulder and the side of my face as well. We continue doing so, and after a bit, Baylee and Jess yell out "time!"

I pull away and say "that was great!"

"Glad you liked it!" She retorts.

I then approach Baylee. We do the same, slowly pressing our lips together. She a bit forcefully grabs me and makes out with me as we continue. In surprise I place my hands on her back as we make out.

"Time!" We hear Leah and Destiny shout out.

"Oh that was fun. You do have a fiery spirit!"

"Oh I am here to win." She excitedly stated as I grin and then approach Jessica. She and I begin to make out. Jessica does use a bit of passion in her as well. After 30 seconds we are told "time!" So We back away and grin. "Great work!" I compliment her.

"Great back at ya."

I then approach Destiny.

She barely even gives me time to prepare as she kisses me. She kisses me and begins to massage my tongue with hers as she presses her body against mine. I can't help but put my hands on her ass as we do so. After 30 seconds we are told "time!" By the others. We slowly stop and I don't even say anything, I back away and then say "this round goes to Destiny. Though it was a close call."

Destiny says "I may not have the sharpest body but I make up for it."

I look at them all a blush as well as we approach the final round.

"So... this last round I guess I'll get to match you all now." My nerves are through the roof at this point. I just think to myself screw it, they're all nude. I reach down and slide my swim suit down and then off. I kick it away. I stand back up to reveal how hard I had become during this whole game. They seemed decently pleased with what they saw, even though I wasn't particularly outstanding in the size department.

I look at them all for a moment.

"Alright, let's do this. Leah, as always, you're up first."

She approaches and starts getting down. "I guess I gotta do well, I'm the only one without a point."

She gets on her knees in front of me. I watch, still in awe of being a part of this, seeing her naked in front of me I couldn't help but wonder how I was going to last now let alone with all four of them.

She reaches up and grabs me, then she slides her mouth around me as she begins. She seems to fo for depth at first, then she keeps it in her mouth and goes to just soak it with her spit, licking it all over, and expands ok that as she licks my balls as well. I can't imagine much feeling any better than this. She then takes the last few seconds to deep throat me. Right as she was told time she just licks me from base to the head. She stands back up and goes back in line.

Baylee approaches next. She gets down and grabs me. "I'll try to top that." She smiles and then starts to suck on me as well. While she holds it. She licks me from side to side as she slowly slides her mouth downward to my base. She does that a couple times and sucks me for a bit longer, then as she is told "time" she slowly pulls back out and then gets in line.

As it's Jessica's turn she approaches and gets on her knees. I sweat a bit as she begins. She sucks on it back and forth a few times, she gently cups my balls while she's at it. She plays with them while sucking on me. "Time!" Destiny yells, eager to get her turn next. Jessica stops and gets back up, returning to line.

Destiny approaches and also gets down. She is the last of the round. I feel a bit less confident I can hold myself at this point but I'll try. She grabs me and puts my head in her mouth. She licks the head while rubbing my shaft with her hand. "Oh shit." I say as she does so as I don't know how I can control myself for much longer. She then used me to deep throat as well, she holds it as long as she can without gagging. As she hears "time!" She pulls back and coughs while getting back in line.

I try to remember how they all felt. I then look at them all and make my decision. "Man, this all was close as well, but this round goes to Leah."

"Yes! I knew I was the best at something." As I think about this, I say "this means that y'all tied. What happens now?"

"Oh, this game is officially over, it only consisted of those rounds. we all know how you scored us and who you like best in terms of the categories." Leah states as They start grabbing their clothes to head inside.

"However if you think the fun is over don't give up yet." Leah says as she passes by me whilst the others already entered the house.

***

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