Adventures in Babysitting Ch. 05: Genevieve

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Experienced friend shares her ways!
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Part 5 of the 5 part series

Updated 11/26/2023
Created 05/02/2023
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My friends Yasmin, Ava and Zoey have told me the craziest things that has happened to them at the end of our senior year of high school. Most of it just makes me laugh. I'm not cruel, I am very happy for them, but part of what my parents raised me to know is treat everyone how you want to be treated and that sex is something personal that is meant to be shared. Part of sharing is the discovery of what you and your partner enjoy. A lot of the fun is just the exploration.

My name is Genevieve or Gen for short. I am 19 years old, about 5'6" tall, have large hazel eyes and long brown hair. My body is very full figured and curvy with 42DD breasts and a bubble butt. I am bi and have for the last year been gaining experience with both men and woman. I am very proud of my body and was raised to appreciate all types of body types and people. I am the youngest of three kids to my parent's Gary and Cassidy Newman. My older sister Eponine (Pronounced Epony) has nothing to do with the family, but my brother Greg and I are as close as peas in a pod even with our 12 year age difference.

I baby sit for the Matthews across the street from us. Their son Max is away at camp all summer so that leaves time for me to hang out with my friend Paul.

Max's older brother Paul is two years older than me. Paul and I used to be real close as kids and then one day all of the sudden in High School, I grew breasts and he turned very shy around me. Paul went away to college and I hardly see him any more. We chat online and play PS4 a bunch but that is not really keeping in touch.

One weekend after graduation, his parent's Mike and Sasha went away on their 25th Anniversary trip and left me in charge of their house while they were away to take care of their dogs, their plants and their mail.

Paul, I learned had started dating a girl named Missy he met in college. I found them on the couch in what I can only describe as an awkward coupling. Missy was kissing his cheek, while Paul was trying his best to get at Missy's fort knox inspired bra. Both were hot and heavy yet very frustrated with themselves.

Paul stands about 6' and has blonde hair cut short and a light 3 day beard, shaved at the jaw line neatly. He is lanky in frame and has small framed glasses. He is wearing kakai shorts and a t shirt. Missy looks maybe 5'8" and has long curly light brown hair that sits loose about her shoulders with glasses. She has a curvy feminine frame under her flowered sun dress. Judging by the four prongs on the bra Paul can't undo, I'd say she has at least EE breasts or larger.

Neither notice me as I stand at the kitchen island and watch them. But some how their awkward attempt at intimacy is begining to turn me on. I always liked Paul and Missy was very cute too. Though I have never been with more than one person at a time I was starting to think that a new opportunity was waiting before me. All I had to do was act on it.

Before I could find a way announce myself, Missy looks back over Paul's shoulder and yelps in surprise when she sees me. "Calm down!" I say, chuckling a bit. "I didn't mean to walk in on the show. But it seems to me you lack direction."

Paul and Missy look at me quizically..."What I mean to say is I can show you how to..."

"Have sex..." Missy says meekly.

"Yes, if you would let me." I respond as I make my way towards them. I'm wearing blue gym shorts and a dark blue tank top with flip flops. I kick a side my shoes and sit between them.

I look lovingly at the inexperienced couple and see I have my hands full with these two. I figure Ill do my best and so I begin. I look back and forth at them both and tell them, rather bluntly "Your kissing is all wrong." And, "Do you two know anything about foreplay?" Both shake their heads no.

"Well then there is only one thing to do. You two need to practice!"

Both look at me confused. But I reassure them that I have thought of everything. "When you kiss, you just don't go for his cock or her breasts. Its a process that is like a sales deal or a contract agreement. You negotiate without saying any words but make your actions say what you want to say. Got it?" Missy looks like she understands but Paul is looking a bit dense after I said the word breasts.

So I do the only thing I could do. I volunteer myself as their,"training dummy." Without explaining myself I turn to Paul and look up deep onto his eyes. He looks like he could melt but I pull his head towards mine and kiss him open mouth as I hold his hand and have another on his thigh. He is resistant at first but gradually he relaxes. He puts a hand on my side and moves his hand up and down my back. He gets it, I think?

I pull away and he has an enlightened look on his face. Missy, with out a bit of jealously in her eyes looks eager for her turn. I turn to her and she assaults me with her full lips on my own. Her large tongue breaks the seal of our lip lock as she finds my tongue and dances the tango with it. I feel a tingle deep down that Missy isn't the problem here! Missy wastes no time caressing the sides of my breasts through my top with one hand and palming my ass cheek with the other, squeezing very hard like I like it.

Missy and I stay entwined just long enough that Paul is beginning to get uncomfortable and slightly jealous. With regret, I part our kissing and turn my distracted attention back to Paul. The next part of foreplay is undressing I don't bother to announce as I kiss Paul again and start to remove his shirt. I tug at his shorts a few times and he finally gets the point and raises his butt up so I can slide them off with his boxers. By this time I shove him back on the couch and lick and kiss him from his neck on down while I use one hand to fondle his semi hard cock. I make sure Missy is watching me, but have no fear, her eyes are glued on me. "Oh my this doesn't look good for Paul later on..."

Pointing at Missy and lip syncing the words, "watch me," I look Paul in the eyes as I take off my tank top and bra in one smoothe motion, freeing my ample breasts as I bring my hands up and run his cock up and down my cleavage as I lick his cock head. I then hold his cock, which has grown to about 8" and lick it up the bottom, avoiding the head. I go down and suck on his balls and as I hold them in my small hands I take his cock in my mouth keeping eye contact with him. Paul groans loudly as I sink down and deep throat him and begin bouncing up and down on him. Missy has her hand on my head and leans against Paul so she doesn't miss a thing. I wink at her and as I come up for air tell her, "your turn!"

Paul gives me a hurt look when I stand up and drop my shorts and panties. My pussy is medium in size and has about two weeks worth of light stubble surrounding it. I look up to see Missy eyeing me up and down. "Oh Paul this really doesn't look good for you," I say in my head as I return Missy's lustful gaze with one of my own.

Missy stands up in front of me. We look each other in the eye as Missy reaches behind her and zips down the half zipper at her back. I reach for the small straps on her shoulders and slowly ease her dress down her arms and off her body on to the floor. I kiss her as with one hand I unclasp the four prong bra, that Paul struggled with earlier, and reach down the front of her very wet panties to feel her pussy with my middle finger. I slide my digit up her slit and she moans into my mouth. I use both hands to drop her panties to the floor and sit her down as I start ravish her!

I nibble on her ears and back of her neck. Missy arches her back and her massive EE breasts entwine with mine as I make sure to kiss and nibble all her erognious zones. I make my way down to her breasts and they simply blow me away. Like my father I am all about breasts! Next to a good cock, breasts are so lovely and so different that I just kind of sit back and marvel at Missy's. Next to their huge cup size her dark pink areola's are at least 5" in diameter, taking up most the front of her mammary, and from excitement are covered in goosebumps. Her nipples are almost pointer finger thick and stick out at least 2 inches. As I suck on them they glide against my teeth like a small finger. Something that I enjoy having done I do to her which is suck in as much breast as possible as I insert a finger into her very wet pussy. Missy cry's out in happy surprise and pushes her sex closer to my probing fingers.

I suck, nibble and lick my way down her body. Missy squirms and groans as I go. Paul is memorized by the two of us together. He strokes his cock as he watches. Eager to join in. I make sure to rub my hardened nipples against hers and it feels like sparks flashed between us. Finally, I make my way down to her pussy. Unlike mine it is freshly shaved smoothe, her large labia lips are red and wet with all her excitement. As I lick her from anus to clit she pulls my hair and holds my head into her sex. She tastes of peaches and honey.

As I tongue her opening I am greeted with a free flow of love juices that I attempt to lap all up. As I pull away from being nearly drowned, Missy squirts three times all over my naked chest. After she sees what her first orgasm has done she looks at me on terror, until I let her know that is perfectly normal and not everyone can do.

Paul makes a point to say, "no one has pleasured me yet?"

By all means I let them decide how they want to handle that. Missy and Paul look at each other and then to me. Missy comes and lays me back on the chase.

She immediately gets between my legs and I feel a tentative tongue lapping at my very wet slit. Paul comes over and attacks my breasts with his hands and mouth. I can feel he was watching me very closely with Missy because I have to hold my breath as he sucks most of my left breast in his mouth while Missy finds my small clit and sucks on it for all she is worth while thrusting two fingers inside me.

At this time I am ready to really play. I sit up and ask Paul to lay down on the chase. I mount his face and Paul wastes no time tasting me and showing how well he could do after watching Missy and I eat each other.

I guide Missy over and have her straddle Paul's groan. Gingerly, she spreads her lips as I hold his throbbing cock in place. First she sinks down and lets the head pass through. Then slowly she takes more inside her. I let her keep her own pace as with one slow drop, Missy inserts most of Paul inside her as her hymen breaks. Her small shriek of pain was followed by a moan of pleasure as she found a rhythm and rode Paul reverse cowgirl style.

I reach over and kiss Missy as we each play with each others breasts. I feel Paul spread my ass cheeks apart to gain further access to my very wet pussy. I feel his increasing groans against my sex, as Missy thrusts herself faster and harder on top of Paul. Her second orgasm is fast approaching.

I pinch and squeeze her thick nipples as she leans back as she and Paul both cry out loud and cum at the same time. Missy thrusts into Paul and eeks out all of the sperm he has left. Missy and I get up off of Paul and Paul exhausted wishes us well and rolls over to fall asleep.

Missy looks at me and says, "I want to play some more!" Since I was so close to cumming I agree that more needs to be done. So I take Missy by the hand and lead her to the Master bedroom where Paul and Max's parents insist I sleep.

I go into my gym bag with my things in it and reach into the bottom to pull out my "special pouch" of toys. Missy's eyes go wide when I pull out a dark blue rubber two sided 12" dildo. I lick the one end of the dildo, as I look at Missy mischievously.

"Ready to play some?"

Missy nods excitedly.

"Get on your hands and knees then," I command her.

Missy gets in position. Her full round ass and her legs spread wide. Her wet bald pussy drips with Paul's cum still in it. The one head of the dildo easily parts her lips as I work it in and out of her. Missy groans and looks back at me with a hurt look in her eyes when I stop.

I get in position behind her, my ass mere inches from hers. I hold the other end and slowly ease it into myself. My loud moan makes Missy turn her head to look at how I am as impaled on the rubber phallus as she is. Looking confused Missy doesn't know what to do next. Without saying a word I push back into her ass with my own driving the dildo further into her. Missy groans with pleasure as she pulls back a bit and does the same to me, our round asses smacking together.

Eventually we get a slow pounding grove going, our breasts swinging beneath us and our hair flying every which way with each thrust. Missy is really enjoying it and I must say she is very good for a fast learner. I reach between us to rub my aching clit as I feel my orgasm building within me. Missy is pushing back against us faster and faster. Her sharp cry's tell me she is so close to cumming. Missy lets out a screaming cry as she freezes mid thrust and collapses on the bed. I let myself go soon after. The dildo slides out of me and with it a huge gusting stream of my love juices spray over Missy and the bed sheets. I have never cummed that hard before to actually squirt! Missy comes and holds me, looking at me with concern. I assure her I am more then fine, and we laid there in our own love mess and fell asleep holding each other.

Paul woke us up way after the time I was supposed to be home. Paul helped us clean up ourselves and the bed. All three of us got together a lot that summer in 2's and 3's. Paul and Missy never lasted longer then that summer, dating wise, but we all became good friends.

The End

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