Babysitting My 16 Year Old Sister Jesse


I walked into the house and plopped my stuff down in the living room. Mom was in a hurry gathering her luggage and such for her 4 day girl’s weekend in Cancun with her friends, so I was enlisted to stay at the house and eyeball my 18 year old sister Jess.

I dropped my bag and sat my laptop and my PS3 down on the coffee table. Mom was a flurry of activity as she rushed her and there in her last minute preparations. Mom handed me $200. 00 in cash, smiled, kissed me and said “Don’t let her drive ya nuts!” I grinned at mom. “It’s cool mom. No worries. You just enjoy your trip and I’ll see ya when ya get home. I love ya…. have a great trip,” I said as I kissed her goodbye. She rushed out, her excitement obvious. Mom needed this getaway.

It had been two years since she and dad split and she hadn’t had a real vacation since before then, so she needed this. I was glad to help her out, so when she asked me to watch Jessica for her for four days I was glad to drag a few things from my apartment and camp at her house ‘til Tuesday. I took Friday and Monday off from work so I could devote myself to Jess.

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   Besides, too much unsupervised time for Jess could lead to trouble.

Jess was 18 We got along pretty well now that I lived elsewhere, so this would be a breeze weekend. She knew she could not have a party or nothing and mom schooled her that her curfew was midnight and she was not to try to manipulate me into stretching it out. I watched mom pull out of the driveway and head for her friend Evelyn’s house where mom would leave her car. The 3 ladies were going to call a cab to the airport. Mom tossed a wave goodbye and off she went.

“Jess, whatcha doin?” I hollered. “Nothing!” she hollered back. “Come on down and say hello!” I asked her. I could hear her trotting down the stairs. As she emerged from the stairwell I was shocked. Jess wore a white and green stripped tight fitting top with spaghetti straps. It clung to her full young tits. Frankly she looked a bit slutty in it, but I knew otherwise. She couldn’t help being built like a vixen, and man oh man she was too.

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   Her black shorts were tight, clinging to her ass and thighs as if painted on. She ran up and hugged me. “Hey Josh! Ready for the big weekend?” she teased.

“Big weekend?” She grinned. “Don’t worry… I just meant ready to have some fun is all…ya know, the cat’s away so the mice can play and all that?” she teased. I shook my head. “Just don’t do anything to get me in hot water with mom. She trusts me to eyeball ya and if ya ever want her to trust ya again ya better behave or next time she’ll send ya to dad’s house, and ya know how boring it is to hang with the old man!” I reminded her. “I will. I won’t do anything to get ya in trouble with mom Josh. I promise!”

“Sounds good! So, what’s first on the agenda?” I asked. She acted as if in deep thought about my rhetorical question. She grinned and blurted out “Cheeseburgers!” “Are you cooking?” I teased. “Nope, but you’re buying with some of that cash mom gave ya. Let’s go to Red Robin,” she enthusiastically offered.

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   “Can I drive?” she asked, hopeful beyond words. I remember being 18 – all I wanted to do was drive. I tossed her the keys. “Wreck my truck and you’re dead meat Bitch!”

We headed out and away we went. Considering I taught Jess to drive, she was good at it. Since our parent’s split two years ago I was kinda dad to Jesse. Although I was only 20, and she 16, the age difference was enough to give me the standing to be an adult in her eyes, although truth be told I was more of a kid than she is. We had a great lunch, shooting the shit, her filling me in on her Summer thus far and her eagerness to begin her junior year in high school. I found myself lost in thought as she talked.

Jesse’s long brown hair lay on her shoulders, framing her soft features well. Her blue eyes sparkled in excitement at every turn. She was quick to flash that toothy grin and her face lit up when she did. No wonder every boy in school was chasing my sister. She was gorgeous, as well as being built more like a woman than a 18 year old girl, albeit nearly 18 Her birthday was next month, in September, and she was so excited. 18 meant only one more year until 18, as if that was the be all and end all.

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   Perhaps to a 18 year old it is.

I went to Gamestop for me to get a new PS3 game for me, and she went to Sephora to get some makeup or something. We met back at the food court and headed home. She drove us as I fondled her bag full of mascara, eyeliner and whatever other things girls paint themselves with, although in truth Jess wore little makeup – she didn’t need it.

I felt guilty as we hopped out of the truck. I was mesmerized at her figure. She had an ass as astounding as her tits. Her thighs were full and muscular. Everything shook just right as she walked and I trailed behind her to take in the view. I felt especially bad that I was thinking sexually of my little sister. I couldn’t help it. Sister or not, Jessica was gorgeous and very, very sexy. I could never tell if she knew it or she was oblivious to the effect she had on men.

Late afternoon found us getting stoned and playing my new PS3 game. We laughed and had a good time.

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   By about 7PM I was ready for some chow and Jess, in a twist of odd events, made us dinner. She made pork chops, rice, peas, gravy and a green salad. I was amazed, not only that she volunteered to do so, but that it was so good and especially that she made killer gravy. I woofed the groceries. “Good?” she teased. “Awesome Jesse! Apparently mom did teach ya to cook!” I eagerly admitted. She smiled and reminded me “I am a girl ya know. Cooking is what I am supposed to be able to do. I don’t want to be just a pretty face. I want to get married and have kids someday so I need to know how to do all this stuff!” she adamantly reminded me.

I was amazed my flighty little sister was so adult and childlike at the same time. I plopped on the couch and turned on the news. Jess went to take a bath and call a girlfriend. I figured I was free for the night – I mean girls and their girlfriend’s on the phone can be an all day affair. I could hear her up there laughing and the occasional OMG! Blurted out as they chatted.

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   Frankly I wished she’d invite her phone pal over – she was talking to Madison, and that was one hot little number for sure. I wouldn’t mind a roll in the hay with Maddy, even if she was a minor and I had just turned 20. Some things are worth the risk.

By about 10:30 I was getting sleepy and bored. I began reading a book on the Germans fighting in Russia during WWII and I guess I drifted off lying on the couch. I awoke to Jess leaning over me. “Josh, go to bed. If ya sleep on the couch you’ll wake up sore, so go to your room young man,” she teased. I let my eyes adjust and boy was I in for a sight. As Jess leaned over me I saw more cleavage than I had ever seen. She wore another spaghetti topped deal, this time PJ’s with tight little shorts that matched, but this time as they were bed clothes, there was no bra. Her nipples were semi-erect and the fullness of her tits began to work on my nether regions.

I sat up and she pulled me by the hand. “come on sleepy head. ” She led me by my hand to my old bedroom.

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   She sort of threw me onto my bed. I watched in awe as all her goodies jiggled and she caught me looking at her not like an older brother, but like a woman. She smiled a very alluring smile at me but never said a word about it. I sat on the edge of the bed and slipped off my shoes. Jess walked out and I rose to close the door so I could change. I undressed and sat in my boxer briefs on the bed as I flipped through the channels on the little 19 inch TV in the bedroom.

I was trying to distract myself, but to no avail. My cock was semi hard and I kept thinking of Jesse in those PJ’s. I lay back on the bed and despite my better judgment, began to rub my cock. I could not stop thinking of Jess and how she looked in her PJ’s. I began to rub my cock in earnest. I slipped off my under britches and stroke my cock as it swelled. My nipples were hard and I felt a bit dizzy. I could still smell Jesse’s shampoo and body wash from her shower and the smell was intoxicating. , fueling my fantasies and desire for her.

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I leaned back and rubbed my cock. I closed my eyes and imagined her naked and near me. I could feel her body in my arms. I found myself lost and disturbed. I wanted to touch my little sister. I wanted to fondle her naked form. I wanted to kiss her and make love with her. I felt embarrassed and angry at myself but the feelings were so powerful and real. I spit in my palm and rubbed my cock. It felt good, filling my hand. I pulled on the head and ran my finger slowly down the underside, heightening the intensity.

I was rather lost in the moment when the door burst open. My eyes opened to a sight I could not believe. Jess was standing in the doorway. The only light in the room was from the TV on the dresser.

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   The hall lights were out but the kitchen night light downstairs flooded the hallway and stairwell with enough light to frame Jess in the doorway. She looked at me as I looked at her. Her form was incredible. The backlight highlighted her womanly attributes to an amazing level. Jess just stood there and never said a word.

My shock was overwhelming as was my initial embarrassment, but Jesse ended that. As she saw me I could see a smile cross her face from the TV’s light. I mean, I was embarrassed, but so far jerking off in the privacy of one’s boudoir wasn’t a crime, so I was more embarrassed at her seeing me than anything else. I mean, she could not know what was fueling my fantasies, I consoled myself.

“Can I help Josh?” she asked, a clear little girl tone in her voice. I leaped up and began to cover my naked cock sticking out from my belly. “Jesse, what are you doing here?” I asked, sounding more angry than I was. She stepped into the room. “I’m sorry Josh, but I heard thunder and I hate thunder. I just wanted to hang out with you until the storm passed.

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   Now I want to hang out and help my big brother with his problem,” she said very quietly as she approached me standing at the foot of the bed.

The room was kind of small and two steps and she was standing in front of me. I was still in shock for the most part, but Jesse was rather intentional and seemingly sure of herself. She put her right hand on my arm. “Josh, don’t be shy. I’m really horny too. I think you made me horny and really came in here to try and seduce you. ” I could not believe how frank and adult she sounded in her words, tone and expression. “I love you Josh. I have had a crush on you since you moved out and I discovered how much I missed you. I want to make love with you Josh. ” Her expression was pleading. I just stood frozen, not sure what to do. My cock however, despite the abrupt interruption, was eagerly hanging at 3/4’s mast.

Jess reached for it with her left hand and very gently fondled me.


   She pulled herself to me and looked up at me. “Make love to me Josh. I know we aren’t supposed to do this, but I want it so bad. I have wanted you for so long. Please Josh,” she asked. Her small hand looked tiny when I looked down at her trying to wrap her hand around my 7 inch cock. “God that’s so nice feeling in my hand. I want it in me Joshua. I need you. ” She leaned up and kissed me. I didn’t return her kiss, but I didn’t push her away either. She pulled me to her more forcefully and kissed me again. She stood at my side more than in front of me and she held my cock more tightly as she probed my mouth with her hot little tongue. I returned her kiss this time.

“Take off my clothes Josh.

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  ” I took a half step back and she looked up at me smiling so sweetly. “I need you,” she added. I pulled at her PJ bottoms and she wiggled her gorgeous ass as the thin cotton bottoms slid past her full hips. She dropped my cock and looked up at me smiling very confidently. She slipped her hands under her top’s hem and pulled it over her head freeing her spectacular breasts. They were full and hung just ever so much. They were fat too and her nipples were hard, the areole covered with little goose bumps. She cupped each breast and whispered. “See how hard my nipples are? That’s what you do to me Josh. Make love to me, please. ”

The moment got to me and I became no longer an observer. I pulled Jesse to me hard and she grabbed me around my neck and kissed me. “God, your body is so hot against my skin,” she whimpered. With no warning at all she pulled at me, leaned her weight against the foot of the bed and let her weight collapse on the bed. She held onto me and pulled me down with her.

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The rest was a whirlwind. With little talk and almost no foreplay at all, she pushed me onto my back. Jesse slid on top of me and rocked herself forward. She then reached down and guided my cock into her. She was so hot and wet. With a few gentle thrusts I was in her tiny pussy and she began to slide forward and back until all of me was in her. Jess grunted at the fullness and leaned down and began kissing me again. Her breasts smashed against my hairless chest. As she slid forward and back I could feel her hard nipples brushing across my own nipples as they too erected to maximum arousal.

“Hold my ass Josh…hold me tight. ” I grasped her cheeks and guided her and she began to shudder. “Oh God that feels so good. It feels even better than I fantasized it would. I fantasize about you all the time Joshy,” she whispered into my ear. She held herself up on her locked elbows and let her glorious orbs hang in my face as she would lean forward before plunging back down to my public bone.

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   I began to bite at her nipples as they brushed my face. She cooed her pleasure as I sucked each nipple into my mouth and she began to breathe heavily, encouraging me to bring her to release. “I’m gonna cum honey…I’m gonna cum…oh God, I’m cumming…” she hissed as her orgasm released.

I held her ass hard to keep her impaled on my cock. She gently rocked up and down as her pleasure passed over her. In the light from the TV is could see a smile cross her lips, her eyes squeezed tightly closed as her orgasm subsided. She slowly released her breath and opened her eyes to look into mine. “I love you Josh,” she again whispered as she began to rock on me again.

“Get on top of me and fuck me Joshy,” she asked. She never let her eyes wander from contact with mine and I was totally engulfed in her heat, my desire and the feelings of incredible satisfaction as I filled my little sister’s tiny pussy. I rolled her over never breaking contact and let my weight rest on her chest. “Yeah, crush me Josh,” she growled. I looked at her. “Put your weight on me. I want to feel all of you.

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   I positioned myself not between her legs but on them. My cock slid across the front of her pussy and distended clit and she began to moan. “That’s it! I feel all of you. My clit is on fire!” I began to pump in and out of her more forcefully.

I worked her over like that until she came again, this time violently and very loudly. She could talk a stream of sex talk, and man did she. “Oh yeah, fuck me big brother! Oh fuck your little sister. God this feels so good. Do you like fucking my little hole? Do ya? It’s all yours Josh. Make me yours. Fuck me Josh, Fuck me hard!” I began to pummel her now. I lifted all the way up and then slammed back into her. She would squeal with every thrust. She then kept me under her spell with her piercing stares into my eyes as we mated. I began to sweat and she rubbed her hands all over my chest, neck and face, encouraging me to fill her with my seed.

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I was hesitant but she read my mind. “I’m on the pill Josh! Cum in me. I want to feel you fill me with your cum. Shoot into me! Shoot it Josh!” She could feel my orgasm build. She placed her hands around my elbows and held onto me as I drove into her, my release on the verge of bursting forth. I pumped once more forcefully and let out a howl as the first spurts of cum shot into Jesse.

“It’s so hard! I’m cumming again!” she screamed, joining me in release. It felt as if a gallon of cum drained from me. The feelings of euphoria were more intense than any I had ever known. My girlfriend is a real hottie, but it never felt like this when she and I were doing the deed. Jess pulled me down to on top of her. “I want to feel you on me Josh,” she pleaded as I continued to slowly pump, then hold still, then pump again. I finally slammed all the way into her and held myself there, my full weight on her, my panting slowly calming. Jesse then wiggled a bit and locked her legs around my waist, her arms around my neck, and she began a dialogue in my ear.

”Oh my God Josh! Oh my God!I can’t believe it! I can’t believe I have made my fantasies come true.

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   Goddamn big brother, you can slam fuck, ya know that?” she teased. I pulled up a bit and she started kissing my entire face and neck. “Don’t pull out Josh. Stay here on me. I need to feel you on me,” she whimpered. My cock was slowly returning to less than rock hard as I gathered my senses. I let my weight collapse back onto her and she held me even tighter to her. I was sure she’d squeeze the life out of me.

I finally rolled from on top of her and lay beside her. She sat up, crossed her legs in Indian style and began a stream of post-coital chatter. I just began to laugh. She playfully hit me. “What’s so funny?” “You are!” I replied. “Oh my God Joshy! I can’t believe it finally happened!” Her smile was warm and sincere as she told me she’d wanted this for so long. She told me when she found out I would be staying here with her for four whole days, she knew we were going to make love.

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   I just stared at her, taking in all she’d said.

The next four days were a repeat of the first. We hardly ever made it out of bed. We had sex about 5 times every day, and were never dressed for more than an hour or two to go out and get food or rent a movie or something. Jess insisted on taking pictures of me masturbating, so I went along. She took some of herself in the bathroom mirror and sent them to my email. She told me they were for me to enjoy whenever I needed her. We spent four whole days pleasuring one another and it was with great trepidation that I waited for mom to get home from the airport. I didn’t want this to end.

I was falling for my little sister, no matter how wrong it was. Our lovemaking was not just sweaty, horny pigs, but actual lovemaking. I began to believe I might be able to love my sister, although I knew for real it wasn’t in the cards, but it was nice to imagine. We played house for four days and I knew then I would forever be jealous of whatever man would be in future taking my place.

Mom got home, gave us both souvenirs, told us about the trip, and we had a welcome home party for mom. It was a little nerve racking because at nearly every turn Jesse would fondle me or some such.

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   I feared her careless little actions might get us caught, but I didn’t fear it enough to make her stop. I too was enjoying the game and the danger.

It wasn’t until Jesse had gone to her room and I was ready to leave that I was gobsmacked with a whole new reality. As I hauled the stuff to my car I came back to holler bye to Jess and to kiss mom goodbye. As I did, mom was busy messing with something. I approached her to give her a hug and a kiss. As I did mom dropped something into her purse and turned to me.

“Josh, are ya sure ya don’t want to stay another night?” “Stay? Why?” I asked. Mom smiled warmly at me and leaned in close. “Well, I know Jess wants more and I could use a good fuck too, so why don’t ya stay tonight and give us both, at once, what we need?” I withdrew in horror. Mom smiled. “Don’t act all weird on me Joshua. I know all about your weekend. Jesse has told me all about it, and here’s the pictures,” she said as she reached back into her purse and pulled out Jesse’s phone and showed it to me. There was the picture of me, my hardon in my hand as cum leaked from my cock when Jess took the picture.

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“Honey” mom whispered at me as I stood frozen in shock, “Jesse and I have many times talked, ya know, like mother’s and daughter’s do. I knew she had a crush on you and I asked you to watch her this weekend so you two could be together. Now I want you for myself too. Jesse and I are both in love with you Josh, and we want to share you, as our own. How about we spend tonight exploring that?” she asked.

Her smile was sincere and welcoming, but I was still so shocked I could not speak. “That’s one mighty cock there young man,” mom said, showing me the photo on Jesse’s phone again. “Got enough left in there for mom too?” she playfully asked as she let her hand fall to my crotch and gently she stroked my cock as it ran down my leg. “I’ll bet you could fill me with that big, pretty thing too, couldn’t ya?” I stood slack jawed as I took in her words, expression and most of all her touch on my cock.

As I stood in disbelief Jesse ran down the stairs. “Stay Josh. Please?” Jess pleaded. I was too afraid to move or say a word until they closed the deal for me.

“Josh,” mom said, “Jesse and I have been lovers for a couple months honey, and we are jealous that we didn’t include you, but we always wanted to . So how about making love to two women who love you more than anything on Earth?” she asked, a tone of pleading, hopefulness and demand all at once.

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   Jess ran to us and kissed mom on the lips. She then placed her forehead on my chin and whispered. “Mom is sooooo hot Josh! Why don’t ya let me and her show ya how much we love each other, and then we can show ya how much we love you?”

Mom grabbed one hand, Jess the other as they led me to the stairs. “I have a huge bed Josh,” mom enticed. “Let’s the three of us go see how well it holds up to the three of us bouncing off the mattress!” I shrugged and figured I was the luckiest man on the planet.

Wait until I tell the story of how that afternoon went. It is one for the record books…. I think!



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