ok guys, this happened a few weeks ago and i just absolutely NEED to tell someone. This story is absolutely full of bad decisions so if you can get past that then read on. Also prepare for horrible grammar and past tense present tense flip flops
Some backstory, im a 25 year old busy (married) professional with children. I hired a nanny (the title says babysitter because come on, thats way hotter. She is in fact a nanny which is basically a babysitter that i pay a lot more.) About 8 months ago. Her name is alyssa. Shes 19 yo petite, long brunette hair that almost touches her bubbly ass, with a perky pair of c cup breasts. Long legs and a very cute face with full pouty lips. Shes very mature and smart as fuck, and insanely professional which helps because it forces me to behave and not say anything too inapropriate around her, and she is absolutely steller at her job. Basically our relationship up to this point has been very professionally platonic though i definitely have jerked off thinking about her often.
So i live in one of those states that was recently hit with one of those pesky hurricanes not too long ago. We live in a part where we were certain it would just pass us until it actually shit all over us. Alyssa was working and it was around 7pm when we realised we were about to get shit on. It was pouring out. Bad thunderstorm. I decided to brave the storm and drive alyssa home in my suv. She lived about 20 minutes away.about halfway through the trecherous drive, it start to get really bad. Like palm trees falling over and shit all in the road bad. Then i heard it. A flat fucking tire. Fuuuck… i found cover at a closed gas station and i got out to change the tire. Even with the cover i was getting whipped by rain. By the time i finished i was soaked to the bone. We start our trek again and finally we get to alyssas neighborhood. Thats when i realised i had another fucking flat tire. We get to her house and i had no choice but to call AAA. 5 plus hour wait. Fucking great. Well atleast i could hang out in alyssas sweet large single story mansion and meet her parents. Maybe they had liqour. “Come on in and let me put your clothes in the dryer” alyssa said “oh, and my parents are out of town” . Son of a bitch i thought to myself. Now im stranded in a sweet mansion with JUST this girl. But, turns out there was liqour so theres that.
“Would you like a drink? My parents keep a stocked liqour cabinet” “yes, absolutely” i browse the selection as i call my wife and tell her whats going on. After pouring a large glass of some expensive whiskey, i start giving myself a tour of alyssas house and its pretty sweet. Huge media room, xbox one, pool table, i quickly realise im soaking her floors. “Hey do you have some dry clothes” i call out into the house hoping alyssa will hear “yeah im looking now. Do you want to shower?”. I see an opportunity “yes absolutely” i need to get this nut out before it gets me in trouble. alyssa finds me and shows me to the bathroom.
I get to business. Strip my soaked clothes off and leave them in a pile on the floor. I start up the shower and as the room steams up i find some lotion and start stroking. Im standing, one hand holding most my weight on the marble counter and the other jerking it. My eyes are closed and im imagining alyssa nude sucking my cock. Her perfect pouty lips kissing my tip as she cradles my balls. Her perfect imaginary tits just bouncing around. *click* FUCK I FORGOT TO LOCK THE DAMN DOOR! I open my eyes and i see alyssa just standing there looking down at my hand wrappes around my hard cock. Literally an eternity passes, me standing frozen looking at her staring at my cock with her mouth gaping open “Holy fuck im so so so sorry” she finally stammers out as she drops the towel and dry clothes in her hand and covers her eyes with both hands and begins frantically backing out, leaving me standing frozen naked and speechless in the bathroom. I jump at the door and close and lock it. My erect dick just bobbing around as if laughing at how stupid it makes me. I reach for the whiskey on the counter and drown it, then i get in the shower, turn it to cold as fuck and just stand there contemplating on if I could just jump out of a window, run into the storm and start a new life as like a crabber or something, I dont know, but i definitely need to change my name. Maybe ill just fire her. After standing there for about 15 minutes screaming on the inside i decide to get out and face what is coming to me. I dry myself off and grab the clothes off the floor and get dressed. Im wearing what i assume is her fathers clothes. Sweat pants and a plain white shirt. No underwear. Great, now i have to free ball in sweats around this girl while having blue balls. Just my luck. I wonder out and i find alyssa sitting in the media room staring at the tv which was playing an infomercial. I see a glass of liqour in her hand. I can hear the storm still raging outside.
I swallow and take my step into the room, she hears me and turns to look at me. “Oh hey…”…. “thinking about buying a shamwow? Heh” i say pointing to the tv “heh yeah”………………..
Awkward as fuck. I try to make small talk but i know all shes thinking about is the fact she just caught her employer jerking off in her bathroom. Fuck it, i have to bring it up “look im really sorry abour that” she downs her drink. “Would you like a drink” she asks looking back at me? Sure. As she jumps up and goes to the kitchen to make me a drink. I decide its probably best that i stop just standing there and have a seat on the couch. She comes back hands me a glass of whiskey and sits down with a full glass in her hands. I take a sip and try again “im really sorry-” “its fine its just… were you… masturbating?” “Uh uhhhh uh, yeah…” and she starts to fucking giggle. “What is funny??” I stammer, confused at her reaction. “Paul (my name is paul) why the fuck were you jerking off in my bathroom” she laughs harder. “I dont fucking know!” and i start to laugh too. After sitting there awkwardly just luaghing we both finally start to calm down. “Lets just never speak of that again” she says wiping tears from her eyes. “Yes please” and we start watching tv.
About 45 minutes go by. We were just talking about random stuff and watching infomercials. I start relaxing about the incedent and i actually begin to enjoy myself. Alyssa seemed to be enjoying our conversation too. We were talking about aliens or something. I begin noticing what shes wearing. She has some purple booty shorts on, a grey wife beater and i can see a fancy red and black lace bra under it. I notice how short her shorts were. She was sitting with her knees together and her feet to the side propped up on the couch. I begin looking at her long tan legs, her sexy thighs. I wonder what kind of panties shes wearing ” paul” she shakes me out of my daydream and i realised im obviously just checking her out. “Yeah sorry what” i lock my eyes on her pretty sparkly blue eyes “day dreaming?” she asks, as her eyes drift downwards straight to my cock. I look down and notice im a little hard and on full display in these fucking sweat pants. Shit! Her eyes flash back to mine “sooo um, like, why did you decide to masturbate in my bathroom? Haha, like what got you going?” My eyes widen as i throw the question around in my head. “Uh, welll..” i studder out not knowing how to answer. She cocks her eyebrow up at me, giving me an almost devious look. Fuck shes hot. “W-well i dont know, just sometimes a guy gets an urge and i thought it was an opportune time” she looks at me dissatisfied. “Well, did you finish..?” She says with an even more devious look on her face “i-i dont think we should be talki-” i start but she cuts me off ” its just a question, haha” im in shock. Is she really asking me if i busted a nut in her bathroom? Is she really insisting on staying on this subject? My mind races until i decide to simply just answer “no. No i didnt. I mean how could i? You walked in. Kinda killed the mood hah” ” well im sorry i interrupted… Dont guys get like blue balls or something?” “Yep” i answer, noticing the uncomfortable sensation in my balls. Where is she going with this conversation. What is she getting at. Then as soon as i think this she answers my question. “Can i just tell you something” i nod my head “ive uh, never seen one that big..” i feel my jaw drop and i just stare at her. Now im not huge, im pretty average, so i was shocked by her remark but i was even more shocked that she would say that to me. Her boss. About my penis. Shes staring at me, awaiting my response. I see her bite her lip. Shits about to get real
The storm outside is intensifying and it’s orchestra is playing mainly percussions. I stare at her, unsure about what to say, her eyes looking into mine. Then her eyes begin to wonder down again and i see her eyes widen. I look down to find my dick standing at full attention, making a perfect tent in those stupid fucking sweat pants. I slip out a “Fuck” and grab a pillow from the couch and slam it onto my lap. I look up at alyssa smiling at me “i guess youre still pretty excited eh” she giggles out. I now notice how close weve slowly shifted to each other on the couch. I start full on panicking. “Look, im really sorry, i know tonight has been weird im so sorry” i start apologizing” “paul, just relax, no need to apologize” she puts her hand on the pillow and she does it in a way that presses her breasts together. I cant not stare at her cleavage. “Ok ok, we’ll talk about something else” she says I draw my eyes from her cleavage and back to her eyes “let you settle down a bit” she teasingly says with a wink. She moves her hand back to her lap and I let out a sigh. “Ok sooo” she ponders, I feel my excitement settle as I calm my mind down. “Oh! Did you know I dance?” Very odd change of subject, I thought to myself, but I’ll take anything to get this sexual tension to settle. “Oh yeah?” “Yeah, I cheered in high school and after I got into hip hop” “oh that’s cool!” I answered blandly “Yeah, I’m really good at twerking”. What. What??!! My mind exploded. This girl is not trying to change the subject. Not at all.. I just stare at her. “Wanna see?” I feel a look of utter surprise flash across my face and I feel my head automatically nod slowly. She smiles at me and gets up. I take in the full extent of what’s about to go down. I watch her as she takes a few steps towards open floor in front of the couch. I watch her ass jiggle with each step, I notice how incredibly short her shorts are and I realise I’ve never seen her in such a revealing outfit. Her bare shoulders arch as she prepares for her show. She kneels down, puts her knees and forearms on the floor. I shift in my chair to prepare myself for whats about to happen, pillow still on my lap hiding my once again excited member. “Oh shit, I need music! Can you grab that remote and put something on pandora on the tv” i look at the remote at the other end of the room on the table. Well shit. I awkwardly stand up, clenching the pillow to my groin, Alyssa laughs, “oh come on, no point in hiding it anymore!” I silently agree and toss the pillow and walk, now almost proudly, to get the remote. Full erection and all. Alyssa just staring at it, on all fours on the floor. I get back to the couch and put some booty shaking music on and hit play. “Ok good. Ready?” I nod. The situation is as awkward as it is hot and I decide to just roll with it. She arches her back, sticks her fine round ass in the air and begins the greatest twerk I’ve ever seen. I’m in awe. I feel my hard on (still openly pitching a tent) quiver with excitement. This is hot as fuck. My babysitter is twerking in front of me. Alyssa keeps looking back at me, her eyes instantly honing in on my excitement. She drops her torso to the floor and and her shorts jack further up, her ass now on full display. I sit on my hand so i dont start touching myself. This goes on until the song ends. She gets up laughing “so am I good?” I look down at my hard cock “absolutely” she walks over to me “….want a lap dance?” She quickly says. My fucks disappear “yes absolutely yes” she smiles and mounts me and begins grinding me as the next song starts. Her breasts are in my face and her pussy is grinding against my hard cock, with only a few pieces of clothing separating the two. She let’s out a soft moan into my ear as her rhythm picks up, basically dry humping me. She dismounts me and turns her body to face away from me. “I can dance better without these” and with that she drops her shorts and kicks them across the room. She’s wearing a black and red laced thong to match her bra. Her ass is gorgeous and her long legs accent it perfectly. I go to grab her ass but before I can she sits on my lap and begins grinding her perfect ass into my erect cock, she leans back, arching her back, separating her legs, and she wraps one of her hands on the back of my head. The other hand, to my shock, goes between her legs. She turns her face towards mine “im so fucking wet” she whispers. This has gone from 0 to 100 real quick.
Finally, the song ends and one of those annoying pandora ads come on. Kind of halts things for a moment. She slides to my left onto the couch, her legs draped over my lap.”did you ever know?” She asks breathlessly, looking at her glistening fingers “know what?” “How into you I’ve always been” “I had no idea, you kept your secret very well” “can’t say the same about you” she said with a laugh, “I always catch you checking me out.” We continue this kind of joking conversation for a bit. The music already started again but we just talked. Talked about how into eachother we are. “When you were in the bathroom…. were you thinking about me?” I look at her “maybe?…” “what were we doing?” I hesitate. Am I really having this conversation with my babysitter? Was I struck by lightening and am now just dead and in heaven? Am I dreaming? Finally I tell her “you were, uh, sucking my dick” she smiles at me “that is my favorite thing to do….” She says with a cute little teasing look on her face, she bites her lip as she peers between her legs at my still throbbing hard on ” Can I see it again?… I didn’t like, get a great view before, hehe”. I hesitate, my actual mind screaming at me through the clouds of hornyness. Do not fuck your babysitter! She broke my inner argument “here let me..” and with that she swooped her tank top off revealing that sexy little red and black bra. She stands, putting her body on full display, doing s little turn with her hands on her hips, letting me see her perfect booty. My instincts take over, I grab her hips and and firmly but gently toss her across my lap, her stomach on my thighs and her ass in perfect position. I give her a firm slap on her ass and she lets out a moan. I give her another “mmm more” she almost whispers. I give her three more with more force. I see my hand print develop across her ass. I don’t know why I decided to do this but I knew she needed a good spanking. She was being very bad. Then I slipped my fingers down between her ass to her pussy. She’s soaked. I can feel it even through her panties i start massaging my fingers on her clit. She’s squirming and moaning, she moves her hands up over my knees and to her panties and she slides them down to her bent knees. I slide my fingers between her lips, across her clit and then I slide two inside of her. She let’s out a loud moan as I feel how incredibly tight she is. I continue twirling her pleasure with my fingers, her body quivering. I take my other hand and unclasp her bra. I need to see her breasts. She must of sensed this because she gets up, pulling away from my fingers, steps one foot out of her panties and mounts me again. She looks me in the eyes and she shifts her shoulders allowing her bra to fall. I gaze at her breasts. Perky and beautiful with little pink puffy nipples. My mouth automatically go to them. My tongue twirling and flicking her now erect nipples. She wraps her arms around my head and squeezes a little. I can feel her hips gyrate her bare dripping wet pussy on my hard cock. She pulls her breasts away from me, lifts her self off of me and drops to her knees in between my legs. I know what she wants. She is silently looking up at me, her eyes begging me. I grasp the sweat pants and slide them off, she quickly assists and before I know it, my dick flops out and is laying against my stomach. A string of pre cum dripping onto my fuzzy stomach. She stares at it a moment then slowly grasps it. Her touch on my cock was the greatest feeling I’ve ever felt. She spit on my cock and began moving both of her hands up and down my member, her eyes locked onto mine. I notice the storm outside. It’s sounding louder than before. The wind making the concrete house creak.
Her lips meet the head of my cock and she lightly kisses my tip, then licks the pre cum off of it and proceeds to swirl her tongue around. She lowers herself, running her tongue along the extent of my cock to my balls. She began heavily licking my balls as her hand massaged my cock. She led her tongue to my taint and she began licking my ever so sensitive taint. Thank God I recently shaved my balls . She lifted her head and pushed my cock into her mouth and down her throat then up and down again, taking in my entirety. I grabbed her long dark hair and began pulsating my hips, holding her head firmly by the hair. Once I knew she could take it, I pushed my cock into her mouth with some force. I was face fucking my babysitter. She came up for air, a string of spit connecting my cock to her lips “told you this was my favorite thing” she went to put my cock back into her mouth but I knew I couldn’t last much longer. I grasped her shoulders and guided her body onto the couch, laying on her back. I move into position between her legs and take my shirt off (I know, finally! I was awkwardly just bottomless for a while.) She reaches up to stroke my hairy chest but I press her torso back down and begin kissing her inner thighs “wait no, I’ve never been eaten out before” I stare at her blankly “what?!”, “Yeah the only two people I’ve been with didn’t like doing it” she said breathlessly “well you’re in for a treat” and with that I begin licking her wet pussy, her excitement soaking my face. She tasted fantastic. I could feel her body squirm as I moved my tongue across her clit. She was moaning loud. I slipped my tongue inside her and and back to her clit, sucking on it while I flicked my tongue across it. I had to hold her thighs down from her squirming so much. Her moaning getting louder and louder and her breath quickening. Then her body went limp and I knew she reached her nervana. Then her thighs grasped my head as she screamed out a satisfied moan and then it happened. A stream of her squirted me in the face, soaking everything. Holy shit Alyssa just squirted on my face.. This is the best night of my life. I could feel her thighs quivering as more gushed out of her. Finally she released her thighs grip on me and I got up. I looked at her as I wiped my face off, her beautiful breasts heaving up and down and and her gorgeous thighs quivering. She laid there with her eyes shut, satisfied. “That was…… fucking amazing…” She managed to say through heavy breaths. She was absolutely beautiful laying there. “I want you inside of me” she said, suddenly lifting her self up on her elbows, desire burning in her eyes. “Please…. fuck me”
I wipe off my face and positioned myself between her legs, running on pure primal urge, I grasped her hips and slide her closer to me. I grasp my cock and begin massaging my head on her swollen clit “mmm put it in, please, don’t make me beg” I look up at her and she’s biting her lip, she wanted it. I teased her a bit more then slowly pushed myself, just the tip. She was incredibly tight. Tighter than I thought so I wanted to be easy. She didn’t. She reached up, grabbed my ass and pushed me into her. My entirety entered her and she threw her self back, her back fully arched and I began the dance of dick. I continued but knew I had to stall. I wanted this to last forever, so I pulled out and flipped her. She instantly obeyed and pushed her ass in the air and stretched her torso down across the couch. I grabbed her hips and pushed myself into her. Her beautiful moans filling the room, drowning out the booty shake music and the storm outside. She responded with my thrusts and we fucked in unity. “I want you to go on my face” Alyssa almost screamed, in full ecstasy as I fucked her hard. “Then you should move. Like now” I felt myself getting close. I stopped and sat back and she went straight between my legs, my dick to her lips and she began licking her off of me, genuinely enjoying every second of it. She took me into her mouth s a few times then began stroking my hard member with one hand while she massaged my swollen balls with the other. This girl was a pro. She looked up at me as she did “don’t hold back, I want it all. I love cum”. I could marry this girl. As she stroked and as she massaged and as she looked up at me with those sparkly blue eyes, she stuck her tonue out and placed it at the head of my dick. I felt it building. I looked down at her perky breasts bouncing with every stroke of her arm. “Please. Cum for me” she whispered. That sent me over the edge. I exploded, shooting cum all over her beautiful face. I shot strings across her lips, into her eye, across her forehead and in her hair. Hours of build up released all over Alyssa. She smiled a big smile as I continued to cum onto her. It dripped and streamed down her chin, dripping on her breasts. She was covered. She continued stroking my cock until she got every drop out of me, then she leaned back and looked up at me “holy shit that was a lot” she said, rubbing it away from her eye. I laid back on the couch, took a deep breath and waited for the guilt to wash over me now that it wasn’t being shrouded by horniness, but it never came. I felt genuinely good about my choices. “Can I grab you a paper towel” I ask, looking at my cum covered babysitter. “No it’s fine” she said smiling, then she started licking it off of her, wiping it with her fingers and licking them. The storm outside seemed to be settling down now. The wind didn’t seem so harsh and the rumbles of the thunder seemed to be distant. I see flashing yellow lights through the window and I jump up, still naked, to go see. It was the AAA tow truck. I quickly go to the restroom to clean up. Alyssa knocks on the door while I’m in there and when I open she hands me my now warm and dry clothes. I get dressed and we walk to the front door “well…” She starts “it’s been fun!” “Yes it certainly has been” we have a quick hug and I run out into the rain to get in the tow truck.
Alyssa still works with me, and actually I gave her a raise. We still hook up occasionally but it’ll never be as great as that night I got stranded at her house.
Source: reddit.com/r/gonewildstories/comments/77b2zo/mf_stranded_with_the_babysitter_very_long