Diary, Anal, Bi-sexual, Blowjob, Consensual Sex, Cum Swallowing, Female / Girl, First Time, Foot or shoe fetish, Lesbian, massage, Mature, Oral Sex, Virginity, Young
My life is pretty much as ordinary as any other teen schoolgirl get up early walk to school do your classes finish your classes walk home have diner shower masturbate then go to bed and repeat the whole process the next day i was over being common i wanted excitement in my life like i don’t want to wake up in a different country every dayor anything like that just a little thrill that makes people look forward to waking up the next day.
My name is Jessica I’m in my early teens slightly flat chested bit chubby around the edges have shoulder length brown hair and the pretty brown eyes to match I’m in the middle of high school and i feel more alone than ever I’m not popular i have a friend here and there never really had a boyfriend i only had a friend with benefits that never really went anywhere past the point of touching my boobs.
Ok got that out of the way so being in a small town i don’t really have a lot of people around my age to interact with apart from the ones i know or the ones that know me but treat me like i don’t exist but the weird thing is i see a lot of older people, I’m talking like people in their 20's older guys and they seem to know how to hold a committed relationship and people always say the older you are the more you know whenever i walked around town i just look at them and think being an adult must be so much more exciting than being a teenager, later on today while i was in computer class i waited till the teacher was away and began to search for porn videos containing young teens with older men obviously i could only find videos with people as young as 18 but that was good enough i guess i did find a range of videos on this porn site i decided to play one luckily for me i was sitting in the very back corner alone, i plugged in my earphones so i wouldn’t get heard as the video played it was very standard porn basic sex cumming inside her done but the part of the video that was so hot for me that the guy was at least 20 something years older than her i kept watching more and more as the videos were playing I guided my hand down to my pants and began rubbing my pussy over my cotton panties i was pretty much in another world i had to shut of the video and get back to work i don’t know how crazy i would’ve gotten but one thing i knew for sure i needed to start talking to new people and getting this experience and i need to find a way to contact them.
Once the weekend arrived i went to my local library to use the Wi-Fi cause my parents are to shit for Wi-Fi, i arrived and connected my phone and began to search on the net for chatrooms , apps whatever i could find i came across an online chat site i made a profile and called myself BabyDoll uploaded a picture of me in my swimming bikini as my profile pic and set my age to 18 i made my way through the chat site there were chatrooms for specific fetishes and towns , some of the fetishes I’ve never even heard of scat , incest , femdom , pov ect i didn’t know what any of them meant but i want to focus on the town specified chatrooms i scrolled through and found a chatroom for people in my town i signed up and found so many member’s i messaged a fair amount of older men and women not saying anything fancy just that I’m new here and looking to try new things with new people. I need the adult attention luckily me being a girl i had a lot of thirsty guys to choose from but right now it was just first in best dressed for me and the guy that could meetup with me the soonest his name was DaddyJoe he 34 and had a picture of his cock as his profile picture, his cock was clean uncut and shaven must of looked about 9 inches i had no idea what he looked like but he sounded nice we chatted for a while...
DaddyJoe: Hey there Dolly you have a beautiful little body there
BabyDoll: Hi you have a nice doodle
DaddyJoe: i bet you would love to have it inside your tight wet pussy
BabyDoll: maybe i do he he would u teach me how to take it I’m a complete virgin
DaddyJoe: I’m sure i can do that I’m free tomorrow if you wanna meetup and fuck
BabyDoll: I’d love to but i just got to let u in on a secret im actually 16 please don’t be mad at me i won’t tell anyone
DaddyJoe: mmm i do love a younger girl but you have to promise me to keep it between us
BabyDoll: I promise ;)
DaddyJoe: i will get us a hotel it will be more discreet I’ll send you the address what time?
BabyDoll: i get dropped off at school at 8am and can sneak out around half past
DaddyJoe: perfect I’ll see you then
Later tonight in bed i just couldn’t get to sleep i just kept on imagining what it’s going to be like and how naughty this is going to be i was feeling a mixture of emotions excitement, fear and horny definitely horny.
After what seemed like a lifetime of waiting the next morning officially arrived i awoke to the sound of my alarm clock going off for me to get ready for school i pretty much leaped out of bed like the opening to American Dad that how happy i was to be going to "school" , my school clothes were ready for me to wear as always i also managed to raid mum’s makeup cabinet while she was asleep to dolly myself up nothing to fancy bit of dark eye shadow not too much around the eyes foundation here and there enough to look slutty with a dash of innocent.
Mum finally dropped me of at school as soon as she left i went to the toilet block to wait out for the bell for rollcall once the bell rung i waited just an extra 2 minutes to give people time to get to their classrooms finally the coast was clear i snuck out of school grounds and made my way down one of the side streets near my school, on my way out i got a text from DaddyJoe telling me the address it was a few blocks away and in a pretty quiet part of town i guess that’s what he meant by being discreet.
I found my way to the hotel i was out the front his room was at the back of the hotel complex i walked to the door and took a deep breath and knocked .
I was greeted by a slightly fit guy not to mention very handsome for a guy of his age he greeted me with a smile and invited me in i got more and more nervous as i walked into his room he seemed nice he introduced himself as John and shook my little hand he offered me a glass of wine he told me it helps with the nervousness I’ve only ever had sips of cider before never really had anything as pure in alcohol as wine but today was going to be a day of firsts for me so i took him up on his offer.
After a few swallows later i became more and more relaxed and my nerves began to recede but still a tad nervous we did chat for a while asking what we enjoyed what kind of porn we watched just getting really social with me while at the same time looking each other up and down.
John came closer to me and put his hand on my thigh and massaged it gently this made my heart skip a beat at his touch i still continued to drink as he moved his hand up and down closer to my pussy his hand was now under my skirt bushing against the edges of my panties he looked into my eyes as his hand brushed over my cotton panties his finger pressed harder on my clit and dragged his finger down my slit my panties were soaked and i was getting very turned on i knew what was going to happen next i needed more alcohol in me i reached out for the glass of wine and skulled it in one big gulp and laid down ready for John to do whatever he wants to me.
John reached around the waist band of my school skirt and pulled it down along with my panties exposing my wet hairless little cunt he began to massage my wet clit you could see the drips of my juices run down his finger as he pushed his finger inside my pussy, my pussy began to puddle the deeper his finger went i was enjoying this feeling until he reached a barrier in my pussy or what i was taught "the hymen" John withdrew from my pussy then moved his tongue up and down my slit and flickered over my clit sending me into waves of little tingles inside me making me shake i couldn’t help but grip his head firmly and smush his face into my cunt it was driving me insane i feel like like my pussy was going to flip inside out my breath got shorter and shorter and my pussy spasmed splashing Johns face in what i thought was pee but then realised for the first time in my life i squirted John went back to lick all the wetness from my pussy making me tingle with every lick.
I had to recover from that intense orgasm as much as i wanted to go further i needed to drink and let my pussy cool of John returned up to me and poured me more wine i drank it like water gasping for air i looked up at him and told him how good it felt like I’ve made myself cum from fingering myself but never came this hard from my finger and this all happened from a man’s tongue.
John came up next to me and asked me if I’d like to make him cum the way he made me cum i was eager to play more all i could do was nod my head and reach into his boxers to grab something big and hard my little hand just managed to grip it all the way around i had no idea how I’m going to fit something this big inside me.
I began to run my hand up and down Johns shaft slowly being a little tease but John wasn’t a patient man i gathered as i felt his hand on the back of my head gently pushing my mouth towards his cock i opened my little mouth to swallow the head of his cock i sucked it like a lollypop at first then moved my mouth deeper down his shaft my little mouth was full of cock after going down 4 inches’ i could feel the head of his cock pushing the back of my throat he kept pushing till a few more gulps his cock was pushing into my throat hole i swear it felt like he was going to hit my tonsils, John lunged out of my throat his cock was glistening wet with my saliva John looked up at me I went on to his cock and took it back down my throat going all the way up and down jerking his cock while sucked hard on the head of his cock pumping it hard and fast flickering my tongue over the pee hole John began to yell out I’m going to cum he withdrew his cock and held my mouth open he furiously jerked of in front of me until shots of cum came flying out of his cock into my mouth all over my lips and chest i swallowed all that was shot in my mouth the cum felt warm and gooey as it travelled down my throat followed by a salty after taste i licked what cum remained on my lips and massaged the cum on my chest into my boobs.
John looked very surprised at what i was doing with his cum i guess as far as first timers go i was a quick learner that and i read that guys love it when girls play with cum in the most kinky ways.
I laid back down on the bed with john as we both recuperated from our intense orgasms we drank the rest of the wine as we sat their panting like crazy by this moment i was really buzzed i could see Johns cock rising under the covers looks like round 2 was on its way i pointed at his hard cock showing him he is hard again he then asked me what i wanna do next at this moment i didn’t know what to do i did tell him i want to do everything within limits i just told John to surprise me, John gave me a smirk and led me of the bed and bent me over he ran his fingers over my back gently while lightly scraping the tender parts of my back with his nails i quite enjoyed this the small amounts of pain was making my pussy drip i guess this got John's attention as he spent more time scratching me this time he scraped harder and went from the tip of my spine to my asscheeks
"Don’t Stop!" i yelled
I rubbed my clit as he dug his nails into my back i felt his hand slap my ass hard making a moan escape my mouth then again his hand went harder across my ass cheeks the pain was really turning me on
"fuck me fuck me" i yelled
i wanted to be fucked hard i wanted the pain to evolve, John positioned his cock at my pussy the head of his cock slid inside me my body shuddered as my virgin pussy stretched he suggested we go slow as its my first time but that’s the thing its my first time i want my first time to be brutal and painful not slow and steady i wanted it to happen this way i told him to go for it John withdrew his cock and ran
it up and down the folds of my pussy lips lubricating my pussy with his precum i tooka deep breath and felt his cock lunge into me piercing my hymen pushing as deep as his large cock could go i felt my pussy tear i could feel blood dripping down my legs i felt like there was a roll of salami inside me the pain was crazy but the feelings it was giving me was amazing i could feel John struggle to move in and out of me my pussy was that tight around his cock my pussy eventually gave way and gave him more room and lubrication to pump my little my pussy he wasn’t holding back he was pumping into me like a jackhammer my screams were to loud even for me i grabbed
the nearest pillow and shoved my face into it muffling my screams.
Johns cock expanded in my pussy letting out a giant blast of cum overflowing my pussy forcefully pushing him out the rest of his cum dripped all over my ass there was so much as i raised myself higher a river of cum poured out of me all over the
floor.
The river of cum inside me began to reseed and managed to keep a good amount of it inside me, John suggested that we prepare my ass for his cock considering its a lot tighter and closed in than my pussy , i laid back on the bed and exposed my asshole to John he rubbed my asshole lightly then with his other finger he pushed deep into my cum filled cunt and started digging his cum out and adding it to his other finger using it as lube to slide his fingers i could feel my asshole clench around his fingers as he slid them inside my ass one by one until he got to his thumb that took a major shot of pain inside me but still bearable he continued fingering my ass as if his fingering my pussy hard and fast the feeling was getting less painful and more pleasurable as i felt my asshole open up more to his adult sized fingers i took my own fingers to my clit and rubbed it hard screaming "finger my ass daddy" i honestly don’t know why i said daddy but it made me feel more slutty and it seemed like john liked it to when he started ramming both my asshole and my pussy with his fingers but he was going hard he loved being called daddy so i yelled at him
"daddy'' "daddy" "daddy"
we were both enjoying the feeling of both my holes being fully pleasured next minute i heard a slight vibrating noise at first i thought John had a vibrator stashed around here somewhere i then realised what time it was and it was my mum calling me i answered quickly
"where are you school was out 5 minutes ago" my mum blabbed at me i really wanted to be fucked in the ass but was short on time i had to come up with some excuse i went back to the phone and tried working my mouth to come up with an excuse but then John comes sits next to me and works his hand on my clit causing my voice to sound more out of out of breath i did everything in my power not to
moan while talking to my mother mum noticed my breathing and asked me where i was and then the excuse came to me i explained to mum that my last school period was a free period so i went jogging at the oval around the block i told her i will be there in 20 minutes thankfully she bought it and i got of the hook i got of the phone and planted a firm kiss right on Johns lips and took his cock in my hand i told him i have to go in 20 minutes John looked disappointed i turned his head to mine and told him
"lets get this big dick in my ass"
John smiled I took Johns cock to the back of my throat just to add that extra saliva on his cock and bent over and guided his cock to my asshole John was definitely taking his time i was worried we wouldn’t have enough time i pushed into john a bit more taking the head of his cock into my ass then that hit the very top of my pain barrier i bit down on my lip as hard as possible i egged him on to keep going John pushed deeper into my ass i shuddered as inch by inch went into my ass my lip was bleeding from my teeth sinking into it John was fully inside my ass I could feel the head of his cock breaching my colon if he pushed any further he would be fucking my stomach
he slowly plunged into me fucking me slow and steady i looked at my phone and saw i only have just over 10 minutes left i told him we need to hurry i gripped both sides of the bed and buried my face in the pillow and wriggled my ass to signal him to fuck my ass hard Johns cock went all the way back out of my ass just so the tip is inside me then BANG deep inside me again he continued ripping into my ass harder than he was in my pussy i clenched at the bed as his cock fills my rectum my mouth was full of pillow at this stage his cock was so big compared to being in my pussy i felt a massive sigh of relief as i head something warm and hot splashing up against my colon now that was the most pleasurable part about anal the dick in my ass hurt like a bitch but having the cum inside my ass was worth the pain, as John removed his cock my asshole morphed back closing me up keeping his warm cum fully inside me.
I had only minutes to clean up i felt bad having to ditch him so quick I’m so glad he understood i gave him a kiss and told him ill message him online.
Once my mum picked me up i felt like a different person i spent the whole night in my room tasting myself and thinking about the fun i just experienced i still had cum leaking out of all three of my holes i was definitely pleasured out all 3 of my freshly fucked holes were aching from the intense pounding they all took.
Over the next few days while i was waiting for my holes to heal i went back to that online site interacting with more people lucky for me there were millions of horny guys keen for a root i knew i would have no trouble in the future if i ever need a quick screw.
I want to try something more exciting so I came across a few women’s profiles sadly there wasn’t much of a variety of women on the site just full of thirsty men there were about 4 women on that i was looking at , i was always straight but going through their profiles seeing their naked bodies and sexy poses kinda made me tingle downstairs.
Three out of four women on the site were into girls and guys so i decided to go ahead and message them after a few minutes of waiting i got 3 responses i told each of them the same thing
"I’m not really 18 and looking to experiment with older people i recently just got my ass mouth and pussy fucked by an older guy from this site but now im curious about trying things with women hopefully somebody can point me in the right direction"
One girl who was 24 told me to fuck off, another woman her name was MaggieCakes who was 53 responded with a kind message asking me how i am and that I’m a naughty girl doing what im doing and that she likes it followed by a bunch of flirty emoji’s she was really tech savvy for her age.
The other woman was quite the opposite to the other woman who replied to me her name was SexySuzzy and she was 22 she was more attractive than the other woman but had less of a welcoming vibe as all she said back to my message
i decided to peruse with the 22-year-old as she seems to reply a lot more quicker we covered a lot in our time of talking we learned she lives by herself and only lives near the local library she then went to ask me to come over and I did have a couple hours left at the library till my mum had to pick me up so i thought why not at least this way i can get pleasured and give my insides a time to recuperate.
SexySuzzy told me to lookout for a woman with long straight light brown hair wearing track pants and a yellow jumper i told her that i was wearing a black crop top and baggy shorts and told her to meet me near the geography section of the library the geography section was pretty big like a maze so we would have a little fun trying to find each other.
Time went by i trotted around the geography section excited and nervous waiting to find this woman i turned a corner and found her she was more attractive in person i was staring at her ass in those pants it was making my pussy drip at the thought of me spanking that ass , she came in eye contact with me and kind of gave me a look to follow her.
i followed the woman through the library to the carpark and got in the car there was nothing but silence for the first 5 minutes the attractive woman broke the silence "nervous huh" she questioned i was actually really nervous to be honest i never thought id see myself having sex with a girl ever i was fine with the guy because i was attracted to guys but this is different.
She introduced herself as Laura and told me she’s only been with a couple girls herself but never with one as young as me so she was a bit nervous to then followed by placing her hand on my thigh i remember when John did this it made me feel all tingly down there i leaned back and parted my legs a little bit being more relaxed i felt Laura move up closer to my panties but not actually touching it she was teasing me and she knew i knew just by the laboured breathing coming out of my mouth she continued to go up and down sometimes taking a little of swipe of my pantie covered pussy with her little finger i felt my panties get damp at her slight touches the next touch turned into a poke and she poked me right in the g spot this flipped a switch in my mind and my hand immediately went to grab Laura's boob Laura gasped at my touch unexpectedly having to pull over to the side of the road i thought "oh shit" i pissed her of she looked at me with fierceness and brought my face to hers and deeply made out with me she was a way better kisser than John her tongue danced with my tongue her lips locking over my lower lip i could feel her breath inside my mouth as she passionately made out with me.
A car started driving behind us Laura broke our sloppy kiss seeing the saliva drip from our mouths as her lips moved away she wiped the corners of her mouth and started driving the rest of the way home like nothing ever happened she didn’t even say a word for the rest of the trip.
My pussy tingled a bit more as Laura drove us into her driveway we got up and i followed her to her front door still nothing but silence.
I found myself on Laura’s couch sitting waiting nervously for her to make the first move I could still taste the flavour of her kiss on my lips each time I think about it it made my pussy drip more I had to be careful what way I position my legs one small shake and my juices would seep through my undies and drip out of me.
Laura was sitting on the couch opposite me staring at me her legs were shaking her lips were smacking together as her eyes looked me up and down I would love to be a fly on the walls of her mind to see what was going on in that pretty head of hers.
Laura made her way to me and held her hand out to me and told me to follow her I followed her down her hallway and into her bedroom she shut the door behind us and locked the door and there we were face to face staring into each others eyes my hands shakingly met her hands Laura took control of our locked hands and began to raise my shirt of as I did the same with hers our hands broke way and began to explore each others bodies my hands slid across her stomach up around her back over her shoulder blades down to her bra strap unclipping and reviling her massive boobs almost smashing into my chest my hands ran all over her boobs gripping them firmly Laura groaned softly at my squeezing she gripped my chin and brought my lips to hers moving her hands to my cheeks pushing me onto her bed making out with me I felt her tongue parting my lips again Laura mounted my abdomen dry humping me and removing my bra she stamped her hands on my boobs, my boobs weren’t as big as hers but big enough to be roughly gripped.
Laura humped as I felt her hands press into my boobs feeling her thumb tickle my nipples then moving to suck on my neck I could feel her teeth stick in my first thought was “oh my god the pain” the pain got me so wet it felt like I peed myself my moans were stretched out thin as I felt the warmness of her breath on my neck and her teeth nibbling on my neck bones and collar bone.
Laura moved down further between my legs tugging my pants and undies down exposing a very wet recently pounded teen pussy Laura looked up at me and gave a very hungry looking evil look towards me and proceeded to take my clit between her lips then managed to cover my entire pussy with her mouth her warm breath spread all over my pussy feeling her tongue wash all over my pussy like a hurricane licking up all my juices.
Next minute Laura parted my pussy lips with two fingers and slowly finger fucked my pussy while still having my clit in her mouth she was hitting my little tingle spot with the vibrations coming from her lips moving like a vibrator I moaned quite louder than a girl like me should but she definitely knew what she was doing down there she broke the kiss between her and my throbbing pussy
“it takes a girl to know what a girl like” Laura smiled at me she tucked a finger inside me pushing me back towards her stack of pillows then withdrawing her finger and sliding that finger in my mouth she asked me if I liked it I moaned in agreement she kept turning me on with her words telling me how good I taste and telling me that im tasting my own cunt while continuing rubbing my clit.
My moans were getting more crazy as Laura continually put my fast paced pressure on my clit I bit my lower lip as I felt my orgasm break through me I sweated and panted and pushed out a river of cum that travelled all the way down Laura’s throat Laura withdrew herself from my flushed pussy and told me to open my mouth I excitedly opened my mouth Laura moved her lips closer to my mouth and poured what was left of my cum into my mouth it was so thick and creamy not to mention salty with a slight hint of sweetness Laura still had a few more drops in her mouth I had to have more I urged her to come closer and openly kissed her swiping all my cum from her mouth into my mine using my tongue to scoop around every nook and cranny of her mouth to savour all of my juices.
As I laid on Laura’s bed panting Laura had other ideas she was red in the face sweating and there was a giant wet patch on her track pants eating a teen girls pussy and tasting her juices must of really made her cum hard or drench beyond relief, Laura moved over to me wiping her hand over my clit swiping my juices and licking her hand while she sat next to me she told me how sweet and amazing my pussy was she loves teen pussy.
After 3 minutes of intense making out Laura whispered in my ear asking if I want to know what she tastes like I rubbed her moist pants covered pussy I nodded my head getting turned on by the touch of her pussy.
Laura stood up on her bed and slowly pulled down her track pants exposing her drenched laced panties then slowly and sensually pulled them down to her ankles filling the room with a sweaty salty odour throughout the room I closed my eyes to savour the smell of another woman’s pussy the smell was a lot more stronger than mine it took no time filling my nose and dampening my pussy.
I opened my eyes to Laura’s pussy staring at me the clit itself was beautiful I could see it hanging much lower then mine in between her pussy lips glistening with the shiny texture of her juices dripping down she had a light amount of hair around her pussy mound neatly trimmed Laura reached into her pussy with one
Finger digging at her pussy and flopping her clit up and own causing more drips from her pussy hit my stomach Laura gently guided my finger inside her the feeling was warm, wet and gooey she moved my finger in and out of her I added another finger inside her and started raming my fingers inside her faster she moved more over my head so I could catch the drops of her pussy juices in my mouth as they drip from her clit from my furious finger fucking.
Laura bucked at my fingers moaning jerking her body till I felt her pussy tighten around my fingers and coated my fingers in a warm liquid she yelled at me to taste my fingers to taste her cum I sucked at my fingers while Laura jumped and sucked at my pussy lips while slowly moving the lower half of her body closer to my face I ripped my nails into her ass pushing her pussy straight onto my face so many thoughts entered my mind as I tasted her mature aged pussy it was like a Smokey salty flavour on my lips I probed my tongue in her fuckhole as further as I can while I reached around and rubbed her clit I could feel more of her wetness gauge my face as I poked at her clit I could smell her asshole on top of my nose I don’t know why but I was really curious to see what her ass tastes like I replaced my tongue with another finger in her pussy and then slid my tongue into her sweaty asshole i felt her growl into my pussy making me growl into her ass the vibrations from her lips and tongue sent jolts of amazement up and down my body I pulled her into my face making my tongue slide furtherer into her ass.
Laura’s tongue kept flickering over my clit picking up her pace meeting the thrusts of my fingers in her pussy and my tongue in her ass we both came to a powerful orgasm drenching each others faces in our juices I had to push her ass of my face and capture the trickles of her mature girl cum into my mouth before I started drowning in her juices.
Here I am still breathing hard from my mutual orgasm with Laura but Laura was not done with me yet I could feel her lips on top of my pubic mound following down my wet throbbing slit with her tongue then moving me on my side and parting my legs
I was in a weird upright scissor position while Laura moved in an opposite scissor position slamming her pussy into mine and started rubbing my wet pussy with hers the scents of our climaxed pussies filled the room while our pussies rubbed on one another my pussy was still sensitive from the orgasmic adventure it experienced I felt Laura’s tongue wrap all over my foot poking her tongue through the gaps in my toes sucking over every toe while working our pussies up to another orgasm she continued kissing my legs pushing into my cunt deeper Laura was the first one to cum squirting warm power liquid into and onto my pussy that was enough for me to return the favour squirting my own juices back at her pussy I immediately went between her legs and licked of the infusions of mine and her juices of her pussy slit.
Laura soon passed out after an amazing session of intense first time lesbian sex I must admit it was enough to make me collapse and fall asleep next to her but once I fall asleep im not waking up for a long time I quickly gathered up all my clothes and snakingly tip toed out of her room and out of her house and made my way back to the library.
I soon arrived back at the library a few moments before my mum arrived, I had enough time to go to the bathroom to fix myself up and dose myself in enough soap dispenser soap to cover up the smell of sex.
By the time the weekend was over and was back at school I felt like a real woman and wasn’t to shy to start exploring witch I will intend to in the many years to come.