Curious Teen Jessica by Captain Boner

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.