Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft, Ma/ft, ft/ft, Fa/ft, Mult, Consensual, Lesbian, BiSexual, Heterosexual, True Story, Gang Bang, Group Sex, Interracial, White Female, Safe Sex, Oral Sex, Anal Sex, Masturbation, Sex Toys, Cream Pie, Double Penetration, Needles, Slow, School, Nudism, .
Desc: Coming of Age Sex Story: Chapter 1 - I make up for lost time, losing my cherry later than most.
You know how they say that no matter how much you try somethings just happen when the time is right? I'd like to think that is what happened to me. I grew up in London and we moved to San Jose, california when I was 15. London was great and we moved in what my parent considered the 'right' circles, always making sure we were part of the 'in' crowd. My dad is a computer programmer and he created some kind of program that was the first step towards making part of the windows operating system. He had his own company which he sold to Microsoft for a boatload of cash and according to him we were 'set for life'. Mom was a lab technician, dad and her met in college and they had been married forever and a day.
We bought a ranch outside the city proper, just about 250 acres that didn't have anything much on it except a huge house with a pool and a garage with space for about 8 cars at the same time. I didn't think I'd ever get used to so much space after homes in london- think of a mini cooper compared to a tank. There wasn't anyone for miles and miles.
It was kinda nice. I discovered a little later that there was a shed about a mile from the house that the previous owners had their help live in (but that comes later).
Dad starting working for Microsoft almost from the 3rd day we landed and he was away for pretty much all day and I got to see him on the weekends if I got up on time. Mom enjoyed the place for a couple of months and then decided she was either going to shoot herself or my dad or both of them from the boredom. I remember the fight they had over why my mom needed to work. Funny thing was dad wasn't even against the idea - mom just had a bug up her ass and needed someone to vent it on. Mom started working and that pretty much left the house to me for about 3 hours after school everyday.
School was kinda fun. I'd always been very studious and had been on the gymnastics, volleyball and football(I know you call it soccer here) teams back home. I decided I'd give tennis a try too. They didn't have a soccer team at the school but I got on the gymnastics team and the volleyball teams at school (what the hell is beach volleyball?).
One of the things I really hadn't given much thought to was boys, just because with the books and the sports I hadn't really had time for all that. Yes, yes, I know that a 16 year old virgin is almost as rare as a unicorn these days, but what can I tell you. It wasn't like
I hadn't gone on dates or had my experiences with snogging (making out), but it really hadn't progressed passed the rubbing my tits stage.
I think I've bored you all with the background enough a little bit about myself. I'm callista not callie - callista winston. My parents may have been a little punch drunk with happiness when they had me as mom had a really hard time getting preggers, hence the name.
Currently (I'm 29 now) I stand a shade under 6 feet, an athletic body, with perky C-cup breast, topped high with pink (pierced) nipples, I've been told I've a nice ass and I can still fit into my jeans from the last year of high school (3 hours at the gym every day). I have fair skin, brown/gray eyes and long brown/black hair. Dad's American and Mom's Indian.
At 16 I was wearing size A bras and had no ass that i knew of.
Sex wasn't on the agenda, I had a game plan, get to flight school - I was crazy about flying.
I won't go into the details, lets just say we travelled a lot and I was crazy about flying.
Life went on like this for a while - with one exception.
Now on to the part you've been waiting for
Due to the move and late school start, I had to do one more year of school and everything changed the summer that I turned 18.
Due to all the time Mom and Dad were away, and I was pretty much alone at home. There is only so much we swimming/internet surfing and tv that you can do. The parental unit had bought me a car for my 18th and the beach was fun for a while. What they had bought me for my 17th was a dog. Oscar was a American English Coonhound who was more interested in his food bowl than anything else. But he was very interested in other things later.
Mom and Dad had rented the farm to a Mexican family, they would farm and reap and pay us
30% from the sale of whatever they grew. Margarite and Alfonso grew onions, tomatoes and broccoli, they had a son, felipe who helped me lose my virginity.
It happened one afternoon during the start of my summer vacation. It was the 4th day I was home,
Bored out of my skull, I had been playing with myself since I was about 15 (yes yes late bloomer) and decided that I would start my morning with nice diddle. I hadn't really used toys - just my god given gifts.
I usually sleep in my panties. The 8 car garage I mentioned before had an nice apartment above it and I had claimed that for myself. Mom and Dad had their space at the opposite end of the house and I could've moaned to my hearts content and they wouldn't have heard it. I woke up feeling horny (some really intense dreams) and decided that since I was already half naked, I'd use the rest of the morning to diddle myself silly - I started by pulling on my nipples which responded to my minstrations very very satisfactorily by hardening up and sending thrumming little jolts to my groin. I keep my bush nice and trimmed with just a little flame shaped bit of fuzz whose wick is right above my little magic button. My fingers followed the shape of the flame till the base and my fingers found my little button. That was it, I couldn't concentrate on playing with my nipples and both my hands found my groin. My cunt was nice and moist and one on merrily diddling on my clit, the other one spreading open my labes and rimming around my hole - don't know what I was saving my hymen for, but it was still there, hadn't penetrated myself much more than half a fingertip. I was rubbing away to high heaven and pushing in a little, with all the gyrating hips and pulling myself to the edge, holding myself on the edge for a great orgasm. All of a sudden I heard barking and scratching at my door. Mom usually lets him out before she leaves but I guess she decided that he would be the perfect interruption to my morning diddle.
Nothing else to do, I got up opened the door and almost kicked the little shit. He stood there looking so forlorn that my heart crumbled at him even though my pussy was screaming for release. I stooped down and hugged him. I guess I'd touched my boobs during my little play session and he scented pussy juice on my nips took his merry way with a couple of licks which got me all hot and bothered again. I pushed him away, shut the door ignoring his whimpering and put on my trackpants, t-shirt and dragged myself to the door to open it and let him out. My level of sexual frustration was about the same a Mt. Vesuvius before the explosion. I cursed oscar to no end - fucking mutt - I loved him, but his sense of timing was excruciating. Nothing to be done - the mood was broken and even though I tried for at least an hour, my clit and pussy were having none of it, and I couldn't cum.
Going to the pool was probably the only other thing I could think of doing - maybe cooling off would help (hah).
I put on my bathing suit - nothing special - a pink, grey and blue two piece that I used for swimming after gymnastics at the school pool. I jumped in, swam a couple of laps and lounged on a deck chair. I guess i feel asleep, having some of the most vivid dreams. I was on a deserted island and just walking along the shore and came upon a man who had been ship wrecked. I pushed his shoulder and he opened his blue blue eyes and just looked at me. Then he reached up and cupped one of my breast and kissed me deep and then he lay me on the ground and went dining at the 'y'. I guess the dream must have made me super horny as all I really remember is the sound of heavy breathing and I woke up to the feeling of a hand on my thigh.
My eyes opened to see Felipe standing over me. He was shirtless, with a straw hat and looking at me with a smirk like he was on the island with me. "Senorita Callista - are you okay" he asked. I was dry throated and felt like I'd just run a 1 mile a minute for an hour. I just nodded. He didn't seem convinced. 'You looked like you was having a bad dream'. I told him I was okay.
But he wouldn't leave, just kept putzing around the pool and looking at me. I decided to ignore him. I jumped back into the pool to cool down and paddled around for a bit. When I got bored of this, I pulled myself up and and decided a wine cooler and a sandwich would hit the spot. I finished off the sandwich, cooler and got another one from the fridge and went back to my chair. Felipe was still there cleaning up around the edge of the pool, but I ignored him. Halfway towards towards the 2nd bottle, I felt the booze kicking in and my tense muscles relaxing. I surreptitiously looked for felipe but he was away at the far edge of the pool and wasn't looking towards me.
My right hand squeezed my right tittie and my left snaked towards my clit. A quick rub and my horniness returned like it was just around the corner. I started squeezing and rubbing harder. I know I'd closed my eyes and was just starting to moan when I felt a presence over me. It was Felipe. "Senorita Callista - are you okay?". I looked at him and his eyes told me he knew exactly what I was doing.
Maybe it was the booze, maybe it was the sexual frustration, but I wanted to cum and cum very very hard. I reached up and before I knew it,
I was kissing him and he was kissing me back. Holy hell, but there was tongue and tongue. His hands were all over me, squeezing my boobs and my ass. He started kissing the side of my neck and lower, pulling my top down as he moved down. Soon he was all over my tits, squeezing, biting and sucking and my pussy was more wet than it had ever had before. He kissed his way down my stomach to my bikini bottoms started moving down pulling my bottoms down. I saw him take in my pubic flame then dart with kisses, sucking and nipping around my clit, labia and darting his tongue into my love canal.
'Take me' I heard myself say. His pants were down in a flash and I saw his cock. It wasn't as big as my imagination, but it must have at least
been 7inches. I felt him spreading my legs and positioning himself. I know I felt him rubbing his cock on me. I was soooooo wet that a subway train would've been able to go through. He put his dick at my hole and started pushing. I didn't know it could feel this good and my fingers weren't a near enough substitute. He went slow but steady, never pulling back, but a slow inexorable pushing inwards. I felt my pussy open up like a tunnel that was designed for this. Surprisingly, there wasn't any pain, just a slight snap that I felt was my hymen deciding to give up my virginity to Felipe. Once he was in to the hilt, Felipe paused for a bit, then started pulling back, making my puss feel like it was giving up something very very precious. I wasn't empty for too long and he pushed back in just a little hard making me wince.
'Senorita Callista - you soooo tight' he moaned. 'Shut up and fuck me' was the only response.
I felt Felipe start to push forward and felt full again. He continued like this for about 5 minutes till I started moving my hips with his motions.
He speeded up. Pushing forward till he was buried to the hilt in me and pulled out making me fear that I wouldn't be this full ever again.
My hips started gyrating. The feeling of his pubes on my clit was amazing and his dick in me was even better. I felt his finger around my asshole and
I spasmed in pleasure, never having hand anything there except toilet paper after pooping. Even as he was pushing his dick in and out, I felt him rubbing my ring and then pushing his fingertip in. Never having had sex before i didn't think anything of this and after a while it even became pleasurable.
The orgasm that had eluded me all morning finally decided to arrive with blast and I don't know if i screamed, but I certainly know that it curled my toes.
I thought that once I came, Felipe would stop, but boy, was I wrong. He didn't even pause. His finger in my ass must've been up to the 2nd knuckle and he continued pushing. His face lowered and his mouth was on my left nipple, sucking like his life depended on it. My nipple must have had direct contact with my pussy, because before I knew it, my second orgasm was coming in for a crash landing. And landed it did. Ladies, I don't know what your first big 'o' was like, but I'm pretty sure I saw stars and planets. Felipe still wasn't done.
He paused for a second to get a better angle, and I felt my legs being lifted till my knees were next to my ears (thank god for gymnastics) and the sensations were even more intense. Felipe must have been a jackhammer in his previous life, because he went to town. The pounding he was giving my pussy - ooooooooh.
I don't know if he was punishing my puss or giving it a just reward, but holy hell. I didn't he'd stop. My pussy was thrumming with all the pounding.
Felipe started moaning deep in his chest and I knew he was close to cumming. "I'm not protected" was something I was barely able to get out before I felt him tense in me. Felipe pulled out his cock and started spraying everywhere. I got a couple of splats on my cheek, nose and lips. I must admit, I was too busy to notice as I was in the throes of another orgasm. He finally finished and splayed out on top of me.
I was just coming down from my last high when I heard Felipe's father calling his name. He jerked up like someone had stuck a cattle prod up his ass, pulled up his pants and was running down the pool deck like he was on fire. I just lay there enjoying the afterglow. One of the things I realized as my senses slowly returned that during all the pounding Felipe gave my puss, he hadn't once kissed me after the intial little bit. Something I had to rectify and soon.