Annie

Even today, looking back fifteen years, I can’t believe what happened to me when I was 14 years old. Not only was it the first full sexual experience of my life, but it was the wildest and always will be.

It was the summer of 1995 and I had just graduated Junior High. I was a pretty and athletic girl, had lots of great friends, and life was good. I was also fortunate to have a good family – Mom and Dad, my 17 year old brother and my my sister, Brittany, age 11. Of course there were the normal parent-teen and sibling conflicts here and there, but underneath that we were a close and loving family.

My body had started to blossom when I was 12 and by age 14 I was pretty developed – no late bloomer. My breasts were and still are of medium proportions, but like most 14 year old girls they stood up nicely on my chest, featuring nipples of the so-called “puffy” variety, capped with thick 1/4″ nipples that, when erect stood out prominently. I played several sports – volleyball in the winter and tennis and swim teams nearly year-round – so my body was toned, though I must say my rear end, though not too wide, was tight and stuck out nicely when I looked at myself in profile. I had jet black hair, light color skin that tanned up nicely in the summer, and a good-girl All-American smile. My friends always commented on my smile. To complete the picture my pussy was sort of on the small size (I spent enough time in girl’s locker rooms to get to know the variety of terrain down there), with little pink lips, a clit that emerged nicely from it’s hiding place when aroused, and topped by a nice tuft of black hair I kept well trimmed to keep hidden under my swimsuits.

By age 14 I remained a virgin, but wasn’t completely sexually inexperienced. Boys were interested in me and I had enjoyed several visits to first and second base at the fairly innocent parties to be had at that age, when girls and boys paired off to make out and get close. To make a long story short, I had been pretty well french-kissed, felt-up, and sexually stimulated by the time the summer of my 14th year rolled around. In turn I had stroked a couple of penises, which tended towards spontaneous molten eruption after a brief amount of stroking at that age. I guess the highlights of my sexual experience to date at that time were stroking a boy’s penis after he came in my hand, using his sperm to slide my hand smoothly up and down his cock. I had been fingered thoroughly as well and had several cums on the hands of my fellow explorers. On the solo front, I started exploring down there with my fingers when I was 12 and by the age of 14 was masturbating regularly – in my beds (lots), in the bathroom (often), and in a few less secure environments (e.g., the school bathroom) when my clit demanded some immediate attention upon being aroused. Being an active girl athletically and having come to enjoy stuffing my pussy with a couple of fingers when getting myself off, my hymen had pretty much been battered into submission, almost without my noticing.

So there I was: a nubile, still fairly innocent, horny teen good-girl hottie, ripe for the picking. My mom had a big talk with me early that summer about the choices and risks ahead of me as I prepared to enter high school. My parents were openly affectionate and I knew from hearing their exertions through the thin walls of our house that they had an active and boisterous sex life. At my mom’s questioning I was embarrassed to admit that I masturbated regularly and had been felt up a couple of times and had done my own touching in turn. My mom accepted this, said it was natural and that she was glad I was exploring my sexuality in healthy ways. When she asked me if I thought that I might go further in the near future, I had to admit that entering high school I thought that was a possibilty. While I was glad I was still a virgin and had refused to go further than I had, my body was telling me that it wanted more. The look and feel of a boy’s cock really turned me on and I liked making them cum, as much or more than I liked getting sexed-up myself. My mom took this all in, said it was probably time to consider birth control, and we agreed to make an appointment at the local family planning clinic to look into this. Within a week I had been examined and began taking birth control pills, all with the support of my practical-minded and supportive mom.

In July of that summer my brother came to me with a surprise proposition: a double date. My brother, Greg, was dating a hot-looking fellow junior, Molly. Though I didn’t know for sure, I was convinced by the way they acted around each other that they were fully sexually involved and horny for each other on a 24/7 basis. Pretty much two happy, healthy, All-American kids fucking their brains out whenever the opportunity arose (which is less often than one would hope for when you are still really just a kid living at home). Anyway, Greg said that his friend Jim, a 16 year old sophomore, had taken notice of me and had inquired as to whether I might be interested in hanging out. He was a little nervous about asking because I was a couple of years younger, sort of on the border of what would be considered acceptable age differences at our age level. I knew Jim a little from him hanging around with Greg and I liked what I saw – a good looking guy, also athletic, but importantly a nice personality as well. He had always noticed me and given me a smile and some attention whenever he was around. While I was 100% good with boys my age, had lots of guy friends, and my sexual experiences to date had been with boys in my grade, I was also intrigued with the prospects of dating an “older”, more “experienced” boy. Let’s face it, girls are often a little more mature and advanced than boys at that age and often match up well with slightly older boys.

After very little thought I jumped at the double date proposition with enthusiasm, feeling proud and mature at being sought out by an older boy. Greg and I ran the idea by our parents and after some negotiation and deliberation they agreed to a Saturday night double-date, double feature drive-in movie night, with a curfew of 1:00 a.m. (the double feature would last until at least midnight). I think they were comforted knowing that my brother would be there to monitor what went on with me and my date and keep me safe. Looking back, I can say that neither they nor myself nor my brother had any idea what that night would bring! I’m not so sure they would have approved if they had known!

Jim called after hearing from my brother and told me he was really looking forward to our date. He was so nice and we chatted for awhile and the ease with which we conversed put me at ease that this would be a good match-up. At the end of the conversation he said, “Ok, pretty Annie, I’ll see you Saturday night”. Every girl likes to be called pretty and I swooned a little bit when I got off the phone.

Boy, was I excited (and a little nervous) by the time the big day rolled around! I practically spent the whole day trying on outfits, debating what to wear for make-up and perfume, and messing with my hair and nails. Of course my whole family noticed and teased me lovingly (but annoyingly), except for my little sister Brittany who I think got as excited as I was, living the experience vicariously through me. In the end everyone contributed to make it a special night: my sister brushed my hair and helped with my nails, my Dad came through and surprisingly agreed to let my brother take his meticulously restored, pimped out, 60’s era Chevy Malibu (boy, did you ever get lots of attention on the road when your were cruising in that thing), and my Mom looked me in the eye and gave me the best advice I ever had: “Whatever you do, if it feels right and natural and good to you, go with it and have the time of your life”. I was a little shocked to hear her say this and wondered if she meant what I thought she was saying, but I just smiled and said “Mommmmmmm” and continued my preparations. In the end I wore summer sandals, a cute strapped little black dress of the mini-skirted variety, which showed a little cleavage at the top too, light make-up, and plenty of perfume. I wanted Jim to sniff me! I knew I was a little over-dressed for the drive-in, but I felt desireable and wanted to show it.

Mark left early to pick up his date and Jim and they all returned to our house to pick me up at 6:00 p.m. I was happy to see that Molly had also gotten dressed up in a similarly tight fitting summer dress, her blonde hair done up very prettily. She was so nice to me, giving me a hug and acting 100% happy to have me along. Jim looked well-groomed and handsome as well and he gave me a little hug too and told me how lovely I looked. I blushed a little but smiled happily and told him how handsome he looked too.

So off we went! With plenty of time to spare we went to a local restaurant and just ordered some soft drinks and appetizers, knowing we’d also be getting more to eat at the drive-in. We talked about school and friends and sports and typical teen stuff. Jim asked me lots of questions about school and my friends and my athletic stuff and so on, putting me at ease. By the time we left the restaurant I was so comfortable with him and my nervousness was gone. He was such a gentleman and he held my hand as we walked back to the car. His touch sent pleasures all the way up my arm, down my chest, and straight to my groin. My sexual self was awakened for the first time that night by such an innocent gesture. The gestures would soon get much less innocent!

On the drive to the Moonlight Drive-In Jim and I held hands again and I was so happy. I felt so grown-up, with everyone, including my brother, treating me like a peer. It was heady stuff for a somewhat younger girl to be with these “older” kids. It was a beautiful night, sunny and warm. As the sun began to set it would get cooler, but four teens in a hot car generate plenty of heat, and it turned out less clothes, not more, would be plenty comfortable! We parked towards the back of the parking lot, hooked up the speakers to the car, and got some drinks and popcorn and candy for the long double feature. The twin bill featured somewhat racy, pretty stupid teen comedies featuring horny boys and hottie girls. Not exactly great cinema, but good for some laughs and just titilating enough to get us all in the mood for some fun!

So the sun went down and we all settled in – Jim and I in the back seat and Greg and Molly up front. The car was a big old thing with plenty of room to stretch out. I hadn’t really thought about this in advance, but I’m sure Greg and Molly were appreciative of the old-school bench seats in the front, making it as easy to cosy-up up there as in the back seat. The first movie started and we pretty much paid attention, eating our snacks and commenting on the movie (mostly making fun of it). By now it was pitch black outside, with just the stars and the light from the screen bringing a little light into our car. The Drive-In was only about half full and towards the back where we were parked there were only a few cars scattered here and there – no doubt other teens out on dates looking for a little privacy.

As the first show proceeded we sort of quieted down over time and watched intently at one of those standard voyeur shower scenes, with the boys peeping into the girl’s shower. It was silly, but also kind of hot. In the seat ahead, Greg had moved over to the passenger’s side of the seat, with Molly towards the middle but leaning back into his arms. Looked comfy. Jim and I had started holding hands early on and then he suggested we get more comfortable like Greg and Molly, so we could see past them to the screen (yeah, that was reason – ha-ha). So Jim slid over to the back seat driver’s side and I climbed over him as he moved (lots of body contact here!), ending up in the middle but following Molly’s example and snuggling over towards Jim, who put his arm around me and brought me in. My nerves were tingling again as I was held in the arms of this cute and hunky older boy. I looked up at him and smiled and he bent down slowly to give me a light kiss on the lips. I held steady there and recriprocated and the first kiss turned into a long one and when Jim sent his tongue forward, gently parting my lips, I welcomed him in and sucked his tongue and pushed back, chasing his tongue back into his mouth tongueing him juicily. This began an increasingly fervid period of Frenching, by the end devolving into quite the episode of tongue slobbering and face sucking. When we finally broke apart to catch our breath, the movie had lost it’s audience and the agenda had changed decisively. Glancing ahead, I noticed that Greg and Molly were going at it as well up in the forward cabin. I couldn’t help but stare through the dim light and think how hot they were together. Back here in the cheap seats hormones were coursing through my veins and I stopped for the time being thinking of Greg as my brother, but more as just another teen guy, and a hot one at that, doing what comes natural. As for this teenbopper, I was getting increasingly excited and I could feel my nipples erecting and my pussy starting to flow with juices. I was in the arms of this hunky boy, we were locked in embrace, my skirt was riding up my creamy thighs to close to my panty lines, and I was filled with desire.

Turning back to Jim, I went in for another kiss and pressed my body to his. Jim got the message and began exloring my body with his hands, first in all the “safe” places, then approaching the zones of erotic delights. For just a moment the question of where and how far this was going came to mind. I was, after all, only 14 years old and I was, after all, in the same car as my brother. But my brother and Molly seemed to have disappeared below view in the front seats and the sighs and mewlings from Molly seemed to suggest that Greg was not at all worried about his sister’s proximity just a few feet away, so lights turned from yellow to green in my head as we rode further into the land of teen horniness.

Perhaps taking his cue from the front seat passgengers, Jim suggested we get more comfortable and eased me down on the back seat. There were a couple of blankets back there and we used them as cushions to get comfy. Thus arranged -me with my hot little teen body spread out on the seat, Jim coming in from above to cover me – we resumed our make-out session with unbridled enthusiam. Jim wriggled around his groin area into mine and I wriggled right back. His kisses covered my lips, my face, and then my neck and ears. He tongued my ear hole and sucked on the lobes, eliciting a little giggle and then a moan from me. As he descended to my neck and sucked on me like a vampire, I stroked him everywhere I could reach. One of his legs had settled between my thighs and I ground into him slowly and lewdly. Oh my! Slinking further south, until his head was at my mid-section, Jim whispered “I want to see your breasts.” Well, I wanted to show him them so I did him the favor, pulled my dress straps down and off my arms, and slowly pushed my dress top and bra down simultaneously, giving Jim a show. And there they were, my lovely teen breasts, sitting proudly up on my chest. My puffy nipples, responding to all the stimulation of the moment, had emerged at their tips as pencil eraser sized erections, two little headbeams of desire pointing right back at Jim’s gaze. The look on his face was precious – some mixture of awe and reverence and then pure lust. “Feel them”, I said. Jim explored them thorougly and seemed content to examine them without end, so when I boldly proclaimed “Suck my nipples” (who was this naughty potty-mouthed girl talking – I didn’t know she resided in me until this moment) to help him along, he zeroed in on the targets and for perhaps the first time since he was a little boy, succulent nipples were enclosed by his lips and sucked like a baby (it turned out Jim was as sexually inexperienced as me, so this was all pretty new for him too). God, that felt so awesome! I encouraged him to move beyond his tender ministrations and suck harder, and I moaned and caressed his hair and ears as he sucked and lapped and kissed my breasts into complete stimulation.

I brought Jim back to my lips and as we kissed again. I reached down and began to stroke both his ass and cock through his pants. His hand descended to my nether regions and found my dress had worked it’s way up to my hips, leaving my pussy mound free to explore beneath my panties. When Jim’s hand worked it’s way up my soft inner thighs and found my mound, he enountered a patch of wet fabric well-soaked from my cuntal secretions. I was hot as a firecracker and ready for action! Much rubbing ensued, accompanied by many moans and groans and sighs and “oh yeahs”. We were reaching a point of no return, and as there was no way a lust-crazed adolescent boy was going to stop without intervention, I had a decision to make. To tell the truth, the internal debate lasted all of about 2 seconds. I was too turned-on to turn back, I was on the Pill and didn’t need to fear pregancy, Jim had been a perfect date so far and I couldn’t think of anyone I wanted more to give myself too, I was fully ready to move from the limbo-land of being between girlhood and womanhood. And, as for my brother, I could only think that from the sounds emanating from the front seat that he was fully on-board with everything that was happening.

I took the iniative and grabbed the bottom of Jim’s shirt and lifted it off from him. Then I reached down and began unzipping and unsnapping him. He helped me out and pulled his pants down and worked them off. “Take off my dress”, I whispered. Already bunched at my waist, Jim worked it down my hips and off. My bra disappeared in the process, leaving us both in our underwear. I sat up, guided Jim to lay back against the other side of the car, and resumed stroking his cock though his underwear. It was erect and straining to get free and I could tell in the dim light that it was bigger than the couple of other cocks I had played with in my life. All my other dealing with penises had been under articles of clothing, but tonight I wanted to see everything so I pulled Jim’s underwear over his dick and down his legs. Oh my, what a nice hard sweet cock! I know now that it was about average in size, maybe just a little over the standard six-incher, but it looked long and thick to my 14 year old eyes. I was intrigued with the smooth skin and purplish helmet and as I reached out to stroke it, a big drop of clear fluid emerged at the head. I was blow-job virgin – even at my age some girls were reported to give these out like handshakes – but now I was drawn to this boy’s dick and I wanted it in my mouth. I lowered myself down, licked the droplet off the head (no taste, nice texture!), then began licking and sucking my way down until it was half-way engulfed by my sweet lips. I may have been a blow-job virgin, but curiosity had compelled me watch a number of talented blow job artists on the internet demonstrate their talents, so I pretty much knew what to do. So I licked and I sucked and I bobbed and jerked, I rubbed his ball sack (ok, let’s admit it girls, guys ball sacks are pretty weird pieces of equipment), and in general I made love to this boy’s cock as best as I could and pretty well, if I do say so myself, for a first-timer. After all, I am an athlete and athlete’s know home to perform! I can say with certainty that Jim was happy and he assisted in my efforts by stroking my head and gently guiding my movements to maximize his pleasure. Given the circumstances it was impressive that Jim lasted as long as he did, maybe five minutes. Once again, the internet had educated me not only as to what to expect (granted, as I said, my hand had first-hand experience with this already), but also the choice I was going to have: revert to a hand job for his ejaculation or suck him dry and swallow him. Commentary on the internet, as well as discussion with my girlfriends, had convinced me that guys loved to cum in girl’s mouths, and I wanted to show Jim how much I cared. So when his breathing and motions suggested that the big moment was about to arrive, I took him down in my mouth about half way, sucked hard, and stroked him firmly and rapidly straight into my mouth. I knew to close up the back of my throat so as not to choke on Jim’s sperm and then it happened – Jim came off like a volcano, spewing squirt after squirt of hot, bittersweet, weird tasting cum into my mouth. There was so much cum I couldn’t hold it all and, not wanting to choke, I opened my lips slightly as I contined to stroke him and let him cum drool out my lips and down his cock. This went on for maybe a full 30 seconds – a long cum I know now – and as Jim’s orgasm began to subside I sucked my way up and off Jim’s penis and swallowed the ample sperm left in my mouth. I think that Jim had just about passed out. As I continued to gently stroke his cock I spotted my underwear down on the floor and picked them up and used them to clean my lips and chin and then Jim’s cock. This brought him to and when I was done he sat up and gave me a hug.

“That was the sexiest thing ever”, he whispered into my ear. “Same for me”, I whispered back. “You’re the hottest girl ever”, he said, and I shocked myself by saying, “I’m hot and horny like a little teen slut, and I love it!”. I think his only comeback to that one was a moan.

As we embraced I finally became aware of my surroundings for the first time in awhile and it could not be ignored that things up front had progressed markedly. Molly had to be flat on her back, because her legs were jacked up and dancing in the air towards the car’s ceiling and my brother was clearly thrusting into her from above. Molly was making all kinds of noises at full volume, having forgotten (or just not caring) that she and her lover were not alone in the car. I then had a perverse yearning to see what they were doing first hand, so I moved back from Jim, gave him the stay-quiet gesture, and leaned forward and peered over the front seat. There was not much to see, as Greg’s body covered most of Molly, but his bare ass was humping, she was humping back, and her face turned up towards the ceiling showed signs of exertion and pleasuring of the highest order. She opened her eyes and, noticing me looking, smiled at me. Greg must have noticed her looking, too, because he glanced up and smiled at me as well. “Like what you see, Sis?” I was a little embarrassed to be caught peeking and blushed, but they seemed comfortable with it and I relaxed and smiled back. “Well, carry on!”, I said. “Same for you, Sis!, Greg shot back. And so I did.

Jim pulled me back, laid me down, and we resumed our making out. My lips were going to be worn out by the end of this night! I appreciated that he didn’t hesitate to kiss me, despite the fact that I undoubtedly had a cummy tasting mouth. Jim moved his way down my body, kissing and licking everywhere, bypassing my pussy to give attention to my thighs, than licking and sucking my deep inner thighs as he approached my cunt mound. What he found there was panty-clad, but so wet as to make the panties practically see-through. He licked and rubbed at the outside of my panties and then wormed his tongue inside the elastic along my crotch, pushing the fabric aside and becoming the boy to explore the terrain of my hot teenage cunt with his mouth. This was nice, this was fantastic, but my panties were in the way and I raised my hips and skinned them down, Jim helping with their complete removal (what a gentleman! – ha-ha). “Oh Jim, I love it. Eat me out!”, I exorted. I could feel myself building towards orgasm and the sooner I got there, the better. Jim returned to his tonguing, licking and sucking my outer cunt lips, my inner ones, running his tongue as deep he could into my dripping vagina, and finally giving my clit just the right amount of attention. “Finger me!”, I told him (hey, a girl knows what she wants!). He ran one, then two fingers up there and I grabbed his hand and began pumping him in and out. “Lick my clit!”. With his fingers fucking me and my engorged and erect clit getting lapped and sucked, it was only a short time before I felt myself on the verge of the biggest orgasm of my life! “Don’t stop, finger me, lick me … you’re doing me so good, Jim!”. When I came, I moaned and groaned and bucked and squeezed his head into my crotch. Poor guy, I think I almost killed him. But he was a trooper and stayed focussed on the job at hand, and I orgasmed and orgasmed for what seemed like a full minute. Finally I began to descend off my high and Jim wound down his ministrations and my mind and body floated back to the back seat of the lust-filled, teen sex-crazed driving machine. When I opened my eyes, I saw Jim’s grinning, glazed face and above the top of the front seat, Greg and Molly’s grinning mugs as well, enjoying the show. “Having a nice time, Annie?”, Greg inquired. I know I should have been embarressed because it was such a private moment and here was my brother looking at my sweaty nude teen body and, apparently, having just watched me getting eaten out and having a mind-blowing orgasm, but everything seemed wonderful and cool and natural so I just smiled and said, “Yeah, pretty nice … now why don’t you get back to taking care of your girlfriend and stop looking at your sister’s tits and pussy, big brother!”. Everyone laughed, and Molly and Greg turned their attention back to each other and hugged.

I retrieved my panties again and gave them to Jim, suggesting “These are pretty good for cleaning up!” He laughed again, and the cum stained dainties were employed again to wipe his face and then my drenched pussy. Boy, were those panties coming in handy! Completing his clean-up duties, Jim pulled me to him and we hugged deeply. “I know this will sound crazy, but I think I love you. I know you don’t know this, but I’ve had a bit of a crush on you for a couple of years now.” I was filled with joy and didn’t even think twice before whispering back, “I love you too, I really do.” It was a beautiful moment and my heart was soaring.

After a minute or two with the car quiet, Molly appeared again over the front seat and suggested, “Why don’t we all get decent, use the restrooms, grab some more food, and take a little break. Maybe even watch a movie!”, she laughed. It turns out the first show of the double feature was ending anyway, which we discovered once we wiped away the condensation that completely covered the windows on the inside of the car. So for a minute the car was full of action and laughter as four sexually satisfied teens recovered their clothes and got dressed (needless to say, I left my panties off). We got out into the cool night air, stretched, and headed for the concession stand.

When we got there Molly said “Come with me”, grabbed my hand, and pulled me into the handicapped, single use bathroom. She asked me if I was good with everything and was happy with how the evening was proceeding. “I loved every bit of it”, I said. “Yeah, it sounded like you did”, said Molly. “It was so hot watching you getting eaten out”, she said. I blushed, but wanted to be cool with this more grown-up girl and said, “Yah, it was the hottest thing I’ve ever done!” Molly smiled at me and reached out and smoothed my hair. I really liked this older girl treating me like a peer and giving me attention. “Ok, time to get cleaned up”, she said. “Can’t be smelling like $20 French whores for our boyfriends!” Molly whipped off her dress and pulled down her panties (apparently she was experienced enough to know to get them off early before sexing them up!). “What are you doing?, I asked. I thought we were just going to wash our hands and faces and re-apply our make-up and perfume. “Honey, our pussies stink. Gotta make them fresh for the boys!” Well, that made sense, so I peeled my dress off too. “Here, I’ll show you how”, said Molly. She got some paper towels wet with warm water, applied a little soap, and shocked me by bringing them between my legs and gently scubbing me down. Then she wiped again with non-soapy wet towels and finally blotted me dry. She looked at me and smiled. “Feel better?” “Yeah, I do”, and I smiled back. “Ok, clean your face and stuff and I’ll take care of myself.” I was kind of relieved she didn’t ask me to do her. When we were done she gave me a hug and told me how pretty I looked. She then surprised me again, by leaning in and giving my lips a short, soft kiss. I accepted it, but didn’t exactly reciprocate, though it did feel nice. She gave me a smile and I smiled back and she moved in again and planted another kiss, though longer and more sensual, on my lips again. This time I kissed back because I liked it and Molly seemed so beautiful and gentle. We even exchanged a little tongue, not deep Frenching but just a little where our lips met. Molly backed off and looked me in the eye and said, “You know, you are such a sweet and beautiful girl and I would like to be your friend. I’d like to get to know you better. A lot better.” She gave me a wink. I think I know what she meant and I hesistated, but said “I’m not sure, but I think I would ilke that too”. She gave me a long and deep hug and I hugged her back. “Ok”, said Molly, “We’d better get out of here before some poor disabled person comes along and needs to use the bathroom!” We laughed, exited, rejoined the boys who were waiting outside, bought a lot of delicious, junky food, and returned to our car just in time for the second show.

(Dear Readers: This site is called My First Time and I’ve already shared with you several first times for me from that evening. I’ve tried to convey that incredibly erotic evening to you and I hope you like my story so far. But I didn’t expect it to take so long, so I think I’ll just post what I’ve written so far, take a break, and come back at a later date and share the rest. Sorry to keep you in suspense! Just as a little preview I can share that as hot as the evening had been so far, the activities during the second show got even hotter and crossed into some territory (think girl-girl, brother-sister) that I had never imagined I would cross. Thanks for reading, hope you’ve enjoyed it so far, and keep on the look out for the next posting from me, Annie!)

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