Kelly's Diary 005 - Losing My Virginity - Cover

Kelly's Diary 005 - Losing My Virginity

Copyright© 2024 by Kelly85

Chapter 1: Getting to Know Steve

Coming of Age Sex Story: Chapter 1: Getting to Know Steve - EVERY girl remembers losing her virginity. After all it's not just your first time, it's your ONLY time. I still remember that day like it just happened yesterday. I was fourteen and horny so what more do I need to say? OK, a LOT more, LOL. In the past month I'd gone from my first real kiss to sucking my boyfriend's cock. Now I've rounded third base and sprinting for home!

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   Consensual   Heterosexual   First   Masturbation   Oral Sex  

It all started about a month ago when I spent a weekend camping with my friend Sharon and few other girlfriends along with her mom and older brother Steve. Despite what I would’ve preferred, I’d never really talked with Steve as he would be a high school junior and I was just entering high school as a lowly freshman. At sixteen he seemed so much older and mature than the boys my age, not to mention he was quite a hunk as well. All of the girls flirted shamelessly with him, even his own sister which seemed sort of weird but who could blame her. Although he pretended to protest saying we were too young and immature, that only caused us to be even more outgoing towards him.

Personally I couldn’t help but feel a little jealous when his eyes would lock onto my friends’ growing boobs, feeling more than a little embarrassed that I seemed to be the one getting the least attention from him thanks to the cruelty of Mother Nature. Steve seemed especially interested in my best friend Beth who was already ready for a C cup with a curvy figure I would’ve killed for. He’d already asked her out on a few dates and she gleefully admitted the rumors about him and her doing the nasty were true. Looking down at my tiny boobs which barely qualified for a training bra (if I’d chosen to wear one), I would wonder why mine couldn’t look like more like hers. Life certainly wasn’t fair!

Considering Steve hadn’t given me so much as the time of day over the weekend I was almost speechless when he called about a week later and asked me if I would like to go out with him. Thank goodness we were on the phone so he couldn’t see my face flush beet red with excitement. Of course I accepted his invitation without hesitation. I’d been out with groups of friends and gone to parties with some boys in my class but nothing that really constituted a “date”, especially anything with a boy his age, not to mention one as smoking hot as Steve.

Steve took me to a Fourth of July carnival where we had all sorts of fun on the rides and playing games. By the end of the day though I was more than a little worried that he didn’t so much as hold my hand while at the fair. Considering his reputation with the girls in school, it made me wonder if he thought maybe I wasn’t sexy enough for him. Yet if I was that immature why did he invite me out in the first place? Boys can be so confusing!

Later that night though, as we laid huddled under a blanket watching the fireworks, he finally made a move and I felt a boy’s hands on my chest for the very first time. My heart was racing a mile a minute as he reached down into my halter top and began to play with my little boobs. What made things even more exciting was we were doing it in the middle of a crowded field packed with families and others there to watch the fireworks. Looking around it was hard to believe nobody had any idea of the fireworks going off inside of me as Steve fondled and groped me!

Whether it was because he liked my bubbly personality or I that let him play with my boobs (yeah, I know the answer), whatever the motivation Steve asked me out again. Although I let him touch my breasts again n our next date it was as far as I’d let him go. Of course I knew he wanted in my pants and I could tell he was getting frustrated more and more each time when I’d push his hand away from my jeans or shorts. From the look on his face and the tone of his voice when he dropped me off at home I began to worry that maybe he wouldn’t call me again if I didn’t start putting out like the other girls he dated.

Although as the girl I knew I was responsible for keeping a boy at bay, to be honest I wanted to make the trip around the bases just as much, if not more, as he did. Here I was, fourteen with my hormones raging, caught between my emerging sexuality and the last vestiges of preteen immaturity. Once I’d started masturbating my mother often commented wryly about how often I was doing it, What would Steve have though if he had any inkling of how often i was doing it the week after I started him. OMG, I was fingering myself every night and usually a couple of times during the day as I’d recall how it felt when his hands were exploring me, touching me all over. Of course my fantasies always ended the same with him eventually fucking me!

Whenever I was with Steve my attention was especially drawn to the large bulge in his pants which magically appeared whenever we were making out. There were times when it took every ounce of willpower for me not to reach over and unzip his jeans, freeing what I was sure had to be the most marvelous cock in the world. The problem was simple that while I was hot and horny, at the same time I couldn’t help but be a bit scared. Like every girl in school, including his sister Sharon, I knew Steve was certainly no virgin. Indeed, the guy had quite the reputation for putting the moves on every girl he dated as verified by my best friend Beth. It was also a well known fact that girls who did NOT put out didn’t get to date him for long. Even so it wasn’t that I didn’t WANT to do more, not even close. No ... it was more I’d never even so much as touched a boy down there and I was deathly afraid I’d embarrass myself by not being as good as the older girls he’d been having sex with.

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