Kelly's Diary 026 - Valentine's Day Surprise - Cover

Kelly's Diary 026 - Valentine's Day Surprise

Copyright© 2024 by Kelly85

Chapter 1: Valentine’s Day Traditions

Coming of Age Sex Story: Chapter 1: Valentine’s Day Traditions - I'd always heard Valentine's Day is supposed to be just for lovers. Well, this was the year I learned just how much fun it could be when it's just for sex!

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

I was fifteen, just a few weeks away from my sixteenth birthday, and thoroughly enjoying my sophomore year in high school. I’d been dating Greg since Christmas after breaking up with John and now it was almost Valentine’s Day already. Greg was an eighteen year-old senior at my high school and one of the top football players. Naturally, he was good looking and quite popular with all the girls. The word in the hallways was he was blessed with one of the biggest cocks of anyone in our school so, of course, I’d been wanting badly to find out for myself. Even though I was just a sophomore, I’d already acquired quite a slutty reputation with the older boys so I begged a few of my closest friends to drop some hints his way about how I was interested in him - VERY interested.

Well, when a girl has a reputation like mine, it didn’t long before he was leaning against my locker and asking me out. Although I tried not to appear TOO eager, I couldn’t wait for our first date. I must’ve masturbated for hours the night before, dreaming of what I hoped he would do to me - not WITH me ... TO me. Let’s just say I discovered on our first date the rumors about his cock were true - he must have been twice the size of some of the guys I’d been with from school! It was the most challenging blowjob I’d ever given up to that point and when he fucked me, oh my god I thought I was going to be split in two!

With all that I guess I don’t have to say Greg was by no stretch of the imagination the first guy I’d had sex with. Steve, the older brother of one of my girlfriends, had taken my virginity two summers before, not long after I had graduated from middle school. Unfortunately his mom’s job was transferred and so he had to move out of state the following winter. Steve and I had shared quite a few enjoyable experiences and many a night in the days after he left I would lay in my bed at night touching myself as I dreamed of him fucking me. Looking back now, I realize that we’d never been truly in love even though at the time I thought I loved him terribly. His cock was my first and I knew one thing from the first time he did me - I LOVED sex. After that I’d do most anything to get more of it - as much as I could. Almost sixteen now, I’m MUCH more mature and I realize now our relationship was really more about mutual physical satisfaction - but then there’s nothing wrong with that, especially when you’re only fourteen. While we dated, Steve was the only boy I’d had sex with (if you don’t count the time I teased his younger brother and things got a bit out of hand).

After Steve’s mom was transferred and Steve’s family moved away it didn’t take long for me to realize while masturbation was a lot of fun, it simply can’t replace the real thing so I started dating a number of guys and developed what I would call a healthy sex life. It didn’t take long for the boys in school to discover how I felt about sex and needless to say, I was never at a loss for a date. Despite the rumors in school to the contrary, I really didn’t fuck all that many of them but when it came to blowjobs, let’s just say I was more than willing to please just about anyone who would let me suck them. Besides, it’s the least a girl can do anyway when the guys is paying for everything else.

Actually, I was quite proud of the reputation I was getting for giving the best blowjob in school and almost every boy I dating went home with a little less cum than he’d started out with. Some of the more prudish girls in my class thought they were being mean by labeling me a slut but I knew they were just jealous of my popularity and so I just ignored them. Besides, I was very active in my church youth group and other community organizations so I like to think that most people, especially the adults I associated with, thought of me as the nice “girl next door”.

Until this year I’d never celebrated Valentine’s Day with a boyfriend. It was more a timing thing than anything else. The first thirteen years of my life I didn’t have a boyfriend to start with so it was a moot point. Sure my dad bought me flowers but that’s different - he was my DAD after all, not my boyfriend. Then last year, Steve had moved away just a couple of weeks before the big day and I was moping around the house crying about how unfair life was being to me! Well, this year was going to be different because now I had Greg and I had a good feeling he had something big planned. By big, I’m of course referring to his nice dick I’d come to crave so badly!

While I may not have had a boyfriend for past Valentine’s Days, I was still lucky in that my dad had a started a family tradition back many years before when he gave my mom a dozen beautiful red roses and me a single yellow rose with a long stem. He would then gave me a quick peck on the cheek after which he led my mom by the hand upstairs to their bedroom and closed the door. Our house is pretty old and the walls are really thin so I could hear more than enough in my bedroom next door to know they weren’t watching TV! When they were done, he would then take us all out to a dinner at some fancy restaurant. I just loved how they included me at least in a small way that day.

The part I looked forward to the most though was when we got home and he would give us each a Valentine’s Day present. Mom’s was always in a pink bag from her favorite store - Victoria’s Secret. One year he gave her a really sexy outfit - a sheer white nightie. Wow, she looked so incredibly sexy in it! It certainly didn’t leave anything to the imagination. As for me, I was thrilled with my present - a cute red and white cheerleader outfit (never mind that my school colors were blue and white!) After that, each subsequent year he always found some cute outfit for me. One year it was the most risqué Tinker Bell costume with a tiny wrap-around lacy skirt and sheer halter top. Last year it had been a Little Mermaid outfit with a tight green cloth tube for my legs and a teensy little bikini top made of just a couple of shells and string.

Each year, my mom and I would put on our new outfits and pose for him while he took our pictures for the family album. He would take the ones of mom as she posed all naughty for him. Afterwards I usually sat in his lap while mom took our picture together. The past year or so I was sexually experienced enough to recognize the bulge in my dad’s crotch for what it was. When I felt it pressing against my bottom I felt good because I knew it meant that he was ready to go back to their bedroom and have a good time with my mom. It never crossed my mind he might be thinking of a going to a different bedroom ... Yeah, it’s easy with 20/20 hindsight to call me naive but why would I think anything else?

This Valentine’s Day was going to be different - of that I was sure. For the first time I had a boyfriend on Valentine’s Day - one who was already fucking me. Greg had asked me out to a fancy dinner and I was thrilled to accept. I’d been out to a lot of high-end restaurants with my parents and sometimes just my dad but never on a real date. It wasn’t until I told my parents at dinner the next day about our plans and saw the crestfallen look on my dad’s face that I remembered our tradition of him taking us out to an elegant meal. He quickly pretended everything was OK and wished me a good time but I still felt a little guilty about things. Somehow I knew deep inside of med as I grew up a lot of things would change between me and dad; but I knew one thing would always stay the same - I would always be my daddy’s little girl! Little did I know back then just how much things WOULD change between my father and me, but even so I still like to think of me as his little girl.

In any case, February 14th finally arrived and I was about to get ready for Greg when my dad stopped by my open bedroom door. I was wearing just my panties and with my sixteenth birthday only weeks away, my boobs were finally starting to look pretty good if I said so myself. The fact my bedroom door was open wasn’t anything unusual. Indeed, it would’ve been a lot more strange had it been shut! In fact, I couldn’t even remember the last time I’d closed it except when we had people over. Nudity was nothing to be ashamed of in our house and I’d seen and been with my parents naked in our hot tub many times over the years. At the same time I would never flaunt myself at home of course. Actually, other than when we are in the hot tub, the only time I was naked around home. other than in the bathroom, was at night when I went to bed. I first started sleeping nude after I started having sex. I figured if you’re old enough for sex then you’re old enough to sleep naked. However, once I got used to it, it felt constricting to wear anything to bed. In any case, I was still a bit surprised when my dad took a REALLY good look at me and then whistled softly.

“Whoa! You’re looking pretty hot there girl,” he said with a grin, “So tell me, is Fred going to get lucky tonight?”

“Oh daddy!” I said in mock protest, “You know his name is Greg; and besides, we’re just going out to dinner.”

My dad knew all about my past experiences from my mom who always insisted on a complete debriefing whenever I returned home from a date. He also knew I knew he knew full well exactly what Greg and I would really be doing before I returned home. My dad was always the type to tease me a bit but I really didn’t mind. Then I noticed his hand was behind his back so I smiled and walked over to him, trying to act like an innocent little girl (even if I was topless at the time!)

“Hmmmmmm, something for me, daddy?” I asked in my best little girl voice.

He leaned down and kissed me gently on my forehead. Then he brought his hand out and I saw it was a box in pretty pink wrapping paper with a pink ribbon bow. My yellow rose was slipped under the bow and he pulled it out and handed it to me first.

“Happy Valentine’s Day baby girl,” he said with a smile, Then he handed me the box saying, “I think you’re old enough now for something a little more grown-up.”

I giggled and snatched the box from his hand and ran over to sit down on the edge of my bed. I was so excited to see what was inside that I unceremoniously ripped off the wrapping paper and opened it up to find the cutest little negligee inside. It was made of light blue lace and totally sheer. Also in the box was a tiny thong made of the same material as the negligee. The whole outfit felt like it made from air it was so light. I held it up in front of me and I could still see my bare boobs right through it. My mom had some pretty sexy lingerie but this was a first for me. Once I tried on some of hers just to see what it felt like but everything she had was too big for me, especially in the bust and hips. Well, this outfit was just my size and I couldn’t wait to try it on! I turned my head up to my dad who was looking at me with a big grin on his face.

“Oh wow!!!! Thank you daddy,” I gushed, “It’s beautiful!”

My dad had a smug look on his face. Of course he knew I would like it! “So ... are you going to try it on for me or what?” he asked anxiously, “Hurry up, your mom’s changing into hers and I can’t wait to see both my sexy girls all dressed up.”

He left the room and I shivered with anticipation. This was soooooo cool! I’d never had an outfit quite like this before and I marveled at the soft feel of it against my bare chest. Well, I didn’t want to keep them waiting so I quickly slipped off my panties and stepped into the sheer thong. It was barely wide enough in front to cover my pussy and in back it was a mere string that slipped up between my butt cheeks, buried out of sight which felt a bit weird actually. Fortunately I had just enough hips developing by then to hold them up! Sure, I had a number of thongs but never one as revealing as this one. It barely felt like I even had anything on! The string felt a little odd wedged up between my butt cheeks and when I looked in the mirror all I could see were the strings that came around my hips as once they joined, the rest was hidden out of sight by my ass. Heck, I may as well been bottomless for all it covered in the rear! The front wasn’t much more generous. The little triangle barely covered my pussy and if I hadn’t started trimming my pussy to where it was almost shaved my pubic hair would’ve been sticking out all over the place.

With the thong in place, the next step was to slip on the negligee. Lifting it up, I dropped it over my outstretched arms above me and let it literally fall into place. It felt as light as feathers falling into place! Once I straightened it out I took another look in the mirror and instantly fell in love with the way it looked on me! The bottom hem barely covered the lower part of my bottom and the material was so incredibly sheer it was like I wasn’t wearing anything at all. Talk about not leaving anything to the imagination! Hen I twisted to get a look at my backside in the mirror and truly loved what I saw. My boobs may have been appearing slower than I would have liked but my ass was definitely running on an accelerated time scale. Every guy I dated commented on how nice and firm my butt was and it was definitely my best “asset” - just as my father always said! Little wonder I loved to wear anything that showed it off - tight pants, short skirts, cutoffs, bikinis, and well, you get the picture.

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