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My name is Caleb. This is my first submission, so please be gently with the comments! 😉 This story is how I lost my virginity to my high school sweetheart in her mother’s office at the school library. I have given everybody a fake alias so as to protect their identity. All sexual relations took place after both parties were 18 years of age. I hope you enjoy and please feel free to comment and vote on my story.


First, the girl. If you’re looking for a story about the hot cheerleader hooking up with the hot quarterback, please continue searching for another story. My girl’s name is Alyson Annette Anderson (Alias of course). All the girls on the basketball team called her Triple-A (AAA). She was about 5’8″, approximately 150 lbs, with b-cup boobs, blonde hair, and brown eyes. Not the Cheerleader mold, but not fat either.

Now me, I was about 5’9″, thin but in shape approximately 120 lbs, brown hair, hazel eyes, and a 7-inch dick.

I had been in love with Alyson ever since she came to my school in the 5th grade. I found her to be absolutely gorgeous and she liked how much I liked her. I was stuck between the nerd world and the jock world. While I played sports all year round, I was never the star. Yet, due to playing sports, I never really fit in with the nerds either. I was picked on by both groups in high school and completely ignored by most girls. Alyson seemed to thoroughly enjoy my company though. Alyson was the epitome of a “church-girl”. Soft-spoken, straight-A student, never got in trouble, never partied. But, due to the lack of female options elsewhere, when I began to notice that she enjoyed being around me at school, I naturally began falling in love.

For two years we would talk and hang out at school and other extra-curricular activities. I desperately wanted to ask her out, but she always had a bf from her church. This was frustrating as hell. We were also sending love notes back-n-forth to each other during classes. (This was like 1-2 years before texting). So, I knew she wanted to be with me, she was just also wanting to be faithful to her bf. Had she been any other girl, I would have said fuck the bf he didn’t go to school with us. But, since she was the goody-two-shoes type, I knew she would never go for it.

Finally our senior year arrived and when we got back to school from summer break I had learned that she was single. I took it slow and tried to be the nice guy friend and console her for it not working out with her bf. It seemed to work because I could tell she was becoming even more interested in me. Finally towards the end of October, I asked her to be my GF and she said yes. She was my first GF and hopefully my soon-to-be first kiss. (Little did I know what else! Ha!)

We were taking it slow with things and just holding hands and hugging at first. It wasn’t until December right before Christmas break that I got my first kiss. With as little as our school was, we only needed one bus to transport our guys and girls basketball teams to our games. After one of our away games neither Aly nor I had been signed out by our parents (meaning we could ride home with them instead of taking the bus) and so we rode the bus home from the game.

Aly told me to sit with her in the back of the bus with her girls. Like I said before I was ignored by all the popular girls and this was no different. I sat with her and I was on the inside against the window while she sat on the outside and talked with her teammates. I was minding my own looking out of the window when she turned towards me pulled my head in and kissed me square on the lips. She then turned around and continued talking with her teammates. My head was spinning faster than the wheels on the bus!! This goody-two-shoes girl just gave me my first-kiss on a dark school bus surrounded by all of her basketball teammates.

Little did I know, but Aly was going to use me to experiment with her sexuality. And I was going to love every minute of it. Like most church-girls, she turned out to be extremely kinky. I could tell you a lot of short quick stories of different places she found to experiment, but I have already ramble on too long away from the core of this story.

So, it was approximately January or February and we were in the heart of basketball season. On this particular game day, our game was at home and the girls varsity game didn’t start until 6:15 or so. I didn’t have to be at the gym until mid-way through the girls’ game, but Alyson had to be in the locker room to start changing by 5:30. This means we had time to kill after school.

Alyson’s mom was the school librarian. Normally Alyson just hangs out in the library with her mom until time to go to the locker room. Today was a little different though. Her mom had a librarians meeting a few towns away and would have to leave directly after school. She allowed Aly to stay in the library but told her that it was closed and nobody was allowed to come in. casino siteleri Alyson told me to show up about 30-minutes after school ended and she would let me in.

So, the time came and I showed up. Aly came over and unlocked the door to allow me in. I gave her a deep kiss and she pulled away and told me to hang on a second. She locked the door and told me to follow her to her mom’s office. Once in her mom’s office, she shut and locked that door as well. We then began passionately kissing each other and my hand massaged her back and slid lower to her beautiful ass. I grabbed two big handfulls and pulled her up into me while we made out. Alyson finally lightly pushed me away and told me we needed to sit down. So, we sat down against one of the walls and continued making out.

My hands then went and pulled her shirt up to reveal her sports bra. Still not being sure if she really wanted to do all of this, but not wanting to miss my opportunity to see my first pair of boobs, I then pulled up her sports bra to reveal two glorious mounds of budding bosoms with quarter size pink areolas and eraser sized nipples pointing straight out. I pulled away from our kiss to take a look down at what I had just unveiled. She asked me what I was looking at and I told her I just wanted to look at her boobs. I then told her they were beautiful as I gently grabbed her right boob and gave it a light squeeze.

Her eyes slowly moved towards the back of her head and she began breathing heavy. I could tell she liked it. I then began rolling her nipple between my thumb and first finger as she squirmed beneath me. I lowered my head and began kissing her again while I was playing with her boob. She broke the kiss just long enough to tell me to take her shirt and bra off. Once hers were off I quickly shed my shirt went back to kissing her and feeling up her boobs. I soon found myself topless on top of her topless body. I began kissing down her neck paying close attention to to the spots that made her squirm the most. I made my way to the top of her chest. Then I could feel the edge of her breasts beginning. My hands were holding hers as our fingers intertwined.

I could feel her squeezing tighter the closer I got to her boobs. I kissed straight down her cleavage till I was at the bottom of her breasts. I then moved around the bottom of her left breast and began kissing a slow circle around to the top. I slowly kissed circles around her boob coming closer and closer to her areola. Right before I would have kissed her areola, I picked my lips up and moved them to the bottom of her right breast. Alyson squirmed and told me I wasn’t being fair! I just smiled as I stared deeply into her eyes. I could see the passion flaming in the forefront of her eyes. It was as if I could see her sole. I knew without a shred of doubt that this is the only place on the planet she wanted to be at this very moment. In her mother’s library office with me.

After what seemed like years staring into her eyes, but was probably only a minute at most, I went back to kissing around her right breast. As I edged her areola, I lifted up slightly and looked into her eyes while I ever so lightly blew on her nipple, which drove her wild. Alyson was squirming underneath me squeezing both my hands almost to the point of pain, but I did not care. I just grinned and kissed her passionately on the lips again. I saw her eyes roll into the back of her head before I closed mine and became lost in our passion.

I lifted my lips off hers, looked deep into her soul, whispered to her I wanted to see her naked and I wanted her to be my first. She did not say a word. I kissed her on the lips. Then the neck. then between her breasts. At the top of her stomach. Just above her button. Kissed her at the top of her jeans as my hands came to join my lips as I began undoing her belt. Once her belt was undone I dared a look up into her eyes. They were locked on me with a wildfire burning ferociously behind them. I undid her button. I could see the top of her underwear.

I slowly pulled the zipper down. I could see the pattern of faded lightly colored pink, white, and yellow flowers on her white panties. She was not yet into lingerie. I moved my hands to either side of her jeans waistband and started giving a light tug on them while staring into the wildfire in front of me. She took the hint and lifted her butt off the ground just enough for me to pull her jeans below the beautiful mounds she was laying on. Once she set her butt down I kissed just above her pussy on the outside of her panties. I could already smell the musky scent coming from between her legs. As I revealed her thighs, I kissed first the inner part of her left thigh. Then the inner of the right.

I pulled the jeans down a few more inches. Kissed the left, then the right. Jeans dwon a few more inches. Left, then right. Jeans just below her knees. I kissed her knee on the inside. Jeans to her ankles. I kissed güvenilir casino a few pecks down the inside of her left calf, then the right calf. I then pulled the jeans off, quickly followed by her socks. I took a second and slowly took in her beautiful body from her toes to her feet. To her ankles, then her shins. My eyes worked their way up her knees to her thighs. They lingered on the sight of her lower half clad only in white panties with faded flowers on them and a wet spot that seemed to be growing by the minute.

Then up her stomach to her beautiful breasts with pink areolas and erect nipples pointing straight up, heaving up and down from her heavy breathing. Then up to her eyes staring passionate lasers at me. I quickly took in the sight of her young adolescent body laying on the floor beneath me. I reached up and grasped either sided of her panties while staring directly into her eyes. I slowly peeled them down while she lifted her butt to allow me to do so. I slowly unveiled a little pubic hair.

I then noticed the top of her slit. Then more. As her panties were pulled from her pussy I could see her juices almost pooling in her panties. They were stringing from her pussy to her panties as if they were the last barrier between her and womanhood. Once the last strand broke, I pulled her panties completely off.

I took it all in. Her beautiful naked body laying before me. The wildfire of passion in her soul staring at me. The scent of her intoxicating perfume that I will forever remember mixing with the musky scent of her untouched womanhood.

I picked up her left foot and brought it to my mouth. I lightly kissed the end of her foot, then the middle, then the front of the ankle. The whole time taking in the sight of her naked body and the way it moved when I moved her leg. I then kissed her shin moving towards the inside. I kissed her knee on the inside. I started shortening the distances between kisses and kissed her inner thigh moving closer and closer to her womanhood.

Her musky yet sweet scent was growing stronger and filling my nostrils. When I reached her inner thigh where it connected with her pussy I pulled out, sat back and picked up her right foot. I began this torturous yet invigorating performance all over again. The end of her foot. The top. Her ankle. Her shin. Her inner shin. Her inner knee. Shortening the distance between kisses. Her inner thigh. Coming closer. And closer. Her breathing was very shallow and she was moaning, egging me to finally touch her sweet spot. To give her the release she so badly desired.

One more kiss where her thigh connected with her pussy. I then snaked my arms under her thighs and my hands reached around and rested on her heaving stomach. I then kissed a small, but quick circle around her trimmed pussy. I took my hands and pulled her lips apart. It was like opening an oven in the middle of cooking. Heat poured out, juices ran down, and that sweet yet musky scent blasted me in the face like a bomb going off. I loved every bit of it.

Like I mentioned before, she was my first. I knew I was good with my kisses, but I had read stories just like this one and had asked a few girls. I knew what to do with kisses on her lips, on her breasts, and all over her body, but I had no idea what to kiss and/or lick on the inside of her pussy.

I had been told her clit was towards the top of her pussy. I did not see anything sticking out that had a sign above it saying “lick here”, or “kiss this.” So, I simply began exploring. I kissed the top of her pussy. I kissed down her left side, then her right side. I licked her left lip, then her right lip. I absolutely loved the taste of her juices. I then licked some of her inner folds. From the middle to the top.

The whole time she was breathing very deeply, moaning, and squirming. I used one hand to keep her lips open and moved the other up to help hold her down. My tongue darted from her left side to her right side, top to bottom. Then, when my tongue hit a piece of skin towards the top of her pussy that was stiffer that the rest of her folds, I heard Alyson suck in a deep breath. My tongue was moving so fast everywhere, that I had lost where that spot was. I began to move my tongue a little slower at the top of her pussy.

I heard her draw in another sharp breath and realized I had touched that spot again. I finally noticed some of her pussy folds appeared to be wrapped around something. It looked like a tiny tree stump. I stuck my tongue out and flicked it up. Her hand grabbed my head and she sucked in air again. I knew I had found her clit. I then zeroed in on her clit and began flicking it up and down, left and right.

After only another flick or two, Alyson contracted her body. Appearing to do a crunch and shoved my head into her pussy while she sucked in air. While she smashed my mouth into her pussy I flicked her clit one more time and she squealed so loud I was sure someone canlı casino would hear us, but I didn’t care. It finally clicked in my head that she had just had an orgasm.

Once she released my head I sat up and looked at her. She looked absolutely gorgeous laying there with her hair all a mess and her boobs heaving up and down. Once she opened her eyes, she looked at me and told me she was ready. That was all I needed and in a flash I was as naked as she was.

I crawled on top of her, with my legs between hers. I laid my chest down on her breasts and kissed her passionately and deeply. I reminded her that I had never done this before and that I didn’t really know where to put my dick. She told me, “That’s ok, I know where it goes.” I told her that I would go slow and that I had been told that a girl’s first time is painful at first. I told her to tell me when I should start and stop when she was in pain. She said ok.

With that she reached between my legs and grabbed my rock hard 7″ dick and placed the head at the entrance to her pussy. It felt like she had dipped the head of my dick into hot water. I then began to push forward and she released my dick saying that he was going in. I could feel the walls of her pussy already squeezing just the head of my dick. Her eyes were closed as I pushed him a little deeper.

Once I had about 2″ of my dick in her I tried to press forward and he wouldn’t slide in any further. She told me I was at her hymen and that I needed to pull out slightly and push past her hymen and take her virginity. I asked her if she was ready for this and she said yes. I kissed her passionately and pulled my dick out till only the head was in. I then thrust forward with everything I had, not wanting to fail like a little league team bouncing off a banner. Next thing I knew, She sharply drew in a deep breath and held it. I noticed that not only had I obviously broken her hymen, but my dick was completely inside her.

All 7″ I was in heaven at the time and I looked down hoping she was there with me when I saw tears rolling down her face and I quickly remembered this part was painful for a girl. I asked her if she was going to be ok and she said to give her a minute. She then told me to pull out. I started to get discouraged thinking she was in too much pain to continue and pulled out. When she noticed I was about to get off of her she grabbed my back and pulled me down and asked me what I was doing. I told her I thought she was in too much pain to continue. She told me that, yes it hurt, but she had been told the quickest way to get passed the pain is to have the guy continue to fuck her. She told me to get back in there, but to go slow.

I did as I was told. I placed my dick back at her entrance and slowly slid in. Now that he was lubricated, he slipped in a little easier. I pushed one inch in and she told me to hold it. She said continue, then a couple more inches in and she said hold it. She did this until I was completely in again. She then told me to start pumping slowly without stopping.

So, I pulled him most of the way out and started pushing in again. I thought just being inside her felt good, but it was nothing compared to the way it felt as I was moving inside of her. I was in complete heaven and she was slowly starting to enjoy herself as well. After a few slow strokes, I tried to speed up. It only took about two or three quicker strokes before I could feel my orgasm just about to burst, so I abruptly stop, trying to contain it, to make it last longer. She asked me why I stopped. I told her that I was about to cum and I wanted it to last longer.

She told me that she had already gotten off once while I was inside her, the big one when I was licking her pussy and a few small ones before that. She said her pussy was feeling good again and it was my turn to get off. I asked her if she was sure and she said yes, my only stipulation was that I had to pull out right before I came. I told her no problem.

So, I reached my arms underneath her back and started pumping quickly into her trying to hold off my orgasm as long as possible. She reached her arms around me and pulled me in tight, she then locked her legs around my torso and after about 6 or 7 more quick pumps I told her I was gonna cum!! She released her hold on me, I lifted up and pulled out.

I grabbed my dick as he began squirting jizz all over Alyson’s stomach and breasts. I continued to jack him while more and more squirts came out of him. Some landed in her hair, behind her head, and some on the floor. It was the best feeling I have ever felt to this day.

We kissed again passionately with our love sticking to both of us. We began cleaning up and getting dressed. As we looked at the clock, we noticed that it was time for Alyson to go to her basketball game.

As we were walking down the hallway towards the gym she looked at me and sarcastically said, “Thanks for making me play in wet underwear!”

I told her “No problem! If you have a good game tonight, I can do that again for ya before your next game!”

She just looked at me and said “I bet!”

The End, remember to let me know what you think and if you want more shorter stories about Alyson.

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