High School Anal Virgin [m/f] | 2016

I haven’t been keeping you guys up to date on my antics with C for the last couple months – I’ve been busy finishing college applications! It’s finally winter break, and I thought you would like to hear about what I did last night.

I describe the two of us in more detail in my first story, but if you’re lazy just remember that we’re both high school seniors. I’m a 115 pound, 5’5” dirty blonde with hazel eyes, and C’s a tall, toned, blue-eyed guy with short light brown hair.

It was our first day of winter break. On one hand, that means more free time and no homework, but on the other, it means that neither of our houses are ever empty. We haven’t had to use my car since the summer, but it would have to do for tonight.

We texted the whole day long, establishing what was going to go down. He told me to wear a short, loose skirt, my youngest-looking panties, two braids in my hair, and extra eye liner. I asked him if he wanted me to resist him at all (we’ve done some rape fantasies in the past), but he said “just do the innocent thing, like you’ve never done this all before.” That was definitely a new fantasy for us.

And then he asked something that I was not expecting: “You have any lube by chance?” He often fingered and ate out my ass, but we had only talked about the possibility of anal once before. I had told him that I was up for trying it, but we never got around to doing it.

I showered for a solid thirty minutes, carefully soaping and shaving every inch of my legs and pussy. I even slipped a soapy finger up my ass to make sure I was completely clean, inside and out. When I stepped out of the shower I moisturized my whole body, paying extra attention to my ass.

I still had a couple hours before we were going to meet up, so I decided to drive to CVS and buy some lube. I thought that it might be pretty empty at this time of day, especially during the holidays, but it seemed especially crowded when I walked through the door.

I quickly walked to the aisle in the back that housed condoms, lube, etc. I grabbed the first tube that didn’t proclaim “ECSTASY FOR HER” in huge letters – I found one that could easily be mistaken for a hand cream or something.

I waited in line, carefully holding the tube so that the KY logo was obscured. I saw one of my classmate’s mothers walk in the door, and she cheerfully waved at me. I smiled weakly back. When I got to the front of the line and put my item on the counter, the slightly nerdy twenty-something male cashier turned beet red. I smiled at him and he immediately dropped eye contact. I thought that he would have gotten used to girls buying things like this by now.

Back at home, I slipped into a pair of polka dotted panties, a short and loose gray skirt, a nude bra, and a modest blouse. I carefully packed my purse with the lube, makeup wipes, eyeliner, a hairbrush, and a small towel. With these incriminating items burning at my side, I told my mom that I was going to hang out with some friends as I headed out the door.

I drove halfway to his house and pulled up on the side of the road. With slightly shaking hands I applied a thick swoosh of eyeliner to each eye and carefully made two braids in my freshly washed hair.

I was ready.

Continued.