I'll admit, I was raised in a sheltered Christian home. Now, that didn't stop me from delving deep into the internet to sate my curiosities when they arose, but it did prevent me from acquiring a lot of practical experience in things deviant from the faith, namely sex. I was also raised in a Christian private school with a strict dress code and many rules meant to dissuade the male and female students from procreating with one another before marriage, but when you lump dozens of hormone-crazed teenagers together, that's something you can't exactly control.

Don't get me wrong, most of us had been indoctrinated well enough to keep it in our pants through high school, but some of us were of a mind that as long as we waited until we were adults, we would be fine. Others considered a relationship in which they assumed they were going to progress to marriage was as good as a marriage, since that's what they were planning on anyway. It was during my tenure there, in my final year, that I lost my purity. My holiness, if you will. To be plain: my virginity.

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It was April. My class of five had just returned from the capital for Spring Break, not a week earlier and had been readjusting well enough, but I was having trouble focusing. You see, in my class, there were three boys and two girls: Josh, Will, and myself were the boys; Tiffany and Rachel the girls. For the trip, we had chaperones with us and our rooms were divided between our sponsors, the boys, and the girls.

There had never been any romances between my classmates or me, though some of us had branched out into the other grades throughout the years. While on vacation, though, something changed for me. All of us had bonded while away, even though we had been close before, but I felt something... spark... with Tiffany, and she felt it too. The entire week, we had been inseparable, and after we got home it seemed like we never stopped texting each other. Of course, it helped that our birthdays were two days apart and we had both turned eighteen in D.C.

Tiffany's parents had recently moved away to Michigan for a job, but since she was a senior, they opted for her to stay in the dorms at the school, to which she didn't object. The "dorm parents" were this couple involved with the church running the school who had been overseeing the dorms for decades, and they were good people, but they could be strict, a common theme among the people of that church. The boys and girls had separate wings of the dorms, which were monitored closely, but not close enough to stop me.

Tiffany and I had been texting for a particularly long time that night, and we were desperate to see each other, so she asked me to come to the dorms. I, of course, objected because there was no way for me to get in since the building was locked at night, and even if I could get in, the dorm parents would probably think I was a thief or an intruder and would not be kind in their response. But she insisted and promised to leave a window open after they had gone to sleep, so I obliged.

-----

I tapped softly on the window, so as not to alert any of her fellow dorm mates. She came to the window quickly and opened it up for me to crawl in. She closed it behind me and we hugged for a few seconds. We weren't allowed to hug on school grounds, but who was going to report us?

"I'm so glad you came," she grinned.

She led me to her bed and we sat. We quietly talked about various things in the twilight hours and found ourselves holding hands after a few minutes. I'm usually one to avoid eye contact out of anxiety, but I couldn't stop staring into her ocean blue eyes. She had fair, freckled skin and long, curly, dirty blond hair. She was perfect. Whenever she smiled, her eyes would crinkle in a way that just melted me.

"So... Since you're here and it's so late, do you want to..."

"Do I want to?" I arched my brow, confused.

"You know."

"Oh." I got it, "Um... Are you sure?"

She looked away, "No, never mind. I'm sorry I asked."

"Hey," I reached out and turned her face toward mine, "If you really want to, then yeah. I just don't want you to waste your first time on me, you know?"

"It wouldn't be wasting it."

"You're perfect, you know that?" she blushed, "I don't want to be disappointing. I want your first time to be amazing."

She rolled her eyes, smiling, "It can still be amazing with you, dummy," she took a breath, "Okay."

In the darkness, with only the light of the bright, full moon outside, we got up and began to undress. I turned away from her, embarrassed at my thin frame. Adrenaline flooded my veins at the prospect of what was about to happen, but I tried not to get jittery; I didn't want to scare her or be creepy. By the time I turned back around in just my boxer shorts, she was still fully clothed, cradling her chest.

I took a step forward and put my hand on her shoulder, "Hey, are you okay?"

"Yeah, I'm fine, I just," she sniffled, "I'm fat."

"Hey, hey, whoa," I stepped around her and got down on my knees to look up into her red eyes, "You're beautiful. Who cares if you're heavier than some other girls?"

She rolled her eyes and smiled sadly.

"Look, if I thought you were you were some fat, ugly girl, I wouldn't have said yes. I wouldn't be almost naked," I chuckled, "I think you're the most beautiful girl in the world, and I count myself as lucky for you to even consider letting me be your first."

Her smile was happy that time and she pulled me up into a hug. We hugged for several seconds before she let go and pulled her shirt over her head. She wore a lacy purple bra, which surprised me. I don't know what I had expected her to be wearing, but it had caught me off guard. Given the circumstances, I suppose I had expected something plainer.

She tugged down her skirt and stepped out of it and I stepped forward and kissed her again. As we pressed our lips together, I slinked my hands around her back and unbuttoned her bra, which was more difficult than I expected. We broke apart long enough for her to toss it aside and continued for what felt like a long time.

Eventually, I pushed her off and onto the bed, where she lay on her back in anticipation, biting her lip as she watched me. I stared at her with an open mouth for several seconds before getting down onto my knees. Now, I'd seen a lot of porn in my days, so I knew I was supposed to eat her out, but I'd never actually seen what I was supposed to do with my tongue, so I just guessed.

I pulled her panties down slowly and was met with a lightly trimmed bush, which is still the best kind, if you ask me. I looked at it for a couple of seconds, then flicked my eyes back up to her face, then back down. I leaned forward and pressed my mouth to her lips and pushed my tongue inside.

I sloshed it up and down like a paintbrush and she moaned, so I assumed I was doing it right. I kept doing that until I felt what I assumed correctly was her clit. I pulled it into my mouth with my tongue and sucked lightly, to which her hands gripped my hair. I grazed it with my teeth, which elicited her first moan, so I did that several more times as my tongue swirled around inside her. I kept going for some time, and even had my arms wrapped around her thighs, but I stopped when she tugged my hair away.

I looked up at her, my mind still dominated by her warm pussy. She smiled down at me, lightly panting, and nodded up. I crawled up on top of her and felt her heat. She gave me a light nod and I nodded in return. She grabbed my stiff cock and guided it down to where my mouth had been just moments ago. I gave her one last earnest look and her eyes assured me she was ready.

Slowly, I pushed the head into her slit and smiled as her eyelids fluttered. I pushed more and more until my entire length was buried deep inside her, by which time she was already hot and heavy. I pulled it out then pushed it back in, still slowly, but a bit more quickly. I picked up speed as I went, eyeing her to make sure it wasn't too fast, but within a minute I had begun thrusting with hard, fast strokes.

When she started to get too loud, I kissed her, but it only worked somewhat. To be honest, It didn't take long for me to pull out and shoot ropes all over her chest. Though, from the way she shook, I assumed I had done well enough. I collapsed next to her and we lay there for a while together talking, neither of us fully coming down or falling asleep.

It was only when the first bit of sunlight broke over the treeline outside that I realized how badly things were going to go if I stayed. I dressed and gave her a quick kiss before stealing away in the dawn.