Virginity Stories - Deflowered Memoirs From Virgin to Vixen Girls' Stories of Losing Their Virginity
First is the Worst

By: Lucy Rae

There he was. Tall, muscular, strong. He had a mustache growing in, which was more than most guys could say at his age. He also had a buzzed haircut, a square jawline, and he wore a Sublime t-shirt. He was sitting at his father's computer desk chatting on AOL Instant Messenger, probably to the million other girls who wanted him. "Did he have a girlfriend?" I wondered.

“Dude, come watch me play Zelda and stop staring at my brother.” My friend Sarah grabbed me and pulled me out of the computer room and into the room with the TV.  Sarah was my best friend and she knew I was boy crazy, which she didn't mind.  But she did mind the minutes I stared longingly at her high school aged brother, Brandon. This might not sound like a problem, but we were in only 7th grade.

Back in Sarah’s room, I lit a half-smoked cigarette that was left in the ashtray by one of Sarah's parents.  They had already been sleeping for a while, so I didn't worry about filling the room with smoke.  At this point, I didn't regularly smoke cigarettes, but I thought it would make me appear older, sexier, and more appealing to Brandon.  Sarah lit one too. We were both rebellious thirteen-year-olds who were trying to push limits.  At our middle school, we were the “bad asses,” always decked out in revealing black clothing and spiked collars.  As we smoked, I walked to the CD player to put on my favorite album, Gwar's Scumdogs of the Universe.

The computer room door slammed open.

“Whoa, Sarah! Your friend likes Gwar?!” Brandon looked me up and down and smirked. “You girls want to watch a movie?”

My heart jumped. A movie, with like, the hottest guy I had ever seen in my life. Maybe he would kiss me! I would love more than anything to tell the girls at school that my first kiss was with a high school boy. What if he asked me out? Wow…maybe I would become popular. I was, for lack of a better expression, shitting my pants with excitement.

“Only if we can watch 'The Craft',” Sarah whined.

We popped the movie into the VCR and Brandon plopped down in the middle of the couch.

“Eew, Brandon, I don't want to sit by you. I want to sit by Lucy. Go over there.” Sarah whined, once again.

I sat in the middle…exactly what I wanted. The movie started, but I couldn't concentrate on it. I could feel his breath on my arm and I was getting goosebumps, and feeling very very warm between my legs, something I don't think I had felt before. Then it happened.

“Do you want to hang out with me upstairs?” he whispered in my ear, as he placed his hand on my thigh.

I looked at Sarah. She kept nodding out. I could tell she was tired and would be asleep soon. I looked back at Brandon. “When she's sleeping, sure,” I whispered.

I turned back to Sarah. She was already snoring lightly. I started to regret what I had just said.  He grabbed my hand and I followed him up the stairs. When he opened his bedroom door, it creaked, and I jumped.

“What if your parents hear us in your room? Won't you get in trouble?” I asked as I was shaking.

“I'm allowed to do whatever I want.” he said. “They don't care, and here, I'll lock my door.”

He slammed his door and used a tiny hook lock to secure it. “You can sit down on my bed if you want,” he offered.

I awkwardly sat at the very edge of the right hand corner of his dirty king-sized mattress. There were no sheets or blankets. A single pillow, once white but stained yellow, lay in the middle of the mattress. He sat next to me.

“So word has it, you're really good at sucking dick,” he said, as he rubbed his hand across my abdomen. His face was so close I could smell his breath as he talked. It smelled like barbecue sauce, or maybe some kind of pork.

I knew what he was talking about. There was a rumor traveling around my middle school that I had given a boy a blow-job. It wasn't true…I hadn't even kissed a boy yet.  But, even though giving a blow-job isn't something especially cool to be proud of, I let the rumor perpetuate because I thought it fit my “bad ass” reputation.

“I guess.” I said. My voice was tight. I was praying he couldn't tell I was lying.

“Wanna try it?” he whispered in my ear. His hand was under my shirt, and I could feel it moving closer to my very padded bra. When his cold, clammy fingertips began to touch my breast, I jumped back, afraid to let my secret out.

“Maybe we could do other things first.” I squeaked. My heart was pounding.  “Maybe we could just have sex.”

As soon as the words slipped from my mouth I regretted it. Sex?! I won't give a blow job but I will have sex? Was I crazy? Why would I even suggest something like that?

Brandon looked shocked. “Have you ever had sex before?”

“Uh... no...” I squeaked back again. “Have you?”

“No, but uh... I guess we can. Here, take off your pants.”

I leaned back on his dingy mattress covered in cum stains and tore off my faded, ripped blue jeans to reveal the floral printed underwear I had owned since the fourth grade. I pulled down my panties to reveal a very different change of scenery. Underneath those little girl garments, I was a mature woman, covered in thick black curly hair. I lifted my head to see him standing there, naked from the waist down. This was only the second time I had seen a penis in my life; and the first was the result of a traumatic freak accident, where I walked into the bathroom as my grandfather was stepping out of the shower. But back to Brandon’s penis. Let’s just say, I wasn't pleasantly surprised. It looked like an alien to me, and I couldn't help but giggle.

“Do you want this?” he asked.

He was so serious! I couldn't help but giggle more. How could I want that weird alien looking thing?

“What are you laughing about?” He was stroking himself furiously. It was beyond anything I had ever seen before, and it wasn't very funny anymore. It looked like such an aggressive, forceful act to me.

“I guess I'm just nervous.” I said, leaning back on the bed. I arched my back and, with my index finger, motioned him to come closer. Isn't that what girls do when they're being sexy?

He climbed on to the bed, and then on top of me. “Touch yourself first,” he said. He must have heard that in a porn. His voice cracked when he said it and I could tell he was embarrassed. I tried to hold back my laughter. I noticed he had a lone chest hair and minimal armpit hair. He was so young, just like me.

I reached down and began rubbing myself, and then got bored and brought my fingers back up so I could fold my hands behind my head. But I noticed something...my fingers were red. I was on my period. I panicked. What was I supposed to do? I had heard that when you lose your virginity, you bleed anyways...So maybe I would just tell him...

“Hey, you should go inside of me now.”

Lucy is now an ex-freight train riding punk chick living in Chicago, IL. She's currently a college drop out, freelance house cleaner, and throws D.I.Y. Punk shows. She never talked to Brandon again, but has heard that he has been in and out of jail ever since.

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