Leveling Jessica Up, Part 1

This is the first of a multi-part story. Hope you enjoy! Comments are always welcome.

My name is Jessica Gilman, and I was definitely not a girl you’d take a second glance at if you saw me on the subway. And no, it’s not because the guys here in New York are particularly polite -- far from it. In fact, I’d see them ogling some blonde 20-something with a tight blouse and short skirt almost every day on the ride to school. Nope. I was not that girl. Far from it.

Call me what you want. Ugly. Plain. Drab. Unremarkable. Brutish. I’d heard it all. I was not attractive. I was maybe 5’2”, with frizzy, slightly curly, dull brown hair down to my almost non-existent a-cup breasts. I was on the heavy side; not morbidly obese. but not fit either.

Back in high school, I never even considered dating. It was out of the question. I had crushes on boys, sure. Boys that would not be considered desirable for most girls, but I knew my limits. But even those boys didn’t give me a second look.

There was no way I’d get a date with anyone. So I’d go home and play one of the many RPG’s I’d accumulated over the years. Final Fantasy, The Elder Scrolls, Pokemon, Fire Emblem, anything like that, I played it. It became a routine. I was content.

I am very smart however, and I got a very good scholarship from NYU after high school, despite not having the best resume when it came to after-school activities. Catching all 151 Pokemon back in sixth grade isn’t really something you put on your transcript.

The first year at NYU was hectic, but exciting. I took the opportunity to start over again, to try and find a group of friends I could hang with. I joined a bunch of different clubs (including a gaming club) and I tagged along to the movies and to parties with my (more attractive) roommate, Kerry. I became less of a wallflower and more active in social scenes.I was leaving my shell, my comfort zone, as best I could.

But the dating thing never happened. I could tell that guys mostly wanted to be friends with me because we shared the same interests, but never more than that. The biggest example was my new friend Steven, a big RPG fan but also very good looking, having been on a hockey team in high school. It was extremely frustrating; I wanted to act on my urges but I knew for sure he’d reject me, making things super awkward and leading to the end of our budding friendship. So I shoved those feelings away and tried not to think about any kind of potential relationship with Steven.

It was manageable enough at first; after all, I had a lot of practice in high school. But it all changed one night when we went to a party just a few blocks from my new apartment in Brooklyn my sophomore year. My old roommate and good friend Kerry invited a bunch of people to her place uptown after class one evening for her kid sister’s 18th birthday party. Kerry wanted to get her sister, Robin, and her friends good and drunk and wanted a fair number of “more experienced” people there to make sure Robin didn’t overdo it.
The party was a lot of fun. It was mostly girls, including a lot of Robin’s short, skinny, 95 lb cheerleader type friends, but there were a few guys, including my crush, Steven. I tried to avoid him; any interaction with him was just fuel for false hope, unfortunately. Besides, he seemed very interested in one of Robin’s friends, a 4’11” brunette without a shred of personality or meat on her bones besides those C-cup tits. Steven’s shallowness bugged the hell out of me, but I ignored my disdain and enjoyed the party.
The party went well into the night, and, of course, Robin and her friends had a few too many. Once it was apparent the party was coming to an end, most of the party guests filed out to grab a cab.

I didn’t see Steven, but I figured he must have left without me noticing. I stayed to help Kerry get Robin, who had passed out in an armchair, into Kerry’s bed. Kerry, who was also quite drunk and built like Robin, wasn’t of much help, but we managed to get her down the hallway toward Kerry’s bedroom. I opened the door to the sound of a rapid, rhythmic slapping noises and muffled moaning. Maybe it was the booze, or maybe it was my virginal inability to recognize sex noises when I heard then, but I flipped the switch to the bedroom to find Steven standing behind that 17-year old bimbo friend of Robin’s, pounding into her from behind, her face stuffed in a pillow by one of Steven’s strong arms. He looked up and saw the three of us standing there, one passed out and one too drunk to notice, but he didn’t stop. He was too close to satisfaction. He looked down, focused on his task at hand. One, two, three, four, five hard thrusts later, let let out a gasp and pulled out of her,just in time. A rope of his seed blasted out of his glistening cock just as he unsheathed it, launching at a 45 degree angle right at me. It landed about six inches in front of my feet. Steven had the sense to aim his cock at her ass cheeks as he fired a few more ropes of cum up her back.

Steven exhaled, smiled at us, and said “Sorry ladies, room is all yours” as he grabbed his clothes headed towards the exit, towards us. His steadily deflating 6” cock brushed against my blue jeans as he turned to squeeze past us. I noticed it let a small dab of wetness on my leg as he walked down the hall, stark naked, towards the bathroom.
Kerry seemed to wake up. I thought she may be mad at Steven, using her bedroom to hook up with some underage biddie at her sister’s birthday party, but she didn’t seem like it. In fact, she was staring at the short brunette, who was still breathing heavily on her stomach, white liquid slowly gliding down her back toward her butt.

The scene had shocked me. Not only was this the first time I’d ever seen two people having sex, but this was the first time I’d ever seen a man cum, or even a man’s erect penis before. The scene seemed to have awoken some dormant beast within me, because I found my inner thighs wet with excitement.
But then there was the boiling anger towards Steven. Steven, my friend, with whom I have so much in common, can’t appreciate me for who I am just because I’m not some cheerleader bimbo high school senior.

Kerry’s voice jolted me from my thoughts. “Jess, I’m going to clean Hannah here up… Can you just bring Robin to the couch in the living room? She’ll be fine there,” Kerry said as she slinked toward Steven’s lover, now seemingly asleep in the same position he left her.
“Sure,” I conceded. I was here to help after all. I supported Robin back down the hall and plopped her on the couch. As I walked back toward Kerry’s room, I saw that Steven had emerged from the bathroom, now fully clothed, and taking pictures at the doorway to Kerry’s room with his cell phone camera.

“Mmm, you like that taste baby”? He said into her room.

Curiosity got the best of me as I marched down the room and shoved Steven out of the way. For the second time in five minutes, I couldn’t believe my eyes. I know Kerry was a little bit of a party girl, but I never expected this from her.

Kerry was slowly and provocatively licking Steven’s cum from her sister’s passed out friend’s back. She looked up at us, unfazed by my unannounced presence in the room, and continued to “clean” the girl’s back. Steven kept snapping pictures. When she was done, Kerry flipped the girl over on to her back, removed her own shirt to reveal her perky B-cups, and stepped out of her short jean shorts.

“Got anything left, big boy?” she said to Steven mischievously. She then pulled Hannah’s legs apart and started lapping at the sleeping girl’s bald cunt.

“I do now, for you, baby,” his voice said behind me. His voice woke me from my shocked trance, and the anger flooded back. Really? The guy I want, first with the skank from high school and now my best friend? I stood there as Steven stripped naked again, cock once again standing tall, as Kerry ate out her sister’s now stirring friend. I turned and slammed the door, which almost drowned out the noise of the first of Kerry’s moans. There was nothing to hide the rest of them as I stormed out of the apartment.
I’d had it. I was tired of everyone else having this kind of fun experience except for me. I consciously sheltered myself from this for the first twenty years of my life; never getting my hopes up for getting a boyfriend or getting laid. Now that I witnessed the events in Kerry’s bedroom, however, there was no more suppressing that urge. I wanted in on the fun, and I was going to do anything in my power to allow me to do so.

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