My first time occurred the summer before e****h grade. I was a grade ahead for my age, and because I was pretty good athlete, most of my friends were a couple years older, and much more sexually mature. I barely had pubic hair, meanwhile my friend Chris was six four and already dating. His girlfriend Kara and her f****y lived upstairs from my f****y. Kara was tall and thin, beautiful face... Possibly one of the best looking girls in school.
One summer afternoon, Chris convinced me to double date with Kara's younger s****r Laura. Laura was a grade behind me, but actually a whole month older. Even though she lived like 20 feet away, we weren't friends, mostly because I was intimidated by how good looking she was. Turned out she was pretty cool, and a little shy herself. The date was mostly Chris and Kara making out and feeling each other up, and Laura and I watching in sheer amazement.
On the walk home, Chris asked if I still had the keys to the apartment building's attic. The attic was full of everyone's extra furniture that didn't fit in the tiny apartments. I still had the key, and my friends and I had been playing football and American Gladiators up there for a few months. The girls stopped off at their apartment to "freshen up", while Chris and I went upstairs.
There was one room with a door in the attic, and Chris asked me to help him move and assemble a bed in there. Shortly there after, the girls arrived. Kara was still wearing just a little yellow tank top and denim miniskirt, legs up to my neck. Laura had been dressed very conservatively, more like she was going to church. Even though it was July, it wasn't that warm in Frankfurt. Laura looked exquisite in a little gray sweater, knee length skirt, and pantyhose. Her brunette hair bounced off her shoulders dreamily. I noticed that despite being more than 3 years younger, Laura's chest was much more developed than Kara's... I was only afforded a brief opportunity to compare as Chris and Kara closed the door to continue their mating ritual. Her gasps, screams, and moans were quite audible.
Laura stared at the door, "That is so gross."
"I know. They wouldn't even come up for air. I could barely finish my ice cream."
She laughed, "Me either... I kept thinking she was just going lay on the table and spread her legs." I turned and our eyes met. "I don't know what she she's in him... He's so immature."
"I think I know," I said, a little embarrassed.
She looked at me, puzzled, so I put my hands up in front of my face, about a foot apart.
"Oh.." She said blushing and looking away. I had seen Chris' adult-sized package once or twice. "Still, she's so smart and pretty... She doesn't need to be such a slut."
"But you're prettier!" I blurted, not sure where it came from. Both of us stammered and searched for responses.
"Naw... Kara... She's a model... Like... I don't know..."
After a few moments, I continued with some cheesy lines. "But I like your eyes better... And your hair is so long and straight... And you are nicer... And smarter..." She blushed again, noticing that I was totally staring at her fuzzy sweater breasts.
"And, yeah. Kara envies these," touching her chest with her right hand and my forearm with her left. It was immediate electricity, and my little cock stirred in my pants. We stood there quietly for several seconds, eyes locked. Her little heels made her an inch or two taller than me. I sensed that I had stopped breathing.
Kara's shrieking orgasm shook us out of then trance, causing us to both laugh... Somehow we bumped heads, and laughed even harder. I put my arm around her to steady her balance, and guided her toward a mattress that had been laid out as a wrestling ring.
"Oh my God! Does she have no shame? She woke the dead." Laura was giddy. I nodded and agreed... She was so beautiful, and she was on a date with me! I stroked her back and soft hair. I could feel her bra snap through her sweater, and my cock swelled as she set her head on my shoulder, hand on my knee. We continued listening to our personal sex show, allowing our adolescent libidos begin asking the questions. Despite her popularity, she had never kissed a boy. I was incredulous.
I quickly leaned in and our lips met. We didn't use tongue at first, but it was perfect. Her hand stroked my leg, and I felt things I had never felt... Hell, I'd never even masturbated before. I moved my other hand to her nyloned leg, heightening our excitement. She was so soft and warm, and her breasts radiated through her sweater. Sensing I wasn't experienced or coordinated to pull it off, she reached back and unhooked her bra through the sweater. Her perky C-cups didn't droop at all. I bravely slid a hand up under her shirt and gently stroked the bottom of her breast. Laura sighed quietly, moving her hand across my crotch and under my t-shirt.
Our shirts came off together, and her bra fell to the mattress between. Her hair fell to the tops of her round breasts, which pointed at me, each areola about the size of a pink silver dollar. I had barely seen this much in a Playboy. As exciting as it was, it was also extremely uncomfortable, neither of us really knowing what to do next. We probably would have content kissing and playing above the waist, but there was something about her pantyhose that was driving me nuts.
"I can take off my skirt, too, if you want." She batted her eyelashes and I nodded, my throat closed off. Rather than standing, Laura unbuttoned her skirt and laid back on the mattress. She arched her back and lifted her ass, allowing me to slide it down her legs. She wasn't wearing panties under her hose, and a thick dark patch of untamed bush stood out from her crotch. Not quite understanding the female anatomy or erogenous zones, I stroked her bush through the nylon and she squirmed silently.
After a couple minutes of petting, she pushed me back and asked, "can I see..." Motioning at my shorts. We sat back up and I slid my shorts off, and she tugged at my tighty whites, which got hung up on my rigid boner. She gasped once it out in the open. My little hairless, uncut cock proudly pointed three inches up at my belly button. It was so hard that when she put her hand around it, she could hardly push it down. She wiggled it some, and it felt so good... The room was spinning.
"You can't pee out any sperm," she said curtly. Before I could respond, she added, "I don't want to get pregnant.". We continued to incorrectly masturbate each other for minutes, and I eventually rolled on top of her, though I feared I might crush her. Our genitals were touching through the hose, but I wanted more. She helped roll down her hose, and I got a close up of her sex. Her slit was still hairless and well concealed... I had my fingers stroking it an she began breathing harder, squirming more. I could finally feel the wet opening to her vagina. I started to insert a finger, but she cried out and pulled me back on top.
I humped her bush for several more minutes, and it felt amazing. I tried to readjust to penetrate, but couldn't find the hole.
"I don't think it will fit," she said confidently, "And I don't want to get pregnant."
She stroked my foreskin, and I felt my legs get all jelly and my vision went blurry, but I did not squirt.
I stroked her hair, and her pubes... She smiled, but eventually we were trying to figure out what next.
"Did you want to give each other blow jobs?" I suggested.
"Well..." I kind of knew what it was, and I was way too embarrassed to say. "I guess... I'm supposed... Well... I lick your vagina and... Yeah... You suck on my penis..."
She paused, "eeeeew! That's disgusting!"
Her response made me laugh, and then she laughed. Then the reality of the situation set in, as we were laying on a strange mattress naked, noticing a small stain of some fluid. The other room was also quiet, and Chris and Kara could emerge at anytime. Also, her parents were in the apartment below and could have been alerted to noises upstairs.
We dressed quickly, still horny as teenagers, but fearing the consequences. We never became boyfriend/girlfriend, and I moved back to the US in the fall. I still have fetishes for nylons and brunettes, even after transitioning to female.