*I have always enjoyed all of your stories and now I feel like sharing a story of my own. This is my very first time writing down and posting this. Im not native in English so i apologize in advance for my errors in grammar and spelling. As this is a real story I have changes the names, except my name.
I grew up in a small suburban townhouse with my mom and my stepdad, without really knowing my dad. Growing up I didn’t have a lot of confidence or self-esteem. We didn’t have a lot of money and as a teenager I didn’t feel I any pretty. My mom had for most of my life been on unemployment benefits and my stepdad was in and out jobs as a truck driver. So, growing up we never had a lot of money. Therefore, I was always dressed in clothes from the supermarket unlike my classmates who were dressed in clothes from the clothes stores and even brands. One day my mom agreed to take me shopping because all my underwear was too small and started ripping up around the elastic.
When looking around the store I found a double pack with black G-strings and a per of low waist light blue ripped jeans. I thought I wound look super cool in these and for once I would could wear a G-string in the locker room like the other girls at school instead of my boring out-used panties. I showed them to my mom and she answered. “You aren’t going to be comfortable with that underwear and I’m not going to buy you jeans that are already broken. I found these for you instead and they are also cheaper.” A six pack of panties for the same price and a per of normal black jeans. I unwillingly accepted her choices.
My looks as a 16 years old girl could at best be described as average. I have dark brown hair with bangs, light blue almost grey eyes and a ring in the side of my nose I had done on my 15th birthday. I am 163cm tall and at that time I had a little round cheeks, chubby around my stomach, and a little too big butt with a few stretch marks on at the sides. Of course, even being a little chubby I still had small breasts which were only B-cups.
In school I didn’t get particularly good grades and even though I was always trying to be nice to people and make friends, it was like I was completely invisible to everyone else. The boys didn’t pay me any attention and the other girls mostly made fun of me because of my looks, clothes, or because I probably was the only girl in class without any sexual experience.
Only exception was Alice who was always nice to me. We would always eat lunch together and per up for group work. Even if she hung out with me at school and didn’t socialize much with the others, they never picked on her like they did with me. I guess because they were a little intimidated by her. She was smart, came from a successful family, and had a killer body. She was 175cm tall, an always suntanned slim body and big D cup sized breasts. However, we wouldn’t really hang out together outside school because she always had homework, family things or played soccer which she played on one of the best teams in the country.
Therefore, after school I would normally just go home and sit in my room listen to music and browse through social media while fantasizing about how my life would be if a had been as smart and pretty as Alice. I was so jealous of her. I always thought she had the perfect life. Sometimes when laying in my bed at night I would fantasies what one of the good-looking boys from the older classes would do to her in bed. Touch her. Kiss her. Thinking of that, would make me aroused.
It was one month into the summer vacation after I finished the 1st year of high school. It was Saturday around 18:00 and I heard my mom calling me down from the kitchen telling me dinner was ready. On my way down the stairs, I saw my stepdad and mom already at the dining table in the middle of the kitchen when someone knocked the front door twice and open it right away. It was my half-brother, Brian. Technically he was the son of my step-dad so I had no biological relationship with him. But I still called him my half-brother. He is 4 years older and had never lived with us. We were not really close and actually he had a way to always pointing out my flaws like asking me I gained weight or why I wasn’t going out with friends.
While all four was eating dinner my mom almost rhetorically asked me if I had any plans tonight even if she knew I wasn’t going anywhere. I shook my head and looked down on my plate.
Brian said: “I got invited to three different parties tonight but I will head over to Jakobs in a bit. His parents are not home so he has the whole house for himself. I think more than 50 people will be there”
Jakob was 3 years older than me and had just graduated from the same high school I went to a month earlier. He was for sure one of the most popular guys at the whole school and only hung out with the other popular boy and girls from the neighborhood. Even the most popular girls from my class weren’t in his league and probably wasn’t going to be at Jacobs party.
“Can I come with please?” I asked. “Please, I won’t bother anyone.”
My mom turned her head and looked at Brian before saying
“You should take her with, otherwise she is going to sit in her room and be miserable the rest of the night”. I weirdly looked at my mom for being that honest.
“I won’t stay for long I just want to go to a party for a change, please, please can I come” I begged.
“Okay but im leaving in 5 minutes and im not gonna wait for you” Brian disappointingly answered.
“5 minutes!?” I surprisingly repeated.
I rushed upstairs and changed my pajamas pants I had been wearing all day with the new black jeans and a grey t-shirt. I didn’t have anything more festive. I put mascara and eyeliner on and ran down the stairs and found my shoes. Brian already had his jacket on and was talking on the phone. I waved and smiled to my mom and stepdad who was still sitting at the table. I turned around and followed Brian out the front door.
We walking around 15 minutes while Brian was talking on the phone all the way there, so I followed just behind him. When we arrived to the house, I felt nervous. I followed him around the house and into the backyard where around 25 people there sitting, talking and laughing. Music came from a big speaker in the garden. Brian pointed to a table full of beers, wine and some sodas which I guess were mostly used to mix with the stronger alcohol like vodka, rum and whiskey.
I went to the table to pour some sprite with a little splash of vodka in a plastic cup. I turned around and couldn’t see Brian anywhere so I sat down on a plastic garden chair next to me and looked over at the other people. A group of girls, clearly a couple of years older than me, came to the table to prepare a drink. They looked at me and wisped something before breaking out in laughter. They then returning back to the other end of the garden.
I sat there taking sips of my drink for a while before a guy came out of the house and poured himself a whiskey and cola. He was kind of good looking. He was tall and skinny and had short machine cut blond hair. He was dressed in jeans and a white tank top exposing the tattoo covering his whole right arm.
He looked at me and asked; “are you enjoying the party?”
I turned around to see if he was talking to someone behind me. To my surprise there was no one so I nodded to him and looked down shy.
He asked “what are you drinking “
“Just some sprite and vodka” I answered.
He poured two shots of whiskey and said “Jakob and I are best friends and he asked me so make sure everyone is having fun”. At the same time, he reached one of them to me while preparing to drink the other himself.
“Cheers” he said and drank the shot.
I hesitated a bit before drinking it. Instantly I felt it burning in my mouth and down my throat. I coughed and felt the heat in my cheeks.
“You aren’t much of a drinker” he proclaimed.
I blushed and looked down. I had never been drunk before.
He poured two more and give me one.
“I can’t” I said.
“Common, you don’t look like someone who goes out a lot. Its good for you” he insisted.
I took the shot and quickly drank it. I was even stronger than the first one. I felt my stomach turn, but managed to keep it down. He came and sat next to me and asked me what school I went to and if I liked it.
I lied and said I liked it a lot and things like that. I felt the alcohol started working its way on me. I don’t remember the next minutes until he suddenly got up and took my hand before saying.
“Come with me”.
I followed him into the house and up the stairs. It wasn’t before we got to a bedroom, I realized his intentions. Even if I wanted to lose my virginity, I didn’t want it to happen like this. Anyway, the alcohol made me unable to think straight and I was also afraid he would be upset and make a scene if I rejected him. I stood in the middle of the room and I was so drunk the whole room was spinning.
He closed the door and went directly to grab my ass with one of his hands while the other grabbed one of my breasts. He come closer to kiss me so opened my mouth as he stuck his whole tongue into my mouth. I stood paralyzed there for what felt like an eternity while he took of my T-shirt and bra exposing my breasts. I had never been naked in front of a guy before so I tried to cover my breasts with my hands. He then opened the top bottom in my jeans and stuck his hand into my panties, before pulling it back out.
“You are not shaved” he said disappointingly while looking weirdly at me.
In the same second, I remembered that I haven’t shaved since the summer break started. Normally, I didn’t care too much about it since I wasn’t sexually active and only did it because the other girls at school would be shaved and would laugh at me and say that why I can’t get laid. I looked down my open jeans and saw my dark pubic hairs sticking out of my panties.
I blushed and felt my cheeks turn red from embarrassment.
He put his hand back down my panties and ungently rubbed a couple of his fingers up and down between my pussy lips while I held my breath. I grabbed around his wrist trying to signal that he was hurting me.
He stopped and took his clothes off exposing his already half stiff cock. It was shaved without a hair on it. He grabbed my shoulder and pressed me down on my knees in front of him. I had never been in this position before. I looked at his cock before nervously grabbing and pulling back on his cock exposing its purple head. His hand went around my neck and pressed me closer. I stuck out my tongue and licking the head of his cock a couple of times. His cock grew and stiffened up to become fully erected. It was quite long, approx. 17cm (6.7 inch.) but was relatively thin.
I then opened my mouth and wrapped by lips around the head. His started moving his hips back and forth while his hand around my neck kept my head steady, making my lips glid up at down his cock. He tightened his grip around my neck and suddenly trusted his hips forward, jamming the whole length of his cock all the way into my month and down my throat.
I instantly gaged on his cock and my eyes teared up. I pulled my head back and gasped.
“You are doing well” he said. “Open up your mouth again”
I opened my mouth once again. This time, he slowly pushed his cock into my mouth until the tip of his cock hit the back of my throat making me gag once again. I felt a tear running down my cheek
He then stopped pushing it further in but kept it down my throat. I gagged again. I could feel my stomach compress like I wanted to vomit. He pulled his cock out again with my drool dripping down from my chin and his cock.
“Your cock is too big, I can’t take it like that” I said.
“Then take of your pants and get up on the bed” he commanded.
I did as he said and sat on the edge of the bed with closed legs. Still influenced from the alcohol, I felt like the room spinning around the bed.
He bended down and got a condom from his jeans and rolled it on his cock, before walking to the bed. He grabbed my legs under the knees and turned me around on all four, with him standing just behind me between my legs. He pulled my panties down to my knees and grabbed my ass with both hands to spread my butt cheeks apart giving him the full view of my hairy pussy and ass.
“You have big pussy lips for a small girl”. He said surprised.
I have quite big labia and a meaty pussy. When comparing myself to the other girls at school, which had nice small pussies, I always had to try and hide my so that they wouldn’t see it. It made me insecure about myself because I didn’t think I had a pretty pussy and also, I had heard that guys only liked pussies with small lips.
He spat down on my ass and put his erect cock between my butt cheeks and slid it back and forth a couple of times over my asshole before starting to press his cock inside my pussy. I reached down between my legs to spread my pussy lips while nervously saying:
“Please be gentle with me”
With both his hands holding my hips he slowly but steady pressed his cock into my pussy. Even thought my tight pussy resisted, he pressed it all the way up. I whimpered and curved my back to ease the pain.
“Damn you are tight” he said.
He pulled his cock out and pressed it all the way in again. The pain felt like a knife went thought my lower stomach and made my legs shake. He continued to fuck my pussy while I whimpered. Every time he thrusted, I could hear the clapping between my ass cheeks and his hips. He put a pillow under my hips and grabbed my neck and pushed my head down the bed making my ass stick right up the air.
He speeded up and started to breathe heavier as he pounded my pussy harder. I clenched my teeth from pain while I sobbed. He pulled out and moaned loudly as I with one second interval waves felt the heat from his warm cum shoot out over my back and ass.
“That was awesome” he said.
He quickly got dressed again and threw me a t-shirt he found on the floor.
“Here, use this to clean yourself up”, he said.
“See you downstairs” he said and left the room.
I fell down on my stomach and froze up. My legs were tired and my pussy was burning. Still affected from the alcohol I got the t-shirt and dried of his cum before I put my clothes back on. I was in no mood to party so I walked down the stairs and out the front door. As I in a fast pace began walking home, I started crying. When I came home my mom and stepdad was asleep so I ran up to my room and threw myself on the bed.
Even if I finally lost my virginity, I was sad because my first time was nothing like I expected. Like most other girls that age I always thought it was going to be romantic with a future boyfriend and not like that night.
This was my first of many sexual experiences to come.
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