Kim's First Time

All characters within this story are 18 or older. This is a story based on my real experience as best I can remember it. The major details I will never forget but some of the words may have been different. I hope you all enjoy.

I was staying overnight with a friend who I had known most of my life. It was the summer after my senior year and I wanted to enjoy my last summer at home. I often stayed at Amanda's house growing up. We would watch television or listen to music and talk about guys. She had a brother that was home most of the time, and I had always thought he was hot. He had chosen to skip college and started working right after he graduated. I never told Amanda about my crush on her brother though. I would clumsily flirt with him at times so I think she had an idea.

On this particular night, she was more tired than usual and had fallen asleep around 11 pm. I was laying on the floor, looking through my social media. I heard her brother down the hall in his room. I got an idea to go see what he was doing since I was not tired yet and was a little bored. So I quietly left her room and walked down to his door. It was closed, but I could hear him inside and see that his light was on. I knocked softly on the door and waited for him to open it. I was feeling a bit nervous because I had never spent time alone with him before. When he opened the door I was surprised by what I saw. He was standing before me wearing just a pair of boxer shorts. He looked at me kind of surprised and asked "What do you want?" I stood there for a few seconds before I was able to respond and then told him "Your sister fell asleep and I was bored so I thought I would see what you were doing." He laughed and told me to come in. And so I did.

"Well you can hang in here if you want to but I am not into that girly shit. So I don't know how much fun it will be."

I looked around his room. It was cleaner than I expected. He had a movie playing on his TV. I moved over and sat on his bed.

"I didn't expect that you would be into girly stuff. I was just not tired yet and wanted to find something to do."

He looked at me and laughed. "So you thought you would come in here and do me?"

My face must have turned all sorts of shades of red and I fumbled over my words, which made it worse. I was finally able to reply "Not exactly what I had in mind."

Growing up my parents were strict. I was not allowed to date until i was 16 and my parents had to meet the boy before i could go anywhere with him.

I was still a virgin and had only had a few boyfriends. I had kissed boys and done some touching and things like that, but I was always nervous about actually taking the next step. Now I am sitting in the room of my biggest secret crush Brad the brother of my best friend. Brad was a few years older than me and very popular. He was athletic, charming, and always fun to be around. His looks were over the top gorgeous with a hypnotic smile.

"Well... what did you have in mind Kim? You come into my room while I am only wearing boxers at Midnight. You know what happens after midnight? Booty calls."

I had not thought about how late it was prior to coming to his room. I had also not really considered how he would take it with me entering his room at this late hour with him dressed in only a pair of boxers.

"Brad I did not come here for a booty call. I was just bored"

He could see how nervous I was, how could he not? I heard him laugh in a flirty way. He then came over and sat next to me. He was so close that our thighs were touching.

"You are a virgin, aren't you Kim? It is okay. You can admit it."

I thought he was going to make fun of me if I had admitted that I was a virgin. I mean here I was at 19 and still a virgin. So, I lied and told him that I was not a virgin and that I had sex a lot. He listened to me but, I could tell he was skeptical of what I was saying.

"So if you are not a virgin then you know what's up." He lifted the leg of his boxers and showed me his cock.

I looked at it trying to hide my shock at actually seeing my fist cock and it is attached to a guy I have had a crush on for years. Honestly, I did not know what to do. I was just frozen there looking at it and then he took my hand and placed it on his cock. I think he was expecting me to get up and run away but, I didn't. It must have been instinctual because I do not know why I did it, but I wrapped my fingers around his cock. I started to just play with it and hold it in my hand. It felt soft and smooth but was also hard. I could feel the muscle that was under the skin as I started to slide it in my hand. Brad was talking to me but I did not hear anything he was saying. I do not know how long I sat there rubbing his cock and staring at it but he did eventually get my attention.

"Have you ever sucked a cock?"

"Oh, umm, of course I have."

"Well?"

I knew by the way he said well that he was wanting me to suck his cock. I had actually never sucked a cock and had no idea what to do. I sat there nervous that if I did do it he would laugh at me like I was an idiot or something. If I did not do it he would realize that I was lying about everything. Why was I lying? I kept asking myself that but could not find an answer.

"You have never sucked a cock have you?"

The question snapped me back to the situation literally at hand, and I slipped down to my knees in front of him. I might not have known how to suck a cock really, but I had watched some adult movies that did give some ideas. As I got down on my knees I reached for the waistband of his boxers and pulled them down. I grabbed his cock again and started to stroke it feeling more confident in that action.

"Yes I have, and I will prove it." I said in a defiant tone trying to sound convincing.

I was determined to show him that I knew what I was doing, but I didn't. I took a deep breath and used every ounce of courage that I could and took his cock into my mouth. I wish I could say I was a natural at giving a blow job, but I would be lying again. It was bad... very bad. I just sucked hard on the head of his cock like I was trying to drink from a straw. I tried to move my head up and down but my suction was just pulling his cock with my head. My teeth also started to get involved, and I heard him say ouch a few times.

I realized that my technique was wrong but did not really know how to fix it. Then a thought came to my mind to suck it more like an ice cream cone. I stopped trying to suck his balls out and started to use my tongue more. This worked better for him but he was starting to leak cum and I was not prepared for the taste. It was bitter and so salty and the texture was like slime. It was only small amounts but it did make me want to gag a few times. I realized that if I used more saliva it would dilute the flavor a little, but it was still bad. I was able to start moving my mouth up and down on his cock letting it slide through my lips and over my tongue. At one point he did try to push my head down to take him deeper but it just choked me. I had to pull up off it and cough and catch my breath. I think it made him nervous that someone would wake up because he did not try that again. After about 10 minutes he pulled my head off of his cock.

"Not bad but I have had better. Now, lay up here in the bed. I don't want to cum in your mouth. I want to see how your pussy feels."

I did not even say a word. I just crawled up into the bed and laid down with my head on his pillow. He kicked his boxers the rest of the way off and then turned to me and pulled off my shorts and panties together in one motion. I was shocked at how quickly I was exposed to him, but I did not say a word. He crawled up over me and I could feel his cock against my thigh. He started to kiss my neck, and then I felt him rub his cock against my pussy. He tried to push into me but I refused to open for him.

I think at this point, he knew I was a virgin. He did not say anything about it. He moved to lay next to me and kept kissing my neck. He started to rub on my pussy and then worked a finger inside me. This is something I had felt before but always with a hand down my pants not with my pussy so exposed. It did feel amazing though, and I did want him to keep doing that. I wished for him to keep rubbing my pussy and use that finger inside me. After a short time, he did push a second finger inside me. This was a new feeling for me. I had not had two fingers inside me before, and I found that it did hurt a little bit. I moaned a little louder, but did not push him away. Even though, in the back of my head, I was screaming at myself to get out now. He worked his fingers in me for a while, and he did get me very wet. Once he was satisfied he crawled back on top of me again.

"You are a tight girl but I think you are ready now."

He pushed my legs wider one at a time and asked me to hold them there. I held my knees apart with my hands for him as he again started to rub his cock against my pussy.

I wanted to get up and run away and was so close to doing so, but I just could not do it. I felt him start to push again, but I was still not opening.

He pushed again and again and again.

Then I started to feel him make progress. At first, I just felt pressure and it did feel kind of good. Then I felt something else. I felt a pop, and I swear I could hear it to. My eyes went wide. I took a sharp breath. My hands went from my knees to his hips to try and push him away. His hand was over my mouth quickly, as soon as he saw me take that sharp breath. I screamed into his hand, but he was able to muffle the sound. He was so strong that I could not push him away. All I could do was grab a handful of his blanket. I buried my face into it and screamed in pain. The pain of having your hymen broken is different for every woman. Mine was very painful and it burned horribly.

I was breathing so heavily and did not think I could take any more. He just kept working his cock deeper and deeper until he was all the way in. To my surprise, he did stop there and let me adjust to him. He just stayed deep inside me for at least a full minute, or maybe five, I have no real idea. When he saw that I was relaxing, he started to move his hips slowly. Pulling out and pushing in again, slowly at first. The pain was still there every time he moved, but it was less pain than at first. I closed my eyes tight as he took my virginity.

I had masturbated before, of course, and had orgasms but never with a cock inside of me. After several minutes, I did have an orgasm on his cock. It was more intense than what I had given myself by rubbing my clit. The feeling came over my whole body. My fingers and toes started to tingle. My eyes closed tightly as my back arched on its own. I pulled the blanket to my face again to muffle my moans of pleasure. That is when I felt it. His cock started to swell, and it felt even harder than before. I had no idea why this was happening at the time, but I soon found out. I felt him rapidly expand inside me and then I felt a gush inside of me then again and again. The feeling was different and nice. I could feel it in my stomach as he pumped into me. When he finished, he just rolled over next to me.

"Well you are definitely not a virgin now. I hope you are on birth control though."

I had not even thought about pregnancy this whole time. I just wanted to not be teased for my virginity.

"Oh, umm, yeah. Of course, I am on birth control."

Just another lie to add to my list, but inside I was terrified that I was now pregnant. At the time, I thought you would instantly get pregnant from sex, but of course, that is not true. You get pregnant if you have unprotected sex around your fertile days. I got lucky, and was not in my fertile window at the time. I did not get pregnant from this experience. After a few minutes I got up and cleaned myself up with a towel that he had next to his bed. Fortunately, it was a maroon colored towel so the blood did not show.

He was not cold to me or cuddly with me. He just remained the exact same way he always had been.

As I left his room, he told me goodnight and asked me to turn out his light. I did and then made my way back down to my friend's bedroom and got back into bed. The thoughts of what I just did raced through my mind. I felt different but also the same. I was unsure what I should do next. Eventually, I did fall asleep.

The next morning when I woke up I was shocked to find that my panties were full of dried cum... a lot of dried cum. I quickly got into my bag and grabbed a fresh pair and changed. Then, I stuffed my dirty pair into the bottom of my bag. I went to the bathroom to pee and was surprised to see cum fall into the toilet while I did. I cleaned myself up again. That was the last of the cum that would leak. I did not have any in my fresh panties when I got home. I took a hot bath shortly after getting home. As I soaked my body my mind kept going back to the events of the evening. My pussy was sore for several days after that night, but eventually, it felt better. My stomach also felt like my guts had been rearranged inside me. It was an amazing night that I will never forget but was also so much more than I was prepared for.