Where it happened: my bed
Langauge: English
Sex: Male
Rating: 5
Category: Straight
As long as I’ve lived, I’ve shared a room with my brother, who is three years older than me. Since we share a room, we’d grown well accustumed to seeing each other naked, and being naked in front of each other. Well, one night when I was in sixth grade and my brother was in ninth, I was unable to sleep, and no matter how hard I tried, I just couldn’t doze off. It was late, and I just layed in my twin bed, staring over at my brother trying to sleep in his bed (our beds were arms reach apart). He looked over at me and whispered my name, but I wasn’t interested in talking, so I just pretended to be asleep. He asked me if I was alseep, and I didn’t reply. I slowly opened my eyes, not worrying that my brother would notice without his glasses in the dark, and saw my brother pull his sheets down to his waist, and stick his hand in and move it for a minute. I was curious as to what he was doing, so I continued watching. After a few moments, he pulled his covers down to his knees, and slid his underwear down past the covers. I was shocked, not to see my brother’s penis, but to see it erect, which I never had before. I watched carefully has he stroked and pumped, and was shocked to see him clench up as some white stuff came out and landed on his belly. He reached for a kleenex, and after he whiped it up, pulled his underwear and the covers back up and went to sleep.
I watched my brother masturbate every night for the next two weeks, but never had the thought to try myself. I noticed that my penis became hard when I watched, but was scared of the white stuff that came out of my brother. After about two weeks, I decided to ask my brother what he was doing. It was a Friday night, and he had just started to pump, when I suprised him with the question. My brother froze, and didn’t make any noise. I asked him again, and he looked over at me as I sat up on the edge of my bed. “Nothing” he replied. I told him he was doing something with his penis, and he told me it was nothing, and to go to sleep. But I knew it was something, so I told him I’d seen him doing it before, and how he clenched up and white stuff came out. He was silent, but then sighed and told me that it was called “masturbating,” and how he did it to feel good. I asked if I could do it, and he sighed again and said why not. I was excited, so I layed back on my bed and slid down my underwear, revealing my already hard penis. My brother got up and sat on the edge of my bed, and told me to stay still. He grabbed my penis, and started to stroke it like he did to his. It felt amazing! After a minute I felt something really weird, and noticed that I clenched up just like him, but no white stuff came out. I asked him why, and he just said I was too young, but it was still amazing.
My brother and I started to masturbate together, and very quickly began masturbating each other. I loved holding my brother’s bigger penis in my hand, and it felt amazing to have him rub me. We even gave each other blowjobs on specail occassions, but that wasn’t often (birthdays, etc), and overall we came way closer as siblings, and continued doing it until he went to college, and continued to do it whenever he came home.
Now onto how I lost my virginity. It happened with a girl I had gone to school with since kindergarten, and who had an older brother the same age as mine. It so happened that we started getting close, and by the time we were in eighth grade were boyfriend and girlfriend. We knew what sex is, but weren’t super desperate to try it, since she was like most girls and didn’t really want a baby or to be a slut, and I was getting handjobs nightly from my brother, and occaisonally shooting a load into his mouth.
It was a cold, snowy December night, and my girlfriend and I were both snowed in at my house, and the rest of my family was snowed in across town (we could get outside just fine, but no one wanted to drive). She lived two doors down and across the street, but here parents were also snowed in somewhere else, so we were both togerther without anyone knowing. She decided to sleep over since she didn’t want to spend the night alone, and I told her she could have my brother’s bed. However, she told me that she wanted to sleep in mine, with me in it! I agreed, and we got ready to go to bed. The only problem was that she didn’t have pajamas. I gave her a shirt and a pair of boxers, which she went to the bathroom to put on. I waited outside, but she called me in, so I entered.
My girlfriend was in the bathroom wearing my shirt and a pair of my boxers, giving me an immediate hard on. She came close to me and hugged me, and we started to kiss. I was only in a pair of boxers, and I pressed my boner to her crotch. She told me how romantic it would be to sleep together on a cold, snowy night as we went into my bedroom, and sat on my bed, staring out my big windown. We started to fool around, and I was quickly on top of her, and her arms were wrapped around my bare back. She pushed me back and layed me backwards on my bed, with her kneeling with me between her legs. She leaned down and kissed me, and I felt her grab my left hand and slowly pull it towards her and into my boxers that she was wearing. I touched her vulva for the first time, and it was really wet! I pushed my way back on top and so we were laying the correct way on my bed, and grabbed my girlfriend’s breasts, which were average for a 13 year old. We kissed some more, and I pulled my shirt off of her, and rubbed her nipples as they got hard. She like it, and crept her hands into my boxers and started to feel my penis, which drove me crazy. I pulled my boxers off of her before removing my own, and we were both naked. She told me to put my penis into her vagina, so I gladly did. As I later found out, she wasn’t a virgin, and it wasn’t very hard to get in. I started to thrust until I felt an orgasm coming, and pushed in deep and filled her with cum. We slept together the rest of the night, doing it several more times, lasting longer and feeling better each time until the morning, when she walked home through the snow, and our families returned.
My girlfriend and I continued having sex whenever we could.
In retrospect, however, I wish we had waited until getting married. Sex came with deep emotional pain, and my girlfriend graduated from eighth grade 5 and a half months pregnant, and everyone knew I was the father. Now I’m married, and it was awkward to tell my wife I’d gotten someone else pregnant, and it just made things awkward between us in bed.
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