How I lost my virginity to my best friend

How I lost my virginity to my life long best friend.

DISCLAMER: This is a Fictional story based on a dream. It features preteens and young teens. It also includes some brother, sister sex. So if your not into that stuff, just pass on this. Also if the grammar is not great, it’s because it was written as if a 12 year old actually wrote it. As for spelling errors. I use a spell checker, and proof read it, but occasionally some miss spells get missed, sorry.


My name is James. I’m 12 years old, I stand five feet four inches tall with a slightly slender build. I have blonde hair and blue eyes. I live in a rural area with my mom, dad and eleven year old brother Timmy.
Living in a rural area I didn’t have many other kids to play with, Timmy is a major bookworm and wont go outside much at all. I also read more than most guys, nothing much else to do when it rains.
The only really close friend I have is Jenny who lives just down the road. She is thirteen, almost fourteen, and she has been my best friend for as long as I can remember. We grew up playing every kind of game we could dream up. I never really thought of her as being different from me, until recently, as her body began to change.
She is also about five foot four With ice blue eyes, and long wavy blonde hair. Her body has always been slender, but now her legs have become more round as has her ass. Her chest also protrudes out with the growth of her breasts.
It wasn’t until the day she came over wearing short shorts, and a tight T- shirt, that I really noticed the shape her body had taken. I also couldn’t help but notice my cock had gotten hard and was throbbing.
As we were playing that day I couldn’t help but stare at her body, which kept my cock hard and throbbing. I couldn’t imagine why it was so hard and throbbing so. It has never done that before.
After a while I began to get worried that something was wrong. I went to the bathroom and removed my jeans and shorts. I examined my long stiff cock, as I had never seen it like this before. I noticed it was getting softer, and soon it had shrunk back down to it’s normal size, as it hung between my legs.
I then remembered the conversations I had heard from the other boys at school as they were talking about spanking the monkey, and boasting about the size of their (cock’s) as they called them. I didn’t really know what they meant when they said it was 8 and 10 inches long, until just now. I realized my cock was about 6 inches long when it was stiff and hard. That memory did comfort me to the fact that there wasn’t any thing wrong with my cock. I guess they just get like that for some reason I didn’t yet know.
I went back out to play with Jenny, and when I looked at her legs and chest again, my cock got hard again. My cock remained hard like this the entire time we played, until she had to go home for dinner. My cock slowly went down as I ate dinner.
When I took my shower, just before bed, my cock was back to normal, and staid that way all night, or at least I think it did as it was not hard when I woke the next morning.
That day I wore a T-shirt and my shorts, which fit fairly tight. Jenny came over and asked me to come out and play catch.
I couldn’t help but watch her body as she caught the ball and then threw it back to me, making my cock get hard again.
After a while she caught the ball, then dropping it she sauntered up to me and quietly said. “My but that’s quite a nice hunk of meat you have in your shorts, I didn’t know you felt that way about me!”
Not knowing what she meant I just said. ”Huh?”
Being as close as we were, we never really kept secrets from each other. Nor were we afraid to ask each other anything, or even touch each other any where. So I wasn’t too surprised when she reached down and grabbed my cock through my shorts, as she said. “You really have a nice piece of meat here.”
“Oh, well it only gets like that when I look at your legs and chest. I don’t know why it does that though.” I muttered back.
Then she whispers. “Didn’t you know, a guys cock always gets hard when he gets turned on, like when he sees a sexy girl he likes? Hey I didn’t know you found me that sexy!!!”
I felt myself flush as I said. “I didn’t realize I thought of you like that either. Or at least I didn’t before yesterday any way.”
She moved close to me and whispered. “Have you started playing with this yet?” as she gently squeezed my cock.
I felt myself flush a little as I said. “Um, what do you mean?”
“You know, Spank the monkey.”
I just stared blankly.
“You know, stroke it.” she said softly.
“Oh. No I’ve never done that.” I said, feeling rather embarrassed, which I have never felt with her before.
“Would you like me to show you how to do it, you’ll really like it?” she replied.
I looked at her for a minute as I thought about it. “Hey, how do you know how to play with a boys cock any way.” I asked.
“You know my aunt, uncle and two cousins are here right?” she asked.
“Yes, so.” I replied.
“Well one day last week I heard noises coming from mom and dad’s bathroom. When I went to see what was going on, I found the door open just a crack, and I could hear soft moans from inside. When I looked in through the crack I could only see the mirror over the sinks. But in the mirror I could see that Andrew and his twin sister Anna were both nude, sitting on the back of the roman tub. They had their legs spread wide with their feet in the tub. Anna had her hand around Andrew’s long hard cock and she was moving it up and down the length if it. While Andrew had his hand between Anna’s legs and was rubbing her pussy in slow circular movements.”
Hey, they did this last week, and you didn’t tell me about it?” I suddenly said interrupting her.
“Well I’m telling you now. ”She said.
“Ha, ha. Just when were you going to tell me, or were you?” I asked.
I was going to tell you after they left, I didn’t want them to know I saw them, and it might slip if I told you sooner.”
“Oh Ha, ha,” I chuckled.
Jenny continued. “They continued this for quite a long while. Then I heard Anna ask him if he wanted her to make him cum now or did he want to fuck her first. He said he wanted to fuck first. She moved in front of him and I watched in amazement as she guided his cock between her legs to her pussy, and she moved down onto it.”
“Then what happened!!” I excitedly asked.
“Anna began slowly moving her body up and down, making his cock move in and out of her pussy. She did this for a really long time, moaning and grunting more and more. Then she squealed a bit and her body tensed and then shuddered a little for about a half a minute. Then she stopped moving.
She got up off his cock and then sat back next to him, and they began playing with each other again. They did this for quite a while. Then Andrew finally said he wanted to cum now. So Anna began moving her hand up and down his cock fast, and soon he grunted, tensed up, and white stuff spurted out of his cock several times. Then they stopped moving and then filled the tub with water.
They got in and took a bath together. Seeing what they had just done, I felt a little strange, so I left at that point..”
“Wow, that story is making my cock throb really hard.” I said.
“I know, I felt it harden as I was talking to you… Do you want me to show you how to play with it now?”
“Ok, but not here.” I said.
“Come on” she said as she took my hand and led me back into the woods.
When we were back in a ways she stopped and facing me she unbuttoned my shorts, and grabbing them and my under pants, she slid them down my legs as she kneeled in front of me. She spit in her hand several times, then looked up at me and said. “I heard this makes it feel better.” as she takes my cock in her hand. I stand there looking at her as I take in the sensations I’m feeling as she begins slowly stroking her hand up and down my cock.
Looking up at me she says. “You like this?”
“Yea, it feels nice, I never new I could feel anything like this.” I replied.
After a while she spit on my cock head some more, then began stroking faster. Now the feelings were growing in intensity and I began involuntarily rocking my hips.
Jenny looked up at me again and said “How does that feel?”
“Great, don’t stop.” I replied.
Jenny spit some more then went even faster. I felt something building as my cock started a tingling burning sensation. Then seconds later I grunted and tensed up as the most intense sensations imaginable pulsed through my cock as it spasmed and pulsed many times before it subsided and then eased off to just nice feelings.
Jenny slowed her stroking as she looked me in the eyes and said. “So how did you like that?”
“Oh man that was incredible, I’m not sure what happened but it felt incredible.” I replied.
“You just had an orgasm silly boy.” she said with a chuckle.
“Oh ok, I never imagined an orgasm would feel like that, you were right though, I did like it.” I replied.