When I was 14 I was a pretty trustworthy kid. I made good grades, stayed out of trouble, and overall pleased my dad and step mom. Most of the time when they went out of town they would call my grandmother to come up and sit at the house with me, my brother, and my step sister. This weekend however, they decided that since my brother had just turned 18 he was more than capable of watching us.
My brother, Todd, was no doubt the trouble maker of the 3 kids. As soon as our parents left he informed me that he would be leaving to go stay with his friends in the city. For a small sum of money I agreed to keep my mouth shut; we lived in the country, nothing ever happened. Todd left and me and Tiff had the house to ourselves.
Tiff had just turned 12 and was starting to blossom. She was rather thin, with strawberry blonde hair and a fairly light complexion. I asked her “What do you want to do?” since we couldn't go anywhere, being I was only 14 and had no license. She replied, “I'm really hungry, you should throw a pizza in the oven.” I had not eaten since early that morning and was starving as well. So I cooked dinner, we watched some TV, and rented a pay per view movie. Just a nice quiet night with nothing out of the ordinary.
About half way through the movie I hit pause on the DVR and called “Bathroom break!. ”
“Thank God!” Tiff replied, and hurried to the bathroom.
I had to pee really bad so I decided not to wait and walked outside to pee off of the back porch. For a 14 year old I had an averaged size dick, about 5 inches rock hard. I hated the way public hair looked as soon as it started sprouting when I was 12 so I kept myself well shaved. I walked back inside to find Tiff had not yet returned from the bathroom so I went to the kitchen to fix myself a drink for the rest of the movie.
Ten minutes later Tiff had still not come out of the bathroom, so I walked to the bathroom door, knocked, and asked “Are you alright in there?”
“That pizza isn't sitting to well with my stomach.” She replied
“Alright” I said, “Do you need anything?”
“No, I'm fine.” She retorted, so I went and hit the record button so she could go back and watch any parts she missed.
After the movie finished I noticed she still had not come out of the bathroom. Once again I went to the door to check on her.
“Do you need some medicine?” I asked, trying to be a good big brother.
“I don't think I can get off of here without making a mess!”
“Well just unlock the door that goes into your room and I will bring you some.” I said, our bathroom had two doors, one leading to the hallway and the other into her bedroom. The one to the bedroom was in reach from the toilet seat.
“Alright.” she said
I went to the kitchen cabinet and grabbed the bottle of Pepto and a glass of water for her. When I returned I went to the door in her bedroom and knocked saying, “I got it, open up”
“I dont want you to see me with my pants down!” she exclaimed
I told her, “Just grab a towel and put it over your lap.”
She did as I said and I opened the door and handed her the medicine and sat the glass of water on the table.
“Do you want me to sit here and keep you some company so sitting on the toilet isn't quite so boring?” I asked
“Sure” she replied “Since we've got this whole problem with you seeing any private parts taken care of”
I then reminded her that it was nothing I haven't seen before since we were once little and bathed together. We both had a good chuckle and just tried to make some small talk and keep her mind off the obvious discomfort that she had in her stomach.
About 30 minutes later she stated that she did feel better and unthinkingly removed her towel to cleanse herself. It took her a few seconds to realize her mistake, but in that few seconds I saw everything she had been hiding. At 14 I was a virgin and hadn't seen a vagina in real life since I was too young to know what one was or care. Instantly I had a raging hard on. Part of me wanted to sit there and stare at her female anatomy, but the good part of me said it was best to act like I had seen something bad and turn and walk away.
I went and sat in the living room contemplating if I wanted to go masturbate or not. Even though I was a pretty level headed kid I was still a boy, a slave to my sex drive, and addiction to getting off. Right before I went to get up, Tiff exited the bathroom and I decided to stay put. I noticed she was walking funny. “Are you raw?” I asked casually
Embarrassed, she replied, “Yes”
“I'll go get you some Vaseline, just go lay on your bed”
I once again went to the cabinet and grabbed the Vaseline. I still had a raging hard on and the thought of my little sister rubbing it on her asshole didn't help it go away the slightest bit. I walked into her bedroom to find her laying on her stomach on the bed sideways, with her feet hanging off the side.
“Here's this Vaseline” I said, and turned to walk out the door.
“I don't wanna rub that on my butt!” she exclaimed
“Well do you expect me to do it for you?” I said being a smart ass but secretly hoping the answer was yes.
“Please?” She said.
It was all I could do not to shoot a wad off in my pants right there. I had never been so excited to lotion anything before.
“Alright” I replied, trying not to show any excitement, “but, this stays between us, understood?”
“I won't tell” She said
She slid off her gym shorts and wiggled her underwear down onto her thighs.
“Spread your cheeks for me” I said
She did as I asked and spread her butt cheeks. And there I was looking at the tightest, pinkest, rosebud off a butt you could ever imagine. Not to mention the view of her slit in the background, but I had not received permission to touch that yet. I got a good amount of the slippery jelly on my index finger and slowly stroked her tiny ass hole. It twitched a little as my finger slip over. I then worked my way all around it and massaged the jelly in as much as I could. When I went for one last pass over her hole before I quit my finger slipped into her freshly greased ass. She twitched a little and said “What are you doing!?”
“My finger slipped!” I tried to explain nervously.
“That kinda felt good” She replied
Amazed at this reply I scooped a little bit more of the jelly onto my finger and began to circle her hole slowly. When I saw that she had relaxed enough I slipped my finder inside again, this time a little bit deeper, but still not fully penetrating. While my index finger rested inside I slowly rubbed with my others and waited for her to relax her anal muscle again. Once she did I pushed my index finger in a little bit harder and fully penetrated down into her bowels. She let out a small sigh but didn't say stop, so I didn't
I slowly began to move my finger in and out of her ass and she began to move with me. At this time I had my other hand in my pants stroking my raging boner in disbelief. I was fingering my little sister! And she was loving it!
When one finger became easy to slide in and out I inserted another, she sighed once again but kept moving with my strokes. She then let her underwear slide down to her ankles and kicked them off into the floor. Slowly Tiff raised her feet up and slid her knees under her giving me a prime view of her beautiful virgin vagina as well. At this point I thought I was going to cum all over myself, but I managed to hold it together long enough to slide off my gym shorts and boxers and position myself behind her, all without my fingers leaving her behind.
“Do you promise to keep this a secret Tiff?” I whispered
“I swear” She half moaned back in pleasure.
I looked down at my penis and decided if it was going to fit in her tiny ass hole that I would need to get at least one more finger in her. This time she moaned in pleasure as my 3rd finger entered her. While I was waiting for her sphincter to relax I took my penis and slowly began to rub against her exposed vagina and all the way back to her butt crack. The runoff from the Vaseline got my dick nice and slippery just in time for her to become relaxed enough for me to get in.
I pulled my fingers out one at a time and then positioned my dick at her now slightly stretched hole. I slowly pushed in, as she moaned loudly in a half pain half pleasure mix. Once my penis was about half way inside her this stopped, and then she started thrusting her ass towards me. The pleasure was incredible and I have never since been in anything so tight. She slowly but surely managed to take the entire length of my dick in her ass. As I pumped she moved with me moaning in pleasure as we went.
I reached my left hand around the front of her and began rubbing her vagina. I had heard from friends the clit was what I needed to get to but I had no idea where it was at. She started moaning really loudly and I just assumed that what I was rubbing was in fact her small clit. As she started to orgasm her asshole tightened around my dick triggering my immediate explosion into her bowels. I stayed inside until my penis began to go limp and started sliding out, with a stream of cum chasing behind.
I rolled her over onto her back and began kissing and licking her vagina as she pushed it into my face harder and harder. I managed to make her orgasm once again before I stopped.
“Did you like that?” I asked shyly
“I think we need to take a shower” She replied with a grin.
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