by Richard Eaton
firstname.lastname@example.org all e-mails will be answered
This story like every other story on Nifty, no matter how real it is, is a work of fiction.
Sex with underage people is illegal no matter how really fun and enjoyable it may be.
Please donate to Nifty so it can continue it’s fine work.
It’s Friday night and I find myself sitting at home in front of my computer staring at Facebook. I could have gone out with my best friend Trey. There was a party we were going to go to, but after the day I had, I just wanted to stay home in my misery. I made sure he went to the party though, no sense in bringing him down.
On the screen is Tiffany’s page… I’ve always liked her and after years of self doubt, a lecture class at school discussing Regrets, where my teacher talked about looking back in your life and saying “What if….” made me decide to ask her out. I decided even though I am 16 years old, for a whole week now, I don’t want to look back and ask myself why I never took a chance with Tiffany. So, I grew a pair and barely asked her out. To my surprise she said she would love to and has always thought I was cute.
I showed up, sweating and worried about doing something stupid and was nervous the entire evening. I took her to dinner and a movie, where half way through, I reached out for her hand. After the movie we went parking and as much as I wanted to make out with her, all I could do was a quick kiss. My mind was reeling from the kiss and the next thing I knew she was kissing me! Her tongue was in my mouth and her hands were rubbing my now extremely hard dick.
I reached up to her chest and started feeling her tits. She started to unbutton her blouse and soon her tits were in my bare hands. My pants were now open and she was removing her own pants saying how glad she was that I was going to be her first.
Then I freaked. I don’t know why, I was about to fuck the girl of my dreams, who like me was virginal and all I had to do was, not freak. But I did. It was awkward and I kept apologizing saying that it was not her, it was me, and by the time I got her home, I didn’t even get a good night kiss.
That was last Friday and Monday when I got to school I heard Jeff, the football jerk, I mean jock talking to some of the guys telling them how he took Tiffany out Saturday night. Not to dinner and a movie but to his house where he told her that as hot as she was, he didn’t want to date her. He told her that he just wanted to fuck the shit out of her. Two minutes later, he was balls deep banging her, listening to her scream. Matter of fact, she screamed so much that his dad came in and asked him to put his underwear in her mouth because it was disturbing the movie his parents were watching.
He then went on saying he fucked her all evening dumping load after load into her. She left barely able to walk being driven home by his dad. He isn’t sure, but he thinks his dad tapped her too. Then early the next day, she showed up and he called a few friends on the team and they spent all day Sunday taking turns split roasting her.
It seems that by not going for what I wanted, I missed the opportunity to get a girlfriend. Now, she appeared to be a slut and if I asked her out, everyone would just think I was getting Jeff’s sloppy seconds, or is it hundred’s? Lost opportunity and a huge regret.
Never again. From now on, I am going for it no matter what!
My thoughts were interrupted by hearing my sister coming in from her date with her boyfriend Tommy. I didn’t think she would be home this early so I got up to see why she was home.
Her bedroom door was open and I saw her moving angrily across her room. She stopped when she saw me and motioned me into the room. Before I could say anything she started yelling, “What the hell is wrong with me? Huh?” She turned towards her mirror and stripped off her shirt, showing off a very sexy red lace bra. Her body was tight, her stomach flat, and her breasts were pushed up and on display.
“What’s wrong Sis?” I asked, walking a little closer.
She looked at me in the mirror and started removing her skirt. Matching red lace panties hugged her hips. The lace was shaped kind of like a thong, only with more lace showing and most of her ass cheeks were showing above her long legs. My dick was hard and I was staring. She looked my way and saw my predicament. Her breath caught in her chest and I saw her tits go hard with excitement. I saw desire in her eyes, before her head looked down at her body. “I guess that means it is not me… it is just that Tommy, he… he doesn’t want to have sex till he is married… and I, I just get excited and horny and…” Then her eyes darted back to my crotch and never looked away.
No Regrets I heard in my head and I stepped up behind her. My hands grasped her waist, feeling her warm skin and I started leaking into my sweats. I pulled her tight against my chest, my hard dick pushed into her panty clad ass and as I moved to her neck, to kiss it, one hand went up to her perky hard tits and the other hand went into the front of her panties.
She moaned as my fingers found her mound and I realized she was dripping wet. I was kissing her neck, fingering her pussy and massaging her now free breast. She was moaning and grinding her ass into me. I left her tits and my hand grasped the side of her panties, pulling and tearing them off of her. Once gone, I pushed her towards the mirror and pulled down the front of my sweats. Before either of us realized what was happening, I slid into her from behind and lost my virginity.
I started slow, using both hands to pull her breast free and while still kissing her neck, I started to pick up speed and strength. Her moans got louder and she started saying “Fuck me… fuck me little brother… make me your bitch!” and I tried. I had to grasp her waist again since I was being so forceful and wanted her to stay standing. Then, all of a sudden, she started shuddering and screaming out as she came. It was too much for me and I came too. I came hard, unloading spurt after spurt of teenage virginal cum into my big sister.
My mind was reeling. I was no longer a virgin because I just came deep and powerfully into my big sister’s pussy. We were both breathing hard and sweating from all the excitement. I looked into the mirror and saw my sister staring at me, both of us with huge grins on our faces. “Thanks Bro, that was… wow. That was not how I thought I would lose my virginity… to you that is, but wow, it was everything I thought it would be and even more…”
Then she stepped away from me and crawled onto the bed. She removed her bra completely from her body and leaned back, spreading her legs wide. I immediately stepped out of my sweats and pulled my t-shirt from my chest. Then crawling up between her legs, I entered her again. We fucked slow and easy, kissing while enjoying ourselves. Our tongues locked together, our hands all over each others body. We fucked until I couldn’t cum any more. My dick was sore and she said she was to. I left her bed and went back to my room in case our parents checked in on us in the morning.
I was happy and strangely enough, still horny. I shut down my computer, thoughts of Tiffany no longer in my head. I threw my sweats next to the bed and crawled into it butt naked. I was so excited that I was afraid I’d never sleep, but in seconds I was out. I slept soundly till a sexy dream, where I was getting my first ever blow job, woke me. It wasn’t a dream. My big sister had pulled the covers off of me and was sucking my dick like no one’s business. Seeing the smile in her eyes as she bobbed up and down on me, I came. A little of my cum leaked out the side of her mouth. I pulled her up and we kissed again getting a taste of my seed from her mouth.
Getting up from the bed, she told me, “Thanks little Brother, for making me happy. I expect you to be home every Friday night from now on to work out my hornyness after my date with Tommy.” Then she walked out wearing the same sexy red lace panties she had on the night before.