Plain Jane Got Pretty

Billy was my best friend for as long as I could remember. My mother told me that Billy, his sister, and his mother moved in when Billy and I were two years old. Then a couple of years later Billy’s mother got knocked up. The guy must have been ugly because Jane was no prize. Billy and I would do almost anything to avoid playing with her. When we turned thirteen Jane was nine. She would let us see her naked and let us feel her up. She realized that that was the only way that we paid any attention to her.

As time went on Jane hit puberty, she got her breasts, she got her periods, and she started to look better to us.

When she was almost thirteen, Billy and I were seventeen. That’s when things got much better. At first neither one of us realized what had happened. Jane became a woman before our eyes. She dressed sexy and what’s more important she looked sexy. She started talking sexier too, if you can understand that.

One day she stepped into Billy’s bedroom and said, “If you guys show me your cocks, I’ll show you my tits and cunt. Remove your clothes and let me see you for a full minute and then I’ll remove my clothes and let you see me. I’ll even spread my legs and open my pussy up for you if I can suck your cocks.”

We were naked in a flash. My cock grew as hard as I’ve ever seen it, so did Billy’s cock. After a full minute Jane sucked the head of my cock into her mouth. It was incredible. Jane’s mouth felt warm and wet and she sucked so nicely. I warned her that I was going to cum but she just held onto my ass and sucked harder. I fired my first shot into her throat and she just swallowed it and wanted more, which I gladly gave her. When I was done she licked my cock clean and kissed it saying, “Thank you.” It was me that needed to thank her. Billy got his cock right in her face and she just kissed the head and said, “You’re my brother. That’s all you get.”

Then Jane undressed keeping our full attention. She took forever to get naked. Then she sat on Billy’s bed, leaned back and spread her legs, and then she opened her pussy up for us. I looked right inside her and it was wonderful, it was very pink, and it was really wet in there. I was close enough to smell her aroma, she was sexually excited and we all knew it. Without any warning I just leaned in closer and kissed her opening then I stuck my tongue in her sweet pussy. I knew what I was doing even though I had never tried it before. Jane loved it and begged me not to stop. After her orgasm I kept it up and she begged me to stop. I took my time but I did stop and pull back. Billy leaned in and kissed her pussy but that was it, Jane pushed him away and said, “You’re my brother. That’s all you get.”

After that first day we got to play with her about once a week. Then one week she said no. When I questioned her she said that she was having her period. I told her that I wanted to see it. She took me into her bedroom but made Billy leave and then we undressed. She lay back on her bed and showed me a string sticking out of her pussy. She tugged on the string and a cotton plug started to come out. There wasn’t much blood on it. Jane looked at it and asked, “Would you fuck me? You can’t tell Billy though. It has to be our secret. You see, a girl can’t get pregnant if she is bleeding. Mom doesn’t trust me to put me on birth control. She knows that I’d let you fuck me and get me pregnant.”

Shocked I asked, “Your mother knows?”

Jane giggled and said, “No silly, I didn’t tell her anything. She just knows how much I like you and that I would do anything that you asked me too.”

I smiled and then I asked, “Anything?”

Jane just pulled my cock closer to her pussy and helped me push it in. It felt a lot better than her mouth had in the past but her pussy was better. I enjoyed fucking Jane. After I came inside her Jane poked another tampon in her hole.

I asked again, “Anything?”

Jane giggled and said, “The girls at school are starting to experiment with their boyfriends. They say that there are a lot of different positions to have sex in and that was just one of them. I’d like to try them all. They also talk about having anal sex but none of them has had the nerve to try it yet. I’d like to be the first if you don’t mind.”

I replied, “Why would I mind? If I can fuck your bloody hole I can sure as hell fuck your shitty ass.”

Jane giggled and said, “It isn’t shitty. I gave myself an enema. It’s clean enough to eat.”

I lifted her legs up higher and rested them on her tits. I leaned in and I started licking her asshole. She was right it was clean. My friends were right too. They had said that if I ever got the chance, to do it with enthusiasm…because sticking your cock in a girl’s ass was the ultimate success story. I left some spit on her puckered ring and then positioned my cock right up to that puckered ring. Then I held onto her hips and pushed it in. I know that Jane felt some pain but she never said a word. The guys were right, her asshole was the tightest thing yet. The friction was almost painful for me. I came and she moaned. I didn’t pull it out because I wanted it to stay inside her for as long as possible. Eventually it softened and fell out on its own.

Jane turned around and sucked it into her mouth. I gave her a funny look and she said, “I need to do this so that I can brag to my girlfriends that I did it.”

I asked, “Do they know that I’m the one that you’re fucking?”

Jane said, “Yes, I just told them the other day. They think you are wonderful.”

I kissed her, I poked my tongue into her mouth, and I said, “I love you.”

Jane said, “I love you too.”

There was a knock on the door. Jane’s mother said, “You two need to get dressed. Jane its time for dinner. Kiss his pecker goodbye and send him home. He can come over after school tomorrow and then you two can have more sex.”

I whispered, “She knows!”

Jane giggled and said, “I figured that out myself.”

Jane then kissed my pecker goodbye. We got dressed and she took me to the kitchen. I watched as Jane kissed her mother and stuck her tongue in her mother’s mouth. They kissed for a long time. I wondered if she knew that my cock had been in Jane’s ass and then in her mouth just moments before Jane put her tongue in her mother’s mouth. She must have known.

Jane’s mother said, “I made an appointment with the doctor to get you on birth control tomorrow. I’ll pick you up at school and return you afterwards.”

Jane kissed me goodbye and stuck her tongue in my mouth too. There was a strong mint taste. It must have been from her mother.

After that Jane and I had all the freedom of her bedroom every day. Billy never bothered us again.

The End
Plain Jane Got Pretty
670