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Bailey Ch. 01

By: Daniel5421



My name is Dean Chase, and this is the story on my life with Bailey. It was a warm summer morning in June; I was ten years old at the time. My family was moving to a town in Illinois, when my dad turned into the drive way I saw two girls sitting in the grass under a sycamore tree. The oldest one looked close to my age and the other looked about six. 

"Why don't you go meet the neighbor's kids?" Mom told me.

I had Jet black hair with sea blue eyes (Which I still have) and I was rather skinny for a ten year old. 

When I went over to the two girls I said, "Hi im Dean I moved here from Berkeley California."

"I'm Bailey, and this is my sister Sara." I'm sorry but I didn't describe Bailey yet she like me was ten, she had brown hair electric blue eyes, when she smiled her nose scrunched up in a cute way, she had the perfect amount of freckles. In other words she was and is perfect.

Sara was seven years old, she had red hair and like her sister had the same eyes, when she smiled she could light up a room with the dimple on her cheek.

"I'm going to go help mom she's making a pie." Sara told Bailey.

I sat down on the ground by Bailey. "Do you like board games?" she asked me with that sweet smile.

"Yea." I replied.

The years past and Bailey and I became best friends about a day after I moved there, but in high school I started to like her. By like I mean I wanted to hold her and kiss her, and in my pervy teenage mind I wanted to fuck her.

When I turned eighteen she slept over at my house, since we'd been best friends since I was ten so they didn't mind. She was about two months older than me so she was already eighteen. 

When Bailey came over to my house she was already in pajamas. Maybe I should tell you what she looks like, she had 36C breasts she was 5'7 and she still had the same crinkly nose when she smiled, and she had the same cute face and laugh. 

"Hey Dean your mom let me in and she said that I looked so cute." She said with a laugh.

"I'm pretty sure she thinks you're the daughter she never had except for my sister." I said with laugh.

"Why are you so weird?" she asked with a smile.

"I think it's having you as a best friend." I said smiling back at her.

"Yea maybe." She said slapping me.

"Are we going to watch the movie or what?" I asked.

"Sure, but first is my present I have to give you."

"Bailey I tell you every year you don't need to give me any presents." I said trying to sound stern.

"Ha that's funny but do I ever listen?" she said.

"No, but you should. Remember that time I saved you from ricky?"

"Yes, I remember your buff body saved me from a rapist okay you don't have to go on and on about it. I was super nice to you for saving me."

"You gave me a hug and said thanks." I said smiling.

"Oh shut up." I should tell you what happened. I went to her house one night and I noticed her ex-boyfriends car was in the drive way. His name was Ricky and he was a total dick. When I went to the door I heard I scream I opened the door to find Bailey naked and crying and Ricky groping her. I went over and punched him in the face and after that I kicked his ass.

"Here," when I opened it I was surprised it was Yahtzee the same one we played as kids.

"I don't know what to say, I love it. Thank you."

"You're welcome now come on lets watch the movie." 

When I put the DVD in a sat on the couch in my room and Bailey cuddled up next to me.

"I feel safer when im in your arms." She said softly. "Can I tell you something?"

"Yeah."

"I think... I think I... I think I love you." She said looking me in the eye.

"I love you too; I think I've loved you since I met you."

"Dean you're the reason my other relationships didn't work, because I wanted you."

"Bailey do you want to go out with me, and maybe be my girlfriend?"

"Yes a thousand times yes!" she said hugging me tight. "Kiss me."

When we kissed it felt like fireworks. I knew at that moment she was the girl for me.

Bailey Ch. 02



That night Bailey and I slept together, not as in sex, but just sleep. I held her in my arms while we slept, I felt so great it felt like I could take on an army. 

When I woke up she had her head on my chest. For another hour I just watched her sleep, she was so beautiful I wanted to paint her and put it in a museum labeled "The Beautiful Woman", but sadly I was not a painter. 

When she woke she saw me watching and said "I love you," 

"I love you too and I will until my heart stops beating. Wait scratch that ill love you even after that." With that she laughed.

"I want you to make love to me. I'm still a virgin, and I want you to have it." She said.

I kissed her lovingly and said "I would be honored Miss Borris, and you can have mine too."

"I thought you had sex with Cassie?"

"No, she tugged me off, and I rubbed her."

"Let's do it. Now that were both eighteen we can do it."

"Okay." With that I got out of bed and took my clothes off. Bailey did the same, when she saw my penis she said

"How big is that?"

"When I'm hard it goes to about eight and a half inches."

"Wow Ricky was only five." 

When she took her panties off her vagina was beautiful, she was bald and I could easily tell she was wet. She noticed I was staring and said "Take a picture it will last longer."

With that I said half joking "Can I?!" I sounded like a kid in a candy store.

"No you idiot, but your my idiot no get over here and make love to me."

I went over to her, and got under the covers. When she whispered "Be gentle." And I nodded.

When I put the head of my dick to her pussy she moaned a little. When I pushed in I was about two inches when I was against her hymen, I looked at her and she nodded. I kissed her passionately before it and said "you can squeeze my arm if it hurts." Instead of grabbing my arm she wrapped her arms around me and told me she was ready.

When I pushed further, it broke. She didn't bleed as much as I thought she would and then I went all the way in. I don't know how to describe it but I'll try, she felt like warm, wet, soft, velvet. It was amazing, I felt like I could stay like this forever.

We made love for close to half an hour before I said "I'm really close what should I do?"

"In me." She responded. She had already come twice before me; to be honest I was really surprised at that.

When I came she moaned and came again. It's supposed to be a magical experience when you cum at the same time as your lover, and I felt that magic. When I was done I fell back onto the bed. 

"We both should take a shower."

"How about together." She said looking into my eyes. God I loved her so much. Since I had my own bathroom in my room it was perfect.

After our shower we went down to the kitchen to get something to eat. My mom and dad were sitting at the table eating and drinking coffee.

"I'm sorry dears you were asleep and we were hungry so we ate, I'm sorry." Mom said looking sad.

"It's fine mom, Bailey do want to help me make some eggs." I said smiling. Which she returned and said,

"Sure ill get the milk and eggs out of the fridge."

When we were done eating we went back up to my bedroom, and watched TV while cuddling. While watching TV we decided we should tell our parents in about a week and say that I asked her out the day before. 

We decided to go to the mall, Bailey loved to shop and this time, sadly I was paying. When we were done I spent $87.73 on her, she said she'd pay me back, but I knew Bailey and she was not the kind of person to pay someone back.

When I dropped her off, we walked into her house. She called out for her mom or dad, but no one responded. "Lets check outside." She said. When we went outside we found her parents, but not the way I would have hoped.

Baileys parents were naked and fucking in her hot tub. When we came out they were so into their fucking the didn't notice us until Bailey said "MOM, DAD WHAT ARE YOU DOING!" obviously she knew but I could tell she was making a point.

When Bailey said that Mrs. Borris (Bailey's mom) slid off her husband's cock and said "Oh calm down, sex is natural. Haven't we taught you that?"

"I think I should go. Ill text you okay Bailey?"

"Okay she said waving me goodbye."

When I got home I went to my room and was going to sit on my bed but noticed a pink stain on my crème colored sheets. It was Bailey's virginity blood. I striped the sheets and remade my bed, then I laid down and fell asleep.



Bailey Ch. 03



The next day I got up and looked at my phone and I got a text from bailey saying "I'm sorry, meet me at our spot." When I went downstairs my sister Colleen was sitting at the table.

"Hey nerd, how was your birthday sex yesterday?"

"What?"

"Don't play dumb I heard you I'm not deaf, plus our rooms are right next to each other."

"Okay so I did, but it's still none of your business."

"It sounded pretty hot; I masturbated to your guys fucking. You really have to fix that little hole I made in your door." When she said that I was so turned on.

Now Colleen was 5'7 and she was a year older than me she had a great figure, and she had 26D breasts. She also had blonde hair like my mom and electric blue eyes like mine. So in other words she was beautiful. 

"You did what?"

"Don't act so surprised, I know you've watched me masturbate before." It was true. "I've been thinking about, your old offer and now that you're eighteen, you can take my virginity. If you want you can invite Bailey, but if I have to ill fuck your huge cock while you're sleeping."

"I'll ask bailey if it's okay, but are you sure?" I asked. She nodded, gave me a kiss, and walked away.

...

When I met up with Bailey at Herrick Lake, she looked so beautiful. I sat down on a huge rock and she jumped into my lap.

"What's happening in your life lover boy?"

"Oh I just made love to this beautiful girl who could be the one."

"Really? Is she amazing in bed?"

"Yes and Yes, plus im in love with her."

"I think she loves you too." With that we passionately kissed.

"I have to tell you something." I told her about my conversation with Colleen. 

"Well I guess we could fuck her together because your my man and no one else's, but I kind of don't want you too."

"I did ask she when we were kids if she wanted to be my first and she said yes, but she told me to wait. But now the only girl I want is you and no one else."

"I love you." She said kissing me again. I also notice she was rubbing her crotch on my leg.

"I want to lick you." I told her after the kiss.

"Okay." When she took her pants off, I saw her beautiful vagina. When I was ready I started to lick it, it tasted like sweet sweat. "Oh yea lick my pussy, oh you're the perfect boyfriend... oh I love you so much...OH!" and with that she came in my mouth and it tasted delicious. "Where did you learn how to do this?" 

"I looked it up on the computer."

"You're the perfect boyfriend." She said giving me a kiss. "I taste pretty good."

"So I'm you boyfriend now?" I said when I sat back on the rock. When she pulled her pants back up she laid down on the rock with her head in my lap. 

"Yep, and I better be your girlfriend or ill rape you."

"That wouldn't be so bad."

"I'd stick one of my mom's dildos in your ass."

"Which one?"

"The 15 inch pink one."

"Oh... then your my girlfriend." With that we both laughed, and kissed. 

When we left the lake we held hands on the walk to my house. We decided that we'd go tell Colleen our decision.

When we got home my parents were still gone, but my sister's car was there. When we went inside my sister was sitting on the couch. She said "Well hello love birds."

"Bailey and I decided that I can't have sex with you, because Bailey is my one and only." I said.

"Wow, you don't want your sisters cunt wrapped around your huge cock. Well did you tell she could join too if she wanted? I'd love to lick that pussy."

Bailey looked at me with a shrug as if to tell me it's my decision. I said "It's up to you babe, you told me before that you wanted to try it with a girl. There's a hot bi girl sitting on my couch begging for sex." 

"I'm not begging it's an offer, but if I have to beg that's not a problem." When she said that bailey looked at me with her one in a million smiles and nodded.

"Fine, but we're doing it in my room. Your room smells like vagina juice."

"That's because I'm always masturbating in there."

When we got in my room we all started to get naked. My sister was so hot and I got to fuck her and my girlfriend at the same time. When they got on the bed my sister started to lick bailey's pussy. Bailey was moaning, but not as much as she was for me. Colleen paused and said "Stick it in." and then continued. 

When I put it in I took my sisters virginity. My sister lost her hymen after years of gymnastics, so I don't know if it hurt but she was moaning with Bailey.

She took her mouth off the pussy and said "Oh... oh yea fuck your sister's tight virgin cunt... yea fuck your sisters dirty cunt." And then she went back to licking furiously. 

"I'm going to cum!" I told them. And Colleen responded with what sounded like in me, so I came in her. When I collapsed bailey laid her head on my chest and Colleen said "Wow that was a great fuck. I've only had lesbian sex with Kim, but man a hard cock feels great." 

"Come cuddle with us." Bailey said. With that Colleen came over and put her head on my chest too. After about ten minutes I fell asleep. 

When I woke up Colleen was gone, which to be honest I was glad. I love my sister don't get me wrong, but not the way I love Bailey. I watched her sleep until she woke up half an hour later and I said "I want you to know that was only a one-time thing. The only woman I want to be with is you from here on."

"Good, because I couldn't stand it that she got you the whole time. So now I think it should be just us from now on too." I kissed her passionately and we turned on the TV and watched The Big Bang Theory, while cuddling. 

After a while, she fell asleep but still holding my arm. I didn't dare let it go, she was so beautiful. I slipped my arm out, and since we were still naked, I saw her pussy was wet and getting even more wet. I started to lick she tasted so good I could live off of it for weeks. When she woke up from all of the pleasure I stopped, but she said "I'm about to cum if you don't keep licking I'll get the dildo." I didn't object so I continued. 

When she came it went all in my mouth, and it tasted delicious. "I want you in me and I need it now." She whispered. I came up and stuck it in her and we made passionate love. 

When we were done, we took a shower together in the bathroom in my room. After the shower we went downstairs, and we found my parents.

"Hey guys, we know that you two are a couple now so there's no need to hide it." Mom said.

"Colleen told you?" I asked.

"Of course your sister told us."

"Is there a problem?" I asked.

"No, actually I think it's about time." Mom said, and with that we left and my mom and dad laughed as we left the house.

"Want to go play Xbox at my house?" Bailey asked.

"Are we really going to play Xbox or are we going to fool around?"

"Probably fool around." When she said it she had her sexy and wicked smile.

"Then that's a definite yes."

We fooled around the whole time and I spent the night.




Thanks for reading if you like the story or have any suggestions or ideas for this story or another one my stories contact me or comment.

-James