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SEXMONKEY101 Member Since October 19, 2009

My new girlfriend and how it came to be and my maid

SEXMONKEY101 on Teen Stories

Well this is the story of how I had sex with one of my very best friends. And the next day when I had sex with the maid that cleans the house

 

So it was Halloween and I went trick or treating with my very good friend Cindy. She is a very nice girl very good body and very nice breasts.  We have known each other for almost 6 years and have never dated or had any thought of doing anything sexual or going out. Well we had been trick or treating for about an hour when she decided to go off

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with some other friends so I asked if she could give me a kiss on the check. She didn’t want to at first but I talked her into it. So as she was just about to kiss me on the cheek I turned my head (as being a guy I always wanted a kiss) and kissed her lips. I expected her to pull back, but she didn’t. Instead she kept kissing me on the lips until I broke the kiss in shock. She had never told me she wanted to do anything like that or kiss me. She said she had been to shy but had liked me since she had met me. Well she decided to stay with me and we went trick or treating for about another hour and kissing and hugging and even laying on the ground making out a couple of times. We ended up back at my house were I said “do you want to come in” she said “yes”. So we went into my house and nobody was there. They were all out trick or treating. So Cindy and I went to my room and laid there kissing for about 15 minutes then I asked if she wanted to start dating now that we’ve done all this. She said “yes”. So we kept kissing then she went to the next step and very slowly put her hand down my pants. I didn’t have a hard on so my penis wasn’t that big. When erect I have a 9 inch penis and only a 5 inch penis when soft. So she didn’t touch my penis yet, she just played with my pubic hair, pulling and twisting and whatever else she did. My penis started to grow. All this time we kept kissing. Then she started to take off my shirt reveling my chiseled 6 pack as she kissed all the way down to my belt. I just looked at her and said nothing. Cindy started to undo my belt buckle. As she saw the bulge in my pants grow to its limits. As she pulled down my pants my 9 inch thick penis sprung straight up almost hitting her. She took my penis in her hand as she started to stroke it. She licked the head and put it in her mouth. Her mouth was so warm and wet, it felt so good. I didn’t know if she could handle all of my cock because she is a lot littler than me. She started off slow only getting about half in her mouth. She started going further down my shaft almost all the way, at least 8 inches. As she did that for about 2 minuets or so I finally pushed her head all the way down to my pubic hair. I could feel the head of my penis in the back of her throat, the amazing thing is that she didn’t even gag she pulled her head back off my penis and then went all the way back down. Cindy did this until I came all over her face and in her mouth. She tried to swallow my huge load of hot slimy cum but some slipped out. Then she got on top of me and adjusted to fit my still hard cock inside her little pussy. She went down slowly until my entire 9 inches of meat was inside of her. She was very tight and completely wet so it was pretty easy to get inside of her. She moaned very loud as she humped my penis. I played with her very nice, plump, firm tits while she did this. She got off of me after some time and we kissed very passionately. Not like before at all, this time it was different. As we lay there naked she told me she loved me. We had said we loved each other before, you know as friends, but never like she meant it. I told her I loved her to and I meant it this time.

I then rolled on top of her and put my penis inside of her little pink pussy and fucked her vigorously. She moaned and yelled so loud I thought someone would hear us. I released my load of cum inside of her and lay on top of her exhausted. We laid there for what seemed like hours. As we got dressed I told Cindy I loved her and she said it back. After that I drove her home said I loved her and dropped her off at her house.

The next morning I didn’t want to go to school because I was so tired because after I dropped Cindy off I went back out and hung out with some friends. I told my mom that I wasn’t feeling to good and I needed to stay home, so she let me and I went back to sleep. When everyone was out of the house the maid showed up, her name is Katie. She is probably in her late 30s or early 40s. She’s not hot at all and she is a bit over weight. But it never bothered me. Well while I was sleeping I was thinking of Cindy and got a hard on. While she was there she came into my room not knowing I was home. She saw me laying there with the blanket in a tent shape. As I woke up the blanket was taken off of me and she was staring at me with her hand in her crouch. I jumped up put a pillow over me and screamed what the fuck are you doing. She said never mind me and go back to sleep. I screamed and said get out. She wouldn’t and then she came closer to me. I yelled and again told her to leave. She just ignored me. She was about to touch my penis. Somehow she managed to get the pillow off of me and grab my penis. I was strangely turned on by this and let her touch my cock. She started stroking very slowly and it felt just like Cindy. Then she brought her mouth down and put my whole 9 inch cock into her mouth. This turned me on so much. I then forgot about everything and told her to get naked. She did. I told her to get on my bed and lay down. I took her legs and put them on my shoulders. I burred my face in her big fat pussy and got her soaking wet. She screamed

 

Oh yes Tyler!! Lick that pussy as much as you can! Get all my juices flowing

As I licked as hard as I could

Yes! Yes! Oh god yes im…im..Im cuuuuummmming she said

Give your juices to me Katie put them all over my face

Yes yes oh god it feels so good said Katie

 

I then sat up and slid my extremely hard cock in her fat pussy

Her pussy was much different than Cindy’s. Hers was very loose and I could fuck as ]hard as I wanted. I shoved my cock inside as she screamed more. I was about to come. And she knew it. She said come inside of me. Let me feel your hot creamy cum. And I did. I think I cumed more than I ever had before. After I slipped my cock out of her she sucked me clean and kept sucking until I got another hard on. Then I fucked her in her ass. Her ass was just as loose as her pussy and it felt so good. I couldn’t stop and ended up cumming inside her ass. She again sucked me clean and kept sucking until I got once again another hard on. She took my cock and shoved it in her mouth and said fuck my mouth and I cumed inside her mouth and all over her face after that we kissed for an hour as I liked all the cum of her body and feed it to her in her mouth out of mine. That was the first and last time we ever did that because I realized I couldn’t loose Cindy because I loved her and I always will. Cindy I love you if you ever read this and call me so we can go fuck again!!!!

 

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