I would never expected my day to turn out like this. While I was at work, me and another busser name Shawn was talking to a server named Jessie. She was cute, she has curves, C or D tits, blonde/brown hair. She is the type of girl likes to joke around and beat the shit out of you if you piss her off. While we were chatting with her, we kept talking about sex. She asked if we would fuck her, Shawn said no do to respect. I said fuck yeah. Some how we got on the subject of anal sex, she said she wouldn’t do it, I asked if she tried it, she said yes and it hurts. All this talk about sex made me horny, so I asked Jessie if she was doing anything after work, she told me just going home. I asked if I could come over. She told me Shawn already asked and she said yes, so I said, so I can’t come over then, gave her the sad puppy look. She broke down and said, yes you can come over.
We got to her apartment, she lives with her younger s****r who also works with us. She wouldn’t be home for another two hours. Jessie said to us, Let me change into something comfortable. She went to her room and 5 minutes later, she came out in a short skirt and a blouse. We sat on the couch, we continue to talk about sex. 10 minutes into the chat, Jessie got up and told us to follow her. So we got up and followed her to her bedroom. She told me to close the door behind me. So after I went in, I shut the door. She laid down on her full size bed and spread her legs open to show that she had no panties on. She had a nice trimmed bush, her pussy looked amazing. My dick got hard as a rock. She told us we have little bit less than two hours before her s****r comes home. She started to finger her pussy, it was wet. She said, Come on boys, I want some cock and I want it now. We both dropped our pants and boxers. Shawn went first, he stuck his cock in and fucked her slow. She started to moan. I was waiting for my turn, I started to stroke my cock while I waited. Shawn fucked her for 5 minutes until I asked if I could have a turn. He pulls out and Jessie had a look on her like she didn’t want me to fuck her. I put my cock in and shove my cock in her repeatedly. She moaned with each thrust. About 3 minutes in, she asked if Shawn can fuck her some more. I said, I guess. I got off and let Shawn back on. She moaned loudly with him, I think she even didn’t want to fuck me. They fucked for 20 minutes until he came. He rolled off and lied there, while my cock was still hard and wanted some more pussy. She looked at her watch and said, Oh look what time it is, my s****r be home soon. She wanted us out, mostly me. Shawn got his clothes and they went to the door and they chatted, I stayed in the bedroom naked.
Jessie comes back in her room and told me to get dressed and get out. I told her she invited us over and I only had 3 minutes of fun. She acted like she was going to give me more but she blames Shawn for fucking too long. She went over to her bed and bent over to pick something up. I came up behind her and stuck my cock in her cum up pussy. She told me no, her s****r will be home soon and got my cock out. I toss Jessie on to the bed, she was on her stomach, I laid on top and try to fuck her, but she had her legs closed. I spit on her ass, she started to bitch at me for spitting on her. She didn’t know I was spitting on her ass hole. I took my dick, rub it in the spit and rubbed it around her ass hole. I shoved the head of my penis in her ass, she jumped and let out a big painful scream. I kept putting my cock down further into her ass. She kept saying ouch and try to get my cock out. I had to hold her firmly and I slowly went up and down on her. She was crying from the pain. After a few minutes of slowly fucking her ass, she relaxed and I started to fuck her normal speed. She started to have an orgasm. I was holding on to her hands, I felt her squeezing my hands as she moaned and started to enjoy the anal fucking. I started to fuck her little bit harder. She told me it was feeling good and wanted me to pound her ass. I told her OK and slam my cock in her hard. She let out a big orgasm after another one. I made her cum, some of Shawn’s and her cum dripped out of her pussy. As I was pounding her ass, her s****r came home. She heard Jessie moaning and having an orgasm. I fucked her ass for 30 minutes until I came. Best feeling, shooting cum in her tight ass.
We both laid there, catching our breath. She said that was the best anal sex she ever had. The boyfriend from before didn’t do it right and hurt her ass. She got on top and got my dick hard again and started to ride me. She told me she was sorry about earlier, the truth was she only wanted to fuck Shawn. She said she will make it up too me right now. She took off her shirt and bra and rode me. She didn’t take off her top when Shawn was fucking her. She bounced on my cock, I played with there tits. I told her I was about to cum again. She told me to go ahead and shoot my load in her. As I started to cum in her, her s****r opens the door and asked if she was done yet. Jessie hopped off my dick, I was still in the middle of cumming so I was shooting my cum up in the air. Her s****r, Katie saw my cock and the cum shooting up. She noticed it was me, and left saying geesh Jess. Jessie covered up and asked me to get dressed and leave please.
Next day at work, I saw Katie but Jessie wasn’t there. So I asked Katie where Jessie was. She told me she wasn’t feeling well and called off. I asked Katie why when she left she said geesh and left. She pulled me to the side and told me, She does this a lot, she fucks a lot of men. Co workers when I’m at work, men I have no clue about at night. So I asked about her, I asked Katie, Do you have sex with guys? She told me yes but not like what Jessie does. I asked if she will with a co worker, she said no.
At the end of the day, I saw Katie. I asked if she wanted to hang out at her place. She told me no, I said please a few times and she finally said yes. We got back to there apartment, she went in first to see if her s****r was in the living room. Jessie was in her bedroom. We went to Katie’s bedroom and we chatted for a bit. Suddenly we heard Jessie having an orgasm. I ask Katie if she ever tried masturbating. Katie laughed. Katie said, She needs too, she sometimes fucks two to three guys a day, one time she fucked three guys at once. I told her that me and Shawn was fucking her yesterday, but I only had three minutes but later she gave me more. I kept hearing Jessie moaning, my dick was getting hard. I asked Katie if she bring any guys home, she told me she did once, that guy ended up fucking Jessie. I told Katie, Well I’m in your room and I already fucked your s****r so you won’t have that problem now. She started to argue with me so I leaned over and kissed her, we started to make out. Katie was little bit different from Jessie, Katie is skinny and her tits is a B cup, small B.
Hearing that moaning and making out with Katie, I was very horny. I took off my shorts, I had no boxers on. Katie saw my dick and kept thinking about yesterday. She was having second doubts. I told her to lay down, you can keep your clothes on and I will dry hump you. She thought that was the dumbest thing she ever heard. She lied down and spread her legs open, I laid on top and started to hump her. We kissed, I asked her, How often you you masturbate? She looked at me and said, What makes you think I masturbate. We heard Jessie moaning some more. I said, I don’t know, seems like you haven’t had a guy in a while, fear of losing him to your s****r. She looks at me and says, once or twice every other day. I lifted her shirt up some and kissed her stomach. I put my cock on her stomach too, the pre cum went on her. She took her shirt off and her bra. I went back making out with her and rubbing her nipples. She got comfortable enough where she took her pants and panties off. I went down and licked her pussy, she liked it. I went back up and slowly put my cock in her. We made out while I slowly fucked her. She was moaning, I started to pick up speed and she was moaning more and more. I could still hear Jessie moaning, while fucking Katie, I was thinking about Jessie’s pussy. I started to pound Katie’s pussy hard. I was about to cum, but I slow down, didn’t want to cum just yet. I pulled out and told Katie to get on all fours. She did and I slid my cock in her and made her scream. I slammed my cock repeatedly. Katie was close to cum, I felt her pussy tightening up some. She had a good orgasm and came, I started to cum in her. Jessie comes busting in on us, Jessie was half naked, I saw her pussy. Katie didn’t move or try to hop off, she let me finish and I kept pounding her pussy in spite of Jessie being right there watching. She didn’t look to happy that I was fucking her s****r. After I was done, we both lay down and just cuddle. My dick was against her nice sweet ass. She didn’t mind I was getting pussy and cum juice on her ass.
Ever since that day, Jessie wouldn’t talk to me. I’m guessing I suppose to only fuck her and not her s****r, but it was her being rude to me when I try to fuck her before. Oh well woman are strange.