Once again, here is a story about a business trip I was on. My business trips are sometimes too busy, so nothing beats going to get a late dinner and then going to the hotel bar for drinks and finding someone to fuck.
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This one time, when I was grabbing a cocktail at my hotel bar after a ridiculously long work day, I started to chat it up with this guy next to me. The whole bar was pretty empty, so I was a bit bored, and he was the only one. A bigger fella, nerdy-looking, and half my age. Now, I’m no supermodel, but I have a very pretty face and a curvy body. Guys tend to gravitate to my ass. Anyways, he was telling me that he works for IT and that his company sent him to help fix a problem at one of their sister companies. I started to tell him my busy schedule that day, and all in all, it was just a normal, basic hotel bar conversation. I kept thinking in my head of how cute it was, how nervous he seemed with his body signals. Almost not knowing if he should start turning towards me or away. After an hour or so, I told them that I was heading up and asked him if he wanted to join me. I was surprised myself that I asked him. At that point, I wasn’t even sure myself what I would do upstairs in my room with him. He wasn’t the typical guy that I looked for at the time. Then again, new things turned me on. He was a pretty big guy, nerdy, had a beard, and told me earlier that he was 24. I was already 40 at this time. He almost reluctantly but excitedly said yes that he would come up to my room.
When we were in the elevator, it hit me that I was totally on my damn period that day. I thought, oh well, I’ll just play around without the pussy getting played with.
In our room he started to almost over talk nervously as I had him sit on the bed. I finally told him to relax and started to unzip his pants. Now, a few things stood out at this point to me. One, not super long but fat dick. Two, uncircumcised. Not against any of it, just wasn’t used to this. It excited me even more. I started to lick his dick all over with my tongue and sucking on it. He was moaning like it was his first blowjob he had ever gotten. I could tell this was going to go quick so I looked up to him and said “just enjoy big boy, just cum whenever you want!” And that he did! A few seconds later he is filling my mouth up with cum. Now after swallowing it all I put my mouth back on his fat dick and started to bob my head up and down again. He got hard again immediately. The young cock always recovers quick. At this point, I told him to take off all his clothes and that I needed to use the bathroom.
In the bathroom I got naked and yet had the problem of being on my period. I just laughed to myself and thought “oh well, looks like my ass is going to hurt tomorrow.”
When I came out naked, I could see the lust and excitement in his eyes. He was laying down completely naked, so I went straight to suck at his dick more. I could tell he was getting more comfortable because he started putting his hands on the back of my head. I encouraged him by putting my hands on top of his hands and forcing my face down on his cock to fuck my mouth. He was getting in his groove at this point and really started to roughly fuck my mouth. After a little while of doing this, I told him that I wanted him to fuck me, but I was on my period. I got off the bed and grabbed a container of lube that was in my purse. At this point, I asked him “ Did you want to fuck me in the ass?” His response was.” oh yeah!” so I bent over, put the lube on the rim of my ass and push it into my ass. He got behind me and pushed himself inside it. He had his hands on my ass and started to pump away. He was fucking really good and was saying stuff like.”oh my god, you’re so hot. This is the best day ever! You like it, baby?” I loved how comfortable he was getting now. So I told him.” I do love it. Fuck so good but you don’t have to be so gentle. Why don’t you tell me what a fucking whore I am?!” This must’ve really excited him because now he was fucking my ass like I was a cheap cock sleeve. He was saying stuff like.” fuck, you’re such a whore. I just met you and now I’m a fucking you in the ass an hour later!” I loved it and I was encouraging him. I was saying stuff like.” that’s right big boy. My husband and kids are at home in a different state while mommy’s on her business trip getting fucked in the ass by some guy she just met and that’s half her age!” All this guys wildest dreams, must’ve been happening because he went from shy nerd to verbally humiliating me in just a few hours. At this point, he couldn’t last much longer so he was really ramming me hard and said.” I’m gonna fill your dirty hole up with cum., bitch! And he started throbbing and pulsating in my asshole.! we laid there silently for a while, then he put his clothes on, kissed me and left.
I never saw that guy again, but I’m almost positive that he jerks off every week thinking about that encounter.