This happened on the third night of a training I had to go to from work. Since the training was over two hours away from where I worked, they paid for the eleven of us who went to stay in a really nice hotel. Let me tell you first about Sandy and me. Sandy is one of my managers and the one who came to somewhat supervise us on this training.
Sandy is one of my managers and the one who came to somewhat supervise us on this training.
Sandy is 36; she is married with two daughters.
Sandy is about 5"10, long straight blonde hair and blue eyes. She isn't gorgeous, but she is really beautiful. I would guess she had about a C cup breast size. She also has a little meat on her bones, but not much to say she is overweight by any means, mostly just somewhat leftover baby fat.
Me, my name is Matt. I am 27. I am 6'0 and about 280 lbs. I am a pretty stocky and big guy. I have short brown hair and hazel eyes. I am pretty average in penis size I would say, about 6 inches and somewhat thick.
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Ok, so this night was like all the other nights so far. After the training was over we would all go to the lobby of the hotel and enjoy the free drinks they were serving. This usually lasted about an hour to an hour and a half. After this, most of us would walk to one of the many restaurants in the area. This time, however about 7 of us decided to order room service and go up and just drink and talk in Todd’s room. Todd is a really big drinker and even brought a suitcase with just beer and alcohol for everyone.
After dinner, we continued to drink and some of the people were playing an Xbox that Todd had brought. With people starting to get really tipsy, all the funny stuff started happening. Here I was in a room full of people I worked with who acted one way at work and was now totally different. On this one instance, I was taking video with my cell phone and I happened to catch my manager Sandy. She was what I would say was drunk. She walked up to Todd and slaps him on the ass. Todd turned around and told her if she liked that then she would love touching this, and stuck his crotch in her face. She gave it a kiss on his pants and sat back against the wall. After seeing that, I started to show some of the guys who didn't see it happen.
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Sandy had since gotten up and came over to the couch where I and another guy were sitting. She asked us what we kept watching on my cell phone. I didn’t tell her anything at first, but she kept bugging us. I finally told her that I recorded her little incident with Todd. She couldn’t believe it. She got a little mad at first and told me to delete it. I told her that I couldn’t. It was too good. She then told me to give her my phone, which I didn’t. She then tried to grab the phone from my hands. I kept moving it away from her. She finally got so mad she sat straddled on my lap trying to get the phone from me. She still couldn’t get it. It didn’t take very long with all the moving she was doing on my lap to get me excited. I started to feel the bulge growing and I had a feeling she would to since I was in sweat pants.
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I just for some reason hoped no one else would notice. After about five minutes of this, and knowing she was drunk, I figured I would take this to the next step. I said if you want my phone that bad, then you will have to get it. I then proceeded to stick the phone in my pants between my cock and my balls. She really didn’t do anything at first and I thought I had just blown it.
Then, out of no where Sandy looked around the room to see if anyone was watching. When no one was paying attention she put her right hand in my pants to get the phone. Fumbling around trying to get it, she kept brushing against my cock which got me even harder than I was before. She finally grabbed my phone and went back to where she had been sitting to try and delete the video.
A half hour had gone by and everyone was still drinking and playing Xbox. I was getting kind of tired, so I told Todd and some of my other friends that I was going to go back to my room to get some sleep. As I walked to the front door Todd stopped me and asked if I could help make sure Sandy gets to her room ok. She hadn’t had anything to drink in a little while, but I could tell she was still a little drunk. I told Todd that it wouldn’t be a problem.
So, I got Sandy down to her room ok and was on my way out when I remembered that she had my phone.
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I went back into her room to get it. Luckily I still had her key she gave me when I first helped her in her room.
I opened the door and walked through the living room part to get back to the bedroom. The door was mostly closed. When I peeked through the crack of the door I noticed she had taken her shirt and pants off and was just laying across her bed in her bra and panties. I started to get aroused looking at her. Just then, I noticed she put her right hand inside of her panties. She was really starting to work her self into a freenzy. I tried playing it off and just opened the door and told her I forgot my phone, that I needed it back. She jumped up and tried to get under the covers really quick. I asked her why she was freaking out and got under the covers? I told her she wasn't wearing anything less than the bikini she wore to the pool. She told me that she was going through a rough time in her personal life. I sat down on the edge of her bed. She started telling me that since her last daughter was born a two years ago that her husband and her had only had sex maybe a handfull of times and that was when he would come home drunk. Also, that she hadn't had any sex in seven or eight months.
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She also said that she believes he was having an affair with a woman he works with. Sandy started to cry and said that maybe it's because she isn't pretty anymore. I told her that can't be, that she was beautiful and that her husband was a very lucky man. She told me that she didn’t think so, but I told her she shouldn’t think that because any guy would be lucky to have someone like her.
Sandy, still crying started to tell me that when she was on my lap back up in Todd's room, that she got really wet from kind of grinding on me to get my phone. Then when I stuck it in my sweatpants that she really didn't know what to do. Sandy told me that she got married right out of highschool because she got pregnant the end of her senior year. She then said she had a miscarriage, but still married the guy who is now still her husband. She said he is the only man's penis that she had ever touched or seen that wasn't in a picture. Then when I stuck my phone in my pants she didn't know what to do. She said between the alcohol and the fact she was horny and wet, she went for my phone. Sandy said she intentionally grabbed my penis a couple times to see how big it was and what it felt like.
What happened next, I will never forget.
Sandy, with tears still in her eyes asked me is she could see my penis again. I looked at her for a second and thought if this is something I want to risk.
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I asked her if she was sure she wanted to see it. She thought for a moment and then said yes. So, I stood up from her bed and kicked my shoes off. Then I pulled my sweatpants down to reveal my thick six inch cock. I stepped out of my sweatpants and just stood there not know what I should do next or what would happen. Sandy just sat in her bed looking at my dick. I decided that I wouldn't hamper her view in any way and then took my t-shirt off and threw it on the floor. So, there I was butt-ass naked standing in my manager's hotel bedroom.
Sandy pushed the covers off of her and stood up next to me. I had all these things running through my head when she did that. I couldn't stop thinking how bad I wanted her. I didn't care if she was my manager, or was ten years older than me, or that she was married and had two kids. Then standing there Sandy looked at me and asked if she could touch it. Without hesitation, I said yes. There Sandy stood, right in front of my naked body and her in her bra and panties reaching out her hand to touch my dick.
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She sent shivers down my spine when her hand first touched it. I just closed my eyes for a second and take a deep breath. She started to slowly stroke my dick. I opened my eyes and looked down at her. We stood there with her stroking my cock in her hand and just staired into each others eyes. When Sandy started to speed up her rythem, I couldn't help my self so I leaned in a kissed her. Her lips felt so good. They were as soft as peaches. Sandy was supprised by this to say the least. I think it kind of hit her, where I wanted this to start going. She broke the kiss and started to tell me how wrong this is, and that I shouldn't kiss her. I asked her how that could be wrong, but her jerking me off was ok. She looked like she had all these things, these feelings running through her head. She told me how horny she is, but that in her eyes, she couldn't have sex with someone that isn't her husband. For one, she said it was wrong.
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Second, she said she isn't on the pill and didn't want to become pregnant. She told me if she did get pregnant her husband would definitly know she was cheating on him. I told her that she shouldn't have sex with anyone but her husband. That we didn't have to have sex to have a good time. I told her that all I wanted to do was please and pleasure her. Make her feel good and special. Sandy looked like she was about to cry. I didn’t know what to do, should I put my cloths back on and leave? Step into the other room? I just came to the point where I just said fuck it. I walked right up to her and started kissing her again on her lips. I was a little shocked when I could tell she was kissing me back. I really didn’t expect her to. So there we are, standing in her bedroom kissing. After only a few minutes our kissing got more passionate, I got a little braver and started rubbing my hands on her breasts. She didn't seem to object to that so I then reached around her back with my right hand and unhooked her bra. I then proceeded to pull her bra off.
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After I had it off and her tits were free, my hands were all over them. It wasn't too long after I had her bra off that I decided to start making our way over to her bed. Once I had gotten her laid down on her on her bed, I started kissing her again, but this time when I kissed her I moved over and kissed the left side of her neck and her left ear. This really started to set her off, for the first time I heard Sandy start to moan as I kissed her neck.
I slowly started to work my kissing down her neck to her breasts. I could tell that she was really getting heated. Her nipples were so perky; I just kept going from one breast to the other sucking and kissing on them.
After doing that for a little while, I decided it was time to move down. I kissed my way down to her belly button, then down to her panty line. I sat up and grabbed one of her legs and started kissing the inside of her thigh. As I was doing this, I placed my hands on her panties and started to pull them down off of her. At first, she put her hands down to stop me. I couldn't think why she would go this far, and not want to finish. When she put her hands back down to stop me a second time, I leaned up on her and started to kiss her mouth again. While on top of her and kissing her, I reached back down and started to pull her panties off again.
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She started to object this time, but I leaned over and wispered in her ear how all I wanted to do was pleasure her, and that I wanted to taste her juices. She stopped objecting and let me finish pulling her panties off. Once I had them off I glanced down at her pussy. She was extremely wet. Her pussy looked so soft and sweet. It had a little hair around the top. I laid back on the bottom of the bed and I spread Sandy’s legs and started to kiss around her pussy. It didn’t take long before I felt her getting even wetter. As I was eating her out, I could hear Sandy’s soft moans. It was really turning me on. I started letting my tounge rub around the outside of her lips and sometimes brushing it against her clit. After a couple minutes of this, I focused just on her clit. Sandy started to go crazy. Right before I thought she was going to have an orgasm, I stopped. She looked at me a little disappointed.
She asked me what was wrong. Nothing, I told her and I started to kiss my way back up her stomach to her breasts, then her mouth.
While kissing Sandy, she started to wrap her legs around the small of my back. Lost in the moment and not really thinking with anything but my dick, I grabbed it and started to line it up to her pussy. I started to rub the head of my dick all over her opening. She was still so wet, so in one quick thrust I now had my cock inside Sandy's pussy. I was in heaven. She was so wet, and so warm, not mention somewhat tight. When I did this Sandy kind of let her grip on me go. She let her legs fall and rest back on the bed and took her arms that were wrapped around my neck off. As I started to slowly pull out, I sunk right back in. She looked at me and asked me what I thought I was doing. I then leaned back down and started kissing her. I told her how could something so wrong, feel so right? As I continued my slow rythem in and out of her, she asked me if I atleasat had a condom to put on. I told her I didn't, that I hadn't expected anything like this to happen.
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She told me to get out of her, that we couldn't go any further. I did what she wanted. I sat up on the edge of the bed. I asked her if she liked what I was doing and she told me it was the best feeling she has had in a very long time. But she didn't want to get pregant so we couldn't go any further.
I asked her if I promised to pull out early and let her finish me off in her mouth or jerking me off would she do that. She thought about it for a second and said yes. So, I climbed back on top of her, my erection never have gone down and grabbed my cock and lined it up to her entrance. I slowly slid into her. As I did, Sandy let out a moan that was heavenly. I starting a nice slow rhythm and would increase it periodically. After about five minutes of this, I told Sandy to get up and turn around on her hands and knees. I slid back into her from behind. This time I was working her pretty good. I was really going at a faster pace now.
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Sandy was also moaning pretty loudly. After getting her from behind, I told her to lie back down on her back. I wanted to finish everything like this. I grabbed her legs and put them over my shoulders. I slid back into her and knew that it wouldn’t be long before I would have to cum. We were both pretty hot by now. We were both sweating something good. I was reallying giving Sandy all that I had. My pace was so fast right now, that she would let out a little scream everytime I would plunge into her. It wasn't long before I could feel that tingle in my balls that told me I was close to cumming. I told Sandy that I was about to pull out.
Sandy asked me if I could hold out for just one more minute, that she was almost there. I told her I would try and just kept pumping. All of a sudden I felt Sandy’s pussy clinch up and I could feel her cumming. That was all it took.
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I couldn’t hold it anymore. I wanted to be as deep as I could, so I lifted her ass a little more off the bed and I just pushed as far into her as I could and started cumming. It was one of the best feelings ever. I didn’t think that I would stop cumming. I just kept filling her with my cum. When I finally finished, I laid her back down on the bed and rolled off of her. I could start to see my cum leak out of her pussy. I just laid down beside her. Sandy was still trying to catch her breath. It was after she caught her breath that things got interesting.
More to come if the story is well liked.
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