This story is a work of fiction and contains descriptions of explicit sexual acts. Some of the parts are real but will leave that up to the reader to decide. If this type of content offends you or you are under the age of 18 do not read it.
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This is a strange story for even a pervert like myself, I am an older guy who lives in a large senior development, a very large one with active adults. To explain first I am 65 years old, a little over weight, married, but wife does not know about the fact I love to play with other guys also. Been having sex with boys since I was a boy and tried many a thing, but as I have gotten older I seem to prefer to bottom. There are times I just like being a submissive slut to another guy and let him do what ever he wants to me or my hole. I tried cross dressing but did not really become my thing but I can understand why some guys like doing it.
So my wife and myself are part of a committee that helps out in arranging parties to raise money for other charities. So we were in a meeting and since I seem to get stuck making the slide presentations, I was paired with one of the other ladies sort of. Let me explain, her name is Linda but all the women treat her like one of them since that is the way she prefers, but the men seem to sense that she may not be a women. She is very thin and just a little shorter then I am and I am 5'8" so she is maybe 5'6". If I was to guess I say she is in her late 50's or early 60's at most. I have never seen her wearing anything other then tight fitting stretch dresses that form to her shape. As she said she sort of looks like a very thin girl, with small tits, at least it looks that way. One of the things that I see as a give a way is that she has excessive make up on, and very perfume, and her face just looks like it belongs to a man, but in truth none of us men are positive what her sex is. And I should add when she talks it at least to me sounds like a man trying to sound like a girl.
So here I am at the meeting and the leader asks me to get together with Linda since she has all the pictures from the last party we had and she is not very computer savvy. In order to get them over to me in the form that I need I made arrangements to go to her house on the following morning. On the ride home my wife says something and I just kid back. This is going to be interesting since in most of the meeting I try to keep my distance from her. Being honest I wondered what would it be like hooking up with her for sex, I at least imagine she gives great blow jobs. Then I said "No big deal I just need to go there and arrange the pictures, then sort them and then copy them off to a USB stick so I can make a slide show for the next party. Depending on how fast her computer is should take me a good part of the morning."
The following morning I get up and tell the wife I am heading over there, she says to me like she always does "be careful", I tell her sure and think to myself what's to be careful. For one thing I have no desire to fuck her and I do not suspect we would get in a situation where she would fuck me, and that is even if she has a cock between her legs. So I arrive at her house and she lives alone, and when I answer the door she is in her normal outfit, a tight form fitting stretch dress. She is friendly like she always is and leads me to her spare room, where she has her computer located. As I am walking behind her I wind up looking at her ass, like I always do when I follow women, and to me she has a firm ass like a tall girl but a young one. Or in truth I have seen the same bubble ass on some young boys but that a different perversion of mine. Once in the office she has me sit down and shows me where the collection of pictures that I need to look at are stored. I thank her and tell her this will take me a while, she says that's fine she had nothing else planned for today. As I am looking at the pictures she stays with me and as she is pointing out some of the better pictures. I agree and select some of them for the project. She is leaning over me and I feel her hand on my leg and I do nothing to stop her from doing that. At one point I had my arm down on the front of the desk and she leaned in real close and seemed to push her crotch into the back of my hand. Hard to feel with the back of my hand but with her crotch touching it seemed a little too big to be a pussy. I did not move my hand and she did not stop pushing her crotch into my hand, and she sort of had a smile on her face as she was doing it. Being honest I was not sure what I should do. If there was a chance that she was a transsexual who liked to fuck then I would go for that idea. I was not sure what to do, after all, myself and my wife worked in the same group I would not want it to get back to her. So I played it safe and did not attempt anything, like say, turn my hand around so when she did it again I would get a real feel of her privates.
I worked on the pictures for a while and while doing them she said she be would back in a few minutes, she had to go outside and explain to the gardener what plants she wanted changed out for more colorful ones. I said "take your time" and off she went. I was finished with my sorting and selecting so I closed the window to set up my next step. After I closed the window I noticed this icon on the screen that just made my eye go to it. I figured what the hell, she said she would be outside a while so I will take a peek. I clicked on the icon and it brought up a folder with many pictures inside, after looking at the first few I realized it was pictures of Linda with other men, some she was getting fucked or sucking cock, but there were quite a few of her fucking some of the guys. In the pictures where she was sucking cock it was not hard to see that she had a good size cock between her legs. In all of the pictures she was dressed in a sexy girls outfit, being honest not my thing, but seeing pictures of her fuck some guys was hot. I guess I was not really being careful and did not realize that she had come back into the house and back into the room I was working in. I suspect before I realized it, I had made a few of the pictures of her fucking guys larger so I could see them better and it was having an effect on me since my cock was getting hard.
I was caught, what could I say? She came over and asked if I liked the pictures and I had to say yes, then she said "I notice the pictures you enlarged looks like you like to be on the receiving side" I had to answer "yes I do". Without saying another word she bent over me and had her hand in my crotch and was fondling my hard cock. She then had me stand up and she pulled down my shorts and underwear and my cock exposed. I am not a big guy maybe that is why I like being on the receiving end, but I say I am maybe six inches and average width. This may sound crazy but in my mind I preferred a cock like mine for sucking since it fits in my mouth so much better then a long cock. But if I was being the one getting fucked then I like guys that are really hung, just something about a long fat cock as it stretches my man pussy.
I was in heaven when she slid down to the floor and started sucking my cock. I am a good cock sucker and have to admit she knew what she was doing. She sucked me a while then got up and pulled off my shirt so I was now naked. I told her "I do not have a lot of time, so let me set up the transfer process so it can run while we are doing something else." She then had a smile on her face and she asked me "Since we're short of time what would you like to do?" I just pointed at the picture of her having some guy bent over and she was fucking his ass.
She said "Fine with me, you set up what you need to and I will be right back, I need to change into something more comfortable" I worked as fast as I could and the photos that I came for were starting to be transferred to the USB drive. This would take a good while, when the process started Linda called out to me and said "if you can, break away for a while." I said "yes the copy started and will be finished in about 45 minutes." She then said "good, that will work, come into my bedroom," so I did. I was still naked but my cock had went down, when I walked in her bedroom Linda was wearing the same outfit that I had seen on the girl in the photo. It was a sheer pink baby-doll sleep wear, she had pink ankle socks and no panties which looked hot because when I entered the room she was just slipping on the socks so her ass was in full view. I looked up at her top and she did have tits, small but on a thin frame I say just like say a twelve year old girl. I forgot to mention young girls are a turn on for me also. She knew I was looking, so she shook her ass a little and said "sure you do not want my pussy, it is nice and tight? But when she turned around her good size cock was visible through the shear fabric that made up the outfit. I had decided that I wanted that cock in me, so I said "if it is ok with you I like to be the one on the receiving end." She then said "since we do not have a lot of time lets not waste any", she had me come over to her makeup table and told me to lean forward and she grabbed a anal plug off the counter and looking at it, I could see it was slick from oil that she must have just applied.
The plug felt so good as she slid it into my ass. I was tight since it been a while since I been fucked. She hit a button on the anal plug and it came to life. The thing was vibrating and also seemed like the very tip was getting bigger, felt like it was growing in my ass. Then she said "while that's working on your hole, I need you to work on this." She then put her hands on my shoulders and pushed them down and I was on my knees, with the anal plug doing a job on my hole and really making me horny. She then positioned her cock in front of my mouth and I opened up my mouth and I leaned in and here I was sucking Linda's cock. Her cock was growing as I did and when she was as hard as she was going to get she was a good 8" and some what thick. I suspected she knew her cock would be hard to take in with out the step to loosen up my ass with the anal plug.
She then had me get up and lean against the makeup table sort of bent over, she then removed the anal plug from my hole. As she took it out and put it on the counter I realized I was right, the plug was a lot larger than it was when she inserted in me. As soon as it was out she had me lean over the counter and she slid her big cock in and started slowly going deeply into my man pussy as she could. It was strange having Linda fucking me but it felt fantastic so I did not care. She fucked me a while and every once in a while she seemed to move my position to the side a little. She had to be fucking me for almost thirty minutes, she would go for a while then slow down or stop and then go again, just teasing my man pussy but at the same time lasting really long. I knew what she was doing when she get close to cumming she would slow down or stop so she would cool down some. I did this myself when fucking knowing that when I did cum my load would be more intense and more cum would come out.
The crazy thing is my wife never liked that, when we were younger she said I fucked her too long and she was not crazy about me cumming a lot. I guess that is why I also liked men I hardly ever met a man or boy cock sucker who did not like a big load.
But then I felt her cock tense and she pulled my hips in and her cock was buried all the way in my body, when she started filling my cavity with her cum I could feel the wetness and I have to say I loved it. The whole experience was sort of strange to me but still very hot, I figured I would have to make some excuse to come back here again. Also at the last moment she let me know she had taken some pictures of her fucking me so she could remember it, but she added "I made sure I blocked your face" just like the other pictures I had seen on her computer.
Before I collected all of my stuff and the photos I needed I sort of let her know that if she had a few guys over and she needed a bottom guy just let me know, I would make some excuse to stop over. She smiled at me and said "did you like you man pussy filled?" and I smiled and said I loved it. She said she knew what it felt like and she loved it also but sometimes she likes to be the top. I said I was glad that was the case this time..
Hope you enjoyed this story email me at woodd_guy@yahoo.com