A Tryst with Ann

This is a copyrighted original work by the author. All rights reserved.

No I did not use an editor so if you don't like to read unedited versions of stories you may choose to look elsewhere. You don't need to leave a comment telling me to use one because I will simply delete it anyway. Yes some of this story is true.

All characters featured herein are at least eighteen years of age, even if not expressly stated. Any resemblance between actual persons, living or dead is entirely coincidental. Thanks, Dean

*****

Sometimes you begin a story and wonder is it really possible that it really happened, and if it did can I actually tell everyone in detail that it did. This story is going to be told from the time Ann was 18 and a cute as hell high school senior. I was married at the time and still am, although that has nothing to do with this, since for my wife marriage and sex did not go together after we had children. It was an afterthought for her and slowly it wasn't even an afterthought anymore. Sex just did not exist. I think part of what got this going was the fact that I had always been infatuated with Ann even from the time she walked into high school. She looked so cute with her light brown hair that curled up on her head to just slightly below her shoulders. At that time she wore large glasses and I thought they were so sexy on her.

This woman, and that was how I saw her, had an ass that just didn't quit and being an ass man I paid careful attention to hers. Her breasts are large and I am guessing at around a 36 large C or D and I just wanted to put my mouth around her nipples and pull on them till they were hard. The problem was I could never tell her that. It just wasn't possible with who or what I was so I never made any advances of any kind toward her. She showed up once to leave on a trip with her blouse almost buttoned and I got an eyeful of her beautiful bouncing breasts even though she had a bra on I still got hard from just the thought of it. Her showing up dressed that way enraged my wife and she asked me if I got to see enough. I of course played it off since it was not uncommon for Ann to be running late. I had to love Ann for it and still do to this day even if it was by accident, although I hoped it was for my benefit.

Ann was that one person who I fell for that I knew I would never get an opportunity to enjoy or at least I thought so at the time. Fast forward several years and we both have grown children and I am still married to the same woman who thinks sex isn't even an afterthought. Why you ask? I don't plan to lose half my retirement to someone who did not earn it. You may think badly of me for that statement but until you walk in my shoes don't judge me too harshly. I work over 70 hours a week and have for years and she works a day a week and thinks she is being asked to do too much. I do my own laundry and the house is a mess.

Let's go back to the good part of this story, Ann. She and I made contact through Facebook I guess and I found out that she was having surgery. She was even having it in the town I lived in so of course I took her flowers and met her husband. She has a beautiful daughter that has her mother in her. I can see it in her eyes and face. I enjoyed the time that I got to spend with her and wished at the time there could have been more but it wasn't to be at that time. I did not hear from here again for about three months until she posted that she was bored. I sent her a text not realizing she was online and told her to hang in there. I was surprised when she responded back to me and we began a long conversation. Somehow we got to talking about books and I don't know if I brought it up or she did. We talked about the fact that what my wife read did nothing for me and she mentioned the Fifty Shades of Grey series. I told her I had it on my kindle and read it but it still was just not kinky enough for me.

Ann asked what exactly was kinky enough for me. I asked her if she could keep a secret and I was sure that she would because I trusted her. I knew she would not tell her husband or anyone else that she was close to. She probably knew that if she just let things play out that I would agree to whatever she wanted and she was right. I told her that I wrote stories that were definitely more on the erotic side. She asked if she could read them and I told her I would let her but my problem was that when you do that it basically opens your soul to someone and I didn't want to be hurt again. I had enough of being hurt. I needed someone who wanted to play with me and just enjoy each other in whatever form that took. Once she had the link to Literotica she started to read what I wrote and what I suggested first. The only problem was I wanted to talk and she wanted to read. I finally gave up after so told me several times to shut up and I told her I would talk to her when she was online again.

The next morning she told me that she stayed up till 2 am reading some of what I had written and she was intrigued by what I had. She told me that she didn't know I was an ass man but had figured me more of a breast man. I guess I was good at covering that anyway. We began to talk again and it took us a while but we both finally admitted that we were interested in seeing each other. She wants to be more dominant and I can go that way if it makes her happy. I will just be happy in getting to enjoy her any way that I can. Talking with her revealed that she might think I will not be impressed by her body, probably due to age but mine has aged as well. I am really more interested in her but having the opportunity to play with her is one that I would never turn down. I looked forward to what she wanted to do to me although she seems to want to keep that part a secret.

I guess women have a right to have secrets and she told me she hoped I could handle what she had to give me. I am salivating at the thought of that. I feel in time she will want to add another woman to the mix and I won't say no that that either. If it is something that two people can share and she has a friend that also wants to play, that she is comfortable with, I trust her enough to be able to make that decision. We talked again in between her telling me to go write because she was reading. I know from where she is in my list of stories that I am definitely not an angel and she will see that very quickly. I am looking forward to her texting me back to talk again as I write this.

We have planned to meet in almost three weeks. I have to work several shifts at work due to an absence and I can't do anything about it. If I could I would be there next week to see her. Through our brief conversations Ann did tell me that her ass is her least favorite part of her body which made my heart sink. I was hoping that I had found someone who was into ass play as much as I was. I guess the upside to this whole thing is that even though I do not know what parts of her body begin to tingle when they are delicately strummed, I do know that she did not say that ass play was out. She seems to be willing to allow me my pleasures and I am more than willing to grovel at her pussy or any other place she chooses.

I continued to text back and forth with her over the weekend which did cause an issue that is mostly my fault. Her phone went off to many times for her family to listen to and they questioned her about it. She just told them it was a friend and they didn't want to hear that so she told them it was me. It is not as if they do not know who I am. They were upset and she told them we were just chatting back and forth because that is what we were doing. I am hoping that this does not cause any problems for her because I would not do anything to hurt her. Walking away would be so very difficult for me but I would do that instead of seeing her hurt.

We had been texting so much because she had asked me to do something for her and the fact that I enjoyed our conversations. We talked about various sex toys and she asked me about some of the things in my stories were true. I told her that all of them have some truth in them because that is how I write. A little imagination goes a long way as well and there is plenty of that in some of them as well. I told her that there were times when I did research on some of the stories as I wrote them so that I knew what it would feel like. I can write more accurately knowing how I felt when it happened to me. She wanted to see pictures of what I had from some of the stories and I told her that I would take them and send them to her.

That evening I took pictures of what she wanted, the golf club from the Dean and Marie series and a picture of a dildo that I told her I had that is rather large. I also planned ahead because she told me she was a visual girl and I just knew in the back of my mind what she would ask next. I sent the pictures and she said, "I thought they would be you using them."

Just as I expected she did ask for that so I sent her a picture of the large dildo shoved up my ass and a picture of the modified golf club before and after entry. I heard nothing from her about them for a long time which was agony on my part since I had hoped I didn't repulse her. I didn't think I had but you never know how people will react. Finally later that evening I got a message saying, "Interesting."

Yes I had hoped for more than that but I guess that is the secretive part to her. She was still having discussions about all the texting with her family and around 9 pm she texted, "Good Night."

I followed her text with, "Good Night, Take Care,"

A few second later I received, "Take Care."

I did not expect to hear from her again that night but around forty five minutes later my phone chimed and it was her asking, "Would you ever be with a man?"

When I received the message it caught me off guard to say the least. I did reply with, "I don't know I guess I never really thought about it. I was in a threesome with a friend and his wife many years before I was even married but it was because she wanted two guys and they both trusted me. My friend and I didn't make much contact with each other than pleasuring his wife. We were the icing to her cake and we did what she asked and nothing more. What are you up to stinker? I am interested if I get you in the deal."

She simply responded with, "Just asking?" She had followed that with a smiley face.

"Call me okay. I hate texting and want to talk to you if you have time, if not that is okay too." I replied.

I did not hear back from her for quite some time. Well it was actually only about twenty minutes but in my state it seemed like hours so I texted back, "Oh gee thanks, now I will never get you off my mind, like I wanted too. Love you but I think you know that, LOL."

I did not hear back from her that night or receive a call. This woman is driving me crazy. When I got to work the following morning I texted her to let her know that I had thought about what she had said, and being with another guy, as in two guys only, would not work for me, although I don't think that is what she was implying. I know I need a woman in the mix so being in a three way with her and another guy or gal would be okay. I hoped she has a great day and that I changed my phone to vibrate so it would be quieter, because I thought she might be texting me back.

Three hours later I changed my phone back to ring because I had not heard from her and my phone is such a piece of crap that trying to feel it vibrate just doesn't cut it. I know that she sees clients at her workplace so her being able to contact me during the day might be an issue, so as much as I hated to admit it to myself, there are things in life more important than my needs, although I really didn't have to like it. I am hoping to hear from her sometime today and I work late so you never know.

While waiting for her to call though my thoughts became fantasy and I sat and pondered what she might want to do to me. She may have a girlfriend that is into everything both of us are interested in and of course my imagination took over with the following.

I arrived at her house about 6 pm and knocked hoping that no one would see me enter her house. I had parked a couple blocks away so that no one would notice my truck that lived near her. Just as I am getting started in my little fantasy my phone goes off and she texted me saying, "Sorry I was in meeting this morning. I am doing some paperwork before seeing clients." I was not surprised by that at all and told her so.

I told her that I was rewriting a story about her and me and that I would send it to her when she got off work if she wanted to see it. "Is all you do all day is write stories, just asking?"

I told her that I came in around 4 am and had my work done before everyone else got here. I can't blame her for being curious and I told her that I was an open book all she had to do was ask and I would tell her, I am not into head games. Thankfully she isn't either. Okay back to the story.

She opened the door and I am still to this day amazed at her beauty. She really hasn't changed all that much in the years that have gone past both of us. Her hair is cut different and the glasses have changed but she is still the same as I remembered her. I entered the house and she told me that things had changed somewhat from what we had discussed during our last conversation.

I cocked an eyebrow in her direction and she said, "Don't worry you will love her."

I knew that Ann like to also play with women and that didn't bother me. I was hoping for it to just be the two of us but if tonight was going to be one of her fantasies I was more than willing to be a part of it. She walked me into the living room and there was a lady about her age sitting having a drink and she was also lovely. Not as lovely as Ann, but lovely in her own right. She introduced her as Pam and we sat and got to know each other over drinks. Ann finally said that it was time to get the party started and she walked over and grabbed me by the hand and led me toward the bedroom. Once we were in there both women began to undress me slowly and I reached out to fondle Ann's breast and received a slap to my hand. "Don't worry naughty boy you will get what is coming to you when I think you have earned it, just stand there and do as you're told."

I liked where this was going and my cock began to harden at the thought of what she might be doing to me or in this case what the two of them might be planning. Once I was undressed and standing before them both stark naked she led me toward the bed and told me to just sit down and enjoy the show. Ann and Pam then began to undress each other slowly for my benefit as my hand slowly went towards my cock. "Don't even think about it." Ann snipped at me.

I moved my hands away knowing I had been caught and sat and continued to watch. Once their blouses had been removed they started to slowly slide their jeans down over their hips. I had hoped they would take off their bras but they were crafty at making me wait. When their jeans finally pooled at their feet they stepped out of them and then Ann turned her back to Pam and her bra was slowly unclasped allowing the edges of the straps to fall down. Ann held her bra up with her arms so that I still could not see her breasts. She turned to Pam and as Pam turned for her to release her bra she allowed it to fall to the floor, knowing I could still not enjoy seeing her breasts. Pam's bra fell to the floor and they both slowly turned to me giving me my first opportunity to look at their breasts. Pam's breasts were not as large as Ann's or as perky in my eyes, but they both were well endowed women.

I wanted to get up off that bed and go over and lock my lips over both of their nipples taking turns at pleasing them both but I knew that doing so would get me into trouble. I almost felt like it might be worth the risk but decided to just stay where I was for the moment and enjoy the show. While they were standing there Pam slowly reached down to Ann's hips and slowly pulled her white panties down to the floor revealing Ann's beautiful pussy to me. She kept it closely shaved and I wanted to get down on my knees and show her my appreciation. I was waiting for her to turn around so that I could see her ass and she knew it. Ann knew of my kinks and she was using them against me so far. Ann had Pam walk in front of her and she then lowered Pam's panties to the floor reveling yet another delight to me. My biggest problem was that I wanted Ann and she was what my thoughts were on even with this other woman in the room. Pam also had a closely shaved pussy and I was hoping that before the night was over I would get the opportunity to please both of them.

Little did I know at the time what they had in store for me and how much pleasure I would give and receive that evening.

My phone chimed again waking me from my dream and it was Ann. The message that followed sat me back on my heels and I felt my heart just about shatter as I read, "I am concerned that all we do is talk about sex..." I don't remember what the rest of it was about, I believe stories that I write, but it floored me to the point that I saved what I was working on and thought about shutting the computer off. We had talked last night briefly and yes it was about sex. I did answer briefly the question that she posed to me the night before and later mentioned that I was working on a story. It must have been enough for her to realize that there had to be more, and I knew it as well. I did not think it was all we talked about over the course of the last week, but when I checked my messages it had been and I knew she was right. It was not a normal conversation anymore. The problem with guys is that once you get them headed in a direction, they have a one track mind, especially when it comes to sex, and it took her telling me to pull my head out of my ass to realize it.

I sent her a text back and explained it to her hoping that she would understand and being the smart woman that she is she already knew what the problem had been and was smart enough to tell me. Most women don't do that they just stay mad at you or quit talking and then nothing gets fixed. This is one very smart lady and I have known that for years. I taught her remember and you know which ones are going to do some great things and she is one of those. I knew she would go places when the time in her life was right for it and when she hit her stride everyone better stay out of the way or she would leave them in a pile of ashes. I didn't want to be in that pile, I wanted to enjoy her and what she had to offer. I actually was not sure I would write anything for a while. I told her that this was my release and so I decided that since I needed that release I would continue, but not bring it up until she wanted to talk about it. I had other issues during that day to bring me back to the real world as well and between her kicking my butt and an issue dealing with an infant I left the computer off until later. It was time to get back to living, and I hope that someday she reads this, not just for the sex fantasies or realities in some cases, but so that she knows just how important she is to me as a woman, a smart and caring woman. I made a few notes about where the fantasy was going and shut the computer off.

It was some time before I came back to continue this but as I left it I was just at the point where both Ann and Pam were naked and standing before me. I decided after almost a week that it was time to continue my fantasy and so I began with; "Can you both turn around so I can see your cute butts?"

"You don't get to ask favors tonight Dean. Tonight is about what we want and yes some of it is what you desire but it will be on our terms, now turn around on the bed and put your ass in the air." I heard a click and saw a flash from the corner of my eye before I heard a 'swoosh' before I felt a paddle hit my ass and then another 'swoosh' before one hit from the opposite side. Both ladies had stood on either side of my ass and began to paddle me thoroughly. They both laid into my ass with only about 10 strokes each. While the strokes to my ass were not given as punishment they were given as a reminder that I was only there to serve them and I needed to remember my place. When they were finished I heard another click and the same flash. Ann was taking pictures of my ass with my phone to show me what it looked like later.