A Dilemma


Caution: This True Sex Story contains strong sexual content, including Ma/Fa, Consensual, Heterosexual, True Story, Oral Sex, Squirting, Big Breasts, .

Desc: True Sex Story: A mostly true story of an event that happened recently. Sadly the best part never happened, hence the dilemma and ethics. My first submission and additional chapters may be coming.

Many thanks go to aerosick for the valuable editing help

****Authors Note: This is a true story, names have been changed, it is also my first attempt and hopefully will be therapeutic and excise some demons.****

This story is full of cliches, but they are important to the story. I am a 57 y/o male, graying, 35lbs over weight, 6’3”, and average in the male appendage area. I was never really good with the ladies, I either took things the wrong way or just flat missed the signals.

I have been married for 34 years to the same woman, and in that time I have never strayed, but I am not 100% sure about her. A few signs but no proof. Mind you I have looked and looked a lot. I’m old not dead.

I am the kind of person who will do anything for anyone, even at my own expense. And when I am in the same bed I would rather my partner get off even if I don’t. I love to eat pussy and I have been known to do so for hours. Once they beg me to stop I go back for a few more.

I was a contractor for most of my life until a freak accident left me with a very screwed up back. 3 years later I was in a car wreck that popped two disks in my neck and the doctors refused to operate on them, telling me that I can’t go back to my job and to have a nice life. This was 15 years into my marriage.

Everything I had worked most of my life to build up came crashing down. That really fucked with my head. No more being a productive citizen, no more providing for my family, it just ate and ate at me but it was nothing compared to what would happen years later. For the last 5 years there has been no sex in my marriage at all. Zip, nada. Not even so much as a fuck you. Yes, I tried everything I could. Nothing. She would not even talk about it so I had no clue what the problem was. I suspected many things again but had no proof.

Now that really fucks with your head, self doubt, pity, feeling inadequate, things stop working, again the doctors said I was depressed ( ya think?) and put me on meds for that, then things really did not work. Erection, what’s that? So pills for that. Nope. More mind fucking. I could briefly get it up, but it would only last for minutes then, droop.

Anyway after my back I spent almost four months in bed, not getting up once and when I did it took many years before I could do even simple things like carry in groceries or even drive, and even more time before doing more strenuous things like mowing the lawn and things of that nature. It was a very slow process.

Many years later some friends of mine Kelly and Sam - Kelly was a walking wet dream and Sam was an old pot head - worked for a local radio station doing a summer long giveaway promotion at a local place similar to BW3’s, where once a week for 12 weeks they would register 10 people for the final drawing to be held in early September. I believe the prize was a Harley, but the point was to get people out and for them to eat and drink spending lots of money and hope they get registered.

So by mid July it was a typical southern summer evening still 85 degrees at 9pm and 1000% humidity, anyway this night I was already registered so I was just hanging with Kelly and Sam and this night we had small water guns dipping them in a cooler of ice water and a good time was had by all.

I was walking around squirting some of the regulars getting a few in the back causing lots of squeals and thanks for the cool shot. Then I missed my target and hit a small girl in the back as her mom was holding her. I got a very dirty look from mom but the girl wanted more. I went and apologized to mom and told her later we would be filling them with tequila and she informed me that they did not drink at their house. Oooookay. As I was on my way back to refill my son said “ I see you met Hanna”. So that was Hanna. I had heard about her from my son and some of their mutual friends, but I don’t normally believe all I hear. Hanna was rather striking, about 5’9” 130 lbs, very nice breasts around 38D, flat stomach and very nice hips. Quite an attractive package, a body like Raquel Welch. That’s close.

It was weeks later when I saw Hanna again when she came to our house to swim in the pool. I was already well on my way to a good buzz and when Hanna and her daughter got there they were sitting on the back porch eating a bite before getting in. Hanna had on a t-shirt and a pair of very short gray shorts, and when a pool toy went errant she reached way over to her left to retrieve it and BAM! No underwear and I am looking right up at her pussy, instant woody. So Hanna goes in and changes into a nice bikini, this woman was classic MILF. I could not keep my eyes off her and got close every chance I could. I guess you could say I was interested in knowing her better, to see if the stories were true. LOL.

She would come to the pool from time to time and as it was always a party a good time was had by all, but because of the children we kept it under control. Every time she was there I would get as close as I could as often as I could. I learned that Hanna had a “small” enhancement to her breasts and some slight work on her nose when she was around 30, now being 37. I have always stated that I don’t like fake tits, but after much thought realized I have never felt any fake ones so with the exception of the ones that were so grotesque I would keep an open mind until I gave some a feel.

So the last pool party before shutting it down for the season Hanna actually had a few drinks. She was really into it with her husband who was the real tee-toataler in the family. She was quite funny and really opened up, even straddling another guy in the pool and whipping out her tits for him to see. Lucky bastard! Later she was standing on the ladder and I came up beside her and AGAIN there was her pussy, this time her suit was bunched towards the middle and it was staring me in the face. Man I wanted to dive in, but instead lightly blew on it and watched her lightly shiver and her pussy lips slightly open wanting more. I was in lust, maybe love and decided right then that my face was going to get in there. Just not sure how yet.

Around this time Hanna and I started texting each other, starting slow but it got to the point that we texted quite a lot during the day, I would tell her good morning, ask how her day was, and talk about anything and everything. I knew the problems she was having with her husband and she knew about mine and more importantly my lack of sex. My wife and I were just roommates at this point.

Well we were tailgating a few months later in late October, and I finally got to meet the husband, ass man. She called him this because his truck smelled like ass, this coming from not using toilet paper and not washing his ass. He’s very weird. Anyway she asked if I could come by and look at the deck on the back of their house to see what could be done with it. They were afraid to get on it and the way their house sat it was the only place her daughter could play.

With as my background was as a contractor I agreed to come look at it. It was on the second floor, 12 X 14 and was rotting away. Most of the decking was shot as were many of the joists, so I worked up the materials cost for her. Then came the question I was dreading: can you build it? With the problems with my back and neck I was very unsure and told her so, offering to supervise.

A few weeks later at another game, while tailgating she poured it on. Told me she would help, so would her brother(s) and her husband but not much there with him. I lined up another guy and reluctantly I agreed to help her, and she asked what I would charge for labor. I told her I could not charge a friend who badly needed the work done. Water, Gatorade and some beer would do. Deal.

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