A Dilemma
Chapter 1

Copyright© 2016 by olddroopy

True Sex Story: Chapter 1 - 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.

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

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.

As it was getting close to winter we decided to start next spring. Oops, Hanna gets pregnant. Yep one of those “accidents”. They hardly had sex according to her and this once on their anniversary had consequences. Well the next year comes around she has the baby and asks if the deck was still on, and on top of that wanted to make it bigger! With that came longer and bigger joists and more weight to lug around. To top everything off from the original deal: no help. No Hanna, no brothers, the other guy I had was busy. Left me and the hubby. He was worthless. So I embarked on building this massive 30 X 18 deck with 2X2 pickets and 2 X 6 top cap with a gate and a band around the top for hanging stuff, plus reworking the siding on the whole back of the house. I went home every day hurting so bad it was almost unbearable. But as I said earlier; I keep my promises and do it even at my own expense. It took me 6 weeks but I got it done.

One day she asked me to give her a hand with something inside so in I go, hey nothing wrong with a break. So I go in and she’s sitting there with this pump contraption on pumping her breast milk. Now I have no problem with breast feeding as it’s the best and most natural way of feeding a baby, and I told her that it was a good look for her. I went to get something for her and when I came back she was taking the pump off. Ok, now we are talking tits. YES! Very, very nice.

The very next day she told me that with the problems she and her hubby were having that he ignores her and had even before she got pregnant this time. She and had taken some tasteful naked pics and sent them to her ex to ask if he thought there was anything wrong with her body. Of course hubby found out a had a fit, Hanna asked me what I thought. I had an immediate answer but decided to try something; I told her before I could make that determination I would need to see the pics, and she said I could look but could not have a copy. I’ll take what I can get.

The next week she told me that she could not find them, her hubby must have deleted them, I told her not to worry. I know I would have liked them, I liked what I was seeing now even after having the baby. So work continues and we talk. This pregnancy has really taken its toll on her, both physically and mentally. Really feeling unattractive, and unwanted, said her “junk” was falling out, worrying about the baby as this is a late in life child. I was doing my best to lift her spirits and she would always claim it was alright this was how things were supposed to be, all bull. So every Monday I started adding to my text wishing her a “Happy MILF Monday” she found it hard to believe I felt that way, even passing a comment about all the old guys that hit on her. Ouch.

So as I was winding down the project she was so delighted that she had a big new safe deck that could be used, but she also seemed to be getting more down at the same time. So the kitchen window at the sink looks right out onto the deck and as I was finishing up the siding and tidying up I noticed her standing at the sink looking out. I waved to her and she gave a small smile and I looked closer and swear I saw a tear running down her cheek.

So I stepped in the sliding glass door to get some water and asked her if she was alright, and her usual response was it will be alright was given. Bullshit. That was the final straw for me.

I walked up behind her and put my hands on her shoulders and slowly ran my hands down her arms until I reached her hands, her arms were straight down her side. I put my chin on her shoulder and took in her smell; absolutely wonderful. I very softly told her that I was going to make love to her using my eyes, my lips, my tongue and my fingers. I promised that I would stay dressed.

So I lifted her left hand and brought it to my lips and kissed it, and then lowered it down lightly holding it in place as I raised the right one and kissed it as well, then lowered it back and held it as well. I then started kissing and nibbling on her neck and ears producing a small moan and a slight shudder from her body. While continuing to do this I slowly moved my hands up her sides going up and down a few times, she whimpered and softly said please, as I had been avoiding her breasts.

Finally I move up one last time and cupped her breasts and she moaned louder and leaned back into me. Fuck she had very nice breasts. So I very gently massaged and fondled them from behind and then I had to see them. So I reached down to the hem of her shirt and lifted it up, and as she raised her arms I stopped the shirt right at her face, that is when I started kissing and licking my way down her back causing an even louder moan. I knelt down behind her and put my hands on her hip and grabbed the waistband of her pants and slowly pulled them and her panties down. When her ass was exposed I just had to kiss and squeeze it. What an fine ass! So I moved her shorts and panties on down licking and kissing the backs of her legs along the way, and when they reached the floor I lifted one leg for her and removed the pants, then did the same for the other.

I grabbed her hips and turned her around and there was her pussy right in front of me and I planted a very soft kiss just above it.

I backed her up until her butt hit the counter and I lifted her up on the edge. I moved to her breasts and licked and nibbled on them going back and forth, licking the undersides, lightly biting the nipples. Slowly I worked my way down and the aroma that was hitting my nose was heaven sent. As I moved farther there in all of it in it’s wonderful glory was her pussy, her tight lips already open in anticipation, moisture already starting to drip. I took in the view and the aroma, damn if I was not in love. I blew softly and her lips opened and closed in reaction; she let out a growl and had her first orgasm. It brought a smile to my face and a patter to my heart. I moved in and started with soft kisses on her lips and clit, moving to her thighs I lightly kissed my way down her left leg, with a few extra kisses and licks behind the knee, and when I reached the bottom I worked my way up the right side doing the same thing.

As I got near the sweet spot I put my hands under her fine ass and lifted so I could get my tongue in there and test the waters. I kissed and licked all around her ass and she had another orgasm and I worked my way back front, kissing and licking her taint, her juices flowing freely. Now already down to there, I moved to the juncture of where her legs meet the groin area. By this time she was moaning and squirming all over, panting in anticipation. After one more very light kiss just above her clit I moved and starting at the bottom of her slit I slowly licked from bottom to the top not touching her clit, she about jumped off the counter. I repeated this a few more times and then started tongue fucking her some, and when it started getting numb I was everywhere; wanting to kiss and lick every place she had. Again and again, and again.

And that is just what I did. Not staying in one place for long, always moving and doing something different. At this point Hanna was in a constant orgasm and was begging me to stop and give her a break, so I went up and paid more homage to her breasts, and just when she thought I was finished I quickly swooped down and sucked her clit into my mouth, sucking hard and lashing at the end with my tongue at the same time, it sent her way over the edge and she squirted and almost fell off the counter as she blacked out.

She came to enough so I helped her to her bedroom and laid her down and after one final light kiss on her pussy, I covered her up and kissed her forehead. She was out.

Is this true? Can I be for real? No and yes. The sex part is all from my head but I truly believe she needed ( needs ) something like this for her morale. Would I do it like this and leave? Yes. Why did I not? Those pesky morals and vows.

I would like to know if I did this does my stuff still work, would it stay up during this? I don’t know, and I may never know, as sadly Hanna stopped talking to me. Texted me one day and said she was to busy to talk. OK. I let her have her space, I had been pushing pretty hard. She knew how I felt, but I never went over the line, those morals again.

Anyway it was two weeks before I heard from her and she asked how I was, and I replied “ Hey Stranger” and she said “I did not mean to be” and it was three more weeks before I heard from her again when she said she was going to the movies and some FAMILY time. Ouch!. Ok again. Nothing since. It has been almost two months now and I am still not over it, and still want to get my face in there as I told myself I would in the pool that fateful day.

I miss our talks, I miss seeing her. I think about her daily. I thought we were friends, but once my intentions were known, I guess the thought was just to repulsive for her.

When this gets posted should I send her a link?

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