I met Dorothy at a community meeting to discuss zoning proposals in our neighborhood. I recognized her as the elderly neighbor who lived behind us, but we had never been formally introduced or spoken to each other. We made small talk about the issues being discussed, how nice the neighborhood was, and so on.
I'm 41. Dorothy was older. Much older. She mentioned that both she and her husband were retired but didn't get out much anymore due to health concerns.
My wife wasn't interested in attending these meetings, hence her absence. When I inquired about Dorothy's husband, she then revealed to me that he was in the end stages of Alzheimer's disease and she was his primary caretaker. He was 76, and she then implied her own age in a statement about him being almost a decade older than her. I put her age between 65 and 66.
I didn't find her sexually attractive, but I could tell that in her younger years she was probably a stone cold fox of a lady. She was still slender, petite, and had bright silver hair that was straight and shoulder length. She still dressed professionally - at least for this meeting she did. She wore a soft gray jacket and dress and a white blouse.
She talked about her husband, and how hard it was caring for him at her age. She was sharp as a tack mentally, very well spoke, and quite humorous. More like sarcastic. She started becoming a little more "forward" with her comments, almost to the point of inappropriateness.
"When you have a sick spouse, the first thing you lose is your sex life. Hell, with him on a catheter now, I can't even suck his beautiful cock anymore." She glanced at me and raised her eyebrow, causing her forehead to wrinkle even more. "He doesn't have to know who he is, where he is, or who I am for that matter for me to enjoy giving him a good blowjob, right?"
I grinned despite the shock of the candor she was exhibiting. Then I tempted fate and pushed the envelope a little farther. Kidding around with this nasty granny might be fun.
"Well," I replied, "my wife hates giving blowjobs. Always has. So I guess I'd just not know the name of who wasn't satisfying me if the roles were reversed."
She told me she knew who my wife was. She became even more forward when she told me that my wife reminded her of a lesbian lover she had in her youth, and if she were a bit younger she'd have to hold herself back from propositioning my wife for one last lesbian fling. This older woman was definitely full of surprises.
In for a penny, in for a pound - so the saying goes. I was feeling feisty, so I wanted to see if I could shock her.
"I've been meaning to ask you, I need to make repairs on the fence between our properties. Do you mind if I replace some of the pickets and posts?" I asked. She told me she didn't mind at all.
"Well," I leaned over and whispered, "I'm going to put one picket in the fence that's directly behind my shed. It's going to have a hole in it about waist high to me. On the first Wednesday of every month, I could, if you'd like, stick my cock through the hole and let you give that blowjob you've been longing to give. That would make us both happy, right?"
I leaned back and half expected her to scream in shock and disgust. She looked at me with no reaction, then leaned over to me and whispered in response, "What time?"
"How about midnight?" I answered.
"Make it 1:00am? I'm a night owl," was her counter proposal.
"I can do that," I finally replied in a somewhat shocked state. She had called my bluff.
She leaned over and made one more statement. "There are a couple of conditions."
I leaned back and whispered in her ear, "Name them."
Her eyes met mine and she said, "First, no one ever knows. Second, I want to taste your pretty wife's pussy on your cock every once in a while." Then she told me how she'd respond when she could tell she could taste my wife on me. Again, I grinned at her lewdness.
I kept my gaze toward her, and without hesitating whispered, "Deal." I shocked myself by saying it.
She started to get up to leave, leaned over to me, and whispered, "The beginning of September is in about a week. You better get started mending that fence tomorrow."
I grinned once again. But she wasn't finished...
"Don't turn chicken shit on me and fail to show up. When I offer a man a blowjob, I don't bullshit around, young man. You'll get my best efforts. You just make damn sure you bring your best load of sperm to give me. I'm very thirsty, so to speak. It's been way too long..."
"I'll knock twice when I'm ready to stick it through for you, and three times just before you get your drink."
Holy. Fuck. Needless to say, the fence was repaired in the next three days. Hidden from plain sight, behind my shed, was a single picket with a good sized hole drilled in it with at doorknob installation drill bit - plenty large enough to slip my cock through with some space to spare. The following day after repairs were complete, I noticed a lawn chair had been moved against the fence on her side immediately below the hole.
The scene was set. Now all I had to do was wait, and hopefully not turn chicken shit.
* * *
It was finally the first Wednesday of the month. It was September. That night, the kids were in bed and my wife and I had just made love. I easily brought her to orgasm, but I withheld mine from her. I lied, saying I was tired and didn't believe I would be able to cum. The anticipation and excitement of what was to come made it even more difficult to do so. My prostate felt like a burning, red-hot coal deep in my groin. I needed sexual release desperately.
My wife had rolled over and drifted off into a restful slumber. The clock showed 11:30pm, then 12:30am, and finally 12:57am as I continued glancing over at it.
It was time.
I arose from bed, still nude from our lovemaking session, and silently padded to the back door on the other side of the house. Once outside on the back porch, I slipped the flip-flops on my feet that sat just outside the door and walked out into my yard and circled behind my storage shed. It was a moonless night, yet cloudless, and the stars were brilliantly bright. The air was just slightly cool against my naked skin.
Obscured by my shed and the surrounding fence corner, I stood in front of the waist-high, make-shift glory hole that I had drilled out of the wooden picket. My cock was rock hard and erect, but I was nervous with anticipation. I had pretty much convinced myself that Dorothy was just bullshitting me and fueling this young man's fantasies. I would soon see for sure.
I knocked softly on the fence twice. There was no response. Damn. I knocked twice again, much more loudly this time. About five seconds later the knocks were returned. I was shocked. I inhaled deeply, summoned up my boldness, and stepped toward the fence. I was so hard that I had to push my cock downward to point toward the hole in the fence, but I did. I stepped forward and aimed it through the entrance, pressing my entire body against the fence.
The contrast between the sensation of my pelvis pressed against the wooden fence and the cool night air of my cock sticking through the other side was fascinating. My cock didn't have to endure the open air for long. To my delight, I felt a warm, wet mouth envelop the head of my cock and a tongue gently start to lick my frenulum. The tongue then began circling the head of my cock and flicking its piss slit. It twitched in response. I felt a surge of precum course through its length and I knew her tongue was getting a generous taste of its sweetness.
She didn't engulf its length with her mouth at first. She took long, slow licks of the shaft starting at its base and working her way toward the tip. Then she momentarily paused. I felt her face close to it, as if she was smelling it. Then she placed three quick kisses on the tip.