What A Night: My 1st Time Cheating by Handymanblues,Handymanblues

(This is a true story, and happened to me just last week. My first time cheating on my wife, and despite my revulsion at my despicable actions, it probably won’t be my last…)

December 28, 2021 – In Toronto, Canada — Late in the evening…

I glanced at the old wooden clock above the fridge. It ticked loudly and seductively. And yet it was the only sound to reverberate throughout the entire house. Not even the usual midnight chirping of any pesky horny crickets could be heard.

I sighed happily at the thought. It meant that my wife Debbie was sound asleep. She always had me bring her a glass of warm milk whenever she went to bed, only tonight I had spiked it with a sleeping pill. Add that to the fact that she was a very heavy sleeper, and I knew she would never wake to find me missing.

I carefully crept to the bottom of the stairs and smiled broadly as the sound of her snoring began in earnest. She had indeed drifted off and would not awaken until her alarm clock sounded some eight hours from now.

I took a swig of mouthwash and let it saturate my gums for about a minute before spitting it out in the sink. Then I combed my freshly cut hair over the growing bald spot until it was hidden.

I sucked in my gut until the loose shirt hid my unflattering girth. Next I slipped into my new expensive Nikes and gave my face a generous splash of Eternity for Men. I wanted to smell really good for the woman of my dreams, Gabby. Tonight would be my first time meeting her.

I crept gingerly to the back door and took a deep breath. I had never really cheated on Debbie before, and a twinge of guilt began to play around the edges of my weary, desperate mind. ‘Cheating’ was a relative term. Did flirting count? Did sex-free dating count? Did mere kisses count? Did emotional attachment count?

A light sweat began to form over my eyebrows, and I found myself breathing heavier than usual. Just what line did I have to cross to be an actual cheater? And more importantly, just what lines would I be crossing tonight?

My hand remained firmly on the shiny brass doorknob, although I hadn’t yet pushed open the door. I was suddenly bathed in fear. Gabby and I had been exchanging online chats and emails for just over six months, and yet, tonight would be our first time actually meeting in person. I had told Gabby about being married, but she would only say she loved me regardless. I had also told her I’d never had any children, but in actual fact, would love one day to have about six kids, three boys and three girls. Gabby seemed to be perfectly fine with becoming my baby making machine, and the thought made me unbearably hot and bothered.

I had spent the last few years of my life married without sex!!!! But things were about to change. Gabby had told me she loved me and would most assuredly give me not only lots of sex but lots of babies as well.

Still, I was afraid to cheat on Debbie, and needed some extra courage to meet with Gabby, the woman of my dreams.

The fear caused a panic attack to take hold of me. If I did actually step through that door, there would be no going back. Meeting the world’s most beautiful sex Goddess, and sweet talking her under the stars, would no doubt cause both our hearts to draw closer.

Still, I wasn’t willing to leave my wife. It made me wonder if tangling up my heart with Gabby’s in some blossoming relationship could only end in disaster.

I had asked that Gabby meet me at midnight at the all night diner on Maple Avenue.

I had made such late night plans because I knew that sneaking out on Debbie while she was awake, would not be easy. And I figured that someone I knew might spot me with a strange woman in daylight, and rat me out to my unsuspecting wife. So I had to sneak out very late.

I also knew from experience that the diner was usually fairly deserted after eleven, and had corner booths that were somewhat dark and secluded. I was confident that no one would be around that could recognize me.

But time was flying by, and if I was going to meet the love of my life, then I was going to have to leave now to meet her on time.

I pushed the door wide open and felt a blast of exhilarating breeze, but my legs wouldn’t move. As excited as I was, and as incredibly horny as I was, my conscience was absolutely killing me. It was one thing to become emotionally attached to a woman other than my wife, but it was another to actually meet her in person, and no doubt end up kissing her and doing at least some ‘touchy feely.’

I sighed at the thought. Just how much touchy feely would Gabby desire or allow? And wouldn’t that, over time, lead to the two of us falling even deeper in love?

I rolled my eyes up at the brilliant stars and cursed the day I was born. Just what the fuck was I getting myself into? I had a stiff cock, and balls full of fertile sperm, but not even so much as one single condom. What kind of result would I receive by getting so close to such an amazing dream girl? The truth was that Gabby was probably going to encourage me to make super sweet love to her, probably even hold me close to ensure I shot it out deep inside of her.

But what if my wife Debbie was to ever find out? She a very sensitive and thoughtful woman. Although we hadn’t had sex in years, she totally trusted me. If I dared go ahead and cheat on her, she might find out and be totally devastated. Three years ago, a medical condition had caused her to have an operation that prevented her from being intimate with me.

Still, despite lingering loyalties toward Debbie, my love for the stunning Goddess Gabby was far too strong to turn back now.

With the back door held wide open, the cool fall air was starting to wrap around my neck. I raised my jacket collar. The afternoon had been sunny, but this evening was nippy and chilled.

My brain began to churn in earnest. If I held the damn door open any longer, then the furnace would come on. That in itself might stir my wife in her bed. Not only was the furnace extra loud whenever it kicked in, but, being the fall, we had lowered the temperature gauge. If she did awake, she would surely get suspicious with me missing, and the furnace blaring, and start to search the house for me.

I therefore finally stepped outside and closed the door tightly behind me, listening for the sound of its automatic lock.

I had already made sure the outside light was turned off. I didn’t want some nosy neighbor to see me leaving just before midnight by the back door. If just one of them were to casually mention it to Debbie, then I would surely be busted. But as things were, the backyard was pitch black and no one was around. I prayed it would be that way when I would return later.

I stepped on the swirling, crispy leaves carefully, trying not to noisily rustle the strewn autumn colors of brown, red, and yellow.

In no time I was under the cover of giant waving Oak trees, hustling along the quiet street like some unseen thief in the night.

I glanced at my Rolex. Ten minutes to twelve.

A twinge of guilt suddenly took hold. Debbie had bought the fancy watch new for my sixtieth birthday, just last year. The six grand had used up most of her life savings. And yet, here I was prowling the streets like some unappreciative fucking bandit, looking to steal some love from one of the world’s most sexiest women. I was good looking, but not a Brad Pitt look a like. It surprised me that Gabby had fallen so hard for me. But then again, fate worked in mysterious ways.

The street lights were now in abundance, and the waving Oak trees far behind me. There was no one around except for the odd passing car and a hungry racoon searching for some grub in the cans by the side of the road.

“Shit.” I muttered the word because it dawned on me that in all the excitement I had forgotten to take out the garbage. I sighed at the thought. Still, I couldn’t worry about that now. Just five minutes away was the most beautiful woman I had ever seen. My darling Gabby!!!!!!

The many pics and vids she had sent to me were absolutely amazing.

Gabby had such silky black hair, which looked amazing no matter what color she dyed it. And she had this intricate way of weaving it into seductive braids, showcasing sweetly sculpted cheeks and breathtaking thick shiny lips. But it was her eyes that I found most alluring, so sensually dovish and hypnotic. She also had such fabulous lashes and could paint a heavenly picture with sexy mascara that made my heart leap with each glance.

She had also sent me some bikini shots, and I salivated as the images toyed with my vulnerable mind. A slender sexy neck…and smooth gorgeous shoulders…large firm breasts with giant nipples that pushed hard against the thin stretchy top…a tiny waist, flowing into wide succulent hips and deliciously large, well rounded bum cheeks that would make any male tongue dangle on the ground…and her legs, so long and silky smooth…with five inch heels to make me pant like the mangy dog I was.

I crossed the street and there it was, a mere two blocks away, the flashing neon sign, heralding the fact that an all night diner was ready and waiting to feed any late night fun seekers.

I kept my head down and my legs moving faster, fueled by the off chance that someone who knew me might be driving by and spot me. But there were no cars and no other people out for a walk.

I turned onto the pathway that led to the diner and stopped at the large glass double doors. I suddenly began to have real second thoughts. Getting closer to Gabby when my heart was already so much in love with her could one day badly break both our hearts. And cheating on Debbie could ruin her life as well.

I sighed at the unexpected bout of repentance, suddenly wishing I had not left my house in the first place. A wave of searing panic suddenly swept over me. Just what the fuck was I doing?

I resisted reaching for the handle of the large glass door, and instead suddenly chickened out, turning around and moving swiftly down the pathway leading back to the street.

I was suddenly determined to get the fuck home without making things any worse than they were.

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