What A Night: My 1st Time Cheating

(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.

I turned left off the pathway, stepping back onto the street, but it was too late.

Gabby was standing there, smiling excitedly, her stunningly beautiful face shimmering under the sexy moonlight. My knees started to buckle, and my breath became labored. She was even more gorgeous in person than in her stunning pics.

I began to shake with worry. And I knew right there and then that I was in over my head. She had so fully expressed a desire to have an affair with me and even get pregnant repeatedly for me. My mind and heart and entire body was now raging with desire and lust.

Months worth of cunning emails, and daily hangout chats had stolen our hearts and left us hopelessly and helplessly in love. What it all meant was that the game I had been playing was not a game anymore. Our love was so very, very real.

Real people were going to get hurt unless I could end it quickly but it was far too late for that now. My mind was totally consumed with a desire to breed her.

"Johnathon, is that you?"

Her voice was velvety and rich, making the hair on my neck stand in awe.

I had to think fast if I were going to somehow end it before it began. I wondered if I might find the strength to tell her we should forget about making love and just be friends.

I smiled nervously and nodded up and down at the sound of her voice. She had the face and body of an angel, and I was so flabbergasted at her sexy shiny lips that the words I needed to say about just being friends stayed locked away in my trembling mouth.

She was suddenly on the offensive, reaching up with her glorious red painted mouth to claim her first kiss.

She arched up slightly on tippy toes so she could reach me flush on my mouth.

Our lips met, feeling like wedges of celestial honey, setting me on fire, and making us both quiver with a burst of shocking pleasure.

"Mmmm, you are a good kisser," she said, almost in a moan.

"My first time kissing a Goddess's lips," I said, my face turning red.

"And what did my lips taste like?" she asked playfully.

"They tasted sweeter than freshly picked strawberries smothered in fine Belgium chocolate."

"You're silly," she said, adding some giggles.

"Let me get you something to eat in the diner," I said softly, our glaring eyes locked together with hope and longing.

"Naww, I'd rather we just stayed outside and walked a while. My hotel is not far, the moon is out, the stars are sparkling, and we can snuggle and steal kisses to stay warm."

My heart started pounding in my chest. I could tell she was almost as smitten with me, as I was with her.

She playfully grabbed my arm and snuggled close, driving me wild as her right bullet tipped breast pressed hard against my thin jacket.

I began to shake with excitement and fear. She was too good to be true, and I could feel my heart start to pound furiously. After so long apart, it seemed as if we were really going gaga over each other.

"You're trembling," she whispered, her darling eyes suddenly serious and filled with bliss.

"I'm a little cold is all."

"Naww, you're not that cold. I really excite you, don't I?"

"I think we excite each other," I said.

"Good answer," she whispered, suddenly stepping in front of me as she planted yet another kiss on my already bliss filled lips.

A wave of ecstasy swept over my body, and my hungry cock was suddenly hard and long.

She spotted it and giggled, saying "don't grow a third leg on my account."

"You're the most beautiful and sexiest woman I have ever met or seen," I managed honestly.

"You've told me that a hundred times before, but treat me right and you'll find out just how sexy I can be," she teased, making me sweat profusely.

She suddenly toyed with me, letting her free hand reach over while allowing its fingers to run up and down the bulge in my pants, setting me ablaze.

"You're killing me," I said, panting like some love sick puppy as my toes curled with glee. Her fingers were really skilful, and I suddenly thought about how wonderful it would be if she would wrap those same fingers around my iron hard cock and turn it into a raging volcano.

She quickened her pace, causing us to walk more briskly, still skilfully rubbing her fingers along the bulge in my jeans, all the while squeezing my arm with her free hand and snuggling closer. I took it as a sign she wanted to stop the teasing and start the lovemaking. And I guessed what she was thinking. There was so much pent up desire on both our parts that we were both ready to explode like a match set to dynamite.

She suddenly began to pepper me with questions. How many kids did I really want? What names would I choose for them? What was I looking for in a lover? What was my favorite position in the bedroom? What was my greatest sex fantasy?

And then, after ten minutes or so, a large hotel, with at least ten floors, rose ominously in front of us.

"This is where I'm staying for now," Gabby said.

She gently steered my face towards her mouth with sexy red fingernails, then arched up again on anxious tippy toes. This time the kiss was longer and more forceful.

I let my arms rest on her back and hips. Then I pressed sensually hard with my mouth.

Gabby moaned slightly and started to lose control. She was the kind of woman that liked to set the stage for a spectacular lovemaking session, and right now her lips were keeping me on the ropes. She was a far greater kisser than I could ever have imagined.

"Maybe we should say goodnight right here," I said, almost pleading. But she wasn't about to let me off the hook. I could tell she was over the edge, and far too hot and bothered to turn back now.

"Don't be silly," Gabby said, playfully nodding her head back and forth. "I didn't come to Toronto just to say hi and bye. I came cause I love you so very much, and I am ready to claim your cock in my pussy.

She took my hand and nudged it under her super short skirt.

"I'm not wearing any panties," she teased.

Her words pushed me over the edge.

My love for Gabby could be supressed no longer. I looked side to side, but no one was around. The street was pitch black and deserted. A large Elm tree blocked the street lamp from illuminating where we stood, behind some bushes.

My fingers moved upward under her skirt, and my index finger gently tapped against her already quivering clit.

An explosion of extasy rolled over her in waves.

I moved Gabby between the massive Elm tree and the lane wall. We were now totally hidden in the utter darkness.

I kept up the gentle pressure against her bliss filled clit, lowering her top as my mouth began sucking on her fabulously firm breasts.

Gabby groaned her approval and was suddenly soaking wet. Her pussy was gushing with unfettered pleasure and wicked turn on.

An unexpected but earth shattering orgasm suddenly took hold of her. She shivered uncontrollably. She was in seventh heaven, taking out my cock into the cool night air as my jeans swished around my ankles.

Her fingers were tight and determined along my cock, and she turned sideways, raising one leg against the concrete wall, while rubbing the head of my cock against her already exploding pussy crack.

Waves of savage bliss now overwhelmed her, and she kept rubbing my cock along her crack for a full five minutes, moaning and teasing herself into a frenzy.

I sucked on her breasts much harder now, occasionally moving my head to smother her face and neck with heartfelt kisses.

And then it happened. My cock slipped inside of her, causing her to erupt with a second wave of orgasmic glory.

"I'm coming again," Gabby squealed, her body shivering once more as a slice of heaven carried her to the pinnacle of her amazing release.

I was soon thrusting harder, our faces red with pleasure as my warm hands squeezed her large sexy bum cheeks, keeping my steel hard cock so very deep inside of her wet tight pussy.

Our lips kept meeting again and again, our tongues swording ever so sweetly. We fucked this way for about half an hour, until she suddenly turned around, allowing my cock to slip out of her. She now wanted it from behind.

Gabby's five inch heels were eye popping sexy, only now she bent over, waving her pussy at me as if daring me to enter it from behind. She knew it would be far too sweet for me to hold out for much longer in that glorious position.

She wanted me to go deep inside from behind so she could trap my swollen cock in her pussy and milk it quickly for spoonfuls of warm sweet cum.

I did her bidding, sticking my cock deep inside of her while grabbing her large sexy ass cheeks.

I pounded away, grunting as the pressure on my pleasure filled cock was beginning to build.

I used one hand to reach around her sides and toy with her dangling breasts. That really made Gabby hotter and she squealed with delight.

She playfully brought her long silky smooth legs closer together, tightening her pussy grip on my trapped thrusting cock.

A surge of mounting sweetness enveloped my cock. Her fabulous tightness had pulled the trigger in my balls. I was going to cum and there was no way to stop it.

"I'm cumming," I yelped, feeling my body start to shiver as wave after wave of bliss swept over me.

My words turned Gabby on like crazy, and she also felt a third surge of orgasmic glory began to build.

I'm cumming too," she squealed,

"Should I pullout?" I then asked, knowing we hadn't discussed how soon she wanted to get knocked up.

"Don't you dare," she squealed, knowing it was far too sweet for both of us to even think about pulling out now.

"Stay inside," Gabby added, reaching behind herself so she could sensually dig her nails into my pumping thighs. She was forcing me to stay in place.