I made a post on TikTok and some random guy named “Asphalt Cowboy” commented on my post by poking fun at my video. Needless to say, it pissed me off. So, I wrote him back, “Oh, you’re some big shit because you can drive a semi?”
‘Who the fuck is this guy anyway?’
He didn’t stop, “Everyone knows that women drivers suck,” he wrote back under my video.
It became a game at first, to see who could insult the other one more. Then one night I posted a video of me making lasagna from scratch. He commented on that video, “Anyone can order take out!”
I posted back my phone number and said, “The first person to call me, I will personally cook for them.”
My phone rang seconds later and on the other end was John, AKA Asphalt Cowboy. More phone calls turned into flirting chats about sex.
Then John would text me in the morning and he would call me every night after I was in bed. We would talk about our days. Sometimes the phone calls would turn into a sexy time. When John talked dirty to me, my body would react.
He would say, “Sweetheart, touch yourself for me, let me hear you.” He then said, “I love you, baby,” after a very hot and steamy phone sex conversation.
One month after we started talking, I responded, “Do you?”
Which he responded, “I never lie, Wendy.”
In truth, I loved him too, but I wasn’t ready to give my heart away, not just yet.
What could this relationship do for either of us? Long-distance love affairs often sound romantic, but that same distance often kills any chance of truly being together. I lived in Michigan and he was a cattle hauler out of Wyoming. Everything else was perfect.
We had so many video chat conversations over the last ten months, so I felt like I could trust John completely. Any woman would consider themselves lucky to have his attention.
John is in his early sixties, six foot four inches, with a muscular build, deep green eyes, gray hair and beard with lots of tattoos. Oh, did I mention, he drives a Harley when he’s not working?
His voice was what got me going. It was both deep and soft at the same time and when he said, “Good morning, sweetheart,” that always made me smile. I’m a sucker for a man with a sexy voice.
We enjoyed each other when we could. We were not overthinking or over-demanding on each other’s lives. We kept it sexy and light, most of the time.
Then one morning, I told John about some vacation time I had coming up in April and that I wasn’t sure what to do with it.
He said, “Wendy, I could manage to be close to Las Vegas if you want to fly out there to see me?”
I was very hesitant at first, yet I knew I was sexually attracted to him. I knew he wanted me too, but nothing is that simple in reality.
‘Am I going to do this? Go have sex with a man I met on TikTok?’
Before I booked my flight, we talked for hours about what each of us wanted. We agreed to meet, have sex, with no promises of more than one weekend together. No love, just sex. We had to scratch that itch and we both knew it. We made a verbal agreement between us for one weekend and nothing was promised after that.
We picked out a weekend, at the end of April and I booked my flight arrangements.
John wanted this to be an amazing grand adventure so he did most of the coordinating, keeping me in the dark about everything. He would be arriving a day in advance.
If you looked at John you wouldn’t think he’s such a soft, romantic, man, as he was not someone to fuck with. To his soul, he’s a lone wolf. Being a truck driver was a lonely existence to bear. He had also warned me about his possessive nature.
John would check into the room and then he would text me the name of the casino and room number when my plane touched down.
I had counted down the days since March. Finally, it was the weekend to be with John. I was waiting at the airport, sitting at Gate 22, my flight from Flint to Las Vegas would be boarding soon.
I got a text from John, “I can’t wait to taste your pussy!” He sent me a dick pic to show me how excited he was. I’m was grinning and blushing at the same time as I thought, ‘Fuck me, he does have a magnificent cock!’
They called to board and I knew there was no turning back. I was sitting on a plane, flying three thousand miles, to have sex with John. This was crazy, but I was so excited and thrilled as I had never done anything like this before and I just hope I don’t end up like the cattle.
My flight landed on time, 9:00 pm. My phone buzzed minutes later with a text message from John, “Hello, sweetheart, I can’t wait to smash you! We are staying at the MGM Grand, room 0514. Look for the MGM limousine outside the arrivals exit. They are waiting for you. Special VIP treatment for my woman!”
I laughed at the text message, but that was John, always making me laugh.
The limo was a great surprise and I felt like a celebrity. Ok, two can play at this game so quickly I made a stop to use the restroom and I snapped a picture of one of my tits. I sent it to him saying, “I want you to suck me until they bleed.”
A few seconds later he texts back, “Send some more!! I’m dying here.”
True to his word, the limo was right out front. The driver was sharply dressed in an all-black suit. He smiled and opened the door for me. My heart was beating fast and my mouth was suddenly so dry.
I was getting nervous and I needed to pull myself together.
I wanted to give the impression that I was in complete control. No love, no commitments, no strings. One weekend together and then we would go back to our lives, that was the plan, right?
The ride from the airport to the casino took about thirty minutes. I was feeling sexy and I put the phone under my skirt and snapped a picture of my blue panties, his favorite color. I hit send and within seconds he sent back a picture of himself licking the phone. I burst out laughing, but I was getting so turned on as well.
He sent another text, “Fuck it, I’m meeting you in the lobby!”
I texted back, “NO, NO, STICK TO THE PLAN, ASPHALT COWBOY!”
He responded with, “Babe, you better be here soon or I’m coming to get you and I’ll throw you over my shoulder, carrying you up to the room!”
“I’m here,” I texted back as the limo was pulling into the casino parking area.
The limo driver stopped at the entrance of the casino. As the car door opened, I knew I was sure now, no more worries, I want this to happen.
I made my way through the busy lobby, my heart was racing. I followed the signs to the elevators and pushed the fifth-floor button. The elevator whisked me up and within moments I was standing in front of room 0514.
One more deep breath and I softly knocked on the door. Seconds later, the door opened and we saw each other face to face.
“Hello, John,” I said and I was smiling.
“Hello, sweetheart, you’re such a dick tease!”
“Am I, John?”
He took my hand and pulled me inside the room. He was holding my hands above my head, his body nailed me against the door as his lips caressed my neck.
Then he whispered, “You’re wearing my favorite color of panties, are you my naughty little fuck toy?”
A shiver moved down my spine and he covered my answer with his mouth, full tongue, French-style a deep, toe-curling kiss.
He moaned and it had only been five seconds in person and I felt my panties were getting damp. I had no time to think and I felt his large calloused hands unbutton my blouse, skimming his hands under my bra.
John caressed my right nipple, he felt the nipple piercing I never told him about.
“You bad girl!”
His other hand was gliding underneath my skirt. The palm of his hand grazed against the silk panties until his hand clenched my trimmed mound.
He unsnapped my bra with one hand and tossed it to the floor as his mouth locked on my nipple. He sucked on the nipple ring and pulled it with his teeth. He was nipping and biting, washing it with his tongue and I was murmuring. My pussy clenched every time he sucked me.
His mouth was going everywhere so quickly. He stopped suddenly and said, “Before we go any further Wendy, tell me you want me.”
My mouth was so dry I could barely speak, “I want you.”
“No Wendy, I want you to say my name. The name you’ll be screaming, as I force you to come over and over again.”
Our eyes locked as I said, “I want you, John.”
Then, his fingers slid inside me, I was so wet. His breathing changed as he got worked up.
I was standing against the door, partially naked, as he pulled his fingers out of my pussy and smelt them. His eyes closed, “Damn, I knew you would smell like heaven.” He licked them clean and then he took my hand and lead me to the bed.
“John, it’s my turn, please undress and lay down on the bed.”
“I don’t think so, baby. I’m driving the truck tonight.”
We stared each other down and I put my leg on the bed. As I reached down between my legs, I started fingering my pussy, groaning as I rubbed my swollen clit.
“You want this, don’t you, Tiger?”
“Yes,” he said almost growling.
“Then undress, and do as I say.”
It made him crazy, but he was enjoying me taunting him. Slowly, I started peeling the rest of my clothes off. The room was dark, cool and candles flickered, giving the scent of honeysuckle. As I pushed my black skirt and silk panties down my legs to the floor, my eyes were pointed at John.
Then, I stood in front of John completely naked, his dark hazel eyes stared at me.
“You want me, baby?” I asked him.
He shook his head, “Yes.”
“You want me to put my panties in your mouth, don’t you?”
“Yes please, baby.”
Slowly, I moved between his hairy legs, my large DD breast brushed against his hairy chest.
“Open your mouth for Mistress Contessa.”
His mouth opened as I pushed the panties inside. Poor John, didn’t know that I had a dark side but he was going to find out very quickly.
He grabbed my ass and tried to pull me on top of him. I pushed him down on the bed and his cock was stiff and at full attention.
“Now, Tiger, I’m going to ask you to please keep your hands to yourself.”
My panties were still in his mouth, so he shook his head no.
“Does Mistress Contessa need to get the rope?”
His head went up and down.
Inside my suitcase was a goodie bag of recreational and pain-inducing toys. John was way too big to tie down, so I just tied his hands together in front of him, but not too tightly. Now it was my turn to play.
“John, have you ever been the one to be teased, and made to cum, over and over?”
His eyes were bugging out, and he was sweating.
“Did I forget to mention John, that I enjoy BDSM?”
His head bobbed up and down.
“John, do you know what a cock ring is? Do you know what they’re used for? I know you do.”
“Do you know what else I have for you baby? Nipple clips! I want you to know how it feels when my nipples are being pinched.”
Teasing him, I pushed my breast around his face. I whispered in his ear, “Mistress Contessa owns your cock. I’m going to suck that cock, until you erupt your thick cum all over my tits. You want that don’t you?”
He smiled with his eyes, his cock was hard and ready for the cock ring. It fit right around the base of his shaft.
“Ready for the nipple clips, handsome? Close your eyes for me, lover.”
Next to the bed was the ice bucket and I reached in and removed an ice cube.
John was watching me as I ran the ice cube over his chest, then over his right nipple. The frozen water made the tiny nub hard. Then my tongue warmed it back up so the clip would cause the right amount of pain. I repeated the same movements with his other nipple.
Now, I was ready to start having some fun. I started by nibbling down his neck, to his chest.
He watched me when I had just noticed the mirror above the bed as I moved my pussy against his thighs. My clit was so hard, sticking out like a small cock between my pussy lips.
“You want me to suck you, don’t you?” A dick head bob was my answer.
It took both of my hands to hold his enormous cock. I reached between my legs for some lubricant and then with firm strokes, I began my torment.
One hand glided up and down his shaft as my mouth sucked in a large heavy ball. I rolled it around in my mouth and then I sucked the other hairy ball sack, soaking his balls in my saliva, they were seeping wet.
I reversed positions so my pussy was in his face. But he was tied up and he had my panties in his mouth. He groaned in frustration and I ground my pussy on his beard. My juices left their existence on his face and he watched me in the mirror.
“I’m sucking your cock for my pleasure John, not yours. If you cum, before I allow you, I’m going to fuck you in the ass with the strap on.”
He moaned again. Without any mercy, I inhaled his cock down my throat until I was choking from it. My face got covered from my spit, up and down, sucking, stroking, milking his cock as I brought his hot load up from the depths of his balls.
His hips rocked up and down and he was ready to burst. I could taste the first spurts of ejaculation as it hit my tongue.
“Did I tell you to cum, John? That was a bad boy, John. Mistress Contessa will need to discipline you.”
I reached my hand into the ice bucket and with a handful of ice, I started rubbing his cock with it. He nearly screamed from the sensation and he twitched and was sweating. His cock flopped on his stomach.
“Mistress Contessa is very upset with you. I’m going to show you what you could be doing to me right now.”
I took my phone from my purse and held it so John could see it as I pushed play on the video.
His eyes got huge as he saw me using my high-powered vibrator going in and out of my pussy. My eyes closed and I moaned. The vibe was slick with my juice as I threw my head back and squirted across my bed.
“That’s a good boy! Look at your cock, hard, just for me. Mistress Contessa is going to fuck you now.”
I straddled his hips as I slowly lowered myself over his cock, until his penis was buried to his balls inside me.
Up and down, faster and faster, my breasts whacked him with each thrust until I saw his eyes close, he groaned, as his soul left his body.
I rewarded his extraordinary behavior by taking my panties from his mouth and stood over him, so he could watch as his white, milky seed, fell from my cunt.
He hefted me on top of him, “Mistress Contessa, I am forever yours.”
He reached for the water as I snuggled next to him, “Now it’s my turn.”
I fell asleep so he covered me up and kissed my face. “Sleep, Mistress, tomorrow, I will make you my fuck toy.”
The sun was shining through the window, slowly waking me up. I couldn’t feel John next to me in the bed, the memories from last night came surging back to me. I heard the shower running so I knew he was still here he hadn’t left me in the middle of the night. I should have gotten up and done something with my wild hair, but the bed was so comfy.
‘I’ll just enjoy the quiet of the room, for a few more minutes.’
I must have fallen asleep again because John was coming out of the bathroom, as I was climbing out of bed. I just gazed at him as he wore a towel around his waist.
‘Fuck, he was even better looking in the morning. His tattoos contrasted against his tanned skin, and those eyes, damn.’
He grinned at me, “What, I know I must look pretty scary!”
He laughed and it was infectious. Now I laughed and he sat on the bed next to me.
“Do you know how amazing you were last night?”
“Was I?” I ask coyly.
He leaned in for a kiss, “Baby, that was the night of a lifetime!”
As he said this, his fingers caressed my nipple ring. “I need to hear the story about this.”
“Can I take a shower first and have some breakfast?”
“Of course, babe, go shower, do your thing. Do you want to go down and eat or stay in?”
“I’d like to stretch my legs, maybe go walk around and see some sights. It’s my first time in Vegas.”
“Then that’s what we’re going to do.”
As I got out of bed, I pulled the sheet with me.
“Oh, now your shy?” He slapped my ass as I headed into the bathroom.
“Hey, I’ve got my secrets, just like Victoria!”
His eyes lit up and he laughed like crazy. “Yes, babe, yes you do!”
We took our time enjoying a great brunch in the casino’s atrium. We were just talking, laughing, enjoying the moment. After brunch, we headed down to the strip and played some slots, had a few drinks, and walked around holding hands.
Then around eight in the evening, we grabbed a cab and went back to the MGM. The room was clean with fresh sheets on the bed.
The view from our room was amazing. The mountains were on one side with the magnificent casinos all around us.
John purchased some snacks and beverages to have tonight in the room. We planned on watching an in-room movie and relax after our busy day. Then we would go out for dinner later tonight.
We both changed into something more comfortable. John put on shorts, while I chose one of his T-shirts, with no panties.
We didn’t see the end of the movie because we both crashed with John holding me the entire time. I must have turned over on my side at some point and I could feel John pulling me back into his arms.
I woke up to John ordering room service. He winked at me as he was talking on the phone.
“I hope you don’t mind but I don’t want to share you tonight.”
“Of course not. How did I get so lucky to find you?”
“Babe, I thought the same thing about you.”
The view at night from our room was even more spectacular than during the day. It was mesmerizing to watch all the people continuously walking around the streets of Las Vegas, no matter what time of day or night.
Room service was delivered and we ate our meal outside on the balcony talking and laughing.
But inside I felt a sense of dread because I will be leaving tomorrow, one weekend no commitments.
After dinner, we had a bottle of wine. John got frisky and I was too. He moved around the room lighting the candles and he went to my goodie bag and started pulling out adult entertainment enhancements, leather restraints, blindfold, supersonic vibrator, and lubricants.
He took my hand and pulled me into his arms, whispering in my ear, “Wendy, you caged a Tiger last night but now he’s free and ready to pounce.”
John placed the blindfold across my eyes and then I felt the leather restraints around my wrists. He led me to the bed and he attached the restraints through the headboard but he left my legs unrestrained.
The air conditioner blew directly onto my chest and my nipples grew hard, minutes passed.
“I’m here baby, I’m enjoying the view of you like this. Your body is naked and open only for me to play with. All mine, sweetheart, all mine.”
The bed creaked as I felt John slide next to me. His arm rested against my chest as he fondled my left nipple, with the diamond nipple ring, that was teasing and fascinating him at the same time.
His mouth captured a nipple as his hand squeezed and pumped my breast. He alternated between them, so every nerve in my body throbbed.
John took his time as he brought me up and then cooled me down. After what felt like an hour, my nipples were swollen and raw.
He had me take a sip of cold water, “Here babe, I don’t want you getting dehydrated.”
“Yes, Daddy,“ I purred back to him.
“Naughty, naughty, but I like it!”
“Daddy, my pussy is aching.”
“Then daddy needs to fix that, sweetheart.”
I felt John making his way to my pussy, he kissed every inch of me and then gradually slid between my legs.
“Bend your legs for me, sweetheart.”
He licked the outer lips first, with his nose pushing almost inside, then I felt his hands spread me apart.
“Damn,” he said, “beautiful big pussy.”
Two fingers pushed in. I felt him scrape some of my lubricants into his hand. I knew he was rubbing it on his cock, jerking himself, before he dove headfirst into my vagina.
I couldn’t see him but I could hear how much he was enjoying the all-you-can-eat taco bar.
The sounds of him slurping and sucking, his finger teased my asshole as they pushed me to an explosion.
“Daddy, can I cum please?”
“Yes, say my name baby, when you cum.”
I thrashed back and forth as John sucked my clit hard and then I felt his finger slide into my ass.
“John, I’m cumming, I’m cumming!”
My wetness squirted out rapidly, filling his mouth. I could hardly catch my breath and I was shaking uncontrollably.
John wasn’t in much better shape. He was so overcome with emotions and with shaking hands, he removed the blindfold and the restraints and pulled me into his arms.
I shook against him, “Oh baby, that was beautiful. Watching you, feeling your body giving up its secrets to me, that is a gift.”
He reached for the water, “Baby, here take some water.” My hands shook as I lifted the glass to my mouth.
“Do you always cum like that?”
My voice was low and soft, “Only for the right man,” I whispered shyly.
My trembling had stopped and John looked into my eyes.
“I want to make love to you now! I’ll wait if you need more time.”
“Take me, daddy.”
John smiled and kissed me until my brain was no longer functional. He placed himself between my legs, he was holding his cock at the opening, then he pushed deep and my body came off the bed.
His head was back, eyes closed, he was gone. He was pumping in and out hard but not uncomfortable.
I murmured his name and we both got lost in the joining of our bodies. My pussy held him like a vice, each time he pumped into me, until he grabbed me into a sitting position.
“Wendy, oh damn,” then I felt his hot load filling me. He rubbed my swollen clit with his cock still in me until I felt like I was flying.
I grabbed a pillow and screamed into it and my body came off the bed. John held on for the ride of his life.
We were spent with nothing more to give away. We cuddled and whispered into the morning before drifting off to sleep.
The next morning, I woke up early. Very quietly, I tiptoed into the bathroom. I was just turning on the shower when John came into the bathroom.
“Wendy, you’re not leaving me.”
“I’m only taking a shower silly, my flight doesn’t leave until 3 pm.”
“I’ll take a shower with you.”
“Ok baby, what’s wrong?”
“Nothing, everything, I’m a mess.”
We showered and John washed my body and my hair. He kissed me gently, so lovingly.
“Wendy, you can’t leave me,” he said as we toweled off.
In my head, I was kinda freaking out, but I held it together.
“Let’s get room service, get you some coffee and we’ll talk about what’s next, ok?”
As I ordered room service, John paced the floor.
As soon as the food arrived, we both drank some coffee.
John stared at me, “Ok, what?”
I was almost hesitant to know what was freaking him out.
“I don’t want you to leave me, not today, not tomorrow, not ever.” His voice quivered.
“John, we had an agreement remember, one weekend, then we go back to our lives.”
“Fuck that, Wendy. I love you and I can’t let you go.”
“John, I have responsibilities, a dog, a house. You really can’t think I’m just driving off with you right now, do you?”
“No John, I can’t, be realistic.”
“You don’t love me, do you?”
I had to handle this carefully before he completely lost his mind.
“John, I love you.”
“But I need to go back to Michigan, today.”
His sigh was breaking my heart.
“You won’t forget me, will you?”
He sobbed so I went to him and sat on his lap. I held his face and looked into his eyes.
“Trust the process, if we’re meant to be, we’ll be.”
We made love one more time.
Three hours later we stood together, both of us bawling our eyes out, as I waited for a cab to take me to the airport.
One last hug and kiss, before I watched John in the review mirror, as the cab slowly pulled away. We had an agreement.