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Cheating With Ashley

"True stories make the best stories"

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She was thirty and her name was Ashley. Her mother and I had dated back when we were much younger and I was in college. I had wanted to marry Dorothy, but she had designs on someone else. Looking back on things, it was probably best that we didn't’t get married. Husband number three of five for Dorothy produced Ashley. I managed to stay in contact with Dorothy through the years, through phone calls every now and then, but what was in the past, remained in the past. Dorothy often told me about Ashley and how much she was adored. Then came the calls about the ‘wild child” and I would remind Dorothy that Ashley was probably an exact copy of herself. Dorothy didn't’t want to hear it and insisted she had been angel, albeit one with a ‘rusted halo.”

Rusted, bent and sold out to the highest bidder.

Then came social media. Social media allowed me to connect with Dorothy on a whole different level. I now had access to photos. Naturally, Ashley became inquisitive about the guy from Texas who was always posting comments on her mother’s Facebook page. I also knew the entire family and was very well thought of, as far as I could tell.

Dorothy had been very much a wild child and I was happy to see it all coming back to roost. Ashley married at 19 and then was divorced a year later. Ashley then decided decided she was a lesbian and was proud to announce on social media, as much even through her Southern Baptist family was absolutely horrified. Ashley back channel messaged me and said she really wasn't’t gay, but just wanted to wake everyone up to the reality that gay people were absolutely okay.

Ashley had a series of boyfriends, but none of them seemed to stick. Frustrated with life in a small town, she decided to go to college and become a nurse. She struggled and when she wanted to quit, I urged her to not do so. I soon became pretty good friends with Ashley through the magic of social media – providing her advice and listening whenever she had issues.

Then one day, out of the clear blue, I got a phone call. I recognized the area code but didn't’t recognize the number.

“Do you know who this is?” the sweet and charming voice asked. I had no clue.

“Ash,” she replied. It took me a second to collect my thoughts.

She laughed, when I finally figured out who she was. I was surprised. Chatting with someone on social media is not the same as talking to them on the phone. We talked for about an hour. It was as though we both had known each other a life-time.

It was great to put a voice with a photo. Ashley was like a carbon copy of her mother.

“Can we just keep this between us?” Ashley asked towards the end of the call.

“Keep what between us?” I asked.

“Our chats,” Ashley responded. “Mom would not be happy to know I’m chatting with a guy twenty years older than me.”

“There’s nothing wrong with us talking,” I replied. “It’s not like were sleeping together. You’re in Georgia and I am in Oklahoma.”

Ashley laughed.

“I know," she replied, “but you never know when I might just decide to come check out Oklahoma.”

“Come on,” I playfully teased. “Bring your thong and your sun tan lotion and a cowboy hat.”

“I don’t wear thongs,” Ashley replied. “I hate the tan lines they leave.”

My text message box 'dinged' and I quickly checked it, thinking it was work related. It was a photo of Ashley laying out on a beach, butt ass naked, and sporting a floppy hat and oversized blue-lensed sun glasses.

“Damn!” I exclaimed.

Ashley giggled.

“Don’t you dare show that to anyone,” she said. “That’s just between you and I.”

“Don’t worry,” I replied. “You’re safe.”

My phone ‘dinged” again, three times and each time it was a different beach photo of Ashley, each one slightly more provocative than the others.

“Have you ever considered modeling?” I asked.

“Oh yeah,” Ashley replied. “I got paid $2000 for this photo set.”

I was impressed. Ashley was very pretty and she knew it.

“Now that you know me,” Ashley said, “What do you think?”

“You’re a very lovely young lady,” I replied.

“You’re a good photographer,” Ashley replied. “I love your photos on Facebook. Do you photograph models?”

“Not normally,” I replied. “I do nature stuff, but if you’re looking to be photographed, I can make an exception. Of course, we would have to find a good neutral place to meet up.”

“How much would you charge?” Ashley asked.

“For you, nothing,” I replied.

Ashley said she couldn't let me do a photo session for free.

“I’ll pay you,” she said.

I told her that I didn't feel right taking money from her, especially since she was just finishing up nursing school and given the fact that her grandmother and her family were old acquaintances.

“Then we’ll work something out, somehow,” Ashley replied.

I didn't’t give my conversation with Ashley a whole lot of weight. First of all, she was in Georgia and I was in Oklahoma. Second, I didn't know her outside of social media and third, the likelihood of us connecting, was slim and none.

We agree to chat again sometime in the future after she had finished school and we agreed to stay in contact.

About six months later, Ashley texted me and said she was going to be in Dallas for a job seminar and she asked how far away from Dallas I lived.

“Three hours,” I texted back.

“Do you want to meet up?” she texted.

I stared at the text for the longest time. I was unsure how to respond. Part of me wanted to meet her and part of me said to be careful. She seemed to be too good to be true.

“Sure,” I texted back.

She provided me the name of the hotel and dates for her stay. I told her I would drive in and suggested we meet up at the bar in the hotel.

“Cool,” she replied by text, followed by three attached red hearts.

It was a short drive to Dallas. I was a bit apprehensive about meeting up with Ashley. Talking to someone on the phone was a whole lot different than meeting then in person.

I parked at the hotel and found my way to the hotel bar. It was about five in the afternoon and it was a hot summer day. There was no one in the bar, except the bartender, who was surprised to see a patron in the bar at 5:00pm. He offered me a drink. I settled on a Coke over ice.

I noticed Ashley the moment she stepped into the doorway of the bar. There was no missing her glamorous look, her bright smile and long brown hair. She was a definite head turner, decked out in heels, skin tight designer jeans and a lose fitting white, button down blouse that showed off her svelte figure very well. She walked straight towards me, her arms open and smiling. I slipped off the bar stool and we hugged. Oh my God, she smelled so wonderful and she was so very refreshingly cute.

“You’re taller than I expected,” Ashley said as she slipped on to a bar stool.

“Six foot four,” I replied. "I was six five, but I shrunk a while back.”

Ashley laughed. She reminded me so very much of her mother.

“You’re really pretty,” I told her.

“Got that and my bitchiness from mom,” Ashley replied.

“Snarkiness to,” I added.

“Yeah,” Ashley replied, “And her sense of humor.”

I took in a deep breath and exhaled. I was nervous. I was out of my league.

Ashley slipped her hand on to my leg.

“Calm down,” she said. “I don’t bite.”

“I wouldn't care if you did,” I jokingly replied.

“Do you want to go somewhere? Ashley asked, casually flipping her long brown hair back over her shoulder.

“Have you ate?” I asked.

“I had a late lunch,” she replied.

“We can just walk around if you want to,” I suggested.

“Sure,” she replied. We walked to the lobby. I asked her if she had ever been to Dallas and she said she had not. She said the job fair didn't start until the next day and that she had come in a day early just to get a feel for the city.

“Oh,” I replied, “I thought you came in early just to see me.”

“That too,” Ashley quickly noted.

There wasn't a lot to see in the lobby. I was about to suggest that we go for a drive, when Ashley asked if I wanted to check out the view of the city from her room.

“It is the coolest view,” Ashley declared.

“Sure,” I replied. Ashley slipped her arm under my arm as we walked towards the elevator. She was a good foot shorter than me, in heels so I suspect she was about five foot four or so.

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She punched the button to the twenty-eighth floor and we watched as the numbers rolled by on the screen over the door.

Ding. “Twenty-eighth floor,” announced the voice from the elevator control box.

Ashley led the way down the narrow hallway to suite twenty-eight fifteen. I walked slightly behind her, admiring her very cute ass. Halfway down the hall she reached back and took my hand in hers.

“Come on silly,” she playfully teased.

She slipped the access card into the door and I followed her into the large suite, with floor to ceiling windows that provided a fantastic view of the cityscape.

“What do you think?” she asked as I stood looking out the windows.

“What a great view!” I told her.

“Yeah, the view is great,” Ashley replied, from behind me.

I turned and chuckled.

“You’re a mess,” I teased. “I was talking about the view outside the window.”

“Yeah,” Ashley replied. “That looks good as well.”

Ashley slipped out of her stiletto heels and launched herself on to the bed, turning on to her side, propping her head up with one hand.

“What about the view over here?” Ashley suggestively replied in a very sultry manner. She couldn't have made her intentions any clearer.

“Are you trying to seduce me?” I asked.

“Maybe,” Ashley replied. “Do you want to be seduced?”

I chuckled as I stepped away from the window and over to the side of the King-sized bed.

“Sure,” I replied. “Seduce me.”

Ashley rolled on to her back and pulled on her satin-like blouse, ripping the front of it open as the buttons popped lose. Her 38c cup boobs were neatly tucked into a white lace bra. She sat up, stripping out of the blouse and tossing it to the side. She slipped the spaghetti straps of her bra past her elbows and then reached behind herself to unfasten the clasps that held the brassiere in place. She held it in place with one hand and looked at me.

“Are you going to just stand there in awe?” she inquired, “or help me?”

I heel kicked off my penny loafers and slipped on to the bed as Ashley discarded her bra. Her nipples were firm and hard, as I leaned in and slipped my mouth on to her left nipple, lightly circling it with my tongue, as I massaged her right boob.

Ashley locked her hands on to my head and held me in place as I sucked and joyfully played with her luscious boobs. Ashley leaned back on the pile of pillows behind her as I stripped out of my polo shirt.

I worked my way up her neck with kisses as she shuddered.

I teasingly worked my mouth across her neck and then to a spot just below her ears.

“I’m going to fuck you,” I whispered.

“I hope so,” Ashley replied. “Give it to me!”

I took her ear lobe in my mouth and as soon as I did, her entire body shook.

“Oh my God!” Ashley exclaimed.

My hand found its way to Ashley’s erogenous zone. She unsnapped the button to the fly of her skin-tight jeans and lowered the zipper, revealing the top of her white satin panties. I pressed my finger-tips past the edge of her panties. They were already soaked with a mix of sweat and her womanly juices.

As soon as my finger tip reached the tip of her vagina, she shuddered again.

“Oh my God,” she repeated.

She arched her back and pushed down on her jeans, as I pulled on the leg portions of her jeans, stripping them from her tight little body. I rolled on to my back as she rolled on top of me, pressing herself against me. My manhood was at full attention and I needed relief from the pressure of it being trapped in my trousers. Ashley sat on top of me, straddling me, her wet pussy pressing against me, the palm of her hands pressing down on my bare chest.

She rocked back and forth very slowly and deliberately.

“Do you want it?” she asked.

“Can you handle it?” I asked in return.

“Oh yeah!” Ashley replied, as she lifted off from my lap. She scooted down and sat on my upper thigh, allowing her the ability to work on my manhood. Biting down on her lower lip, her face framed by her long brown hair, she focused on lowering the zipper to my jeans. I arched my back, allowing her to pull my jeans and my underwear down, exposing the bulbous head of my manhood. She worked her way farther down my legs, stripping me of both my pants and my boxer briefs. My elongated steel rod arched upwards and rested on my lower abdomen.

Ashley took my manhood into her hands and studied it.

“What a lovely cock!” Ashley declared, just before she kissed the tip end of my manhood, her long brown hair tickling me.

She slipped her hand around the shaft of my tool and then inserted it into her mouth.

Now it was my turn to exclaim, “Oh My God."

Ashley knew how to give a blow job!

Just as I was about to blow my load, she stopped and rolled on to her back, stripping out of panties. Her pussy was cleanly shaven. She didn't’t have any pubic hair, which I really liked.

She spread her legs and welcomed my repositioning between them, hovering over her, the head of my cock resting at the very entry to her glory. He reached between her legs and guided the head of my cock up to her pussy, working it around the outer bands before pushing the end of it in towards the opening.

I slowly worked my tool into her very tight pussy, as her eyes widened. My pubic bone met hers and she shook. I worked my tool back and forth in her pussy, the walls of her vagina clamping down and then releasing their grip on me.

Ashley stretched out her hands over her head, interlocking her fingers. Her boobs bounced wildly as I pummeled her. She let out “uhs” every time I slammed my pubes into hers.

She let out a string of “oh my God” exclamations as I worked my tool back and forth in a feverish manner. I grabbed her hands and held on to them over her head. She shuddered and shook like crazy, orgasm after orgasm rocking her tiny body.

I was ready to explode. Ashley pushed me on to my back and mounted me, pushing my pole into her warm moist pussy. She rocked back and forth on top of me, pressing her hands into my chest. She bit down on her lower lip, then tossed her head back wildly, her arms shaking and trembling as she clinched her fists.

“Ooohhh myyyy Gawd!” Ashley cried out.

I couldn't’t believe how very intense things had gotten.

“Give it to me!” Ashley pleaded.

“Doggie style,” I said. “I want to slap your ass.”

“Oh my God, I love it!” Ashley declared, slipping off from on top of me. She turned and pointed her ass at me. I slipped off the bed and pulled her to the side of it. Her little brown starfish stared back at me. I slipped my cock up to her ass and attempted to put it in her ass.

“No!” Ashley declared. “Not there!”

I jammed my cock into her asshole and she shrieked. I quickly pulled out and pushed my cock into her pussy. She fell forward on to the bed and rolled on to her back.

“Oh Fuck!” she screamed. “You are crazy!”

I laughed, and grabbed her feet, spreading them as far wide as I could. I leaned in, placing her long muscular legs over my shoulders, jamming my tool into her pussy as I looked down on her. Her eyes widened as I shot my load deep into her steaming hot pussy. She shook and shuddered as I unloaded everything I had inside of her.

“I can feel you coming!” she declared.

I emptied myself and then pulled out. I let go of her legs and she rolled over on to her stomach, red-faced and flushed.

"Oh my God!” Ashley declared. “That was intense!”

I slipped on to the bed beside her, looking up at the ceiling. She tossed an arm across me.

“Oh my God!” she said, “I can still feel you in me.”

I was happy and Ashley’s apparent satisfaction made me feel good. We lay on the bed motionless for the longest time.

Eventually, Ashley took it upon herself to rework my tool back into a semi-excited state. I told her there was no way I would be able to give her a second cuming, but she was intent on trying. She remounted me and rocked back and forth on my lap for several minutes.

Once again, she was not going to be denied the pleasure she so desperately desired. I closed my eyes. I managed a small spurt, and while it was, to me, anti-climatic, Ashley seemed happy with my efforts and the end result. She collapsed on to my chest, her head coming to rest on my left shoulder, her eyes closed and her hand resting on my chest.

I explained to Ashley that as much as I wanted to stay and spend the night, I’d end up divorced if I did. She said she understood and thanked me for making her trip to Dallas more enjoyable.

I dressed and excused myself from her hotel room as she lay curled up on the bed in the bedsheets. As I made my way to the lobby, my phone dinged with a text message, “Thank you!” accompanied with a selfie photo of a very happy Ashley, her hair a mess and a mischievous smile.

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Written by CommunicationDirectr
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