Loving Wife to Online Slut

Authors Note:

Thanks to smoothed for his editing assistance and making this story a much more readable one!

smoothed has submitted three very well received stories over the last year. If you haven't read his works, please look him up. You're in for a treat.

TSG

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Present Day In His Home Office

I sat behind the large wooden desk in my home office with grim determination. After reviewing my checklist for the tenth time and being satisfied that my plans were properly prepared, I leaned back, closed my eyes and thought back over the last two weeks.

Our first email exchange happened twelve days earlier, while I was traveling on business to Memphis. My email was sent to a woman with a sexually explicit user name. I'll call her Ashley. Ashley is a member of a popular, well known, worldwide cheaters website.

I was attracted to Ashley's profile. Her profile title read, "Sweet and Married wants to Explore." The profile continued, "I am a forty-eight year old married woman. I've spent over half of my life being a loving wife and mother, while devoting myself to my family, friends and community. At this point, I selfishly want to explore sex with men other than my husband. I am incredibly discreet and will only meet with those who will play within my rules. If interested, take a chance and introduce yourself."

With a great deal of interest, I wrote:

(Me) Hi! My name is Mike. I'm thirty-nine, married (and want to remain married), well-educated and have a professional career. I am employed as a senior project manager in the computer hardware industry and I am currently overseeing a project near you. I travel to Hartford every week and will continue that schedule until the project is completed in eighteen months.

Physically, I am 6'1", 190 lbs., with a trim and athletic build. I have short black hair and dark eyes. I am told that I am a good looking man. Sexually, I tend toward the dominant side and like to take control. I'm not looking for love. I get that at home. Instead, I'm looking for raw, physical and uninhibited sex.

Like you, I am 100% discreet. I can meet you in public, at a place away from your hometown. That will allow you the privacy that you need and we can get to know each other in a safe setting. Assuming we decide that we match-up and want to start an intimate friendship, I stay at a hotel, when I'm in town and will host you in my room.

I'd love the opportunity to get to know you through emails and will look forward to the possibility of meeting you sometime in the future. (End)

After sending the email, I checked a number of other profiles, but didn't find anyone else as interesting as Ashley. After a quick trip to a nearly empty hotel bar, I went to bed and slept soundly.

The following day was busy. My Memphis clients had a number of technical meetings scheduled and I was on the run into the early evening. I took two of the clients to dinner at an upscale seafood restaurant. We were able to put the busy day behind us and had an enjoyable meal.

I grabbed a bourbon on the rocks, as I walked through the hotel's lobby/bar area and took the drink to my room. After changing into a pair of gym shorts and tee shirt, I booted up my computer.

I was thrilled to see a response from Ashley had been forwarded through the website, to my secret email account.

The email read:

(Ashley) Hi Mike. Thanks for introducing yourself. Your email was much more informative than most of the ones I've received. To be honest, the majority say, "Wanna fuck?" Or something similar. Yours was refreshing. Thanks.

More about me: I've been married over twenty years to the same man. My husband works as an executive in the construction industry. He travels for business and while he's away (and only when he travels), I date.

I'm a successful real estate agent. As is usual with my industry, I have a chaotic schedule. With proper communication and planning, I can schedule dates during the day or early evenings.

I've been a member of this website for over a year and I joined when my youngest child left for college. I'll admit that the combination of being an empty-nester, having a husband who travels extensively and a close divorced girlfriend who brags about her many sexual exploits gave me the inclination to have an affair.

I'm attracted to you for a few reasons. I only date married men. I think the political term is "mutually assured destruction." I'm also glad that you are from out-of-town and have a hotel room. Three of my past friends were fairly local. I was constantly worried that I'd run into them, while I was out with my husband. In fact, I saw one of my boyfriends, after we had broken up, at our local airport, when I was leaving on vacation with Hubby. Luckily, he didn't see me. I'm also thrilled that you are ten years younger than me. I've never been with a man ten years my junior.

Since joining this site, I've received thousands of emails. (I've heard women receive many more than men). I've had in depth online relationships with over twenty-five men and met eight for a coffee or drink. I've only had six affairs, if you include three one night stands. The other three friendships lasted for a few months each and all were exciting in different ways.

I have some questions for you.

Are you currently involved with any other women (not including your wife)?

Is this your first affair?

What do you like the most and least about your affairs?

What do you look for in a playmate?

I want you to understand that we will need to get to know each other through emails. I won't jump into your bed after a few days. I can also promise you that I'm worth the effort. I'll look forward to the possibility of your continued interest. (End)

I didn't want to seem anxious, so after reading Ashley's email, I shut down my computer and headed to the hotel gym. I ran on the treadmill for thirty minutes, lifted dumbbells and stretched afterward, before heading back to my room and bed.

At six the next morning, I arrived at the Memphis Airport and flew home. I stopped at the office for a couple of hours. I cleaned up a few emails and put out a fire, before calling it a day.

As we had planned, I met my wife Bonnie at a local bistro, along with longtime friend Kelly and her fuck buddy of the week. The dinner and drinks were outstanding. The company was barely tolerable. I didn't like Kelly. She was a man-hating slut.

Bonnie had driven to the restaurant with Kelly and Roy. She drove home with me.

As we left the restaurant parking lot, Bonnie knelt on the front passenger seat, leaned over the console, unbuckled my pants and fished out my rapidly expanding cock.

"Keep your eyes on the road, lover," was Bonnie's instruction, as she swallowed my rock hard dick. Bonnie is an incredible cock sucker. If she wants, she can use her lips, tongue and throat and have me pumping cum into her mouth within seconds. Tonight was the opposite and equally enjoyable. She slowly pushed my cock into her throat, at times gagging around my shaft, without letting me cum.

The drive home was just over thirty minutes and Bonnie slowly bobbed her head in my lap the entire time. Early in the drive, I reached over Bonnie's back and ran my hand up her sexy, gym toned thighs and under her skirt. I wasn't surprised, when I reached the junction of her legs, to find a sopping wet pussy.

"My little slut forgot her panties," I observed. Bonnie groaned around my erection, as I traced my fingers along her wet lips. Occasionally, I'd slip the tip of a well lubed finger into her pussy or butt hole and was rewarded by a deep grunt from Bonnie's cock-filled mouth.

After pulling into the garage and closing the door, I met Bonnie at the front of the car. I lay her back onto the car hood, spread her legs and dove face first into her bald dripping snatch.

I licked my wife's delicious pussy. Every few strokes, I probed her cute tight asshole with my tongue, before slashing it through her folds and circling her clit.

"Fingers! Fingers! Use your fingers!" Bonnie begged, as she neared her orgasm. When I slipped two fingers into her throbbing pussy, rubbed her g-spot and latched my lips to her clit, she reared off the hood of the car and bucked against my face.

After letting Bonnie enjoy a long grunting cum, I flipped her onto her front and bent her over the car hood. She automatically spread her legs and screeched, as I drove my cock into her pussy. Holding tight to her hips, I fucked her, until I came deep in her cunt.

I woke up early on Saturday's and with a pot of coffee went to my home office to finish any week-ending paperwork. I knew Bonnie would be in bed for the next couple of hours, so I felt safe opening my secret email account and replying to Ashley.

(Me) Good Morning Ashley! I'm sorry for the delay in responding. I flew home yesterday morning, spent the afternoon in the office and last evening had a date with my wife. As we are both very discreet, can we agree that we won't get upset if responses become delayed? I hope so!

To your questions:

I am not involved with anyone, at this time. For the last three months, I've been overseeing six small projects. I haven't spent a great deal of time in any single city and as a result, haven't looked for a friend with benefits.

Our group has completely finished four of the projects and I've been assigned the newest one, in Hartford. The Hartford project is very extensive and requires constant onsite supervision. I'll be visiting often. In the evenings, I'll have the opportunity to regularly host a friend at my hotel.

I started traveling seven years ago and I have had a total of sixteen affairs. Five have been one-nighters, eight have lasted several months and three have discreetly continued for a year or more.

What do I like the least? Liars! I make it a habit of being upfront and honest. If I don't want to answer a question, I'll let you know. I won't lie. All of the one night stands involved incredible sex, with women looking for an ongoing friendship. All of the women disappeared after the first date.

Ashley, you might be saying to yourself, "if so many women "ghosted" this guy after the first date, maybe he's just a poor partner." It's a valid conclusion. But when each of the women left my room, they were gushing with happiness over the orgasms and sex and promising more dates. Anyway - that's my biggest "bitch" about online dating. I hate liars.

What do I like best? That's easy. I love the variety that's offered by new, uninhibited women. Over the last number of years, I've had the opportunity to explore beyond vanilla sex. Women have brought sex toys and restraints to our play dates. Two women have invited girlfriends to join us for a MFF and one asked me to find an extra guy for her.

Your last question was - "What am I looking for?" I'm looking for a woman interested in an ongoing and hopefully long term affair. She'll be attractive and height/weight proportional. She'll be able to meet a couple of times a month. She'll be a lady in public and a slut behind closed doors. I like women who are verbal and in private will use sexually charged words. Ideally, she is married. She is a take-charge type, who wants a man to take control from her, during sex.

I hope my answers meet with your approval.

In your last email you mentioned that your longer term affairs were "exciting in different ways." How was each exciting?

Have a good weekend and I'll look forward to sharing more next week. (End)

My weekend flew by. I worked in the yard for a number of hours on Saturday and Bonnie and I went to a neighborhood BBQ Saturday evening. After returning home, we undressed each other, climbed into bed and positioned ourselves in a girl on top 69. After cumming over my face, Bonnie shimmied down my body and impaled herself on my throbbing cock. She leaned over and hugged herself against my legs in a reverse cowgirl position. I let my eyes fest upon my cock sliding in and out of her pink wet hole. On every down stroke, her ass cheeks opened and her sexy asshole peeked out from between her round tight cheeks.

On Sunday after church, Bonnie and I headed to the Country Club. We exercised together in the gym, before showering and having a late brunch in the member's dining room. That afternoon, Bonnie cleaned the house, while I went to the grocery store and stocked up on a week's worth of food.

Late Sunday evening, after Bonnie went to bed, I closed my office door and checked my email. Ashley had responded that afternoon. She wrote:

(Ashley) Mike, I agree completely! I'll always respond, as soon as possible, but if life gets in the way, you might have to wait for a day or two. I'll also commit that I won't disappear. If I decide that you aren't a match, I'll be honest and tell you! I promise!

I also agree that the fakes and liars are the worst part of online dating. Like you, each of my one-night stands were with men who were drained, when we finished. Each promised that our date was the first of many to come and then disappeared. It's very discouraging.

Thank you for your detailed answers to my questions. At this point, I haven't been disappointed with anything you've shared. You excite me! That's a good thing.

I'm also impressed that you haven't demanded a picture or asked what I look like. In your last email, you told me that you are looking for an attractive woman. I am attractive. I'm 5'5" tall and weigh 138 lbs. My stylish, shoulder length hair is red and my eyes are brown. I have C-cup breasts that are (mostly) high and firm and are capped with incredibly sensitive small pink nipples. I exercise almost daily and have a toned flat stomach, great legs and an ass that makes the men at the gym drool. Other than the hair on my head, I'm completely hairless and my pussy is easily excitable (as it is when I read your emails or write to you).

I did tell you that each of my three longer term affairs was exciting in different ways. One man was very forceful and took what he wanted, within my limits. It was very exciting for me to be used for his pleasure. Luckily, he also made sure that I was well pleased! The second man was black. I still get very excited when I think about how erotic it was to watch his dark body mesh together with my white body. It was so fucking hot and made up for the disappointing size of his cock. I'll admit to hoping that the "black man" myth was true. Unfortunately, my black lover had an average size cock.

The third man (my last) was a wicked treat, although I didn't know it, when we emailed. His penis ... cock was a bit longer than average, but very thin. Initially, I was disappointed. He was amazing with his mouth and tongue, but vaginal sex wasn't very "fulfilling". On our third date, Paul talked me into anal sex, for the first time ever. And it was amazing. I fingered myself and rubbed my clit and he pounded my tush and had the most incredible orgasms. I'm left wondering what anal sex would be like with a thicker cock.

I've been thinking of ways to introduce anal sex into the intimate times with my husband, as he is well endowed. However, after years of denying him access to my bottom, I don't want to change my behavior and make him suspicious.

My husband has been out for the afternoon and will be getting home shortly, so I'm going to sign-off. I am sending an anonymous faceless picture, so you can check out my hot, old lady body. I hope you like it! (End)

The picture was very sexy and highlighted Ashley from the neck down. She was wearing a wet white tee shirt, similar to the type that girls wear at spring break wet tee shirt contests. The thin, nearly transparent shirt stuck to her hard nipples and firm round tits. The shirt ended just above her flat stomach. Ashely's bottom half was covered by a tiny black thong. She looked amazing.

As usual, Monday morning was busy with updates and planning meetings. I needed everything completed by the end of the day. I was heading out of town the next morning. At lunch, I closed my office door and replied to Ashley.

(Me) Wow! You are a very attractive woman. Hot! Fucking hot! I'm flying into Hartford tomorrow and need to be satisfied knowing you are close and continue to email with me. That will be enough ... for now.

In my first email to you, I gave you a general description of me. I'm also happy to tell you that I exercise daily. I run twenty miles a week and lift weights every other day. I'm toned and still have some definition in my arms, shoulders and chest.

Like your last boyfriend, I'm well hung and an inch longer than average. I am thick too. Very thick.

I'm sorry this email is so short. Work is hectic today and I need to get to my next meeting. I've attached some pictures for you. (End)

The four pictures were very provocative. The first was from the neck down, highlighting a gym toned body wearing sweat soaked shorts and t-shirt.. The next picture was approximately the same pose, but naked with an erection. The third showed a long thick erect white cock between the lips of a very sexy African American woman. The last picture showed the same woman, with her lips pressed against a flat groin. She had deep throated the entire cock. The top half of the woman's face was blurred, so she couldn't be identified.

I added a PS to my email and wrote, "I think black on white sex is erotic too."

Between my travel schedule and problems getting the final sign-off on a project, my day was packed. I worked late into the night, the next two days. I didn't sign on to my private email for those days. When I did, I found two emails from Ashley.

She wrote me on Monday night:

(Ashley) Your emails have me dripping. I'm going through three sets of panties a day! God, I'm horny! The blowjob pictures were so fucking sexy. I used my favorite vibrator (a rabbit) and came ... three times. I sure slept well.

Just like your pictures with that sexy black woman, I've kept one trophy picture of each of my affairs. They are anonymous, but I think they are so fucking hot. I have them hidden in a subdirectory on my work computer and occasionally look at them and masturbate, when I need to cum. I've attached each of the trophies. I hope they make you horny and hot for me! (End)

Six pictures were attached. In each, Ashley was on her hands and knees with a different man tucked in behind her. With a camera held high, the male took a picture of his cock entering Ashley's slick pussy. I could see her pussy being invaded in each picture. I also clearly saw her little brown asshole surrounded by two firm tight ass cheeks. Ashley had a surprisingly sexy, large light brown birthmark that covered the upper portion of her left cheek.

On Wednesday morning, Ashley wrote again:

(Ashley) My mind is clouded with lust, as I've waited for your next email. I'm going crazy, knowing you are in the Hartford area. I lay in bed last night with my rabbit buzzing over my clit and thought about you. I wondered what hotel you stay at, when you're here on business.

My company signed contracts for three new listings yesterday. I visited each, so I could familiarize myself with the homes. While I walked through each house, I fantasized that you were a prospective client. I used my fingers in each homes master bathroom and fingered myself as I thought about having sex with you. God! I came hard!

Tell me what you hope our first date will be like?

I took three very dirty pictures for you! (End)

The pictures were amazing. I'll guess Ashley set her phone/camera on her bedroom bureau and pointed it at her bed. Using the built-in timer, she was able to climb onto the bed. The first picture showed her ass facing the camera. Ashley's head was down and resting on the mattress, her legs were spread in a wide upside down "V". Her pussy and asshole were centered perfectly. In between her spread thighs, on the sheet were two dildos. The second pose was identical, except the end of the smaller blue dildo was sticking out of Ashley's ass. She was double penetrated in the third picture, with a pink dildo in her cunt and the blue one still in her ass.