This is the story of how I recruited my perfect mistress on a dating website.
I'm a mature married man in my mid-forties, just at the middle age crisis point. I have my own successful business with about a hundred employees that almost runs itself with the great managers I've recruited and trained over the years. I'm a demanding boss but pay well for the right people. This all gives me the freedom of time plus the resources to pursue a great sex life.
Don't get me wrong, my wife is truly wonderful. She's beautiful, a great mother and volunteers for community charities. A perfect executive spouse. But I just want to have a sweet, young bit of pussy on the side. It's totally egocentric. Call me a narcissist. Hate me. But that's the simple truth. Any man in my position would be thinking along these lines.
When I decided to find a great mistress, I listed what I wanted in the woman and then plotted my strategy to fulfill my desires. First and foremost, I wanted a normal woman, not some skanky wench that dressed like a tramp with makeup an inch thick. No, I wanted a nice, attractive woman in her mid-twenties to early thirties. She would be a stay-at-home single mom who needed some money for her household and had her priorities straight. I could see myself dropping in for a booty call once or twice a week. Being my companion on short business trips would also be part of it. I envisioned paying her four or five thousand dollars a month. That kind of generous allowance would tempt even the most prudish young lady. A simple win-win arrangement for both of us and her young family.
Online dating services are a great way to meet lots of women. I subscribed to several and posted a phony profile posing as a mid-forties successful executive looking for a causal relationship. I added a picture of mine that was a distance shot that nobody could recognize. My thinking was that a woman in her twenties might go out with a successful man in his forties. With about a twenty year spread, my thinking was that this type of person would be more interested catching a wealthy mate than true romance. Even if she is looking for marriage, when I gave her a lucrative proposal for a long term sexual arrangement with a mature gentleman, she might go for that while she keeps looking for a true marriage partner.
Soon I was receiving messages from dozens of young ladies as well as me trolling the site's female profiles and sending out my own messages to likely looking prospects.
I had a huge number of names to follow up on but I was only interested in attractive, single stay-at-home moms. But after filtering for attractiveness and other key attributes, that still left dozens to choose from. I spent many hours trading messages telling them my made up life story while hearing theirs which likely were true. It was a fascinating case study in human psychology.
If a girl seemed right, after we traded five or six messages, I would ask for a few photos. If none were revealing of their figure, I would ask for a swimsuit photo. They got the message immediately and sent back some pics that showed off their sexy bodies. Or if they refused, I would stop communicating. I didn't like it when a girl sent back a picture of a super skimpy bikini. I prefer a more conservative, modest woman. Somebody who hasn't had a lot of lovers. Skanky slutty types turn me off.
Finally, a nice girl named Wendy, of all the women seemed perfect. She was twenty-six. She had moved across the country with her husband but their marriage fell on the rocks and they had divorced about a year ago. She liked her new city but had no family here for support. She wanted to go back to college to get a teaching certificate. She has a three-year-old boy who is the center of her life. She was anxious to meet. We had progressed to phone calls. Here is the first one. I recorded it.
"Hello Wendy, this is Robert from the dating site. I've really enjoyed trading messages with you. You sound like the type of woman I've been looking for."
"Me, too Robert. I feel a real connection. It's been great getting to know you. You seem like such a perfect gentleman." Her voice was sweet and very feminine.
"Wendy, how long have you been on the website?"
"Gee, it's only been a couple of weeks. It took all my nerve to give it a try. My ex-husband is the only man I've been with. I'm actually a bit shy with men. You're the first man I've talked to like this since my divorce almost a year ago."
My mind reeled at the thought of teaching this sexual novice about real sex with a lusty mature man. She must be incredibly horny after not being fucked for a year. What a nice tight pussy she must have. I got a titanium hard on as we spoke.
"Wendy, that's a real shame. You are such a lovely looking young lady in your pictures. I love the way you don't have a lot of makeup on. You have real natural beauty. You should get out and have a bit of fun."
"Robert, you're making me blush. That's such a nice thing to say."
"Plus, Wendy, you are such a great mom, congratulations. The pictures of your son show he's quite the nice young man. I think it's great for a son to be at home with his mother during their formative years. Fortunately, my business is doing so well that any woman with me can do that."
"Robert, that's so nice of you to say. Most men want their mates to go out working."
"Well there's a place for that too but at the right time and only if my mate wants that. Did you say that you wanted to go back to school?"
"That's my dream. They have daycare right at the college for Tommy. But there's no way I can afford that."
"Well, maybe I can help."
After a long pause, "Robert, I'd really love to meet you. Geez, I can't believe I just said that. What must you think of me? I'm never this forward."
"No Wendy, that's quite okay. I can tell you are a very proper young lady and mother. Nothing to apologize about. I'm extremely interested in getting to know you better. Unfortunately, I'm off on a business trip for a couple of days. We can get together when I get back. Meanwhile I'm going to hide my website profile. I want to concentrate just on getting to know you and nobody else."
"Oh, Robert, I'm going to do the same. I feel so lucky to have met you. I want to try to be with you. Oh, shame on me. There I go again. You must think I'm some kind of hussy."
"No of course not, my dear. But there is one thing."
"What's that?"
"None of the extra photos you sent me show you in a bathing suit. I can see from those pics of you in a dress that you have a nice body but it would be so nice to have one of you in a nice revealing outfit so I can fantasize about being with you."
"Oh, Robert, you're making me blush. No man has ever talked to me like that."
"Well, my sweet, I believe sex is a big part of a successful relationship. And I do like sex."
There was a long pause and I could hear her heavy breathing.
"Sure, Robert, let me send you some pictures. I hope you'll like them."
"Bye Wendy."
"Bye Robert"
I got off the phone and my mind was swirling. The call had gone better than I ever imagined. At first as I was pressing forward, I thought maybe I was going too fast but she seemed shy although eager to move our new relationship along. She's obviously not experienced.
Her wanting to go to college could easily be done if she becomes my mistress. My company makes over a million dollars a year. What the hell, I can't take it with me. I'm not taking advantage of her. It's win-win for both of us.
Late that evening, I got three pictures from her texted to my phone with a little note. 'I loved our chat tonight Robert. I look forward to more. Believe it or not, I don't have a swim suit. It's been years since I was swimming. Her are a few selfies I just took. I'm in my bra and panties. I can't believe I got the nerve to take them but I finally said to myself, these are about as revealing as a swim suit but not too risqué. You asked for some revealing images and I wanted to please you.'
I loved the way she said she wanted to please me. That's one of the key things I'm looking for in a mistress. The pictures were fantastic. Wendy is gorgeous standing in front of her bathroom mirror with her cellphone in her hand. She has long, flowing blonde hair past her shoulders. Her face is very pretty with high cheekbones and full pink lips. Her perfect eyebrows match her golden hair. The first picture had her big blue eyes looking a bit nervous. No doubt because she was nervous taking a sexy picture for a man she'd never met.
She had on a pink bra with a sweet little bow in the middle between the full cups. Her 36B breasts (my guess) were spilling a bit over the top of each cup. It was nice to see her nipples were stiffly erect and showing through the fabric. Wendy was getting turned on when she took this pic.
Her waist was slim and her abs were fit. She must exercise to keep in shape. Her matching pink panties were the full conservative type that I really love. They fit snugly on nice slim but womanly hips, not the boyish hips that are the fashion nowadays. This picture had her standing close to the bathroom sink so I couldn't see the crotch area.
