I found a Perfect Mistress Online

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.

The next photo had a trace of a smile and I could see she had puffed out her chest a bit to show off her firm tits. She looked eager to please. Maddeningly, I still couldn't see her pussy area.

The last pic was a mind blower. She was standing back so I could see her from her mid-thigh up. There was a glorious camel-toe notch at the Y where her thighs met her abdomen. I could see a slight dark coloring and a some roughness showing through the thin satin cloth in the area that must be pubic hair. Fuck, I love hairy pussy. It's so natural. I love stroking a full beaver and even running my nose through it. As I looked at the photo, I got a raging, steel-hard erection and massaged it through my pants.

When I finally looked up at her face in the photo. Her face and upper chest had a pinkish tone of a large blush. I could also see a look of sexual hunger and submission. Or that could have been my sexual hunger and raw desire to rip off those panties and open up her tight pussy with the head of my dick.

In a fit of sexual lust, I texted her. 'Thanks for the wonderful pics, my dear. They are all beautiful but I especially like the last one. Under your panties, I could see the faint outline of your natural hair down there. That is so wonderful. It's the custom today to shave it away but I think that is so unnatural.'

As soon as I had sent the text, I regretted it. What if I was too aggressive? Maybe she will run away if she thinks I'm a pervert or something. But to my relief she replied, ''I'm glad you like the pictures. I look forward to meeting you."

That sent my world spinning. I had just more or less told this beautiful young lady not to shave her pussy before I fuck it and she just replied, let's get together soon so you can fuck my hairy cunny. Or was that just my wishful thinking reading what I wanted to hear. I'll call her tomorrow to book a date.

Wendy's Viewpoint.

Robert is by far the best match for me on this dating website. So many of the men are footloose and just wanting to date for sex with no commitment. I'm a mother and I must be more practical. Robert is successful and he is so very masculine in the way he talks. The other men who contact me sound like boys in comparison.

I almost died when he asked me to send some revealing pictures of myself in a swimsuit. But the more I thought about it, the more it seemed reasonable. After all, he is the kind of man that doesn't like to waste his or anyone else's time. If I want to be with a high-powered man, I guess I must do what he says. Sex will be a part of our relationship. Plus, I don't want to look like a prude or something.

But I don't have a swimsuit. Should I go out and buy one? If I was back in my home state, I'd borrow one from my sis. Hell, why don't I just wear a bra and panties. That's about the same as a swimsuit. Geez, a bikini is a lot more revealing.

I strip off my jeans and dig way down into the bottom drawer to find the matching pink bra and panty set I wore at my sister's wedding as one of her bridesmaids. I only wore them the once, so they are like new. I'll go into the bathroom and take a photo facing into the mirror. That should work. Should I put on makeup? Robert likes women looking natural so I'll just put on a little powder on my face and maybe a little in the space between my breasts. That looks better. I should brush my long hair. I'm feeling so sexy as I get ready to send this man a naughty photo of myself. I can feel my nipples getting so hard and my girlie parts are starting to throb and moisten.

There we go, I don't look too bad there is the mirror. I hope I'm attractive enough for him to want me on his arm. Here goes, picture one. Hmmm. Not the greatest. I better thrust out my chest a bit to make my breasts look nicer for the second shot. Now smile Wendy. Hmmm. That's a lot better picture. But there's something missing. Ahh, I see it. You can't see the bottom of my panties. Oh my goodness, should I let him see that private area? Wendy, don't be a prude. Robert is a grown man who has seen a lot of women's panties. In my mind, I get a vision of his big erect penis. I can feel a hot sensation of a growing blush on my face and chest as I take the naughty full body picture. Oh, goodness gracious, you can see a little bit of darkness around my crotch where my pubic hair shows through the shear fabric. Will he think I'm some kind of tart? It's subtle and maybe Robert won't notice it.

I text the three to Robert's cell with a note and go quickly to my bedroom to find my vibrator to quell the heat in my throbbing pussy. I find it, strip off my bra and panties, turn off the light and lie on the bed in the darkness. I twist the base of my pleasure wand and the reassuring buzz hits my ears and my crotch is moistening and throbbing in Pavlovian anticipation. I stroke the tool up and down my slit. It feels incredibly good. But I need a real man's penis to satisfy me. I bet a man like Robert has impressive equipment down there. A vision of an erect large penis flashes into my mind as my vibrator stimulates my most private areas.

Suddenly my phone beside me on the bed buzzes to indicate a text had arrived. It's from Robert.

'Thanks for the wonderful pics, my dear. They are all beautiful but I especially like the last one. Under your panties, I could see the faint outline of your natural hair down there. That is so wonderful. It's the custom today to shave it away but I think that is so unnatural.'

I can't believe he just said that. He's talking about my pubic hair and we haven't even met. But as I stroke my pussy with this vibrator and feel my pubic hair slide by against the side of my palm, it seems so very right. What a sexy man. I take my phone and text back. ''I'm glad you like them. I look forward to meeting you." As soon as my finger hits the send button I regret it. Jeepers, I just more or less said, 'Glad you like my hairy crotch. Let's have sex soon.' What will he think of me? Then I run the delicious buzzing vibrator down the slit between my pussy lips and back up to my clit and I think, "He will think I'm a horny woman that needs a solid fucking. And he'll be very right." I turn up the vibrator setting and gallop to an explosive orgasm.

The Big First Date Night

Robert is picking me up for a dinner date in twenty minutes. Tommy is with a nice older lady in an apartment down the hall. She loves kids and tell me to stay out as late as I want. My goodness, I haven't been on a date in almost forever. I went out and bought a flowery, summer dress at a consignment store. It has a tight waist with a nice full skirt that ends modestly just above my knees. I hope it's not too conservative a style. But the top is shoulderless and there is much more cleavage showing than I'm used to. I hope Robert likes it. I put on a small amount of eye makeup followed by some light pink lipstick. Beneath it all, there is the pink panty and bra set that I wore in the selfie picks. My sister told me to shave away my pubic hair but I remembered what Robert had said about liking natural hair down there. Not that we will be having sex tonight. The thought of having sex just made my knees weak. Girl, it's been way to long. A spray of French perfume on my neck and wrists makes me feel very girlie. My nails just have on clear polish since I can't afford manicures. I broke my budget on the dress. I finish with some white open-toes sandals and go down to the street to wait for Robert.

The day is just turning to dusk as Robert pulls up in an expensive forest green BMW. The tires screech to a stop and he leaps out and runs around to my side. He looks me up and down with a big smile.

Robert's Viewpoint.

She is standing there, so beautiful in a bright flowery patterned summer dress clutching a small white handbag in front with both hands about pussy high. I give her a New York air kiss as she smiles demurely. Her perfume is intoxicating. She is my ideal girl, very natural, very pretty, very young, very shy and very in need of my help.

"You look absolutely amazing. I'm the luckiest man in town."

She looks down modestly, "You're so kind Robert." My goodness I thought, she doesn't know how special she is.

I open the car door and she slides into the black leather seat. As she bends to get in, I can see down her dress to her perfect alabaster breasts almost to her nipples. I can't wait to cup those beauties in my hands.

I get in behind the wheel.

"Robert, your car is so wonderful. I've never been in one so nice."

"And this car has never had as wonderful a woman in it." She smiles sweetly at the compliment. "I love your summer dress. Its so fun and perfect. Let's go and have a great meal."

We drive to a five-star restaurant where I had reserved a small private dining room downstairs. Its walls are rich wood paneled and the carpet is deep and blood red. There is a long dining table that can fit eight but we sit at one end with me at the head and beautiful, young Wendy on my right.

Wendy's Viewpoint.

This room is so ritzy and Robert's car is so amazing. He drove here so fast my heart was in my throat the whole way. The room in just lit with candles. It's so romantic. I feel so lucky to be with this handsome rich man.

A waiter comes in with two martinis.

Robert says, "I thought you might join me in a cocktail." He raises his glass for a toast and signals me to raise my long-stemmed glass. "Here's to us getting to know each other much better."

I say, "Yes, much better." He finishes his martini in one go and I struggle to get mine down but manage it. There is an instant warmth radiating in my chest and I feel slightly dizzy.

"Dear, I took the liberty of ordering our food. I'm sure, you'll love it." I smile in acceptance.

A waiter sweeps into the room with a large shrimp cocktail for each of us. Another server arrives with cold white wine and fills our wine glasses. The shrimp is delicious and so huge.

Robert proposes another toast. "Here's to me, the luckiest guy in the world to be with the most sexy woman." He downs his glass of wine completely as I sip mine. "Wendy, it's unlucky not to finish your wine on a special toast like that." I drain the glass to be a sport.

A large platter of beef tenderloin surrounded by roasted vegetables arrives along with red wine in new large glasses. The server dishes the food onto our plates with the flourish of an expert.

Robert looks at me. "Why don't you propose a toast?"

"Here's to me a lucky girl who has met a great guy." We drink the glass of wine down. It tastes so wonderful. I can feel myself getting a bit tipsy. I eat some of the meal. It's perfect and better than I've ever had before. I feel like a princess being courted by a prince.