Dating Service Dilemma

by Phoenix Arrow

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Reluctant, MaleDom, Spanking, Humiliation, Oral Sex, Size, .

Desc: Sex Story: A woman enters a dating service looking for a mate. Soon she must choose between a good looking romantic, or a rude womanizing pig. I wonder which she will choose?

This work is copyright © 2002 by Phoenix Arrow. You may download and keep copies for your personal use as long as the author's byline and e-mail address and this paragraph remain on the copies. Please do not post this story to any web site without permission from the author. All other rights reserved. No alteration of the contents is permitted.

Hello, my name is Jessica and would consider myself to be a successful woman. I am vice-president of an accounting firm, have my very own house, and just bought a new jaguar. All in all, I'd say I was doing all right for myself. However, the one thing that I am lacking is a man. I am a very independent woman and a slight feminist, but most women have that need to be held by a loving husband.

However, my lack of a man is not because I'm not good looking. At 28 I'm no model, but I still have all my charms, from curvy hips, to long legs, to my C cup breasts, and what all my friends tell me is an attractive face. And its not to say that I haven't tried, but most of the men I've dated either had one problem or the other, and I never quite found the one I really wanted to marry.

It was late on Friday when Sally, a fellow vice president and my very good friend walked through the door and rushed up to my desk.

"Hey Jess, you've got to try this".

She came around and started typing a web link on my computer.

"I was walking down the hall this afternoon and saw some of the secretaries huddled around one of the computers. When I asked then what was going on, they showed me this".

On the screen was apparently a dating website.

"When I asked the girls about it, they told me it works really well. Several of them have already been dating men from this site, and they all seemed very excited about it".

I took a closer look at the screen. It appeared to be a legitimate online dating service, with links for men or women.

Sally looked over at me with a wink.

"Come on Jess, lets give it a try."

I looked at her and gave her a sarcastic laugh. "Oh don't be silly, these things never work."

"How would you know, have you ever tried it?"


"See, and it couldn't be any worse than what ever you've been trying so far."


"Sorry, but its true. Now come on, lets give it a go."

I sighed and gave in. "Ok ok, but only if you do one to."

"But I already have a boyfriend".

"Than I guess I won't be doing it."

"Ok, I'll just do it for fun."

Sally took the mouse and clicked on "Find a Man for You".

The next page revealed a type of pole. On it was a list of 5 questions with answers that asked for all things I would look for in a man.

The questions were:

1. How successful should he be?

A. Very Successful B. Moderately Successful C. Success not important

2. How Good Looking should he be?

A. Very attractive B. Moderately attractive C. Looks aren't important

3. When at a restaurant, he should?

A. Let me order for myself B. Ask me what I like and order for me C. Order for me without asking

4. How would you prefer an argument to end?

A. A compromise B. I win C. Always he'd win

5. In bed, how would you prefer he act

A. Romantic B. Plain C. Rough

Sally encouraged me to take this seriously, so after studying each question, I choose: Very Successful, Moderately Attractive, Let me order for myself, A compromise, and Romantic.

I clicked submit. We waited for about a minute for it to process. I could tell Sally was excited for the results. Soon a list of about 15 men popped up. Apparently they were the ones that most closely matched my answers.

After looking at all the men, one caught my eye. His name was John. He was a lawyer and a partner for a very large law firm, about 35, and from his picture looked quite attractive.

I pointed him out to Sally and she clicked on his name and up popped his profile.

John, 35. Very Successful, charming, good sense of humor, handsome. Is looking for a woman that will be his best friend and lover.

Sally printed his phone number and handed it to me. "There you go, your perfect man. You really should call him. What's the worst that can happen?"

I smiled, then folded the paper and put it in my purse.

"Ok, my turn. Since I already have a boyfriend I'm doing this just for fun remember."

We reloaded the poll page and the list of questions came up again.

"Hmmm, I have an idea. Why don't we choose all the worst traits we could possibly want in a man. I mean select all the bad answers to each question. I wonder if there are any real guys that pathetic out there."

So with both of us giggling the whole time, she choose: Success not important, Looks aren't important, order for me without asking, For him to always win arguments, and for him to be Rough in bed.

We giggled as the results loaded onto the page. Then a list popped up, if you could call it that.

There was just one person, and judging from his picture, was a very unkept disappointing man. Sally and me both laughed as we read his description.

Billy, 37. Very Demanding. Has trouble keeping jobs. Has tendency to be very opinionated. Is looking for a special kind of girl that will take care of his needs.

Sally wickedly laughed as she hit the print button. She took the paper and shoved it into my purse. "Here Jessica, if the other guy doesn't work out, you can always try this winner." and she ran for the door laughing.

Before leaving she turned. "But seriously, you should give that guy John a call, it couldn't hurt." Then she left.

I laughed to myself at her amusement with this dating game, then went to reach over for my purse to remove the low life's paper. Just then a client called. By the time I was done with the phone, I had forgotten all about the date papers.

Later that night, after I arrived home, I dug into my purse to get my keys when I found John's profile. After looking it over for a little bit, I thought to myself: "What the hell, I'll ask him to one date and if it doesn't go well, then that'll be it".

I picked up the phone and introduced myself to him. After we started talking, I discovered that I was really enjoying the conversation. So when he offered to meet me for dinner on Saturday at this nice restaurant downtown, I agreed.

By Saturday evening I was getting really excited about the date. I was having a really good feeling about this. I arrived right on time, 7:30, and saw he was already there. I was really impressed with his looks. The picture on the web did not do him justice. He was a real hunk.

He was also a perfect gentleman. He gave me flowers, then held my chair out for me. When the waiter came he sat back and allowed me to order. Through out dinner, I got to know him even better. He was well off and very successful, but his work never gave him the time he wanted for dating. Now at 35 he wanted to start a family.

After a wonderful dinner, he paid and then walked me to my car. Here he again acted the perfect gentlemen, kissing my hand and suggesting another date. I told him he could call me and we'd arrange it.

When I got home I was so excited, I just had a fantastic date with the perfect guy. I called Sally immediately told her the good news, and she was just as excited.

"I'm so happy for you Jess, I knew this would be good for you. Was he really that impressive? Wow. I guess you won't be calling the other Mr. Right than huh?" I could hear her laughing on the other end.

I laughed a little to, then we said our goodbyes and hung up. This reminded me of the other dating profile still folded in my purse. I even forgot his name.

I grabbed my purse and began searching for it and found it buried at the bottom. I looked at the name one last time. Billy Thorpe. A special girl in deed. Laughing to myself, I crumpled up the paper and threw it at the wastebasket. However, it just missed, bounced off the top and landed behind the basket.

As I fell asleep, all I could think about was how wonderful this new guy in my life was, and dreamt of the possibilities.

During the next two weeks I had dated John 5 more times. I was completely falling in love with him. He was the perfect guy, always caring about my needs, giving me flowers, treating me with respect. By the sixth date he invited me to his beautiful house and we ended up sleeping together. He was so passionate and sensual it was unbelievable.

It was around this time on a tuesday that I decided to clean my room. When I began cleaning the over flowing wastebasket, I noticed a crumpled paper behind it. Making sure it wasn't anything important, I picked it up and uncrumpled it. It was Billy's profile.

I decided to read the profile again.

Billy, 37. Very Demanding. Has trouble keeping jobs. Has tendency to be very opinionated. Is looking for a special kind of girl that will take care of his needs.

For a second I thought how horrible it would have been if I had met Billy on my date, instead of the love of my life. I feel really bad for any girls that managed to be fixed up with him. What must have it been like to have gone on a date with a guy like this.

When I saw his phone number at the bottom of the page, a wicked idea came into my head. With me seemingly being the luckiest girl in the world by finding the perfect guy, I wanted to see what the other end of the spectrum looked like. I wanted to give this loser Billy a call and see just how much of a creep he really is. Not that I'd actually go on a date with this guy, but I'd just like to hear how it could have been.

.... There is more of this story ...

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Story tagged with:
Ma/Fa / Reluctant / MaleDom / Spanking / Humiliation / Oral Sex / Size /