The One That Almost Got Away

by Tony Tiger

Copyright© 2019 by Tony Tiger

Romantic Sex Story: Optimal Stopping almost got me.

Caution: This Romantic Sex Story contains strong sexual content, including Romantic   Sharing   Swinging   Pregnancy   .

Being a tekkie and math guy, I like to think I make logical choices and decisions. This story is about one such big one that almost didn’t work out for the best.

I was one of the fortunate ones who got into an emerging technology early, got well vested and got out at the top. With a few million in the bank at age twenty-three, it was time to develop the family I wanted. I’d learned about Optimal Stopping, an exercise that guides you into how much time to study a decision you need to make without missing out on a good choice. While mainly applied to such things as apartment shopping or searching for a parking place, it can be applied to lots of situations. I wanted to use it to find a good mate. In retrospect I realize that I ignored the influence of feelings (both mine and a prospective mate’s) and the unpredictability of women in my figuring.

So here is what happened:

I started by listing my desired attributes, age, size, hair color, intelligence, etc. I set up a spreadsheet to rate any candidates on these and other factors I might discover along the way. I’d usually had a girlfriend throughout college and after so I entered them into the database.

The Optimal Stopping formula said I should keep “shopping” until I reached age 26, then make a decision from the best available. I decided to date a woman for about three months to get to know her well, then move on to a new one when another candidate was found. This was not hard-hearted as I treated them well and made no promises.

Some were gold-diggers; some were shopping like I was; some were just out for a good time and a hard cock. No matter, each one added to my knowledge.

When I was twenty-four I met and began dating Kaitlyn who was twenty, the lower end of my age range. She was a redhead (a plus), athletic yet full bosomed (two plusses), working on a Master’s degree (a plus) with a quiet but intense personality (two plusses).

On the third date I invited her for a gourmet meal at my luxury apartment. A guest chef prepared and served it. She was appreciative of the experience but not overwhelmed. When I opened a second bottle of champagne and invited her to my Jacuzzi, a standard ploy to get a woman naked and in the mood for copulation, she acted as if she did that every day. When I began to get physically intimate she had to say, “I’m a virgin although I’ve had some sexual experience short of intercourse. You are attractive so if you can enjoy my body without vaginal penetration we can go on from here.”

I agreed and we dried off and retired to my bedroom. Her body was delightful to explore. Oral sex with her was better than full coitus with some others I had fucked so I asked her to spend the night. We went out on the balcony naked and played some more before sleeping the night through.

When she left in the morning she said, “I hope I wasn’t a disappointment to you. You respected my limits and that is why I will see you again if you wish. I’m not against full intimacy; it just has to be right.” A kiss and she was gone.

But not from my head and I asked her out again. Two dates later I was balls deep in her absolutely delightful pussy and she was squirming and squealing with her first cock-induced orgasm. We became a couple.

But then the clock ran out on the relationship. I’d found a busty blond that was itching to fuck me so I took Kaitlyn away for a luxury weekend and broke up with her when I took her home. Her passion had been considerable that whole weekend but I did what I had to do. She took it surprisingly well and thanked me for all the nice things I had done for her.

On my twenty-sixth birthday, the “shopping” would be over. I would spend much of the day going through the long list of possibilities. But four days before that I received a card in the mail.

It read, “You are invited to Katie’s second birthday party. We hope you can attend”. Enclosed was the picture of a cute little girl with red hair. On the back was her name and “Yes, she is yours.”

I had moved away from my home town and was involved in another venture by that time so I hollered for my P/A, Mildred. “Cancel my appointments for the days on both sides of this one. Book me a flight to my home town and get me a hotel room for then too.”

She was startled since I am rarely so spontaneous and inquired, “Am I going with you?” She often accompanied me on business trips and we shared a bed, not for economy but for enjoyment.

“Not this time. Personal business.”

I had texted Kaitlyn on her old number that I would be attending and wondered if we could get together the night before. She sent her regrets but said I could have the evening after the party.

My night in the hotel was restless. The party was Saturday afternoon at two PM and I was on time. I had no idea what to buy a two-year-old-girl so decided to make an offer of an activity of her choice at the party.

I was almost the only man there. Three other moms and their kids plus one dad were present. I was introduced as a friend and just hovered in the background, totally out of my element. When it was over and the guests had left, Kaitlyn gave me a simple kiss and announced, “One of my friends will keep Katie tonight so we can spend some time together”

We went to a little lakeside bar and restaurant where we had often gone on dates. I selected an outdoor table and ordered a bottle of the wine I remembered she liked. The first chitchat was basic, reestablishing contact after all that time. Finally I moved into deeper water, “Tell me about Katie.” A simple question.

Kaitlyn took a big slug of wine, turned to face me directly, and launched into her story. “I knew from one of your past girlfriends that you were setting it up to break off with me when you made plans for the fancy weekend. I stalled a little bit so that it would coincide with my fertile time and had my IUD taken out. I was and still am very much in love with you and wanted to keep a part of you with me. You even commented how amorous I was those last days together. Since it was my idea, I didn’t think you had any responsibility and, other than putting your name on the birth certificate, I have not asked for any help at all. I contacted you now because Katie is getting old enough to wonder about her father like her other friends have.”

My turn to talk, “She certainly is a cutie and after seeing her I don’t doubt that she is mine. I also know that you are an honest person. Let me tell you about the process that has guided the last several years of my life and perhaps that will explain why I did what I did with our relationship.”

I spent the next half hour explaining what I was doing to find a life mate. Sometimes Kaitlyn smiled, sometimes she frowned, sometimes she just shook her head, but made no comments. When I told her that I was in the decision-making phase she did say, “Maybe my timing was good after all.”

“You certainly were at the top of my list.”

With an unhappy look on her face, I heard, “So you were going to pick me out like an apartment or new car? Do you have no feelings?”

I was taken aback by the tone of voice. “Well, we got along together quite well and I like being with you.”

She was still worked up, “So you don’t feel any love for me?”

“I’m not sure I know what love feels like. My parents were not affectionate to me or each other. They always treated me well and took good care of me so I guess that’s all I expect.”

Kaitlyn poured another glass of wine, finishing the bottle, and then polished it off. “Take me to your hotel room. Katie is gone for the night I might as well make the best use of it. I’m horny and, as I remember, you are pretty decent in the sack. I’m sure you’ve had plenty of practice the last two years and I’ve had some too.”

We did the Jacuzzi thing, dried each other off and got on the bed. Other than a few light stretch marks, she was as pretty as I remembered. Her tits might even be a little bigger. Her mouth got reacquainted with my pecker and mine with her nicely trimmed pussy.

We fucked furiously and wordlessly until we fell asleep. Sometime in the wee hours we woke and coupled much more gently, not in a hurry for orgasm. Kaitlyn brought up the topic with, “You’re still pretty good. How do I rank on your scale?”

Ignoring the dig at my objectifying everything, I responded in the dark, “You were pretty damn good for a beginner, as I recall. Whatever you’ve been doing seems to have made it better and I’m really enjoying you.”

She kissed me, clenched my embedded cock, with her pussy muscles, and said, “If you do decide you want me, and I’m not saying I will accept, I want you to know what you’re getting. During parts of my pregnancy I got terribly horny and would fuck any guy that reminded me of you. It didn’t take much either. Since Katie was born I’ve been very selective and there’s been only one guy for the past year and a half. He helps me feel female but he’s not you, even though he looks a lot like you, so I can’t be in love with him.”

We finished and slept some more. I did a lot of thinking in the dawn’s early light as the pretty redhead snored quietly next to me. When she got up to pee I made coffee and we sat in bed sipping it. “Do you have a picture of this surrogate?”

She got out her phone and showed me a recent selfie. “Is his name Derek?”

Her jaw dropped, “Do you know him?”

I chuckled, “He’s my cousin on my mother side. It’s been a family joke since he was born that my father snuck over and nailed my mother’s younger sister. Neither one of them will deny or admit to it.”

She shook her head, “Well, it’s a small town after all. FYI, his cock, and yours feel identical.” She had her hand on mine and continued, “Enough about me. What has this thing been into lately?”

“Only my personal assistant a few times a month when we travel together, never at home.”

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