Serendipity

Serendipity

All characters in this offering that are in a sexual situation are at least 18 years old, including the main character Bradley Prentice.

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According to the dictionary the definition of "serendipity" is:

"noun

• 1.the occurrence and development of events by chance in a happy or beneficial way"

Synonyms include fate, destiny, providence, karma, and coincidence. I've never been one to believe in fate -- and therefore not in serendipity -- however it is the only thing that can explain what happened to me when I was twenty one years old and had just graduated from college with a degree in mechanical engineering. But the origin of my story of serendipity starts well before that.

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I grew up in a typical upper middle class neighborhood. I was a pretty ordinary kid, had pretty ordinary things that I was into such as baseball, basketball, grilled cheese sandwiches, ice cream cones, heavy machinery, and pets. I wasn't really into girls until my sophomore year in High School but I was "into" a woman from the time that I was ten years old.

That may sound strange, but is true.

The woman that I was "into" was a neighbor and a good friend of my mom's. Her name is Caroline Watkins. Even though she was good friends with my mom from their many conversations, which I often was able to eavesdrop on, she was ten years younger than my mom and about fifteen years older than me.

Although I'm not sure what terms I used in my mind to describe Caroline when I was a kid, using my brand of adult adjectives she is an enticing, alluring, and sensuous woman. A noun used to describe her might be "walking wet dream."

In addition to being the most beautiful of any woman in my orbit when I was a kid my attraction to her was because of the way that she treated me. She always talked to me like I was an adult, always had a smile for me, and was always touchy-feely.

When I started having wet dreams I was certain in my mind who was responsible for them.

The best day of my life up until that point was when I saw her in a string bikini at our next door neighbor's pool.

When Caroline was one of the invited guests (the only non-family member over twenty) during my eighteenth birthday party (which was held, for convenience, a week after my actual date) I spontaneously ejaculated in my pants for the first time ever when Caroline gave me a big long hug. I had to change my pants mid-party.

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In addition to being a walking wet dream, Caroline was also a mystery to me. Her husband was a kind of dour guy who seemed to be older than she was by a significant amount. I guess -- as best a male can evaluate another male -- he was handsome, but there was something about him that rubbed me -- and many other people -- the wrong way.

In some of the conversations my mother and Caroline had that I overheard I know that Caroline complained about him being stingy, but despite that, and despite the fact that Caroline didn't ever have a job that she talked about, she always had nice things.

My infatuation with Caroline became a problem after I turned 18 and started having sexual liaisons because often Caroline -- or some of her body parts -- would pop into my mind. When that happened I normally busted my nut, even if it was too early.

After I graduated from college my parents decided that they wanted to throw a graduation party for me. Several of my friends came in for the event and stayed in local hotels. My friend Morton was from a very wealthy family so he stayed in the Four Seasons, while the other three stayed in a Motel 6.

Unfortunately Caroline couldn't attend the party because of "another commitment," but she came by in the afternoon and gave me a big hug. Thankfully I avoided cumming in my pants when she did, but just barely. She looked just as good as the last time that I saw her. There might have been a few lines in her face but her body had more lean muscle -- which was very attractive. When I mentioned it to her she said "Thanks for noticing Bradley; I've been doing Pilates and some light weight-lifting."

The night after my graduation party I took my three buddies from the Motel 6 to the airport. Morton had left earlier because of a family emergency. However, on my way back from the airport he called my cellphone and said "I still have my room at the Four Seasons because I had made arrangements to stay tonight but because of the emergency I had to leave. Someone is coming there at 9 p. m. to deliver something that I prepaid for. So that it doesn't go to waste why don't you go and pick it up?"

"What is it?" I inquired.

"A mystery," he chuckled. "Please, do me a favor and just be there Brad."

"How will I get into your room?"

"I called the Four Seasons, gave them my information and told them to have a key card for Room 2120 ready for Bradley C. Prentice at the front desk. You will have to show your driver's license and tip the desk clerk $10, but if my 'package' is a disappointment I'll refund your ten bucks."

"OK," I laughed. I thanked him for coming, he thanked me for inviting him, and we mutually terminated the call.

It was already 8:29 and the Four Seasons was ten minutes away and my house thirty, so I just drove to the Four Seasons. As expected the clerk had my key card, I tipped her $10, and I went up to Room 2120.

Morton's room was more luxurious than any hotel room I had ever stayed in. It had all the amenities including a whirlpool bath and a fully stocked bar (not a minibar), and a California king bed (even though we're not in California, ha, ha).

I was nosing around waiting for the delivery that was supposedly to occur at 9 p. m. and found a watch and a ring that in his haste to get home Morton inadvertently left behind. He had lots of watches and rings so that's probably why he missed them. I put them in my pants pocket to take them home and mail them to him the next day.

By the time that I finished my snooping a doorbell rang. At first I was puzzled, but then I realized that this room was so fancy that it had a doorbell. I quickly moved to it and then opened it up. That's when I got the surprise of my life.

Standing at the door dressed to kill was Caroline Watkins!

Caroline and I just stared and each other, wide-eyed and gap-jawed for what seemed like a good thirty seconds. Then she got a tear in her eye and was about to bolt. I grabbed her arm and pulled her into the room and closed the door. She had the look of a deer in headlights.

"What are you doing here, Caroline," I asked in a completely non-confrontational tone -- pretending it was a simple normal inquiry.

"Brad, please let me leave. I was supposed to meet a guy named Morton but he's not here so I should go."

"Why were you supposed to meet Morton?"

Caroline started crying. I sure didn't want that. I sat her down on one of the couches in Morton's suite and sat next to her holding her hand. It was breaking my heart to see the heart throb of my life crying. I decided to change the subject.

"I had a good time at my party. Thank you so much for the high end calculator that you gave me as a present. You really didn't have to do that, but it's just the one I wanted," I said in a happy voice, changing the subject.

Caroline controlled her tears a little and then happy with the change in subject she replied "I talked to your mom and she told me you would really like that; I'm so happy that you did. So what was your party like?"

We engaged in light-hearted banter for the next ten or fifteen minutes, and Caroline seemed to calm down. I, however, was getting charged up looking at her thighs -- which were almost completely exposed in the small black cocktail dress she almost had on -- and her cleavage.

I think that she caught me staring down her dress so I quickly asked "How about a drink; there's a complete bar here, not just a minibar. What would you like?"

"Uh...a margarita would be nice, if it's not too much trouble," she responded.

"No trouble at all," I replied when I saw all of the items behind the bar. I made her a small pitcher of margaritas and for me a glass of Bloody Mary mix, no vodka, but it looked like a real Bloody Mary.

We chatted some more about the party, my time in school, her activities including her gardening and the charities she was involved with, for a long time. She was apparently nervous because she polished off the entire small pitchers. Once her words started to slur a little I got back to the reason she was there.

"Caroline, I'm sorry to ask again but I really need to know why you're here. I swear that the mystery will ruin my life for the next decade if you don't tell me." When she hesitated but looked like she might answer I continued with "I guarantee that I will tell no one -- and I mean no one -- the reason. I'll take it to my grave." She looked a little more like she wanted to tell me so I again continued with "You know that I've always been honest; please tell me."

"I need another margarita," she said, holding out her glass.

I took it and made another one as quickly as I could, and gave her the glass. She downed it in one gulp and then said "Promise that you won't judge me Bradley."

"Caroline, I have judged you in one way my entire life. You are the most enticing, alluring, and sensuous women on the planet. You are my ideal woman. That opinion of you will NOT change even if you tell me you came here as a hit man to kill Morton." The last line was delivered with a smile. She actually smiled in return.

She took a deep breath and then said "I'm a high priced call girl."

If she had told me that yesterday I would have been shocked, but given the circumstances tonight that was the logical conclusion so I wasn't really surprised -- although it did make my little soldier salute.

"Has anyone you know ever figured it out?" I asked.

"Absolutely not," she replied. "I only meet people from out of town in high class hotels. I never do anything local."

"You're so sexy, I'm sure that you can have anyone you want," I smiled.

"I do reject lots of guys. If I don't have a good feeling about them, or if they are gross, then I don't sleep with them," she sternly replied.

I asked a few more open-ended questions and she started telling me everything. It was almost like she never had anyone to confide in before and that she needed to. I just let her talk with as few interruptions as possible although I did give her one more margarita, and then only club soda.

Some of the many things that I found out were: her husband was so cheap that if she wanted anything more than basic she needed to get it herself; while he had been charming and romantic when she first married him he was now disinterested, was a lousy lay, and had a low libido; she was saving money to divorce him since she was sure that he was hiding his money and she would get little in a divorce; she got into being a call girl by accident but then realized since she was constantly getting hit on she might as well profit from it; she always practices safe sex and requires an STD test from a respected lab and extra payment if no condom; she has a sly website that doesn't show her face or any distinguishing marks although it does display her assets; she is honest (within a few years so detailed accurate information that would allow someone to trace her isn't provided) about her age of 36; there is a detailed procedure to go through to contact her; and she is highly paid.

She regurgitated much more than that above -- those are just the highlights.

When she finally ran out of steam I asked "So Morton knew that you were 36?"

"Actually, 34," she replied, "like I said the information was generally accurate but not precise. I did lie about being a mom because some guys seem to get off on MILFs and from my first conversation with him it was clear that he was one of them."

"How much did he pay you?"

"Uh...about $2,000 in bitcoin."

I chuckled -- she looked a little miffed until I said "That's about 1/100th of what a night with you would be worth."

"Do you really mean it?" she sincerely asked after a long pause.

I pulled her to me and kissed her lightly on the lips. Then in the most sincere voice I could muster I said "A night with you would be the highlight of my life, never to be surpassed if I live to be 100, my dream since I was mature enough to have such dreams," and then lightly kissed her again.

She stared at me the longest time. "Do you want to make love to me Bradley? Tonight?"

"More than anything else in the world," I responded giving her another light kiss on the lips.

With the pull of one string she was naked, and as soon as her dress hit the floor she was on my lap feverishly kissing me with a passion I've never seen before in a human being. After five minutes of touching each other's tonsils I stood up lifting her with me, threw her on the bed and then vigorously devoured her pussy lips and clitoris while using two digits to find and stroke her G-spot.

Caroline kept moaning "Oh yes, Bradley, Oh yes," over and over again through three orgasms before I let up.

When I finally let up her eyes were half closed when she stared at me as I stood up, quickly removed my pullover shirt, footwear, pants and boxers not taking the time to bother with my socks, and then I mounted her. "Oh shit, do you have a condom?" I asked when my brain started working for a few seconds.

"I don't need one with you, lover," she said with a smile. I said nothing more.

Every dream that I ever had had about Caroline swept through my brain as I slowly buried my sword in her scabbard. By the time that I was fully ensconced I realized that the reality was better than any dream. She was tight, soft, wet, and muscular all at the same time. She also really knew how to fuck -- or make love, which it was for me but I didn't know yet if it was for her.

She worked her hips and pc muscles with an alacrity so far beyond my experience that it was like I was in another solar system. Her nipples moved back and forth until I latched onto them first with my hands, and then periodically with my mouth. She continuously moaned "Oh Yes, Bradley, Oh Yes," as I pistoned in sync with her bucking. After a delicious time she yelped and I groaned as I deposited the largest load of my life where my entire adult life I fantasized it would be, as I almost passed out.

I think that the only reason that I didn't pass out was because my subconscious mind was afraid that I might hurt her if my entire body weight came down upon her and it kept me cognizant.

After we survived several aftershocks, each of which was better than any fuck that I had ever had before, we lay next to each other staring into each other's eyes.

"You're a goddess," I smiled.

"You're amazing," she smiled back.

"That was the best thing that ever happened to me," I honestly replied.

"I know why -- because I felt it too," she sighed.

"What?" I asked.

"Because it wasn't just physical; it was emotional. I could tell that you really cherished being with me and that made me feel so special. I wasn't a high priced call girl during our copulation -- I was a lover."

Emotion blasted out of all of my pores, and overcame me. I zealously kissed her on her lips, neck, nipples, and chest. She purred and giggled. When I went down on her and started eating her again she was truly surprised -- but, of course, didn't try to stop me.

By the time of her next oral orgasm my cock we re-energized. I abruptly turned her on her hands and knees, licked her pussy one more time, and then buried my cock once again. With one hand I grabbed a nipple, and I inserted the thumb on my other hand into her pucker hole. We banged like percussionists until once again she screamed, and I grunted, as the largest second payload of my life was blasted into her anxious pussy.

Somehow, sometime after that, we ended up with our arms wrapped around each other, face to face, in dreamland knowing that our reality had been better than any dream.

We woke up almost simultaneously mid-morning, took a pee, and then took a shower together. I ran my hands over her perfect body as we periodically kissed then washed each other off. We were barely dry when we returned to the bed, she sucked me for a minute -- which was all that it took -- and then rode me like a rented mule while I mauled her tits. When she looked like she was about to cum -- and my cock wanted to discharge -- I flicked her clit and pinched a nipple. She spasmed in orgasm and when her pc muscles clamped on my cock it released two testicles worth of seminal fluid into her vagina.

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We woke for real when the digital clock next to the bed said 8:54 a. m. We wordlessly smiled at each other, occasionally exchanging snappy kisses on each other's lips. While I vowed that I wouldn't say it, when Caroline lovingly stroked the side of my face I blurted out "I love you."

Her smile got a little brighter when she replied "I felt it last night and this morning. As a married call girl I'm sorry for you that you do; but as a woman it fills my heart with joy. It makes me feel special."

"You are special; I worship you!"

Caroline laughed. "Worship is a little too strong of a word, Bradley, you poor boy; but you do make me feel serene and that the world is a wonderful place."

We took a joyful whirlpool bath together, and got dressed in the clothes from last night that were strewn all around the room.

While Caroline was putting on her makeup on her naturally gorgeous face -- a totally useless activity as far as I was concerned -- I called Morton. I told him about the bar tab, I told him about finding his watch and ring, and without going into detail I told him that his "package" was perfect and that he was now my favorite friend of all time. He laughed, told me that he was happy to help, said that if I returned his ring and watch he'd handle any extra charges for the bar and for breakfast, and we terminated the call with mutual "Thanks, bro."

During breakfast, charged to Morton's room, the banter was light. "Will I ever be able to make love to you again?" I asked Caroline just before we parted.

Caroline smiled and replied "Maybe something can be arranged!"

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Actually lots of somethings were arranged. I stayed at my parents' house for another week, and three of those days I had to go over to Caroline's house to help her with some chore or the other. Usually the chore was servicing her plumbing (not her house's, but hers, ha. ha).

When I left in my recently purchased used car to drive to the city where my new job and apartment were, I met Caroline at a local park on the way so that we could say goodbye with passionate kisses without my parents or neighbors seeing us.

Since I moved to my new city six months ago Caroline has visited me two long weekends, and I went back home for a few days when I knew that her hubby would be out of town.

I love her -- I guess that I always have -- and while she has never said it I can tell from her eyes and the way that she looks at me after we have copulated and are nose to nose that she loves me too. I would marry her in a heartbeat, but her consistent refrain -- which unfortunately I know she is serious about -- is "You need to fall in love with someone your own age and have the love and family that you deserve. I can see you occasionally until that day comes, but if I sense that my relationship is precluding you from finding Ms. Right then it's over between us."

Actually, since she's "Ms. Right" I'm afraid that this is going to end in heartbreak for me when she realizes that I can never love someone else like I love her.

C'est la vie!