Best Experience Ever

I'm Dale Markham. In some ways it could be considered tragic that my best sexual experience was when I was twenty one years old. But that was my reality -- at least for a long time.

My older brother Alex and I were always close, despite the fact that we're three years apart, and even though we both had strong, and sometimes conflicting, personalities. Also, he's really odd -- maybe "a divergent thinker" is a better way to put it -- in some ways. His oddness/divergent thinking has really been good to him in one way. By the time that he had turned twenty four he was already a millionaire, having developed and sold several apps that are some of the most popular in the Apple store.

Although his concern wasn't actually justified my brother thought that as a senior at what he considered to be a stuffy Northeastern U S University that I wasn't getting laid enough. He had recently gotten his biggest check ever for the sale of his latest app and he wanted to treat me. With a weeklong school break coming up just a few days before my twenty first birthday he demanded that I meet him in Miami, Florida, for five or six days of fun. He sent me a first class airplane ticket and told me to get an STD test and bring the results with me.

Actually at that point I needed a break from studies since I was trying to end my college career with a bang so I went along -- I mean what college kid is going to pass up an all-expenses paid trip to Miami when it's still cold in the Northeast. Also, knowing my brother's taste in women I was probably really going to enjoy myself.

Alex and I did water sports for the first two days in Miami, competing whenever we could, had extravagant dinners and went to clubs, me with the fake ID I had used the last two years but soon would no longer need. I don't really drink much -- although Alex can -- but I had a great time. I was sure that some babe at a club was who he would set me up with.

The third day in Miami was my actual birthday. We palled around most of the day but since he knew that I wasn't interested in getting drunk he kept getting my curiosity up by telling me that he was going to introduce me to someone I'd really like. Just before dinner he opened up about my surprise.

"Remember how you used to go on in High School about Mom's friend Mrs. Baldwin?" he rhetorically asked with a big shit-eating grin on his face.

Boy did I ever remember her. Most of my teen masturbation sessions were inspired by a photo of her in a bikini that I surreptitiously took at a neighborhood pool party. I didn't want to drool when I replied to Alex's question so I simply said "Yeah -- she was plasma hot!"

"Well, little bro; what would you say if I said that I arranged for an organization called 'Real Soccer Moms' to provide you with an even better looking version of Mrs. Baldwin for the next three nights?"

I was sure that he was blowing smoke about the "even better looking" but if she looked at all like Mrs. Baldwin and I got three nights with her my life would instantly triple in happiness. "If she's even half as good looking at Mrs. Baldwin I'll be in your debt forever," I laughed.

With a Cheshire Cat grin he grabbed me by the arm and led me to the entrance of a nearby high-end restaurant. Standing in front was the sexiest woman that I had ever seen in my life. She did look like Mrs. Baldwin since clothed she looked like she had the same size tits, same round ass, and from what could be seen by her relatively conservative outfit, long sculptured legs. However, her face was significantly more beautiful than Mrs. Baldwin's -- and that's saying something since Emma Baldwin was the most beautiful woman in our hometown (aside from my mother, of course).

"Dale, this is Cindy, Cindy, Dale. Cindy is staying at the Four Seasons and has all of the cash necessary to pay all expenses and instructions to make you a kept man for three nights. I'll see you Saturday and get you to the airport; happy 21st bro," Alex said and then gave me a hug and took off.

"You look a little startled, Dale; did Alex surprise you by hooking you up with a thirty two year old soccer mom instead of some lithe young thing?" Cindy (I was sure not her real name) asked while rubbing her hand over my chest.

"Uh...no...uh...well...not...you see..." I started stammering while looking into eyes so blue that they almost looked unreal and had completely captivated me.

"Never mind," Cindy laughed, taking my arm and then leading me into the restaurant. "The reservations are in your name; I'm paying but you take charge in every way; treat me like you want to make the best impression ever so that you have a chance of getting into my pants tonight," she chuckled.

It took me half the dinner before I started to relax I was so overcome by not only her beauty and sex appeal but also by her charm. I finally did snap out of it and I became as charming as was possible for me.

Shockingly, Cindy really was a soccer mom or a first class actress who had done her homework on what soccer moms are really like because she presented in as cheerful and interesting manner as possible what her life was like, not hiding at all the fact that she had a husband and two young daughters, twelve and ten.

Although not a college graduate she was whip smart, actually able to carry on an intelligent conversation with me about two of my passions, cubist era art and water sports. Plus she had more knowledge of current events than I did.

After dinner she excused herself for fifteen minutes to call her family (she didn't make any secret about the reason for her call) and then we went on a ninety minute long harbor cruise. We followed that with a walk in the lively South Beach area (where she was the most conservatively dressed woman, but also by far the most beautiful) before she gave me a quick kiss on the lips and said "I'm horny -- let's go to my hotel room."

We were in a cab shortly thereafter and once we got into Room 1402 at the Four Seasons -- which had a beautiful view and lavish furnishings and decor -- Cindy was no longer a charming older date; she quickly became an aggressive, determined, high priced call girl.

After she disrobed in record time as she was intermittently kissing me while removing my clothes she whispered into my ear "If you want a life changing experience eat me to orgasm tonight and then hold on for dear life!"

Once she got me completely naked -- hard to do since my cock was so rigid that she almost couldn't get my boxers off over it -- she dragged me into the shower. I washed her off completely, and she me without causing me to blast cum all over the shower stall wall -- which was a real possibility I was so charged up.

We made it to the king sized bed in the room without me spontaneously ejaculating, and then she growled "Get your face in my pussy now, stud."

Her pussy looked heavenly, with sparse pubic hair, a small slit with labia that looked like they wanted to grab my cock, and a protruding clit just begging to be sucked. The fact that her pussy was framed by the best pair of thighs I had ever seen, and a flat stomach, enhanced the view even more.

I went after her twat like a starving man after a taco, using every finger, my lips, my tongue, and my nose. Once I was sucking on her clit with two fingers in her pussy I used my other hand to alternate nipple grabs on her supple natural breasts. It wasn't long before she came with the ferocity of a charging tiger. I continued to manipulate her tits until she came down from her high. Then she grabbed my face, gave me a kiss hot enough to set off a smoke alarm, and then growled "You are going to get so fucked..." and then kissed me again.

Somehow she maneuvered me onto my back and with a smile as big as the Atlantic held my titanium-hard cock upright while she slowly impaled her snug pussy on it. Not familiar with what child birth does to a vagina I was surprised at how tight a mother of two could be -- well that thought was only fleeting because I was already almost in sensory overload.

Cindy could tell how excited I was so in order to prevent premature ejaculation she pulled herself mostly off my cock, and with her thumb and forefinger gently squeezed my cock just below the head until I calmed down a little. She repeated this technique two more times, while vigorously bouncing up and down in between squeezes, until at one point her eyes seemed to glass over and she went wild, squeezing and releasing powerful pc muscles as she moved like on a bungee cord. After one particularly powerful squeeze of my cock with her pc muscles I ejaculated into her with such a force that I was surprised that I didn't eject her completely off of me. Instead she screamed, shook, and after my last salvo into her perfect pussy went limp.

As a wilted though moaning Cindy lay on my chest it was all that I could do to maintain awareness. Pleasure chemicals were coursing through me like the Amazon after a heavy rain and I wanted to experience every moment of the euphoria that it brought. Fortunately I did maintain lucidity and Cindy seemed to snap out of her stupor after a short while. When she did she sat up, my cock still in her twat and mostly still hard, and stared into my eyes like she was trying to reach my soul. "Hey, I'm supposed to give you your best fuck ever, not the other way around," she snickered.

"Don't worry," I chuckled, "you succeeded." I wasn't lying.

After a few minutes more of pleasant dick-still-in-pussy talk she moved off of me, sending what seemed like a 240 volt electrical charge up our spines. When she collapsed next to me we faced each other. I gently ran my hand over her body while staring into her impossibly beautiful face, while she stroked the side of my face, then moved her hand onto my testicles to gently knead them.

"So, what would you like to do tomorrow -- assuming that we have any energy left by the time we're finished tonight?" she cackled.

"I'd honestly like to do anything that allows me to ogle or touch you. I feel like you're a walking version of the most famous and masterful art objects ever," I replied.

"Wow, are you a golden tongued devil," she snickered.

"Let's play it by ear, but probably paddle boarding, jet skiing, going to local art exhibits, and of course a nooner," I grinned.

"Of course, a nooner," she smiled.

"But for right now there's something I am compelled to do that I have never done before," I chuckled.

With that I surprised the hell out of her by going down on her after I had ejaculated in her. At first she was so startled that she seemed to put up some resistance -- but that lasted only a few seconds, until I got my lips on her clit and the fingers of my right hand started massaging her labia majora.

Given how enthusiastically Cindy responded I quickly got the feeling that not only was this the first time I had orally attacked a pussy after ejaculating into it but it was the first time anyone had ever done that for her. This seemed to be confirmed when while I was massaging her clit with two fingers I licked her labia minora and she came with what seemed like the explosive power of a stick of dynamite. When she finally stopped convulsing and screaming her entire body went limp and her eyes glassed over.

As I looked down at her beautiful wasted body my cock inflated with the speed of a balloon connected to a helium canister. Even though she was still partially out of it she groaned in satisfaction when my cock buried itself in her snug pussy with one thrust. After I pumped for a while she seemed to come out of her lethargy with a roar she wrapped her sculptured thighs around my waist, dug her fingers into my back, and pulsated her vagina like a heartbeat. That was too much to take and for the second time in forty five minutes I came with the power of a querulous bull. Her climax was just as ferocious.

Ultimately I withdrew my deflating phallus from her magical chamber, and I spooned her with one hand on one of her breasts. Neither of us had the energy to do anything except fall into a deep slumber.

Sometime in the early morning hours -- I think that the alarm clock next to the bed said something like 3:10, but I can't be sure -- the goddess who called herself Cindy shook me awake. "I'm a little cold Dale because we were so excited to get with it that we're lying on top of the bed, not under the sheets. Let's take a quick shower and then get between the sheets."

"OK Aphrodite," I snickered, and I helped her perfect bubble butt get out of bed, even though I'm sure it didn't need any help.

We showered, showed how comfortable we had become with each other in less than twelve hours by both peeing in the shower, and after relieving our bladders washed each other thoroughly. After we dried off we got between the sheets, again with me spooning her, only before we fell back to sleep I fingered her pussy until it was moist and she was moaning. Then I slowly inserted my rock hard dick into her wet pussy. We had the most leisurely fuck imaginable. What it lacked in intensity it more than made up for in pleasure. When we finally did substantially simultaneously cum our muted orgasms seemed to last an hour. When we finally came down from our highs my shrinking cock was still in her vagina, and we again fell into a deep sleep.

One thing that I wondered as Cindy was getting dressed after our unsurpassable night together I blurted out as soon as it popped into my mind. "Cindy weren't you taking a risk by agreeing to be with me for three nights. How did you know that I wasn't a pervert or ax murderer?"

Cindy laughed, and while still dressing said "Real Soccer Moms does very thorough background checks. While I was never told your name, and never will be, just like you will never know my name, the investigators did and checked you out thoroughly. They even gave me a photo of you before I committed, along with information as detailed as what some of your past girlfriends said about you. What cinched it for me that I could trust you was that two of your unnamed girlfriends were disappointed that you dumped them but had nothing but glowing things to say about how you put them first when you were in a relationship."

That surprised me. "I wonder what ruses they used to get people to talk?" I asked.

"Beats me," Cindy chuckled. "I just reviewed the information; I don't know anything about their investigative techniques. Now stop asking stuff like that, zip me up, and kiss me."

I smiled, and then complied.

The next two days and nights with Cindy were like heaven on earth. We packed a week's worth of activities into two days and nights but made sure that our activities included regular and other-worldly sex; around noon, before dinner, and a couple of times each night. The grand finale at 8 a. m. of our last morning was doing it doggy with a butt plug up Cindy's ass, causing us both to cum even more powerfully than during any of our previous copulations.

There was one thing that disturbed me, however. As absolutely phenomenal as all of the sex with Cindy and activities had been what thrilled me as much -- or maybe even more, though I didn't want to admit it -- as anything else was one hour where we simply cuddled on the couch in our hotel room and watched a dumb situation comedy. We laughed at it as much as with it, and periodically exchanged smiles, kisses, and back rubs. Why that disturbed me was because I knew what it meant -- I had fallen in love with her!

At breakfast of the morning after our last night together, and the finale, I held one of her hands and said "Cindy it's almost impossible to believe but your personality and inner self are as beautiful as you are physically. You're always upbeat and have a smile on your face."

"It's easy to be upbeat around you, Dale," she smiled.

"The last three days and nights with you were the most fun of my life; more fun than all of the Christmases, birthdays, and Fourth of July's in my life combined," I earnestly said.

I actually saw Cindy swallow hard when I said that. She regained her composure within a few seconds then said "That's the nicest thing that anyone has ever said to me," as she squeezed my hand and a small tear formed in one eye.

We chatted some more, she paid the bill and we walked out of the Four Seasons restaurant about 11:30 and gave me all of the receipts for our activities and the cash that he had given her that wasn't spent to give to Alex. "I need to get going," she said, "and I know that you need to meet Alex."

"Again, thank you for the time of my life," I said as I gave her a final kiss, hoping that there was no moisture in my eyes. She gave me a last smile, turned, and walked out of the hotel.

I was standing there pensively -- maybe even in shock -- when Alex approached from the same direction that Cindy had exited. He had a surprised look on his face. He gave me a hug then took the receipts and extra cash from me. Then Alex gobsmacked me when he said "I saw Cindy leaving as I was entering the hotel, although I doubt that she saw me. She was crying -- what did you do to her?"

"What?" was my intelligent reply.

"Also, why was she still here when it's almost noon; I only paid her until eight o'clock this morning," Alex said.

My immediate thought was "8 a. m. was when we were in the throes of passion, making love." That's when it hit me. We were making love. Was it possible that not only had I fallen in love with a married call girl with two children but that she had fallen in love with me too?

Fortunately I quickly brought my mind back to the real world. I looked Alex in the eye and said "She probably stayed another few hours because we really hit it off. Thank you Alex for the best experience of my life, I'll always be in your debt -- except..."

"Except what?" he asked.

"Except that she's probably ruined me for any other woman. I just realized that I fell madly in love with her," I sighed.

"You didn't tell her that, did you?" Alex huffed.

"No, but she's smart -- she figured it out," I sighed again. "I need for you to answer one question and then no more talk about the goddess, ever."

"Maybe," he curtly replied.

"How much did you pay her -- not the total cost of my trip to Miami or what you paid Real Soccer Moms, because I know that it was exorbitant; how much did you pay her personally?"

Alex looked like he wasn't going to answer, so I prodded, "Please, bro; I need to know for many reasons that I'm too embarrassed to enumerate."

He stopped walking, looked me in the eye, and said "You're not going to let this go, are you?"

"No; please be my favorite person ever," I continued while thinking to myself "except for Cindy," "and tell me. I'll do anything you want!"

"Anything I want, huh? OK, I'm sending you a technical proposal; look it over and give me your honest and technically complete assessment of it," he replied.

"Got it," I smiled.

"$12,000 plus expenses," was his reply.

I hugged him then laughed "To me it was worth 100 times that much."

We grinned, walked to his car, and started talking about college basketball teams on the way to the airport.

***********

When I got back to school I was in a total funk. Falling in love with a call girl who was married with two kids and eleven years older than I was certainly was not predictable or sane, but true nevertheless. Only by briskly working out when I wasn't studying or in class was I able to come out of my malaise and get with the program; I had no desire to date.

I finished college as strongly as I wanted to and had acceptances to two prestigious graduate schools and three great job offers by the time that I graduated, although I was still unsure what I was going to do. I gave Alex a response to his technical proposal that he was very happy with, and which I'm sure he'll turn into another million dollar app.