Lolita

After going over it in my head for days, I always came up with the same conclusion;  I was going to meet an online lover.

My policy on that has changed back and forth the last couple of years. Initially, after talking on the phone and getting one another off, and if geography wasn’t an issue, I would meet the sexy voice in person.

I would have to say after a few of those encounters; my batting average was very low.

Let’s take the last one for example. It went something like this during the initial awkward first minute.

“Uh, you’re Butterfly_350?”

I would ask with my head tilted to the right to see if maybe my eyes were out of whack. Butterfly_350 was supposed to be 5’7”, and 120 pounds.

In her profile pic, her hair was long, wavy and luxurious.

Naturally, the face in that same pic had virtually no resemblance to the one standing in front of me then.

Gone were the rich full lips coated in pink lip gloss. Those lips were now just one thin line smeared with a red grease pencil. The same could be said of those sparkling blue eyes that were now as red as her hair, and basically just two slits gouged into puffy cheeks.

I shuddered as she shouted, “Gosh…it’s really you! Tommy Crown is standing right here in front of me. Gee, I’d recognize you anywhere. You look exactly like your profile pic!”

At that moment I wanted to run, but my parents raised me to be polite.

“Aww, thanks hon…you look …well, you look great yourself!”

Naturally, she’d fluff at her hair and say something like, “I was afraid you wouldn’t recognize me. I did change my hairstyle a bit, and uh…put on a few pounds.”

The long wavy hair, (if that was even hers in the first place) had been whacked to little patches of fine red hair that reminded me of a half plucked chicken. The few pounds had latched onto her entire body. I should have asked more questions about the ‘350’ in her user name, so chalk that one up to me.

Then I gave her a tiny peck on the forehead and dragged her by the elbow away from the crowded airport foot traffic. I wanted the darkest, least conspicuous place I could find to deliver the news.

I settled for a closed coffee shop that had open seating.

As I dropped her in the orange plastic chair, she yanked my tie and pulled my head down even with hers.

Fuck.

I closed my eyes as she proceeded to kiss me over and over. It reminded me of my Aunt Alice who never kissed me once when she greeted me when a dozen suited her more. I was only 8 years old, and found it annoying as hell.

After butterfly_350 finished her assault, she released my tie, and I stood quickly. There were no fears of an erection betraying me, as my cock had disengaged on first glance of my online lover.

Ok, that one didn’t quite live up to the billing.

I dragged her back to the ticket counter and laid down my Platinum American Express and urgently said, “one way ticket to anywhere asap!”

Butterfly_350 patted my hand and calmly said, ‘It’s ok dear. I can pay to get myself back to Rock Island. You don’t feel bad about this; it happens all the time.”

OK, I’m an asshole, but I do have some sense of decorum. I found myself leaning down and raising her flabby chin with my forefinger, then kissed her little red mouth quickly.

I spun on my heels and waved goodbye over my shoulder without looking back.

My point is that I had already discovered that the small step from cyber world to planet earth was a free fall into the abyss.

But, damn it, this new little waif that snuck up on me in the comment section of my blog just had my heart racing.

Even her screen name turned me on. Lolita!

After hours and hours of hammering out messages back and forth, and countless sexy pictures being exchanged, we made the decision that this was probably more than a casual fantasy.

Skype was out of the question since two women live with me 98% of the time here at my Florida home on Sanibel Island.

Phone sex was also tricky for much the same reasons, so once again, I hopped on a plane and headed to our agreed upon rendezvous.

After dozens of emails we discovered something wrong with just about every place on earth that favored a fuck fest.

How about an Alaskan cruise? Well, we’re stuck together for 8 days which is cool if we hit it off. But, if she turned out to be a goat instead of a Lolita, well, look for me overboard!

A weekend of horseback riding at Scotty’s Dude Ranch at the base of the Grand Canyon looked promising until Lolita claimed she was allergic to hay.

It was the beginning of summer, and Arizona’s Red Rock Canyon was nice and remote in Sedona, but also hotter than Hades.

Anywhere north was cold and neither of us fared well with red cheeks and sniffles.

So, the most logical place for our rendezvous to me was my old standby.

New Orleans.

Ah, yes… ‘The Crescent City” full of grace and charm, well…except for the four thousand FEMA trailers that had been abandoned over in the ninth ward, but to most folks, Katrina was well behind them now, and the ‘new’ New Orleans was in full swing again.

Since I considered this to be a chance to impress,  I booked the penthouse at ‘The Banks’, which as the name implies sits on the banks of the Mississippi. It is known to be the best of the best in luxury hotels on the river.

My plans included dinner at 8:30 p.m. at Pat O’Briens in the French Quarter, and a midnight cruise on the Delta Queen, an old fashioned riverboat that catered to young lovers.

Then, if all went as planned, we should end up in bed back at the Bank’s by 2:00 am, where we would make passionate love until daybreak, and then fall fast asleep with her leg draped over my thigh as our mixed results trickled down to the satin sheets.

But, right now, it was time to go to the airport to pick up Lolita.

Naturally, a white stretch limo was under the canopy at the Banks, curbside with the driver standing rather stately holding the right rear door open for me.

The driver nodded as I slid in and as he walked around to the driver’s door, it suddenly occurred to me how foolish this whole thing was.

Now, remorse isn’t usually an emotion that I easily embrace. I tend to make decisions and see them through. So far, with the exception of a few minor bumps in the road, I’ve managed quite well in the pursuit of women, so I had no idea why I was suddenly questioning myself.

But, as I gazed out the darkened windows and watched New Orleans speed by as we zipped down I-10, that’s exactly what I was doing.

Why in the world would this stunning 19 year old girl want to meet someone like me?

According to her, she’s read every one of my stories, and understands that while they may not be 100% true in terms of names and dates, the overall description of who I am is pretty accurate.

From my profile pic to my descriptions of my countless indiscretions, she knows exactly what she’s getting into.

The driver pulled up to the international terminal, since my Lolita was flying all the way from South Africa for this crazy adventure.

The driver let me out and I quick stepped through the ground level portion of the terminal and hopped on the escalator. I was to meet her at the bottom of the escalator, but simply couldn’t wait.

I stepped off and headed for gate 57 which was at the far end of the terminal. My mind raced as I looked at my Rolex for the fifteenth time in the last ten minutes.

In my mind’s eye, I imagined a small woman around 46kgs, or 101 pounds, with dark brown hair, and chocolate eyes. She would probably be wearing something comfy like teenage girls do. I’m guessing those expensive jeans that have shredded knees, and some kind of cutesy tee shirt from some fabulous hot spot in Johannesburg, and comfy flip flops.

I nervously lit a cigarette and dragged on it heavily. The calming sensation was instant and gratifying. Then I remember she didn’t smoke! I stubbed it out and fanned my face.

I leaned forward and rested with my elbows perched on my knees and once again, wondered if I was doing the right thing. After all the ‘chats’ and emails, I suddenly realized that I didn’t really know her at all.

All that cyber stuff was supposedly just a fantasyland for adults. It wasn’t real, everyone would say. It didn’t matter if the other person was married, single, bi sexual, lesbian, gay, or even a real person.

She could have been a ‘bot’, a ruse to get wealthy men like me to agree to meet somewhere, only to be bush whacked for my Rolex and Amex card.

Once again, I found myself rubbing my wrist subconsciously hoping I felt my watch.

Just as I started to bolt, the passengers from her flight were deplaning about forty feet away. They were all dragging those wobbly suitcases as they shuffled along. I didn’t see one happy face.

I guessed the 15 hour flight had made them weary, and once again, I kicked myself for my stupidity. With all my travel experience, why did I make dinner reservations for 8:30 p.m. when the plane was scheduled to arrive at 7:50 p.m.?

Surely, she would be tired and would need some recovery time, and time of course to shower and make herself beautiful.

My stupidity was overwhelming me until I saw her.

Well, actually I heard her before I saw her. The click clacks of her stilettos were music to my ears compared to those damn carry-on bags with loose wheels.

It must be her. She was the last to pass through the gate and I’d not seen any beautiful women in ragged jeans and too tight tee shirts pass by.

This stunner wasn’t wearing jeans or a tee shirt.

Lolita was drop dead gorgeous in a little black cocktail dress, a string of pearls around her delicate neck, and a huge white, wide brimmed floppy hat.

The Kentucky derby came to mind where the women, even the not so pretty ones looked sensational in hats just like the one she was wearing.

How was it possible that there wasn’t a hair out of place, her makeup was perfect, and her clothes showed no signs of travel?

Before I knew it, she was right in front of me.

I looked down as she looked up, “Hi, Tommy darling!” then ran her pink lips across mine slowly.

The kiss was long, slow and dreamy as she held the back of my neck and caressed it with her fingers. There was no tongue; as that would have ruined it.

It was the kiss she had longed for from somebody all her young life. It certainly was worth waiting for on my end as well.

My cock pushed up to my waistband to see what all the commotion was that had stirred him from his nest above my balls. It was all I could do to keep from grabbing her ass and pulling her to me just so she would know what she had done to me.

The urge subsided when I saw people gawking at us. The kiss ended as we gazed in each other’s eyes.

“So, you’re the Lolita?”

“Uh huh…and you’re the player…Tommy Crown.”

I caressed her face with the palm of my hand and remarked, “You’re stunning” then kissed her once again softly, grabbed her hand, and headed for the limo.

“Thanks baby. You’re pretty stunning yourself.”

With those words, my cock snuck up to my waist band to take a peek.

It was uncomfortable walking to the escalators, so I let him go back to sleep.

The white stretch was curbside and the prim driver had the door open wide as we slid in.

As we left the curb Lolita asked, “So, where are you taking me player?”

“I made reservations for dinner. I thought you might be hungry.”

“Oh, I’m hungry alright, but not for food. I had dinner on the plane.”

I’m not ordinarily caught off guard by such comments, but coming from the mouth of someone that looked so elegant and refined did throw me. Lolita had the face and voice of an angel and had me completely off my game.

But, she was expecting a strong, decisive man that could take control of any situation. That used to be me, but she had me so flustered.

There wasn’t a single sign that she was a teenager other than her young face. No bubble gum, no earphones stuck in her ears, and certainly no jeans or tee shirts.

So, after I regained my composure, I took control.

“Well, we don’t have to go to dinner. The Hotel is only twenty minutes away. Maybe we should just go there and get you settled in.”

“Yes, my love. That sounds perfect. I’d like a chance to get out of these clothes and maybe take a hot bath.”

Then she gracefully removed her hat and released the pin that held her hair in place. She shook her head and tousled her hair until it fell into place framing her face with ringlets of silky hair.

Lolita was certainly breathtaking as she lay against my arm and turned her head up to me for a kiss. My lips pressed hers gently and her cherry lip gloss smelled great and tasted even better. I thought it was the perfect kiss at the perfect time.

But, apparently she didn’t.

“Baby, I won’t break. Where’s that player that always knew how to turn me on with just a few words. The one that French kissed me on the screen and I felt it. I’m here now, so I’d like to actually have one in person.”

For once in my life I felt completely awkward as the teenager crawled in my lap and took my face between her small hands.

“Now, this is what I want.”

Suddenly, she took my face in her hands, leaned to my parted lips and slid her tongue in my mouth. My cock quickly sprang up in my slacks knowing he was about to see some action. Our mouths clamped together tightly as our tongues danced. Saliva dripped from our chins and she caught the stringers with her fingers and dangled them back in her mouth.

Oh, she was hungry alright. But, her hunger didn’t match mine.

I said to the driver, ‘Take the long way. About an hours worth.”

I saw him looking at us in the rear view mirror as he smiled and said, “As you wish Mr. Crown. How about a nice long drive down by the river?”

“Sounds perfect.”

I hit the power button for the privacy curtain that turned the backseat dark and quiet.

We began making out and undressing simultaneously.

Now, completely naked, I laid her back on the soft leather and pushed her knees apart. My lips kissed her ankles, then the backs of her knees. A hand touched my long salt and pepper hair as I moved to her inner thighs. I kissed them softly; first one then the other as my Lolita moaned. My hands lifted her thighs as she placed her legs over my shoulders. I could smell her arousal. I wrapped my arms around her thighs and slid my hands to her delicate pussy. It was moist and shiny from our hot kissing. I used both thumbs to slide up and down her juicy slit preparing it for my tongue.

“Oh my God!” she whispered as my tongue slipped up her slit like a kid on an ice cream cone.

Again and again, I licked and again and again, she said, “Oh my God!”

I nudged her pussy open with my nose and darted my long warm tongue in and out as she wiggled and panted.

My right thumb brushed her clit as my tongue slurped on her.

“Ohhhh...FUCK!” she screamed as her legs began to tremble. Finally, I knew I was in my element. I wet my right forefinger from her juices and rubbed it around her tiny asshole.

She flinched and squirmed and almost protested as my wet finger urged its way up her ass.

“Oh God...Oh fuck...Baby...you’re driving me crazy!”

That was all the inspiration that I needed. My finger picked up the pace in her ass, matching my tongue in her hot pussy until I sensed a wave of pleasure uncoiling from inside her.

Lolita bucked against my mouth and finger and as I looked over her tummy I watched her toss her head back and forth as she cried, “Oh, fuck me, fuck me, fuck me …FUCK ME!”

My finger pounded into her hot ass quickly as my tongue sucked on her puffy clit. Her juices began to flow over my chin inspiring me to fuck her. I was on top of her burying my big thick cock in her tiny cunt before she knew what happened.

“Oh God yesss..I’ve waited so long for this baby! Fuck my little pussy!”

She hooked her arms around my neck tightly as her legs wrapped around my ass. I kissed her harder than I had kissed anyone in a long time, and she made me feel like no one had ever kissed her that way before.

Now, stuffed with my big cock, she rode me perfectly to a mind blowing orgasm.

Lolita sobbed as she arched her back and kept thrusting, sending our mixture squirting from her pussy.

“Oh dear God…I never EVER imagined this!!”

It was one of those moments that we get to experience in life that imprints your brain.

I lay on top of her and kissed her all the way down River Street.

She was still kissing my neck as the drivers voice came through the speaker, “Excuse me Mr. Crown. Shall I do another lap or take you to the hotel ?”

We looked in each other’s eyes grinning.

I pushed the intercom button and replied, ‘The hotel!”

My Lolita grinned as she massaged my heavy balls, “Oh player…you sure about that?” then kissed and slurped on my throbbing cock.


Then lit a cigarette and French inhaled slowly.

This online lover was more than I expected.

Meet Lolita!!