When I was younger I would look forward to the serendipity section of "real" letters to skin magazines, those unbelievable stories that, upon reflection, may or may not have actually occurred in real life.
I mean I'd never thought I'd get a blow job on a train, but well, it happened...just like I had once read in a magazine. I'd never screwed my sister, but then, who would want to?
Reading those stories back then was so very exciting. Now we have Literotica, where people spin yarns of all kinds, many of which undoubtedly are based in part on real live life occurrences while others, well, are the results of active, wishful imaginations.
My buddy Steve, for instance, and I were sharing some brews when he just had to tell me how he'd banged a woman at work he'd been flirting with for years. He did her in a storage closet. No reason it wasn't true!
Those mind blowing, out of the ordinary experiences are way too few and are way too far apart for this guy. Most of mine centered on the unfaithfulness of my fucking whore of an ex-wife, which by itself proved there are a lot of those serendipity experiences out there because she played a starring role. Not bad, except for the fact she was having them with a score of other guys, not yours truly.
Still I have had a fair share of hot experiences. The best are mere happenstance. Unplanned moments in time that you have to tell someone about - but by the same token, you can't tell your better half, your significant other, your wife or partner. They might be innocent, or sometimes pre-meditated adultery.
I had dated a sweet, innocent girl in high school, Chloe, for months of my senior year. She was a pretty young sweetheart of a girl. We went to dances, dinners, movies and hung out together, not as a couple because we weren't steady or anything, but we were close. She did date a couple other guys, but we had something special.
Over the months we'd kiss, hell we'd made out and let our hands wander all over each other's clothed bodies. So much wandering that I'd had several wet dates rubbing against her or with her.
I'd asked, begged, cajoled and tried every trick in the book to have her jerk me off, blow me and even offered to lick her pussy. "No way, Rob, no way." It wasn't to be. No matter how I asked her in the car at Crum Creek Park among the parked cars other lovers, no actual insertion sex was going to happen.
Yet playing with those boobies covered by thick and soft sweaters wasn't exactly a chore, and fake fucking her on the floor of her parent's basement was pretty hot as well. We shared a lot of youth together as 18-year-olds before going out separate ways to colleges on different coasts. Oh we kept in touch, but from afar wasn't the same. We each dated others and after a bit the being in touch got farther and farther apart.
She got married right after college to a future lawyer, working herself as an accounting manager before kids came into the picture. Her husband ultimately because a prominent lawyer, and around the holiday season I'd occasionally see them at her parent's stately brick house.
Our ways had parted, each had our own lives, but every once in a while I'd think of her just wondering what she was up to, how she was doing.
I'd do the same for other girls I had dated, guys I'd known to for that matter, just wondering.
It was surprising when the "friend" request came in from one of those business card sharing sites.
Chloe Simpson wants to link up with you online, a friend.
Clicking though, I saw her photo, smiling in a business setting, and of course I clicked yes.
That led to being able to see her business background and her mine, and over time we exchanged hellos and how are you doing notes.
Nothing untoward, just old friends reminiscing and talking about our families, our worlds and the things we were now doing with our lives. She gave me a shoulder to cry on when Nancy Jean was doing her Blowjob Queen imitation, sucking off guys behind my back that I'd ultimately found out about. Chloe advised me to kick her ass out, but gracefully, which ultimately I did. I'd counseled Chloe ongoing part-time so she could spend more time with her kids, especially since her hubby was a prominent lawyer and they didn't need her salary.
We saw each other a couple times over holidays when they flew in - first class - from the coast, and actually had dinner once when her hubby was speaking in Wilmington at a conference. It was worth the hour drive, as she was just like I remembered, only more mature and, well, pretty.
Statuesque I'd say. She worked out a couple times a week and did yoga as well.
That night she smiled and kissed me on the cheek when the night ended, and I watched longingly as she strode into the lobby of her hotel and presumably into the arms of her husband. Still, it was great seeing her, discussing the good old days, jobs, kids, politics and the economy.
Our friendship continued and we'd regularly e-mail and we made a habit of talking at least once a month. Texting was out - no reason to get our spouses reason to suspect anything, because there was nothing happening between us but friendship!
In a lot of ways we were like old friends chatting, mostly about work, friends and our relationships. Chloe was very helpful with my problem of Nancy Jean, and when she hit me that Charles, her husband, was, possibly having an affair with his executive assistant I tried to be supportive.
Her situation was different than mine had been. I caught Nancy Jean in the act. She merely suspected Charles was straying, but there were late nights and excuses for not making love when he arrived home - even when she dressed inappropriately appropriate for the occasion. In her case, he was the huge main breadwinner and she was on a pre-nuptial agreement that was crucify her, not him, if they split up for any reason.
They continued on, living life, humping on Saturday nights, and traveling royally to this vacation place or that. Always looking good, always being perfect.
The rumor and innuendo phase ended when she was doing the laundry and accidentally found lipstick streaks on his boxers. How he could have been so stupid one can only surmise, but she knew lipstick and she knew his boxers and putting two and two together didn't take CSI. The man was cheating, getting his whistle blown, by someone who wore crimson maestro on their lips.
She looked the other way or was merely resigned at the fact of his transgressions, made the best of it, and I helped her navigate those shark filled waters to remain sane.
It wasn't that she and I weren't inappropriate at times, as we'd disclose intimate details about our relationships when there were intimate details to disclose. She'd talk about how Charles loved going down on her and then banging fast and furious without regard to her orgasm. I'd laugh and complain when my current lover did this or that, or even give her the details of my naughty behavior with Nancy Jean who regularly called on me to help ends meet. That was fine with me, as long as the end of my cock met her mouth!
Chloe was very interested in Nancy Jean from an almost serendipity story angle. I'd tell a tale, embellish when I could, and smiled to myself when I believed Chloe was actually Jilling off to my stories. She particularly liked those centering on Nancy Jean coming to my office to plead for an increase in my monthly stipend to supplement her teacher's pay.
Those naughty calls were exciting for me as well, as I knew I was an incorrigible jerk "making" Nancy Jean suck me off in the office with my secretary right outside the door. But also so very exciting because Chloe got off on the differing ways I'd humiliate my serial cheating ex-wife.
Chloe and I'd trade naughty stories, and every once in a while we'd talk on the phone about those high school days, doing, well, phone sex about rubbing each other off on the basement of her parent's house.
Thinking about it always brought a smile to my face from the fond memories.
All of which brings us to the present, as a couple months back Chloe emailed to say she'd be in Philadelphia with Charles as he would be speaking at a another hoity conference. One thing led to another and we agreed that we'd meet for dinner on the night he'd be sequestered with co-workers and competitors in the conference cocktail party and dinner.
Believe me, I had no false expectations about the night. Dinner and a walk or something, and I was not even remotely thinking "anything" naughty would happen. Just two old friends getting together and having a nice night out.
She met me at the restaurant Moshulu, a legendary Scottish sailing vessel, the world's oldest and largest square rigged sailing vessel still afloat. A fixture on the Delaware River just off Philadelphia's Society Hill, I felt it would be an away from prying eyes location for a fun dinner. It was that and more. Her husband was across town at his convention so the coast was clear. She just said she was visiting some high school friends for dinner while he listened to droning on speakers.
Sitting at a table next to a window overlooking the river I glanced twice at the woman who stepped into the dining room and stopped, looking around. The first look was, well, wow, what a pretty woman. The second one ignited my brain into realizing the woman in the striking black dress was Chloe.
We hugged and sat, enjoying wine and the view of the river in a half moon booth. It was noisy in the restaurant so I slid my ass over toward her and we sat side-by-side where we didn't have to speak loudly to hear each other.
The food was good, the company better, and the night flew by quickly. We talked about today, but focused heavily on the past where we'd trade stories about the people we grew up with and what they were doing now. About people we'd dated, and there was of course some innuendo about the two of us doing naughty things in the car or basement floor. She even joked that she should have "given it up" for me back in the day, and I explained that then I'd have been her "butt boy" forever.
We laughed.
I smiled when I noticed a guy at a table across from us kept looking at our table. He's start at Chloe's legs, which I surmised were encased by black pantyhose.
After dinner we walked the outside of the ship, enjoying the night, and we hugged. She kissed my cheek and we walked arm and arm from the vessel.
There was no wait for a taxi and I told the cabbie where we were heading, but to take a circuitous route along the riverside, Market Street, and the parkway to the Art Museum before heading to her hotel.
