Road Journey

Preface

My wife is a stunning, gorgeous brunette who is at once the most genuine and endearing sweetheart you will ever meet, and a sexual force that washes through me like a hot, chaotic wind. The mother of incredible children, and the epicenter of a family one never wants to leave, and rejoices to reunite with, I have the kind a partner in life that a man would want brag to the world about, but decides to leave unsaid because it makes it all the better. So you ask: why would I share her with another man? What follows is my answer to that seemingly simple question, and the real-life account of what was a most thrilling sexual vignette for us. You may decide to read this at arms length and enjoy as a voyeur, or you may find it a helpful inspiration to do something you and your partner have only discussed coyly in hushed voices even when no one was around.

To begin, let me describe my wife, whom I'll call "Amanda." Amanda has just turned 50, and is one of the most selfless people you will ever meet. A product of an Irish/Italian family steeped in Catholic faith and traditions, she is the kind of girl you want to bring home to your mother (and I did). She grew up in the shadow four older siblings, and was told she was the "looks" of the family. While that was certainly true, time has proven she is perhaps the most intelligent of the bunch, as I will describe a bit later. She has married once before, and as dysfunctional as that arrangement was, it changed her for the better in ways only adversity does.

Through the travails of that stormy relationship, Amanda gradually blossomed into a corporate rock star. Leveraging her ability to build partnerships, along with her resourcefulness and ingenuity, she created professional opportunities for herself and never looked back. I'm guessing her siblings look at her from afar and say, "Wow, our little sister is all grown up." That's right, she has.

But perhaps the most stunning transformation was in a sexual sense. When we first met, I saw Amanda as a sweet, innocent and caring soul -- and I mean "soul." Although she was absolutely stunning physically (I'll get into that more later), there was a deep and introspective side to her. There was a depth and warmth I felt from Amanda from the moment we met, and it hooked me immediately. I would spend hours through email asking her questions, delving into her past, trying to understand her at the most basic level, because I was utterly fascinated by her story. I knew, however, that there was a sexual being deep inside -- someone who was locked up through years of oppression and convention; suppressed by selfish motives and "the ideal." And while it was never my intent to "set her free," I have learned that through years of trust, bonding and mutual respect, that the most incredible sexual being will emerge. Fortunately for me, that being is my wife.

So I suppose I should describe my wife physically, because as trite and vapid as it may seem, I feel compelled to paint the picture a bit. Trust me, later on you will appreciate this description. So as I said, Amanda has just turned 50, and has a mature allure that younger men yearn for, and older men understand. She has short brunette hair, a smile that will disarm the most hard-hearted of men, and big, brown eyes that will draw you in like the most addictive of opiates. And that body: those wonderful, womanly curves. My particular favorite is the area between her upper thigh to her midsection -- that inviting hand-drawn indentation that would make a Bezier tool jealous. Her legs are simply gorgeous, with thick, pleasing thighs and muscular calves, she makes quite a statement in high heels and a skirt. In fact, she is at her absolute sexiest when she goes to church. I can't even get into those fantasies.

Now that you have some background on my wife, and can appreciate why she is so amazing, maybe you're beginning to understand why sharing her with another man is so thrilling to think about. Or maybe you're still wondering.

Broached Topic

Let's table the musings for a moment and let me offer a glimpse into our intimate life. Making love to Amanda is something that happens well beyond the bedroom. A quick glance, or locking gaze, lets each other know we still find one another irresistible. A slight wink is a simple and subtle punctuation to those feelings of mutual desire. I think about Amanda in a sexual context often, playing out scenarios and fantasies, constructing erotic storylines in which she is the protagonist. I am able to do this because she is so willing and open to talk about these things, and doesn't think I'm any less of a partner, or vice versa.

Like many couples, we've explored the usual fantasies, even if just as light pillow talk: sex in a public place, involving another woman, another couple, other ethnicities, celebrities (lord help us if we ever bump into L.L. Cool J) and any number of other carnal scenarios. While the conversation was mostly light, erotic fun, my wife is adventuresome enough to talk a bit more seriously about some of these possibilities. One fantasy in particular, however, really reached down inside me and planted like a stubborn seed.

Maybe it's because I'm in my late 40's, or maybe it's because I love my wife so much and trust her, but the thought of including another man in a sexual encounter is what I most want to do. The reason I mention my age is because I wonder if younger men are less open to this arrangement as they are still trying to prove their manhood; in other words, their "machismo" prevents them from exploring this very erotic thought. And that's fair, after all, the male competition is fierce at this age, and coupled with the normal insecurities of a young man facing the inevitable crush of responsibilities of adulthood, the furthest thing from his mind is sharing his girlfriend with some other punk who will undoubtedly try to steal her away. From a young woman's perspective, perhaps she may feel "loaned out," and not desired enough after all. In any case, I believe this fantasy -- this need -- is that of an older, established man who is married to an incredible and trusted partner in life.

So when I broached the topic to Amanda (beyond the usual "wouldn't-it-be-cool-if" fantasy talk), I was anxious to hear her perspective. Even though we had a pretty open discussions around these kinds of topics, I was pleasantly surprised by her answer: "Yeah, I think it would hot!" came the cheerful reply.

Exploring this possibility a bit more, and pressing her for assurance that she would consider such an arrangement as much for her pleasure as mine, she did inquire as to why I felt this way. Secretly, I loved the question. It demonstrated to me that while she wanted to explore this with me, she also wanted to understand my intentions and motivations. "Well, " I explained, "there is some sexual thrill on a number of levels." I proceeded to deconstruct the fantasy a bit, from the emotional to the physical.

First, I explained, there is an emotional force at work here. If this amazing, wholesome and upstanding woman, who loves me unconditionally, could have the opportunity to fuck another man, devoid of guilt or fear, well, how cool would that be? If I could finally repay all the wonderful moments, in and out of the bedroom she has provided me and others, by arranging this amazing experience, how content and satisfied would I be? There was something emotionally potent about the very thought of Amanda fucking another man.

Second, there is the physical. Yes, the sights, sounds (and scents) of my loving wife having sex with another man. I can only imagine what my gorgeous, hot Amanda (remember the description?) would look like sucking a hard cock, or laying back taking him into her wet pussy or perhaps on all fours thrusting back on him. I have masturbated many times to these very visualizations.

Lastly, there is the sexual journey, or "road trip" as I call it. It's really cool to talk about all these fantasies, but to actualize some of them? Well, that's just fucking hot. It's like talking about visiting Paris, or Milan, or Mars, but never going. Sometimes, you just gotta pack your bags.

I think that explanation helped her understand where I was coming from, because her response was, "Well, set something up dude!" The use of 'dude' punctuated her encouragement a bit, and provided some levity. With her approval, and with confident ambition, I was ready to set out on a search for a suitor. I was sure the world was teeming with hot, available men who had a high emotional IQ and literacy rate.

Looking for Mr. Right

So finding a qualified candidate was sure to be a piece of cake. After all, I had read "Penthouse Forum" and "Hustler Letters" growing up, and all those factual accounts recalled the ease and convenience with which suitable partners came out of the woodwork to fulfill every fantasy. It was as if the authors of these letters drove up to some "fantasy drive through" and simply ordered a stud muffin with cheese.

I didn't wanted to look too close to home, or consider someone we knew, for all the obvious reasons. Besides, I'm not sure how I would even start that conversation ("So... hey man, if you're not doing anything Saturday night, would you like to fuck my wife?") Nah, that wasn't going to work.

The obvious thing to do was to turn to the Internet for help. I quickly dismissed the idea of services like Craig's List, or any swinger listings and I wasn't about to answer some random ad posted by "Big John Stud" only to be greeted by Little Pudge Pervert weeks later. No, my wife deserved a hot, educated guy who was a good lay.

I found a few sites that listed plenty of hot guys, but they all catered to the gay market. Apparently, gay guys fuck a lot. And pay for it. And pay for it, I thought. Hmm, the thought of paying for sex had never entered my mind. But it made sense: Amanda and I could tailor the experience to our specifications, without worry of ego, sensitivities, preferences or -- to be blunt -- their "feelings." Who gives a fuck? This ain't no love connection, homeboy. We're paying you for your looks, your body and your hard dick -- nothing else. But... let's talk about that. No, this isn't romance, but in discussing the matter with Amanda, we were looking for more than just a human dildo. We required a little gray matter, someone who could carry on a thoughtful conversation, as well as get hard on command. So, when I proposed the prospects of a "hired gun" to Amanda, to my surprise she was in. What an awesome wife I thought! Plus, it narrowed my search down to hot guys who would do what we told him to do. For money.

With renewed confidence, I began to scour online for hot guys who required a fee for their services. How hard could this be? I thought. Shit, paying a guy to be with my sexy wife -- they would be lining up! But alas, there are a million male escorts out there who are more interested in serving the gay market. I guess bending over for some old, fat C-level exec of a financial institution beats working for a living. No thanks, I'll take the daily grind.

Over time, my frustration grew along with my intimate knowledge of homosexual acronyms and catch phrases as I searched for the right partner. Eventually, using the search term "straight male escort," I stumbled upon a guy with some potential, and checked out his website.

His name was Slate, and he was currently living in the Great White North (Toronto, specifically). I'm sure his name wasn't really "Slate," but it sounded a lot more manly and erotic than "Bob" or "Clifford." Originally from upstate New York, he was 37, a former fitness instructor and was in Toronto for the next year to get a license in physical therapy. On top of that, he volunteered for an organization that reunited returning war vets with their service dogs. From what I could tell from the website, he seemed educated, intelligent and articulate. The tone of his website was at times sincere and genuine, or whimsical and irreverent. From a guy's perspective, he was a "man's man." He had a few photos posted too, mostly classy shots in a suit or tuxedo, no doubt escorting some GILF to a bridge game or something. According to the "Stats" section of the site, he was 6' 2", 220 lbs, wavy brown hair, hazel eyes and an athletic build, with an extra pound or two. The few less formal photos confirmed this description, one with his shirt off at the beach. While he was no L.L. Cool J, he was a really good candidate. So, I sent him an email.

I explained to him what we were looking for, but in veiled terms because I didn't want to come off like some hard up pervert. I mentioned that we were hard-working professionals in our 50s, and very much in love. Without being specific or graphic, I described an "arranged date" for my wife in which she would enjoy the company and conversation of an attractive man, and that it would progress "as necessary," purposely adding the business-like touch at the end to establish our intentions. Hitting the send button, I hoped I might hear something from him soon. I'm impatient, so if something doesn't happen instantly, I'm officially annoyed. Three weeks went by.

During this time, I had reached out to a few other guys. Most were monosyllabic meatheads who could only manage terse responses like, "Sure, name time and place," or some who insisted on PayPal deposits before proceeding. One "dick" even offered the ultimate cuckhold experience in which he would pound my wife while humiliating me. Oh cool! Name your price, Raging Bull!

I laid back a bit on my search because frankly, I was getting a fatigued and there were more important family matters that could not be neglected. Then, almost randomly, Slate responded to my inquiry.

Scott, so sorry for the delay. I was in North Carolina at an event for veterans and I just got back last night. Thanks for your interest! You and your wife sound like a fun couple, and I'm honored you would consider me to fulfill your fantasies.

In his response, he went on to describe how he had experience in this area, and had worked with other couples wishing to explore and push their boundaries. Since his website clearly spelled out prices, there was no need to go there. Instead, he asked me for a bit more information, and was curious if my wife was truly interested in making this fantasy a reality. He had mentioned some bad experiences in which husbands had "surprised" their wives with his services, and how those situations never turned out well. I insisted Amanda was not only in agreement, but looking forward to the experience. With that, we agreed to talk over the phone later in the week.

I know this sounds crazy, but I was super-clandestine in my approach to this situation. Insistent on preserving our identities, I never disclosed any personal information except our general geography. So, in order to call him and not expose our number, I purchased a Trac phone in cash at a local retail store. I had learned about this after reading how drug dealers buy these phones and then discard them before authorities can track them. I never thought I would have something in common with common, low-level drug pimps.

A few days later, as agreed, I called him. I have to admit, I was very nervous and actually needed to psych myself up before tapping the numbers. It didn't help that the country code + Trac code + some other bullshit code was like the launch sequence of a fucking ICBM. I screwed it up multiple times and had to use my company-issued iPhone to look up the country code. Finally, I deciphered the secret decoder ring and heard the familiar tones of a dialing phone. Several rings later, he answered with a cheerful "Hello?" His greeting was disarming, but not cheesy. I identified myself as Steve, and that we had planned on touching base. "Of course!" he cheerfully acknowledged, his attention to customer service being evident right away. His voice was a combination of cool, suave tones, with an underlayment of educated sophistication and worldly experiences. It was like talking to a really smart and genuine rockstar. Or L.L Cool J. ;)

We talked for about 15 minutes, which was much longer than I had anticipated. I was actually surprised Slate would spend that much time talking, and further impressed with his gentle line of question regarding my wife. He asked about her personality, her sensitivities, her simple pleasures. I said I didn't know anything about any of that crap and that we were looking for a good man to fuck her. There was silence for a moment, and then a burst of laughter as he realized I was joking. I quickly followed with my appreciation of his willingness to learn about her, and how that knowledge was key to a successful adventure. We chatted a bit more and it was obvious there was chemistry. Over the next few weeks, we had set a date for our encounter, and exchanged several emails in which I laid out the "rules of engagement" and tied up some other loose ends. We were set to meet him in Toronto on May 25.

The Date I

We drove to Toronto on Friday and checked into our hotel -- The Trump International Plaza. As I wanted the most memorable experience, I reserved a suite will all the trimmings -- including a heated bathroom floor! I mean, who has a heated floor in the bathroom? Oh well, nothing is too good for my wife.

There were two "dates" planned for the weekend. The first would be a get-to-know-you meet up over drinks. We decided to meet at this new, trendy speakeasy-inspired bar called 70 Down. It featured quiet lounge areas perfect for intimate conversation, which would be important for us to get comfortable with each other. The last thing we need is to shout over the din of throbbing techno music is, "SO ARE LOOKING FOR DOUBLE PENETRATION OR JUST A ONE-TIMER?"

We arrived a few minutes early and quickly found an intimate corner . We wasted no time in ordering drinks from the waitress, a young woman with pierced midriff named Cally . Amanda ordered a Belvedere Martini, up with a stuffed olives. I ordered very sophisticated Rob Roy. And of course, Amanda ordered two shots of whiskey like she always does. This is the playful, reckless abandon side of my wife I always loved.

We made small talk about insignificant things, such as the bar tender's crooked bowtie and weird hair piece. It's comforting to make fun of people while you're waiting for the guy who will be fucking your wife the next night.

Just a couple minutes late, Slate coasted down the steps of the faux-speakeasy and quickly identified us. He gracefully moved to me and extended his hand with a firm and friendly handshake. Next, he gave Amanda a respectful peck on the cheek and a quick brush of his hand on her shoulder. He apologized for being late -- there was an accident a few blocks away. The pictures on the website must have been recent because they were a spot-on match. I could tell from Amanda's initial reaction she was pleased with his looks and even detected a faint blush on her gorgeous face in the flickering glow of the small, scented oil lamps on the table. When Cally came over with our drinks, he ordered a scotch and soda. Good choice I thought. We asked her to add a third shot -- symbolic for the experience in store for us the next night.

We sat and made the small, idle conversation one would expect in this situation. I was pleasantly surprised by Amanda's assertiveness, but I could tell she was a little nervous. So was I, but Slate was adept at diffusing this energy, and put us at ease with light, non-invasive questions about our drive to Toronto and our stay in this wonderful international city. He had a charm and sense of humor that was surely a turn on for woman, and acceptance into "guydom" clubs the world over. He was no L.L. Cool J, but he was making an impression on us.