What a Long, Strange Trip It's Been

In some ways the path that lead me to this place in my life is clear, but in other ways it is murky and hard to follow.

I'm in my late forties, married with no children, and with a comfortable life. We are best friends and love each other very much, but my wife and I have always had a difficult and unsatisfying sex life and much of the reason for that lay in both our pasts. When we met in our mid-20's we were both virgins, which is unusual for this day and age. Not that we hadn't both fooled around in our younger days with petting, groping, etc. It's just that neither of us had quite made it to fucking someone. Maybe we were both just too shy, but there were other reasons.

I must admit that the main reason for my sexual dysfunction was my overindulgence with too much porn; I became addicted to it early in life. I've learned to understand over time that excessive reliance on porn leads to less drive to seek out real-life encounters. Why would you when it is so much easier to live out many encounters in your head (and in hand) as many times a day as you want? In those younger days it was often several times a day that I pleasured myself.

My wife's reasons are more complex. She has always been a bit prudish about sex and it likely stems from some childhood abuse. Her young male cousin experimented with his newfound sexual appetite by involving her as a young girl. It's a sad story, but unfortunately not unique. It certainly left scars on my wife's psyche and I believe it made sex mentally difficult for her in her adult years.

So, when we finally met and began to have sex, we were both timid, inexperienced, and just plain bad at it. Frustrated to some extent I continued to satisfy my appetites just as I always had done; alone with pictures and my imagination. Over time my wife simply stopped trying and I blame myself for not pursuing the matter; instead I took the easy way out. We are still very affectionate and loving together with lots of touching, kissing and caressing, but sex has become more and more infrequent.

My sexual interests and the type of porn I chose to enjoy also changed over time, sometimes due to changing technology and simple exposure. Of course, the advent of the internet changed everything. Suddenly there was no content that was unavailable and I saw more and more.

My childhood exposure to porn was the same as every other male of my generation, starting by sneaking looks at Playboy and Penthouse, thrilled just to see pictures of naked women. Over time my topic of choice became lesbian porn, and that has been a constant in my life ever since. What has changed with that particular topic has been the various subcategories as well as the level of explicitness of this porn.

The first big shift in my lesbian porn interest that gave me an extra thrill was lesbian analingus. Watching one beautiful woman tongue another woman's ass was simply amazing to me, but my interests grew more aberrant from there. Next came sloppy kissing and then explicit spit play; women freely sharing saliva together. Wow! It still gets to me.

You can probably guess what came next; lesbian watersports, which led to the ultimate thrill of seeing a woman catch her lesbian lover's piss in her mouth and then show her appreciation by swallowing it all down. I don't think I will ever tire of watching lesbian porn.

But there has been another large branch of porn interest in my life and that started about five years into my marriage; interracial sex. Specifically, black men having sex with white women, and I have my wife to blame (thank?) for this interest.

It was in those early days of our marriage that I first noticed my wife's apparent interest in attractive black men. Normally she was very subtle about it and I wasn't always sure that it was really happening, but over time a pattern emerged and I could more easily tell when someone caught her attention on television or in a movie.

I even noticed her watching attractive black men in social situations and I could see how her level of interest and flirtatiousness increased. Even with this little lustful interest of hers she is still prudish and doesn't overtly show her desires publicly.

When I first learned of her secret 'dark' desires, I was naturally jealous, but over time this too became a source of arousal for me. Eventually I even started to seek out interracial porn where the white female resembled my wife: tall with long, curly blonde hair. This helped my newfound fantasies of my wife having an interracial encounter that I would imagine during some of my masturbation sessions.

The best scenes entailed the blonde woman being seduced for her first time by a strong and attractive black man with a very large penis, the size of which would cause her stunned amazement. Watching these scenes, I would imagine that it was my wife seeing and then tasting for the first time a big, black cock as she succumbed to her lust and hungrily devoured his throbbing dick.

After sucking his big cock, I imagined the black man would move my wife to the bed where he passionately fucked her, powerfully thrusting himself deep inside her while she moaned and cried out from the intense pleasure that she felt for the first time in her life. Sometimes he would climax deep in her pussy, but more often my wife would show her appreciation by accepting his thick load of cum in her mouth, eagerly swallowing it down as she locked eyes with the dark stranger.

These became the standard fantasies for me and I busily amassed a great quantity of interracial porn, always searching for the ones that best fit my wife's appearance and fit neatly with my imagined scenes. When found, these would be the prized photos or videos that I would return to again and again. Until very recently that is.

Things started to change about a year ago when I first came across an interracial cuckold video and I was surprised at how intensely arousing I found it. I gathered more and more, with my favorites being the ones where the woman verbally humiliates her white husband while she praises her black lover's big cock and his ability to pleasure her.

I never really went for the videos where the cuckold husband was made to clean up his wife's 'creampie' by licking up the black man's cum. I could understand the thrill that some might find in this, but it just wasn't my thing. What did give me an unexpected thrill though was when the wife threatened to make the husband suck her lover's cock, or where they shared it together. Again, I was surprised at my arousal at this development and I sought out more of those types of videos.

What was going on inside of me? Was I harboring gay or bisexual tendencies? I didn't think so, but I tested my suspicions by watching some interracial gay videos. They did nothing for me, and I'll admit I was a little relieved, but I was still aroused at the thought of a woman forcing her husband to suck black cock. I suspect that it is the domination aspect; forcing the man to perform a sex act that is forbidden or taboo. I don't know for sure.

At this point I made yet another discovery. While seeking out more of those "wife domineering the husband with a black lover" videos I came across one where instead of a black man it was a black transsexual, albeit one with a huge penis. I watched this video in amazement as the white husband was forced to suck the big, black cock that was between the legs of a relatively attractive black female. My mind was blown and I suddenly had a new pathway to explore.

For the next six months I searched for images and videos of black transsexuals, trannies, she-males, Tgirls, or whatever other term you'd like to use. The more I searched the more I honed my taste and focus. The best was finding a very attractive and very feminine looking T-girl with natural-looking breasts and, of course, the biggest and best-looking cock between her legs. These are the transsexuals that when walking down the street would cause ANY straight man to do a double-take and make their own dicks swell as they assumed they were simply admiring a beautiful woman.

They are out there, believe me, and a few of them are making very good porn videos that will satisfy your desires if they are similar to mine. Over the last several months I have spent many happy hours watching these videos and fantasizing that it is me there with these ebony beauties. I've never sucked a dick in my life but watching these gorgeous black Tgirls swinging a thick cock between their legs made me want to try it!

And I also discovered something else out there during my searches for black T-girl porn; which was black T-girl escorts. It was when I was searching out these porn images that I found a few that were connected to escort agencies, some of them in my own home city! What the fuck? The thought that this type of encounter could easily be arranged made it even more exciting, although I knew the chance of meeting up with someone like that in my own city was just too risky to consider. As usual I let the fantasy play out in my mind without acting on it in real life, content to just jerk off to the thought of it.

"Idiot!" Right? That's what you're thinking. You've read my story this far and accurately determined that I am a 'watcher' in this world, not a participant and certainly not an adventurer. I've resigned myself to watching others and living vicariously through them while developing calluses on my hand as I keep jacking myself off. And you're right! That has been my life so far, no doubt about it.

But maybe that's starting to change...

In my searches online, I came across a black Tgirl escort that ticked off all my boxes. She's tall and gorgeous. Her face is like a model with big eyes, full lips and a great smile. Her body is full-figured with great curves, full round ass and large, natural-looking breasts. She boldly touts that her endowment is an impressive and cut nine-inch length with thick girth. Although she's coy in her online images, not fully revealing her penis, there's just enough visible to support her claims.

This holy grail of Tgirls is located in Las Vegas, far from my home city, and I'll call her 'TS-Ebony.' But Ebony was just like the holy grail in that she was also elusive and out of reach for me. I contented myself to keep her photos as part of my collection and keep searching for more, that is until that recent day my boss called me into his office.

I stood there in his office with two other coworkers as he explained the situation. Someone in our west coast branch had screwed up on a project. The client was very upset and wanted someone else onsite immediately. Although the work wasn't hard, he explained that this assignment was going to mean personal sacrifice because it would likely last a duration of two to three months out of town and away from our family. He didn't want to force someone to go; but rather he was hoping for a volunteer to spend the next few months in Las Vegas.

"I'll go, sir!" I spoke the words almost before my boss finished asking the question. I caught everyone by surprise, even me. My coworkers were also relieved that they didn't have to go themselves. They both shook my hand and wished me well and then quickly left the room lest I change my mind. Then I had to go tell my wife.

My wife was unhappy at the situation, but even more unhappy that I hadn't talked to her first before agreeing to go. I lied and told her that I was sort of being forced to go, that my boss said I was 'the only man for the job' and other shit like that. I felt the guilt eating me deep down in my gut because I was secretly thrilled to be going to the same town as Ebony and hoping beyond hope that I could build up the courage to actually do something real for a change instead of just jerking off.

The next two weeks were a whirlwind of activity packing and traveling to Vegas and then jumping into the project and getting up to speed. My boss was wrong about one thing, it was hard work! Things were much worse than we had been told and I was working twelve to sixteen-hour days, six days a week to get things back on track.

After three weeks of this, things settled down some and I could even tell that the next weekend would be the first time I could actually take off two consecutive days and try to forget about work for a while. I told myself I deserved a reward, so that night I went online to Ebony's website and got up the courage to login and send a message. "Are you free this Saturday? I would love to meet you!" I attached an obligatory picture of myself and hit send. "But how could she be free," I thought. "That was only two days away. Not a chance!"

I was almost asleep when I heard the 'Ding' from my phone. I held my breath when I saw it was her reply. It said, "Hi Sweetie! You're so cute. Lucky for you I just had a cancellation for that day! Where can we meet and how much time do you want to reserve?"

I couldn't believe this was happening. My fingers were flying across the keypad as I tried to rush a response. Then I had to go back and retype it slowly because I had misspelled every word in my haste. I told her we could meet in the bar lounge of my hotel. My final two words simply said, "All night!"

She quickly replied, "Good for you, honey! You are aware of my rates, right? We will have a good time together, I promise! Look for me at nine o'clock sharp on Saturday."

My heartrate was through the roof at my excitement. I couldn't believe I had actually done it. I immediately pulled up her pictures on my computer and jerked myself off to release some of my abundant sexual energy or else I knew I would lie awake thinking about her all night. I was really wishing that I could see more of her in her pictures, but I let my imagination fill in the blanks about what it might be like. Afterward I finally drifted off to sleep.

Ebony had reminded me of her rates, and for good reason. I had asked for her to stay the whole night and according to her website that was going to cost me $3,000. Normally that would have been a problem; I could never had spent that kind of money without my wife finding out, but luckily, I had this covered.

Because I was making this personal sacrifice for the company and potentially saving them from a lawsuit that could have cost them millions, my boss showed his appreciation by opening an account in Las Vegas in my name with an extra $15,000. He told me that he wanted me to use this money to treat myself to an occasional extravagance: special food, entertainment, or activity. He said I could even fly my wife out to stay with me from time to time. He told me that I didn't have to submit receipts or anything. It was mine to use as I pleased with no questions asked.

I had conveniently neglected to inform my wife of my boss' extra generosity. I felt another pang of guilt as I realized this, but I told myself that I could still bring my wife out once or twice and still have plenty of money for other 'entertainment.' After all, I hadn't spent a dime of that money yet.

As Saturday night approached, I nervously got ready, making myself as presentable as possible. I even went down to the bar two hours early to make sure I could find a good table with a clear view of the door so I wouldn't miss her arrival. I also needed a couple drinks to calm my nerves and raise my courage. I kept looking at my watch and then at the door every few minutes as time crawled along at glacial speed. When I looked down to see my watch say nine o'clock sharp my heart jumped in excitement.

I quickly looked up at the door just in time to see a stunning black woman enter and begin to scan the room. She was just like in her photos except for some very minor differences. She had tinted her dark wavy hair with some blonde highlights and she was wearing a skin-tight, white dress that accentuated her curvaceous figure.

I quickly stood up and waved to her and then realized that I probably looked like an overeager schoolboy on a first date, but she sweetly smiled and walked over to greet me with a hug and kiss and then sat down. I proudly noticed the hungry eyes of other men in the bar area as they ogled her beauty.

I was afraid that when Ebony saw me in person, I would register the disappointment in her face, but there was none of that. I know I can't match up to most men she probably meets, but I'm not too bad. I'm in relatively good shape, and in fact I had started to exercise on this trip, even more so in the last couple of days since I called Ebony.

I ordered her a drink as she asked me about myself. I was so excited to be with her that I started babbling about my work, but she kindly listened and even seemed interested enough to ask a few pertinent questions. Her voice was like liquid honey, smooth and sultry thick. After we finished our drinks Ebony finally got around to the reason for our meeting.

She spoke quietly so no one else could hear us and I had to lean in close to listen. Her sweet aroma filled my head and excited me even more. "Do you still want me for the whole night, darlin, and do you have the full amount?" When I quickly nodded and reached toward my pocket she smiled and said, "That's fine. We can deal with it later in private, sweetie. You didn't tell me if you wanted 'Top' or 'Bottom' service from me tonight; I can do both you know."

I paused, not realizing what she was asking. I started to stammer an answer, "Well, I like many positions. We can do whatever you think is best."

Ebony smiled and laughed and then said, "No, what I mean is do you want..." She paused and then asked, "Sugar, is this your first time doing this?" Embarrassed, I swallowed and then sheepishly nodded, but this only caused Ebony to smile even more. She said, "Oh good! I like first timers. You are definitely getting 'Top' treatment from me, baby! It's what I do best. I am really going to enjoy this night!" She gave me a smile that melted my heart but paired with a look on her face that made me very nervous and very aroused at the same time.

Ebony took my hand as I stood up to follow her lead and we walked to the elevators. My head was swimming and I don't think it was caused by the drinks. The ride up was a blur and the next thing I remember was standing in my hotel room with music coming from the radio and Ebony starting to unbutton my shirt. She cooed in my ear as she kissed and nibbled at my neck, then she whispered, "Now you can give me the fee, sugar." I didn't hesitate to reach in my pocket and pull out thirty one-hundred-dollar bills.

Ebony laughed as she took the money with one hand while with her other hand she felt across the front of my pants and said, "Well that only leaves one other bulge in your pants and I'm going to want that one too!" She then leaned forward and placed her soft lips on my mine and pulled me toward her for a long deep kiss. I felt her tongue move past my lips and then delve deeply into my mouth and start to wrestle with my own tongue. I reveled in the taste of her!

Ebony became more aggressive and soon she had me stripped bare. My penis was rigid, hard as a rock from her kisses and attention to my body. She giggled and said, "My, my sugar! How gentlemanly of you to stand up in the presence of a lady! I'll just have to do something about that soon, but first I want you to undress me."

I jumped at the chance, although my hands were trembling as I unhooked the back of her dress and then peeled it down from her shoulders. As I pulled the tight dress downward, I freed her breasts and now I could see them fully exposed. They were just as I had seen in the online photos, full and round with large dark nipples that were now erect. Ebony said, "What are you waiting for, hun? Have a taste!"

My mouth was immediately on one of her stiff nipples as I kissed and sucked, feeling her other breast with one hand while my other hand moved around to her ass. As much as I would have enjoyed licking and sucking her tits for hours, I knew that what I really wanted to experience lay below. Still latched onto one nipple I knelt downward farther while using my hands to lower her dress more.