Lt and How It All Started

It was early Autumn about 20 years ago now. We were living in a tiny town called Cedar Creek, about 30 minutes southeast of Austin, Texas. The nights were finally starting to get cooler, with lows in the 50s, a much-needed break from sticky central Texas summers. In fact, that weekend was promising to bring a rare, and oddly early, frost. This usually would have been a cause for excitement, as it was, and still is, my favorite type of weather.

But the mood was instead one of worry. As ours was a rural home, we had to rely on the butane tank behind the house, not having access to the town gas utility. Our tank was dangerously low as it was, and the dropping temps would cause that to condense, dropping the pressure too low. If that happened, we'd be without the ability to cook, heat water, or worse still, heat the house. The wife and I could probably manage it, but as parents we couldn't let it happen.

The timing was awful. Had it been a few days later, or even a little earlier, we'd have had options. But that isn't how these things work, it seems. But Murphy's Laws are immutable, and one of the harshest corollaries is "it will go wrong at the worst possible moment". So true to form, we were flat stuck.

We still had our admittedly shitty internet connection. I sat down to have a cup of tea and logged into a local chat to vent. A guy I had talked with before was on, and we got to talking. Let's call him LT. He was a lonely, kind, and kinky, older man in his mid-60s. We'd played a time or two in the past, always a gentle but thoroughly enjoyable experience. While never pretty or intricate, his rope work was consistently safe, comfortable, and effective. It was one of the only people with whom I indulged my crossdressing sides (I hadn't come out to the fact that I was actually transgender at this point in my life). It was a refuge and an outlet for me, and a pleasure for him. LT lived two small towns over, and he'd always tied me in the shotgun seat of his truck for the trip out to his house in the deep woods of Bastrop County. Road bondage is one of my favorite joys in life, so it was a real treat. We'd chat about life, the universe and everything on the long trips home afterward. A confirmed gentleman farmer type.

Because of that history, I trusted him enough to tell him the whole story. I even told him I was thinking of posting to the M4M chat room where we'd met that I was willing to do whatever it took to get the rest of that gas bill. I knew that was a risk, being deep in the heart of a Red state, but it seemed I had a family to keep fed and warm. LT was worried about that but understood the situation. Surprisingly, rather than try to talk me out of it, he simply asked, "How about I take your offer?"

I honestly hadn't considered that option. I knew him to be safe and fun, and a good match in terms of chemistry. I just didn't think of him agreeing to such a thing.

"Are... are you sure you'd be okay with that? I mean, I'd totally game if you are, but I wasn't hinting I promise. I was just..."

"...I don't mind. Honestly, I think it would be fun. I already love playing with you, and if it'll help y'all out at the same time all the better."

I sat stunned for another couple of minutes and then checked in with my wife. We have always been open in our relationship, and even though she wears my Collar, we discuss everything. It is just how we take care of one another. She was fine with it as long as I was. So, having cleared my head and my conscience, I turned back to the keyboard and replied that I was good to go.

We agreed to meet in a grocery store parking lot in the town nearest to him, to save him two full round trips to Cedar Creek. I got ready; shaved, showered, put on my favorite black satin thong, thigh high stockings, no bra at his request. My wife helped with hair and makeup, and I put on my favorite black stretch mini dress. It was super clingy, and it did wonderful things for my breasts. Whether from undiagnosed gynecomastia or Klinefelter's syndrome I still don't know. But I developed breasts right about the same age as my sisters had done. I hated the bullying growing up, but made peace with it, even counted them as a blessing when it came time to exploring my gender identity later in life.

On went the black faux-suede strappy heels. I took a deep breath, gave the mirror a nervous last look, and headed out the door. The drive to Elgin took about 40 minutes, and to be truthful I don't remember much of it. I expect I was a jangled mass of nerves, apprehension, and maybe a little thrill. But I cannot say for sure. My memory jumps from leaving our home to arriving in that parking lot on the other side of the county. I remember seeing his old black and green Ford pickup truck pull up next to me. LT wove and kindly smile at me from behind the wheel. I took another deep breath, ran a self-diagnostic of my nerves, and got out of my car. I locked it up, knowing that it would be busy enough for the next few hours, since it was the only store in 20 miles any direction. However, I also knew the staff (including my father) and most of the customers and didn't want to waste any time getting into his truck. "Bad gas travels fast in a small town" as they say, and if I was spotted it would be back to my dad in no time. So, I moved it over to his passenger do and promptly slid up onto the bench seat.

We said our hellos and pleasantries, because there's no Emily Post etiquette handbook for this kind of social interaction. I was electrically nervous, but his voice was soft as ever. From behind his visor, he pulled a pair of nice police-style handcuffs. Nice heavy steel, not the tinny nonsense that so many of us settle for, it occurred to me that I never had asked LT what he did for a living before he retired. I took the cue and turned in my seat to present my wrists behind my back. He locked the cuffs into place, just snuggly enough to feel them, but not so tight as to be painful. I settled in and he locked the seatbelt into place and latched it.

"You all set now?" he asked with a soft but sly grin. I nodded my assent, trying to seem more stoic than I felt. I expected the play to be fun, and I knew what kinds of things he'd likely want to do that night, but I couldn't shake the fear that when it was over the guilt would be overwhelming. I was terrified about how I was going to live with that. But there was nothing to be done about it now. And I needed to do whatever it took to take care our home. As the old Ford grumbled grouchily into gear and backed out of the parking space, I closed my eyes and resigned myself to whatever was coming. We pulled onto Highway 290, the main throughfare through the town, and were on our way.

Elgin, Texas had a small population of about 8,000 back then, with a really small city proper and the rest spread out on farms, family plots, and stretches of nothing. We were out of town and away from the residential streets in about 5 minutes, on to FM (Farm to Market) backroads in no time. Even as rural as Elgin was, LT lived in the wooded middle of nowhere. He pulled over to a disused cattle path on the side of the road and parked the truck, turning the lights off. I was confused, as having been to his place before I knew we were still miles away. Around he went to my door, and as he opened it he reached across to undo my seatbelt. His arm brushed across my nipples that had already been hardening both in anticipation and the chill of the oncoming evening. The stretchy fabric was tight yet slightly textured, and it created delicious friction as his skin slid across. Familiar electric pulses flew through me, and I couldn't help but moan and arch. He chuckled to himself, let the seatbelt retract, and put a hand on either side of my waist.

"Step on out now," he told me. I eased over and stretched out one foot to find the ground. I tentatively placed some weight upon it. Confident that the ground was suitable for my novice experience with heels and compromised balance, I brought the other leg to bear and nervously stood up. I was painfully aware of how much harder it was to pull this off without using my arms. But thankfully LT's arms were more than capable of steadying me. Once established on my feet he slowly slid a hand up my back. He reached into my hair and pulled back slowly. My head followed, now looking up at the stars breaking their way through the fading twilight. I felt his lips kiss behind my right ear, then travel down my neck, across my collarbone to the sternum, and then suddenly his teeth found my right nipple and clamped down hard.

I gasped and arched again, feeling the miasma of pleasure and exquisite pain send sharp shockwaves all the way through my body. His head pulled back, teeth as unrelenting in their grip as the hold his hand had on my hair. He lingered at full extension, then released my breast. In a flash he changed target to my left and repeated the same beautiful cruel gambit. I shifted my weight between my legs, my body instinctively trying to find relief even though I didn't truthfully want any. When he finally let go my whole body was alive and tingling. He told me to turn around, and I couldn't have resisted if I had wanted to. I wanted, needed more, and was ready to anything. I turned back facing the inside of the truck. The hand in my hair moved to grip the cuffs while the other took my hip. He slowly bent me face down into the seat and lifted my dress up over my hands.

With a thumb he moved the back of my thong to the left, fully exposing my ass to him. I heard a rustling of denim behind me, which I first took to expect he was undo his jeans, but it was too brief, and I didn't hear the sounds of a buckle or zipper. I realized he had drawn something from his pocket. I felt my ass being grabbed by one strong, calloused hand, spreading me open. I drew a sharp breath, not really knowing exactly what was coming. An almost silent, wet noise followed. A sticky, wet, warm pressure met my asshole, moving north then south. My body automatically tried to clench, but his grip was too strong for that. He circled once or twice more, then moved to the very center, and worked his way into me. He was lubricating me. I didn't know how to react. My mind was screaming "wait!" but I was so overwhelmed with emotions and lust that the body won out. His skin was hard from a life of labor, but the slick lubrication was making the sensation in any way abrasive or uncomfortable. Despite my hesitations, I leaned back into the touch.

To my confusion and disappointment, his hands withdrew. I shook a little. My mind raced. Where the hell are you going now?!, I though to myself. I heard the sound of the pocket again, with a series of muffled staccatos throughout. Once again something was at the entry to my ass, but much softer and smaller this time. No wider than a pencil, and blunt. It slid into me easily, but after only about an inch, it stopped as a wider pressure replaced it. Slowly but firmly, he pressed that into me, and my ring slammed shut as the width diminished. Then another...

This repeated about eight more times. I was completely lost as to what was happening. After the last one, I could feel something narrow but tall filling the crack of my ass, which I took to be the base of whatever was now inside me. LT toyed with it, as if checking his handiwork, and moved my thong back into its assigned seat. This pressed the mystery item firmly into place. I shivered in response. He stood me up and helped me back into the struck. I shuddered again as my body weight pressed the toy further into me. The seat belt was snapped back into place. He then opened the glove box and pulled out a long black scarf. It was folded lengthwise, then tied around my head as a blindfold.

As everything went dark, I heard the truck door shut with a heavy thud. A few moments later he was back in the drivers seat, and off we went again. We drove through the now full dark night. Occasionally his hand would reach over to fondle a breast, pinch a nipple, play under the hem of my dress while maddeningly missing my desperate cock. All the while I felt every bump and rock in the mostly unpaved roads, causing whatever it was inside me to writhe and shake. I lost all sense of time or distance, but he must have driven every inch of those rural backroads to draw out the length of the journey. From time to time his fingers would work into my mouth for me to suck, which I did, greedily. I whimpered with frustration every time he withdrew them.

Finally, I felt vehicle slow down and not regain speed after making a 90 degree turn to the left. After about 15 more seconds the old Ford groaned to a stop, and the engine went silent. He got out, walked to my door, and opened it. He grazed my chest again as he unbuckled the seat belt. One hand slid between my legs and cupped me, the first real time that night. I felt his breath on my ear as I heard him whisper.

"Well, we're home. You ready to really get started?"