Long Lonesome Highway Ch. 02

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Tags: Transgender, anal, bareback, big cock.

My name is Bruce.

I drive trucks for a living, and I get to meet so many beautiful people on the road.

I'm 38 years old, Divorced, and a bit over weight around the middle, like most truck drivers are.

I was headed north, another trip up into tropical Queensland.

I love it up there. Warm weather, green tropical rain forest everywhere.

Arguably, some of the best fishing in Australia.

I never leave home without my fishing rods.

As a long distance truck driver, you just never know where you might get stuck, or for how long.

So if I get caught between loads, I go fishing.

Queensland's tropical coast was still a long way away. It would be another two days before I got where I was going. I was driving through outback New South Wales at the moment.

My whole world reduced to just a ribbon of black bitumen running through a sea of red dirt and brown, dry grass.

About an hour ago the sun had set in a huge red fireball which had painted the entire western sky with it's vivid colors. It is easy to see why artists love to paint pictures of these outback sunsets, but the pictures really don't do the real thing justice. I started looking for a place to pull up and camp for the night.

Before I found a roadside parking area, I saw the lights of a small town. "That will do me," I thought, "haven't had a beer for two days, and I've earned one."

I pulled the truck into a large parking area across the road from a little country hotel / motel.

I shut down the truck, locked her up, and headed across the road.

Walking into the pub I was surprised, there was almost nobody in the place.

A couple of older men, looked to be local farmers were sitting at a table with a beer each.

An attractive woman sat at another table sipping a glass of red wine, and me standing at the door, wondering why the place was so empty on a Thursday night.

I walked up to the bar, "Hi! Can I get a pint of Pale, and if the kitchen is still open, a menu?"

The girl smiled at me, "Sure, you scraped it in for the kitchen by just five minutes. Hurry up and choose so I can order it for you, or the cook will bugger off and you'll go hungry."

"Easily done," I said, "Steak, medium rare, two eggs, sunny side up, and chips. Thanks sweetheart."

"You're welcome, let me get this to the kitchen and then I'll get you the beer."

I looked around the bar. Typical outback bar. Farming and bush paraphernalia hanging on the walls.

An old mouldboard plough bolted to one of the ceiling rafters.

Over the toilet doors somebody with a bit of artistic flair had mounted a set of old Lanes Ace rabbit traps, the old fashioned steel jaw types now illegal throughout the country. Over the men's room door a trap with it's jaws closed. Over the ladies room, a trap with it's jaws open. Subtle, but clear enough to understand.

I took a look at the woman sitting at the table. I hadn't noticed it when I came in, but she was very good looking. Probably mid thirties. A redhead, long wavy locks of hair down to just past her shoulders, and sparkling green eyes. A light sprinkle of freckles over her cute little nose and across her upper cheeks. She had full luscious lips, the kind that make kissing a sensual pleasure.

Her body was something to write home about. Full breasts, probably about 38 DD.

The waist, from what little I could see with the table in the way, looked to be slim.

Under the table her legs looked to be strong, but very shapely. Nicely shaped calves, and well rounded thighs. I looked back up at her face. She was regarding me with a slight smile on her lips, and what looked like an extra sparkle in her green eyes. "Like what you're seeing?" she asked me, without breaking eye contact.

"Here's your beer, Honey." the barmaid said. "Dinner will be about ten minutes."

"Mine should be here shortly too." the redhead said to me, "care to join me?"

"I'd like that." I replied.

I took my beer, and joined her at her table. "You didn't answer my question." she said with a grin.

"Of course I like what I'm seeing, What's not to like?" I said with a smile

When the barmaid brought out our meals I asked her if there were any rooms available,as it would save me sleeping in the truck. "Sorry, Honey." she said, then indicated the redhead, "This lady got the last one, I'm afraid."

"No problem, the truck will have to do." I said.

We started to eat our meals. The steak was done spot on. It always annoys me when the so called professional cook can't get a simple steak right. The eggs were also right. Whites totally cooked, and yolks soft and runny. "So. What's your name?" asked my dinner companion.

"Sorry, rude of me not to introduce myself earlier, my name's Bruce. And you are?"

"Jessica. Nice to meet you, Bruce."

We shook hands and went back to eating our meals. "Bruce I hate to think of you sleeping in a cramped truck cabin. The room I've booked is a twin. I don't mind sharing, if you don't."

"Thank you for the offer Jessica, but I couldn't do that, besides, the truck isn't that cramped."

After we finished eating Jessica ordered another wine, and I got another beer. Half way through our second drink Jessica said, "Bruce, Let me put the offer another way," she looked me in the eye, and continued " I have a twin room, and I insist you share it with me!"

"I guess you've decided I don't get a choice in the matter." I said.

"Very good, now you've got the idea." she responded.

We enjoyed a very pleasant evening together.

Jessica had a couple more glasses of red wine, and I had a couple more pints of beer.

About nine o'clock, Jessica said, "I'm going to go to bed. You can come along when you're ready, it's room 5."

"It's been a long day on the road, I guess I'm ready too."

We both stood up, and I went to the bar to pay the tab. "Thank you Honey," The barmaid said, with a smile "Have a good night."

"You too." I said, before turning and joining Jessica at the door.

We walked along the path, past the other units, Jessica linked her arm through mine. When we came to room 5 Jessica turned to me, "You didn't have to pay my tab you know."

"I know, but sometimes I like to pretend I'm a gentleman." I grinned

We went into the room. A pretty normal room for a small outback pub. A bit of flaking paint around the ceiling. A small wall mounted air conditioner. Two beds with the standard red tartan blankets, and two small beside cabinets. That was it, apart from the en-suite bathroom.

"Do you want to use the bathroom before I go in and take a shower?" I asked, "Because it's been a long day and I'm a bit on the nose."

"No, It's fine, you go ahead."

I'd been in the shower for a few minutes when Jessica stuck her head around the corner, "Want me to wash your back?" she asked.

"I would like that very much." I said.

I thought to myself, that's nice, what's not to like about a hot woman coming in and washing your back for you.

Jessica walked into the bathroom, naked. The first thing I noticed was her breasts. Full round, big nipples, and most definitely DD. A slim waist as I'd already noticed before. Broad hips.

Oh my God. A big cock. I mean A BIG COCK. I'm a solid eight inches, she was probably about that, even while she was flaccid. I didn't know what to say. "Umm, You don't think it would have been polite to at least give me a little warning?" I asked.

"I'm sorry, Bruce. Really, I am sorry, but I've found that a little warning usually results in the guy either running away, or belting me in the mouth. So I thought, with you, I would try and use surprise to my advantage."

"That is not a good idea." I said, very seriously. "In fact its bloody dangerous, and a good way to get yourself killed. The wrong guy could get really violent if you surprised him like that."

"Jeez, I'm an idiot," She said, "I'll leave."

"NO YOU WON'T!" I barked, "You offered to wash my back, get on with it."

"But, but, you just said."

I interrupted her. "I said, the wrong guy!, I'm not the wrong guy. You are not the first trans woman I've met, or the first one I've been intimate with. All I said was, A little warning would have been a good thing." I smiled at her, "Now will you get your sexy arse in here and wash my back."

She squealed with delight as she rushed into the shower, and grabbed the soap.

Jessica washed my back, then went on to wash the rest of me, every inch of me, from head to toe.

She paid particular attention to washing my cock. Over and over again she washed it. Rubbing it back and forth again and again to make sure it was spotless. Or at least that's what she said she was doing. We both laughed. She washed my front, my back, my butt. She also took great pleasure in washing my toes multiple times, because that had me in fits of laughter. My toes are very ticklish.

After she had me clean, I returned the favor. I washed her from head to toe. I paid particular attention to her big, beautiful, breasts. I wasn't sure I could get her nipples clean enough with my fingers, so I licked them thoroughly and then gave them a good hard sucking just to be sure they were spotless. I didn't know that cleaning a woman could make her moan so much.

I washed my way down her body. Her belly button needed a bit of extra cleaning so I washed it really well with my tongue. She squealed, and giggled the whole time I was doing it.

I moved down to her cock, it was totally shaved bare. I hesitated before touching it, "Do you mind?" I asked.

"Mind what?" Jessica asked.

"May I touch your cock?"

"Of course, why would you ask me that?"

"I know many trans women see it as a dirty little appendage that they are forced to carry around."

"AH, Thank you for asking, but of course, mine isn't a little appendage, and I'm rightfully proud of it, and in just a little while you will have made sure it isn't dirty." She said, as she grasped my head in her hands and guided me towards her.

I washed it with soap and my hands, then washed it again with my mouth just to make sure. After I had washed it really well with my mouth, I stopped and took a look at it. She had a solid nine inches of thick hard cock. This woman was packing a lot more than I was. After I finished washing Jessica we got out of the shower and toweled each other dry. We were standing in the bathroom face to face, and I reached out, took her in my arms and kissed her luscious lips. She responded instantly, sucking my lips, and gently biting them, and between sucking and biting, she just used her lips to sensually kiss me. She felt so good on my mouth, I actually started to get harder, just from her kiss.

We moved from the bathroom to the bedroom.

I pulled back the covers on one of the beds and lowered Jessica down onto the bed, following her down. I loved the feel of her body against mine, soft, warm, and feminine.

We kissed and fondled each other, just enjoying the feel of each other.

After a while she said to me, "I want you to fuck me."

"Are you sure?" I asked

"Mhmm, I'm sure."

She handed me a small tube of lube, I squeezed out a small amount on my finger,

I slid my fingers down past her cock and balls, to her butt, and started to gently massage her puckered pussy. I kept massaging and gently applying pressure until she opened up to me and allowed my finger to slip inside a little.

Once my finger was inside her enough I began moving it gently around rubbing lube all over the inside of her. I added a little more lube, and then began slowly slipping a second finger inside her.

Just gently stroking back and forth until I had both fingers deeply embedded in her warm, tight, body. I continued to work on stretching her, and relaxing her. It took a little while, "You haven't done this for a while." I said.

"Not for at least a year." she said.

I continued to work on opening her butt, until she sprung a bit of a surprise on me. "I think I'm ready."

"Are you sure?" I asked with some trepidation, "You still feel very tight."

"And you don't want me tight?" she asked me, with a giggle.

I squirted out a bit more lube and gave my cock a good coating. Then I nestled with my cock between her cheeks, and looked into her pretty face.

She looked back at me and nodded her head, "I am ready." she said

She wrapped one arm around my neck, and the other went down, and her hand put pressure on my butt. I reached down and guided myself to her opening. Gently I pushed forward, feeling the head of my cock nestle against her puckered pussy, until it popped inside her. I stopped pushing to allow her time to get adjusted to the invasion. "MMMM, that already feels so good." she whispered in my ear.

I slowly, gently moved my hips forward to push more of myself into her tight, puckered pussy.

She never took her eyes off me, so I could easily see if I was moving too fast. Once inside her as far as I could go in missionary position, I rested and allowed my churning balls to stop, and to allow her to adjust to me. "Oh God, you are so unbelievably tight. If I move I'm going to cum. Please, please, don't move." I pleaded.

She held perfectly still, as did I.

Once I had control of myself again I started to slowly grind against her, all of her. I loved the feel of her full lips against mine, and her full breasts against my chest, and every other part of our bodies rubbing against each other.

It felt strange, we were two strangers. We only met tonight, but we weren't just having sex. We were making love. Each giving to the other, for their pleasure instead of just for our own.

I dipped my head and suckled her breasts. I nibbled her ears, and used my fingers to stroke her erogenous places. She reached up and nibbled my nipples, and gently bit them till she felt my cock jump at the stimulation. She ran her fingers down the crack of my butt, and gently massaged my anus. We did everything we could to bring pleasure to each other.

After a while she said to me, "I need you to fuck me."

"Um, what have I been doing for the last half an hour?"

"Making love to me," she said "and it has been beautiful, having a man make love to me like this, but now, I need you to fuck me."

I knew what she meant. I withdrew my cock, and wrapped my right arm around her.

I flipped her over so she was face down on the bed, then slid my cock back inside her.

I slid deeply into her, deliberately angling my cock so it put pressure against her prostate.

"OH FUCK, That's it." she said, "That is what I need, Fuck me deep, make me cum."

I continued to stroke deeply into her, making every stroke push against her prostate.

After several minutes she could not contain her orgasm any longer. "FUCK ME BRUCE, I'M CUMMING!" She cried, "OH FUCK, I'M CUMMING SO HARD!"

I couldn't hold off any longer. I drove my cock into her as far as it would go, and grunted my release, again and again I ejaculated deep inside her. I gave her all I had, not a drop left in me.

I collapsed on her back. Slowly I recovered my breathe. I reached my hands up to gently stroke the sides of her breasts with my fingertips. "You OK?" I asked.

"Silly question." She said "I've never felt so beautifully fucked. Thank you."

"Why thank me? I assure you it was my absolute pleasure." I said with a chuckle.

"But I think now, it might be time for a shower again."

"Not yet." She said "Stay inside me a little longer. It feels so good with you on me, and inside me, like this."

So we lay like that for several more minutes until my cock had shrunk to the point where it slipped out of her. I eased off her back, and turned her over to face me.

I bent down and kissed her gently. We shared a gentle kissing session, both of us sucking and nibbling each others lips in a caring, sharing fashion, totally unlike our earlier hungry devouring of each others mouths. After we finished kissing I moved down her body until I reached her cock, which I took in my mouth and sucked clean. "We do need a shower." I said "Both of us."

I got up, and taking her hand, I led her to the bathroom.

Together we showered again, washing each other again from head to toe. This time in a gentle post intimate way.

Both of us enjoying the gentle intimacy of post sex, physical contact.

We stayed in the shower, gently stroking, kissing, and touching each other, until we ran out of hot water. Then we got out, and toweled each other dry.

As we walked back into the bedroom we looked at the bed we had just used. "Yeah, we sure made a mess of that one." I said wryly. "We should probably sleep in the other one."

Jessica giggled, "Um, I think you might be right."

She peeled back the covers on the second bed and we got in.

We lay on our sides initially. Our faces touching each other, gently nipping and sucking each others lips in a gentle act of intimacy. Our fingers tracing lines on each others bodies. I traced lines over her breasts and across her nipples, she traced lines down my cock and across my balls.

Neither of us doing it as a buildup toward sex, rather, we were just enjoying the post sex intimacy.

After a while, I started to get some excitement back into my body, and I had noticed that Jessica was starting to get an erection. She whispered in my ear, "have you ever been made love to by a trans woman?"

I said, "Didn't we just do that?"

"Not with me on top, we didn't!"

It dawned on me what she meant. Jessica wanted to fuck my butt. I'd never had anything in my butt before. I wasn't sure I was going to go for this idea.

"Um, never." I responded

"Would you like to try?" Jessica asked. "I promise I will be just as caring and gentle as you were with me."

"Oh God, I'm not too sure about this. I've never had anything like it done to me before."

Jessica held me in her arms. One hand gently stroking my back and my butt, the other stroking my face and my neck. "Trust me. You have my word that I wont do any more than you are comfortable with."

I don't know why, but I nodded my head. She gently kissed my lips, continuing to stroke me.

"I will be gentle, and I promise, you will learn to enjoy it." She continued, "You saw how you made me cum by fucking me. You'll do the same. You'll have the most intense orgasm you've ever experienced, and it isn't over in seconds, it will go on, and on."

Jessica reached for the lube on the bedside table, and applied a little to her finger.

We were still face to face, so she reached down behind my back until she reached my butt crack.

She started to rub the lube into my butt crack and over my puckered butt hole.

She squeezed more lube onto her finger, "Turn over baby, let me in."

I turned over and gave her access to my butt. Jessica slid her lubed fingers between my cheeks and gently massaged my puckered anus with one finger. She applied pressure, slowly until she felt the resistance reduce a little. Surprisingly it felt good having my puckered ring massaged. I felt myself relax, felt myself welcoming the pressure of her finger on my butt hole.

Then I felt her finger go into my butt. It was only the first joint, but I froze. It hurt. A sort of high pressure pain, and a burning sensation.

I noticed straight away that she had stopped moving. We were in suspended animation. Not a single movement from either of us. Jessica was waiting for me to relax, waiting for me to breath again.

When she felt me relax and heard me start to breath again, Jessica slowly slid her finger in, a little more, until I froze again.