Long Lonesome Highway

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Tags: Cross dresser, Sissy, Gay anal

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I'm a long distance truck driver. My name is Bruce.

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

Not too long ago I was on one of my regular trips across the country with a load of freight.

I called in at a truckstop in the middle of the desert to use the toilet and grab a shower.

I don't usually stay in these places, preferring the peace and quiet of a roadside camp.

I pulled the truck up and pulled the air brakes on. The hiss of air being released caused a cloud of dust to roil out from under the truck.

I grabbed my toiletries bag and towel, and headed inside.

A leisurely dump, and a good long hot shower and I was good to go.

Total time at the truckstop, 45 minutes. Great, that keeps the logbook honest.

I walked out the door.

Halfway between the amenities and my truck, there is a picnic table. At the table sat a young woman with a suitcase, she was in tears.

"Whats up sweetie?" I asked.

I gave her the once over.

Wavy Strawberry Blonde hair. Big bright green eyes. A cute little button nose, and puffy bow shaped lips.

A tight little body, flat chested, but with a flat midriff showing under her crop top, and a fantastic pair of long legs under her shorts.

"my boyfriend and I had a fight and he dumped me here," she said.

"what, out here, in the middle of nowhere?" I responded.

"Uh ha, where do I go from here?" she asked

I told her there is a bus comes through about once a day, or maybe every two days.

"I don't have money for the fare"

I told her she had two choices then. Truck drivers, or tourists.

A third choice might be to take a job in the truckstop. These outback truckstops are always looking for staff.

"I would," she said, "but I need to get home. Mum isn't in the best of health and needs some help with some things"

"That leaves truck drivers and tourists," I told her.

"Which way are you going?" she asked me.

"East, but I will be pulling up to camp not far down the road, and my truck isn't like the big American rigs. There is no big double bed, just a cosy little bunk."

"I don't mind," she said, "I can sleep in the front seat, but I need a lift, Please?"

What was I going to do? Leave her out here in the middle of the desert? "Get in."

She grabbed her suitcase and jumped into the passenger seat.

I cranked up the old truck and shoved her into gear. We left the truckstop in a cloud of dust and headed east down the highway. "what's yer name?" I asked her.

"Robyn"

About a hundred clicks down the highway I pulled into a roadside truck parking area, and shut down the truck for the night.

I opened the little fridge in the cab and grabbed a beer, "want one? Robyn" I asked.

"I don't drink" she said.

I got out of the cab and headed for a tree to relieve myself.

Then I opened the tucker box and got out a few basic food items to rustle up a feed.

"Bacon and beans" I said, handing her the pan and a fork.

"Leave me half"

"Thank you" she mumbled around a mouth full of food, "I will"

She handed me the pan, then went and washed the fork under the trucks underbody water tank.

She handed me the fork, "Thank You," she said

"Welcome" I responded, as I shoveled food into my mouth.

After eating I washed the pan and fork and put them away in the tucker box.

"Bed time, We will hit the road not long after sunup" I got up and headed for the truck cab.

Getting into the cab I stripped down to my jocks and slid back into the sleeper bunk, and pulled a blanket over myself. "Night"

"Good night" she said, before stretching out across the two front seats of the truck, with her suitcase shoved into the gap between the seats.

I went to sleep. I wasn't asleep very long when the sounds of her tossing and turning in the seats woke me. Sticking my head out from under the blanket I noticed the cold.

"Robyn, I promise to be a proper gentleman, but you need to get your arse back here in the bunk. You will freeze to death out there on the front seats."

"I need you to understand something first," She said.

"What's that?" I asked.

"I'm not what you think I am"

"Your not a lost kid sleeping across the front seats of a cold truck?"

"Well, yes, but I'm not a girl." she said. "I'm actually a boy."

"Are you kidding me?"

"Uh Uh. No, I really am a boy. My name was Robin with an I, but I changed it to Robyn with a Y so it would be more feminine."

"Well, fuck me. Hang on, never mind that. OK, but you still need to get in the bunk, or you really will freeze to death out there."

She did, or should I say He did.

He climbed back into the bunk and lay down beside me. Trying hard to keep a bit of distance between us in the tight confines of the narrow bed.

I was soon asleep again.

The sun was just starting to lighten up the eastern sky when I woke up.

The first thing I noticed was that I was not alone in the bunk.

The second thing I noticed was that I had my arm wrapped around Robyn, and my morning wood pushed hard between her, His, arse cheeks. And the third thing,

I didn't want to move, it felt so good having a nice pair of arse cheeks wrapped around my hard cock.

I was obviously not the only one who was awake. I could feel Robyn grinding his arse back against my cock. I was getting confused about how this was turning me on. I was straight. I wasn't into fucking guys, never have been. So why was my cock rock hard? And, why was Robyn's grinding making me want to shove my cock into him?

"Robyn, Stop, or so help me God I'm going to fuck the shit out of you."

"MMMM, I think I would like that. Although from what I'm feeling, there is no way you could do it."

"Meaning?"

"Bruce, your cock feels like a fence post jammed into my butt. There is no way you could fuck me with that."

"Are you challenging me?" I asked

"No, just stating a fact. Your cock is fucking huge. It would never fit inside me"

"I think you are challenging me. I think you want me to fuck you."

"Would you want to, knowing I'm a boy, and not a girl."

"You are the prettiest boy I have ever seen. I think I would like to try fucking you." I said, "If you are willing?" I added.

"Oh, I'm willing." Robyn said, looking over his shoulder and and licking his lips.

He got up and moved down the bunk. Kneeling beside my legs he slid his fingers into the waist band of my jocks and slid them down. My rock hard 8" cock bounced up. My ex used to tell me I was built like a red bull can. I never drink the stuff so I wouldn't know.

Robyn looked at it, "Fuck, that is the biggest cock I've ever seen"

"Oh come on," I said, "it may be a bit above average, but it isn't a porn star class monster."

Robyn wrapped his fingers around my throbbing shaft. He started to slowly stroke my cock.

"Considering what I'm thinking about doing to you, I really should ask how old you are?"

"almost 20" she giggled.

I found it hard to think of Robyn as a HE, So pretty, so feminine and such a girlish giggle.

It just seemed totally natural to think of Robyn as a SHE.

I slid my fingers into her strawberry blonde waves and gently pulled her pretty face towards my cock.

With her pretty face turned a little sideways so I could watch, she stuck out her tongue and licked the length of the underside of my cock from it's base all the way to the head. I convulsed on the bunk, from the intense pleasure that shot through my body. Then she took the head of my cock in her pretty mouth and sucked up the pre-cum that was oozing out of my cock.

"OH, FUCK, you deserve a masters degree in cock sucking, Gurl!" I whispered.

She released my cock and looked up at me, "You called me gurl, does that mean you don't see me as a boy."

"I can't think of you as a boy. Everything about you just seems to say HOT BABE." I said "and when you giggle, you are just the sweetest little gurl."

She came up the bed, and kissed me. Fully on the mouth, with her tongue pressing for entry.

I hesitated for a moment, was I really ready for that? I parted my lips and allowed her tongue entry to my mouth. Her kiss was soft and gentle, her tongue swirling slowly around mine. Feeling my tongue, tasting my tongue. Sucking my tongue. She was an extremely sensual kisser, and I enthusiastically kissed her back.

She slid back down my body and again took my cock into her warm, wet mouth. I gently wrapped my fingers in her hair and started pulling her head down harder on my cock. She resisted, so I let her up. "Please don't force me down. I can't do deep throat. It makes me choke, and puke!"

"I'm sorry." I apologized, "I'll make sure to remember that."

She wrapped her pretty lips around my cock head and sucked it like a big lollipop.

My body was convulsing with the sheer pleasure of it.

Soon, much too soon, I had to wrap my fingers in her hair again, and ease her away from my throbbing cock. "If you don't stop, I will cum down your throat, and I have other plans for my first load."

I put my arms around her and pulled her back up my body.

Again she gave me one of her sweet sensual kisses.

I reached into the storage pocket in the back of the seat in front of the bunk and withdrew a tube of lube which I kept there for those long lonesome nights on the highway.

Squeezing a bit of lube on my fingers I slid my hand down over her back and started to caress between her butt cheeks. I rubbed lube between her cheeks, over and around her puckered little anus, and gently started to eased a finger inside.

She was so tight I had to work hard to get my finger in even half way.

With my other arm I pulled her down on top of me so my head was beside her ear. "You need to relax, Babe. Relax, relax, relax," I whispered, "Let me in, just relax, and let me in."

I slowly continued to rub my finger gently in and out of her tight little anus until I felt her start to open up to me. Then I added more lube, and slowly started to insert a second finger, and eventually a third.

When I thought she might be ready to go the next step I put my arms around her and flipped us both over so she was on the bottom.

Robyn looked up at me with uncertainty, and a little fear. I took her in my arms holding, her body close, and then reached down and nibbled her ear, causing her to moan. "Relax," I whispered, "relax, relax, relax, relax." I whispered again and again. "I will not hurt you. I will do this gently, but I will need to stretch you to accommodate me, and that will cause you some discomfort."

She nodded, "I know, but I've never tried to take a dick as big as yours before."

I squeezed some lube out and slicked up my cock.

Then I gently eased Robyn's legs up to my shoulders to expose her lovely little butt.

I looked down into her beautiful green eyes, and whispered again, "Relax for me. This will be much better if you relax and willingly open yourself up to me."

She nodded, and I gently placed the head of my cock against her tiny puckered anus.

Gently, and with infinite patience, I slowly applied pressure with the head of my cock.

I never once took my eyes away from hers. I was watching constantly so I would see if discomfort was turning to pain.

I kept up a constant pressure on her anus, constantly whispering, "relax relax relax."

It took a little while, but suddenly the head of my cock popped into her anus and her sphincter muscle grabbed me like a vise.

Her eyes, which had, up till now been shut tight with discomfort, suddenly popped open and went as wide as saucers. Her mouth opened in a silent scream of pain.

I froze, I didn't move. I looked down into her eyes, and I whispered, "just relax, relax, it's ok, just relax."

I waited patiently while she learned to accept this invasion into her body.

Eventually Robyn began to relax and I could feel her sphincter start to release it's vise like grip on me. "OK?" I asked.

She nodded "m,hmm,"

Slowly, gently I started to easy my cock deeper into her rectum. Warm and tight, her body squeezed my cock exquisitely. I had to control myself or I would explode inside her long before I was ready.

I slowly started to stroke my cock in and out of her rectum. Feeling the tightness of her sphincter wrapped around the base of my cock and milking a constant stream of pre-cum which kept her insides well lubed, along with the lube I had already used.

After a little while Robyn started to relax fully, and I could see the discomfort turn to pleasure.

She was starting to moan each time I pushed my cock in and over her prostate.

Again and again I slid over her P spot. Each time making her moan her pleasure.

Her sphincter was still squeezing me tightly and her rectum was so warm. I was starting to build pressure. I was so close to cumming. I was starting to lose control. "I'm going to cum, Baby." I said "I'm going to cum."

With the full length of my cock deep inside her rectum, I came. I could feel one pulse after another of my cum surging up my cock and deep into her body.

I looked down into Robyn's eyes, "are you OK?" I asked

With a dreamy look on her face she whispered, "I'm wonderful."

I slowly eased my cock out of her anus. Then looked down at her.

I saw that Robyn had cum too. A hands free orgasm. Her pretty little dick was covered in her cum, and there was a trail of it up her belly and pooled in her belly button.

I did something I couldn't believe I would ever do.

I bent down and took her dick in my mouth. I sucked her dick and her pretty little ball bag into my mouth, together, and sucked them clean of her cum. Then I licked up the cum on her belly and slurped up the little pool of it in her belly button. The belly button slurp earned me another of her little gurly giggles, "that tickles." she giggled.

After cleaning up our mess in the sleeper we made coffee, and then hit the highway.

That night Robyn was much too sore for us to fuck again, but she did give me one of her wonderful blowjobs. She sucked out every drop of cum in me, and didn't spill a single drop.

Next day we arrived at Robyn's mothers house in the late afternoon.

I pulled the truck up out front, and we both got out.

We stood together on the front lawn. I reached down and kissed her pretty mouth.

I don't think I would ever get used to the feeling of her soft and sensual kisses.

After releasing my mouth she said "Give me your phone."

I handed her my mobile, and she put her name and number into it.

"Any time you are in town, I would love to be your gurl."

"I will take you up on that" I told her.

I got in the truck and drove down the road, headed for the highway.

My phone pinged to say I had a message. I pressed the open button. It was a picture.

A beautiful face, with wavy, strawberry blond hair, and pretty, green eyes, and a pair of soft, sensual lips puckered up in a kiss.

The message read "Thank you for the ride"

As I turned the truck out onto the long lonesome highway, I couldn't help but smile.