West Texas

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Old Cowboy picks up a cute hitchhiker in West Texas.
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The drive through West Texas can be long and straight and boring. I've traveled these roads all my life and rarely found them anything but long, boring and straight until one such trip a couple months ago. I had been at a meeting on a Friday afternoon and was driving back to my place when I saw a cute, young thing hitching on the highway. As I was half-way between nowhere really, I decided to pull over my old pick-up and offer her a ride. She said she was heading to Phoenix and as I was heading West, I told her to climb in the truck. I should tell you that I'm 64 and retired but I still raise some cattle on my ranch. She couldn't have been more than 23, though she later told me she is 22.

It was late Spring but the temps were already in the eighties on this afternoon. She had on a loose button-down shirt over a tank top, a pair of cut-off shorts that barely covered her ass and crotch and lace-up hiking boots. I admired her thin, tanned legs as she sat on the opposite side of the bench seat. Her dark hair was below her ears and she wore a New Orleans Saints ballcap. We drove onward and she told me her name is Sheila and I shared mine as Jack. Her voice was soft but confident when she spoke to me. I told her I was going to stop for dinner and asked her if she was hungry. Her answer told me she likely hadn't eaten much in the last couple days. I pulled off at a burger joint along the highway and told her to go clean herself up and I'd get us a booth.

When Sheila walked out of the ladies room, she almost looked like a new girl. She'd washed the road off her face, applied a bit of red to her lips and something dark around her eyes. She put her over-sized backpack on the seat and slid into her side of the booth. She smiled as I handed her a menu. "Order up, it's on me." Her smile grew just a bit wider. I'd never seen a girl eat so much as she put away a double cheeseburger, fries and a big ol' chocolate shake. I asked her a couple questions but it seemed her mouth was always too full to answer. I did learn she was going to Phoenix to meet up with her sister but she didn't have any idea when she'd get there. She had been hitching' for a week and sleeping in truck stops or county parks along the way.

When it seemed she was slowing down on eating, I figured I'd better ask her what was next. I told her we were a couple miles from a bus stop where I could drop her. She didn't say anything and since we'd gotten along so far, I figured I might as well ask. "Or you could sleep at my house tonight and I can drop you in the morning." She eyed me a bit suspiciously. "No hanky-panky, Sheila. I have a guest room you can sleep in for the night." To be honest, the guest room wasn't my first choice for her but I definitely am not the type to force myself either.

"A soft bed would be nice, if it's no trouble Jack." I paid the check and we headed out to the pick-up truck for the drive to my ranch. With a full belly, Sheila nodded off to sleep on the hour drive. I tried to sneak a peek of her body as she slept but the setting sun made the light difficult. She woke as we bounced down the dirt road to my little farm house.

#

I hopped out and slammed the door behind me. When I noticed she hadn't gotten out, i turned and hollered "You comin' in or sleeping in the truck?" She hesitated one more moment then slid out the passenger side and followed me up the steps. I flipped on a couple lights and showed her the guest room and bath. Sheila checked the bed and set her backpack down on the floor. I gave her some space as I walked to the kitchen. "I'm gonna have a beer. You want one?" I asked. When I didn't hear her response, I walked down the short hallway with two bottles opened. The bathroom door was shut. Standing in the bedroom, I asked again and this time I heard her say yes just before the sound of a flushing toilet. Sheila walked through the door in just her tank top and shorts. I had noticed her boots and socks by the bed. I could see her small tithes and nipples pressing against the ribbed tank.

We drank the beer and nibbled on some potato chips. "Would you mind if I go and take a shower, Jack?"

"Not at all, Sheila. There should be towels and soap, but let me know if you need something." I watched her cute little ass swish as she moved down the hall. I could feel a bit of an ache in my jeans as I watched. There was something about Sheila, but I just couldn't put my finger on it. I flipped open my laptop and checked mail and to see if I missed any news of the day. After opening a second bottle of beer, I walked down the hall. I opened a drawer in the spare bedroom, pulled out a pair of ladies pajamas and lay them on the bed.

A few minutes later, Sheila appeared wearing them. They were a bit big but she had rolled up the pants above her knees. She had only managed to button half the buttons on the top. "These were for me, weren't they?" she asked with a devilish smile.

"I thought you might need something to wear after your shower." And I definitely took note that the top was noticeably unbuttoned. Her short, dark hair lay lazily around her head. Maybe she had brushed it, but I didn't think so. "Can I get you another beer?"

She asked me about myself, sitting curled up in a lazy-boy rocker. I told her I lived alone. When she asked about the pajamas, I told her they were left over from a friend who used to spend some time here. I said I used to travel the World for work, something with electronics but this area had always been home. I retired a few years back and now just raise some cattle and farm some vegetables. An hour or so past and we seem to become more comfortable with one another.

"So do you pick up young girls often, Jack?" the question was followed by quite the grin. She nimbly unbuttoned all but the bottom button on the pajama top. As she shifted in the rocker, I could see most of her small tits.

"Well Sheila ... West Texas has lots of long, lonely roads. I've given a lift to many a hitchers, if they don't look too grubby." I gave her a look letting her know she'd passed that standard on the roadside. "As for young girls, not too many." I noted a hint of a pout. "But you are the first I've offered my spare bed." We talked a little longer with the tone bordering on foreplay.

Sheila shifted in the chair again and her left tit slipped from the pajama top. "Jack ... I think you have a question for me and you're not sure if you should ask." I smiled as I sipped my beer. Sheila was right. "Just ask and then you'll know."

"You're right. I do have a question and it's really not like me to be bashful." Sheila waited as I formed the question. "Are you a boy?"

Sheila smiled and stood up from the chair. I watched as she walked five steps to be standing beside me. She unbuttoned the last button as she covered the space. "That's quite a question to ask Jack since I've been flashing my tits at you the last hour or so. Why don't you check for yourself." It was said as a dare. Trying to call an old man's bluff. I'm really not sure what she expected me to do and I never asked her. I sat down my beer and pulled her pajama bottoms down over her hips. I really wasn't surprised when i saw her little dick hanging down between her thighs. She had lots of dark pubes all around it.

"I was born a boy but I'm a woman now, Jack. I just have a penis. But then you knew that before you looked, didn't you?" But it really wasn't a question that she needed answered. "I'm sure you were just being a good guy when you picked me up on the highway. And I really appreciate that. But somewhere through dinner you got the idea i might be just a little different and that's why you invited me back here." She was pretty much right and I told her so. "So the question now is what do you think about what you see. And it's been my experience there's only one way to really find out."

Sheila reached out and unbuckled my belt and then my jeans. She pulled open the fly and my cock was tenting my shorts. "I think we have our answer, don't we Jack?" I've been with many women in my days and even sucked on a few men in my time, but I'd never actually seen a girl like Sheila. Oh, I'd seen pictures on the internet but had never run across anyone like her in West Texas. She had a cute face, sexy little mounds for titties and a sexy ass. Of course, I was hard just thinking about her as she squirmed in my rocker and flashed me.

Sheila dropped down to her knees and helped me slip my jeans and shorts to my ankles. Her right hand grabbed hold of my seven and a half inch cock and stroked it. I looked downward as she bent her neck and lowered her lips to the tip of my cock. She kissed it lightly and I felt her tongue rubbing around the tip. Her hand was steady and slow on my cock. I slunk down in my chair and spread my legs a little wider. Sheila's mouth bobbed on the crown before she began sliding further down my cock. I could feel her gobbling me up as her soft lips inched down my erection. When she had nearly taken my entire cock, she started to slide her mouth up and down in a fucking motion until her lips nearly left my crown before sliding back down. I let out a low moan of gratitude to her skill.

And then finally she let me cock slip from her lips. I was about to cry foul, when I felt her mouth sucking on my balls. She had both of them in her mouth and was tonguing my sac while sucking. Her hand had returned to stroking my cock and I began feeling an entirely new form of satisfaction. I had never had anyone take my sac so completely like Sheila. She could feel this old man getting closer so she deftly slipped her mouth over my cock and took my entire erection. Her tongue was rubbing the underside of my cock as my tip played with her tonsils. My body tightened and I shot my first load of cum down her throat. Sheila gagged slightly but held firm and pulled a second stream from me. This one she captured in her mouth. She pumped my cock a few more times before lifting her lips from my tip. A drop or two escaped her lips but she deftly swept it up with her tongue. She opened her mouth to show me all my cum filling her before swallowing. Sheila reached over and took a swig from my bottle. "I guess the answer is you like what you see very much!"

#

We crawled into my bed a little while later. I invited Sheila to join me and she quickly accepted. Neither one of us had on a stitch of clothes as we got under the covers. Me with my grey body hair and slightly sagging body and Sheila with her tight, young body were quite the site if anyone had seen it. We kissed and fooled around under the covers but nothing more. I did play with her little cock as we spooned, her tight ass pressed firmly against my cock before we finally fell asleep for the night.

I was awake early as is my custom but I let the girl sleep. I was dressed and nearly out the door when she called out, "You leaving me without a word?" Sheila sat up in bed, the covers falling below her chest.

"I'm going to meet my buddies for coffee. I figured I'd let you sleep but help yourself to breakfast." She looked at me a little surprised that I was leaving her in my house, "I'll only be gone a couple hours." And I waived as I went out the door. I get together with a variety of other farmers about three days a week to drink coffee and shoot the shit. Didn't figure today should be any different though I'm sure they'd have quite the expression if I told them about the girl that got me off last night!

I returned home a little after nine to the sound of the shower. I poked my head in the door and called out, "I'm home Sheila."

"Jack," she waited for a response, "I could use someone to wash my back." I hadn't been asked to do that in quite a few years. I pulled off my flannel shirt, kicked off my boots and scooted out of my jeans. When I stepped in the shower, she wrapped her arms around my neck and pulled me close to her. We kissed under the shower water. Then I turned her around and washed her back and shoulders. My hands moved down and caressed her asscheeks with soapy water. Sheila wiggled her ass as I did. Once the water was off, I grabbed a towel but Sheila kissed me first. And then she took my nearly erect cock and quickly I was cumming in her mouth. Then she let me dry us both off before we got out of the shower.

While she ate a bowl of cereal, she asked me if I had horses on the ranch. I told her I had five and asked her if she wanted to go for a ride. Sheila said she got to ride horses when she was young but hadn't in some years. Convincing her I had a gentle one, she agreed to give it a try. I gave her an old pair of my jeans to ride in as she only had shorts. They were a few inches too big, but we rolled them up and I tied a belt around the waist to keep them on her skinny hips.

#

We rode for a little more than an hour as I took her around my ranch and the surrounding land. Every so often, we'd go on a gallop and she'd let out a little girl scream at the sensation. By the time we got back to the house, it was getting near noon and the sun was pretty warm. I helped her off the horse and watched her walk a little funny back to the house as I put the horses away. It took me a few minutes to get the horses taken care of in the yard. When I walked inside, Sheila was standing in the kitchen with two large glasses of ice water. She had on the long-sleeved shirt I'd given her to wear but no sign of her boots or the jeans. As she brought me the glass, I had to smile at the way she walked. "My ASS is sore!" I took a long drink from the ice water and laughed.

"Perhaps I should rub some liniment on it to take away the soreness." Sheila kidded me about I'd like to feel her tight ass and that's why i took her riding in the first place. I finished the water in another long gulp and then picked her up in my arms and carried her down the hallway. I tossed her on the bed and the shirt flew up over her waist. Panties were not an option today it seemed.

"Do you want to fuck me, Jack?" I had to think about her question. I had never done anal with anyone in my life. I had always considered the asshole to be the end of a one-way pipe, but now I was being presented the opportunity. And she didn't have a pussy for me to fuck. Sheila was lying on her side, twisted at the waist so her reddened asscheeks were presenting themselves to me.

I pulled my t-shirt over my head and unfastened my jeans. I reached down and pulled off my boots before sliding my jeans and shorts off. My cock was nearly two-thirds erect as I crawled on the bed beside her. Sheila reached down and pulled on my cock. I told her I'd done lots of things but had never fucked anyone's asshole. She smiled at the realization she was my first after all these years on this Earth. She rolled onto her hands and knees and put a pillow under her head. I got behind her, pulled her cheeks apart and spat into her crack like I'd seen in a hundred videos. She reached back and pushed my spit around her rim and then I moved in close behind her.

Our bodies are actually a pretty good fit. I'm 5'9" and 165 pounds. Sheila is 5'7" but probably not more than 130 pounds. I pressed my cock to her rim and felt it opening to take me. I pushed harder and felt my cock exploring an area I'd never been. Sheila lifted her head as she felt me sliding inside. I soon had my cock buried fully inside her asshole and she felt so nice and tight around me. "Now fuck me Jack. Use your big cock get us both off!" I started thrusting my hips and pulling them back. Sheila reached under her body and was stroking her cock. My hips were slapping into her tight ass as I fucked her. She howled, her ass still sore from the horseback ride not an hour earlier.

Having cum twice in the past 12 hours, I had a feeling this might take a little longer for me. At Sheila's urging, we rolled onto our sides. My cock never left her heavenly hole. I watched as she stroked her cock and I played with her nipples. The additional stimulation certainly helped and I found myself thrusting into her with renewed vigor. I kissed Sheila on the neck just before I spurted my cum into her asshole. It wasn't nearly as strong as earlier, but I haven't cum three times in a day in a few years! As she felt me cum, I watched as her cock spurted cum onto her belly. She continued to stroke herself for another minute before absent-mindedly using her cock to rub her cum into her skin.

"You're going to kill this old man with all this sucking and fucking!" Sheila laughed loudly at my comment. I could feel my cock getting softer but I had no intention of pulling it out. It had taken me 64 years to get it in an asshole, I was in no hurry to take it out. After a few minutes, it fell from her still tight hole. My juices dripped out of her as it did. I finally got up and took a piss to clear the tubes. While I was washing my face, she sat down on the toilet beside me and peed herself before wiping away the rest of me from her backside.

#

A few hours later, I grilled a couple steaks for us and Sheila fixed some vegetables. We ate and talked a little while watching the news on my television. "If you're not in a hurry to get to Phoenix, you can stay here a while with me."

Sheila looked up from her plate. "Won't your friends think it's pretty odd ... you are a couple years older than me."

"The guys will love it and the women can go to hell if they don't like it."

"Can I use your phone after dinner to tell my sister where I'll be ... for a while."

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10 Comments
AnonymousAnonymousover 7 years ago
Cowgirl

Would like Sheila to ride me cowgirl!

AngelaKAngelaKalmost 8 years ago

Love it, especially since my lover is twenty years older than I am!

AnonymousAnonymousover 11 years ago
A great story.

This was a great story because all during it I wanted to be Shelia. It was romantic and yet very sexy.

AnonymousAnonymousover 12 years ago
I liked the story

Thanks.

AnonymousAnonymousover 12 years ago
great

we are friends on hamster I Loved your stories wish i was in cali to make some of your dreams a reality

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