Bad Luck Cowboy – Part 1

 New for 2023!  Special thanks to 2 horny and hung Oklahoma cowboys!

 

I grew up in Caddo, Oklahoma.  It was a small town where all the boys in High School basically went out for football in the fall and rodeo in the Spring.  I went for both tie-down roping and team roping.  I was pretty good and placed in several of the rodeos.  For team roping I partnered with my best friend Jeb.

Our families both had working ranches, so we had plenty of time to practice our roping.  It was a great way to grow up.  Jeb and I spent most weekends taking turns who’s ranch we’d spend the days roping and just having fun together.

After we graduated high school, both of us worked on our family ranches and during the summer went around to the local rodeos around Oklahoma and surrounding states.  We did pretty well and we both really enjoyed the rodeo life.  While we won some rodeos, we didn’t have much money so we spent many nights in our pickup truck as we couldn’t afford to stay in a motel.

Jeb and I loved the summer cuz we would work Monday through Thursday around our farms and at our jobs and then head out on Friday for a rodeo.  We’d drive hard all day, dippin’ Cope or Skoal and sipping Mt Dew and Red Bull.  We’d rodeo all weekend and Sunday night drive home taking turns sleeping and driving.  To stay awake, we’d again down our Mt Dew and Red Bull while dippin’ so we would be ready to work Monday morning.  It was a rough life, but hell, we loved it.

Occasionally we’d get invited to spend the night in a motel room with some of the other rodeo cowboys.  There could be up to six cowboys crashed all over the motel room.  Those generally turned into big party nights before we crashed for the night.

During our second year of rodeoing, Jeb and I were at a small rodeo at Ardmore, Oklahoma.  We were planning on sleeping in our pickup when we met two rough rider cowboys.  They were in their late 20s and invited us to spend the weekend with them in their motel room.  Jeb and I were excited to sleep in a real bed.

Friday night go-round, Jeb and I placed second in team roping.  We were excited.  Our new friends took us out the bars to celebrate.  Even though Jeb and I were only 20, they got us into the bars and we had fun drinking.  The two rough riders always seemed to make sure Jeb and I had beers or drinks in our hands.  By midnight Jeb and I were pretty plastered.

The rough riders took us back to the motel.  They helped Jeb and I undress and put us in bed.  We had almost passed out when the two rough riders suddenly were standing over us in our bed.  Both had put on their rodeo gear.  They were bare chested, wearing their hats, chaps, and spurs.  They each had a rope in their hand and before we knew it, they had both Jeb and I bound at the wrists.  We tried to resist, but they over powered us.

They each took one of us and started tying each of us face down on separate beds.  Bandana gags were put in our mouths to keep us quiet.  We’d both heard of guys at the rodeo who enjoyed a rough man fuck.  Jeb and I had never had any man sex.  Jeb even had a girlfriend that was starting to get serious.

Next, both cowboys put in fresh dips and then started to lube our holes.

“Well boys”, the first cowboy said, “Time you two pay for the room.  Damn, we’re horny and ready to pluck us some cherries, boys.  Get ready to put out for two horny cowboys!”

“Shit, think these boys ever been fucked before”, the second cowboy joked. “Well boys, this is how rodeos go.  I expect this won’t be your first rodeo to have some fucking man sex.  But Cade and I are looking forward to fucking you boys hard tonight.  We definitely got you drunk enough and now we’re boned up and ready to ride.”

Both of us were now tied up and our holes lubed up.

Cade responded, “Abe, I’ll bet ya that I can ride my pony boy and cum first.”

“You’re on Cade”, said Abe.

Before Jeb and I knew it, both rough riders mounted us and started to thrust their hot dicks up our asses.  Damn it hurt like hell.  There was no time for us to get used to having thick horny cowboy cock up our fuck holes.  Both Jeb and I screamed into our gags.  The rough riders didn’t seem to care and both started humping our asses hard.  We both felt like we were being cut in two.

“Yee Haw boys”, shouted Cade.  “Nothing like hot boys to ride and fuck!”

“Rodeo has just started boys”, said Abe.  “You’ll be taking Cade and my cock several times tonight.  And hell, you’ll get our morning woods too.”

Abe shot his load up my ass first, almost at the same time that Cade was shooting into Jeb.  Both cowboys rode us until they were well drained.  They collapsed on top of us and quickly fell asleep.  Their dicks deflated and naturally fell out of our holes.  I could feel Abe’s cum dripping out of my hole.

Sometime during the night, both cowboys woke up.  They decided to trade boys and both humped us again.  While the second fuck wasn’t quite as bad as the first one, it still hurt like hell.

In the morning, the two cowboys slowly woke up.  Both had huge morning woods.  They decided they needed to show us how to suck cock.  Together the two cowboys first tied up Jeb.  He was kneeling with his hands tied behind his back and then tied to his ankles.  Another rope around his neck.  They did the same to me.

“Now boys, you can see that Abe and I both have hard morning woods that we need taken care of.  Just open your mouths up and we’ll take care of the rest.  If you resist, well, it might go pretty rough on ya this morning.”

Both cowboys had in fresh dips and both spit some dip on their cocks.  I couldn’t believe it but I had to take Cade’s cock in my throat covered in brown speckled spittle.  I looked over and Abe was in Jeb’s mouth too.  They took the rope around our necks and pulled them tight.  Forced their hard cocks in our throats and used their free hand on the top of head holding our hair to keep us from moving as they thrust their cocks in and out of our mouths.  Just before they came, they pulled out and shot their loads on our faces.  It was humiliating to have man cum dripping down my chin.

The rough riders decided that we need to take care of each other’s morning woods so they left us tied up and placed us lying next to each on the bed.  Jeb’s dick was forced into my mouth and mine in Jeb’s.

The cowboys told us to start sucking to be let go.  Then they took bets on which one of us would cum first.

I have to admit, while at first, I was embarrassed, I enjoyed the feeling of Jeb’s mouth on my dick.  Yeah, I could see why these rough riders enjoyed rough man sex.  It didn’t take long for me to unload in Jeb’s mouth.  I had to really coax Jeb to cum, but his finally did.

Then we were untied and like nothing happened, the cowboys asked if we wanted to clean up and go to breakfast.

Jeb was hesitant at first, but I coaxed him into going along.

Saturday, we placed second again in the rodeo.  We were stoked.  Afterwards, we were drinking again with Cade and Abe.  We were a bit more careful.  Around midnight we all drove back to the motel.

Cade and Abe wanted to fuck us again.  They said they wouldn’t tie us up if we’d be willing participants.

“Well cowboys”, I said, “if you’re gonna fuck our asses, I figure that Jeb and I get to fuck your cowboy butts next.”

“Yeah cowboys, I guess it’s all part of the rodeo”, said Abe.

The rough riders stripped naked and put on their chaps, boots, spurs, and hat and mounted Jeb and I.  They rode us and came up our fuck chutes.  While it was uncomfortable, it was way more bearable than the first time.

I couldn’t wait to get into some cowboy ass.  I took a dip of Cope and handed the can to Jeb who also put in a wad.  I choose Cade because I thought he was the best looking one and damn his ass looked hot.  I couldn’t believe once I lubed his ass how great it felt to have my cock up his ass.  Jeb and I rode them until we came.

Jeb and I fell into our bed and fell fast asleep.  In the morning, the two cowboys wanted to watch us fuck.  I let Jeb fuck my ass.  He wasn’t ready to take cowboy cock.  I really enjoyed having my best friend inside me.  I was surprised at how this weekend was turning out.

We finished the rodeo on Sunday in second place.  We went home stoked.  We talked a bit about the weekend on the way home.  Jeb wasn’t ready to play again.  I knew that I really enjoyed the rough man sex.  The two rough cowboys were right.  While I enjoyed sex with women, the man sex was definitely much more fun in that you could be as rough as you wanted.

Jeb and I continued to rodeo.  A couple of times a year, I found a hot rodeo cowboy who enjoyed rough man sex and I definitely played with the cowboy.  I’d tell Jeb I’d found a buckle bunny and would see him in the morning and go off with the cowboy.

After our third year of rodeo, Jeb and his girl Sarah got hitched.  Jeb didn’t want to rodeo anymore.  I needed to find me a new partner.

I rodeoed off and on the next year.  At various rodeos, I’d find a partner for team roping and concentrated on my tie-down roping.  I loved the rodeo circuit and I was starting to get into the money at many of the local rodeos.  But I needed to find a team roping partner.

Towards the end of the rodeo season, I was at a rodeo in Decatur, Texas when this older roper approached me.  Said he’d heard I was looking for a heeler.  His header just left and he wanted to know if we could team up.  We did and came in first place.  At the end of the rodeo, the cowboy, his name was Blake, asked me if I was interested in finishing the season together.

“Hell yeah”, I replied.  Damn, we’d just hit first place.

“Well, Landry”, said Blake, “I’ve watched ya rope.  I know you’re good, but I think if you let me I can help you improve.”

I was a little pissed off.  Like “who the hell are you?” I thought.  I realized it was just my pride and that this roper really did have a few more trophy buckles than me.

“Yeah, I’d be interested in becoming a team”, I replied.

“Good, Landry.  Do you think your folks would let you stay at my place so we have more time to practice?”

“Yeah, my younger brother can pretty much run the place with my dad.”

“Good.  One more thing Landry, my training approach is a bit unique.  I’ve had great success training cowboys.  But you’ll have to completely do whatever I tell you.  Including taking my discipline when you fuck up.”

“Who was this asshole”, I was thinking?

Blake could see I was hesitating.  “I tell you what Landry, come out to my place this week for a few days.  We’ll train and rodeo at Wichita Falls next weekend.  Then you can see if you want to team up.

“Sounds good Blake.  Shoot me your ranch address in Gainsville and I’ll be there late on Tuesday.”

“See you Tuesday Landry.”

 

~~~~~  ∞ж∞  ~~~~~

 

I pulled into Blake’s Gainsville ranch on Tuesday with my horse.  My parents were thrilled I’d find a new partner who wanted to help me improve my roping.

Blake showed me the barn and helped me get my horse settled.  It was time for dinner and Blake had dinner ready.  We enjoyed a nice steak dinner.

Blake ran down his proposal that if I stayed, he wanted me to work as his ranch foreman.  He was in IT and worked during the week, mainly from home, but went into the office when needed.  He needed someone to run the ranch for him he trusted.  I’d be paid for my work.

Everything sounded good to me.  I noticed that Blake kept bushing close to me.  Touching me through-out the evening.  I hadn’t really thought about it until after dinner we took our beers into the living room.

Blake asked if I was aware of the rodeo way of life and rough man sex?

I was surprised by his bluntness.  I sort of stammered, “Well yeah, Blake.  I’m familiar that cowboys hook up from time to time.  And well, yeah, I’ve had a few encounters myself.”

“Good, Landry”, Blake said.  “I was hoping that you’d be open to us having some rough man sex too.”

Again, I was stunned by the conversation and calmness in Blake’s request.  I hadn’t really noticed before how good looking his was.  Suddenly my dick got hard.  I hoped Blake hadn’t noticed, but I think he did.

Blake changed the subject and we finished the evening.

The next morning, Blake took the day off from work and watched me rope calves in his corral.  My timing was off and Blake kept giving me tips.  Nothing seemed to help.

We had lunch in the house and afterwards Blake took me to the living room.  He told me to lean over the saddle in his living room where he strapped me down with rope.  I was surprised.

“Landry, I told you that my training was not standard.  You agreed to be my student.  Since you fucked up so much this morning, I figured it was time to start your training.  You’re gonna get paddled for your fucked up roping this morning.  You need to concentrate your mind on roping.  Hopefully this whipping will help you focus this afternoon.”

I protested which caused Blake to put a ball gag on me and then he used a wooden paddle to whip my ass 30 times.  I couldn’t believe it.  I hadn’t been paddled for years.

After Blake finished, he let me stew for about 15 minutes alone before he came back and took off my ball gag.

“What the fuck was that”, I shouted.

“Your punishment Landry.  I told you that my methods were unconventional.  You will be similarly punished every time you fuck up your roping.”

Blake was now standing with his crotch in my face.  I could see his bulge in his Wranglers surrounded by his leather chaps.

“I think paddling your ass has made me horny.  Maybe you want to suck your Sir off next?”

“Yes Sir, feed me your cock.”

Blake didn’t waste any time unleashing his rock-hard cock and forcing it into my mouth.  I took his cock in and started sucking him.  Blake started groaning.  I enjoyed taking him in being tied up.  It reminded of my first experience with those two rugged rough riders.

It didn’t take long for Blake to unload down my throat.  After that first time, I’d had enough man sex experiences that this wasn’t my first-time drinking man cum.

Blake was satisfied and untied me from the saddle.  He ordered me back outside and to get back to roping.  He knew how much the saddle would hurt with my ass tanned by his wood paddle.

I was surprised but I actually started roping better in the afternoon even though my ass smarted in the saddle.  I definitely had new motivation to rope my calves.

As we got ready for bed, Blake came into my room as asked if I wanted to spend the night with him.  I decided it would be fun to have some man sex.

Blake was horny and rode me hard in his bed.  After he came inside me, he turned me over and buried his head in my crotch and started sucking me off.  Fuck, it was so hot.  I enjoyed Blake and his sexual prowess.  It didn’t take me long to explode in his mouth.  We fell asleep spooning each other in bed.

 

~~~~~  ∞ж∞  ~~~~~

 

Friday at the rodeo in Wichita Falls, I screwed up as the header and missed the calf.  That night in the motel, Blake took out the wooden paddle and whipped my ass.

Saturday and Sunday we made up for Friday and came in third place in team roping.

Blake asked me if I was ready to become his fulltime ranch foreman.

“Hell yeah cowboy”, I responded.

“Good, boy.  I think we’ll get along just fine cowboy.  We make a pretty good team.”

Both of us enjoyed the drive back to the ranch.  Just like when I rode with Jeb, we both took turns driving and definitely enjoyed taking our dips along with Mt Dew.

I enjoyed taking care of the ranch for Blake.  That gave Blake more time to focus on work.  We constantly had roping practice during the week and then hit the road most weekends for rodeos.  We were placing in most rodeos each week.  Damn, I was enjoying my new life and we basically spent most nights in bed together.

Once a week, we’d have a rodeo play night.  Blake would take me to different places in the house, barn or outdoors on the ranch and he would enjoy putting me into different bondage scenarios.  Fuck, I loved being his boy and having him bind me with rope and leather and then have his way sexually with me.  He was very creative and we had so many damn hot sex scenes.  The year flew by quickly.

 

~~~~~  ∞ж∞  ~~~~~

 

Trace was an Oklahoma rough rider rodeo cowboy who primarily rode bulls.  His first year as a professional at 21 years of age, he was a golden boy and managed to win some money and trophy buckles in the local rodeos in Oklahoma and Texas.  Trace enjoyed the attention he received on the rodeo circuit and enjoyed living the rodeo cowboy life with buckle bunnies for him to chase and fuck at each rodeo.  Trace was good enough that a couple of small-town feed and tack stores sponsored him, which paid his entry fees and gave him a little spending money.  He partnered up with a couple of other rough rider cowboys traveling together from rodeo to rodeo.

Early in Trace’s second year, he took a hard landing and getting stepped on by a bull at a rodeo in Amarillo.  That messed up his timing and gave him some pain when he rode that was causing him to slip in the standings and he was not placing.

The rodeo life rarely has much money.  Most cowboys do it for the adrenaline thrill and have another job that provides money.  Trace didn’t have another job at the moment and was quickly out of money to travel and pay his rodeo entry fee.  Both his sponsors dropped out after his wreck with the bull, so Trace was really hurting for money.

There was an older ex-rodeo cowboy who would loan money to cowboys who needed their entry fee paid.  Of course, it came with pretty high repayment from winning a rodeo purse.  If you didn’t pay up there were consequences that weren’t pleasant.

Trace was desperate and met up with the cowboy who gave him money for the next rodeo in Durant.

Trace rode his bull the best he had all season, but still only managed to place fourth – out of the money purse.  Damn, Trace was pissed.

Before he left the rodeo, the older cowboy asked what Trace was going to do about his debt.  Trace pleaded for another entry fee to pursue winning another purse.  He knew that he’s found his groove and would win next week.  Trace convinced him to do a double or nothing proposal.  The cowboy laughed and told Trace he’d seem him next week in Broken Bow.

Trace was stoked and placed second place on Friday night.  He knew this would be his rodeo.  Saturday he was bucked off before the buzzer, but still could place with a good ride on Sunday.

Sunday the bull did an unexpected twist at 7-seconds that threw Trace to the ground.

“Shit”, thought Trace.  He knew his ass was in trouble.

Behind the chutes, the cowboy who loaned the money came up to Trace.  “So, cowboy, now what are you going to do to pay me back my money?”

“Please give me one more chance.  You see I’m so close to winning.”

“Well Trace, you had a good year last year.  Okay, I’ll spot you one more fee.  You lose, and you’re a three-time loser.  That means I will find any cowboy to buy your debt and you’ll be his cowboy for however long it takes you pay that off.”

“Okay, I’ll do it.  You won’t regret it.”

“I know I won’t regret it Trace.  I always get paid.  And just to be sure you know you owe me; my boys have a surprise behind the chutes.”

I followed the cowboy behind the chutes.  Suddenly several young cowboys came around me and grabbed my hands.  My face was pushed into the chute’s metal fence and my wrists and ankles tied to the fence.  I started to holler and a dirty bandana was thrust into my open mouth gagging me.

One of the cowboys had a propane tank with a brush burner that he lit.  I was scared as hell wondering what he was going to do with that.

Another cowboy handed the ex-rodeo cowboy a branding iron.  He showed it to me and said, “I told you Trace that you won’t forget the debt you owed me.  Well Trace, now you’ll always remember that I get paid.  My brand will remind you.”

I struggled and tried to escape but the ropes were too tight.  The cowboys were enjoying my dilemma.

They unbuckled my trophy buckle and dropped my Wranglers to my knees and pulled down my underwear.  My bare ass was exposed as one of the cowboys heated up the branding iron with that brush burner to a bright red glow.

The younger cowboy pressed the red-hot brand into my ass.  As sickly smell of burning human flesh filled the air as the brand seared my ass.

I was untied and let go.  The cowboys were laughing a hollering.  We headed to the area behind the rodeo arena were all the cowboys had their trailers.  The cowboys all congregated outside the older cowboy’s trailer.  A beer was thrust into my hand and all the cowboys were laughing and joking with me.  More than one made sure to slap my ass hard when I wasn’t looking, which hurt like hell.  I hung out for an hour drinking with the cowboys before I head home.  Longest ride home as I couldn’t get comfortable with that fresh brand stinging my ass.

The next week at the rodeo in Amarillo I rode my bull hard.  Still, I couldn’t place into the money.  The brand on my ass didn’t help me either with my ride.

On Sunday after the rodeo, I met the cowboy I owed money to at the local bar where most of the rodeo cowboys had gone to celebrate.

I tried to ask for more time to pay.  Instead, the cowboy told me he found a cowboy who bought my debt.  The cowboy was smiling ear-to-ear because I’m sure whoever bought my debt wanted a young stud hung cowboy for sexual reasons.

A cowboy came up and introduced himself as Blake and that he had bought my debt.  I recognized Blake as one of the team ropers from the rodeo.  That I would work for him for at least a month to pay it off.  He had a ranch outside Gainsville, Texas and I would travel back with him and Landry, his ranch foreman and team roping partner.

I was happy to at least be with some other rodeo cowboys.  We loaded up Blake and Landry’s horses and headed to the ranch.

 

~~~~~  ∞ж∞  ~~~~~

 Liked Part 1? Read the Conclusion Here!