My Mexican Vacation
by Flier1948
Copyright© 2026 by Flier1948
BDSM Sex Story: My mid-term Mexican vacation turned into a nightmare.
Caution: This BDSM Sex Story contains strong sexual content, including Ma/Ma NonConsensual Rape Gay Fiction BDSM Humiliation Rough Spanking Gang Bang Interracial White Male Hispanic Male Anal Sex Cream Pie Oral Sex .
It had been a long two days.
My Black friend Jerry and I had decided to take a trip to Cancun between high school and college. It was going to be a nice break between studies and, since the drinking age in Mexico was 18, we looked forward to having a good time.
After arrival, we checked into our hotel room and, within only a few minutes, there was a pounding at the door.
It was the local Policia and they had a search warrant to search our room. We were seriously confused, but they came in and began searching.
In the bathroom, behind the sink, they found a ‘crack pipe’. Of course, we didn’t bring it and hadn’t been in the room long enough to have hidden it, but, before we knew it, we were in handcuffs heading for the police station.
I had never imagined such a quick arrest, trial, and sentencing. They assigned us a Mexican lawyer who barely spoke English and our ‘trial’ was held entirely in Spanish, which neither of us understood. The whole process lasted maybe 1/2 hour.
When it was over, our ‘lawyer’, in broken English, told us that we had been convicted of having drug paraphernalia and have each been sentenced to 12 strokes of the cane and six months in prison.
There was also a guy from the US consulate there who told us, in confidence, that the corrupt legal system in Mexico periodically sentenced ‘fresh meat’ to keep the prison gangs entertained since the gangs ran the prisons in Mexico. He said there wasn’t anything to be done about it, but to be careful, while in prison, to do EXACTLY as we were told by the prisoners. Do that, and we would survive the six months.
Things were a blur after that. The quick trial, then a long ride in the back of a prison van with several others. There were no windows, so we had no clue where the prison was.
Inside the prison, I was stripped and restrained, bent over, face down, with my legs wide-spread, to a bench in the prison yard; it was on some kind of elevated stage and surrounded by prisoners and guards.
A fire erupted on the top of my ass, right near where the crack began. It felt like a hot poker had been applied across my butt cheeks. I struggled against the restraints, but could not get away.
After my head cleared from the first stroke, I saw all the prisoners standing around, watching my torment, and cheering. There were two caning benches on the stage; I was on one and Jerry was on the other one. I could feel the skin on my ass was stretched tight with a stripe of pain across it.
A loud yell to my left and I knew Jerry had gotten his first stroke.
Now, it was my turn again.
The guard doing the caning looked like a body builder with muscles on top of his muscles. The cane was about five feet long and maybe 3/4 inch in diameter. I could only imagine; then, ‘tap’ ‘tap’ on my ass and a loud hiss as the cane flew through the air and landed at the base of my cheeks, where they met the thighs, the ‘sit spot’.
I didn’t have to imagine any more. Another stripe of fire erupted and I yelled loudly followed by a cheer from the crowd. They were sure enjoying this.
And so it went. Me, then Jerry, back and forth. The first two strokes marked the top and bottom of my ass and the rest filled in the space in between. I felt blood trickling down my leg. Both of us were a sobbing mess; my ass had never been roasted like that.
When it was over, we were sent to the cell block where, although there were individual cells, all of the doors were open and the inmates roamed freely. The guards stayed on the outside. They cared little about what went on inside the prison; their only job was to keep prisoners from getting out.
I was lying on the floor, naked, curled up in the fetal position. My ass was a mass of fire and itching that I couldn’t get to stop. Across the room was Jerry, also naked. He was on his stomach; I watched as his ass clenched and unclenched, trying to relieve the results of his caning.
The biggest Mexican I had ever seen in my life walked up to me; he had a half dozen other men behind him. Luckily, he spoke English.
“Well there boy, I see you and your friend got your asses torn up. That’s what happens when you break the law here. It looks like your friend is in a lot of pain. Why don’t you go over and make him feel better with a nice blow job.”
It was an order, not a question.
I started to say, “But, I’m not...,” when all I saw is a flash of brown as he slapped me so hard it caused me to see stars. I shook my head and remembered what I had been told. I went over to Jerry and gently rolled him on his side. He had a substantial cock; it was uncut, black as coal, and around six inches long, soft.
Getting between his legs, I took his cock in my mouth. It was the first time I had given a guy a blowjob; in fact the first time I had any kind of sex with another male.
Instinct took over and soon I was bobbing my head up and down. Hormones hit Jerry and his cock started to get longer and harden. Soon, I was sucking on 11 inches of rock hard dick and he was moaning loudly.
The Mexicans in the room were staring and making comments like, “Can’t wait until it’s my turn,” and, “Look at those two hot holes we get to fuck.”
I was scared to death, but not scared enough to forget that, if both of us didn’t so what we were told, things could be a lot worse.
Soon, Jerry started pumping rope after rope of thick sperm into my mouth. The taste wasn’t bad at all and I was sort of proud of myself for giving him a distraction. I swallowed as fast as I could, but still a little leaked out around my lips. When he was done and started to soften, I used my hand to milk the last few drops from his cock and then, with a loud slurp, let him go. I gently licked his cock and balls clean and started to roll out from between his legs.
When I tried to get up, the big Mexican grabbed me around the waist and threw me over a bunk, face down, with my ass hanging off one side and my head hanging off the other side. I was shocked. I’m not very little, about 160 pounds, and he picked me up like I weighed nothing. This guy was definitely strong and nobody to mess with. They left Jerry alone and l, later, I found out that Mexicans were partial to whites and not Blacks. So, good for him, he got mostly left alone while we were in jail.
I was a different story. Lying across that bunk, I found out what I was good for, to them. I had never had anything in my ass before, but that was about to change.
Someone began spreading my ass cheeks and, when I clenched them to keep them together, a hard slap on my already damaged ass, got a yelp from me and made me relax, real quick. I felt someone’s wet finger probing my asshole and, without much grace, it was shoved into me. He began finger fucking my ass, which was uncomfortable at first, but then began to feel good. About the time I was beginning to like it more, a second finger went in and the pain started all over. Again, the finger fucking and my asshole relaxed more.
A waist appeared in front of me and he dropped his pants and shorts revealing a fair sized cock. This one was cut, but smelled awful. It was clear that showers weren’t a big deal in the prison. The guy in front of me moved closer, grabbed my hair, pulled my head up, and said, “abre tu boca”. I sensed what he wanted and found out later he was telling me to open my mouth. Not wanting to aggravate anyone, I did what I was told.
He shoved his cock into my mouth; it smelled and tasted of pee. I began sucking while trying to avoid throwing up due to the smell and taste. He hardened quickly and I did my best to pleasure him.
Behind me, the fingers came out of my ass. There was a nudging between my butt cheeks of something bigger, much, much bigger. I knew I was about to take the first cock in my ass. I was terrified and couldn’t even say anything because I was gagged by the cock in my mouth.
He tried to push his cock into me, but my ass resisted, not because I wanted it to; it just did. The cock was quickly withdrawn and something hard, like a board, hit my ass four or five times. I was screaming even though my mouth was stuffed with dick. The pain was incredible.
The cock started pushing against my asshole again. He pushed, hard, and I tried to relax. With almost an audible “pop”, my asshole gave up and the head of his cock slipped into me. The pain was like nothing I had ever felt before, but he didn’t care and kept on pushing. More and more of his cock entered my bowels until I felt his pubic hair scraping my ass.
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