Over the Christmas holiday, my fiance, Stacy, and I joined her parents for two weeks in Puerto Vallarta, Mexico. The warm but mostly overcast sky was a welcome break from the snow back at home. Half of the clothes we brought remained in our suitcases and not once did we wear socks. My sandals with the tire tread soles held up quite well but my girlfriend's leather sandals were needing repair as a strap had separated from the side. We asked the hotel concierge if there was a local shoe repair shop and she pointed us in the direction of a leather expert not more than four blocks away.
Stacy's mom joined us on our walk to the shop. We showed the sandal to a man behind the counter and he assured us it was repairable and he could do it as we waited. I chose to wait as Stacy and her mom visited the adjacent boutiques. I ventured to the far reaches of the shop and found an assortment of riding gear and whips hanging from the walls. I reached up to grab a small whip - maybe a foot in length.
"Cuarta," said a man as he emerged from a back room.
I nodded as the handsome gentleman approached my side.
I continued to look at the whips and then asked if he actually made all those.
"Si, si. I make," he said as he struggled for the right words. His English was about as bad as my Spanish so we didn't say much more. He took a long whip down and began showing me how well it was braided. He really did a good job making it and could tell I was impressed.
"You give cuarta?" he asked.
I thought he was asking if I would want to give it as a present.
"No, gracias. No me interesa."
He hummed and then asked, "You like cuarta? You get whip?"
I processed his words for a second and then he made the classic whipping sound: Whoop-pshhh!!
My face suddenly turned red as I realized he was asking if I enjoyed being whipped. There was no hiding my response so I just shook my head and smiled. In fact, the whip has long been a major fetish of mine and in truth I was always curious about how it might feel on my skin. This was something I could never explore with Stacy or any other woman I'd been with. Had Stacy been standing right there with me I would have turned and moved onto something else. But she wasn't there and this whip expert was asking if I was interested in being whipped.
I replied, "Maybe someday."
That took a lot more courage than to deny this desire. What's the worst outcome? We were leaving soon and I'd never see this guy again. I didn't really care enough to respond falsely.
The man reached over to a work bench and picked up his business card.
"How long in Mexico?" he asked.
I told him we were leaving the following day. Then it occurred to me Stacy and her parents were leaving the following day. I would be leaving a day later because I had decided at the last minute to join the three. Their flights were booked and I went with a different airline entirely.
The gentleman wrote his name on the back of the card and handed it to me. He had signed his name 'Sergio' with a heart above the 'i.'
"I train you. Call this."
I dropped his card into my shirt pocket after I pulled out my sunglasses. I was feeling strangely excited but decided to leave the shop and go looking for the girls.
I spent the next 15 minutes going shop to shop but did not find them until I saw the two returning to the shoe repair place. We went back inside and paid for the great work. The sandal appeared to be new and as Stacy thanked the man, Sergio walked from the back room. I smiled and put my hand on Stacy's shoulder just before we turned to leave.
Once we returned to the hotel I emptied the loose change from my pockets and took the business card out as well. I tossed it in the trash but couldn't stop thinking about the display of whips. And what did Sergio mean by training? Was he going to teach me how to handle a whip or was he going to train me how to take it?
Later that evening Stacy's parents invited us to dinner at the resort's fancy restaurant. The heat and humidity make regular showers necessary and I definitely needed one before heading downstairs. The heat also did not help my libido as I was semi-erect the moment I disrobed. Thoughts of the whips and, admittedly, thoughts of Sergio wielding one gave me a hard-on. I don't know why. I lathered up and jerked off to the thought of being whipped. I'd never been whipped or even spanked. Not as an adult and never as a child but for some reason I masturbated over the years to the thought of being stripped and whipped. Usually the fantasy involved a leather or latex-wearing dominatrix but a man holding a whip had some new appeal.
The next morning was spent cleaning and packing up. I helped Stacy and her parents down to the lobby and we summoned a taxi to the airport. Vacation definitely seemed to be winding down even though I was not to leave for 24 more hours. We got to the airport and waited with them as long as I could before they were about to board the airplane. I wasn't wild about the idea of flying home alone but it wasn't such a big deal. By the time I arrived back at the hotel I'd decided to retrieve Sergio's card from the garbage. Unfortunately, housekeeping had already been through and had taken out the trash. I did not need the card. Calling Sergio would've been pointless because of the language barrier. I needed to go see him in person. First, I went down to the bar and ordered a gin and tonic to help suppress any voice telling me this was a mistake. I did not feel the alcohol much as I walked to the leather shop. Sergio was standing behind the counter where the other man had been. His face lit up as he immediately recognized me. He glanced out the window for a moment half-expecting Stacy to walk in behind me.
"No womens today?" he asked.
I shook my head but didn't attempt to explain why I'd returned. I stared at the floor a moment waiting for his next words.
Sergio looked me up and down and then looked to the back of the store. His partner was back there. Quietly he wrote something down on another business card and then handed it to me. He seemed to understand why I'd returned. There was no more pressure to explain or even talk about what I was seeking. Sergio knew and when I saw the place and time I was to meet him, I was relieved.
I don't remember much in the hours between the time I left his shop and the time I got into the cab that evening. I was nervous and slightly drunk after my third gin. I showed the cabbie the address on my card and he began driving toward town. Ten minutes later we stopped on the cobblestone street in front of a bar. The rustic buildings all look the same so I made note of the cross street. There seemed to be a lot of nightlife for a Wednesday night. I went inside the bar and saw Sergio right away. This was obviously a gay bar as the only woman I saw was serving drinks. Sergio had a bag similar to a bowler's bag next to him. I ordered us drinks and paid for his.
"Are you ready for pain"? he asked.
I was surprised at his straightforward question and how well he'd asked it.
I looked at my drink and then back at him. His gaze did not stray from me.
"I am ready for your whip. How many times will I be whipped?"
Sergio's eyes sort of squinted and then he replied, "Cincuenta."
I had to process his answer and once he saw the look on his face he put his hand on my shoulder.
"Si. You take 50. If no, you say 'caliente.' Then I stop."
I realized this was the safe word. He repeated 'caliente' two or three more times and I let him know I understood.
We finished our drinks and he led me to the back of the small room. The bartender said something to him just as we passed by and handed him a key. I was getting a little nervous since I did not like the idea of being isolated or away from a public place. The room had no windows but it was right behind the bar and Sergio had propped the door open. The room had a few benches and an X I've seen in movies where people are fastened for punishment. A few people came in behind us holding drinks as though they were casual observers. Against the wall I noticed what looked like a short telephone pole. There was a hook near the top and two sets of foot pegs on each side.
Sergio tried to tell me something but could not translate at all. Instead, he started to undress me. Once I got what he was asking, I undressed myself. I was soon standing in my underwear and he pointed at them with a disapproving look.
Once I was stark naked he approached me with ten feet of soft, white rope. I brought my hands together and he quickly wrapped my wrists together and then led me to the pole. He guided my arms upward and hooked the rope over the hook. My feet were flat against the floor but I was completely stretched upright.
Sergio removed his shirt and hung it on a hook. A couple more people shuffled in as Sergio removed from his bag a narrow leather paddle. My heart pounded and I closed my eyes. What in the hell was I doing there? I wondered. A conversation or two in Spanish added to my concern. Sergio joined in a conversation and the men's response in laughter did not help, either. The room got quiet as my punisher took his place behind and to my left. I heard the slight tap of leather against his hand. Five seconds later I heard the paddle and then felt it slap against my butt cheek. Ouch! That wasn't too bad. I thought a man in the corner said, 'Oooh' but he was counting off with 'Uno.'
The next nine strikes against my butt cheeks were hardly tolerable. In fact the strikes of that paddle burned in the worst way. Sergio decided to change it up by replacing the paddle with a six foot-long whip and striking across my upper back. This time the strike made a 'pop' sound and I felt the burn immediately. I tensed up but still did not say anything. Every lashing after that stung worse than previous strike. I was panting and covered in a sheen of sweat. Sergio expertly landed the whip in various places from my neck to the back of my calves. I could tell the welts were beginning to rise and the pain from repeated strikes in the same place was almost too much. Still, I had yet to scream. In some weird way I justified my punishment based on the fact I was there in the first place.
"Veinticuatro" a man murmured as though he didn't want to be heard.
I was only halfway through my ordeal yet I could barely catch my breath.