The first time I was single tail whipped was a life-changing experience for me. I was young; probably too young to be looking for play like this. I had found this Navy guy on Grindr who wasn’t too far away. He was pretty hot, said he was from Iowa / southern Illinois, had this cowboy/farmboy aesthetic to him. He wore wranglers, boots, tight shirts. He was a volunteer firefighter/ paramedic too! He was kind of pudgy, but in a has lots of muscle but loves his carbs kinda way. Kind of hit the fetish jackpot, at least for me. I talked to him for 3 or 4 weeks before I finally consented to play. We had worked out limits and what I needed in a scene and what he wanted to do to me. I had agreed (stupidly) to allow him to judge when I had enough. I drove down to his place, about 40 min from me, and followed his instructions to enter the side door and restrain myself in the garage with what he had laid out. I went into the garage and it was super organized: perfectly clean floor, tools hanging on the walls, two immaculate motorcycles one parked on each side, and some chain and hooks hanging down from the center. In a square taped out on the floor in bright yellow were wrist and ankle restraints, padlocks, and a gag. I stripped off my clothes and placed them in a box with my phone and wallet and placed a lock on the box. I put the restraints on and put the tiny padlocks through the lock holes securing them on. I then used larger padlocks to secure my wrists on the chain while I was on my tiptoes as he instructed in our last text. I waited there stretched out for maybe 10 minutes. It was just long enough for me to start regretting being stretch out and sore. He entered through a doorway and was only wearing jeans and his cowboy boots. I was so relieved I hadn’t been catfished.

Since we had talked for a few weeks, he knew all the buttons to push on me. He went behind me and blindfolded me and places a sawhorse under me and clipped my ankles to it so I was balancing painfully on my taint. He got close to my ear and started doing a ton of mind fucky verbal. “I’m glad you showed up faggot, I love that I can do things to you I can to my wife” “God you fags are annoying and pathetic” “Make no mistake I hate you and I’m just using you to get off, if I did what I’m about to do to you to a real person I’d be in jail” He kept the verbal up and in-between getting in my head he was warming up my back with a flogger. This continued until I was squirming and asking for a break. Eventually, he removed the sawhorse and put my weight back on my sore and slightly numb arms. I thought we were close to done so I was begging him through the gag to just fuck me so I could leave. He disappeared into the house for a few minutes and I heard him behind me I felt him slightly lube my hole and I breathed a sigh of relief. Then suddenly I feel a large hard object pressing into my hole. Its not his dick its far to hard and big.  It’s way too big, it’s stretching me too far, I feel a stinging, I know I’m bleeding. I scream. I beg. He leans in and tells me, “I don’t stick my dick in fags, dick is for women. Not faggot trash like you. Go ahead and scream the neighbors are gone and the wife is deployed. No one can hear you.”

He removes the blindfold and I’m staring at him holding a whip. I had never been whipped before. I knew this would be rough. We had talked about it and discussed me trying a few strokes with it to see if I liked it. But I knew at this point nothing was going to be easy and he was keeping our agreement that he decided when I was done. He went behind me and I heard him shuffling about in his boots. Then I heard it. I heard a crack. I figured he missed my back. Then I felt it, like lightning shooting across my back. An instant line of stinging, electrifying, scorching heat. I let out a scream and curled into a ball suspended by my arms. He shouted at me that if I didn’t hold still he’d restrain me further and I’d regret it. I uncurled from my acrobatic fetal position. And only seconds after I felt the pain again. I curled up again in a natural response. He was not happy. He drug some weights out of the corner and roped my feet to them and spread them apart so my legs were painfully split apart. He then returned to the whip. Lash after lash I could only slightly move my torso; arms completely numb now and unresponsive. I lost count of how many times he hit me. I was just crying and my throat was sore from screaming through the gag. At some point, I just gave up. I had no fight left. I stopped screaming, I stopped squirming. He kept going for a few strokes, came over, and checked to see I was still conscious. Shined a light in my eyes. And I honestly don’t remember much past that. I remember vaguely him removing the gag and asking if I needed more and I guess I said something like, “whatever, I don’t care Sir.“ He chuckled and had the most smug douchebag look on his face and said, “perfect” and went back behind me and continued his assault on my backside. But honestly, my memory of the whole thing after that is fuzzy until I remember being laid down on the could concrete floor. It was so cool and felt amazing on my back.

After he let me down to the floor he put his boots under my face and shoved the toe of one in my mouth while he laughed and kept doing some heavy verbal about how stupid I was to do this and a lot of very nonpolitically correct verbal that surpasses my ability to type them out, mainly out of shame that I was so wildly turned on by his abuse. He left me on the floor and went back into the house. I don’t know for how long. He opened the door and threw a bottle of water at me from the door, he told me to hydrate. He kicked me over on to my stomach and sprayed some alcohol on my back and ass, my world lit on fire again but I dare not move out of fear he’d start back up to punish me. He said he’d be back in a few minutes and disappeared into the house. I laid on the floor and sipped from the bottle. I looked over at my reflection in the chrome of one of his bikes. I was a complete wreck. Tears and snot on my face, hair completely disheveled.  He came back out, he told me to look up at him. He said, “I guess you earned this” and pulled a used condom out of his closed hand and then drained it out all over my face. He pulled his phone out and took a picture of my cum covered face with the condom thrown across my forehead.  Told me not to move. Then he went over to the box and pulled out my wallet. He held up my ID next to my face and took another picture. He told me if I ever told anyone about him he’d print the pic out and send it to my family or post it online. He then threw a towel down on me and told me to clean up and get out. He went back in the house. I still was unable to move and I was very very pain drunk (I’m not sure what other masochists call it but its that state were your brain is swimming in so many chemicals and hormones its impossible to form thoughts or move in intentional ways.)  Slowly recovering on his garage floor was my first time feeling that wonderful glow that comes after a super heavy pain session, where the whole world just moves slow and you cant really feel anything at all. 

He ended up calling my friend to come and get me to drive me home. We went back later that night and retrieved my car. I was very regretful of that meeting for about 2 days. I was pissed. I was afraid of him. But I kept coming back to the thought of how good it felt and that he never broke any limit I had stated, I told him it was okay to push me beyond when I wanted and he was a trained paramedic and fireman. So it was about as safe as I could be for being a completely dumb thing to do. I knew that nothing that happened was completely dangerous, risky yes, but not dangerous. After I got over that second day of tossing and turning over whether what happened was okay, I decided that while it was painful, scary, and disturbing, I had jerked off to it dozens of times in a few days. He had texted me repeatedly in those days to check on me and I ignored him. I finally replied and thanked him. He never used me again sadly, he moved shortly after this experience. And to be honest I wasn’t aware he was married until we were playing and him fooling around on the side without her knowing felt wrong. 

He lives somewhere in Maryland now. Occasionally, I’ll pull up his profile and want to message him but I don’t. Partly out of fear, partly because he’s married, partly out of not wanting to alter my experience of what happened that day or tarnish it with a lesser experience. That experience changed me. I can pinpoint when I crossed a line and became addicted to pain and the feelings after some heavy use — it was that day. It was that day also I developed a need for the heavy verbal and mindfuckery that he did. I have been chasing scenes and trying to replicate that helpless feeling I had crumpled on the floor with his boot painfully shoved my mouth and him finding amusement at my weakness and pain. It changed my entire sexual life. Granted I wanted all these things, but without being ‘forced’ to experience them, I doubt I ever would have had the balls to intentionally seek it out.