My First Real Training

In my day to day life, I am a web consultant. I develop web and interactive media projects … generally creating and managing neat doodads that go whiz bang on computer screens. I don’t travel as much as I used to, but I enjoy it, and I like to meet the locals if I can. And by meet the locals, I mean get kinky of course.

One of my favorite clients had a project in Nashville, and lucky circumstances meant I was going alone – without having to dodge or ditch my colleagues that typically come along on these trips. A multi-day trip, with limited responsibilities, meant the perfect opportunity for getting into some trouble. I put feelers out there, then T and I started chatting. And he was awesome. A switch player – often a sub, but occasionally Dom – intelligent, well spoken, and clearly knew how to have a good time. We concocted various ideas, but ultimately it was settled that we’d start with a meet, get comfortable, and he’d start showing me the ropes. My first assignment? To “smuggle” something potentially embarrassing in my carry-on luggage and wear some sort of cartoonish underwear.

The rest of this story is long – it was a two day experience and a whole lot of different things to try. In it you’ll find my lessons of cock sucking, being rendered a footstool, being tied up and tortured with wax and ice, getting fucked, getting milked, learning to use poppers – and generally getting tuckered out in my first real training experience, all after the jump:

The First Day

To say I was excited was an understatement; I even changed my flights to get into Nashville earlier so I could check in with the work site ahead of schedule and have an uninterrupted evening in which to play. I got ready, I laid out what toys and such I brought, from candles and rope to butt plugs and clothes pins. I took a shower, got cleaned up, cleaned out, and went downstairs to wait in the hotel lobby. Boy was I nervous, but excited. Before long, a tall imposing bear of a man walked in wearing a button shirt, jeans, and cowboy boots carrying a duffle. It could be no one else but T. He found me, and said “Hello, boy. Let’s go to your room,” and walked off toward the elevators.

In my room, he stood me at attention and inspected me. Tested me. Hit me upside the head. Grabbed my shirt and brought me close to his face. He had me open my shirt and tweaked my nipples – he twisted them so hard I nearly cried. That’s when I got my first lesson. “Breathe, take a deep breath.”  I learned – and had to be reminded many times with the way he tortured my nipples – that deep breaths help even out the shock of the pain.

Introductions over – and my nipples tender to the slightest touch – it was time to humiliate me. It’s something I’ve never been sure about – playing in public is rough for someone so easily embarrassed. But out came the baby pacifier anyway. I had to go with him to pick it up, and he made me wear it in my mouth on the drive back to the hotel. Then he made me walk to the elevator with it, and carry it in my pocket should I step out of line. I didn’t enjoy that – at any time someone could have discovered a grown man with a pacifier and think I was a nut!

In the elevator came the order – “Get down and kiss my boot.” My mind flashed  – was he serious? What if someone got on it while I was down? What if he didn’t let me get up? What if there are cameras? But the longer I waited, the greater the risk, so I got down, kissed his cowboy boot, and got back up. It was scary, it was exhilarating, it was hot.  Later at dinner, I couldn’t order my own food or even talk to the waiter. Soon, though, it was back to the hotel, where I was introduced to his cock.

I’ve never done well with a big cock. My boyfriend has a big one, and it’s hard to suck. But T decided to shove his cock down my throat whether I liked it or not. “Take a breath.” And down it went. I gagged, I choked. Over the rest of the night he put me in different positions, taught me how to relax and not freak out, and taught me to be a better cock sucker. He’d shove it down my throat and hold it there; he loved feeling the muscles of my throat contract against it while they instinctively swallowed. By the end of our two nights together – and by the time I got home to my boyfriend – I got much better at taking a big ol’ cock down my little throat.

We played some more. I sucked his cock. He tortured my nipples. “Breathe, just breathe,” he kept saying. I served as hit foot rest for a while, too. As I was there on all fours, he took off his socks and forced his bare feet into face and mouth. I kissed them, I sucked on his toes, and he rested them on me. It was the closest I’ve ever gotten to what I imagine “sub space” is like.

Before long, though, it was time for the main event. Before this week I’d never really been tied up, but I desperately wanted to be and I love playing with wax and intense sensations. He combined them. Told to leave my shirt unbuttoned, I went to get him a bucket of ice. Returning to the room, I found a cheap shower curtain on the bed and T preparing rope. He taught me a useful knot, and then laid me down on the bed.

The game was simple. He tied me down, blindfolded me, and began asking questions. For everything I got right, nothing would happen. For everything I got wrong, I would be dosed with either hot wax or freezing ice. I couldn’t know which until it hit. I couldn’t tell which half the time – my senses were confused I though the ice was wax or vice versa half the time. Even the hit itself wasn’t so terrible, but it was the anticipation – the expectation – that I would cringe at and he would laugh, and then dose me again. The ropes were too loose, I asked him to tighten them, and then we continued with my torture.

I’m not a dumb guy, but he is wicked smart. With all the stimulation, and the pressure, and the blood rushing to my cock, I couldn’t think straight and got a lot of answers wrong that I should have known. It was an incredible experience, and by the time we were done, I was covered in wax. In the shower, I sucked his cock some more. Once the wax was cleaned off, he had me lay down in the tub, he stood over me, and pissed on me while allowing me to jack off. He then jacked off on me and we cleaned up for the night.

The Second Day

I wasn’t even expecting to play on the second day. Frankly I was pretty worn out from the first one, and even a little overstimulated. But he called and wanted to see me, so I figured we could at least hang, chat, and get to know each other better. He came over. We chatted. We cuddled. He opened my shirt and tweaked my nipples again. He reminded me to breathe deep, and twisted them until I almost cried. And then, of course, I sucked his cock.

He laid me on my back with my head hanging over the edge of the bed, creating a straight-line shot down my throat. He teased my mouth with his hard cock. He went a little further in, and then out, and then said “Are you ready?”  “Yes sir,” I barely had time to reply before he shoved his cock deep and hard into my throat. I gagged hard, choked, teared up a bit. It was a lot to take, and he made sure I was okay. We made out a bit, I sucked him some more, and then asked about fucking me.

Generally I wasn’t keen on fucking but I knew I could trust him. My ass generally does not cooperate. To say I have a tight hole is an understatement. I can rarely take my boyfriend’s cock. I rarely get much of anything up my hole, but he was willing to practice a bit, and he really wanted to fuck me.

He laid me on the bed and started to work on my hole. He lubed me up, he fingered me, adding fingers over time. He found my prostate and massaged it. It felt great. He put on a condom and tried to fuck me. It was tough going in, “Wow you really do have a tight hole.” He suggested poppers. I’d never liked the idea, because it always sounded like a drug. But since he was actually a research scientist he helped explain them, and gave me a small dose. It helped a bit, and he tried to go in me again.

Ultimately it didn’t work out to fuck me, but he had a different idea. I wanted to be milked, so that’s where we went. He lubed up his fingers and dove into for my prostate. He worked it hard. I came, I nearly came again. It was a flood of fire and sensation I felt in my ass, my balls, my cock, my spine – my whole body. It was one of the most intense things I’ve ever felt, to have his hand working my prostate hard, making me cum more than once – making me cum when and how and where he wanted to. It was almost too much, I begged him to stop. He wouldn’t – he said to be milked is to be subjected to the will of the milker, to give as much as is demanded of you. I tried to take more, but ultimately had to use a safe word to stop that play – it felt like my ass was being torn apart … and it was great!

We cleaned up, I sucked his cock, he pissed on me again, and that was the end.

Looking Back

I’ve been really fortunate with my three real-life Doms to date that they’ve all been patient, understanding, and good teachers as well as good dominant men. With T, I didn’t just have a great Dom, I had a fellow sub who knew what it was like to feel what I felt. Best of all, he demonstrated he was trust worthy beyond any doubt. Before I even went to Nashville we chatted on the phone, we chatted about limits and safe words, he made sure I had someone who could call in for safety and call the police if something was wrong. He gave tips on safety. He taught me how to be a better cock sucker, a better sub, a better bottom. He taught me a little about rope bondage.

Circumstances are such that I don’t or can’t play with them regularly, mainly because of distance or just unavailability. I would submit to T again in a heartbeat, I would even travel to Nashville again just to submit to him. He was awesome, a good teacher, and crafted the kind of experience I needed. I think what I would really need now is a regular Dom or partner to explore with, but T will always be the man who really started my training experience.

Comments (2)

  1. Romain

    Amazing 🙂 it is great to see you met with such patient Doms 🙂

  2. I’m so happy for you my friend.
    Really hot and such a good and patient Dom for you. 😉
    Did you try the new cocksucking techniques on the bf?
    what did he think? 😉

Leave a Reply

Your email address will not be published. Required fields are marked *