My First Time Dominating a Man

Do you remember your first time?

I was 19, and had been chatting with a 38 year old Orthodox Jewish man from NYC named Mark from the sugar daddy site Seeking Arrangement. Not just chatting, though--at this point we were in some sort of long-distance relationship that consisted of daily texts, FaceTime calls, and him sending me gifts and money over the course of 4 months.

When April came, we were both ready and available to meet.

When we first started talking, he asked me what I like in bed. I told him "a lot of things". On one hand, I was an inexperienced 19 year old who had only had sex with 2 men, and those men were vanilla. Sex consisted of oral, missionary, and doggy.
I thought, what more does he expect me to say?

On the other hand, I had a ravenous appetite for adventure and kink. I had coaxed the two vanilla men into threesomes and public sex, only to be judged for wanting more than they could handle.

I didn't want to share that with Mark.

I asked him what he liked, and he told me he was more submissive.

I had never been with a submissive man before. The men around me were predictably masculine and vanilla. I had choked and slapped one of the two men I had been with, just to see how far I could push. But he didn’t like it.

With Mark, I could finally have my fun.

He was in Miami for Passover with his family, but planned to sneak away to see me in my hotel, have dinner, and go shopping; what a naughty, little Jew. I always told him he was a bad boy for breaking the rules and going against his religion to be with me. But the will of a submissive man is a dangerous thing--especially when he’s willing to forsake everything for the chance to submit.

I arrived in Miami ready to play with my pet. After months of talking, teasing, and building this moment up, we were finally going to be face-to-face, or rather him on his knees and me towering above him.

I sat on my hotel bed, waiting for him to finish playing Scrabble with his kids. There was something thrilling and humorous about him sneaking around: one moment he'd be wearing a Kippah and playing devoted father, and the next he would be with me dipping into his depravity. Moments later, I got a text saying he was on his way, and a knock on my door followed soon after. My pussy was tingling.

We greeted each other with an enthusiastic kiss and pleasantries about my flight and how his family was. In the back of my mind, I was sizing him up and thinking about what was to come. When the small talk faded, I told him to show me what was in the bag of goodies he bought:

• La Perla bra, panties, garter belt, and stockings

• Dildo with strapon harness

• Collar and leash

• Butt plug

I was already in domme-mode by the time he stepped foot in the door, but seeing the toys and gifts made me ready to have my way with him. I knew he was yearning for it, he was hard the moment we hugged after he stepped through the door.

I told him to undress and put the butt plug in and collar and leash on, while I slipped into the bathroom to put on the lingerie. I felt sexy, and looked even hotter. This was the cherry on top of me.

I came out to a grown man on his knees, looking like a sad puppy dog. I laughed at the sight of this grown man reduced to nothing but an obedient pet, waiting to be owned.

I patted him on the head, called him a good boy, and grabbed the leash pulling him close to me. He stared up at me, mesmerized, with his mouth open. This was what worship is, I thought. I had never seen anyone look at me like that before; it was as if he was in a trance.

Part of me didn't know what to do next, but I knew this was my time and I could do whatever I wanted.

I tugged the leash and led him around the room. Having him sit, lay down, heel, and bark. He was my puppy and had to follow my commands. What owner would I be without properly training him?

I had him repeat commands, instilling my authority while also trying to gauge what he was into. He seemed to like humiliation, so I told him he was pathetic, had a small cock, he was a horrible Jew and if only his Rabbi knew what a degenerate is was, and that he was a loser who couldn't satisfy a woman and that's why his wife cheated on him. There was nothing off limits, and I gave it to him like he deserved.

I loved that he moaned and cowered after every degrading thing I said to him. I watched his dick twitch as it got harder and harder.

My pussy had gone from tingly to dripping wet, too. I let go of the leash, and took my panties off. I brushed my fingers over my thigh that was covered in my juices, and told him to lick it off my finger.

"Good boy", I said. He said he wanted to eat my pussy and lick up every drop. But I wanted to see how much he could take down his throat. I put my finger back in his mouth and told him to suck on it like a good boy. One by one, I put all of my fingers in his mouth; watching him gag made me smile.

I instructed him to the bed and to lay on his back. Straddling his chest, I told him to beg for my pussy and to tell me how much he wanted me to ride his face.

I had never ridden a mans face before--I hadn't done anything I did tonight, ever. Did I put my full weight on his face? Do I hover over his mouth? Can he breathe? Should I move, or just sit there while he licks my clit?

He begged, and I slapped his face.
He begged, and I spit in his mouth.
He begged, and I told him I'm going to use his mouth because his small cock is useless to me.

I moved closer, and placed my perfect pussy on his mouth. He grabbed my ass, pulling me closer. I felt like I was smothering him, but he was devouring me. He moaned and his legs were shaking uncontrollably.

I had never been with someone so obsessed and turned on by eating pussy before. Once I knew he liked me smothering him with my pussy, I started riding back and forth more aggressively, pulling his head closer by pulling his hair, and closed his nose shut occasionally--totally using him for my pleasure, and having my way with him. He wanted to be my pet, owned, and used, and I knew I could take full advantage of that, and he'd be more than willing to oblige with anything I subjected him to.

After I used his mouth and left him licking his lips, it was time for me to use his ass.

I had never even seen a man's asshole before, nonetheless stuck anything up there. Would he cum from it? Would there be shit involved? I didn't know, but I would find out. I remember thinking that I'd just fuck him how I've been fucked.

I ordered him to lay on his stomach. After all, good boys need spankings before they get fucked. I used my bare hand, and with every strike his ass got redder and redder, and he screamed and squirmed in agony. But he never told me to stop.

I laughed.

I grabbed his balls, pulling them toward me, slapping them too.

He loved it.

When I took the butt plug out, it was clean. No shit, great.

I put the dildo in the strap on, and slipped on the harness. Is this how men feel with a hard cock? I had him lay on his back, legs bent toward him. He was going to look in my eyes the entire time I was fucking his tight, little asshole. I drench his hole with lube, and put a finger in. No shit, great.

Even though he had a decent size butt plug in, he moaned when I inserted my much smaller finger. I didn't know what I was feeling for, or if I was hitting his prostate, but he was enjoying it so I just continued. I threw out every nasty thing I could think of: more degradation, humiliation, and having him beg me to fuck him.

There's something about a man begging that turns me on. I think it has to do with having something someone else wants, but you are in the position of power to say yes or no; he was at my whim. Add to that, a man spread open like a whore, begging me to fuck him with a big dildo? He's even more at my mercy.

I poured more lube on his hole and the dildo, and slowly started filling him up. I started thrusting, going deeper and deeper each time. I thought about how men who have fucked me, fuck. I thought about porn. I thought wow this is tiring, men really put in work when they're on top.

With each stroke he moaned and squirmed. Once his ass was warmed up, I knew I wanted to really give him a pounding. I pushed his thighs back, grabbed his hard cock, and started fucking him deeper and deeper while I stroked his cock.

He came so hard, I genuinely panicked for a second. His face turned bright red, and the guttural moan he made was so loud, and with an intensity I had never heard before. He was overweight, so I thought he might've been having a heart attack. Was he dying?Would I be left alone in this hotel room with a dead man? How would I explain any of this to hotel staff or the police?

I asked him if he was okay and he laughed. I was relieved.

The next day, we went to the beach. At some point, he got a work call. He wasn't supposed to be getting work calls during Passover, and was pissed.

As I laid on the beach, baking in the sun, I listened as he barked orders into the phone, tearing into whoever was on the other end. I smirked, loving the contrast. At work, he was powerful and sharp. But with me? Behind closed doors? He was obedient and docile.

I realized then that a lot of men who are in charge all day, making decisions and holding power, crave a moment where they don’t have to make any choices at all. They want to turn their brains off, surrender, and be on the opposite end of that power dynamic.

Later that evening at dinner, I persuaded him to try shrimp for the first time--something against Kashrut law. Now, I was determined to turn him completely out. I told him I'd be a bad influence on him, but I knew that was exactly what he wanted.