My first hookup with this man was incredibly hot. I was in my early twenties, and he was in his late fifties. I am not sure what he did for a living, but he must have been successful. He basically had a guest house that, as far as I could tell, was just dedicated to sex. The first time when I got to his place, he took me into one room of this guest house and had me get entirely naked and lie on a massage table. He gave me a deep, long, rough massage. He teased the hell out of me for what seemed like an eternity. I think this was more for his pleasure than mine, as he was overflowing with eagerness when the massage finally ended.
He fucked my brains out. He was incredibly muscular and put all of his strength into railing me. I was screaming by the end of it. He growled right in my ear when he came inside of me.
The second time we hooked up, we went into his actual house for a bit first. We chatted and drank a little. Then more or less repeated the first hookup. The only difference was that this time I wore a thong under my clothes and kept it on during the massage. He pulled it to the side when he fucked me this time. Just as hard as the first time. I often think that the little flair I added is what sparked such a quick escalation in our hookups.
The third time, after another long, teasing massage, he led me into a new room in his guest house. Instead of a simple massage chair, this room had what I can only describe as a fuck table. It was padded and adjustable, and there were a plethora of different ways one could be strapped to it. He strapped me to the table so I was face down, ass up. My wrists, knees, and ankles were bound to the table. He teased my hole with the tip of his cock, then SMACK. He slapped my ass hard and without warning. I literally yelped. He paused. I assume this was to give me an opportunity to protest. I did not. SMACK. Yelp. SMACK. Yelp. SMACK. Yelp. Tears started welling in my eyes. He paused again. This time, instead of an opportunity to protest, it was a demand for supplication. He told me he would only continue if I begged for more. Only if I said, 'Daddy please spank me!' would he continue. So, of course, I begged. I screamed 'Daddy please spank me!'
He did what I implored him to do. He spanked me. Hard. In between spanks, he called me dirty names. Slut. Bitch. Sissy. Hole. Then, he made me parrot his degradation back to him. 'Yes, I'm a stupid slut.' 'Yes, I'm a little bitch.' 'Yes, I'm a brainless sissy.' 'Yes, I'm just a hole for you to use.' The pain, the yelling, the horniness, and the crying made it so I was barely conscious when he finally told me to beg for his dick, but when he did, I blurted out the most desperate, pathetic sequence of pleading possible. I was so turned on by this point that when he slowly slid his dick inside of me, cum squirted out of mine. Each thrust, every impact on my prostate, caused me to eject even more. I tensed and pulled on the straps as he ramped up the speed, but the restraints didn't budge. When he finally got to full-on hard fucking, I pressed my face into the padding and lost all control of the noises being emitted from my mouth. I felt like I was having a perpetual anal orgasm and was on the verge of passing out, but each hard thrust jolted me back to consciousness. When he finally came in me, my mind was mush, and I was no longer in control of my body. He just left me there for a while. My face planted in a puddle of drool, all of my cum pumped out of my dick, and all of his cum pumped into mine. Living, breathing proof that his humiliating insults were, in fact, true.
Afterward, instead of sending me on my way like the first two times, he invited me into his house for a drink. I maybe had two sips of a beer before I fell asleep, cuddled up to him with my head on his chest. The gesture was important. In his sex house, he used me like a toy, but in his actual house, he treated me like a person. This made it so that the nature of the fourth hookup was only slightly terrifying. When he woke me up, we chatted a little before he sent me on my way. I remember him asking me about the rest of my sex life. I confessed that there wasn't much outside of our little thing. I was busy with school and was also an extremely introverted person in general. Hooking up was mostly just stress relief, I said, though that was mostly a lie. He then said, playfully, 'You are too good of a slut to restrict yourself to one man.' At that moment, I just took that as a compliment. It was not until the next time that we hooked up that I realized he meant that literally.
Our communication for the first three hookups was extremely minimal. I met him on Grindr. We exchanged pics. He sent me an address. I went over. Got fucked. I asked for his number. For the next two hookups, I just messaged him when I was free and horny, and he told me when to come over. This time, however, he messaged me first. He asked me if I would be free on a Saturday night three weeks in advance. I said 'yes', then he told me to be at his place at a certain time, no later or earlier. 'Ok, Daddy,' I thought, 'Whatever you say.'
What happened when Saturday finally arrived wasn't entirely a surprise. When the Uber driver dropped me off at the man's place, he asked 'Big party happening?' since there were about a dozen cars parked outside of the house. I mumbled some answer to him, before exiting the car and walking tentatively to the house. The man was waiting outside for me, and he indicated toward the guest house.
When we walked inside, I stripped down to just my thong, anticipating that we would still start with the typical massage. "This is cute," he said and snapped my thong, "but I got you something better." What he got me was a full lingerie set. Black, frilly, and feminine, complete with stockings and garters. Instead of a thong, it had bottomless underwear that kept my ass exposed. Additionally, he had me wear straps on my ankles and wrists, and a collar for my neck. Each of them was thickly padded and had metal rings attached to them.
Instead of having me lie down on the massage table, he led me to a recliner in the corner of the room. He sat down and had me sit on his lap. "Do you know what a safe word is?" he asked. I told him I did. He told me that my safe word is 'peacock'.
"Do you understand?" He asked.
"Yes, I understand."
"Ok, now lie down on my lap."
I was told and laid over his lap with my ass exposed. I was expecting a beating, but I only got a teasing. He gently fingered my hold and patted my ass. He asked me if I wanted to be a good slut tonight.
