I’ve been thinking back on so many experiences that shaped me sexually. I would be doing a major disservice to not mention my summer as Greg’s pet. I had just turned 21 and was firmly in an alt-girl style; my bright red hair had pink and purple streaks, my lip was pierced, And a half sleeve of tattoos. Greg lived in a very swanky apartment complex, where I got invited to a pool party by an artist friend of a friend of a friend. It was the type of fancy pool party where nobody wears clothing to actually get wet because the only people that go in the pool are rolling hard on molly. I felt completely out of place. I looked across the pool to the bar and there he was. Standing out in a sharply tailored blue suit, holding a glass of dark liquor, turned away from the bar, watching me with a twinkle in his bright eyes. I smirked as he tilted his head slightly to the open seat next to him, wordlessly beckoning me to him. Every step I took tightened my chest, as if I was getting sucked into an aura stronger than my own. As I arrived, the bartender dropped a fresh drink in front of me and took the empty glass I was clutching.
“Figured I’d order you another, anything to liven this party up, right?” His eyes crinkled slightly when we smiled, but were so deeply green and bright that they seems to emanate light. His hair was salt and pepper, looking very distinguished. I was guessing him to be in his mid-fifties. He kicked his drink back and I caught sight of his Rolex, and his glass had barely hit the bar when another was set in front of him. He felt so important. I felt my body start to warm up, I was getting turned on by the power he exuded. When he asked me if I wanted to go to dinner the next night I immediately agreed. When I left the party, he had his car service take me home, giving me a kiss on the cheek with his hand at the small of my back. I could smell his cologne when he leaned close and immediately felt dizzy with lust. His eyes looked hungry too, and he huskily whispered “until tomorrow”
The next day I had a knock on my door and opened it to see the driver of the car last night, dropping off a large box. The card read, “I dreamed of you wearing this last night. Humor me, I hope it all fits. -Greg”. He had chosen my outfit that night; a short pink dress that looked like it was dripping off of my body, like melted metal, and high stiletto sandals. I thought about putting panties on because I knew that the dress was so short that I wouldn’t be able to bend over without showing everything, but I deviously decided against it. I walked out of the house to see him standing outside the car, in a black suit and a silk paisley tie in the same shade as my dress, ready for me like a perfect gentleman.
Over dinner at a restaurant I could never have afforded, we made small talk. He started and ran a successful company, and was a self-made multimillionaire by the time he was 30. By the end of the meal, I knew he barely had to work anymore, owned several properties, and had been feeling a little tired of the monotony of high society.
“Is that why you asked me out? I have to admit, we don’t look like a match.” I said playfully.
“You underestimate me. I think you’re otherworldly. Nobody at that party came close to catching my eye more than you yesterday. I wish I had experimented more back when I was in my twenties. I made up for it in my later years, but I was a bit too tame in my young bachelor days. But you- the tattoos, that sexy lip ring, you would have ruined me if I knew you then.”
“And what about now?”
SEXY PART STARTS HERE:
“Oh red,” he chuckled, “If I were you, I’d be more worried that I’ll be ruining you. That’s the blessing my years give me; I know what I want, I know what I’m doing, I can get whatever I want, and right now I want you to go to the bathroom, take your panties off, and bring them back to me.”
“A little problem there… I’m not wearing any!” I could tell he was pleasantly surprised, and he muttered ‘good girl’ quietly to me. I bit my lip and pretended that I wasn’t getting wet at his quiet sense of control, shrugged, and said slyly, “there weren’t any panties in the box”.
“This night can proceed two ways, how I see it,” Greg started, “the first version has me dropping you at your place. We could have a little kiss, I could send some flowers in the morning, and we can plan to have another night out soon. Or, the second option, where you come back to my home, and you give me complete control over your body for the night. You’ll be a good little girl and follow orders, and I’ll take care of you.”
My voice wavered with nerves, “the second one, please.”
His eyes flashed with energy. “Good girl. Now go to the car now while your Master pays.”
On the ride back, he sat opposite of me so we faced one another, and electricity buzzed between us. I had no idea what I was in for, but he knew exactly what he was about to do to me.
“Open your legs and show me your pussy.”
I did what I was told, silently thanking myself for getting waxed. His gaze was focused on my smooth pussy as he adjusted his hard cock in his trousers. I could see that it was averagely sized but incredibly thick. We arrived back to the building, he walked me through the lobby of the apartment and into the elevator, and pressed the top button. Of course, he lived in the penthouse. As the elevator started its climb, I felt him pull one strap of my dress down my shoulder.
“I want you to take this dress off, and when the elevator opens you are going to crawl on your hands and knees to the last room on the left. Is that understood?”
“Yes, understood.” I felt high with lust.
“Yes MASTER.” he growled, and I felt my pussy gush with excitement. “Yes, master!” I answered obediently. I pulled the other strap of my dress down and wiggled it down my body, showing off every curve before falling to my knees and leaning forward as the doors opened to start crawling. He walked behind me slowly through his opulent apartment, enjoying the view. I heard him toss his suit jacket aside and by the time I reached the closed door to look up at him, he had rolled the sleeves of his white dress shirt up, and loosened his tie.
“This room is my play room, Red. The contents within can unlock deep pleasure, but only if you submit yourself completely. I need you to be totally submissive in this room, and I will make sure that you experience a night of pure ecstasy. Are you ready to do this?”
“ I’m ready, Master”. And with that, he unlocked the door and sat on a red velvet chair by the huge window. “Crawl to me and make sure your master’s cock is hard” he ordered. My knees were already getting sore from the hard marble floor, but I quickly approached him undid his belt and fished his cock out to see it for the first time. I was right that it was thick, but my hand couldn’t even wrap around it fully! I opened my mouth as wide as possible to suck it, flicking my tongue over the head before swallowing as much as I could down my throat. I felt him pull my head up, and he pulled his tie off and secured it around my neck tightly. He used it like a leash, pulling and pushing my head around, ordering me to lick the head, suck the balls, eat his asshole, and then deepthroat his cock again. I was a good little sex slave, and did what he said, hearing him quietly moan “good god, Red.”. He rewarded me by slapping his cock against my face while he pulled the tie even tighter to restrict my airflow. He stood up and pulled me to another wall, and I finally looked around the play room. There was a giant bed with black silk sheets, a sex swing, a glass cabinet full of every toy I could imagine, and a concrete wall with chains and shackles hanging from it, which is where he was leading me. He hoisted me up, still in my stilettos, and chained my hands together above me so high that my feet were dangling above the ground, grabbing my tits as he brought his hands down my body. I was completely helpless in an older mans sex dungeon, about to be fucked by someone who very clearly knows what he’s doing…I was in heaven.
“Touch me please, Master. I’m so wet” I whined, as I was met with a sharp slap in my face. I had forgotten the rule, I was so impatient to have his hands and mouth on my pussy. My face stung and I felt my juices start to run down my legs. He spun me around and pushed my face against the rough concrete, taking out a whip from the cabinet with dozens of leather tassels to punish me. He cracked them across my ass loudly, and I squealed in pleasurable pain. He whipped me again and again, and I felt the tassels snap over my ass, against my puckered asshole, curling around to my sensitive clit. Drooling against the wall, I came as he whipped me hard one last time. He twirled me around again and saw my chest and face blushed red from my orgasm.
“Cumming for Master already? You’re cute. Let me taste that sweet cunt now.” And with that he lifted me by my ass all the way up to his mouth as he stood upright, tossing my legs over his shoulders as his mouth connected to my pussy lips. I was surprised at how strong he was, and was using the chains my hands were still connected to for leverage, my head hanging almost upside down. It gave me a head rush, and on top of everything, Greg was groaning In pleasure as he sloppily lapped up my juicy pussy. I couldn’t help but echo his moan and arch my back to allow his full access to me. I could tell he loved eating pussy, and he savored every moment until I came again, shaking and screaming out, knowing that this room was probably soundproofed. He eased me down again with incredible control, he clearly kept his body in great shape, and I giggled as he took my shackles off and carried me to the bed, where he threw me down and dove his face back between my thighs again. I whimpered and grabbed the silky sheets in pure pleasure. When he stood back up again, his face was shiny with my juices and he was grinning like a younger man, his hard cock bobbing slightly from out of his trousers. He smoothly removed his clothes down to his black boxer briefs, which were stretched down so his cock and balls spilled out over top. He rubbed the head of his cock against my soaked pussy lips.
“Now, Red,” he warned, “I’m going to fuck you raw, no condom, and I’m going to cum wherever I want. Maybe all over that pretty face, or in your hot little mouth. Maybe deep in your ass, or I may cum inside your pussy to see my cream pie drip out of those pretty pink lips. Would you like that?”
“Oh yes please, Master! I want to feel your cock stretch my pussy!” And with that he picked me up again and sat me on the swing, positioning his cock back at my vulva and looking me deeply in the eyes.
He growled as he pushed the head in with some effort. Before standing still and rocking the swing back and forth in tiny movements. Even with him fucking me with just the tip, I was biting my lip and stifling my moans. With each push and pull of the swing, he allowed his cock to sink a little deeper inside of me, but agonizingly slow. I felt my pussy envelope itself around his thick cock, stretched wide like my jaw had been when I was sucking him off earlier.
“Fuck, your sweet cunt is so tight, Red. I haven’t fucked a little pussy like this in so long.” He was pushing and pulling the swing so quickly now, I felt him slap wet and hard against me, my tits bouncing from the force of it all. He ordered me to slip my feet into the stirrups that adorned each rope of the swing. As I did this, he walked back to the cabinet to grab some items; a grooved butt plug, some lube, and a small sleek metal vibrator. He flipped the vibrator on and nestled it against my clit. The focused buzzing made me immediately start moaning and shaking, and he slapped my face again as if to remind me that I was HIS plaything, not the other way around. Making me hold the plug, he lubed it one handed and then took it and slowly worked it into my ass, restarting the swinging motion to help stuff his cock back inside my pussy. With the plug in my ass, the cock in my pussy, and the vibratory on my clit, I was driven over the edge. I squirted, coating Greg and dripping a puddle on the floor beneath us.
“FUCK FUCK ohhhh fuck yes, oh my god I can’t believe I fucking squirted. Master, you made me squirt for the first time!” I moaned giddily, my whole body jiggling with each pump he was pushing me on the swing. With that he started pushing the plug deeper into my asshole, swirling it around to stretch me out for him. Then he pulled it out completely. His finger pushed the little vibrator harder on my clit, making me jump and groan as I felt my asshole tighten up again.
“You liked this on your clit, huh? Maybe it’ll help me make you cum again while I ruin this perfect pink asshole you’ve got.” He sucked on his finger before squeezing it into me, and the laughed. “It was difficult just getting my finger in, i can imagine how hard it’ll be to shove this cock in, but we’re going to make it happen. I want to use every one of your holes tonight.”
He carried me back to the bed, laying me on my stomach and pulling my legs wide apart. He pushed the vibrator into my pussy, and I moaned into a pillow as he squeezed a little lube on his dick and slowly starting to work it into my ass. With patience, half of his cock was inside of me, which is when he started to rock his hips to fuck me. I had only done anal once before with a much smaller dick, so he never went deeper than halfway that night, huskily telling me that it will take a few times before my asshole was ready to take his full length. He made me feel so primal, and I grunted in wordless joy feeling my holes filled together. I could tell Greg felt the vibration from his position too, and marveled at the tricks he had to intensify the pleasure we were sharing. He was talking dirty, but with a quiet measured voice, telling me how good my pussy felt, how I was his little fuck slave, how he owned all of my holes. He grabbed the tie still around my neck and pulled it back, forcing my head up and my back to arch as he choked me. I know I could have tapped out at any time (we had agreed on a safe word), but the lack of oxygen while I was being fucked made me feel like I was high, like one continuous orgasm. Just as I started to black out, I heard him groan and my back and ass was splashed with his hot cum. He loosened his grip and I collapsed completely limp, letting him carefully slide the tie off my neck. I heard him leave the room, but I was completely drained. I felt like I was floating, and was just riding the wave, my brain felt kinda broken…but in a great way.
A few minutes later, Greg returned and led me through his bedroom into the master bathroom, where we had a huge black marble jacuzzi tub filling with steamy water and bubbles. I was surprised after I had been fucked so roughly, and Greg seemed to read my mind and chuckled, “When you’re a middle aged man with a play room, you figure out how to give good aftercare”. We climbed into the tub, and he turned on jets that massaged my sore body. Using a loofah, he washed me carefully with soap that smelled like orange blossoms. Greg was so tender, and we sat in the tub sharing silly stories and giggling. He wrapped me in a fluffy bathrobe afterwards and told me to lay out on his big bed with white puffy sheets; so opposite from the black silk sheets his other bed had. We watched a movie and ate fruit salad in bed. I fell soundly asleep after one of the most mind blowing nights of my life.
Greg and I saw one another for a few months over that summer. It was clear there was an expiration date. I would stay at the penthouse for long weekends, rode his private jet with him (and sucked his cock on it of course), I was his arm candy and his personal fuck doll. He loved to dress me, and I’d often spend over a full day in the play room just getting the absolute life fucked out of me by Greg until I couldn’t walk, and he’d nurse me back after. He married a woman more age appropriate for him shortly after we called it off; she does charity and seems like an amazing lady living the perfect life. At the very least, she’s getting fucked well.
Source: reddit.com/r/gonewildstories/comments/fwyyhl/mf_thinking_back_on_boyfriends_past4greg_the