I have a habit of fucking the wrong men. To clarify, habit is probably not the right word. I should have said passion, compulsion, or addiction. That works better. I’m addicted to fucking the wrong men, and I’ve long since lost any regret or shame I might have once felt. We can only struggle with ourselves so long before we begin to collapse, and for me, it was easier to accept who I am than to justify or explain it.
The fantasies started long before I did anything about it. There were babysitters I wanted to catch me in the shower, teachers whose attention I’d do anything for, and friends of my parents who made me wet when they walked into the room. And the more wrong it was, the bigger my fantasy. I didn’t want any of dad’s friends, I wanted his boss. I didn’t want all of my teachers, just the married ones, and when it came to my babysitters, let’s just say none of them lasted very long in our household.
The first time I did more than flirt, tease, or spend hours in my bed with a vivid imagination, was a week before I graduated high school. I had just turned eighteen, and my mother was finally marrying her long-term boyfriend. For weeks my plan kept on getting worse. At first, I just wanted to fuck him because he was marrying my mom. For a while, I wanted to call him Daddy and fuck him on mom’s bed, but my fantasy kept on getting more intense right up until the day of their wedding when I couldn’t hold back any longer.
Mom’s best friend came to pick her up early in the morning to get their hair done. I was going to join them later, but for a few brief hours, I would be home alone with Jeff. There was no way I was going to pass up on my one chance to do the worst thing imaginable. Up until then, it had been a fantasy that got me off plenty but didn’t need to go anywhere else. But then it all fell together, and I suddenly knew I couldn’t go back. I was going to lose my virginity to my mom’s boyfriend on the morning of their wedding. Just the thought made me come before I even got out of bed.
When I walked into their bedroom in just a pair of panties and a teddy bear covering my tits, he didn’t know what the fuck to do. I smiled as I tiptoed over to the bed, and before he could say a thing I had the blanket off him, and I was straddling his naked body.
“What the hell are you doing Kaity?”
“I have a wedding present for you,” I whispered, my cunt now pressed against his already hard cock. This was going to be too easy.
“A teddy bear?” he asked, one eyebrow raised. I dropped it to the floor giving him his first glimpse of my tits, and his mouth just hung open. He was staring at me, and I knew he wanted it as much as I did. In fact, he had been staring at me for months, and that was just adding to my own fantasy. He was a good guy. A nice guy. But he wanted me all the same, and the idea of making him do something he was both terrified of and excited by made it so much better.
“Don’t be silly,” I said in my best little girl voice. “It’s my virginity.”
He was still staring at me as I rocked my hips back and forth, and I was already so wet I could have had him inside me in seconds. But there was no need to rush. I had waited long enough, and I could wait a bit longer. Especially if it meant seeing the expression on his face move from horror to desire no matter how hard he tried to fight it.
“Babe, this isn’t really funny. You’re a pretty girl, but the joke is over. Let’s get up and pretend this never happened, okay?”
He was straining against me, his cock so hard he was trembling, and even his words were starting to sound hollow. I pushed back against him, and I leaned down until his face was inches from my own. I could see him struggling not to move his hands up to my body, but no matter what he did I was going to win.
“It’s just my little gift to you,” I whispered, my lips now against his ear. “I’ve waited for so long, but now I can’t wait any longer. Besides, today is your special day, and I want it to be perfect. I want it to start with you getting fucked so hard you can hardly walk. You should have everything you want today, no matter what it is. Don’t you want me?”
“Fuck, I can’t even answer that,” he moaned, his hands finally moving to my hips. He dug his fingers into my skin and he twitched beneath me at the touch. I watched the muscles in his arms as he tried to pull away and touch me more all at the same time.
I was going to have to step it up.
“And later,” I continued. “At the wedding? I want you to look across the room at me as you stand there taking your vows, and know that your cum is dripping out of my tight little pussy. I want you to know that I was the last girl you fucked as you stand there next to my mom, and when you fuck her tonight, I want you to be thinking of me.”
When I slid my panties to one side he moaned so loudly I knew it was done. His eyes were glued to my smooth pussy, and I knew then that he had to have it. When I rubbed the head of his dick between my lips, I thought he might pass out.
“Kaity, please,” he groaned, as I opened myself with two fingers. He couldn’t look away, and neither could I. There was no going back for either of us and in just a few more seconds I was going to have a cock inside me for the first time. More importantly, I was going to have his cock inside me for the first time.
“Please what?” I asked. “Don’t you want to fuck me, Daddy?”
He thrust up so hard I thought was going to split me open, but I was ready and willing. I guided him into me, my whole body tensing up as he entered me all at once, and I was on fire. After all those years of longing, I finally had a big thick cock inside me, and I would never forget it. I started to moved my hips before kissing him on the lips, and all his hesitation was gone in a second. He moved within me, pulling me down onto him with his strong hands.
“That’s right, Daddy,” I continued. “Fuck my tight little pussy. I want you to come inside me so I know that you were my first. Oh God, it’s so big. It’s so hard and so big.”
I was screaming and moaning, and a minute later he flipped me onto my back and tore my panties off my hips. He sat there above me staring at my eighteen-year-old body, and all his hesitation was gone. All that was left was an animal desire. He bit my neck as he thrust back inside me, and I bucked my hips up to meet him over and over again. Each time he was the deepest inside me, I kissed his mouth and lifted my hips off the bed. His hands mauled my breasts, but even then I didn’t care. He wanted to do things to me that he couldn’t even begin to describe, and I was loving every second of it.
“Oh fuck, you’re so tight,” he moaned.
“Am I tighter than mommy?” I asked as I clenched around him.
“Oh god yes,” he moaned. “So much tighter than your mom.”
“Are you going to come in me? I want you to look at me all day long, knowing that you’re still inside me. Would you like that? When you kiss me after the ceremony, I’m going to whisper in your ear. I’ll tell you how wet I still am, and you’ll remember this moment, right now.”
“Oh god yes, Kaity. I’ll never fucking forget this.”
“That’s right Daddy,” I moaned, suddenly needing him to come more than anything. “Harder,” I moaned. “Please, fuck me harder.”
He closed his eyes and grunted, pushing so far into me I would feel it for days. And then he was coming and screaming, and I wrapped my legs around him as he thrust into me over and over again. The second I felt his orgasm start, my own ripped through my body in wave after wave of pleasure. I had made myself come hundreds of times, but this was something completely new. I clenched around his cock, and I swear I could feel him pulsing inside me. I shook and trembled, and I bit my lip so hard I nearly drew blood. I called out a million times, begging him not to stop, not to ever stop, and he held me so tightly I could hardly breathe.
I held him there for a long time, wanting to make sure it was real, and when he finally pulled out, I covered my pussy with my hand so I could feel the mess we made. I was still shaking and laughing, and I knew nothing would ever be the same. For the rest of my life, I would be looking to come that hard again, and I was completely looking forward to trying. I held his cock against my lips as he grew soft, and I played with the sticky come he left with complete glee.
“I can’t believe I did that,” he finally said, said looking down at my tiny body.
“Well, you better remember it,” I said, “because it’s never going to happen again.”
He frowned but didn’t say anything as I moved to the edge of the bed and struggled to stand. My legs were wobbly and my head dizzy, but I was happy and satisfied in ways I didn’t know were possible. I stopped at the doorway and watched him staring at my little ass, still not believing what we had just done. I waited just long enough to see the look on his face move from relief back into horror.
And then I was out the door, and back in my own room. For a long time, I thought he might come find me, but he never did. We both got dressed like nothing happened, and I kissed my mom on the cheek at the salon when I arrived.
“Did you have a good morning?” she asked when I sat down next to her.
“It was perfect,” I replied. “I am so happy for you. Jeff will be the best new Daddy ever.”
Later that night as I was dancing with him, I secretly slipped a finger into my cunt, still slick with his come. I reached up to his mouth and pushed it between his lips.
“Don’t forget,” I moaned into his ear. “Tonight, when you’re fucking my mother, I want you to think of me.”
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