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A few days after that wild night, something had changed between Kate and me, and I felt it in every glance, every brush of skin. She moved with a new confidence—playful, almost defiant—and I couldn’t shake what had happened, or rather, what I imagined had happened. That time she came home late, breath heavy with alcohol, she told me everything while straddling me and riding me with an urgency I’d never seen in her: the kisses in Alan’s car, his hands slipping under her shirt, her rubbing his cock over his pants until he was practically unraveling. The words spilled from her mouth between gasps, and I came three times in a row, as if my body couldn’t hold back what my mind was barely processing.
After that, sex became daily, and it always circled back to him. We talked about Alan while we touched each other, imagining what it would be like if we stopped fantasizing and made it real.
We decided to go out one Friday night, supposedly to “clear our heads.” I picked the same bar near the plaza—the one she’d been to with him that time. It wasn’t random; I suggested it because I wanted to feel that sting of jealousy again, that uncomfortable electricity that got me so hard. The place was packed, music loud, tables mostly taken. We sat in a corner with a couple of beers. Kate wore a short black dress that rode up whenever she crossed her legs, showing everything I already knew by heart.
At first we talked about nothing important. But the tension was there, hovering. She gave me that mischievous smile I’d learned to recognize, biting her lower lip when something turned her on. I slid my hand up her thigh under the table, and she leaned in, her warm breath against my ear.
“Baby… I’ve been thinking about what you said the other night. About photos, videos… there’s something even more intense, you know?”
I froze, beer bottle halfway to my mouth. My heart lurched, blood rushing straight to my cock.
“What do you mean?” I asked, trying to sound calm, but my voice betrayed me.
She let out a low laugh, squeezed the hand I had on her thigh, and went on:
“That he comes here. To our place. That Alan comes over and we do something for real. Not just talk about it while we fuck. That you watch it live.”
I nearly choked. The idea hit me like a punch to the gut—half panic, half brutal excitement. I tried to push back, not because I didn’t want it, but because the fear of losing her, of her getting so hooked she’d never look at me the same again, was driving me insane.
“I don’t know, Kate… talking about it is one thing, actually doing it is another. What if everything gets fucked up afterward? I’m not sure it’s a good idea,” I said, staring at the table, even though my erection was already giving me away, pressing against my jeans.
She noticed, of course. Her hand dropped casually and brushed over me.
“Look at you already, Matteo… you say no, but your body says something else. It turns you on so much, doesn’t it? Imagining him walking into our place, kissing me in front of you, touching me…”
I tried to move her hand away, but without any real conviction.
“It’s just… I don’t know if I can handle it. Seeing it for real, not just imagining it.”
“That’s why we set rules, baby,” she said, locking eyes with me, those eyes that always undid me. “So you don’t lose your mind.”
I swallowed hard. My cock throbbed against her hand.
“Okay… I’ll just watch,” I agreed, barely audible.
“First: you only watch. Nothing else. You can peek through the cracked door or we set up the phone to record so you watch from the hallway. But you don’t come in, you don’t interrupt.”
“Okay.”
“Second: you don’t touch me until it’s over. You have to be naked, jerking off alone, watching him fuck me. If you come too soon, you keep watching anyway.”
That pierced me. I pictured myself in the hallway, hand on my cock, watching them in our bed.
“Kate… that’s too much.”
She smiled wider, squeezed me harder.
“Third: I can stop anytime if I don’t like it. But you can’t. You have to stay until the end, even if it hurts. Even if you see things you don’t want to see.”
The bar noise faded. All I heard was my own pulse. I nodded slowly, unable to say no.
Kate bit her lip, nipples hard against the fabric of her dress. She lowered her voice even more, whispering cruel and sweet at once:
“What would you do if you saw him sliding into me, Matteo? If you saw Alan’s cock spreading me open, going in and out while I moan looking toward the door where you are?”
I squirmed in my seat. My erection ached.
“I don’t know… I’d jerk off like crazy, I guess.”
“And if I moan louder than I do with you? If I say his name while I come? Are you going to stay there quietly, without interrupting? Or are you just going to come from watching me enjoy another guy so much?”
“Kate, please…” I groaned softly, glancing around to see if anyone could hear.
She laughed quietly, kissed my neck.
“Good boy. Tomorrow I’ll message him. Tell him to come over this weekend. Sound good?”
I couldn’t say no. I nodded. We paid quickly and left.
In the Uber home, she slipped her hand inside my pants and stroked me slowly, whispering more details about what was going to happen. I came in her hand before we even got home, shaking like a teenager.
The second we stepped through the apartment door, she shoved me against the wall and took me right there, standing, dress hiked up, my back against the wall.
“This is just the beginning, cuckold,” she said between thrusts. “Get ready to see the real thing.”
The next day around noon I was still nursing the mild hangover from the beers the night before, flipping channels without really watching. Kate came out of the bathroom wrapped in a small towel, hair still dripping onto her shoulders, leaving that vanilla scent that always drove me wild. She walked straight to me, that mischievous smile still plastered on her face, and sat on my lap without asking, spreading her legs just enough that the towel rode up and I felt the heat of her pussy against my shorts.
“Baby… you still thinking about last night?” she whispered, kissing my cheek.
I was already getting hard just from that, from her weight on me and the slow grind she started.
“Fuck, Kate… how could I not,” I answered, grabbing her ass with both hands, feeling how she registered my erection and pressed harder against it.
“Then… should I message Alan now? To start setting it up,” she said, reaching for her phone from the bag beside us. She opened the chat and showed me: the last message was from last night, something innocent about books. But now everything was about to change.
I swallowed, heart pounding.
“Message him,” I said, voice shaky.
She let out a low laugh, eyes never leaving mine.
“Tell me what to write, cuckold. You suggest it and I type it. That’ll turn you on even more.”
I pulled my shorts down a bit to free my cock, already swollen and wet at the tip. Kate shifted, rubbing her bare pussy against me, not letting me inside yet, just torturing me with the heat and wetness she already had.
“Start soft… something like ‘Hey, Alan, how’s it going? I was thinking about the other day at the bar… it was fun,’” I suggested, panting because she’d started moving slowly.
She typed exactly that and looked at me.
“Say it out loud, Matteo. So I hear you while I send it.”
“Hey, Alan, how’s it going? I was thinking about the other day at the bar… it was fun,” I said, feeling ridiculous and burning at the same time, my cock throbbing against her entrance.
She pressed down just enough to take the head, letting out a short moan.
“Sent,” she said, and kissed me deep, tongue and all, while the phone buzzed almost instantly.
She read aloud:
“Lol, yeah, we had a great time. You were especially gorgeous that night Matteo doesn’t get jealous?”
She laughed, reached down and started stroking me slowly while still grinding.
“Look how hard you get when he mentions you… What should I reply?”
I was thrusting upward, desperate to sink deeper, but she lifted herself each time to deny me.
“Tell him… that I’m weird, that the idea of you two seeing each other more often—alone or however—turns me on.”
She grinned wide and typed:
“Matteo is a little weird… he says the idea of us seeing each other more often, alone or however, turns him on.”
She made me repeat the whole thing, drawing a loud groan out of me.
“Repeat it, cuckold.”
I said it and she sent it. Then she dropped down hard, swallowing my cock to the hilt, hot and tight. The towel fell to the floor and her small tits started bouncing as she rode up and down.
The phone buzzed again.
“Lol, seriously? How weird exactly? Tell me more, I’m intrigued.”
Kate sped up, fucking me hard, grabbing my hair to force me to look at the screen.
“Suggest something stronger, baby. Tell me what to write so he gets it.”
“Tell him… that I’m dying to see you with him, to watch him touch you,” I stammered, already on the edge.
She stopped dead, squeezing the base of my cock to hold me back.
“Not yet, little cuck. Say it right: ‘My boyfriend is dying to watch me have sex with you… he says he wants to watch.’”
It was way too direct, but I said it, voice shaking.
Kate softened it a bit as she typed:
“Matteo is super weird… he’s dying to see me go out more with you, he says it even turns him on to imagine things What would you think about that?”
She sent it and started riding me again.
“Good boy… look at how hard you get saying those things out loud. You’re harder than ever.”
I was moaning uncontrollably, her juices running down my balls.
“Kate… please…”
But she stopped again when the phone buzzed. Alan took a little longer this time.
“Wow, didn’t see that coming. But it sounds hot. If he likes to watch… I’m down. Tell me when and I’m there ”
Kate came just a little, her pussy pulsing around me, and grabbed my face.
“Listen to this, Matteo. Repeat: ‘Alan, come whenever you want… Matteo wants to watch you fuck me.’”
She typed something similar:
“Lol, then let’s get ready. How about next Friday? You come over, we have some drinks… and Matteo watches from the hallway like a good cuckold ”
I repeated it all, groaning, while she fucked me harder, her tits bouncing against my face. I sucked a hard nipple and she let out a short cry.
She sent it and waited. I couldn’t hold it anymore.
“I’m gonna come, Kate…”
“No, wait for the reply,” she said, climbed off and knelt. She took my cock in her mouth, sucking hard, but stopping every time she felt me about to explode.
It buzzed again.
“Perfect. Friday it is. Matteo better watch close when I make you come like crazy. I’m gonna show him how you really fuck a slut like you ”
Kate read it slowly, staring right at me while she jerked me fast.
“You heard that, cuckold… Alan says he’s going to fuck me like a slut right in front of you and that you better watch close when he makes me come.”
That broke me. I came in her hand in long spurts, moaning her name and his mixed together. She licked a little, laughing, and replied quickly:
“Yeah, come ready. Matteo already came just from reading that. We’ll be waiting ”
Then she climbed back on, sliding over my mess, and we kept fucking while we planned the details: how she was going to dress like a slut for him, how she was going to keep me naked at the door, jerking off without permission to come until they were done.
Friday was getting closer and I couldn’t think about anything else. I was scared to death and more turned on than I’d ever been in my life. Kate had me completely in her hands, and Alan… fuck, Alan was coming to fuck my girlfriend right in front of my eyes.
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