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Chapter 14
How do I get Grace to go all the way?
If she wants Henri, give her Henri
She was stuck on Henri, her boyfriend. But maybe that was the answer...
“Grace, when you look at me tonight, you see Henri.”
Her face twisted in confusion, but then relaxed. “Henri?” she asked, putting her hand on my cheek and caressing it.
“Yes dear,” I replied. Damn, how do they talk to each other? Should I use lovey-dovey language?
“Are you ready for bed?” she asked with a sweet, tender smile.
“Bed?” I teased. “Are you sleepy?”
“Not yet,”she giggled. Then she loudly whispered, “I'm horny tonight.”
“Lucky me,” I smiled.
“Oh yeah,” she nodded. I quickly stood up and took her hand. Pulling her into a standing position, I helped her stumble her way to the bedroom. By the time we got there, she had already removed her shirt and tossed it god-knows-where. I stared for a few seconds, appreciating my first look at her nearly-naked form. A form that fell onto the bed in a fit of giggles.
“You're acting like you've never seen my boobs before,” she said.
“Just... just appreciating how beautiful you are,” I said, removing my own shirt.
“Well, I don't want to be appreeshy... appretiash... I just want you to make love to me right now.” As she spoke, she was trying to wiggle out of her panties. I helped slip them down her legs, rubbing her smooth skin as I went. Then, quickly removing my boxers, I crawled onto the bed. Just as I was taking my place between her legs, Grace said, “Condom baby, hurry.” She raised an arm in the air and flopped it down onto the bed, her finger pointing at the nightstand farthest from us. I looked at where the condoms were undoubtedly stored and debated honoring her request. But by that point, I had already forsaken all pretense of doing the right thing. If I didn't want to use a condom, I didn't have to use a condom. It was a simple as that.
“Not this time, babe,” I said to her. A bit of anger and confusion made its way to her expression, despite her inebriation. “Let me do you bare- as intimate as possible,” I said. “Just this one time.” That was all it took. I knew it wasn't persuasive. It was a command – she had to obey. Without any argument or comment, Grace spread her legs and smiled up at me.
“Well, what are you waiting for?” she asked. That was my cue.
I took hold of my cock and placed the tip at her entrance. She had a patch of hair around her entrance, the same strawberry blonde as the hair that was now fanned out on the bad around her face. Her bush was trimmed enough that I could easily see her lips just holding on to my tip.
I looked at her face, and it was beaming with affection. A small part of me – growing smaller by the minute – felt bad for what I was doing. But my hormones made the compelling argument that, thanks to the app, there would be no consequences for my actions. Sure of that, I pressed forward. Grace's eyes grew big as I entered her, and she took a deep breath when I paused. One more thrust, and I was fully inside her.
“Oh... oh wow, that's different,” she said quietly.
“What is?” I asked, wondering if there was a big size difference between my cock and Henri's.
“I've never” she started, then paused. “Never without a condom, you know. It's... it's nice.”
I had to agree. My strongest fantasies involve impregnation – **** or willing. But I've almost never had the chance to even pretend. The one girl I used to date who was on the pill and who would sometimes let us fuck without a condom was still worried enough about pregnancy that she shut down any joking or pretending that I was going to knock her up. This app might be a dangerous, dangerous thing. It wasn't just a harem that I could start - it was a whole brood of my children popping up across town.
As I thought through the possibilities, my body was already instinctively beginning a slow thrusting rhythm. I was so distracted by imagining the possibilities before me that Grace almost had to shout to get my attention. “Kiss me, babe! Why aren't you kissing me?”
Called to task, I cradled her head with one hand (the other trying to touch as much of her body as I could reach) and pulled her face close to mine. Her mouth tasted like her drink, but the fervency of her kiss easily kept my mind off the smell.
After a few minutes, I asked, “Do you want to change positions?”
Grace put her head back on the pillow, stopped rubbing my back and chest and let he hands flop out to her sides and answered in a dreamy voice, “No. Not at all. You know I love this position best. I like how you feel on top of me. I like you just pounding into me. I like watching your face when you cum. I like feeling how strong you are when you fuck me like this.” She giggled, as if saying the word “fuck” was somehow naughty.
Grace didn't know it, but she was pushing all my buttons. Everything she had just said – I loved it, too. I loved being on top, I loved the feeling of intimacy and power. It was driving me to the edge. And with Grace pushing her hips up at me and moaning softly with each thrust, I didn't have the strength to hold out much longer.
“I'm close, baby,” I warned her.
'OK,” she smiled.
“Can I help you... you know...get closer?” I had told her not to cum while masturbating, but that was clearly over. It was time to give the girl some relief.
“What?” she laughed, giving me a peck on the lips. “Sweetie, you know I can't cum during sex. I'll finish later.”
Oh no, that was not going to work for me.
“Just this once,” I said.
“Hmm?” she queried.
“Doesn't it feel good, me being in you without a condom?”
“Yeah, but I'm a little worried. I mean, are you gonna pull out? I'm drunk, but I'm not that drunk,” she joked.
That was just fuel for the fire. I started moving faster, pushing as deep as I could, loving the way she grunted in response to our bodies colliding. “Just this once,” I said again, “let me cum inside you like this, and when I do, you cum, too, OK? Like... a really satisfying cum, while my seed fills you up...”
“Babe?” she seemed worried.
“Let it happen,” I told her, “and whatever happens, happens, OK? Don't stop my seed from taking root inside you – just this once. You're going to love it. I want you to cum thinking about your body finally doing what nature designed it to do.”
Grace could only moan in response. A moan of mixed arousal and concern. But she did nothing to stop me. She couldn't. And only seconds after I finished giving her those instructions, I reached my limit. I was finally fucking a woman who was not only going to let me cum inside her, but who might even get pregnant.
“Babe, are you on the pill or anything?” I grunted as I reached my peak.
“What? No! That's why we always-”
She was cut off by my last, most urgent thrust. My whole body pressed forward, both my hands gripping her perfect little ass and holding her tight against me. Even if she hadn't been ordered to let this happen, there was no way her body was pulling away from mine. I was deep, I felt her entrance gripping the base of my cock. I held my breath for just a second, and then... release.
“OHHHHHFFFFUUUCK!” I shouted, blast after blast filling my helpless partner beneath me. My orgasm was the cue for Grace - her expression moving from confusion to ecstasy - to cum with me. I felt her contractions begin and groaned one last command, “Squeeze me with your pussy, babe.”
The pressure of her walls suddenly pressing tightly around my staff only made me cum harder with each successive blast. I pulled back and thrust in again two, three times. Grace lost control of her limbs for a few moments, gripping me with arms and legs, then flailing open and clasping at the bed sheets before embracing me again. “Ohmygod, ohmygod, ohmygod,” she whispered over and over and varying volumes. Perhaps overwhelmed, she tried to pull her hips away from mine, but I hadn't yet released her. I wasn't ready to pull out yet. I could still press into her and **** out a little more cum into her untouched depths. Only when I felt like I had nothing more left in me did I let go and pull out. Grace stared at the ceiling, her arms limp at her sides, and exclaimed one final “oh my god.”
I cleaned up and got dressed while she slowly recovered. I had already decided how to play this out, so just before leaving, I put my mouth next to Grace's ear and said, “Remember this as an intense drunken dream. You got drunk alone and masturbated until you came. Forget that Ron was ever here tonight.”
That should do the trick, I thought. I whistled as I headed out, eager to try my new bag of tricks on another unwitting woman.
Who do I meet the next day?
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The Ultimate Dating App
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Updated on Nov 17, 2025
by Cmello
Created on Jun 18, 2021
by Lucasstar
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