CASE
“I’msorry,what?”Iask, wondering if I heard him properly.
He lets out a huge sigh. “I’ve never been with another man. I’m sorry, I understand if you’re not interested anymore. I should have told you before we got to this point. I’m just… Fuck, I just really want you.” He laughs ruefully. “But I get it if you aren’t interested in spending your night with someone who doesn’t have a clue what he’s doing, and apparently can’t even fake it till he makes it.”
My brain spins for a few moments as I process what he’s telling me.He’s never been with a man before?Jesus, do I want to be his first experience with another guy? I just wanted to have a good time, not become someone’s lifelong memory. But it’s clear he wants this. My protective instincts bubble up in my chest. I’ll be careful not to hurt him, but not everyone he meets is going to be as concerned about that. When I look at him, he’s biting down on his bottom lip so hard I’m surprised it’s not bleeding. He looks so young and unsure of himself, but he’s beautiful in the soft, white light spilling in through the window.
“I don’t care that it’s the first time you’ve done this with a man,” I say, reaching for his hand. “But are you absolutely sure this is something you want?”
He turns to me, his eyes full of uncertainty, but there’s lust in them as well. His cheeks are flushed, and his pupils are still dilated. “I’ve never been more sure of anything. I want you so much. I need this. Please. I need you.” His voice trails off.
I reach out, extracting his abused bottom lip from between his teeth, and brush my mouth against his.
“Do you promise to tell me if I do something you don’t want?” I say, staring into his eyes, trying to see if there’s any doubt there.
“I promise,” he whispers back. “But I want everything. I want you inside me. I want to be filled up and fucked. I want your hands, your mouth, your fingers on me, inside me. I want it all.” He hesitates for a second before blurting out, “I want you to take charge. Tell me what to do, how to make it good. I need you to lead me.”
A shudder of lust hits me like a freight train. We’re essentially strangers, but he’s un-inhibited enough to beg me to fuck him. I suppose since we’re in our forties, the whole reluctant, blushing virgin routine isn’t really a thing anymore, but the honesty and lack of fear in asking for what he wants is sexy as fuck.
“Okay,” I whisper back to him. “I’ll take care of you, Matt. Just like I promised.” Desire and relief mix together on his face as he curls his hand around the back of my neck and pulls me down into him, his mouth hard and demanding on mine.
I smile into his mouth, and when I relax, he does too. I run my hands over his abs and chest slowly. Moving so I’m between his legs, I lean in and take all of him into my mouth without warning. He lets out a surprised shout, which gives way to breathless laughter as I suck hard, his cock filling and hardening immediately.
“Oh, god,” he moans as I work him until he’s writhing with desire.
I take my mouth off him so I can shift his hips into a better angle and grab the lube from beside him. He sucks in a breath when the cold fluid drips down between the cheeks of his ass, making me chuckle. “Sorry, baby, should have warmed it up first.” I lean over to take his mouth, my hand still working between his legs, gently exploring until I reach his hole. Then I rub and circle him with one finger, gently increasing the pressure until I can feel him soften for me. Slowly, I push my finger into him, stopping at the first knuckle to let him get used to the feeling of being penetrated. It doesn’t take long before he’s writhing and pressing down onto my finger, craving more. I take him into my mouth again as I slide another finger inside him, and he shudders.
“Fuck,” he gasps. “Feels so good.”
Gently, I slide my finger in and out of him, with each thrust going just a tiny bit deeper until he's writhing and pressing down onto my hand, begging for more. Once I think he's almost at the edge, I slide a second finger into him, pausing as he gasps and stills.
"It's okay baby, give your body time to adjust." I stop moving my hand and lean forward to kiss him. By the time I've dragged my tongue down his torso, stopping to pay his nipples some attention on the way, his cock is hard again. Tentatively, I start moving my fingers in and out of him once more. Once he seems loose and relaxed enough, I slide a third into him, and he pauses again, squeezing his eyes shut and breathing through it while I rub soothing circles over his belly with my free hand. He relaxes much faster this time, and it doesn't take long before I'm spreading my fingers inside him, stretching him open slowly.
"How are you doing, are you okay?" I ask him, and he looks up at me with such raw vulnerability on his face that I almost well up. The level of trust he's placing in me right now, letting me guide him through this experience, sparks a strong urge to protect him inside me. I've never felt that way with anyone.
"I'm okay… I'm good," he whispers. "I need more, please, god. I need you inside me."
I have to close my eyes and swallow hard when I see the naked emotion on his face. I don't think anyone has ever looked at me like that. All the protective armor everyone uses to protect themselves with others is gone from his eyes. It sounds ridiculous, I know, but I feel like I can look into his eyes and I can see who he is at his very core. I know we're strangers to each other, but right now it doesn't feel that way. I don't think I've ever felt closer to another person in my life.
Taking his mouth with mine again, I slowly withdraw my fingers from his body as gently as I can. He gasps and writhes under me as I sit back on my heels to get a condom on and add a generous amount of additional lube.
"Do you want to get on all fours for me? It might be easier for you." I say softly. It's true, but if I'm totally honest, switching to that position might give me a little emotional distance from this man who's supposed to be a stranger, but doesn't feel that way at all. But as I'm quickly learning, he doesn't back away from his emotions. He blinks up at me and shakes his head.
"I need to see you. I need to see your face."
My chest gets strangely tight at his words. I feel like he needs to see me so he knows he's not alone, and no matter how uncomfortable it makes me, I'm not going to leave him alone. I'll be here for him to help him with this.
"Okay, baby. I'll do whatever you need," I say tenderly, pressing my palm to the side of his face and taking his mouth in a soft, gentle kiss. "I'm here."
MATTHEW
The world outside this room has completely ceased to exist as Case looks at me with the most gentle expression and promises he'll do what feels right for me."This experience is nothing like what I imagined. The tenderness he's showing me, the care with which he's checking in to make sure I'm alright. This is not what I imagined sex with a stranger to be.
After getting the condom on and adding a bunch more lube to both my body and his dick, he leans forward and I feel the head of his dick at my entrance. There's a feeling of inevitability. Like this was always meant to happen just like this. I realize I'm being ridiculous, but I can't shake the feeling that even though I'm nervous, this is supposed to be happening exactly like it is.
He presses into me so slowly, I almost beg him to go faster, but I trust him. I don't know why, but I trust this stranger with whom I'm sharing one of the most important moments of my life.. My body burns as it stretches around him, but I focus on his gentle hands caressing my abdomen. Finally, he leans back and looks down at where we're joined, letting out a deep groan. One more small movement and I can feel his balls press up against me.
"That's it, I'm inside," Case whispers, lifting his gaze from where I'm impaled on him to my eyes. "Do you feel okay?"
