“Sure, I can’t do all the work,” I tease as I grab the bottle of lube to pump more on my free hand. I awkwardly lean back and slip two fingers inside of myself to prep quickly while still fingering him. “Put some lube on the plug.”
He nods and does just that, and I pull out of both our asses and turn for him, straddling his lap with my ass in his face. He rubs his palm against my skin, whispering, “You’re so sexy.” Then I feel the cold toy circling my rim before he slowly presses it inside of me. “You should see your hole sucking this in right now. Oh my god, P.”
There’s so much awe in his voice, and it lights up something inside of me as I remind myself thatWill is my boyfriend. We get to keep doing this for as long as we want. I’m aware this is new and things could change, but it’s such a different mindset than I was in during our previous hookups. Will is in love with me. He talked about being together years from now.
“Feels so good,” I tell him once it’s fully inside of me, I flip back over to give him a sloppy kiss before I go back to prepping him.
I take my time sucking his dick and licking his balls while I enter him again with two fingers. His cock flags a little, so I go slow, pumping and twisting while I suck, giving his balls equal attention to distract him when he’s ready for a third finger.
“Ngh,” he moans at the addition.
“You’re opening up so well for me, Daddy,” I praise, knowing what that word does to him.
“You make it easy, Kitten. I trust you.” Fuck. How does he keep making me so emotional while still being so fucking sexy? I swallow the words that are threatening to break free.I will not say I love you for the first time during sex. I refuse.I need to focus on making sure he’s ready for me.
I scissor my fingers inside him to the best of my ability, and fuck, he’s perfect. Even though I don’t usually top, I can’t wait to be inside of him. To share this moment with him. To be the first one inside his perfect ass.
“Fuck, I’m getting close from just your fingers and your mouth,” he assures me. “I think I’m ready for you.”
I pull off his dick and nod. “Alright, but if anything hurts, tell me.”
“Yeah, of course,” he agrees as I reach to grab a condom. Once it’s on, I squeeze lube over my dick and add more to his hole.
“I can put a pillow under your hips to help or you can straddle me to control the pace,” I offer. I’ve never taken anyone’s bottom virginity before, and my nerves are starting to creep up my throat, worried he won’t have a good experience.
“Pillow. Want to see you as you slide into me,” he answers confidently, already reaching behind him to grab it and position it under his hips.
I nod as I guide his legs back and line my dick up against his hole. “Relax and breathe out,” I instruct, and when he does, I grip the base of my cock with one hand, pressing into the tight ring of muscle.
“Oh, holy shit,” Will breathes, and I freeze.
42
WILL
“We’ll go as slow as you need, just breathe with me,” Porter instructs.
I look into his eyes, reassured by the concern I see shining in them.I want this, I remind myself as I let out a big exhale. I want Porter to fuck me, to share this moment with him, and it’s okay if I don’t end up loving it. I want to at least try. I nod, encouraging him to continue, and the steady pressure against my hole increases. I try to relax, but I tense up slightly despite my best efforts.
“Breathe out again,” Porter coaches, maintaining the pressure and this time the intense stretching fullness shifts as my body allows him in.
“Oh god,” I hiss, gripping the sheets in my fists as the new sensation overwhelms me.
“Too much?” Porter asks, obviously concerned.
“No, no, just weird,” I assure him through a shaky voice. “Keep going, P.”
He nods, holding onto my legs as he continues to push in slowly. “That’s it, you’re doing so well.”
“It feels like you shoved a lacrosse stickup my ass,” I joke, trying to distract myself from the burning pressure that I’m hoping improves soon. I loved when he used his fingers, so I’m sure I just need a minute to adjust.
“Well, this feels absolutely incredible for me. You’re perfect. I’m almost all the way in,” he says on a sigh as he continues to slowly slide deeper inside of me. He adjusts his hold on my legs to stroke my dick, and the positive distraction is very welcome. My entire body seems to relax as he works his hand up and down my cock.
“Fuck, that’s good,” I mutter, focusing on that and not the fact that it feels like he’s splitting me in half right now.
“If you think me touching your dick is good, you wouldn’t believe how it feels to be inside of you right now.”
I love knowing that he’s enjoying this so much—that alone makes this worth it, although each stroke of his hand seems to elevate my experience as well. The mild burn associated with the fullness is shifting to positive pressure that’s making his movements on my dick even more pleasurable.
