“That’s not the end game here, Lucy.” I push a little deeper, through the ring of muscle, and he sucks in a ragged breath. “Still okay?”
There’s an extended pause before he says, “I don’t hate it, but I don’t love it either.”
“What about now?” I slide my finger in and out with exaggerated care, mimicking what I’ll do with my dick when he’s ready, and his hips start to chase my finger on the retreat.
“Better.” He tries to grind on my finger. “It’s kind of intriguing, but not in agive me moreway. At the same time it’s also—”
“Not enough,” I suggest when he doesn’t finish that sentence.
“Yeah.” He blows out a measured breath. “I know that doesn’t make sense,” he says, wriggling his ass on my finger despite the fact he’s not sure he really likes it.
“It makes perfect sense,” I reassure him, rubbing his back while I let my finger creep deeper, paying careful attention to his breathing so I know when to back off, when to push forward, and when I’ve found the spot that’ll make him feral with need.
My own first time bottoming was like this, curiosity and excitement mixing with confusion and doubt. And while my partner wasn’t as gentle with me as I’m being with Bennet—more because we were both inexperienced than because he didn’t care about my well-being—I firmly believe that the confusion and doubt comes from fear of the unknown.
Boys grow up exploring their junk—it’s just a fact—so getting off that way is inherently more familiar than getting off from having something in your ass. The more familiar you get with anal the more enjoyable it is. And with the right person? It’s nirvana.
The first time I took Bennet inside me, I knew he was that person for me. Actually, I knew it before then, but I reaffirmed that belief when we fit together perfectly. And I’m sure he’ll feel the same way after tonight. If I go slow and make sure to take away the fear as I give him pleasure, the way I’m doing right now, he’ll crave this experience again.
Having him spread out beneath me like this, pliant and trusting, has my slit leaking with anticipation that’s it’s impossible to stifle. But I don’t rush, keeping my movements measured so that Bennet will feel more pleasure than discomfort when I finally enter him.
The longer I work his channel, the easier he is to stretch. Soon, I’m able to slide in and out without any resistance, allowing me to delve a little deeper. And when his body tenses with a guttural moan, I double down, knowing I found that sacred, euphoric place.
The one that will have him addicted.
The one that could make him mine. Forever.
“Holy…” Bennet lifts his chest off the bed and clenches around my finger, going still for a minute until the initial shock wears off. “Was that my prostate? I felt iteverywhere.”
Licking my lips, I nod, still toying with that magic button. “I’m gonna add another finger, stretch you a little more, okay?” I ask, peppering his lower back with tiny kisses.
He flops back down on the bed. “Yeah. Okay.”
I add another drop of lube to ease the burn, scissoring my fingers as they pump in and out of his tight channel. Bennet does his best to stay still, though it’s obvious by the way his muscles are coiled with tension that he’s not fully relaxed. I get it—my dick isn’t exactly small, and he’s worried about the fit—so I take extra care working him open, rubbing and kissing those tight muscles to help loosen him up.
“That’s it, Lucy.” I work in a third, twisting my wrist slightly so I can nudge his prostate and take this from tolerable to pleasurable. “Relax.”
Bennet grunts as I push deeper, but when my finger brushes that spongy surface, a loud moan explodes from his lips. Unabashed, he starts grinding into the mattress as I tease that bundle of nerves.
“Gonna move like that when I have my cock inside of you?” I give his ass a little love bite, holding in a groan of my own as that causes him to clamp down on my fingers.
“Only one way to find out.”
“It’s gonna hurt at first. It just is, no way to avoid it.” I pull my fingers out and roll on a condom, coating myself with more lube. “But I’ll hold still when I’m all the way in, and whenever you’re ready you start grinding like you just were. Use my dick to make yourself feel good. I won’t move until you ask for more. Ready?” I line myself up with his hole.
“Ready.”
Despite being absurdly slick, I still have to push to get inside, and I have to tell him more than once to relax and breathe before I’m fully seated. When the base of my cock rests against his ass, I press my chest to his back, mindful not to put my full weight on him, and wait.
It’s torture, pure and fucking simple. Being buried in his vice-like grip and not being able to move is worse than two-a-days, worse than sitting on the sidelines, worse than failing to make a play when I get in the game. My limbs damn near shake with the effort of staying immobile long enough for him to get his bearings.
All I can do is whisper encouragements about how good he’s doing, but if I’m honest, they’re just as much for me as they are for him.
Thighs and abs cramping from the strain of holding still, I’m damn close to giving him my full weight when he mercifully starts to move.
Slowly at first, just a slight circle of his hips, my first thought is that I imagined the movement. Then I feel it again. And again. And finally I can pull a full breath into my lungs.
As the circles get bigger, he starts to rut against me, and I find myself moaning in relief. Not that it isn’t torture to hold steady while he uses my body… my dick… It’s more bearable.