Chapter 5
“Tomorrow night, I’m claiming that last hole.”
I freeze.
It’s been almost four weeks since that first time I was bent over his desk with his cum dripping down my thighs and my brain so scrambled from the amazing orgasm that I told him he could have me in whatever hole he picked.
At the time, it sounded hot. The kind of thing you say when you’re high on a man who fucks like a god.
Then I reminded him on Monday that the offer was still available.
I didn’t take into account that I’ve never had anal sex before.
Now, I’ve been fucking him for a month, and he’s finally ready to take what I offered.
“Tomorrow,” I repeat. My voice is steady, which is a small miracle.
His mouth curves. “Get some rest tonight.”
I swallow. “Yes, sir.”
He holds my gaze a beat longer, then walks back to his office. I’m left at my desk with my knees doing their best impression of cooked linguine.
Holy hell.
I get through Friday on adrenaline and the kind of denial that has carried me through every bad decision in my life. I’m wearing a wrap dress that will come off with a single pull. My inner slut didn’t want anything to impede getting his cock in my ass as soon as possible.
At 5:55, my phone buzzes.
Bren: Come here.
Lily: OMW.
I guess an ass-fucking appointment is a texting type of thing instead of office messenger.
All day, I’ve vacillated between horny and low-grade panic while I tried not to think about all the ways this could go bad.
At some point, I probably should have told him I’ve never had anal sex because that requires more trust than I’ve ever given anyone.
But I didn’t want to admit how stupid I was when I offered him my ass.
My legs are steadier than I expected, which I’m choosing to interpret as bravery rather than the numbness that comes from wondering if I’m crazy for eight hours.
Who lets their boss fuck their ass in his office after work as their first anal experience?
My nipples harden as if saying, “Hi, it’s me. ”
His door is closed. I knock once.
“Come in.”
I open the door, and the first thing I see is the bag sitting on the floor beside his desk. It’s a black nylon duffel bag. Bren is in front of his desk, his hip resting on it. His expression is calm in a way that means he’s in total control. That makes one of us.
I can’t tell which version of me is louder right now—the one that wants his cock in my ass or the one mad he’s not going to unload in my pussy.
“Close the door and lock it.”
You’d think by now I’d just do that. Whenever I come in here, it always ends up with me in a very unprofessional position.
He watches me, and once I do as he says, I stand by the door and lift my chin. I’ll be damned if I let him see me shake, especially since I’m the one who offered up all my holes like a deranged slut the first day I met him.
“Come here.”
He doesn’t move as I walk to him. The flush is heading straight to my pussy by the time I stop in front of him.
He takes my hand and holds it, his thumb running across my knuckles. The gentleness throws me off more than if he had yanked on the sash of my dress and shoved me against the desk.
“Before we start.” His voice is soft. “Colors?”
“Green means go. Yellow means slow down. Red means stop.”
“And you’ll use them.”
“I’ll use them.”
“Good girl.” He releases my hand, and the absence of his touch leaves a cold spot. “Take off the dress.”
I pull the tie at my waist. The fabric falls open and pools at my feet, and I’m standing in front of him in a black lace bra and matching panties I bought specifically for him.
“Beautiful.” His eyes take inventory. “Now take off the rest.”
I unclasp my bra and slide the straps down. My nipples harden even further in the cool air. The panties go next, and I’m standing naked in front of a fully clothed man. The imbalance—him dressed, me bare—makes me shiver and press my thighs together.
“On your hands and knees.” He steps closer. “Right here on the carpet.”
I lower to the floor, palms flat, knees apart. I know this carpet, but I’ve never been on my hands and knees, and definitely not naked. My ass is in the air, and I know exactly what he’s about to do with it.
The sound of the zipper of the bag makes me glance over my shoulder before I can stop myself.
The bag is open, and I catch a flash of what’s inside—the lube he’s reaching for, but also a coil of black rope and a leather strap with a buckle that looks suspiciously like a collar.
I’m not going to think about whether it’s a collar.
That’s a door I’ve spent a decade keeping closed, and tonight is not the time to examine how I feel about the idea with him.
“Eyes forward.”
I snap my head back and stare at the wall across from me as my body buzzes in anticipation. This is definitely one of the top ten filthiest things I’ve done. If he was trying to make this temp position the most memorable, he’s winning, hands down.
I hear the rustle of him removing his clothes and then the snap of the lube cap. “I’m going to warm you up first.” His hand settles on my lower back, and I exhale shakily. “We go at your pace. Not mine.”
“Okay.” My voice is surprisingly small. Where is that slut who offered this hole? I need some of that reckless bravery back right now.
His hand drops between my thighs—not where I’m expecting—and he strokes my clit until my hips are rocking backwards from pleasure. I’ve been wet since 5:55 yesterday, give or take, and the mess between my legs makes it obvious.
“You’ve been thinking about this all day,” he says.
I drop my forearms to the floor and rest my forehead on them. “All day.”
“Good.”
He slides two fingers inside my pussy, curling them deep, and I moan into my arm. The stretch is familiar and grounding, and I sink into it. He alternates between finger fucking me and playing with my clit while pings of bliss make me roll my hips and moan.
Then his lubed finger traces my asshole, and my whole body goes rigid. He pulls his hand from my pussy and presses it on my lower back gently.
“Breathe, Lily.”
The air shudders out of me. I focus on the warmth and wetness of his palm against my spine. His finger circles lube around the tight ring, and when he pushes the tip in, I gasp.
“Color?”
“Green.” It comes out strained. The pressure is full and strange and lights up every nerve ending in the area. He slowly works his finger in deeper while his other hand keeps stroking my clit. The dual sensation is dizzying.
“You’re doing so well,” he murmurs.
The praise makes my muscles relax a fraction, and he slides his finger in deeper. The stretch is fuller now, a pressure that makes me fight the instinct to clench. I dig my fingers into the carpet and breathe deeply.
He adds a second finger, and I whimper.
“Talk to me,” he says, and I almost laugh. What am I going to say? He’s got two fingers in my ass.
“I’m good.” I press my lips together to hold in a moan as he presses in deeper. “It doesn’t hurt. It’s just a lot.”
“Do you want me to slow down?”
“No.” I push back against his hand, testing. “No, keep going.”
He works his fingers slowly in and out of my ass while he rubs my clit. The pleasure builds as I rock backwards, meeting every thrust of his fingers.
“More,” I moan, and I realize the brave slut is returning.
He pulls his fingers out, and I hear the squirt of more lube. I think he’s using it on his cock, but I don’t look. He grasps my hip, and the head of his cock presses against my ass.
Everything inside me goes still.
“Lily.” His voice is controlled with a tightness underneath. “Look at me.”
I look over my shoulder. He’s kneeling behind me on the carpet, one hand on my hip, the other wrapped around his shaft, guiding himself. His jaw is tight, his eyes dark and locked on mine. He’s looking at me like he cares whether I’m okay.
“I’m going to go slow,” he says. “Keep talking to me. If you need to stop—”
“Green.” I hold his gaze. “I’m green.”
He pushes in. The pressure is immediate and enormous. A stretch that takes my breath, and for a second, the only thing I can focus on is the painful pressure as he sinks in. I panic. What the fuck am I doing?
He stops. His hand finds my lower back again.
“Breathe.”
I breathe, but it sounds like a sob.
“Color?”
“Yellow.”
The word pops out without me deciding to say it, pulled from some honest place. Everything stops. For a heartbeat, I’m sure I just told the wrong man the wrong word at the wrong time and just ruined everything. I panic further, and the words tumble out. “Yellow. I need—just—hold on.”
His breathing is heavier than normal, but he doesn’t move.
I breathe. In, out. In, out. The stretch becomes manageable. The pressure finds a plateau and settles, and my body adjusts around him.
“Green,” I say. My voice cracks on the word. “I’m green.”
He pushes deeper, every millimeter registering. The fullness is staggering, but it’s not painful.
“You’re so fucking tight.” His voice is rough now.
The fact that letting him fuck my ass is making this controlled man come apart sends a wave of heat through my belly that surprises me.
His grasp on my hip tightens. “Every hole. That’s what you promised me.
” His voice drops into a filthy register that makes my clit throb.
“My dirty little slut, on her hands and knees on my office floor, giving me the last thing she was holding back.”
My pussy clenches and my hips push back against him before my brain can vote on it. I can barely think, but I am his slut. Every hole.
He reaches around, and his fingers find my clit.
The combination of him in my ass and his finger on my clit makes me moan loudly.
The pleasure is different from regular sex, deeper, coming from a place I didn’t know could feel good, layered with the clit stimulation until my thighs are trembling and my elbows are about to give.
“Bren,” I moan, “Oh god. Oh god, that’s—”
He thrusts deeper into my ass. “Mine.”
“Yours.” There’s no thinking required.
“That’s right.” His groan vibrates through his body and into mine. His thrusts speed up, but he’s holding steady and measured. “My good little fucktoy, taking my cock in whatever hole I want.”
He’s never called me a fucktoy before, but the way my entire body clenches around him tells me I love it. His fingers circle my clit quicker, and the pleasure builds. It’s not the sharp peak I’m used to, but a slow rolling pressure that makes me moan.
“Come for me,” he says, voice rough at the edges, so commanding that my body obeys before my brain can catch up.
The orgasm hits in a wave that starts at my core and radiates outward, and it’s different from anything I’ve had before—deeper, pulling instead of crashing.
My inner walls clench around him in a rhythm that makes him groan and grip my hip harder.
I cry out into my forearm while my body shakes.
The waves of ecstasy are long, undulating pulses that go on longer than any orgasm I’ve ever had.
My orgasm triggers his. His entire body shudders as he unloads deep inside me. He pulls out halfway, and then presses in again, fucking his cum deep into my ass as he finishes.
He withdraws gently, checking my reaction with every movement. I whimper at the loss, not from pain, but I don’t know if he knows the difference.
“Easy,” he murmurs. “Stay right there.”
I almost snort as I collapse and melt into the carpet. There’s no moving. I’m wrung out and trembling.
Out of the corner of my eye, I see him reach into his bag and pull out a washcloth and a bottle of water.
He wets the cloth, and I’m so dazed I don’t even realize what it’s for until he’s cleaning me.
He’s careful, but the fabric against tender skin pulls a sound out of me that’s closer to a whimper than anything I’d willingly admit to.
He planned this.
My eyes sting. I blink hard and stare at the carpet. I refuse to cry after he fucked my ass just because he cleaned me up. Not happening.
He puts the washcloth into a plastic baggy and tucks it into the gym bag before curling up against me.
“Come here.”
Suddenly, my arms are around him like he’s a lifeline, and I’m shaking worse. He wraps his arms around me, and I press my face into his chest, feeling it move as he breathes.
“Are you okay?” His voice is normal. Just a man asking a woman if she’s okay.
“Yeah.” My voice is hoarse. “I’m okay.”
“Was that too much?”
I pull back enough to look at him. His eyes search my face, and there’s a crease of concern between his brows I haven’t seen before.
“It was a lot,” I say honestly. “But I’d do it again.”
The crease softens. His thumb traces my cheekbone, and I lean into his palm before I think about it.
I open my mouth before my brain can stop me. “That was my first time.”
He goes very still. “I wondered.”
“You did?”
“You hesitated when I touched you there.” His thumb hasn’t stopped on my cheek. “I wasn’t sure until you said yellow. But I was being cautious either way.”
He knew.
“You used your safeword,” he says. “That was brave.”
“It didn’t feel brave.”
I don’t add that, for one moment, I thought I ruined everything.
He is quiet for a moment, and I almost think the conversation is over, when he asks, “Why me?”
Uh…my brain scrambles for a deflection or joke. Anything. The truth comes out instead.
“Because I trusted you enough.”
He tips my chin up and kisses me softly. “Thank you.”
We stay wrapped up together for a long time, and for once I’m not telling myself this is just aftercare or him being a good dom. I don’t know what this is, but it’s not nothing, and that’s all that matters right now.
Eventually he stirs. “Let me help you get dressed.”
I dress slowly, my body heavy. Yeah, I’m going to sleep well tonight. He fastens the tie of my wrap dress because my fingers are clumsy, and I giggle when I see he did the bow better than I would have.
“Protein bar.” He pulls one from his desk drawer. Peanut butter chocolate. I lean to peek over his arm into the drawer. “Do you have other flavors?”
“Do you want a different flavor?”
“Nope, this is my favorite kind.”
“Water.” He hands me that, too.
I take them both. “Thank you.”
“Eat before you drive. And text me when you get home.”
“Bren…” I stop because I don’t know what I want to say. Something true, probably, which is dangerous.
He waits.
“Thank you,” I say. The safe thing.
He smiles. “Good girl. Drive safe.”