by Max Monroe
Maybe Willis is Evan’s little sister. I should not engage in talk about sexting with her.
Me: I don’t know if I’m really comfortable talking about this, kid. Sexting can get…intense.
Maybe: So, you have done it. You do it.
I groan and type out what I think is a fairly innocuous message. If she’s not going to drop it, I’ll just have to keep things in check.
Me: I mean, it’s not on my appointment calendar, but it’s happened before.
Maybe: What do you say when you sext?
Fucking hell. I bite my lip as my mind automatically plays through a list of things I want to say to her.
I dare you to rub your fingers over the top of your panties. But do it exactly how you love to touch yourself when the panties aren’t in the way.
Slide a finger inside yourself. But imagine it’s me. Imagine it’s my hard cock filling you up.
If I were there, I’d taste you. I’d slide my tongue inside you and feel how wet you are. And I’d rub my cock on your clit, make you beg me to slide inside you.
Shiiiit. I’m in so much trouble here.
I take a deep breath to recenter myself and succumb to the fact that I’m going to have a rock-hard cock until I do something about it later tonight.
I can’t tell her the things I want to say, so I go with something a little more textbook than romance novel and hit send.
Me: I don’t have pre-planned sext messages that I send out to women, Maybe. It’s more of an in-the-moment kind of thing.
Maybe: I think I want to do it. Sext message, that is. It’s time.
I rub at my face roughly. Good God, she’s trying to kill me.
Me: It doesn’t exactly work like that. You don’t just start randomly sexting people.
Maybe: I KNOW THAT. I’m just saying I want to experience it.
Before I can respond, another text message pops onto the screen.
Maybe: Why don’t we just do some sexting now?
Me: WHAT?
Maybe: C’mon, Milo. It’s not a big ask. Just help me practice a bit.
She wants me to practice sexting with her? I open and close my eyes just to make sure what I’m seeing is real.
But it is. And she doesn’t hesitate to continue her crazy campaign to make it happen.
Maybe: Evan asked you to help me!
I laugh. Outright.
Me: He asked me to help you find a job in publishing. I’m absolutely positive he did not ask me to sext with you. I don’t even think Evan’s ever used the word sext in conversation.
Maybe: It’s not like I’m going to send you pictures of my boobs and demand dick pics. I just want to rehearse. Like a sound check.
Sound check. Christ. The fact that she’s never done something like this before and wants to experience it for the first time with me is almost too much to handle.
Why does she have to be so goddamn irresistible?
Maybe: It’s either you or some random dude on TapNext.
TapNext? Fuck. I abhor the thought of her sexting some asshole on a dating app.
Maybe: What are you wearing right now?
She’s relentless. I sigh. But I also smile.
She’s so damn disarming, I don’t even know what I’m thinking anymore. It’s like I’ve lost all control of myself.
Maybe: Please, Milo.
Me: You’re not giving up on this, are you?
Maybe: Nope.
Son of a bitch. This is a bad idea.
I know this is a bad idea.
But despite my better judgment, my fingers tap across the screen slowly while my heart speeds up in my chest.
Maybe
Okay, so I don’t think I started Phase 2 exactly like Lena explained.
In fact, I’m pretty sure I did the exact opposite of what she advised.
But when absolutely no natural segue came to mind, I found myself reciting a lesson from my childhood with Betty Willis over and over again in my head—honesty is always the best policy.
The fact that I used Betty’s advice on something as unorthodox as sexting Milo is completely disturbing, but there’s no going back now.
All I can do is wait.
Nervously.
When two minutes pass, I start to freak out and throw myself face first into the comforter on my bed. The down material compresses at my face, allowing my continued breathing with ease. When a third minute comes to a close, I start to wish the material were a little more unyielding.
Jesus. What have I done? I completely fucked Phase 2, and now he is probably never going to speak to me again! Abort! Abort the mission!
I’m seconds away from typing out a rambling apology when my phone vibrates in my hands.
Milo: Boxer briefs and a T-shirt.
Oh. My. God. He’s doing it.
We’re doing it.
Well, we’re not actually doing it, but we’re doing sexting, the virtual form of doing it, and holy hell, I cannot breathe.
Calm the hell down! Take a breath, you lunatic.
I force myself to breathe and read his text message with slightly less crazy eyes.
Boxer briefs and a T-shirt.
Milo in just boxer briefs and a T-shirt?
Yeah, that’s hot.
Shit. Okay. Sexting. Sexting.
What in the hell do I say next?
Are they big boxer briefs?
What the hell? That doesn’t even make sense, Maybe.
Delete.
Do you have a big ole ball bulge?
Seriously?
Delete.
After another four awful attempts, I come up with something I think seems appropriate and hit send.
Me: Can I see?
Milo: Only if you show me too.
I swallow hard and look down at my stupid pizza pajama pants and white camisole.
Oh. My. God. I’m an idiot. Who wears pizza pajamas to a sexting party?!
That’s another Betty lesson I should have paid attention to—always be prepared!
Me: Uh… I feel stupid now. I should’ve dressed better for this conversation.
Milo: I can assure you, kid. I’ll be happy with whatever your wearing.
Me: I don’t know about that…
Do I take them off?
I lift the elastic of my pants up and peer down at my underwear.
Pink boy shorts.
Okay, they’re not bad.
I jump up off the bed and wiggle my pants haphazardly down my legs. Breathing hard, I bounce back on the bed and settle in again. But before I can contemplate my next move, my phone vibrates with another message. A picture message.
Taken from the chest down, it’s a picture of him, sitting on his couch, with exactly what he said on—a white T-shirt and black boxer briefs.
And yes, there is a bulge.
A big bulge.
Holy. Flapjacking. Shit.
It’s at this exact, inopportune moment that I realize Bruce’s creative cursing has rubbed off on me.
Jesus, Maybe. Do you really want to think about your father right now?
I shake my head, trying to physically force the ridiculous thoughts to fall out, and throw myself backward. I bring the arm with the hand holding my phone up to cover my eyes when it vibrates again.
Milo: Now, it’s your turn.
Fuck. My turn.
Just go with it. You may never get another opportunity at this.
I lift my phone up, snap an angled picture from my chest down and send it before I can back out.
The longest minute of my life passes by before my phone vibrates with a response.
Milo: Monday panties on a Tuesday?
I glance down to see he’s right, I am wearing my days of the week underwear, and they are, in fact, sporting the wrong day. For some reason, the fact that he focused his message on that makes me relax a little. I even laugh as I type out a response.
Me: I like to live dangerously.
Milo: If you really want to live dangerously, touch yourself and t
ell me how it feels.
Holy. F-bombs.
Time slows down and my brain starts to bleed, and I think I’m really going to pass out this time.
Did Milo Ives just say that to me?
Did Milo Ives Just. Say. That. To. Me?
I swallow hard against the nerves moving up my throat, but at the same time, I do as I’m told. At least, the touching myself part. The ache between my legs all but challenges me not to. Giving him the details, though, that’s probably going to take me a minute.
I work on typing out the words as shakily as I can. How I’m rubbing my clit in tight, round circles and putting pressure on the top each time.
My thumb hovers over the send button for the briefest of seconds, just long enough to take a deep breath, but that’s all it takes for Milo’s message to come in and stop me cold in my tracks.
Milo: And that’s how you sext, kid.
My hand arrests and my adrenaline crashes. I wanted Milo to teach me how to sext, and he taught me, all right.
He taught me so well, I almost believed it was really happening.
Milo
Maybe stands in front of me, completely bare, and my eyes turn hungry. Greedy. Fucking ravenous to take in every inch of her soft, perfectly tanned skin.
God, she’s something. My brain can’t even put together words to describe the sight of her naked, wanton, and waiting for me to make a move.
“Milo,” she whispers, and I don’t miss the way her teeth bite into her bottom lip or the way her thighs tremble as she fidgets underneath my gaze.
“What do you want?” I ask her, but she doesn’t respond.
She just looks at me with those big brown eyes of hers and traps me in the never-ending depths.
“Maybe, what do you want?” I prompt again.
“You.” One word. Three letters. And powerful enough to make my cock harden and twitch beneath my boxer briefs.
I act on instinct, on desire, on fucking need, and I’m on my feet, striding toward her.
We’re in my bedroom.
And before I know it, we’re on my bed, Maybe beneath me and my boxer briefs a distant memory on the floor.
My cock is at her entrance, the tip sliding through her wetness, and I groan at the painfully delicious feel of it.
Fuck, I want her. I’ve been wanting her.
Since the moment I saw her in Bruce & Sons and didn’t even know it was her.
A day hasn’t gone by where I haven’t wondered how this would feel.
How she would look, how she would taste, what she would feel like wrapped around my cock.
“Please,” she begs, and her hips gyrate from side to side. Her movement pushes the tip of my cock inside her, and I come unglued.
I can’t resist her anymore.
Not for even a second longer.
I’m going to slide inside her and make her mine.
Slowly, so slowly I had no idea I had it in me, I slide my cock inside the perfect heat of her tight pussy. I’m halfway inside and so close to bliss I can taste it when a persistent, annoying-as-fuck sound picks up a steady beat and volume.
I don’t know where it’s coming from, but goddamn, it needs to stop.
I blink my eyes with the intent to look down at Maybe, but she’s no longer beneath me.
What the hell?
I blink my eyes again, and her smell disappears.
Piece by piece, my world falls away, the sound getting louder and louder and louder until…I wake up.
Fucking motherfucking hell.
I reach out toward my nightstand and slam my palm against my alarm, permanently ending the obnoxious sound.
My cock screams inside my boxer briefs, and my stomach aches with the need to come and do it hard.
I check the time to see it’s already ten past seven.
I was dreaming. About Maybe.
Which is no surprise, given how far I let it go last night like a fucking idiot.
With my heart pounding inside my chest and my breaths coming out in erratic pants, I look down at my primed cock and groan.
I rub at my eyes and take deep, steady breaths until my heart slows down to a normal pace.
What in the hell was I thinking?
About Maybe’s perfect, untouched, tight pussy, you bastard.
Completely unsure what to do with this insane realization, I scrub a hand over my face and stand up from my bed. I adjust my now half-hard cock beneath my boxer briefs and head into the hall and toward the kitchen to make some coffee.
As the pot brews, I grab my phone from the kitchen counter and scroll through work emails. But before I’ve even managed to pour myself a cup of coffee, I’ve found my way back to my text conversation with Maybe.
And that’s how you sext, kid.
Such a douche thing to say, I almost choked on it.
I just didn’t know how else to stop my one-way train to hell.
I set down my phone on the counter and pour myself a coffee before I do something stupid like text her to explain.
But my distraction technique only works for about two minutes. I pick up my phone again, ready to lay it all out there when it pings with a text.
Only this time, it’s not her. It’s her fucking brother.
Evan: Mind if I conference into the morning meeting today? I have some things I want to update the marketing and finance teams about related to Simply Baby. And you’re a real dick for passing the torch on crazy Frank Wright. LOL. His daily calls are a true joy. Right up there with a root canal.
Evan: Oh, and I talked to Maybe yesterday after her interview with Rainbow Press. Just wanted to say thanks for helping her out. I owe you big time, bro.
Oh yeah, you helped her out, all right, you dirty bastard, my mind taunts.
Jesus Christ, I am in serious trouble.
Maybe
At exactly noon, I let Bruce know I’m taking a long lunch and head to Jovial Grinds.
I’ve been a powder keg of nausea and excitement and uncertainty since last night, and a morning full of Bruce, his -isms, and his favorite Doo Wop CD have not done anything to help the situation.
I know the whole sexting thing with Milo ended unconventionally, but no matter how much I dissect our every exchange for technical merit and artistic value, I can’t forget that he did, in fact, request an actual picture of me in my underwear and sent me one of his own.
That has to mean something.
Practice-run, instructional-value-only sexting shouldn’t include show-and-tell…right?
RIGHT?
It’s the second, intense-inflection RIGHT? that has me here, in search of another opinion.
And oh baby, I’m getting it. From the instant—and I do mean instant—I stepped through the door, Lena has been in full investigation mode regarding what she calls “Phase 2” of the plan.
Thankfully, there’s only one customer inside the coffee shop, a sixty-year-old regular by the name of Winston who loves naps as much as he loves coffee.
While he snoozes behind the New York Post, I sit across from Lena and ramble through the events of last night as calmly as humanly possible.
Which is to say…not in the least bit calmly at all.
“I don’t think I did the whole segue from interview talk into dirty talk like you probably pictured… I mean, I know I didn’t. We were joking and stuff like usual, and then I pretty much just asked him how often he sexts with people. He didn’t really give me an answer, but I asked him to sext with me. He seemed hesitant in the beginning, but eventually, he did it. I mean, we did it. We sexted,” I spit out in a rush. “I actually sexted with him, Lena. He even sent me a picture of his bulge, and dear God—”
“Wait a minute.” Lena stops me mid-sentence, and a giant, amused smile spreads across her lips. “You mean to tell me you actually sexted with him last night? Full-on junk pictures exchanged, dirty-talking sexting?”
Eyes as wide as saucers, I nod. “The pictures were in our underwear, but yeah.” I pause briefly be
fore jumping to add, “And he ended it abruptly.”
She waves a hand wildly and then smacks it down on the table so hard, Winston jumps, snorts, and then falls back to sleep.
“Don’t worry about the ending. If you were in the throes of pictures and pornographic material, he was invested. He probably just panicked.”
“Panicked? Why in the heck would he panic? I’m the one with no experience here!”
She laughs. “You’re his best friend’s little sister. They probably swore on a blood pact that he’d never touch your lady bits when they were kids, and now, he’s exchanging soft-core pictures with you.”
Her overzealous joy spurs a laugh from my lips. “You’re insane.”
She shakes her head. “Nah, girl, you are insane—in the best damn way. I am so proud of you!”
I giggle shakily and take a sip of coffee. “Man,” I jabber. “I still can hardly believe I did it. I mean, I had to read through our conversation again this morning just to make sure that it was real.”
“Fast learner, you are, Obi-Wan.”
Her response makes me snort. “First of all, I don’t think that reference is right.” She shrugs. “And let’s not get too ahead of ourselves here. I mean, I don’t even know if he…you know…enjoyed it.”
“Did you enjoy it?”
“What?”
“Come on. Don’t be a prude,” she says with a grin. “Were his messages focused on making you come?”
Uh. Ha. Yeah. I mean, I was touching myself at his command when he ended it. When my cheeks start to heat, she points an index finger in my direction.