Mommy's Boy

From Bailey's Point of View

I pack a few things into my purse. Every few weeks, I go out to the club on Friday in attempts to distract myself from the stresses of work.

I head out to the club. I have one drink and dance.

A guy approaches me.

I have no problem with that, it all depends on what they say that determines whether or not I even bother with them.

He leans up close to my ear, dancing in step with me, "you look like you could use a fuck, old lady."

I smile a little, "old lady huh?"

He motions to my skirt, "well that's not a very trendy skirt so you have to be what mid-thirties."

I hold my purse closer, "I am 25 for your information."

He winks, "you didn't say no to a good fuck though."

I motion him closer, "I only peg cocky boys like you."

He gets a little shy, "is that so?"

I nod a little, "yeah."

He stares at me, "I have always wanted to try that."

I hum softly, "why don't you come home with me then?"

I think about where I keep the pepper spray at my place. I mean, in no manner am I scared of this guy.

He's thin, small. I am not sure that he could hurt me if he wanted to.

He stares at me, "I would be down."

I get us a uber back to my place. I always bring a uber to the club just to make it easier if I get drunk and can't drive home.

He has his hands in his lap on the way to my place.

I unlock the door for us, slipping my shoes off by the door.

I look at his feet, "take off your shoes please."

He obeys me. I sense that he might be submissive.

He follows me up the stairs to my bedroom.

He stands a little awkward.

I smile a little, "don't be nervous, I will be gentle."

I put my purse by the bed.

He motions a little, "I would just like to say that you look really good with your lip rings and your nose ring. Those gauges are on point too."

I smile a little, sitting on the bed, "come here pretty boy."

He moves over to the bed sitting by me.

I stare at him, "you are sober, yes?"

He nods, "I am. I am not much of a drinker. I do like to go to the club and dance and stuff."

I softly pull him closer by his hip, "there's only a few things you need to know before we do this. Are you ready?"

He nods again, "yes."

I kiss him softly once, "you will call me mommy."

He blushes a little, kissing back slowly, "yes mommy."

I smile a little, "you will use the color system as your safe word, do you understand how that works?"

He shakes his head a little, "no mommy."

I stare at him, "green is you're all good, keep going. Yellow is that you're getting close to your limit. And red means stop and if you say red, I will stop immediately. If you say yellow, I will check in and see if it is okay to continue. It is to ensure that we both have a good time."

He is listening closely and staring into my eyes. Admittedly, I am not much for someone staring at me so intently, but I am glad he is listening to me.

He nods, "I understand mommy."

I lay him back on the bed, kissing him slowly.

I kiss along his neck slowly.

He moans softly.

I sit up and slip my shirt of.

He watches me, "you have nice boobs mommy."

I laugh a little, "do you want to touch them?"

He sits up and unfastens my bra before softly cupping my boobs.

He leans down and bites one of my nipples softly.

I slip my fingers into his hair.

He moves to the other, biting it softly.

I moan softly, "good boy."

He sucks softly.

I lay him back and slip from the bed, getting the strap on.

I slip off my skirt and put on the strap on.

He whispers, "mommy, can I get undressed?"

I smile a little again at how shy he seems, "yes pretty boy."

I get some lube from the drawer, watching as he gets undressed.

I hum softly, "now, get on your hands and knees boy."

He obeys me.

I move onto the bed behind him, "I am going to lube you up good, if I don't lube you enough just let me know, okay?"

He nods, "yes mommy."

I lube him slowly before slipping a finger in. I finger him slowly, before adding another finger.

He moans softly, "fuck."

I slowly spread my fingers, "you are a good boy for mommy."

He moans softly, "yes mommy."

I add more lube before I add a third finger and spread them.

I lube the strap on before I softly press the tip inside him.

He groans softly, "fuck."

I grip his hips softly, pressing the strap in slowly, "is it too much boy?"

He shakes his head, "no mommy."

I thrust into him nice and slow.

He moans, "oh fuck."

I thrust the strap a little faster, "do you like that pretty boy?"

He moans softly, "yes mommy."

I press on his back just a little, pressing the strap deep. He lowers himself a little.

I reach under him, rubbing his cock, "do you want to cum for me boy?"

He moans, "yes mommy."

I stroke him in time with the thrusts of my strap, "whenever you are ready boy."

He grips the sheets, moaning a little louder.

I keep my pace steady, "faster? Or just like this?"

He rolls his head back a little, "harder mommy."

I thrust the strap into him harder, still stroking at the same pace.

He groans heavily, cumming.

I thrust a few more times before pulling out slowly.

He lays flat on the bed, panting very softly.

I run my fingers through his hair, "are you okay, pretty boy?"

He looks over at me, "you don't like have a boyfriend or husband that is about to come in here and be mad at you, do you?"

I smile a little, "no I am single."

He mouths a word and then decides on another, "would you like to change that?"

I laugh softly, "I mean, I don't know. I work a lot. Was being pegged that good?"

He shyly nods, "it was really good mommy."

He blushes after a second, "I should get you off."

I smile, "no it's okay."

He stares at me, "I didn't realize you had a belly button ring."

I nod a little, "just my nose stud, the lip rings, and the belly button."

He sits up a little, "if you work a lot, I assume I should go."

He gets his phone from his pants pocket, "can I get your number?"

I put it into his phone under mommy.

He blushes a little when he sees what I decided to put it under.

I hold out my phone for him to put his number in, "just put it under boy."

He gives me a look, "you'll remember it's me?"

Admittedly, he is gorgeous, and I don't think I could forget him even if he never texted me.

I wave a hand playfully, "eh, I will just pretend like I do even if I don't."

He smiles a little and gets dressed, "I would really like to see you again. I had a good time."

I watch him, "I will think about it. I might have to make you complete some kind of task to see me again though."

He nods a little, "anything you say mommy."

I get him an uber and he goes home. I lock up the door before I go to bed.