Filling The Hole

The night sky is dark and desolate. Stars cannot be seen from this little apartment balcony within the city. I look down upon the street as cars fly by on their way to wherever. Everyone knows where they are going but me. I hear a faint voice calling my name but do not respond. I am utterly lost in thought.

“Earth to Elijah. I was talking to you man. You still haven’t answered my question. So how long has it been?” the voice approaching behind me asks again.

“How long since what Charles?” I ask back. I turn around to see my friend Charles standing there.

“How long since you got some, my man.” Charles smirks as he asks.

Charles is my best friend and roommate. We grew up together and he has been gracious enough to let me stay with him these last few years rent free in his apartment while I get back on my feet. Well free provided I make him the hot beats that he likes to rap on so much.

“It’s been a minute. For real. Not since Olivia left me for that Wall Street prick.” I say back reluctantly.

“Man, we need to get you some soon. Like for real for real. They say if you don’t use it you lose it you know.” Charles laughs and pats me on the back.

“Man, I ain’t worried about none of that. I’m just trying to make this music and live out here. Women cause too many problems for me.” I cut back rather bluntly.

“Why are you bringing this up now?” I ask him while we walk back into the apartment to the keyboard to lay out some drums over a smooth piano melody.

“Well, you know we got that show tonight and you are DJ-ing my set. Maybe you might find a cutie in the audience to bring home. I know I am going to find one for myself. This apartment is big enough for us to both get our freak on quietly in our own space you know. These walls are pretty thick.” Charles says laughing and bobbing his head to the rhythm coming from the speakers.

“Just thought I would offer man. You have been looking a little down lately. Especially when I find you staring at the street like that. Makes a man think you might jump or something. I don’t want no dead bodies on me you know.” I look back and see Charles joking smile has turned to worry.

I reassure him “I am alright man. I may take you up on that though. We will just see how the night plays out. How much time do we got before the show?”

Charles checks the clock “Show is at 9 PM. Shit it is 5:30 PM. Finish this beat that you are working on later. It is fire though. I got a few things to do before the show. I need you to get down there and set the equipment up.”

I save the beat on my computer, shower, get dressed, pack up my things, and head down to the venue. I walk into the building and quickly locate the stage to setup. While setting up I begin to think to myself that maybe Charles is right. I mean it has been quite a long time. A man can only beat his meat to internet porn for so many years without wanting true physical intimacy again. I should test my luck tonight. Find a nice consenting adult woman and have some fun. Once again, I was so deep in thought that I did not notice the person that appeared in front of me.

“Hello? Need any help sir.” I look up to see a cute face staring at me. I look her up and down briefly to take her in. She has dyed blue hair, a bit of a tummy, blue eyes, huge tits that are displaying ample cleavage in her “Peace, Love, and Hip-Hop” top, and extremely thick thighs that I know must have an even thicker ass attached. I stare for a second.

She speaks again. “Need any help sir.”

I shake out of my trance and force myself to utter a word. “No, I think I am good. Who are you anyway?” I ask so curiously.

“My name is Isabella. I am the owner of this venue.” She outstretches her hand waiting for a handshake. Her big tits and tummy jiggle in the process.

I stand up and shake her hand. “My name is Elijah. I am the DJ for the night. The artist Char…..er I mean C-money will be here soon.” I look around and say with a smile “Nice place you got here. Very excited to play a show here. The sound will be crazy.”

Isabella smiles brightly at the compliment. “Well thank you. I have had this place for many years. I have seen all kinds of acts come through here.”

I awkwardly exclaim “Many years!? Wow, you don’t look that old at all. I thought we were the same age.” I mentally face palm myself after my statement.

She laughs and blushes. “Didn’t your mom ever teach you that a lady must never reveal her age? But if you must know. I am 32.” She winks at me with a smile.

My jaw dropped at what I was hearing this beautiful lady in front of me is almost a decade older than me. I couldn’t believe it.

She must have noticed my surprise and quickly changed the subject with another question. “Are you a rapper too?”

I laughed and scratch the back of my head. “Yeah, I write some rhymes here and there, but I mainly work on beats for C-money.”

Isabella looks at me again. “Can I hear one?”

“Hear a beat?” I ask.

“If you want to play one sure. But I want to hear you rap.” She says this with a beautiful smile.

I ask her back a little embarrassed. “W-w-why would you want to hear that?”

She puts her hands on her hips and her tits and tummy jiggle again. She starts again “Well I have two reasons. 1) I think it would be a good mic check. 2) I want to hear one, and I always get what I want.” After the second reason she smiles and winks at me.

I summon the courage to get up and turn on a beat from my computer. I turn up the volume and step up to the mic. I think in my head to what this lady might want to hear. I find a verse that seems good enough. I begin

>Failure follows feelings of fear
>
>Fake fools fear knowing I’m near
>
>Hear horse hooves trotting along
>
>The same system of energy I bring to a song

I stop and look at Isabella down on the floor. I turn the beat off and walk over to her.

“Sorry, that is about all I got for that one.” I tell her laughing and scratching the back of my head.

“No, no, no. I was very impressed. I think you are very talented. Talented people are kind of my type.” Isabella laughs and says with a smile.

Her smile quickly turns into a smirk as she speaks. “Elijah, I want to give you a reward for performing for me.”

I laugh and say “Sure. What kind of reward?”

Isabella looks me dead in my eyes with a very mischievous smile and says, “I want to suck your cock and let you cum down my throat.”

I take a step back and almost trip over my own feet from what I am hearing. I stand there for a second processing this proposal from Isabella. I almost choke on my next words as I speak them “Run that by me again.”

Isabella sighs “I said I want to suck your cock and let you cum down my throat. It isn’t rocket science Elijah. Are you in or are you out?”

I look at Isabella again trying to see how serious she was about this. I can tell she is extremely serious from her eyes. I respond to her with a puzzled smile “Sure. But, why?”

She laughs. “I told you, talented people are my type, and I always get what I want.” After speaking she looks me up and down and bites her lip.

Isabella speaks again. “Now Elijah follow me to my office so we can get a bit more privacy.”

I follow Isabella from the stage area into a hallway. I look down at her ass and sure enough I was right about the thickness. I also contemplate the chain of events that lead me to this point and remember Charles advice from earlier * if you don’t use it you lose it*. We stop at a door that spells Isabella’s name. She opens the door and I walk inside. She locks it behind her. I turn around and see her licking her lips in anticipation.

She breaks the silence “Alright Elijah, now that I have you alone drop your pants for me. Now.”

Almost on command I pull down my shorts and boxers to reveal the stiff erection that had been forming in my pants. Isabella walks slowly to me and gives my cock a nice slow stroke. I still can’t believe what is happening right now. A beautiful chunky woman is stroking my cock in her office. It is almost something out of a dream.

Isabella whispers in my ear “I saw the way you stared at me when you first noticed me. I have seen that stare from hundreds of guys before. You probably were turned on by these big tits of mine. Weren’t you? Tell me.” She pulls back and uses her free hand to cup her tit through her shirt and the other hand to squeeze my cock hard.

I moan a little and say “Yes. I was.”

She looks at me and says “Well I will just have to let you see them then. Pull them out for me. I don’t want to let go of this cock.”

I use both of my hands and pull her shirt down revealing that she had not been wearing a bra. My eyes widen and I lick my lips. I try to grab her tits, but she swats away my hand and says playfully “You can look, but don’t touch until I tell you to.”

She pulls close and whispers in my ear again. “I bet you like the fact that I’m not wearing a bra. Don’t you Elijah? I saw you staring at my jiggly tits and my tummy when I shook your hand. You can grab them if you want but gently. I want one hand on each.”

I follow her instructions and have one hand gripping her big tit and another up her shirt squeezing her tummy. I am extremely turned on by this point.

“You have a nice decently sized cock. Not too big. Not too small. Pretty girthy too. Just about right for me. Maybe if you are a good boy, I will let you try it out for my size in my other hole.” She laughs as she bends down and starts licking my cock from base to head.

I had forgotten how much I loved getting head. My ex had never been good at it and it always seemed like a chore for her when she did it. But this lady knows how to work a cock.

Isabella puts the tip of my cock head in between her lips and pushes it all the way into her mouth. My cock completely disappears down the throat of this beautiful woman.

She begins to bob her head back and forth. Almost to the same rhythm of the beat I rapped to on stage. She also starts fondling my balls which drives me wild. I don’t feel like I can last long at this rate. In fact, after one more bob of her magical head. I feel myself shooting a huge load down her throat. My orgasm is so strong that my body shakes. She sucks every last drop of my cum out of my cock until I am soft and shows it for me on her tongue. She then swallows it.

“Wow you sure did cum a lot. Must have been a while since you had some good head. I think I will have to keep you around.” She winks at me as she stands up to get a towel to clean her face.

She checks the clock and speaks. “Oh well we better get going to prepare for the show. Looks like I will have to take my turn later.” She grabs her phone and says “Put your number in. I will definitely be seeing you later.”

I put my number into her phone and clean up with a towel as well. I leave her in the office and head back to the stage to get ready. When I reach the stage, I see Charles rehearsing there.

He looks at me and asks “Yo Elijah. Where have you been? We got a performance tonight you know.”

I look at him grinning while I speak “Charles man do I have a story for you later. But, for now everything is set up and we should be good to go.”

Charles looks at me and responds to my grin with his own grin and a wink “You will have to tell me about her later. She must be a master in va-jitsu to have you grinning like that.”

I laugh and say, “Something like that man.”

Charles keeps rehearsing until Isabella appears from the hallway to greet him and tell him the rules of the stage. While Charles is looking around, she looks at me and gives me a wink. They finish their chat and Isabella turns around to walk off.

Minutes later my phone buzzes with a text from a new number that reads “Hey it is Isabella. Your friend is funny. Have a good show. Here is my address come over after so we can celebrate, and I can have my turn next ?. Also, no need for condoms. I am on the pill.”

I had the stupidest smile on my face after reading the message and was happy to get this show over with as quick as possible.

The show came and Charles was in rare form tonight. He really was looking for a cutie to impress with his lyrics. He was gliding across the stage. Spitting his rhymes in the best way over the beats. The show didn’t last very long, but after it was over, I knew I couldn’t pack up faster. After I was all packed, I told Charles that I would see him back at the apartment. I ran like fire to shower at our place before heading to Isabella.

Isabella’s apartment was not far from the venue. It was merely five miles from it. I got there with a hard cock and a face full of sweat. I go up to her door and knock on it. It feels like forever until she opens it, but she finally does peak her head out. I walk in and look at her. When I see her I can’t believe my eyes. She looks stunning in a red lingerie piece that shows off her tummy and has her tits almost spilling out the top. I begin to stare.

Isabella catches my stare, laughs, and says “Take a picture it will last longer. Glad you like the outfit.”

I laugh too and slowly walk towards her about to grab whatever I can of her.

Isabella stops me and says “Settle down there. It is my turn now remember. Now you have to do whatever I say to make me cum.”

I stop dead in my tracks and say “Sure. What do you want me to do?”

She winks and says, “Follow me to the bedroom.”

I walk after her gazing at Isabella’s ass in her lingerie. Thinking about having that ass bent over.

We reach her bedroom. We both walk in and she lays on the bed, takes off the bottoms of her lingerie, and spreads her legs.

“You are going to eat me until I cum. Any problems with that?” She says in a very commanding voice.

I shake my head no and get on the bed in between her legs and spread her beautiful pussy lips. I lick in slowly circles around her labia trying hard to not touch the clit. I notice this gets a big reaction from her and I keep dragging my tongue across her slowly.

I start to slowly take her clit in between my lips and suck on the hood while I lick the tip of it gently. This really sends her wild. She closes her thick thighs around my head squeezing me. It gets a little hard to breathe but I keep persevering. I reach my hands up to her chest and squeeze her soft full tits. My cock grows from the taste of her delicious juices and the tits in my palms.

I hear her fumbling around in a drawer until she pulls something out. She takes my hand off her tit and puts a long hard thing in my hand that I can only assume is a dildo. I lift my face from in between her thighs and examine the thing she has given me. It is a big pink veiny dildo.

Isabella looks at me with a smile and lust in her eyes and says “I want you to use that on me while you eat me out. You have gotten me quite close. Just a little more.”

I do as I’m told and stick the big pink dildo deep inside her pussy. I move it in and out while I continue my clit sucking. After a few more minutes of this Isabella’s legs once again tighten around my head while her breathing speeds up. I know what is about to happen. I keep up my pace and sure enough. I hear her orgasm when she lets out a long moan followed by her collapsing on the bed.

I let her lay there for a few minutes bathing in her own pleasure. I’m about to ask if she can do a round two when she sits up pushes me down on the bed, rips my pants off, and starts sucking my cock.

She looks me in my eyes and says “You better not come yet. After I’m done sucking you. I am going to ride you until you cum deep inside me.”

Hearing her talk about riding me really gets my cock so hard. I am ready to burst but I hold it in and continue to enjoy Isabella’s sucking. She licks it up and down once more and teases the tip with her tongue. She knows I can’t take it anymore and is gripping it tightly at the base to delay my cumming.

“Okay, time for me to ride this cock.” Isabella says this as she straddles me. I look at her slowly descend her hips and her pussy swallows my cock. It feels so amazing. I haven’t had pussy in so long especially raw. I feel like I am about to explode but I must keep enjoying this for as long as possible.

Isabella rocks her hips back and forth. I see her tits jiggle in my face. I am so hard watching this sexy woman on top of me pounding. I can’t hold myself back anymore and use one hand to grab her tummy and the other hand to squeeze her tit. They are both so soft. Her pussy is gripping my dick so tight.

She looks down at me, giggles, and says “Tell me how much you like this sexy chubby body. Tell me how much you love my tummy, my big fat titties, and my fat ass. I want to hear it.”

At this point. I am the hardest I have ever been in my life. I can’t take it. I am going to cum in this pussy. I NEED TO CUM IN THIS PUSSY. I tell her. “I love your big sexy body. I love your tummy. Your big titties.”

“Is that all you love?” She licks her lips and looks at me with a wink.

I move my hands from her tummy and titties to her ass and grip it hard. “I also love your big fat ass.”

As soon as I say that I feel my body shake and erupt with a violent orgasm deep into this beautiful woman. I cum so hard that I feel like my cock will fall off. I can’t move and Isabella rolls off me.

“Wow. I haven’t fucked like that in a long time.” Isabella says panting and laughing.

We lay there on the bed side by side for some time. She looks into my eyes while I investigate hers. Without words we have reached an understanding. We are both searching for something that maybe the other can fulfill. We don’t know what the future may hold but we can try and figure it out together in the morning.

Source: reddit.com/r/eroticliterature/comments/daxzt1/filling_the_hole