Paying The Rent Pt 05

It's not even a week since I last punished the ladies. I am replying to emails from different contractors so I know when they would be free for a cookout.

I turn from email to porn sites and squeezing my dick through my pants. It's midnight and I am thinking I am going to jerk off to porn when I remember. I have a Sex Slave downstairs. She is probably asleep but I have the master key. I can get into her apartment at anytime. I think I will go pay her a visit.

I walk downstairs and open her door and quietly close it behind me. The apartment is pitch dark except for the streetlights filtering through her blinds. I look in her bedroom door and she is asleep naked. Her sheets are layered over her hips hiding her pussy but her tits are bare and her legs are sticking out. I walk to the side of her bed, and strip. My plan all along was to rub my cock over her lips. Pushing myself into her mouth and waking her up until I saw the dildo on her bed. I picked it up and sniffed it. It smells of fresh pussy juice.

I get pissed. I had warned her Any sex or masturbation was to be photographed and texted to me. I didn't get any texts.

I put one hand over her nose and mouth and pinch her nipple. Increasing the pressure until she wakes up and screams. First in pain, and then in fear because someone is in her home. She recognizes me and I am pretty sure I hear a "I am sorry." Muffled under my hand. I am laughing inside, but I keep a stern look.

"What are you sorry for?" I ask, and I release my hand and easy up on her nipple but I don't release it.

"Whatever I did I am sorry." She pleads.

"You did two things. First you said you were mine for 30 days as long as it doesn't interfere with your work. Second what did I tell you to do whenever you have sex or rub one out?" I say as I hold up the dildo.

"I did. I did. I am sorry I fell asleep before sending them."

"You show me the pictures and I will apologize by showing you how nice I can be. I will make you cum and cum, but if they aren't from earlier tonight god are you going to regret it." I warn her.

She starts patting the bed looking for her phone. "No I promise." She unlocks the phone, and opens the pictures. "Look!" and she hands me the phone.

Sure enough there are about 6 pictures from earlier tonight around 11pm. Her rubbing her clit, pulling the hood back to expose it, 3 with the dildo pushed into her at different depths, and finally her twisting her nipples.

I flip the sheet off her, and get on the bed between her legs. I put her legs up over my shoulders. "Now I owe you an apology." I dive into her pussy face first. Licking, kissing and sucking on her pussy and clit. I am not being rough but firm. I want her to know someone is going down on her.

I don't get my first lick across her clit and her loud moaning changes and she groans out "Oh god"

I have her nice and wet after just a little licking. She had herself very worked up before falling asleep. I take my two fingers I was holding her lips spread with, and push them into her pussy. She lets out a satisfying gasp that turns to a moan as I start finger fucking her.

I want more though. I lay on the bed next to her but facing the other direction. I don't even have to say anything. She climbs over me to 69. She hasn't even settled her hips down for me to continue and my dick is being sucked into her mouth.

I lick and suck her clit while alternating licking up between her pussy lips. I pull her hips down a bit and she pivots as she feels me trying to tongue fuck her. That turns into more upward licking. Which becomes licking and tongue fucking her ass.

Chris moans as I tongue fuck her ass. "Please. You promised to be gentle tonight."

I tap and push her hips for her to roll off me. I crawl up between her legs. I push myself in slowly and gently. I lean down to nuzzle her neck as I start a slow sensual fuck. "Trust me I am going to be gentle, and tonight you are going to get a gentle ass fucking.

"Oh god." She moans. It kind of sounds like a Holy Shit this is nice or maybe, what have I gotten into. To be honest I don't care. I slowly stroke in and out of her. She is softly moaning, and humping her hips as we fuck. I bend my head down and try to get her nipple in my mouth. I can't quite manage it. Chris pushes her tit up with her hand and puts the nipple in my mouth. I suck it into my mouth and gently grab it between my teeth.

She holds my head against her and gasps while I softly chew on her nipple. "Oh my god. I can't believe you are going to make me cum. Please don't stop."

"I have no plan on stopping but I want you on your hands and knees. I am going to fuck you from behind. While I do I am going to use the lube you used on your toy earlier and slide a finger into your ass. Then after a few minutes my finger will become my thumb. Once your ass will let my thumb slide in and out I am going to pull my thumb out of your ass, pour some lube right in your open asshole, pour some on my hard dick after pulling out of your pussy and I am to fuck your ass. I promise if you are not enjoying it after two minutes I will stop for tonight."

I pull out of her and she moves to get onto her hands and knees with no prompting. I nudge her hips so she is at the edge of the bed and I can stand on the floor. Not quite gentle, I push back into her pussy. She gasps out and the sudden invasion.

"Is this not gentle? Tell me it's not and I will ease up." I tell her.

"It's not gentle, but it's not hard." She says as she moans.

"Are you asking me to stop or ease up?" As I pour some lube down her ass crack.

"No I am not."

I slip a finger in her ass.

"Oh god." She moans

For the next few minutes I am just semi gently fucking her pussy while I finger her ass. I then pull out my finger, pour more lube on her and push in my thumb. I feel her instinctively clench down on my thumb and groan. This is taking too long. I start pushing my thumb in and out vigorously.

About a minute later I pull my dick and thumb out of her. I rub some lube on me and then pour more onto her. I push just the tip of my dick into her open ass. I don't want it to close.

Nervously Chris starts chanting "Oh god. Oh god."

"Chris, did I not promise to be gentle?"

"Yes."

"Have I ever lied to you?" I don't give her a moment to answer. I nudge myself all the way in and hold it.

"Nnnnnooooo." She answers as I push in, and stop after her ass swallows the head of my dick. "Thank you. I need a minute."

"I said I would be gentle. I never said I would take my time." I slowly push all the way in balls deep. Chris just lets out a long groan. "Now I will allow you a moment to get used to the feeling of my entire cock shoved in your ass. When that moment is up I am going to enjoy fucking your tight ass until I cum."

"Oh fuck." Is her only response

I start slow. A small pull out a small push in. No complaints. Halfway out and back in a few times. Some light moaning that sounds like she likes it.

While I slowly fuck in and out about halfway. "Chris it doesn't sound like you are hating this."

"No. It's different, but no I am not hating it."

I keep the slow steady strokes going but now about ¾ strokes. When I get a kinky thought. "Chris when you use your vibe do you like to fuck yourself with it or just rub your clit?"

"I like both."

"Reach out for your toy, turn it on and push it into that wet pussy."

"What? Now? With you in my butt?" Chris asks a bit shocked.

"Yes right now. It's called DP or Double Penetration. It's supposed to be 2 guys on 1 girl but I am improvising."

"Oh my god I can't imagine that."

"Well if you don't do it Now. The gentle promise is off. I will flip you on your back. Fuck your ass as I see fit and shove that vibrator in your pussy at the same time."

Chris reaches out to grab the dildo. "No, no. I am not saying no. I was just surprised." I hear the toy turn on and feel it as she rubs it around her pussy lips. After a few rubs she pushes it in. "Oh god I feel so full. Oh god."

Without me telling her to she starts fucking herself faster with the toy. I match her speed. I can't help it. Her tight ass gripping me, the vibe rubbing me inside her. I give one final push and I cumm in her ass.

I pull out and Chris whines. "I am so close."

I pull out the vibe. "No don't make me stoooppp."

I push it into her open ass. "Fuck your ass until you cumm."

I grab her hand and put it on the vibe. "Fuck your ass until you orgasm or I will."

She starts fucking herself and moaning simultaneously. I watch her for a moment and it's not pain or discomfort she is moaning about. They are moans of pleasure. I crawl up on the bed next to her. "That's a girl. You don't want to say it out loud do you? Did Mommy tell you only bad girls like anal? Maybe good girls don't do those things? Right now you are neither. You are my personal sex slave and I want to watch you cumm from my nice gentle fucking. I know you like it rough, you can admit it. You like when I fuck you hard don't you?"

"Oh god I can't win." She gasps out.

"That's not an answer. Yes or No do you like when I fuck you hard?" I ask.

"Yes. Yes I like it hard." She answers

"Do you want to fuck your ass or do you want me to jam that vibrator into your ass? I ask.

Chris keeps pushing the vibe in and out of her ass. I reach under her and rub her pussy and clit. I am whispering in her ear. "Your pussy is so wet. You are loving the vibrator in your ass aren't you? I want to watch you cum. Once you cum, gentle is done. You are getting on your knees on the floor and I am going to face fuck you. When I am hard again, and your face is covered in drool...". I don't get to finish.

"Ffuuucccckkkk." Chris groans.

I feel her pussy juice just pour out over my hand. She collapses flat on the bed. I keep my hand under her rubbing her clit.

Her whole body shivers. "Please stop too much." She reaches down trying to pull my hand away. I won't move my hand.

I get evil. "I told you, once you cum gentle is over. Now your ass is mine. I am fucking you Hard. Until you get on your knees I will keep rubbing your clit harder and harder. If you are too sensitive get on your knees."

She groans and rolls over and slides off the bed. She has her back to the bed. She doesn't realize it, but she just put herself in a bad position. With her feet under the bed, and the bed behind her she will be trapped. I will be able the fuck her mouth and she won't be able to pull away. I get off the bed and stand up. She is slumped forward a bit. I grab her hair and pull her up straight. I don't have to say a word. She opens her mouth and sucks my half hard cock in her mouth. She is running her tongue around me and sucking on me.

I use my foot and kick her knees back. She shuffles back and I can see in her eyes she realizes her mistake as her back hits the bed. I smile and push forward into her mouth and her head hits the mattress. "That's right, you aren't going anywhere." I keep a hold of her hair and start fucking her mouth. I am going to the back of her mouth and throat with each stroke. Just far enough to be too far for her. She is gurgling and gagging. Every few strokes I pull out to allow her a gasp of air and shove myself back in.

I keep this up for a few minutes. Her hair is a mess in my hand, her eyes are watering and she has drool all over her chin dripping onto her tits. I pull out of her mouth and pull her up onto her feet by her hair. She moans in pain and stands up. I pull her to her mirror.

"Look into the mirror. This is what a good slut looks like." She looks down with her eyes, not wanting to see herself like this. I pull her hair harder pulling her head back. "I said Look."

"Ow ow ow. I am sorry." She yelps as I pull harder on her hair.

"What do you see?"

Chris quietly moans. "A slut."

"That's right. Do you know what else Sluts are good for?"

She is whining now. "No."

"Taking my cock nice and hard in Any Hole at Anytime." I spin us around and bend her over the bed and push myself between her ass cheeks.

Chris screams at the sudden fucking. I wasn't sure where I would land. Would I slip in her pussy or have to push a tad to get in her ass. I slip deep in her pussy and shove her face into the bed. "It's after midnight, stop screaming. If someone knocks at the door you are answering it naked. If I get a complaint I will come back some night and spank your ass raw. Do you understand?"

"Yes I am...sorry."

Her voice catches as I start fucking her. I am fucking her hard against the side of the bed. I am holding her at her waist just above her hip bone. I have a nice firm hold and as I am fucking in I am pulling her to me. Her face is buried in the bedding. She is grunting, gasping and moaning as I fuck her.

"That's my good slut. Your pussy is so wet. You are dripping so bad my balls are wet."

She keeps her face in the bedding as I talk to her. I slap her ass rather hard. "Someone compliments you and you say nothing?"

"Thank you" she gasps out.

I slap her other ass cheek a little harder. "Thank you for what? Spanking you?"

"No, no thank you for complimenting my wet pussy. It's wet because you make me wet fucking me hard."

"That's my good girl. Say it again. How do you like to get Fucked"

"I like to get fucked hard."

"Beg me. Beg me to fuck you hard."

"Jeff please fuck me hard. Please pound me until I scream."

"You want me to make you scream? You better make sure no one hears you scream." Almost in one motion I squirt some lube on her ass, pull out and push hardon into her ass. She screams into the bed spread. "You told me to make you scream"

Chris starts crying almost immediately. "Please Jeff no. Not so hard in my ass. It hurts so bad. It burns. PLEASE!!"

I pull out and smile at her wide open ass. I squirt a bunch of lube right in her ass and shove back in. "Nnnooooo!" She screams into the bed.

"No more bargaining Chris. I tried to bargain your late rent, you kicked me out and then came back begging. I told you and Kristen you would be punished. We bargained for Kristen to take it all, and you changed your mind. You said you would be mine for a month to do Anything. You beg me to make you scream, and here you are asking me not to." I yell at her.

"I am sorry." She cries out.

"Nope no more sorry. Now I am actually threatening you. You change your mind one more Fucking time and I will post both your and Kristen's videos with your faces clearly visible on every porn site I can find. I will make you both amateur porn stars. Do I make myself clear?"

She is sobbing now. "I am sorry. Please don't post Kristen."

"So it's ok to post your face?"

Harder sobbing. "Please...No...Please don't."

"So then you do want me to make you scream?"

"Yes Jeff. Please make me scream."

I waste no time I pull back and continue fucking her ass hard. She pushes her face back into the bed and cries as I fuck her ass hard. Between her clenching ass, her submissiveness and the power trip I am about to cum. I pull out of her ass and push her on her knees. She knows what I want and gets back on her knees against the bed and opens her mouth

I push in her mouth and I don't get 5 strokes in and I am cumming again. She chokes a bit and gags. I keep my cock on her mouth forcing her to swallow the cum in the back of her throat.

I pull out and she gasps. I step over to her bed and start wiping my dick clean on her bedding. "So have you learned to be careful what you ask for?" I ask her

"Yes I have."

"Do you realize no more bargains or negotiations, you are mine for the month period?"

With her head down. "Yes I am your personal sex slave."

I pick up my shorts and pull out my phone and start recording. She is a mess. Her hair is all messed up from me pulling it. Her eyes are red from crying, there is cumm on her chin. She is kneeling/sitting on the floor holding her ass with one hand.

I focus in on Chris. "Chris please answer yes or no. Did you ask me to make you scream?"

Still sniffling with her face Dow. "Yes."

"So you have learn from me fucking your ass hard until you screamed to be careful what you ask for?"

"Yes."

"You realize if you do anything but be my personal sex slave for the next month I will make you and Kristen amateur porn stars right?"

She looks up at me with tears in her eyes. "Yes I am sorry. I will do whatever you ask without complaint."

"Good girl." I stop recording, pick up my clothes and walk out of her apartment naked.

Sunday I stop my cleaning lady Michelle and ask her for a moment. She and I have talked about a lot of different things and I really like her, but I don't want to think I am ignoring her if I don't invite her to the cookout.

I try to gently talk around it when she interrupts me. "So you are getting a hooker for the guys and don't want me to feel uncomfortable?"

"Not a hooker no."

"That's what you call a woman you pay to entertain at a party."

"Oh I am not paying her. She owes me." I say

"So it's not a hooker?" Michelle asks.

"Not at all. Just a woman that made a deal with me for help."

"You mean someone in this building don't you?" She looks at me for a moment and I say nothing. "You do you dog." She laughs "Come on, come clean. What's your plan?"

"Alright. I was going to do a contractors cookout next Sunday. She and a friend are going to entertain upstairs during the cookout."

She laughs again. "A friend too?"

"I want you to come to the cookout, but I don't want you to be uncomfortable."

"You mean uncomfortable being the only person not getting their rocks off?"

I laugh. "Well yeah."

"What time is the cookout?"

"1pm." I say

Michelle thinks for a minute. "Ok I will show up early to clean say 9:30am or so. Can you have her upstairs say around 11am?"

"Why 11AM?"

"So I can have some private play time with the lady or ladies before the guys show up."

"Wow ok. Well let's see. I will text her now." I text the two of them.

ME - Next Sunday 11AM for the cookout. Plan on being here the day.

It takes a minute or two so we continue talking.

"Well I didn't see that coming." I tell her.

"I've played with women before, and with this damn pandemic I haven't felt another person's touch in way too long." Michelle smiles at me. "Do you have a problem with that?"

I laugh. "No ma'am"

"I want first dibs. I don't want her after she has fucked a half a dozen guys, and Not a word to the guys or I will kill you." Michelle warns with a stern face.

"Mums the word."

Kristen is first to respond.

Kristen - I can't come that early. Monthly School Meeting after Mass

Chris - ok 11am

ME - hhhmmm Kristen watching you get fucked and used in you Sunday Best sounds hot. I expect you in a nice semi sexy dress. No Mother Theresa crap. Too bad you will miss a special guest I am giving early access to. I guess Chris gets All the fun.

Kristen - I will arrive as soon as I can

I show Michelle the text. "Meeting after Mass? A goodie two shoes?"

"I have found they both have a real submissive side. I have had fun with them."

She smiles. "I bet you have. I don't want butch though. I like a pretty, soft, sensual woman."

I text

ME - Chris since Kristen will be wholesome in Sunday Dress. I want you in the first lingerie I got you. Full make up and perfume. I want a sexy sensual lady. The first guest wants a sexy lady to have sex with.

"Hey it sounds like I am a guy." Michelle says

"Yes I like to keep her on her toes."

Michelle laughs. "You are evil."

"I can be."

"Do you have a picture?"

"I will show you a body shot. I promised to keep the pictures private." I pull up a picture of Chris tied to the bed with Kristen's face in her pussy. I put my thumb over Chris's face.