Paying the Rent Pt. 01

I push my finger all the way in with one hard push. She cries out. "What did I tell you about saying no to me?"

Half crying "I am sorry. It hurts."

"I was going to be nice and go slow, and then you said No. I warned you about that "

"I am sorry. I am so sorry."

"Will you be nice to me so I can be nice to you, or should I just Fuck you?"

"No nice please. I am so sorry."

I ease my finger out. "Ok easy it is." I take the smallest butt plug, put some numbing anal lube on it, and push it in. It slides right in until the big end. It hesitates for just a moment and then pops in her ass with a small Oh. "See nice. In a little while we will pull it out for the next bigger one. Little by little I will open that ass so I can fuck it." She just moans. I hop back on the bed and spread my legs. "Now I believe you are supposed to be blowing me."

She climbs up on the bed and feels her way. She crawls between my thighs, grabs me with one hand and sucks my right into her mouth. On her up stroke she is sucking as she pulls her mouth off me. She then swirls her tongue around me teasing the head of my dick. This over and over while stroking me between head bobs. She is giving it a good effort but I want her throat.

She bobs down, I put my hand on the back of her head and put steady pressure on the back of her head forcing her deeper. I let her back off when she gags or coughs. After she gets a good breath I slowly push her back down. Before I know it she is fighting it with gurgling and her body spasms a bit but her nose is in my pubes.

It's been a good few minutes of her blowing me. To avoid cumming too soon I pull her head up. "Catch you breath." I move off the bed, grab the next plug and lube it up. She jumps when my hand slides across her ass. I grab the base of the plug. "Time for this to come out." Ever so slowly I pull it out to make her ass stretch around it. I gets past the wide part and her ass pushes it out. She lets out a sigh as I remove it. I think she has forgotten a bigger one is taking its place. I touch the tip of the next on the her ass.

"You just took it out. Why are you putting it back in? She whines

I put the first one in her hand. "This is what I took out." I watch as her fingers run around it. Trying to see it by feel. I push a little on the next one. "This one is a little bigger." The first ¾ slide right in and she moans. The last bit with a small push, and a groan from Chris pops right in. I climb back on the bed, take her hand and put it back on my dick. "Sorry for the interruption, please continue." She hesitates for a moment and then sucks me back into her mouth

She has been blowing my now for a few minutes and doing a good job of it when I have an idea. I pull her head off me. "I will make a deal with you. You are getting me close now. Let me pull out the plug and put my first load in your ass. I have a bigger plug I was going to put in you while we fuck, and after I came in your pussy I was going to make your ass round two. It would have taken longer to cum but you would have been more stretched. Now it might be a bit tight, but it will be quicker.

"Oh shit." She says. "I don't know. I told you I don't do this."

"That's why I was nice and got a nice bottle of anal lube to numb things up a tad and the plugs."

"Numbing?"

"Yes the lube I am using on you ass has some numbing gel in it."

"Thank you. Promise you will be gentle."

"I will be."

"If I say stop you will stop?" She asks.

"I promise to stop to give you a breather, but I won't pull out. I told you, I expected anal when you agreed."

"Fuck. Fuck. Fuck." Half crying "Please be gentle. Do it now.

"Ok." I pull her arm over towards the middle of the bed. "Lay flat with your legs together."

"What?" She is confused.

"With you like that your ass cheeks will keep me from getting too deep. That is of course you want a nice deep and hard ass fucking?"

"No no." She says quickly as she lays flat.

I straddle her thighs and just rub her cheeks for a minute or two. "I have heard for a woman it's like having sex again for the first time. Hopefully that pain is eased by the plugs. Then it's a 3way coin toss. It hurts, neutral or it feels weird and I have known women that love it. I hope for you it's not the first." I then reach down and pull the plug out with slow steady pressure. With just a little pull it pops right out. I toss it on the bed near her hand. "Reach out with your hand to feel the 2nd plug."

Her hand starts patting the bed as I drizzle some more numbing lube right on and in her ass. I use my finger and rub it around her asshole. After a minute or so. I follow the lube with the tip of my dick. Her ass easily takes ¾ of my head and then I get resistance. I push a little harder and I pop in.

"Oh shit. It doesn't get smaller like the plug. Please give me a minute." She just lays there panting and letting out little Ohs. I figure that's enough time and push in some more. She starts some really deep heavy panting. Almost begging. "Slow. Please slow."

"One more push and it's all the way in. Then I will give you a breather." Other then that I give her no warning I just push. She lets out a big gasp and then a long deep groan. Now you have earned a short breather."

Panting rather heavy and fast after the last push. "Thank you. Just a minute or two. I need to adjust to your size."

"Come on I am not that big."

With more even breathing. "It feels big to me right now."

"I bet once you get used to it you will like it. There is nothing like feeling a woman's ass squeeze down on you when she orgasms."

"What? No way." She says with pretty even breathing.

"Did you notice something?" I ask.

"What?"

"You aren't panting anymore. No strain in your voice." I tell her as I pull back a little and push back.

"Oh"

"Just a small Oh?" I pull back about halfway and push in and repeat.

"Jesus" she gasps.

"See again no stress. That almost sounded like you liked it." I pump in and out again about halfway a about six times and again stay buried in her. The entire time the panting sounds almost like she is liking it. "That almost sounds like you liked it. Did you like it?"

"I am not sure. I think so. It's weird. PLEASE BE GENTLE. I don't think I am ready for hard fucking."

I pat an ass cheek "See you be nice and I will be nice." I slowly pull out leaving just my head in and then push back in. Back and forth slow and easy. After a few strokes I pull out, and look at her open ass for a moment.

"Why did you pull out? Did you cum?"

"Oh no. You will know when I cum. Your ass has squeezed all the lube off me. I am re-applying some lube." I squeeze some right in her ass, I rub some around her asshole. Again rubbing my finger all around her asshole.

"Can I ask a favor?" She asks

"What would you like?"

"Can I take off the mask please?"

"Why?"

"It's getting stuffy."

"One condition. You replace it with a blindfold I got. I don't want you to see anything tonight. I want you to feel it all."

"Oh I am feeling it."

"Keep your eyes closed when you swap." I grab the blindfold and put it in her hand. "If I catch you peeking it's 5 whacks with the paddle per eye you open."

"I think you want to paddle me."

"I do, so don't give me a reason." I tell her.

She has the mask off and looks back at me with her eyes closed and with a little laugh in her voice "Yes sir." She turns back forward and puts on the blindfold on. I don't wait, I push back in. I bottom out and pull back and start fucking her ass. She lets out a surprise gasp and just keeps muttering "Oh shit. Oh shit."

"That certainly doesn't look like a face of pain."

"No, so full. So big. I can't believe it doesn't hurt. I am not going to say it feels good, but it certainly doesn't hurt."

"Good then I can really give it to you." I grab her by the hips and start fucking her hard and fast. She starts moaning and gasping with the harder fucking. I keep up the fucking, and watching her ass cheeks wiggle.

I start breathing heavy and grunting myself and then I push as deep into her as I can and I cum. I shoot into her as over and over. I stay deep in her ass as I catch my breath. I finally roll off her and her ass is left gaping open. She reaches back to rub her ass.

"Oh my god it's still open." She gasps.

"Don't worry. It will close in a moment."

"I don't believe I felt you cum in my ass."

"I am going to cum in you and on you, but I promise you as long as you continue to be nice and I will continue to be nice to you and make you cum."

"I am amazed I was close to cumming when you came in my ass." Says Chris.

I roll her over and climb between her legs and put her thighs over my shoulders. "If you were close I am going to put you over the top." I dive into her pussy. I lick between her lips and up to her clit. I give her clit a few licks and slide my tongue back between her lips. She instantly starts moaning and gasping as I flick her clit so I suck her clit. I pull back as she start humping her hips.

"Please don't stop. Please I am so close."

I notice my cum running down her ass. I use two fingers and scoop it up. I put my fingers in her mouth and she sucks them clean. I lean back down and suck on her clit like I was trying to get milk from a tit. I suck ease up a tad and suck again. Her hips are bucking. She has her hands in my hair holding me to her. Her gasping and moaning is getting louder until she tries to push my head away half moaning and half screaming. "FUCKKKKK I AM CUMMMMMINGGG."

She manages to push me away. I wrap my arms around her thighs and hold her tight as I resume flicking her clit with my tongue. She is fighting me and trying to pull away. "PLEASE STOP......TOO SENSITIVE.....PLEASSSEEEE."

After about 30 seconds I stop and let her go. She is literally panting with little shivers running through her. I watch her calm down from her orgasm and realize I am hard again. I climb off the bed and grab another gel I ordered. I dab a little on my finger and go to rub it on her.

She grabs my wrist. "Please no I need a few minutes."

"I promise I will give it to you once I rub in this gel." I promise her.

"I don't need lube to have sex."

I pull her hand off my wrist and gently say. "Let go."

She releases my wrist and I finish rubbing into her clit and reach for more to put on her nipples. "Now you can rest for a few minutes. Would you like some water?"

"Yes please."

"Stay put. I will be right back."

I get up and grab 2 bottles of water and head back to the bedroom. Chris is sitting up on the bed. I put the water in her hand. She twists off the top and takes a drink. She shifts a little on the bed.

"Are you ok?" I ask.

"I just need a minute or two. It was a fantastic orgasm."

"When was the last time you had sex?"

"I am not answering that."

"Why not? Bad enough you work long hours with your own business, but then the pandemic. I bet it's about as long as me at least."

"So tell me how long since you have had sex?" She asks.

"At a wedding last summer. I got a room that I never slept in. Typical wedding story. Met at table, danced and drank and went back to her room. So now your story."

"Ugh. OK. Old boyfriend. We ran into each other at a bar last St Patrick's Day weekend. I brought him home and he was gone when I woke up."

"Did he make you cum like I did?"

She turns her head with the blindfold on it towards me. "Really?"

"Yes really. Don't forget no refusing me."

"Fine no. I haven't cum that hard in a long long time. Does that make you feel like a big man."

"That's it!" I grab her and pull her over my lap. "Five whacks for smart ass remarks."

She tries to fight me but I have the leverage. The paddle lands with a smack and she yells ow, and gets a pink spot. The next shot is harder, and she screams louder. "I am sorry please no more." This leaves a light red mark. Much better. I rain the remaining ones one after another cheek to cheek. She is damn near hyperventilating trying to hold it in. I start rubbing her cheeks to lessen the sting. "I have warned you multiple times tonight. You want to be a smart ass, and your ass will smart."

"I am sorry. I won't do it again." She pants trying to hold in tears.

"With a little pain comes pleasure. Answer me honestly are you turned on?"

"No it hurt."

I reach down with one hand and feel her nipples. "Then why are your nipples hard?" She is still over my lap, and I use my two hands to hold her ass cheeks and pussy lips apart. "There is literally pussy juice leaking out of you. If you aren't turned on why is that?"

"God help me. OK I haven't stopped feeling turned on since I came."

"I know why."

"Yes because you made me cum real hard."

"And because that wasn't lotion I rubbed on you after you came. It was a sensitizing gel I put on your nipples and clit."

"What?"

"I bought a bunch of things when we made our agreement. The blindfold, mask, vibrator, your outfit, some different lubes and a few other things you might discover another time. For now I am going to help keep you out of trouble." I take the ball gag and push the ball in her mouth, and buckle it behind her head.

She tries to complain but all she gets out is garbled moaning. I pull her off my lap and stand her up in front of me. Her nipples are rock hard. I flick them with a finger on each hand. She moans and drools a little out of her mouth. I pinch them just a tad hard, and she moans.

"Nod your head. Moans of pleasure?"

She nods her head yes.

"Is you clit still tingling?"

She nods her head yes again.

"Get on the bed. Lay on your back and spread your legs. I am going to fuck you and hopefully your tingling clit is going to go off like fireworks. Again she tries to reply but I get nothing but garbled moans. I climb between her legs. I flick her clit back and forth with my dick and she moans. I then use my dick to smack her clit a few times and again she moans. I then aim my dick between her lips pushing right in with one steady stroke back and forth, back and forth. Nice steady strokes working her in if you will. Making sure I am fully coated in her juices and sliding in and out rather than feeling unlubed skin pulling.

She is constantly moaning with each stroke. I then go from nice steady strokes and hard fast fucking. This causes her to gasp and let out a loud HHRRGGGHHH. I am pounding her now. All I can hear in the room is my heavy breathing, the wet sloppy sounds of me pounding her wet pussy and her gurgled responses. My balls actually get hurt one or twice smacking into her ass.

Between gurgled sounds Chris looks at me and points to the gag and puts her hands together as is to ask For the gag out. I stop fucking and stay deep in her. Now that I have stopped I can feel little quivers through her pussy. "Do you want that out?" She nods yes. "Were you close to cumming when I stopped?" Again she nods yes. "If I allow you to take it off there are conditions." She nods yes. If you mouth off 1 more time or don't do as you are told I will tie you down and spank you so hard I will raise welts. What you got earlier will feel like a love tap do you understand? Again a yes nod. "Take it off." She raises her head up and reaches back and unbuckles it.

After she pulls it out she swallows and looks at me. "Thank you. I was having trouble swallowing. I was choking on my drool."

"Ok so next time no gag with you on your back. You need to be able to let the drool, drool out of your mouth. Now I want you to embrace your submissive side. I see you fighting it. You don't want to give in with our arrangement. I want the submissive Chris from here on out. Don't forget I can still make this pleasurable for me only."

"Yes sir I understand. I am sorry. I will do better." She quickly responds.

"Good. Now as I fuck you I want you rubbing your clit until you cum. I want to feel your pussy orgasming as I fuck you."

I resume fucking her and her hand reaches down to rub her clit. It takes just a few minutes of fucking her with a nice steady pace and her breathing has quickened and I can feel her quiver as we fuck.

"Please. So close." She begs between gasps.

"Should I stop so you can rub it out?"

"NO. Don't stop. Please fuck me harder."

I double down and grab her by her legs and fuck away. It doesn't take a minute and deep groan and "Oh Fuucckkkk". Her pussy pulses around me. I pull out and lay on the bed beside her. Once she catches her breath she looks towards me. "You didn't cum did you?"

"Oh no. You are going to work for my second load."

"That wasn't enough work?"

"Oh no. You have more fucking to do before I cum. I want you on top. I want to watch you bouncing and grinding on me. Do you need more sensitizing gel?"

"No no, please no more. I still feel weird and am getting worked up quick. I haven't had sex like this in a long time."

"Climb on top of me now." She starts by feeling for me and then starts to straddle me. She grabs my hardon and lines it up with her pussy and sinks down with a moan. I get an idea and reach for my phone and hit record. "Do you like that dick in you?"

"Yes it's just the right size."

"It's amazing watching you bounce up and down on me. To watch the pleasure on you face, your boobs bouncing and to see your juices coating my dick."

"I am glad you like it Sir." She says smiling at me.

"Lean back a tad."

She leans back and I reach in and start rubbing her clit with my thumb. "Oh god. Jesus I can't believe that gel is getting me so amp'd up."

"I am going to keep rubbing until you cum. I want to feel your pussy squeeze my dick when you cum. I want to feel your juice leak out around me. I want to watch your face as you cum."

She is beginning to pant again. "Yes sir."

"Then I want you to lick and suck all your juices off me. If you are lucky and do a good job I might reward you with a mouthful of cum, or I might just fuck you doggy style until I come in you pussy."

"Yes Sir. Whatever you prefer."

I start pressing and rubbing her clit harder. She lets out a groan of pain. "Am I pressing too hard?"

"Yes Sir a little easier please."

I ease up the pressure but rub faster. She has now stopped bouncing on my and is rolling her hips on me. Every here and there she rolls her hips too much and my hand falls off. I reach back in and get back too it. Which always gets a loud gasp as I start over.

She again gets to the point of sounding like she is hyperventilating, and she jams her hips down onto me pushing my hand away. She tilts her head back and loudly moans "FFFUUCCCKKK". She then just collapses off me to the side. Her body shivering slightly every now and then.

I point the camera at my glistening dick and then back at her face. She is still panting a bit. Her mouth is open a bit trying to gulp in air. She keeps licking her lips as if her heavy breathing is drying them. "You realize you have a cleaning job to do."

"Yes I will. May I please have a minute or two to catch my breath?"

"Since you asked nicely." I lay there quietly watching the clock. She is down to her last 30 seconds when she reaches out to feel for me and starts moving. I aim the camera back down at her and my hard on. First she starts with my balls. She licks them and then gently sucks one and then the other into her mouth. She then moves to my thighs and licks those clean. Finally she puts her mouth on my dick and takes it in until it's right at her throat. She gags a tad and then pulls off me sucking as she goes. She repeats this 3 times and then lets me pop out of her mouth.

"So do you like the taste of yourself when you suck a guys dick after he has fucked you?"

"You really want to know?"

"If I didn't I wouldn't have asked. Now answer me." I tell her.