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The Best Roommates A Guy Could Ask For pt. 6 [M28F27F27] [BDSM] [Roommates] [Master/pet/Sir]
Author Summary
HotWetErotica is in Master/pet/Sir
Post Body

I get out of work and call Cassidy. "Hey! I know you said you had something planned but I was wondering if you and Caitlin wanted to go out with me tonight, like on a date?" Cassidy giggles and I hear, "Caitlin get over here!"

Caitlin says, "Hey Damien I can't wait for you to get home!"

"Can you repeat what you just asked, Damien?" Cassidy asks.

I smile to myself and say, "I asked if you two beautiful ladies would like to go out with me tonight?" I hear Caitlin squeal and Cassidy laugh. I ask, "So is that a yes?"

"Of course! We can't wait and we will be ready when you get home Damien!" Caitlin exclaims and I hear her run off.

"She is so cute." Cassidy laughs.

"So we can do what you had planned after the date then?" I ask.

She laughs and says, "we will see, it will take a lot of energy out of Caitlin so we will see how she is doing during foreplay."

"Sounds good! I will see you beautiful ladies soon!" I say and hang up.


"Cassidy can you fucking believe he asked us out on a date!!" Caitlin exclaims as she races around our room trying to put together outfits for us. I still don't know how to feel about Damien err, Sir asking us out. We have never been asked out by any of our Sirs we found through the lifestyle and just going out meeting people. Damien though, he is a different breed.

I snap out of it and say, "I know I'm surprised too Caitlin, but we have only known him for a few days so, let's just see."

Caitlin holds up a white lace dress for me with a plunging neckline. It has sparkles and hints of silver in the lace. I hold it up to my body and it goes to her mid thigh, too low. "I want both our skirts to be just below our asses tonight, Damien should be able to put whatever he wants in us at anytime."

Caitlin's eyes bulge and she shrieks in excitement. She comes back out with an all black lace dress. This one will barely cover my ass and will leave the bottoms of my ass cheeks exposed and of course my pussy. The dress has two thin leather straps that hold it up and two straps hanging down so I can strap it into boots and keep it from riding up all night.

"That's the one!" I say and watch her disappear into the closet as I sit on the bed with my legs crossed and my hands in my lap waiting.

She then comes out with what is supposed to be her dress. It is just a mini skirt that is a little longer than mine and a piece of velvety looking fabric that is connected to either side. "Is that even a dress?" I ask.

Caitlin smiles and starts to put it on. She is of course already naked. When it's just Caitlin and I at home, she is always naked. She's just too beautiful to not be. The "dress" is a velvet fabric skirt that pulls tightly over her big bubbly ass. It covers the whole thing but barely. She bends over and flashes me her wet pussy, her big tits hang down and she looks back at me biting her lip. I smile at her and say, "That's perfect, pet. You are lucky Damien is coming home or I would be fucking your brains out right now."

Caitlin smiles and finishes putting on the dress. She takes the fabric and hangs it around her neck and then puts the fabric that is hanging in front over her tits, her tit's are so big though that there is a lot of soft creamy white skin showing. We are talking about the side boob of the century.

"How do you expect those things to stay in there Caitlin?" I ask, shaking my head.

She opens up her drawer and pulls out a roll of tape. She turns to me and exclaims, "boob tape!"

"What if he wants to play with them and they fall out in the club?" I ask.

"I don't think he is going to be focused on me tonight." She says with a devilish smile.

"Why is that, he usually is enamored with your big tits, you will be the sexiest woman at any place we go tonight Caitlin, you always are." I say feeling my cheeks get hot. I look away and bite my lip and then look back at my gorgeous lover.

She stands up and crosses the room and sits in my lap and puts her head on my shoulder and says, "and I'm always yours my love."

I kiss her passionately and grab her thick ass through her skirt, and say "Ooooh Damien is going to love this on his dick tonight."

We both laugh and kiss some more. Caitlin stands up and walks over to our dresser with our toys and gets something out. I'm putting my dress on when she comes over and holds up a box with two metal balls.

She looks at me and smiles, "I'm using my win from this morning."

When we do a slut contest the winner gets to pick something ultra slutty and gets to make the loser do it. "Master I present you with the balls I used that one time and blacked out from how hard I cam. This way you will be so horny you won't be able to say no to Sir's cock." She says smiling.

I blush because she's not wrong and ignore her while I finish putting on my boots. Caitlin gets down on her knees and rolls up my dress. She starts licking my clit and my lips making sure I'm nice and wet. She spreads my pussy lips and darts her tongue in my folds. "Oh pet that feels so good!" I moan and run my nails through her hair.

She slides two fingers in my pussy, I close my eyes and Damien thick cock pops into my head. At that moment I feel Caitlin slide both balls into my pussy and I let out a low moan and run my hand through her hair, she takes two fingers and pushes the balls up deep inside of me. I moan as she gets them lodged up in me, she kisses my clit one more time and rolls my dress down. She straps me into my boots, I suck in my breath and realize it's going to be a wild night!


I get home to find Cassidy and Caitlin waiting for me all dressed up. Cassidy is in this tight black dress with black leather boots. It has lace all over the outside and shows off her perky breasts. Caitlin sits in her usual position with her hands in her lap and an insane amount of cleavage, her whole tit is practically out. She has cleavage, side boob and under boob showing it's so hot! Her velvet skirt is pressed tightly to her upper thigh.

I smile and say, "Hey ladies! You two look incredible. I guess I need to change!"

"Where are we going Sir?" Cassidy asks.

"I found this club in the area, I already made a reservation for us so we had a table!" I tell them hoping they will love the idea.

"Was it at The Mystic?" She asks.

"Ya! How did you know." I ask.

She laughs, "Oh Sir, pet and I have been at this for a long time, we know all the places to go. I honestly thought I was going to have to tell you we needed to go to a different place. I'm very impressed."

I beam at them and say, "Thanks, I did a lot of research to find it! I will be back."

I come out of my room in a black shirt, my favorite pair of dark blue jeans with a thick black leather belt. I put on my nice watch and head into the bathroom to trim up my beard. I come out of the room and see both girls sitting on the couch.

"Okay, I'm ready!" I say and they both resume the position they were in before.

"Sir you look very sexy, I think I speak for both pet and myself when I say that." Cassidy says, "in fact pet please go show Sir how much we missed him today."

Caitlin crawled over to me and unbuckled my belt and unbuttons my jeans. She moans as she slides them down and my semi-hard cock pops up in her face. She looks so hot with her big tits out and her nipples covered. She licks my cock and kisses the head.

"Oh Sir, we missed you so much. I can't wait to suck and fuck your cock all night." She moans.

She puts me back in my pants and buckles me back up. Cassidy walks up and grips my cock through my jeans and says, "I missed you and your cock Sir, pet and I are yours tonight whenever and however you please."

She kisses me and says, "pet stand up."

Caitlin gets up and Cassidy leads her to the couch. They both bend over so I can see both their pink wet pussies. Both of them are already so wet...

"We are ready Sir!" They say together and kiss before standing up and turning to me smiling.

We are all in the Uber going to the club and that's where I found out that Caitlin used her win from the slut contest. Cassidy blushes when Caitlin tells me what she made Cassidy do and how I can't put my cock in her pussy until the balls come out.

I turn to Cassidy and reach down to her pussy. She is dripping wet, there is cum all over her thighs. She looks up at me and bites her lip holding back a moan. I lean in and kiss her as I slide my fingertips into her folds to feel the metal spheres deep inside of her.

She reaches down and grabs my wrist where my watch is and feels the thick metal band and moans, "Sir I'm going to cum in this Uber if you aren't careful."

"We will wait for the club, then you can have a release." I say. Her eyes bulge and she lets out a soft groan. I withdraw my fingers and turn to Caitlin who is staring at us biting her lip.

"You look beautiful tonight Cat, these tits are going to be hard to ignore." I say as I slide the hand I touched Cassidy with around the exposed part of her breasts. She moans as she sees a strand of Cassidy's grool shining on the side of her soft creamy boob.

"That was the point Sir, I love when you play with them, they are very sensitive if you haven't noticed and your hard hands feel so hot on my soft skin. Especially with that sexy watch you have on." She looks at the watch on my wrist, bites her lip and takes my hand off her boob. She guides it to her pussy and my fingers graze her creamy lips. She is so hot when she is breaking the rules, but this time I let it happen. I pull away from her hand and stick two fingers up her skirt to feel her soft thighs. I move my hand between them and find a wet gooey mess. I slide further up and the tips of my two fingers slide into her wet lips. She stifled a moan and bit her lower lip. I use my fingers to get up a glob of her cum, withdraw my hand and slide my two fingers into my mouth.

I hear both ladies moan and look up at the Uber driver who looks at me and then looks down at the road. 5 minutes later a very flustered older man says, "We are here, The Mystic, have a great night!"

"Tell the nice man thank you ladies." I say in a commanding tone.

They laugh and in chorus say, "Thank you Sir, it was a great ride!" We all laugh and exit the car, I get a beautiful view of Caitlin's wet pussy as we get out of the car.

We get inside the club and they lead me straight to the dance floor and start dancing on each other right in front of me. The music is popular electronic music and they look so sexy in the lights dancing. Caitlin's massive tits swaying around in the dark with her juicy ass hanging out of her skirt. Cassidy looks like a Victoria Secret model with her lace dress that goes down just enough to cover her big ass and her long sexy knee high boots. Her ass is held in place perfectly by the straps and when they both turn around and shake their asses their wet tight pussies are on display. They kiss and I walk up and rub their pussies.

They stand up and Caitlin starts grinding on my dick with her thick ass. "Oh Sir, this is so much fun! I can't wait to show my appreciation tonight." I move my hand up and grip her tit and kiss her.

Cassidy was grinding on Caitlin but turns around and they switched places. Caitlin dances away and then comes back and starts grinding on Cassidy. "This is great Sir, you look so hot tonight." Cassidy says as she takes my hand into hers.

I laugh and say, "You two are the ones that look good. I'm so hard right now we should have fucked before we came here."

Cassidy laughs and kisses me, she pulls back and says, "Sir, we can fuck here, not like we can at home of course, but we can if we are discreet about it."

I look around and see she is right! A lot of people are on this dance floor and the music is so loud you can't hear most of what is going on around you. I slide my hand down her thigh and dip two fingers into her wet folds and she moans into my ear.

"I'm so horny Sir, I think I will be ready to take your cock tonight." She moans. I massage her clit and kiss her neck.

"Good because I want to feel your pussy Cassidy, I know I pay a lot of attention to Caitlin and her massive tits, but I think you are so sexy." I say as I slide my fingers into her pussy from behind.

Caitlin turns around and smiles and says, "what about my big tits?!?!"

We both laugh and I withdraw my fingers as another couple look over and laugh. Caitlin blushes and squishes her tits up to us. "Cat, rub her clit while I finger her, let's make her cum!"

Caitlin's eyes bulge and she adjusts her position so she has her palm on Cassidy's skirt and her fingers can access her clit. "Oh Master, you are so wet." She says.

After about 3 minutes of us fucking her pussy with our hands she moans in my ear, "I'm cumming, oh fuck, they are coming out!"

Caitlin holds her hand under Cassidy's pussy to make sure they don't fall and slides them back up with her fingers and then licks them clean. I loosen my grip on Cassidy and she turns around and kisses me and then turns around and kisses Caitlin. Caitlin switches with her and starts dancing on me and Cassidy starts dancing on Caitlin.

"That was so hot!" Caitlin says. She grinds her big ass on my cock and it's so squishy and soft I can't stop running my hands from her butt to moving them up over her waist and then caressing her tits and then back down. Cassidy turns around leans up over Caitlin and whispers, "Sir I want you to fuck pet on the dance floor. She will be a good girl and stay quiet while you have your way with her. I will dance in front of you two while you do it and keep looking out and blocking you." Caitlin moans and looks up at me and bites her lip.

"Let's get some drinks first and a bite to eat, you two haven't eaten since we got here." I say, because I know they are hungry and are just to horny to admit it.

We go back to the table to order some food and drinks. I try to have some normal conversation, I do really like these girls and want our relationship to be more than this amazing sex we have been having. They tell me about their college life and how they were in a sorority together. After school they moved in together and told their families they were together. Caitlin is close with her dad but her mom passed away before she went to college. "It was hard but I found Cassidy my sophomore year of college and she really helped me!"

Cassidy is close to both of her parents but has had a hard time with her parents. They accept her now but for a few years they were estranged because she was dating Caitlin. "They had visions of grandchildren and a white picket fence and that just was never what I wanted."

I told them how I was close with my parents but that they lived across the country. I had to move out here for work a couple years ago and so I only see them once or twice a year.

After we ate we all looked at each other and smiled. "Before we go back out there I just want to say I really like both of you and hope that we can be more than roommates and friends. I would really like to officially date both of you." They both smile.

Cassidy says, "We would like that very much Sir! We can make our throuple exclusive. One rule that pet and I share is that we can only invite another person to join if we all agree."

I laugh and say, "Cassidy I have the two of you! What else could I possibly need!"

We head out to the dance floor and find a dark corner of the club. Caitlin is facing away from me grinding on my cock. Cassidy is dancing in front of Caitlin grinding her ass against Caitlin. I unzip my pants and pull out my cock. It flops out and is sandwiched between Carlin's thick ass. I slide her skirt up a little more and rub my cock against her bare ass and wet pussy. She moans and looks back at me. "I need your cock Sir, my pussy is on fire from you making us wait." She moans.

I laugh and kiss her as I slide inside of her soft wet folds. We both let out a moan as my cock inches its way deep inside her pussy. She opens her eyes and says, "You are so hard, Sir, I love how you feel when you stretch my wet pussy in new ways."

She was right this position was one I hadn't fucked her in before and she felt tighter. I had her standing up in a grinding position with her juicy ass out and in my hands, but her arms locked around my neck.

I gulp and start pumping my cock into this beautiful girl, her big tits are flopping around as I pump hard and slow into her pussy. "Oh Sir, this feels so good, and doing it here in the club is so hot."

I start pumping to the beat of the song that is playing which is a little faster than the speed I was going before and she cries out. I cover her mouth and turn toward the wall as a couple close by looks over. Cassidy dances in front of us and makes another loud moan. She gives the guy of the couple fuck me eyes and turns around and shakes her ass. The woman grabs the guy's hand and pulls him away as he's still staring at Cassidy. I laugh at almost getting caught and whisper in Caitlin's ear, "Cat baby we almost got caught, so I need you to cum as soon as possible. I'm going to fuck you really hard now so you can cum, just tell me when you are about to so we can make out through your orgasm so you don't scream out again."

She moans at my commands and pushes herself down on me more so I'm all the way in, she looks up at me and moans, "I'm ready Sir, I can cum for you."

I pick Caitlin up a little and push her to the wall. I start pumping my cock in and out of her, making sure to fill her up with each thrust. "Cum for me Cat, I know you have been thinking about my hard cock all day. Tonight I'm going to fuck you and Cassidy, I know you want to see me pump her full of this cock."

"Oh Sir, yes I want her to feel like this, oh Sir, please don't stop, I'm so close." She cries out.

Cassidy turns around and laughs, "Will you two hurry up the songs about to change.

"Cum Cat, I won't let you go." I whisper in her ear and then start kissing her as she cums hard around my cock. It's so hard not to explode inside of her but if I do we will have a mess on our hands so I hold back and let her pussy dance around my cock as she quivers and moans into my mouth. I spank her and savor her warm pussy and then pull out. I pull her skirt down and turn her around.

The last waves of her orgasm radiate through her body and I grip my cock with the hand I have the watch on. She gets on her knees and looks up at me as she licks my cock clean.

"You look really hot with that gold watch on and your cock in your hand." Caitlin says. I caress her head as she licks down my cock to my head and then puts me in her throat to make sure I'm clean.

"Finish cleaning him and put him away so we can go home and fuck." Cassidy says as she turns around to see my cock down Caitlin's throat.

"Yes Master, he just tastes so good with my cum on him." She smiles up at me and licks my cock one more time before tucking him back in my jeans. My cock bulges out the thigh of my jeans giving anyone a view of how hard I am. Cassidy reaches down and rubs me through my jeans.

"I can't wait to spend all night pleasuring your cock Sir!" She winks and gives me another squeeze. Cassidy takes Caitlin's hand and Caitlin takes mine and we leave the dance floor. I know we got a lot of looks and stares but I'm not sure if it's because I just made Caitlin cum on my cock or because of how sexy my two ladies are dressed. It was probably a mix of both.

As we walk out of the club and wait for our uber I grip both of their asses and say, "That was so hot, I was expecting a normal date!" They laugh and we get in the Uber and go home.

We walk through the door and Caitlin immediately pulls the fabric off of her tits and slides the skirt down. She steps out of the skirt and seductively walks to the living room swaying her big ass from side to side. Cassidy and I watch as she shakes her ass and then turns around and makes her big tits bounce. She stretches with her arms in the air and puts her hands together high over head and rises up on her tiptoes. She sways back and forth making her tits jiggle and sway. "Mmm, it feels so good to be naked again, I had a great time tonight Sir! Thank you for the nice evening and letting me have your cock." Caitlin says. She sits down back in her position with her head down and waits.

Cassidy kisses me and says, "Wait here I will call you when I'm ready Sir. I just have one question. Do you want to take the balls out or shall I have pet do it?"

"Have Cat do it but I want to watch." I say. Cassidy bites her lip and spins around.

"Come on pet, let's go get ready for Sir." She calls Caitlin.

I sit on the couch and wait for them to call me in, these girls are so sexy I just can't believe I am about fuck Cassidy. I honestly didn't know if that would ever happen once I understood the relationship, but I'm happy it is. My cock aches from being teased and I change into athletic shorts and take off my shirt so I'm just in my boxers and shorts. I leave my watch on since they mentioned it earlier. I walk out of my room and they are standing by the couch.

They both have teddies on. Cassidy's is blood red with black lace and Caitlin's is dark blue with black lace. Both teddies have breast cups so their tits are on display and they have buttons at the crotch. They turn around and both their asses are out. I walk up and spank them. They moan and Cassidy says, "What do you think Sir?"

"These are perfect but I will need Alice and I will need the materials we had last time". I say.

They both kiss me and head into their room. I hear some rummaging around and then that beautiful chorus, "We are ready Sir!"

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