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The Bet With My Landlord

John loses a bet with his landlord.
Ms Parker is kind of an outcast. Despite being kind and outgoing and just a normal member of society, people shun her. Men didn't seem to be attracted to her since she was a bit overweight. Or it could be the weird living partners she had, compared to the societal norms in this conservative little town. She lived in a fairly big house with her two roommates. Marcus was a smallish fellow. Very thin and very effeminate and a few years younger than Ms Parker. Peggy was younger also, but she was built like a brick shit house. Well put together. Raven black hair, perfect skin and complexion, big beautiful high breasts, and a tight ass. (Can you tell I've been checking Peggy out?)

The three of them are always in public together. They shop together, they go to the park together, they go to the salon together. Everything they do, is together. There is always just a little bit more touching than is necessary, even though it's never sexual or overt. Just enough to make you wonder. For months people have wondered if Ms. Parker and Peggy were lovers. No one knows where Marcus fits into the puzzle.

People ask me all the time if I know something more. They ask because I rent out the apartment over Ms. Parker's garage. I always tell them that I don't know anything. But even if I did, I wouldn't tell. And truth be told, I don't KNOW anything. I have my suspicions like everyone else. But nothing is certain in my mind. Plus, being just out of college and still looking for a good job this place is cheap enough to let me keep my head above water. No use fucking that up. Everything in my little world is just fine. I mind my own business and that keeps me out of trouble.

Until the day I started running my mouth. Ms. Parker has a Philadelphia Eagles bumper sticker on her car. So I razz her about her Eagles, telling her my Cowboys are going to whip them. She always tells me to put my money where my mouth is, but I just laugh it off and go on about my business.

One day as I come out of my apartment, she is watering her plants.

"Happy Monday morning John. Tonight is the Eagles/Cowgirls game, you ready to make that bet yet?"

"Yea, tonight is the game Ms. P. But you know I'm still looking for a real job. And my little college job doesn't pay me that much. I can't afford to lose. Even though I KNOW the Cowboys have this game in the bag."

"Tell you what, care to make it interesting?"

"Hmm, that sounds cryptic. What do you have in mind?" I'm thinking, maybe a months free rent vs. me doing some yard work, gutter cleaning, window washing sort of thing.

"Well my dear boy, as I told you when you first moved it. I don't like nosey people. And I've had a couple of my spies ask you the questions that everyone is asked when they live in my apartment. You never once divulged or guessed at anything. So I know you can keep secrets. I see the way you look at Peggy. How could I not notice. As you might guess, the three of us are lovers. To varying degrees. And we've been known to share with the right people."

"Wow Ms. P. I don't really know what to say. I, umm, I really don't think..."

"Ah settle down John, don't get your little man panties in a wad. Here's my bet, you can accept or decline. And it has no bearing on your living status here. Other than knowing that you'll be admitting the Cowgirls will lose. But if you win the bet, Peggy will be your sex slave for the evening. You can do to her whatever you wish. She's already agreed to this. If I win the bet, you'll have to be my sex slave for the night. Which somewhere along the line will involve Peggy anyway, so it's really a win win for you. And don't worry, you don't have fret over Marcus plowing you up your rear."

My head is spinning. Ms. P. isn't my type. But I mean, fucking her couldn't be all that bad, could it? It mean free pussy, right? Maybe I'll have to lick her hairy (I assume) pussy or lick out her ass or something but I can handle that. And I'll get to fuck Peggy either way. And the Cowboys have the Eagles number. This is going to be easy.

"Well Ms. P., if you put it like that.. you've got yourself a bet!"

I'm a nervous wreck as I watch the game. It is going back and forth. Neither team getting a big lead or gaining full control over momentum. As the final minutes of the game approach, the Cowboys have the upper hand, but not the lead. Tonight it's good Romo, I'm pacing all around the living room as he leads Dallas down the field and into field goal position. Trailing by two points, it's all but in the bag. It's a chip shot from here.

I look on in total disbelief and disgust as bad Romo comes out at the worst possible moment. The fucking moron has bobbled the snap. Ball down late, kick up... shanked wide left. Holy fuck, that son of a bitch did it again. I'm having a full on bitch session alone in my own apartment lambasting Romo, when my tirade is interrupted by my cell phone.

"Hello!"

"Hi John. It's Ms. P, time to pay up on our bet."

"Oh Ms. P. tonight, really? I didn't know you meant the evening as in THIS evening." I say, even though I knew had I won I'd be expecting Peggy at my door in a silk robe. "I'm not quite ready tonight. I'm just in my pj pants and I thought I could pay up this weekend."

"No-go John, tonight's the night. No need to get dressed, those pj pants won't last long anyway. But you can do one thing. Be sure to brush your teeth. I don't want to kiss or have my pussy tongue fucked by someone with Nacho Cheese Dorito breath."

After brushing my teeth, I slip on my flip flops and head out the door. It's damn cold outside on the short trip to her garage door. My shirtless nipples are hard. When I knock on the door I'm pleasantly surprised to see Peggy answer. Wearing a black silk teddy with lacy fringe above her tits. I follow her into the house to Ms. P. She is wearing yoga pants and a tight shirt. The old broad looks pretty good. Marcus is wearing gym shorts and a t-shirt and is sitting on the couch. As I enter the room she stands walks towards me, with Marcus following her lead. She stand in front of me, and I'm flanked by Peggy and Marcus. No matter what the fucking bet is, I'm not doing ANYTHING with Marcus.

"Here's the deal John. I'm a bit of a control freak. You'll follow my orders and do everything I tell you. No questions asked. I see you're a little anxious with Marcus being here. You needn't worry about your anal cherry, at least not from him. He's quite the voyeur. Understand?"

"Yes, that's fine Ms. P. As long as he doesnt' touch me, I'll be fine."

"Good! Now push those pajama pants down and let's take a look at what you're working with."

I'm a little shocked that we're going to just jump right into it like this. Drop trou and show your dick. Fuck me! I'm nervous and I'm still cold from being outside and barely dressed. I push down and step out of my pj pants and see smirks and hear small audible sounds of, dare I say, disapproval. But holy fuck, I'm cold.. hello... Seinfeld... Shrinkage. Here I am being judged on my out of character cold shrunken dick right here in the middle of Ms. Parker and her vicious circle.

"Marcus, go sit down. Let's not exacerbate the problem with you making him nervous. Peggy, get down there and see if you can fluff that thing up a bit."

In a flash Peggy is on her knees before me, grabbing my dick with her fingers and stroking it until she can get it into her mouth. Mmm, very nice. Now things are starting to go the way they should. With Peggy expertly handling me, my cock is rising to the occasion. It's only a minute or two before she's slobbering up and down my fully erect shaft.

"Peggy, damn it! That's enough. Don't you dare make him cum so fast. Back off of that thing so I can see it." Peggy obeys, rises and steps away from me. "Oh boy! Thank the heavens, he's a grower and not a shower. That little puny dick you first showed me was a disappointment. But it has certainly risen to the occasion. It's not huge, but that 6 1/2 inches is a hell of a lot better than the 4 inches I thought you'd have."

Ms. P. pulls her top over her head. Wow, those knockers! Big, mature tits with huge pink areolae. Nipples hard as ice. I can feel the blood surging into my cock. Then she puts her thumbs in the waistband of her yoga pants and pushes them down. Revealing her perfectly smooth pussy. With big flappy cuntlips hanging out.

"I see you like my bald pussy, John. I made Marcus shave it for me tonight." She sits on an over sized chair, legs spread wide and heels pulled up against ass. "Get on your knees and lick my pussy John. Lick it good and make me cum."

Jumping into action I'm kneeling before her, taking my time licking all around her swollen pussy. Teasing her meatflaps with my tongue. She's oohing and ahhhing, but gets impatient. She grabs me by the hair and centers my face right on her steamy snatch. Pulling me into her and forcing my face into her pussy.

"Ooh now your doing something boy. Yea, just like that. Mmmm, suck on my clit you little bitch. Get my cunt nice and wet for a good fucking. You'd better be glad Aunt Flow left me last week. Or you'd be fucking me through the red tide." I paused and looked up and her with a bit of disgust in my eyes. "Oh you stupid young kids. You'll have to get over that fear of period fucking when you get married. Women love it then. If you can walk through mud, you can fuck through blood."

I'll have to think about that one later. Right now my fucking scalp is about to to be ripped off while she had a death grip on my hair. Fucking and bucking into my face. I need to get this bitch off now! I reach up and put two fingers inside her twat. Curving them upwards I stroke her g-spot. My mouth concentrates on her clit. Sucking it while my tongue flicks back and forth over it. An all out assault on her.

"Oh god! Yes, just like that. Mmmmm... holy fuck. Yes, make me cum you fucking pervert. Ahhhhhhhh" With one last buck of her hips, she grinds my face into her pussy. Nearly smothering me. She cums. With a flood of cum. If my face weren't plastered to her pussy I think she'd would have squirted across the room.

"Good damn job John. You're a champion pussy licker. I can't wait to bet on the another game with you if you always eat like that. Lay down on your back, babe. There you go. Look at that shiny purple helmet. Peggy, you know what to do."

I lay there in amazement as Peggy stand between my legs and lowers the straps of her lingerie. Unveiling her superior tits to my eyes. They are a nice round handful. Dark brown nipples that are standing straight out. Pushing her teddy down I can see her flat stomach... the top of her waistline.... down until her pussy is revealed. She has a prominent mound topped by a landing strip of black hair. My cock is aching. Standing with her feet on each side of my hips she begins to lower herself down to me.

Finally!!! Her body is against mine. My quivering cock trapped between us, she lays on me and I can feel her nipples pressing into my chest. Ms. P. moves and is kneeling between my open legs. She gives a playful swat on Peggy's ass. Peggy raises her hips slightly, freeing my cock. Ms. P. reaches in and grabs hold of it and places it at the entrance to heavenly bliss. One more swat on Peggy's ass and she lowers herself onto my dick. Mmmm yes. The velvety warmth and smoothness is incredible. My cock is oozing with precum as she pumps her hips up and down, ever so S L O W L Y!!! Stopping on occasion to grind into me. Rolling her pussy around on my cock, which gives me time to reach up and take her tits in my hands. These nipples are perfect. I pull them, tug them, twist them. Each causing a moan and whimper of varying degrees.

My hips are moving in time with hers. Ms. P. is playing with my balls and occasionally touching my shaft when Peggy is on an upstroke. The feelings are pulling me to the edge. Sensing my heightened arousal, Ms. P. grabs hold of my nut sack between my two balls. When Peggy moves up again, Ms. P. grabs my shaft, pulling it upwards as she pulls down extremely hard on my scrotum.

"Owwww! Mutherfucker. What the hell?! That shit fucking hurt."

"Don't be a pussy John. It's way too soon for you to cum. We'll need to churn up more of that spooge before you get to let it out. And when you do, it will be even better. Trust me. You're getting too excited. We need to curb your senses. Marcus, get me the hood and the ball gag."

Oh shit, what the hell have I gotten myself into? Hood and ball gag? I watch as Marcus returns to the room with the two items. His gym shorts tenting out from his hard-on. Fuck, I hate to think that this guy might be jerking off later thinking of me. He gives them to Ms. P. I'm relieved to see her rise and begin fastening the ball gag to Peggy's mouth.

"As you can see, for now, Peggy is getting the gag. She's a naughty cumslut anyway and when she cums she says some really filthy shit. Hearing that might put you over the edge. So I'm just going to just shut the bitch up. The hood is for you." As she begins placing it over my head. "With your eyes covered you won't be able to stare at her spectacular tits, and the zippered mouth will prevent you from sucking on her nipples. There we go.... See No Evil, Hear No Evil... now, put your palms on the floor under your ass. They are to stay there and you'll not be able to touch. With your senses denied maybe you'll last longer. If you move your hands I'll squeeze your nuts and it won't be pleasant. Understand? You may not touch her again until I say so."

"Fine." I huff in agreement. Even though inside I'm loving every bit of it.

"Peggy, fuck him senseless." Ms. P. says from between my legs. Her hands still in my crotch.

Peggy wastes no time and is fucking me. Bouncing on my cock. I can hear her whimper and moan, but not much. I can hear that she's trying to speak but with the hood also covering my ears and her ball gag, I have no idea what. Sensing the tightening of my muscles, Ms. P. does the cock/nutsack maneuver again. The pain is exquisite but it does the trick. For her. It stops my orgasm again. And again. My frustration level is at an all time high. I need to cum.

Peg is nearing her own orgasm. Finally. Her body is tensing. Her pumping hips get rapid and short. Maybe I'll get to cum with her. Just as I feel your slam down hard onto me and her pussy is clamping down on me, bucking on top of me in a scream inducing orgasm.... my balls are churning up my own load. But once again I have my own release halted.

"God damn, fuck, shit, bitch! Let me fucking cum. I'm following all your orders. Let me cum Ms. P."

"UP!" Ms. P. orders and Peggy dismounts my cock. "John, your time is getting close. I love the taste of Peggy's pussy. Let's see how it tastes on your cock. You'll cum soon, but not yet." I feel her mouth engulf my dick. It feels heavenly. My cock and balls are covered in female flavor. Her fingers still toying with my balls, then move lower. And I feel her pressing a finger against my ass. I've never had that before, but I hear it's good and I've been wanting to try it so I relax. She grunts in amusement and pushing into me. And as quickly as she began, she stops. Releases my cock and frees her finger from my ass.

"You, get my ass shoes"

What the fuck are ass shoes? I wonder as I hear Marcus, forgot about him in the room, padding off to get her 'ass shoes'.

"You, get in position over the side of the sofa. Time for that ass to be filled with cum so I can lick it out of there. John take my hand and I'll lead you there."

I reach out my hand and she takes it to help me up. Then she grabs my cock and pulls me in the direction of Peggy. In my mind I'm trying to picture her bent over the sofa with that glorious ass on display.

"John, you will get to cum now. But I don't want you to pop off as soon as you're in that ass. Keep your fingers interlocked on the back of your head. I'll guide you in and I'll be behind you controlling you some. While I finger my pussy at the same time. I gotta get mine too. Just before she cums I'll tell you and you'll reach down and stroke her clit. She cums extra hard from anal with clit play at the end. She'll probably squirt."

I nod and answer in agreement. I just want to cum. And get this damn hood off my head.

With my cock in her hand, she leads me to Peggy. Rubbing the head up and down her ass until my cock is pressed against her chocolate starfish. The head pushes in past her sphincter and I hear a muffled groan escape from her. Ms. P. puts her hands on my hips and slowly moves me in and out. Long, slow, methodical strokes. All I feel now is the tightness of her ass.

"Hold your ass and body steady, push back against him so he can keep fucking you like that. I want to rub my cunt." she orders. Peggy obeys and I continue thrusting at the same pace. It feels good, but with the slow pace and my lack of touching or holding her hips or hair, my cock isn't screaming for release.

Ms. P. sits back behind me in a chair. She puts her feet on the table, I can feel her ass shoes against my hips. I didn't even notice Marcus' return. She has me between her legs and I can hear her fingers sloshing in and out of her wet pussy. Her palm slapping against her mound.

"I bet you're wondering what ass shoes are? My ass shoes are 4 inch black heels. The heel is smooth and rounded, and a little larger than the average heel. Which makes them good for.."

As she speaks, she moves one foot and I can feel the heel pushing between my ass cheeks. Until I feel the smooth heel against my own anus. "Don't stop with your hip action, keep moving exactly the same way." She tells me.

From behind she is moving her leg and foot with my slow thrusting hips. Just enough pressure to feel her heel on my backdoor. "By the way, my heel has already been lubed. Just so you won't have to worry." Each time I pull back from Peggy's ass, Ms. P. puts a little more pressure onto my rosebud until the tip of her heel slips inside my ass. I throw my head back in pleasure, wanting so hard to grab the ass in front of me and bang it until I cum. But this game has all my senses more on edge than ever before and I'm loving every second of it.

"Mmmm, I see you like that." Each time I pull back from Peg, more of the heel goes into my ass. Until I feel the bottom of her shoe against my ass cheek and her heel is in me as far as it can go. I can feel Peggy's is getting more and more aroused. She is holding steady but I can feel her wriggle her bottom, she needs more. Harder, deeper, and faster.

Ms. P. knows it too. She begins to hasten my thrusting with the action of her heel in my ass. We have built up to a good speed and rhythm. Peggy is backing her ass up to me and bouncing her ass off of me. My balls begin to tingle. My thrusts are less sure and accurate. I'm torn between thrusting forward into one lady's ass and pushing backwards into the other lady's shoe. My breathing is getting shorter. Peggy is emitting low guttural moans through the ball gag.

"That's it my boy. You're getting close aren't you. Are you ready to cum?"

"Yes Ms. P. I've never wanted to cum so badly in my life. Let me cum this time, please!"

With a husky voice and through the slapping palm against her pussy she answers me, "Yes, you may finally cum. When she feels the cum splashing inside her ass it will push her over the edge. Right after you begin to cum, reach down to thumb her clit and pull her back into you and fill her tight little ass."

I am thoroughly enjoying our little cat and mouse game. Not being able to touch,hear (much), or see Peggy, denying those senses has intensified the sensations in my groin. But hearing Ms. P. say I can finally cum is like someone has opened the floodgate. The tingle in my balls is radiating up my shaft. My thrusting into Peggy's ass is fast and shallow, concentrating on the head. Urged on by the heel shoved up my ass.

"Oh yes. Let it go John. Fill that tight ass with that huge load of man milk."

I can feel the cum surging up my dick. My hips bucking wildly as it is about to erupt from within.

"Finger her clit! Finger her clit!" Ms. P. orders.

Just as the first powerful rope of cum shoots from my cock, I scream with delight and lower my hands at the same time. Happy to finally touch Peggy again. Reaching around and down to her soaking wet cunt.

"WHAT THE FUCK?!" I yell as my hand is filled by a stiff dick! Ripping the hood from my face I see that it is MARCUS before me. In a matter of seconds my world has collapsed. My cock is still jerking and spewing cum into his ass. Yet I'm unable to pull out because the traitor behind me has her heel stuck up my ass with full force. Holding me in place. Trapped with my dick inside of this guy, my body betraying me as it continues to pump shot after shot of my cum inside Marcus.

With all of my cumming and jerking about behind him, Marcus has reached his boiling point and with my still semi-hard cock in his ass he begins to cum. Right over the arm of the couch to Peggy's waiting mouth. Which she then holds in her mouth as she walks around to Ms. P. and shares it with her. My ever softening cock pops out of his ass. I never thought I'd have my cock pop out of any man's ass.

Finally she bitch behind me removes her heel from my invaded ass and releases me from her clutches. I turn to her with rage in my eyes.

"Now John, a bet is a bet. You agreed to be my sex slave for the night. I promised you'd get Peggy. I promised you that Marcus would not fuck you up the ass. I did not promise you wouldn't fuck him. I was true to my word. I don't think you're the violent type, but just to be sure this whole night has been video recorded. I have no plans to blackmail you with the video, but I doubt you'd want any of this to be seen in court someday. You're more than welcome to stay with us if you like. We always have room for one more. How do you think I got Peggy and Marcus to be my sluts?"

With a glare, I head out the back door back to my apartment. Throw on some clothes and start packing. Then it hits me, I still have 6 months left of my lease so I'm stuck. I think I'm going to call in sick to work tomorrow. It's time I plot my revenge.

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