Tag: erotic roleplaying

Sissy maid training for hubby

Sissy maid training

I have decided to train my sissy hubby as a sissy maid. I got him a maid outfit complete with stocking, panties, a bra and a little maid hat. I told him he would be wearing this for training and I would decide if it were to be his standard uniform when in sissy mode, so to speak. I hand it to him and point to the bedroom for him to change.

When he comes out I laugh at what a candy ass pussy bitch he looks like. “Oh what an interesting sissy maid slut you make, let’s get you to work you faggot.” I said and he didn’t seem to know where to start. “What’s the problem?” I asked and as I thought, he didn’t know what to do. I said simply to work from highest to lowest.

A few hours later he came to my den where I was working and told me he was finished. “Get on your knees until I come back from inspecting it.” I said to him “there was good and bad news. Good news it isn’t horrible, bad news is you didn’t try that hard. I think until I get a better effort, you will be in a cock cage. As a reward for a good first time effort I am going to let you lick my pussy.” A grin came across his face until I said he was going to lick my pussy after I’ve put the cock cage on.

He loves licking my pussy but of course the cock cage made it uncomfortable. He flicked my clit with is tongue and slid 2 fingers inside me, I had been horny all day and relaxed into it and came all over his face. He looked like a glazed sissy donut.

Next time, he learns what else a sissy slut in training needs to know. And why he suddenly has a tail?

sexy babe needs new sugar daddy

sexy babe

Okay so I need to find a new sugar daddy. One that will fuck me all the time. My current daddy is always gone on business. I hate it. He leaves me all alone.  I end up going to bars and clubs just to get my young tight cunnie off. I want a sugar daddy who will take me with him on business trips. I will dress up all nice and be his arm candy. All his associates will love me. When we get back to the hotel I will make sure you have everything you need. I’ll suck on that big hard cock daddy. Then when your all nice and rock hard I will ride you. I’ll Bounce up and Down on that cock. Faster and faster I will go up and down. I promise you will love my tight soaking pussy as you glide in and out of me. When that nice big shaft starts throbbing I will get off top of you and shove it back into my mouth. I’ll lick all my yummy pussy juices off. I will stick that throbbing dick down my throat, sucking hard until you cum in the back of my throat. I’ll drink all of it up. Wouldn’t that be so hot to watch. I’ll give you everything you need baby. Will you be my sugar daddy?

Erotic roleplaying, you’re the boss

Erotic roleplaying

Good morning Sir as you walk into the office. You stare at me; I wore something very sexy but still business dress. After all I’m not just some cheap whore. Ok I am a little, but that’s only because I love sex that much. You went into your office and closed the door. About an hour later you are buzzing my phone for various things, then the last one you asked me to come into your office and bring a ruler and a pen.

I softly knock on your door, and hear “Enter.” I walk in and take a seat at front of your desk. “Well Ms. Whitney, are you ready for some dictation?” My eyebrows went up as you start to say dic…I was hoping you would ask if I am ready for some dick. You begin your list of letters and emails. “Ms. Whitney, stand up.” I stand and you come around the desk and grab my shirt and rip it open. Shocked, I can’t move. I have no bra on and my nipples are hard as rocks. You immediately take one into your mouth.
As soon as I begin to moan and tell you, you are making my pussy wet, you stop sucking on my nipple and push me face down onto the desk. You hike my skirt up and of course I am not wearing panties. Grabbing the ruler you begin to spank me with it. As my ass turns red and I start to flinch away from the strikes, you put two fingers in my pussy. And with each blow you slide your fingers into me then swat my ass. You say “Good girl, I can feel your pussy squeezing on my fingers when I spank you, keep it going.” You move directly behind me and thrust your huge cock inside me and lay a crack across my ass. You love how my pussy tightens when you spank me. You reach up and pull a nipple, swat my ass again and drive into me over and over. I tell you I’m going to cum. Your smacks on my ass get harder, and you are fucking me deep and fast, pounding into me.
With the last crack of the ruler, I start to cum; pounding my pussy it’s sloppy and wet from my orgasm. You grab hold of my ass and ram your hips into me, getting close to cumming, you tell me to turn around. I turn around kneel and take your whole load in my mouth and it drips all over my tits.
Thanks boss!

Erotic Roleplaying at the Doctor’s Office

erotic roleplayingI  had a very anal week last. Literally. From students to my doctor, guys obsessed over my ass last week. Do you enjoy erotic roleplaying? I sure do. I just was not expecting to be role playing with my cute doctor. I went in for a physical. As a teacher, I need one every two years. If it wasn’t for physicals and yearly gynecological exams, I would never go to the doctor. I am very healthy. Just look at my lungs! Anyway, my heart beat was racing in his presence. I mean this guy was George Clooney on ER hot. He leaned in really close to me and whispered in my ear, “Perhaps we need to check your rectum too. Make sure everything is okay there too.” The hot doctor wanted to make ass sex porn with his patient! I played along. I bent over the patient table, lifted up my gown and spread my ass cheeks. He pressed up against me in his lab coat. I could feel his throbbing cock. I heard the latex glove go on. Does a man get this aroused I thought to myself as he inserted a lubed finger up my ass. I let out a sigh, then I sank into his hand. His finger deep inside me probing as his hands cupped my ass cheeks. I found myself wishing I had a prostate. I started moaning. The more I moaned, the deeper he probed my asshole. I was creaming everywhere. I was so drenched; he had not even touched my clit yet. I tilted my face for an erotic French kiss. That is when he reached around and rubbed my clit. I came so hard. “Beg for it Farah,” he said softly. I begged for him to fuck my ass. His 8 inch hard cock felt a lot better than his finger and made me cum over and over again. As I was leaving, he slipped me his personal number and a smile that told me my ass would be seeing him again soon.

ass sex porn

Sexy Babe & Sensual Fucking

We’d had a lovely date night – dinner, dancing, and a walk under the stars. You walked me to the door, and pulled me in for a deliciously sinful kiss. Your hands wrapped under each of my cheeks right there on my stoop, pulling me in against your already hard cock. When we finally broke apart, I went to unlock my door. Your arms stayed around me, and you pressed up against my ass as I turned the key and twisted the knob. We barely made it into my place before your hands were pushing my tight little mini skirt down off of my hips, slipping my panties down along with it. Then, your hands were sliding down my shirt, pushing it down under my tits so you could knead at them. You bent me over the couch first, plunging a couple of fingers inside of my already dripping cunt and massaging my clit while your tongue licked at my neck and ears. I managed to spin us around and push you back down onto the couch so I could suck you, but you pulled me back down on top of you before I could spin out of your hold. I felt your cock under my ass, bare and ready to go, and realized you’d released it while you fingered me. When you slid my pussy down over it, you filled me up so perfectly, it was all I could do to hold on. My head fell back as you started thrusting in and out of me, your huge dick stretching my cunt so perfectly. We spent hours just making love on my couch, your massive shaft forcing my cunt to expand to fit every inch of it.Sexy babe

Fantasy Phone Sex Gone Bad!

He pulled my skirt up, bent me over my desk, and slit right into me. I was already wet from my last session; I hadn’t expected to have him barge into my office as soon as the door was open. Then, manhandling me, it was all so sudden and surprising that I was full of cock before I fully understood. He pounded into me so hard that the desk cut patterns into my thighs, bruising me. He grabbed my hair, pulling back hard, and that’s when reality hit. I reached back and clawed his face, dragging my nails down either side. He slammed my head down hard onto my desk, dazing me. He flipped me, then, further tilting my world, as he lifted my legs high in a wide “v”. He pounded even harder into me, brutalizing my already tender cunt. When he finally finished, he finished inside of me, hard and deep. I felt it flood my cunt, even as I lay there trying to catch my bearings. He walked away after cleaning up on my skirt, and I heard the door slam shut behind him. I heard my next client knock on the door, but I couldn’t have responded if I had wanted to.Fantasy phone sex

Biggest Whore On The Block

Best phone sexI would love to get my pussy fucking rammed every night by a big thick fucking cock. I absolutely love getting creampied in my fucking asshole and cunt. I am the biggest whore in my neighborhood and I have at least fucked every husband and most of the wives. I have gotten a lot dick in my time do I defiantly know how to please you baby. I can take cock and cum like no other. You can cum all over my face and these big titties of mine, they are big enough so I can suck all the cum off my nipples. Does that make you fucking hard thinking about baby? You should call me so I can make you cum all over yourself.

Lesbian phone sex turns Orgy

Lesbian phone sex“Darline! Your pussy is so pretty. You have to show everyone!’ Brittany was begging me. We were at a party and surrounded by our girlfriends while the men all watched sports. So, we were bored with all our cocks busy jacking off to other men. How could I say no to Brittany when she’s asking like that and we don’t have anything else to do. So of course I lifted my skirt up letting the other girls see my pretty pink pussy. Having those girls ooo and ah over it was making me rather wet. The next thing I knew the next girl was showing me her pussy. Putting it right by mine and then another. Soon we were all showing each other our pussies! It was amazing, we were all so pretty and different. I couldn’t help but lean over to one girl and kiss her as another reaches over and teased her fingers up my own wet pussy. The next thing I knew I was nibbling on a girls nipple, a tongue lapping at my pussy, sucking my clit. All of these girls all kissing, sucking, fucking each other while the men watched the game. I can’t remember how often I came, or how long it took the boys to notice. But we all fucked in this giant orgy until we all passed out for the night.

He was watching me all day long

naughty neighbor pornMy neighbor was watching me all day long yesterday, I could feel his eyes on me no matter where I was! It started when I was outside getting some sun, he was in his backyard too staring at me. And when I went inside he did too, he went from window to window in his house, changing rooms when I did, I could see his curtains twitching! I wasn’t even doing anything sexy, it was crazy! I figured if he was gonna spend the whole day staring at me, I might as well give him something good to look at so I went upstairs and put on something sexy. When I came back down, I opened all the curtains wide and started stripping, his curtains were shaking, at one point he almost pulled them down! By the time I started masturbating he gave up all pretenses of hiding and just flung his curtains open so that I could see he was masturbating too. We even came together! I’m hoping next time instead of just watching me, maybe he will come over for some real fun!

Naughty neighbor phone sex

Naughty neighbor phone sexI invited him in and lead him to the kitchen; I lay back on the table and said “What do you want to taste first?” He pointed to my pussy and started to lick. He was so eager but I was shocked when he did some amazing tongue moves. He got me so close to cumming so quick I had to stop him and tell him to fuck me with his big cock. He hesitated for a moment; he was enjoying licking my pussy. He dropped his pants and a really large cock came out. My expression must have been one of surprise because he looked alarmed until I said how great his cock was. He slid into my cunt like he was a master. Grabbing the table to fuck me harder, and deeper, he flipped me over and fucked me from behind. In and out pounding my pussy, I put a leg up on the table and he started to cum. He fucked me even harder and when he pulled out to cum I turned around as fast as I could and got his cock in my mouth in time for him to blow his wad down my throat. He was so young and sweet tasting I wanted more so I sucked as much out of his rod as I could. He asked if I came…aw what a sweet sweet thought, but he smiled shyly and said can I fuck you again. I will go long enough to make you cum, I promise. I let him fuck me 3 more times and gave him a promise he could return. He made me cum more than once and was very proud of himself.

He snapped a pic with his phone I said he could keep it. He was excited to have something to jerk off to. He calls me now and then to help, then visits after school to fuck some more. Naughty neighbor phone sex can lead to even better things.