Category: Roleplay phone sex

Erotic Roleplaying: Sometimes, I Like to be the Student

erotic roleplayingI love erotic roleplaying on the phone and in the bedroom. I am known best as a therapist, but I enjoy roleplaying calls too, just like I do in my real life. I have this hung guy I met in a bookstore recently. Do not laugh. I am a smart woman. I have a Ph.D. and I am a professor of psychology too. I am a far cry from a dumb phone sex woman, so bookstores are my meat markets. David is a grad student at UCLA, and we met by chance. We have been fucking ever since. Barnes and Nobles is a great place to troll for cubs if you are a cougar. I love smart boys, especially when they are hung. He wanted to do a role reversal last night. Normally, I am the naughty teacher because I am always banging my students. He wanted to be the professor with me as the naughty schoolgirl. Since I am a mature woman, I have not been a schoolgirl in several decades. I put on my daughter’s old Catholic school girl outfit and went to see my hot teacher. Think Britney Spears in Baby One More Time. My hair is not long, so no pigtails, but I had the knee-high socks on, and the white shirt tied at my waist. I flirted my way into a bare bottom spanking from the hot teacher. Now, I am not a sub. So, the spanking part is not common. Do not let that give you any ideas. My lover is young and hung, and since I wanted to fuck him and help him with his fantasy, I let him spank my hot round ass. He spanked it good too. Made my pussy wet. He fucked me bent over my home office desk that he used as his prop. We fucked all night long with me in my schoolgirl outfit. Honestly, it felt amazing to be the student for once.

Sissy Maid stories to live by

sissy maid stories The bubbles lapped my skin as the water swooshed back and forth. I had been reading some new sissy maid stories and was lost in the thought of my newest sissy. My body was alive at the thought of my sissy Sucking the UPS driver’s cock as a tip. We had been making good progress, and the outfits He bought to dress up in had become more sissified every weekend. He had taken my strap once and had taken three weeks to come back and see me. I was sure that would be the last session we had. But this morning I received a sissy novel on my doorstep and A bottle of wine and a Bath set. We had a “date” soon, and I was crafting a plan to keep him in my care for a long time.
I had fired my part time housekeeper and the house looked like a single busy business woman, lived alone. I stepped over discarded hose and panties, over towels and lotion bottles; giggling to myself. I had added to the mess with Hiding sissies butt plug under a pile of jackets and leaving a note beside it. Sissy was going to clean my house and sissy was going to either Present herself fully, or find another Mistress, My boots and black leather outfit With the crotch cut out would set the scene. It was Sissie’s favorite outfit. A leather loving sissy who would orgasm if he was allowed to click my boots too long.
The note read: Things you need, Your butt plug. (lube or no lube) The shopping bag in the closet behind My favorite Boots and Paddles.
If you wish to submit fully to me, and give me control to lead you into true sissydom, You know what to do. If you wish to end your contract you may gather your things and walk out the back door to hide your shame, No refunds on my Mistress tributes.

It took him 15 minutes. I waited dressed with my legs propped up on the couch. Sissy came crawling with her ass in the air, one pair of panties on and a pink leather paddle in his mouth. Sissy whined at my feet like a good puppy sissy.

We would begin his sissy maid training fresh. I had new ideas from his book.

Horny Hungarian Hunny

Sexy Legs

Men flock to me because they love my rolling accent and the devilish innocence of my mind. I took a modeling gig as one of those horny Hungarian hunnies and oh fuck it paid so well! Some bitches insist on being paid in cash, or coke. But, I prefer to be paid in something a little harder to come by: a nice, fat cock! I don’t care what photos they want whether it’s long, panned shots of my sexy legs or a close up of my pulsating pussy hole! I’ll give it to them, but in return I expect to be given a hot fucking stud to ride and grind on.

I’ll be bouncing on that cock in between takes, and from the moment we’re done until the sun comes back up. Oh, you want to film the way I ride him? Well baby I guess that’s okay too. Just bring the camera in real close. I want the perfect view on the way he stretches and creams out my cunt. I promise it’ll sell, these sexy audio and video clips of me being a whore. And you won’t hear any complaining from me. I love the attention as much as I love getting stuffed with cum.

Phone Chat Lines

Submissive MILF for your pleasure

Domination Phone Sex
       Hello, my name is Anna. But I can call you Master, I want to be tied up and fucked till I can’t stand it. Until my legs are shaking, and you have to literally carry me to the bed in order to fuck me some more. I will be your kinky, submissive MILF that you won’t be able to get enough of Master. I want you to have my every hole. Fuck my mouth, fuck my cunt, even fuck my tight, tiny little asshole until I scream in delight. Who knows, I might be so loud you’ll have to gag me with my own panties in order to quieten me down! I’ve been dreaming of this every night, Master. My husband is away, so now we can play. First, you’ll tie me to a chair. Then you’ll fuck my face while I was the biggest dildo on my cunt that I can. Finally, you’ll pick me up, tie me to the bed, and have your way with my tiny asshole. How does that sound, Master? Or do you have other tricks and treats for us to enjoy? I’m already so wet just thinking about all the time we’re going to spend together. Please don’t keep me waiting…

Gwens a phone sex mommy

phone sex mommy Oh my sweet snookems do you need a phone sex mommy? I know baby, you’re such a bad boy. You’ve been doing things like sneaking into my wardrobe and dresser. I notice a couple of nighties are gone,and more than a few pairs of panties have been worn and returned all crusty with cum. Naughty! But I think the worst thing you did was put my dildo back with your ass juices all over it! You wanted to be caught !I think you deserve a spanking, my lovely! A nice firm spanking!
Look at me, why are you so bad, you could have asked me to play dress up. Now come here and let me dress you proper! First a pair of silky sheer panty hose, and let’s not forget some special panties with a little extra material to hide that erection! I even have tucking panties for a sissy slut who is a little bigger than most of my slaves. Give Mistress Gwen a good show. Dance around and twerk real nice and slow! Oh, baby you make my milf cunt so wet as I insert a bejeweled butt plug in your sweet sissy hole! Oh now watch as I lay back and play with my pussy and direct you to properly use every toy I have in my arsenal!
You know you love sexy women masturbating while you show me what a good slave you will be for me!sexy women masturbating

Fresh Meat is the Best Meat

Coed phone sex

I have to admit I was pretty nervous about going back on campus for classes this fall. Between the pandemic and the fact that I’m not a traditional college freshman, I was having second thoughts. It was the first day and just as I suspected, I was the oldest person in the class besides the professor. Even with a mask on, I couldn’t hide my embarrassment when I was called on to introduce myself. I sucked my teeth when it was my turn to introduce myself. I fumbled through my quick introduction forgetting to mention a special fact about myself. I could feel you watching me the entire time. I looked in your direction, but you never looked away. Your intense stare had an unexpected effect on me and I felt my panties getting warm and moist. I shifted in my chair and I swear I saw your cock stiffen. I needed a bathroom break, quick! I quietly excused myself from the lecture hall and made my way to the ladies room. I needed to splash cold water on my face and take a deep breath. I took off my mask and turned on the faucet to let the cool water run on my hands. The water felt so good on my hot flesh. I suddenly felt someone pressing against my round ass. I knew it was you. Something told me you would be cumming after me. You lifted my skirt and moved my silk thong panties to the side, revealing my perfectly manicured ebony pussy. You held the back of my neck down and rubbed your spongy dickhead up and down my pink wet slit. My pussy got wetter and wetter as you fed me your cock inch by heavenly inch. You deepstroaked my dripping wet pussy until she overflowed with sweet pussy juices. Then you shot your hot cum load on my round, juicy ass. That one quickie changed my entire outlook on going back to school. I know I’m going to earn straight A’s this semester because this super senior is not ever missing this class. 

Mutual Masturbation With My Boss

Mutual masturbation stories

I masturbated in front of my boss and he loved it. He is always checking me out and being flirty. I knew I was the hottie he dreams about fucking; I have perky tits and a nice tight body. I made sure to tease him a few times by not wearing any panties so when I bent down, he could have a good view of my cunt and asshole. A few times I “accidently “rubbed my ass on him and I could feel his boner. This time I wanted more I figured it would get me a raise. I waited until we were the last2 in the office. I got close to him and put his hand on me, he jumped back and said that he couldn’t lay a finger on me but that doesn’t mean he can’t watch me lay fingers on myself. That is when I sat back on the chair and spread my legs so he could get a good look into my cunt. I took my fingers and played with my clit and then used my other hand to finger my cunt hole. He pulled his cock out and started stroking not blinking as he stared at me while I played with my cunt. It felt so good I stuck my other finger in my asshole as I finger fucked my cunt, we locked eyes while masturbating until we both started cumming hard. He told me since I ‘showed” him how dedicated I am that he was giving me a raise.  

Happy Ending Halloweekend!

Sex Therapy Porn

I’ve picked up some extra hours down at the spa giving very special massages for Halloweekend! Just last night, I was giving a very sexy man a deep tissue massage and I couldn’t help but notice how huge his boner was under the sheets! Well I made him roll over, and I ripped the sheet away so I could see that uncut horse cock! Holy fuck it was just as sexy as my husbands! I oiled up my hand, and starting jacking him off right away. he was going to get his halloweekend alright! He was getting harder and harder as my soft little hand stroked and squeezed all over his girth. That’s when I hopped up onto the table so I could straddle and ride that throbbing trick or treat.

Confidence is Key: Cock Worship Session 1

Phone sex therapy

My life was so boring until I started my new job. When I first saw the job posting for a part time sex therapists, I knew it was the job for me. Making copies, answering phones, and punching the clock had become mundane and I was craving something more exciting. The very first week I had a client who needed some assistance getting over his performance anxiety in the bedroom. Here he was, tall, dark, handsome, and sporting a thick 10 inch cock, struggling to handle his business in the bed. I was determined to help my newest client get over his confidence issues and learn to fuck like a pornstar. I made him strip completely naked and stand in front of the full length mirror in my office. I got on my knees still wearing my heels and blazer. I took my glasses off and removed my hair pins letting my thick curly hair fall to my shoulders. I lifted his heavy cock to my face and kissed it gently. I thanked my client for allowing me the opportunity to worship his amazingly beautiful dick. I kissed the head of it again adding a bit more tongue. I marveled at how his cock hardened and stiffened to my touch. With each kiss and compliment my client became less and less tense. I sucked and licked the head of his cock while thanking my client for gracing my tongue and lips with his beautiful, lengthy fuckstick. He watched in the mirror as I worshiped and devoured his cock. My goal was to touch him the way I want him to feel about himself when he’s about to fuck. Our sexy reflections and my superior cock sucking skills boosted his confidence and he filled my mouth and throat with his warm cum juices. I wasn’t even finished cleaning him off when he booked and paid for ten more sessions in advance. I have officially found my calling and I love offering my services to my loyal clients.

Swalloween In Cocktober

GFE Phone Sex

My favorite holiday is Swalloween! I love to masturbate my sexy little pussy while having some hot GFE phone sex, but it isn’t the same if I don’t have a throbbing cock pumping down my throat and all of my girlfriends agree. The reason we love sucking cock and slobbing those knobs around here is the fact that me and my girlfriends are all sluts. This year, we got all dressed up and posted some racy photos of us on our social media; asses out, nipples flashing, and pussy juice soaking into the tops of our thigh high stockings. This year’s costume was American Milk Maid Breeder, and I think I hit the cock on the head if you know what I mean. Well, one of the little boy toys that lives down the street got caught peeping in my window, trying to catch a peek of our tits and tight little asses. I decided to make him the star of our costume show, and really made myself out to be a cock milking maid. I was guzzling down his dick like I was starving, and the way he started to throat fuck me was surely both the trick and treat I was looking for.

Sexy Girlfriend Porn