Category: Roleplay phone sex

Pegging for rule breaking

Ass fetish

Most of my clients are pretty good about catering to my rules of fucking me each time I see them, but there is always that one. This guy in particular always has some excuse why he isn’t following my you must fuck me rule.
I brought him in for a special meeting using his parole as the motivation. When he got here I immediately locked the door behind him and instructed him to get naked. He resisted quite a lot, but eventually caved and was standing in front of me naked and looking incredible. I walked around him and inspected. I asked what the issue is with fucking me and he finally tells me he thinks his cock is too small. It wasn’t too big looking when he was soft but he was a perfect 7 when hard. I told him not to worry he wasn’t going to have to use his cock today. I walked him to the bathroom, told him to put his hands on the sink and spread his legs. While he did that, I slipped my strap on cock up my legs and put the clit stimulator in a perfect spot. I ran my hand down his back with my nails scratching. I quickly lube my cock and start pushing it toward his asshole. He started to stiffen up and I told him this was going to happen either way so he might as well try to enjoy it.
My strap on spread his asshole open and he took my big cock like a champ, I was fairly impressed. I gave him a reach around and started jerking off his cock. I felt the pulsing of him when he started to cum, he grunted and groaned and sounded relieved. “Next time you fuck me.”

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Sissy Maid Training with Gwen

sissy maid trainingI have so much fun with sissy maid training. I always keep your little cocks in a cock ring because after all once I make the transformation of turning you into little sissy girls you no longer have a cock. You have a pussy instead. Sometimes I like to dress you up in a maids outfit and shove a feather duster up your tight little puckered assholes. I tell you that you had better do a good job dusting and laugh as you are wiggling your ass trying to dust the coffee table. You knocked a lamp off of the end table and that just won’t do. So I have you bend over and place your hands on the coffee table. I have found that my riding crop always helps you to remember to be more careful. After a dozen of well-placed smacks on that ass. I start fucking your ass with the feather duster. You are begging me to release your cock ring and allow you to cum. But I don’t. Instead, I tell you to go do the dishes and leave that feather duster up your ass. Maybe if you do a really good job cleaning I will allow you to come…..only time will tell.

Best Phone Sex in the Sky

best phone sexThe best phone sex is with sexy mature women. We love to get naughty. I am a classy woman in appearance, but a dirty slut in reality. I flew to visit my daughter recently. She lives in Yosemite Park for the summer. She is in her last year of college and doing an internship there. I thought, this may be my only chance to see one of the Seven Wonders of the word. I found the 8th wonder on the plane. Bob, the co pilot of the Delta flight I was on, caught my eye. Or, I should say, I caught his eye. He gave me a tour of the pit. He even let me play with the knobs. I just wanted his knob. I wanted to join the mile high club. I took a risk and unzipped his pants. I mean we were in the cock pit. I wanted some cock. We were flying somewhere over Colorado and I was blowing the co pilot in front of the pilot. I don’t think great blowjobs are cause for emergency landings. I was deep throating his shaft when the pilot pulled out his cock too. Equally as big and thick. I was the queen of the mile high club. I missed my calling. I should have been a sexy stewardess, then I could have flown and blown daily. After the pilots tag teamed me, I went back to my upright position with cum leaking out of me. I had almost as fun on the plane as I did seeing Yosemite National Park.

mature phone sex

Mature or Experienced?

Mature phone sex

Every now and then I need that guy, that mature guy who I don’t have to show anything to, that I don’t have to train or instruct. I got to have such an encounter recently. He knew just the right places to touch and tease, so fucking hot.
As soon as he saw me he was kissing my neck and sliding my shirt and bra off but dragging his hands over all of me as he took each item off. My nipples were rock hard and my pussy was already pulsing and throbbing like mad. When it came time to fuck, he wasn’t like a jack rabbit like the younger guys tend to be, he fucked me with control and purpose. It didn’t take much of his expert hands to getting me cumming all over his cock. Finally, at the end, he flipped me over and fucked the hell out of me and we came together. Ah, sometimes you just need that mature guy to fuck you silly.

My Dream Night

best phone sexMe and my girlfriends love to be freaky. We enjoy the finer things and conduct ourselves like ladies, but behind closed doors we get dirty. I imagine a lovely day that includes manicures and pedicures and a dazzling night out on the town, complete with wine and fine cuisine. Then me and my girls will go out for a massage before we return to my house to gossip about who has fucked who. Then we will compare our tits to one another and taste each other’s seductive skin. Then, I will slip off my pink bra and panties and we will lick and tease each other’s tender juicy pussies! Then I’ll call you over while I’m still dripping wet. I want you to lift me up and slowly slide you cock into me. We can start slow and intense as I gaze into your eyes and moan for more. You can feel my wet pussy contracting and longing to pull you in deeper. I’ll kiss you deeply and passionately, and ask you to go deeper. I want you so deep inside of me, deeper than anyone else. Give it to me faster until I want to surrender because your dick is pleasing me so much! I want you to make me squirt right in front of my girlfriends. I’m not ashamed. I want to do it with you whenever, and wherever. Then each of my girlfriends will suck your gorgeous cock until you scream in pleasure! Doesn’t that sound magnificent, darling? If you want it, join me for live phone sex so I can give it to you hot and heavy like you deserve!

A raise for Dr Rebecca

Its so hard to be taken seriously sometimes in my profession. I went to my boss today and asked him if he had a moment to discuss my performance review. I have an outstanding record with my clients and I do anything and everything I can to keep them completely satisfied with my services. My boss tells me to close the door and to have a seat. As I sit down I can tell he is holding his cock behind his desk, he tells me that he has received mixed reviews about my services and wants to determine for himself if I should be getting a raise. He tells me to prove I have earned it. At this point I know exactly what he means and although I usually save this treatment for my clients, I go around his desk, pull his hard cock out and give him a raise. I suck his balls dry. I think he agrees that I have an outstanding performance review, because we both got a raise. Me in my bank account and him in his pants.

 

Cocksucking phone sex

Roleplay Phone Sex – Rescued

Roleplay phone sexHe had the most delicious fantasy the other day. He wanted me to roleplay like I was a damsel in distress, being molested by a stranger in a dark alley, and he wanted to swoop in and rescue me. I was so grateful to him that I invited him back to my place for coffee, and immediately offered him my body as a reward for his help. I slowly stripped my dress off, then my panties and bra and stockings. He was hard by the time I finished, but kept saying that it wouldn’t be right. I knelt on the floor in front of him, ran my hands up his thighs til they were just grazing the bulge at the center. I looked up at him and asked if he was sure, and he gulped. I ran my hand gently over that bulge and watched his face as I slowly massaged it through the fabric. Then, I pulled the fly down and reached into the pants to pull that cock out. I stroked it and ran my tongue over the head, finding moisture already beading there. I wrapped my tits around his cock, looking up into his eyes as I started to bounce up and down, tit-fucking him. He pulled me up then, and settled me on his lap. I reached between us, grabbed his cock and fitted it straight into my entrance, sliding my hot, wet cunt right down over that huge shaft. He filled me up, stretching me perfectly, and touching all the right places. I rode him to a fantastic orgasm, and took him over the edge with me as my muscles worked his cock over.

Jump Parole Jump my Bones

Fantasy phone sexOne of my parolees skipped town and I tracked him down to this tiny beach town south of here. I was pissed but a little happy that my job was going to lead me to the beach, but hey business first right? I found the jumper at a nudist beach; I thought how perfect I can gain his trust that I’m not going to arrest him. I’ll be naked and nowhere to put the cuffs.
I walk up naked as naked can be, I purposely stand in his sunlight. He doesn’t look up right away just says “Hey get out of my sun.” “Just your sun, huh?” Parolee sits up startled, a few oh shits and oh fuck I’m goin to jail come out of his mouth and I just smile until he gains composure. He settles down and then finally notices that I am standing in front of him totally naked. His mouth drops open and I say “Since your mouth is open, why don’t you stick that tongue out and put it to good use.” Still, a little shell shocked he grabs me and pulls me down on top of him and slams his cock right into me. My pussy swallows his cock, and to be honest I was a little wet from being nude and showing my body to everyone, ok more than a little wet. We fucked and fucked, even had some people watch and enjoy but we just kept going. He fucked my pussy into forgiveness for him skipping out on his parole obligations to me. Pretty damn good fuck, I don’t usually dole out forgiveness for that.

Fucking in church

Fantasy phone sexWho knew that church could be so fun? The hubby and I go to this new church every Sunday. It’s a laid back, come-as-you-are kinda place and everyone is friendly. I just didn’t know how friendly.

I decided to wear a proper black mini skirt topped with a white silk blouse that showed my cleavage off, topped with a cute black blazer. I added black pumps and a spritz of something delicious. You have to understand. We are used to the looks. I’ve been married to my husband since I was a young girl. He is much, much older than me and yes he is quite wealthy. He has a huge penis but it barely works so he encourages me to get side cock and share with him. It’s the only way he can cum.

Anyway, I was getting appreciative looks from the ushers all the way down to the choirboys. A lot of husbands got elbowed, too. But I caught those smiles.

The preacher walked by and whispered to me. “Meet me in my office after service.”

I walked in to find him looking a bit flushed. “Mrs. Robinson. People are saying you are dressing too provocatively for this church. It upsets the wives.” I moved closer. “Don’t you like what you see, preacher.” He seemed to flinch. “Maybe you need to pray the evil out of me. Tell Satan to leave me alone.”  I sat on his desk, parting my legs. I reached for his hand and placed it against my panties.

We fucked hard right there in his office, cheating on his wife and before the almighty. He began screaming as his cum boiled, bursting into my waiting cunt. “Deliver me from evil, Lord. Take this demon from me.” I giggled. I think he really meant semen. We shall see. Next time I will hold the bible while he fucks me. Or maybe I’ll just crawl under the pulpit and give him a blowjob as he tries to preach.

Edging phone sex with submissive K.

Edgeplay phone sex

I have a sub that I adore playing with; edging him is the highlight of my week most of the time. We will call him sub K. I instructed him to write me an email about our last edging session and his words turned even me on. We had an hour long session where I edged him so many times he could never cool down with his need to cum. I made him beg me and he did, I made him get into different positions and he did. He told me all about how much his cock was aching to cum, filled to the top with his hot load I was enjoying not letting him release it.
He told me at one point he couldn’t catch his breath, he needed me to give him that permission to cum. I wasn’t going to. I loved hearing him beg me, the intensity was very heavy and sexually charged, makes my body tingle. I played with my pussy while I controlled him. That’s how much I enjoy it, and I came as many times as I wanted.

When I finally allowed him to cum, he came for so long and so hard I could feel it through the phone. He told me how it was so much more intense than cumming a bunch of smaller times, one big one was what he needed.