Category: Roleplay Phone Sex

Mature Phone Sex Fantasies

mature phone sexMature phone sex is for guys who like older women. Even if a guy is older than or my age, he can still role play a mature fantasy. Most men have a fantasy about a hot woman in their life past or present. I have had my share of older women fantasies cum true in my life. My stepsons, their friends, nephews, neighbor boys… have all had a shot at fucking me. I like younger guys. They want to please you. They want you to teach them how to please you. They have zero problems getting hard. They need very little recuperation time. They cum a lot. They rabbit fuck. And, they don’t want to marry you. They just want to fuck you. Oh, and bonus, they have no hang ups or inhibitions. When I fuck my stepsons, for example, they are completely cool with their balls touching as they tag team me and they are brothers. I love men secure in their masculinity that they don’t care about being near another naked  man. Young guys are all about the pussy. Not that older guys aren’t either, they just can be more difficult to contend with because they have dick issues. I have no time to wait for a little blue pill to work. When I want to fuck, I want to fuck. This guy my age picked me the other night. We were back at his place getting hot and heavy when his dick was flaccid. He blamed it on blood pressure pills. I blamed it on old age. He popped a Viagra and suggested we cuddle until it worked. Do I look like I cuddle? He had a teen son in the house who didn’t need a pill. Can you guess which one I fucked? Daddy wasn’t happy. Don’t want me picking your son over you? Make sure your dick works.  So when I say I can deliver roleplay phone sex for whatever your mature fantasies are, I mean it. I have lived every older woman fantasy you have ever had and some you never imagined.

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Sexy ghost haunts the B-n-B

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I feel that truly hot phone sex can be simply a well told story, and being the season for ghost stories, here’s one of my favorites!

She floated, unseen, room to room, no concept of time passing, only the pain that ached in her soul. She had been so very in love, then suddenly, she was dead. She wanted to scream, to cry her agony to the world, but no one could hear her, save for the little whispers and shadows at the corner of someone’s eye. She couldn’t tell, but nearly a century had passed since the saloon she died in had existed. Now in it’s place stood a B-n-B, all alone under the weeping willows. So peaceful, and quiet… mostly.

There was a new resident for the weekend. He was laying on the bed, stretched lazily out over the covers, naked. She hovered, unseen and unheard above him. Was this her lost love? Memories are so fluid when you’re of a different plane of existence.

She lowered down over him, breathing on his skin, raising gooseflesh along his body. She played her fingers around his member, making it rise. He moaned gently in his sleep. She focused her energy and took him in her mouth. He gasped, but did not stir otherwise. She kept working her head up and down on his cock, teasing and licking as it started to drip precum.

Readjusting, she crouched over him, yet made no impression upon the blankets. Lowering her hips, she impaled herself upon him, burying his cock deep within her pussy.

She rocked back and fourth, harder and harder.

He came as he woke, knowing only the seemingly empty room, and a hauntingly good wet dream…

Blowjobs Phone Sex

Midnight Rape Fantasies

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I could feel him behind me so I started walking quicker. I was tipsy and scandalously dressed…a girl my age should never be alone. I could hear him getting closer and I started to run in my heels, a little light jog at first but that surly wasn’t enough because I was being dragged down an alley with my feet kicking and my mouth covered. He was so much stronger than me, a helpless little girl under that big body – I stood no chance. I tried to plead with him, beg him to let me go and I would never tell anyone but he was coming for what he wanted and not leaving till he had it. I knew I was dressed like a whore but I’d not been fucked as much as most sluts and my young bald holes were still tight as a little virgin. He went it dry, slamming his cock in and making me his dirty worthless victim. I cried and begged but he punched and slapped me till I shut up. He used me and cummed in my cunt no matter how much I tried to squirm away he slammed it in deep – showing me he’d do whatever the fuck he wanted. I was scared and turned on… this was not what I wanted! Or was it?

Wet Bald Pussy Makes Men Cum

Wet bald pussyGuys really seem to love a nice, clean-shaven pussy. To that end, I have long celebrated Bald and Free day. I love sitting in the tub, spreading my legs onto each side of it, and then running my hand over my cunt with my shave gel. I love the feel of a fresh razor grazing the creases where my thighs bend in to my cunt, caressing over the skin and lips, shearing away every inch of hair. Rinsing myself off, I often have trouble refraining from running my hands over my now smooth little cunt. I usually find my fingers working their way into the clean-shaven folds of flesh, straight to my nub and into my pussy. I work the bath water over and around my clit, and into my sweet little cunt over and over again, until I bring myself to a full-blown orgasm that rocks my world. Once I complete my bath, I almost always go that entire day commando. Who needs panties when your cunt is as lovely and clean as mine?

Ass to Mouth Phone Sex at the Club

I did a private show with a man the other night. I pushed him onto the bench and climbed onto the table to start a dance for him. After a few minutes, I stepped down onto the bench, straddling him, so that I could use his body as my pole to grind and rub against. I worked my way DOWN his body, until I was grinding directly on his lap. My hands pushed his shirt aside and worked his nipples for a few minutes, then found their way down to his fly. I undid that and freed his cock, then proceeded to grind a bit more.Ass to mouth phone sex

I slid down between his legs and ran my tongue over his cock, licking the precum off the tip as I went. Then, I swallowed his cock in one breath, and proceeded to suck him hard and fast. When he got close, he tapped me, and I stopped. I stood back up, turned around, and did a dance for him, showing him my sweet little ass in that little g-string. I moved my hands to my hips and played with the waistband for a few, teasing him with the prospect of the panties coming off. When I finally did remove them, I bent ALL of the way over directly in front of him, giving him the PERFECT view of my wet little cunt and tight, puckered ass. He sat up and started eating my ass hole, grinding his tongue all around inside of me, before moving to my pussy and driving me to a quick orgasm. When he finished that, he stood up and plunged that cock into my tight vag, plowing me for all he was worth, hitting it so hard that the shock waves from my orgasm couldn’t dissipate. Once he drove me to one more orgasm that way, he pulled out and SLAMMED home into my ass hole. He fucked that hole as hard as he’d fucked my pussy, never stopping until he shot his wad into me. It was such an amazing session!

MILF Phone Sex: Sheila Turns Boys into Men

milf phone sexMILF phone sex sluts get laid all the time. I swear the older I get, the more I fuck. Those young boys can’t resist big tits and a round ass. I was walking the dog today when a young boy got off the school bus. He was clearly following me, so I made sure to really shake my ass. I had on yoga pants with no underwear and a sports bra that barely contained my 44 EEs. He followed me around the neighborhood. He didn’t even realize that he had come full circle. So, once he was back in front of my house, I invited him inside. He was skinny, socially awkward and screamed virgin. I love virgins. When a MILF makes a boy a man, she forever ruins him for girls his own age. Even when he grows up, he will still want older women. So, because of that, it is important that a MILF teach a young man how to please a woman. Not all women like the same things, but if you teach him the basics, the next MILF he meets can direct him on just how to please her. At least he will have some basic navigation skills. I began by showing this boy my pussy in all its glory. Spread wide to reveal my pretty pink folds and wet creamy inside. I showed him the basic parts; taught him how to use his fingers and tongue to work some pussy magic. He was a quick study too. Gave me a hot squirting pussy  within an hour. I had to return the favor by letting him fuck the wet cunt he created. He grinned from ear to ear as he pumped his long skinny dick in and out of my MILF pussy. He got off the school bus today a boy. He gets on it tomorrow a man.

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Sissy Training Phone Sex with Shannon

Sissy training phone sexMy sissy boy lover came back to call. My problem was that he came dressed down, looking a little frumpy for my tastes in some jeans and a t-shirt. So, I pulled him inside and put him on the floor. On his hands and knees, I undressed him before spanking his tight little ass for showing up so shoddily attired. When I finally had him down to his bare skin and had sufficiently punished him for his lack of good judgment, I pulled out an outfit I had made him leave here in the past. I handed him the box, and ordered him to get dressed right there in front of me.

He pulled the panties on first, tucking his cock gingerly into the thickest part before adjusting the g-string into his ass crack. Then, he put his bra on, filling it out with the little silicone pads I had found for him. At this point, I told him to stop and follow me. When we got to the bathroom, I pulled a razor and my shaving gel out of the cabinet. I forced him to shave, and watched as he did it. I popped his ass every time he missed a spot, and he missed a few.

Once he finished shaving, I brought him back into the living room, and held his dress up for him. He pulled the sexy, slinky little pale blue slip of a dress up his legs and over his hips. The dress hugged every curve of his sweet body, and his hard cock was a bulge pressed against it. When he had finally finished dressing, I brought out the wig I had bought just for him. It was close to his natural medium brown, but with some natural red shot through it. It was a sleek style that would complement his facial structure. I sat him at my vanity, and watched patiently as he put on makeup, receiving approval for each item before using it. He was such a sexy sissy. When he finished, I rewarded him with my pussy on his face.

Babysitting or Training session?

 

Sissy Training Phone Sex

I hate watching boys. Puberty has them going wild and honestly if it walks and talks I really don’t want anything to do with them. I like them so young they can’t say no! I was watching Chris. The annoying bitch boy who hated it and threw a fucking fit every time his mommy and daddy left. They knew he was a monster just like I did. This little shit was acting like a pussy ass bitch. Crying and screaming on the floor. I grabbed him by his ear and pulled him up off the ground, Almost ripping it off. Slapped his little bitch face which shut him up. I told him if he was going to act like a little crying bitch he was going to be treated like one. I had my costume wig with me for Halloween and I put it on him. We went into his precious mommies room and put her make up on him. He kept screaming and crying as I was trying to do his make up. Its ruined, tear running down his face. I slapped him again and dressed him in his mommies clothes. Made him duct tape his tiny cock back by his asshole. Put on a thong and a bra as well as a sexy see through nighty. Strapped some heels on him and shoved him outside. I made this crying bitch walk up to each one of his neighbors and tell them what he was. ” I am Christina, your new neighbor. I am a sissy faggot whore. Can I suck your cock?” He was a brand new sissy bitch and he was going to be trained so well!

I Am A Bald Brother Fucker

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We had tried to get you to shave that comb over for years, so when you show up at my door with a razor and shaving creme telling me it was time, I was shocked. You were planning on surprising y sis for Bald And Free Day. I had never heard of Bald And Free Day, but didn’t really care what the day was so long as we got rid of that scraggly comb-over. Before you could change your mind I led you to the bathroom and spread the shaving creme. I was so into my work, I didn’t notice my tits were rubbing your head as I leaned across, getting saturated with the shaving creme. When I notice you were staring, I looked down, seeing my shirt soaked with the shaving creme. My white top had become virtually see through and my dark nipples were visible holding your attention. The sexual tension was thick in the air. When finally your hands cupped my tits, lifting my shirt, a soft moan escaped me. Your mouth was hot as it closed around my hard nipple. Leaning into it, I had your head wedged perfectly between my mounds. I rubbed the smoothness of your head, becoming even more horny. Without a care that you were married, or my brother-in law, I quickly stripped out of my shorts as you dropped your pants and boxers. Straddling you, I lowered my bald wet pussy onto your cock, I fucked you there in the bathroom without even finishing removing the shaving creme. I had dreamed of fucking you since I first met you and now that I had your cock in my snatch I didn’t plan on stopping. What my prudish sister did not know wouldn’t hurt her, and this huge cock would defiantly help me, anytime we could sneak away for a fuck. Who knows it may make your marriage better, since he wont be suffering from the blue balls anymore. Think of it as my sisterly gift!  I giggled as it hit me that now i am not only a father fucker, but a brother fucker too.