Category: Roleplay Phone Sex

From Tranny Phone Sex to Shemale Escorts

tranny phone sexHe started with tranny phone sex, but it wasn’t enough. He wanted to meet a real transsexual. He has been calling me weekly for a year now. We always talked about what it would be like for him to fuck a real shemale. I guess you could say I have been prepping him for the real thing. In the beginning, it was just sexy talk and role play about my pretty 10 inch cock. I talked him through sucking his first cock. Like most of my callers and most of the men I encounter off the phone, he considers himself straight. I consider myself female, so it works. Over time, I had him buy some sex toys, specifically a big dildo so his ass could get the feel of a cock. Once he had his first G-spot orgasm from a dildo up his ass, I knew he would want the real thing. I helped him look up places in his area where he is likely to find shemales. I even looked at personal hook up and tranny escort ads. He wanted a dominant tranny with a big dick like me. Last night, when he called me, he was not alone. He was in a hotel with a real shemale. He wanted me to hear him get the real thing up his ass. He even sent me pictures. She was an escort. Let me tell you what a hot phone sex call it was for me to hear a longtime caller getting fucked in the ass by a T-girl for the first time. I jacked my cock listening to his sexy moaning noises and her telling him how tight his ass felt on her 9 inch dick. I was also super aroused because I helped a long time caller make his naughty fantasy cum true. If you have a shemale fetish, let me help you too.

Hot Phonesex – Naughty Secret

Hot phonesex have a naughty little secret – I love to tease my boyfriend. One of my favorite things to do is have everything done, dinner ready, and be lying on the couch when he comes in. I love being in something comfy that makes me feel sexy, lying on the couch with my body all pointed toward the door. Then, I start playing with myself before he ever even gets home, so that my pussy is already wet and my nipples are hard, and my hands are all over my still-clothed body, driving myself into a hyper-sexual state. By the time he walks in the door, I’m writhing on the couch, touching myself, moaning, and it instantly gets him hard as a rock. He pitches such a beautiful tent. I love how hot and bothered he gets when he walks in on me playing with myself, because it always means a hot, hard, fast, frenzied fuck-fest, followed by a night of slow, sensual love-making. Makes me hot as fuck!

Cum Shots On Tits Is So Fucking Hot

cum shots on tits

This guy and I watched some videos of cum shots on tits the other day. I sucked his cock while he watched girls getting showered with a load of creamy cum. We were talking about how much we both love watching guys cum. Seeing it shoot out of the tip of their cock and spray their huge load of cum onto a set of nice tits is so fucking hot. So, I invited him over and found a compilation video of cum shots and then I started to suck his cock. He was loving watching guys cum all over those hot girls and having me sucking his nice cock all the way down my throat. He was watching a massive cock shoot a huge fucking load all over this girl’s set of nice fake tits when he grabbed my head and slammed it down on his cock and held it there. Then I could taste his own load filling up my mouth.

Roleplay Phone Sex: Naughty Teacher Blair

roelplay phone sexDo you like roleplay phone sex? Men call me mostly for dirty mommy fantasies, but every now and then, a guy wants me to play another mature woman. I love fantasy fucking. I am fucking this teen neighbor boy as much as I can. He goes to private school, so my boys leave for school an hour before him. As soon as they leave for the bus, he is fucking the hot MILF next door. This morning, he wanted me to be his teacher. My young lover is hot for teacher. I dressed up like a sexy teacher ready to rock his cock. I had a ruler and everything. I mean, he does go to Catholic school. I told him he was a bad boy who needed some punishment. I had him pull his pants down so I could spank his bare ass with the ruler. As I had him on my lap for some old school corporal punishment, I felt his cock grow harder with every whack. He liked a dominant teacher; I liked his hard cock. I was set to bend over the desk and get fucked by the student, but he wanted to be the one bent over the desk. The naughty little boy wanted to be pegged. Pegged he got. I put on my strap-on and showed the student how seriously I take paying attention in class. What is your favorite phone sex roleplay?

Phone Sex Whore

phone sexI love phone sex. I have been in the adult industry for over a decade now. This is by far my favorite adult industry job. I can explore all my fantasies safely, especially my dark fantasies. I look like a goddess, but I am a whore. A whore for cock and cum. Lately, I have been insatiable. I think it is because I have become spoiled. I have a sugar daddy that even though I don’t get to see him much because of his exotic travels, I find myself comparing other men to him. It pisses many white men off when I make comparisons to his big black cock. I mean he has a monster cock. White dick rarely measures up to BBC, but guys get upset when I try to tell them my pussy is used to something bigger when they fall out of me. They don’t want to believe a pussy can be ruined. Tim was not happy when he fucked me the other night. He kept falling out of me. He called me a dirty whore then shoved his cock up my ass because it was the only fuck hole not yet ruined by big black cock. I like a good hardcore ass fucking, but for some men, it’s their only option because my pussy has been spoiled!

Guided masturbation fun with the boss

Guided masturbationMy boss and I have been sneaking around lately and sometimes we are a bit impatient when we can’t meet up. So I came up with a way to keep us both really pleased. It actually came about one day we were fucking. I asked him if he masturbates when we aren’t together and of course I knew the answer was yes. He’s not fucking his wife so he is thinking about me. I told him everytime he cums he has to think of me and shoot me a text while he is doing it. A bit of guided masturbation fun together. It’s so hot to now he is getting off thinking about all the times he has fucked me right next to his wife. I love being able to control his headspace. When we aren’t together we are surely thinking about each other. I love sending him pics of me and my toys just to show him how excited he has me.

Pissing

Tranny Phone SexI love pissing on sissy boys. In them or on them. Sometimes I piss on the floor and make them lick it up like a doggy would. Or have them roll around in my golden present. All depends on my mood and how sadistic I feel. Pissing on a bitch boy is such a power trip. Truly marking my territory. Showing you how beneath me you are. That I use you as my toilet. I love to use sissy boys as furniture, whipping post, ashtrays, servants, and fuck holes. But pissing on them or in them. Is a thrill like no other thrill. Watching the piss splash off their flesh. Using their sissy boy mouths clean my cock after ever piss. Filling those bellies full. I am precumming now. I am going to have to piss on my sissy bitch boy and then shove my cock down his throat.

Fantasy Phone Sex with Shannon

Fantasy Phone SexWhen a girl sees something she wants, she goes after it. I saw him from the plaza, and I just knew that if I didn’t take the chance, I’d regret it. I walked up to him and introduced myself, asked him if he’d like to buy me a drink so we could talk. I guess he liked what he saw, too, because he took me up on my offer without any hesitation. By the end of our drink, we both knew what was about to happen. He walked me back to his place, which happened to be a few buildings down from where I saw him. He had a small place, but it was very nice, and when he took off into the kitchen to make coffee for us, I saw my opportunity. By the time he came back, I was standing next to the door into the living room, completely naked, ready for whatever he could bring. When he saw me standing there like that, it was over. He wrapped me up in his arms, lifted me, and kissed me all the way to the bedroom, while I held myself wrapped around him. His hands ran up and down my skin, touching every place he could reach, as his tongue explored my mouth, then my nipples, then my pussy. His fingers dipped into me, and I felt that strumming that meant I was closing in on an orgasm. Then, he pulled his fingers, slid up my body, and his cock drove its way straight into my core. That pushed me right over the edge, and I was flying, wrapped around him, moaning and screaming his name, as he kept fucking up into me, keeping that beautiful orgasm going.

Mommy Phone Sex Helper

mommy phone sexMy mother has been around all month helping me with mommy phone sex calls. She is retired now, so she can travel all she wants. She loves spending time with me and her grandsons. We enjoy having her too. When I am working on the weekends, she entertains the boys for me. It is no longer summer, so they don’t just go out to play or go to the pool. They get cabin fever in the colder months, which means they want to fuck more. I have them trained to not make noise when I am on the phone because they aren’t exactly legal age for phone sex. But one day, they will be able to fuck me while I talk dirty and be heard! My mother fucks them while I work. She doesn’t mind. That is why she visits us so often. She wants that boy cock as much as I do. She is a P mommy. She fucked my brother all through my youth. It is great that she can enjoy my sons in their peak. At their age, they can go all night long. So, can my mother with a little white powder. I love talking dirty on the phone, but doing it while watch my sons tag team their grandma makes it even hotter. I hate to see her go. Watching her in action gives me a glimpse of myself in the future!

MILF Phone Sex Slut

This milf phone sex slut is always on the prowl for fresh young meat. My stepsons are college age boys now, but they gave me my taste for teen cock. The older I get, the younger my lovers have become. Men have been fucking young women for centuries. Guys high five each other but other women shame women who are getting some young dick. I have been fucking this new neighbor boy for months now. Sure, he is still in high school, but I didn’t take his cherry. This boy had game long before me. His mother came home early from work and busted me giving him head. She was not upset he skipped school. She was upset I was blowing him. She started calling me a molester and a slew of other horrible names.  Turns out mommy dearest was jealous. She wanted her son’s cock and was upset another hot woman got there first. I told her we could share him. The boy has ten inches and is horny 24/7. One milf isn’t enough for a teen boy. I had her take a Xanax to relax her. Before long, she was naked blowing her son while I munched on her cunt. She was super wet. What started out as a hot MILF fucking a teen boy, turned into a dirty threesome. I got to help a mother fuck her biological son. That was a first, but it was very hot. I don’t mind sharing a young boy. I shared my stepsons with my friends all the time. Made me start thinking about finding a hot man with a young girl to fuck. I would share daddy’s cock as well as a son’s cock.  What can I say? I’m not just a phone sex whore. I am a real whore too.