Tag: prostate phone sex

Roleplay Phone Sex Lets Us Play Doctor So I Can Milk Your Prostate

roleplay phone sexRoleplay phone sex excites me because I get to be somebody else. Sometimes I even get to be somebody smart like a doctor. I know a lot of people enjoy playing doctor. Sometimes men in the VIP room want to play doctor. Usually, they want a round of show me yours and I’ll show you mine. But occasionally, I get an older guy in the VIP room who struggles to orgasm. And men like that need the bend over and cough type of doctor roleplay.

It’s a dirty job, but somebody needs to do it. And if they pay me right, I will milk a man’s prostate the way a doctor would. Many men experience erectile dysfunction with age. Unfortunately, I do believe it’s a sad part of the aging process. Just like women’s libidos tend to decrease with age.

So, when Charlie came into the club, I couldn’t tell by looking at him that he struggled with orgasms. But he picked me for the VIP room I think because of my age. Maybe he thought the younger girls wouldn’t know how to deliver prostate phone sex. Or he thought they might laugh at him.

But not me. I only laugh at men who come at me with big dick energy but sport a pinky dick. Charlie seemed like a nice man. He sat on the chair as I gave him a lap dance, and he had this rejected look on his face. So, I stopped dancing, pulled a chair in front of him and asked him what was on his mind. And he confessed that he’s tried many things and he cannot get his cock erect again.

Some Men Need Some Extra Help and TLC Cumming

 He feels horny, but his dick just will not cooperate. Viagra barely gives him a hard cock. He thought a lap dance might help. But I suggested something different. And he agreed to try it. So sitting on the edge of the chair, I pulled his pants down, and then I took his boxers down to his ankles. I had him switch positions on the chair, so he faced away from me. Then I instructed him to push his ass over the edge of the seat so I could reach his butt hole. I lubed up my finger and worked it in his old asshole.

Charlie started moaning loudly and I could see his arm jerking up and down his cock. Apparently, I found the right spot to give him the erection he desperately sought. I just wanted to get the biggest cum shot from his backed up old balls. And I wanted to make him feel good. At the end of the day, I’m a GFE provider who likes to take care of men one way or another.

He tipped me very well for cleaning out his pipes. I gave him two prostate orgasms, a blow job orgasm and a fourth load he shot on my tits. To say that Charlie was backed up feels like an understatement. He gave me four massive loads of cum. Plus a few grand for playing doctor with him. My pleasure. Somebody’s got to do the dirty work. And when it’s a nice older man like Charlie, I never mind milking a man’s prostate.

Prostate Phone Sex is Something a Sexy Tranny Delivers Best

prostate phone sexI’m uniquely qualified for prostate phone sex. And that’s because I have a prostate of my own. I can milk myself anytime I want. Men call me daily to fuck their ass. And that’s a form of prostate milking. If you ask me, it might be the best form of prostate milking. Why settle for a sex toy, your finger or even a garden vegetable when you can have a cock cleaning your pipes.

But some men need a little extra TLC. They don’t cum as easily as they once did. And I get it. Between the stress of life and medical conditions, plus age, older men just need a little extra help orgasming.  And that’s usually where I come in. Men find it less gay if the cock that cleans their pipes is attached to a feminine looking creature like me. But I don’t judge. I help. I help men enjoy the most intense orgasms.

Sometimes men call me for phone sex because they just need help cumming. They don’t want to roleplay. And they don’t want to pretend that they don’t know about my sexy tranny cock. They just want help masturbating. And I enjoy guided and mutual masturbation. I can stroke my cock while guiding some poor backed up old man on how to properly drain his balls

A Sexy Shemale is in a Unique Position to Drain Your Balls

I walked Leo through it all. The poor man is experiencing lots of loneliness, as well as medical issues, both of which affect his ability to enjoy intense orgasms. Leo does not own any sex toys. However, I can get creative. I’ve instructed men to fuck their asses with curling irons, ears of corn, beer bottles, and even garden vegetables. Leo did have a cucumber and Vaseline and that’s all he needed. Well, he needed my guidance too.

He listened to my directions. And my soothing voice helped relax him enough to work that cucumber into his tight asshole. Other than a doctor’s finger, nothing has ever entered his asshole. But desperate times call for desperate measures. And this poor man can’t remember the last time he had orgasm, but he speculates he came about five years ago. Some days I can’t go five minutes without masturbating. But Leo tries to masturbate. However, he seems like one of those men who needs a little extra help.

And me and that cucumber gave him all the help he needed. He ended up, enjoying the biggest cum shot of his life with a cucumber up his ass and me directing him every step of the way. He told me he shot a massive load on his chest. And I heard him orgasm. I suspect everybody in my building heard him orgasm. It sounded that loud. But he needed it. And I was happy to help him. There are many ways to orgasm. Let me help you enjoy a massive ball draining too with some creative masturbation too.

Prostate Phone Sex is Not Fun, But Very Necessary to Older Men

prostate phone sexAnything can happen in a strip club, including prostate phone sex. Even though I rarely take the stage anymore because I’m in charge of the girls, I still take requests for the VIP room. This sweet old guy came into the club to celebrate his 75th birthday. According to the owner of the club Ross first visited the strip club over 30 years ago, when the club opened. And he used to spend a lot of money. Then he got married and stopped coming into the club.

My boss told me he lost his wife last year and he seems lonely. I felt kind of honored that out of all the girls in the club, he picked me for the VIP room. Perhaps because I’m the oldest woman in the club. When we entered the room, I put on some 70s music and started dancing to a Donna Summer song. He seemed to love my music selection. But as I started twerking my ass in his face, he told me I didn’t need to take my clothes off.

Some Men Come into the Club Just to Talk

I get some phone sex calls where men just want to talk. No roleplay. Sometimes not even sexual talk. And I can switch gears easily. So, I grabbed a chair and sat in front of him. And I asked him some questions about his life. Sweet, lonely, old man. I encouraged him to tell me about his wife and his eyes just lit up.

He wanted to brag about her. I could tell that, even though this was his second wife, it appeared to be true love. When he told me he had not enjoyed an orgasm in a decade because of his wife’s illness, I never wanted to suck a cock so badly. But he didn’t want to cheat on her memory. It was all I could do to hold back the tears.

So, I explained prostate milking to him. And that it’s more medical than sexual. Plus, I don’t think anybody would consider prostate milking cheating. I asked him to just think of it as medically necessary to relieve some tension in his body. He clearly needed it. It took some convincing, but I got him to understand that backed up balls cannot be good for a man’s health. So, I lubed my finger up and slipped it into his asshole.

The Best Things in Life are Free

I told him the orgasm will feel more satisfying if I stroke his cock too. And he just laid back and let me. But it didn’t take long. I could feel the tension mounting quickly. I expected a volcanic eruption. And likely he would give me the biggest cum shot of his life. I called that one. His old dick shot off like a fire hydrant. He sprayed my face and my tits with chunky backed up cum.

But I don’t milk every old guy’s prostate. It’s not something I enjoy necessarily. But it is something that feels necessary to many men. And the sweet old guy needed an orgasm more than anybody I’ve met recently. Plus, he seemed so sweet and romantic that I wanted to help him. I almost felt bad when he tipped me $1000. I need money like everybody. But some things in life seem priceless. Like giving a sweet old man, a much-needed prostate milking.

Hot Phonesex Lets Me Take Care of Lonely, Neglected Cocks

hot phonesexI love hot phonesex. When I entered the phone bone world, I started doing this part-time. Just to supplement my income from the strip club. But now I do this full-time and the strip club is more part-time. I love talking dirty. But I really enjoy taking care of men.

And I really like talking to lonely men. Lonely men come into the club all the time. And they’re not much different from some of my callers. Married men seem taken for granted, and sex starved. Some just need somebody who cares and listens and wants to make their day better.

Perhaps this contributes to my perpetual singleness. I talk to too many men, and I meet them too, who are married, but have not fucked in years or decades. Why get married if you’re not going to fuck your husband?

So, this phone sex babe loves delivering the girlfriend experience. I don’t need a husband when I have my lonely men at the club and on the phone. Last night, I met a lonely widower at the club. Likely 30 years older than me.

But age doesn’t matter to me. Lonely men come in all ages and races. In my head, I called this man Mr. Howell from Gilligan’s Island. I used to love that show when it came on Nick at Night in the 90s. But this man came into the club dressed in an all-white suit before Memorial Day. He did look dapper though.

And he took a shine to me. I did not dance last night. But he wanted me in the VIP room anyway. Poor man became a caregiver to his wife who passed away from cancer. After the lap dance, I gave him a hand job.

I Love Taking Care of Neglected Men on the Phone and in the Club

Honestly, I would’ve fucked him. Such a sweet old man. Believe it or not, a decent cock on him too. Not sure if he took Viagra or not, but I don’t believe I ever felt a cock quite as hard as his. At 68 he still gets boners. But a woman has not touched his cock in 25 years.

And I knew his wife was sick. But she was not sick for 25 years. They got married in the 80s. This sweet old man gave me the biggest cum shot from a hand job I’ve ever experienced. His load shot across the room. And he let out a guttural moan that suggested he needed to bust a nut. I thought he might pass out from exhaustion afterwards. My pussy never touched his dick. The best paid hand job of my life.

For a bit, I wondered if this mirrored those playboy models trying to satisfy Hugh Hefner when he was in his 80s. Although, me Mr. Howell seemed closer to 70, he sported a neglected old dick. But what a sweet man. I would’ve jacked him off for free.

Although in my profession as a phone whore and a stripper, I’ve met my share of assholes, Mr. Howell, I would not include him among them. The sweetest old man. Afterwards, the owner of the club told me that man’s last name. In my town parks and buildings appeared named after his great grandfather. Old school money family.  So, I’ll help him out if he comes to the club again. That’s what I love about my jobs. I get to meet such interesting people and help them feel better.

Shemale Phone Sex Because I Can Milk Your Prostate

shemale phone sexMen need a shemale phone sex star fucking them. Never met a tight ass I would not fuck. This will be my last week in Florida. I decided to go back home earlier since the weather warmed up. But I made a pack with myself that I would fuck a few more assholes before I head home.

Now my sugar daddy just left to go back to New York. And I filled his ass up before he caught his plane. I enjoyed hanging out with him for a few weeks. He paid me handsomely too. Although I do not consider myself an escort, I will be a sugar baby for the right man occasionally. However, I will always be a dominant sugar baby. No amount of money will make me a bottom bitch.

I like being the one to give the hardcore ass fucking. And most men prefer a dominant tranny fucking them. That’s because they want fucked in the ass. They want me to massage their prostate. Think about it. If you want to experience a mind-altering orgasm as a man that requires something in your ass to find your G spot. You’ll never find that spot fucking a pussy unless you’ve also got a cock in your ass. I can thank the Internet for making special girls like me a lot more popular.

Men Always Want a Sexy Shemale Milking Their Prostate

Last night I went to a trans friendly bar here in Florida. I wanted to see what I could find. And I found Michael. He seemed like he might be looking for a girl like me. I took him back to my place and gave him that ass pounding he needed. And he begged for it like a little bitch too. Now this guy seems nothing like my sugar daddy. Some men seem like bottoms to me, but I don’t treat them like bitches. Yet others seem more like bottom beta bitch boys. And that’s what Michael appeared to be. So, he got my dick up his ass with no mercy.

Michael needed a prostate phone sex exam. I shoved my dick so deep inside his asshole that he squirted all over my floor. And because I could tell he was a bottom bitch boy Michael, I made him lick up his own cum off the floor. And he did it. Not all men will eat their own cum. But I love encouraging it, and sometimes even forcing it. What a great night. I’m going to find another bitch boy just like him tonight too before I return home. Too many asses to fuck, never enough time.

Shemale Phone Sex Getting A Guy To Fuck a Tranny

People ask me how many straight dudes love shemale phone sex surprises to fuck a tranny. Well, I’ve got a few tricks up my sleeve. First of all, I make sure to dress and present myself as femininely as possible. My curves are accentuated by form-fitting clothing that emphasizes my huge tits and round ass. When it comes time for intimacy, I slowly undress in front of them while maintaining eye contact – teasingly revealing more skin each step of the way until finally standing before them completely naked with my big cock hidden beneath folds of flesh.

I then invite him into bed or onto the couch where we can get comfortable together under blankets or sheets if needed so he doesn’t see what lies ahead just yet; this creates an air sexual anticipation between us both! Once settled down snuggle close enough for me to feel his warmth against mine – at which point things start getting hotter…

As our bodies press closer together unintentionally (or maybe intentionally), there’s no denying how aroused we both become from being so close physically like this…and emotionally too since you know deep down inside that something exciting is about happen soon enough once those final layers come off!

With one swift move on your part—whether its pulling back some fabric yourself out curiosity/desire–you find yourself staring straight into eyes wide open shock when they first lay eyes upon not only massive breasts but also their prize catch: A HUGE TRANNY COCK!!! It takes some guys longer than others process such revelations but eventually most succumb either because they were curious all along secret fetishists themselves or simply too turned on by the sight of my big cock to resist. Some guys might try denying it at first, but I reassure them that they’re not gay for wanting a shemale like me; after all, everyone has their preferences and fantasies! And let’s face it – who wouldn’t want an experienced tranny slut like Louise taking control?

Prostate Phone Sex From Guy’s POV After Lacey Fucked His ASS

Prostate phone sex was so hot the other night, I found my boyfriend had written this in his journal.  Sharing because I didn’t know he haProstate phone sexAs I lay on the bed, my eyes closed and my breathing steady, I felt your warm hands gently massaging my lower back. The sensation was soothing and comforting, making me feel safe and open to whatever you had in store for me. Suddenly, there was a subtle pressure against my prostate – just enough to make me take notice but not too much to alarm me. You began slowly circling your fingers around that sensitive spot, teasing it with gentle strokes that sent shivers down my spine.

“You like that?” you whispered in my ear as you continued your ministrations.

I moaned softly in response, arching my hips up towards your touch. It felt incredible – almost too good to be true. You increased the pressure slightly, still circling but now applying more focused attention on that small area of nerve endings deep within me. My cock twitched at the sensation; even though we weren’t focusing on it directly yet, its tip leaked pre-cum onto the sheets beneath us.

“That’s it,” you murmured approvingly before sliding one finger inside of me while continuing to work over my prostate from outside with another hand.”So fucking tight…” Your voice was low and husky as if savoring every moment of our intimacy together.”Just relax into it…let yourself enjoy this feeling.”

With each stroke both inside and out—in tandem now—my body started melting under yours; tension draining away as pleasure built up within every fiber of being until finally…oh

finally, I couldn’t contain myself any longer. My hips bucked off the bed as an intense wave of pleasure washed over me – a prostate orgasm unlike anything I had ever experienced before! It felt like every nerve ending in my lower body was on fire with ecstasy while at the same time cool relief coursed through my veins leaving me weak-kneed and panting for air.

“Fuck…yes…” The words tumbled out of my mouth involuntarily as you continued to work your magic on both ends; milking every last drop of pleasure from deep within me until finally releasing me into blissful oblivion once more. As the aftershocks subsided and our hearts slowed down their frantic race together, we lay there entwined; sweaty skin sticking together but contentment filling every crevice where lust had moments ago resided.

“That,” you said softly against my ear, “was just a taste.”

Cock Control So You Can Enjoy Better Orgasms is Something a Sexy Tranny Excels At

cock controlMany men I fuck enjoy the way I cock control them. So many men do not fully enjoy their orgasms. They simply cum too quickly. And I know something about this. As a teenage boy, I jacked my cock nonstop. And an early lover in my college days while I transitioned, taught me all about edging my dick to enjoy a better orgasm. Since I learned from him the secret to a fulfilling orgasm, I’ve edged my cock ever since. So, you might consider me an expert in helping you enjoy a little control of your orgasms.

My sugar daddy down here in Florida can be a quick cummer. He needs me to help him. Although I am a top and I can make myself last long fucking a tight ass, sometimes men beat their dick quickly with my cock inside them, and they lose momentum as soon as they cum. So, I like men to last with me, so they don’t try to pull away from my cock before I cum.

Nothing pisses me off more than a man who cums and does not wait for me to cum too. My sugar daddy does not do that. But that’s because he’s extremely submissive and knows my rules. However, that does not mean I do not want him to enjoy prostate phone sex as long as possible. When I’m fucking a tight ass, I’m hitting the man’s G spot. So sometimes you don’t even need to touch the cock and a man’s cumming quickly.

A Sexy Shemale Can Help You Enjoy Better Orgasms

And a prostate orgasm feels like one of the best orgasms you will ever experience in your entire life. But I can still make you cum again while I’m pumping your ass. So, I edge men. I’ll pound their ass hard for a few minutes, then slow it down and then pick it back up again. And sometimes I even pull almost all the way out and just tease the asshole with the head of my dick.

I do what I can to help a man enjoy not only my cock in his tight asshole, but his own cock and his own orgasms too. My sugar daddy and I fucked for hours last night. And it marked the first time that he lasted longer than 20 minutes with me pumping his asshole. He’s been taking notes. Not only did I enjoy the biggest cum shot in his ass, but I think he enjoyed the same thing with his cock too.

When you last longer the cum trajectory seems so much more intense. You cum more. You shoot further. And you feel better drained. So let me help you gain a little control over your cock and your orgasms too. I know how to make you cum harder than any woman.

Prostate Phone Sex Leaves Your Balls Thoroughly Drained

prostate phone sexProstate phone sex a sexy tranny knows how to deliver. Not every man is comfortable, exploring his own prostate. And many still don’t want anybody else exploring it either. But if you’re a bottom boy with a shemale, she will explore your prostate. And trust me, you will love it. Best ball draining of your life, guaranteed. 

When I met Oscar, he knew what he wanted from me. He wanted to experience a prostate orgasm. And he knew my sexy 10-inch cock would likely do the trick. Even much smaller cocks than mine could do the trick. Of course, every man is built a bit differently, but a cock at least 5 inches should find that hidden magic button.

I met Oscar six years ago. He learned about my panty surprise from a friend. A happily married guy, but recently as an older man, he started experiencing dick issues. I think he told me he recently turned 60. His wife does not seem interested in sex anymore and although he admitted to slowing down, he still wants to cum. But he can no longer cum simply from beating his meat.

He thought as a shemale domination porn star, I could drain his balls for him. And get this. He even asked his wife if it would be OK. And she loves me, so she gave him the go ahead. Oscar will never leave his wife. And I’m not a homewrecker. I looked at this more like a good deed. A man I know is experiencing erectile dysfunction. And I could help him experience thorough ball draining.

A Sexy Shemale Knows How to Drain Your Balls

He came over last night and seemed incredibly nervous. I think he feared that he would want this more than once. And I told him that it happens often. But we agreed on a one-time fuck to drain his balls. Show him that his cock still works. Perhaps, it just might need a little manual stimulation from the inside to cum. So not only did I fuck his ass hard, but I also showed him with a dildo how to do it himself.

I drained his balls completely. Better than they’ve been drained in a very long time. And I showed him how to milk his own prostate. Every man should know how to drain his own prostate. Because let’s face it. We’re all human. And at some point, we might experience some erectile dysfunction, or our balls might get so backed up that merely jacking off alone will not rectify the issue.

And nobody better to show you how to milk your own prostate than a sexy tranny phone sex babe. Of course, the preferred way to milk your prostate would be with a sexy tranny cock up your ass, but I know that’s not possible for everyone. So, at the very least let me show you how to milk your own prostate with a sex toy. And you can even use your wife’s toy and I won’t tell her. Our secret.

Guided Masturbation Teaches Men That There is More Than One Way to Cum

guided masturbationI experienced a wildly erotic guided masturbation session last night. Perhaps the reason I enjoyed it so much is because this guy appeared so submissive. He jacked his dick off any way I told him. And I got a bit wild. At one point, he fucked himself in the ass with a cucumber just to please his mistress.

I’m not submissive. However, I don’t consider myself dominant either. At least not dominant in the whips and chains arena. I never experienced BDSM. I’ve spanked men, tied them up with pantyhose and things like that. And I never see myself in a dungeon wearing a latex suit, cracking a whip down a guy’s back.

But I will instruct a man how to masturbate for me. And he will do more than just stroke his cock for me. I think all men should experience prostate phone sex fun. For men who do not fuck on a regular basis, they especially need guided prostate milking. It’s the best way to drain your balls completely.

And I know a thing or two about training balls, the old-fashioned way. Most of my married lovers appear older than me. And when I meet them, they usually have not experienced an orgasm in over a year. And you can jack your dick every damn day, but it will never feel the same as a pussy.

There are Many Ways to Cum

So, after I determined that my caller could not locate his wife’s dildo, I directed him to his refrigerator. I thought about a carrot stick. But he suggested the cucumber. He found some Vaseline, so he used that as lubrication for the cucumber. Now a cucumber possesses some girth to it. So, it’s not always the best first thing to put in your ass. But if you’re desperately horny and desperately backed up, it will feel good eventually.

Prostate milking requires an experienced mistress like me helping you. But also, deep regular breathing helps too. You take a deep breath in and as you exhale with your entire body, you work some of that cucumber up your back door. And before long, it disappears in your ass. Perhaps the best sensation comes from a suction cup dildo. However, most men do not have access to one of those unless they go to their local adult bookstore and purchase one or buy one on Amazon.

Some Men Just Need a Different Way to Ejaculate, Sometimes

After a few deep breaths and exhales, my caller inserted that cucumber deep enough inside his ass to hit his magic button. And after that everything seemed simple. In the squatting position, he could push the cucumber in and out of his ass in rhythmic fashion.

Think of it as Morse code on your prostate. Hot ass sex Morse Code, LOL. A few short taps followed by a few long taps on that magic button, and your cock explodes. Explodes big chunks of backed up semen. And afterwards you will feel so much better. Like a heavy load lifted off your shoulders.

I love helping men experience, intense orgasms. With the right tools and instruction, I can help you experience the best orgasm you’ve ever had too.