Category: Prostate Phone Sex

Random Enounter with an Ex: Tranny Surprise

Right out of school, before I decided to transform myself into the beautiful goddess I am today, I tried just being a gay man. I had a secret boyfriend. Not because I was ashamed or embarrassed but because he was too concerned with what others thought. You know the type. School jock, most popular boy in school… Would tarnish his all American image if folks knew he liked to get fucked in the ass. I have always embraced my sexuality so that relationship didn’t last long. Being Tom’s dirty little secret actually gave me the impetus I needed to transform myself. I was a girl trapped in a man’s body anyway. Look at me? Nothing manly about me, well expect for my hard cock!

I have not seen or thought about Tom in years until I spotted him today at the mall while I was holiday shopping. “I wonder if he would recognize me now,” I thought? I approached him. Blank look when I said we went to school together. He had no clue I use to fuck his ass in the back of his Dad’s Ranger. He agreed to lunch with me. I noticed a ring on his finger and thought his poor wife is probably clueless he likes to have big cock rammed up his asshole.

After a couple hours of chit chat and catching up, I invited him to my place. He was more than willing. He thought I was some girl from school he just couldn’t remember because I use to be a wallflower. I mean I have changed quite a bit since those school days! He was about to remember me though. As soon as we were in the elevator going up to my loft we started kissing. I have this special tongue trick that always drove him wild. At that moment he knew we had kissed before, but still no idea who I was! Once we entered my loft, I went right down on my knees and sucked his cock. He was having trouble containing himself. I have mad cocksucking skills and they have only improved over the years.

I slid a finger up his ass and started to pleasure his prostate, which any guys loves if they just relax enough to let their partner do it. I had him right on the edge of cumming when he begged to fuck me. This was going to be epic, I told myself. When he ripped off all my clothes and saw my throbbing ten inch cock, he knew exactly who I was and fell to his knees like the cocksucking faggot he was so many years ago. Once a cocksucker, always a cocksucker. He was too into the heat of the moment to say much else but, “Fuck my ass.” Which, I gladly did. His ass was just as tight as it was when we were in school. Just this time we got to fuck in a bed.  I deposited the largest load of spunk I have left in a man’s ass in a long time. I think the thrill of surprising him with my transformation made me extra horny.

Of course he is still closeted.  He trolls the adult bookstores and public parks late at night for some occasional cock, much like a vampire trolls for blood, to keep his cravings under control. He suggested I be his weekly secret and I told him to step out of the closet its almost 2015. I won’t be his dirty little secret, but I will be yours. Are you on the down low? Trolling for random gay encounters? Thinking of cock as you fuck your wife? Blaming stress and high blood pressure on your lack of a hard on with chicks? If yes to any of those questions, then you need me. Consider me your sex therapist. I can satisfy your cock cravings while saving your bogus relationship!

Have You Had Your Prostate Milked Lately?

A few years ago I was reading an article on milking your man’s prostate. The home prostate massage has become one of the sexiest things women can do for their men. And according to many articles and doctors, it is very healthy. Milking your man’s prostate increases blood flow and releases backed up cum. Now, my husband is much older than me, and his cock doesn’t work like it use too. He enjoys watching me fuck other men, including his boys, but often he gets hard and just deflates. So, I knew he had some backed up fluid. Letting me play with his ass, however, took some convincing. But I find wine makes it easier to convince him of anything.

I started by pouring some sweet red wine over his cock. I used it as lube, then slurped it off his cock. When he was feeling good, I gave him what’s called a perineum massage. There is this tiny smooth patch of skin between the balls and ass. If you press your thumb firmly there, it stimulates the prostate indirectly. My hubby began moaning and his old dick started getting hard. I pulled him off the chair a bit, put some KY warming jelly on my finger, and slipped my finger right up his asshole. Just quickly, then pulled it out to see if he even noticed. He was still moaning.

While my finger was working itself in and out of his tight asshole, I started massaging his balls, cock and perineum with the KY warming jelly. I spread his ass cheeks and poured some lube directly on his anus. I slipped my finger back in about an inch deep. He sighed but did not protest. I moved my finger gently around until I found the little walnut sized prostate. I pushed my finger towards the base of his cock, and went back and forth between his prostate and the base of his dick. OMG he moaned so loudly. I started jacking his cock as I moved my finger all over his prostate. I would go fast, then slow down. I wanted to make him last. I could feel his balls welling up with cum.

 This was as hard as his old dick has been since I married him. I just kept playing with his prostate, moving my finger in and out of his asshole while tugging at his wiener until he shot an enormous amount of cum on my face. I looked like someone had poured a glass of milk in my face. According to all those men’s health magazines, guys will cum much more and much harder this way. Since my hubby has not shot a load in decades, I have to agree.

 Have you ever had your prostate milked? Well, I have some mad prostate milking skills now. I bet I can give you the hardest cum of your life.

Rim Job Phone Sex with Shemale Carla: The Tongue Piercing Surprise

Right after a lovely patron bought me my kick ass tits, I got my tongue pierced. I had read a story in Penthouse Forum about a traditional woman getting hers pierced for the pleasure of her husband’s anal region. I am a very anal special girl. I love giving and receiving it up the ass and I love rim jobs.  I love tonguing that pretty little pink shebang. And with a tongue piercing, that little pink shebang puckers up and pulsates with pleasure. Right after I got it pierced, I picked up this hot young stud at the gym and brought him home.  I drew us a bubble bath because the cardinal rule of a hot rim job is a squeaky clean rosebud. You want that ass fresh out of the shower for your maximum enjoyment! Especially if you are like me, and can spend hour with your face buried in an ass.

Now, this fellow was not gay, but he knew I was special and seemed turned on. I told him I was about to blow his mind and his wad. I got down on my knees and began to worship that pretty cock. Long licks up and down the shaft, licking the balls too, making sure the ball of my tongue ring traced every throbbing vein and went right along that pee hole. He was shaking from the sensation. Shaking  in a good way. That tongue ring traced every ounce of tasty flesh on his cock. And since I was already between his legs, I slowly licked my way to his back door. I held his ass checks in my hand, alternating between squeezes and tugs to part his crack. I had provided a fellatio smorgasbord and he was about to experience an anal sensation like none before.

As I placed that tongue ring on his perineum and ran it back and forth in a steady tongue lashing extravaganza along his happy trail, I had one hand jacking his dick and the other hand slipping a finger into his ass. He was moaning loudly, and palming my head as to go faster and deeper. I worked my tongue stud all over his taint, sending shivers all over his body. Then without warning, I slipped my finger out of his ass, and put my tongue in. I tongue fucked his backdoor with that stud ring flicking his anus ever so sensually. A matter of minutes and he shot a huge thick load of spunk all over the place. The biggest trajectory of cum I had ever seen. Like a volcano erupting. I have to thank my little tongue piercing for putting my companion over the edge.

I gave him some down time while he worked on returning the favor. By the time he got my cock good and hard, his dick was ready to explode again. He put it up my ass and fucked my ass better than I bet he ever fucked a pussy. I swear by my tongue piercing to give a guy a prostate party he will never forget. Every ass I have licked and tongued, squirms and begs for more.  I promise you a good rim job gives you unconditional adoration, regardless if you are packing a panty surprise. So, who needs their ass licked today?

Tossed Salad Any One?

Do you love a good rim job? Love to have a tongue or finger in your tight little poot chute while your cock is being sucked? Well guess what sugar I love to have my salad tossed just as much. You know it is true what they say no one knows a woman like another woman. I want my ass licked just like my cunt, soft and sweet and sensual. Do you have what it takes to toss my salad and make me cum so hard I squirt in your face. If you want a full fledged, straight on, drown your face in sweet, hot cum, learn to lick my ass the way it’s supposed to be licked. Master the art of a good salad tossing. Female rim job heaven for me and the face covering orgasm of your dreams can be yours. Are you game or are you lame?

Roleplay Phone Sex with BBW Glenda: Naughty Nurse

Roleplay phone sex I find very hot because it allows me to be creative with my naughty fantasies. I recently had the chance to do a live roleplay of one of my longtime fantasies with a well endowed friend of mine. I told him I always wanted to be a naughty nurse giving a patient a very special exam. Turns out he always fantasized about a hot, voluptuous nurse giving him a prostate exam. And, he could make our roleplay even hotter and more realistic because he had access to his brother’s exam room who is a neurologist. I put on my naughty nurse outfit for him and when we got to the office we went into our characters. He waited outside in the waiting room, and I came out and asked for “Mr. Nowlan.” He came into the room with me and I asked him to undress and slip into a gown and leave the back open. He went behind the partition as instructed, but began to talk all nervous like. “Are you sure this okay? I’ve never had a prostate exam from a nurse before. What if I get hard? I mean you are really beautiful,” he said. I explained getting hard was a natural reaction to having a finger in your rectum. And, I added, the male G-spot is actually in the ass, which is why so many men, gay and straight, enjoy anal sex. He emerges from behind the curtain with a sheepish grin and an obvious hard on. He apologizes profusely, but I can’t take my eyes off of the gown because he is so hard and so huge. I tell him not to worry; I am a professional and have seen lots of guys get hard. Truth be told though, I’m wet and all worked up because his cock is so big.

I instruct him to bend over the table, spread his legs slightly and relax. I press my body up against him from behind, my nipples erect. I then slide a finger up his rectum. I hear him gasp, and I whisper in his ear, “It’s okay, this is just procedure.” He turns around and I push him on to the table and begin stroking his cock. I say, I need a semen sample for the lab. I begin milking his cock. At first I am using my hands, then my tits, and then finally I slide a finger back up his ass to get him to cum. I assure him this is just the lengths some nurse are willing to go for special patients. I tell him it I need to make sure his penis is in working order, so I fall to my knees and begin to suck it. I say, if it’s a great healthy penis, it will be able to ejaculate a second time and will taste a certain way. He tries to grab my breasts, which are now exposed, but I explain my lack of clothing is just to facilitate a nice visual to help him ejaculate but that this exam was about him, not me. I milk a second sample out of him and tell him he appears to be in tip top shape with a very well working penis.

By this time, my cunt was dripping down my thigh from such a hot naughty roleplay. My friend was also wicked horny and he had already cum twice. We fucked like rabbits for a couple hours in his brother’s exam room. I love all kinds of roleplays. I am a creative phone whore, so whatever your hot roleplay scenario, I promise you creativity, enthusiasm and a wet pussy.

Message In A Bottle

I am your message in a bottle. I washed up on the shore of your life. When you opened the bottle you got the message you had been looking for. A woman that would do all the things she never would and not expect anything in return. A no strings attached, kinky affair. I got what I wanted to, someone that had bottled up sexual frustration and tension that would scratch every kinky and perverted itch I have, no questions asked. You come to me not because you have to, but because you want to. She would tell you what a sick fucking freak you are for wanting to do the things that make your blood boil and make you cum hard fulfilling your needs. But I don’t, I know what you want, what you like and how you like it. With me your fantasies are fulfilled, your desires are met. I know that you want me to lick your balls and ass while rubbing that hard cock up and down with my hands. I know that you almost cum on the spot when I stick my tongue in that tight ass of yours. I know that you love to shove that cock in my mouth while spitting all that jizz down my throat. I don’t think it is nasty or gross but instead I swallow every drop and beg for more. Just like the slutty whore you need. And you give me all of it in return, fucking me, satisfying me, it is the perfect arrangement. Each time I think about you cumming to me my pussy gets wet and I get excited, knowing that we are about to do things we shouldn’t yet we can’t help it. The best sex is taboo and secret. It is oh so wrong, yet oh so right!

You Cough, Bitch!

I had my physical this week.  I’ve been with the same physician ever since I was a little girl.  He’s seen me my body change, and my cock grow over the years.  He’s been there to answer all my questions, and helped me through my very confusing puberty years.  He’s a dear, old friend…and lover.  My doctor loves sucking my dick!

My mom stopped accompanying me into the exam room once I could speak for myself, and my dad has always been too embarrassed to even go to the doctor’s with me.  So, my doctor’s been sucking my snake since before I needed the hormones he prescribed for me.  As a teen, I got addicted to the power I felt, when fucking a man’s face.  Once I finished puberty, and he saw that I was working with a big clack cock, he started talking to me about ass play.  My doctor gave me my first taste of twinky hole.

Now, I he begs for my weapon of ass destruction, even when I don’t have an appointment.

 

 

Pretty In Prostate

There is nothing better then getting your salad tossed, a great rim job and the perfect prostate massage. I call that the holy trinity!  Will you give me a work over and include the holy trinity?No one knows how to give the holy trinity like like a tranny out of control! My dick is getting hard just thinking about spreading my ass and letting you cum inside, no pun intended! If your not sure how to give the holy trinity, don’t worry I will show you first hand. I will lay you down and take my time showing you exactly what the holy trinity is all about. Before I am done you will be repeating “Oh God, Oh God” And so the name, the holy trinity. I love it when I watch your dick grow knowing that I am the one making you hard as a rock as I turn you inside out with my mouth and fingers and all my tranny tricks. If I am lucky, you will learn quickly and  you will reward me by sharing the trinity with me and filling  my ass with hot, hard, stiff cock and lots of sticky jizz.

Switch Hitter

I am sitting here rubbing my perky tits the nipples are so hard! I slide my other hand down to my crotch and start stroking my huge cock as I think about our date tonight. Last night was so much fun. The movie was perfect, dinner was divine. You are a wonderful kisser and making out drove me crazy. I could tell by our conversation that you are very adventurous sexually and I am pretty sure tonight I will share my huge fuck stick with you. I can’t wait to get down on my knees for you and suck your cock like no one has ever sucked it before. I would love to put my dick between your lips and feel your tongue roll around my shaft. We are going to have such a great time you and I. I hope you will let me pour sweet coconut oil all over you and give you an intense massage which will eventually lead to a prostate massage and rim job before I take your ass for my own. I will gladly give you mine as well. Ahhhh I am going to cum just thinking about it, it is going to be so fucking hot. See you soon big boy.

Your Switch Hitter

Jingle Balls

It was so cold out last night and I knew the Santa outside of the department store ringing that bell all night had to be cold. I stopped and talked to him for a long time. He looked so cute with that fake beard and that suit that didn’t fit right. We talked for a long time and it seemed like the natural progression to things when he finished his shift and I offered to buy him a drink at the local bar. Before we knew it the bartender was calling last call and we were pretty fucking trashed. Of course I asked him if he wold like to come to my place and keep drinking. I was so happy when he said yes. It wasn’t long before we were making out and getting undressed and that is when I introduced him to my jingle balls. He gave the most delicious prostate massage and in return I gave him a rim job he will never forget. I was he queen for the night and he was my queen. I think I will be visiting the department store again tonight!