Category: Shemale 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!

Tranny Locker Room Lolita

I go to the gym several times a week. This small little local gym I belong to understands I am a special girl and they allow me to use the girls’ locker room. Even though I have a dick, I identify more with my female side. Today, however, I was feeling particularly masculine after a workout. I decided to shower with the boys. It was crowded too. I walked right in, dropped my towel and hopped in the group shower. All eyes were on me. Just the reaction I was hoping for. In fact you could say I got a rise out of a few of the guys. None of the guys in that locker room seemed to realize that I was a chick with a dick. They knew now.

My cock was rock hard. I love attention. I was not the only one hard. I felt like a Locker Room Lolita. I got on my knees and sucked off 5 guys. I deep throated each one of their cocks. Balls deep I believe is what it is called. I swallowed every load of cum that was shot down my throat too. Steam was all around me, I was wet from the shower water and I had a mouth full of yummy spunk.  I was all set to call it a day and clean myself up when a super well hung guy stepped out of the bathroom. He was like, “Not so soon pretty lady. I want my turn.” He came up to me, pushed me down on his anaconda and skull fucked me until my eyes almost popped out of my socket. He shot one of the largest loads of jizz I have ever swallowed.

I was a little cum dump tranny in that locker room today and I loved it. I might have to shower in the boys room more often.

Two Cocks are Better than One: Tranny Phone Sex with Carla and Diamond

I remember the first time I met Diamond.  It was at her holiday office party a few years ago. I was her asshole boss’s date. He was a total prick to his employees, this I knew, but he had a big wallet and spoiled me with designer shoes, jewelry, spa days and trips. He knew I was a special girl, but no one else did. I was his dirty little secret. He considered himself a straight man with a reputation to uphold that would have been tarnished if it was discovered he loved having a 10 inch cock up his ass.

Well at this party, I saw Diamond and I just knew she was special like me. Pretty thing. In fact some folks at the party thought we were sisters. I was flattered. I wondered if he knew she was packing meat in her panties too.  I followed Diamond into the ladies room and told her I knew her secret. She asked how I could I know, and I whipped my cock out. Her eyes got big. I was the first special girl she had ever met. We got to talking. Turns out my date, her boss, found out her secret and fired her earlier that day. He told her she could come to the party if she said nothing to anyone. Essentially he was going to give her a severance package to just go away quietly.

Well seeing how I had been fucking his ass and sucking his cock for months now, I found his decision just a tad hypercritical. I told Diamond I was going to get her job back for her.  We walked back out together holding hands and watched him squirm. I whispered in his ear, “Hypocrite. Hire her back, give her a raise, or everyone will know you are a fudge packer.” He looked mortified. I texted him a few pics of us. One of me fisting his ass, another of him sucking my cock with cum all over his face, so he knew I had evidence against him. Some may call it blackmail, I prefer to think of it as social justice. I am proud to be a chick with a dick. No amount of pampering would let me ignore his hypocrisy.  I hate a closet fag.

I never saw him again after that, but Diamond is one of my best friends now. We have gotten into all sorts of mischief together, including blackmailing other closet fags. In fact, she the best kind of friend. We can shop together, pick up men together and fuck each other. Last week we threw our own holiday party to celebrate our 3 year anniversary. We got to drinking, then making out, then we both had hard cocks to contend with! I had mistletoe hanging from my throbbing rod, and of course Diamond kissed my balls and my cock. Her presence gets me hard. Next thing you know I am riding her pretty cock and she is cumming all over my tits. 

Now Diamond and I fuck each other all the time. How can we not, look at us? But, we love sharing cock together too. Especially unsuspecting cock. You know two cocks are always better than one. Don’t worry, your dirty little secret will be safe with us, well maybe!

Sissy play time with pony boy!

I had an absolute hell of a time with a sexy man who thought that he was a big manly man. Turns out he just needed a real big dick lady to dress him up and make him my bitch. I loved every minute of it, and so did he. He makes my little pony look like shit.  He is the my little pony who cums when he is told.

I love my first time sissy in training pony boy. He was so much fun. I dressed him up and made him swallow My foot long cock all the way down to my balls. I sprinkled glitter all over his head while he licked my balls, and we turned on the rainbow  lights in the living room so I could watch my cum run down his face the feeling was wonderful.

I enjoyed my time having fun with my sissy in training. I am always looking for a sissy to play with. I f you would love to play with me, and let me take you to new levels of pleasure, or even help you be my nice sissy sex boy toy for a day. i will be here waiting to hear from you.

Virgin Phone Sex: The Tranny and the Teen Snowed In

A few winters ago, I went on a solo skiing trip. Hit a major snow storm. My car got stuck in the snow and I had to walk quite a bit to get to the cabin area.  Before I got there, I found a cute young girl who was making a snowman. She was clearly a snow bunny. She was frolicking in the snow naked. The cold wet snow she claimed felt good between her butt cheeks, and invigorated her cunnie. I thought she was crazy. I was freezing my balls off. She didn’t yet know I had balls, and it was so cold I was beginning to wonder if I still had them. She double dog dared me to take my clothes off and make snow angels with her. Well, I never refuse a dare. No matter how cold I am.

When she saw my cock she could not help but get all wide eyed. Apparently she had never seen a chick with a dick, didn’t even know we really existed. I played in the snow with her for a bit, then I told her we needed to find a warm place. Her cabin was close, so we went there. The snow continued to fall, stranding us inside for several days. My preference is hard cock, but I have been known to play with pussy. And, this sweet barely legal girl had a sweet tight muff on her. I started a fire in the fireplace and between her legs.

I’m best known as cocksucker extraordinaire, but that weekend I was a supreme snatch licker. I made that girl squirt for the first time with my talented tongue. I also taught her how to be a better cock sucker. She was a natural, just needed some pointers like licking  that backdoor pussy. Turns out she was a virgin. I was her first BJ. She had given a handjob before, but was saving herself for marriage. My naked snow bunny was a virgin? Whoa. Didn’t know virgins existed still. Because I was not all man, she felt like she could fuck me and still be a virgin. I was not going to argue with her about a technicality. I slid my hard cock in her tight cunt.  For a moment, I understood what dirty old men were thinking. Something so tight on your cock feels amazing. Her cunt was tighter than any virgin ass I had ever fucked.

I came so hard in her virgin cunt. Biggest load I had shot in a long time.  She was convinced she couldn’t get pregnant by me, but I still got swimmers, so I can knock a chick up. We fucked for days until the snow let up and her family returned from where they were stranded. They never knew  I was not all female nor that I had popped their baby girl’s cherry. They thanked me for taking care of their angel. They never knew I was a naughty tranny. We washed the bear skin rug to hide the evidence.  Not a snow day goes by now that I don’t want to frolic in the cold wet snow. And I get hard thinking of the sweet tight young cherry I popped and wonder if I am a mother.

Dominatrix Phone Sex with Carla: Be Thankful for Cock in Your Holes

I want to wish all the horny men out there a Happy Thanksgiving tranny style. You see this is one of my favorite holidays because I get to do a lot of stuffing.  I get to stuff my big cock into pretty mouths and tight asses; and fill them with my special gravy. The best part is when a guy thinks he is going to be stuffing a pretty pink pussy and  he gets stuffed instead. But the reality is that many guys, you included if you are reading this, want to be stuffed and not just for the holiday. So many guys are bi curious, and afraid for myriad reasons to actually be with another guy. I am the best of both worlds. I have a nice beautiful cock to stuff mouths and asses with, but soft boobs and a smoking body to hold and kiss. I promise you, once you taste my gravy, pussy juice will never measure up.

I picked up just such a guy today as I was holiday food shopping. He acted like he didn’t know I had a special package in my panties. And once he saw it, rather felt it, he tried to resist. But as soon as I stuffed his mouth with my cock, he got weak in the knees. He polished my knob like a Hoover vacuum cleaner and tried to convince me I was his first cock. If that was the truth, then he had been thinking about sucking cock since he could walk. I gave him a huge load of gravy. Of course he was thankful for it. I even let him drink a special holiday sauce mixture of my cock gravy and piss.

Of course I had to stuff his ass too. I mean really, it is not Thanksgiving without something being stuffed inside an ass, right? My new fuck slave is such a dirty bird. He begged me to jizz in his ass, which I would have done with or with his pleading. Tight ass too. Not sure how long it will stay tight since I love stuffing asses, especially over the holidays. Of course when you are fucking a virgin ass, you always run the risk of a little extra gravy on your dick than planned, but we should be thankful for the food before us. That is why I made my fuck slave clean off all that extra gravy from my dick. He needs to be thankful I’m fucking him so good anyway.

Do you need some Thanksgiving stuffing? I’m happy to fill you up with my special gravy sauce. If you are new to the shemale thing and get scared, don’t worry, I won’t let you back out. I know your darkest desires. And trust me, once you have been stuffed with my cock, you will be very very thankful you met me.

 

Let Me Be Your First Cock

I consider myself a woman, but I still have some male instincts I guess. I love the outdoors. Hiking, white river rafting, camping, cross country skiing… And the Fall is the best season to enjoy the outdoors. Last weekend, I decided to go camping. The intent was to go solo, do some hiking in the day time and at night, in my tent, listen to nature, relax and maybe even read a book or two. Masturbate under the stars.

My alone time changed when I caught the fancy of a rugged park ranger.  He wore one of those sexy Smokey the Bear hats like Pharrell does in that cute Happy video. He was worried about a pretty girl camping in the woods all by herself. So sweet and old fashioned. He came by my tent the first night to check on me. Of course I invited him in for drinks. I had a couple bottles of wine with me.

I am a sucker for a gentleman, and he was a sucker for a pretty face. As soon as he kissed me, he pitched his own tent in his pants. I love getting guys hard. Especially unsuspecting ones. Very rarely do any leave once they discover my pleasant present. My sexy ranger was no different. After I sucked his hard cock, he went down to eat my pussy, saw my throbbing cock instead, and said, “Well, how do I know unless I try.” He went right down on my cock and as a newbie, swallowed all ten inches until my balls were against his chin.

I let him fuck my ass. It was his first time with a cock. He fucked me good too. Shot a big load of jizz in my ass. Better than starting a fire to stay warm. I’ll take hot cum up my ass any day over a fire. He came back every night I was in that tent too. The last night he let me take his ass for the first time.  It was tight. I love a tight ass. A virgin ass is even better. Once a straight man has my cock in his ass, he doesn’t look at pussy the same way again.

Let me be your first cock!

Fall Is Time For Hunting

The leaves are changing colors and dropping from the trees. Animals are foraging for food and preparing to hunker down for the winter. Hunters are dressed in camouflage with their manly guns, hunting for meat like cave men.
It is a very primitive time of year. And very erotic in a way.
Some friends of mine that enjoy the sport of hunting invited me on a hunting trip last week. Laughing hysterically I told them I don’t know how to shoot a gun nor could I ever kill a living creature.
They told me not to worry I could sit at the hunting cabin, enjoy the peace and quiet of the woods, as long as I made sure they had dinner when they got home from the hunt.
After thinking about it I agreed, and I am glad I did!
I spent my days reading, listening to the radio and sitting out side in the open jerking my cock that seemed to stay hard more then normal out there in nature.
It was fun making sure the manly men were fed and taken care of in the evenings. And I liked sitting around the fire with them listening to the stories of the day and drinking beer.
On the very last day of our trip, one of them came in early and there I was, eyes closed sitting outside, cock in hand beating my meat hard and fast.
I felt someone looking at me but I was to far gone to stop, look or care.
When I finally blew my load and opened my eyes there he was with his dick in his hand.
He came to me and told me that he had never had the guts to approach me and that inviting me was his idea. He knew this was his last chance to come to me and tell me what he had always wanted.
I took him by the hand and led him inside. By the cabin fire I kissed him gently working my way down to his throbbing cock. Taking it into my mouth and working my magic, my dick got hard again as his body responded.
I sat back and asked him what he wanted to experience. I told him not to speak it to just lead me and I would follow.
Tentatively he put his mouth on my dick. I knew he had never sucked a dick before. But he mimicked what I did to him and he was fabulous.
He looked at me and asked if it would be OK if he stopped before I came. He wanted to feel me inside him and he wanted to be inside me.
I was delighted and took him gently, licking his tight virgin ass before stroking him as I eased in. He responded by rocking back against me and moaning. His desire brought me to orgasm quickly and before I knew it he was inside me fucking me with all the passion he had pent up.
He came deep inside me and kissed me hard, thanking me.
We laid on the blanket in each others arms for a while before cleaning each other up and cooking dinner together.
I guess my hunter bagged a deer on this trip. Just not a four legged one, a three legged one.

Panty Woshiping Phone Sex

I had to put an ad in the paper for house keeping help. There was just no way around it.
I interviewed so many people that I lost count but when I met Rory, a sweet young man that was a touch on the feminine side, I just knew he was was the one.
I am only particular about one thing, my panties. I guess you could say I have a panty fetish. I have two drawers full of nothing but silky soft panties in every color, shape and style you could imagine!
I came home early yesterday and to my surprise Rory was sitting on the floor in my bathroom surrounded by every pair of panties that was in my hamper with one pair that was full of cum in his face licking them.
WHAT A NAUGHTY MAID!
Despite the original rush of anger at the site of him with my precious panties. The vision of him licking the cum out of them made my dick instantly hard.
I didn’t give away how fucking hot I was, instead I acted upset.
Begging me not to fire him, pleading that he needed this job, Rory confessed his secret. Rory is a panty worshiper. Which I guess is just about the same as having a panty fetish.
He explained just how he felt, how the silky feel of the material stirred something in him, not only when he held them but when he wore them and felt them against his body or when he saw them on others and touched and licked them. How he could cum with out touching himself when he smelled and licked panties.
It really didn’t matter if they belonged to a woman and were filled with her juices. Or if they were filled with the cum of her lover that dripped into them mixed with her own juices. Or if they belonged to a man or a transgendered person and were soaked with sperm.
It wasn’t the fluid as much as the panties and the idea that he was licking the sex off them, and how they felt in his hands and on his mouth and face or being rubbed on his body.
He never had to touch his cock, which was so much smaller then other men. for it to spew cum from his love for panties.
By the time he was done explaining all this to me, stirring the same feelings that I have, I was ready to explode. My own dick was throbbing in the silky pink panties that I had on.
Yanking him up from the floor, I ripped my skirt off and pushed his head into my dick as it spew cum all in my panties, making him lick it all off.
He was as surprised to see my cock as he was pleased to be licking the cum off me.
I think I am keeping my naughty maid.

T-Girl’s First Time: Popping the Cherry on That Back Door Pussy

Every girl remembers the first time she lost her virginity. Even though I am not a traditional girl, I am no different. I was nervous too. Girls are worried about making a mess when they pop their cherry. No girl wants a guy to see all the blood that usually accompanies the first time, nor does she want to endure the pain that is rumored to come with losing one’s virginity. My traditional girlfriends talked about doing things to prep themselves for their first time. So when I was ready to pop my cherry, I tweaked some of the advice my girlfriends gave me to fit my unique situation.

I bought a big dildo and began using it on my ass so it would not be quite as tight. Every day for weeks I fucked my ass for hours with my special toy. I was afraid of shitting myself  when the guy I was seeing popped my cherry. I read about enemas, found a video online, and decided to make my own coffee bean enema. I was too embarrassed to go into a drugstore and buy a pre-made one.

The day before I planned on letting Ryan fuck me, I gave myself a homemade enema so my ass was cleaned out and I would have no embarrassing accidents to ruin the moment. I pretty much just drank water until I met him. After our date, I told him I was ready. He was not prepared. I had been stalling him for months. I told him I wanted him bareback in me. I mean, he didn’t know I could not get pregnant. We had to do it in his parents SUV in the back seat as we had no private place to go.

I was nervous for lots of reasons. Would it hurt? Would I make a mess? Would he realize I was not 100% female. I was in school still and only a few teachers and friends knew my secret. I fit in as a girl. Anything else I was a freak and I desperately wanted to fit in, but I could not avoid the first time forever. I had him take me from behind to hide my cock. It was dark. I had inserted all sorts of lube to make my ass feel like a wet pussy. It was his first time too so I figured he would have no baseline to judge.

It worked. He slid his hard cock in my back door pussy for the first time, popping my cherry. It felt so good. Better than I could have imagined. I don’t know if it was because I prepared myself for the first time, or that I was just meant to have cock in my pretty back door pussy, but I started fucking all the time. Soon my secret was out. But so many guys had fucked me and they didn’t want folks to know they had been with a T-girl so they kept their mouths shut. Now I don’t hide who I am. I am proud of my duality.  Proud of my big throbbing cock.