Category Archive: Tranny sex stories

Collecting Tranny Phone Numbers

date a tranny darlaMy sweet sissy boy, born Harley, now known as Hailey most of the time, saw her first tranny porn. She had so many questions that I had to slow her down to answer them. I always knew that some day she may transgender and have reassignment surgery but now I believe there is no turning back. She has always wanted titties like mommy and I have told her often that we could make that happen when she got older. But now that she has seen real trannies and knows for sure they exist she is over the moon. She is dying to meet as many trannies as she can now. So I put an ad on Craigs List on the personal page looking to get some tranny phone numbers and introduce my sweet sissy boy to as many as I can. I hope that they will not only play with and guide my sweet son but that they will stuff his mommy full of tranny dick while they are at it.tranny phone numbers darla1

Tranny Lover Mommy Darla

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Tranny Phone Sex In This Teen Cunt Makes Me One Happy Slut!

Tranny Phone Sex

Everyone knows that I love to party. However, sometimes I get a little bit too trashed. I would have to say, a little is an understatement. I get way too trashed. In fact, when I thought that I had this sexy chick hitting on my I knew I had scored. She took me upstairs and started to lick on my cunt. I was in love with that tongue of hers. As I stumbled across the bed to lick on her pretty pussy found myself a tranny phone sex surprise. It was not a puss that I found but a big beefy cock. Without hesitation I shouted out that I loved chicks with dicks and started to suck her tranny cock. She pushed my head down onto her till I had her rod balls deep in my mouth. Her pre-cum tasted so good that I just did not want to stop. That was nothing compared to the way that perfect shemale fucked my cunt. She bent my drunk ass over and spit a big loogie onto my tight ass hole.  Without hesitation she shoved her full length into me. She was hung too so all of that dick stretched out my ass hole to the max. She was nice enough to even stroke my pussy while she fucked me. The two of us came together and she left me laying up there. She fucked me right to bed. Left her number on my arm in lipstick. I sent her a text a few days later telling her my cunt missed her cock, but sadly she never answered. I would be keeping an eye out for my mystery tranny. Although, my memory is clouded from all of the drugs and booze. HaHa oh well! 

PArty Slut Ryder

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Dressing Room Delema

tranny phone sex zettaI was shopping for a new summer out fit for a T-girl cook out a friend of mine was having the cumming up weekend. I love shopping so it was kind of hard to conceal my nine inch cock.
I was looking for a particularly cute little number that would allow my balls to hang out just enough to tease a certain someone that would be at the cook out.
When I arrived at my favorite boutique there was a new sales person there. A very hot little number that wore his pants a bit to tight for modern day standards but showed off his sexy round ass.
He pounced on me as soon as I walked in and was very attentive to my needs. Together we found a couple of really cute things and he sent me into the dressing room.
I heard him walk away as I was getting undressed to try on the first outfit. The next thing I knew the dressing room curtain was being flung back and there he was holding a few more things.
I stood there in my panties and bra with the head of my cock peeking out of the top and balls spilling out of the bottom.
Before I had time to cover up, he was in the tiny room with me, the curtain closed and my dick was in his hand. Without saying a word he kissed me passionately and then fell to his knees and took me in his mouth.
In no time at all I exploded in his mouth but wanted so much more. I had been looking at that tight ass since I walked in.
As I reached for him he shook his head and let me know there was no time. I finished trying on the clothes, and made my selection. As I paid I slipped him my name, number, address and an invite to the cook out.
He showed up and was the life of the party, sucking every shemale there he filled up on jizz. He loves being a bitch for big dick! And we all loved letting him!

T-Girl Zetta

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Tranny and Granny

tranny phone sex camillaHe has always had a feminine side while growing up. Always wanting to be with the girls. always wanting to wear my clothes and under clothes. When all the girls would get together for a make up party, he would sit with wide eyed wonder and watch us. We often let him apply the make up for us and would even put it on him. He would act shy like he didn’t like it but we all knew he did. We would often huddle together and giggle about it while we played with our pussies and told stories about what we thought was up with him, was he gay? Did he just like cross dressing? Was he a Sissy in the making? None of us could figure him out ad trying to made us all so fucking horny!
He is all grown up now and called me yesterday asking if we could talk over lunch. My heart skipped a beat and my pussy got wet, he was always one of my favorites, perhaps because he was so odd….
When the door bell rang and I answered it, there stood a beautiful young women. Something about her was familiar but I couldn’t place it. When she wrapped her arms around me and gave me a hug I felt the hard dick under her short skirt and was taken aback. But when I pulled away and looked in her eyes I saw the familiar loving look that couldn’t be changed ever,
It was him.
We had a long talk about his transitional surgery and how he was now transgender and happier them ever.
We went into my room and fucked just like we always had, only now along with her glorious dick she had phenomenal tits! It was the best of both worlds for me.
Calling him a her is going to take some getting used to. But fucking her now is something I am already used to!

Nana Camilla

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Pay Back Bitch

Tranny phone sex EllaA lonely trucker pulled up at the gas station in town. It was daytime and he treated me like shit like all these other fuckers do, calling me a fag and jeering at me. He was cute so I let it slide. Later that night, as I was walking home from fucking one of my regular bitch boys, he pulled up and asked me to get in his truck. He said he was sorry for calling me a fag and asked how he could make it up. I made him suck my cock right there in his truck and I could tell it wasn’t the first time the little sissy had done it either. He begged me to fuck his face, slap him with my balls, and he drank all of my cum with no problem. Of course I had to fuck his ass just to show him the type of bitch he really is. After I was done he thanked me and asked me could he see me whenever he came to town. I think I have a new regular bitch boy.

Tranny Slut Ella

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Tranny Phone Sex School Principal Prank Gone Wrong

It is not very often that I have to try to get things done. Most of the time it is as simple as a wave of my hand or bat of my seductive eye lashes that gets any guy to do what I want. However that was not the case when I got in trouble on my first day of school already. In fact, the principal gave me a detention. I was not going to be having that, no way not how. So I decided to have some fun with him, and pull a tranny phone sex prank. 

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I made a fake facebook and added the principal. I told him I wanted to tell him about my ladyboy teen parts that I had. How i secretly felt like a freak and just wanted someone to love me. At first he was not biting. Then I told him that I always wanted him to fuck me in my ass hole and that was all she wrote. My principal was on my fake shemale nuts just like that. I told him I would be going to the principals office and having some fun with him, he even told me just what time to get sent to him. 

Ladyboy teen

A friend of mine was waiting outside of his window discreetly holding a camera to record the whole thing. I had on a nice size strap on under my big skirt and went to the office just as he wanted. As I seduced the principal he was jumpy and ready to put my tranny cock into his mouth. That was until he lifted my skirt. The rubber dildo slapped him right in the eye and he jumped back, knocking into the window and spotting my friend. 

Shemale surprise

I started laughing so hard, holding onto my side and tears running down my cheeks. He hollered for my friend to come into his office. She ran around and busted through the door laughing forgetting the camera was attached to her hand. He asked what it was and then decided to punish us. He fucked the two of us in our asses hard! He did not even use any lube. Claimed we were too bad for the pleasure of anal fucking. I still put on the strap on and fucked him just like the T-girl he always wanted.

Sweet teen pussy Candy

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Hot Ass Phone Sex with Shemales

shemale chat MarianaYou love to call in for phone sex with shemales, but this time, I surprise you with something different. Usually, all you want to do is suck my tranny dick, but not this time. When you bend down to take me in your mouth, I have just one word for you. “No.”

I gesture for you to turn around, so you are now on your hands and knees before me. You feel me run my hands over your legs, up over your hips, and run them over your soft ass cheeks. I make a movement behind you, then you try not to jump when you feel a cool, wet finger touch your sensitive skin. The slippery finger slides its way right into your pretty little pussy and begins wiggling around. One finger at first, then two. I spread the two fingers wide, priming your ass for what is coming, making you ready. When I hear you begin to whimper, I know you’re ready for more.

I pull my fingers out and grasp my huge, hard cock. Leaning forward, I start poking at your sweet little ass. My tip begins to force you open and to enter just a little bit, enough to stretch you wide open enough to hold just my head. You’re not used to this, and you cry out with the shock, so I pause for a moment before continuing. Then, gradually, fraction by fraction of an inch, I begin to fill you, forcing my cock into your sensitive flesh. I move slowly, pushing in, then pulling out a bit, only to push myself in again, deeper each time.

I continue to fuck you slowly until I’ve filled you completely, and then… well, if you need a reminder on what happened next in our shemale chat, you can give me a ring, loverboy.

12-inch Tranny Mariana

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Tranny Phone Sex Slut Avery Makes Phone Sex With Shemales Too Hot To Handle!

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It is hot hot hot outside and this sexy tranny phone sex babe need to get her sexy ass wet. Unfortunately my pool is down so that means I need to seduce my way to sexy pool play time. It is never really hard, just have to find someone sexy with a sexier pool! I was walking along the beach sporting a sexy yellow bikini when that very person caught my attention. He stopped dead in his tracks to watch me walk past him. My ass cheeks looked amazing in that bikini, it is no wonder he stopped so suddenly. I turned around and started talking to the handsome piece of man meat and found out he was fairly wealthy. He invited me back to his place for a dip in his pool, I did not object. 

When we go there his intentions are very clear which is something I already could sense. I grabbed his stiff rod and held onto it. Not only was it long but super thick. All i could think about was how good it was going to feel stretching out my tranny ass. He started to pull down my bikini bottoms and my cock popped out. I expected him to be surprised but he told me he loved having sex with shemales and sucked right on. I started to face fuck his little mouth, listening to him choke on me made me smile. He then stood up and tossed me over spreading my ass hole wide just like I imagined. HE filled up my mouth with his cum when he was done. Said he did not want me cream pieing his pool. I could understand that, it was a perfect pool, worth the fuck! 

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Lil boy tranny dick Avery

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Tranny Phone Sex Wonder Women Force Fuck

Tranny Phone Sex

There is something about nerd herd conventions that I just can not get enough of. I thought I would find me some nice little boy meat to satisfy my cunt but i was quickly put into my place. I met a tranny phone sex slut who also had the hottest Wonder Women costume on. At first I was hating but that monster cock she had could not be hidden. I asked her if she would tell me what makes her women so wonderful, drawing my eyes to the bulge in her costume. She did not like that at all and told me I was a rude nasty bitch. I started to whimper, I knew I was not worthy of her sexy cock in my pussy, but knelt down in front of her anyway. Kneeling down she squeezed my cheeks between her hand and pulled my face close to hers. She ordered me to crawl like a puppy and follow her. I loved how forceful she was. This little subby needed to be put in her place sometimes. She took me into a back room and wrapped her hand around my throat. She pulled my skirt up and questioned if this was what i wanted throwing me across a table. I felt her force her cock deep into my ass hole. I went to let out a shriek and she slapped me across the back of my face and told me to shut up. I whimpered and smiled. We came together. I never got my wonder women’s number, and it is ashamed too! 

Subby Cum Slut October

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Tranny Phone Sex for the Man Looking for a Tranny

tranny phone sexTranny phone sex is for all you bi curious men looking for a down low experience. It is hard to spot us in public because we look just like 100%women when clothed. In fact many of us look better than most real women. I bet I look better than your wife, with or without clothes. When I have my clothes on, no one ever guesses that I have a hidden panty surprise. So, most of the men I fuck are not even looking for a tranny. They just think they are successfully picking up a hot bitch at the club. But if you call a sexy shemale, you know what you are getting. And, you know what you want. You want a beautiful cock up your ass or you want your cock up a beautiful ass. I’m a switch so with me you can have it either way. Shemale chat is the perfect introduction to chicks with pretty dicks. But be prepared. Once you have had a taste of tranny cock, you will find yourself cruising the gay clubs and personals looking for the real thing. Phone sex with a sexy shemale is not a novelty experience. Once you go tranny, you never go back.

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Tranny Carla

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