Category Archive: Ladyboy teen

Confession

tranny phone sex camillaMy grandson has always been a Sissy. She has always been sweet and loves to please. She is very subservient and loves being on bottom. We know this is how she is and we love her just the way she is. Sso yesterday when she was staring at my huge Nana tits with a dreamy look in her eye, it didn’t surprise me that she started up a conmversation that ended in a confession that I had secretly suspected for a long time. She is sure she wants to be a girl and she needs to know how to do that. She knows it is possible she just doesn’t know the details. It wasn’t hard for me to get a hold of an old Tranny friend and she was more then willing to take my grandson under her wing and show her all the in’s and out’s from the most intament to the clinical aspects. It was fun to watch my grandson learn about the knew Tranny life that she wants so badly!

Nana Camilla

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Tranny Phone Sex Shemale Seeking Man For Deep Anal Penetration!

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I love cock! I mean, of course I do. They other night I was longing to feel a stiff hard rod deep inside of my tranny phone sex ass hole. What better way for a shemale seeking man to find one then to dress like a super slut and go out. I had everything going for me, tight red dress and slutty heels. Me and my beautiful body just screamed “Fuck me” to anyone who laid eyes on me. It did not take long for me to attract someone who was as ready to fuck as I was. We had a few more drinks and then went to the dance floor. I could feel his cock pushing against my ass. I bit my lower lip and looked at him. That was it, we could not take anymore! He grabbed my arm and took me to his car. He jumped in the drivers side and me in the passenger. He pulled his hand up my leg as he was driving till he reached my cock. I moaned as he began to tease me. Once we reached his place there was no more holding it in! I stripped off my dress and pulled me down so that I could suck on his big cock. Then he flipped me over onto the couch. He started to tease my ass hole with the tip of his pre-cumming member. He slammed his cock all the way int my tight ass hole. I moaned as he fucked me over and over again. Fuck it felt so good! He came filling up my ass right as my own cock exploded all over my sexy tight belly. What a man!

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Little Boy Cock Avery

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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, Lady Boy Phone Sex or Both?

tranny phone sex mature slutTranny phone sex is my newest obsession. I have been going on tranny dates; watching tranny porn; even trying to find sexy shemales to go clubbing. The best of both worlds thing as me super horny. I love cock, yet something about a pretty face and nice boobs gets me hot and bothered too. I have tried a variety of shemales, but not a lady boy phone sex chick until last night. I found a bunch with escort ads on the back pages and decided to hire one.

Most lady boys are Asian, very young looking. Barely legal I suspect, but as long as 18 I won’t lose my job! Something so exotic about Lucy. I was drawn to her pretty face, her tiny features and her nice big thick cock. She was a submissive tranny, but that was fine because I am a switch. I was feeling rather dominant anyway. I picked her up, felt her package to make sure no bait and switch. Hard as a rock. She said I was the hottest MILF she had ever seen.

lady boy phone sexI said screw dinner. We went back inside, had wine and fucked. I brought my strap on! I had her suck it to get it wet, before I slid it into her tight little ass. She had such a tiny frame. I think the contrast between her small figure and big cock is what attracted me. I reached around to stroke her cock while I slowly pumped in and out of her back door pussy. She moaned so softly it was a huge turn on. I wanted to feel her inside me too. I sat on her cock and rode her up and down while kissing her.

Softest lips ever. She was an amazing kisser. I’m not sure what has gotten into me lately. Well tranny dick has gotten into me! I cannot get enough sexy shemale cock. She came deep inside me and I came so hard with her. Have you ever been with a tranny? I highly recommend it.

Farah

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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. 

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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. 

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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.

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Tranny Phone Sex Surprise: My Son Wants to Fuck a Lady Boy

tranny phone sexTranny phone sex is nothing I ever thought my son would be into. He has always been mommy’s little mother fucker, literally. One of the best fucks of my life. I was his first pussy. But lately, I have been snooping in his room and on his computer because he just has not been fucking me the same as in the past. I was shocked to see a bunch of lady boy and sexy shemale pictures on his computer. He even had a fuck a lady boy site up. This little thing looked so young too. Pretty little Asian chick with a dick. Small soft breasts; hairless body; pretty much looked like my teen granddaughter. Suddenly, I heard noises from my son’s bathroom. I peeked in and there was the little lady boy getting her dick sucked by my son. No wonder he was not into fucking me lately. He wants cock. Lady boy cock.

fuck a lady boyI was shocked at first, but as I spied on them, I found myself turned on by not only that cute little shemale, but my son’s bisexuality. I started rubbing my clit and fingering my puss as I watched my flesh and blood butt fuck a lady boy. I let out a moan, which got their attention. I was embarrassed, but my son said I should join them. What the fuck. I will try anything once. I stripped naked, got in the shower with them and sucked my first tranny cock. My son was suddenly alive for his mommy again. He fucked me up the ass as I sucked that tiny t-girl dick. Blew a big load of cum in my ass. So, my son is bisexual. If it makes him fuck my ass like that a again, I will suck an army of sexy tranny cock.

Samantha

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Tranny Phone Sex Panty Boy Days

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I was not always such a tranny phone sex hottie. In fact, before I was such a shemale chat slut I used to be a teen boy who was nothing but confused in the world. When my mom and dad were together I used to wait until they were at work and then sneak into her room. I would try on her silk panties and bras and look at how pretty I was in the mirror. I got in trouble one time when she caught me after I took a pair.

shemales chat They were lacy, I loved the feel of my balls through the fabric. How they would push through and I could run my fingers over my teen ball hairs. I took a second silk pair and started to stroke my cock with it. I could just picture mommy wearing then. Stuck a third used pair over my face and sniffed up the smell of her cunt juices. I could smell daddy’s seamen in them from when they had sex. She was pissed when she caught me. Told Dad he needed to punish me. I do not think she had his cock in my ass in mind.

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Lil Boy tranny Dick Avery

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Shemale Chat Bring Me To Tranny Dream Land

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I was on the phone with a client who was absolutely in love with shemale chat. I have to admit tranny phone sex has been something that I have always wanted to try myself. The idea of a beautiful lady boy to make me her bitch for the night makes my fat cunt start to get wet. I went to bed that night thinking that would be the last of it only to wake up in a strange new world. When I went to the bathroom I looked at my chubby cunt and lo and behold there was a meaty cock in its place!
I shrieked with excitement and started to stroke it. What a surprise. I went back into my bedroom and grabbed my new stiff rod and started to stroke it up and down. I had so much girth and I loved it. I jazzed all the way up my fat rolls and over my gigantic tits. My cum tasted sweet too, I tasted every last drop. The night I went out to the club and was a little T-slut. I fucked all kinds of pussies, ass and mouth. I had so much on my cock I lost track. When I went to sleep I woke up the next morning back in my own bed. It had only been a dream, but my panties were soaked, showing the fun time I had in dreamland.

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Chubby Cockwhore Katrina

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