Calypso

Ladyboy Incest Phone Sex

by Calypso on April 30, 2016

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As a child I was one of those special little “boys” who loved to dress up in girls’ clothing and everybody already knew what I would grow up to be. I demanded that my parents let me grow my hair long and never cut it before we had a long talk about me being a girl!

I got lots of attention everywhere I went, especially on trips to my uncle’s house. My parents let me stay over all the time and we had some of the most perverse playtimes you can imagine. We had these sessions of almost ceremonious crossdressing phone sex, where I would wear intricate outfits for my uncle’s amusement. He’d take special care to dress me in tight silky panties… After all the pictures we’d take he really loved to start by lifting my skirt and gazing again at my panties!

All of my first sexual experiences were with him on those trips to uncle’s house. None of my family ever suspected a thing, but we were having Ladyboy Incest Phone Sex all the time! I sucked all the yummy juice from his cock over and over until one day he said he just couldn’t wait anymore, he had to feel how tight his little princess was. I laid back and lifted my legs so he could pull my pink panties off, then inch by inch took his cock inside me!

Big Dick Tranny Calypso
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Tranny in a Bikini Phone Sex

by Calypso on March 31, 2016

Calypso

SHEMALE CALYPSO MAKES SUCH A HOT BIKINI BABE! 

There’s nothing like carrying a big beach towel down to the beach and laying out to catch some sun. I can get pretty bored out there though, so I make sure to keep my phone on for Tranny in a Bikini Phone Sex to keep me entertained while I’m out there tanning my sexy long legs and skimpy bikini-clad body. I was out there all oiled up when this guy called me for some dirty talk. I thought I was all alone out there, I hadn’t seen anyone walk past in quite a while. I had pulled off my top so I wouldn’t get tan lines, and subconsciously my hands had wandered to my breasts, squeezing them and twisting my hard nipples as the waves crashed onto the shore next to me. His fantasy was to suck on a fat tranny dick for the first time, and I can’t resist a first-timer. It makes my cock so hard thinking about corrupting “straight” guys and getting them to wrap their lips around my throbbing erection. My cock grew so hard almost instantly, it was making a tent in my bikini bottoms. I was all alone so I thought why not? I reached my hand down and wrapped it around my thick cock and began stroking, imagining a hot mouth around my dick and the harder I jerked the more precum began oozing out. I laid on my side and blew my load in the sand… Just as I noticed a guy watching me ten feet away. Had he been there all along? Had he heard my entire phone call? I was freaking out but didn’t want to let it show…

CHECK BACK FOR PART 2 OF THIS KINKY PHONE SEX ON THE BEACH FANTASY! 

Give me a call today…

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8 1/2 Inches of Phone Sex Tranny Cock

by Calypso on January 27, 2016

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SHE DICK SO BIG YOU CAN’T SAY NO

Don’t try to resist it, pick your jaw up off the floor and realize what your position will be from now on… That is, wherever I tell you to be! I’m a very Dominant Phone Sex Shemale and you’re going to be worshipping me around the clock because I’ve got so much cum and you have to get it all out. There’s nothing like having the no limits rough sex with me, find out for yourself. You will be begging for me to fuck you harder and deeper with my 8 1/2 inches of Phone Sex Tranny Cock!

Of course you’ll have to get it hard first… on your knees… say “ahhhh!” Be the dirty tranny dick sucker you’ve always dreamed of. I love hearing guys gag and choke on this big fat dick, it’s usually always bigger than the cocks on the guys I bring home too. Haha it makes me giggle to look down at you, past my luscious tranny titties of course, to see you there blowing me like a hurricane all the while your dick is hard, throbbing and oozing precum in anticipation of the deep and hard fucking I’ll give you next! Don’t be scared, we’ll use plenty of lube on that booty and you’ll be crawling back for more time and time again!

Give me a call today…

Big Dick Tranny Calypso
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Shemale Stepmommy Phone Sex

by Calypso on January 11, 2016

calypsopic

YOUR NEW STEP-MOM HAS A SURPRISE…

You’ve come to stay this whole winter break with your father but he will be away a lot on business. I guess it will be just you and me, little fella! I know it’s been hard since your parent’s divorce but Daddy’s moved on and with someone as sexy as me I’m sure you see why! Your new step-mommy is really nice and sweet, and curvy, sexy and cool too… Don’t worry, over here we don’t have all the same rules as your strict mother and I’ll make sure that you’re having a great time while you’re staying with us.

Wait a minute! Did I just catch you staring at my ass? Ok, you’re not the first young teen boy I’ve caught staring… Hmm why don’t you join me in here in the bedroom? No, don’t worry about what your Daddy will say, he doesn’t have to know! I see that cock of yours is so stiff that you’re about to burst through your shorts. Come now, don’t be shy, go ahead and pop it on out for me. You’re blushing and nervous I can tell, but your step mom has got a surprise for you, I’ll get on my knees right in front of you. You can’t resist as I’m opening my mouth wide to take all of that yummy little teen boy cock into my mouth!

I didn’t think you’d notice when I reached down to start stroking myself under my dress while I sucked you off but it seems you’re a bit curious about my body now. I begin to strip down and show you my perfectly round tits, my supple ass and best of all my huge shemale dick! Since you’re so curious why don’t you get on your knees and put this big cock in your mouth, it’s time for some Shemale Stepmommy Phone Sex!

Give me a call today…

Shemale Mommy Calypso
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TS Mommy Phone Sex

by Calypso on January 9, 2016

Calypso (7)

SHEMALE MOMMY CALYPSO    855-553-2339

That’s right, I may be a hot-bodied transsexual but I know just what this little Momma’s boy needs… you need the tender loving care of a dominant Mommy and I’m here to give you the nurturing you so desire. You see these giant sweater puppies here under Mommy’s shirt? Those are going to be your pillow today, for you to rest on my chest and feel close to me and hear me softly coo to you as you get ready for some Tranny Breastfeeding Phone Sex. I’ve been taking all the proper supplements to make these tits nice and full of milk and you’re going to suck it all out of me today. They’re practically bursting now and my little baby boy can suck on Mommy’s nipples while I reach down and play with his little dick, rubbing it and making it feel real good while you’re in Mommy’s lap.

Don’t be shy. You know you need something a little outside the box, something dirty and comforting, hardcore and filthy yet nurturing all at the same time. These are the powerful emotions that get stirred in TS Mommy Phone Sex. I’ll have you suck on my yummy cock just like a pacifier too, num num num you suckie and Mommy will cummie, give you something yummy for your tummy. I love to baby talk and give my little tot something fun to play with, unless he’s a bad baby. This Shemale Mommy has a lot of punishments up her sleeve for those bad babies out there in fantasy land…

Give me a call today…

Shemale Mommy Calypso
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Kinky Threesome Phone Sex

by Calypso on January 2, 2016

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KINKY THREESOME! CALYPSO – 855-553-2339

Happy New Year’s to all! I’ve already started the year off with a BANG! A gang-bang that is. With one of our very own sluts here from the dirtiest place on the web… I had a very dirty tryst with two sensational bodies, one a hard-body muscular guy with a nice large cock, and nice perky-tit blonde babe Randi… I tossed myself into the mix for some Kinky Threesome Phone Sex!

The best part, I think, was when Randi was on her knees. She’s such a good little blonde cock sucker, she really knows how to twirl her tongue around a dick and make your eyes roll back in your head. Our frisky fella friend would grab onto my cock and stroke it while she was blowing him, it made the whole experience that much naughtier. We couldn’t keep our hands off of each other!

Finally he got his cock inside her, right up her ass. This left her pretty pink pussy wide open for none other than my own hard shecock. I slid it inside her, but only after teasing her clit, licking and sucking on it and making my way up to her puffy pink nipples with my mouth. She moaned so loudly when I pushed my big cock in her, it made me want to fuck her really hard. The guy on bottom loved that he could feel our balls slapping against each other as we fucked her holes, stretching them out. We both came in her at the same time!

Calypso
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BBC and Shemale Cuckolding Phone Sex

by Calypso on December 9, 2015

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 SPH ~ BITCH BOY ~ SHEMALE CUCKOLDING
CALYPSO ~ 855-553-2339

Come here you pathetic little shrimp dick. Your wife and I have been talking, girl talk. I bet you know just what we’re thinking. Yup, after we dress you up in our lingerie, you can be our bbc fluffer. High heels, silky stockings, panties for your prissy tiny clittie and a padded sparkley bra… the perfect outfit for you to wear while wifey gets stuffed with cock in front of you. Your limp dick is only a fraction of the size of what a real woman needs, so now you’re going to get BBC and Shemale Cuckolding Phone Sex! It’s going to be your wildest fantasy come true when three black guys with huge cocks are pounding in and out of your wife’s holes. It’s time for some breeding, after I get her pussy ready for those bbc’s. My eight inch cock needs you to suck it and choke on it first, on your knees slut boy!

Your wife takes pictures for us as you suck on my cock and set this whole thing in motion! She bends over right in front of me and I slide my wet cock from your mouth into her wet pussy and back again, letting you taste her sweet juices before I plow into her again! She moans so loudly and I command you not to touch your miniature boner until you’re told to. It’s so throbbing and hard for the tranny cuckolding right in front of you.

YOU STAY ON YOUR KNEES ~ IT’S TIME FOR SOME BBC FLUFFING! You’ll have to CLICK HERE to read the rest of the story…

Calypso
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Double Anal Phone Sex

by Calypso on December 3, 2015

Recently a guy asked me on a phone sex call what’s the dirtiest thing I’d ever done. I had to think long and hard about that one… From shemale gangbang phone sex to abdl play, I have done it all. And loved every minute! I’ve got a lot of dirty tranny experience in fucking and sucking, and regularly push myself to the limits and try to broaden my spectrum of kink. After much debate, I decided the dirtiest thing I’d ever done is have Double Anal Phone Sex with two guys I met at a bar. I invited them back to my place and things got really wild. I got on my knees and started sucking them both off at the same time. Then, I stood up, took my top off and watching them marvel at my perfectly round tits, I lifted my skirt. You see, I hadn’t told them I was a shemale before. They were so shocked! One guy looked to the other and said, “How are we both supposed to fuck her at the same time if she’s only got one hole? Let’s teach this lying bitch a lesson…”

Calypso (7)

They pushed me down on the couch, bent me over and ripped off my skirt and panties. I didn’t know what to expect, but suddenly felt one huge cock push into my tranny asshole. I thought the other guy would come around and fuck my face, but he stood back and watched for a minute or two and then hopped on top and slid his dick in too. I’d never been so full of cock in all my life!

Calypso
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Glory Hole Phone Sex

by Calypso on November 22, 2015

It had been a while since I got down on my knees in that bathroom and waited by the hole for a big cock to pop through. As I kneeled in anticipation, I wondered about the guy who would thrust his cock into this stranger’s mouth next. Would he have a big, long cock? Or, maybe a short and hairy dick? The truth is, in Glory Hole Phone Sex you never really know what you’ll end up with… But, I’m such a shemale jizz junkie I just keep coming back!!!

Before too long, I heard someone go into the stall next to me. He pissed and grunted something I couldn’t make out, and then a few minutes later a semi-erect cock emerged in front of me. I opened my mouth wide, taking the full length of the dick right into my mouth. I sucked on it, feeling it grow inside my mouth. That made my shecock so hard and throbbing! I began squeezing my own dick and sucking intently.

I pushed my mouth vigorously towards the hole, giving a peek of my pink lips to the man on the other side. Almost instantly after deep-throating his big dick, I felt it begin to ooze hot cum inside my mouth. I sucked and slurped, getting every hot drop of cum out of his balls before taking my mouth off his cock and watching it disappear through the glory hole.

Hmm.. Maybe I should go into the other side and wait for another cum slut to take my place here on their knees… After all, I now have a throbbing hard she-dick!

Calypso
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Ass Licking Phone Sex

by Calypso on November 16, 2015

Feeling naughty? Pick up the phone today and we will have some kinky fun. I’ve got a hard cock and a lot of dirty thoughts. I love having Ass Licking Phone Sex the very most. You know you really want to feel my wet tongue sliding around your asshole baby, don’t be shy. I’ll make you feel really good and stroke that cock of yours at the same time! Or, if you’re feeling like burying your face in my perfect shemale ass, you can lick all over my tight little hole! Slide your tongue up and down my ass and all over my perfectly round cheeks! Tongue-fuck my tranny asshole, nothing makes my cock harder!

TRANNY WHORE CALYPSOI’ve got no limits baby, so if you want to get real nasty after we get started in the ass licking fun then let’s do it! I bet you’d like to slide something besides your tongue in me anyways! wink wink! Bend me over and find out what that hot ass of mine feels like! I want your thick dick inside me so bad… I’ve been thinking about twerking on your big dick since the first time I saw it get hard!

Reach around and grab onto my huge bouncy titties as you’re driving that cock inside me. Mmm, I get so hard while you fuck me… I’ll be stroking my shecock while you fuck me harder and harder. As soon as I feel you begin to shoot your hot load inside me I know I’ll jizz too! Let’s have some kinky shemale phone sex tonight!

Calypso
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