Freaky Deaky Phone Sex Blogs

I’m in LOVE!  Real love this time I swear!  And you’ll never guess with who!!

That one guy I had such a crush on from the Pharmacy… the short, super buff guy with the tats and goatee and punkrock hair do?  Turns out he is a trannie too.. but the other direction.  A female-to-male transsexual.  I never would have guessed in a million years he had been born a woman.  In fact the only reason I found out was because he outed himself to me when I came to the pharmacy to pick up my estrogen patches.  He gave me a total discount on the patches even tho my insurance card totally expired and I was prepared to pay full price… I said thanks handsome, but why are you being so nice to me again?  And he says “I always try to look out for family.”   And so I said “oh so you’re gay.  Too bad.  The hot ones are always gay.”  and I sighed a big sigh. 

Then he says “Actually I’m alot closer family than that.”  I looked at him for a couple of beats, not understanding what he meant by that.. and then it slowly dawned on me… 

“OMG so you’re… you’re…”

“Yup. I’m a trannie all right.”   He said it with this sexy little growl tho…

“But but… I had no idea.. you look so…”

“Haha thanks, Sherry.  But I’m sure you hear the same thing all the time.:

I thought about it.  “Actually I do.”   And then I realized I was blushing… he was absolutely beaming at me from ear to ear…looking OH so sexy in his short sleeved polo and those muscles.. where did he get those muscles from?

So I continued.. “Well.. trannie to trannie.. can I ask you a personal question?”

“Shoot,” he says.

“Did you get… everything done…?  I mean.. everything?”

He went on to explain that while he’d had his Top Surgery done (removing his breasts so his chest could be nice and flat) he hadn’t had any lower surgery.  Apparently the docs aren’t so good at making reliable cocks from scratch just yet.  But he assured me that he had a HUGE clit that was alot like a small penis.  And that when it came to bedtime, he had the advantage of being able to have any size cock a girl could want.

Long story short.. we are totally going out on a date early next week!!  And he told me to “be prepared to find out eveyrthing I’ve been wondering…”   GAH!!!  I have no idea what to expect!  but I damn sure can’t wait to find out.  I feel weird tho… I really really like him.  Like I feel he could be the ONE i like him so much.  And he totally makes me hard… will that make him jealous?  Will he let me play with his vag ?  What if I end up knocking him up???  Wouldn’t that be some weird shit.  I knock up my new boyfriend and end up becoming a father!!  This is making me want a stiff drink!

SHERRY CHERRY 1 888 434 1588

http://freakydeakyphonesex.com/sherry.html

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Sadly, and inexplicably, my cum problem continues!!  I’ve managed to figure out how to get myself off, but it’s only after completing something extremely kinky and high risk.  I knew this would happen… like any addict, you start to need a bigger and bigger high until it finally kills you!

That’s right folks… I’ve entered the dangerous world of autoerotic asphyxiation.  DO NOT TRY THIS AT HOME KIDS!!  I shouldn’t even be doing it, since I’m no professional.  But I was so desperate with not being able to get off that I had to do something.  I noticed one day while jerking off furiously that i was getting closer and closer and as I got closer I was holding my breath altogether.  When I finally did squeeze out a few drops of cum, I exhaled with this headspinning gasp for air that nearly made me pass out.  It was… INTENSE.   The next day I had to see if it could happen again.  But holding my breath while i jerked off wasn’t doing it.  It was like too much  having to hold my breath in and concentrate on making that cum spark grow and grow and grow.  Suddenly I remembered the hottest times I’d had was when the guy I was with was choking me a little while he fucked me.  I thought it was the violence and helplessness of it that made it so hot, but in retrospect I realize it was not being able to breathe that had made the orgasm so hot!

So I did what no one should ever do.  I got one of my silk winter scarves… a hot pink one (my fave color if you haven’t guessed)… tied it snugly around my neck…   and held the end of the scarf in one hand while I pulled my pud with the other.  IT was a bit uncomfortable at first, but as the sensation grew and grew, I pulled on the scarf tighter and tighter… making it harder and harder to breathe….. sure enough that was doing the trick…. by the time I popped one off I was turning quite blue in the face. But oh MAN what a rush.   Literally… I stood up, drenched in my sweat and cum and immediately fell back down on the bed.  I couldn’t walk for a good half hour.   I am totally playing with fire… but man.. oh man.. I hope I don’t get carried away.  I’ve only done it two more times since then… I need to quit it before I get in some real trouble.  NO sense in going out like David Carradine, right?  I always thought he was hot, by the way.. total kinkmaster top daddy type.  He could have showed me a few things…. but I’m in no hurry to meet him any time soon, if you know what I mean.  Why oh why must I be a sex addict?  Why can’t I have easy little orgasms like the other girls. *sniff sniff*  boo hoo hoo….  I’m soooo horny woe is me lol

SHERRY CHERRY 1 888 434 1588

http://freakydeakyphonesex.com/sherry.html

A horrible thing has happened!  I’m unable to have an orgasm!!!   I don’t know what happened to me… one day I was shooting loads left and right.. and the next… well like last night I’m with the boyfriend and I’m hard as a rock and feeling GOOOOOD and he is working his magic tongue on me.  So he goes down on my fishstick and does his usual that makes me explode.  Fingered my asshole at the same time and everything.  So the tension is building and building and building.. and I get right up to the edge and then… NOTHING. 

Nada. Zip. Zero!  I’m going insane!!  And my boyfriend is too….  He gave himself lockjaw trying to make me get off last night….  he must have slobbed my knob for two hours and NOTHING… i got so close but… UNGH.   Finally he got mad and flipped me over on my face and pounded my asshole raw til I bled. I guess he really was upset  becuz I haven’t heard from him since.  He’s not much of a giver in bed, but he loves to get me off orally.  Just goes to show  you think you know somebody!   You think they care and want to please you and go the extra mile to make you happy…  but all they care about is that you dump your load down their greedy little throats!  

Oh well.  I’m sure it will work itself out.  But what if something IS wrong with me?  What if I’m cursed and I never get to cum again?  Is there some sort of cum doctor I can go too?  Even tho he’s kind of a hunk, I don’t think my family physician wants to hear about this particular problem.  Then again, maybe he would…. I’d be more than willing to give him a demonstration of the trouble I’m having.  Maybe I’d better call his office and make an appointment for this week!!  If it doesn’t clear up on its own by then… then I’ll need a professional to help me get to the “bottom” of all this sudden orgasm denial!!  Hrmph!

SHERRY CHERRY 1 888 434 1588

http://freakydeakyphonesex.com/sherry.html

Sherry be nimble, Sherry be quick!  Sherry jump on top of that candlestick!!  Yup.. that’s right.  Today I got fucked by a candlestick.  And a broom handle.  And a plunger.  And the nozzle of a vacuum cleaner.  And a series of other household items?.  Why?  Because my boyfriend is a FREAK!!  A true freak.  Seriously, he’s intense.  He would have made Rick James uncomfortable in the men’s room!   He’s a sadistic top and he  loves to make me submit to his bizarre sexual punishments.  This morning he woke up with morning wood.  I was excited because i love sausage for breakfast but he had something else in mind.  He dragged me to the kitchen,   set the egg  timer to 3 minutes, forced me down on my knees  to start sucking his cock and told me to make him cum before time was up.  I failed.  My punishment was to watch him jerk himself off into a bowl of Corn flakes (I can’t start the day without my Flakes!!) ….  he came in a huge roaring load into my cornflakes :(    But then he began to piss into the bowl as well.   It was brimming with piss .. pungent, smelly yellow piss and strings of sticky white cum drowning my sugar coated cornflakes…   “BREAKFAST IS READY BITCH!”  He barked at me.   I was like are you serious???    He grabbed a handful of my hair and lowered my face down to the bowl… he was serious alright.   I only got a few mouthfuls choked down before I started gagging.   It was so gross.  So kinky.  And as soon as I was finished throwing up, I was hornier than I’ve ever been!  It was too soon after cumming for him to get hard again, so that’s when he started grabbing the nearest by items  to fill my ass with.  He started with a rolling pin.. then it escalated to the broomhandle… and so on til we were all over the house looking for new things to fuck me with.  I’m pretty sore.  I’m also pretty sick in the head.  Who puts random objects int heir ass at MY age???   What’s gotten into me?? 

SHERRY CHERRY 1 888 434 1588

http://freakydeakyphonesex.com/sherry.html

Lately I’m obsessed with NUT SACKS. TESTICLES!  TEABAGS!!    Like, I REALLY love balls in my mouth.  And I love my balls in your mouth too.  There is something fascinating about the scrotum, don’t you think… It seems so unnatural when you think about it.Like…  why would evolution put these things out there in the open?  They are super delicate and if you make the wrong move PAIN CITY.  of course some guys love the pain.  the torture… One guy I knew loved me to use his balls as a punching bag.  Literally.  He would stand over me with his legs spread wide, fruitbowl a dangling.. and I would ball up my fists and bat at his nutsack and his dick like  I was Mike Tyson.  He loved it and would scream HARDER HARDER SMACK MY SACK!   And it was never hard enough for him, even tho his balls would be swollen red and big as tennis balls by the time I was done.  DIFFERENT STROKES!  I sure as hell don’t like being punched and kicked in MY nads, but I do love a nice skillful tongue running from my crack to my sack.  I like it soft and wet and hot… handle with care.  But if ball torture is your thing, I’m always happy to give you what you need.  Don’t believe me?  Ask the guy I talked to the other day. I told him to make a video of himself for  slamming his balls with a frying pan.  I didn’t think he had the… *ahem*.. balls to do it.. but lo and behold  SCRAMBLED EGGS TO GO!!  He is a good little painslut.  I hope I find another like him some day. Know anybody?

SHERRY CHERRY 1 888 434 1588

http://freakydeakyphonesex.com/sherry.html

Good god it’s been a long time since I’ve gotten laid!!  I am approaching a personal record.. i havent gone more than a week without getting my face fucked, my dick sucked, my hole pounded or pounding somebody else’s mangina… but its been like… two or three weeks alreadty.   I’m so horny I could scream.  In fact I think I will !!  AAAAAAAAAAAAAAHHHHHHHHHHHHHHHHHHHHHHH!!!!    Speaking of screaming, I am definitely a screamer and I prefer guys who are really loud as well.  One time when I was seeing this married guy we were iat a hotel… a fancy hotel, he was very well to do, kind of high profile politician or lobbyist type.. and he LOVED him some shemales.  He also loved to play really rough… so of course I would holler and scream alot.  However, he was trying to be really discreet, but I couldn’t seem to keep my mouth shut.  One time the bellhops had to come to our door and ask us to please keep it down.   He ended up putting his hand over my mouth and grdugefucking the hell out of my tiny little ass raw.  It was one of the hottest fucks I’ve had, for sure.  He was all “If you don’t shut the fuck up I am going to smother you til you lose consciousness, you little whore!!”  And then he proceeded to do just that!!  I swear he had my folded up like a pretzel, my knees by my ears, his hands on my throat, and the room was all spinning and started going dim as I passed out.   When I woke up my ass was dripping with cum and he was tucking his shirt into his pants.  I should have felt violated. I should have felt dirty and ashamed of myself.  But all I could think was.. OMFG that was the hottest fuck EVER!!   I’d love to go for more of that!!  I’m climbing up the walls….  help help!  Anybody want to help me reenact my encounter with The Strangler???  call me!!!

SHERRY CHERRY 1 888 434 1588

http://freakydeakyphonesex.com/sherry.html

One thing I haven’t tried yet is double penetration.  I’m DYING to do this…  its alot easier for your regular gal to do this.. being that they have the two special holes for special purposes.  But me, I really only have the backdoor entrance and the front porch is all blocked off with a meat barricade, if you know what I mean.  Maybe you don’t get it.  I’m saying that I hang out at the Y… get it?   I’m saying… that I was born to be a DJ…. two turntables and a MICROPHONE.    I’m saying…I grew up  in DICKSEELAND… follow me??     Good!!   But none of that means I shouldnt be able to take on two guys at once, like any hot porno slut!!    I’m pretty sure I could get two dicks stuffed into this tight round ass of mine!!  Mmmmm… I just thought… maybe I could get stuffed by two guys and be stuffing another guy’s ass or mouth with my fishstick…   hot damn!!!  Now I’ve really gotta try.  I wonder where I could find two or three willing male partners???  Any suggestions??   Call me!!

SHERRY CHERRY 1 888 434 1588

http://freakydeakyphonesex.com/sherry.html

Remind me to tell you about this summer when I worked as a Candy Striper for the hospital.  They don’t really call them that anymore, but I was a good little assistant.  I wanted to dress up like a naughty nurse, but I had to make do with boring old hospital scrubs.  I made sure to wear the bottoms a little tight, to show off all my curves and um… bulges.   But  do remind me to tell you about all the hot young college guys in traction who had gotten in bike and car accidents, guys needing help with sponge baths, bedpans, and being fed.  You might also want to remind me to include the one senior kid in highschool who had just come down with mono on his 18th birthday.  He kept passing out in my arms, so I gave him mouth to mouth as soon as the docs left the exam room… and since he was running a bit of a fever.. I had to take his temperature…  rectally.. with my meat thermometer.. which I reserve exclusively for this purpose, you see.  He may have been pretty sick, but he felt alot better after I was done with my little exam.   I like playing doctor I guess.  Some things you never outgrow.  In fact, some symptoms only seem to get bigger and stronger with time.  Hrmmmmmmm….

SHERRY CHERRY 1 888 434 1588

http://freakydeakyphonesex.com/sherry.html

Ooooooo…didn’t I just hit the jackpot?!  I met a new Daddy!  He is such a lovely man.  He never tires of telling me how much he worships my gorgeous ass; my long, supple legs; my beautiful, full breasts and, lol, my hot 7-1/2 inches.  What’s more, he’s married: a devoted family man who adores his wife and kids.  But he finds ample space in his heart for li’l ol’ me, too.  We play basketball, go running, go out to romantic dinners and we also have hot and nasty times that blow both our minds…and our wads!  He loves to suck my cock and I love taking his tasty dick up my ass and having him pump me hard until we both cum like crazy.  I don’t even have to touch my cock to cum when he’s fucking my ass!   And as if all this isn’t good enough, he insists on being my sugar daddy, to boot.  Now I was raised as independent girl and I know how to take care of myself and I don’t look to anybody but Sherry to take care of Sherry’s tasty ass.  But Daddy just loves to shower me with presents and always makes sure that I have money for lovely luxuries, like the hottest lingerie, a pair of high Jimmy Choo’s or a bottle of fiiiiiine champagne.  What a man.  But, pouty-pout-pout…Daddy’s other life can keep him very occupied at times leaving me a little lonely and with plenty of time to fill.  Why not give me a call and maybe we can make each other feel reeeeeeal good, baby?  A girl can never have too many Daddies, as far as I’m concerned.  xoxoxo

Sherry Cherry

1-888-434-1588

Hey, Folks! Sherry Cherry here!

Sherry baby loooooooves being with first timers, and first timers just loooooove them some Cherry.

I was out clubbin’ on Wednesday night at my fav-o-rite straight bar (They have those!), and I notice I am being like majorly scoped out by a real stud. This guy is tall, tan and ready for yours truly. I strut on over to his fine self and introduce myself, and he’s buying me drinks and flirting up a storm –and we’re dancing — and eats biting my ear, and grabbing my rear and it, my darlings is all good! When he suggests we head on over to his place, little Miss Thang (that’s me) is pumped up and ready to rumble. I’m so hard at this point, keeping my cock tucked up in my panties is rapidly becoming a losing proposition.

We don’t even get half-way thru his door, before he throws me down on my knees and starts unbuckling his pants.

Well Woweeee –the shoes are on the other foot THIS time! Because I am looking at one helluva beautiful lookin’ PUSSY! That’s right! Mr. Handsome with a tan was another tranny from the other direction! An ever lovin’ female to male transexual super-stud! Rock hard abs, pecks to die for, broad shoulders and everything ya want in a man –BUT HE HAD A SNATCH!

“Didn’t I tell you?” He purred in a low soft voice.

Well no he didn’t, but I went for that man-pussy of his like a cat goes for fish. I was licking that snatch, like a full on dyke and loving it! Teasing his huge clit (it was damn big) with my teeth, and playing with his ass.

Mr. Tan with a snatch was arching his back, and bellowing like a TomCat, and his cum was just pouring all over my face! I ripped off my dress, and told him it was my turn now and he was very eager to return the favor. So I stood up, and he knelt down –and he was suddenly shocked when I slapped him in the face with my cock. He looked up at me very surprised.

“Didn’t I tell you?” I purred in a low soft voice.

Sherry - 1-888-434-1588