Freaky Deaky Phone Sex Blogs

  Normally I don’t talk about my sissy boys or what I do with them, but I just had to share this one.

From time to time I have Dommes asking me to help them ‘train’ a sissy-boy sub, and every so often I have a sissy boy of my own to train.  This was one of the “every so oftens” … Darren, or ‘Darla’, came to me asking to be sissified.  Since I didn’t have any current slut-boys to work on, I agreed.

He came over to my place dressed in tight jeans and a tight, bright tee shirt, so first thing I did was order him to change into his Darla outfit.  He changed into a little french maid outfit that barely covered his ass, and a tiny white thong that hardly even cupped his family jewels.  He topped off the outfit with a cheap brown wig, white bobbie socks and black pumps.  I noticed he had done a meticulous job on his make-up, with his lipstick just a little too red, and his eyelashes a little too thick.  I gave him a feather duster and assigned him to dusting my blinds. 

He started in on the chore with vigor, then stopped suddenly, starting out across the street.   I asked him what the problem was as I looked out the window … there was a small crowd gathered under a large tree where there was a young girl calling up into the tree.  We went over and joined the crowd (no, I didn’t let him change first), and found out the girl’s cat had gotten stuck in the tree.   I was quick to offer help … I volunteered to boost ‘Darla’ into the tree in order to rescue the cat.  Darren looked quite pale, but was too scared to disagree with me.  I hoisted ‘Darla’ up by the waist, allowing the maid uniform to ride up a bit, exposing even more than before.  Then I boosted my sissy maid on up, with one hand planted firmly on his asscheek.  ‘Darla’ scurried up the tree and out onto the right branches to comlpete a quick rescue of the grateful kitty.  He cupped the poor kitten carefully until he could safely drop it down to waiting arms below.   ‘Darla’ climbed down out of the tree with his uniform riding up so high his belly button was exposed … his ass having that one thin line of white fabric highlighting his crack.  Only a few of the crowd stayed around long enough to thank ‘Darla’, most of them scurrying off as they noticed the extra bulge in the front of the panties.  ‘Darla’s make-up was all smeared and his wig was crooked, but he was all smiles accepting the thanks from those that stayed.

Once back at my place, I rewarded him by allowing him to suck my rod … a treat very few first-timers are allowed.  Give me a call if you want to be sissified … I’ll make sure you’re treated like the sissy-slut you know is inside you.

Axel, 1.888.455.6723

http://freakydeakyphonesex.com/axel.html

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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  Damn!  Cops really do need to go find themselves a sense of humor … and what gives them the right to decide what is or isn’t indecent behaviour?

I mean, c’mon … my dick’s not indecent … I think it’s pretty decent.  Ok, so when I squirted on him, I guess I shouldn’t have made that Monica Lewenski joke, but still … he should have taken it for what it was, a joke.  Not MY fault he popped out of nowhere right as I was getting ready to blast a New Year’s blast.  He should have been watching the fireworks like everyone else around us.

  That judge didn’t have to be such a dick about it, either.  I even offered him a blowjob if he’d call it time served for good behaviour.  Shit, I just got home from jail yesterday.  I do apologize to all of you that tried calling over the last week … I was detained, incarcerated, locked up.  I mean, it was a fun vacation … sit back and do nothing but jack off all day, and I think the officer that was standing over me during my one free phone call actually smiled when I tried calling a phone sex company for the call.

Still, now I’m more in debt than ever since I missed a week of calls.  Think I can get a few of you to help me out and call extra for a couple weeks … at least until I get caught up?

1-888-559-9971, ask for Jesse

http://freakydeakyphonesex.com/jesse.html

Anyone else out there already broke a New Year Resolution?

Mine wasn’t supposed to be that hard to keep, but there’s something about making a resolution that gets the fates to decide to MAKE you break them.

Just a simple resolution … “I will not suck a stranger’s cock until I get to know them”.  Maybe I could have kept that one if I hadn’t also made the resolution about going to the gym at least once a week as part of my workout regimen.  It was at the gym.  I had just renewed a membership that I had let lapse … I usually do my training at home, but sometimes the machines at the gym give a better all-round workout than the exercises you can do at home.  I headed on into the changing room and saw a young man with a slim swimmers body, smooth-shaved all over.  Our eyes locked for just a moment, but that moment was enough that we both knew … it was happening.  My workout went quickly, but seemed forever … I could see him working out in a different area of the facility, and I just couldn’t wait for both our regimens to end.  Sure enough, we finished up at just about the same time, so right as I was coming out of the showers, he was stripping down to head into them.  I approached him to initiate conversation, and he grabbed me, planting his lips on mine as he pulled me around the corner of the lockers.   This was in a back area, and very few people were still here, so the risk of being caught was minimal, but it did add to the excitement.  There was an animal urgency in which we groped each others’ bodies, and I found myself sliding my clean body down his, still smelling of his musty sweat from earlier.  I wrapped my lips around his shaft – slender and long, just like him.  My hand slid up between his legs to cup his balls, then further back to pull his firm ass against me, while his hands ran over my bald head, and forced it against his steamy groin.  I felt his hot load shoot down my throat, and drank every bit of it, only briefly thinking about resolutions broken.  Rising to my feet, I pushed him against the wall and raised one of his legs high into the air.  I pressed my raging hard-on foreward, and used my free hand to work my cock to his asshole.  I could feel his slippery cock growing hard again as it pressed between our bellies, and we gazed once more into each others’ eyes as I used his weight to force my cock up into his asshole.  I could see the pain in his eyes as it started, but the joy and relief there as well, as he felt my fullness forging its way into him.  I fucked him good right there, passionately kissing each other, our bodies pressed tight against each other.

Afterwards, we took a shower together and exchanged names and numbers.  Who knows … maybe THIS resolution was worth breaking.

AXEL, 1.888.455.6723

http://freakydeakyphonesex.com/axel.html

I’m waiting in line on New Year’s day for the store to open, like a good consumer, when this bitch that’s a couple people in front of me starts calling a bunch of her friends from farther back in line to come join her up where she is.

Well, I’m not going to stand for that, and I start telling her exactly what I think of her and her inconsiderate actions.  She decides to stand her ground in front of her friends, declaring “What are you gonna do about it?”  Now, why’d she have to go and say that?

Next thing you know, we’re both at each other … nails gouging, hair pulling, rolling onto the sidewalk, ripping at each others’ clothes … all that stuff that men love (and there was starting to be quite a few men in the crowd of onlookers).  I had just about gotten the upper hand when one of her friends yells out “Look! That chicks got a dick!”  Sure enough, with all that tussling, my schlong had slipped out of its hiding spot in my tiny thong panties, and was swinging free under my ripped mini skirt.

This brought the fight to a halt, and we both just looked at each other as we noticed that most of the line had already made it into the store.  We got up & brushed ourselves off and headed into the store.  I tucked my willie back into its security zone as best I could, and that would have been the end of my story … except one onlooker really liked what he saw.

While in the store, this guy sidled up close to me and whispered loudly “You really got a dick?  What’s it like?” to which I gave him a bemused smile and answered “Why? Want to take it for a test-spin?”  He looked shyly at me and then dropped his gaze to my feet as he nodded slowly.  I had him hold my purchases for me until I got done shopping, then got him to help me out to the car with them.  From there, I had him follow me to a nearby motel.  He paid for the room, and I met up with him there shortly after he went on inside.

Once in the room, I pulled my torn skrt up just a bit, and my thong to the side, letting my surprise package out once more.  He dropped to his knees and started licking and sucking on my pole like it was made of honey.  In no time, he had me wanting more, with his hands creeping up my thighs to my ass and holding tight for dear life.  I got him standing up and had him drop his pants.  His cock was stiff as iron, and I grinned as I told him to turn around.  I bent him slightly over the bed and ran my dick up and down his asscrack.  Sliding my shaft into his ass was so easy after all I’d been through that day.  He gave out a yelp as I shoved deeper, but I just smiled as I started to fuck his lily-white ass silly.

“What’s it like”?” … give me a call and I’ll tell you.

1.888.205.3279, ask for Ryan

http://freakydeakyphonesex.com/ryan.html