Sissy Boy Phone Sex with Courtney

Hey Sissy boy! Have you ever complimented a girl on her dress or shoes? Bet you have! You seem like the type who would go around noticing how a girl is dressed. Sure that girl is all pleased as punch some random guy paid her a compliment on how she looked. Except I bet if she knew who was paying her that compliment she wouldnt be so happy.

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The man paying such close attention to that jersey knit dress was someone who just finished dressing up for a sissy boy phone sex call. Oh dont act all surprise. I know your type far too well. I talk to you on the phone.

Your secret stash of clothes tucked away in a box in the back of the closet so no one will find them. The lingerie you buy around the holidays saying its for your “girlfriend” but really you havent had one in fucking years cause well.

Why dont you have a girlfriend?

Afraid she will discover your secret fetish for dressing up in women’s clothing? Well dont worry I wont laugh. Much! A soft giggle as I tell you what a sissy bitch you are for dressing up so pretty. Then I may make you venture off to compliment random girls to see if they can figure out who you really are. A sissy boy!

Ya sure sounds cruel but in the world of femination domination I am merely a sensual domme which means you havent met mean. Now your curious right? Curious what a sissy boy phone sex call with me would be like?

Well why wonder when you can simply call and find out for yourself. Just ask for Courtney!

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Become Phone Sex Domina Shiva Girlie Elf

Its rather true I am not one for the holiday season. I mean the day doesnt revolve around my glorious self so why should I really be all gun ho. Yes the presents are nice but as a phone sex Domina you should be showering myself with gifts every week.

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So how does this ultimate phone Domina opt to celebrate the day. Well I was thinking with a little feminization phone sex scenario with a jolly holly add on. See I was thinking for those sissy boys its time for you to dress up like a girlie little elf and help Santa relieve some stress before he has to dive down those chimneys.

Yes since we are talking about sissy boys I will ensure to take great time on transforming you into the perfect girl elf. From the rosy cheeks and freckles to the stripped knee high socks with black mary jane shoes.

But I dont have any good girl elves at my North Pole. Oh no this phone sex Domina has nothing but naughty elves who perhaps were ex strippers and they are more than happy to perform on those candy cane poles in the middle of the shop to ensure there is a happy and well horny work environment.

Once you have performed in your peppermint green string bikini for all those elves its off for you to show Santa how amazing your mouth skills are from sucking on all those candy canes. Yes Santa has noticed you were extra naughty this year with putting all your focus on teasing the other elves. Now its time to show him you can suck the cum from his big fat ball sack.

No need to be shy for Santa has seen it all this year. Yes even that time behind the barn. Naughty sissy elf.

Tell the dispatcher you wish to speak with Domina Shiva.

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Cross Dressing Phone Sex with Raine

Yesterday I was walking the down town area. Just window shopping and enjoying the sun before the anticipated storms the weatherman was calling for. As I was staring in the window of some kitchen shop the reflection of a passerby caught my eye.

This amazonian type woman with rather masculine features. Gotta say at first I thought it was the reflections distorting the image like a fun house mirror. Making things seem opposite to what they were. When I turned around I half expected some petite woman standing behind me.

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Nope the reflection was rather correct for it was a very tall man dressed up in ladies clothes out doing their afternoon shopping. The cross dresser just gave me the once over and proceeded down the sidewalk letting her black 4 inch heels click confidently on the brick.

Now I have to say most my interactions with men dressed up in ladies clothing has been via cross dressing phone sex calls. Well thats being full blow from the make up to the shoes dressed up. I have engaged with men who wear some item of ladies clothing like a panty boy or something who enjoys stockings. Garments that they could hide away under their “traditional” clothes so no one would find out their secret.

Which is all well and good. Rather interesting really. Nothing like playing footsie with a guy and discovering his foot is encased with silky stockings. Not sure who had a more befuddled look on their face to be honest.

Anyways I am totally back tracking with that rather limited interaction it got me wondering if cross dressing phone sex was where men who enjoy ladies clothing get their start towards public interaction?

Sort of that test the waters out with how girls on the phone interact with them and then poof venture out into the real world. Love to hear what your opinion is on that. Inquiring minds need to know.

Maybe I am over thinking the process. Either way I think this weekend should be all about some cross dressing phone sex be it humiliation or just what you should wear for a holiday party.

Raine is the name and the number is down below 😉

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Bisexual Phone Sex Fantasy with Jillian

My friend has the worst pick in men. No really she goes for these guys who spend hours in the gym think are drop dead gorgeous. He is the real deal. Gonna pick me up and toss me on the bed. The typical bull shit. Now I have been around her long enough to know that I just have to let her run the dance cause this muscle bound guy is going to be like every other one she brought around me. Complete bisexual phone sex submissive who is looking for some woman to smack him down to his knees and either make him worship her feet all the way up to her ass. OR bend him over and fuck his ass. Now I am all for some role reversals in the bedroom.

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Nothing like bending someone over in the bedroom for a little ass play. I do happen to own a very nice 9 inch strap on for such occasion. However being an older woman I have come to the conclusion that you can not judge a book by their cover particularly when it comes to men. Many have a hidden freak in them and want to dive into some submissive role play. Especially those big bound muscle gym rats. I often picture them in the gym wanting to suck each other off before or after a work out after they have heard an orgasm increase their work out abilities.

Yes I am thinking of a particular couple of men who are work out partners while I am typing this. They are very buddy buddy when spotting each other. Those smacks on the asses to encourage the other, well those hands are left there a bit longer than I usually see. Bet there is some ass pounding going on in the shower and yes my girlfriend has the hots for one of those bisexual phone sex craving men.

So why not give me a call and tell me your secret bisexual fantasy cause I am sure you have one or two fantasies that run through your mind. Perhaps its the guy who signs you in or the one who has the locker near yours. Honestly the bisexual phone sex fantasies can go on and on.

Jillian

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Sissy Phone Sex Daddy with Dani

hiii its me dani! wiggles me bum at you in my cute pink polka dotted panties. i know all the sissy phone sex daddy ‘s love my cotton panties! well most the sissy daddies do any way cause I keep finding you guys wearing my cotton bikini panties well maybe not all of you wearing them but you sure do like to beg to wear them.

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like this one sissy phone sex daddy ask if we could have a panty party he wanted to wear the same kind of panties as me he even sent me a gift card to victoria secret so that we could buy matching ones. it was so much fun cause i got a ton of panties with it and they all match him so like all week long i get to wear panties just like my sissy daddy.

wait maybe he isnt wearing the panties all week but i am. they are super cute cause i got some bikini ones and some cheeky ones those are my favorites cause they show off a bit of a my cute little 19teen bum. who doesnt to show off some of their bum right?

even sissy daddies like to show their bum off. it so funny when they do too.

do you have a favorite panty you like to wear when you get dressed up? call me and lets have some panty fun!

I am dani the cute barely legal phone sex girl who loves playing on the phone with sissy daddies.

Dani!

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Sissy Babies Love Phone Sex Granny Gail

Yes honey its hard to find that special one to understand what a sissy baby needs in the way of care. Well baby, my name is Gail and as a phone sex granny I know exactly the care phone sex sissy babies need.

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See as an older more mature woman I have not only looked after my own kids but have looked after my grandkids and well babysat in general. So looking after a grown man who loves to dress up in pretty frilly baby clothes is easy for me.

I am sure your wondering just what sort of phone sex granny I will be towards you, shall I be strict or a nurturing. Well I can honestly say that I am a bit of both. With my ab/dl I enjoy having fun like most grandmas but if your naughty I will also enjoy punishing you. So the type of fun we have is really up to you. Are you gonna be a good sissy baby or a naughty adult baby?

Good sissy babies get lots of time sitting on granny’s knee snuggling and there is also dress up time cause you are my special baby dolly. Bad sissy babies are often spanked over their diaper covered bum and tied to their high chair while granny makes them eat stewed prunes from a jar.

I really hope your a good sissy baby for Granny Gail as I am looking forward to dressing you up in all sorts of pretty frilly girlie dresses. Lots of ribbons, bows and lace for my lil sissy adult baby.

Bye Bye Baby your phone sex Granny Gail will talk to you very soon. Till then a sweet little kiss on the forehead.

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Sissy Boy Phone Sex with Raine

I was at my girlfriend’s house on the weekend. Suppose to be picking out courses for the coming fall semester. Alright so it was mostly watching movies and chatting about who was dating who now. Never ending drama in the friends circle. We paused the movie we were only half watching so I could head off for a washroom break. The washroom was right next to my friend’s brothers bedroom and his door was partially open.

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As I walked by I could hear Taylor Swift playing softly which I thought was super odd since he was a hard core metal fan. Never heard anything but that since I known him. So of course I had to look in thinking he might of snuck a girl in there. Yes even a kinky phone sex coed can be a bit of a pervert too. Not gonna lie was a touch horny and would of loved watching him get a blow job from some hottie.

I wasnt really ready for what I did see. It was my girlfriend’s brother dressed up in his mom’s lingerie.

Ya! It was a bit of a shocker to say the least.

He was dancing around in black panties and bra and some silk robe. I tried really hard not to giggle but really how can you not laugh at seeing a sissy boy dance around in what can only be his mother’s undergarments.

Sure I have seen pictures of sissy boys who call me for some kinky phone sex fun all dolled up in their favorite frilly outfits.  But to see it in person from someone you have known for a really long time. Gotta say I was a bit stunned.

Well not stunned for too long cause as soon as my brain comprehend what I was seeing I had to run off to the bathroom and laugh. Didnt wanna get caught peeking in on the sissy boy.

Bet your wondering if I told my girlfriend about what her brother was up too?

That little info you will just have to call me for.

Dial the number below and ask for Raine!

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Cuckold Phone Sex Sissy Boyfriend with Kassidy

Its really no surprise that I enjoy cuckolding men be it my real life boyfriends or those special boyfriends over the phone. See I pretty much view you all the same. You soon gonna be my cuckold phone sex boyfriend.

For I will be able to do what ever and who ever I want. Now you might be going ya thats happened before Kassidy. What you dont know is that I wont do it behind your back there is no “cheating” in the classic sense of the word. I will bring over my bulls to fuck me right in front of you. Why hid the fact that your not able to satisfy me in the orgasm department.

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I am beyond faking in the bedroom. I want you to not only know but see that you are not capable of keeping me pleased. To actually see how strong of a sexual appetite I reallly have.

Now course with you often watching that makes things a bit complicated. For I know your gonna be sitting in the corner jerking off your tiny cock and well that wont do. For the way I see it as my cuckolded boyfriend you will have to endure some humiliation. So why not make you my cuckold phone sex sissy.

Yes you read that right!

Cuckold Sissy Boy.

See before my date shows up to fuck me we will both be getting all pretty. Each of us wearing some sexy little outfit. Mine of course will be to turn him on and well yours just to show us how pathetic you are.

You see where this is going?

It starts with you in panties and could very well end up with your wrapping your lips around something other than my dildo. Ooops am I letting a few secrets out?

Well how about you give your sexy girlfriend a call and let your cuckold training begin.

Just ask for Kassidy. Dare you to tell the dispatcher you wish to be my cuckold phone sex sissy boyfriend.

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Cock Sucking Instructions From Shemale Dru

We all know you love a little JOI when it comes to rubbing that clitty but I am gonna give you a different time of jerk off instructions today. Well actually its just some helpful instructions over all its how to suck a cock 101. Since your have already found your way into dressing up pretty the cock sucking will be the next adventure for you.

I know you will want to be the best at that. Hate to be the disappointment to that gentleman who so graciously gave you his cock to suck. Right?

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That is where I come in for you gonna grab the best and biggest dildo from your collection. Now dont look at me all innocent and doe eye like you are stunned I said dildo collection. Sissy sluts always have a collection of cock in some drawer. Never know when your gonna wanna see how a new lipstick will look on a dick. So I am sure you have various sizes and colors of dildos in that drawer.

Grab your favorite cause I am gonna give you a detail description on how to work that cock like a nasty cock sucking phone sex slut. Yup when you drop to your knees to work a man’s dick over that guy will be doing his best to try and not to blow his massive load down your throat.

Course with these amazing cock sucking phone sex instruction you will have all the wonderful ability to take control of his orgasm. Working that jizz right to the edge leaving him breathless and begging for more of your sweet sissy cum dumpster of a mouth.

So while you work on figuring out which cock goes best with the lipstick you have on currently I will be sitting here by the phone. Patiently waiting to instruct you into being the perfect cock sucking phone sex whore.

Just ask for Dru.

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Sissy Bitch Becomes Whisper’s Cock Sucking Trainee

You know your wife is out fucking another man. Sure you should be deeply upset by this little discovery but yet your not. Instead you are searching the internet on ways to be a pretty little bitch boy so that your wife may invite you to the party. She has told you a thousand which ways she isnt into having two men but perhaps you can convince her into having that real man and you the new sissy bitch.

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Welcome to being a cuckold to your wife’s latest sex fantasy. Its the one she was hiding away from you but trust me as someone who is use to transforming men into pretty girls I have you covered from helping you choose the perfect panty to tuck your useless nuts into all the way to what lipstick will leave a nice ring around a cock.

Oh ya I did say cock! For your gonna be the sexy fluffer that ensures any guy fucking your wife will be rock hard by the time they hit that pussy. So best work on your cock sucking skills. Hell as a sexy shemale I will be more than happy to help you work on your oral abilities. But how about first we start with your pretty little outfit.

I know that is what you sissy phone sex bitches are eager to start with anyways. Must always be pretty for those impending erections. Just ask for Whisper when the dispatcher answers your call.

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