Sissy Boy Phone Sex

Small Penis Humiliation Phone Sex

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I want to thank the small dick men out there that wear panties. You are making it so easy for a girl like me to figure out who is under endowed in the penis department. Sure I just though guys wearing panties were secret little sissy boys but come to think back to all the small penis humiliation phone sex call and how many of you little dick guys who like to wear panties. I know realize those panty lines your sporting are actually excellent way to weed you out.

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Now dont get all worried your never going to get near a hot girl. Thats not the case cause even a hot girl wants a good laugh and well lets face it what you are tucking under those pretty little panties gives us a very good laugh. Course the great thing about small penis humiliation the more we laugh at your itty bitty thing the smaller it shrinks.

Good news for you guys I love to laugh and well I have a great laugh.

Now all I ask is that you wear some pretty panties for me. I dont care if they are used but between you and i we know picking a pair of panties out of the hamper is the only way your small dick is ever going to get near a pussy.

I have to say though if you fit comfortably in a thong pair of panties then expect my laughter to be hard on those small penis humiliation phone sex calls. Yes if your asking I will watch you on your cam. Why I am agreeing to this is beyond me but I do happen to enjoy the pathetic show your small dick men in panties put on.

Get ready for some small penis humiliation when you call

Courtney

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Sissy Boy, Strap ons and Ass Fucking Fantasies.

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How to get a phone sex sissy boy rather excited all one needs to do is mention how big their strapon cock is!

Always laugh at you pretty sissy boys for the moment I mention I have a thick strap on cock your instantly asking how big is it? When was the last time you used it? Then that gulp of are you in the mood to use it now?

Well it would be a shame not to fuck your pretty sissy ass now wouldn’t it?

I mean after you have gone to all this trouble of getting dressed up for your hot cougar. Hear what you put on for me did get me looking over at my bedside table and thinking “Hmmm wouldn’t it be nice to break out my cock and give it to you?”

Yes I should be fucking your sissy boy ass with my thick purple jelly dick. Oh I know your a touch disappointed its not one of those realistic looking cocks. So am I but just think of this as a magical unicorn dick that will be transporting you off into the land of cock hungry sissy whores. One fuck with my strap on cock and you will be begging to always have something shoved up your ass!

Rather admit I do enjoy using the jelly variety of strap on for I tend to be a touch more aggressive when ass fucking and well this style will protect your sissy bottom from getting too sore and tender. After all getting fucked by myself is sort of that middle ground between fantasy and well the real thing.

Not that I have anything against putting a bit of punishment on your pucker hole but I dont want to turn you off that full feeling.

Now that I have you rather intrigued about being my phone sex sissy boy you can reach me by calling the number below. Just ask for Jillian.

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Sissy Boy Phone Sex with Courtney

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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

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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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Crossdresser Phone Sex with Courtney

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Its the day before Halloween and wouldnt you know it last night I get some guy calling me up who is prancing around in his “Halloween costume”. Well actually that is what he is telling his friends but really he loves dressing up in womens clothing so when Halloween comes around its the one day he can actually dress up in some pretty womens costume and everyone will comment how pretty he looks rather than give him those weird looks cause he is a crossdresser phone sex freak.

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He has a few costumes to choose from one was the school girl, which had me laughing at. There is a plaid skirt, white button up shirt, white knee high socks, mary jane shoes and if that wasnt enough he got a wig that he could put into some pig tails. I want him to wear that one. The other one was more a stripper attire, which ya that would turn some head too. Short black pleather skirt, fish net stockings, red skin tight tank top and fish net style arm gloves, knee high boots and he was going to wear his red fuck me wig.

Either way he was going to be heading down to the MAC store and having them do his make up for the Halloween party. I so want to see some pictures of how he turns out. Think either costume will look hot as hell and get people to turn their heads. He is 6’2 after all without any heels.

Have a great night Mr CrossDresser hope everyone loves your “costume”

Just ask for Courtney if you too have a crossdresser phone sex fantasy or wanna discuss your Halloween costumes past/present or future.

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Kassidy’s Cum Fetish makes you a Bukkake Princess

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So I have said that I may had a bit of a cum fetish, I love hot loads of jizz being squirted over my face and tits. Any where over my body really. So of course I am a bit preoccupied with bukkake fantasies. I guess that is why I end up with sissy boys coming to me to talk about their cum fetish fantasies.

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Not so much that they want to shoot their own cum on themselves oh no! These sissy boys want to be on their knees feeling what its like to be a bukkake slut. To take multiple nut batter loads all over their made up faces.

Probably my last favorite bukkake phone sex call was making the sissy become a cheer leader. Ya you probably know where this is going. I had to take that sissy cheerleader into the boy locker room where all those foot ball guys were hanging out after the game. They were in a bad mood since they lost the game and well needed a bit of a cheer me up. What wouldnt do that other than a slutty little cheer leader.

Mind you my cheerleader had all these guys to satisfy at once and only a few holes. What to do? Ok so you know where this is going. That sissy just dropped down on her knees to say boys get ready to jerk off and me and coat me in your ejaculate. Let the jizz fly!

What guy wouldnt want to be apart of humiliating a sissy bitch like that?

Every where she turned there was a cock with cum dripping out. There heads swelling up more and more as their balls are filing about ready to burst. Not knowing when that cum would blow out.

Ya describing each cock in detail.

Only made that sissy beg for those cocks to blow hard and fast.

How many cocks do you fantasize about squirting over you?

Call Kassidy and let her transform you into a little bukkake princess.

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Sissy Adult Baby with Mommy Jennifer

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Mommy Jennifer got to have some special fun with a certain phone sex adult baby who came crawling into her nursery. That he was in desperate need of a changing. So he was put up on the change table and carefully striped down. Getting rid of those boring clothes and put into the clothes that would make him feel more comfortable. As she powered that bottom with lavender powder this adult baby knew he was in for something special.

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He watched his phone sex mommy reach for the diapers on the top shelf above the change table where all the pretty pink things where kept. He tried his best to squirm but nope it wouldnt. For Mommy was too strong and quick with that diaper change.

On that pink diaper went.

That wasnt the only pink thing that phone sex adult baby got either. For Mommy Jennifer was giggling away as she was laying out all the pretty pink sissy baby clothes she was ready to put him in.

I know your going to wonder what all happened.

What did Mommy Jennifer do to that sissy adult baby? Well your just going to have to call and find out in your own sissy phone sex call with Mommy Jennifer.

The number is below is how you can reach Mommy Jennifer

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Sissy Boy Phone Sex with Raine

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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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Strapon Phone Sex Fantasy with Savannah

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All dressed up and ready for a strapon phone sex fantasy?

Well my name is Savannah and I have my plastic cock right here beside me just waiting for that perfect sissy boy ass to violate. I know you went to all that wonderful effort to get ready and here I am just like a guy only wanting to put my dick in you.

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Dont worry I do appreciate all the time it took you to get ready for me.

The extra attention you put into your makeup.

How you flipped through your outfits so you could find the right one that didnt scream anal slut. Even thought I know you been wanting a dick in your ass all day long been fantasizing about getting fucked for days. How your ass been puckering the whole time you sat there getting ready.

Oh and those panties you picked just perfect. I will make sure to rub my hands over them extra slow. So you can savor this ass pounding.

I will have to refrain myself there is just something about fucking a sissy with a long, thick strapon that gets me so excited that I can hardly hold back. Usually I have a need to just push my thick dick right deep into that waiting ass. We are talking balls deep.

But since you went to all that effort of looking so pretty for me, I think we will just have to make this fucking last a bit longer.

Are you ready for a strapon phone sex fucking with me?

I know I am.

Just ask for Savannah

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Cuckold Phone Sex Sissy Boyfriend with Kassidy

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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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