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Sissy Boy Shopping

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When I was younger I use to work in a lingerie shop and one time a sissy boy came into the store. Always enjoyed when a sissy ventured into the shop, it wasnt an every day occurrence but every so often a guy would get up the nerve to come in. I could tell he was nervous. Probably his first time coming into a store to buy something sexy specifically for himself.

Think most sissy’s always buy on line but really where is the fun in that you can’t go out and touch the clothes and feel how soft it is and what it will feel like against your girlie parts.

I had fun with him pointing out all the new panties and bras to that sissy boy. I know your wondering how I knew it was a sissy boy and that he wasnt buying for his “girlfriend”. Well he just had a certain aura about him well that and he was trying to feminize his movement along with the slight hint of lip gloss and the eyeliner he didnt quite remove from his play session the night before.

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I was giggling and laughing with every item I made him buy. it was lots of fun. Pretty sure his sissy boy clitty was getting excited with all he was buying.

With doing phone sex calls especially feminization type fantasies it makes me long for the days of working in the lingerie store and interacting with nervous sissy boys. Which is probably why I give you sissy phone sex boys so many go out and buy lingerie from an actual store assignments. Love hearing that rush in your voice when you call me after that assignment is done.

You can reach me at the number below to set up your own sissy boy shopping phone sex fantasy. Never know might start out as a fantasy and lead to a real assignment.

The name is Arianna

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Sissy Phone Sex: Dru Makes You a Pretty Girl

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How many sissy phone sex boys are just loving this time of year? Can venture out into the stores to stock up on your lingerie and make up without a sales girl blinking an eye. Ok so maybe only a few of you sissy boys have clued in that you should be running out to get your pretty on this time of year.

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Seems this sexy shemale had to pass that little info on to a few. Sure some of you sissy phone sex boys LOVE the element of getting caught so this really doesnt pertain to you. The bold bitch that will walk into a store during prime time shopping hours. When anyone and everyone are watching you hold that hot 1950’s inspire dress up to your body in the public mirror. This by far doesnt apply to you.

I am more talking to the ones who hit up Walmart in the middle of night when only the bare minimal of crew are around. So ya can by your cheap ass panties with generic make up. Now is the time to have some fucking fun! Go out and enjoy the fact you can sit down at the Sephora make up counter and get a consultation for your new “Halloween face”. They buy all the products.

Yes that is what I am talking about.

Oh and once your all made up give me a call for some hot sissy phone sex! I mean you cant let that pretty face go to waste. Or maybe you need to call me first so we can work out your plan of shopping attack. The stores to hit and what you should say to the sales clerk.

Ya that sounds about right!

Just ask for Dru the sexy shemale ready to help you pretty up your girlie ass.

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Sissy Phone Sex Boy Confessions with Arianna

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So sissy phone sex boy how is your girlie voice?

Have you been off practicing it? Sitting in rush hour working on that feminine voice that will match your alter sissy ego. Hmm what is her name? Jessica Carmen? Jennifer? Barbie?

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Its always interesting what names you boys come up with for your pretty girlie side. I have to admit over the years of doing sissy boy phone sex calls I have wondered about the process that goes in before your call. Like do you dabble in the lingerie and consider yourself a guy with a fetish for women’s lingerie? Or do you honestly know your a sissy bitch the moment those silky nylons slip over your feet?

Does your name come to you while your applying your lipstick? That first pucker of your lips as your kissing the air make you think oooo I feel like a Kylie. Or does your name come from someone you knew at school. The slut of the high school that girl you admired for sucking so many dick. Your girlie side surely desires to be just like her.

See so many questions for you sissy boys. I know we could focus on the clothes and the make up and all things pretty and girlie but really wouldnt it be fun to focus on the how’s an why’s?

How did you come to that dressing style? Why that name? Where did you learn your make up techniques?

Ok so some of them are not quite how’s and why’s but you know what I mean. Dont you long for a gossip session where you just let all your secrets out. Why you became a sissy boy is the question I would like to know.

So when your in the mood to divulge those inner most secrets give me a call. I know I cant wait to hear them. Then after the sexy question period I could fuck you with my strapon. A good sissy phone sex boy does deserve a treat.

Talk to you soon, Arianna.

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Jillian loves to exploit a Sissy Boy

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As a sexy blonde woman I definitely draw the attention of men. So when a man doesnt glance my way I have to wonder what is up with them. Now before you tell me they are perhaps married? Oh darling! You havent been around many married men for they are the first to look and take the longest drink with their eyes. Just cause their is a wedding ring on their finger means absolutely nothing in my experience.

Sure you can ask me what brought this thought process up? Very simple I was at the mall grabbing a gift card for my nieces birthday. So thought I would run into the lingerie store and see if they had any cute jammies for her. There was a man in there looking up the sale rack of bra and panties.

First I thought he was excited to be buying such things for his girlfriend and  didnt notice me coming in well that was till I walked up and down the store. Still no look from him. He was too infatuated with the delicate fabric twisting over his fingers. Hmmm.

So I stood and watch him.

My time as a phone sex cougar has done nothing if not taught me about men who have a fetish for lingerie and their shopping habits. You guys are so willing to tell me your dirty secrets over the  phone. So there I was watching him and he was oblivious due to the delectable delights in front of him.

Hmmm what is your fetish…..

Panty boy?

Sissy boy?

Cross dresser?

All worked well with how he was behaving in the store. Avoiding eye contact with clerks and customers. Picking the rack in the back of the store. Choosing a time of day when it would be busy enough not to get overly noticed. The fact he went back and forth matching the panties to the bra I took him for either a sissy boy or a cross dresser.

Rather leaned to him being a sissy boy doing some pretty sissy assignment for his phone sex mistress. Love to find out what it was. The only reason I didnt choose cross dresser is there was a sense of embarrassment to the act and most men who dress in women’s clothing are far from embarrassed about dressing up.

What do you think? Am I right in it being a sissy boy? Or better yet are you a sissy boy craving a similar experience. Give me a call for something just as hot.

Jillian

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