How’s It Hanging

~~~Olivia ~~~ 844~332~2639~x~226~~~

How’s it hanging? lol, wonder when the last time you heard that?  I’m thinking it may lay the same length as those worthless balls.  There’s no need for it to be any longer is there?  If it were any longer it wouldn’t tuck so well in that lacy underwear would it? Being one of my first “Darlings” you’ve been updating and keeping up with current fashion and style.  You were the first to use a mask that was already covered with makeup.  Using the mask was a way to go out into the early morning or later after dark at night.  I wish more of my “Darlings” were as adventurous.  The only downfall with the mask is heading to the glory hole; can’t suck many cocks through that little pouty red mouth.  Being able to put that lacy panty-covered rump up in the air to have some fun. 

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Olivia’s Darlings

~~~Olivia ~~~ 844~332~2639~x~226~~~

Olivia’s Darlings is a group of well-trained ladies who have taken extra steps to exceed in feminism.  I bet you would be a great candidate for one of my Darlings.  The most important aspect of being one of my Darlings is to just be yourself.  You know if it’s in you to be a Darling already.  Do you like the feel of smooth fine material next to your hairless body? What about fitted or frilly outerwear?  Is it important to you to look your best when you get the opportunity to shine? Can you choose the perfect color for your cheeks, lips, and nails? How long have you enjoyed being who you really are or are you still working on that?  This is a sisterhood you will enjoy being in. I’m looking forward to our first connection be it chat or phone. 

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Crossdressing Sissies

~~~Olivia ~~~ 844~332~2639~x~226~~~

Crossdressing sissies are so interesting to me.  I have a few who have been with me for a long time even after training is over.  Girls, you know how we shop for that special outfit. Every thread is to be inspected.  The color has to be a certain hue, and the shape has to be just so therefore has to have all accessories matching. The newest photo I received shows her walking her dog early morning in full dress.  Her navy blue leggings with a matching hoody pulled over her head. The face is in full makeup and the wig is brushed, the nail polish to match, Ugg’s shoes round out her outfit.  You would never believe it is the same sissy I started out with. For one thing, I couldn’t get her to go out even at the night.

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Small Dick Humiliation

~~~Olivia ~~~ 844~332~2639~x~226~~~

Small dick humiliation. There is a new guy working at the gym and I’m sure with a little bit of coaxing I will be fucking him very soon.  He is there every time I am and we always strike up a conversation filled with sexual innuendos.  Even his eyes read how much he wanted to fuck with me.  You know how I love to flirt and tease and I certainly did my part.  My nipples felt like they were going to pop through my top.  I felt like I could force him to the floor right there and take him.  Asking him to join me in the steam room; he told me he had an appointment in a few minutes and it wasn’t enough time to have the fun he wanted.   

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Hypnotic Feminization

~~~Olivia ~~~ 844~332~2639~x~226~~~

Hypnotic Feminization is something I enjoy using while training some of my “Darlings”.  Not all need the hypnosis but it’s easier for me to work through some stalls they go through.  One of my students was having issues going out when dressed so I just played on that.  As we were getting dressed to out to the club together I slipped on my beautiful shiny silver bracelet.  Moving close to her I drew her attention to the bracelet while telling her how beautiful she had dressed.  Telling her others would love to see her pretty outfit and they wouldn’t if she didn’t go out.  By the second session with the shiny bracelet, she was ready to go out.  Now I can’t say every sissy student does that well but usually, that is the case.  Hypnosis is a wonderful element to help with jitters. 

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Club Catfight

~~~Olivia ~~~ 844~332~2639~x~226~~~

Club Catfight broke out as we were celebrating the newest “Darling” at the club and having a big time.  We actually celebrate her birthday. I like to welcome the new member by getting as many “Darlings” as possible together to meet.  There are always small sandwiches and salty snacks with wine overflowing.  “Darling”s share information, and get to know each other.  Everyone dresses in their best; you may think it’s a group of beauty consultants.    I am so proud of them as I look around. One “Darling” is dressed in a skin-tight cocktail dress yet there is no tail tell signs of anything amuck.  *if you know what I mean*  Everything was going along beautifully.  As some started drifting away I heard a crash followed by shouting and screaming. 

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Olivia’s Newest “Darling”

~~~Olivia ~~~ 844~332~2639~x~226~~~

Olivia’s Newest “Darling“; as you know when you graduate from Olivia’s Sissy Training you are a “Darling”.  My “Darlings” learn how to be the perfect sissy and gain the self-confidence to move smoothly through their world.  Member how you were so scared to be who you are?  That will all change once you gain your diploma. By the time you finish my lessons, you will use your lessons to be the sissy you want to be.  Sissies are different you know.  Like I helped my most recent sissy be relaxed enough to meet her shemale and fuck the entire weekend.  She called me today and thanked me over and over; telling me all the sorted details.  She was so excited when telling me how she was brought to more than one climax she actually got off two times sharing her weekend adventures.  

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Panty Stealing Sissy Slut

~~~Olivia ~~~ 844~332~2639~x~226~~~

Panty stealing sissy slut is caught.  I’ve been noticing that my laundry seemed riffled through lately. Tonight I walked in as the neighbor upstairs was pulling my red pair of thongs up over his hips.  Screaming at him I told him I should have known it would be his sissy ass.  Eyes looking like a dear caught in the headlights he was muttering some kind of excuse.  What excuse could he have for having my camisole and panties on?  I told him to gather everything up and come with me to my apartment.  He kept stuttering and muttering excuses.  Getting to the apartment; I again scream at him about being in my panties and cami. Making him stand in front of the full-length mirror I pointed out how he looked.  There he stands and he is scared.

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Double Sissification Phone Sex

~~~Olivia ~~~ 844~332~2639~x~226~~~

~~~Zoey ~~~844~332~2639~x~403~~~

Double Sissification is for you. We know how much you crave attention sissy so what would you do for two coaches helping you shred what little manhood you have left?  Zoey and I decided to take pity on you and give you the tips to be the beautiful woman you desire to be.  Starting from scratch, from top to bottom you’ll get the tips that will become the blueprints to your feminine ways. Undergarments are the shapers to misshaped, no curve bodies.  I mean, if you’re gonna be female be an attention-getter.  You will be able to catch more of the boys at the glory hole that way.  Suck more cocks without being picked over like before.  We love sissies with perky personalities and that could rub off of us after spending time with us.  We realize that you know all about the tuck system, making it smooth where it needs to be.

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Sissy Model Sales Clerk Phone Sex

 

~~~Olivia ~~~ 844~332~2639~x~226~~~

The Sissy Model Sales Clerk approached me as I was getting my outfits and cues for my newest assignment.   Walking over to meet her I couldn’t help but notice how well she looked.  Her figure was very trim and she had great taste in what she wore.  She told me that the department head had asked her about helping out with the store’s small show in the afternoon.  I could tell she was so excited she was almost trembling. Watching as she folded the bras and matching panties I couldn’t help but feel some familiarity.  There was something about the whole situation.  The way she touched each item, lingering with each one.  I asked her if she would be modeling and she assured me not even though the small gasp in her voice told me that would be Heaven for her.  Wonder if I were to put in a word for her……

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