Olivia’s Newest “Darling”

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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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A Personal Performance

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I know this dirty old perv who loves to watch when I bring home a sissy boy. I guess you could say it’s as if I put on a personal performance, like a live porno just for him. He has built a two-way mirror in one of the guest rooms so that I could put on a show for him without the other party even knowing.

This weekend I found this delicate young man who’d never been with a shemale before. I took him back to our special room to play with me. The lights were dim as we sat on the bed to make out. Our tongues were twisting together, and his hands were eager to get under my skirt. However, I wanted to slow my new toy down so I could really put on a show for the old perv.

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Time For Deep Throat Training Sissy Girl

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Sissy training can be rigorous! There is so much a good girl needs to know! Today I want to work on your deep throating tolerance. Crawl over to the deep throat station and check out the contraption I’ve set up to help you. You’ll see this spotless mirror with the strapon harness about mouth level. I want you to be able to watch yourself as you choke and gag.

Glued to the mirror above where the dildo will attach is a counter. You’ll have to deep throat far enough to have your nose bump the clicker on the counter. After you reach fifty strokes, we’ll increase the size and thickness of the dildo.

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Suck A Dick Phone Sex

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Suck a dick. Yes, you. We all know that sissy sluts suck a lot of dick. It’s a well known fact that sissy boys have a natural affinity for cocksucking. So you might as well just admit it. You are a dirty little sissy slut. Everyone already knows, so why keep trying to hide it? Just look at those DSL’s, dick sucking lips. I’m sure you can suck the chrome off a trailer hitch with the best of them. It’s so fucking obvious.

Once you start sucking I’m sure you will beg for more. It’s in your nature to crave cock. You crave cocks 24/7 don’t you? Every time you meet a new man you are staring at his crotch. You perv on every cock you encounter. Just admit the fact that you are a complete faggot.

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Sissy Shemale Games With Alexus

TS alexus peels panties down her curvaceous ass

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Do you like to play games? I have one for us. So you come over, and I dress you up in a slutty little outfit, no panties, of course, because this game requires both your holes. My TS best friend Maria comes over with her sissy girl; games are always more fun when you can play with teams! So, of course, you and I are a team (and we better win), and Maria and her little whore are a team.

Right here in the living room, I’ve dragged two barstools out and slapped an eight-inch suction cup dildo to each seat. The game is going to get super fun, really fast! You and the sissy will start to throat those dildos while Maria and I stuff your boipussys.

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A Girl’s First Love

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A girl’s first love MUST be herself. Being a woman comes with so much pressure and so many expectations. It can be very difficult to give yourself to others if you aren’t sure how to love yourself first. I love when a new sissy dials me up and asks if I can help them become more of a girl.

Mmm, such a beautiful opportunity for me. To take a blank canvas of a body and show her how to love herself as a woman. Sure, we can call it guided masturbation if you’d like. I so enjoy showing you how to take cock in your mouth as well as in your pussy. I get so excited to show you how to rub your clit through your new panties.

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Stroke You As You Ride Me Phonesex

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I love to stroke a nice fat faggot cock as I’m being rode. It’s such an amazing feeling to have a tight pucker sucking on my cock while my hand jerks off a hard cock. Mostly, I don’t even have to stroke or jerk; the horny sissy riding me does all the work for me. Every thrust of her hips pumps her cock through my fist.

Watching it bubble with precum makes me so hard. The horny girl just oozes over my fist, and it makes me fuck my hips up into her. Harder and harder. Jack hammering my cock up into that boypussi while my fist clenches.

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My Brother’s Run A Train Phone Sex

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My Brothers Run A Train Phone Sex – So, you say you want to be a sissy. The problem is you have absolutely no clue as to how to suck cock. I am here to offer your sissy ass up to some guys I know really well. You have always dreamed about it and fantasized about choking on a big cock. But you are so scared and timid. It’s fucking pathetic. I can help you with that faggot. Let me introduce you to my sexy as fuck older brothers – Mac, Mason and Miles. Now, remember, these are my brothers so of course they are good looking and hot.They also all have big, swinging cocks. I’m sure they will appreciate your pretty, little sissy mouth.

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Beg For Cock Cum Phonesex With Feisty Wifey Felicity

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Cock cum is like coffee to Sissies. Think about the similarities. They wake up wishing for a hot load while most of us wake up ready to sip from a hot cup.

It’s addicting! Much like the rest of us, after that first sip when caffeine takes over your soul, cum has done the same to what used to be average men! After that first hit of cum, all those sissies think about is their next taste! They’ll beg and plead for cock cum.

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Lori Teaches Alexus To Lick Pussy Phonesex

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I’m a woman of many talents, a jack of all trades if you will, but I have a small confession. I’ve never been very good at eating pussy. Sure, sure, I love to fuck pussy and tease it with my fingers, but I guess I’m a little shy about licking pussy.

Those things are weird, and not having one myself, I’ve never really felt confident enough to enjoy it. I confessed this to Lori, who laughed a loud laugh at the idea. She said she would help me get over that fear real quick.

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