From Frat Boy to Sissy Boi Pt. 1 Phone Sex

His name was Chad. Of course it was. Aren’t these frat dudes all named Chad, or Tad, or Brad? He was about 6’2″, blonde blue-eyed All American man’s man. Handsome, masculine, and dumb. Oh so dumb, but very sweet. I was tutoring him in English, and we had been working together for a couple of semesters, so we had gotten to know each other well. We hadn’t hooked up or anything, which was pretty surprising for a whore like myself.

I found out his secret when he opened the wrong tab on his laptop one tutoring session. It was a video clip of a hot guy in women’s panties going down on some huge dude. Chad shut the laptop, embarrassed, but I poked him in the ribs and asked him to dish. He shyly admitted that he got turned on by wearing ladies’ panties. Not only that, he added, but he wanted to be made to do things like the guy in the clip, to suck a dude’s cock, preferably in front of other people.

Read moreFrom Frat Boy to Sissy Boi Pt. 1 Phone Sex

Sucking BBC With My Sissy! Hot Sissy Phone Sex

Avery  1-844-332-2639 ext. 228


It may be confusing to some why I call some of my sissy friends ‘he’ and some of them ‘she’. It depends sometimes on their preference and sometimes on my preference. In other words, it’s a world where they often need to earn the right to have a preference.

Well, my girl Cherry has earned the right to be called whatever the fuck she wants. She goes all out and spares no expense in putting herself together to WOW everyone who sees her and has the pleasure of her pussy and mouth.

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When Maneaters Attack Phonesex: The Cross-Dresser-Part 2

RHIANNA 1-844-332-2639 x 253

“Are you ready,” he asked, his head poking out of the bathroom door, his voice cracking with nerves. “Yes,” I said, making sure to give my voice that innocent tone that makes most men drop their guard. “I’ve been waiting since foreveeeeerrrrrr.” “Okay, here goes.” The bathroom door slowly creaked open and out stepped Jeff, wobbling a bit in his brand new high heels, almost tripping. He paused a moment, steadied his feet, made some adjustments to his tight blue dress and pantyhose and stepped forward. With his composure fully regained, he did a 360 turn and with a big smile on his face asked, “Well, how do I look?”

“Stunning,” I replied with a smile that no doubt did not reach my flint-like eyes but, of course, he was too stupid and caught up in himself to notice….

Read moreWhen Maneaters Attack Phonesex: The Cross-Dresser-Part 2

Pop Goes The Sissy’s Cherry! Phonesex, Part 3

 *~ Princess Natalie (844) 332-2639, ext. 275 ~*

Did you miss Parts 1 and 2? Find them here and over here!

“Oooh, poor sissy! Bet you’re just ACHING to cum now, aren’t you?” giggles one of my teen best friends as we watch poor Sissy straining to remain on her knees with her hairy thighs spread wide open and her wrists crossed behind her back.

Read morePop Goes The Sissy’s Cherry! Phonesex, Part 3

Pop Goes The Sissy’s Cherry! Phonesex

*~Princess Natalie:  (844) 332-2639 ext. 275~*

I caught one of my sissies stealing dirty panties out of my bedroom again the other day. The silly fool looked like a deer in headlights. It was all I could do not to burst out laughing right there. Did he think he was being sneaky?

Read morePop Goes The Sissy’s Cherry! Phonesex

Kinky Phone Sex Sissy Confessions

Hi sissy slut! Cum in! Cum in! I want to hear all about your “parties” (gangbangs)!! Hehehe. You think you are going to shock me but I only have kinkier sluttier stuff to make you do the next time! But keep talking. I know your clitty gets so hard in your panties when you tell me the way you suck and get fucked by so many cocks! You ARE SUCH a KINKY sissy slut though. I luv it! Cum tell me more. Tell me if you’ve gotten fucked in your sissy ass since our last session!!

Licks & Slurps,
<3 Taylor <3
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