To be a man. It gives me such pleasure to laugh at him when he is wearing men’s clothing. We all know that costume is a front! What he wants, is strap-on sex with me, or the real thing. If you’ve ever done a call with me then you know how ready I am to oblige a sissy with my cock. My sissy goes by the name “Sam”, and she likes it when I dress her up and then use her until she is cock drunk and sore.
Tonight, I picked out my favorite piece of lingerie. A sweet white bra and pantie set. Sam’s favorite roleplay was being the shy virgin girl who discovers she loves strap-on sex. Of course, I would wear something more masculine, and commanding, make Sam feel like I was a man about to take her virginity by force. You know how it goes at first, I’m sweet, “Come on baby, you know you like me and want what I have” I’d coo in her ear. She would play the blushing girl and refuse me.
Eventually, my hands would become too free, and would grab at her bare knees. Sam would push my hands away and act horrified that I was politely forcing myself on her. By this point, I would become frustrated and take from her what she wasn’t giving me freely. I’d leave my pants buttoned but would unzip and pull my strap out.
“Get the fuck on your knees, and suck my cock, bitch!” I’d command. She wouldn’t even have an opportunity to refuse. I would overpower her and stuff my 8-inch cock deep into her throat. “Oh, please Mistress, Hailey, I can’t take anymore” Sam would beg. Of course, I knew she wanted me to escalate things. I could hear her pussy throbbing while I pumped my cock in and out of her drooling mouth. She was obsessed with anal phone sex, and that’s how we got started.
And she was embarrassed to admit it and felt less guilty when I “made” her take my cock. “Good slut. Now, lay on your back and let me see that pretty little pussy of yours”. Sam pretended to be full of fear and said “Please! I’m a virgin, I’ve never had sex before!” the look of fear was almost believable. “Shhh, I’ll be the judge of that. Stop talking, and roll onto your back, whore”. Sam did as she was told
I put a generous amount of lube on my cock. Sam tries to wiggle away as I touch and tear at her panties. She won’t stop moving, so I pin her down reach between us, and yank her panties to the side. Immediately, she started bucking her hips trying to throw me off. “Oh no sweetheart, you’re in for a long night of strap-on sex. That hole is going to be mighty sore by the time I’m done”.
She let out a loud moan. “Fucking, whore! I knew you couldn’t resist. Wrap your legs around me and take my cock!” I took her by the hips and began a hard deep fuck journey into her pussy. It took all of 2-minutes before she was begging to cum. Of course, I wasn’t so generous…not yet. “You wanna cum? Aww, that’s so cute. How bad do you wanna cum?” I taughtened.
“I’ll do anything, Mistress! Please!” She said. “Admit you’re a whore and you love strap-on sex, and you can’t get enough of sissy boy sex toys“.
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Had a long and lovely call with Avalon this weekend. She is a wonderful person who is fun to speak with about anything, but of course, she is especially good at the phonesex part of the conversation. She listens intently, knows what her client likes, and contributes her own ideas to the calls. I switched things up in the middle of our call and she didn’t miss a beat, figured out quickly where I was going and met me there in a way that completely fulfilled the fantasy. She is, and remains, extraordinary.
Honestly, Scarlett is absolutely incredible. She is far from an average operator. In fact, she is sexy, passionate, and mesmerizing. I never wanted the call to end, and you won’t either!
Aileen~ Awesome as Usual!
Aileen is the best! We have had quite a few date nights now and she drives me crazy each time. She knows me and what I like now and plays until I can’t take it anymore…in a good way of course. It’s also fun to laugh with her during “pillow talk”. The time always goes too fast! As always, looking forward to next time.
On our latest call Aileen deemed me to be Her sickest disciple, after previously telling me I am the most pathetic. I am so honored to be Her sickest most pathetic disciple. Aileen has brought me so far. I love ❤️ and worship Her and pray that our journey continues forever. Aileen rules!
Michelle’s voice and ideas were very exciting!! I can’t wait until our next adventure!! Everyone should give her a call she won’t disappoint you. When you call her, I’m sure you’ll be feeling the same way!!
Simply put, Vicky is and always has been amazing. She is so much fun to play with and talk to!
Zoey was amazing. The minute our call started, she knew what I needed and delivered like no other has. She is Spectacular!
This red-headed vixen blew more than my fantasy away! Talk about knowing what to do and how to do it…. This was by far the best I have had in a long time.
I feel Mistress Megan is in charge even when not online. I’m her slave.
Megan is extremely open minded. Plays along with even the most taboo fantasies. Close your eyes and enjoy!
Jamie has gotten insanely popular, so she is often “busy” or “offline,” but a call with her is well worth the wait. Sweet, attentive, and often funny as well as dirty, she has raised my fantasy role-play into something hotter than I ever imagined it could be.