Clint has always been different regarding being the stereotypical male. He knew he wasn’t like the other boys in school. He always admired watching his step-mom prepare for the day. When she puts on her makeup or her pantyhose. Often, Clint would sneak his step-mom’s pair of panties because he loved feeling feminine. Consequently, now that Clint is older he has quite a collection of sexy clothes. However, now this is a chapter in Clint’s life that he would love to explore. He’s always had this feeling deep down but never had the nerve to try. But not until he found this ad that said, “Hailey’s Sissy Pegging Sessions: Embracing the unknown: First Time Anal. Call 888-823-9243.”All of a sudden, his curiosity got the better of him and he picked up the phone.
When Hailey picked up the phone to introduce herself to Clint. He knew he was in a safe place immediately. Because the tone in her voice was welcoming. After he told her a bit about himself, Hailey coached him by saying. “Since this is your very first time, we will need to do a little ass training. Then after that, we can enjoy a sissy-pegging session. This week I want you to get a couple of butt plugs of different sizes. You will start with the small one first. Next, do your homework, and I’ll see you next week.”
Clint loved that she was assertive. He was eager to quickly gather what he needed. He made it an all-day event by getting a bath and shaving all over. Even putting on his sexy lingerie and wearing heels and a wig. It made his little clitty so hard to finally use the butt plugs.
First, starting with the smaller one, it slipped in perfectly. Next, he called her on the phone. “I have my butt plug in, and I’m ass training like a good sissy slut.” Hailey instructed him on how to use the butt plug. And to rub his little clitty in his panties. “Mmm, good sissy! Now the large one, we have to get that ass ready for me to pound that sissy whore ass, with my huge strap on.” Clint did everything she asked, he loved how she told him what to do. The thought of a sexy powerful woman in a sissy pegging session, nearly made his clitty squirt. The big butt plug was about six inches and it vibrated hard. “I’m going to fuck that sissy ass out when we meet. Because I’m going to make you take every inch of my girl cock.”
At the hotel room for their first sissy-pegging session. I walk out of the bathroom with a tight black mini skirt, red bottom high heels, thigh highs, and a push-up bra. She is deliciously sexy with a glow on her face, ready to use Clint. She had him dressed up like the proper sissy slut that he was. Then when he looks down between her thighs. And there it was peeking out from her mini skirt, a nine-inch thick strap-on dildo just hanging there. “On your knees, Bitch, and show me what a good cock sucking whore you can be.” Clint was eager to be the true sissy he was. So he sucked and swallowed and sucked her girl’s cock like he was a thirsty bitch. He felt so submissive under her feminine power and was willing to do anything she said.
Finally, Hailey pulls his panties to the side and slides her big cock in that little sissy ass. He pumps deeper and deeper and could feel his boy pussy stretching out like a two-dollar whore. Next her perfect tits bounced and jiggled as she drove it in deeper. “Please FUCK ME! Turn me into a sissy ass whore!” Hailey demands, “Cum for me sissy, and make that little clitty squirt.” And with her permission, Clint explodes all over his belly. Are you a sissy that needs your boy pussy pegged?
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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.
