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?
Hardcore sissy training begins with the wardrobe. A sissy shopp... Read More
Bye Bye Tight Virgin Ass Your tight virgin ass deserves a perfe... Read More
When men get caught being pathetic, they will do anything. I ca... Read More
In my sissy outfit training sessions, I want my sissies to realize jus... Read More
A paradise floating in the sky. Come in worthless peasant, don&... Read More
A sissy bitch called wanting to report his quest for cock. He s... Read More
Your Sissy Slut Confession is Safe with Me Do you have a Sissy... Read More
In a world of my own. That’s where my nympho MILF persona tak... Read More
Sissy slut bitch boys are my favorite!! Sissy slut bitch boy, d... Read More
You know you think about dick all the time. So, tell me when di... Read More
Blackmail My Coworker To Suck Cock I want to tell you a story a... Read More
He has a panty fetish and loves that silky material on his pathetic ex... Read More
Raven is Smart, Funny, Attentive and Super Sexy!
Aileen is in a class all her own. A Mistress with the depth of sociologist, and the flexibility and balance of a trapeze artist. She is masterful at giving me the most stimulating sessions possible for me in a wide range of areas. She also happens to be a delightful human. I’m convinced her expertise is probably limitless. Aileen for president, 2024!
Outstanding call!! May took her time to learn what I wanted. Then brought a ton of enthusiasm to the call!! It was a great first call and I think it will just get better next time!!
There is a reason Jesse is always busy every time she works and that’s because she is the best at what she does. She is so easy to relate to and connect with, regardless of what you want out of a call. She is class with sass. Call her!
Raven is the best in every way! She listens to your requests, very open minded and none judgmental. She remembers you when you call back and she really knows how to get the most kinky naughtiness out of you. I never feel rushed. I’ve selected Raven enough times that I now feel I’m talking to a friend that truly wants to see me enjoy myself until I explode with excitement. Simply the best!
Wow! My first call with Chloe far exceeded my expectations and my bar was set high. The best compliment I can give is Chloe’s reality was better than my fantasy and that never happens. She is beautiful, smart, sexy, has an intoxicating voice and an infectious laugh. She is so genuine, thoughtful, and can adapt to any kink. Simply put, Call Her!!
Sage is amazing. She has taken complete control of the cock, the erections, and the orgasms that used to be mine. I was licking her bulls cum off her perfect breasts while she locked me in the chastity device. Wish me luck on my next call!
Kayla was so sweet, smart and fun to talk to. Getting to know her made our experience even greater. I can’t say enough great things about her. This is the start to some fun in the future.
Hailey is absolutely the best. Knew exactly what I wanted. Sexy voice an very pleasant. 10 stars
Wow. Kali understood exactly what I was after and delivered. Great voice, great actress. Great experience. Only thing I forgot was ask how to tip her after the call. New fan of the site here.
Brittany was magical. She took the time to get to know me and make me feel comfortable with her. Then we explored each other and my time with her was amazing. I had told her I just called the service for the first time that day and was thrilled with my first call and she assured me her and I would have a great time. We did!! You are amazing Brittany.
Her voice is amazing. Raven remembers you, from call to call she gets to know you, and once she knows what kinks drive you, she will drive you wild!