Last weekend my good friend came over and admitted a secret: He secretly wanted to be a sissy, but didn’t know how. Moreover, he wanted to live his life as a sissy slut and fuck and suck big, black cocks, but had no idea what to do. So I offered to be his teacher and guide him through my sissy training course.
First, I had to make sure he looked like a good little sissy. But when I saw his lingerie collection, it wasn’t slutty enough. He needed more sheer panels to show off that little sissy cock. Although he was hesitant, he knew he was in good hands with me for sissy training. I put him in a black g-string that barely covered his boy pussy. Even though his cock and balls were small enough to make him popular in small penis humiliation circles, the sheer material on the g-string didn’t do much to contain his small balls. Then I put him in a lacy, black bralette, his nipples on display. Then I topped it all off with a black leather collar that read “Sissy Slut” in large, gold letters.
Next, it was time for a makeup crash course, sissy training style. I explained that he should always use mascara so it runs when he’s getting facefucked. Of course, he should also always wear lip gloss or a moisturizing lip gloss. Since he never had experience as a sissy slut before, I knew he had a lot to learn. I explained the importance of his lipstick or lip gloss smearing on a cock and how smudged lipstick makes a sissy look even sluttier. His eyes lit up when I explained that the makeup was for making him look like a messy whore. After all, as a sissy training instructor, it was my job to make him look like a pro sissy slut.
Finally, it was time for him to get his first taste of big, black cock. While he watched my sissy training cock sucking porn compilation, I texted my two friends, who were well known for having the thickest, blackest cocks in the state and invited them over to break in a new sissy. Without a doubt, they were happy to oblige.
Soon after I texted them, they were at my front door, cocks bulging. As they came into my living room, they saw my sissy training student sitting on my couch watching porn education. Once he looked up and caught sight of those big, black daddies, his mouth dropped open. I told him to kneel on the floor as my friends took out their massive black cocks. As their respective 10-inch and 12-inch cocks popped out of their pants, I instructed my student to show me what a good sissy does when he sees large cocks in his face.
Without hesitation, he took the 10-incher in his mouth first. Once the black cock entered his slutty sissy mouth, his lips slid down to the base. Unsurprisingly, the eager little sissy gagged as he went balls deep on that big, black cock. My friend grabbed my sissy friend’s head, vigorously face-fucking him. Once I felt like my sissy had learned the fundamentals of sucking a big, black cock, it was time for him to take the bigger black cock. At first, he struggled and gagged on the 12-incher. But after holding his head down on the thick, black cock, my little sissy managed to take it all down his throat like a porn star. This time, my sissy friend didn’t even stop to breathe, so his mascara was already running down his face by the end of this course in sissy training.
Once my sissy finished sucking those big black cocks, mascara ran down his cheeks. Now it was time for him to get spit-roasted. The 10-inch cock penetrated my sissy slut’s tight little boy pussy while the 12-incher simultaneously fucked his face. As his body was filled with black cock as he took both cocks in both of his holes, I noticed he was stroking his small cock pleasurably. With all the thrusting, my sissy was so full he didn’t even notice as I filmed his sissy technique with my phone for review later.
After an hour of hardcore face fucking, I felt that my sissy training pupil was ready to take his first exam. I instructed both of my friends to cum in the sissy’s holes. As both black cocks exploded in my sissy slut’s fuck holes, my little sissy also came. His little cock spurted a small load of jizz that paled in comparison to the massive loads pumped into him. Once the black cocks slid out of my sissy, I asked him how his first sissy training lesson was. He smiled happily as he thanked me. Little does he know, but lesson number two features three even bigger, black cocks.
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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.