Sissy training his 1st time sucking cock.

Sissy training session heads down to the glory hole.

It was finally time to take his sissy training to the next level. My eyes sparkled with mischief as I looked at Tommy, my sissy protégé, in the mirror. “Tonight, my dear, you’re going to learn a whole new level of pleasure,” I purred, my blond hair cascading down my shoulders. Tommy, dressed in a slutty little black dress, wig, and makeup, looked like a vixen ready to pounce. I’d been giving Tommy sissy training lessons for a while now, but tonight was special. I  was taking my little sissy to the glory hole.  It’s one of my favorite places where men and sissies get to explore their wildest fantasies. I could see the nervous excitement in Tommy’s eyes, and it made my pussy wet with anticipation.

“Remember, Tommy, it’s all about the tease,” I reminded, adjusting Tommy’s wig. “Make them beg for it, and then, when they least expect it, take their dick in your mouth.” Tommy nodded, his heart pounding in his chest.  As we walked into the dimly lit room, I could feel the sexual tension in the air. Men of all shapes and sizes were waiting for their turn at the glory hole.  I led Tommy to a booth and closed the door behind us. I could see the outline of a hard dick through the hole in the wall. “Go on, Tommy,” I whispered. “Show me what you’ve learned so far in your sissy training.” Tommy hesitated for a moment before dropping to his knees. He reached out and wrapped his hand around the stranger’s dick, feeling it throb in his hand.

Sissy training session starts now.

Slowly, Tommy began to stroke the stranger’s dick, his own cock hardening in his panties. He leaned forward and flicked his tongue over the tip, tasting the salty precum. The stranger moaned, and Tommy felt a surge of power. “That’s it, Tommy,” I whispered, my hand slipping between my legs. “Take it all in.” Tommy opened his mouth wide and took the stranger’s cock deep into his throat. He gagged slightly, but the sensation only turned him on more. As Tommy sucked the stranger’s cock,  I couldn’t help but touch myself.  I watched as Tommy’s lips wrapped around the thick shaft, his eyes closed in ecstasy. I could feel my own orgasm building, and I knew I wouldn’t be able to hold back much longer. “Fuck, Tommy,” I moaned, my fingers rubbing my clit in circles. I was so proud of how the sissy training was going.

“You’re such a good little slut.” Tommy moaned in response, the vibrations sending the stranger over the edge. He came hard, filling Tommy’s mouth with his first cum load. Tommy swallowed every last drop, feeling it slide down his throat. He looked up at me, his eyes filled with desire. “I want more,” he said, his voice husky. I smiled and opened the door to the booth. “Then let’s give them something to remember,” she said, leading Tommy to the next booth. As the night wore on, Tommy sucked cock after cock, his cock aching for release. I’d watched him, my pussy soaked. I knew I  wouldn’t hold back much longer. “Tommy,” I said, my voice thick with lust. “I need you to eat this orgasm out of my pussy.” Tommy looked up at me, his eyes wide.  I grabbed his hand and led him to a private booth.

My turn

I pushed him down onto the bench and straddled his face. “I want you to tongue fuck me like the slutty little sissy you are,” I whispered in his ear. Tommy groaned and dove face-first between my legs, burying his tongue deep inside my pussy.  I moaned, feeling him devour my pussy like a buffet.  Tommy slurped hard and fast, his own orgasm building. I, too, could feel myself on the edge again, and I couldn’t hold back any longer. “I’m gonna come,” I moaned, my fingers digging into Tommy’s shoulders. “Fuck, I’m gonna come!” Tommy’s tongue fucked me even faster, feeling his own orgasm building. He could feel his balls tightening, and he knew he was close. “Fuck, I’m coming!” he cried out, his dick exploding all over my thigh. I moaned, feeling his hot cum cover my thigh. I’d cum hard, my pussy throbbing.

As we both lay there, panting and sweating, I couldn’t help but smile. “You did good, Tommy,” I said, kissing him gently on the cheek. “You’re a natural.” Tommy smiled back, feeling a sense of satisfaction he had never felt before. He knew that this was just the beginning of his sissy training journey, and he couldn’t wait to see where it would take him. As we left the glory hole, I turned to Tommy with a wink. “Next time, we’re gonna try something even wilder,” I informed him. Tommy could only nod, his heart still pounding in his chest. He knew he was in for one hell of a ride with a kinky phone slut like me.  Do you want to try your own sissy phone sex session?  Pick up the phone and let’s have some fun.

Call Mallory 1-877-729-7626