Mommy’s New Sissy in Training Part 1

Hello from mommy! I’ve been so excited to share this with you all. My new sissy has finally arrived right at my doorstep like I told him to! I was looking for a new Sissy girl to take under my wing and mold into the perfect little girl I knew I could love, though I’ll use the term lightly at the start until I get her trained more thoroughly. But for now, His name is Mark and he’s been harboring a secret desire to becoming a sissy for most of his life. He’s never had the courage to fully explore this side of himself he’s desired for so long, until now. and I’m here to help him make sure he learns how to be the best sissy he can be.

I welcomed Mark into my home last weekend and we sat down for a long chat about what was to come while he’d be with me. I could see the nervousness in his eyes, but also excitement, a glimmer of hope that he might finally get to experience being the sissy girl he’s always dreamed of being. I reassured him that this was going to be a fun, loving, hands on process and that we’ll go slow at first. That I would guide him every step of the way in his sissy training. He nodded, taking a deep breath as he realized this was really happening.

We started with the basics. I pulled out a pink frilly nightgown and held it up to Mark’s tall, slim frame. He blushed deeply and I could see him processing the idea of wearing such a girly garment. “This will be your new bedtime sleepwear, my dear, you’ll start wearing this every night before you go to sleep” I purred. “It’s important for a sissy to embrace her feminine side, even in the most intimate of moments.” Mark hesitantly reached out and took the nightgown from me, running his fingers over the delicate lace trim. A small gasp escaped his lips. His protest was weak, “But this is so… girly. I don’t know if I should be wearing this.” I chuckled, seeing through his faint protest, which of course i thought was cute. “Of course it’s girly, sweetie. That’s the whole point of this! Now, why don’t you try it on for me? just so we can see if it fits you”

Trembling slightly, Mark stood up and removed his shirt and pants, now just in his boxers. I averted my eyes playfully, letting him retain some modesty for now. He pulled the nightgown over his head and it fell to his thighs, the hemline just grazing his boxer covered manhood. “Oh my, just look at you sweetheart!” I cooed. “You’re going to make such a pretty little sissy girl. Don’t you feel nice and comfortable in your new nightie?” I could see Mark’s Adam’s apple bob as he swallowed hard. “It’s… soft and a bit airy,” he admitted. “And the lace feels nice against my skin.” I clapped my hands together gleefully. “See? I told you you’d like it! Now, let’s find you some matching panties and a bra to complete the look…we can’t have you in those briefs”