Crossdressing Sissy Feminization Date: Lace & Makeup Makeover

Finally, he gets the full sissy makeover of his dreams.

He thought he was a big macho man until I took all his masculinity away. A crossdressing sissy feminization date was all it took to convert a masculine, hot-shot boyfriend into a prissy posh blonde bimbo. He really didn’t see it coming, either. See, Brian always portrayed himself as such a ladies’ man! He was always at the gym, pounding pre-workout and protein shakes, and everything he could to make himself the sexiest man around. But I’d known him for quite a long time, and I’d found some flaws in the armor. For one, he had low testosterone — what a clear giveaway that he was meant for something different! And two, he always sounded too enthusiastic about what lingerie I was wearing.

Now, there’s a difference between a horny man who wants to know what panties you have on so he can rip them off and a man who’s secretly wondering how they feel. I knew which one Brian was. But I had to coax it out of him a little more. He hadn’t even stumbled across sissy porn until I ‘accidentally’ came across it one day. We had a little giggle about it, but I saw the look in his eyes. A whole new world had been uncovered. And that’s when I came up with a plan. Little by little, I’d expose him to more sissy play. And one day I would kick off the big reveal, the crossdressing sissy feminization that would turn him into a full-blown bimbo.

My crossdressing sissy feminization plans started off subtly.

First, it was a funny porn video that we giggled about. Then, I started making little jokes whenever the subject of lingerie or panties came up. And trust me, they came up often! He was frequently horny and asking what color my panties were, or what lingerie I was wearing. And soon my answers turned into “Why? You wanna try them on?” or little jokes about how cute and pink they were, and how they’d look great on him instead. Every time I said something like that, he blushed rapidly. My crossdressing sissy feminization plans were starting off with a bang! He turned so bashful and giddy when I turned it on him.

And one day, he wanted to ‘spoil me’ and take me to the mall. Of course, his favorite stores to stop by were the lingerie stores. I always wondered about it. Usually, the bored husbands and dads wait outside the store, waiting for it to be over. But he was right there with me, looking everything over cautiously. And I decided to start the real crossdressing sissy feminization makeover right there. As I picked out a cute little pink thong, I twirled it around my finger. “Bri, I want you to try this on for me.” He stood like a deer in headlights, unsure if he heard me right. “You heard me right! Come on, I want you to try this bra on too.. it’d look cute on you.” He was both embarrassed and amused, hopeful and fearful. I giggled and led him over to the fitting room area anyways.

I made him strip down naked for me.

With the door locked behind us, he was lulled into a sense of security. In the moody store lighting, he looked deliciously sexy as he pulled on his little pink thong. It was almost neon pink against his tan. And then I helped him put on the little bra too. He was still blushing red as a tomato as he looked at himself in the mirror. I giggled and spanked my hand against his ass. “Look at that! You look like you stepped out of those sissy videos…” He gasped as I said that, mortified that someone might have heard us in the hallway. And they did because we heard some giggling from some of the other girls in the fitting rooms. The crossdressing sissy feminization was going so perfectly, I even noticed him getting hard in his little thong.

He was so excited that he even poked out of it a little bit. “Well, now we’re gonna have to buy it, you’re hard and rubbing all on it!” He blushed even harder, practically melting and trying to hide his boner with his hands. But it was hopeless, and I continued teasing him about it. “You know what’ll make this even better?” I teased, looking through my purse to get a little pink lipstick. He stood perfectly still as I applied it to his lips. I even did his makeup, adding a little bit of blush, and a sparkly nude eyeshadow, and did his eyebrows. With a little on-the-go contour, he was looking so glamorous after his crossdressing sissy feminization. And that was just the beginning! I had more plans and more shopping to do. Up next: high heels, a skirt, and a sexy top.

What should I make my new sissy wear?

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