MILF Turns Me Into a Sissy

Hello, everyone. My name is Jason, and I am completely mad about MILFs. I’ve also recently developed an interest in crossdressing and am now a sissy.

At first, I was embarrassed about the fact that I like to wear women’s lingerie. It was something I did in secret for a while because I was so mortified by these desires. At first, I started out just as a panty boy. But, eventually, my fetish became more powerful.

I started watching Femdom porn that involved older women and younger crossdressing men. Seeing a mature lady feminizing a younger man turns me on more than any other kind of porn. In fact, it didn’t take long before I couldn’t get off without watching feminization porn or wearing my panties. It was at that point that I realized there was no use in even trying to deny my desires any longer.

Finding A Mature Femdom

Shortly thereafter, I managed to stumble my way upon a fetish personals website or two. At first, my search was pretty much fruitless, but I persevered. I became active in the forums and learned to engage with people in a friendly manner. And, lo and behold, I began to become a well-known denizen of the sites I frequented, and soon, ladies began approaching me!

Having always been attracted to mature women, I couldn’t help but naturally gravitate toward the older ladies who introduced themselves to me. As it turned out, one of them stood out so far in front of the others that I found I couldn’t resist her. And once I confessed my secret forays into crossdressing, she couldn’t wait to meet me, either.

We sent emails and instant messages back and forth for a few days until we transitioned to talking on the phone. And, yes, I must admit that we had more than one MILF phone sex session late at night before bed. Because she lives a couple of hours away from me, we had to wait for about a month before we were both able to synchronize our schedules so we could meet in person. But, boy, oh boy, when we did meet….

MILF Feminizes Me and Turns Me Into a Sissy!

The two of us got together on a weekend. She had driven down to my town and had gotten a hotel room. As it turned out, she didn’t need it.  We spent the majority of the weekend at my house, where she took quite a bit of time turning me into the crossdresser of her dreams.

I could tell that she had a lot of experience with feminization and transforming men like me into sissy boys. I was extremely nervous, as you can imagine, but my mature Mistress quickly put me at ease with her authoritative demeanor and her obvious familiarity with what she was doing.

She’d had me go out and select what I thought was the perfect outfit the day before she came to visit. I took it out at her command and began to get dressed in the short black shorts I’d picked out and a soft pink tank top. Underneath, I wore a pair of pink panties that were the same color as my shirt. To top it all off, I had a pair of cute black wedge sandals to wear as well.

I began modeling my outfit for my Femdom Mistress. She smiled at me, and I felt encouraged that I’d pleased her.

Makeup For the Sissy Boy

It seemed, however, that my MILF Mistress had more plans for this sissy. She was, in fact, pleased with my outfit selection, but she wanted to go a little further. She sat me down on a stool in front of my dresser and began teaching me how to do my own makeup! I watched her transform me from a guy wearing girly clothes into a genuine sissy right before my very eyes. It was pretty amazing, actually.

After she finished making me up, she took me to the bed and began to slip into her strap on harness. She said that if I looked like a girl, she was going to have to fuck me like one! That very night, she taught me to love being fucked by a strap on Femdom!

I loved every moment of it…and I haven’t looked back since!

Give one of our MILF Mistresses a call, today!