Hello, naughty ones. As we prepare to say goodbye to 2023, I’m reminded of all the interesting people I’ve met since my divorce, including my first sissy.
It all started innocently enough. One margarita with a guy I’ll call Eduardo turned into a dinner date. That dinner date turned into more dates and lots of late-night conversations. And before I knew it, Eduardo and I were an item.
He was like a breath of fresh air in my post-divorce life. And as our relationship progressed, so did the layers of his personality. One major revelation happened when we were at that point in our relationship where comfort began to override initial nervousness, and vulnerability started to peek through the cracks.
I remember the night vividly. Eduardo and I were lying in bed, discussing our fantasies and desires when he told me he was into sissification. And he wanted to be my first sissy.
Sissification, on the other hand, was still uncharted territory for me at that point in my life. I didn’t know exactly what it entailed or how it fit into Eduardo’s life, or, by extension, our budding relationship. So I had a lot to learn and consider. And in the days that followed, I took a step back to reflect and educate myself about sissification.
I delved into online resources, seeking to grasp the psychology and nuances of sissification. And as I absorbed this newfound knowledge, I initiated several conversations with Eduardo. We discussed his desires, boundaries, and the emotional aspects tied to his kink. In turn, I shared my thoughts and concerns with him. And one day while we were watching vintage music videos, an idea struck me: Why not have Eduardo embrace the boundary-pushing spirit of Madonna via her “Like a Virgin” video?
I gently broached the subject with Eduardo, gauging his reaction. And to my surprise, he was intrigued and willing to give it a try. So we perused different boutiques and selected pieces that captured the essence of Madonna’s daring ‘80s style. And later that evening, Eduardo, the mild-mannered accountant, shed his conservative attire and became my first sissy.
The addition of stockings and a garter belt added an extra layer of sensuality to the ensemble. And I continued to take note of the changes as Eduardo carefully fastened the stockings, his hands moving with a deliberate yet delicate touch. The wisp of fabric against his skin became a symphony of self-discovery, each article of clothing contributing to the creation of a persona that resonated with his desires.
The hesitancy that lingered earlier had given way to a palpable enthusiasm. His eyes met mine in the mirror, and a smile that can only be described as a mix of excitement and satisfaction spread across his face as “Like a Virgin” played in the background. It was a moment of revelation, a glimpse into the transformative power of clothing.
I sat by my makeup vanity and hit repeat. Then I nodded at Eduardo, and he instinctively began to sing all the words to the song while mimicking Madonna’s dance moves. When the song ended, I grabbed my hairbrush and called him over to me. Then I took him across my knee, lifted his wedding dress, and proceeded to spank his ass while I mock-taunted him for being so eager to dress provocatively and sing suggestive lyrics.
Eduardo’s cock was pressed against my thighs, and I could feel it getting harder with each smack and the subsequent gasps of pleasure that escaped his lips. And I taunted him for that as well by making him say he was a slut who couldn’t wait to get fucked. Then I tossed the hairbrush and started fucking him with a strap-on until cum stained his wedding dress.
I still marvel at the beauty of self-discovery within the context of our relationship in general. Eduardo’s sissification kink wasn’t just about dressing up and affecting an effeminate demeanor. It was also about him embracing a facet of his identity that had found a safe haven in our connection.
Call me for more!
My stepfather loved giving Bare Bottom Spankings as punishment ... Read More
Denver sat back in her plush leather chair The glow of h... Read More
Unleashing the Power of Findom: How I Seduced Him into Giving Me Every... Read More
Tie Up And Use – Finding The Perfect Chair Living in a ho... Read More
I will never again underestimate how horny men constantly are. ... Read More
I’m Your Sex Slave! I want you to have your way with me. I wa... Read More
I belong to my kinky domme Master I am my kinky domme Master’... Read More
Showing off the goods The door opened and Jim was greeted by an... Read More
Oath to Mistress Sofia At the same time, he didn’t want to ri... Read More
Pussy licking nerd needed for insatiable Librarian. I love my j... Read More
Orgasm Denial Scarlett had been a bad girl, She was craving coc... Read More
My Bedroom Dom I met my bedroom Dom during one of the Kinky Kar... Read More
Tremendous customer service and professionalism. Aileen took the time and interest to start getting to know me. Just a delight to have a conversation with, aside from her sexy voice.
I had a great time with my two beautiful and sexy ladies Carmen and Kayla. It has been a while since we played together. It was definitely worth the wait!
I had a great time with my two beautiful and sexy ladies Carmen and Kayla. It has been a while since we played together. It was definitely worth the wait!
Ariel is truly amazing. Her voice is seductive and she really knows how to bring out the dirtiest version of me, hehe!!
Aileen is hot as they cum. She really knows what she is doing and is always the most satisfying!
WOW, I had an absolutely wonderful and memorable call with Jade! She listened to the role play that I wanted to work through with her and she was beyond perfect. She was able to step into her role as my milf neighbor growing up and really made my phone sex fantasy come to life! I can’t wait till I am working out of town again and have another chance to call her as I have other role plays to do with her.
Joey OUTSHINES everybody!! She is the ABSOLUTE PERFECT combination of everything. Sweetness ✔️, Compassion ✔️, Sincerity ✔️, Intelligence ✔️. And her Sexiness. . . OMG!!! Joey makes my life AMAZING!!!
Bailee was super enthusiastic and rolled right into playing out the fantasy I had. She is phenomenal.
Amber is kind and understanding of my needs. She would make a good friend!
This was only my second call with Addison, and I am already addicted to her sexy voice. She knows exactly how to command and control me. Love the way she takes me all the way to the edge, before she gives me the hands off command. Looking forward to obeying her more often.
Vanessa is simply amazing. She can be so precious or be so fucking wicked. Her oral skills are insane. She will make your cock cum, cum and cum again. If you want a spicy and wicked good time, Call Vanessa!!
Had a super hot call with Gracie! Her voice sounds so innocent and seductive at the same time. She is so sexy and we always conclude with an explosive finish.