Date Crossdressers


A Date With Two Crossdressers Who Really Know How to Please

It was a night I will never forget. I had just met two crossdressers at a club. I had heard about them before, but I hadn’t had the chance to meet any before. I was so intrigued that I got their numbers and decided to take them out on a date. Little did I know that this double date would be one of the most exhilarating and pleasurable experiences I had ever had.

I invited them over to my place so that we could get to know each other a little better. They were both dressed in sexy and revealing lingerie. I couldn’t believe my eyes. It was the stuff of my wildest fantasies. I immediately felt a stirring in my loose fitting boxers as I looked at the two gorgeous crossdressers.

We spent some time talking, getting to know each other better and discussing our shared fantasies. After a while, one of the crossdressers, let’s call him Jack, suggested we move on to something a bit more exciting. I was all for the idea and eagerly asked what he had in mind.

He gave me a sly smile and said he and his friend were both up to no good and wanted to show me a good time that I would never forget. A wave of anticipation ran through my body. I was ready for whatever Jack had in store for me.

The three of us moved from the living room to the bedroom, where I laid out on the bed and waited for them to join me. I watched as Jack and his friend, who we shall call Jenny, undressed each other and stood before me in all their glory. My breath was taken away by their beauty, and I couldn’t wait for them to make their move.

Jenny started things off by straddling me and kissing me deeply, her tongue exploring my mouth in ways that had me wanting more. She then moved down my body, leaving trails of wet, passionate kisses as she went. By the time she reached my thighs, I was already more aroused than I had ever been in my life.

Jack took my hand and guided it to his member, which was already rock-hard and begging to be touched. I ran my fingers all over his shaft, thrilling in the sensation of his smooth, tight foreskin. He moaned in pleasure and rewarded me with a deep, wet kiss.

Jenny continued her voyage of pleasure, stopping at my pulsing hard-on and taking it into her mouth. She licked and sucked me with an intensity that I had never felt before, sending waves of pleasure coursing through my body.

Jack then joined us and the two of them pleasured me to the point of no return. They took turns licking and sucking my penis, and Jenny even used her fingers to insert a toy and stroke my inner walls to add to the sensation. I exploded with ecstasy, my body shuddering with pleasure.

The two of them then lay on either side of me and got to work, using their tongues and hands to bring each other to climax. I watched as they pleasured each other and felt a new wave of arousal at the sight. Jack then rolled on top of me and entered me, showing me how much pleasure two crossdressers could bring when they worked together.

The trio of us spent the next few hours exploring each other’s bodies in every way imaginable. It was an experience that I will never forget, and I am so grateful that I decided to take a chance on these two amazing crossdressers. They taught me that pleasure truly knows no bounds, and that no matter who you are, you can find sexual satisfaction if you just put yourself out there and explore.