After coming out to the woman I had tried dating, she and I had became friends. As months went by I began confided in her more and more, until she knew I was also a crossdressing sissy. She had began to help me in my journey by gifting me spare makeup and nail polish she had. Then she started giving me advice on where and what to shop for. She made me a purple handbag so I could keep my personal items in, carrying it allowed me to wear feminine fitting clothing. We even shared wine on evenings when we would both wear dresses on her sofa and I would tell her about my latest sissy fantasies. Eventually she suggested that I join Grindr and explore relationships with men. 

It was the natural next step to take, so I listened to her, joined Grindr, and wrote my bio. I was candid about what I was looking for, and quickly had taps and responses. It was fun to chat and flirt with guys. Soon they began to ask for me to dress up for them and send them pictures, which I gladly did. In my messages I was warm, playful, and showed a willingness to put their desires first. I enjoyed their attention, and could feel myself growing as a sissy. After just a couple of weeks of chatting and flirting I decided to invite along one of my new interests for a hookup. 

We both had similar tendencies, and had been able to chat with an easy friskiness. He was much older than me, but I didn’t mind, as I was learning that I seemed to find older men attractive. He’d agreed to come by one morning. So I thoroughly cleaned my apartment, changed the bed, showered, put on seductive music, and used perfume everywhere. I was a mixture of excitement and nervousness as I saw him approach the building. Whilst opening the front door I took a deep breath, he stepped in, and I shut the door behind him. I greeted him in my Barbie pink pyjamas, and pointed to where the restroom was if he needed it. Then I showed him a clothes horse for him put all his things on, and then I said with a smile ‘when you are ready, join me in the bedroom’. I went to wait lying on the bed. A couple of minutes passed and then he appeared by the bed wearing only a thong. Without hesitating we both leaned in and began kissing. It was then we realised a problem. 

Neither of us were Alphas. We both wanted to give pleasure, not to receive it. We failed to recognise that neither of us was strong enough. Alphas want to be gratified, and we were just two sissies, physically and mentally, all we could do is kiss and cuddle. We both enjoyed holding and being wrapped around each other, caressing, touching, smooching and being close. We were both indulging in those moments, but we were also still limp. Time was passing and we lacked any firmness, we were flaccid. I had listened to a lot of online content aimed at sissies, and suddenly all of that conditioning I consumed was making itself felt. I knew confidence wasn’t meant for me. And being satisfied wasn’t meant for me either. ‘I’m weak and belong in panties’, I thought. For 2 hours we kept on trying again and again, but like two negative ends of a magnet, we just couldn’t. 

It was still a lovely experience. Despite our low libido, the gentle time laying with another guy was a wonderful way to start the day. After showing him out with an affectionate kiss, I showered, changed into fresh panties, and then thought about the hookup. I liked that from trying and failing we had both learned something. We knew now what we were looking for and what we would not be able to do. In the end our natures were too much the same, it didn’t matter how much effort we put in and how many times we tried. In my reflections I began to understand, that although we both felt good holding each other, we couldn’t stop being sissies.