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A Very Sissy Hookup (true story)
After coming out to the woman I had tried dating, she and I became friends. As months went by, I began confiding in her more and more, until she knew I was also a crossdressing sissy. She had begun 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, and 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, 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 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 one of my new interests for a hookup.
A Very Sissy Hookup
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