My ex loved to push my boundaries with my sexuality

A few years ago, I (28M at the time) met a girl (24F) on a dating app and we quickly got chatting. Some background - I have always been curious about guys but never felt comfortable enough to talk about it with any girl I was dating. This girl gave me good vibes straight away, and told me she was bi very early on. I took that as a green light to be honest, and I told her about my curiosity for guys. To my surprise she wasn't phased by it, and actually took an interest and asked questions to help me feel comfortable.

We'd been dating for a few months when she brought it up with me again. She asked what I'm curious about, why I haven't explored it before, and how she can help me explore it. I loved how open she was, and it felt so refreshing to be honest and upfront about my sexuality. One night, during sex, she grabbed her laptop and pulled up Pornhub - "let's watch something you like" - and navigated to the gay category. I was stunned, but super turned on. I selected a video that looked good, and we watched it while I fucked her from behind. She asked what I liked about it, telling me to go into detail and why I liked it. Everything I said seemed to turn her on more.

This became a regular thing for us. I'd get home from work and she'd be waiting for me with the hub open, ready with a suggestion of what we could watch today. Pretty quickly I could tell she was enjoying it just as much as me, and one day she told me to download Grindr, which I happily did. We sat there and made my account together. She picked my photos, helped me with my bio, and pretty soon I was chatting to guys while she watched and helped me with what to say. I'd chat to all kinds of guys, swapping pics, sexting, and generally exploring this for the first time. She'd have me rate guys and their cocks, and she'd take pics for me to send back to them.

She also helped me explore dressing up. I had a thing for wearing women's panties, so she would give me a pair of hers to wear, or sometimes come home with something special she'd bought for me. Then it was trying on her dresses, skirts, bras, tops and anything else I could fit into. I loved dressing up for her. It made me feel extremely sexy, especially with how she would react to me wearing it. Sometimes I'd fuck her while I was dressed up, and it would escalate to her playing with my ass while she called me a "good girl".

One Saturday, we woke up and she said "I have a plan for us today". I was expecting a trip to the farmers market or something, but she had different plans. She wanted to fully dress me up, so she took me to the mall and we picked out some clothes, shoes (hard to find in my size) and a wig to take home. We spent the day getting me dressed up, she put makeup on me, and really went to town with making me look and feel sexy. Then she told me she was taking me to a gay/trans bar...

I'd never been to a gay bar before, let alone dressed up like I was. She drove us there and explained that tonight she was going to be my chaperone, and she was going to make me feel sexier than I've ever felt before. We arrived to the bar, she ordered us some drinks, and then sat back as we were approached by countless men. She would lead the conversation, as she could tell I was nervous, but the whole time she never let me feel unsafe. She was there for me, and she wanted me to feel sexy and wanted. After some time, we hit the dancefloor. I was already feeling sexy and extremely horny, but I wasn't prepared for the amount of guys ready to feel me up. I had hands all over me, some up my skirt, some on my ass, some moving up my thigh. I felt intoxicated by the attention I was getting, and I could tell she was enjoying it too.

I loved how comfortable she made me feel with my sexuality. She really helped me explore something I had always felt unsure about, and she made me feel so safe.