Now to preface, I understand that there is only so straight you can be while openly dressing as a girl. I probably wouldnt have gotten as far as I did with it if it wasnt for a driend of my family having a daughter that was a year younger than me and felt very much like a little sister. When I confided in her about my desire to dress like a girl, she got super excited and invited me for a makeover right away! Ever since then she continually pushed me out of my shell and eventually into shopping malls and bars. I’ve had quite a few guys tell me I’m very pretty, generally I always tried to pick up girls when dressed up, to a surprising amount of success. This one time though, I was at a bar wearing my usual red wig, blue dress, and black heels when a confident man in his mid 30s came up and ordered me a cosmo. I was already a little tipsy and there was something about this man that I found rather interesting. He had a birthmark in his hair, a smashed fingernail that he said he got in his carpentry job, and it felt like no matter what we talked about, he always had something interesting to say while always keeping me engaged in the conversation. I don’t know if it was the mood, the booze, or my own repressed sexuality but I was really starting to have a crush on this guy! When I told him I was crossdressed, he leaned over, kissed my forehead and told me I was beautiful. He had me hook, line and sinker at that point. He finally invited me back to his place which I quickly accepted! I found my friend dancing and when I told her where I was going, she grinned from ear to ear and told me to have a good time.
The lyft to his apartment was mercifully short and as soon as we closed the door to his apartment he immediately started making out with me. It was nice feeling a man take the lead and I felt very comfortable submitting to him. We eventually made our way to his bedroom, which was a bit of a mess and kinda smelled like his cat but it wasn’t that bad. I laid on my back as he undressed down to his undershirt and boxershorts. At this point he asked me how far I wanted go. I paused for a second before uttering that I consented to him taking my virginity. He smiled, ran his hands up my legs, under my dress, and pulled my panties off. He then knelt between my legs and put on a condom. He pushed my knees to my chest as he slowly started to enter me. To be honest, until he was fully inside me, it really hurt! I was not used to anything that big. Once he made it all the way in, he told me I was being a good girl and then started to pump in and out of me. It still hurt but the fullness mixed with the friction inside me started to cause me to moan as we built up a rhythm. Eventually he came, pulled out and went to the bathroom to clean up leaving me in shock at what I had just done. He came back and we cuddled before falling asleep together. Sadly I never heard from him again. Overall the whole experience left a real bittersweet taste in my mouth. I’m proud I did something so far out of my comfort zone but I doubt the stars would align for me to do it again.