Trans Love Is hard to find

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I was always small for my age and always seemed more feminine than masculine despite the fact that I have a very small penis. I enjoyed feminine things, especially clothing and jewelry and upon growing up, I identified more as a woman than a man. I also was blessed with little to no facial hair in the traditional male sense of a beard or mustache. In fact, I had high cheekbones and ice blue eyes that contrasted with my brunette hair.

I really enjoyed wearing women’s clothes, especially panties and my tiny penis didn’t need the traditional pouch of a men’s brief. I learned how to apply makeup and walk in high heeled shoes and also learned the mannerisms of a female as they are quite different from a man’s. I could dress either part but felt more comfortable as a female.

When it came to relationships, I began dating women in college but it never felt right. I never tried dating a man until after college and often when I would identify with them early on that I was a woman trapped in a man’s body, they would run off or ghost me which was painful.

This continued for a few years until my late 20’s when I met Gabe. I was out with a few friends after work and was having a few drinks when a round was sent over. He specifically made the waitress say the drinks were from him and it was because of me. I have to admit I looked particularly cute this evening as I dressed in a navy Pencil Skirt, black nylons with red pumps and a white silk blouse with a camel hair blazer. My hair was shoulder length and my makeup was nice: not too much but enough. At this point of my life, I was identifying as a woman and dressing the part. And while many of my co-workers did not know, I had confided in a few that did and they were great about it! The bond of womanhood is strong, even as a trans!

Anyways, we accepted the drinks and before long, Gabe made his way over and introduced himself and asked to speak with me in private. I replied with my femme name of Sydney and I got up from the table and grabbed my near empty drink and we walked over to his spot at the bar. He said, “I can’t take my eyes of you. I noticed you from the moment I got here and have been mesmerized ever since. I am glad you accepted my drink and was wondering if you would like to have dinner with me sometime?” I could feel the rush of blood come to my head as he complimented me as I try very hard to be a woman and am glad he saw me that way but I have also learned that heartache comes eventually and since my mid twenties, I have been honest and up front about who I am so as to not give any false expectations or have myself put in danger when I eventually reveal my penis which has caused a few minor beatings in my life.

So, I said, “Listen Gabe, I am flattered by your compliments and grateful for the drink you sent over. I also think. You are cute and I would love to have dinner with you. But, before I do so, I need you to know something about me. I am actually a man but identify as a woman. As you can see I am not very manly but I do have a tiny penis and I want to say that up front so that you can run away now without embarrassment.”

He took a pull from his whisky and it seemed like he was trying to figure out the right words to say but when he put the glass down, he simply said, “I was drawn to you when I walked in here and the rest of it doesn’t matter as I think your honesty is admirable and your looks are amazing.” And he gave me a kiss on the cheek before continuing, “Your honesty took a lot of courage, especially since you don’t know me nor what my reaction would be but you are incredibly brave by telling me the most vulnerable thing about you without much passing of time. I would like to say that my offer for dinner still stands. We can figure the rest out as we go. Sound fair?” I gave him a hug as a small tear fell down my face and said, “Yes, I’d love dinner with you and I appreciate your sincerity.”

My friends witnessed it all and when I walked back to gather my purse, they were teasing me about hooking up. I blushed a bit more and as I told them I was going to grab dinner with Gabe they all said they would see me in the morning. My bestie, Cassidy, got up and pulled me aside and asked how it was going. I told her the sweet things Gabe said and how he wasn’t;t shocked that I was a woman trapped in a mans body and that he was open to seeing how things went. She hugged me and said I was very brave to put that out there so soon but it was the right thing to do if any relationship was going to happen. She knows about the past heartbreaks where I waited to tell only to be abandoned and heartbroken.

I met Gabe at his seat as he settled his tab and we walked outside and found a nice outside Bistro where, ever the gentleman, he pull my chair out as I sat down and pushed it in once seated. Our discussion was pleasant and nice and did not solely focus on my penis although he did ask permission to ask me a few questions about how and when I knew I was a woman in a man’s body. I answered honestly and openly and he seemed to appreciate the answers, I certainly appreciated his respect and kindness shown to me.

We finished dinner and we went to bar for a nightcap. When finished, I said I was going to go home and he offered to walk me there since it was just a few blocks away. As we walked, he was sweet in his gesture to hold my hand and over dinner he shared some vulnerable moments in his life that helped us bridge a relationship. At my doorstep, I gave him a kiss on the cheek and he promised to text and call me for another date soon. Although I was hopeful, I have had many a date end right here, just like this on my stoop.

I got into my apartment and looked at my texts. Cassidy had written a few asking how it was going and was he nice so I FaceTimed her and filled her in to say I had a nice time with a promise fo another call and Cassidy could here the dejection in my voice and said, “Sy

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Written by shyguy654
Cargado June 9, 2021
Notes Finding love as a Trans is not easy. Trapped as a woman in a mans body is tougher but understanding is key to fun sex and adventure
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