I met my guy on an online dating app. His bio and picture were super cute, a little nerdy, and very intriguing to me.
I agreed for us to meet in a nearby café for a non-alcoholic beverage before an appointment I had scheduled, so I had both a reason to leave early if things didn’t go well and enough time to stay and see if I wanted to learn more about him.
I walked into the café and saw him right away, sitting in a chair looking completely comfortable with himself. I, on the other hand, was a bit nervous but wasn’t about to show it. I strolled in with a smile and gave a quick hug hello, ordered my drink, and then sat to talk to this handsome stranger. We spoke long enough for me to decide that I would like to see him again – on a real date – and see if we clicked.
For our second date, we met at a restaurant. This time, I got there first and tried to look completely comfortable while waiting for him to arrive. When he walked in, his eyes lit up as he saw me and a big smile spread across his face. He’d brought me a gift-wrapped present! I was surprised, as this was a first for me – and I liked it! It was a book that we had talked about during our first date. I was impressed that he was so thoughtful. I left that date with the knowledge that I would very much like to see him again and get to know him, as he was not only cute, he was smart too!!!
On our third date, he invited me to his place for dinner. I remembered thinking “and he can cook too?!” He also asked me to bring my bathing suit, and I had an idea that things might get a little heated, but I had decided before heading over that kissing would be the extent of our physical connection that evening, if that happened at all.
We had dinner, drinks, and great conversation before getting into the hot tub. In the hot tub, things definitely got a bit heated when he pulled me close and kissed me.
I don’t remember much once the kissing began. Somewhere between the hot tub and couch, amidst all the making out, we got dried off and changed into our clothes. As we were intertwined on the couch, he said to me that he would like to keep things “sweet and innocent” for a while. I remember thinking to myself – “cute, smart, can cook AND wants to get to know me before we have sex! Am I dreaming?!”
I’d decided that I was going to keep things sweet and innocent before having even arrived, but him telling me this, seemed to make it much more challenging to stick to the plan. As things got progressively more heated, he suddenly stopped me with “there’s something I need to tell you…” I thought, “oh no! He has a sexually transmitted disease!” He looked so sweet, very innocent and scared as he told me that he wasn’t born biologically male. I’m not sure of the exact words he used, but I understood what he was telling me.
He looked so sweet, very innocent and scared as he told me that he wasn’t born biologically male. I’m not sure of the exact words he used, but I understood what he was telling me.
I was taken aback, not entirely sure if he was being serious, but only for a moment. When I realized that he was indeed serious, I also realized that it didn’t make one bit of difference to me that he was transgender. Everything about him screamed MAN to me!!! I think he was a bit distrustful at how easily and quickly I seemed to process this information. And in all honesty, had I been asked the theoretical question “would I date a trans person” the week before, I probably would have said no, but if it feels right, it feels right.
Yes, there were many thoughts racing through my mind, given that I’d never considered being with a trans man prior to this very moment. Amongst the first were “What was that I felt in his pants?” “What would sex be like?” “Would I like it?” and “What if I have more attachment to a biological penis than I had ever given thought to before?”
But the thoughts were fleeting, as I wanted to keep kissing him. He just tasted so good! I was enjoying this moment and keeping things sweet and innocent. I had time later to think about all the questions I might have. But then, he asked if I would like to sleepover! I only had to check in with my body for a moment before realizing that my answer was an enthusiastic yes! I was nervous as we got into bed. I had no idea how this was going to happen, but I was up for the adventure. I was happy to find that he had, what I later understood to be called, a Joystick! And wow… It looks so real, feels amazing and it vibrates too!
Over the past few months, our relationship has grown a lot. I’m loving the man I am getting to know. In all honesty, I just don’t think about him being trans. Yes, I do sometimes wish he had his penis permanently attached to him – mostly because I’m used to pleasuring my man in a certain way. However, I am learning new ways to pleasure him, as we build respect and trust for each other, and I’m enjoying every second of it!