Dating and Sex Since June
Let’s talk about sex, baby. Anyone who knows me, knows that my sex stories are my favorite tales to tell. Since coming out, people wonder if my dating and sex life has been effected; the reactions from my past relationships and my new ones. Dating apps, and their ability to lead to social media pages have played a major part in my dating life. Before my Instagram became flooded with promoting my blog posts, it was almost impossible for a potential date to uncover that I was transgender, unless we had a mutual friend who decided to rudely spill the beans to them first. There have been cases where guys are “disappointed” that I’m trans, apparently it ruins the facade that I’m some perfect womanly being on this earth, but I couldn’t care less. Now, with my Instagram still attached to my dating apps, the men who choose to continue the conversation and ask me out have truly intrigued me. If they weren’t savvy enough to check out my social media first, telling the guy on our first date has become routine for me, and successful for the most part.
Recently I’ve been having sex with guys who have known I’m transgender. Overall the sex is better, yes. Knowing that they know about me, and that it’s not bothering them or hindering their attraction to me is a turn on, and also makes me 100% more comfortable having sexual experiences with them. Before, I would be scared to hook up during the day or sleep at a guy's place. I would think about all the possibilities that happen to a transgender person. One thought that always crossed my mind was “what if in the morning he decides to go down on me and sees my scars?” Of course I found ways around it, like suffocating them under the sheets or keeping my legs firmly wrapped around their heads. If I wasn’t cautious or didn't have my sexual tactics, what would have happened to me? I don’t even want to think about it.
Because I have been out openly since June, I felt it was time to update my dating apps and give online dating one last shot. I went on a dating app bender and re-downloaded all the apps I had ever had to see if 1. my profile was still up and 2. if anyone worthwhile was on it or had messaged me. I saw multiple people from my hometown on JSwipe (which I previously had for all of 20 minutes), and I matched with a few of them. One of my matches was a guy I had played soccer with in the 4th grade, and had thought was cute in high school. He wasn’t the coolest guy, but was always very nice to me. Anyway, we matched and he immediately messaged me saying how he thought it was great that I was educating people on such an important topic, and that he enjoyed reading my writing. We talked on the app over the next few days and then I told him I was going to delete it (Jewish guys looking to settle down and get married to a Jewish girl are really not my type) and he asked for my number. Still, I was confused if he was trying to flirt or just be friendly. Turns out he was trying to flirt. After much hesitation and a few weeks of talking, I invited him over to my house. We sat in my living room for a good amount of time to talk and then I brought him to my room so I could get ready to meet up with my friends for Magic Fountain (best ice cream place ever). One thing led to another and we went from talking on my bed to having sex. I was surprised by how good the sex felt, but that might have just been because of how hot the situation was to me; he wasn’t the hottest guy in the world but the experience, and him wanting me, turned me on… and nearly got me off. Afterwards he drove me to meet my friends and we made out for a little in his car. We said we would do it again sometime soon, and I think we both meant it, it was a lot of fun, but if it doesn't ever happen again I will still be just as satisfied. Although there was sexual chemistry, and him knowing me throughout my entire transition made things hotter, it still wasn't the best sex of my life.
With that said, I slept with a guy two weekends ago who didn't know that I'm transgender, yet the sex was passionate and real and amazing. Probably one of the most passionate and best sexual experiences I’ve ever had. I think there is something to be said for someone who just really knows how to be a good lover, regardless of how deeply you know them. Connection is key when it comes to sex; I think that can trump how long or well you’ve known someone. I had met him just that afternoon, day drinking with my friend Ali, and the night unfolded into something very real. I’m still waiting for the day when I meet a guy and we start dating and I can express to him (or he could read this post and know from this) that I want that romantic first time with him, I want it to be special. Something super corny and yet romantic all at the same time. I want to get to know him, make that connection, feel our sexual tension, and then finally be able to have him in me, and then have him forever (or until our relationship has run its course); I long for that. I am so lucky to have been able to even have sex, have men attracted to me, wait on me, treat me, etc. I am blessed to have the experiences that I have had, but that doesn’t mean I want to stop achieving my relationship goals.
Now, just because some guy accepts that I’m transgender doesn’t mean I’m going to throw myself at him. You’ll definitely be cooler and more attractive in my eyes, but I am not desperate enough to lower my standards of love, just because one guy thinks I’m beautiful as I am. Once again, connection is key. And even if there is a connection, sexual or romantic, once you start seeing a person and getting to know them, that’s when you can tell how things will play out. Like I’ve said in my second post, I usually go out with men I think won’t have an issue with me being transgender, and then scope them out on the date. Now that I’ve come out, I send them my blog or have them check my social media out and take it from there based on their reaction. I don't have time anymore to meet all these suitors in real life to either be denied or nervous the entire date and then have a successful response. It’s gone from me being more comfortable with them knowing on the first date, to me wanting them to know beforehand. But, that is a case by case thing. Sometimes I feel like it's more appropriate to still meet them in person and have them see me for me, and sometimes I want to weed out if they're gonna be a douche about it, it all really depends, but the point is that being open and honest from the beginning is crucial. Not only for my own romantic preference, but for my own safety. Just because this is 2016 and Bruce has become Caitlyn does not mean everyone is a-okay with the transgender movement.
I did go on one other date from JSwipe before the kid from my town. I was unsure if he had looked into my social media before our date, because he hadn’t said anything about me being transgender. During our date I realized he had no idea, and felt the urge to tell him. When I did bring it up towards the end of our fantastic steak dinner, he didn't even flinch. He had no idea, but wasn't bothered by it. What he did say was “It’s something I have to think about, but most definitely is not a deal breaker.” Turns out the deal breaker was that I wasn't upfront with him from minute one of the date. So, although he was accepting of me being trans he “felt deceived” that I hadn't told him immediately when we sat down. Mind you, this conversation took place two days after the date, via text. We went back and forth about how “honesty is important from the start” and that me having no idea he didn't know was clearly the issue, and in the end our miscommunication became the downfall of that potential relationship.
Speaking of other potential relationships, I once dated a slightly older guy who seemed to be the perfect man. We had two dates before I left for Amsterdam, and decided to wait to have sex until I returned. When we rekindled our romance the summer I came back from studying abroad, everything seemed to be going perfectly, except for the fact that he didn't know I was transgender. I always knew he would be accepting of it, but never had the perfect moment to tell him. Fast forward two years and he’s practically engaged, and I couldn't be more happy for him! Out of respect for what he and I shared, I sent him the link to my website. With the link, I sent him a beautifully crafted message thanking him for letting me go (he made the decision for the both of us that I should experience life and not "be tethered down to an older guy looking to get married”) and that I was happy for him and his relationship, etc. When he responded the next day, he told me he “simply had no idea” that I was transgender and praised my braveness to transition. It was to much surprise though that he became defensive about his relationship, and felt the need to tell me not to write about him in any capacity. I responded letting him know my intentions with telling him were out of respect for what he and I shared, and nothing more. I added that if I were to ever mention my relationship with him in my work, that he would be the only to know it’s him. It's interesting that the past men in my life feel threatened that I’m going to write about them, and even more so that I will mention their names. It’s as if they feel nervous about their family and friends finding out they were with a transgender woman. Right after my blog came out a guy I had hooked up with in college once or twice (and we both don't even remember if I slept with) messaged me on Snapchat and asked if he could call me. When he did, he asked if I was going to write about him or mention his name. I was offended. He was so insignificant to my life and my story, yet he felt that his privacy was in some sort danger. He then began to say that the reason he and I didn't continue to date as because he might have been talking to another girl at the time and summer was just a few weeks away. He could tell I got angry and we hung up, to which he called me back asking that we don’t have bad blood, and wanted to be reassured that he wouldn't be mentioned. Shake my head, well now you have been, but still I respect each and every one of my past hook ups to not mention their name.
For my future dates or potential relationships, check up on my social media, read my blog posts, and if you decide you’re cool enough to take things further, let me know. Now more than ever I have zero time to waste on anyone who won’t accept me for the person that I am entirely. I’ve experienced moments on dating apps where I’ll be having a great conversation with this guy and then all of the sudden his profile disappears. Instances like that do hurt... for about half a second and then I get over it. There have been a few guys who have expressed to me that they felt I should have told them on dating apps or had transgender written in my bio. Being transgender is not what defines me. I am loud, blonde, fun, white, straight, and I happen to be transgender. Recently people have told me they feel sorry that that is something I have to do, and will probably always have to deal with in some capacity. When I do think about it, it does make me sad, but I don’t allow it to keep me down, I can’t allow it to. All I can do is keep the power of positive thought in the forefront of my mind, and believe in its work. I’ve come to realize throughout my dating app journey, that I’m just simply not interested in the type of guy who’s on dating apps, not in New York at least. I feel it’s really important, at least for my circumstances, to meet someone more organically.
Written by Corey Rae --- Edited by Emily Turner