Hello my darling readers. I hope this new year is off to a good start for you. My new year has certainly been an interesting one thus far, and last night was no exception.
I write to you this morning on the other side of an experience I’d been both looking forward to and dreading at the same time. I have recently asserted to someone that I am, in small way, going through a second adolescence (I might have even mentioned it in the previous entry). Well, along with going through a second puberty, learning the art of feminine expression, fashion, and makeup, I’m also having to go through a second virginity.
Obviously, I have had sex before so virginity isn’t really 100% accurate but I cannot find another word that better describes the emotions I feel or the experience I’m having. When you are a virgin and you take your first steps into the realm of sexuality you are (or at least I was and am again) met with both excitement and fear of the unknown. Sex is an intense experience and can be terrible, bad, okay, good, great, or earth shattering and you never really know what it’s going to be like with someone new (or your first time).
I had never had sex as Emma, at least not really. The few encounters I had with my wife towards the end of our marriage were anything but gender-confirming experiences. I do not fault her for her inability to excitedly embrace the new sex dynamic I truly desired and honestly needed in order to feel comfortable. For her, it was still a very heterosexual dynamic that she wanted, and for me it was the opposite. I wanted to be a girl with a girl who wanted to be with a girl because she was a girl (say that 5 times fast). My ex and I could never have that because, as she put it so many times, she wasn’t a lesbian.
So, coming from this place of never having sex as this new identity I’ve taken on, I very much felt like a virgin as I considered my next sexual encounter. I didn’t know how to be a girl with a girl because I’d never really done that. I also didn’t really know how to navigate having boy parts while at the same time wanting to take on a feminine role (I do recognize how binary I’m being about this but we have to begin somewhere; never fear, when Emma is near, it’s rarely long before it becomes queer) ;)
How would this dynamic look? What would it feel like to be seen as a girl and then to introduce a penis into the mix? Sure, lesbians play with strap-ons all the time, but that’s a fun and foreign experience for them because they are playfully stepping into the phallic role. For me, it’s an old experience that I no longer really care for and actually contradicts how I view myself on a pretty fundamental level. I understand that penis does not = male, but some aspects to using one REALLY reminds me of being male; of having to play a role I didn’t like, didn’t want, and never felt at home within. I believe the only reason I was ever all that comfortable taking on a binary male role in my previous sexual encounters was because testosterone is a very powerful hormone that creates very specific urges in a person. In short, T makes you want to fuck, a lot… everything, all the time… whenever, however, and sometimes even with whomever is willing.
Estrogen is NOT like that, at least not for me. Estrogen has fundamentally changed me, my body, my thinking, and the way I experience sexuality. No longer is it about the physical yearning of needing to release something that’s been building up (thanks to Spiro there really isn’t much stockpiling going on, lol). It has now become much more of an emotional need for connection, for harmony, for passion, and for physical intertwining for the sake of erotic closeness. Can you see the difference between the two? One says “let’s cum!!” the other says, “Let’s make love, let’s get lost in each other for a while, and let’s feel ourselves become one.”
I can guarantee that very few heterosexual cisgender men ever even think the words “let’s feel ourselves become one” in their entire lives. Maybe they actually enjoy that oneness but testosterone is about getting it done. It’s about spreading seeds into fertile soils… as many as possible and as often as possible with as much soil as possible. Estrogen (for me at least) is about savoring the experience, about basking in that moment. Testosterone is to taking vodka shots to get fucked up as fast as possible as estrogen is to savoring the scent and taste of a fine wine for the pleasure of the experience. They are as vastly and fundamentally different for me as living as Emma was to living as Robert.
But, as with most things, when such a remarkable shift in perception occurs it can be scary or intimidating to move forward with such an unfamiliar paradigm. Well, my darlings, I have now done exactly that.
As many of you know, I have been dating and I recently acquired/became a girlfriend. I have been talking to/seeing this person (Rose) for probably five or six weeks now, but before the last 24 hours, we hadn’t done much more than kiss a few times. Last night, however, she decided to spend the night with me, and a lot happened.
She arrived after she got off work and we hung out for a short while just talking. We eventually went out to dinner which was a nice experience. It was really nice to be out in public with a woman and to have her not only be okay with public displays of affection, but actively engaging in it. She didn’t care if other people looked at us or if others saw us as lesbians. She didn’t care that people might make assumptions about her, me, or both of us together. She was too excited to be spending the evening with me to even notice if someone gave us a funny look.
We ate a lovely meal, and after we finished we decided to head out to a bar where some of her friends were hanging out. These friends were, as she puts it “lifestyle” friends in that they knew one another because of their polyamory/swinging backgrounds. Again, it was wonderful to be in such a busy place with a woman who was not afraid or worried about being publicly affectionate with me. She held my hand and kissed me a few times all while others looked on in that hetero, “did those two girls just kiss?” way, and wasn’t bothered by it at all.
An exciting part about this trip to the bar and me meeting these “lifestyle” friends was that one of them was… how can I put it… sexy. She was cute and frisky, and totally my type. Better still, I think she thought I was quite cute because she was making eyes at me the entire time (she even complimented how beautiful my eyes were at one point). Rose, who is polyamorous and who is actively engaging in an open relationship with me wasn’t even bothered that her friend and I were kind of flirtatious. If anything, she was excited about it! Can we say holy non-monogamy culture shock batman?
As a serial monogamist who has never been in an open relationship it is weird to find a woman attractive and to have the woman I’m on a date with be excited about it. Even more than that, her friend invited me to join them at their next “lifestyle” party (I’m guessing she had personal reasons for doing so), which Rose was totally excited about. She WANTS to take me to a sex party where I might sleep with some of her friends… where we both might sleep with her friends either together or apart…
I just don’t even know how to begin processing that. It is soooo different than what I’m used to, and I like it. It was nice to not have to worry about jealousy (or at least not worry that much about it). She brought me to meet these friends because she wants me to join her in this poly-open-swinging lifestyle and introducing me to people in that lifestyle is a big first step. She wants to have me herself, and then share me with others because she cares more about me having fun and experiencing new things than she does about needing me to fulfill her every need.
When I told my therapist about this proposed sleep over and we discussed the polyamorous dynamic Rose and I were entering into, she was thrilled to pieces about it. She said (and I agree with her on this) that this new experience was going to really help me grow and would fundamentally change the way I view love/sex relationships. Mutually agreed upon non-monogamy is a difficult path to walk, but it has the potential for such amazing fulfillment. Sure there are traps and pitfalls to deal with, but that’s the same case with monogamy. Non-monogamy offers the opportunity to have more fulfilling relationships with other people while at the same time not pressuring them to fulfill all of your needs and not having the pressure placed on you to fulfill all of their needs.
Marriage and monogamy has a great deal of pressure to be the be-all-save-all of the relationship. If your spouse isn’t fulfilled by you because they are under the impression that you must fulfill all of their needs, then resentment starts to grow and the foundation of the relationship starts to crumble under the weight of those unfulfilled needs. My marriage crumbled, despite such a loving and devoted friendship because we couldn’t meet each other’s needs anymore. She went and had an affair/one-night-stand because she felt sexually unfulfilled by me, in no small part because I felt sexually unfulfilled by her for a very long time. Resentments built up and eventually everything collapsed because of it.
Non-monogamy is a solution to that. True, it’s not the only one and it’s not even the best one for many, but it holds the potential within it of circumventing that unfulfilled-needs-become-resentments formula. True, it requires a great deal of maturity, communication, boundary setting, and flexibility in the willingness to test what’s okay and not okay, but that’s not that different from monogamy or marriage. The only real difference is the level of honesty, but we can get more into this later. We have a story to tell still!
So, we hung out at the bar for a while and eventually decided to head back to my house. When we got there it was fairly late and so we pretty much went straight to bed, even though we did not go to sleep for quite some time afterwards. Long story short, no, we did not have sex. Remember, this is Emma’s virginity-loss story, and most of the time those stories don’t skip right to sex (despite what porn might make you believe).
No, instead, we spent a long while simply talking, kissing, slowly but surely removing clothing, and exploring each other’s bodies… you know, the way two teenagers who are new to sex often do. It was slow and affectionate and exciting. It was also frustrating, but in the best possible way. Eventually we fell asleep in each other’s arms, wearing little to no clothing at all and that’s how we spent the night together.
The morning, however, was a bit more… uh… how do I put this… intense? Let’s just say that it is really hard for two adults who want to have sex together to wake up in the morning and cuddle in the mostly nude without it escalating into more.
It’s at this point that I’m going to have to disappoint because I don’t kiss and tell, at least not fully. We sort of picked up where we left off the night before and it wasn’t long before all the clothes were gone and we became extremely intimate.
At first it was amazing. I was having sexual experiences while being perceived and desired as Emma. She found me, as a woman, sexy and that was the best feeling ever; far better than any of the physical components, although those were pretty amazing too. The benefit of being perceived as and desired as a woman is that you aren’t expected, per se, to take on the masculine role. Instead it was a very mutual, lesbian-quality connection… until it wasn’t anymore.
I do not want to go into too many details but everything was going along quite well, I was having fun, it was pleasurable and exciting. I felt sexy, I felt wanted, I felt desired, and I felt lovely sensations I’d never felt before. I did not feel uncomfortable being a girl with a penis one bit, until we made a change to what we were doing and it was suddenly far too reminiscent of being a man. The fun and excitement quickly fizzled as my brain struggled to process what I was doing with who I knew myself to be.
We were a woman (mostly) and what we were doing was anything but. The way we saw ourselves, the way things felt, and the way the interaction was playing out wasn’t right and the unexpected discomfort quickly drained the sexual excitement out of the room. What had moments earlier been an amazing experience suddenly became an almost nauseating experience. I don’t know if you’ve ever experienced full-fledge cognitive dissonance, but it’s not a good feeling. It’s a very uncomfortable, overwhelming, and confusing feeling.
I tried to play the sudden decrease in libido off and she was running so late because of our early-morning fun that she didn’t ask too many questions. She got in the shower, got dressed, and left shortly thereafter. When she drove away I was left with a very strange feeling. I didn’t understand what had happened but I’d somehow gone from having amazing and fulfilling fun to feeling wrong and uncomfortable. It wasn’t until I spent a while writing in my journal about the way I felt that I realized where things had gone south and why they had gone south so quickly.
Put simply, I’m okay having my male genitalia and even enjoy utilizing it during sexual intimacy but there are just some things I don’t think I can do anymore, at least not right now. There are certain ways of having sex that are TOO masculine/hetero for me to be able to enjoy or to experience without having a sudden and debilitating bout of cognitive dissonance. When we were engaging in activity that was not overtly hetero (in my mind anyway) or was very lesbian-esque it was great and fun. When things got too heteronormative that’s when it all fell apart. This is the second time this has happened, too. The very last time my ex and I had sex, I had to stop in the middle because of the cognitive dissonance I felt about the experience. I couldn’t have sex the way she wanted anymore, not without feeling uncomfortably out-of-body.
So, I have lost my second virginity and it was great, but I have also realized that there are limitations to what I feel comfortable with these days. I don’t know where all those limitations are, which is tragic, but it has become apparent to me that delving into a second round of intro-to-sexuality as a woman is going to be vastly different than it was as a man. The only thing I can hope is that Rose is willing to explore these new boundaries with me so that I can learn what I’m okay with and not okay with.
Sadly, that is where I must leave this entry. I do not know what the future of my sex life holds for me and I do not know how it’s eventually going to look when I’m entirely comfortable within my trans* body. All I can do is hope that the fun and good outweigh the uncomfortable and bad. Overall, though, I’m feeling quite excited to have taken my first steps into the realm of trans* sexuality and non-monogamy. I sense that a great deal of adventure lies ahead of me, and never fear, I’m going to bring you all along with me. 2016 brings with it a new chapter in our life, and we think this chapter is going to get a bit more steamy than the previous one. ;)