sex

I was asked to write about sex. 

One might think that's an easy request but as I thought about it I began to realize it's actually an elusive and evolving subject for me.

In the past several years sex has changed for me in so many ways. 

In the far past as a girl with a penis, I typically performed the top role. I enjoyed it to the extent that I almost always came, and could also find pleasure in knowing that my partner had also reached orgasm.

During those early days, menstrual sex was a big turn on and sometimes I got to partake in it. Ive also pretty much always been into waterspouts; and got to experience that rarely. The feeling of the extra lubrication in both of those fetishes was divine and guaranteed I would cum very hard.

I began to realize I was trans and sex while exploring my femininity with lingerie and and bottoming also made sex hotter and more satisfying; but I was still the de facto top and still had a penis. 

My first wife and sex partner did not really embrace that, although she was tolerant. 

I had a couple other sexual partners during the 18 years I was married and had a defined open relationship. Of them, Sandy was the best and we did it a few times. She was also the first woman I had an ED episode with.

In those early days, and I assume because of high T, I was always horny and always wanted more for the most part. 

My first demigirl experience was with K.C. ... I remember getting to know her well enough that we eventually slept together, but that night I was fearful that actually doing it would damage the care we felt for each other. So we did not have sex that night. I have some regrets that I wasn't really aware of the power of my sexuality then. Kasey also tried a couple of times to tempt me when she was on her period, and I resisted because of stupid monogamous ideals even though there was no committed relationship happening. I regret that also. I wonder how primal those experiences might have been. I think she was either a switch or a top.

shortly before the time my current wife and I decided to be a couple. She was very high sex drive and I think I may have been on the decline; I remember worrying that I couldn't keep up. 

We had great sex and I believe it was so great because it was based on profound love and caring empathy. In 2007, she had a surgery to put in a bladder sling. Unfortunately as a side effect, penetrative sex became extremely painful for her. For a couple years our activities dried up almost completely. We eventually figured out we could still have lesbian sex and through fingering and cunnilingus we discovered her squirting orgasms. For her, I think the experiences were even better than the old way we did it. Making her squirt and cum gave me great pleasure and I usually finished myself off by masturbating; or on the best days she gave me a hand job while I made her squirt and it felt like cumming together. During those times I came to terms with my wet fetish and we explored face sitting also. I came hard when she did that for me.

All that being said, sex always seemed to be an activity in which I had no influence over. the more I allowed myself to feel desire, and the more I showed that affection in the hopes of being intimate, MY wishes and needs were never important. more and more over the next decade + the times "yes" was said became fewer and fewer until I stopped asking. in 2016 the entire year passed without a single bedroom experience. It would not be wrong to say that during this time I was in El, but not without a partner.

And I more or less stopped masturbating too. I believed that if my wife didn't want me, then I was unworthy of any pleasure, and only when it became undeniable did I allow myself pleasure. I stopped watching porn, stopped reading erotica, and most tragic of all I stopped having fantasies and writing about them. I was a fucking amazing erotica writer; but all of it was lost when I deleted my old, male FetLife profile.

It wasn't so terrible to be honest. I think my testosterone levels were at the bare minimum for cis men, and this is the time when I began actively transitioning as well. I was becoming my true self, and there was very little that was erotic about it. It may have been helpful for me to not feel shame, to not own the societal definition of trans being a perversion. I felt gender euphoria but it was rarely sexual in nature.

I began to get painfully lonely. It felt like nobody wanted ME, and I started believing I was not worthy or attractive. I spent 2 or 3 mornings every week at the beach, alone. It became my respite from all of the other judgements and responsibilities of the world. I had lunch with a guy I knew who had a non traditional marriage where his partner lived out of state but they were still friends, and still married. I started to wonder if that was what we needed in our relationship; if my wife was as miserable as I. We took more than one trip to Tacoma to consider moving there.

Everything changed in November of 2018 when I met someone irl that turned into a crush. And SHE responded in kind. For the first time in a decade I felt desirable and that I was lovable; that I could have value physically to another human again. it was about a 5 month romance that ended with a crushing blow; and my sexual irrelevance was again reinforced.

About the same time I met my partner. she had empathy in those days and took me in so to speak. We had an incredible night of lesbian sex with a 3rd; and the experience emotionally was so affirming. I actually began to develop confidence again. We had sex, the 3 of us, but although it was extremely special and empowering, I didn't feel pleasure, I didn't orgasm, and the satisfaction I felt was solely from knowing I could give pleasure to, and have value to another person again.

We embarked on "The dream" where my partner tried to set me up with sexual partners as parts of threesomes. It was a good dream, and I was overjoyed to take part. One high point for her was when she got me laid for the first time and I lost my anal virginity. It was a wonderful experience; but again I took all of my pleasure from being lusted after and being of service; and did not experience an orgasm or even a lot of arousal. We repeated these adventures a handful of other times and hooked up twice more with Grindr guys. 

As a parallell, I did also meet, date, and begin having solo sex with a man who is probably my fondest memory as a male sexual partner. We got together a half dozen times before he ghosted me. I still don't really understand it. He was caring and attentive as a lover. He went slow, and put attention into foreplay, and highlighted on caressing me and compliments that reinforced my femininity. I really felt wonderful when I was with him; and I guess it's true that I fell for him even though it was supposed to be NSA. But how could I not when he treated me the way my soul had been craving for all of my life?

I began to think I wanted hookup sex like my partner enjoyed. I made some effort to get dates that went that way; and was disappointed every time - usually when the man ghosted me one way or another.

At a local dungeon I met another man, a mutual friend of a friend, and I felt there was chemistry there. I went down on him twice and he choked me as in breath play; and I really loved that feeling of being completely under his control and even helpless. I wanted to go all the way with him but didn't in the end and im not sure why - but I think it's the demigirl in me. I think its because I knew there was no heart in it even if there was physical attraction.  And also I was pretty sure I still wouldn't have a lot of pleasure and certainly not an orgasm under those terms.

I did resume masturbating though and finally after a hiatus of so many years I learned how to cum again. My orgasms are so much different on estrogen. I learned I can cum so hard I get dizzy and almost black out from the blood pressure drop ha ha. It is incredible. and so is cumming dozens of times in a session.

I have hope now that my surgery is complete; and Jill's ability to orgasm has been established. I still am mostly numb inside and cunnilingus is what is the most thrilling for me from a sensation point of view. Im pretty confident that as she wakes up inside I will be able to cum from g-spot stimulation, and it seems really likely that penetrative sex will directly stimulate that area. Hopes are high that someday I will orgasm from being penetrated and I'll once again get to experience pleasure from actual sex. My partner and I are working on it together, she's getting in farther each time as dilation loosens my canal up enough to actually accommodate her. Interestingly, dilating is also pleasurable when I hit my g spot. 

Ome day im sure well get there, and Ill reach the orgasms from penetration and I know ill enjoy the feeling. I also hope Ill have the ability to squirt. Ive already done that from cunnilingus. Either way it will be great to have sex and orgasm, but it remains to be seen how much intimacy that will also involve. I hope that it will be a loving, caring act that nurtures my soul when I get there the first time. 

 I guess time will tell as that chapter is yet to be revealed.