on dating femmes: a faggy trans boy rants

I'd been locked out for hours. I was almost certain of it, even though time was starting to blur together. The sun was high up in the sky, but thankfully there was a cool breeze from time to time and some shade. Whenever I got tired of banging on the one window looking into the 5th floor hallway or sitting on the dilapidated plastic chair I'd strategically placed in front of the window, I'd pace around contemplating shit like my life and how I happened to be trapped on the rooftop of my building, the one roof in this entire city without a fire escape or any other way of getting out save for the door I was now pounding on…desperately.

I'd been seeing this beautiful femme woman of color for a couple weeks. We met on one of those dating sites us queers like the use. Y’know, the really crappy one that stubbornly refuses to broaden their gender or sexuality categories (despite the oodles of queers who populate that virtual space.) We met in person one evening. She took me to a film screening, some director I'd never heard of. While we waited for the film to start we chatted. The conversation was free flowing and somewhat relaxing. I mean as relaxing as a first date can be given all the unsaid things that weigh on your mind while you're in the midst of a 1st date. But for us the convo was great - films (we're both serious movie buffs), gender theory (what self respecting queer doesn't infuse this into ANY conversation), family history and trauma, exes, etc. By the time the movie started I was optimistic about this girl. She seemed smart, funny, artistic and hella cute. I felt ready for whatever "dating story" awaited us.

Little did I know.

But before I delve further into this story let me take a minute or two to (softly) rant on the woes of dating cis femme women when you’re a passable, albeit quite faggy, trans boy. Once upon a time, all I wanted was cock. It's true. Yes, I had sexual desires for other genders; that was always in the background. But my foreground became my lust and fascination for cis male fucking. I've written at length about my experiences and my co-blogger still writes at length about this. However, as my sexuality is wont to do, the pendulum swung and gradually space opened up in my life for other types of sex and expressions particularly with femme cis women. And the journey, folks, has been rich, hot, and affirming in a lot of ways. 

What I'm about to write will incense some and probably make you feel "some kind of way", but I'll risk it for the sake of more open dialogue on this. In almost every dating situation I've found myself in with cis femme women, I've been made to feel that only one role is available to me and that is the resident 'butch'. Don't get me wrong, I know how I look. I know that in every public space I move through, "the public" sees me as a dude. They may think I'm a particularly homo-rific dude, but a dude nonetheless. However, does being a dude automatically make me butch? Hell do I ever feel butch? With the femme women I've dated, 'butch' becomes my de factor identity. I tried hard to resist at first, but often times it’s hard to buck the trend and not fall easily into a hetereosexual-esque relationship. Also, in the same vein, in these relationships I'm also the Top. Again, I like topping, just as much as I like bottoming or fucking in any kind of "power-ed" context. However, it's the automatic and permanent relegation to this category that I find rather off-putting. And in every dating situation I find myself with cis femme women, even the ones who claim to not subscribe to such notions of relationship and sexual roles may say shit like:

"I like a guy who's chivalrous and will open doors for me and make me feel safe and protected."

or

"I forgot to go to the ATM, can you pay for this one?" (Meanwhile she's been 'forgetting' to go to the ATM every single time we've been out to eat, drink, etc.)

or

"Wait...you don't love me back?! You're such a guy!" (Meanwhile we've only been going out for a couple weeks.)

or

"What do you mean you need space?!" (I meant I can't spend 5 days a week with you.)

or

"I know we agreed to have a non-monogamous situation, but I don't want to share my man with other women...so change."

or

"I'm ready to be serious with you." (Even though we've been hanging out for a couple weeks and we agreed to keep things casual and light.)

Now, as a one-time cis femme woman and a now faggy trans guy, I understand through and through that we live in an extremely femme-phobic and misogynistic world. In fact I’ve written firsthand accounts on femme-phobia in the hook up scene. I know there's a particular way in which patriarchy plays out for women, queer folk, trans folk, etc. And even within that it looks different if you're femme, butch, gender nonconforming, androgynous, pre-op, post-op, no-ho, etc. I also remember what it was like when I dated masculine people or masculine cis men as a femme woman. I remember how easily I got attached if the masculine person satisfied the 'protector' role I'd set up for them. Sometimes I got attached if said masculine person fucked me the way I wanted to, i.e. mistaking intense sexual chemistry for a solid relationship/emotional connection. These were all behaviors or patterns I was socialized and encouraged to have or exhibit by virtue of being a 'girl'. Back then I resented being expected to act this way, and yet in relationships with masculine folks the same patterns would emerge. As I got older and my gendered experiences grew vaster and gained more depth, this 'easy attachment' or 'quest for a protector' eventually gave way to something a lot more nuanced. I realized that sexually I wanted to 'act out' the power inherent in a protector/protectee relationship, whereas emotionally, I wanted to tease out 'attachment' from 'ownership' and this is what I've found in my romantic dealings with cis femme women - there always seems to be a battle (subtle at first) for ownership, i.e. liking/caring for someone is often confused with owning someone and (indirectly) limiting that person's interaction with their communities. I know this plays out in many types of relationships, not just those involving trans guys and cis femme women. However, given how often trans male and cis women date each other, our overlapping communities and the depth of shared experiences around gender/forced gendering, there's a way in which gender/sexual roles, attachment and ownership plays out in these types of dating relationships that feels particularly problematic to me. I've had numerous conversations with other trans guys of color who are nervous dating cis femme women for fear of being forced to ALWAYS be: the butch, the top, the protector and all of that jazz. One trans guy I talked to, who dated femme women in the past, said "It looked differently in each relationship, but, yeah, I always had to be chivalrous or 'act like a guy' in some way."

I thought about all these things on that roof as time trickled by. I thought about the cis femme woman I was currently dating - the very same one that I'd had that fun 1st date with, who was now comfortably chilling in my one bedroom apartment 3 floors below. How long will it take before she notices that I've been gone for hours and starts looking for me? I was not optimistic. After our fateful fun 1st date a month ago and an equally fun 2 weeks together, things were quickly going downhill. During week 3, as the honeymoon phase gave way to reality, I realized I was in the midst of a full on heterosexual relationship where I was expected to essentially be "the man" - paying for everything, making her feel safe and protected in public, only talking about her life/problems/experiences (she liked to talk, but listening, not so much) among other things. By week 4, she wanted to spend almost day together, became obsessed with changing our poly status (even though we spent an extremely long time talking about this during our 1st week together) and altering my close relationships with friends. Early one morning at the end of week 4, I went up to the rooftop of my building to have a quick smoke and enjoy a few minutes of peace and solitude; It was just going to be me and the sunrise. She knew what time I'd left and where I was and approximately when I'd be back, so when the wind slammed the rooftop door shut, effectively trapping me there, I wasn't super worried because I figured surely after an hour, she'd wonder what was keeping me and come looking for me. I waited and waited, pounded on the door and window, yelled at the top of my lungs for someone to come unlock the door and let me back in. No one came. Not other residents. Not the girl I'd been seeing for a month, who was right now just hanging out in my apartment. Doesn’t she miss me, I wondered? Hasn't enough time gone by for her to worry that something is amiss?

After pacing the rooftop for a looonnnnggg time, I sat down on that plastic chair, my head in my hands, frustration and hopelessness crowding it. I stayed seated for a long time, until out of the corner of my eyes I saw her. She opened the door and I jumped out of that chair like it was on fire! I was so happy to see someone. She looked mildly puzzled, not concerned, just slightly puzzled. When I asked her what time it was, I was surprised to hear 4 hours had gone by. 4 fucking hours! She'd been chilling in my apartment, taking a nice leisurely shower, watching tv, playing on my laptop and doing all sorts of fun Sunday morning activities, while I'd been stuck and slowly losing my mind on the roof...for 4 miserable hours. 

"After 2 hours, weren't you worried? Didn't you think that perhaps something was wrong?"

"I guess I should have come check on you earlier," was her only response.

No "I'm sorry I didn't come up sooner" or "Are you okay? Do you need some water?" Nothing. I was shocked...especially because I'd been her Mr. Protector for weeks. The one chance she had to watch out for me, she sits back and lets me languish on the roof for 4 hours.

Needless to say, I'm no longer seeing this girl.

Can faggy trans boys date femme women and not be expected to play “the guy”? Are there any trans folk out there who’ve had similar or completely different experiences?

changes

folks who follow this blog know that i am very NSA (no strings attached).  i have been in a place for sometime now where i am not looking for a relationship or even to date.  there are many reasons for this.  and i've been really happy and content in this current place.  i've been reveling in being single.

for my entire adult life i've been in one relationship or another.  after i ended my last relationship i made a promise to myself that i would stay single for a while.  that i wouldn't just jump into another relationship.  for sometime now i've managed to keep this promise to myself and honestly i would have been content to continue reveling in my bachelor status.

but sometimes shit just happens.

i had been playing around with this guy for a couple months.  sexy non trans dude of color, stick thin (which is not usually my thing i like a little meat).  i like him, he likes me, we have amazing fucking sexual chemistry.  and sometimes we hang outside of the bedroom.  not often but once in a while.  i've met some of his friends on these outer bedroom excursions.  however throughout all this i was very clear that we're just playing around, that i'm not looking to date or anything like that, in fact the outside of the bedroom hang time felt like a bit of an adventure to me.

at different points he would say he was starting to have feelings for me.  to which i always responded that i was not looking for more than nsa play.  to which he always responded that he knew and was cool with it but just wanted to be honest with me.  this went on for sometime and we had alot of fun together.

then one night recently he came over and he didn't look happy.  i asked how he was doing and he said not ok.  i said 'what's going on'.  at which point he totally broke down, sobbing and said that he has really strong feelings for me and he can't just keep doing this NSA thing.  to which i said 'you know that i'm just not in a place right now to have a relationship' he said he knows. i felt like a major fucking ass.  it was very sad.  soon after he left and wished me the best.  

i have definitely had hookups who wanted more.  i was always clear with them that i only wanted to play.  i've had regular situations come to an end before i.e. favorite guy.  when it ended i did feel sad, but this felt different.  i realized despite all my 'nsa' stance i had started to develop feelings for this guy.  the thought of never seeing him again made me incredibly sad.

fuck me man.

i called him the next day and we talked it out.  so now we're dating - its an open kind of thing so my posts on this blog will continue, but with maybe a little different spin.

the skilled cock

dude used to be one of my regulars however we had not hooked up in over six months for multiple reasons mostly due to scheduling.  we had been hooking up pretty regularly at one point, light skin gay guy of color, slim, average build.  he'd been with trans guys before.  total dom top.  

he's the kind of hook up that i appreciate.  we would chit chat some but not alot, he prefers to get right to the fucking and then the post fuck chat is minimal.  it was not an in and out type of situation, we would fuck then cuddle some, maybe watch something on tv, he'd invited me to stay for dinner before (which i declined but thought was nice).  a good number of my regulars like to chat and i'm into that sometimes, but other times i just want to fuck and that's it.  so this dude i have an appreciation for. 

we finally arranged to meet up.  he looks a little more worn down than the last time i saw him.  hard times all around these days....  we don't chat much and get right to fucking.  we both strip immediately and we kiss and grind our bodies together.  his lips are really chapped which i'm not so into.  but he is hard immediately.  and he has a beautiful cock, it has a slight curve in it.  i quickly  wrap my lips around it and slide my mouth up and down its smoothness.  he moans. 

i grab a condom, slip it on and lube him up.  i put the tip of his cock to my cunt and slowly slide him in.  i moan as he enters me.  i ride him slowly at first getting used to the feel of his cock.  he feels so good, his cock deep inside me, i luv the way it feels as i slide up and down its smoothness.  i ride him with a silly grin on my face thinking why did we wait so long to do this again.   however now i want him on top.  i pull him over so he's fucking me missionary (missionary is my favorite position). 

he strokes me slowly our bodies tight against each other.  i grab his ass pushing him deep inside me.  i raise my hips to meet his strokes and clench my cunt around his dick in a way that also hits my clit hard.  its majorly hot.  then he starts fucking me hard and fast, pounding into me, rough fast strokes til he cums shooting inside me. 

he lies on top of me his cock still pretty hard inside me.  he keeps stroking me.  its very hot.  then he stops and starts doing this incredible thing with his cock that i've never experienced before.  i can feel his cock pulsate inside me.  its like his cock is expanding and contracting inside me over and over again it feels like he is cumming non stop.  i cum multiple times from this.  he keeps this up for a good while it feels like we are both cumming over and over again.  until he collapses on top of me his cock now soft and i slide him out.  

as we lie there catching our breath i say to him, that was incredible.  did you cum multiple times or what was happening.  he said he only came once but its something he learned to do with his cock even after cumming.  hot. 

we lie around a bit just resting, however i need to go so we clean up and part ways with a quick kiss. 

disappointing fuck

dude hits me up on one of the sites.  his profile says he is 45 years old.  however in his pics he looks barely into his 20's.  Japanese guy.  i message him back and say there is no way you are 45 years old.  though i'm also thinking there is no way those pics are current.  however, i know alot of people of color look way younger than their age...  case in point myself transness aside.  we bond over getting carded regularly at bars and even at times for cigarettes.  i'm still a little suspicious about the pics but we keep chatting.  he's interesting.  i've found that older guys often have lots of interesting stories and he seems interesting.  he has strong racial politics which is also a major plus.

he has never done a trans guy, in fact he has only been with non trans guys his entire life.  he states he is not sure about how he will react but thinks i'm majorly hot.  we get into a pattern of sending at least daily messages to each other discussing a wide range of topics from what we want to do sexually to gentrification.

after about a week or so of this he mentions getting together to explore my body i.e. fuck.  we decide to arrange a date however i'm feeling conflicted.  on one hand he seems like a real interesting guy and his pics are cute and he said he prefers a slow sensual fuck and right now i mostly have rough dom types.  on the other i have a feeling his pics are inaccurate and he is not gonna by attractive to me.  i also have this feeling that maybe his pics are very, very old and he will not look anything like his pics.  don't get me wrong i get majorly into a hot daddy but i'm unsure if this dude is that.  however, i decide to just go for it mostly cuz i find him interesting, i tell him to meet me at a coffee shop near my place so i can feel it out.

we meet up one week night evening.  he shows up and he doesn't look like his pics.  however he's cute in a round, brown boi kind of way that i find very attractive.  we chat some and then i ask if he wants to go back to my place.  he says sure.  we get back to my apartment and resume chatting on my couch.  now i'm realizing maybe he's not so attractive to me.  the coffee shop lighting was a bit dim....  he also is not really as interesting in person.  we chat for a while, random usual prefuck chat, nothing inspiring.  I'm feeling disappointed as he was so interesting via email....

he seems like he could keep on chatting all night so i realize i'm gonna have to make the first move.  i ask if he wants to go to the bedroom.  he says ok and we head to my room.  this is when things start going even more down hill.  we strip and i realize he really is even less attractive to me without his clothes on.  however, i hold out for that sensual fuck he described. 

we fuck.  its not short, but not long and just not that great.  the whole slow sensual fuck he described to me is no where near what happens.  basically i ride him til i cum then he cums soon after.  nothing sensual about that.  after we are done i decide i want him to leave though its clear he wouldn't mind staying and chatting.  i toss him a towel and ask if he wants to clean off.   he cleans up, i thank him for coming over and show him out. 

you can't make this stuff up...

sometimes what happens on a hook up is almost too much to be believed.  this guy and i had been messaging on and off for a while.  tall, white, dark featured guy.  older.  a runner. 

we finally arrange to meet up and i kid you not, this is what happened.  dude show's up. he's a little less toned than in his pics, but whatever doesn't matter all that much to me.  he's a talker.  kind of talk's non stop.  he's a magician by trade.  interesting.  he has been doing it for a really long time.  he says he wants to show me a clip from one of his shows.  we watch it for a bit.  he is pretty good.  this is all fine. 

we are sitting side by side on my bed continuing to chat.  then he tells me how he's learning hypnotism.  interesting.  he says the first thing you learn is self hypnotism.  i say are you serious - what's that.  he says let me show you.  then dude, i almost can't write this, seriously fucking closes his eyes, sits with his palms up on each knee like he's meditating and says "i am powerful" or some shit like that and then just sits there with his eyes closed.  after about a minute or so during which i am really questioning how i allowed this person into my bedroom, he says the same phrase he started with "i am powerful" or whatever and all of a sudden open's his eyes.  They he says "see, that's how it works".

at this point i'm really unsure about all this, i mean perhaps self hypnotism really does exist, but why would you choose to do it on a hook up, then he leans in and plays with my nipples.  this is an immediate turn on for me and the ridiculousness of the last few minutes somehow leaves my mind.  we fuck, its good, not amazing or worth going into too much detail about, but soon after we are done i show him to the door.

lessons learned - anal cleansing

i've been doing alot more anal these days.  just a mood i've been in.  i choose the dudes i do anal with carefully though.  i prefer a cock that is medium to long in length but not thick.  i mean i've been ass fucked by quite sizable and thick members before and had a lot of fun with it, but i can often only go so long.  

the rest of this post may be tmi for some so please skip it if needed.

the other thing about anal for me is that i have an issue with feces.  its just not my thing.  no judgement for those into it, its just not what turns me on.  even though all the guys who fuck my ass don't care how 'clean' i am and if there's some mess which there is apt to be with anal fucking it doesn't bother them.  however it bothers me, which means i can't relax and just have fun with it.  clearly my issue.  i know that some mess is par for the course with anal fucking and there is nothing wrong with it.  again all my issue.

but i like to get fucked in the ass now and again and i like it to be fun for me.  this had led me to get into anal cleansing/douching.  i understand that it increases risk of hiv/stds to douche before sex but except for with one special person (with whom I have an agreement and arrangement) I use condoms and lots of lube. 

this all led me to purchase my first anal douche.  i went for the low budget model as that is my current situation plus who knew if i would be into it or not.  the thing is it comes with very little instructions so i did some reading on the internet and generally got a sense of what needs to happen.  i just use warm water.  i know there are solutions and mixtures but those seem to come with more possible negative consequences.

the very first time i tried it i didn't use lube.  maybe its just the way my ass works but i could not get the nozzle in and quickly realized i needed to lube it up just a little and then it slid in just fine.

however then another challenge arose.

the first few times it was really hard for me to squeeze that water into my ass.  like i would have to really strain and squeeze the bulb of water really hard.  even then it could only get about half of it in.  however it generally seemed to do the trick.  though i noticed sometimes i would be totally clean and other times not.  after maybe the 3rd or 4th time i realized what i was doing wrong.  basically i think i was inserting the nozzle (for lack of a better word) so far that it was blocked by whatever part of my inner lining it stopped at.  if i pushed it in then pulled it out just a little i was able to get all of the water in with no problem with much better results.

great.  seemed like i was getting the hang of it.  however, in my effort to be clean one time i over did it.  lets just say i did one more bulb of water than i should have and didn't properly evacuate.  luckily when i felt a weird gurgling in my lower region i was alone at that point and able to make it to the bathroom just in time.   

after all this i think i've pretty much got it down now i.e. how to get the water in my ass and how to make sure it all comes out.  feel free to share tips if you'all have them : )

itchy

it had been a lazy day.  i had hung with a friend earlier and i was just at home drinking some wine, cooking some food, i was looking for a hook up but in a kind of lazy way.  not having any luck on any of the sites - slow day when i got a call on my cell.  i didn't know the number so i didn't pick up - as is my practice.  i listened to the message and it was some dude who said we'd been emailing, that we had met through CL and wanted to know if i was free to fuck.

i have no idea who the hell this guy is.  i had not posted on CL in a number of months.  so i went back through my email to try and figure it out cuz clearly we had been chatting since he had my number.  after some investigation i figured it out.  its this dude that had responded to an add almost six months ago.  we had emailed on and off but neither of us could host and i'm not into motels.  also he was ok looking in his pic like it could go either way. so i'm feeling indecisive, i'm not incredibly horny, can't decide what to do. 

i text him back and he calls.  i hate talking to hook ups on the phone, i would rather text, but whatever.  turns out he lives three blocks away.  for folks who follow this blog you know i have two major weaknesses:  1) anything local, 2)  dom tops.  so 3 blocks is fucking hot.  i think what the hell, lets do it.

he says he can host, but he'll have to sneak me in.  i'm not sure what that means, but whatever i'm game.  i say i'll be there in a few minutes.  i walk over to his place.  he comes to the door and does not at all look like his pics, not attractive to me, however i'm here and now horny and i've learned that physical hotness and sexual hotness do not always equate meaning i've fucked hot dudes who suck in bed and i've fucked unattractive dudes who are majorly hot in the sack and really i'm just here to fuck.

it turns out that sneaking me in just means tip toeing past his roomie.  he lives in his studio, he's an artist.  cool art.  no bed but i don't care there are lost of places to fuck.  we kiss, he showered right before i came which i appreciate however it means his long hair is damp which sometimes is hot but in his case is not.  he lays me down on some blankets on the floor.  he sucks my nipples, blows me, all good.  however i want to be fucked.  i suck his cock but he can't get hard.  he jerks himself off, i suck him some more but no go.  he apologizes says he did some coke earlier and has coke dick.  great.....

it turns into an oral session, he sucks me off, finger fucks me, i cum, but its not really doing it for me.  afterwards i get up to leave and he says 'no stay a little longer'.  i lie back down but realize something about this is making me feel itchie.  so i get up, grab my shit and bounce.

i was feeling bad about this hook up.  not so attractive dude, high on coke, limp dick.  my thoughts ran on these lines - what the hell is wrong with me.  if there is ever a time to walk away that was it.  why don't i have enough self respect.  why am i such a chicken shit. 

I have never shown up at a hook up and walked away.  While i feel confident that if a situation ever felt unsafe I would walk away I have been fortunate so far.  my best friend has no problem walking away from a hook up.  he does it with ease.  though the times he has had to walk away are mostly when its been a sketchy situation.  however, its hard for me to do and i know that i have a problem rejecting people - clearly my issue - that maternal, self sacrificing, put others over myself instinct that i can't seem to get rid of.

i was feeling really down on myself, went to bed feeling like shit.  however i woke up the next morning and decided to give myself a break.  while i acknowledge my areas of needed growth and the hookup did make me feel itchy....  at least i did take enough control over the situation to get what i wanted out of it - which was simply to get off...  the rest i'll keep working on