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My Dating Life As A Transwoman: BUST True Story


Tags:
trans
, woman
, transwoman
, transgender
, dating
, Tinder
, OKCupid
, pre op
, post op

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This post by Shaikina Nayfack originally appeared on brokeassstuart.com
Last year was a hectic one, recovering from gender confirmation surgery (while writing a show about it), running a theatre company, getting on the scene as a trans actress... So much of my energy was spent working on and talking about becoming a woman in the world that I spent very little time actually being one. Year one is over, and I’m ready to get out there and take my new self for a spin. Dating pre-op was its own adventure. I’d been relatively celibate for a while, my last few years posing as a gay man stunted by the knowledge that whatever sex appeal I could generate was really just false advertising. When I started my transition I became suddenly aware of the new sexual economy afforded to me: The world is full of hot straight guys who want to get fucked by chicks with dicks. Topping isn’t really my thing, but I had a narrow window of opportunity to enjoy being a commodity fetish and wanted to make the most of it. Feeling sexy and desired just by being honest about myself was really gratifying, especially after hating my body for so many years. There weren’t a lot of dating options available to me at the time. Miscellaneous Romance on Craigslist was the first personals site I found that had m4t or t4m options. I was on OKCupid too, but after getting a death-threat from some dude I wrote the company a strongly worded email about their need to diversify gender options, and closed my account. I also had a profile up on anon.com and tryatranny.xxx — Yeah, try a tranny, that’s a thing. Let’s be real, this wasn’t about dating, this was hooking up. The guys I would meet, they were just regular dudes with one thing in common: an attraction to pre-op trans women. I’m sure they had seen their fair share of tranny porn, but watching their faces as I undressed, or as they undressed me, was like watching Columbus discover America! (Historically inaccurate, but you get the idea). The sex was fun, exploratory, intriguing. I was learning how to get into my body, my breasts were growing and increasing in sensitivity, and I was gaining confidence in my feminine form. My relationship with my penis changed as well, from one of loathing to one of tenderness. And these straight guys were into it. They handled me better than most of the gay dudes I’d been with. They’d be sucking or stroking it and call it my pussy or clit, I’d just laugh and let them go to town. Once this younger guy told me, “you’re pretty cool, most of the other girls charge.” — I’ll let you work out the problematics of that statement on your own.
To be fair, not every woman with a penis is interested in being sexually objectified; I’m simply reflecting on a chapter of my personal journey in which I was. Also, not every woman with a penis is interested in getting rid of it; the transgender umbrella is broad and covers a wide range of people with different relationships to and plans for their bodies. In my 15+ years as a gender non-conformist I’ve met a lot of guys who are into what I’m bringing, but our encounters are almost always shadowed in taboo, discretion, or fantasy. None of these dudes wanted to take me to dinner, none of these dudes were comfortable being seen in public with transwoman on their arm. We have T-girl porn and we have transwoman celebrities, but we lack a mediatized understanding of what it means to date—or dare I say fall in love with—a transgender person. I’m hoping ours will be the last generation with that problem. If more non-trans people would openly acknowledge their attraction to trans folk we could really start changing cultural attitudes about sex and gender on a fundamental level. Post-op, things have changed. I don’t have the unique combination of equipment that satisfied my previous lovers, and having gone through a brutal year-long recovery, I’m in no hurry to give up what I fought for. Don’t get me wrong, I enjoy getting choked and fingered as much as the next third-wave feminist, but I’ve started to value my newfound virginity as a source of power, and I’m both excited and intimidated by the thought of letting someone else inside me. And I will always keep a special place in my heart for the first guy who made me cum, stayed over, and went out for coffee with me in the morning. It was a radical orgasm, but it was an even more radical latte. A few months ago I re-opened an OKCupid account. I was surprised to see that there was a whole new matrix for listing one’s sexual and gender identities. On my profile I’m currently listed as a straight, queer, sapiosexual, women and transwoman. Unfortunately, most other sites haven’t gotten up to speed. Last month I was blocked from Tinder because a fair share of my matches reported me for being trans. The alternative, trying to swipe right while stealth, could lead to something far more dangerous, like harassment or violence. Tinder is well aware of the problem and—as of this writing—has yet to take action toward trans inclusion.
There’s also been a remarkable shift in the responses I’ve gotten from non-trans guys on the online dating scene these past two years. More dudes are asking respectful questions, or sending supportive messages. More dudes have a grasp of the transgender lexicon and know how to use trans terminology. Admittedly, I still feel like a curiosity. I still have to sift through tons of hypersexed advances just to forge a conversation that may, one day, lead to a proper date. And I’ve lost count of the number of times I’ve been stood up or flaked on at the last minute. Maybe all ladies are subject to this online, but these are certainly the romantic misadventures of a post-op transwoman in her mid 30s. So to the fellas out there who do wanna get with that hot trans gal, here’s some friendly advice from one who knows: • Do not call her a tran or a trans or a transgender. No one is a transgender, unless you’re not transgender, then you’re a-transgender. She is a woman, or a transwoman, or whatever she prefers to be called. • Paying attention is the most erotic act. Try to be mindful of her struggle with her body, and see if you can combine your own pleasure seeking with the intention to offer her an experience of physical harmony. • Lead with respect. Tell her she’s awesome for being true to herself, because she is. • Your dick pics are worth a fraction of a face pic with a loving gaze. Her dick pics are her prerogative. • Your penis is not a weapon. Neither is hers. • Never underestimate the value of an intense make-out session. • Let her take the lead and she’ll show you what she wants. If there’s a question, ask. • Anal sex is not a consolation prize. • The three-day rule is for losers. • No teeth. Xo, Shakina
Shakina Nayfack is writer, director, actor, and performance artist based in New York City. Follow her on Twitter, Facebook, Instagram and YouTube. 
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I showered with my mom and things got awkward
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I broke my hand a couple days ago and I can't shower with my broken hand so my mom decided to shower with me to help me. She take all her clothes off and take my clothes off and went to the shower. My mom was washing me and i was trying to not have a boner but I can't help it and I got an erection right in her face and I said I'm so so sorry she said “That’s okay it just means you’re in good health!” so then she was washing my penis and balls she wash it just like she was trying to make have an orgasm then I can't help it and let it all out right in front my mom! she was a little shocked but then she said “I’m glad you’re enjoying this” then she cleaned the mess and washed my penis and then we finished the shower. Since then I haven’t talked to her and I don't think i can get myself to talk to her ever again. What do I do now?
Reading your post history... clearly a troll.
What you do next is r/quityourbullshirt Per your history you have killed people including family members, 3-ways with teachers, fucked your dad, sister, mother while camping and you're clearly a fucked up troll.
Found Sigmund Freud’s Reddit account.
Put a waterproof bag over your busted arm and wash with the other good hand / arm for fucks sake.
She is very fat , he thought the rolls on her leg was her pussy.
Shower with her again, but tell her you read online that mouths clean better than hands.
Now you should tell all your friends and relatives
Well well boy aren't you lucky what are you do? Should you even have to ask if she did that enough and you allowed it to make you come then both of you were enjoying it. So do what you want to do because that's what we should all do. Instead of what some book or some other person said it isn't okay if you liked it then ask her to help you with the shower again. Just cuz people say it isn't okay it doesn't mean it isn't do what makes you feel good do what makes you happy whatever it may be

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I walked into my son’s school a few weeks ago to pick him up. He was sitting with all his friends waiting for me by the door and immediately got up when he saw me coming. Clearly, he didn’t want me coming anywhere near his friends. I got the feeling he didn’t want anyone to know he was with me. I was right.
As he got closer, he whispered, “Mom, why do you have to dress like that? Everyone stares at you.”
“No they don’t. They are probably staring at you because you are so handsome,” I told him.
“I blend in. They aren’t staring at me. They are looking at you. Why do you have to wear dresses and high heels?” For the record, I was wearing the outfit below. The nerve, right?
I decided I wanted to try something with my teenage son that day. I asked him if he wanted to dress me for a little while. I told him he could pick out my outfits and I would wear whatever he wanted me to wear as long as he had an open mind and would listen to a few things I had to say about people and the way they choose to dress, so that’s what we did.
I wanted to talk to him more about the subject and why he was feeling the way he was. And by having him choose my clothes for a while I would better understand why he wanted me to wear certain things, and maybe he would understand why I like to dress the way I do and that, really, it shouldn’t affect him as much as it does.
This was his choice for the first day. He picked out a very casual, sporty outfit, and I loved it.
While I dress like this about half the time and like this look, it doesn’t always suit me. Sometimes I feel like dressing up more, so I do. When I asked my son why he picked this out, he said because I “blended in and didn’t look out of place.” In his mind, when I dress up, I look like I don’t belong. If he only knew how many women I saw throughout the day wearing suits and heels maybe he would have a different opinion.
Regardless, I told him nobody should be judged based on how they dress — not even your very embarrassing mother . Most people wear what they are comfortable in, what makes them feel good. It doesn’t matter where it came from because this isn’t how we judge others. We focus on how they make us feel, if they are kind, how they treat people. I told him judging people for what they wear is very transparent, and he will be missing out on a lot in life if he is going to focus on making friends because of what they wear, what they have, or what they look like.
If he is comfortable dressing in a way that makes him feel like he blends in, I think that is great. However, I want him to have the inner confidence to step out of the box if he wants. If he feels like wearing something, even though none of his peers are, I want him to feel like he can.
I also let him know what someone puts on their body isn’t an invitation, for him or anyone else, ever. And he should always take heed on how he looks at people, especially women. There is a way to look at a woman without staring or gawking. No matter how you see her, she deserves respect. I don’t care what she’s wearing.
I also want my son to realize just because I am a mother it doesn’t mean I have to dress a certain way. I loved the outfits he picked for me, and dress like that on my own accord often. But I also love wearing dresses, heels, skinny jeans, and trying out new trends because that is who I am, and who I was long before I became his mother. It’s not my intention to embarrass him. It is my intention to be myself, and him making comments or telling me he doesn’t want to go anywhere with me because of the way I dress is hurtful (as normal as it is).
A few days ago, I discussed these “lessons” I was trying to teach him with a friend and she told me he would “take all these lessons and bake them into a gentleman pie.” I really hope she is right.


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