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Most Awkward Sexual Experiences Thread

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File: King David.png (486KB, 453x546px)
King David.png
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I told a friend this story the other day and realized it's actually pretty funny. Wondering if other trans people have comparable or worse.

>FtM, doing a random hookup at a hotel with some cis boy
>guy calls me up on his way to hotel, says he's never had NSA sex or fucked a trans person before, can I tell him about myself
>I'm baffled because hookups never want to know anything about me. tell him depressing shit about family's reaction to me being trans
>he seems oddly comforted
>shows up to hotel, we fuck
>afterwards he keeps running his hands through his hair anxiously on the end of the bed
>what's up
>he says nothing, you're just...a guy
>I know...? did you...not have a good time or
>no it was really really good and I enjoyed it, I just didn't know you'd be so obviously a...dude
>uhhhh
>he starts crying
>I try to be supportive as far as my mental health allows and then scoot on outta there
>>
>>8816704
that's honestly my least favorite thing about sex with random cis people- how fucking broken up they are after
like yeah, I get it, we're such disgusting monsters that you can't believe you just had sex with us.

It's like, I understand it, they're working through some shit that they didn't think they'd go through, but aren't we supposed to be the ones who break down during/after sex or whatever?
>>
>>8816704
My most awkward experience is never having it.
>>
File: clap clap urban.gif (2MB, 450x251px)
clap clap urban.gif
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>gay male
>at a party
>drank a little too much yet enough to remember everything
>some girl I barely know starts hitting on me
>told her I'm not interested
>she insists
>I'm trying to tell her why
>she still doesn't care, wants the D
>whatever at this point just rolling with it
>went to the bathroom with her
>she blows me for like 15 minutes
>I'm still soft, it's not working at all
>she gets up and slaps me in the face
>I sit there for half an hour coping and thinking how it was my fault she got upset
Yay, best first time I could ever think of.
>>
>>8816712
Yeah, it was sad, but I guess a compliment in a fucked-up way.
I think he wanted a soft butch reverse trap
Instead he got a fem gay dude
¯\_(ツ)_/¯
>>
File: 1489403782123.png (457KB, 700x558px) Image search: [Google]
1489403782123.png
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Guess most times with my first and hitherto last bf. I hadn't been with anyone before and he wasn't terribly communicative so it was all rather clumsy and awkward.
>>
I am a swimmer - It was my first time going out with a trans chick and I asked her on tips about how to keep body hair short like hers, since she mentioned something about it - But the thing is that I am a hairy fucker, and It probably sounded like I was calling her hairy right after we had sex.

God, I was such a fucking sperg.
Thread posts: 7
Thread images: 3


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