Like most guys, I occasionally try out Grindr before realising that my local guys aren't exactly exactly an attractive bunch.
Now, I'm an absolute slut on paper. I have a lot of out-there fetishes that I fantasize about so much; in my profile I've listed that I want to try group sex, glory holes, leather, amyl, and cross-dressing. I fantasize so often about sex and getting my throat pumped full of cum that I end up jerking off while I chat to guys on Grindr, after which the post-masturbation guilt sets in and I end up canceling any meetup plans with these guys.
One morning on my usual morning wood-fuelled trawls through the list of local guys, I get a message from this 35 year old man. He looked nice and approachable, so I messaged him back. I mean, I'm not gonna turn down a guy slightly older than me if the dick is good enough.
We begin chatting, and he seems really nice - like the kind of guy I'd want to get to know better and *then* fuck. He's currently in Sydney for work, and he mentions that instead of just wanting to fuck me, he wants to do something else:
He wants me to wear a nice set of lacy lingerie under my normal clothes while we go out to dinner. After dinner, he'll take me back to his hotel room, I'll strip down to my lingerie and put on makeup, and we'll spend the night having sex. I asked if I could film it, seeing as being filmed is another huge fetish of mine, and he happily agreed.
We've got a night in April planned, and he's buying me lingerie to wear, seeing as I don't have my own. He's not sleazy at all; he's really charming. Better yet, I don't want to cancel the night out when I get that post-jerkoff guilt. Even when I asked him if we could cancel at one point, he kept talking to me like a human being (instead of the usual "fuck you anyway ugly cunt" sour grapes shit I get) and being really sweet.
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Thoughts? Do I go through with it? Is this suss at all?
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