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Bumping this old ass thread so I don't shit up the catalog with a new one.
I'm in a similar situation to OP. However, for further detail, my boyfriend and I have already done some Femdom and light butt stuff, and now he's super keen to be fucked by me. However, although he has taken a dildo in the ass before, it was stationary. Tips pls, from anons who have fucked guy's asses and can tell me how to make it as comfortable and pleasurable for him as possible?
so, i had this fuckbuddy who literally was a wizard. as in, an occultist. think styxhexenhammer, but less educated and fat.
he would casually talk about fapping to bailey jay, which was a nice change because i really hate disingenuous guys who like futa/dickgirls/trannies, but won't admit it. i saw some stats on who looks at tranny porn, and it's usually heteros who look at the shit, so i'm not really worried about any potential mates being gay. but i'm still cautious. not that them being gay is a problem. it's just i hate it when someone is being disingenuous about ANYTHING. if they can't open up about what they jerk off to, i'm not even gonna bother.
anyway, i was dating this guy who gradually became an omega male. i was revenge pegging him because i kept telling him anal isn't that easy for me. i mean, i liked it in a sadistic way, but it wasn't my first choice.
broke up with him, told the wizard guy about it, asked him how he felt about pegging and said he was down. the only reason i asked is i wanted to see the difference between my ex and this more confident guy.
it worked out pretty well in the end because he went power bottom on me. i'm 5'4" and he's 5'9", which is perfect for me. he even started lifting to lose some weight. he has stronk arms and some minor chest gainz, but the gut isn't going anywhere soon. which is actually ok because i have a thing for plump guys, tbh.
so i got out the "device" and went in for the kill and he stopped me. he said "anon, you're coming with me. there's a secret orgasm in my ass, and you're going to find it." deadpan.
he fucking moved away and removed me from facebook without a single word.
sorry for blogposting.
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>ex gf always grabbing my butt and saying she'd like to try pegging
>end up warming up to the idea
>tell her "ok let's do it"
>she freaks out "anon I didn't know you were into this stuff, y-you aren't gay are you?"
Now I'm just afraid she's going to tell everyone I'm a huge faggot.
>didn't even get pegged in the end
I'm the poster who bumped originally. Although I haven't pegged him ye obviously I've fingered him and given him rimjobs before. If you're at all concerned about things like stank and taste and w/e, try doing stuff for the first time straight out the shower. use a lube that's relaible and inoffensively flavoured if you're using your mouth. If he's hairy, it's not unreasonable at all to ask him to trim at the very least, I asked mine to and he actually shaved which was a nice and welcome surprise.
It regards to being dominant, you don't have to necessarily "take the lead". tell him to let you know when he's ready (ie clean) and ask him what he wants. he can still guide you while you're doing it in a way that means you're not in control so to speak, even though you're the one doing things to him. I make my boyfriend fuck me when I'm domming him and he's still very much the sub because I'm telling him exactly how to do it and have all the control.
Also, sage goes in the email field. Good luck!
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>have a FB who's 100% into pegging
>prostate kills my boner instead of causing it