u/mongojunge18

PHOTOS ARE REALLY MY OWN!!

Hey there:) I really need some advice from guys experienced in (anal-) gay sex😉

I'm a skinny, younger-looking 27-years old dude & I'm apparently the real-life version of gay porn's ultimate sex fantasy character: The young, willing 'Straight 2 Gay'/guy with a fully-shaved, large plug-& Dildo-experienced, well-rounded butt & asshole (countless men/women complimented me on how pretty/sexy my ass looks over the years, same with women and my apparently above-average dick (ca ~20cm), so no arrogant self-aggrandizement here😏)
who only ever had sex with women (yet). But now I'm single again and super horny for big(ger) hard cock in my ass. Preferably the nice cock of a hot man over the age of 50.

Yeah, I totally want an older dick up my tight anus 😍 which has been a regular masturbation-fantasy to me since my teen years.

I was always bi-curious (closeted) & been playing/let females play with my butthole for yrs - but now, as a single guy again, this fantasy could finally become a reality. I had some experience with two dicks (of the same age) when I was ca 13 yrs old, which was very innocent butt-play and some BJ attempts, but I never had a real man's cock up the ass/in my mouth before. But I'm eager to try it.... or am I?

I placed an "experienced gay da**y wanted" ad on a local site and I've talked to A LOT of horny hot gay guys online in the last few weeks, all of them older than me & willing to fuck me from behind in a more dominant way (my biggest fantasy🥵). My *nbox was literally bombarded with men horny for my tight grip hehe😉

One guy really interested me, seemed experienced enough, discreet (important!), and well-build enough and I took it as far as even exchanging numbers, currently exchanging pics & sexting on WhatsApp (I'm from Germany). I made countless new pics of my body, cock, asshole to send to him, even bought myself a larger dildo, new lube especially designed for anal sex and a clyster (if that's what you call it?) for cleaning my hole. We're constantly sexting/chatting, talking about boundaries & fantasies, even talked about meeting up THIS weekend!

So I'm already pretty deep into it & horny but I'm somehow still asking myself & this subs people:

should I really do this? Does it feel really that good to be fucked in the ass as I imagined it over the years? What if I chicken out because I suddenly realize it's just a fantasy?
do you have some advice to tell here if he's the right one to pop my anal cherry? What are gay dating red flags? what should I keep in mind when meeting older men for fuck dates?
what should I do before getting fucked? How do I really prepare for hot gay sex?
do you had an experience with an older top guy when you were younger?
anything else to know? important details?

and finally: please Convince me with your hottest story about such encounters to REALLY let someone hot fuck my needy asshole!

SORRY FOR THE SUPER-LONG TEXT, English is not my 1st language, but I really needed to get it out, I have nobody else to give me advice on this....

Thanks for reading❤️ cheers, a young wannabe-slut

I'm usually attracted to women only, but I'm can't stop thinking about a hard cock in my asshole lately...should I go for it? Tell me now what you would do to my tight boyhole, please...

beginner-bottom (27yo)- filled my hole with my biggest plug yet, how do you'll like my small gape? Tell me what you would do to my tight ass..!

I'm going to be fucked in the ass for the first time this weekend, now asking myself if I'm really ready to be turned...? Would you like to penetrate me too?

is my boy hole attractive to men older than me? (m/27)

I'm going to be fucked in the ass for the 1st time this weekend, any important advice for a beginner-bottom?

I'm a true (ex-)straight guy, newly single, should I really let an older man fuck my holes? Should I finally try this long-time fantasy of mine?