Your preferred position to pop a guy’s cherry

[backtails]

Fucking virgins is the most overrated thing in all of gay sex. It's hot to know, later on, that you were the first, but in the moment it's always awkward. It's never a good fuck.

"The body must learn to accept what the mind craves" -- truer words have rarely been spoken about the popping of cherries. They've been stroking to the idea of a man's cock in their ass for years, and they've probably taken everything from fingers to carrots to dildos, but they don't know that it's going to hurt the first few times they actually get fucked.

All that said, I like having him face down with a pillow under his ass. Some might think it's good to have him ride you, because he's in control, but a first-time bottom really shouldn't be in control at all. If you're really lucky, he might enjoy it, but he probably won't. A few days later, though, he'll probably be begging for it.

[Harryass]

That’s the way it was with me it hurt but It was great and now I am gay.

[Guest CuriousDallas]

I’ve kind of become the virgin whisperer, not by choice but because I like talking to guys and getting to know them and out them at ease first. I find both them riding my dick and them on their back both work well as you’re facing each other and I can read his facial expressions and eyes. I usually start out with them riding me but often find that’s awkward and they just don’t know how to get my dick in the ass and I lose my boner pretty quick. If they trust me I start with them on their back and start with a lot of lube but the best is jacking hem off and using their cum for lube, but that’s super risky as some guys are finished once they cum. I take my time working my dickin them but honestly my first load comes pretty quick fucking so I usually go off inside them pretty fast. Once they’re over that sudden initial shock it gets easier as they hole has a load in it and I can get deeper. Of course some guys want it over once I shoot that first load cause they’re freaked out. Others get the relief knowing they got what they wanted.

[Guest SecretCumWhore]

4 hours ago, CuriousDallas said:

I’ve kind of become the virgin whisperer, not by choice but because I like talking to guys and getting to know them and out them at ease first. I find both them riding my dick and them on their back both work well as you’re facing each other and I can read his facial expressions and eyes. I usually start out with them riding me but often find that’s awkward and they just don’t know how to get my dick in the ass and I lose my boner pretty quick. If they trust me I start with them on their back and start with a lot of lube but the best is jacking hem off and using their cum for lube, but that’s super risky as some guys are finished once they cum. I take my time working my dickin them but honestly my first load comes pretty quick fucking so I usually go off inside them pretty fast. Once they’re over that sudden initial shock it gets easier as they hole has a load in it and I can get deeper. Of course some guys want it over once I shoot that first load cause they’re freaked out. Others get the relief knowing they got what they wanted.

Keep spreading that seed stud 😈🔥

[Bibttmmiami]

My first time the top had me ride him. I took him deep and rode him pretty hard. He made me stop because he was afraid I’d make him cum too quick and he wanted it to last. We went to doggy and then spooning.  I really liked doggy and riding him the best. In doggy I was begging him to fuck me harder and deeper. 

[downtownswallow]

On my back ...legs spread and the Top's hands wrapped around my ankles. I need to be taken...raped...where'd for a fuck. All I needed was to watch the Top getting ready to breed me. He was turned on by my reactions, sounds and my expression when he started injecting his breeding load. I needed it balls deep.