Anal massage seems to be a problem for some.

[+ StLouisOct]

I need guidance from the more experienced. My two recent escorts had no problem having my dick up their ass, but they didn’t want a finger inserted there. I showed them that my fingernails were trimmed, but that didn’t seem to make much difference. I like including anal massage in the experience. I know personal preference is important, so I can’t be critical of those I’ve been with. Regardless, it would be good to hear the perspective from other escorts.

[Trick]

Did they give any reason?

[+ BenjaminNicholas]

Fingers aren't as sexy as a dick. Bottom line.

[big-n-tall]

Not an escort...

 

A finger may be smaller, but of course, it's stiffer and harder than a dick. Hell, even a hard penis is somewhat flexible. If it's not done right inserting a finger or fingering can be very painful for a lot of people. I have personal experience. LOL!!!

 

Maybe the guys you saw had bad experiences and just prefer not to have a finger in their ass. If you see these guys often, maybe ask them.

[+ FrankR]

Fingers aren't as sexy as a dick. Bottom line.

Sounds like you have a scale of sexiness going? Where does the tongue fall??? ?

[+ BenjaminNicholas]

Sounds like you have a scale of sexiness going? Where does the tongue fall??? ?

 

 

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[+ OliverSaks]

People unfamiliar with assplay / unskilled with assplay can cause a lot of pain and discomfort and hurt a provider’s ability to conduct business. People seem to be less delicate with a finger, in my experience.

[+ Keith30309]

Having a finger hovering over your ass is a little unnerving if you don’t know what it’s going to do A rough finger with jagged nails and cuticles rammed in with a little spit for lube can be really unpleasant.

 

The percentage of guys who allow... much less enjoy... this is at most 20% based on my limited experience.

I regularly meet two guys who happen to love this and found that moving REALLY slowly with lots of verbalizations about what I’m going to do and not do is helpful in building trust. When I seen them now I feel like the fear has been replaced by trust and eager anticipation but I still move super-slowly with rhythmic predictable movements.

 

To the OP I’d say see them multiple times and very gradually work up to a place where you are predictable and trusted. That doesn’t mean they’ll like it but it’s a good first step.

[Pulgasari1991]

From anecdotal first-hand experience, it changes from uncomfortable and mildly painful to very smooth and pleasuring, depending on the lube (so far found myself noticeably better with durex eternal) and most importantly, on using disposable gloves; as mentioned above, bare fingers can be quite rough.

[desertguy1954]

I find the rimming can help to relax, also not rushing, then gradually with lube slowly massaging the hole slowly move the fingers to find the prostrate. Can be enjoyable for both and make taking that nice cock easier to take up the ass.

[+ azdr0710]

(flexible) knuckles seems to be a concern, too......fingers can (unintentionally) bend a bit and add to some discomfort, I suppose.......reaction from dudes I've fingered range from pleasant silence to a rapid "NO, this isn't going to work!!!!".........no surprise, I guess........

[liubit]

I find the rimming can help to relax, also not rushing, then gradually with lube slowly massaging the hole slowly move the fingers to find the prostrate. Can be enjoyable for both and make taking that nice cock easier to take up the ass.

Exactly. I have been complimented by several escorts on my fingering technique, and my regulars never fail to ask me for it.

[+ nycman]

Never been into fingering.

 

Caressing? Licking? Fucking?

 

Yes. Yes. And Yes!

 

Most men don’t seem to derive pleasure from it, so I rarely even attempt it.

I find a nice wet tongue does more to relax a tight hole and open a guy up.

[marylander1940]

One finger with lubricant to open up it’s all the fingering I ever needed...

[+ Keith30309]

It always starts with... just.... one.... pinky....

Then before you know it you’re slung upside down with a gas mask and pint of poppers having your molars checked by a guy named “none of your fucking business”.