Not-So-Gentle Femdom

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Question.

How much anal play do you want? What constitutes gentle vs not?

Let's take "rough pounding" off the table. I'm wondering more about other stuff. Insertions, dilation, enemas.

Would it be the difference between fingering your hole vs using a long dildo? Or can both be "gentle"? Is it just a matter of how deep? How wide? How forceful?
My first wife was not into strap-ons but we both enjoyed rimming and a finger, however she did like dp so I did get her ass hole several times but she never reciprocated. For a birthday present she got a dominatrix to peg me all night at a hotel room which did include rough pounding, while she went out and fucked her boyfriend (that I did not know about)

After our divorce I met a woman that loved pegging after sex. We hooked up and she used a way thinner strap-on than my cock which is 5inch around hard and 2 inches longer than mine, I am 7.5 inches long,and spent another 2 plus hours sensually using her strap-on to make love to my ass hole. We did it in several different positions and we changed positions after I would cum. The last time I came it was a dry orgasm.
I loved the sensual pegging.

Current wife has no interest in the back door, she freaked out when I rimmed her and fingered her to an awesome orgasm. 😎
 
Leather cuffs: $45

Leather cock ring with ball separator: $27

Gates of hell CBT harness: $19

Sadistic crop-weilding master: Priceless



Sorry, not exactly femdom, but I sure would love my Mistress (meaning my wife) to do this to me....
I agree, where is the second half
 
I have been locked up in chastity and haven’t cum in about 3 1/2 weeks. Very horny, very submissive, very attentive to my wife’s needs.

For some reason, I was fantasizing about her kicking me in the balls the last few days. I’m not really into pain, altho I do enjoy a good hard spanking once in a while.

Last nite when I got home, my wife was outside by the pool, naked. I got undressed and joined her. She started playing with my caged dick and balls with her feet to get me aroused (it worked).

I told her about my fantasy of getting kicked. She wasn’t so sure… she kicked me very lightly… not too bad… I asked for one a little harder…

Now I know why I don’t like pain! Second one hurt like hell!! I was hot and sweaty from work so I ovwreaggerated an “Igor” walk (made her laugh after she felt bad abt it) and jumped into the pool.

I still don’t love pain, but I have to admit, it turned me on a bit… there is something about submitting to a trusting partner.
 
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