I have always loved to develop a woman, sexually, make her comfortable doing things, she wasnt ready to do when we met.
I did this on multiple occasions, sometimes with success, and many times this lead to the demise of my relationships, but every time, it was a fun ride.
For instance, my college gf, didnt like cum, but ended up as a cum hungry bitch, who would, in the end, be disapointed if we had sex without a cum play.
My ex wife, total prude, from being body self aware, to wearing no panties, sunbathing topless, and sucking and fucking in public parks, on parking lots, in the cinema...
My newest conquest is this divorced woman, my age (early 40s). Successful doctor, cardiologist, her marriage collapsed due to long working hours, so we started off as fuck buddies. Still slim, still hot, brunette, she got a boob job soon after we started messing around (and right after her divorce).
For a woman of that age, she is, of course, experienced, but like all, she had her weakness. When she was on top of me, I reached with my hand towards her anus, wanting to stimulate it with my finger, and she moved my hand.
It took me over a year, but gradually, I made her enjoy her asshole being used.
I started by licking it. It wasnt that easy, she moved away at first, but one time, I offered her a foot massage. She was on her stomach, as I massaged her, until she felt totally comfortable. I would move her legs aside, so that her pussy and asshole were visible to me. Moved my hands up, and started working her clit with my hands, while my cheek was pressed against hers. As she was close to orgasm, I moved in a way, that she could feel my breath on her asshole, and she started arching back, so I went for it - she came instantly.
This was a thing for a while, and the next step was the finger. By that time, I introduced dirty talk, and as she was on top of me, I was just telling her what a great cock rider she is, and pushed my finger in her mouth, asking her, if she is a bad, bad girl. She noded yes. Are you sure? Again yes. With my left hand, I moved her cheek to the side, she knew what was up, and as I moved my wet finger back, she followed it with her eyes, as far as she could. I didnt go in, just started rubbing the exit - she came like she was obsessed.
Then, slowly, things moved along. It was a finger, then two, and when I showed her the first but plug I bought, a small one, she smiled.
Soon enough, I was fucking her in the ass, and she loved it.
But that wasnt enough.
Again, she was on top, with a plug in her ass, when I decided to pull it out. She was moaning from joy, as I spread her cheeks wide, knowing her asshole is gaping back there. "you want a cock in your ass, right now, dont you?" Of course she did, so I put the plug back in, and again, she came like crazy.
The plug was substituted with a dildo, then a bigger one, until double penetration became something normal for us. And every time, I was telling her, that she needs another cock to be completed, and she would shiver in extasy.
The night I invited my friend over, after we were in a local bar, to join us at my place, while we were going up the stairs, behind him, I whispered to her "he is here to complete you".
She almost fell, but kept going up.
He knew why he is there, we did all sorts of things together, and this wasnt our first rodeo, so as soon as we came in, I started undressing her, and kissing her, and she was ready.
It was like when we practiced - her on top, only this time, it was another mans cock up her ass.
It was unbelievable.
Tomorrow morning, she told me, that it was great, but that she feels ashamed, and that we shall never do it again. I said ok, but I know that that was a lie.
Will keep you posted.
