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Pre Marriage it would have been a toss up between my first threesome and the afternoon I found out that my girlfriend was a submissive who would do nearly anything. The two involve different people and happened several years apart but both of them led to a lot of shenanigans.
Post Marriage it's a tie between my wife managing to accidentally self-discover she liked anal (a truly funny and hot story that does not involve a dick) and a few days later when she purposely tried DP and found out that it gives her a rolling orgasm.
I think you’ve got to tell the story about your wife accidentally discovering anal.
This is a bit of a story so bear with it.
I spent nearly three days doing what I've heard called "GentleDom"; politely tell her to do something then praise her for doing it when its done, sprinkled with compliments about her and her body throughout the day. There's no sex or sex related tasks with this, what I ask for is all traditional housewife type stuff like put the laundry away, update the seasonal decorations, go pick out new curtains so I can hang them, that kind of thing.
My wife is a smart woman with two Masters Degrees and works full time as Professional so she knows what I'm up to with this but she has a submissive streak and normally responds pretty well. I normallly only do it for a day as a run-up to sex that night but this time I just carried on without starting Sex in the evening.
Apparently two plus days of this was her limit. In the late afternoon of day three she pulled me into the bedroom and initiated with me, which is rare, and I figured since she started it I'd let her run the show. We fooled around for awhile and she was naked lying in bed on her back when she asked for a toy. While I walked across the bedroom she elevated the top of our adjustable bed so that she was sitting up. I came back with the really basic Rabbit G-Spot / Clit vibrator that she likes and with some lube and teasing she's having a good time.
Here's where it takes a turn in the "Dear Playboy" direction. She's worked up and obviously wanting some stronger vibes because she breathily asks me to grab her smaller vibrator, it's like a Hitachi but battery powered and about 1/2 the size. Again, she's running the show so off I go, intentionally leaving the first toy inserted and running but with the clit vibrator part aimed down. The idea was to keep the G-Spot vibes going but nothing else. I walked back to the ToyBox and as I'm rummaging up what she asked for I looked over to see that her hands are still behind her pillow and she's got some hip rocking motion going. I smirked and mentally patted myself on the back.
When I got back around the bed with the 2nd toy I realized that the 1st one had shifted and the woman who wouldn't even discuss anal play now had Toy #1 halfway up her ass! After my brain was done Blue Screening I rolled with it by adding more lube and slowly pushing it all the way inside, then I added Toy #2 in the customary place. Since it was already there I made sure that Toy1 stayed lubed while I slowly worked it in and out and continued to run Toy2. I did that for a few minutes and then put the wand at the entrance to her Kitty and applied some pressure while continuing with what I was doing with Toy1. The result was her having one hell of an orgasm, which was no surprise to me (obviously not my first rodeo with this stuff) but it was to her.
In discussion afterwards I found out what happened. Toy #1 slid out when I walked away, however because of the angle of the bed it couldn't get away completely. It was only able to back out until the battery end hit the bed, it was still vibrating and with how slick everything was the tip end slid down her crack and re-aimed itself. She was extremely turned on and with everything being so slick she just...hip rocked herself onto it. To be clear she knew what was happening she just didn't care enough to stop as she chased the sensation. The situation was odd but the experience was hot as hell. When I asked her if she liked it she smiled and gave a somewhat vague answer about how it was a lot of sensation. I honestly think she was embarrassed to admit at the time how enjoyable it was for her. She got over that before the end of the week.
If you are wondering Toy1 is pretty damn basic, it doesn't have all the curves and swoops that a lot of Rabbits do. It's firm, straight, and maybe 1" across at its widest point with a blunt tapered (but vibrating) tip. It was never in danger of going all the way in because the clit vibrator part wouldn't allow it. It's actually a near ideal design for what it ended up doing.
So there you go, the story of how my wife managed to accidentally self-discover that she enjoyed anal.
I second that proposal.
Posted.
Where'd you post it?
Same thread, but if you can also click on my profile and read it there.