And it’s not how the title sounds lol. Basically ever since me and my wife got together I had been stern about no butt stuff either direction even though she’s periodically joked about strap ons. In fact every time we go to a sex shop she almost wistfully stares at various strap ons. Anyway as I’m nuts about her a few weeks ago I decided to pick up a small cheap silicone dildo and a small butt plug to experiment on myself to even see if itd even be viable…all without her knowing lol. Totally hated the butt plug. The six inch dildo on the other hand…that wasn’t so bad. The first night I used it it was tolerable and the second night almost pleasurable. Third night the idea of it being hooked to her sexy hips and thighs actually caused to have a full rager. So I’ve decided to moved on to conditioning my rear end. Going to continue to use the six inch till this weekend then move up to a bit girthier 8".
Guess a lil more backstory. I myself have periodically crossdressed usually in secret for the erotic factor. A few women who were actually bi but living as lesbians would occasionally use me as a booty call whenever they wanted male physical attention…with their significant others permission… sometimes their s/o would drink with us. Anyway a few of them would occasionally make me dress in drag before we hooked up…tucked, fake boobs etc. Then pull my Wang out for our activities. One would make me retuck after before going to sleep. As this stuff happened when I was still young crossdressing for sex with a woman as well as her being rough with my 
makes my heart race.
On my wife she is actually split down the middle bi sexual. And was in a serious lesbian relationship for a number of years. Basically one day they both decided strap ons weren’t doing it for them. So they both made a point to date men…but are still very close. In fact her ex refers to herself as my other wife.
We took several of those “dom or sub” quizzes and I ranged from 60-70% Dom and 30-40% sub and she was basically reversed. So basically I’m a Dom that occasionally likes to be dominated and she’s a sub that occasionally likes to dominate. Issue is we always do things where I’m the Dom. And she always goes on about my girly butt and legs. As we live in a very small city we go to a very large city a couple counties over and rent a hotel room in a very large city a couple nights every few months to have a night out where she can dress wild before going to the room for animal like sex. So she’s generally more open to experiment (tried 69 one of the times simply because neither of had done it before despite both of us constantly making 69 jokes… didn’t work so well for us lol) on those outtings. And if I have her a full rig along with what I want her to wear while pounding me on top of me telling her I “prepped” for months she’ll likely go for it. I’ll likely dress in drag too. She’s not one aware that I do it though she does know I did it with at least one other woman.
Issues I’m running into…
Knowing my wife she tends to get off seeing other people orgasm. So if she gets into it I’ll end up on my back with her pegging me missionary style so she can more easily jack me off while she’s going to town. Problem is I’ve found I have trouble ejaculating with the dildo in. Stuff comes out but not exactly a rush. Im guessing that I need to practice male kegels to get around that.
Tonights “training” involved me wearing a sports bra with some hokey fake boobs (though properly weighted and decently springy) the 6" dildo in my butt with my junk properly tucked in some tight panties with some vinyl boy shorts over under my clothes while I worked in the backyard. Kept that attire in place over 2.5 hours. Before I came inside I made a point to run around the backyard and do some jumping jacks… noticed with dildo in i developed a more womanly way of moving when I walked ran and jumped. Aside from when I sat funny it got to where I didn’t even notice it back there. So I think after a month about being serious about training my rear ill be ready. Do have more stuff to buy but that’s not an issue.
There was more stuff I was going to say but people kept coming up and distracting me by talking as slowly as possible so I forgot lol
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