I don't know what it is about me but blokes have never been as shy as they perhaps should have been to ask me to do weird things.
I mean blokes always ask the usual stuff, like threesomes, anal sex, to let them take dirty pictures. Those I've been quite happy to say no to, because they can have adverse affects on me (though saying that I have done them at various times so maybe I'm just easy)
Anywho other stuff I didn't have a problem with like guys wanting to wear my undies (so long as they buy me new stuff) or for me to dress up or talk dirty or role-play whatever, stuff like that typically didn't take a lot of effort on my part and was a big deal to them. It didn't affect my opinion of them if they did want to say wear my knickers for a day, and I think they generally appreciated it.
I was always pretty lucky with my bf's even the weirdo's were decent enough guys and we typically ended on good terms. I think I was pretty good at spotting the type of guy that would ask you to do stuff and then think you were a slut for agreeing.
Anywho two guys I've been with have asked me to shag them up the bum.
The first time was with a bloke who asked me If I'd take it up the bum. I said no and asked him how he'd feel taking a cock up his arse. (this was what he was hoping for I discovered) he said okay go ahead.
I told him that it wouldn't make any difference to me agreeing to take it anally, but I could tell he was keen (he wasn't actually that interested in giving just receiving)
So I used my regular vibrator (plus a condom) on him, I could tell straight away that he'd done it before because I got it in on my first go, which I could never do.
So I'm banging away at him, I'm getting rougher and rougher cause I'm getting kind of into the power trip. I didn't actually realize that it would give him a hard on or cause him to orgasm (you learn something new every day). In retrospect I was way too rough with him, I was treating it as a bit of fun but I could have injured him. He was just lying there taking it and not telling me what to do – whether I was being too rough or what, I think the whole macho uncomplaining thing might have been dangerous. If it had been me I would have verbally telling the guy what to do and checking that he didn't lose the run of himself and injure me.
After we finished he was just like me after the he wanted a little cuddle which was strange to me cause he wasn't usually like that.
I think I went a bit far with the power aspect though, Even though I didn't make a big thing out of it so as not to humiliate him, I did want to explore it more. Not really in a sexual way (in fact I was getting less sex) but I just found it exciting. I wanted to buy a strap on which he wouldn't go for. One day I kind of surprised him in the kitchen got him to bend over the table he went along with it but I think he kind of had second thoughts afterwards.... I was getting a bit too aggressive. He started to get a lot more aggressive with me as well when we'd shag normally, I didn't mind it and I thought it was good for him to assert himself, but in retrospect I think he wasn't enjoying fucking me as much as he was before. He was being aggressive not out of choice but as kind of a way of protecting his dignity.
We split up shortly afterwards though on good terms, I think he appreciated that he could trust me enough to know that what happened in the bedroom stayed in the bedroom.
I realized that other guys might like it, years later I offered to do it with another bf.
That went a lot differently because he hadn't had anal sex before and it was a bit of a struggle and not that sexy, he orgasmd from it but to be honest as like before it didn't do that much for the sex generally. So after him I never offered to do it again.
