Need advice... Anus play

[UnicornBatman]

So, I've been with my boyfriend almost a year. He mentioned to me some time ago that he was into something that he was really embarrassed about that his ex made fun of him for and used against him. She was the only person he ever told. He wasn't ready at the time to share with me. Fast forward, some things happened and he finally opened up to me. When he masturbates, he likes to put objects in his ass. I don't see anything wrong with that. It actually turns me on. One of my biggest fantasies is pegging. Things are getting spicy. He's not ready to include me yet, as it's a new thing for him to be able to share and engage openly about it. I found one of his toys the other night. He left it out. It was homemade and very large. I was impressed by the size but a little concerned with the quality. i thought maybe he's had to use homemade toys because he's too ashamed to buy the real thing. I'm very laid back and sex positive so as we've been talking more about it, he admits that he likes to use strange objects because there is an element of pain. Sometimes he feels like he has to go bigger and bigger in order to get pleasure from it.

I'm on board with most of this, and I'm grateful that he has realized that he can trust me and be more open. My biggest concern is the dangers that could be involved. And I expressed that the best way that I could, because the last thing I want is for him to feel like I am judging.

He wasn't upset by my concerns and even admitted that he has the same concerns.

I guess the question I am asking is, how do I remain positive and open minded with him while also keeping his safety in mind?

There's also an element of him being sexually attracted to himself. He said he likes "taboo" undergarments" and likes taking pictures of himself to masturbate to but he's not willing to share that with me yet. I don't want to be pushy. I just want him to know that I am a safe space, and my imagination has been going wild with all of this. Fantasizing about all the things we could do. I've never been in a relationship where I could explore my own kinks.

Oh, and with the legging, he is concerned about the power dynamic. Is there a way/positions that I could peg him and that would be minimized?

Sorry for the layout of this post. I'm trying to get all of my thoughts out.

Thanks in advance.

 

[subzzzero]

First things first. Yes to him and you both on get real toys. You’re adults. There are plenty of ways to get sex toys without going into a shop. An online store delivering them in a plain brown box. Even your delivery person won’t know what it is. The risk in anal play is sharp edges or seams for plastic molds. Also just quality of some material you don’t want parts breaking off inside and getting lost.


With the dressing up part. If you’re saying he’s worried you won’t see him as dominant because he dresses. That’s entirely up to you. If you don’t see it as an issue then do your best to tell/show him. Or maybe the cross dressing is done outside of your power play sessions then it won’t matter. The other possibility is with him into anal and pegging and cross dress it is possible he’s a switch. Which might be another talk you both can have. You do have an uphill road given his ex was negative about it all. Just keep with the open talks, support, and positive reinforcement he will gain comfort and more trust to share more with you in time. He’s basically put up walls from the ex and it takes time to bring them down. He’s clearly working on it as you’ve seen progress. I think you’re doing great so far.

Edit. You wrote legging I thought you meant clothes. Sorry I see peg in the second part of the sentence.
Positions and power is all mental. Him on all fours might seem sub to him. He could ride you while you’re on your back or you could peg him while he’s on his back with you both face to face put a pillow under his waist to hike his ass up to reach easier. I used this method on my sub and she likes it being face to face.