How to...🍑

UPDATE #2:

SUCCESS! Thank you ladies for all of your advice, I'm very open about my sexuality but for some reason anal has been difficult for me to talk about. Last night I was riding him, and we decided we wanted to try again. I put lube on my ass and he fingered it as a normally rode him. It felt great and made me feel less nervous about actually doing anal.

We switched positions and I laid on my side and rubbed more lube on myself and him. He slowly was putting it in and although it hurt still, I was more comfortable and confident about it. After the discomfort passed it was actually really enjoyable! My boyfriend put my leg up and played with my clit as we were still doing it and it felt great. However, I did make him stop because I felt the urge to use the bathroom😳😳😳 so I went and it was a very uhh, farty moment and I didn't even end up using the bathroom🤦🏼‍♀️😂 but thank you everyone for your advice and experiences ❤️

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UPDATE:

So I brought up toys to him and he says he doesn't really want to do toys he'd rather try to get me used to it with his fingers. But his dick is a lot wider than his finger so I'm unsure how it'll work 🤔 I bought new lube that should work better than the one we have. We'll try his finger, and work from there I guess

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My boyfriend and I are very much into rough sex. I love being called names (slut, whore, etc), he loves being called daddy. We scratch, bite, choke. We have restraints, collars, ball gags.

However, we are trying to do anal and are having troubles...

Little backstory-

So over a year ago we tried anal and it did NOT work. He barely got the head in and I shot forward in pain. We used condoms and lube to make it easier and it didn't help.

In March I was sexually assaulted by someone else. (My bf and I broke up for a few months) I blacked out at a party and fell asleep and this guy brought me into a room. I woke up the next morning and he said he brought me there to sleep. However, throughout the next day my asshole was bleeding and was in a lot of pain. It was hard for me to walk and sit and use the bathroom so I went to the ER. I told the guy I went to the er and why and he said the night before while I was laying in bed he asked if he could fuck me anally and I supposedly said yes. I don't remember any of this at all and i had said before many times to many people anal isn't my thing and I didn't want to try it for a long time (im very open about my sexuality to my close friends and partners and he was a good friend at the time) so I told the dr at the emergency room what I found out and they did a rape kit and I had tears on my anus, multiple hemorrhoids, and bruising all around my anal and vaginal area. (I reported it and he is now facing either a signature bond and/or prison time because turns out he's done this to many others)

I've been back with my boyfriend for a while now and I finally feel comfortable trying anal again. I was scared for so long because of the pain afterwards from being raped but I know my boyfriend will be as gentle as I ask and we have plenty of lube.

Last night we tried and he got a third of the way in and I got a burning feeling so I told him to stop and the feeling lasted for a few hours after.

My question is- how can we make it easier? He says he got a third way in and it felt nice for him and I'd really like to find out if this is something I like. I'm really curious about it. Is there a way to ease into it? A way to not have the burning feeling? The length of my bf won't be a problem (he's on the larger side, 10.5inches) but it's the width that i think hurts me. What can we do????