[UPDATE] My first time trying anal with my boyfriend + text from my deleted post
Note: I accidentally deleted my original post a moment ago, so I’m reposting the original context below first, followed by the update!
I recently started dating my boyfriend, but we’ve both had feelings for each other long before making it official. Up until a couple of days ago, we hadn’t done anything sexual just kissing, holding hands, and innocent stuff like that.
Two days ago, he invited me over to a jacuzzi. We both felt ready to take the next step and have sex. I leaned more toward being a bottom, but since I wasn’t entirely sure, he suggested we switch positions so I could figure out what I actually enjoy more. He is actually a top, but he was open to switching just for my sake.
I tried topping first, but I didn’t really feel it. So, we switched, and I bottomed.
Honestly, it was terrible. It hurt like hell. Even though he took his time to prepare me and we used plenty of lube, the pain was so intense that I literally started crying.
I feel so embarrassed. He was incredibly sweet about it he comforted me and said it was totally fine, and that my comfort is what matters most, even if we don't do anything. But I can't help but overthink it. Like, okay, he's fine with it now, but for how long? Especially since he is a top. I don’t want this to be a permanent issue, but I genuinely don’t know what to do next or how to make it better.
For context, I’m bi and this is my first gay relationship, so I’m still figuring things out. Has anyone else gone through this their first time? Any advice would be highly appreciated.
Update: So I followed your advice, guys! I’ve been practicing with toys on my own, and today my boyfriend and I tried again. This time we used the spooning position, and it went so much better it was way less painful! It still hurt a little bit, but in a beautiful way.
Thank you all so much for the amazing tips, it really made a huge difference!