Anal Sex Update - ok, this one is done too! 
Sorry in advance, this is a long one! I know lots of people on here have anal sex regularly, so I feel like it isn’t that big of a deal that I finally did it, but just thought I’d share my experience, especially for those who have also had bad experiences that put them off anal! 
So, the biggest obstacle for this one wasn’t just getting stretched out enough to take a cock, but mentally overcoming the fear of pain that kept me from being relaxed enough to enjoy anal play.
From the start, I preferred letting my husband do the work with his fingers and toys behind me while I leaned forward on my knees or between my legs while on my back, but that was only during foreplay before we’d have piv sex, so it was only once a week, sometimes twice, and when solo, I’d finger myself (one finger in a finger cot). Several weeks ago, my nails grew out too long to comfortably finger my own ass without feeling like I was going to slice it open 
so I started using toys when solo, but I couldn’t relax because I felt like I really had to contort myself to reach my ass, and I ended up hurting myself a little, it felt like I gave myself a silicone burn 
I know I’m supposed to use a ton of lube, and I felt like I did, but my ass was like a squeegee just wiping the lube off the toy while I’d be pushing it in and while pulling it out… It was really uncomfortable, so I got a little discouraged. I went on a little LH hunt looking for a new plug because the ones I had weren’t working for me. Because I was feeling like I couldn’t really do anal play solo, I asked my husband if he would just finger me a little every day, even if he wasn’t in the mood, just to give me a bit of a stretch 
I showed him my posts on this thread because he was starting to wonder why I had gotten so obsessed with my ass 
He was really surprised! After that, sometimes I’d forget, and he’d grin and ask me, Wanna do some butt training? or just, Can I play with your butt? 
I got to where I could take two of his fingers pretty comfortably during foreplay without feeling any fear or nervousness when they would penetrate.
anal sex not to completion - Last week, he had two fingers in while I was on my back using my womanizer on my clit. I was feeling good and wanted to try something a little bigger and firmer, so I asked him to try putting in my glass dildo since it has a pretty narrow girth (3.5”). Since it doesn’t have a flared base, he held one end securely (with a non-lubed hand ) and only let it penetrate about a third of its length. It felt quite good. I didn’t feel any pain from friction, and the stretch was comfortable. The nubs on the dildo felt good bumping and rubbing me as they were twisted and were slowly going in and out. After I had a nice orgasm, I thought, That didn’t hurt, and I’m relaxed, I bet I could take him 
He lubed up his cock, thrilled to not wear a condom, and pressed in slowly about halfway and did some slow thrusts. I couldn’t believe that it didn’t hurt, but there was more of a stretching sensation than before, so I started tensing up and got scared it would hurt so he pulled out and finished with his hand while the other hand had fingers back in my butt. The next day, my new butt plug arrived in the mail 
so I spent a few days doing solo anal play with it!
anal sex to completion - This past weekend, we were ready to try again 
I wore my plug for about an hour while I was working on a review while he was finishing up work, then when he was ready, I laid on my back and let him play with the plug a bit - pulling it out and pushing it in, holding it right before it pops out and pushing it back in, twisting it and rubbing it against the walls inside. Because I had been wearing the plug, two fingers slid in easily, so he lubed up a third finger to really stretch me out. It didn’t hurt, but the stretch two knuckles deep was a little uncomfortable, so he pulled them out a little and twisted them more slowly, and I was fine He wanted to try to penetrate in doggy, so I got on my knees while he lubed up his cock. I tried to get in a good position to hold my clit vibe in place because I wanted to be able to have an orgasm while he was in my ass (the times we did anal in the past, he came and I just laid there until he was done). I swear, it was the longest penetrative session we’ve ever had because usually piv, I like it hard and fast. He was moving really slowly because he was worried about hurting me (afterward, he said he was trying so hard not to cum ). It felt so sensual. He kept kissing my back and neck, which he never does 
The stretching didn’t hurt at all, and he was able to get in pretty deep, but because he was still moving slowly, it didn’t hurt. I was trying to just focus on his movements and on the sensation on my clit. I was right on the edge for a while and I kept thinking, I’m almost there, I hope he doesn’t cum, and I finally tipped over the edge and climaxed 
and I know he was so relieved that he could finally blow his load 
We had so much sex in the couple weeks leading up to this… (pro tip: ask your husband to finger your ass once daily without planning on sex to follow, and he will get horny and want to have sex more just kidding, but really…) He said he would’ve cum in 10 seconds if we hadn’t been so sexually active the past few weeks. Anyways, anal play is here to stay! There will be lots of plug wearing and fingering in my future. We probably won’t have anal sex super often, but probably whenever he wants it, he’ll get it (with plenty of prep of course) 
