I opened the jar of petroleum jelly and Divi watched as I pulled out a glob with my index and middle fingers. I placed the glob on her anus and smeared it around her rosebud. Then I explained that I would push my index finger inside her anus to push the jelly in. She groaned hard when I did that. I explained that she needed to consciously relax her sphincter muscle like when she was trying to pass a poop. She giggled at the crudeness of my explanation but I immediately felt her anus relax a little. I didn’t move my finger in and out of her like I was fucking her with it. I just slowly pushed it in so she could adapt to it. I could feel her relaxing. I left it there for a couple minutes and then pulled it out slowly. I moved forward and pushed my hard cock between her thighs. She rocked her hips forward to present her anus but I pulled her hips back. She was confused by this move and I explained that I was going to put my cock in her pussy to coat it with her lubrication. She was all in on that as she pushed herself back hard on my cock and groaned as I penetrated deep into her vagina. I was conscious of her cervix, even if she wasn’t, and stopped short of causing her any pain.
I gently pushed my thumb inside her anus and she flinched and pulled away from me. I held my thumb inside and with my free hand I gripped her hip and fucked her pussy for several strokes and then stopped. As I expected, she didn’t want to stop and she whimpered, “Oh fuck Jack. Don’t stop. That’s amazing.” I started to pull my cock out but she followed it back to keep it embedded. She had forgotten about the thumb in her ass.
I said,” Divi, honey. If you want to abandon the butt-fucking thing, I’m okay with that but if you want to continue, it’s awful hard to fuck your ass from inside your pussy.” She burst out laughing and pulled herself forward and off my cock. I followed her forward with my thumb keeping the same depth. She groaned hard when I eased my thumb from her ass. I looked down and saw that her anus was gaped open to the size of my thumb. I spread more petroleum jelly on my glans and up my shaft and then told her that I was going to put my glans on her anus and that she was to hold her position by pushing back as I pushed forward. I guided my cock to her anus and the moment that my cock touched her she went rigid.
I whispered, “Relax Divi. Relax your anus like you did on my finger. She was already breathing erratically. I had my doubts that she was going to be able to do this. I pressed forward harder and pulled her hips to me. She groaned and then let out a yelp. She was wagging her head from side to side as she started a constant moan. I told her to relax again but I didn’t feel anything from her. I eased my grip on her hips and pulled back.
She pushed back on me and said, “Don’t give up on me yet. It hurts. I knew it would hurt. Just do it like you did when you took Molly’s cherry.”
I groaned with that analogy and said, “Divi, sweetheart. It’s not the same thing. If I force it, I could do damage.”