Want to support CHYOA?
Disable your Ad Blocker! Thanks :)

Chapter 2 by storywriter2018 storywriter2018

First Night

First Night of being "positive"

I knew this was going to happen. We don't do anal often but he brings it up regularly so I already expected this to be one of his first things. After we had a great dinner and some drinks to celebrate, we went to bed. I took a shower and cleaned myself extra well, knowing what would likely happen.

As soon as I stepped out of the shower, he was waiting for me. He kissed deeply and then took my hand and walked me to the bed. He guided me onto the bed and without any hesitation, rolled me to my stomach. He started massaging my back with coconut oil. He slowly moved down to my butt and legs. And soon after had my legs spread and was teasing my pussy. I was so wet and horny at this point already.

Then he started licking and playing with my asshole. It felt so good I just wanted to let him do that forever. He was sticking his tongue into my asshole and beginning to "soften" me up for what was coming next. After a few more minutes, he turned me to my side and laid next to me in a side 69 position. He said I would want to get his cock as wet as I could so I started sloppily sucking and licking his cock from the head to the balls. He was already fully hard at about 7 inches long and girthy. It was always the girth that made me nervous.

Meanwhile, he was fingering and licking my asshole to stretch me out. Soon after, he got up and said "I want to see your face when I put this is your ass" and turned my onto my back.

He got some more coconut oil and rubbed it into my asshole. I was smiling at him and blew him a kiss. He leaned over, kissed me, and whispered 'I love you' before going back to his position between my legs. He put his cock right on my asshole and slowly started pushing in. It hurt right away and tried not to show it too much but instead kept smiling.

But as soon as the whole head popped in, I could help but to moan. He loved to hear me moan. He stopped right there and leaned in to kiss me again. But that made it hurt a bit more and I moaned again. And then I said "You love my asshole, don't you?"

With that he pushed further in. I felt like I was completely stretched and let out an even longer and louder moan. That was his final queue as he started slowly going in and out, warming me up. I was trying to not think about the pain but focus on the pleasure I was giving him. A few times, he would pull all the way out and go back in. I think he did it just to watch and listen to my reaction. It didn't take him long to announce he was cumming and I could feel his cock stretching my ass as it pulsated several times before he collapsed onto my body.

Then he told me not to move but he went into the bathroom. He came back with a wet towel and wiped off my asshole and his cock. Then he put his cock back into my mouth. I had never sucked his cock after sex without a good cleaning, not just a wiping, and for sure never after anal. But I told him "anything" so I started sucking it. Luckily for me, I couldn't taste anything weird so I was happy oblige. Plus, my ass was still sore as it shrunk back to normal.

Within a minute or so he was already hard again. I complimented him for that but I really knew it was because he was very very horny. He told me I was a "good girl" and that it was time for my pleasure. I thought he was going to lick my pussy but instead he flipped me back to my stomach and pushed his cock into my pussy in the prone position. He loved this position but he knew it hurts me a bit because he goes in so far.

He pushed in and my pussy accepted him easily. I was so wet. He grabbed my hands and put them to my sides and trapped them in between my legs and his legs. He then spread my ass and put his fingers into my asshole stretching me out again. I was now thinking I was going to get another round of anal soon. But in the meantime, I was just enjoying the fucking he was giving my pussy as I needed to have him in me. After a minute or so, he let my ass go and wrapped his hands around my neck and face.

He leaned over me and moved my head to side and started whispering in my ear that he was in love with his slut wife and was looking forward to the rest of the pregnancy. He also told me to "get used to this" because we'd be having sex every day. This went on for several minutes and I just laid there and kept saying "yes" and moaning in pleasure. Then he said he wasn't going to let me cum today. He wanted me to wait. With that, he pulled out of my pussy and plunged his cock back into my sore asshole. I yelled and grunted but was being completely held down and had to take it.

He pushed in and came, again, draining more cum into my asshole. I was hurting but also so turned on by his actions and the way he just owned me. He pulled out and put his cock in front of my face and said "clean it". I looked up at him and shook my head. He gave me that "you promised" look. I grudgingly took his cock into my mouth and twirled my tongue around it for a minute. It wasn't so bad and I felt proud that I had kept my promise.

When he was done, he kissed me deeply again and told me how much he loved me, how sexy I was, and that he had so much fun doing this. He thanked me for a great time and told me that he just had to get that one out of his system and that anal would not be something he would do too often. Then he reminded me that I was not to cum until he told me so -- which would happen soo.

I was satisfied either way and totally happy to be his slut. What I didn't fully realize is that this was really just a warmup. He had much bigger and kinkier plans for me over the next few months.

Next weekend?

Want to support CHYOA?
Disable your Ad Blocker! Thanks :)