Sir and I had discussed the idea of anal before as it was something that he was very interested in. I had never had anything in my ass although I had always been curious. He had discussed in detail how he would work up to it with different toys and fingering. I liked the idea of that. That is not how the story goes though….
We discussed a timeline of when I would be ready and we could start incorporating a bit of anal play in and I knew it would be soon. Sir sent me a text and told me to be ready for it when I came over for the night. I texted back letting him know how excited I was and how the anticipation had me very aroused. Sir requested that I did not play with my pussy and that I saved my excitement for him.
I wasn’t sure what to expect so I took a little extra time in the shower and made sure I was extra clean. While in the shower I couldn’t help but think about what was in store for me. My clit had been throbbing since sir sent me that text. While washing my body I grazed my clit and I got an urge and needed to release. I knew sir asked me not to but if tonight was going to be focused on my ass I didn’t see the harm. I rubbed my clit fast and hard and it didn’t take me long at all before I was cumming. It felt so good and I was able to focus for the next few hours until going to see sir.
That night I arrived at his place and he had an unusual excitement to him. He is usually so calm and collected. I could tell he had been looking forward to tonight. We discussed the usual pleasantries about each other’s days before heading to the bedroom.
Sir asked me to undress for him as he sat at the foot of the bed. I went extra slow today as I know how much he enjoys this part. Sir then asked me to lay on my stomach on the bed and when I did he grabbed his ties and placed one around each wrist and each ankle. Sir then started with some light flogging since he knows that gets me going. Suddenly he stopped and rubbed my clit. He told me something felt off and that he had expected me to be instantly dripping since I knew what was in store. He then asked if I had followed his orders of not touching my pussy today. I instantly got a pit in my stomach. How did he know? I hesitated before answering but told him that I had played just for a few minutes because I was so excited and that I had only touched my clit. I could tell that I had let him down and that he wasn’t nearly as excited as when I entered for the evening.
Sir then left the room. Left me naked and tied to the bed. I am not sure how long he was gone but it felt like an eternity. When he returned the entire mood was different. He explained to me that since I had disobeyed he was going to use the cane (which he knows is my least favorite) and that I was going to count them out loud to ten. This first one came down on my ass and startled me even though I knew it was coming. One. The next one was a bit harder and the sting seemed to linger. Two. The next two came very fast. Three. Four. The fifth one came harder than the others. Five. I was really regretting playing with my clit at this point. Six. Seven. My ass was on fire. Eight. I wasn’t sure if I could take another. Nine. The last one came and I screamed. Ten. He came and grabbed me face gently and said “good girl”.
I had taken my punishment and thought we could now get back to it. I was once again excited to start my anal training. At this point sir was still fully clothed which was typical. He usually stayed clothed until he wanted me to suck him or he was ready to enter me. He walked around the bed to where I couldn’t see him and I heard him unzip his pants and take his clothes off.
He drizzled some lube on my asshole and moved his finger in and out. I was a little unsure of this since I hadn’t had anything in my virgin ass before and the way he described training my ass was a bit different from this. Sir placed a vibrator under my clit and told me I could have it on my clit to help ease the pain and that I could keep it as long as I as I was good while he was entering my ass. Wait… what? What happens to the anal play? No warm up? I objected telling him that I wasn’t ready and questioned working up to that. He told me that because I hadn’t followed the rules he was going to take my ass how he saw fit. I couldn’t believe this was happening. I had a mix of fear and yet still trusted him. I had wanted this but wanted it differently.
I tried to relax because in all of our talks prior he told me that was a must. I tried to focus on my breathing but couldn’t help but be nervous. I felt him now on top of me. He placed the tip of his cock right on my asshole and circled it in the lube. He told me to take a deep breath and I complied. As I exhaled I felt the head push into me. It felt as though my ass was going to break. Instantly everything felt warm and I got a bit dizzy. I cried out telling him that it hurt. He told me he knew it did but it was just the tip and that it would be better in a minute. I tried to relax my body. My poor asshole felt so violated by being stretched my his cock. He had only pushed the tip in and then just waited, not moving. Once the pain started to lessen I happened to notice that my pussy was incredibly wet.
Sir slowly started thrusting his cock into my ass going just a bit deeper each time. It hurt. I couldn’t believe how much it hurt and I couldn’t believe it wasn’t going to rip me open. Yet at the same time with each slow thrust there was a bit of pleasure too. Sir paused for a second to tell me that it was all the way in and that he was proud of me. All of me felt better at that moment. My ass relaxed and embraced his thick cock. He kept thrusting eventually picking up speed. The discomfort started to fade and was replaced by pure pleasure. I couldn’t believe I was doing it. I had taken sirs thick cock in my ass and was loving it.
I could tell sir was enjoying himself as he was a bit more vocal in his pleasure than usual. He bent down and whispered into my ear that he was going to fill my ass with his cum. I was so excited. I felt his cock throb and his warm cum fill my ass. After, he slowly pulled his cock out of my ass.
He then untied me and flipped me over. He ate my pussy like never before and I came right away. After laying for a moment in bliss he told me to go clean up.
Not how I imagined it but was still just as great.
Source: reddit.com/r/Erotica/comments/dsiax0/my_first_anal_experience