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Anal Sex….My First Time and then some! The Good, Bad and The Overwhelming. 

A few weeks ago I wrote a post on my tips for anal exploration before anal sex with fingers and toys. You can find that post HERE (don’t worry it will open in a separate tab 🙂 ) . It will tell you all about my interest in anal, what made me want to try it, my experience and tips. At that point I hadn’t had anal sex yet but as promised I said I’d come back and give you my thoughts and any tips I may have once I did. Since that post I did lose my anal virginity lol and have done it four times. All my anal experiences have been with my partner Wicked. I’ve had a different experience with each of those times and I’m happy that I’ve gotten to experience it in different ways so that I can give my full thoughts on it. I can give you the perspective of a real woman completely new to the world of anal. I hope it helps – Sadie ❤ 

There’s a first time for everything (My 1st Time)

Well nothing is better then Christmas…but it felt really good lol

My first experience with anal sex was not at all like I was expecting and it was quite unexpected. You would think that since I had anal sex before that I might’ve picked a special date and not have just randomly decided that tonight was to be the night that I wanted to try. Its important to say that he never asked me for anal, when I was ready I spoke to him about it. On the night it happened I was certain I was ready to move to the next level in my anal exploration but I wasn’t sure that I was ready for full on penetration. I remember being a little anxious and asking him when he thought I’d be ready for anal sex and telling him my thoughts on wanting more but not being sure on how much more. I wanted to try just the tip and see if that would work. He informed me that it doesn’t work that way lol it’s never just the tip. He started with just fingering which I enjoy there’s something about anal fingering that makes me orgasm pretty fast. He inserted his finger and that went in with ease which was different from when we had first started this process weeks before. I remember him looking at me and telling that I was ready and I responded with “are your sure?”. I trusted his judgement but I thought that I would’ve needed to graduate to the next size in my anal plug first or maybe play with bigger toys. I wasn’t sure that my little ass was ready for what he had to offer. It would be a big jump from my small butt plug to his penis. But by this point I had been playing with plug for months even before meeting him. Up until that night I had only had practice with my small anal plug and fingering. I was both nervous and excited. We sat on the bed and talked about the pace and how everything would be slow before we got started. He does a good job at easing my nerves.

We decided to try it in the missionary position because that’s what had felt the most comfortable for me in all of our previous play. I laid on my back and tried to relax to the best of my ability. He warmed up the lube with his hands and placed a generous amount on him and I . He handed me the Hitachi wand and I placed it on my clit which felt all sorts of wonderful. He aimed his penis in the right place and very very slowly started pushing it in. He instructed me to push down (I explain this in my first blog post on anal ) so I took a deep breath and pushed forward. I could feel pressure and a slight sting. I focused on my breathing…a lot of breathing in and out through the uncomfortable feelings. I was literally breathing out loud like how you would do at the doctors office when they put the stethoscope on your chest. There really was only two parts that felt uncomfortable but there was no crazy pain, no extra burning sensation and no excruciating feelings at all. Next thing you know it he said it was all the way in and I was shocked. I couldn’t believe it. I opened my eyes and saw it to be true. I was so overwhelmed with emotion and I smiled, laughed and said “oh my goodness I feel like I could cry” . And by the end of that sentence I actually started crying, tears and all. Obviously tears of joy, totally unexpected.

I was sooo happy that it worked, happy I made it through the uncomfortable parts and I couldn’t believe how easy it was. After a few tears and embarrassment over said crying I wiped my face and we continued on with slow strokes. It was odd because I enjoyed it when he would stroke back and forth but was totally uncomfortable when he’d just be still and not moving. When he wasn’t moving I felt extra full. I wanted him to continue moving during this process. I used the Hitachi while he stroked and I orgasmed rather fast while he was still inside of me. It was such a good experience, one I won’t ever forget….it was much better then losing my actual virginity many moons ago. It was intimate and special to me. I’m happy I waited all these years even with all the desire I had because he was the best choice.

Ohhhh Shit That Hurt……A Lot (My 2nd Time)

[I have to preface this next section with stating that this is a special situation and it happened during my most recent BDSM evaluation session with Sir. It was apart of a D/s dynamic and wouldn’t be typical in a romantic relationship. Since I’m apart of a dual relationship this was during the D/s time and not our peer to peer romantic relationship like during times one, three and four. I understand that this would be a bit confusing for those who don’t understand but since it’s about my personal anal experiences it needs to be left in the sequence. For first time readers Wicked and Sir are the same person. ]

My second experience with anal was with Sir. I recently posted the first part about that session HERE. I couldn’t cum when Sir asked after he waited patiently for some time. The price for not cumming when he asked was that he’d fuck my ass. And boy was I worried because I just recently lost my anal virginity and only had anal sex once. It was not what I had expected and I was convinced that all the people who said it burned and it hurt were wrong….but I learned that day. I remember telling Wicked that I was surprised that my first time experience was so good and I didn’t experience the discomfort that I’ve always read about. He told me at that time that the people were telling the truth and it feels that way if it’s done wrong or if the intent was for it to hurt because he could make it hurt if that was what he was going for . Well…..when he leaned into to my ass as a consequence for not getting what he requested I felt what all the people were talking about. Because unlike in my first experience where he worked it in, massaged it and where he took his time to ensure that it was good…that did not happen. He put on some lube and just penetrated me. There was no warm up or extra preparation .

I was laid back arms chained to each other , legs chained as well and with his first stroke into my ass my eyes popped open and I saw the sun moon and stars. My little ass was on fire and if I could’ve ran I would’ve . He intended for it to hurt and by golly it sure did. It took me a while to say that it hurt because my bodies first reaction was to try and get away from that awful feeling. The pain surged through my body in such a way. It burned and I felt stretched with every thrust. I was on a couch at the time and by about the fourth stroke half my body was off the couch and my head was on the floor. The natural instinct was to run far away from that feeling. I’m sure if my body could have detached itself from my head it would have ran off. I learned in that moment that if he wanted it to hurt that it will. And all I could think was if this was my first experience I would never want to try it again in my life .

After that I was very unsure on if I wanted to try again. I was scared that every time after that it might feel bad because unlike in my first experience my bum hurt for at least a week after that . And when I went to the bathroom after that experience, it also hurt which up until that point I didn’t have that issue. Ultimately after that I decided I needed to jump back on the saddle because I understood that it was situational . I knew it was done with the intention for it to hurt and I learned the lesson that he needed me to. I knew that the my whole point for wanting to try anal to begin with was because I wanted to see if it could be like the books. I wanted to see if all the talk about great orgasms was true. It helped that I had a good initial experience with it so I decided to try again.

It was worth the try (My 3rd Time)

This meme sums up my third time precisely , it wasn’t all painful

After my second experience I was most certainly leery but I also was on a mission to try it again so I wouldn’t be scared away. I knew the next time we would have sex that I’d ask him for anal. I was scared but I really wanted to rid myself of that feeling so I figured taking it head on would be the best choice. The next time we had sex after my session with Sir in our romantic relationship was four days later. My ass was still a bit sore but not as bad as the previous days. I could still feel some soreness when I sat but I was on a mission. I just needed to feel it again so my last memory wouldn’t be the worse . We tried again, this time in our peer to peer romantic relationship so it was done with ease and extra patience. When he slowly penetrated this time, it hurt but not nearly as much as my second time. It was uncomfortable and I could feel the stinging sensation but it was also starting to feel better . We did that for only a little bit and that was what I needed at the moment. It hurt bc I still had residual pain but it was much better and I could see that it would be worth trying again. He told me that it usually takes at least a week for all the micro tears to heal and he was right . We talked about trying it again similar to my first time after everything healed nicely. After about a week I could sit and not feel my sore asshole. 

Sensory Overload…What the heck was that? (My 4th Time)

I recently had my fourth experience and overall all it was really really good. I had made sure to express my interest in trying again. It was important for me to continue to be persistent in showing my desire because I wanted to make sure I didn’t let my second experience completely scare me away. I knew that it could feel good based off of my first experience and I also knew that I didn’t want to quit. I’m happy I didn’t because my fourth experience was the best yet in ways that I can’t fully describe. I was so overwhelmed by the sensation. This time we began the same way from the first time with a good amount of lube on the both us and going really slowly. I used my vibrating friend and after a few strokes it was in and feeling good. I’ll admit I was scared initially but so happy when it went in with ease and I didn’t feel any pain. We started in missionary again because that’s the way I’ve been most comfortable and have the best feeling from. It was good and I was able to cum while he was inside of me using the vibrator. I tend to come faster from anal for some reason. This time it took a bit longer because I knew I’d squirt…I’ll explain that a little later in this post. There were a few different things about this experience that didn’t happen in the first few. For starters this was the first time that the anal sex portion lasted so long and it could’ve gone longer if I wasn’t so overwhelmed.

Prior to this time there hadn’t been much practice in the doggy style position because missionary had been what I was most comfortable with. There also was more depth this time. In the previous experiences his penis had been all the way in but there’s a difference between the length being fully in and it being pushed in deeply with every thrust. I wasn’t on all fours, it was more face down ass up for as long I could keep it that way because of the intense feeling. By the end of it I think I was in a bit of a ball on my knees. When I say I was overwhelmed it was a good thing because I was experiencing a sensation and feelings that I never had before. And I wasn’t sure how to deal with that. I’ve recently found that I squirt sometimes when I orgasm and by recently I mean this year. I would say sorry TMI but you’re reading a blog about me having sex so we’re already cool and you know what you’ve gotten yourself into lol. I don’t exactly know what triggers it so I don’t have much control of it. My not having control of it makes me very nervous sometimes and even a bit scared to orgasm when I can feel it coming on because there’s a very intense feeling that I get before it happens. During anal in that position It got to a point where it felt like with every deep stroke he made that I could cum.

Now I’ve never orgasmed on my own from just penetrative sex which seems to be common among women. It was super intense to feel that almost orgasmic feeling from penetration alone without any clitoral stimulation. And it was even more intense because it felt like I’d squirt and that feeling makes me nervous . On top of that with almost every stroke it felt like he pressed up against something that made me shiver which made my voice quiver a bit. I’m sure I sounded like I was in a combination of total bliss and like I was going to die from sensory overload . By the end of it I was asking him to cum because it was a lot for my mind and body but in a good way. I was just too overwhelmed and he sensed something was up. We talked about it afterwards because in the moment I just couldn’t explain what I was feeling and I’m not sure I’m doing a good job of explaining it now. It’s something I’d like to experience again in exactly in the same position at the same angle but in smaller doses. I feel like now I could be better prepared for the overload of sensations. 

My Current Overall Thoughts

I can attest to the fact that if done right you can have a very good experience with anal. I’ve had different experiences each time so I can tell you that it’s worth a try. Your first time does not have to be a complete horrible shit show. It doesn’t have to burn and you feel every tear because you’re being stretched when you’re not ready. It can feel amazing. But if done speedily with no preparation it could be awfully painful. If done with the intent to hurt it will hurt. Now I’ll never be excited about the sensation of painals and I don’t look forward to anymore painful anal. The thought of it right now makes me squirm. But I can also tell you that those hurts heal and it can go back to feeling good. I’m excited to explore it more and to see exactly how orgasmic it could be. My fourth experience was an eye opener. I started this wondering if it could be like the books says a good addition to my sex life, full of great orgasms because of the number of nerves involved etc. I think the books just might be right. I’ll continue to share as I journey through the wonderful wonderful world of anal sex . 

My Tips

  1. Make sure it’s something you want to do and it’s not something that you feel pressured into. I think my genuine interest in it even before meeting my current partner was helpful. I feel like it helped me work through the slight pain I felt initially during the first time. I was interested in the end result so I feel my desire helped me push through 
  2. Use a vibrator on your clit to help distract you. The sensation of something that feels good is very helpful. 
  3. Breath – I found that breathing when it hurt a bit helped. I focused on the good feeling sensation from my vibrator and breathed. And I’m not talking about your normally daily breathing. I know you’ll die if you don’t breath. I’m talking about focused breathing. Taking a deep breath in and breathing out slowly through your mouth and focusing solely on that. I have no clue what I looked like during this process but I’m sure it was crazy. Breathing helps. 
  4. Make sure you do it with someone who you trust and is patient. It’s one of the most important tips. I felt more at ease because I trusted that he wouldn’t jam it in, that he wouldn’t hurt me intentionally and wouldn’t get lost in the good feelings and let that take over . 
  5. I’d suggest trying a butt plug and fingering first before jumping in head first . 
  6. Don’t be crazy……use lube and a lot of it!
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