The world can end now. I'm not going to be a dying a virgin in any capacity. As I mentioned in my last post, Mr Good-Company and I were exploring the idea of trying anal. We were slowly working our way towards it through the use of toys and fingering, so I could become accustomed to the feel and try and avoid any eventual pain.
On Thursday night, just two weeks after I had lost my virginity, that final frontier was crossed. I was over at Mr Good-Company's place again, we went into his bedroom and began to play. Everything started of as per usual, removal of clothes, making out and a little bit of biting, before we re-arranged ourselves into the 69 position with him on top of me.
At some point while Mr Good-Company was licking and fingering me I realised that he was starting to work his hand inside of me, without lube. It wasn't hurting me at all, but he certainly wasn't having too much success either. He asked me if I'd brought the lube. Of course I had, along with most of my toy collection since I really had no idea what he was thinking of doing with me that night. I am a believer in always be prepared.
Mr Good-Company came back with the lube and several toys. He knelt between my legs, poured a liberal amount of lube onto me and also onto his hand. He started to slide his hand inside of me and I, as was my usual gig, grabbed hold of his wrist. His hand seemed to slide inside of me much easier than our previous attempts. It didn't even hurt at all until he had his entire hand inside of me. I felt him begin to move his hand in and out of me slightly until the pain finally reached a point where I just had to say 'Stop'.
He withdrew his hand and began to play with my clit, before slowly working his way down to my anus. Mr Good-Company rubbed his finger over it for a little while before moving it inside. At the same time he slid a dildo inside of my pussy. He played with me in this manner for a while before he asked me if I wanted to try something else, if I wanted to try him. I nodded.
Mr Good-Company moved himself close to me and tried to slide himself inside of me. It hurt and once again I was tensing up, forgetting to relax. Once I finally relaxed and Mr Good-Company was inside of me, he slowly started to move. My first reaction was to place my feet on his shoulders, almost pushing him away. His moving inside of me just felt so very strange. It wasn't painful, just extremely unsettling. For a moment I had the feeling I get when I see too much blood. The feeling of all the blood rushing out of my head and that I'm about to pass out. After a moment however, I was able to regain control of myself and Mr Good-Company once again started to move.
I believe I had to stop, or at least ask Mr Good-Company to slow down on several more occasions. He obliged and then when it was okay again he would once again start thrusting. Mr Good-Company started to rub my clit as he began to thrust faster. This felt quite good. I wasn't attaining any pleasure from the sex as such, but the clit rubbing was of course quite nice. By the time Mr Good-Company was close to coming, the 'unsettling' feeling had disappeared and I was able to focus a bit more on what was happening.
All in all, it wasn't as terrifying of an experience as I had expected. I think my fear would probably have come from my repulsion in regards to faeces and also the fact that when Mr Good-Company did put the vibrator in me that first time, it was quite painful. I was expecting to be in quite a lot of pain the next day, as I had been the day after the vibrator, but there was no pain at all. Even the fisting didn't have any after effects in regards to pain.
At this point in time I would have to say that I prefer fisting to anal sex. Fisting gives me that endorphin rush, while at this stage I don't really get anything at all from anal sex other than an unsettled feeling in my stomach. I assume it's entirely possible that this may change over time and I imagine that I will definitely try it again at some point, but for now I'm happy with vaginal sex and fisting. They're both just so much more pleasurable than anal.