NOT Your Grandma's Book of Progressive Erotica: Vol 1

Once

Fingering one's own asshole was not a topic that came up very often in my circle of friends – in a group of men I never questioned it as it may have come off as being a bit queer. However, this didn't deter me from talking about it with the girl I was dating and also wanting to experiment by myself.

The relationship was the first I had ever had where sexual desires were spoken openly about. She was younger than myself and somehow much more experienced. I was an open-minded person – or so I classified myself as such – but when it came to being a freak in the sheets, I relied mainly on my love for going down on a woman and my stamina for fucking her for a rather long time.

I prided myself on being selfless, giving my full attention to my partner and never really yearned for anything more than having my one orgasm per session.

There comes a time in everyone's life when their partner is unavailable for an extended period of time and I just so happened to be in one of those droughts. I had been so used to fucking once during the work week and then an unlimited time on weekends, which sometimes meant more than three times a day.

She was studying for exams and said that focusing on them would be the best thing for her. She also admitted that a good fuck would let some of the stress pass, but she knew it wouldn't be just five minutes of fun. We loved being in each other's company, so a quick booty call never happened. I would visit her for a few hours at least, which would usually entail us fucking twice – once when I got there and once before I left – and also involved eating, getting high and watching Netflix. It was quite the strict routine that we had in place, so it was hard to deviate from it.

Weekends were full of sex, walks, hikes, playing pool, camping and other various activities that were simple and cheap. We both enjoyed the outdoors and we also loved going for our weekly Sunday breakfast where we could just get away from all the distractions by visiting a small, local restaurant.

Laying there in my bed one night, unable to fall asleep, I got curious about pleasuring myself without her. I turned on the television and put one of my favourite movies on for some light noise and then grabbed the bottle of cherry lube she had left in my sock drawer from our previous encounters.

In all honesty, I wasn't sure what I was doing, or expecting to happen when I got back into bed with the bottle of lube. I pulled the sheets back so that my dick was out in the open and then squeezed some lube onto it. The advantage of sleeping naked was something that I had grown accustomed to with her since we were constantly aroused and fucking like rabbits. Laying in the dark as the movie played on my large screen television, I slowly stroked myself and imagined I was fucking her pussy. For some reason it just wasn't doing it for me. I hadn't fucked her in a couple of weeks now and I guess I needed to try something new. That's when I squeezed lube onto my finger and then started rubbing my asshole with it.

It felt weird caressing my own rim, but it did feel rather good. I eventually relaxed more and then added more lube so that I could stick my finger inside. Due to playing with the outside so much, my finger slid right in. I wiggled it a bit at first, then slowly pulled outward and then inward for a different sensation. I was enjoying it for the most part. There was no pain, no awkwardness and it felt quite pleasurable once I found where my prostate was located.

Once I found my prostate, I held my finger in one spot and then started jerking myself again with my other hand. The contractions that occurred around my finger pressed it into my gland and actually stimulated my erection even more.

On a side note, it's rather difficult to explain all of this to you since I can't write at the same time while performing the act.

I eventually found the perfect spot for my finger to rest and allowed the new stimulation to take me to a form of orgasm that I never thought possible. Having orgasmed from watching porn while jerking myself and cumming in my girlfriend's pussy, it allowed me to see what I was missing out on.

I would assume – correctly, most likely – that most men wouldn't attempt something such as this, nor would they write about their experience and post it for others to read. I guess the whole point of this was to shed some light on something that most find to be taboo. In an ever changing world, we need to explore all options and ideas to get the most out of life. For me, that was finding a new – and easier way, I might add – of getting to orgasm without the aid of my preferred female partner. There was nothing queer about it and nobody even had to know it occurred.

Allowing this story to be told was a huge step for me into potentially dangerous territory, but I didn't care. If you can't live your life the way you want without hurting someone, or be open to new ideas, you will never get far in life. Just because I did it and enjoyed it, doesn't mean you have to take my word for it and do it yourself. You are free to do whatever it is that makes you happy. In my case, I was curious and longing for a new form of pleasure without my girlfriend around.

Laughing now in my room, I know my girlfriend will surely have something to say about me asking her for a rimjob and to finger my ass as she jerks me off. I think it will be fun if she does it right and I might even return the favour if she's up for it.

For any of you wondering about what happened when I finally came, let's just say that I recommend you point your dick towards a towel, or something other than straight up, or towards you. My cum shot nearly straight up and landed on my stomach. Do you have any idea how hard it is to remove that shit from a treasure trail?