I was 37 when I first had anal sex.
We met in a chat room. Spent weeks typing utter filth back and forth until we will both desperate for one another. He was nervous about meeting up but I convinced that all I wanted was a onetime thing. He bunked off work for a day and drove all the way from Birmingham to my home and spent the day in bed with me playing out many of the things we had so perfectly role played together in the chat room. He knew I had never had anal sex before. He was gentle and kind, using lube and his fingers to get me ready and asking me repeatedly if I was sure. I came a lot of times that day but the most powerful orgasm was the one I had when he slowly pushed his cock into my arse.
I have fantasised about anal sex a lot before that day and even used toys on myself when masturbating so I knew it was a turn on for me but there is a big difference between fucking yourself in the arse, where you are in control and can set the pace perfectly and trusting someone else enough to share that with them especially when it is a first time. Luckily he was a good man, who wanted me to have a good time, my pleasure was important to him and as a result I have absolutely no regrets whatsoever about him being the first man who did that with me.
For me anal sex has always seemed like a more intimate sex act than vaginal sex. Maybe it is because I am more confident when it comes to that or maybe it is because I like anal sex in a very specific way that I wouldn’t contemplate doing it with someone who I was in a casual relationship with. I need to feel a strong sense of trust and connection with someone to want to have anal sex but when I do then we are onto a winner because it is a massive turn on to me.
The only time I have broken that rule was back in my swinging days where I ended up having an unplanned double penetration fuck with my partner and a guy who was part of a 5some we were having. He suggested it after witnessing how much I got off on my partner fingering me and I decided to throw caution to the wind and go for it. I sat across my partners lap his cock buried in my cunt and laid forward over his chest while the other guy guided himself slowly into the ass. I guess I should have been nervous but I wasn’t. Having a DP was something I have long fantasised about and my then partner knew that and had often talked to me about arranging one. The only thing I felt was hugely turned on.
The guy in my arse felt so damn good and I was rubbing at my clit while he slowly fucked me from behind. After what seemed like a few minutes he stopped. I think to check that I was OK but I was so disappointed. I had been so close to coming and suddenly he was gone. I made my disappointment very clear though and he was happy to resume. It was an amazing experience, a fucking moaning orgasmic one at that. I have repeated it, well not with two cocks, only with dildos but it is something that with the right people I would fucking love to do again. Sadly it is absolutely definitely not Michael’s thing so the chances of that are slim to non-existent but I am damn glad I took the chance when I had it and whenever I think about it I can’t help grinning at the filthy memories of that day.
I think anal sex works for me on two levels, there is of course the physical sensation. The way it makes me feel full but I can get that sensation from butt plugs and toys. In fact they work really well because I am not keen on a lot of thrusting. I like shallow kind of rocking movements. However there is nothing quite like the sensation of the real thing and that also plays into the second part of what turns me on about it and that is the strong element of taboo and how it speaks to my submissive kink. In my mind it is insanely hot. Just the words “I am going to fuck your arse later” whispered into my ear will make me throb, in fact talking about fucking my arse while you finger or fuck me will nearly always push me over the edge.
Being fucked in the arse is dirty and filthy and raw and so not what good girl do…. but if you make me, hold me down a little, whisper it will be OK into my ear as you pour lube onto my arse, tell you are going to do it no matter what I say so I might as well co-operate, or, that when I fight it I only make it feel better for you, use your body weight to pin me in place as you push your cock into my ass…. well then what choice do I have but to be a very dirty girl.
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