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Come from behind

Close up shot of mollys face. Out of focus over her shoulder is mans hand on her hip and his body up against her as they have anal sex

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 him that all I wanted was a one-time 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.

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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  • Molly Moore - Author, Blogger, Photographer, Speaker, Director of Operations @Eroticon Find me in my corner of the internet at Molly's Daily Kiss and on Twitter @mollysdailykiss

  • Show Comments (27)

  • Melinda

    Oh dear Lord, I so want to know this feeling! Paul’s cock hurts me every time we try and he is so gentle, slow and I am amply lubed. His fingers make me burn (he has large hands!) when he plays with my arse but it also feels wonderful.

    I am literally soaking my panties here, at work!

    • Molly Moore

      Hi Mel

      My advice would be to try to work up to anal sex. Start with lots of lube and just a finger and then maybe progress to a toy or a butt plug before trying with his cock. Set aside a nice bit of time to do this during one session. You might also find it helpful to try wearing a small butt plug now and then to help get used to the sensation. Other things to try are stimulating your clit as he pushes in either yourself or with a vibe. Sometimes it can feel a bit stingy as it goes in, try to relax and breathe through that as once that initial sensation has gone then along comes ALL the pleasure. Tell him to be still in you while you let that subside.

      oh and this toy is BRILLIANT for anal



      • Melinda

        Thank you for your insight. This is definitely helpful and I will ask Paul to give it another go. He gets so worried about hurting me and has a tendency to give up. Do you use condoms or does your husband enter you, naturally?

        That toy looks perfect to get me started.


        • Molly Moore

          Try to reassure him that you will make it clear if you want him to stop but otherwise you want him to go slow and give you time to relax into it. Also we don’t use condoms as we are in a fluid bound relationship but I have had anal sex using condoms and it was fine but again, plenty of lube, always plenty of lube. You might want to try a silicone lube too as it doesn’t dry out so quickly as a water based


          • Melinda

            Thank you, Molly. I will talk with Paul and make that clear that I want this to happen and to just hold when I need him to. I like how you say that you don’t like the pounding but the gentle movements. That sounds like what will make this nice for me.

            We don’t use condoms. I hate the way they feel and smell. I prefer to have him release inside of me and this seems to be a way to further experience my husband’s cum inside of me.


  • Nick

    amazing words and image

  • missy

    I loved this and can really relate to the way it makes you feel. It was super hot to read and the last paragraph summarised it perfectly ?

  • Mr Minx

    Great post – very raw and sensual! Krystal and I have explored this area too, and hope to post about it soon!

  • Mrs Fever

    Oh, your DP experience sounds scrumptious! It’s something I’ve not yet done (not with live cocks anyway; toys are another story), but I think it may be on the horizon in 2018.

    • Molly Moore

      Ohh how very exciting. I hope you write about it if you get to do it


  • Cara Thereon

    Oh my. That was a sexy read to go with a hot as fuck photo. I’ll have to go reminisce on my experience now

  • Indigo

    Excellent story with lashings of lovely detail. A shame it’s not Michaels thing, but brilliant that you were about to experience it earlier.

  • Nilla

    Wow! Freaking gut churning hot! There’s nothing like anal sex to tumble me fully into sub space. You’re so right…good girls don’t! Dirty dark and raw..primal sex at its darkest. And so incredibly hot. Kissy reading this made me…smile. And hot. Well said!

  • Cammies on the floor

    Oh god the last part where you describe the scenario is so deliciously hot. As is your photo, very well done

  • fondles

    Hot. And like you I prefer small rocking motions to deep thrusts too. And the thing about dirty girls? I suppose it’s why I feel the most “able” to receive such play when I’m feeling at my most submissive. Thanks for the pic and the descriptions. Loved reading about your experience with DP too! Not something I’ve ever done (except with toys…)

  • May More

    Great to hear about your early experiences – I have already written a post about the men in my life and anal sex earlier this year but I really want to participate in this KOTW so i am scratching my head for an angle so I don’t repeat myself. Awesome photo – good enough to go on the sideboard 😉 x

  • Marie Rebelle

    I’m definitely a huge fan of anal sex too, but that’s no secret. I still have one thing on my fucketlist: a DP. Hopefully one day 😉
    Love your image!

    Rebel xox

  • Brigit Delaney

    Yep, on the anal! You pretty much nailed the way I feel about it, too, with your second to last paragraph. I always get a twinge of “oh…my…you want to what?” every time he suggests it. But then the suggestion turns into a directive and my hands are tied. What’s a girl to do at that point, right? It took me until my thirties to accept that I actually like it.

  • Sweeten Dirty

    Those are some very sexy words, Molly. I look forward to and hope that someday I can achieve the anal pleasure that I hear and read about every day.

  • Jo

    Your DP experience sounds super hot – I fantasize about doing that a lot. Like you, I need to be in a relationship with a partner whom I can trust to be able to relax enough to enjoy anal (although I’m sure if someone asked me mid-orgy and I were high on orgasm endorphins, I might change my mind!).

  • Bee

    I have all the envy for your DP experience, it’s something that’s high up on my fuckit list!

    And damn woman, that image is so fucking hot!

  • Kayla Lords

    I almost wish I enjoyed anal more after reading this. Your experiences sound amazing!

  • Focused and filthy

    I think we are very similar in lots of sexual ways. This post is another indicator of why. I haven’t had a proper DP yet but with lots of toys and I’ll be honest I can’t wait. I was about 34 before I was able to get into anal too. Super hot
    Missy x

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