[Sex] The Anal Adventure Begins

I’ve read three posts on anal sex this past week. It started with this beauty from Girl on the Net, followed up by The good, the bad, and the anal by Cara Thereon and then when I perusing the Sinful Sunday posts I read Reclaim my arse by Sweetgirl. These are all interesting posts for me because as I have previously discussed, I have not yet had a complete experience of anal sex. In fact, up until very recently, it was closer to a hard limit than it was to anything I’d like to try. 

When I started my adventures in fuckery, with the now aptly named Mr Fuckery, I did mention that anal wasn’t really my bag. Which wasn’t a problem, seems it wasn’t really his thing either. Communication done, we both know where we stand, how excellent, so how is it that his finger has been in my ass and I feel certain that one day his dick will follow. 

I don’t know if this is personal development or if it’s insanely good sexual chemistry at work, but god damn I want that man to fuck me in all the ways possible, including the kind that means his dick sliding into my ass. We’ve started slow, first is was a tentative finger massaging my asshole, then one day in it went and OH. MY. FUCKING. GOD!!! It was intense. I honestly didn’t know how to process all the extra sensations I was feeling. 

We’ve done the finger thing a few more times since and it amazes me how easy it feels with him. One of the times I couldn’t get however how simple it seemed for him to slide in and out of me. I know one finger might not seem like a lot, but in the past, even that would have felt uncomfortable or painful. There his finger was though, in, out, harder, faster and the whole time my body is just accepting it and revelling in how it felt. 

I think about anal a lot when I am on my own and masturbating. Which I do a lot more these days because we can’t fuck every day and I can’t go a day without thinking about fucking him. So masturbating over thoughts of him is my only option sometimes. I think about lots of things, but him fucking me in the ass achieves almost instant results. 

The time we seemed to fully decide to embark on this adventure, he’d sent me a message detailing a dream he’d had where he’d fucked me in this way and I couldn’t get over how hot it was reading about how he had those thoughts in his mind. I knew there and then that I wanted us to try it if indeed he was up for it as well. We have since had a few message exchanges involving my ass and its availability and it never fails to turn me on.  

Prior to these conversations, I’d sent him a picture of me wearing a butt plug while he was on the longest holiday of my life. Did you know when you’re super hot for someone 2 weeks last approximately 5 years? He’s away again at the moment, I have to not see him for 5 days, which will feel like two years! Pictures are a good way to keep up the momentum we have built between us and the butt plug images definitely did that.

My header image is a cropped version of one I sent him, all the others are strangely for his eyes only. Despite all the images I’ve shared on the blog these ones, of my ass plugged and my cunt on full display just feel far too intimate to be displayed here. 

When I put the plug in, which was the first time I’d done that in a very long while, I did actually enjoy it. There was some getting used to it again, though this particular plug is extremely comfortable for me, after that though I wondered if I could do enjoy some other kinds of anal play on my own, to help us along the way. 

I started with my own finger, whilst the Doxy was on my clit and my index finger was in my cunt I started to slide my middle finger slowly into my lubed ass. At this point, I was about halfway to an orgasm, so I felt very turned on and I’d be talking out loud about sucking his dick, having him come on me, the usual things I say to woo myself into coming. As my finger went inside, I changed my chatter to talk of his dick being in my ass and when I say I came hard to all of this, holy fuck folks, I came so hard it took my breath away, which isn’t a normal occurrence for masturbation. 

I know the times I’ve tentatively tried this before it hasn’t worked because I wasn’t relaxed and I didn’t really want it, I was largely always doing it to appease someone else and to get them to shut up about trying anal. To be trying it with someone out of desire clearly makes a whole load of difference, and the fact I can be actively fucked in the ass, even with just a single finger gives me high hopes for the future of ass fucking. 

He also makes me feel unbelievably relaxed, not just with fucking, but in general. One of the things I always enjoyed about FemDom sessions was how it silenced my brain, I loved the focus that came with topping Bakji and it was freeing to shut out the world for the duration of a session. What I never expected was to discover that kind of calm just by hanging out with someone! 

As someone who has a brain that brings anxiety along for the ride, including at bedtime, which means disordered sleep is a big thing in my life, the idea of my brain just going quiet is baffling. The fact it has, on more than one occasion, gone quiet enough for me to sleep through the night is a testament to how freakin’ chilled this dude makes me. Honestly, if I can lie beside him at night, fall asleep and not wake up until morning and not recall my dreams the next day, then I can absolutely relax enough to let him fuck me in the ass. 

In reading the three posts I linked to at the beginning of this post I felt a lot of things. Firstly, even as an anal noob, I could see where GOTN was coming from. All of what she said made complete sense and I can only envisage those sensations increasing the further into this we go. Secondly, when I read Cara’s post I felt comforted by the fact that sometimes these incredible moments happen with people we may not be destined to be with forever. 

A lot of people upon reading my recent posts have commented or got in touch saying ‘wow, this seems like the start of something special’, no who knows, maybe they’re right. Got to say though, knowing the more intricate details of our set-up I’m still preparing myself for it to end in chaos. I do not see how I can possibly get to keep something this good, it feels too good to be true in all honesty, in so many ways, not just from a sexual point of view. 

Then I read Sweetgirl’s post though and I know her and Mr H have something special and for the briefest of moments my heart races, my cunt twitches, my mind wanders, my tummy flutters, my skin tingles and all of me unites in thinking ‘what if’, what if anal sex is just one small part of a much bigger adventure and that my friends is why I think I’m destined for a fall, that ‘what if’ shows much that I am hoping for so much more than I can possibly get. 

On the plus side though I can almost certainly get fucked in the ass in the near future and that is definitely a moment I am looking forward too!

12 thoughts on “[Sex] The Anal Adventure Begins

  1. I’m so exciting reading this, the ancipation and the desire to have anal sex. You will do it and you will have to tell us. For littlegem and I anal was enjoyable but we couldn’t really go that far without issues for years. Then something changed, all of a sudden I can bend her over and she can take it and I can tell her deep I am inside her because she loves to know and it feels so intense.

    Let the adventure in!

    1. Thank you PS, I will definitely be sharing as things progress ☺️ it was actually reading some of yours and little gems posts that helped me further relax into the idea of anal. You both write about it in such an accessible way, which is helpful to those of us who are new to it x

    1. I’m excited for all your new adventures but as a fellow anal sex lover myself- I’m super excited for this adventure for you!!

      Also- I am a firm believer to let relationships become what they want. Hold on loosely- you’ll know what it’s supposed to be. Half the fun is the getting to know one another and figuring it all out! I’m glad he makes you feel so chill and lovely!

  2. No idea how this thing with Mr Fuckery will go! But enjoy the moment! When I met my Queen sparks flew. We had volcanic sex right from the very first time. 17 years later we still have volcanic sex. I regard her as my soulmate. But I didn’t know that then. I didn’t label it or try to understand it so much as just living and enjoying it!! Stay well Floss. Enjoy Mr F. Who knows in 17 years you may be happy with him as your soul mate. Or you may remember him fondly as a remarkable time in your life. The point is no one knows. So live, enjoy and experience!! It’s a great time to be alive!

  3. Oh Floss! I love this and am so excited for you!
    As others have said, enjoy and live with this time and experience. It is a blessing to find a person you respond to so incredibly well with! Absolutely can’t wait for you to share more 😉
    Kurvy recently posted…Thoughts and MoreMy Profile

  4. “To be trying it with someone out of desire clearly makes a whole load of difference…”

    Ummm…yes. the first times I tried it, I hated it, because I wasnt completely physically open and relaxed. Even now, there are times it doesn’t work, even though I like anal.

    I love how you describe the journey between you. It feels like I’m being let along for the ride. Expectation is the root of heartache, but it is nearly impossible not to expect…dream…hope…especially when things are so good. We all deserve good things, though. So it is best to let them happen as they will and appreciate them every day for the wondrous gifts that they are!

  5. Wonderful! How exciting that you are feeling so fulfilled and eager to explore new terrain with Mr Fuckery. I hope that time flies until you get to be together again.

  6. What a lovely post Floss, and thank you for mentioning my post in yours, especially in terms of how you see our relationship. I am glad I manage to convey our relationship so well.

    Anal is something, I think, clicks at some point if you are open to it, and perhaps when it is right for you. It isn’t for everyone.

    I hope you continue to enjoy your explorations. Building up is definitely a good plan, a small dildo or vibrator for example. I generally cover anal toys with a condom as it makes cleaning so much easier!


    Sweetgirl x
    Sweetgirl recently posted…You make meMy Profile

  7. This was really enjoyable to read because the way you thought this was never something you’d like to do, and then somehow you get to a point of actively wanting it, is so relatable – though I haven’t had it with anal, like you. It sounds like you and him have something special, at least in the moment right now it is and that’s all that counts right now. I’m happy to read that you appear to be quite happy right now!

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