GOING BEHIND – first experiences (KOTW)

By | 4th January 2018

For Kink of the Week’s Anal Sex topic I am going to revisit two earlier sessions, both of which were firsts for the person involved. In one I was very much the submissive, in the other I was more the guide.

Until I met Elita my only experience of anal sex had been an occasional excursion with a gloved finger from a Mistress. I’d always found it surprising but mildly pleasurable, a sensual rather than masochistic experience. Very early in our exploration of my kinks and assuming, I think, that I was at least moderately experienced with this type of treatment, Elita introduced me to hard anal fucking. At the time, it was just about the most intense session I had had.

In stages she pushes her strap-on into me. I feel my body resisting and have to force myself to relax. “Take it,” she commands, “take it all,” moving in and out with increasing speed. This is new. This is unusual, scary and demanding. I can feel the end of the strap-on deep inside me. I let out a small moan as sensation turns to pain. Her response is to thrust harder, faster. Now I am moaning with each thrust, fighting to get on top of the sensation. I can feel her exertion, the physical effort of what she is doing. Her breathing, like mine, is short and fast. She adjusts her position so she can go deeper; it feels like she is deliberately pushing me to the safeword and I have it ready because I don’t think I can handle this. I am gripping the bench hard, fighting, each push taking me further beyond what I would have thought was my limit for this kind of treatment.

I think Elita had really wanted the safe word here, was working hard for it, but I can be an obstinate bastard and even though I was really struggling, I hung on till she stopped. I realised afterwards that, had the session only been about pain, I would have called a halt earlier. But this felt like having sex; it was having sex.

Later in the session Elita had another go at me:

Her strap-on is inside me again thrusting hard. I am so sensitive from the first session that this feels brutal; feels, in fact, one of the most brutal things that has ever been done to me. I am gasping in exertion and pain. But through all the anguish I can feel her beautiful pianists hands on my back. I can feel the front of her thighs moving against the back of mine. I want these sensations to continue so I wrestle the safe word down once more, way over the pain/pleasure boundary but not wanting it to end.

This was over two years ago and I still remember the visceral intensity of the session. I understand much better now how my willingness to tolerate pain goes up exponentially if a small amount of intimacy is served up with it.

man grabs ass

The other “first” experience is more recent – a chance to introduce a willing novice to a first, or certainly very early, experience of anal play. I had planned quite carefully how I was going to approach this part of the session.

woman underwear small

I have her kneel on a wide leather bench, locking her ankles and wrists to the sides. She’s exposed and vulnerable. I blindfold her, so all she has is sensation. We’ve had quite a detailed consent discussion about anal play but she’s still shocked as my gloved finger pushes the rope aside and starts to explore her tight little bottom, resisting then accepting; gasping at the new sensations. This is exciting for me, remembering my first time, remembering the surprise and shock of the broken taboo. My other hand  starts to stroke her clitoris, then penetrates her so my fingers become aware of each other through the thin veil of her vagina wall. She’s noisy now, sighing and gasping, not knowing how to respond, but I push on, sliding my fingers in and out together, until she comes again, shaking and squirming. I let her rest and drink some water. 

I pull her back down. This time I have a small butt plug I’ve bought for her. It’s wider than my finger so she squirms and breathes hard as I inch it forward, gauging when she’s ready for me to push again. Just as she thinks she can’t take any more, I reveal that it’s not just a plug, it’s a vibrator, the new, buzzy vibrations bringing a surprised gasp as they run though her, pushing her towards another orgasm.

“Ask for it” I tell her, wanting her to beg to be allowed to come.

“I caaaan’t,”she almost cries.

Can’t ask? Can’t speak? Just can’t?

She’s in very deep now as I push her over the edge again.

It was one of the hottest thing I’ve ever done with a submissive. What really made it hot and intimate and wonderful was the trust she showed. I could see she was uncomfortable: physically uncomfortable at the unfamiliar sensations, emotionally uncomfortable at the way I had violated the taboo, yet she overcame these things and allowed herself to dive deep into the waves of feeling I was causing, becoming completely, incoherently lost in them at the end.

It was a very special moment for me, not least because, as you saw earlier, I understood exactly how that felt.

stock stick man


More anal kinkiness here:

All images in this post are from Shutterstock

12 thoughts on “GOING BEHIND – first experiences (KOTW)

  1. Kayla Lords

    I love this…”my willingness to tolerate pain goes up exponentially if a small amount of intimacy is served up with it” – I can relate to this so much even though my pain tolerance is much lower.

  2. Bee

    I love the way you describe both experiences here. How you put up with the pain intrigues me, anal pain would always concern me more than my desire to please someone else.

  3. Mrs Fever

    I think that pain, where anal sex is concerned, is often described as the “turns to pleasure” variety. There is an almost rote method to it: Resistance, stretching, uncomfortable breaching, a violation of muscle, and then… Relaxation. Tingling. Overwhelming intensity and pleasure.

    Or, in not-good anal penetration experiences, it’s often just PAIN. Period.

    One thing that intrigues me about this post is that – as I understand it – from your masochistic perspective, the pain never “became” pleasure in your experience with Elita. Instead, you kept the pain, bore it out, and found pleasure in something different. I find that fascinating.

    A scintillating read. Thank you for sharing.

  4. Cara Thereon

    Very much enjoyed reading both ends of this. Your experience seemed very very intense. I liked the care you took to intro the sub into the experience.

  5. May More

    Yes you have a great advantage when giving because you have received – This undoubtedly made you more sensitive to your subs needs

  6. Indigo

    Fascinating to read from both perspectives. That sensation of both openings being filled and the pressure on the membrane between is so intense.

  7. Molly

    This is a really interesting piece looking at both sides of the anal coin so to speak. I remember that post about your and Elita when you wrote it. It was a very powerful piece and those snippets you have included took me right back to it. I love how your writing stays with me like that


  8. Marie Rebelle

    I love the hard session you had, but also how respectful and gentle you were with the willing novice 🙂
    Beautiful writing!

    Rebel xox

  9. Posy Churchgate

    Very well crafted piece, I liked how you viewed it / described it from both sides, and I’m convinced (like you) that the session with your sub was extra hot for you because you’d been on the other end of it previously. Analysis aside, it was very hot – particularly the scene with your sub (less pain – but that’s just me!)

  10. Missy

    As usual you bring such great insight and sensitivity to such a divisice topic . Wonderful to have seen both sides of the D/s position too.
    Thank you.


Leave a Reply

Your email address will not be published. Required fields are marked *