A Bumpy Ride: First Time Pegging

Most of what I write here at Scandarella is either toy reviews or complete fiction. I don’t often write about myself, about the Fella, or what we do with and to each other when the sun goes down. But I’m gonna look at real life for a change. I’m gonna take y’all way back when to the first time I ever shimmied my ass into a strap-on harness so that I could fuck the Fella with a faux cock.

Of all the things we’ve tried together, him deciding that he wanted to be on the receiving end of anal was the one that surprised me the most.

See, my everyday self is antagonistic, stubborn, and basically a self-diagnosed pain in the arse. I’m difficult, demanding, and I have a touch of the control freak about me if the Fella is to be believed. But when it comes to the bedroom, I readily hand over every iota of power that I possess. Why? Because I don’t want control. I don’t know what to do with it, I need the Fella to take charge, to guide me, to lead me. To wrap everything that he is around me so that I feel small, safe, and cared for. In return, I strive to please him, to show him the respect I sometimes neglect to give him during the day. I work hard to give him what he needs and to make sure he knows he’s appreciated and loved.

But when I would look at him lying on his back like a toppled tortoise, waving his legs in the air and asking me to put stuff up his butt… that felt like a very submissive act to me. In some ways, it felt to me like he was diminished somehow. That laying himself open to me in such a way weakened him. Or rather, it diluted the strength younger me needed to feel coming from him.

I’ve never told him this, but I really wished he hadn’t decided to try anal at all. It took him a few times to decide that he liked it, but I secretly prayed that he’d hate it. Looking back, I can see that I subtly tried to encourage his uncertainty towards dislike. I tried to make him uncomfortable with anal because I truly dreaded the day arriving when he wanted to upgrade from hand propelled penetration to the pelvis led stuff. Thrusting a probe into him while I stroked his cock or gave him head was one thing, but rising above him,  guiding a faux cock into his ass, then gripping his hips as I drove into him was something else altogether.

There was no fanfare when he asked me to do it. No forward planning. In fact, he was a bit short and matter of fact. It went something like, “Get the harness out. No, I’m not wearing it, you are. I want you to fuck me.”

I’d never felt so afraid of a sex act and I haven’t since. I admit that I stalled. My mouth suddenly became obsessed with his cock and I launched into the greediest of blowjobs. Then I did that at the beginning of every sex session purely because I knew that he’d come super quickly, lose interest in anything more than giving me my orgasm in turn, and I’d get another day’s reprieve.

Yeah, I know. I shoulda just told him I didn’t want to do it but…deep breath…I didn’t want to disappoint him. Okay, that’s a lie, he wouldn’t have been disappointed at all. He would never have made me do something I was uncomfortable with. The truth is, I didn’t want there to be something he wanted that I didn’t. I feared not meeting that need for him.

So, the time came when I couldn’t reasonably put it off anymore. On went the harness, making me aware of every ounce of belly fat I possessed. Off came the harness, on went a basque, then back on with the harness. In went the dildo and I felt weird. On my own in the bedroom, I liked how my pretendy cock felt. I kinda liked how it looked. Yes, I wiggled my hips to make it slap off my thighs. And yes, I did jog on the spot to make it bob up and down while I said ‘boing-boing-boing’ like the utter tit that I am.

But as soon as the Fella came into the room I wanted to die. I mentally hollered at Zeus and said he was about as weak as a 5-watt bulb in a bid to get him to thunderbolt me. I don’t know if I looked like I was about to expire or if he suddenly got the jitters, but rather than lying down or getting on all fours as he had for other anal play, the Fella pointed at the bed and told me to lie down. Once I did that, he got on top of me.

What the fuck was I supposed to do? Did I do the stuff he did when I got on top of him? Should I hold the dildo upright for him or would he prefer to angle it himself? Should I part his cheeks so I could watch the initial penetration like he sometimes did? Or should I hold his hips, rub his back, try to reach his cock or…god for-fucking-bid, should I spank him?

It was everything I didn’t want. Uncertainty, confusion, discomfort. Control felt like it was mine and I didn’t want it. Decisions felt like they were mine to make, and I didn’t know how to make them.

In the end, I didn’t have to.

Little Hitler might have wanted his butt fucking, but he had no intentions of handing over the reins. He topped from the bottom, kinda, and I was bloody elated. Barking orders at me, telling me to shift my legs, move up a bit, to the left a bit, do something with my hips but slowly. He was in charge of depth, speed, duration of play. And he also decided when it was time to flip the switch and make use of the crotchless nature of my harness.

After that, I didn’t look at pegging with the absolute terror I once had. I still felt uncomfortable for a while when the time came for him to stop riding my faux cock and for me to start fucking him with it. If you’ve never done it before you might not realise how different the movement of thrusting into someone is compared to thrusting on them. It’s hard bloody work at first. My back, thighs, and knees didn’t know what the fuck I thought I was playing at.

It took me a helluva long time to find my stroke. The rhythm still doesn’t feel natural to me, if I’m honest. Maybe it’s because I can’t feel any real physical sensation while I do it. I feel it emotionally and psychologically, but all my body really feels is external thumping. Yeah, using plugs, love eggs, and clit vibes gives me plenty to focus on, but that isn’t me getting physical stimulation from pegging.

I don’t mind, though. If I still had that fear of being given power I didn’t want, I’d probably hate it altogether, but the Fella hasn’t ever made me take control. He still bosses me from the bottom. He’s still in complete control over how deep, how hard, how fast I go. Whenever I poke him in a way he doesn’t like (I have a terrible habit of trying to make a new hole an inch too high when the dildo slips out, lol) he somehow manages to smack my arse even though he’s flat on his face beneath me.

These days, I feel pretty much the same way about pegging as I do about blowjobs. I love giving him what he wants, what he needs, in whatever way he asks for it. The only power I feel in me is the power to please, and that pleases me no end.

Now I just hope I can get to that happy place with his latest favourite thing. No, my early feels about pegging weren’t good ones, but they were nothing compared to the feels I have about rimming.


Week #219


Prompt – Female Domination


Prompt #337 – Control

17 thoughts on “A Bumpy Ride: First Time Pegging

  1. I found this really interesting.

    It’s often easiest (and safest, from a “let’s not tear any sensitive tissue” perspective) for the penetratee to guide the movements at first, whether from an on-top ‘riding’ position or by backing themselves onto something from all fours. So in terms of physical approach, I found myself going “of course,” nodnodnod.

    That he managed to be toppy/bossy about it kind of made me go “…hmnh.” Less in a general “expected-role-reversal” power exchange way than in a “pegging does not equate to power for me” way. While my overall relationships tend to be M/f flavored, specific acts within that/those relationship{s} are not necessarily about power, but about pleasure.

    By that, I mean:

    I realize that for many, the roles assumed during the act of pegging are very specifically ‘dominant’ or ‘submissive’; it’s kind of the norm in how it’s popularly presented, I think.

    For my partners… Yes, they may *feel* submissive, or somehow “feel my dominance” through that particular penetrative act. But for me, pegging is not something that makes me feel all Dommely-Dom McCockypants. It’s not about that. It’s just about exploration and – ultimately – pleasure.

    To be absolutely clear: One is not better than the other. They are just different mindsets/approaches, and the way you wrote this really made that stand out to me.

    So as I said: this was really interesting to me.

    .

    (Sorry to be all “me-Me-ME!” in your comments section; sometimes my attempts at clarification are a bit autbiographically long-winded. Please feel free to truncate as you see fit.) 🙂

    1. Comment whichever way you fancy, lovely, I ain’t ever gonna stop you 😉

      My OH sees things similarly to you (he’s read this piece post publishing so I’m getting a running commentary from him, lol).

      He doesn’t see any sex acts as being exclusively submissive or dominant, he believes that it’s the intent/nature of the people performing them that gives them their label, should they need one. He says that, contrary to what I think, he isn’t intentionally topping when he bosses me around, but that the prompts and orders come because he knows that I need them to keep me in the moment, much in the same way he knows when I need to hear dirty talk or sweet nothings.

      He thinks the real truth behind my discomfort is that I actually enjoy being in control and that it scares me because it’s outside of what I’ve come to expect from our play. I’ll be thinking about my approach to our Ds all night now, cos I didn’t realise how differently we interpret the things we do. I’m also gonna explore my feelings about pegging a bit deeper to see if I’ve maybe allowed myself to let stereotypical presentation of it to colour how I perceive it.

      I did use the word ‘weak’ when talking about him bending over for me and I regret that already. I don’t see men who enjoy pegging as weak in the slightest, I meant it only in connection to my own personal dynamic with my guy at a very specific point in time. I should have clarified that in the post but this was train of thought writing (much like this reply) and (as ever) I didn’t do any editing.x

  2. First of all, feel free to write about yourself whenever you want. This was an absolutely fascinating look into your sex life.

    Also, you described so many of my concerns about pegging…and yet, it makes total sense to me that he took control in your situation. One, he knows you, and two, you are who you are.

    If JB and I ever tried it, I would expect him to do the same. He’s always in control, no matter what we’re doing — this would be no different. All that being said, I still don’t have any desire to try it, lol. But never say never.

    1. I’m glad you enjoyed reading it, Kayla 😀

      I’ve had a good think about my past and current feels where pegging (and control) is concerned and I think my OH is wrong. I really don’t get any kicks from feeling like I’m driving the bus.

      He asked me if I would still want to don the harness if he kept quiet and let me take the lead, and I can honestly say the answer is no. I wouldn’t stop play in its tracks if he suddenly went silent (or passive, as I’d likely interpret it) but I’d definitely be reluctant to peg him the next time it cropped up.

      I dunno, maybe that’s selfish of me cos it could be seen as denying him for no other reason than he wouldn’t be doing it the way I like it, but it is what it is, and luckily I don’t think he could keep his mouth shut anyway, lol.x

  3. Thank you for sharing your thoughts on this, as I can see this coming up in the future for me and my mostly Dom guy, and while we’ve explored other anal play for him, I am also a bit uncomfortable with the idea of pegging, but I do see it on the horizon… so this thought exploration was very interesting and helpful to me! 🙂

    1. Ah, I’m so pleased you found my ramblings helpful 🙂

      I wish I understood what it is about it that makes my mind connect his enjoyment of pegging to submission. I’m not someone who subscribes to the old ‘it’s not manly to whatever’ and I do understand that receptive doesn’t equate to submissive, but at the same time I do know that I wouldn’t feel like I was being handed control that I didn’t want if I was the giver in strap-on sex with a woman, be it vaginal or anal. It’s odd and I really don’t get it.x

  4. I love that it seems he has kept the control all through the pegging session and I think he might do exactly the same with the rimming. Lovely post, not only of control but also of love 😊

    Rebel xox

    1. Thanks, Rebel, I’m glad you enjoyed it. And eeek, the rimming thing is gonna kill me. I’ve done it a few times but you don’t want to see the face I pull when I’m down there. I must look as sour as month-old milk, lol.

  5. I’ve still only barely explored pegging, and entirely at his bidding, and yes, he kept in control the whole time too. But now, having done it, and knowing it gives him pleasure, I think bout doing it again sometime. So Incan really relate to what you’ve said here. I love how frank and matter-of-fact you are. It makes me feel like my flighty, eh, er, what?!? feelings aren’t all that alien.

    1. I’m so pleased that you found something in this piece that resonated with you. It delights me that folks can relate, because reading that others have similar feels to mine helps me, too <3

  6. I echo other peoples sentiments about you writing more posts like this. As with all your writing it is excellent and very thought-provoking. Even though this is not Michael’s thing it is something I have thought quite a bit about, what if he wanted that? And no matter how I frame it I really don’t think I could do it for him and would have to encourage him to find someone else who could.

    Mollyx

    1. Thanks, Molly 😀
      I love that you’ve looked at it from all angles to maybe find a way of making it work for you, just in case Michael should want to try it.

      I’ve been thinking about it since I wrote this post and I think part of me gendered pegging in a negative way at first. I saw my OH as taking a passive, feminine role while I took the masculine one. Part of me felt manly and because of my PCOS symptoms that feeling really messed with me.

      I know now that this was a bollocks way to look at it, but back then I can see that really was how I felt. These days, any discomfort that creeps in comes from the feeling that my own personal submission is being threatened, and I’m happy that my OH will deal with it, cos he always sees when it happens.x

  7. I’ve absolutely loved reading about you ‘please Sir, can I have some more?’

    I love what you’ve said here. I think my mind is somewhat warped and don’t see particular acts as submissive, it’s more about the mind set and attitude.

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