Two Little Peggings Go To Market Part II

Now the second time was wholly different. This guy was just as good in bed, but he didn’t ever want me to dominate him – suited me mostly fine. So it surprised me when he suggested that he wanted to be pegged. Now that we are no longer in touch I can be candid about this. I was very tentative about doing it this time because he himself didn’t seem sure. I couldn’t tell what was actually driving his decision to do this, it certainly wasn’t anything that I was advocating or angling for. But he did want to do it and I do like to please.

He came out of the shower and asked me was I ready. I wasn’t, I hadn’t realised what he had wanted to do. I hastily threw on the stockings, suspenders and killer lingerie set I’d brought for this occasion and then pulled on the harness.

If I was doing this, I needed to be attired appropriately. I had blindfolded him before I started, as he lay on the bed. When I was all ready, I told him he could take it off. And I walked over to the bed and stepped up on it. So I was standing over him looking him in the eye, and stroking my rubber cock. ‘Oh god, you look amazing. That, the underwear, that’s the best thing you’ve ever worn’. I’m glad he liked it, it was for maximum effect.

I ran my toe up his inner thigh to his cock as his hand went to stroke it.

I nudged his hand away, told him softly that he wasn’t allowed to touch anything until I said. And then I straddled him and knelt down, my rubber cock in one hand his hardening cock in my other.

I sucked his shaft, glanced up at him. Licked his balls, glanced back up at him. Still I couldn’t tell if he was happy with me dictating the pace so I entertained myself for a few minutes then crawled up him, cat like and leant down next to his face. He didn’t look tentative, he looked scared. I’m not sure what he wanted, I’m not sure what he needed me to be. I think I might have broken the spell and asked him if he was ok? Whether I did or not I know I kissed him, made him reach for my lips and then whispered in his ear ‘Turn over and get on your knees, because I want that arse’.


He duly did but before I did anything he was asking where the lube was, not in his haste to get going but more in a panic that I would start without it. I might have, but I wasn’t going to do it with nothing… I had planned on using spit.

I spread his cheeks and get my tongue in there. Then I spit on it and go back to it, this time working a little finger in.

There’s not much noise from him so I’m not sure if he’s enjoying it. I keep going because I am. But after I switch to a bigger finger I reach through his legs to feel his cock. It’s not hard. I don’t draw attention to this but I ask again if he’s ok. He assures me he is and that he is turned on.


I get the lube and start working it around his hole and into it. I tell him what I’m doing as I do it, because I love that, when someone does it to me, telling me what they’re doing, working two fingers in and then three. I wish there wasn’t lube on everything as I want to lick it with my fingers in there.

I ask if he’s ready, he says he is. I work lube all over the shaft of my cock and more into his arse and I start to try to get it in, I think after three fingers this dildo wouldn’t be tight but it is. It takes ages, loads of different positions, just like the first time, but I do manage it. I do manage to get my rubber cock in there and fuck him. This feels different, this is me finally thrusting into someone, into a guy. And I like it. I like how I look doing it, I like the sensation. I like how dirty and wrong it feels and I just like the whole idea of it.

What I don’t like is the look on his face – for two reasons. He looks scared. Is that what girls look like when guys fuck us? I don’t want to make someone look like that, I don’t enjoy it, it doesn’t make me feel good. And this isn’t what I wanted from this; I’m not wearing a strap on to make myself feel powerful and him feel scared or anxious and untrusting, I’m doing it for his pleasure. And to hear those gorgeous sounds I thought I was going to hear – that’s what was in it for me. But the overarching emotion that seemed to be on his face was anxiousness, anxiousness that I would go too hard, or too fast or somehow lose myself. Which is really redundant because from his male point of view, he seems to have forgotten one pretty important factor; this is not a real dick that I’m wearing! and I’m not about to come from this. I was monitoring his reactions the whole time, because his reactions were all I wanted.


But what I took from it was that he didn’t trust me. And that saddened me. What also was a shame was that this was something that he wanted and he didn’t seem to be able to let go and embrace it. He was still trying to control and make sure I didn’t hurt him. Which was disappointing to me.


I was very glad when he said after that it was a box ticked and we didn’t need to do it again. What was also worth noting was that for the rest of the weekend he said he had no interest in fucking my arse! After him being only just about able to take the dildo, which was a good third smaller than his cock, he had a renewed respect for how I’d taken all of his up mine.



I don’t regret it and I don’t view it as a bad experience at all. I finally got to properly fuck someone in the arse and I’m delighted with that. But that’s not what I want out of a pegging situation. And I know that it’s not something that will niggle at the back of my head as something that I wasn’t able to do properly.

I think the key thing with it is, if you’re not sure, then you don’t have to do it. If you don’t think you can relax and enjoy it then you DON’T have to do it! It’s ok to change your mind.

But mostly I’m happy that I’ve sent one bloke out in to the world with a better appreciation of penetration in general – and to be a hell of a lot more grateful to any girl who’s willing to take his cock up her arse.







And so concludes Abbi’s adventures with pegging – for now.

Leave a Reply

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