Guest blog: My first pegging session

Image by the brilliant Stuart F Taylor

As regular readers will know, I am a complete sucker for stories of first times. The thrill of doing something you’ve never done before is a beautiful thing to capture and share. The fabulous @EuphemiseThis has written before about getting invited to her first threesome, as well as the first forbidden fuck she had with a friend. Go check out all her fabulous guest posts here, but not before you read today’s incredibly hot story – about her first pegging session.

My first pegging: How it started…

I straddled him on the sofa and he removed my bra, sucking eagerly on my nipples until I shuddered and came noisily. That was the amuse bouche.

He knelt at my feet, pulled me to the edge of the sofa and hungrily buried his face and fingers in my cunt until I gripped the cushions and loudly moaned in ecstasy. That was the starter.

Then we moved into the bedroom so that we’d have space for me to ride his cock while he buried his face in my tits. So he could fuck me hard from behind until I instinctively grabbed a pillow to muffle the screams from the thunderous orgasm that coursed through my body.

But that still wasn’t the main course.

Back when we first connected, via a dating app, it wasn’t long before we started discussing our sexual preferences, likes/dislikes and boundaries. He told me he was really into pegging, and I was intrigued because it’s something I’ve never tried. Any men I’d discussed ass play with previously had been very clear that they definitely did not want to be on the receiving end, so I had stopped even raising it as an option with new male partners. But this guy was super keen, and his enthusiasm quickly rubbed off on me.

After a fantastic initial fuck date, he expressed an interest in me fucking him next time. I was apprehensive, but that was more a matter of logistics than anything else so I thought it best to be honest. I explained that I didn’t have a strap on (he already has one) and then, once I was reassured that I wasn’t expected to have all the answers, I asked what his favourtite position was (on his back) so that I could start to imagine the fuck in my head.

At this stage I was very much up for it but have to admit to doing a bit of Googling to reassure me that I wasn’t missing any vital information. I’d used a strap on before, but not for anal fucking so was assuming that I’d probably need lots more lube, different angles and a more careful pace, at least to begin with. Everything I read seemed to mostly be aimed at first timers on the receiving end, or people looking to buy a strap on for this type of sex, but I deduced that my instincts were probably right and so I set about trimming my fingernails very short and imagining the look on his face as I slipped a lubed finger or two inside to prepare us both for the main event.

My first pegging: How it’s going…

When he first led me into the bedroom, I spotted that the strap on was already laid out on the bed. It had sturdy adjustable nylon straps and a big realistic dildo securely attached. It was definitely not like the ‘beginners pegging’ dildos I’d seen when browsing online and I told him I was impressed. He replied that he had a bigger one. Definitely a man who knows what he wants!

After we both recovered from the tremendously good fucking he gave me, the time had come for me to return the favour. I stepped into the harness and adjusted the straps while he grabbed a towel to lie on (just in case!) and reached for a large bottle of lube, plus some poppers to aid relaxation. He admired my cock as I climbed back onto the bed.

He laid on his back and I lubed up his arsehole, sliding one finger in at first to some very appreciative noises. He was comfortable and keen, so I slid a second finger straight away and pushed them in as far as they would go. I have very short fingers and so I really hoped that I would be able to reach his prostate. The feeling of being inside his hot tight hole while he moaned with pleasure was so fucking intense, and I instantly went from being curious about fucking him to being utterly desperate for it.

Pretty soon, he was desperate for it too, so I lubed up the dildo and attempted to get into position. With my knees either side of his bum, I nudged the tip of the cock into his hole and then we both guided its length as far into him as the position would allow. It was seriously hot. Almost unbelievably so. All my worries about being awkward and getting the angle wrong vanished as soon I looked at his face and saw how much he was loving it. How much he wanted more.

I’d been worried I wouldn’t have enough energy to keep thrusting, but his enjoyment turned me on so much that I managed to find my reserves. I fucked him extremely lustfully that night (twice!) and I hope to one day be able to fuck him as hard as he fucks me.

Afterwards, he told me that I’m only the second person who’s pegged him, and the first time didn’t go nearly so well. The reason he was so relaxed was all down to the amount of solo ass play he’d been doing, so I can highly recommend buying yourself some toys and lube to experiment if you’re keen. Knowing exactly what you want and being prepared will massively help when it comes to looking for a partner who can join you on this adventure. I’ll be forever grateful to him for sharing this with me, and for adding something new to my list of things I really fucking enjoy.

 

2 Comments

  • SpaceCaptainSmith says:

    Wow! Sounds good for a first try. :)
    And some good advice here, which I’ll bear in mind next time I have a go at it myself… like the guy in the story, my own first attempt wasn’t a great success. But still love the idea of it.

    • Girl on the net says:

      I do wonder if a lot of advice articles on this kind of thing miss out what I think is one of the key lessons I’ve learned from shagging – the first time you do something will often be a bit pants. The excitement of newness is all well and good, but with stuff that can be complex (and I reckon pegging definitely is, even if just because you don’t have physical/tactile sensation in the penis you’re wielding) you’d do well to lower your expectations. Naturally when I’m shagging people, the phrase ‘lower your expectations’ does not win me many plaudits, but it’s sometimes useful I think =) I hope you get to have a go yourself with more success at some point!

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