• Guest blog: My first pegging session

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    Guest blog: My first pegging session
    October 15, 2021
    Guest contributions
    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.



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