Pegging an older first timer [FM] [mild femdom] [lengthy exposition] [affirmative consent] [aftercare]

I have many favorite sexual things: giving and receiving oral, being just bratty enough in public places to provoke an immediate dicking down in private (or private enough) places, strapping-on for a willing partner, and even lately, after the miserable touch-starved year we’ve all lived through together, just laying next to another human, feeling the heat and sweat and perfection of skin to skin touch with them, ideally in the afterglow between round N and round N+1. But my most favorite thing is edging my partner until they tip into the wild throes of an intense whole-body orgasm, the kind of orgasm that demands long stillness before the recipient is capable of ego recollection after its dissolution into the vast sea of nothingness that is ultimate reality. (Aka Switch’s grand unified theory of what happens when we orgasm, as heavily influenced by popular conceptions of Eastern philosophy.) The kind of orgasm where, once they’ve regained their executive functioning enough to words, the first thing they tell me is either that it feels like I’ve just sucked their soul outthrough their genitals (*leaving me to wear it on my face, yummmmm*), or, as with my recent Tinder date, in the same bed he shares with his long-distance wife, to incoherently babble to me about how “by far – far far far away – that was the best sex I’ve ever had.”

Is it wrong to brag about what a ridiculously high percentage of my partners have told me this? Like, every single one of them since I learned wtf I was doing in bed, mostly by getting myself right with myself and more comfortable with my present feminine embodiment in my early 20s. Maybe it is wrong, but if I can’t share this with anonymous, slut-loving strangers on reddit then tell me who I can share it with? I am so talented in so many diverse, well-recognized ways in my real life and pursuits. Yet it still tickles me pink knowing that lurking beneath my librarian-like reserve and sometimes poise sometimes hella awkwardness is this one set of hidden talents that only a dozen or so lucky humans can attest to. It gets me off just thinking about how much higher I could push that number if I wanted to, how many more people could recognize me as “their best,” jerking off to memories of me for years to come. These are the life goals I feel but never say out loud.

I felt a slight pang for my recent lay (older doctor who gave off strong daddy vibes in photos, but stronger switchy sub vibes in bed, *mmmmm, love the role reversal*) when he told me this. What sad variety of vanilla sex was he typically having? Why would he marry someone who didn’t equally enjoy sex? Did he not realize that was barely even my blowjob B-game, that I save my best for dicks attached or strapped onto people I actually love? That the first time I had sex with a partner was only ever the best with me if it was our only time together? Reader, I know it kind of makes me an asshole to like, go into something with no future with the intent of low-key ruining that activity for my partner in their future life without me in it, but honestly when he told me that it only made me more determined to give him a taste of what “my best” actually might be.

Especially since he was into ass-play. Strapping-on for a wanting bottom always gets me insanely hot, but there’s something about the dynamic when it’s a dude – specifically a cis-het dude – asking that gets me even wetter. So, on only the second time we met (presciently intuiting that there wouldn’t be many more, alas), I brought him a present: a 5” long, totally non-threatening, a-realistic purple dildo, and my personal bottle of lube because if I was going to eat wet ass while warming him up that shit best be organic. Standards are important.

I let him eat me out for over an hour before we broke out the harness. Occasionally I deigned to tease his dick with my stray, brushing hand, or graze his foreskin with my tongue before moving to suck his balls or gently nibble on his nipples. I’m ordinarily far more generous than this kind of pillow princess behavior, but he came too easily to give a ton of stimulation to early on, so this was actually by request. After riding his face through my own series of orgasms, I lay back, somewhat spent until he asked me if we could try the dildo now. I leapt out of bed, recollected myself (after all, he is a person, not just an object for me to fuck) and leaned back in to kiss him passionately before eagerly stepping into the waiting harness.

Strap-on harnesses are such fidgety things. I tried to fill the awkward lag between him asking for my girldick and me being set and able to fill him with my girldick with a mix of dirty talk and affirmative consent reminders. (I wanted our safe word to be pineapple, but he chose eggplant, which still makes me lol in hindsight because it was indicative of a broader lack of creative thinking that, ultimately, is just not very sexy to me.) Girldick at the ready, I readied him by putting a pillow under his hips and leaned in to give him a B+ level blowjob; good enough to make it memorable af but not so over-the-top that he would blow in my mouth before the real fun got started. Sloppy, loose but constant hand action, lots of breaks to suckle his balls and lick and tease his perineum.

By the time my tongue made contact with his asshole he was moaning intensely and even pushed my still working hand off his dick to lessen the stimulation. I moved up to lick his ballsack while slowly inserting my first saliva wet finger up to the knuckle. “Oh my god,” he gasped, his body beginning to flex and tense up. “Too much?” I asked, pausing. “No keep going, give me the dildo,” he begged. I moved up to kiss him, holding him close a moment. “I’m gonna fuck you so good, baby.” “Please fuck me so good,” he said, holding my gaze so tenderly that just for that moment I loved him, and promised myself I’d go real slow, not being a dick about this as I maybe have on more than one occasion before with more than one partner even in my less kind youth. I slowly lubed up the dildo, working the extra around his hole before again taking his length in my mouth, teasing him, edging him still closer and closer as I warmed him up once again with my fingers.

I stopped. “I’m ready” he told me, spreading open his legs for me a bit further. “You are so hot, baby” I told him, kissing up his inner thigh before grasping his leg with one hand, stabilizing the slippery dildo with the other as I started to push in. He moaned unintelligibly, drawing large breaths like he was already going to cum. I slowed, feeding him my girldick inch by inch until I was fully holstered in him. I wanted to make this beautiful for him, to reinforce his masculinity even as I topped him. I leaned in to kiss him, holding him closely before slowly rocking my hips into his ass in a steady rhythm. I wanted to say dirty things to him, to make sure he knew who was the top now, who would always be the top whenever we were together (like I said, sub vibes). But I didn’t want to push him away or scar him. It was enough that this man – older than me, professional, established in the world – had begged me for my strap, taken me into him, and now squirmed under me in pleasure.

I wanted to keep going, to turn him around and fuck him from behind while working his shaft with my hand until he came shouting my name in a messy explosion of cum all over the bedspread his wife had probably picked out. But he asked if he could finish in my mouth, and never being one to turn down a possible facial of course I obliged. Afterwards I held all 6’ of his body against my substantially shorter body, spooning him while I kissed his neck, ran my fingers through his chest hair, and generally provided all the aftercare I wished my first partner had given me after my first time (another story, another time). We laid that way, him lost to words, for nearly an hour before I rode his face one last time and left, cum still crusted into my cheeks, to go sleep at home in my own bed.

Source: reddit.com/r/gonewildstories/comments/nino6i/pegging_an_older_first_timer_fm_mild_femdom

1 comment

Comments are closed.