So I’ve posted on and off here about the various escapades that I used to get up to with my (now ex) girlfriend. It was a pretty wild time in my life – being two rather horny young adults with a raft of kinks you’re desperate to try will do that to you, after all.
This particular encounter occurred during one of our lazy Saturday mornings together, where I’d been mouthing off a touch too much about my gym progress. For context, I’m a 6’, 72kg, fairly slim to average build – and my actual gym progress during this period could well have been described as having changed from ‘nothing doing’ to ‘maybe-something-minor doing’. Regardless, I was very proud, and way too smug about it.
Which is how my girlfriend came to suggest a bet, ostensibly with the intention of shutting me up about my ‘progress’ for the foreseeable future. It was a simple concept – if I could complete 50 pushups in front of her with a ‘minor’ handicap, I could continue bragging about my alleged fitness to my heart’s content. And if I couldn’t, she’d just have to gag me for the evening, to be rid of my arrogance.
Of course, 50 pushups is a relatively easy target – most people can get through that without breaking too much of a sweat, even if being mildly uncomfortable. However, my ex being my ex, she’d set this target knowing exactly the kind of ‘handicap’ she’d like to force on me.
First, she’d had me strip naked for her in her room, even as she remained completely clothed, with the usual predatory smirk on her face that usually accompanied her enacting one of her latest twisted ploys. Already slightly aroused by the changed power imbalance between us in this situation, she then handed me my spandex catsuit – the bodysuit she’d use frequently when playing the top in our relationship. It’s form-fitting, almost-invasive tightness, and my inability to remove it on my own had a tendency to screw with me as a sub, making it the perfect uniform for whenever my girlfriend wanted to fuck me over both figuratively and literally.
As a side effect, wearing a bodysuit also makes it that much easier to apply rope, tape, or any other kind of restraint easily over the body, without fear of ripping out hair or leaving highly-suspicious marks all over. It was this secondary use that had me worried (though ashamedly also slightly excited) about what was meant to be a simple, relatively non-kinky challenge between partners.
Perhaps sensing my suspicion, my girlfriend assured me that I wasn’t being tied up – as ‘that’d just be mean’ (clearly), and that she just wanted to give me an incentive to finish the challenge a bit faster. That incentive, she explained, was the magic wand that she was going to tape on the inside of my thigh, positioned with it’s head rested gently but firmly on the base of my shaft, with only the thin material of my bodysuit between the two.
Naturally this made me a bit more nervous about the challenge, as my girlfriend shepherded me over to her mattress to begin. 50 pushups without any hindrances holding you back was easy enough, but 50 with a vibrator buzzing away beneath me? That was a more difficult proposition.
Assuming the push-up position on my hands and toes in front of her, she asked if I was ready to begin. Nodding, I felt her hands (seemingly very deliberately) feel their way teasingly around my thighs for a few seconds, before the switch was flicked and the vibrator rumbled into action.
Fuck. Within seconds, I’d realised I’d clearly underestimated the impact of the vibe was going to have. Already aroused by having to strip down and effectively give a show to my girlfriend, I was already hard enough for the wand to buzz away at my shaft in a spot that was unforgivingly pleasurable. And with only a thin layer of spandex between me and it’s vibrating head, I was bearing the full attentions of a toy usually employed to give orgasms to girls who struggle with orgasms.
Four push-ups in and I’d elicited my first moan, all-too involuntarily and drawing a crack of a smile from my ex. What I’d discovered was that every dip into the lowest part of my push-up would push the wand ever so slightly into the mattress, and in turn press it back up against my cock, effectively making every push-up a stroke of myself with the wand.
Trying to think of anything but the situation I was in, I battled through to fifteen pushups, to sixteen and seventeen, even as I could feel the constant and relentless stimulation building the throes of an orgasm in me.
My ex, kneeled beside me and greatly enjoying the show, took to feeling me up as I struggled through the repetitions. By the early twenties though, I pretty much already knew it was over. I was effectively past the point of no return, and actively struggling to avoid the next, slightest stimulation that would push me over the edge.
That came on the twenty-fifth repetition, as I dipped myself down and the vibe pressed into me again ever so maddeningly. Perhaps sensing the opportunity to screw with me at the halfway mark of the challenge, I felt my ex’s hand on my ass as I hit the lowest point of my rep, firmly and decisively pushing me much deeper into the mattress than I’d anticipated or aimed for.
The additional pressure from the wand was all I’d needed to lose what little control I’d had left over my building orgasm. I remember a gasped ‘no… fuck’ leaving my mouth as I came, and came hard into the mattress underneath me, my girlfriend’s guiding hand keeping me firmly in place as the spasms ripped through my body.
In my post-orgasmic comedown I could only roll over back onto my back and close my eyes, completely exerted, as the wand continued to vibrate against my now spent cock, and my girlfriend lay down very smugly to cuddle up next to me. I was going to have to be gagged for the rest of the day, no doubt – but perhaps it was worth it?
Source: reddit.com/r/gonewildstories/comments/d77eb8/that_time_my_girlfriend_f_made_me_m_a_kinky_bet_i
Not too bad of an ending? Sounds glorious.
“50 pushups is a relatively easy target” what.
you did push ups on a mattress?