I wrote a whole hunk of text about my meet, but for whatever reason I can’t seem to post it. So, here’s the extremely abridged version:

Within about two weeks of posting my ad on this subreddit I was sharing a BDSM session with a gorgeous and extremely friendly lady. The entire encounter went as smoothly and naturally as anything. It was a real testament to how well we communicated from the starting line: our correspondence was light-hearted, evenly-paced, and candid. It created a certain sense of trust and comfort which I think is really key between two perfect strangers in a situation like this.

We met at a hotel I was staying at one weekend. I came out to greet her in the car park, having donned my chastity cage, a rather large buttplug, and a purple man thong per her request. To the world, I was nought but an unassuming bloke, but my mistress for the day (let’s call he Lady T) knew better. She wore a corporate-chic black pencil skirt and pink blouse, already sporting an air of dominance; the heels also helped.

Having wandered back up to the room, we hold a quick show and tell of all the toys we collectively brought, including some weird and wonderful dildos and Lady T’s heavy-duty leather strap-on harness. She directed me to undress, leans me against the wall, and starts playing with my plug. She slaps my ass here and there, leaving scarlet hand prints whenever she does, and tells me I have “a slutty hole” — it’s the sort of enthused degradation I had been missing, and yearning for, in my ordinary sex life.

Afterwards, I help her take those heels off by providing myself as a foot stool. The sensation of the soles of her feet on my bare back is surprisingly really nice. She allows me the privilege of undressing her the rest of the way, down to her black, lacy lingerie. The harness comes on and, before long, I’m deepthroating a pink 8-incher. Lady T’s impressed gasps make me feel really good about myself, and encourages me to do more…maybe too much, as I gagged hard once or twice, leaving trails of thick saliva running down my chin.

She lets me clean up right before leading me to the bed to remove the plug. A feeling of relief courses through my body, only to have the plug quickly replaced by her fingers. I moan as she explores, she tells me how easily her fingers slip in and out, and by this point I’m sure I’m already leaking through my cage.

Eventually, the head of the dildo is pushed into my anus and the real pegging begins. All sense of time after that point is lost to me. How much of the three hours we had together was spent purely drilling my asshole? I’d wager a lot. We tried all sorts of different positions, introducing different accoutrements like ball gags, ankle/wrist restraints, vibrators. I could go on and on and on.

By the end of the session, I just had to say stop. As much as I wanted to yield to every wish and whim of my mistress, fatigue had set in, I was truly at my limit. It’s like the opposite of that one R. Kelly song (my mind is telling me yes. But my body, my body is telling me no!) We tried something a little more gentle to finish: Lady T queened me whilst I jerked off with a free hand, having been released from my cage. We both came to orgasm in unison, and so ended our kinky session, coincidentally right on time as originally planned.

We cleaned up, said our goodbyes, and both shared the hope that, circumstances permitting, we might have another session in the future. I glossed over a lot of details but hopefully the success story encourages and motivates those reading who have not yet been met with a lot of success that their efforts are not all in vain. There’s somebody out there, you just have to be patient and positive and take everything in stride.

TL;DR met with a nice lady at a hotel, pegged a lot, great time had by all.

Thanks for reading x