(32) Pegged on my birthday – the rush to find a room for buttsex late on a Friday night [MF]

I don’t tell a lot of people this but the greatest birthday present I ever received was a vigorous assfucking by the most talented pegger to cross my path.

It was all the more special because I was at a difficult point in my life. I was sleeping on my mother’s couch, my bank account was basically nothing and I was pretty unsure about any of my prospects. Despite that I do remember it as a bright time because I was seeing someone who as much a fiend for pegging as I was.

It was late on my birthday and I happened to be at Waterloo in the early evening. I’d seen friends out of town and was coming back on a cold winter evening to spend the night on the couch. I lingered at the station for a while, not wanting to officially end the day there. I got my phone out several times and put it back several times. I was thinking of her. We weren’t anything serious as a couple and as things turned out we never would be but I had real puppy-dog eyes for her. I made the fateful choice to look back at some very flattering shots she’d sent me of her new lingerie a few months ago, back when it was warm enough to be casual about that sort of thing. That sealed it and I texted her. A photo of me drinking a McDonalds tea in a setting that we both knew was about fifteen minutes away from her flat. I had never seen her flat, incidentally – she had said that she didn’t get on with her flatmates. I didn’t want to push the matter and felt that was as good an explanation as any.

(31) My first pegging – dommed, dressed up then dicked down [MF]

I would have been 25 at the time, quite skinny, clean shaven with long curly hair. We met on Adult Friend Finder – is that still a thing? – and I had a very bi profile looking for MF couples I could be pals with. There was some success on that front but those are stories for another day.

She was a lot taller, a little older and definitely more experienced than me. She started me off by reading her erotica – there was one particularly vivid one about facesitting and pussy worship that I still think about sometimes. I mean, I think about everything about her a lot but that one bubbles up from time to time and surprises me.

She encouraged me to write erotica of my own and to send it to her so she could get a sense of my fantasies. I had never done this before so had to think long and hard about what I felt was hot and what the gist of my daydreams were. She gave a pretty strict deadline for them and became angry when they came a little later than set – I didn’t realise that was all part of the game.