[explorer98]

I've been fortunate enough to participate in a number of ladies' first anal sex over the part 40-odd years but I think only two occasions merit entry here.

The first was long ago when we were both 19. We hadn't been together long and out first sex had been quite eventful when the young lady very confidently dropped herself astride me in the back of my 1970 Mini Van, promptly launching herself vertically as I invaded more of her 'personal space' than she'd anticipated, almost reshaping the van roof in the process!

Note to our transatlantic friends at this point; a 1970 Mini Van in the UK wasn't like an Astro/Aerostar/Voyager kind of thing - it was a nasty, little box on wheels, derived from Alec Issigonis' 1959 automotive masterpiece. Google Austin Mini Van and you'll see what I mean.

Anyway....

Some weeks later while babysitting for her sister, Jackie and I ended up pretty much naked and exploring each other after the small types had gone to bed and somehow - with her on all fours - I found myself fucking her cute little ass - and this didn't give her the slightest problem!

From that day forward, she was always more easily able to accommodate me up in her tight little ass than she ever was in her pussy!

Fast-forward 23 years or so, by which time I was very involved with the delightfully GILFY Amelia and between us, up to all kinds of mischief!!

She was having a change-round in her office (Head of HR doncha know!) and was moving the furniture. She asked if I'd help with the heavier pieces and of course I obliged. She must have been feeling particularly mischievous that day because every time we came within arm's length of each other, she grabbed my cock through my trousers and gave me a squeeze or a rub!

I could see the minx in her face and at one point 'warned' her; "DO that again and that will be going right up your arse!" We'd tried anal once before - her first experience at 57 - and I just couldn't get inside her without hurting her too much so we'd abandoned it.

Two years later and here with are in her office - between the Managing and Technical Directors - and she's playing up for all she's worth!!

I'd got the tall filing cupboard across her doorway and she very delightfully unzipped me, took my cock out and very quickly brought me to a size I hadn't experienced in a long time!! She gave me that slightly 'coy-but-naughty' look from under her eyelashes (she has SUCH expressive eyes) so I really couldn't help but respond!

I pushed her face down across her desk and flipped her long skirt up around her waist. She was wearing the customary thong underneath which I pulled to one slide and slipped a couple of fingers into her.

She was soaking wet as usual!!

I slid my cock into her going full depth in a single stroke, gave her a couple more to make things well and truly juicy then pulled out before embedding myself balls deep in her delicious arse!!

Using her own juice as lube was delightful and she barely flinched as I forced my way fully home inside her. Probably for the best considering the two guys resident in the adjacent offices (would have made for an interesting disciplinary!) and I fucked her quite firmly across her own desk.

Her first (successful) anal sex at 59!!

It wasn't long before I was pumping cum deep inside her and I have to admit there was a certain perverse delight about leaving the lovely lady just fucked and pumped full of hot cum at 2 in the afternoon with another three hours to go! All she could do was carry on as if nothing had happened while my cum tried to make its way out of her!!

Glorious!!!