I've been attracted to older women for as long as I can remember. So much so that I was never very interested in dating younger women or even women my own age. When I was in my late teens I started sleeping with a woman in her mid-40s. We met in a bar and she took me back to her place at the end of the night.
I was very inexperienced and incredibly nervous to say the least. I'd only ever been with a couple of partners at that point and she was bigger than anybody I'd ever been with, she was the 1st "real" woman I'd ever been with... curves in all the right places and some of the wrongs ones... she was incredibly sexy and I was a bundle of nerves.
Being so inexperienced I was keen to follow her instruction and the time I spent with her taught me the most important aspect of good sex - "active listening". By that point I'd only eaten pussy once or twice before and didn't really have a clue what I was doing. She told me when and how to lick her and I kept at it until long after my jaw started to ache, in-fact my jaw still clicks to this day after that single night.
I was using my fingers to penetrate her whilst caressing her clit with my tongue when she prompted me to insert more fingers and I happily obliged. It wasn't long before I had my fist wrist deep in her pussy and she rode my arm till she gushed. Afterwards she returned the favour and gave some amazing head before telling me she wanted me to fuck her ass. That was another 1st for me and for a long time after this was the gold standard which I measured all my subsequent sexual encounters against.
In my early 20s I struck up a friendship with a couple of swingers. The guy was in his 40s and woman in her early 50s. Not to toot my own horn but I was an award winning photographer and they were keen on producing some amateur porn. I went out to their place and we filmed a couple of scenes, voyeur with her in the shower. I cut a hole in a shower bag to create the illusion of a hidden camera. We did a solo masturbation scene of her pleasuring herself, her partner walking in and then her sucking cock and getting fucked from behind. We also did a lingerie shoot, when we were about done she declared to her partner that she was going to give me a blowjob.
My participation hadn't been discussed prior so I was a little taken aback as her partner encouraged me to enjoy her mouth. I'd clearly been very aroused throughout the session but had tried to maintain a level of professionalism but that quickly went out the window when I had this sexy older woman offering to suck my cock.
Although having someone's partner watch them giving me oral was a bit far outside my comfort zone it was a very erotic experience and I don't regret choosing to participate. Years later I bumped into the woman and we became quite close. I was in my early 30s and she's in her early 60s. Her previous partner had died and was living with someone else but they were sexually mismatched and she was sexually frustrated.
We met up at least a dozen times or more and had some of the best sex I've ever had. Dominating a much older woman was thrilling and she had very few hard limits. She is perhaps the most insatiable woman I've ever had the pleasure to meet. The problem was that she wanted me to fill the emotional role of her previous partner which was problematic for a number of complicated reasons, so things cooled down but we still remain friends and I'd be lying if I said there weren't times that I'm tempted to call her and ask if she wanted to meet up for one last last hurrah! |
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I am beyond tempted but only have her landline number and wouldn't want to rock the boat with her current spouse, hoping to bump into her in person again so can chat naturally and catch up rather than hounding her for sex. |
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