[SlyBry2010]

I was 28 and she was 42. In the late 1980s we met at a local singles group (pre-Internet) that put notices in the free advert sheet that came out every week. We talked while having brunch a couple of times. There wasn't really anyone in my age group- mostly older like her. Eventually she talked me into coming over to her place after dinner. I say that because she wasn't actually very attractive- definitely horse-faced and dumpy body shape. Very nice boobs, actually - not huge but a great handful with large (and quite sensitive) nipples. But, I wasn't getting anything anywhere else and thought what the hell - give it a shot.

Anyway we lay around her living room while we watched a couple of (regular) movies and I drank beer. She steered the conversation toward sex, and to the point of showing me an adult mail-order catalog that she regularly got that had all kinds of toys and sexy things and movies (on VHS, of course). She pointed to a pic of a dildo and said something like, "That one is mine."

Holy crap, it was HUGE. It was supposedly molded from a guy who went by "Jeff Stryker", a porn star of the 80s. The next thing I know she scampered off to her bedroom and brought out "Jeff" to show off. She talked about how sometimes it hurt her to fuck herself with the dildo and I advised her to get the usual lube from the drug store. She was like, "Wow- thanks!" Apparently it never occurred to her?

In time we started kissing and she was grabbing my cock through my shorts. I don't think she was getting much action at the time, either, so she was happy to latch on. We made it to her bedroom and she kept the lights off, with her master bathroom light on to give us a little illumination.

Well, not the most stellar sex ever. Like lovethempuffy told us, lots of enthusiasm but no skills per se. Nice to be in her mouth but couldn't stick with any action long enough. I loved playing with her tits and she definitely enjoyed. I don't recall the 'blow-by-blow', so to speak, too much but when I entered her it quite a disappointment.

I am not small but still was no match for a pussy that had been abused by ole "Jeff" for who knows how long. To be fair, I was more used to the grip of my hand than a pussy at that point in my life, but still. She had a great time because I banged her in every position she wanted to try. She was the first I experienced to actually get on top and pull her legs up into a squat and bounce up and down. Still didn't work. I know she came a few times but I never did.

We got together a few more times with largely equally unsatisfactory results. She came to my place and watched a bit of decent 'couples' porn with me. We got naked and masturbated together on my couch but she wanted the D so after a bit she stood up and turned her back to me and sat on my cock and bounced on me while we both continued to watch the porn. I really gave her nipples attention then and she just about came from that.

The only time I came was with us laying on her living room floor and making out while she tried to suck me off. Just like lovethempuffy related, she was not Ginger Lynn, and in time I just jacked it off while she licked the head and then had me shoot in her mouth.

In retrospect I was at a bad place in life then and not overly thrilled with women in general. She really didn't get a fair shake from me. I wish now that I was paying closer attention and appreciating what she did have to offer rather than just focused on the negative. Both of us definitely would have had more fun. She got married to some pathetic bastard a few years later and if she's still alive I think she's quite happy.