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Back in the days before the internet, you could buy these weekly sex newspapers at liquor stores and adult theaters. They were loaded with classified sex ads, all worded much like a paper Craigslist. One ad caught my eye: “Widow looking for gentleman for physical fun.” and then a P.O. box. I wrote to the PO box, described myself and got a phone number in return. Not expecting much I called the number and got this low, male sounding voice who immediately said something along the lines of “I have got a low voice but I am 100% woman and my ad is legit”. This was before the days of transgender so I accepted that as the truth and we chatted. It turns out she was a widow in her early 70s and wanted to screw around some more before it was too late. I certainly couldn’t argue with her logic and immediately got a boner when she said she was in her 70s. I have always had an attraction for women older than 20-30 years than me and they were absolutely prime in my eyes. I don’t know where that attraction came from but I remember as just a little boy wanting to rub my penis and balls over girdles, hose, and high heels of family women friends. At this time, I was in my late 40s and horny as hell and could not wait to meet this lonesome widow.
At the appointed hour I knocked on her door in a very plain apartment complex similar to the kind all over southern California with a pool surrounded by a second story and balconies. Zelma opened the door and I was presented with probably one of the homeliest women I have ever seen. From the neck down she had the usual grandma body of big saggy tits, thunder thighs, a big soft ass but very nice feet. Her hands and fingernails were well kept up and they were very handy later. But her face only a mother could love as she had a prominent overhanging forehead above her eyes that would look fine on a man but not a woman. The actress Missi Pyle has the same type of forehead but not to the extent that Zelma had. I noticed that the wrinkles on her face also included around her mouth, probably due to a life of sucking cocks, I hoped. Having said that, she had a wonderful personality but it took me a while to get used to that low voice.
She invited me in and we chatted on the couch and she told me that her dead husband was a jerk, cheated on her, liked young men to suck his dick, and she was happy to be through with him. She was estranged from her kids and never talked about them much but found herself living on social security in a low rent apartment and too old to be hired for anything. That said, she wanted to do some fucking before health problems even took that away from her and that is where the ad came in. I asked if she had any luck with the ad and she said very much so. In fact, she had to keep the appointments in an appointment book but also admitted that most never came back. Finally, she stood up and said “OK, lets see what you got” and walked into the bedroom. Jeez, Louise, I had never run into anything like this before.
Walking into the bedroom she took off her thin house coat sat at the foot of the bed and motioned me to stand in front of her (I had peeled off my clothes at this point). With her big saggy tits jiggling she rolled a condom on me and lay back on the bed and pulled her legs up. Her next words were “OK, Go to it”. In spite of this touching and tender welcome, I actually had a hard-on and could not wait to bury it between those big labia. My greased boner went in so smoothly and she gave me encouragement along the lines of “That’s it. Pump that cock. Get it in me. Don’t stop.” And pump I did and watching her titties bounce up and down pushed me over the edge in far too short of time. I squirted cum again and again until I was absolutely empty and slowly slid out.
Getting dressed, we talked a bit more and then she informs me that she usually gets $20 as a thank you gift from the guys she sees. Well, that was news but $20 even back then was pretty reasonable for a professional orgasm so I had no heartburn on leaving a bill on the dresser. Besides I liked it. I did leave, though, totally underwhelmed by the whole experience but a week later I needed a fuck again and gave Zelma a call. Men are pigs, I admit, but things got better.