I have now shared 4 confessions on erotic encounters with 4 different women, but now I want to go back a little earlier in time and describe some encounters I had with woman I met on telephone chat lines. In the late 1990s and into the next decade, this was how I’d try to meet women. The services ran ads in the back pages of the local alternative weekly, Quest and Nightline being the two most prominent. Men were expected to pay for their time, but I discovered that first-time callers got a certain number of free minutes, and this sent me scrambling around town in search of phone booths — yes, they existed then in abundance — to get as much free time as I could. I even called from all 6 of our office lines, and the fax line too. Sometimes after a few weeks, the chat lines would expunge their record of which phones had already used up their free minutes, so you could start all over again. I did not want to pay for a chat line service, as my wife might discover this on our credit card bill.
The way these worked is that you’d scroll through the women who described themselves and what they were after, and you could send them a message or ask to connect live with them. It was mostly a complete waste of time, with low-class women of limited intelligence and it got worse as the years rolled by, but I was so climbing-the-walls horny that this did not stop me. You had to wade through these women and the escorts and men trying to pass themselves off as women to find the rare jewels. And of course there were far more men than women. I confess that I sometimes played childish pranks, either because a woman did not respond to my messages or they were too stupid sounding for words. For example, I would record myself taking a piss and flushing the toilet and send that to them in a message. That always got a response! I am laughing now remembering this. It was fun.
But I had some successes for sure. One evening I connected with a younger Black woman who was a single mother. I was visiting my mother’s place at the time while she was out of town, and calling from my mother’s phone … how naughty is that? I talked her into inviting me over, and she asked me to call her from a phone booth at a gas station next to her apartment complex. She did this so she could check me out from her second story bedroom window, looking over the privacy fence. I charmed her into inviting me in, but she made me hop over that fence and enter through her downstairs patio. She said too many men in the complex were hitting on her and she did not want them to see me come in the front door. I can’t believe I actually managed to scale that fence, which was taller than me. That’s what desire will do to you.
This was late at night and her children were asleep upstairs. We sat on her couch chatting for a while. She was cute and busty and a good deal shorter than my 6 ft frame. I wondered where it was heading when finally she said, I feel this overwhelming need to kiss you! We kissed and squeezed each other, hands roaming over each other’s bodies. She pulled off her blouse and removed her bra, revealing two wonderful boobs, with big brown nipples, way more that a handful of flesh and plenty of fun to squeeze and lick. When I removed her pants, I found a nice patch of curly back hair above her pussy, which I set myself to devouring as I fingered her. This woman loved to be eaten more than anything in the world, and she would delay her orgasm to get the most out of it. Then I would eat her again, and then — oh joy! — she’d set herself to sucking my dick until I came in her mouth. Once she said, Does my baby need to cum? That was such a turn-on that exploded in her mouth right away. My wife has never enjoyed giving me head, so I craved blowjobs far more than fucking.
This was the first Black woman I was intimate with but not my last. I am not at all racist and am pleased to have enjoyed her company. I used to call her when I worked late and ask myself over. She never said no. The only time we ever fucked was that one evening when I asked her to meet me in a motel. We did our usual thing and then she asked me to jack off and cum on her face. No one had ever done that to her, she said. I was more than happy to send streams of hot cum on her cheeks and lips, and then have her her lick the head of my cock clean. That is a huge turn-on for me. I stopped calling her after a time, moving on to craigslist. I know she found herself a boyfriend after a while, and I was happy for her.
Source: reddit.com/r/gonewildstories/comments/hva574/before_there_was_craigslist_there_were_chat_lines