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My [M61] First Successful Craigslist Hook-up
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I am reposting a series of confessions that I posted during the pandemic under another handle, then pulled down. Too bad I did that; it led to some memorable email discussions and one splendid virtual friendship, and maybe reposting these stories will lead to more. Let us see.

This will be the first installment in a series of confessions on my erotic deeds / misdeeds. I offer these not to brag, though there was often joy and exhilaration, or with a sense of conquest. And I offer them without moralizing, though there was also at times degradation. I tell them because we are all storytellers and where else but on an anonymous board like this one can I tell these stories? You can judge them and me if you want, but I can promise you that they are all true. So read on.

About me -- I am now in my mid 60s, well liked and respected in my profession, a 'success' I suppose in that sense, and also have grown children and a few grandchildren who hold me in esteem. And I have been married to the same woman for several decades, the only woman I have ever been married to ... unless you count that period of my great affair, when I loved and was loved by two women and somehow managed to get through it with family intact. But that is not the story for your ears, no offense, as I hold my experience with the other *her*, may she rest in peace, as sacred. But I digress.

A final few words on me ... I hold an advanced degree in the liberal arts, lived a number of years in Europe, speak a couple of foreign languages, and am fit and attractive for my age. I was a wallflower in high school and overlooked, but bloomed late. I came into my own, sexually and otherwise, well after high school. I now live in a major Texas city, in a house that is paid for, not wealthy but comfortable. I know how fortunate I have been.

I begin my confessions with a story about craigslist, long before the moment when the personal pages were pulled down. You know the ones. I can't begin to count the hours I spent -- wasted? -- browsing those ads. This would have been in the early 2000s. I had answered and posted ads before, but with no luck, till one Friday when my wife was away for the weekend, on an impulse, I posted an ad on Casual Encounters with the unoriginal title: Playtime? I had the idea to pretend that I was from out of town, visiting family but staying in a hotel, or able to get away ... I can't recall that detail. But I can tell you that saying you are from out of town, whether it's true or not, will increase your chances of getting laid if you are a man. Some women do want a true one-time no-strings experience, and what better way than with an out-of-towner? I did this many times after this, and it always seemed to increase my chances. Sometimes it was even true,

What I do recall is that I almost immediately got a response -- it only takes one -- from a woman living on the other side of our growing town. We swapped a few emails and Yes, she wrote, she would love to meet me, in a hotel that very evening. She just needed time to get ready. So I chose a modest (OK, maybe a bit less than modest) hotel close to her place, a good 50 minute drive from my home -- I used it several times after this with several different women -- and communicated its location and off I went. I prefer hotels that do not have a lobby, so neither of us has to expose ourselves to the prying eyes of staff, and to lessen the chances of being seen by someone who knows one of us. Motels, really, I suppose. Motel 6s can be dumps (this was not a Motel 6) but some are perfectly fine for trysting.
I feel the need to get to the room before the woman, always, whether she is a regular -- I did eventually find some regulars and am so grateful to them -- or a one-time thing. I like to get the feel of a place, clean myself a bit more, peek out the window in anticipation. pace a bit ... it builds my excitement. I am at a place now where just being in a hotel or motel room arouses me. Even the smell of motel soap calls back memories.

This was one of those places off the frontage road of a major highway, backing up to some apartments (the room was in the back), near a couple of shopping centers... perfect for a tryst. We were on the second level, and there is no lobby here. You park, walk up steps, and find the room.
The knock came and I opened. I remember peering through the curtain to make sure she was as she said, and alone. I opened and in she stepped, very attractive, blonde, voluptuous, all dolled up. I knew she liked me right away, as she released a sigh of what struck me as pleasant surprise, and broke into a big smile. She asked that I be patient as we embraced and kissed, sensing my hunger. I certainly liked her. So we took it nice and slow.

We caressed and kissed for a few minutes while standing just inside the doorway, and then I took to undressing her slowly. I discovered to my delight that she was wearing shear black crotchless panties. This is a huge turn-on for me. She later offered to wear red ones for me, but that's getting ahead. For now, I pushed her to the bed, kissing, hands on her thighs and tits ... did I mention how lovely her tits were? Natural and grand, with pink responsive nipple ... and grinding away. I kissed my way down her breasts and torso, licking, kissing, then to her thighs, and then to her sweet pussy, licking and kissing. I love to eat pussy and know that I am highly skilled at it, as many women have assured me of this, and they tell me with their oohs and aahs, and most of them beg for more. I can eat pussy for a long time, and have enjoyed some trysts where that was the only reason we were there. These stories will come soon enough. So I took to eating her with relish. But this is not what she met me for, and she made that known to me in short order. No, she wanted to fuck, pure and simple.

I will confess this now --- I did not read this woman accurately, was still green at this sort of thing, and my experience was too limited to know just how to handle her. She really wanted me to dominate her, spank her, turn her around and fuck her hard from behind. She even said this after a time.. Will you fuck me hard from behind? Please? Which I did as best as I could, puling her ass towards me as I slammed into her, which she loved. She was loud, a true screamer, and I was certain that whoever was on the other side of the thin motel room walls would hear us and complain. This made me a bit uneasy.

Here is another confession with this confession: my erectile disfunction prevented me from fucking her as well as I should have. I later began procuring pills for this, first on the black marker by way of craigslist, then from my MD But this did not stop her from cumming long and loud, one time only. Alas, I know if I'd used viaga, we could have gone for several more rounds. I had not yet climaxed, so she inviting me to titfuck her. This was a first for me, and I came hard all over those nipples in short order. This I liked and so did she! We cleaned up, said and kissed our goodbyes, and I walked her back to her car.

We never met again. But I did write her again and said I was coming back to town, and did she want to meet again? She said yes, as I was highly erotic in a gentlemanly sort of way, and did I prefer that she wear red panties next time? I said sure. But I canceled it, told her I had lost my job and could no longer come down. I think I felt bad about not admitting I was married. I wish I had met her one more time at least, and fucked her rotten with ED meds coursing through me, just as she wanted. I know now that she was the proverbial freak in the sheets. I ran her email address through a search engine a time or two and learned her real name and more. I never abused this knowledge, but was just curious about her. Ladies --- never use your real email address for this sort of thing! Not everyone out there will be as gentlemanly as I am.

So this was my first craigslist adventure, and I still masturbate from time to time remembering the whole of that lovely encounter. But future encounters awaited, and many were oh so much better. These will be stories for a additional posts. Thanks for reading!

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7 months ago