Talking about online connections (NSFW)

Jessica is another rather strange case and one that will take more than one post. I met Jessica on AFF. She had a photo of a voluptuous woman in lingere but didn't show her face.  For the first couple of weeks, she seemed aloof and distant. We did not write back and forth too much, but at least once every two or three days. I asked for her picture a couple of times and she finally sent me one around the third week we were talking. She was amazingly beautiful and I told her so. Our discussion finally evolved more into our wishes and desires. Unfortunately she lives a long way from me and the odds of a meetup are slim for the near future.  We exchanged photos a few times and I was absolutely mesmerized but it made me a little suspicious. Why would such a beauty be interested in someone across the country when she should be overwhelmed with suitors?  Our discussion evolved a little and I learned more. She apparently had come out of a very emotional and damaging relationship ...

Charlotte was one of the first people I started regularly talking with from AdultFriendFinder. She lost her husband 3 years prior and was ready to find a good guy to be her friend with benefits. She specifically says she doesn't want to get married again because "she's too old for that nonsense." I think she is in her 40s. We began talking offline from the website using text messagaing sometime in July and have been talking ever since. Charlotte is a real enigma. She and I have discussed everything you can imagine from our past pains to our current struggles, and finally our future hopes. She talks about sex, but not in the typical way you would find from the scammers. She is interested in hooking up with a man but doesn't talk dirty or try to entice me like so many others have. She wants to meet up some day and spend days together having fun and loving each other, but she has never once said she loves me. She does not display the typical traits I've seen from...

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My time with Olivia began very differently than I thought my first online encounter would be. I spent weeks trying to figure out how I would possibly pursue an online romance. Olivia reached out to me on Mastodon and chatted a small amount for a couple of days, but then suggested security was poor and she wanted me to contact her through Telegram. Yes, my very first attempt reached out to me without any pretext from me. I thought maybe karma was being good to me! On Telegram, our conversation turned to our desires and she offered me a "menu" of possibilities, stating she was a content creator and an escort. I spent the next week trying to determine if any of this was legal and if I could be getting entrapped... I was clueless on what an escort even does (well not clueless but unsure what all that entailed). I agreed that I would love the boyfriend experience and wanted to hang out with her and see where it went. I viewed it as dating and paying for her time on the date, nothi...

I could write a book about how I got to this point, but I think you would get bored. But understanding my background is probably important to understand how I got into these situations.  I have been married a long time but I am extremely lonely. You see, my wife was injured in a car accident and now lives under constant care in a nursing home. She's been there over a decade and I miss our relationship. I visit her almost every day but I don't know if she recognizes me or even knows what's going on around her.  At some point this year, the loneliness became crushing. I miss the contact of a woman's skin, and the smile she gives, the little hugs, and funny quips. I miss the sex. I don't even know how long it's been, but I assure you, it's been too long. I've dealt with the ethical and social repercussions of finding someone to hook up with and I decided I need to do something for my own life too. My mental health has suffered and I have found that depressi...