Before I get started with the story. Thank you for all the messages! I've had some inquiries that I thought I'd share and cover off on:

1. "How big is your cock?" I am very average in length ... not quite 7", a bit thicker than average girth ... I'll work on getting a pic posted. Also, catch the reference in the story below!
2. "We're all of these adventures short term things?" ... even though I tell the ending, some were ongoing. For example the Wisconsin Girl lasted about 18 months. I continued fucking the crazy hot young chick into 2015. So, lots of overlapping.
3. "Are you currently seeing anyone?" Yes, I have two women (both of them I met prior to Covid) that I am seeing and I just had a promising first meetup with an old neighbor of mine. She's still extremely attractive and even though we hadn't seen each other in at least 18 years, I think there is still something there!

The Pilot! I had resisted reposting my award winning "S.A.A.D" ad for most of 2012 after my experience with Thunder Thighs (ch. 6). I figured .. hey, it's a new year, what the hell! Posted! Almost instant results! Several replies, but two very promising ones. One of those was the Pilot!

I figured she was at least 12-15 years older than me at the time, had an adorable face and smile, short, petite brunette with huge tits, a great toned tummy and legs. I was instantly attracted to her because she was a mix, in looks, between a gal I used to work with and a friend of my wife's! She was from a neighboring state, but willing to make the drive to visit me.

She was married to an older guy that was also a Pilot. It seemed that over the course of a few years, he lost the inability/need for sex. She had cheated previously with other flight staff on over night trips, but really wanted something regular/long term.

We chatted for a few weeks, exchanged pics, had plenty of cyber sex/sexting. When we found a day that would work for both of us, we set it up right away! She booked the room and told me to meet her at 1 PM, sent me the room number and instructions what to do, and how she wanted to fuck.

As per the instructions, the door was partially open when I arrived at the room, she was laying on her side on the bed, facing the door, she was wearing a white dress shirt with nothing on underneath! The top few buttons were open to show off her huge cleavage. She looked amazing! She was super tiny on that huge bed, maybe all of 5 feet tall!

I am pretty sure I said "hi", but not much else was said. I made my way to the bed, opened her shirt the rest of the way and we made out, me clothed and her fully naked! I went down on her first and then she finally pushed me off her and unto my back and undressed me from the waist down, shoes first, then pants, boxers and then socks! She gave me a really good blow job, lots of spit and good suction! She eventually scooted up and slipped my cock in her and fucked me until she had her first orgasm. She fell forward and just layed on my chest, saying she needed a break! I was still hard as a rock and remained inside her.

She had a full bush of hair, and an extremely tight pussy - no kids. She seemed shocked that her pussy could get wet with me! Age thing? She was really loud when she would have an orgasm, oh god, oh god, oh god! It was definitely a job to get her there, both orally and with penetration. Speaking of penetration, that first meetup, I remember fondly (or not so fondly) as I entered her, her saying "Oh god! (well) AT LEAST you have really nice girth!" I took that to mean either she wasn't happy with my length or she REALLY liked my girth.

Either way we fucked until I had to get going and get home for "family" dinner at 6 PM ... there was never a mention of condoms being used or not used until later that evening when she wrote over email "god (there it is again), I really hope you don't have any diseases! I didn't realize we were going to fuck without a condom. And you came in me all three times without asking!"

That's pretty much how it went after each meetup, possibly a guilt thing? I'd have to talk her off the ledge each time and then the next day she was ready to set the next meetup date. Hot sex, but way too much drama in between!

During the time with the Pilot, I was still on Craigslist and still chatting with others. Even though the S.A.A.D ad was no longer being posted, the Pilot was smart enough to recognize my writing style and found at least four other ads that were running. I denied that they were mine, but it was clearly time for departure!

One of the women that I was chatting with while I was still fucking the Pilot was Hot Ski Chick, she would send me a new nude everyday to "keep my interest" until she could get away and meet!

Stay tuned for another hot chapter ... Ch. 15 the Hot Ski Chick!