Mermaid hair and swing chair: an IG love story [FM]

I’ve had plenty of opportunities to gain a moment of clear mindedness after an orgasm the past 17 or so months. But I thought I’d take a different approach an instead focus on a moment of post-nut clarity for my counterpart in the story. This particular event happened just over a year ago, on 5.10.21.

I was coming off a ridiculously successful week, one that was actually my most “productive” week of the year. It started with Kate, the 25 year-old, married Australian art teacher at my kids’ school on Monday; Gina, a divorced 31 year-old mom of another kid on my son’s baseball team on Tuesday; Janet, a 30 year-old barista on Wednesday; Stephanie a 31 year-old physical therapist FWB, who I also hooked up with on Wednesday; Dana and Kelli (44 and 46, respectively), two divorcees who I met after a happy hour (you can read more about that event [here]( https://www.reddit.com/r/gonewildstories/comments/qn727o/how_leaving_a_happy_hour_early_to_get_groceries/)) on Thursday; Jaime, another 44 year-old divorced mom, on Friday, and who I actually met at the *same* happy hour the night before; Stephanie again on Saturday; and Megan, a 33 year-old sales rep I met at my new gym a couple weeks prior on Sunday. Eight different girls (one of them twice) in seven days, leading to 19 total orgasms on my part. A hell of a week I would say.

The one that got away – my nympho nursing student neighbor [MF]

I loved the April theme of the One that Got Away, and started thinking back to any I would characterize as that from my 2021 exploits. When you’ve been fishing in the catch and release pond for the better part of a year, it’s really hard to characterize anyone as the one that got away. So that led me to think back even further, all the way back to the early spring of 2010, when I was in my fourth and final year of medical school.

The university to which my program was affiliated also had a nursing program, and the cliché’s notwithstanding, there was the occasional mingling between some of the the med school students and the nursing students. At the time, I was living in an off-campus apartment complex that was popular with the students in both programs, and there would often be parties attended by both the grad and undergrad students.

It was at such a party, shortly after we had submitted our applications for residency where I first met Amy. I had been a pretty buckled down student for most of my time, so my attendance at parties was less frequent than some of my peers. But after an excruciating first half of my fourth year, when I was proving myself to the program that was at the top of my list, I decided it was time to relax a bit.

A Very Successful New Year’s Resolution – Or How I Kept an Unlikely Streak Alive [MF]

I was excited to see the January contest, as a New Year’s resolution is the entire raison d’etre of this reddit account. After a 2020 divorce and quarantine, I decided my post-divorce dating live needed to hit the ground running into 2021.

When I decided to re-enter dating, several of my friends who were either divorced or perpetually single con convinced me to go all in on apps, and so I joined a few of them, from traditional dating apps, to the hookup apps, and even put a profile in on Seeking. Plunging in with both feet, I found myself finding a good amount of potential romantic relationships in no time, and now just had to figure out how to turn some swipes and matches into dates. Once I overcame that hurdle, I decided that my best approach was volume, and tried to arrange as many dates as I could, and early on, had a pretty consistent rhythm of 5-10 dates from dating apps a week.

A continuation of my beach bar hookup in Cabo [FM]

This is a continuation of a fantastic Cabo trip with some good friends. If you didn’t read [this story]( https://www.reddit.com/r/gonewildstories/comments/qy6ksf/a_beach_bar_hookup_with_a_just_graduated_college/), it has the background that led up to this point.

After several hours at the pool, our group all headed back to the respective villas to rst and get ready for dinner Several of the group were frequent Cabo visitors, while others were on their first or second trip. The restaurant we were headed to, Tres Sirenas, was new-ish, in the last couple years, so even the frequent visitors were excited to try it.

We had grabbed drinks at the bar before going to our table and were being seated a quarter of an hour or more after the reservation time. There was no sign of McKenna, so I figured that the awkward invitation I had extended, coupled with no follow up from me, meant there was little to no chance she was going to join us. Besides, she was 21 and celebrating graduation with her friends, the last thing she’d want to do would be to hang out with a group of people anywhere from 16 to 40+ years older than her.

The one with the chubby single mom and the concert [MF]

In response to a question about some favorite hookups in the year, I shared this story about No. 92, Arielle, on 4.10.2021. Concerts had just sort of re-started up in March, but it was still very much an atypical concert experience, with long lines to get in, mask requirements, etc. This was the second concert I had gone to since things had been re-opened, used to be something my ex and I would do regularly. I was standing in line to get a water, and when the girl in front of me got to the front of the line, she realized that it was a no-cash, card only situation. I could tell she was about to get upset about it, so stepped in and said they could put her beer on my card. She said thank you, and went to hand me the cash, and I said not to worry about it.

A beach bar hookup with a just graduated college student in Cabo [MF]

I had discussed either in a gonewildstories post, or in one of the NSFWIAMA posts, that towards the end of last year, I had a bit of a windfall from an investment I had made with my friends’ real estate company. One of the things they wanted to do to celebrate that was a trip to one of our favorite spots, Cabo San Lucas. Due to travel restrictions and some scheduling conflicts, our trip got delayed to May. But man oh man, was it worth it from my perspective. I decided to share this story now, as we just came upon the 6 month anniversary of that trip, and because the girl who plays a starring role in this episode has been my girlfriend now for a good portion of the subsequent months since.

My friends have always been incredibly generous, and this trip was no exception. They wanted to fly private, and all but one of us were able to leave to Cabo on Friday the 15th, not too terribly early in the morning, but early enough that we would effectively have a full day to start our trip. So that friend had to fly commercial the next day while the rest of our little group (the principals of the company and a handful of friend and family investors who had been with them since the start) took a Gulfstream down to Mexico.

Giving a 30yo her first creampie in wine country [MF]

So back in February, I was going stir-crazy. I was vaccinated, but hadn’t really pulled the trigger on taking advantage of that and going anywhere. I decided to check out flights, and saw I could get up to the Bay Area pretty cheaply, and found a cool place to stay in Napa. I figured a few day trip to wine country could be fun. Also, wine country tends to attract women, so why not see if I could continue to score in a road-game situation.

I ended up having some good success my first three days there, as there were a lot of women in their 40s and 50s, either doing girls trips, or, like me, doing something for themselves. Also, had a good amount of great wine, and probably joined more wine clubs than I needed to, but when you have some offsite storage, what’s a few more cases a quarter, right?

By the time Saturday morning rolled around, I was definitely feeling like the wanderlust I was sensing at home was fulfilled. The short-term nature of my planning had made it challenging to get any tastings in for that day, so I started to make other plans for my last full day in Napa.

How leaving a happy hour early to get groceries led to a threesome with two MILFs [MFF]

This story came out of a request to talk about a specific girl, Kelli, who I met on 5.6.2021. So, the night before I met Kelli, I had gone out to a Mexican bar to celebrate Cinco de Mayo with a girl I had hooked up with several times before, Stephanie. Stephanie is great, lots of fun, wild in bed, and in crazy good shape and just has energy for days. She and I got after it, and ended up back at her place afterwards, and went a few rounds. It was probably 3am when I left her place, so technically, I think I had already met my 5.6.2021 quota, but I digress.

Needless to say, I was a little tired, and was planning on taking it easy on the 6th. A good friend of mine is an exec at a med-tech company and wanted me to grab a drink with him and some others at a bar near his office, which was in a business park right near a residential area. I reluctantly said I would and rolled over to the bar in the late afternoon. It was your stereotypical happy hour bar, and even in the earlier hours of what can be considered happy hour, it was getting loud, and you could tell some people were going to make some bad decisions that night.

The one with the Persian woman and the cum splashed bra (and couch) [MF]

The wife of a good friend of mine owns an art gallery, and covid had been a blessing and a curse. People were spending lots of money on art for their houses, but one of her favorite things was doing art shows/exhibitions, and that had been pretty much ruled out for 9 months. So, on the Sunday after New Year, she decided to kick off 2021 with her first exhibition, doing it in the garden area outside her gallery in the late afternoon.

My day was off to a good start, having exchanged some hot sexts with Hannah, who I had hooked up with the day before while lounging around and watching the start of the last day of regular season NFL games on TV, then heading to the gym where I ran into Kimberly, who I had met before Christmas. She and I then scheduled a late lunch, which ended in a blowjob before she had to run to pick up her kid from ex-boyfriend’s house. So I headed to the art show in a good mood.

The one with the chubby single mom and the concert [MF]

In response to a question about some favorite hookups in the year, I shared this story about No. 92, Arielle, on 4.10.2021. Concerts had just sort of re-started up in March, but it was still very much an atypical concert experience, with long lines to get in, mask requirements, etc. This was the second concert I had gone to since things had been re-opened, used to be something my ex and I would do regularly. I was standing in line to get a water, and when the girl in front of me got to the front of the line, she realized that it was a no-cash, card only situation. I could tell she was about to get upset about it, so stepped in and said they could put her beer on my card. She said thank you, and went to hand me the cash, and I said not to worry about it.