[MF] Hooked up in her car, in Alaska, in the middle of winter

Once a year, I have to go up to Anchorage to visit clients for work. This happened my very first year I went up there. I did what I typically do when I go on a work trip – go on Tinder and try to find someone to have some fun with in the evenings. However, my hopes weren’t as high as usual just because I had no idea how many people in Alaska even used Tinder.

I was 26 at the time. I had got a few matches but nothing of substance, a couple bots and a couple fizzled out. However, there was still a match that was hidden that I hadn’t stumbled across yet. I changed the age range to as wide as it could be just to see what would happen. Sure enough, I quickly matched on a girl named Lily. Her age said 18 which makes sense why I wouldn’t have seen her originally.

[M]eeting a stranger [f]rom a dating site – texting only (for now)

I’m in my late 20’s, coming off a fairly painful breakup. Needing something to take my mind off things, I downloaded some dating apps mainly just looking for someone to talk to. I felt I wasn’t at the point where a hook up, FWB or another relationship were good ideas. I went through the usual dating apps (Tinder and Bumble mainly) but there just really wasn’t anybody particularly exciting. So few people can actually hold a decent conversation.

After deleting the apps, I remembered I had a Meetme account before my ex made me delete it. I got back into it but wasn’t really sure where to go from there besides add some more recent photos of myself. I hadn’t talked to any of these people in years even though there were some old chats saved. I started going through who was online near me and one profile really struck me. She was gorgeous and said she was only looking for conversation and nothing else. Perfect. I shot her a message immediately.

[MF] Tinder hook up, in a car, in Alaska, in the middle of winter

I travel for work a lot and in February of this year I ended up needing to go to Anchorage. COVID was just starting to be talked about and spreading in some Seattle-area nursing homes. Seems like forever ago. Anyway, I went with a business partner of mine who happened to have friends in the area, so we ended up staying with them and not in a hotel.

I was scheduled to be in Anchorage for 6 days, and I knew I would be really busy most of the time. However, I figured in the evenings I could browse Tinder just for fun on the off chance I get to talking with someone. Upon arriving and getting settled in, I made the first initial swipes, got to the end before starting the 12-hour waiting period, and fell asleep.

The next morning I woke up to 6 matches! It was a record for me. However, 4 of them were bots, so only 2 were legit. One of them never responded to my amazing pick up lines, but the other one had actually messaged me first. I’m 30 currently and this girl was only 18 which I was a little sketched out by, but as usual with these apps, my penis does the majority of the thinking for me.

[FM] I hooked up with a girl I met on Omegle

I posted this once before but I got shy and deleted it. This happened probably 8 years ago now back when Omegle was a little more popular (or maybe it’s still popular, haven’t been on it in a while). I’ve always been a bit of a “sex addict” and I used those apps to find girls to skype with, sometimes sexual and other times just as friends.

I was on one afternoon and got matched with 2 girls from a state about as far away from mine as possible. Both of them were pretty cute but one of them really got my attention – she was 21, red hair which I’m a sucker for, and had a really cute smile. We ended up exchanging numbers. Over the next few weeks, we texted all the time and had some phone conversations as well.

At this point, we really hadn’t talked about anything sexual, so I figured this was a platonic friendship. Totally fine, I still enjoyed talking to her and she lived too far away to plan on meeting. At least that’s what I thought until she called me one day when I was at work.

[MF] Choked and fingered her in the theater

I wrote a couple stories on here recently which got me thinking about some other experiences I’ve had. This one involves Amy, a girl I met on a dating site called Hot or Not. I don’t know why, but I’ve had really good luck on that site, way better luck than Tinder or Bumble.

I was 28 at the time, so my age range on Hot or Not was set at something like 21 to 35. I’m not particularly picky when it comes to age, I care more about maturity and if our personalities mesh. From there, it’s game on. Anyway, I notice I had a new “like” but I kept going through the encounters section, liking girls and just not finding who it was. If I ended up not liking them, it would show the like disappear. This thing never disappeared yet I didn’t match with anyone new. I thought maybe there was a glitch in the system or something.

[MF] Fucking the valedictorian part 2

I posted part 1 yesterday intending to just write the whole story but it got way longer than I expected and I had to go back to work. This part isn’t as long but has more of the good stuff and less backstory.

Picking up where I left off, Macie had just drained my cock down to the very last drop (or so I thought). At this point I figured we were done as we both got to cum, and it takes me a little while to recover. Macie though, was immediately ready for round 2. It felt like there was only a few seconds before she was back at it again, desperately trying to keep me hard. She was vigorously sucking my balls and licking from them all the way up my shaft to the head while looking at me with her big brown eyes.

“Fuck, Macie…” I sighed as she continued to work my dick.

“I’m not done with this yet,” she said in between mouthfuls.

The saving grace here is that I had already cum, so I knew I could fuck her for longer. I told her to turn around, so that her little ass was right in my face. I fingered her for a bit from behind, teasing her and rimming her asshole.

[MF] Fucking the vale-dick-torian from my high school

This happened after we graduated high school, but I always had a big thing for Macie. We never dated due to one of us being in a relationship and it seemed like there was never a time where both of us were single. I’m 5’11”, 160 lbs, and was about that same size in hs, maybe a little lighter but not much. Macie was just over 5′ tall, about 115 pounds, yet had curves in all the right places.

Macie and I were really close throughout high school. I was close with her whole family, really. Her twin brother, Caleb, and I were the two best clarinet players in the school (and yes, I did play clarinet to get close to the cuties). We also played a lot of paintball together at his house, incidentally also Macie’s house. Their older brother, Trev, was the drummer in jazz band and I played guitar so I got to know him really well too. Trev and I were into the same type of music and saw a bunch of concerts together. Anyway, my interactions with Caleb and Trev led me to get to know Macie really well too.