The Bet, The Bond, The Night That Could Of Been (m/f)

[Dc_guy15]

Hey everyone! It’s been a while since I last posted, so I figured I’d start again. Just a heads-up—I’m using some AI to help with structure and corrections, but I’m making sure it doesn’t change the style or content of the story. Just using it as an aid.

This story is about a close friend of mine who ended up in a pretty interesting bet that turned into something else entirely. To be honest, I don’t remember exactly how or why the bet happened since it’s been so long, but I’ll do my best to fill in the details.

Let’s call my friend Cindy (not her real name). We met about nine years ago while out for job training. We were both around 20 at the time, but we weren’t exactly close—more like acquaintances than real friends. Fast forward a year, and I ended up moving to her state on the West Coast. Somehow, we reconnected through Snapchat and started catching up, though nothing we talked about ever really had to do with TUGs.

At the time, both of us were single, and one day, we decided to hang out. We hit it off pretty well and eventually started spending more time together. Fast forward again about 6–8 months. I was just chilling at home when Cindy messaged me, asking what my plans were for the night. Since it was a Saturday, I told her I planned on staying in and playing video games. She immediately called me out, saying that was lame and that I should meet her and some friends for a drink.

After thinking about it, I asked if I could bring a friend along, and she said sure. So, I got ready and headed out, driving about 30 minutes to meet up with her. I had assumed we’d be going to a bar to grab some food, but when I arrived, I realized the address she sent me was for a club. Not exactly what I had mentally prepared for, but at that point, I was already committed.

Cindy and I had always just been friends—nothing more. But when I showed up that night, she was already two or three drinks in. The moment she saw me, she jumped on me with a big hug—definitely more enthusiastic than usual. My friend hadn’t arrived yet, so it was just me and her girl friends for the time being.

Now, let me describe Cindy a little. She’s a tiny, fiery redhead, about 5’3” and full of energy. She’s always been outgoing and never holds back when she speaks her mind. She has an athletic build, green eyes, and long red hair. That night, she was wearing cowgirl boots, jeans, and a flannel.

After greeting me, she immediately dragged me onto the dance floor. That’s where things started getting interesting. She was actively grinding on me, moving against me, and dancing in a way that made it clear she was interested. I had never danced like that with her before, but I went along with it. And every time I responded even a little, she pushed things even further.

As the night went on, she eventually said she was ready to leave. I was feeling tired and debated getting a hotel since the drive back was on a dark road. But when I mentioned it, she said that was dumb and told me to just come with her and her friends to their place to hang out and watch a movie. I agreed, and my friend ended up tagging along too.

When we got to the house, I sat on the couch while Cindy changed into her pajamas. She came back wearing a thin tank top with no bra and some short shorts—nothing else. Her friend put on Thor: Ragnarok, which, honestly, was maybe a 5/10 at best, but we went with it. Everyone was joking around and having snacks when Cindy came over and laid down on the couch with me.

At first, she just lay next to me, but then she rested her head on my lap. I wasn’t sure if she was just getting comfortable as a friend or if this meant something more. She was sobering up, so I knew she was aware of what she was doing.

Then, she started playing with my hand while still chatting with her friends. I kept cool and went with it. Next thing I knew, she placed my hand on her stomach. I left it there. Then, she slid my hand under her shirt, still on her stomach. I took the opportunity to softly run my fingers along her skin. That’s when I noticed her subtly pushing my hand lower, towards the waistband of her shorts.

There was a blanket over us, so no one else knew what was happening in the dark. I didn’t want to misread the situation or cross any boundaries, but it definitely felt like she wanted more. Just as I was about to test the waters, my friend came over and sat next to us—completely unaware that he had just killed the moment. And that was the end of that night.

The next morning, we started getting ready to leave, and at some point, we got into a playful back-and-forth where I told her she “failed” at something. As a result, I jokingly said that meant she had to let me tie her up. To my surprise, she just laughed and said, “Sure, I don’t care.”

At the time, it was just me, Cindy, and her friend (the one who owned the place). Her friend, who was super nice, happened to have a roll of duct tape on hand and eagerly handed it over when I asked. Cindy sat on the floor with zero hesitation.

She was wearing a red sweater, blue jeans, and socks, with a bright neon pink shirt underneath. I started by wrapping duct tape around her upper arms, just above her chest. I should’ve gone lower to accentuate things, but I kept it simple. Then, I taped her legs—above her knees and at her ankles—before finally taping her wrists behind her back. I placed her on her stomach and did a half-assed hogtie. I didn’t go all out since her friend was watching, but I was definitely enjoying it more than I let on.

To finish it off, I laid her on her side and applied several strips of tape across her lips, nearly reaching from ear to ear. Seeing her bound and gagged for me was incredible. She arched her body slightly, showing off her curves, and I told her I was going to time how long it took her to escape.

Before starting, I flipped her onto her stomach and quickly pulled off her socks, joking that they were a little too dirty. She just laughed under her gag. Then, I said, “Go,” and she immediately started struggling.

She quickly broke free from the hogtie and wiggled around, completely immersed in the challenge. She rolled onto her back, managed to take off her sweater despite the tape, and worked her way out of the bindings. I called her out for “cheating,” but honestly, she was just being smart. In the end, she escaped in under a minute and 30 seconds.

The whole thing was recorded—both by me and her friend. Her friend even posted a clip on Snapchat, and I still regret not saving it. It was an awesome moment overall.

After that, Cindy and I went for a drive and talked a bit. The night had been exciting in so many ways, but nothing more came of it. We never spoke about it again, and about a year later, I moved away. Cindy eventually got married and moved on with her life.

Even now, I sometimes wonder what might’ve happened if we had just a little more time together.

It wasn’t the craziest story, but I hope you enjoyed it! I’ll try to write more soon and not wait years to post again.

[SilverLinings]

Really fun story, thank you for sharing! And yes, "if only"....hahaha

[ZiptieFriend]

What a near hit!! Sorry for you man, she sounded fun. Have you found someone to tie up since?

[Dc_guy15]

Yup! But it’s definitely been more sporadic. I’m trying to get back into it more consistently