Super long, definitely NSFW, has play details as relevant to the story. Ya'll, I've been driving myself up the wall for 8 months with one of my friends, confused, frustrated, trying to figure out if he actually liked me or not. Because I'm apparently the fucking idiot who doesn't know how to take someone at face value when they say what they want.

He's one of the friends I wrote about in my CNC green flags post, because we had a truly awesome time playing, but I was still confused after at points. He wasn't as handsy as he promised and I tried asking him for a kiss and he pulled away and awkwardly changed the subject, among other things that just made me question if he was actually truly interested in my flirting like he said.

I would sit down and talk to him and he would say yes, flirt with me. Yes I enjoy this. I like brats. I like forward kinky sluts. I get off on vulnerability and authenticity. Etc... and ya'll, I was a fool. I heard those words and decided, clearly that wasn't what he wanted.

We saw each other again in person this past weekend, 6 months since the last time. He said he wanted to see me beg and crawl and be a depraved slut (things I offered first and he was like "yes please"). And... I somehow didn't believe him. We both traveled multiple states to meet up for two nights, and I was quiet and awkward and demure subby sub because I was scared to brat and be forward, I decided he clearly didn't actually want that. We got to our hotel, we fucked, but I didn't resist, and something just felt... off. I felt like he was going through the motions, but wasn't actually interested. Then he fell asleep for a few hours.

We had tickets to a show that night, I wore a revealing thigh slit gown, visible garter and stockings, and played pretty demure sexy subby sub. He kept walking down the sidewalk ahead of me not touching me, I was so confused I couldn't understand what was happening, I asked him if things were fine and he said they were. He was cautious in his touch at the show, but there were outside factors impacting what we could do, so I assumed that. We got back to the room... and he slept for another 10 hours.

He was cutesy at brunch, we went back to the hotel and he beat me for a bit. He started to seem to relax some, and I noticed him perk up a bit when I resisted, so it turned into a fun wrestling match, every time he subspaced me out he pulled back and waited for me to fight back before continuing... you would think this would be the clue I needed to figure it out (he already told me what he wanted) but apparently I'm obtuse as fuck.

After a while of laughing and wrestling and impact... he fell asleep again. I curled up in his arms confused. Convinced he was avoiding me. I felt horrible and self conscious and wrong. I couldn't understand what was happening, that this man who said I was hot and sexy and he wanted to do depraved things to me, wasn't. After I while I began crying, I couldn't stop myself. I accidentally woke him up and he asked what was wrong, and I told him that I was afraid he didn't want me, and I thought I was bad and wrong. He was immediately soothing, grabbed me and forced my mouth on his cock and decided to spend the next 30 mins deciding whether I was allowed to breathe or not before fucking me, but despite this, something still felt off.

I was ready to call the date. I felt so confused and lost. But, we had spoken before hand about how I struggled with fear and shame and embarrassment, and I had told him before the weekend I 120% wanted to do the things I said over text, but struggle with my inhibitions. We had weeks before this discussed having a drink or two, just enough to get my brain to stop screaming at me and relax. So instead of calling it I suggested drinks.

We found a small intimate cocktail lounge, that had couches at the tables, and we sat down and I tried cuddling up against him... and he pulled away. I was done. I felt like shit. And he had a call come in and had to step away. And I sat there with my drink confused, and I faced the crossroads in my brain as I drank my drink alone. And I realized three things in that moment.

1) he traveled multiple states to stay with me for multiple nights. CLEARLY he was interested, even if I didn't feel it.

2) frustrated as I was that he wasn't doing the things he promised... I wasn't doing any of the things I promised (crawling, begging, bratting, resisting) things he told me clearly he wanted.

3) I may as well enjoy the drink, and let it give me the courage to do all the things my scared ashamed heart was afraid to do. If he still rebuffed me after that I just wouldn't seek him for play anymore.

He returned, we finished our drinks and decided to head back to the hotel for another. I decided to snark him on the way back, and his eyes lit up and he smacked my ass. And so I bounced and snarked him some more and he smacked me again and pulled me close for the first time all weekend. His eyes were dancing when we got to the hotel, and he ordered us both another drink while I needed to step out a moment. I returned and rested my hand high on his leg while giving him the "I want you" look, he watched me finish my drink and practically grabbed me from my chair. Holding me close the whole way back to our room for the first time, hands running down my thighs over my dress in the elevator, digging into the bruises from earlier.

We stepped into the room, and he looked at me, and I commented that I better get my dress off (favorite and irreplaceable) before he destroyed it huh, and he agreed. He motioned me over as he sat and grabbed me by my hair pulling me onto his dress boot. I almost pulled away, I almost cried, he knows/knew how ashamed I am of my boot fetish and had spent the past 8 months trying to convince me he wanted that and wouldn't judge me. So, I let the alcohol tell the weasels to take a hike, and I rode his boot for a moment before he pulled me off and told me to hold on.

He switched into a kilt and his combat boots, told me packing those boots for me were the only reason he had to bring such a large bag. Then, pulled out a strap on and a vibrating dildo. I knelt there on the floor while he set up, shaking, trying not to cry in shame, and I remembered his previous words for me "good thing for you fucking kinky sluts are just my type" and I finally realized I had been the biggest fucking idiot. He really had been telling me EXACTLY what he wanted, and my anxiety refused to listen. And this fucking man had the patience of a saint, meeting with me, because he knew how much I said over text I wanted those things too, and he believed me, and he knew I was just scared, and he waited.

And he finished setting up this strap on and I crawled onto it and almost immediately orgasmed in a cry of shame and joy and relief. And I began to ride his boot desperately, and I told my anxiety to take a long hike off a short pier, and I looked up into his eyes, and he was in fucking power drunk bliss watching me. And I remembered an earlier conversation where he told me he wasn't a sadist, but his biggest kinks/ turn ons were vulnerability and authenticity, which would overlap into appearing like sadism a lot in the moment. And I realized by allowing myself to give into one of my kinks I was most ashamed of for the first time ever with anyone in this moment, I gave him my vulnerability. I rode his boot, I begged and cried for his cock, I never bothered to track how many times I came, he apparently gave up counting for me at 20. He looked the happiest I had seen him all weekend, and was the hardest too.

I rode him until I couldn't hold myself upright anymore and he was barely keeping me up by my hair. He pulled me off his boot, he held me as my knees locked up and lifted me onto the bed gently. He brought me my water before he went to clean himself up. Then, he returned and held me close while I was melted into bliss. He nuzzled his face into my shoulder while he seemed to think for a moment, and then... he leaned in and kissed me. It was the most gentle, sweet thing. And we held each other and he kept kissing me. And we curled up and fell asleep.

The next morning, instead of sleeping as late as possible, he woke up 2 hours before his alarm. I almost put my walls up, I was afraid his reaction to me the night before was only because of the alcohol. But I decided to uphold my promise, that I would only use the alcohol once to see it was safe to lower my barriers, and after that, I would leave them down. I bratted and sassed him, and his eyes lit up. We both relaxed and half wrestled and smacked each other and were all over each other. We went out to find breakfast before we had to check out of the hotel, and for the first time he held me close as we walked down the street. We were like your stereotypical PDA couple. I would poke him and waggle my butt, he would grab me, run his hand down my bruises, or hold the back of my neck and "give me a massage" but it was 100% that sadistic "did you want to go there?" Then he would flip me around and kiss me. He couldn't keep his hands and eyes off me.

We finished packing and went to the train station to catch our respective trains. We snuggled close in the lounge, me trying to poke his nose while he tried to bite my finger, switching to him rubbing my bruises more.

When they started announcing our tracks, he gave me a kiss and started walking off, and he saw me watching him walk away and turned and ran back to give me more kisses, and his eyes glowed as he told me he'd see me in 3 weeks, and the whole way to his train he couldn't keep his eyes off me.