I hooked up with a high schooler (who was my age) [MF]

Well this is awkward. It really took me a long time to name this story. This is also more comical than sexy.

He was- so weirdly- some of the best head of my life. I think I’ll always have a tiny crush on him.

I usually don’t name people in my stories but it got confusing so I’m calling high schooler “Sam.”

Technically Sam was six months younger than me, but I believe we were both 19 when we met. However he was a senior in high school and I was a junior in college. I skipped a grade once and he had been held back… A couple of times.

One weekend I had nothing to do and my good guy friend (who I’m going to call “Dave”) was like, “Come see my brother play football. He’s really good.”

“Like your high school brother? We’re going to your hometown to see him play?”

“Yeah! I’m telling you it’s fun to watch and he’s so cool to hang with.”

“I don’t want to go hang out with high schoolers,” I laughed.

I hooked up with my ex GF after she basically broke up with my BF for me [FF]

I’ve been sitting on this story for a hot minute.

Someone asked me what the best sex was of my life the other day and I truly don’t know. I’ve had so many incredible experiences in so many different ways that it’s impossible for me to quantify.

However, the best buildup to sex? I think it’s this story…

I have written how much I hate my ex-boyfriend who started out as my boss. Really. I HATE him. I always give this disclaimer because it’s not just me being cute. He’s an ass.

This is the story of how he got fucking OWNED by my ex-girlfriend.

*She is my self-proclaimed “crazy ex.” I write about her in a way that you can sometimes see my frustration because she was a hard person to date, but I care deeply about her.*

So after EXBF and I broke up we regularly hooked up and I sometimes spent the night. One morning before work I was in the shower and I walk out to the sight of him holding my phone with a huge grin.

One of my classier moments at the symphony [FM]

God damn it, I hate how many good sex stories I have with this asshole. I addressed this in my AMA, but I’m not being cute when I say I genuinely hated this man.

He was my boss when I was an intern and then we started officially dating after a few office hookups. However, even though he was ten years older than me, he was an insecure little bitch who didn’t quite know how to handle me.

*I swore off dating other lawyers after him.*

Anyway, one time we went to the symphony. It was one of the few times we genuinely had a nice time beforehand.

First off, I looked beautiful. I still remember that damn red dress and how long I took to actually do my full hair and makeup (I’m usually kind of a mess). He also wore this really hot suit that had me thinking dirty thoughts. Sometimes I forget he was actually hella attractive.

We went to dinner and were both just super giggly and cute. He could be sweet on occasion.

He tells me he used to take all his dates to this restaurant.

The heartbreaking impracticality of hooking up in a hostel [FM]

*I tried to write this a million ways without it coming out like a tale where Nicolas Sparks fucked Casablanca, but here we are.*

This is the ONLY time I will ever use someone’s real name.

Noah I hope you see this. You should have gotten my number, Dude. I wish we had stayed friends.

When I was young I traveled a lot by myself. I was writing then and had an online job. Sometimes I didn’t use the best judgment of where I landed.

I took a day trip to one country in particular that was not somewhere I probably should have gone. Like, their government collapsed on my way there and I landed in the middle of a protest. I was so naive this barely even phased me. I literally just holed up in a cafe and waited for things to chill.

A dude approached me.

I was not into meeting other people at this point in life. Tbh I was hyper-fixated on finishing my first book and felt any friend I made was a distraction from writing.

THAT CNC story [FM]

*I’ve written and rewritten this so many times. It’s hard because I’m afraid of assumptions that will be made and what it might trigger. After a lot of thought, I am posting because I also think it’s important to understand what CNC looks like in reality.*

*The person in this story remained my best and dearest friend for years. He was at my wedding, damn it. I even texted him this before posting.*

*All the damn TWs. This shits gets dark.*

So someone asked for my CNC stories. I wrote one a couple days ago about “experimenting.” It was very important to me that I wrote that one first and I went through the process of communicating through CNC. Also the first time I engaged in this kind of sex, it was actually my partner who really struggled with it and needed a lot of aftercare.

*Just read it if you haven’t- it’s not hard to find on my profile.*

Anyway, this one gets a little darker. I almost didn’t post it because it gets so dark I’m legit afraid of it being upsetting.

My accidental public orgasm [FM]

I once was traveling with my boyfriend and we “experimented” in ways that were more than just sexual. We never went too hard, but we were in a country where more things were legal. That’s all I’m going to say about that, but just know we were a little fucked up in this story.

*He was also super wealthy and just kind of paid for us to have these crazy adventures. My life was much cooler before I became a lawyer and started working for the man.*

We went to a rave in said country and got a little crazy.

For one thing, this dude was obsessed with me on a normal day. He would have fucked me several times a day if I’d let him. In fact, we fooled around in a train bathroom on the way to this rave and almost got kicked off.

Back then I also dressed very conservative but decided to go all out that night. I wore a crop top and very short skirt. He was falling over me all night and I was having a lot of fun touching him.

This was a recipe for disaster.

One of my hard limits is a very common fantasy [FM]

This is going to be purely comical btw. I’ve been getting too deep lately and working on a couple of stories that get rough.

*Btw, if this is your kink, you get no shame or judgement from me. It’s just not personally my thing.*

So I get real weird in bed. Although I have hard limits, it’s actually been pretty rare a partner has suggested something I wasn’t down for.

Except this one thing…

The first dude I ever fucked once asked if he could spank me. I was all about it. I would soon learn I love getting spanked. He full on bent me over his knee (*hot*) and fondled my ass for a solid minute before he just reared his hand back and went for it. I was so fucking turned on. He asked me if I liked it and I said absolutely.

“Then say thank you, daddy.”

*Oh. Um…*

This was before I understood I could set boundaries and went to too great of lengths to please. So I awkwardly stumbled into possibly the least sexy sentence I have ever uttered during sex, “Oh ok, thanks dad.”

Experimenting with CNC [MF]

A couple of y’all asked me about this because I’ve mentioned I’ve been into CNC. I will deliver because I’ve had some great consensual non-consensual sex, but I am not going to do it without a few healthy disclaimers and advice.

First off, do not jump into this. CNC takes more than your average safe words and signals. It requires more than just trusting your partner. It can bring up shit on both sides. The first time my partner and I really got into it, it actually deeply affected him more than me. Make an aftercare plan.

So I dated a guy for a while and then we moved to different places. We’d regularly Skype or sext for years after and sometimes visit each other. Bro, we had some weird ass sex that got rough. I dare say we were pretty close to CNC during some of our sessions. We got even fucking weirder when we weren’t in person.

*Which is natural. It’s much easier to write kinky things out. Some of it got so weird though I really can’t even write it on here. I tried and I just could not put it in a context that doesn’t make us sound like psychopaths.*

I bet my best friend $100 our waiter wanted me [MF]

I finally have a recent story I can write!

A group of my girlfriends went to Vegas recently for a mini vacation. It’s been a while since we went all out and we got a little crazy.

I also just made the decision to dress VERY slutty all weekend. I basically bought a new wardrobe for the occasion. On one particular night I was skin tight leather pants and a top that couldnt quite be described as a “shirt.” It was more of a play on a shirt.

I looked good. I was cold AF but it was worth it.

We went out to dinner and our waiter was CRAZY hot and was 100% flirting with me.

*Funny enough: he kind of looked like my husband.*

My best friend made a comment about how men in Vegas really know how to get tips by flirting and I whole-heartedly disagreed.

“I don’t think he’s just flirting for a tip. That dude is into me.”

My friend laughed and was like, “He’s flirting with every table!”

“Nope, this dude wants me.”

First time fucking the dude who taught me BDSM [FM]

*Disclaimer: this story was by popular request because a lot of y’all were like, “How the fuck did this happen to you?” As such, I’m telling it the long way to be true to the narrative. That’s why I’ve had to write to write this in multiple parts and pages. Forgive the novella but at least this one is like 90% actual sex. Enjoy*

This is kind of part 3 in that’s it’s a continuation of how I got into a relationship like this, but you don’t necessarily have to read my last two posts to get it. Basically what you need to know is I met a person and we hit it off as friends. We hooked up pretty quickly but had not actually fucked. He then told me I had to wait for it and was not allowed to get myself off before we finally I had sex because he wanted it to be mind blowing.

I did not do well in this scenario.

The morning after we hooked up I woke up going a bit crazy. The moment he opened his eyes I slid my hand into his pants and watched his face light up. “You’re welcome to do that, but you realize I’m not going to get you off in return, right?”