*Smutty stuff in here* This is just about me and my most recent dating and sexual experiences. Honestly, it's a lot of failed relationships and a lot of sadness but it's my life so idk.


8. Date #2 with Stan

A/N Okay, so, Simi, there is one thing in here that I feel like you might judge me for. I know I share practically everything with you, especially when it comes to the things I write about in here, but please don’t judge me on this. I really didn’t want to send you a message saying, ‘oh, by the way, since you’re my friend and all you should know that I’m into _____.’ Because that would’ve been fucking weird. So, this is my way of telling you this thing without actually messaging you about it.



I was studying with one of my college friends that next morning and Stan asked me to hang out. So after my friend and I were done studying, she and I headed to a nearby bakery (we’re both in the baking program at our college). I bought a two-dollar macaroon there, but it wasn’t for me, and my friend didn’t get anything for herself either.

When I mentioned I was going to call an uber, she offered to give me a ride, so we walked to her car and headed to Stan’s house.


When I got there, Stan let me in and the pets greeted me. I pushed them away until I set down my purse (it was a Kate Spade, okay? I didn’t want it to get hurt) and then pet the dogs.

Stan and I walked into the living room, closely followed by the dogs, and I gave him his macaroon, but only after clarifying that he wasn’t allergic to almonds.

He was very confused as to what it was, but ate it anyways and thanked me for it.

We watched some TV, I was sitting by him, but his arms were wrapped all the way around me, and his chin was resting on my shoulder.

Every once in a while he would either kiss my shoulder or my neck, and I’d smile every time even though he couldn’t see my face, but hey, it made me happy.

Eventually, we started kissing, and there was boob grabbing and neck kissing, and tongue sucking, and I don’t know why, but at some point I decided to take off my shirt.

So, I’m sitting there in my bra (I do wear spanx, so my spanx went up right under my bra, and my leggings went up pretty far too, and he wasn’t really seeing much more cleavage because I normally wear pretty low-cut shirts) (I promise I’m not a whore) and we’re kissing and I start pulling on his shirt and I start lifting it up because, well, I don’t want to be the only one without a shirt at this point.

So he takes the hint and takes off his shirt and my kisses trail away from the neck, more towards the nipple. I bring it into my mouth and I start sucking and licking and Stan is totally enjoying it, at least I really hope he was.

At some point (Sorry for this not being super detailed and exact, I have a shit memory and this happened like a week ago and I’m going off what I remembered and the things I texted my friends while I was at his place, and right after I got home) we moved to the futon in what will soon be his room.

When we walked over there, I kept the blanket that was on the couch around my shoulders because I felt kinda whoreish walking around without a shirt on. He pulled the futon out and we laid on it and started kissing again.


Things were getting a little more intense, and I said to him, “You know, you can do anything and if I don’t like it, I’ll stop you.”

“We’re not going to have sex,” he told me and I chuckled.

“That’s not what I meant.”

So we kept kissing, and I decided to progress things a little farther, so I slipped the strap of my bra off my left shoulder. Stan got the hint and slid his hand in through the cup of my bra, and grabbed my boob, this time no clothing was between his hand and my chest.

The kissing and boob grabbing continued to go on, and the neck kisses trailed lower and lower. At this point I was straddling Stan’s lap as he was laying down, and he positioned himself to be able to kiss lower on my chest. When he pushed the fabric of my bra aside and took my nipple into his mouth, I let out a gasp. As his tongue flicked over it, I could feel myself growing wetter and wetter. My legs were shaking slightly and it felt so fucking good, but eventually I stopped it because I remembered how sore my nipples were after Conner sucked on them for so long and I didn’t want to go through that pain again.

Many times during our kisses Stan would cup my face, I’d have a thought flicker though my mind.

“What are you into?” I asked him and he was confused.

“What do you mean?”

I paused, trying to figure out how to explain it. “Like, you like hair pulling and you like your neck kissed. What else do you like?”

“I don’t know, nothing really?”

“Do you like your hair being pulled?” I asked and he shrugged.

“I mean, yeah.”

“Okay, but…” I said, trailing off. I was embarrassed by what I wanted to say.

“But what?” He asked and I shrugged. “Are you into something.”

“Yeah,” I sighed, “But it’s weird and I don’t want to tell you and I've never told anyone. And I don’t know if I’m actually into it because I’ve never tried it before but I like the idea of it.”

“Come on, tell me,” he begged.

I shook my head. “No, but I might show you at some point though.”

So we started kissing again, and when things started to get hot and heavy again, I made up my mind. I was going to let him know.

I did it when he cupped my face again.

I grabbed his hand and I moved it to my neck.


Eventually we moved back to the couch and things continued on. That’s when thought’s started flickering through my mind again. They were very inappropriate thoughts, but hey, I was already making out with the guy and he made me feel good with the nipple sucking and such so I might as well make him feel good.

“You know, I’d really like to rub you off through your pants, but I don’t want to feel like we’re moving too fast.” I told him.

That shocked him. “You do what you’re comfortable with.”

“Do you have an extra pair of jeans?” I asked.


So I started rubbing him through his pants and after a few minutes kissing I asked him if that felt good, and he was like, “Sort of.”

“Then tell me what to do.”

He didn’t know what to say, so we just keep kissing and I kept rubbing my hand against his dick.

Now, I would like to point out that I thought his dick was pretty small with the way it was laying.

“Hey babe?” he asked and I pulled back and stopped kissing him.


He then proceeded to ask me if it would be okay if I rubbed him over his boxers, and I agreed because I really had no problem with it.

So he unbuckled his pants and took them off.

When I laid my hand back down on his crotch, I was in for a very pleasant surprise.

He wasn’t small.

Not even close.

I was rubbing him over his boxers, and after a few minutes of that and more kissing, he said, “You know you can do whatever you want to, right babe?”

“Of course,” I said back.

It was like he was reading my mind, because every time the front whole of the boxers would open, I’d want to like stick my hand in there and make him feel really good, but I was afraid to.

So, after another minute or two, I moved my hand to the waistband of his boxers, and I slipped under and grabbed him full on.

His boxers slipped down a bit, or maybe Stan pushed them down, but yeah, I was giving a hand job on the second date, but you know what? I didn’t give one on the first date!

“Do you like it dry or…” I trailed off and Stan shrugged.

“Doesn’t matter to me.”

So eventually I moved my kisses to his neck and his nipples and then I moved my hand from his dick and I spit on it.

As soon as I start jerking him off again, he moans out a ‘fuck!’ and took some desperate breaths.

“Does that feel good?” I asked.

“Yeah,” he gasped, panting.

It didn’t take long for him to moan out, “I’m gonna cum,” and then spurt over my hand and his chest.

I was pleasantly surprised by the amount he was able to produce, because with Connor it was maybe, maybe a few drops.

I don’t know why, but the first thing that came to my mind was about how easily it would be to have a kid with him because one, he had a pretty big dick, and two, he had large loads.

The thought terrified me.


So I sat there, grinning like a fool with cum covering my hand, when Stan jumped up.

“It’s starting to drip into my armpit,” he said in a rush as he grabbed some tissues that were on the coffee table in front of us.

I burst out laughing.

That’s when we noticed it.

That’s when we noticed Buddy laying under the coffee table.

“You pervert!” Stan said to him, and the cat crawled out and rubbed into my legs.

I couldn’t stop laughing.

It was so fucking funny.

And I still had cum on my hand.

So after Stan and I calmed down (he had joined in on my laughing at some point), I excused myself to go and wash off my hand.

When I got back, I used some hand sanitizer from my backpack, and told Stan to go and wash his hands.

“But I wiped them off,” he said and I shook my head.

“That’s not good enough. Cum freaks me out because as of currently, my biggest fear is getting pregnant and I really really don’t want that to somehow happen.” So Stan went and washed off his hands.

At this point, I had told Stan that I was going to inform my friend Simi as to what was going on, and he said, ‘just don’t make too detailed.’ So:


Me- Just gave him a hand job

Simi- And

Me- Just wanted to keep you updated

Simi- How did he react

Me- Very positively

       Like, it was so hot

Simi- Better than before?

Me- Much


When Stan he came back, I made him use hand sanitizer that was Vanilla Bean Noel scented.

“This smells like vanilla beer,” he said.

“Deal with it.”


There wasn’t much kissing after that, but I understood why and that was fine with me. I did have an important talk with him though.

“Just so you know, I’m not having sex until I’m in love,” I told him and he nodded.

“That’s okay with me.”

“And I don’t care how horny either of us are, it is your responsibility to not pressure me into sex, or allow me to have sex with you until I’m in love, because that last guy I dated tried to pressure me and I’m not going to deal with that again.”

He spoke slowly. “Don’t worry, I’m not an asshole. I won’t pressure you.”

I let out a deep breath that I’d been holding. “Good because I really like you.”

“And I really like you too.”

“But don’t expect the hand job to be an every time thing, because the last guy I dated expected one every time and it sort of pissed me off.”

“Like I said,” Stan repeated, “I’m not an asshole.”


He took me home after that, and he held my hand as he drove. We talked about how he was planning on leaving on Monday (it was Saturday night), and how he probably won’t have time to hang out tomorrow because that’s when his parents got back home, so this would most likely be the last time I’d see him before he left, and how we won’t see each other again until he sold his truck and moved back.

When we got to my house, he got out of the car and gave me a hug, then kissed me goodbye.

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