*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.


17. March-24-2017



Late last night I got back from my trip and earlier today I got to my sister’s house. I saw Stan again today and him and I hung out for a few hours.

He picked me up from his house and we ran over to his place to drop stuff off and then headed to get some dinner.

Since he was still broke I paid, and he gave me a five-dollar bill to help contribute. We took the Panda Express and headed to my place where we ate the food while starting the first Pirates of the Caribbean while sitting on the couch. Eventually we moved to my bed because I figured it would be more comfortable there.

I was once again on my period and at some point during this I told Stan that, not expecting anything too serious to happen between us today. Like, I was thinking we’d make out and I’d give him a hand job or blow job but nothing more than that.

So, as he and I are making at, I pull on his shirt so he’d remove it and as he was taking off his shirt, I took off mine, but I left my bra on as always. Things continued on and a few minutes later his arms move around me and start to slowly undo my bra; I appreciated that he did it slowly because I know that he was giving me the chance to stop him if I felt uncomfortable or something because this would be the first time he’d see my boobs completely uncovered.

The two of us kept making out and I undid his belt, only to not be able to undo it all the way and so Stan had to help me. He pulled them down a little bit and I stroked him a few times before going back to strictly making out because I knew that as soon as he came, the kissing would be over.

As we were making out, he kept slipping his hands down the back of my leggings and pass my underwear to grab my ass, and it was at this point I told him I was on my period and he was like, “Okay.”


I should add in that I know that all guys aren’t grossed out by periods, but my dad will leave the room if he hears a good say the word ‘pad’ or ‘tampon’ because he finds it uncomfortable or something, so I was afraid that Stan might by like that. I really wanted to ask him if he was grossed out by periods, but I wanted him to instigate the next time we had sex, so I held back because I felt like if I asked him, that’d be a gateway to sex.


He and I were just going to town making out and I was teasing him my stroking him every once in a while and eventfully he started pulling down my leggings, so I took them off, thinking that he just wanted more skin-to-skin contact which I was okay with.

Then the moved one of his hands to my stomach and started sliding downward and as he got to my underwear, I said, “You know I’m on my period, right?” just in case he had forgotten.

Hand to God he had the best response you could possibly give a horny girl who just told you she was on her period. “Yeah, so?”

I just looked at him with a smile on my face and was like, “Okay,” while giving him a slight nod and I took off my underwear.

“I have a condom in my wallet,” he told me and I held in my smile because I didn’t want him to know how happy I was that he instigated it this time by asking that!

I told him to go get it and I went and grabbed a towel because I did not feel like getting blood on my bed and I laid it down in the middle. I told him that we still needed more foreplay (mainly because I thought that the reason the last time sucked was because I wasn’t as turned on as I should’ve been) and he was okay with that.

So I’m laying on my back and he’s on his side and we’re making out and then he slips his hand downward and starts rubbing my clit. I really wanted him to finger me, but I knew that he probably wasn’t going to since, you know, blood, and that was okay with me…well not really but I accepted it.

I kept doing that thing where I’d go limp/flinch whenever it’d feel really good, and I knew there was one more thing I needed done before I’d be ready to go.

“Choke me,” I whispered and Stan moved his hand up to my throat. He barely applied any pressure, but it was the perfect amount. I like the feeling of someone holding me there, not the feeling of not being able to breathe.

I moved his hand back down to my clit and after another minute or two, I said, “Okay.”

Then a minute later, I said, “Okay,” again.

“Okay,” I told him for the third time and he still wasn’t getting it, so this time I added, “Let’s fuck.” That felt fucking weird to say, but I quickly got over it.


Actually, that part was a lie, I’m not over it. I regret saying that, just like I regret saying ‘cum for me’ to Stan over a month ago. NEVER EVER SAY ‘CUM FOR ME’ TO A GUY IT IS SO FUCKING EMBARASSING!


But back to the smut.

As he put on the condom, I moved over and laid directly on top of the towel. By doing that, I let him know what position we were doing (missionary) because I wasn’t up for doing anything that might get blood everywhere.

I helped him line up and as he pushed in it felt almost as good as the first time.

We kissed a few times as he pounded into me but mostly it was him holding his head above mine, his eyes closed, his mouth slightly open.


I am happy to say that he lasted longer than he had previously. It was probably over two minutes, which I know is still really low, but it’s much better than a little over a minute.

I might be completely wrong with my guestimation times, but I don’t really think that I am.


So when we were done, (there was still some kissing after he had came, kinda as a calm down. I was the one to stop it and I told him to clean himself up since I had a feeling that having a cum filled condom wasn’t the most comfortable) Stan went and cleaned up as I got dressed. I moved my laptop back to my bed (I had moved it to the floor at some point during the make out so it wouldn’t fall off) and the movie was still playing.

Stan came back in and laid on the bed with me before playfully giving me shit for having a heavy period because apparently it had gotten everywhere on him like his dick and his thighs, but he made it clear that it wasn’t a big deal.

He and I cuddled for the remainder of the movie before he headed home.




I would like to add in that at this point, I’m not hesitant about my relationship anymore. I don’t doubt that he actually likes me because I know that he does.

It was during that second date in the last update where I playfully told him that I hated him and he said, “No you don’t, you like me. And I like you, a lot.”

He made a point to let me know how he felt, which he really didn’t have to do, and that made me happy. It washed away all my worries and insecurities and now I know that he genuinely likes me. 


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