*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.


3. Date #2

Date #2

It’s been about a month since I went on this date so things are a little foggy, but I’ll let you know what I remember.

Okay, so this one started with me convincing my sister to drive me to Connors college so we could hang out in his dorm. The entire way there, Libby kept saying ‘I’m either a horrible mother figure, or a great big sister,’ and I decided that she was classified as both.

When we go to Conner’s place, I stood outside and waiting for him to come out and get me. It took a few minutes but eventually he walked out the doors. Now, I knew that Libby was still in the car watching me, making sure I was okay, so I did the adult thing, I ignored her and as Connor neared me, I said, “Don’t kiss me, Libby’s watching,” and thankfully, he didn’t. If he had, Libby never would’ve let me live it down. She’d probably also mention something like ‘you’re moving too fast to be kissing a boy’ but she wouldn’t be wrong, we were moving too fast, and this ‘date’ didn’t help.

As soon as we walked into the building, Connor put his arm around me and we headed through a door into the stairwell since the dorm didn’t have an elevator and his room was on the second floor.

Now, this is when Connor decided to stop walking, and kiss me.

It was sweet of his to do, but I’m not one for PDA. And yes, I know, no one could see us in the stairwell, but that didn’t matter to me. I wasn’t comfortable doing anything that might be considered ‘inappropriate’ in any place that wasn’t a bedroom/a house.

So, I soon stopped the kiss, telling him I was uncomfortable kissing in a semi-public place. Thankfully, he understood and didn’t pressure me to kiss him again here.

As soon as we got to his dorm (one that he shared with three other guys) I met the guy he shares his room with.

Joel, well, I’m pretty sure he was high on something. I’m not sure what it was, but he was pretty off. He was laying on the couch in their living room and was just like dazed. Connor did the polite thing and introduced me; well, I actually introduced myself and Joel didn’t say anything so Connor told me his name and then we headed to their bedroom.

The room looked like what you’d expect a boys’ room to look like. It was filthy. Now why he wouldn’t have picked up at all when he knew I was coming over was beyond me, but there was barely any room to walk in the already small room. Conner had a twin sized bed with a flag with some football logo on it pinned to the wall above the headboard.

I sat on the bed as I felt awkward standing in the middle of the tiny room. Connor sat buy me and we made some small talk before we did the obvious thing.

Once we started making out, things got sort of awkward. Our teeth kept bumping into each other and since we both had glasses on, they kept clinking together. I had to stop us so we could talk off our glasses (and our shoes since I had on knee high boots and he had on clunky tennis shoe).

The make out started to get better after that, and things progressed fairly quickly. Connor’s shirt was removed and so was mine (I kept on my bra because I hate my boobs) and I unbuttoned his pants and started jerking him off.

“I hate to see you not get any pleasure,” Conner said to me, which just turned me on more

I am a very awkward person so I did the obvious thing. I put my hand on his shoulder and looked him in the eyes and said, “Don’t worry, I’m fine,” in the most casual tone ever; and I was fine. I knew we were moving too fast and so I didn’t want to say anything that would progress us any farther. I told him that too, and that we wouldn’t be moving any farther than this for a while. He said okay and you know what happened with in like fifteen minutes?

His fingers were inside me.

Let me tell you something though, there is a huge difference in masturbating and being finger-fucked by someone, and having someone else do all the work feels much better.

It started with him rubbing me through my pants, and saying things like, “You’re soaked,” which didn’t help my wetness, and whenever he’d hit my clit, I’d let out a soft moan. It didn’t take long for my horny mind to take over my actions and I grabbed his hand and moved it to the top of my leggings and have him go down them.

Hot damn.

That’s all I can say.


I don’t know what’s wrong with my body, but every time I got really sensitive, I’d, well, I’d basically… flinch. Connor calls it going limp, but I think it’s more like flinching.

Now, as good as this felt, I knew it would feel better if he had better access, to I took off my pants (not my underwear because I’m self conscious of how my vag looks since I’m fairly fat and, well, all of me is at least a little fat-looking) and when his fingers slipped inside me, I was in heaven.

I’m normally not one for penetration, like, when I masturbate, I have a dildo and I’m just not in love with it. I like my vibrators more so I’ve always thought I was more of a clit person, but well, I am more of a clit person, though the fingers of someone else up inside me may have started to change my mind.

I was jerking him off and he was fingering me. I’d get so overwhelmed that I’d tighten my hand on his dick before releasing it completely, then after like a few seconds remember that he needs pleasure too so I’d go back to jerking him off.

Conner kept saying the same thing; “You’re soaked.” That might not sound like the most arousing thing to be said, but trust me, in the moment, it was hot as hell.

At some point, he pushed my hand away from his dick and continued finger-fucking me. I let out semi-loud moans and there was the…slopping like sound of his fingers in my wet vagina. You know the sound, it’s like in porn the wet slapping like sound. Well, that sound turned me on even more.

While Connors pointer and middle finger were inside me, he’d use his thumb on that hand to rub over my clit which would make me moan and flinch/go limp.

Eventually I was overly sensitive and I honestly couldn’t think straight but I physically couldn’t take it any longer so I had him stop.

I jerked him off until he once again pushed my hand away and he started jerking himself off. Since he hadn’t washed his hands yet, he still had the… liquid or whatever you want to call it from my vag on his hand and the sound started up again. I watched and he pleasured himself and I asked him if he was close. When he grunted out the appropriate answer, I whispered, “Cum for me,” and he soon did.

Now, as soon as the mood was over, I said the thing that any sane girl says. “Wash your hands before you touch me again.” That earned an odd look from Connor so I went on to explain my number one fear. Getting pregnant. Now, I know the chances of getting pregnant without having sex are slim-to-none, but if you finger a girl with the same hand you just used to jerk yourself off, then that slim-to-none chance turns to slim-to-some.

When we walked out of the room so we could both wash our hands, I was traumatized to see Joel laying on the couch still. So I rushed back into Connors room, blushing hard.

I had not been very quite during the previous events and I was very embarrassed to know that someone other that Connor had heard me. When Connor joined me back in the room, asking me what was wrong, I explained it to him. He didn’t seem bothered by it at all and tried to make me feel better by telling me that both Joel and his had heard their other two roommates having sex with their girlfriends in the shower, but still, it bothered me.

So, the lesion learned here is to remember when other are in close proximity to you when you’re being loud and doing inappropriate things.



(Also, I barely read these things over so please excuse any typo’s and such)

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