*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.


2. Date #1

This could possibly be considered my first ever actual date. Like, I went on one a few months back with this guy, and we hung out a few times and mostly just made out, and I never really liked him so I ended things pretty quickly. That guy was also my first ever actual kiss.

To sum of my dates with that guy, it was basically, he started messaging me, that day we skyped, and then met up for lunch. It was a recipe for disaster. We met up at the outdoor mall like five minutes from my house, and it was basically us going around into stores and it was just really awkward, and then we were behind one of the stores and he stopped and we kissed and it was weird and wet and pretty awkward and I made it even more awkward before he even kissed me by saying, “I’ve never actually kissed someone outside of spin the bottle,” and then and he leaned down, he had his arm around me and we were standing side-by-side so both our necks were craned to the side and it was just terrible, but as he leaned down, I swear to god I said, “I won’t be good at this,” and his kissed me and it was awkward and terrible and is literally what probably made me not like him. Eventually I walked him to his car and he left.

We started hanging out at the elementary school park in my neighborhood to make out. IT WAS DURING THE SUMMER SO NO LITTLE KIDS SAW but we were interrupted by family’s enough times that we just started going to my house. We’d make out in the basement and we wouldn’t really talk. It was basically friends with benefits, though all we did was make out. Everything else we did was only ever over the clothes, so he’d grab my boobs and he kept trying to rub me through my leggings, but I wasn’t really ready for that so I’d just move his hand back to my boob where it was more comfortable for me.

Oh, did I mention that after the during the third date I told him that I didn’t have feelings for him and then he looked sad so I told him we could still make out? Did I mention that? No? Well, like it says in my MeetMe profile, I’m pretty blunt.

We got in a really good rhythm of how we’d make out, we both knew what the other liked, as in we both liked to have our tongues sucked on. We also both enjoyed the sound it would make when I’d pull my tongue from his mouth and it’s make like a small suction cup noise.

Eventually, I realized that I was leading him on, since he said he liked me and I literally felt nothing for him, so, I did the adult thing. I stopped responding to his texts and blocked him on MeetMe and just waited for him to stop messaging me.


I started talking to Connor probably a little over six weeks ago, and after two weeks of talking, we skyped. Things went well and I said that I might have an extra ticket to a concert and we planned on him going, until my dad said he couldn’t come, and since it was my dad who paid for the ticket (and I’m an obedient child) I told Connor that he couldn’t come.

I legit thought that would’ve been the end of it, since we made plans and I canceled, but we kept talking. Both of us were totally talking to other people on MeetMe, don’t get me wrong, but the fact that we continued talking for like a month was awesome.

About two and a half weeks ago, Connor and I made plans to hang out the next day. We were going to meet at my work and eat there, but as I was waiting for him, my sister (it is a family business so she works there too) decided to announce to the entire staff that I was about to go on a date, and one of the bartenders, Carrie, started harassing me about him. So, when Connor texted me and said he was nearby, I told him to just meet me outside.

I walked out, leaving my sister, Carrie, and the TWO OTHERS THERE WHO WERE ANNOYING ME FOR DETAILS and met Connor. It was kinda awkward, and we walked around downtown to Panera where we talked for a little while, getting to know each other better. I thought he was a little weird at first, then he told me about his social anxiety, which made the weirdness make complete sense. Since we both had some sort of social anxiety, it was awkward for a while, but by the time we walked to the nearby bakery, things had chilled out and it was easier to talk.

We got some donuts and headed to a coffee house for some caffeine and then we sat in a both and kept talking.

I’m not sure how it was brought up, but I think I mentioned wanting/needing to make a cake since I had bought several baking books earlier that week. He asked if I wanted any help and since things were going good, I accepted the offer.

I called us an Uber (sadly neither of us drive. My anxiety is too bad and Connor apparently can’t pass a driving test) and we had it stop at the store on the way. We bought what we needed, and might I just point out that going grocery shopping with someone you don’t really know is a lot more awkward than going on a date with them, and then got back into the Uber to my house.

I should probably mention that my dad house is an hour away, while I am currently living with my sister and her boyfriend, so yeah, two houses, but back to the topic on hand.

We got back to my sister’s house, and I gave him a quick tour. Jay, my sister’s boyfriend, was still at work so we had like two hours before he got home. During the tour, I had him meet Dean, my cat who HATES men, and, to no surprise, Dean ran and hid under my bed. I tried to get Connor to leave my bedroom, but he was being playful and wouldn’t move. We ended up kissing, and with was nice and sweet and unlike my last first kiss with a guy. This one felt more…natural. Less forced and awkward.

We ended up heading back upstairs (I live in the basement while Libby and Jay live upstairs) to start on the cakes I wanted to make.

It was fun, playful, and just really enjoyable. At one point he did slap my ass, which caught me off guard but, as I said, it was ‘not unappreciated,’ and that seriously confused Connor, which was cute.

Once the cakes were in the oven, we did the most obvious thing to fill time, we went back into the basement and started making out. Kissing Connor was a lot more enjoyable than kissing the last guy, and I moved a lot quicker with Connor than I had with him.

The making out was a little messy, but hey, we still needed to get into a rhythm with each other. Unlike with Joe (the previous guy), I let Connor grab my boobs on the first night. In fact, I let him suck on my nipples that very same day too, within the hour in fact.

So we were making out, and he was grabbing my boobs, and he had used his hand to lead my hand down to his crotch, and I started rubbing him through his pants. Keep in mind that the farthest I ever got with Joe was him grabbing my boobs OVER THE CLOTHES and on the last date I had with him (which was like the fifth date), me rubbing him through his jeans WHICH IS OVER THE CLOTHES. Got that? Okay.

We continued to do that, basically until my alarm for the cakes went off. So we went upstairs and took the cakes out of the oven, and as we waited the ten minutes before taking them out of the pan, Jay came home.

Now, I thought that Libby had texted Jay, telling him that I had a guy over, just so he had a warning. Apparently Jay hadn’t looked at him phone from the time he left work to the time he got into his bedroom, so when he walked in and saw Connor and I in the kitchen, he was a little confused.

I introduced them to each other and Jay quickly headed to him and Libby’s room. I turned the cakes out of their pans and Connor and I headed back downstairs.

We sat on the couch and quickly started making out again, and things got hot and heavy quicker than before.

At this point, he had figured out that I liked to have my tongue sucked on, and would growl out a, “You like that?” which was hot as hell.

Then, for whatever reason, I had to pee, and so I pulled away and told him that and the conversation goes like this.


“Yes, really. Would you rather me go now, or in like ten minutes when things are a little heavier?”


So I went pee, and found that I was quite wet, which wasn’t too unexpected but it still surprised me by how quickly I had gotten that wet just from making out. So I cleaned myself up, and headed back out.

As I neared him, I noticed that he had…undone his jeans a little and pulled himself out. I grinned, you know, seeing a dick for the first time that wasn’t on my computer screen, but I was worried we were moving too fast, but, given my social anxiety, I didn’t say anything.

I sat on the couch my him and we immediately started making out again. Oh, did I mention that by this point, I had made him remove his shirt and yeah, that would be important. So, as we were making out, I trailed my hand down his chest and to the on waiting dick. I wasn’t really sure what I was expecting it to feel like, given I made never touched a penis before, but as my heart was raising, I gripped him and started to jerk him off.

I’m not sure if you’ve ever given a hand job before, but doing if your first time is a lot of work. Your arm gets tired and you’re not quite sure how to grip it or what to do with the balls, and don’t forget about the random precum that slips out and suddenly there’s a little liquid that wasn’t there before that makes everything a little wet.

That continued on for a little bit, until he leaned me onto my back so I was now laying down. We continued to make out as he climbed on top of me and started grinding on me. It was a surreal feeling, feeling the head of a penis touch my clothed vagina, knowing that I could easily lose my virginity if I wasn’t wearing pants. Eventually, I sat him up again, and took it upon myself to continue the hand job.

He pulled lightly on my shirt, and I took that as a hint to take it off, so I removed my shirt, leaving on my tank top since I’m self conscious, and he started going to town on my boobs. It started out with just grabbing them, then, with my consent, he pulled them out of my bra and started kissing and sucking on my nipples which felt good. His mouth would be on one while his fingers would be pinching the other. Since no one had ever sucked on my nipples before, they quickly got sore and so I had him stop, which he did without question.

As we started making out again, I was jerking him off and my arm, of course got tired, so since I’m VERY blunt, I told him and he goes, “Want me to finish for you?” or something like that, but the way he said it just made me suddenly feel suddenly very soaked. He pulled down his jeans some more and I rested my head on his chest, watching him jerk himself off.

It was very odd to be doing all this so quickly, but I guess that we just clicked and things went really well. I wasn’t uncomfortable anymore, and it was…nice watching a guy jerk off to you and it was a good feeling knowing that you had gotten him hard.

I kissed him chest, leaving hickeys over his heart, and sucked on his nipples while he continued to pleasure himself. When I asked if he was close, he grunted out a yeah, and I stared at the dick until small amounts of cum dripped out.

“I masturbated this morning, sorry if there isn’t much,” he said and I turned and smiled up at him.

“It’s fine, don’t worry,” I told him and then kissed him again.

That was the end of the making out for a while. We talked for a little while and I pulled out my laptop and we watched YouTube videos. My friend Simi, who lives a few states away, messaged me, and I pulled out my phone and turned on Snapchat and Snapchat videoed her. So, Connor met Simi and things were good.

Eventually it got dark out, and Connor went on his way, but everything that had happened that day made me smile.

Did I mention that my nipples were sore the next two days? Because they were sore. So ladies and gents, if your partner likes to suck on your nipples, make sure they take it easy, because, seriously, they’ll hurt like a bitch.

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