The first time I ever gave a handjob was with my second boyfriend, “Austin”. I never actually slept with him, but fooling around in his car that last summer after high school made some of my favorite memories, partly because I was young and stupid and he seemed so cocky and cute. The first guy I ever did anything sexual with, he definitely got me going. Since I know you all care, I unfortunately was too naïve to care or reeeeally notice dick size at this point. However, he did have a bigger dick than my later “serious” boyfriend would. It was honestly barely longer, if much at all, but a decent bit thicker. Though, he never got it inside me, so too bad for him!
As we usually did in those days, we had pulled into a 24 hour drive-through at an A&W, and he was being his usual really funny and flirty self. We hadn’t done much beyond kissing and some heavy petting, and he’d been teasing me the entire time about how much of a good girl/virgin/nervous mess I was.
Making little mocking (in a cute way) comments about how I’d probably lose my mind the moment he even touched me. He was really getting to me a bit, but he was smooth enough that it was real charming. I don’t remember exactly what I was wearing, though it was probably one of my dorky gaming shirts and a cute fluttery black skirt. He wasn’t dressed up, just wearing these whitish grey sweatpants, and a plain black tee-shirt, but he looked really good in them. He filled his clothes out pretty nicely, almost athletic, though he was still dorky enough to be attractive.
We parked behind the building, looking out onto the snowy landscape. There was actually a great view that was pretty romantic (despite a fast food burger place being behind us. There were still some lights on us, but we were mostly covered, and it was late and the weather was bad enough that I wasn’t very worried. Till this day I still think he intentionally brought us here to make out, but he swears the mood just progressed naturally. After we made some cute conversation (he made some dumb joke about pie rates and pirates and I called him a loser), he made his move. This was early days of dating, but he was pretty smooth about it.
After I called him a loser, he made some comment about what that made me if I desperately wanted a loser (but it was smoother than that), and he leaned in to kiss me.
We went at it for a bit before his tongue slipped into my mouth, and his hand went under my shirt.
I remember he played with me for a bit before he pinched my nipple and I squealed into his mouth, which pissed me off cause he pulled away for a second and smirked this cocky smirk at me.
Clearly he was getting a big head about it, and I thought back to his comment about me losing my mind when he touched me. We continued to make out and I was annoyed and really didn’t want to be outdone, so I reached into his crotch and grabbed him. It wasn’t hard to find even with my face mashed against his, cause like I said he was pretty big and making an obvious outline in those sweats. It was definitely not pornstar level or anything, maybe like 6ish inches or so? I don’t know, I never measured, but it was thick enough that it felt meaty in my hands, which was nice.
Wanting a bit of control, I teased his head and then grabbed and stroked him through his clothes, which caught him off guard and make him stop for a moment. Honestly, I felt a bit superior just then but he took it in stride and just went right back to kissing me. The jerk even slipped his other hand under my shirt, and started to pull on both my left nipple and knead my right breast at the same time, so I was still the only one moaning. It kind of annoyed me that Austin seemed to know what he was doing tbh. He drew little circles around my areola before really lightly pinching and just barely pulling my nipple. He didn’t focus exclusively on it either, he’d tease and pull his fingers away, circling back once I caught my breath.
I’ll admit, it felt really nice but I mostly remember annoyance haha.
After a bit of this I decided – and it was a hard decision to make lol – I needed to actually make my move. I pushed him back onto his seat, pulled down his sweats and finally freed his cock. He seemed to know what I had in mind, so he moved his seat back, and I got between his legs. He tried to reach for me again but I slapped his arm away, gave him my best “my turn bitch” look, grabbed his cock, and went at it. I stroked him hard with one hand and kinda held his chest back against the seat with the other.
I remember the first groan I got out of him was when I stopped, sort of sat up and made a big show of slurping on my fingers to get them nice and wet, hovered them over his dick, and then grabbed and jerked him off as well as I could.
He didn’t last too much longer after that. I didn’t have the greatest technique, but I guess it doesn’t really matter that young, cause he came all over himself anyways. He had enough to sense to have pulled his shirt just high enough to mostly cum on his bare stomach, but a drop or two dripped into his sweats anyways.
Just to be a bit of a brat I wiped my hands on his sweats while he caught his breath haha, and I “licked” my fingers after, though it was pretty much all off.
Source: reddit.com/r/gonewildstories/comments/r9ua83/a_slutty_gingers_first_handjob
10/10 story. More please