NSFW

My First Handjob

Filed under : Filthy Stories

Story 70 of 365

Est. Reading Time 6 minutes

I was in my Sophomore year Drama class. I overheard the hot, busty blonde girl behind me talking to the girl sitting next to her : “…I mean, I was kinda drunk, so I don’t remember but apparently I sucked his dick…”. My ears perked up. I turned my head slightly, making it known I heard her. She said “oh my god… did you hear that?”. I assured her she needn’t be embarrassed, I was just curious if I heard correctly. She, in a near-whisper, said “yeah, I … don’t know.. my boyfriend says I sucked his dick, but I don’t remember”. I’m still skeptical of people not remembering things — especially important things — when they’re drunk, and that’s extremely rare even for me and I drink quite a lot. At the time, I fully didn’t understand as I’d never been drunk, or done any drugs (outside of smoking cigarettes and having the occasional shot, or beer).

For many years — and I mean until I was in my mid-20s — I refused to engage in anything sexual with a woman who seemed drunker than I was. I still kinda have that rule, but it’s context-dependent. Like, if it’s a first date or someone who’d rejected me in the past. I’m much more more lax if it’s someone I’ve fucked around with before and we’re not doing anything we hadn’t done before. At that age, however, I had it in my head that even a 2-beer buzz would suddenly render a woman’s decision-making centers null and void and I thought anyone who even attempted hooking up with them was a borderline predator.

You can imagine my thought process upon hearing about a girl giving a blowjob she didn’t remember while drunk.

I asked her “doesn’t that bother you that he would take advantage of you like that?”. She said “ohh, no, no. I don’t care that I sucked his dick – I just don’t remember doing it. Would’ve been nice to remember giving my first blowjob is all”. A few days later, I overheard her say she finally sucked him off while sober. She saw my head turn and we got into another of our semi-whisper conversations where she gave more details, like “it was fun!”. At that point, my concern for her safety drifted away and was replaced with “ahh… so she likes sucking dicks, eh?”. That was very enticing to me. As luck would have it — for me, anyway — her and the boyfriend were in a rocky relationship and it was only maybe a week or two later that they broke up.

Luck was on my side again about a week later, when the teacher paired people up for a two-person scene and I got paired with her. Amy was her name. Being “forced to” spend time alone with Amy helped me out a lot. I found out she was a Christian girl, and I invited her to join me for a youth group night. I wasn’t going to those with any regularity by that point, but I figured it was an easy way to arrange a date both of our parents would be fine with us doing.

It worked.

When we got to the church, it being nighttime and all, no one knew we were coming to the group and couldn’t really see us anyway. While they all shuffled into one of the classroom-style rooms in the hall outside the church, she grabbed my hand and said “do you wanna skip this and just makeout instead?”. Yes, I very much did. We made-out for a good 20-30 minutes, until someone from the group saw us on their way to the bathroom. We weren’t in trouble or anything, we just decided we should probably go somewhere more private. So, we went into the church and made-out and felt each other up while lying on a church pew.

When we heard the group let out, we just snuck in behind them and waited for our respective parents to come pick us up. As her dad pulled up, she turned to give me a hug and I whispered in her ear “did you wanna go out?” and she let out a little squeal “OHMYGOD YEAH!”. Amy was now my girlfriend, as per the rules of our time and age.

A few days later, I invited her over to my house after school. Since my mom was a Drama teacher at the middle school across the street, and currently in the middle of producing a play, I knew she wouldn’t be home until at least 6pm. That gave Amy and I a solid 3+ hours of alone time.

When we walked into my room, I honestly didn’t even know what to do. I’d never before been alone in a room with a woman who wanted to, and enjoyed, making out with me and we were free to do whatever we wanted for a few hours. My first plan of action was to put on some music 1which hilariously continues to this day — I always have a soundtrack prepared when women enter my room. Since I’d recently gotten the new NIN album The Downward Spiral, that was the soundtrack I chose 2It’s a weird thing to realize that I’ve since had sex with women who weren’t even born when I got my first handjob.

She sat down on my futon/bed combo, and pulled me close to her. We made-out, we groped, and she started undoing my belt buckle a little bit. That’s when I heard my mom come home. I put Amy in the closet, in case my mom came in, but she never did. She apparently just ran into the house to grab something and ran back out again. We went back to the futon, and she started in on my belt. Since apparently women at — it seems — just about any age never quite figure out how belts and pant buttons work 3I’ve honestly lost track how many times women have tried to remove my pants only to give up and say “can you do it?”, I had some time to spare. I pulled the straps of her top and her bra down along her arms, and said “is this okay?” 4I had asked that at every step along the way, cause I was so fucking nervous and didn’t know what I was “allowed” to do. I’m ...continue. She laughed “yeah, do you want me to take it off instead?”. Ohhh yes, yes I did. That was the first time I ever saw — with my own eyes, in real life — a pair of boobs. And goddamn if it isn’t still just as exciting to see a new pair of titties today as it was 20 years ago. I got to touch them, and tease them, and pinch them, and lick them. Holy shit I was in heaven.

Until she undid my belt, and started unzipping my pants.

All my life, until that point, I was convinced I had an embarrassingly small penis. I’ve mentioned this before. I knew I couldn’t hide, or make excuses, or run away this time. I had to just man up and let a woman pull out my dick and laugh at me. I figured “well, at least I got to play with some boobs for a bit”. When she finally pulled my boxers down with one hand while pulling out my dick with her other hand, my eyes were closed, my hands were still, and I was frozen in fear. When I didn’t hear something like “you call that a dick?”, I opened my eyes and she was … smiling. Just like I’d been while playing with her boobs. She was just having a good ol’ time. There was suddenly nothing at all to be afraid of. She saw my dick, made no remarks on its size — for better or worse — and we were just two young hornballs having fun.

She and I only dated for a little over 2 weeks before she ran off with a kid I used to be on the wrestling team with in middle school (I wasn’t exactly friends with him, but he and I were always cool with each other, even after she started dating him), but in the course of that few weeks, many “firsts” were had.

That being said, no sexual experience I’ve ever had, or will ever have, can top the moment I found out that I didn’t have the world’s tiniest dick.

Footnotes   [ + ]

1. which hilariously continues to this day — I always have a soundtrack prepared when women enter my room
2. It’s a weird thing to realize that I’ve since had sex with women who weren’t even born when I got my first handjob
3. I’ve honestly lost track how many times women have tried to remove my pants only to give up and say “can you do it?”
4. I had asked that at every step along the way, cause I was so fucking nervous and didn’t know what I was “allowed” to do. I’m not sure at what age I stopped asking those questions along the way to women I was with, but — while I prefer enthusiastic consent — I’ve since learned what a “nope!” looks and sounds like