Being somewhat of an Instagram personality, I get guys in my DMs (that’s “direct messages” for those unfamiliar) pretty much on a daily basis. The majority of the messages are some form of flirting, but usually from guys that, I’ll be perfectly honest, I’d probably never go out with. Truth be told, half the time I don’t even read my messages because I’m almost positive they’ll be something weird, a dick pic, or some foreign man asking to see my “bobs and vegana.” But then, every once in a while I’ll see a message from a guy who looks like there’s a chance he could be attractive, so I stalk his instagram account (if it’s public) and determine whether or not I want to answer.
Bro tip: if you slide into my DMs, make your profile public. You’re far more likely to get a response that way.
After a disappointing couple of days being let down by a couple of men I’d been interested in, I resolved to spend the Fourth of July alone on the beach, which was equal parts depressing and liberating as I love fireworks but people can be annoying. I was scrolling through my messages when a DM from Sam popped up. He was drunk and partying with his friends in San Francisco, but he lived in the South Bay near me and wanted to take me out for drinks when he was back in town. Naturally, I played hard to get and engaged in some playful banter while I carefully and methodically stalked his entire Instagram account to determine if he was cute or not. He didn’t have a ton of photos of himself and the few he had were mostly him making ridiculous faces, so I really couldn’t tell much other than he had the bald and bearded thing going on and appeared to be in shape, but I figured why not. At the very least I’d get some free drinks out of the deal and maybe a dinner and a friend.
Once Sam was back in town he asked if I wanted to go to Strand House in Manhattan Beach at 8pm. Not really my vibe, and since 8pm could be a drinks time or a dinner time, I casually asked “are you feeding me or should I eat first?” Sam laughed and said he’d be happy to feed me and suggested going to Fishing With Dynamite instead. Considering that’s my favorite restaurant in Manhattan Beach and I love oysters, Sam was already winning some points, so couldn’t help but respond so politely with:
“So are you actively trying to fuck me, or…?’
He laughed and said “well, yeah obviously” and we agreed to meet at 8. I never really get super excited about dates, perhaps out of self-preservation or just because I’m a bitch, but I was at least looking forward to oysters and possibly some dick. I threw on a casual beach dress and headed to the restaurant, which I arrived to early but Sam had the foresight to make a reservation so they seated me right away. I sat down and ordered a glass of sparkling rose’ (because I can’t be TOTALLY devoid of my basic bitch tendencies) and waiting for Sam to arrive. Just a few minutes passed and he walked in with a huge smile on his face. Sam was cute, not totally my type but I could see he had a couple of tattoos and seemed to have a cool chill vibe about him and the conversation began to flow as easily as it had in text messages. We ordered oysters and a bottle of the same sparkling rose’ I’d been sipping on to get started, and then another round of each, and then more food, and then when we were already tipsy and probably had no business continuing to drink we made the (probably) ill-advised decision to go to Manhattan Beach’s loveliest dive, Shellback’s Tavern.
Two pitchers of Kona Big Wave and my rousing rendition of Toto’s “Africa” while it played on the jukebox later, we began sloppily making out at the bar. Gross. I HATE when people do that. But also, when Meredith has had *just* the right amount to drink, her drunken alter-ego Jackie appears and Jackie gives even fewer fucks than Meredith does.
Hoe tip: Give your drunk self a different name so you can blame your bad behavior on your alter-ego and not take any responsibility.
The bar was emptying and I decided I was going home with Sam. Sam called us a Lyft and we were headed to his place in Redondo. As we’re on our way I begin to ask Sam about his living situation, like if he was in a house or an apartment or had roommates or what.
Oh god. This was where the ball was going to drop. Not knowing where this was going next he began explaining to me that his lease had ended recently and he wasn’t moving into a new place for a couple of months so he was currently living at his grandmother’s house.
Yes. He was bringing me home to his GRANDMA’S HOUSE.
What the fuck. He explained that it was a split level house and he has his own entrance and total privacy but he was basically sneaking me in and out like we were in high school. Sober me probably wouldn’t have been too excited about it, but Jackie was drunk and horny and didn’t really give a fuck. So away we went to Sam’s grandma’s house.
Once in his room we picked up where we left off and began making out aggressively. As I was only wearing a dress with nothing underneath (I almost never wear a bra or panties) I was naked before I knew it and he was going down on me. I always appreciate a man who gets me off first because I’m not one of those women who regularly cums from penetration. Once I came it was sort of whirlwind of Sam getting undressed and we commenced the sloppy drunk fucking. Sam was pretty average size wise, but I was really too drunk to care either way and as we went from position to position Sam started with the ass play. I was totally down to get weird and gave him the green light, and just like that, we were doing anal on the first date. It wasn’t long before Sam was ready to cum, and I guess Jackie was really taking over that night because I told him to cum in my ass…so he did. Anal creampie on the first date, my mother would be so proud.
After the awkward cleanup that is always associated with an anal creampie, it was definitely time to pass the fuck out. After some solid drunken sleep, we woke up around 8 or 9 the next morning and Sam kindly offered me a ride home and some breakfast. I mean, a gentleman always buys a lady breakfast after cumming in her asshole, right? That like some kind of etiquette rule I think. I don’t know, cotillion was a long time ago. After sneaking me out past grandma and taking me to breakfast, Sam took me home and we agreed we should do it again sometime.
My summer schedule was all over the place and we were both in and out-of-town quite a bit, so we never really made it happen again and the appeal faded, but we’re still in touch and always laugh about the first date anal. While the majority of the guys who slide into DMs on Instagram are usually weird, creepy, or just not cute, don’t count them all out because every once in a while you find yourself a cute guy like Sam who takes you out to an expensive dinner, fucks you in the ass, and buys you breakfast the next morning. That’s modern romance, y’all.