Awkward Sex Stories: Meeting the Family

Hang on for a minute...we're trying to find some more stories you might like.


Email This Story






Okay, tonight is the night. I’m about to lose my virginity … to a cute 26-year-old guy I found on Tinder.

We matched a few days before, and he kept sending me messages that had me blushing and ready to pounce on him.

So, the night finally comes when we’re both free, and I decide to give sex a try — I’m excited.

I get out of a meeting, and he tells me to pick him up from a bar downtown where he’s having a drink with his brother. Kind of odd to be stone-cold sober picking up a buzzed stranger, but no big deal. Soon enough, he’s in my car, grabbing onto my right thigh while my foot’s pressing on the gas, and we’re heading to his place, my phone’s GPS leading the way.

Then he tells me that he left his wallet at a friend’s house and asks to stop there on the way. This is weird because he was literally just in a bar — how did he manage to get in or pay without his ID or any cash? Whatever, this doesn’t matter — I’m getting laid.

After waiting awkwardly alone while he fetched his wallet, we meander down residential streets and arrive at a surprisingly large house — with a boat in the driveway. Now I’m starting to wonder: who the heck is this guy? As we’re getting out of the car, he asks me, “You don’t have a problem with guns or animals, do you?”

Uhhhh. This is an odd question. What is he suggesting is inside? Doesn’t matter — I’m getting laid.

We walk into a dark hallway and make our way to a large den with a well-stocked bar. Neat. Then I take a look around, glancing up at the walls. Then I see them. So many huge African animals mounted proudly. Amidst my subsequent verbal freak out, he remains silent and nonchalant. Okay, I can look past this — I’m just here to get laid.

He offers me some top-shelf whiskey, and I take it, wanting to calm my nerves a bit. We sit outside by a fancy pool with exquisite landscaping. After chatting for a while and allowing the alcohol to take effect, I decide to make a move. “Let’s go.”

He leads the way, and close to the stairs I see a room with a light on. We get closer to the room, and Tinder Boy says, “Hey Dad.” I stop in my tracks. How freaking weird. I’m about to lose my virginity to an older guy that still lives with his parents? And his dad knows what’s about to happen? Weird, but I’m on a mission — I’m going to get laid.

We make it to his room, and I end up supplying the condom. I’d figured a guy like him would have a box of them nearby, but apparently not. Then it happened. My mission was accomplished. It was pretty fun, but then I looked down and noticed that the condom was no longer there. Mayday, Mayday … what happened? Do condoms “slip off?”

After a little freak out and explanation that I don’t want to get pregnant and that I’m not interested in his offer to “just pull out,” I supply a second condom. Then, just as things start getting good again, there’s a thunderous pounding on the door. “What the fuck, man! Open this door and get out of my room!” Very startled, confused, vulnerable, I clumsily pull on my clothes.

What is going on? Did Tinder Boy seriously just do me on his brother’s bed? Without my knowledge? Then act like his brother was the asshole in the situation?

I rush out of the room, profusely apologizing to the brother whose bed I’d just corrupted, and attempting to find my way out. Tinder Boy escorts me downstairs then audaciously points to a couch and asks if I wanted to “finish up” there. I nearly slap him. With a curt goodbye, I leave.

The sex with Tinder Boy was good, but the situation was just too uncomfy. Tinder hookup: 3/10, would not recommend.