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TIFUpate: allowing my coworker to set me up

TIFU by getting caught by my Mom using a dildo for the first time...on Christmas Eve

So I'm a guy and I've been struggling with my sexuality, wondering if I'm bi or gay. I've never done anything with another guy and have always heavily repressed any thoughts, pushed them out of my head. I got to the point almost two weeks ago where I thought "Fuck it, I need to start experimenting to at least know who I am, I don't want to be an old man and not know." So I order a dildo and a couple things online.

Now, I live in an apartment with my Mom and this is the first Christmas we're spending without my Dad, who passed away from cancer in the last year. Mom decides that spending Christmas at home with just me like we always did as a family would remind her too much of Dad, because it would just be all the things we normally do...without him. So instead she arranges to go spend Christmas with some friends a few cities over. She offers for me to come too but I say no because I don't know them well and honestly, in the back of my mind I thought, "This is my chance to really have a weekend to myself, and that's the perfect time to try this dildo".

Today we exchange presents early and my Mom leaves and I prep like I'm expecting the Santa of sex to show up, even though I'm alone. I take a long hot bath, I groom myself, I put on the nice bed sheets. In a way, this is all partly a way to have me forget about my Dad too, do something so wild that I just don't think about Christmas.

Here come the fuck ups. One, I shut off my phone because I wanted no distractions. Two, because I assumed my Mom would be gone til Tuesday, I didn't lock my bedroom door. Three, I put on gay porn on noise-canceling headphones.

Oh and fourth, I didn't check any weather reports, because if I did I would've known about massive snow storms, more severe than both me and my Mom were expecting. I would've known that the highway my Mom was going to be traveling on ended up getting temporarily shut down, and I would've had my phone on to either check with her or receive calls from her that she was coming home.

But I didn't. I didn't hear those calls, I didn't lock those doors. You know what's happening and the timing couldn't be worse, because of ALL THE TIMES during this day she could've come home, she had to come home when I was using the dildo for the first time. When I was having a formative sexual experience that may have changed the way I viewed my sexuality. She could've come 40 minutes earlier and caught me masturbating, she could've come 60 minutes later and caught me, I don't know, eating a sandwich or something.

Instead, my Mom saw me on my bed, on my hands and knees, in front of a laptop playing gay porn, my ass facing my door, pushing a dildo in and out of my ass. She immediately closed the door and just shouted "WHY WASN'T YOUR PHONE ON" in a tone that immediately let me know she was angry at me, and God, and the concept of snow, for putting her in a position to see her son stuffed with seven inches of fake dong.

Oh, and she was holding two bags full of delicious food she had brought back as a surprise since she was going to have to stay home for the holidays with me.

We had a very brief, very awkward conversation but I can tell she doesn't want to talk about it right now and honestly neither do I. We've both hidden in our rooms, the food has gone uneaten.

I am such a fucking idiot. If I had taken just one of three or four precautions, just one of them, I wouldn't be in this situation. Now, this kind of huge moment in my life, is always going to be tied to the most embarrassing memory of my life and meanwhile I've ruined the first Christmas my Mom has had without her husband. Because I was horny. Merry Christmas

TL;DR My Mom caught me on Christmas Eve, the first one since my Dad died, having my first gay experience fucking myself with a dildo because I wasn't smart enough to do even one of four simple things that would've prevented her from catching me

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