Sex
3 min

The Masturbatory Tales: Volume 1

To mark Masturbation Month, David Benjamin Tomlinson shares his most harrowing story of self-pleasure

To mark Masturbation Month, David-Benjamin Tomlinson relates his hilarious story of self-pleasure. Credit: XTRA FILE PHOTO

Christmas Eve. I’m at my mom’s house, drunk on tequila and high on pot cookies. In my hands, I’m holding a vibrating anal egg, a thoughtful Christmas gift from my roommate (I had stuffed it in my bag before I left the city, unsure if I would have an opportunity to give it a whirl over the holidays, but you know: better safe than sorry). There, with my family asleep and me the last one standing, alone in the basement, medicated and horny, opportunity is indeed a-knockin.’ 

I’m prepared, of course. I had brought lube, for ease, and a condom to pop the egg into, to simplify clean-up — I’m a planner. My family is snoring above me on all sides in different rooms, and before you can say “Pa-rum-pa-pum-pum,” there I am squatting on the basement floor with a hard-on, easing the lubed, egg-filled condom into my asshole. Merry Christmas to me. It pops inside, a thin black wire extending from my ass to the handset, which I immediately grab and fire up. It’s fantastic (thank you, makers of all things vibrate-y — thank you very, very much). I go to business, switching vibratory speeds, yanking away on my dick, thinking about sexy Santas and having a jolly (but respectfully quiet) old time. Things ultimately go as things of this nature often do: there is a highly enjoyable climax, after which I lay back, congratulating myself on a job very well done. After a few moments of festive bliss, it’s time to clean up. I reach down, grab the wire and prepare to gently pull the egg out of my ass.

There are moments in life when you are so absolutely sure of one outcome that when a different and wholly unexpected outcome presents itself, you are tossed into a blind panic. I anticipate that I will tug the wire, the egg will be released, I’ll sigh, dispose of the condom, pack everything away, and get some sleep before Santa swings ’round.

I gently tug the wire, and . . . nothing happens. The egg does not budge. I tug again . . . a little more insistently, and . . . nothing. The thing that was supposed to happen hasn’t, and suddenly I’m panicking. And because I’m panicking, I’m clenching, and because I’m clenching, that egg isn’t going anywhere. I know I have to relax; I lay back and take a breath . . . and that’s when all the shame voices start. I’m sitting covered in cum on Christmas Eve in my mom’s basement with a wire hanging out of my ass; I’m a pervert. What kind of a monster does this? It’s at this point that my medicated state turns against me; paranoia sets in. What kind of a pig are youYou’re going to have to pull so hard on that wire, it’s going to tear loose, leaving the egg inside. You’re going to have to go upstairs and wake somebody up and get them to take you to the hospital because there’s a vibrating egg up your ass. How are you going to explain that? You have just broken Christmas

Luckily, I have a lot of experience with anxiety and the demon voices in my head. EVERYBODY SHUT THE FUCK UP. A sudden, graceful silence fills my head (my demon voices know who’s boss). Lying there, I turn the egg back on, hoping it will soothe the muscles in the surrounding area into a less alarmed state. Once again, the egg does its magic, and I briefly contemplate going for round two but decide against it. I realize it’s possible that my ass just doesn’t want the egg to go, like a little boy faced with having to surrender his brand new fire truck on Christmas morning. I think happy thoughts and stealthily wrap the wire around my right hand. When the moment feels right (and my ass feels reasonably distracted), I yank. PLIP! Out pops the egg. I lay back on the bed, grateful and victorious. In that moment, it’s the very best Christmas gift I could ever get. 

I become immediately cocky as I clean up and pack everything away. I’m not a monster, I’m sexy. Who doesn’t masturbate with a new sexy toy in their mother’s basement on Christmas Eve when they go home for the holidays? 

It’s a question I’m still not sure I want the answer to.