Sex. Celebrity. Politics. With Teeth
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Sex. Celebrity. Politics. With Teeth

The 10 Worst Masturbation Stories We've Ever Heard

We may earn a commission from links on this page.

We asked, and did you ever answer! We learned about the many uses of a teddy bear, the perils of faulty locks and "an excellent way to get rid of undesirable roommates." And now it's time to pick the worst.


1. Grin and Bear It.
I got this giant (relative to 7 year old me) white teddy bear for Christmas one year and made an effort to sleep with it, since that's what girls are supposed to do with stuffed animals. But I wasn't really a stuffed animal person, and the thing was really too big. I must've wrapped my legs around it at some point and put the needle on the record, as it were, because I soon figured out that I could basically get on top of it and hump it and have orgasms. At seven. I was so excited about it that, during a sleepover. I showed a girl friend from school how to do it because I assumed she had a teddy bear, too, and deserved to know this information. I'll be damned if she didn't tell all of our friends at school that I humped my teddy bear. It took me about a decade and going away to boarding school to live that one down, but I think having a 23 year orgasmic success record has been worth it. Eventually I moved on to pillows and then one of those vibrating Squiggle writers and eventually to real, grown-up sex toys. I do still prefer to be on top, though.

2.School Daze.
My tale of woe was at the ripe age of 13. I was running late for school, and would have to get a lift in anyhow. I decided as I had the time and the night before had been particularly..arousing, dream wise, I'd enjoy myself. As I was reaching climax my mother burst through the door, having heard the noise, raving and screaming. This could have been the end of it, but oh no. She dragged me out of the bath (first incident of blue balls to boot.) Grabbed me by my arm, had me get dressed, and drove me in to school. Lecturing the entire way ( catholic family.) Once we reached school I thought it was over. How wrong I was. She marched me into school, into the morning assembly and up to the deputy headmaster, declaring 'I'm sorry the little sinners late, he was playing with himself in the bath."


Suffice to say, I died a little that day.

3. Mama's Revenge
I had just finished the deed, when my four year old decided to wake up, open my bedroom door and asked to come up into my bed. I toss the vibrator under my pillow, natch, and pull the covers a little tighter around me so the little one doesn't catch mommy without her bottoms on.

He curls up next to me, slides his arm under my neck and lo and behold, grabs my vibe. He slides it out from under my pillow, holds it up like the Statue of Liberty torch and said "Mama, wut's dis?" Trying to think quickly, I replied..."Oh honey, that's just something for making headaches go away. Give it to mommy."


With that, my beautiful, mop-topped, brown eyed baby boy finds the "on" switch and starts running my big ol' dildo all over his head. "Like this, Mama? You do it like this?"

Wanted. To. Die.

Next day, his father comes to pick him up for the weekend. (We're divorced). Comes in and says, "Cher, you got anything for a headache? My head is killing me."


With that, my son runs into my room, dives under my pillow, finds my vibrator again (I had shoved it back under there after regaining control of it the night before) and comes running out, waving it.

"Here, Daddy! Mommy showed me this last night! She said it helps for headaches."

Wanted. To. Die...Again.

Apparently, my little boy has forgotten this story over the years (he is 15 now), but I do believe that when he hits 21 or becomes engaged to that special someone, I will break out the story at the most inopportune and inappropriate time in his life.


Call it "Mama's Revenge".

4. LolCat
Earlier this week, I came home from work to find my male (neutered) cat aggressively humping one of the couch pillows. Startled by my presence, he stops, and I see the gears in his little head thinking, "Oh, fuck! What do I do? What do I do????!" He then hid under the couch for most of the evening until it was dinnertime. I told him that it was a natural thing and you should do it in private. He head butted me in gratitude for not yelling at him.


5. Adventures In Babysitting.
This summer I was babysitting these two girls- the oldest five and the youngest three. I was dragging them in a wagon towards the ice cream store and the youngest was conspiciously quiet (this girl is non stop chatter even with strangers, inanimate objects, herself). Worried that she was sick I looked back to check on her and to my surprise her hand is down her pants and she is going at it. Had we not been in a crowded public place I would have ignored it, but instead I told her that now was not the time, that was something for her to do in private. She was a little put out but I got them each an extra scoop of ice cream so all was forgiven.
Later that night, after their bath I'm dressing the youngest and I ask the oldest if she can choose her pajamas and get dressed. Out of the corner of my eye I notice she hasn't made a move toward her dresser so I turn toward her to ask again. She is spread eagle on her bed, with a brush handle up her butt. I shrieked! My mother is an ER nurse and is constantly coming home with sex stories gone awry, things getting stuck, puncturing important body parts so I'm just imagining all the terrible possibilities. "TAKE THAT OUT! TAKE IT OUT!" She does, confused and a little scared (I never scream at them). I'm running around with this brush now looking for rubbing alcohol when, of course, her parents come home. I look frantic. They assume I need the alcohol for an injury. I awkwardly explain what happened. While the mother gives her a stern lecture that this is, "not what Italian girls do!" The father and I stand awkwardly in the hallway, avoiding eye contact, me still holding the brush.

I came back the next night to watch them, and the oldest daughter had made me an apology card. Which was really adorable. Until I noticed she had included a drawing of the scene.


6. Steel Magnolias
At some point in my early adolescence, I developed a fondness for masturbating with magnolia buds (take a look at them some spring, and you'll see why). I lived on a street with lots of old mansions that had huge yards, and there was this place where I would go to read or daydream, in the corner of a neighbor's yard, between some bushes and a wall. Well, one day, I decided that it would be awesome to pluck a bud, ride my bike to my little hideaway, and enjoy myself in the great outdoors. It went pretty well, until I woke up to find a woman standing a few feet away - presumably the person who owned the house - looking at me, with her hands on her hips.

I leaped up, jumped on my bike, hightailed it home, and refused to go outside again for the rest of the day. For weeks, I was terrified that she would figure out who I was and tell my parents. I never went back to that yard. 13-14 years later, I still feel that mortification wash over me when I remember the incident or drive past that house.


7. Daddy Issues
I was about 14 or so, and a regular self-diddler. One day I woke up from a nap on the couch & felt a little horn-ay & since I thought I was alone I decided to go at it, using my patented middle-finger technique.

I finished with a huge moan...then suddenly I heard something, like a person clearing his throat. MY DAD WAS IN THE ROOM, sitting in his recliner—he had been there the entire time!


I pretended I was sleeping and stayed there for at least an hour on the couch until my dad left the room. I was so utterly and totally mortified I have never even spoken of this until now. My dad, thankfully, never mentioned it either.

8. The Grandmother
I don't know if I'm a natural nymphomaniac or just that horniness is in my blood, but 2 weeks after my dad gave me the "birds and bees" speech, I began 'experimenting.'


I started with JUST TOUCHING 'down there', then graduated to inserting toilet paper 'penises' (toilet paper rolled probably like the size of tampons) for stimulation after I started reading those romance novels that are basically novel porn. Then I got to sneakily watching "skinemax" or whatever super-cable channel that features porn (on my mom's boyfriend's TV while they were out on dates), so I figured out what it looks like to have sex.

Anyways, one night while I was at my grandma's house, I'm talking to my pretend 'lover,' a large german shepherd stuffed animal, telling him I can't wait for him to "make love" to me, and I straddle him and start humping him like I learned about through my 'research,' when all of a sudden I realized the bedroom door was opened and there was a shadow of someone standing in the door frame (my back had been to the door). I turn to see my fucking Grandma - totally southern, religious, and shocked.


She yelled "WHAT ARE YOU DOING??!!" and then walked out. When the blood eventually leaves my face and recirculates, I finally fall asleep. Next morning I wake up to seeing a stack of my paperback romances by the bathroom, and a toilet plunger in Grandma's hand. She methodically ripped up every book I'd had at her house, stuffed it down the toilet, and flushed - and anything that didn't immediately flush got the plunger treatment.

It sounds horrible and I love her to pieces, but at that moment I pondered how long it would take until she got Alzheimer's and forgot about the whole thing. 16 years later and I'm still mortified.


9. Fuzzy-Wuzzy
I was around 6 years old watching my mom use an electric lint remover (a small vibrate-y thing that uses revolving blades to rip off lint) and I was so fascinated by how it buzzed that I just KNEW that it'd feel good on my genitals since I had already experimented with a vibrating Furby key chain prior — how wrong was I.

Later on I sneaked into the laundry room to "borrow" it and the moment I put the nifty little gadget on my crotch I SCREAMED. It had cut my privates up and I went bawling to my mom hysterically repeating "I HURT MY PEEPEE, I HURT MY PEEPEE".


I still have a minor scar where it clipped the skin off and to this day I can't look at one of those things without closing my legs and wincing. Ack.

10. Ken
This is mortifying. I still shiver and block it out when the memory arises: I tended to use whatever was available at the age of 16; in my case, my little sister's ken doll was just the right size. Being widely uneducated about how it all worked down there at that point, I would just sit on it and rock.


Well, we all know how easily those ken heads popped off.... yep. Into the the vajayjay. The problem was, I could not get it out myself. I flipped completely out, thoughts of it going up into my uterus and damaging my internal organs (again, not properly educated!) flying through my panic-induced brain.

What did I do? I told my mother. Took a deep breath, then blurted, "I was masturbating with a ken doll and the head came off inside me!"


The look on her face was a mixture of anger, disappointment and embarrassment. But she took me upstairs, and attempted to get it out. I was crying, mortified to the core.

It got worse. She couldn't get it out. So she: got. my. FATHER.

...who then got his pliers. That worked.

Dad never talked about it again; mom walked out of the room, scolding me, saying "come talk to me next time you want to do that!"


At least I didn't wind up at the hospital?

(Top that, someone. I dare you.)