“Bet you can’t jump that ditch.” Four hours later the guy had dislocated one of shoulders the doctor told us.

10. Jealous Times At University

In my first or second year of UNI my group of friends and I were having a get together after finals ended. Considering finals had just ended and it was only about 7 of us, consuming alcohol seemed like the go to activity.

So once the buzz started to hit us one of my friends tried to start a game of spin the bottle, but being a group of three couples and one single guy we decided to play truth or dare instead.

Like all truth or dare games it started out pretty innocently (Take more shots, who’s your celebrity crush, ect), but eventually things turned a bit weird. Our one single guy decided to dare one of the girls to lick whipped cream off of his schlong, and with a reluctant nod from her boyfriend she got to action. Or…at least tried to.

Once she took off the dude’s pants and saw his (well) hung appendage she yells “Damn I’ve never seen one this big!” And before she could even uncap the whipped cream her boyfriend was swinging full force at the guy.
Me and my other friend had to get in between a half naked guy and a drunk ape, and by the time we split them up everyone was uncomfortable as hell.
After we resolved it and me and my girlfriend started leaving I just remember her leaning up to my ear and telling me “She knew her boyfriend was self conscious about his dick.”

11. At McDonald’s, In Your Underwear

Probably 20years old at the time. Gf her sister and girl cousin from Germany were in the car. Cousin says let’s play and so we all said OK. All fun and games till we pull over into a McDonald’s parking lot and I get dared to walk in and order fries in my underwear. They drove off and I had to borrow the phone to call my gf to make them come back for me. Saw all the tits though, so it was worth it.

12. It Just Became A Giant Orgy

I found out my fiance’s bachelorette party was basically an orgy. I found out years later from someone who was in attendance. I think the fun began as a Truth or Dare game. A co-worker of my wife’s ate her out. Two men staying on the same hotel floor fucked my wife-to-be and her friend. I had no idea until after our divorce. It’s funny…my bachelor party was so tame. We grilled and walked downtown to a couple bars and were back by midnight. Who knew?

13. Why Not Both…Or All?

At my first job, back when I was a teenager, about 6 of us were playing this mid-shift. 3 girls, 3 guys. It was barely starting to get risqué and one of the guys is asked “have you ever masturbated to thoughts of a coworker?” And he says yes.

This is as juicy as it’s gotten, so we latch onto it. The next time around, he’s asked if he’s masturbated to anyone else playing. He says yes. Next round, he’s asked to name which of us he’s jerked it to. He looks at us one by one, then says “all of you.” The guys all got flustered as hell, they’d never even realized they were on the roster.

14. It Was All He Had

I think my most exciting game of truth or dare was cut down in its prime when a guy dared his girlfriend to flash everyone and then broke down crying because now everyone had seen her bikini zone and he no longer felt special.

15. The Wrong Hole

When I was 17, I was “studying” with a girl who started a game of truth or dare with me. I hadn’t kissed since 4th grade, and we were clearly into each other. The game started with me as the asker. She chose dare. Me being the naive, socially awkward individual that I am, dared her to touch the bottom of my family’s shared toilet (which was actually really clean). She resisted, but eventually did it. When my turn came around I chose dare, it was only fair to do so after what I just put her through. She dared me to finger her. At the moment I was ecstatic. As we made our way to the sauna adjoining the bathroom a rush of terror came over me. I had no idea how to do what I was about to do. I’d basically never kissed, and now I was about to finger this chick. Anyways, we get into the sauna and its pitch black. I feel around and find her pelvic region. As I work my way down I try to recollect the very few pornos I’d seen to that point. I start feeling around and wiggling my finger side to side. She jerked her whole body back and exclaimed, “too low!” I quickly realized that I had fingered the wrong hole. And slide it (the same finger) up to her vag. After about 10 seconds she said I was doing it too hard, and about 20 seconds later she stopped me completely. Needless to say, it was a short lived study session.

16. She Went Above And Waaaay Beyond

We told her she had to kiss the dog, we didn’t think she was going to use tongue. After that we just didn’t want to play anymore.

17. A Disastrous Ending

This is a growing up pre-internet disclaimer. Seeing boobs was elusive if you had no access to a “porn stash”. I didn’t. So you’d see them in movies…and no pausing them mind you. No VCR. You’d see the boobs then poof their gone. So over my friends house when I was 13 his older stepsister and her friend were bored and actually talking to us. They were 15. It just started. I had never played before, but I knew the rules. We had a round of Truths. Then Dares. I dared my friends stepsister to flash her boobs. SHE DID!. Real boobs. It was magical. I got dared to strip naked. All the way naked. I did very reluctantly. I had a boner and out of nowhere the stepsister touches it and instant launch. It was awful. There were screams of “ewww” and gross. She shoved me and I fell backwards. It wasn’t a good ending to what could have been a spectacular evening.

18. Lucy And Kyle Break Up

A few years ago now my friends and I all decided to try and make jello shots for the first time. We added way too much vodka to them but we all felt obligated to finish them. We took the empty handle of Smirnoff and one of my friends decided to play truth or dare spin the bottle. With all of us pretty trashed already it seemed like a good idea.

For the first few rounds it was all fine, pretty normal stuff; take a shot, go outside and eat some snow (it was winter break). But then one friend, let’s call him Kevin, decided to dare one of the girls to take off her top. Now no one at the party was single, and everyone’s respective partner was in attendance, which will be important later.

The girl Kevin asked to take her top off decided to play along and that was fine. But her boyfriend, we’ll call him Kyle, seemed to get jealous because he then made it his mission to get Kevin’s girlfriend naked. Every time it was Kyle’s turn he would find a way to target Kevin’s girlfriend. The bottle pointed to me at one point and he dared me to take off Kevin’s girlfriend’s bra (of course I did it being a team player). It didn’t take long for Kevin to pick up on this so he started to target Kyle’s girlfriend for the same purpose.

I should also mention that truth became all but ruled out around this time because anyone who opted for it would be ridiculed for choosing the “pussy option”.

Eventually Kevin, Kyle, their girlfriends (call them Emily and Lucy respectively), and everyone else in the circle, 8 of us total, we’re down to nothing but underwear bottoms. Kevin gets a turn and dares Lucy to let him take off her panties. She blushes and and tries to say no but everyone begins to cheer for her to do it. Eventually she gets up, walks over to Kevin, and he just rips off her panties and immediately buries his face in her crotch and she starts to moan and stays on his face. The room goes silent, Emily gets up and storms out of the room.

Apparently Lucy and Kevin had been cheating with each other. Kyle had been suspicious but didn’t want to risk accusing Lucy without proof. Obviously this let the cat out of the bag and what followed were some very choice words and us never hanging out with Kevin or Lucy again.

19. Middle School Is So Awful

This was at a birthday party in middle school. A late-blooming boy chose “truth” and was asked if he had pubes. He was silent for what seemed like forever, then said “no” softly, causing the room to erupt with laughter. He began to cry and had to leave the room. He didn’t come out for HOURS. He had a girlfriend at the party so I’m sure it added to the embarrassment.

20. “It Was Terrifying”

We (3 guys and 3 girls) were all in the hottub at this chick’s house playing ‘Truth or Dare’, and I get dared to go mash my dick/balls up against her parents’ bedroom window. Granted, it’s like 1am, and the whole house is completely dark, so I thought it would be no big deal.

Get out of the hottub, run over to the window, drop my suit, and smash my junk up against the window for a few moments. Then, in the reflective light of the pool, I catch a glimpse of her parents sitting right inside the window, watching us from inside. They didn’t even blink, just just watched me. It was fucking terrifying. TERRIFYING. Like, I saw them for a split fucking second as the light passed over the glass, just inches away from my mashed up dick on the other side of the window. Something from a horror movie. I gasped and ran back to the hottub, got back in, and just sat there in complete silence.

A couple minutes later, her dad comes outside laughing, hands me a beer, and then reminisces with all of us for a minute about the crazy shit he did when he was a kid.

I’ve never felt a shock like I did when I saw their faces. It still haunts me sometimes, but it all turned out better than expected.

…I was 25.

21. The Lamest House Party Ever

I was at my first ever house party. I was pretty drunk, didn’t really know many people there and wanted to impress. So naturally, when we were playing truth or dare and someone dared me to strip to my boxers and run around the garden (fully expecting me not to do it and to instead take the forfeit of five tequila shots), I actually did it. Instead of cheers of “haha, he actually did it the madman” everyone just thought I was some sort of weird pervert and hardly anyone would talk to me for the rest of the party.