High School Experience (Non-Fiction)

[ChloeThompson87]

This story may be a bit more tame than the more extreme dares on here, but it is completely true.

When I was in high school (about four years ago), we had a tight group of friends that included five of us - Kayla, Jason, Tyler, Amy and myself. We usually hung around Kayla's house since her parents were almost never home. Not that we were ever up to anything mischievous, we just enjoyed the feeling of independence that came with an empty house. Plenty of memorable things happened between the five of us during high school, but the one that I remember the most happened our Junior year.

We were hanging out at Kayla's house one Saturday and were generally pretty bored. I think it was Amy that came up with the idea for us to play truth or dare. We all thought it was funny since most of us hadn't played something like that since we were little kids. We had nothing better to do, so we all agreed. After a lot of talking and kidding around, Amy also had the idea to have everyone throw in $10 to the side in order to prevent someone from backing out on a dare. If someone refused to do a dare or to tell a truth, that person would forfeit their $10. Jason didn't like that idea for some reason, but we eventually talked him into coughing up the money.

So we all sat down in the living room ready to play. I was feeling a little bit nervous, but it was also kind of exciting to be doing something different for a change. We all rolled dice to see who would be going first, which ended up being Jason. Since he's a guy, we all pretty much knew he would be daring one of the girls first.

Jason: Ok, Amy - Truth or Dare?

Amy: Truth.

Jason: Aw, you're lame. Ok, shit... hold on, I've gotta think of something to ask you.

We all ended up getting kind of annoyed with him since he took forever to think of a question to ask her.

Jason: Ok, ok, got one. Have you ever given a blowjob?

Amy: Um, no. I think it's safe to say that I don't plan on it any time soon either.

None of us were really surprised. Amy was pretty religious and innocent, so we scolded Jason for asking such a dumb question. Since we were going clockwise from Jason, it was now my turn.

Me: Tyler, truth or dare?

Tyler: I'm feeling ballsy. Dare.

Me: I dare you to go into Kayla's parents' bedroom and grab a pair of her mom's pantyhose then put them on in the bathroom.

Tyler: What? What kind of dare is that? Come on, that's lame. Think of another one.

Me: Don't be such a pussy. Come on, it's just pantyhose, it's not going to make your balls fall off. I don't think Kayla will mind.

Kayla: Um, well, as creepy and weird as it is, I guess I'm ok with it for the sake of the game.

Tyler: Fine, whatever. It's better than losing my 10 bucks, so I guess I'll do it. What drawer does she keep them in?

Kayla: The second drawer from the top next to the bed. There's a bunch of different colors, so just pick one.

Jason got up and went into Kayla's parents' bedroom. A couple of minutes later he came out and went straight to the bathroom. When he finally came out, he was smiling.

Tyler: I found a loophole anyway. Since I can just put my jeans and socks on over the pantyhose, no one can even tell I'm wearing them anyway.

Me: Whatever Tyler, maybe you won't be so lucky next time someone dares you. Let's see the hose to make sure you're not lying.

Tyler pulled up the bottom of his jeans slightly to show that he was wearing tan pantyhose under it. He seemed kind of embarrassed and uncomfortable so he quickly sat back down so that we could get on with the game.

[ChloeThompson87]

Since this story has so much detail to it, I'm going to post it in segments. I might post another one tonight, but the rest will have to be done another day.

Oh, and if any of the characters in this story happen to stumble upon this site and read this (as unlikely as that is), don't worry about me not changing your names since there are no last names mentioned. And um, sorry for publicly telling this story lol.

[ChloeThompson87]

Now it was Amy's turn.

Amy: Chloe, truth or dare?

Me: Dare.

Amy: Um, I don't know... I dare you to call one of your ex-boyfriends and pretend to be a telemarketer.

Me: Pfft, sure, no problem.

There's no need to go into any detail about the call, since there wasn't really much to it. I called my old boyfriend, Joe and asked him if he was happy with his telephone service. He said yeah and and that he was busy, then I said thank you and have a nice day. End of conversation. Moving on.

Now it was Kayla's turn and she looked like she had been boiling up an idea and was anxious to let it out.

Kayla: Tyler, I dare you to kiss Jason on the lips.

Tyler: Oh come on, what the fuck? This is getting too gay for me. Fuck the ten dollars, I'm out.

Kayla: Awww, come on. We all know you're straight, just do it and get it over with. We all promise never to tell anyone about it.

Jason: Dude, I get a say in this too. There's no way in hell I'm kissing Tyler.

Kayla: I'll tell you what - give each other one little peck on the lips and I promise to make out with you both at some point today.

Jason and Tyler looked at each other, weighing out their options. Finally they figured that getting to make out with Kayla canceled out the whole gay aspect to it. They turned to each other and gave each other one tiny peck on the lips, then immediately turned away to wipe their mouth. We all found out later that Kayla was lying to them. Not only did she have no intention of making out with either of them, she told a whole bunch of people at school about it later that week.

Finally it was Tyler's turn and he looked ready to exact revenge on me.

Tyler: Chloe, truth or dare? *He smiled*

Me: Truth *Now I smiled*

Tyler: Dammit, ok, now I have to think of a truth. I was expecting you to say dare. Ha, ok, fine - I thought of one that can embarrass you enough. Tell us, in detail, what you were thinking about the last time you masturbated.

I really wasn't expecting a question like that, so I started to blush a little bit. He really did think of a question that would embarrass me. I could always lie to him, but Kayla would know if I were lying since I had actually told her about it the other day. This was by far the worst part of the day for me (I still cringe when I think about it).

Me: I was um... I was thinking about you.

Tyler: Whoa, damn. Well, keep going. I told you to tell us in detail.

Me: *deep sigh* I thought about us having sex in my bed. You were naked, I was naked. That's it, that's all the details I have. Can we please move on now?

Tyler high-fived Jason with a smirk on his face. I don't think our friendship was ever the same after I told him that - I always ended up feeling uncomfortable around him. It was actually kind of traumatic now that I think about it. But anyways, on with the story.

[ChloeThompson87]

Now that I was thoroughly embarrassed, it was on to the second round and it was Jason's turn again.

Jason: Kayla, truth or dare?

Kayla: I don't think I'm up for answering a question like Chloe's, so dare.

Jason: I dare you to take off your shirt and keep it off for until we're done playing.

Kayla: Jeez, we really should have established some kind of rules or boundaries before we started playing. Ok, I'll do it, but we have to take a break to make some rules.

Jason: Fine, rules sound good. But after you take your shirt off.

Kayla went ahead and took her shirt off to reveal that she was wearing a white bra under it. She didn't seem too embarrassed as she sat the shirt next to her. We went ahead and established that no one could be dared to do anything dangerous, nothing in public, and nothing too disgusting. I think we were all a little relieved that we had done this.

It was my turn again finally and I had been cooking up something that would get Tyler back for the Truth that he had asked me. He thought he was so clever in covering up the pantyhose with his socks and jeans, so I figured I should test exactly how much he could cover up. And if he picked truth, I had an equally crushing question to ask him.

Me: Tyler, truth or dare?

Tyler: I know better than to pick truth. You're just going to ask me the same question I asked you. So, dare.

Me: Ok. Then I dare you to let Kayla and I turn you into a girl with a full makeover. We get to decide on everything that you wear.

Tyler blushed a little bit, but for some reason he wasn't protesting as much as he did when we asked he and Jason to kiss. To this day I don't know why he didn't protest much. Maybe he liked it or something.

Tyler: Ok, fine. I'm already wearing the pantyhose, so lets get this over with.

Kayla: Hold on, I never agreed to let him wear my clothes and my mom would definitely notice if anyone messed around with any of her other clothes.

Me: Come on, I'm sure you have some old clothes that you never wear anymore. Think about it, this is going to be hilarious. We'll get to pick on him about this forever.

Kayla: Yeah, I guess I have something that I don't ever wear. I'm in.

I took Tyler by the hand and winked at him, lifting him up off the couch. I was still frustrated with how he had embarrassed me, so I was ready to go all out and make him pay.

Me: Come on Trisha, let's go make you pretty.

[monkeysrock]

this is really good!!! I'm hooked! Keep it up!

[thenuddydudemfbiz]

Very Good, can't wait for more :-)

[dareboy2]

good job keep it coming

[Officelover]

I LOVE this story. Keep going!

By the way, I love how you scripted some of it like a play.

[ChloeThompson87]

By the look in Tyler's eyes, I could tell that he was irritated that I had called him Trisha. Of course this just provoked me to keep on calling him that for the rest of the day. Dressing Tyler up was probably the most entertaining part of the day and certainly the part that I'll always remember the most.

So Kayla and I went on to look for some clothes in her closet. It turned out being a pretty easy decision. We agreed on a blue pleated plaid skirt, a plain black spaghetti strap shirt, along with one of Kayla's old bras that she no longer wore. Along with these clothes we told him that he had to keep the tan pantyhose on. We handed him all of the clothes and told him to go get dressed. He got dressed in the bathroom again, then came out looking very, very uncomfortable. We all laughed our asses off of course, whistling at him and telling him how pretty he was. We weren't done just yet though.

Next came the makeup. Kayla and I decided on the slut look. This included firetruck-red lipstick, black eyeshadow, black eyeliner, black mascara and a little bit of pink blush. We made sure to go extremely heavy on the eyeliner and eyeshadow which is what really made him look like a whole other person. To finish it off, we made sure to stuff his bra with toilet paper and put one of Kayla's hair bands on his head. He kept tugging at his skirt as if that would somehow make it longer so that his pantyhosed legs wouldn't be exposed, which of course didn't work.

This was it - I finally felt thoroughly satisfied with the job we had done in embarrassing him. We didn't hear another smartass remark from him through that whole day. It's like the clothes had magically made him timid and fragile. I really don't get that whole macho thing where guys feel all embarrassed when their masculinity is threatened, but it certainly is entertaining. Well, more than entertaining. This was the day when I had discovered a side to myself that I had never known.

I had always been a perfectly normal, perfectly straight girl. But something about seeing Tyler that way made me feel kind of weird inside. It wasn't until college that I finally accepted that it was ok for me to be involved in the kind of lifestyle that involved controlling and humiliating guys. But that's a whole different story that I'll probably never tell (since I still keep in contact with my college sweetheart).

Anyways, that was pretty much the height of our truth or dare session. There were a bunch more dares, such as one that involved me having to suck Amy's finger for 20 seconds (which obviously made Amy very uncomfortable) and one that involved Tyler having to do a little dance to a Christina Aguilera cd while he was still dressed up. Needless to say, my fantasy about having Tyler in my bedroom changed just a little to include what I had seen that day. Telling any more about that day would just be anticlimactic and, well, boring. I hope you all enjoyed my not only true, but very personal story about the day that changed the course of my life.

[profoundslave]

awesome story...keep up the good work