Author: MrJDWebber

[Group] Pulled into a Dare Game

One night, I’m walking alone down the deserted streets of my neighborhood as I often did. I had been walking by where my old babysitter lived, I had always had a crush on her and she had only been 3 years older than me.

Suddenly, Laney came running out from her garage, butt naked.
“JD! Fuck. Ummm… Do you want to come inside for a blowjob?” Laney said nervously as she approached me, making no attempt to hide her DDs or landing strip of blonde hair.
“Absolutely.” I replied, getting the feeling I knew what was happening.

Laney dragged me inside her garage where Sandy, Sheila, and Eric were sitting in various stages of undress and drinking.

“Yes!’ Sandy shouted when she noticed it was me. “I thought that was you. This is great, I know you’ve always wanted this. Swallow him down Laney.”

Laney proceeded to pull my very erect cock free and slide it between her lips. It didn’t take long before I was ready to cum and Sandy could tell.

“Remember to wear it on your face!!” Sandy said. Read more »

[MM] How I Discovered I Wasn’t Gay

So far, I have posted a few dares that mainly displayed girls being mean to girls in a sense. Here I have a story about myself that is just as troublesome. This takes place on the same night that I did my streak. Indeed, a lot happened that night.

After swallowing my cum, Mandy had it out to get me back somehow. Even though I didn’t issue that dare. At any rate, she dared me to blow my friend. I didn’t know that I wouldn’t be able to do it. I was straight as far as I knew, but I hadn’t ever tried anything gay. Read more »

[F] Extended Dares

After a while of giving out dares and punishment dares, Mandy, the leader of our little group, came up with a new addition to our games. Extended punishment dares. This is going to be quite a short little story to introduce the concept and detail an actual event.

The first person to ever receive this was a girl named Stacy. She had accidentally forgotten the rotation of dares and who had just dared her and ended up breaking the rules by daring Mandy, who had just dared. She was given the punishment dare for to wear nothing but this little sundress she owned for two months. Sounds simple enough, except this was a very sheer and thin dress that barely came to her knees and was probably too small. When she wore it the first day, it was clear there wasn’t anything underneath. It wasn’t obscene, except in certain light. Mandy took Stacey everywhere with her for the first week. I guess she got bored because one day at the lake she instigated a fight with Stacey. I came late enough to see them facing off, practically the whole lake watching. It was over before it began, within seconds Mandy was ripping Stacey’s dress right off, shredding it in the process. Read more »

[Group] The most extreme punishment dare I’ve seen.

This was at a party, some of us had strayed away from the party and gone to a separate room to play. It was a big party, there was at least 30 people there and five in our little group alone. Two girls, Lindsey and Grace, and three guys. Lindsey and Grace were “friends” according to everyone. However, it was more like Lindsey was Grace’s friend and Grace only tolerated her presence. The game was again more about the girls trying to push each other sexually, but we were following my rules. Lindsey was rather shy when it came down to just dares, after three dares in a row anyone can abolish truths. But Grace wasn’t kind at all and by the time she gave Lindsey the final punishment dare for not being able to completely deepthroat one of the other guys, she had Lindsey naked only wearing all three guys cum and on her face and she wasn’t allowed to touch it. And I had came twice on her face. Read more »

[Group] Women can be vicious in Truth or Dare.

So, I have had a very different life than most people. Suffice it to say, I played a lot of Truth or Dare and have a lot of stories. I thought I would post a few of the craziest dares I’ve seen. I already posted my big streaking dare. So, here’s one that happened that same night.

So, two girls had been rather aggressive with each other, let’s call them Sandy and Lisa. Now, Sandy was the one that had started the game, she was also the one who had the rules. So, it started with Sandy daring Lisa to completely remove her top. This ended up with Lisa instinctively covering her nipples, which violated the rules. And as per the rules, she was given a punishment dare by Sandy which resulted in Lisa being nude. A little later, Sandy dared Lisa to give oral to one of the guys for 30 seconds and Sandy would count. Sandy counted so slow that the guy came in her mouth. When Lisa had a little freakout about it and argued with Sandy, Sandy said she wasn’t finished and because she failed to complete the dare she had to do another punishment dare. This resulted in her giving another one of the guys oral and deepthroating for 60 seconds and Sandy counted. This time it was made clear that if he came she had to swallow and keep going. Again, it was a very slow count and the guy definitely came. We almost had to hold him down until she finished. Which had Sandy in stitches from laughter. Read more »

[M] When I got a handjob in Church

So, I was young and so was she, I wasn’t dating this girl. We were close friends and had actually fooled around in a game of truth or dare, but we weren’t together. She was shorter than I, with brown eyes and black hair. It had actually started on the way to church, she was cuddled up with me in the backseat using my jacket as a blanket. She had inched her hand onto my leg and slowly toward my cock. Her head was on my shoulder and she was watching her hand as she found my bulge and gently started running her fingers up and down it. She never pulled me free, we got to the church to quickly.

Now, I don’t know what kind of churches you have been to, but this was more like a shack. After rearranging to hide my boner, we went inside. Once inside, we sat on the back row, alone, after she argued with her mother for a moment. Throughout the entirety of the sermon, after all the singing, she stroked my cock. Once everyone was seated, she wasted no time covering my lap with my coat and pulling my piece out. Do you know how hard it is to listen to the pastor talk about the price of bread in leviticus or some shit with a hot young lady stroking your cock? Read more »

[M] A Dare I Did

So, when I was young and playing Truth or Dare with my cousin and some family friends at our family’s vacation home. Actually at this point it had just become dares. There were rules in place and suffice it to say it was much easier to do this dare than face the consequences of not.
So, I got dared to run to this corner gas station, that no longer exists last time I was there, and steal a sign, then run back. Keeping the sign as proof.
Sounds simple and easy enough, it was the middle of the night after everything was closed after all. There was one small catch. The reason it was easier to just do this dare was because of the rules. There was a rule that said you could get out of any dare by removing an article of clothing, but you couldn’t cover any part of your body that clothing had been covering and you couldn’t put any clothing back on. Also, if you’re naked, you can only not do the dare by quitting and doing a much more difficult punishment dare. At this point, I was completely naked and not allowed to even put on shoes for the run. Which really was more of a half jog after that assertion. I had completely misjudged the distance I would be running too. It ended up being 2.8 miles there and back. I got seen by at least some people in a tent. Who knows who else. Here is the actual route. I was reminiscing and actually found the Route as best I could on Google Maps. Read more »