[Non-Fiction] My Dare Log

[Dare Lord]

I have a confession: I haven't always been the most daring person in the world. Still, I occasionally find myself in situations where I'm dared to do things. This won't be the most extreme story out there, but it will be true.

Let's start it off!

About three years ago, my girlfriend Cassie (not real name) and I were sitting in the back of a 15-passenger van together on a lengthy trip. For those of you who are interested, Cassie is short, has darkish blonde hair, and C-cup, almost D-cup breasts. Long story short, we got bored and started playing truth or dare.

Since we were in the van and had limited mobility, we stuck to truths for most of the time. They got more and more probing as we went, but since she was my girlfriend, I wasn't afraid of being honest. Finally, the truths got old, and we moved on to dare.

"Taylor (not my real name), I dare you to..." Cassie looked around to see if anyone else in the van was watching. "Unzip your pants!"

This might not sound like much to a lot of you, but for me it was a big deal. I tried to look confident, but I was really nervous. Hands sweating, I reached down to my waistband and first unbottoned, then slowly unzipped my cargo shorts. To me, the zipper seemed to echo through the whole van, but no one turned around. (There were at least ten other people on the van at the time.) Now my boxer briefs were on display, and there was a noticeable bulge in them.

Cassie and I hadn't been together for very long at this point, and we hadn't done anything yet. So it came as a shock to me when she reached over and slipped her hand into my underwear. At that point, my bulge got, well, bulgier. My face flushed.

Cassie squeezed the tip of my hardening member, and the world around us fell away. Not caring about the other passengers anymore, I slipped my hand up the leg of Cassie's shorts in a desperate struggle to reach her "pot o' gold". Unfortunately, they were really tight shorts, and the word "struggle" became appropriate. Still, I managed to get to her crotch and shift her panties to the side. I slipped the only finger that would reach in and did my best to pleasure her.

It wasn't easy to keep from gasping or moaning, but we held it together for about five minutes. Then, just as I was about to climax, we reached our destination. Frantically, Cassie and I got our hands back to ourselves, and I re-zipped my pants. Before we got out of the van, though, Cassie loaned me a travel bottle hand gel to clean off. We smiled awkwardly.

Ok, that's all for now! I'll post again with more dares when I get the chance!

[tripers]

This sounds very promising You have your first subscriber.

[Dare Lord]

Chapter 2 - A Day at the Pool Part One (Changing)

After my van dare, Cassie and I got more daring together. Just about every time we were around each other, we did dares.

Now Cassie had a small aboveground pool in her backyard, so I went over all the time to go swimming. Cassie had two younger sisters who were always hanging around us and giving us a hard time, which made the dares all the more risky.

One time, we had decided to go swimming, and Cassie got a gleam in her eye. I knew what this meant. The first time she had gotten it was in the van. She was about to dare me.

Sure enough, she grinned and spoke up. "Taylor, I dare you to let me get you into your swimsuit!"

I gulped. While we had dared each other a lot before, neither one of us had seen the other completely naked. But I never backed down from a dare, and I wasn't going to start now.

"Okay," I said, getting an idea, "but only if you let me get you into your swimsuit, too."

Cassie's grin widened. "You've got a deal," she said.

We snuck into her room together and shut the door. We stood there for a minute awkwardly. "You start," I finally said.

Without speaking, Cassie came over to me and took off my shirt. No big deal. So I reached over and pulled off hers. Now she was wearing a white bra with a little bow in the front. I noticed the bra was a tiny bit small for her. I reached around her back with all the smoothness I could muster and took hold of her bra clasp.

This was my first time to attempt to undo a girl's bra. Guys, you know this awkward rite of passage. There was a good thirty second period where I couldn't figure it out. I felt two or three little hooks back there, but I was too embarrassed to ask her to turn around so I could figure it out. Finally, she sighed. "Just let me," she said. She turned anyway so I could see and, with the arm flexibility only girls have, reached around and undid the hooks. She spun back around, facing me, so I could finish the task. My hands were shaking a little from anticipation, but I slowly, sloooowly slid the straps down her arms.

Her breasts, the first pair I'd ever seen, were revealed to me, and instinctively I ran my hands over them for a moment, feeling their smoothness and the perkiness of her nipples. And she was obviously turned on.

Next, she pulled down my pants, with about as much speed as I'd been removing her clothing. I did the same for her. It was about then that it hit me. I was almost naked, and so was she. It also hit me that her door didn't lock and we had a chance of one of her sisters bursting in on us. It seemed the thought had hit Cassie, too, because she togged down my underwear in one smooth motion. My now-erect penis bounced up like a Jack in the box, but to Cassie's credit, she didn't laugh. I pulled down her tight pink panties about as quickly.

The first naked girl I had ever seen. Her pussy wasn't shaven, but I was fairly certain I could see a little wetness down there. To be fair, there was a little dab of precum on my penis as well.

"Cassie! Taylor!"

It was the sound of one of Cassie's little sisters from downstairs. We were running out of time, so I frantically pulled up Cassie's bikini bottoms and pulled the straps of her top up to her shoulders. Since I had failed miserably with the bra earlier, Cassie tied her own strings, and she raced to tug my swimsuit up my legs. We rushed out of the room and downstairs where Annie, who was 13, was waiting for us. She was wearing her pink bikini and holding a towel. "About time," she said. "What took you guys so long, anyway?"

Cassie and I looked at each other and tried to hide our smiles. Little did I know that I would still have more dares today...

[Dare Lord]

Chapter 3 - A Day at the Pool Part Two (Water Games)

Cassie, Annie, her sister Katelyn, and I all went out to the pool. For those of you keeping track, Cassie was wearing a two-piece green swimsuit, I was wearing brown swim shorts, Annie was wearing a pink bikini, and Katelyn was wearing a blue tankini.

We all swam around for a little while, until Katelyn and Annie got into an argument and left the pool for a while. This gave Cassie and I the chance for another session of dares, with the added risk of Cassie's sisters coming back at any moment.

I was the first to speak up. "Cassie, I dare you to swim for the next minute topless!"

Let it also be known that Cassie's backyard where the pool was only had a chainlink fence in between it and the other backyards. So there was a serious chance of exposure. But we were both still kind of horny from earlier, so Cassie agreed. She untied her top and let it go, then floated on her back for a minute. It was one of the hottest things I'd seen: Cassie with her eyes closed, her boobs uncovered and floating atop the water.

When the minute was up, I splashed her, making sure as much water hit her boobs as possible. She slipped her top back on. "Taylor," she said, "I dare you to pull down your suit to your ankles!"

Cue another check to make sure nobody was watching except Cassie. Then down they went, and sure enough, Little Taylor was hard again. Cassie swam over to where I was and kissed me. This time I didn't dare her, just pulled down her bottoms. If I had dared her to, she would have done it anyway, and besides, my mouth was otherwise occupied.

Cassie reached out, took hold of my penis, and started jerking me off. I did the only thing I could, and slipped two fingers inside of her. I have to make a little side note here: if you ever get a chance to be pleasured underwater, TAKE IT. It feels amazing.

There was no one out, so we allowed ourselves some moaning. I slipped another finger inside her. Cassie gasped and whispered, "More." I used my other hand to spread her lips as far apart as possible, then started pleasuring the top of her clit with both hands. Her moaning was definitely getting louder, and she started pumping on me more vigorously.

We couldn't hold on much longer anymore, so we finally let go about the same time, our juices flowing unseen into the water. We were breathing heavily, and we made out a little more before pulling our suits back up.

We were about to go back inside when Annie and a clearly unhappy Katelyn came out the back door...

[Dare Lord]

Chapter 4 - A Day at the Pool Part Three (Annie and Katelyn)

"We came to an agreement," Annie said. "Since Katelyn lost the argument, I can embarrass her whenever I want in the pool without warning." She and Katelyn climbed back into the pool.

This was getting to be a very strange day for me. I had just been jerked off by Cassie, yet I was starting to get hard again. I wasn't sure what exactly Annie had in mind for her sister, but since I was happening while a guy was here (me), I could only assume Katelyn was going to be exposed.

Sure enough, they had only been in the water for about a minute before Annie snuck up behind Katelyn and ripped her top off. Katelyn's smallish boobs popped out and she squealed. Her nipples were a bit large for the size of her breasts, which wasn't the same case for Cassie. Annie snickerered, then said something that surprised me a lot.

"I've decided Taylor will spank Katelyn," Annie announced. She then yanked Katelyn's bottoms down. Two girls naked in the same day. Guys, I think I was living the dream. "Ten spanks ought to do it. Taylor, take your time."

I looked over at the slightly shocked Cassie, wondering what to do. She nodded as if to say, Go ahead.

I went over to where Katelyn stood, blushing. She had shaved down there recently, I noticed. We went to the ladder on the edge of the pool, where I awkwardly sat down. I lifted Katelyn onto my lap face down, out of the water so she wouldn't drown or anything stupid like that.

The ten spanks must have taken forever for Katelyn, but before I knew it they were over. Her butt was red now, and I could see a little of the lips of her pussy. I dropped her into the water, where she swam over and got her suit from Annie.

"I think it's time we went back inside," Cassie said. I agreed, though I groaned inwardly. I wasn't able to change with Cassie that time, instead changing in the bathroom. But the day had one more surprise for me.

Just as I left the bathroom, Katelyn decided to get her revenge on Annie. As Annie went up the stairs, Katelyn climbed behind her and took off her bikini top in the same way she had earlier been stripped. My third pair of boobs for the day. Not bad at all.

This was not the end of my dares with Cassie, though...

[Dare Lord]

A Question for Anyone Who Might be Reading This

I'm not sure which dares to talk about next. There's another set of dares I did with Cassie at her house, and there's some dares my cousins and I did on the 4th of July several years back. Which should I post about next?

[santa_majic]

just post all of them in order
great dares and you are one lucky guy!

[Dare Lord]

Chapter 5 - Independence Day Part One (Getting Warmed Up)

It was the fourth of July, and my cousins came in as they always did from out of town. We had had a history of playing Truth or Dare, and I think I did some of my first dares for them. My male cousin, Calvin, was about my age, really skinny with dark brown hair. My female cousin, Rebecca, was a couple of years younger.

We had been upstairs at my house for a little while, just hanging out, when the dares started coming. We didn't bother with truths anymore. Calvin was the first to speak: "Taylor, I dare you to strip down to your underwear and dance around while speaking in an Irish accent!" We had a running joke about leprechauns, and since I had reddish hair, it was easy to get what picture they were making. I agreed, and both my cousins laughed like crazy.

It was my turn to give a dare now. "Rebecca, I dare you to let me and Calvin both give you a wedgie at the same time!" Rebecca sighed, but then nodded, as she knew any punishment would be far worse.

Calvin went to her back, I went to her front. Since she was wearing tight jeans though, I couldn't reach her panties. I asked her to unbutton and unzip her jeans. She groaned, but complied.

I yanked up on her pink panties at the same time as Calvin, and Rebecca squealed. She was hoisted by us into the air, and I noticed her panties were stretching a lot. Her jeans began to slide down her legs, and I saw that a cameltoe had formed. It was also apparent that she was a little wet. I nodded at Calvin, and we set her down, but not before bouncing her once to make her squirm.

It was Rebecca's turn now. "Cavin," she said. "There's an extra pair of underwear in my suitcase. Get yourself some panties and a bra, and put them on in here."

Suddenly the dares had escalated. Calvin turned bright red. "There's no way," he said.

"Very well," Rebecca said. "Then you will strip naked and masturbate for us."

We weren't warming up anymore. Now, we were in it for the long haul...

[dcoen111]

amazing stories please post more

[Dare Lord]

Chapter 6 - Independence Day Part Two (The Jerk)

Calvin and I both gaped at Rebecca. Neither of us were expecting the dares to escalate so quickly. "Seriously?" Calvin said.

Rebecca nodded. "And it's your punishment, so you can back out this time."

Calvin just stood there, his eyebrows raised, still shocked.

"You'd better get started," Rebecca said.

Calvin finally pulled off his pants. There was a slight bulge visible. Then he removed his shirt, leaving him only in a pair of boxers. He stood for a second, hesitating. Rebecca reached over and tugged them down. "About time," she said. "Come on, I know you do this all the time at home."

Calvin turned bright red. "WHAT?" he said.

"Our rooms are right next to each other. I can hear your bed thunking against the wall." Rebecca looked down at Calvin's penis. "I have to say, I was expecting something bigger."

"Shut up," Calvin said. He closed his eyes and started jerking off. He picked up speed as he went, adding in some grunting as well. I couldn't help but think of a caveman.

Finally, he spewed, but he put out a hand in front to keep the cum from getting everywhere. "There," he said, a little out of breath. "Happy?"

"Very," Rebecca replied sarcastically. "Your turn now."

"Fine," Calvin said. It wa obvious he wanted to get Rebecca back. "I dare you to strip to your panties, and Taylor will act like the Coppetone dog and pull them off."

I was a little less than sure about this...