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Teenage Truth or Dare

Posted by: Author: Age: 23 Posted on: 2 comments
6 likes 3945 views Category: Masturbation Female-Male Tags: truth or dare, show me yours, , Hall of Fame


First I'd like to say that this is a great site, and I enjoy reading all of the stories. This is a story that happened a long time ago, and started me on my fetish.

I'm an only child, and was about 13 years old at the time this story takes place. My best friend, who was also 13, had a twin brother. I'll call them Sally and Tom. Sally and I were both cheerleaders in Middle School, and Tom played football, basketball, and swimming at the local pool in the summer. Tom was a pretty cute guy with an excellent body. He looked like some of the 15 and 16-year-olds. He was about three inches taller than everyone in our class, but wasn't scrawny like most younger boys are when they grow quickly and suddenly. He was well muscled with wide shoulders and defined arms and chest, tight abs and a fantastic ass.

One summer day Sally and I decided we would set up their tent in the back yard and 'camp out' that night. It was just after dark, and Sally and I were talking about boys, and both admitted we hadn't done much. I had kissed a boy, and Sally had kissed a boy with tongue, but that was about the extent of it.

Sally had accidentally walked in on Tom in the bathtub about a year ago, but other than that, neither of us had seen a boy naked. We had, of course, seen movies with naked guys in them, but were complaining that you barely get to see anything - either just their butts, or a very quick glance at their dick. This talk was making us both kind of horny when Tom came home from his friends' house. Seeing the tent in the back yard, he came to investigate, unzipping and crawling into the four person tent.

At first we were angry with him, but then I had an idea. I told him he could stay, but only if he promised to play truth or dare with us. Sally quickly caught on to what I was thinking, and looked at me rather nervously, but said nothing. Tom must've thought that he'd come out on top, because he quickly agreed.

We quietened down, and started playing. At first, everyone was picking 'truth', and the questions quickly turned sexual in nature. 'How far have you gone?' 'Have you ever seen a girl naked?' 'How often do you masturbate?' (Sally - about once a week, Tom - every day, Me - about twice a month)

I broke the proverbial ice when I picked dare from Tom. He thought for a moment, and asked me to flash him my bra for 15 seconds. I felt my face flush, both from embarrassment and excitement, as I lifted my shirt. The 15-second count, done out loud by Sally, seemed to take forever. This, however, loosened everyone up. It was my turn, and I went right back to Tom. He picked Dare, and I dared him to take off his shirt. He then dared his sister to flash her bra, but for only 10 seconds. I counted quickly as I could see how red Sally's face was. Sally then dared me to lick his nipple. I dared Tom to moon us, and I got to see that awesome butt of his naked from two feet away. The only bad thing was that he was wearing tighty-whitey's. I'm definitely a boxers girl! Then Tom, who was now just as red as his sister was when showing her bra, dared me to show my butt. I got to my knees, turned away from him, and dropped my shorts and panties to my thighs. I started to get more aroused thinking about Tom looking at my naked butt from so close. Time was up, and I pulled up my panties and shorts and turned back to the game. I dared Tom to take off his underwear, then put his shorts back on. He balked a bit at this, but relented fairly quickly. He had quite a difficult time trying to hide himself from us while removing his shorts and underwear in a tent that he could barely kneel in - I got a quick glimpse of his dick twice, and got to stare at his naked butt for over a minute!

Tom then started playing for keeps. Since he had to play in just his shorts, he dared me to play in just my bra and panties. I dared Sally to do the same as Tom had just done - take off her panties and shorts, then put back just her shorts. She seemed a little upset with me, but did it. Tom was openly staring at her butt the whole time. Sally then, I think out of retaliation, made me flash my boobs. I was really getting turned on by this point, so I was sad that it was only for five seconds. I thought Tom's eyes were going to leave his head and bore into my boobs!

Tom picked dare again, and I told him that he had to swap his shorts for Sally's panties. Boy, was he angry. He said he absolutely wouldn't, and was holding them up, indignant at how small and sheer they were. I told him that I had just showed him my boobs, and that he had to do this if he wanted to keep playing - otherwise we'd throw him out of the tent and put his underwear somewhere for his mom to find. He finally agreed, and I got to see a few more quick flashes of dick while he was changing into Sally's panties. When he turned around, it was awesome. They were low-rise panties, so they barely came to the top of his pubic hair. Tom was slender, but not nearly as much so as his sister, so they were stretched very tight, and you could almost see through them. The outline of his dick was very plain to see. He opted now to sit with his legs together and his feet directly under his butt quickly covering his lap with his hands. Tom then dared me to play without my bra. I didn't want to spoil the game, and was really getting turned on, so I didn't object, but could feel my face flushing when I took it off. I forced myself not to cover my breasts, which made me flush even more, and I suddenly shivered and felt my nipples pop to full erection. Tom's eyes were glued to me.

I felt that Sally was far too clothed, and dared her to take off her shirt, leaving her in just her shorts and bra. Sally then shocked us all by daring her brother to flash us his dick for 30 seconds. Tom really complained at that, and I finally got him to agree to 20 seconds by pointing out that I had already been sitting topless for over two minutes already. Tom was really nervous, and Sally and I were very anxious. Tom made the show even better by getting up on his knees, and then stalling for about half a minute before finally having the guts to pull the panties down. For all that time, we could see the sheer fabric and the outline of what we were about to see. I started counting 1-mississippi, 2-mississippi, 3-mississippi, then suddenly inspiration hit, and I counted 4-tommyspenis, 5-tommyspenis... This sent all three of us into a giggle fit, and the 20 seconds probably lasted closer to 45. His dick was about four inches, with dark blonde pubic hair just above, and a light fuzz on his balls, which were pulled tight to his body, and just a little bigger than two golf balls.

Tom then felt the need to 'get even' with his sister, so he dared her to take off her bra. Sally almost stopped the game right there, but between the two of us pointing out everything we'd had to do so far, she finally, however reluctantly, agreed. She removed her bra, and immediately covered her chest with her arms. Tom was complaining about this when I finally told him that we'd make her do jumping jacks later if she didn't get more comfortable.

Sally's face was burning, but I think she was getting horny, too, because she dared me to kiss Tom on the lips for 30 seconds. I didn't need to be asked twice, and almost jumped on him. I felt his naked chest against my breasts, and it really made me even more horny. My tongue parted his lips and explored his mouth while my hands felt his shoulders and back until Sally called time. When I moved away from him, he was flush and didn't move at first, caught up in the moment, I suppose, but I looked down and actually gasped out loud. His dick was now erect, and probably about five or six inches of it was sticking out the top of the panties that he was wearing. He suddenly realised what Sally and I were staring at, and grabbed his shirt to cover it up. I protested, saying that I couldn't cover my boobs, and he said that he needed to go inside. I told him to stay, please, and he was very embarrassed. Then I offered to let him keep the shirt and I'd take off my panties if he'd stay, but he'd have to play totally fair from here on - no more complaining, or talking us out of things. He quickly agreed, most likely because he couldn't believe that he was going to see me naked. I was so horny, and the rush of showing off my body to him was getting me even more turned on, so I decided to continue to sit cross-legged even after I had taken off my panties. He was openly staring at the thin wisps of light blonde (almost white) pubic hair that grew over my slit, which was swollen and red and juicy from because of how turned on I was at the time.

I looked at Sally, and she was so disbelieving of the whole situation, that she was no longer remembering to cover her boobs. I reminded everyone that it was my turn, and offered truth or dare to Tom. Afraid that I was going to dare him to show us his boner, he picked truth. Sally started to get upset, calling him a wimp, but I just asked him if he was going to masturbate tonight. He turned red, Sally immediately shut up and looked at him with a sly grin, and he finally answered very quietly that yes, he was.

Tom then dared me to touch Sally's boobs, which I did (no problem). Then I went right back to Tom - truth or dare. Tom again picked truth, and I reminded him of the rule that you couldn't pick truth three times in a row. I then asked him what part of my body he liked best, and kicked my legs out, laying back in a seductive pose (totally naked, if you remember). Tom was staring at me, taking every inch of me in, and then asked me to roll over so he could see my butt again. I laughed, and flipped over onto my stomach, showing him my butt. After about 20 seconds, I turned over to my back again, and pushed 'well?'

Tom then, very sweetly, said that he had always like my smile, and that was going to be his answer. Sally complained that was a lame answer, but I said it was sweet, and leaned over to kiss his cheek before sitting back down again. Tom then dared Sally to take off her shorts. Sally again balked at this, saying it was weird to just be sitting there naked in front of your brother. He said that she didn't seem to mind staring at his dick when he had to flash that earlier, and so she finally agreed, but sat with her knees together and drawn up next to her, hiding everything from view.

Sally then dared me to take Tom's hand and run it over my breasts. I was happy to let his fingers feel my flesh, and got even more turned on. Now it was my turn, and I reminded Tom that he couldn't pick truth again, so just dared him to lose the shirt from his lap and the panties. He said 'yeah, I figured this was coming', and smiled as he pulled the panties off, making no motion to hide his erect dick from us. He was about seven inches long, thick, and his balls were tight against his body. His erection stood straight up against his body along his 'happy-trail', with the head coming even with his navel.

Now it was Tom's turn. Truth or Dare Becka. I picked Dare. Because the yard was surrounded by bushes, and the tent blocked the view from the house, he dared me to get out of the tent and do one of my cheers - naked - while he held the flashlight on me. I giggled, and the thought of it was quite a turn-on, so I quickly crawled out the door of the tent and stood up. I looked toward the house - no lights on in the back, so it was safe. Tom and Sally stuck their heads out the tent flaps, and Tom pulled the flashlight out, shining it like a spotlight right on my pussy. I suggested pulling the lantern out of the tent, saying that I didn't want to have to do it again if he couldn't keep up with the flashlight. Tom quickly disappeared, and returned with the lantern on full, which lit up the area right behind the tent like daytime. I chose to do one of the longer cheers that we do during halftime of basketball games - it's about a full minute long, and has me facing both ways for part of the time, and ends with me in the splits.

When I finished, Tom clapped quietly, and before letting them go back into the tent, I dared Sally to do a cheer with me. With very little protest, she agreed, and the two of us stood naked, side by side and started the same cheer again. Tom said that was the best thing he had ever seen, and we all crawled back into the tent. Sally was a lot less modest with the way she was sitting, and Tom still had his erection, and was making no effort to hide it.

Sally then dared Tom to masturbate for us. He was a little apprehensive until I said that I'd do it with him - we could watch each other to help each other get off. I was so horny that I had been fighting to keep myself from touching myself, and this was the excuse I was waiting for to get off. Tom agreed, and I immediately laid back and started fingering my clit with my right hand and massaging my breasts with my left. Tom, still kneeling just to my left stared at me for a minute, then began stroking his dick with his right hand. I was fixated on him, and felt myself go over the top to climax. I had come hard, but I was still horny, and it still felt good. I kept watching Tom stroke, when I heard moaning from the other side. I looked right, and saw that Sally was watching Tom intently, and had her hand buried in her crotch, rubbing furiously as well. I turned back to look at Tom, and our eyes locked. Suddenly he threw his head back, let out a stifled moan, and a rope of cum shot from the end of his dick, striking the roof of the tent. Several more ropes of come spewed forth, and at the same time I felt myself climaxing again, even harder than before. Then I heard Sally coming to my right, and once again I felt the waves of orgasm crashing over me. I struggled to open my eyes, and saw Tom staring intently at my right hand, which was still rubbing furiously over my clit, which now felt larger and harder than it ever had before. I looked down and saw his hand, still clasped over his now half-hard dick, still absently, slowly stroking, with drops of come welling up and out of his now spent shaft, and I came again, this time not able to stifle the sounds of my pleasure, screaming out load while almost crushing my hand between my thighs, and nearly tearing my breast off with my left hand, bucking my hips wildly in the rhythm of my fourth, and most intense orgasm. When the spasm subsided, I pulled my hand away from my drenched pussy to find my fingers wetter than if I'd just dipped them in water. Sally was laughing hysterically at me for screaming, and Tom was just staring, open mouthed, with his hand still on his dick, which was now almost erect again. I suddenly felt embarrassed for being so loud, but both Tom and Sally assured me that it was the most sexy thing they'd ever seen, and Sally admitted that she wished she could be that free. We used Tom's shirt to wipe up his come from our sleeping bags and the walls of the tent, then we all sat and talked for a while, all comfortable now with our nakedness. I revealed that I'd never come that many times before - I didn't know about multiple orgasms yet, but Tom had read something about it in a dirty magazine that a friend of his had. We asked about the dirty magazine, and he told us about how the girls pose, and then admitted that we were both a lot hotter than any of the girls in that magazine.

We all agreed that we'd never tell anyone else about this. Tom eventually went inside to go to bed, although he admitted that he was going to be jacking off as soon as he got into bed. Sally and I slept in the tent, and the next morning it reeked of sex, and we had to turn it inside out to keep her mom from smelling it. Nothing like that ever happened again with Sally - she felt too weird doing anything like that with her brother. Tom and I became good friends, and although we never officially dated, we spent quite a lot of time together exploring our sexuality.

I learned through him that I am both an exhibitionist and a voyeur. I get very aroused showing off my body, slowly revealing my flesh, and letting people glimpse what they're not supposed to see. Tom and I had some fun times after we turned 16 and could drive. We would go to other towns, hours away from home, and I would go into full-service shoe stores to try on shoes with mini skirts and no panties, or we would go to the beach where I would 'accidentally' lose my bikini top in front of a large group of guys. Tom was always my safety net, always there to make me feel like things wouldn't get out of control, and that no one would attack me. I just wanted them to look, after all.

I also learned that I get incredibly turned on by the male body. Just the sight of a hard dick gets me going even now, ten years after that night in the tent. Watching a man masturbate is almost better than having sex! Twice, I've been able to have an orgasm just watching Tom masturbate for me.

Tom and I have still never had sex together. He's had girlfriends, and I've had boyfriends. Some of my boyfriends won't masturbate in front of me - they're never my boyfriends for long. The trouble is that you're usually dating someone for a few months before you're comfortable bringing up your kinks, so I've wasted a lot of my time on guys who are just way too closed-minded. Tom seems to be the guy I just keep going back to. He respects me and my kinks, and doesn't judge. I've been thinking about getting him to date me, but I don't want to ruin what we have... what if he gets possessive once we become a couple? What if he won't take me out to show off any more, because I'm his? I do love him, though.

Let me know what you all think. Sorry this story is so long... it got out of hand when I wrote it!



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