Natasha’s Truth or Dare

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This story is a submission for the Winter Holidays Story Contest. If you like it, please vote for it!


It’s quite amazing that I was a good girl all through high school growing up in New York City. But that changed during the Christmas vacation of my first year of college. My brother, Gavin, and I had a holiday party for our friends in the basement of our brownstone on east 81st Street. My father owns a gallery in NYC and he was on an art-buying trip in Europe and due back on Christmas Eve. My mom is French and preferred for us to have parties at home rather than to go out downtown, so when Gavin and I asked if we could have a few friends over on the first Saturday night we got home on break, she was like, “Sure… Have fun, kids.” My mom has always been pretty cool and knew to make herself scarce during our parties.

Gavin is two years older than me and was in his third year at UCLA, had a fake ID and so was able to stock us up with plenty of beer, bourbon and tequila. I was really excited about how this party was shaping up because Gavin’s best friend in high school, Sebastian, would be there. I had had a crush on him since they were freshmen in high school and I was like 12. Sebastian’s family ancestry is Swedish and he looked like a Calvin Klein underwear model—tall, athletic build, with dirty blond hair almost down to his shoulders and a beautiful grin. They both had played on the varsity soccer team at school, and a few of their old teammates were likely to show up, as well as other old friends and girlfriends.

I invited some of my friends to come who were also in NYC for Christmas. One was, Alina, a model I had become friendly with at my agency because we had done our modeling training together. We had learned to walk runways, and had gone on a lot of “go sees” with photographers and creative directors. I have since become somewhat famous, and there’s a good chance you have seen me in ads for Gucci or Dior, or in gossip sites like TMZ, but this party took place a couple of years before I really hit it big as a model and became known. And I was still pretty much a “good girl” despite growing up in New York.

Sebastian had a sister, Theresa, who was my age and who was going to come to the party. I generally don’t find too many people intimidating, but Theresa had the most amazing full mouth, piercing blue eyes, a mane of blazing golden hair and striking eyebrows like Cara Delevingne. I had gone to Dalton for high school, while she went to the even more elite Spence. Besides the fact that our brothers were friends, she and I played against each other in field hockey, so we were both well aware of each other, and we had an unspoken rivalry. She had dated my brother for a few months when he was a junior in high school. Most people would say I am very pretty, being a fashion model and all, at 5 foot 10 with long brown, naturally wavy hair, lithe, thin body, and perky and full c cup boobs. My big boobs (for a model) have gotten me a lot of lingerie bookings, and eventually got me a starring spot on the Victoria’s Secret runway shows that have become such a big deal. But Theresa was mesmerizing, and when she entered a room, sucked the air out of it.

Anyway, I was getting really excited for the party to start, and spent a couple of hours doing my make up and getting dressed with Alina. She has jet black hair and her pale skin has this amazing glow in her fashion pictures. Together with her plump kewpie bow lips, she kind of looks like a real-life Snow White. I let Alina have the run of my closet and choose my outfit. She picked out a pleated leather mini skirt from Alice & Olivia, a semi-transparent ribbed white tank top from Vince, combined with a flowery lace bra from La Perla that you could totally see through the tank’s thin stretch fabric. To make things more interesting, Alina took some scissors from my mom’s sewing kit and shortened my tank so that it became a crop top. Now it showed off my mid-riff, from my belly button to the top of the low-slung mini. I felt very exposed and kind of like a trailer trash slut! I poked at her, saying, “You’re making me look like a ho, bitch!” She laughed, indicating that was indeed her intention.

Alina made me do a runway walk for her as she inspected me and picked out a pair of Gucci strappy sandals with five-inch heels. “You said you haven’t been laid in ages, right, Nat? I think you should go commando,” She declared.


“Yup. Come on. Hand them over.” She held out her hand.

“You too, then.”

“Of course.”

I reached up under my skirt and hooking my thumbs in my thong, pulled it down my legs. I had to sit down on an ottoman to thread the underwear off my feet. I was totally flashing Alina my naked pussy as I did that, and she giggled as she watched me struggle to remove the thong over my high heels. I finally handed them over and she put them back in my panty drawer. I straightened my skirt back over my legs and the feel of its buttery leather on my naked ass was totally sexy. It was true that I hadn’t gotten gaziantep escort ilanları laid in quite a while. The academics at my college were intense, and in my first semester I hadn’t yet found a guy that was suitable either for dating, or even a quick hook up. Most of the guys I had met in college so far seemed a little intimidated by my looks.

For her, I picked out a black leather Versace mini dress, so we would kind of match. And I loaned her five-inch, black patent leather Louboutin pumps too. While we put on our make up, Alina asked me, “Is there any guy you have your eyes on tonight?”

I nodded. “My brother’s friend Sebastian.”

Her face lit up. “Oh, my God, Sebastian’s coming? He’s SO gorge.”

I giggled like a little teeny bopper. “Yup. I’ve had a crush on him since I was twelve I think. But he’s always treated me like I’m a little girl and not worth the time of day.”

Alina took my eye-liner and saying, “Hold still, Nat,” accentuated the lines at the corner of my eyes. “He’s not going to think you’re a little girl in this outfit,” she continued.

I added a last touch of glistening pink lip gloss and puckered my lips. “I hope not.”

* * *

The party started off fairly quietly, with our friends sitting around our basement lounge chatting and drinking. There were probably around 20 or 25 of them who came by in all. I kept circulating, making sure new arrivals were getting a drink, and I was definitely getting some attention from the boys because of how revealing and sexy my outfit was. Then around midnight, the group got smaller and we started playing quarters. A bunch of people had left early, but there were about ten left, with only three girls—me, Theresa and Alina—and the rest of them boys. Everyone was getting a really good buzz when Sebastian, who has a dark streak in him, said, “Let’s play truth or dare.” No one would contradict him so we all gathered together in a big circle around an oversized leather ottoman in the middle of which there was an empty beer bottle sitting on its side on a tray. Sebastian spun it and it landed on my brother, Gavin. He immediately looked over at Theresa and asked, “Truth or dare?”

Theresa thought a moment, and then said, “Truth.”

“How many guys in this room have you given a blowjob to?” My brother was smirking, I think because she had given him one a couple of years ago when they dated for like six months. She thought for a second.


Everyone had the same thought. If she had sucked Gavin off, who was the other guy? Everyone looked around, I didn’t see any candidates for people who Theresa would have blown among the boys that were there. I saw Sebastian turn red. What? Was it possible she had blown her brother? Whoah. That family was crazy! Maybe it came with the territory of being ridiculously hot. You just couldn’t not have sexual relations. She was wearing a black knit dress that was a sensible length at just above the knee, but with a crazy plunging neckline, that went down almost down to her belly button and revealed a lot of cleavage. I could see her nipples had gotten hard and were easily visible through the thin fabric. I think it was a Louis Vuitton dress because I had seen Miranda Kerr wearing the same one, and there was no way she could wear a bra with it. It made me wonder if she was going commando too, like Alina and me.

Theresa gave the bottle a spin and it landed on Tom, a cute, preppy guy who had been on Gavin’s soccer team who always wore his Lacoste polo shirts with the collar up. Tom looked at me and asked, “Truth or dare?” I was pretty buzzed so I just blurted, “Dare!”

He narrowed his eyes, “I dare you to have a three-way French kiss with Theresa and Alina for no less than two minutes!” There were cheers from most of the guys. I began to blush and looked over at Theresa, then Alina. Theresa looked back at me, eyes glistening and smiled. “Fine with me,” she purred.

Alina smiled and shrugged, and in her little girl voice said, “Okay.”

I shrugged and said, “Okay, let’s do it.”

All three of us stood up, giggling a little nervously, and gathered in the center of the circle. I was wobbling slightly on my five-inch heels, as was Alina. We steadied each other with our forearms, and the soft touch of her fingers was comforting. I was surprised to feel a little slickness between my legs as I though about kissing both of these girls’ lips. I had kissed a girl just once before during a game of spin the bottle, but that had been a quick peck a couple of years ago, and the girl wasn’t nearly as hot as these two. I felt Theresa’s hand circle my waist. The feeling of her fingers on my bare skin set of a wave of slight dizziness and heat in my chest. Her touch was electric.

Theresa turned to look at me. I closed my eyes and I felt her soft lips touch mine. It was magical—soft, sensual magic. I opened my mouth a little and I felt her tongue enter, like a little garden snake slithering into its hole in the ground. I met her tongue with mine. Two garden snakes doing a mating dance in the dark. It was delicious—so sensual, and so forbidden! I was flushed with embarrassment to be kissing a girl in front of a bunch of people, but was also overcome with the sensuality of this mesmerizing moment. I hadn’t had a boyfriend in like a year, and hadn’t even been kissed in several months and there was a pent up hunger in me that was released in that feverish kiss. I inhaled her scent and drank in her saliva. I kissed her even more passionately, feeling a real love for her. I had discovered that I was bisexual! I knew I liked boys, but I was liking this too. A lot!

I felt Alina’s head join ours, pushing in between us, like a lamb searching for its mother’s nipple. Theresa and I parted and Alina leaned in to kiss Theresa first. I watched them lock lips and it was really beautiful. They were both such pretty girls, and they were really into it. Neither was holding back. The boys were hooting and clapping. Then Alina turned her head, and it was our turn to kiss. It was weird to French kiss my best friend. But it was nice too. Not as dizzying as kissing Theresa, but still very sensual, and a bit taboo somehow. After a few seconds of our tongues wrestling, she pulled back and smiled at me, and said, “I had no idea you were such a good kisser, Nat.” I giggled, “Me neither, Alina!”

At that, we sat down in our places and I spinned the bottle. It landed on Alina. She looked at me and gave me a wink. Uh oh, what was she thinking? “Truth or dare?”

One of the guys, Tim, protested, “Why does everyone keep picking her? How about spreading the wealth around?”

Sebastian turned and glared at the complainer. “You want to leave?”

“No,” Tim whimpered.

I said, “Dare.” It was too late to pick truth.

Alina grinned. “I dare you to suck Sebastian’s cock in front of everyone for a full minute, but no more, in front of everyone.”

She knew I was hot for Sebastian. She was teeing it up for me, but did she have to make it so public? Why didn’t she let us go to a room or something? I looked at Sebastian and his eyes had lit up. He liked the idea. This was what he had been waiting for.

I stood and grabbed a cushion from a chair. Then I got down on my knees in the center of the circle. Sebastian slowly approached and stopped just in front of me. He smiled, “Natasha, you don’t have to if you don’t want to, you know…” I smiled back at him and reached up to unbuckle his belt.

“I’m not going to wuss out, mister.”

I unzipped his black jeans and slipped my hand in, reaching in to feel his hard cock straining against his boxers. Sebastian unbuttoned his jeans and I slid them down his legs, along with the boxers. This released his erection, which suddenly sprung out straight at me, its tip leaking a drop of pre-cum, just a few inches from my face.

“Suck it, then, Natasha,” he commanded.

I couldn’t believe it. Right in front, in the flesh, was Sebastian’s beautiful, large, perfect cock. I looked around the room at the others before taking the plunge. My brother was staring at me as if under a spell, beads of sweat forming on his forehead. Was it stressful to watch his sister pleasure another man? Was this really hard for Gavin?

Everyone else in the room was riveted too. It almost seemed like no one was even breathing as they waited for my next move. I reached out and gently wrapped my hand around his member, feeling the silky texture of its skin, which contrasted so amazingly with the intense hardness under the surface. I was caught up in a conflicting whirl of emotions—of shame to be such a slut in front of all these people and crazy lust for this beautiful man. I slowly leaned forward, getting closer and then opened my mouth and took his cock in my mouth sucking it deep into my warm, wet throat. His pre-cum’s slightly salty taste was amazing. I pulled back and swirled my tongue around the cock’s helmet, relishing its smoothness and slickness.

“Oh, yeah, that is amazing, Natasha. You are good!” Sebastian moaned. Kneeling at his feet, he looked incredibly tall when I looked up at him. He gave me an approving grin as I began to move my head back and forth, relaxing my throat to let as much of his glistening shaft slide in as possible. This was so wrong and yet so right. I liked feeling sexy, and having this man lust for me in front of all these people. I had had feelings for Sebastian in secret for so many of my teenage years, and here I was finally pleasuring him with my mouth. How many times had I masturbated thinking of sucking him off, of him fucking me? Many.

Closing my eyes in order to better concentrate, I laced my fingers around his shaft and slid them back and forth, jacking him off, even as I encouraged him to fuck my mouth. I had read that guys like that. I heard him say, “Gavin, your sister is an unbelievable cocksucker. She’s going to fucking make me cum, dude!” He pushed a little harder down my throat and I gagged a little and my eyes watered a little, but that was okay. Sebastian shivered at the sensation of my warm, wet throat around his throbbing cock.

His comment to my brother on my cocksucking skills reminded me of how weird and how inappropriate this situation was, and I flushed with embarrassment again. But at the same time, I loved the idea of making him cum and increased the tempo of my fingers and my bobbing head. Maybe this would make him want to go up to my room with me after the party… Or even more. What I wouldn’t do to have him ask me to be his girlfriend!!

Sucking on his cock had made me very horny, and I had become very wet. I couldn’t believe what a horny slut I was being. I had never done anything like this in my entire life! Yet here I was, sucking cock in front of a rowdy, horny audience. My clitoris ached for attention, and I could feel juices running down my thighs as I didn’t have any panties on. Would anyone notice? Could I just drag Sebastian into a bedroom and have him fuck my brains out? That’s what I really wanted. I had placed my left hand on his butt to guide his thrusts back and forth in my mouth, and I felt a tightening of his ass cheeks. Was he about to cum?

At that moment Gavin shouted out, “Time!” I reluctantly pulled off of Sebastian’s glistening cock, tendrils of pre-cum stretching from my mouth to its tip. I gave it another lick to clean up the juices.

Sebastian looked at Gavin, pointing at his angry tumescent prick and said, “Seriously, dude? You’re not going to let her finish me? I need to cum!”

Gavin grinned, “Rules are rules. Times up!”

Sebastian pointed an index at him as he stuffed his hard member back in his pants, and said, “You’ll get yours, buddy. Just you wait.”

I sat down and wiped my brow, as I was now covered in a sheen of sweat from both my exertions and my crazy sexual excitement.

Theresa leaned over and licked my chin to clean off some spillage. “That was crazy hot, Natasha. You are one sexy chick,” she murmured. Wow she was licking her brother’s juices off me. Whoah. I basked in the warm glow of her approval.

Alina gave the bottle a spin and it landed on Tim, the complainer. He looked at me. “Okay, since we’re focusing on Natasha tonight, truth or dare?”

“Truth.” I didn’t really want to take a dare from him. He had turned me off with his whiny attitude. He seemed crestfallen at my answer.

“Uhm, would you be into having a threesome tonight?”

I thought about it for a second. I decided it was best to act as if it wouldn’t be a big deal. “Sure, that could be fun… With the right guy, or girl.” Looked over at Theresa and Alina and gave them a wink. Alina looked slightly shocked, but Theresa smirked and gave me a wink back. I saw some of the guys, including Gavin and Sebastian, looking at each other. I had opened some kind of conceptual door by acknowledging that, and I could assume their lascivious imaginations were whirling full bore. He spinned the bottle and it landed on Gavin.

My brother looked over at me, then at Theresa, then at Alina, stroking his chin as he thought about his dare. He looked at Theresa and asked, “Truth or dare?” She sat up, ready to take on a challenge, and smiled at him. “Dare.”

“I dare you to undress Alina and yourself and eat each other out in a sixty nine for two minutes.” This would be fun to watch! I wondered if secretly he wanted me to join in, but hadn’t asked because that’s not something you ask your sister to do.

Theresa and Alina stood, and stepping into the middle of the circle, began to undress each other. It didn’t take long. Theresa unzipped Alina’s leather mini dress and lowered it down her body so that Alina could step out of it. Alina then reached over and pulled the stretchy black dress that Theresa was wearing off her shoulders, and down her hips and legs. Alina tossed their dresses to the side and then lay down on the floor on her back. She looked so sexy, her lithe little body completely naked except for her Louboutin pumps. Theresa also looked amazing, wearing just the little zippered booties that were in fashion, and nothing else. Her breasts rivaled mine in size, and she had these pretty little nipples that pointed up at the sky. Alina’s nipples were the bigger kind, like a half dollar, and a darker brick red. The fact that they both kept their shoes on somehow made their nudity even hotter.

Theresa straddled Alina, placing her knees on either side of her torso, and was about to lean forward to get into position, when we heard a door creak, and the sound of footsteps coming down the stairs. Thank God we had the music on low and could hear the warning signal!

Gavin whispered in a panic, “Shit, that’s my mom! You guys, hide, quick!”

By “guys” he meant the naked girls! My adrenalin kicking in, I grabbed Theresa by the wrist and pulled her up on her feet, and she stumbled behind me as I dragged her behind the couch. She got the idea and fell down on her knees and folded her body into a crouch. Alina was just behind her and just managed to duck when my mom came around the corner. I had just managed to sit down on the couch between Gavin and Sebastian and grab a beer that I could nonchalantly pretend I was drinking.

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