Never Have I Ever (Part-1)

Don't get me wrong, I have always loved my little brother Sammy. He was always just sort of, I don't know, a dork. I think that she came out of the womb with a certain social awkwardness and a unique ability to make himself invisible in plain sight. Sammy is a total nerd and always has been. I am not saying that to put him down. Like I said, I really do love my little brother. We never had that sort of torturous older sister/younger brother thing that you see on television and movies. I just want you to know what we are dealing with here.

So, this story I am going to tell you about my brother and I happened about two years ago. At the time I was 20 years old and a sophomore in college. My brother was 18 and a senior in high school. Not that he looked it. He was always painfully shrimpy and reaching the age of adulthood hadn't changed that. I am not a tall girl, only around 5'5, but I was still taller than my brother at 5'3. On top of that he was string bean thin, probably only 110lbs. He had short brown hair and dark brown eyes. He had a handsome face, but it was a bit childish and he couldn't even begin to grow facial hair. His skin was always very pale and he was incapable of tanning. Worst of all, he always wore really baggy clothes and slouched. He looked like a pouty kid more than a man just a few months short of college.

If you just looked at us, you'd never know that we are related. As I already stated, I am taller than my brother. I have very long light blonde hair and bright, wide blue eyes. I have thick pink lips and a pretty, oval face. The only thing I don't like about my face is that I have slightly rotated eyeteeth, but some people tell me they look cute. Whatever. I have small, round breasts (34-B) and a flat stomach. I have hips slightly wider than my breasts, a toned butt, and shapely legs. On top of all that, I take after our mother and tan very easily. You wouldn't think we were cousins, let alone brother and sister.

It all started on a Friday morning. It was in December, near the end of the first semester. I would be going home for Christmas break in a few weeks and classes were just starting to wind down before exams started. As I said, my brother was a senior in high school so he was deciding where he wanted to go to college. His applications were all due in early January, so he was really running out of time.

I went to a big public university. Very much a party school. Also very affordable. My brother was always much smarter than me and he wanted to go to some small liberal arts school in the middle of nowhere. It was prestigious and quiet, which suited my brother's personality perfectly. Unfortunately it was also wildly expensive. My dad had called me on Thursday to tell me that he was sending my brother to my school. He wanted me to show my brother around and try to convince him that my school, or a similar school, would be a better fit for him. I knew that meant my dad didn't want to pay for my brother's prestigious choice.

I was not really excited about showing my brother around on a Friday night. I had plans, I'd been invited to a party and I wanted to dance (things that I would not be able to do with my sulking brother lingering around). But, when the man who is paying for your education (and giving you money for food and gas) asks you to do something, you have to suck it up and agree to it. So on Friday morning (a day I don't have classes) I was at the train station in town, picking up my brother.

"What's up nerd?" I asked when he sat down in the passenger seat next to me. He gave me a sad little smile and threw his duffel bag in the backseat.

"Hey Lynn," he said, "Sorry dad is making you do this." He looked almost embarrassed, like he knew that I had been bitching about him the entire drive to the train station. I smiled at him.

"Don't be a doofus," I said, "It'd be an honor to show you around." And with that I kicked the car into gear and headed back towards campus. While we drove I asked my brother about school and about his extracurricular activities (he was president of a thousand socially suicidal clubs, but I tried not to give him a hard time about it). He gave me short, embarrassed answers, so I mostly let things dropped.

"New girlfriend or anything?" I asked finally, trying to make him talk. My brother has a hard time warming up to conversation, even with my parents or me. He gets shy around people he's known his entire life. You have get him started, then he can almost manage a normal human conversation.

"No," he said and he looked over at me with the most pathetic face I'd ever seen, "I have pretty much realized that that is never going to happen." He sounded sad, but not in an acute way. He seemed...resigned. Like he really had given up on the opposite sex. My heart broke for him. He was so smart and he could be funny when he allowed himself to be. He could be cute if he dressed himself properly. There was no reason for him to give up. I felt like I was going to cry. I reached over and gave his hand a squeeze.

"Don't think like that Sammy, you will have a beautiful girlfriend someday very soon. I know it. And someday you will get married and have an army of cute little nerdy children with glasses and pocket protectors," I said. He laughed a little and I felt better, even though I was pretty sure I hadn't convinced him of anything.

It was around ten in the morning when I parked my car outside of my dorm. I had begged my dad to let me move off campus for my sophomore year. I knew a bunch of people and could have stayed at any number of houses. But he said he didn't like the things that happened at off-campus housing and said I would be in the dorms at least through my junior year. Like you can't get drunk in a dorm or something! Sometimes, my dad is kind of dense.

Luckily, two girls that I knew, Adrienne and Carrie, were both on full-ride academic scholarships. Because they were on scholarship, they received a grant to pay for their student housing. They'd lose the grant if they moved off campus so they stayed in the dorms as well. Since we were friendly (if not friends) we got a suite together. The suite was on the fifth floor of a large brick building and it had four rooms. There was a living room with a small kitchen essentially in one corner, a bathroom with a slim shower stall, and then two bedrooms. We'd had a coin flip to start the year and I'd won. So I had a private room and Adrienne and Carrie shared the other.

We took Sammy's duffel bag up to the dorm and dropped it in the living room. I'd already discussed it with Adrienne and Carrie, and they were cool with Sammy sleeping on the couch. When we came up, Adrienne and Carrie were sitting on the couch watching television.

"Hey Lynn" Adrienne said, "Is this the rug rat?" she pointed to my brother. He almost flinched away from her finger and Adrienne laughed. She was the boisterous and friendly roommate. She was very pretty with long black hair, grey eyes, and olive skin. She was tall and lithe with small breasts and pretty legs that she poured into tight jeans to show off her small, muscled butt.

"You're giving him a complex," Carrie said. She was the sweet and shy roommate. Not shy by my brother's standard, but by normal human standards. Carrie was short and curvy with long auburn hair and green eyes. She was almost as pale as my brother, but she pulled it off better, like a Victorian-era lady or something.

"Yeah this is Sammy," I said, throwing his bag on the floor, "Sammy this is Adrienne and this is Carrie." He stared at them blankly. His lips moved a little, but he didn't say anything.

"Nice to meet you," Carrie said, finally. Adrienne smiled and nodded.

"Same to you," My brother said in a squeaky little voice. Adrienne looked like she was about to make a joke, but I shook my head. She would think it was funny and wouldn't mean to hurt, but any little teasing would crush Sammy. We stood awkwardly and quietly for a few moments. It was like Sammy was capable of bringing discomfort with him.

"So what are you guys doing today?" Adrienne asked finally.

"Oh you know, doing the tour thing. Taking him out to Florentine's for lunch, not really sure exactly," I said.

"What are you kids doing tonight?" Adrienne asked, "Are the Sampson children going to go wild on a Friday night at the state college?"

"No," Sammy said and I was surprised, "I don't much like parties." Well that was the end of that. I was hoping to take him out, to loosen him up and make him see the opportunities that were available in college. No dice.

"Well Adrienne and I are staying in tonight. Habitat for Humanity in the morning. If you guys want to hang out with us this evening, that's cool," Carrie said. I thanked them and then dragged my brother out of the dorm. We might not be able to go to a party tonight, but I wasn't going to let him hang out in his room all day. It wasn't like he was at home.

As I promised I took my brother out to Florentine's. It's a surprisingly good, and inexpensive, Italian restaurant that is sort of a hangout for the students at my school. He looked sullen most of the time, but that was normal. He seemed to like the food. When we were done eating we checked out the things I knew he'd like. I showed him the library and the computer labs. We walked around the gardens (though they didn't look great in the winter) and the portrait gallery. We even looked in some of the darkened classrooms and dining facilities. I kept him away from the things most people would want to see, the bars and the frat houses.

But it was nice. During the day he started to warm up a bit. We had a conversation, an honest to god talk, about college. What he was looking and everything else. I knew from what he was saying that my school could be a decent fit for him. That's the nice thing about a big college; there is plenty of space for everyone.

"I told dad I wanted to go to that little school we took you to in Springfield," he explained as the sun was starting to go down, "The little liberal arts college. I did it just to get a rise out of him." He explained and I laughed. My dad was paranoid.

"Where do you want to go? Here?" I asked and he shook his head.

"I want to go to an urban school somewhere, like New York or Boston or something. I just, I like being anonymous. I want to go somewhere where no one would notice me," he explained. I guess I knew that feeling. But I felt bad for him. Part of his problem was that he was already too anonymous. He needed to branch out.

"Don't go trying to disappear on me little brother," I said, "I love you and if you try to become completely anonymous, I will hunt you down and find you." Then he did something very strange. He reached over and grabbed my hand and held it.

"I love you too sis," he said, "Sometimes you're the only person I love, but I do love you." I was touched. I mean, I really felt lovely when he said that. And we walked the rest of the way back to the dorm, hand in hand.

We arrived back at the dorm around 5:30 and the sun was almost completely out of the sky. Carrie was still sitting on the couch watching television, but I didn't see Adrienne anywhere. Carrie didn't look like she'd moved all day and she stretched and yawned when she saw us.

"How was the tour?" she asked. Sammy shrugged.

"It was fine," I said, "We ran into that mouth-breather guy who likes you at the library."

"Oh God!" Carrie said and we both started giggling. Then I heard Adrienne's voice.

"Hey Carrie, are we taking your care to Habitat tomorrow? I was just...Oh!" I turned and looked Adrienne was walking out of the bathroom. She had clearly just showered. She had a towel wrapped around the top of her breasts but it was incredibly short. A triangle of flesh was exposed on the open side and one entire ass cheek was in the open air. If she moved slightly, she vagina would have been clearly visible. Normally this wouldn't have been a huge issue. I, and to a greater extent Carrie, would have liked Adrienne to be more discreet, but if it was just us girls, who care? The problem was Sammy.

I looked over at him and he was staring at Adrienne's hip. His eyes were wide as saucer's and I swear his mouth was actually hanging open. This was probably the closest he'd ever come to a naked woman and I think I could feel his heart beating.

"What are you doing?" I said, laughing, "You knew my brother was going to be here, you pervert." Adrienne put on a shocked face.

"How was I supposed to know you'd be back? You're the pervert, staring at me!' she said and I saw Sammy look away quickly, even though Adrienne was talking to me.

"Whatever," I said, "Go get changed." And Adrienne went into her bedroom. She came out a few minutes later in soft pajama pants and a tank top. He outfit was almost identical to what Carrie was wearing, except Carrie had a t-shirt on instead of a tank top. They looked comfortable.

"I am going to put my pajamas on too," I said, "I will get changed in my room. You can get more comfortable if you'd like Sammy. Just use the bathroom. Please don't come out half naked, that is Adrienne's job." Adrienne stuck her tongue out at me as I went to my room. I came back out a few minutes later wearing a pair of tight gym shorts and a long-sleeved t-shirt. Sammy was already back, wearing sweat pants and a t-shirt. Both black, as fit his sense of style (if you could call it that).

We sat around for a while and watched television. I ordered a pizza and we all ate dinner. For a while the girls tried to get Sammy to talk. I did as well. But it was no use, he was too shy. Eventually, even Adrienne started to give up.

I was thinking about my brother's eyes when Adrienne walked out of the shower. He clearly found her attractive. He hadn't given up on girls because he didn't think they were sexy, he did it because talking to girls stressed him out too much. If there was just some way I could show him that talking to girls didn't have to be difficult, that it could be fun, I'd maybe make his trip here worthwhile. But how did I do that? Then I thought of something.

"Let's play a game!" I said. Sammy would be forced to talk, and maybe even attempt to flirt, if we played a board game or something.

"Yeah, this show sucks," Carrie said and clicked it off, "What do you want to play?"

"I don't know. We have Risk, Monopoly, and Scrabble. But I am not in the mood for Scrabble," I said. Scrabble is a quiet game; we needed something that required talking.

"Ah! No Board games let's play something else. How about Kings!" Adrienne said. I shook my head.

"Even if we wanted to we don't have any alcohol. How do you play a boring drinking game sober?" I asked. I looked at Sammy out of the corner of my eye. He was watching everything happen, but didn't seem to be taking much of a rooting interest in anything.

"Well I won't play if we play a board game," Adrienne said.

"How about Poker?" I asked. Everyone else groaned at once.

"You always win, that's no fun," Carrie said and I laughed. It was true, but I still would have liked to play.

"I know!" Adrienne said, "I played this game with some people last week. You know that game 'never have I ever?' well it's like that, except you have dares mixed in!" I was just about to decline to play that game when my brother spoke up.

"I don't know that game," Sammy said and I was shocked to hear him talk. Adrienne was so excited about her idea that she didn't even notice that Sammy was awkward, she just engaged him, which is what I was looking for.

"Oh I'm sorry," she said, "Okay so like everyone will put up a hand and then whoever's turn it is will say something like 'never have I ever eaten a peach pie,' and if you ate a peach pie then you have to put your hand down. You can play it with beer, so like if you put your hand down you have to drink."

"We aren't drinking," I said. Adrienne turned to me and rolled her eyes.

"I know that Lynn!" she said in an exaggerated tone, "That's why I said it can be played with dares. If you play it that way, anytime you play a round everyone who puts their hands down it 'out.' Whoever is out, they have to do a dare that the people are 'in' make up together. So like on that last thing. If Carrie and I put our hands down because we both have eaten peach pie and the Sampson Siblings kept their hands up because they are sociopaths who've never had peach pie, the brother and sister team has to come up with a dare for Carrie and me to do." She said it all in one breath; it was exhausting just to hear her.

"I don't know," Carrie said, she looked a little nervous about the room this game had for potential dangers. I was about to add my voice to the chorus, when I saw that Sammy looked a little bit excited. He was staring at Adrienne in the same way he had when she was nearly naked. Like she'd accidentally forgotten he existed and he was going to get to take advantage of it. I wasn't happy about this game, but I'd do it for my brother.

"Come on Carrie, it's this or more Jersey Shore," I said. And now it was Carrie's turn to roll her eyes.

"Fine, let's play," she said. I didn't ask Sammy, I just assumed he was on board and figured he didn't want me to point out his presence to the girls.

"I will go first since it was my idea," Adrienne said and we all booed. She laughed and said, "hands up everybody. Okay, never have I ever... slept in Lynn's dorm room when she was out of town!" Adrienne said and the laughed. Carrie blushed as her hand slowly went to her side.

"You bitch!" I said, "I can't believe you slept in my bed!" I was trying not to giggle, I could care less if she took a nap in my bed.

"I cleaned the sheets! It was because Adrienne had a boy over. It was her fault," Carrie said. I shot a look at Adrienne and she just shrugged.

"Carrie is the only one out, so we have to make a dare for her," Adrienne explained. So Adrienne, Sammy and I huddled up and decided on a dare. Since my bed was defiled, I got to announce it.

"Carrie, we dare you to take off your tank-top and play the rest of the game in your bra!" I said. It was harmless, and I knew that Sammy would get a kick out of it. Carrie's fair skin turned a deep crimson.

"I don't know..." Carrie said, and I saw her eye dark to Sammy.

"He's seen way more of Adrienne than he will see of you," I said. Carrie saw that we weren't going to budge. Deftly she slipped her tank top up over her head and threw it onto the floor. She was wearing a pretty pink demi-bra with white lace. Her breasts looked large and round in it. Sammy noticed as well, but did a decent job of hiding his interest.

"I think we should let Carrie go next, she is half-nude," Adrienne said.

"Fine," Carrie said looking right at Adrienne, "Never have I ever had sex in Lynn's bed when she was out of town." Now I was actually pretty angry.

"I assume you didn't wash the sheets," I said to Adrienne and she gave me a devilish smile. I looked around and saw, thankfully, Adrienne's hand was the only one down.

"Shouldn't you have a hand down, Lynn? I am sure you've fucked in your bed. I mean three weeks ago..." Adrienne started but I cut her off.

"She said while I was out of town. It is impossible for me to have sex in my bed when I am not in it," I said. I didn't really want to talk about my sex life in front of Sammy. I was a little nervous about where this was going.

"Fine, come up with a dare then," Adrienne said. We huddled together. Sammy didn't do much talking, but Carrie and I came up with one. Carrie announced it.

"Adrienne, we dare you to moon out our window for thirty second! Pull the window down too, the December weather is good for your ass!" Carrie said and we all giggled. Even Sammy laughed a bit.

Adrienne moved like she wanted to prove she was stronger than Carrie had been. When she reached our window, she pulled it down quickly and turned. The freezing air poured in and I wrapped my arms around my chest. Adrienne pulled down the back of her pajama pants and pushed her ass out the window. It was darkening outside, but there were lights on the side of the building. Our dorm faced into the middle of the quad and we heard someone laugh and we hoped it was because of Adrienne's ass. I noticed that Sammy wasn't watching Adrienne, his eyes were on Carrie's chest, where the cold breeze from the window had made Carrie's nipples hard. She didn't notice.