Drinking Games Ch. 01

Story Info
Brother discovers younger sister loves wine bottles.
4.6k words
4.53
278k
107

Part 1 of the 2 part series

Updated 10/27/2022
Created 03/11/2008
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

My sister Jessica came to town that October to check out the university's undergrad program. She'd gone to community college for a year and wanted to transfer. I had a small apartment and she asked if she could stay with me for the week. I told her sure, but with this being my final year I was pretty busy and wouldn't be able to hang out much. Jessica said that was fine, she would find ways to entertain herself.

She arrived on Thursday morning. I met her at the train station. It was unseasonably warm that October and she wasn't wearing a coat. I noticed a few heads turn to watch this 20-year-old girl in a pleated black skirt and low-cut red blouse stride across the terminal floor to greet her brother. Jessica's short black hair was cut into a bob, framing her face. Her large blue eyes were bright and her full lips parted for a dazzling smile when she saw me. I knew the other men in the terminal weren't looking at her eyes or hair, though; they were staring at her full, pert breasts and the shapely butt wiggling under that skirt. I had never admitted it to anyone, but I'd noticed too.

Jessica dropped her bags and gave me a hug. We hadn't laid eyes on each other in four months. She smelled sweet.

I took her to my apartment and gave her the ten-cent tour. She would have the bedroom. I'd stay on the couch. My next class started in an hour so I had to go. She said she had an appointment with an admissions officer and she'd see me later that night.

Classes dragged. By the time I got home it was after seven and I was starving. The stereo was on when I opened the apartment door and Jessica was in the kitchen. Her clothes were the same she'd been wearing that morning. She was bent over, getting a pan out of a low cupboard. For a moment I caught a glimpse of lacy, plum-colored panties. I said hi and she looked over her shoulder and smiled.

"I'm making pasta," she said.

"Sounds great. What can I do?"

"You could go get some wine."

She must have seen the hesitation on my face. Before I could say anything she said, "I just turned 20 two months ago. That means it's only ten months before I'm 21."

"I don't know..."

"Then look at it this way: now's your chance to make up for missing my birthday party."

She had me there. I walked down the street to the liquor store and picked up a bottle of red wine. When I got back she had two plates of sauce-covered pasta ready, complete with grated cheese. She also had two shot glasses full of whisky.

"Someone's been snooping," I said.

"Yes," said Jessica. "And I am appalled that you drink such cheap shit."

She insisted we take the shots. I wished her a happy birthday and she winked and we downed the whiskies.

We sat on the floor in my living room, eating and drinking wine while music played in the background. She told me about her appointment that day and the tour of the campus. We talked about movies and friends and our parents and our love lives. Jessica's last boyfriend had been handed his pink slip a few weeks ago.

"He got a little freaked out," she said.

"What?"

"He was nice and everything but he just wasn't, well..."

I poured the last of the wine into my glass. "He wasn't what?"

"Adventurous," she said, blushing a little. "There were some things I wanted him to do and, well, he wasn't up for them."

"Like what?"

"Like, you know, sexual things."

I laughed and so did she and I told her to say no more.

"Are you sure?" she asked.

"What?"

"What about you? Any special ladies?"

I shrugged and told her there'd been some dates but nothing substantial. Jessica stared at me without saying anything and finally I laughed and asked what she was thinking. She just smiled and shrugged and took another drink of wine.

An hour later the bottle was empty, we both had a good buzz going, and the best idea in the world right then was getting some more wine. I stumbled down the stairs and walked down to the store to get another bottle of red. There was a line and the girl in front of me couldn't find her ID, so a ten minute trip quickly turned into twenty. When I got back to the apartment, my head wasn't swimming quite as much.

Jessica wasn't in the living room. I shut the door and looked around. The stereo was still on, but louder than I remembered. I opened the bottle of red and poured two more glasses. The bottle we had finished was not on the counter, I noticed. I took a sip and then walked back to the bedroom to see if Jessica had fallen asleep. The door was open and the light was on. What I saw stopped me in my tracks.

My sister's panties were on the floor. She was lying on the bed, on her back with her black skirt up around her waist. Her long legs were spread and her milky white thighs were delicious in the light. Her eyes were closed and she was biting her bottom lip. Two of her fingers were knuckle-deep in her shaved pussy. Her other hand held the empty wine bottle as she worked the bottle's neck in and out of her perfect ass.

My mind reeled at the sight. I was frozen.

Jessica moaned and gasped. She pumped the bottle into her ass faster now, her asshole stretched and wet. She withdrew her fingers from her pussy and stuffed them in her mouth.

My cock was hard. I took a step back from the door but kept watching.

"Fuck me," she moaned. "Fuck my ass harder. Do it."

She rubbed her clit and her moaning became louder and her full red lips were glistening just as much as the lips between her thighs. She began to orgasm. Her eyes popped open.

I stepped back quickly and retreated to the front door. I counted to five and then opened the door and shut it hard, yelling that I was back.

I waited in the kitchen, trying to get my hard-on to subside and failing miserably.

A couple minutes later Jessica came out of the bedroom. Her face was flushed and if I hadn't seen her fucking herself with a wine bottle just minutes before, I would have thought she'd just woken up from a nap.

"I thought I heard you," she said. "I fell asleep."

I wondered if she had put her panties back on. I held up a glass of wine. She held up the wine bottle; she'd brought it out from the bedroom.

"There's still a few sips in here," she said. "Why don't you finish it off?"

I stared at the bottle. Did she know I'd seen? No, of course not. I took the bottle and moved to pour it into my glass.

"Just drink from the bottle," she said.

"I don't like to," I said. She took the bottle and drank from it and licked her lips. She handed it back to me. "Don't be a baby."

I put the bottle to my lips. I could smell her ass on it but pretended not to. The scent was intoxicating. There were a few drops of wine in the bottle. I couldn't help myself: I licked the glass. Jessica smiled and watched me drink.

We sat on the couch and killed the other bottle. Her cheeks were flushed and she stumbled getting up, falling back on the couch and landing in my lap.

"Sorry," she said, giggled, stood back up, bending over and putting her hands on the coffee table to steady herself. Her skirt rode up and I had an unobstructed view of everything beneath: two firm and delicious ass cheeks with a thin red thong wedged deep between them. She had changed her panties. Jessica stood like that for I don't know how long.

"I think I'm going to fall over," she said. "Will you—help me—the bed?"

I didn't say anything. I stood up and there was my sister bent over in front of me. My cock was like steel in my pants.

She looked over her shoulder at me. Her blue eyes dark. Her lips parted and her breathing heavy.

Suddenly she pushed back and that luscious ass—the same ass she'd been shoving a bottle in—collided with my crotch. I fell back and she fell on top of me. On the couch now, my sister grinding her butt into my stiff dick. She was almost panting.

Then she stood up and straightened her skirt and said I was drunk and she disappeared stumbling into the bedroom, leaving me stunned and speechless on the sofa.

An hour went by. I couldn't sleep.

She had drunk too much. What if she got sick? If she was lying on her back she might choke. I should check on her. That's what I told myself, and it seemed like a great excuse to go see her, so I got up and went to the bedroom and opened the door slowly.

Jessica had fallen asleep on the bed. She was on her back. Her black thong was down around her ankles. Her skirt was bunched up around her waist. Her hand rested on her crotch. The lamp was on. She was asleep. My guess was that she'd fallen asleep while trying to get herself off.

I walked over to the bed to turn the light off. She didn't stir. My eyes ran over her long legs and red toenails. Her breathing was slow and deep.

It couldn't be helped. I can't say it was the wine in me, or simple curiosity. It was lust. And it had such a hold of me that leaving the room without at least touching her was out of the question. I gently moved her hand aside.

A strip of dark pubic hair crowned my little sister's pussy. I wetted my finger and, trembling, put it between her legs. She was wet still. Her lips were soft. I ran my finger along her slit. She didn't respond. I did it again, and again, and this time she gasped. A small gasp.

I had to leave, I knew it, but not before one more thing:

I slid my finger inside her. She was warm and slick and tight. A moan escaped her. I withdrew slowly, savoring the feeling. Then I put my finger in my mouth and tasted the rich sweetness of my sister's pussy.

I wanted to dive between her legs. I wanted to pull my cock out and stick it in her mouth and fuck her exquisite face until I came. Instead I went back into the living room and jerked off and went to sleep. Too much had happened that night. I wasn't about to make a huge mistake.

The next morning I woke up to find Jessica had left. There was a note on the bathroom mirror saying she had gone out to shop for a costume for the party. It took me a moment to figure that one out, then I remembered I'd told her about a Halloween party this weekend and she was welcome to come. I was having second thoughts about that offer now.

The note also said that Jessica would meet me for lunch if I wanted. She would be at the bookstore on the east side of campus.

I only had one class that day and it ended at eleven. I made it to the bookstore around noon. It was a huge place, two stories, with smaller rooms within it. Finding someone wasn't easy. I had made it to the cooking section when I overheard one male employee say to another, "You gotta see the girl in erotica, she's totally fuckin' hot."

"Yeah?"

"Yeah. She's been over there for like fifteen minutes just flipping through books. I'm pretty sure I saw her pinch her nipple."

I had the sinking feeling that I knew who the girl in the erotica section was. I made my way over there. There was indeed a girl there, the same height as Jessica and wearing tight blue jeans that highlighted her long legs and tight ass. She wore a tight black T-shirt. I would have thought it was Jessica except she had dark red hair that fell to the middle of her back. She was turned away from me, engrossed in a book.

I'd had enough searching. I called Jessica's cell phone. The redhead's small purse started vibrating. She pulled a phone out and before she said anything I said, "Jessica?"

The redhead turned. It was Jessica. Apparently she owned a wig.

I was about to ask her why she was wearing a wig, but her expression stopped me. Her cheeks were red and her eyes were hungry. Her nipples were hard and protruding through her tight t-shirt. She mumbled something under her breath and walked away quickly. I followed her, asking if she was ready to go. Jessica didn't answer. Instead she went to the back of the bookstore where the bathrooms were. She jerked open the women's door and disappeared inside. She was in there ten minutes before another woman knocked on the door. I heard my sister swear and when she came out she was breathing hard and didn't look happy.

"You okay?" I asked.

"Let's go."

I guess she didn't get to finish what she started.

At lunch Jessica told me she'd found her Halloween costume. She wouldn't, however, tell me what it was. I was at staring her long red hair.

"Do you like the wig? It was on sale and I thought it'd be fun. I think I look good as a redhead."

"C'mon, Jess, you'd look good bald."

"How do you know I'm not?"

"What? You're..." Then I realized we weren't talking about her head and I changed the subject.

That I evening I came back to the apartment not knowing what to expect. Normally I would have been at a study group session on Thursday night, but I was eager to spend more time with Jessica. Eager and terrified, all at once.

She was on the phone with a friend and waved to me from the living room. I set my bag down on the floor and spotted some boxes of takeout on the small kitchen counter. Next to the boxes were a frosty bottle of vodka and two shot glasses.

Jessica finished her call. She had taken the wig off. At first I thought she was wearing the same outfit as earlier, but I realized she'd changed her jeans. This new pair, just as tight as the old, had holes and tears in them. Especially around the thighs and butt.

"Before you say anything," she said, "let me explain. I met one of your neighbors and she said she was buying party supplies for Halloween."

"One of my neighbors?"

"So I asked if she would mind picking up some liquor for us since I still had to make dinner..."

"Okay, I get it. You convinced her to commit a crime. That's great."

"I didn't tell her I wasn't 21!"

"She didn't ask?"

"Not about that. But she asked about you."

"Who was she?"

"The girl down the hall. Blonde, long legs, really pretty eyes? Nice full lips, too."

I knew who she meant. I'd helped that girl move a chair in a few weeks back.

"She's cute," said Jessica. "You should ask her out. I bet she gives great head."

"Okay, are we going to eat or what?"

We did. Then Jessica demanded we take some shots. I said no and almost meant it.

"Come on," she pleaded. "I can't go to the bar with you and I probably won't see you again until Christmas! When do we ever get a chance to party together?"

Like I said, I almost meant it. We did two shots and started a game of scrabble. I don't remember the drinking rules, but I knew Jessica was pouring more shots and pretty soon I couldn't spell anything without giggling. Jessica was laughing too, but not nearly as much. Then, for some reason, I had the brilliant idea of asking about the bookstore.

"Were you getting off in the erotica section?"

"What?"

"At the bookstore. You were breathin' all heavy and then you went into the bathroom and you just, you just disappeared..."

"I was," she said. "I got really turned on. I love reading erotica.'

"You should see the library. The library's got a lot."

"What are you talking about?"

She was by the sink pouring more shots. I was staring at her ass and thinking that I should probably look someplace else, but my eyes were locked on those curves and the creamy skin showing through the holes and tears.

"How many have I had?"

"Six. No: seven."

"Is this seven?"

"This is eight."

"How many have you had, Jess?"

"What's at the library?"

"Oh yeah, the library! There's an erotica section on the fourth floor. Not huge, but there are, like, three or four shelves of it. That's a lot for a library, I think."

"Is the library open?" She handed me the shot and sat on my lap.

"You're sitting on my lap."

"You noticed."

"Yeah the library's open, it's open all the time."

"Drink."

I did. So did she.

"I want to go," she said. "Let's go right now, we'll take the bus."

I'm sure I protested, but for how long I can't remember. Not that long, I figure.

She insisted on wearing her new red wig. We stumbled outside and down to the bus stop. It was chilly out that night. The bus was empty except for us. We sat near the back.

I was warm and reeling. I knew I was drunk and I felt bad that my little sister was drunk, but not that bad. She was hugging me because she was cold and hadn't grabbed a jacket and her nipples were hard and I could feel them through her shirt pushing into my arm. She wasn't wearing a bra.

Lemme ask you something, Jess."

Yeah?"

How do your tits stay so perfect without a bra?"

She laughed. "How do you know I'm not wearing one?"

"I can see you're not."

"Well you're wrong."

"I am not."

"How do you know?"

"Because..."

Jessica took my hand and placed it on her left breast. I could feel her stiff nipple under my palm. My hand slid down to cup her breast. She closed her eyes.

I took my hand away and said, "I told you you weren't."

Her mouth was near my ear and she was telling me things that I forgot immediately because her whispers and breasts were turning me on. Her tongue flicked my ear and I jumped a little. She laughed softly and sucked on my earlobe. I told her she shouldn't do that.

"Why not?"

"Because..."

"My jeans have all these holes in them."

"Yes they do. Yes they do, Jessica."

"I'm getting cold, could you put your hands over the holes to warm me up."

She pulled my hand between her thighs, near her knees. I could feel her skin. It was really was cold.

"Jessica, you're freezing...!"

"I know, that's why you have to warm me up."

I rubbed her skin. She nuzzled my neck. Then she grabbed my hand and pulled it up to her crotch and said, "There's another hole."

Indeed. There was a tear right near her crotch. The wig helped; it was like she was some girl I'd only just met. A girl who wanted me to finger her on the bus.

I was in the middle of deciding whether this was a good idea when the bus stopped and she slid forward. My finger brushed her pussy and I jerked my hand out of her lap. Jessica just laughed.

It was a short walk to the university library. The building was quiet. She was giggling about something but I wasn't sure what and I was too busy trying not to walk like I was drunk. Then she became very serious and asked me where we were going. I said the third floor. We took the elevator. I showed her the row of erotica. Just a few shelves, really, maybe sixty books. She started reading to herself, then out loud. After a few minutes of staring at her while she read, I was hard as a rock.

Suddenly she stopped. "This is too much," she said. "I've got to get off."

Jessica grabbed my hand and dragged me back towards the elevator. There was a bathroom nearby. She told me to stand guard outside. She disappeared behind the door.

I stood there about a minute, wondering what the fuck I was doing in the library, holding a book of smut, with a hard-on for my little sister who was no doubt fingering herself to orgasm not even twenty feet from me.

Then I heard her call: "I need help."

"What?"

"Open the door!"

I peeked my head in. She was in one of the two stalls. I couldn't see her.

"I want you to read to me," said Jessica. "I can't get off."

"I can't do..."

"Just shut the door behind you and read!"

I did. The story was something about a young girl of eighteen getting finger-fucked by a woman in an elevator. Then a security guard got on the elevator and both of the women proceeded to suck his cock until he came all over the young girl's. The other woman then licked the cum off her face.

Wet sounds were coming from the bathroom stall. My sister was panting.

I unzipped my pants and pulled my dick out. It was wet with pre-cum. I started stroking myself listening to her.

"Come over here and read to me," she said. "I can't hear you."

I went over to the stall and pulled the door open. There she was, sitting on the toilet, her jeans and panties down around her ankles. Rubbing her clit with one hand and squeezing her breasts with the other, pinching her nipples through her tight black shirt. She looked up at me and her eyes went to my cock.

12