Pushing Boundaries

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All characters are 18 years of age or older.

This story can be read as a standalone story and is my tribute to all the strip poker stories I have enjoyed on Literotica over the years. If you want to learn more about the main characters, check out the First Time Button Pushing category. The story involves anal, exhibitionism, groups (two guys and a girl and several guys and a girl), mild reluctance, toys, lesbianism, and of course, lots of sex.

Austin, Alana and their roommates play strip poker on a rainy day and everyone gets really turned on.

Thanks to Antmatter for keeping my Canadianism in check.

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“Austin, wake up.”

It’s not that I’m lazy. Sure, I’ve missed a few college classes over the past few years due to sleeping in, but over the past two weeks I’ve been sleeping in more than most, and for good reason.

I slowly opened my eyes and quickly sat up when I saw Alana standing in my bedroom doorway. We were my best friends since childhood, inseparable, and became roommates in college. The reason I slept so long is that Alana and I started having sex two weeks ago. I had loved her for years, but she had always been a Venus lesbian and I felt she was never interested in me “that way.”

Turns out I was wrong.

Alana stood at my door, a fresh towel tied around her waist. Her thick blonde hair, dark and wet, fell in curls over her bare shoulders. Drops of water clung to her arms and plump, athletic body. Her large breasts stood high on her chest, jutting out slightly as she smiled at me, her dark pink nipples hard and exposed to the air.

“Good morning, beautiful,” I said.

Without a word, Alana walked over to my bed, pulled a towel around her waist and got under the quilt I had covered her with. Pressing her naked body against mine, she kissed me tightly, a teasing smile on her lips as she felt my swollen cock grow hard against her thigh.

“I love you.” It came out.

Alana blinked, and I almost panicked. Best friends for nearly twenty years and in a relationship for two weeks, but neither of us had ever said those words. At least not like that, and not to each other.

How miserable I am! I cried to myself.

On our first night together Alana told me she didn’t want to see or date anyone else. This wasn’t a “let’s keep it steady and be exclusive” or even a “boyfriend/girlfriend” conversation; we decided to move in quietly without telling the other roommates because Alana said this was our only chance. Everything was pointing to us being together , but I may have messed it up.

Alana’s slightly surprised expression turned to joy and she pulled us into a tight hug. “I love you too, butthead.” When she kissed me again, I felt my heart beating a mile a minute in my throat, a swarm of butterflies taking over my stomach and chest.

he loves me.

“But we need to talk about something.”

The paradise I was experiencing suddenly stopped, like a DJ playing a cover record. “Okay,” I said softly, filled with fear.

“Austin, I really love you so much . You’re the only man I’ll ever have in the whole world. I want to be old and have ninety years of dirty sex with you. But there’s something you can’t give me. Another thing I really like is pussy.

My mind was having a hard time adjusting after two dramatic 180s from nervousness to excitement and back again. “So do you want to date other girls?”

“No, not really. I just want to fuck other girls. I only want a relationship with you.”

I’m too busy trying to figure out how I feel about this. In terms of physics, I mean… sproinngggg. I always fantasized about Alanna being with other girls because she would often tell me about her lesbian activities. I didn’t realize until recently that she was doing this to attract me to her, but I was too stupid to do that. My heart was saying yes too; I knew Alanna was bisexual, or in my case, lesbian, so agreeing with her and letting her be happy was the right and proper thing to do.

Still, my heart was screaming, NO. Or more appropriately, “It’s over!” I finally brought the love of my life back to reality. Alana had been in over a dozen relationships since coming out as a lesbian in tenth grade. What were the chances that she had gotten in touch with a girl and cosmic events revealed that they were closer soulmates than we knew? What if I eventually lost Alana after finding her?

“Okay.” The answer came from the part of me that was imagining the lesbian activities Alana had once told me about. My penis was in the middle of them.

“Okay?” Her eyes were wide open and she placed her hands on my chest as we lay together. “Do you…do you want to have sex with other people?”

“I’ve never been like that,” I said. “I don’t even know if I can. Of course, I’ve fantasized about other girls, but it’s always you.”

How foolish I am.

Alana raised her eyebrows slightly. “What if I want you to fuck another girl with me?”

Oh what? Come again?

“Uh,” I stuttered, “really?”

She just smiled, snuggled into my arms, slid her hands up my back, and buried her face in my chest. After a few moments of silence, she asked, “Who do you want to see first? We know so many beauties.”

**********

We stood at the bay window at the front of the house, six roommates, looking out at the torrential rain. Honestly, we needed rain, but did it have to come on our roommate bonding day? Beth had prepared for our outing and was alone with her packed picnic basket that morning while the sky was still clear and blue.

“Monopoly?” Josh, our only other male roommate in the room, asked.

We all groaned.

“Jeopardy?” Josh loves the board game, and we’ve all played at least a few rounds with him since the beginning of the school year. His latest suggestion has been met with more complaints. At least he’s not pointing to one of his weird non-mainstream games “I bought it online from Korea.”

“How about something cool like blackjack or poker?” Marlena asked. We all raised our eyebrows and said “that’s a good idea”. Malina smiled like an American girl next door and pushed a lock of light brown hair out of her face. After Alana, Marlena was always at the top of my “date” list, but I never pursued her. Always telling myself it was because we lived together, deep inside I knew it was because I kept up hope.

“How about we have a picnic and play cards?” I suggested. “We could take out all the furniture and sit on the floor in the common area.”

“And drinks,” Beth smiled, putting down the picnic basket. “Put out the wine, no need for a bottle.”

We all laughed and soon began moving the couch as far out of our tiny living room as possible, leaving the center of the room free for Beth to spread out the classic red and white plaid blanket. While Alana, Ricky and Josh disappeared into their rooms or the kitchen to get wine, Marlena and I helped Beth set up the meal she had prepared. It wasn’t a gourmet feast by any means, we were college students after all, but the sandwiches looked good, and she spent some money to buy us chocolate bars and snack bags of chips.

It was only a few minutes before we sat in a circle, eating our sandwiches, each holding a red plastic cup filled with a Coke and our choice of wine or beer. I took the last sip of my second beer as thunder rumbled in the house and the weather outside continued to be chaotic. “So,” I asked, “what are we going to play? We need to make some bets.”

“Snacks,” Ricky said, pointing to the chocolate and chips in front of his crossed legs. “Anything open counts as a point.”

“Yeah,” Josh mumbled angrily, his mouth stuffed with a handful of potato chips.

“I like it,” Alana said, “but let’s split it. Josh is going to lose soon.”

The girls laughed and said something when Josh swallowed, then sighed and gave up. Instead, he picked up a deck of cards from across the room and started shuffling the cards around while we sorted out the snacks — once they were all distributed, everyone got a combo of either five bags of chips or a chocolate bar.

The first step took a while to get through, as it turned out we needed to clarify the rules in a few areas. We all knew what poker hands usually were, but when Beth said “Hit me” on the first turn, we realized we needed to do some work.

“Well, the game is five-card draw,” Marina explained. “I learned this by watching poker on TV, so if anyone thinks I’m wrong, please speak up. We were each dealt five cards face-up, as it is now.” “Like this,” Marina explained. “Once you’ve seen your cards, we’ll begin a betting round. We won’t play blinds or antes because we don’t have a lot of betting snacks. After bets are placed, each of us can fold up as many cards as possible, then draw new cards to replace them, and then we reveal.

We all nodded silently, knowing how to play, and the game began. In the first hand, we had to repeat the rules several times and no one turned, so when Ricky turned over three cards of the same type, he earned a dozen prizes, making him the rich bitch in the game.

“I knew it,” Josh accused, “Ricky was too quiet and she was trying to trick us.”

“I’m not!” the dark-haired football player complained. “I’m very lucky.”

“Of course,” I joked, “we’ll see who wins all the snacks.”

We were all on our third drink, or fourth in Beth and Alana’s case, drinking together while Josh was dealt the next hand. I had a pair of deuces and an ace high, which wasn’t great, but there was a little hope, so I threw down the last bag of chips, and I was left with a pair of Mr. Big chocolate bars. Everyone except Josh threw down gifts and our dealer decided to fold it early. I threw down the other two cards, keeping the 2 and the ace, and I had to hide my smile when I saw the 8th and another ace face down. Two pairs!

Alanna took the lead in the betting and cautiously placed a second snack, forcing everyone except Ricky to have one, leaving herself with only one snack. I was nearby, glancing sideways at Alanna, trying to gauge her reaction, but she just winked at me, causing our roommates to laugh.

“I’m on the phone,” I said, tossing the chocolate bar.

Malena turned to my other side. Ricky casually tossed down another bag of chips, his winnings lying haphazardly on the floor beside him. Little Beth’s eyes shifted from the pot to the poker player in front of her, she licked her lip ring a few times with her tongue, and then dumped the remaining two snacks into the pot. “Everyone?”

I groaned, and Alana’s voice echoed. Ricky smiled and shrugged, eager to throw in another snack to match the bet. Technically it was Alana’s turn now, and she was hesitating about whether or not to throw in the last snack. If one of us lost, we would be out.

“I’m calling too, all-in,” she said finally, putting down the last piece of chocolate.

I looked at my cards again. Two pair, two pair and an ace. It’s a good hand, but with Alana and Beth both betting, what are the chances of them playing a better hand? I took a deep breath and glanced at my remaining crisp bars. An extra hand helps me play. “I fold,” I groaned, throwing my cards face down at Josh.

“Okay,” he said, looking at the three girls who were still holding him. “Let’s see who wins.”

Beth flipped her cards, revealing two pairs of eights and nines, and I let out another groan. I’ll beat that hand. Ridge just shook his head and smiled, tossing the cards down towards Josh – he didn’t beat Beth. But Alana was grinning like a demon, flipping her cards. Teams of three and four, winning hands.

“Oh!” Alana meowed, reaching out to pull her skillet back onto her seat. “I’m telling you, I’m rich. Make it rain!” She threw the bags of chips into the air and most of us laughed. Beth was sitting across the circle and she was unhappy.

“Well, I guess I’m out,” he sighed, taking the last of his rum and coke and starting to pour himself another.

“Oh, poor baby Pierce, she’s so sad she lost it.” Alana calls Beth “Piercings” because she’s quite liberal with her body adornments. Beth has several piercings on the side of each ear, and she also has two small silver eyebrow piercings, a septum piercing on her nose, and a lip ring. She has also shown off her tongue piercing before, although it wasn’t very visible. “Don’t worry, I’ll bring you some snacks so you can keep playing, but it’ll cost you money.”

Beth finished mixing the drinks and turned her eyes to Alana, “Well, I don’t want to just watch. What do you want to do?”

Alana smiled triumphantly, leaned into the circle and whispered from the stage: “I’ll give you three snacks to fill your bra with.”

I know my reaction was to raise my eyebrows in surprise and purse my lips, and I saw Josh’s mouth stay open for a long time, trying to move the deal forward.

“Oh, I’d like another beer,” Marlena said with a smile, handing Ricky another beer.

Beth is an outgoing girl and a tomboy – she plays bass in our garage band and co-leads it with Josh. She’s been a troublemaker ever since I knew her as a freshman in college, but I had never seen her do something so risqué. She was wearing only a pair of knee-length shorts made from old skinny jeans, a men’s white wife-beater vest, and a black bra. Her black hair wasn’t even parted sideways, as she had it cut short and disheveled like a boy’s.

She thought about it clearly, immersed in her heady thoughts, curled her lips to one side, and looked at Alana with squinting eyes. “Okay, I’ll do it right away.”

Hearing Beth say these words, I adjusted my sitting position to accommodate the rise of my shorts. Beth got down on her knees, reached behind her back and unhooked her bra. She hesitated, then quickly took a sip of rum and coke and then removed her bra from under her thin shirt and threw it at Alana.

Beth leaned back in her chair and crossed her arms over her chest, “Happy?”

“Yeah,” Josh said, smiling.

“It’s not you, asshole,” Beth said, patting his arm on the side. She has nice small tits, maybe a little more than a handful, but what’s really interesting is that both of her nipples are clearly pierced, with bumps from her nails on either side of her nipples.

“I just have one question,” Alana said, smiling.

“What is that?” Beth asked.

“Are you pierced there too?”

Beth blushed and clutched her breasts, “No, I’m not a big pervert, just a little one.”

Everyone laughed, and Josh picked up the cards and began shuffling them, while he was clearly distracted by Beth’s gaze.

I leaned back, watching everyone else get distracted by her nearly free breasts, and looked at Alana. She smiled and winked at me, then nodded at Marlena and raised her eyebrows a few times. I took a deep breath and tried to calm my nerves and try to understand what she meant. It may have started with Beth, but Alana’s goal was to find Marlena because she knew I had a crush on our roommate.

Malena wore an old black band shirt with most of the sleeves and hem cut off, turning it into a sleeveless t-shirt. The ruffled edges showed off her slim stomach and the rounded edges of her sports bra-covered breasts. Her white stretchy yoga pants clung to her skin and if we went on a picnic as planned, I would have been staring at the park all day.

“Okay, enough staring, you idiots,” Beth complained, re-wrapping herself. “The cards have been dealt, I want to win back some snacks.”

Josh dealt the cards, but he was clearly distracted. I looked at my cards, I had an 8, Queen, King, Ace of Hearts, and Four of Clubs. That’s fine if I don’t pick anything good, or I can discard these four and hope someone else deals Josh a Heart. Or, if I’m really brave, I can avoid the 8 and hope to get the Jack of Hearts and the 10, making a royal flush.

I threw in my only Mr. Boss to show I was in, and everyone else threw in other items. No one picked up, so I folded the four of clubs and waited for my hand, deciding to be cautious and not go for a royal flush. Josh handed it to me, and my hand hovered over the red and white blanket for a moment. Any hearts, I want any hearts.

My chest heaved as I peered around the corner and tried hard not to make a sound. It’s three hearts that make me blush. If I could, I would have bet bigger – in fact, Ricky raised the bet to two snacks, and Alanna and Josh called, though that forced Josh to bet as well. Beth folded quickly, trying to preserve her dwindling stock, and all eyes were on Marlena, who had just one snack left. She hummed for a long time and looked suspiciously at Alanna and Ricky. “Go for it,” she said, holding out the last bag of chips.

“That’s for a bet,” Josh said, flipping his cards over. “Two pairs, beat him.”

Alana and Ricky both laughed and threw down their cards, and I smiled triumphantly, “My heart is red. The pot is mine.”

“What the heck!” Marlena cheered, flipping her cards dramatically. “Four identical bitches, I win.”

“Fuck you,” I said, laughing at her antics. Marlena is usually quiet and dignified, but feels more comfortable alone with friends and roommates than at parties. I like this side of her, even if it means I’ll fail. It’s a bit like Alana.

“Oh, talk about rain,” he laughed, pouring his winnings over his head and placing them in his lap. “Okay guys. Who wants to be in the game?”

Josh and I hadn’t had any breakfast, and given Marlena’s enthusiasm, I had a feeling we’d have to pay to have fun.

“What do you want?” I asked, a little cautiously.

“I’ll give you each…umm…three snacks. But I want your pants!”

The other girls cheered and I looked at Josh on the other side of the circle and he shrugged at me. We both stood up and I started to unbutton my shorts and she did the same.

“Wait, wait,” Alana said. “Everyone finish your drinks before we start.”

“Why?” Ricky asked.

“Just trust me and do it.”

Josh and I sat down again and we all finished our drinks, some of us taking deep breaths to avoid feeling dizzy. We had been drinking since we started eating lunch late and maybe we all deserved a break, if not more.

“Well, that’s what I thought,” Alana said. “We’re headed in that direction anyway, so let’s play strip poker.” The rest of us went quiet for a while at her suggestion. “The way I think about it, we say no more folding. The worst cards have to take some.”

“What does the winner get?” Marlena asked, but Beth quickly followed up.

“What happens when you’re naked, are you outside?”

“I don’t know,” Alana said. “If the losers were naked, would the winners have the courage to let them do something?”

“I like it,” Marlena said, smiling, clearly enjoying her drunken state.

“Here we go,” Beth said, “Fuck it, I’m halfway there.”

Ricky just smiled and nodded.

Josh and I looked at each other again. It is said that women can communicate silently, or they can be spouses, or they can be best friends. Alana and I sometimes have some silent conversations, but it is usually more about understanding each other’s thoughts. Girls don’t understand how brothers communicate silently. Josh and I looked at each other and had the entire conversation without so much as a twitch of an eyebrow.

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