Pushing Boundaries

Both of us stood up and sort of awkwardly waited for Beth to feel like she was ready. Eventually she stood up with us and put a hand on each of our dicks, squeezing lightly as she nervously played with her lip ring. She silently moved her hands to our shoulders and Josh and I quickly figured out how to lift her up, him holding her under her armpits and me first by her hips, then supporting her under her knees as she lowered, legs splitting out on either side of us.

"Hold on," I said, looking down her back to the ass in front of me. I'd just spent fifteen minutes easing Malena into receiving a buttplug and now it looked like I was going to fuck Beth the same way in a fraction of the time. "I'm gonna need some lube."

"Yes please," Beth said quickly.

Malena grabbed the bottle, "Ricki, why don't you make sure Josh is good and hard? I'll get Austin ready."

Both girls got on their knees in front of us, Beth hanging over them, and then Malena was blowing me. I wanted that condom off immediately, wanted to feel her lips on my shaft and her tongue playing along my head, but it wasn't to be. The sensations were there it just didn't feel like it should. Soon she stopped and spurted a large dollop of lube onto her hand, quickly rubbing it all over my cock and then slowly jerking me, looking up into my eyes, until Ricki coughed lightly and said, "I think he's ready."

"I think the important thing is if Beth is ready," I said. This might have been a game and the girls were getting competitive, but I wasn't about to force Beth into anything she didn't want.

"Just, Josh you put it in first, ok?" She asked. "Then Austin. I've done anal before just, uh, not like this."

He nodded, and out of my view must have entered her with a bit of navigation help from Ricki. Beth shuddered and her ass bumped back into me as Josh thrust a few times. After about twenty seconds Beth turned her face to me, a pleading look in her eye, "Go slow please?"

I kissed her cheek and said, "Of course." Malena was still kneeling below us and took my dick in her hand, maneuvering until I was pointed to the right spot. I could feel warmth through the condom, but all of the texture had disappeared. I pressed more firmly and felt something giving way and Beth took in a deep breath. "Ricki," I said, "Rub Beth's clit while I get in."

She didn't respond but Beth sucked in another breath. I pushed again and the copious amount of lube Malena had doused my dick with did it's work, allowing my head to pop into Beth's ass when she relaxed. She grunted and tensed so I froze, her sphincter clamping firmly less than an inch down my shaft. She shook for a moment and I was worried I had really hurt her, but then she took a deep breath and her body relaxed.

"Fuck," she groaned. "This feels so weird."

"Tell me about it," Malena mumbled.

"Okokok, umm, I think I can take more," Beth groaned, and in response I pushed in another couple of inches. "Whoooaa," she said, lifting herself up and away a bit with her arms on Josh's shoulders, "Okok, hold on, let me just-" She lowered herself down, impaling both her holes on Josh and I until she had taken me to the root. "Fuuuuuuuuuckk," she moaned in her throat.

Josh and I stood there awkwardly. Beth had her head thrown back, resting on my shoulder as she looked at the ceiling, which left us guys almost eye to eye. The fact that we happened to also be sack-to-sack, his pubic hair brushing against me, and that we could feel each other through Beth's interior walls had us both looking away quickly.

"Well, you've officially been DP'd," I said in Beth's ear, my lips brushing some of her piercings.

"It's- I don't even know how to describe it," She moaned, shifting her hips and moving both of us inside her, clenching her ass around my shaft. "I'm so... full."

She shifted again, raising herself a bit, and then letting herself settle. I took the initiative and used her legs to lift her up, higher than she had herself, and dropped her back down. Josh started helping as we lifted and dropped her on our cocks, the condom taking away some of the sensations but still stimulating me like crazy, her ass trying to grab hold of me but the lube doing it's work.

Beth started moaning more, her mouth hanging open, and leaned her back against my chest. Josh bent his head and caught one of her pierced nipples in his mouth, the up and down motion tugging it away from him over and over. He released her and Beth leaned forward, pulling his face to hers as they started to kiss. The up and down movement stopped as she thrust her hips towards Josh a few times, taking him deeper, and I met the backswing by thrusting at her firmly enough that her ass slapped against my pelvic bone. She was moaning into Josh's mouth now as we practically played ping pong with her, each of us counter-thrusting as her hips slapped back and forth between us.

"Fuuuyuuuuuuuck," Beth cried out.

"Oh damn, I'm gonna come," Josh said, and I realized that he hadn't actually gotten any relief yet through the whole game. His stamina so far amazed me; I'd already gotten off once and was feeling the effects of Beth's tight asshole acutely.

"I'm gonna come, fuck I'm gonna come," he kept saying, and then Beth tensed up and stopped moving her hips as her moans turned into a silent scream, her mouth pressed to Josh's. He grunted several times and I had the unfortunate experience of learning exactly what my friend's vinegar strokes looked like.

I stayed completely still, and as soon as Beth loosened up Josh stumbled back with a slick slurp as he disengaged from her. I was now holding Beth up alone, and despite the fact that she was a smaller girl and the smallest of all our roommates, I was starting to get tired. I carefully lifted her, her ass dragging along my cock as if it didn't want to let go, until I felt myself released and my dick bounced down and up, smacking her butt cheek wetly.

Ricki met me halfway and helped me ease Beth down to the ground, where she rolled over and took a deep breath, her chest rising and falling. Josh had left a hickey on her tit and I had to admit it looked sexy, reminding me of the one I had left on Alanna our first time together. "Mmmwow," Beth groaned, reaching down and rubbing at her pussy lightly, then moving between her legs and probing at her ass. "That was intense."

"Did you like it?" Malena asked.

Beth smiled lazily, "I mean, yeah. I didn't know if I would, but yeah. I'll still get you back though."

We gave Beth a minute to collect herself, Alanna going to the kitchen and bringing back water for everyone to hydrate. Josh was back with us shortly, recovering from his own intense orgasm, full condom disposed of.

"You guys ready?" Ricki asked both of them, and they nodded. "What are you waiting for then?"

Cards. Alanna won, I wasn't even sure what she had. All I knew was that I didn't lose, Ricki and Josh gaining that honor.

"I think we need an easy one," Alanna said. "Ricki, I dare you to get Josh hard again."

"My pleasure," she grinned, "Or, well, his pleasure."

Ricki quickly had Josh lying back, her ass in the air as she knelt beside him and took his deflated dick into her mouth. "Mm, salty," she commented, tasting the residue of his last orgasm as she started working him over.

Malena was sitting closer to me than before and her hand settled on my leg, fingers brushing back and forth as she watched Ricki for a moment.

"Hey," I said quietly, getting her attention. "How's the butt?"

She flashed me an embarrassed smile, "It's actually ok. Sort of like what Beth said, I feel really full. I kind of like it though, it's different and I feel really dirty." She glanced at the others, who were watching Ricki except that I could tell Alanna was only pretending and was actually listening in on our conversation. "Not as dirty as when you were tonguing my ass though. That was just all kinds of wow. Thank you for being so amazing for me."

Malena tilted her head to mine and kissed me on the lips, not with the heated wild passion like we had out in the rain over an hour ago now, but lightly and lingering. I would have said lovingly, if it weren't for the fact that her hand had moved from my leg to my cock, stroking it a few times before she separated from me.

"Done," Ricki said, sitting up, and she was. Josh was hard again, standing up like a flagpole. "Next hand, I hope I lose again." We all laughed, but quickly got pack to our spots as Josh got the cards.

"Ooh, karma strikes again," Ricki said as she turned over her winning hand. I hadn't lost, but Josh and Alanna had, and now I was in something of an emotional pickle. Alanna was more than ok with the fact that I was getting to experience other girls, especially since she was watching and getting to do the same. But with the way the dares had been going, and with her and Josh, that meant his dick was involved.

How far was I willing to go for the game, and our secret? Alanna had declared to me she didn't want to fuck any other guys, but did that include this game? Where was the line? Handjob or blowjob? I didn't like the thought of either of them. Fuck, I didn't even like Josh getting to feel up Malena earlier and we aren't even in a relationship.

Ricki was grinning, "Things get interesting now. Lot's of people's firsts getting popped, so what about one more? Alanna, I dare you to let Josh fuck you."

Josh was clearly alright with this. Alanna took in a breath and looked around the room. Her eyes lingered on mine and for the first time through the whole game she blushed. "Umm, so... and Josh this is no way meant to be an offense to you... but if I'm going to have my first time with a guy, I'd really rather it be with Austin, since he's always been my best friend."

"Awww," Beth, Ricki and Malena all said.

Josh sighed and shrugged, "I guess that's alright. Virgin."

Alanna chuckled weakly at his tease then turned to me, "Is that ok Austin?" Two weeks ago I probably would have came in my pants, or rather in the open air since I was currently pantsless. Now, my heart was beating in my chest with a huge force because I knew Alanna was leveraging our sneaking around to keep herself just for me. We'd only said it that morning, but she was proving over and over again how much she loved me. I wanted to go to her and kiss her and tell her over and over again how much I loved and appreciated her.

Instead I had to keep up the lie. "Ye-yeah," I stuttered, trying to act as surprised and happy as I could. "I'd love to."

"Of course he would," Beth giggled, "Everyone knows-"

"Shutup," Ricki told her.

Alanna looked over questioningly at the two, but I knew Beth was about to say 'Everyone knows Austin is in love with Alanna.' Before we'd gotten together it had been true, I'd been in love with my best friend practically since middle school and most people we knew and were friends with had been aware of it. I'd always been Austin, the guy in the friendzone with that crazy lesbian girl. The only person who hadn't been aware of it was Alanna, who'd admitted to me she'd loved me for just as long, she just hadn't known how to make a move. Until the night she threw herself at me, we'd both been total morons when it came to our feelings for each other.

"I'm fine with changing the dare, but you change something so I change something, ok?" Ricki continued, trying to be a good friend to me and not 'reveal' the secret.

"Ok," Alanna said hesitantly.

"You get to change the person to Austin, but you have to take him front and back. Austin gets both your dude-cherries."

"I'm ok with that," Alanna said, then smiled and reached out and took my hand, "That ok with you?"

"Um," I said, blinking, "Absolutely."

"Well, get to it," Ricki said, making a shushing gesture.

"Before we, uh- I want to do something," Alanna said, getting up on her knees and shuffling closer to me. She bent her head to mine and kissed me lightly, then more firmly, her tongue exploring my lips and then my mouth and I met hers with mine. It's funny, even though almost every private moment we had spent together since we hooked up had been spent holding and kissing each other - if we weren't full on having sex - pretending that this was our first kiss put a thrill through me. It all felt new, doing it in front of other people, the purposefully tentative way we did it.

The kiss ended and she pulled back an inch, looking into my eyes for a long moment, passing me the silent message, I love you. She turned to the others, blushing again, and Ricki clapped her hands excitedly.

"That was so cute," the brunette said, and Beth sighed happily, nodding her agreement.

I glanced at Malena, who was sitting on her knees with her hands folded in her lap. She smiled when I looked at her, but she had an oddly distant look in her eyes, like she'd been thinking of something else.

Alanna took my hand and led me over to the couch, letting go to lay down on it lengthwise and spreading her legs so that one was hooked on the top of the headrest and the other was on the floor. She was totally opened for me and gave me a hungry look. "Well," she asked, false-nervousness in her voice, "Do you want... do you like this?"

"You look beautiful," I said, kneeling on the couch in between her legs. "And delicious, and sexy as hell." I bent at the waist and started to eat her out, feeling like I was returning home. I knew what she liked and I gave it to her, prodding with firm lips and dipping my tongue into her before I pushed her clit firmly with it. She moaned and I moved up from her pussy, kissing her bald pubic mound and then nuzzling the light blonde hair on her lower abdomen, the thin golden treasure trail there as sexy as I had ever thought it was. I kissed up her fit, taut stomach to her breasts, which I teased quickly with kisses and a nibble on one nipple, then up her chest and across her collarbone until I was face to face with her. I kissed her lips, tasting her again, and her mouth followed mine a fraction as I went to pull away..

"Ready?" I asked, as if this was our first time.

"Yeah," she breathed.

"I need a condom," I said, turning to Ricki, but Alanna grabbed my head and pulled me back into a kiss.

"No, if we're doing this, I want to feel you perfectly. I'm safe."

I heard another 'Awww,' from someone, though I couldn't say who it was. I entered her slowly, her body accepting mine quickly as if our genitals knew exactly who each other were and how to match. Alanna's breath got shallow and her chest pressed up against mine as I thrust a few times, slowly and as gracefully as I could manage.

"How's it feel?" Ricki asked from nearby. "Better than a dildo?"

"Yeah, but not 'cause it's a dick," Alanna breathed out. "Because it's him." She sighed a soft laugh. "I'll admit the warmth inside is nice though, that's one thing they haven't tried giving a vibrator yet; lifelike warmth."

Alanna and I fucked for another couple of minutes, our rhythm falling into sync quickly. I didn't push any of her usual buttons, didn't tweak her nipples or fuck her hard or restrain her in some way. She liked a hand pressing on her chest, or loosely gripping her throat, if we weren't using her bondage kit. This wasn't the time though, not while we were putting on an innocent 'first time together' show.

Eventually she kissed me and whispered we should try the 'other thing.' I pulled out and backed off of her, watching as her now vacant pussy slowly closed as if it was expecting me back at any moment. She flipped over and raised herself up on her knees. "I think we'll need the lube," she said, and Beth quickly handed it to me. Alanna rested her head on the sofa cushion, reaching back with both hands to spread her ass open for me, giving me even more of an opening by putting one leg on the ground next to the couch and widening her stance.

"Lube away," she said, and sighed as I spurted a glob onto her asshole. "I'm not going to need as much working over as Malena did, so don't be shy." I soon had my middle finger buried to the knuckle in her ass and added a second, working them back and forth. While I did this, Malena stepped forward and took the bottle from me. "I'll get you ready," she said, and started giving me a lubricated handjob just as she had before I fucked Beth. She was standing next to me as I knelt on the couch, her breasts at head level and waving back and forth, nipples hard and areolas puffed with excitement. This time I didn't suppress my urges and leaned my neck forward, catching the closer one in my mouth and suckling on it lightly for a moment.

"Mmm," Malena moaned lightly in her chest, but Ricki quickly called out Malena wasn't supposed to be part of the dare.

"No more touchy-touchy you two, Austin's ready to go." Malena stopped stroking my shaft, her fingers tracing my length as they left me, but she didn't move from her position next to us.

I leaned down and kissed Alanna on the small of her back as I withdrew my fingers from her. "You think you're ready?" I asked.

"I've taken dildo's up there before," Alanna said, "Let's see if this is different with you, too."

I adjusted my stance and put the head of my dick at Alanna's slightly open hole. It didn't take much effort to slide in, though she instinctively clenched up a couple of times before forcing herself to relax. I stroked about half my length into her for a little bit before I started pushing farther, Alanna grunting girlish little noises as I began to edge my entire length into her.

"That's everything," I said, her ass pressed tightly against my hips and legs.

"It's good," Alanna groaned. "Fuck me?"

I pulled back and stroked in fully, then again. "Mmmm," she groaned, "Yeah, this is definitely better with a real dick."

This made me smile and pump her a little harder. One of the reasons we hadn't done full on anal yet was because all of her past experiences with one girlfriend or another had been mediocre at best. One chick, during our first year in university, had gone so far as to try and stick a vibrator up Alanna's ass dry. That relationship had not ended well.

I started building up a rhythm as I thrust into her ass, using my hands to spread her cheeks wide so that I could watch my dick disappear into her back door, her tight ring spreading around my cock reminding me off a porn video. She started moaning more and I could feel her fingers brushing against my shaft and balls as she played with her pussy while I reamed her. I stopped spreading her and instead pushed her cheeks together, which shortened my stroke as I ran into her firm ass almost three inches earlier but gave me another great view as her butt cleavage swallowed me up. One of my favourite little quirks about Alanna that I've discovered is that her ass, while in panties or when pressed together, had a sexy little cleavage v at the top of her crack.

I was just starting to pick up the pace into a more forceful fucking when Ricki cleared her throat, causing both Alanna and I to turn to her. "So, are either of you close to coming?"

"Uhm," Alanna said, "I mean if we keep going I'm pretty sure I will."

"I'm sort of close?" I said.

"Ok, I think the dare is done then. You two have been fucking for like almost twenty minutes, and you're super hot and all but fuck I want some dick."

I stroked Alanna two more times, then slowly disengaged. Her ass winked back at me, closing in stages as the muscles tried to return to normal. I slipped backwards onto the far seat of the couch and Alanna rolled onto her side. "Cockblocker," she sighed to Ricki, who just shook her head and laughed.

Alanna and I were the last to get to our spots, she holding onto my hand for a lingering moment, fingers intertwined.

Cards. I was feeling extremely heady, whether it was the booze we had been drinking or just my natural reaction to fucking Alanna I'm not sure. It didn't matter how much attention I was paying though because I had a pair in hand.