The Roommate Challenge

I walked into the apartment and heard unmistakable sex noises coming from the room of our roommate, Leah. There was loud moaning and grunting, and the bed rhythmically slamming against the wall.

OK, I should start from the beginning.

Early in my relationship with my girlfriend, Lauren, we had a two-bedroom apartment downtown. The second room was mostly unused until Lauren's friend Stacy had mentioned that her best friend, Leah, was starting law school nearby and needed a place to live.

Neither of us knew Leah very well. I knew she was smokin' hot — 6 feet tall and skinny but fit, since she had been an athlete in college. She had long, straight, golden-brown hair that framed a gorgeous face with smooth, olive skin. She literally could have been a runway model. She rarely showed off her boobs, to the point that I assumed they were small, but I had overheard some "girl talk" one day and it turned out she had D-cups.

The living arrangement had been great so far. Leah turned out to be a lot of fun — she actually became one of my favorite friends of Lauren's. And let's just say I didn't mind when she walked around in a towel after showering; she had no reservations about walking around the apartment with her smooth shoulders and amazingly long legs exposed. I always prayed that the towel would slip just once, but it never happened.

Anyway, on the day in question, a Wednesday, I had gotten out of work a few hours earlier than usual. Lauren and I both had regular 9-to-5 jobs, but Leah was home most of the time, usually studying.

When I heard the sex noises, I decided to give Leah — and whoever the lucky bastard was — some privacy. I shut the door quietly and placed my briefcase on the counter, figuring I'd just go run some errands. As I turned to walk away, though, something caught my eye. It was a money clip sitting on the counter — and the face staring back at my from the ID on top was John, Stacy's fiancé.

I froze for a second, subconsciously not wanting to put two and two together. But it was unmistakable. The guy in there screwing Leah's brains out — her moans were getting louder and louder — was her best friend's fiancé.

Lauren would never believe this. That's the only reason I can think of to explain what I did next: I picked up Joe's money clip, walked quietly to Leah's door, and pulled out my iPhone. Turning on the camera and setting it to video, I pressed record and held up Joe's ID next to the "Leah" sign on her door. I kept it recording for about 20 seconds, and like clockwork, toward the end Leah said, "Fuck me harder," and John answered, "You mean like this? You like that?"

Satisfied, I turned off the camera and silently left the apartment. I called Lauren as soon as I got down to the street, but she didn't pick up. That was one of the best things that ever happened to me.

I started to text Lauren about what I had witnessed, but I stopped just before hitting "send." Was there something better that I could do with this video than just showing my girlfriend and probably having her tell her friends? This would be juicy gossip, but what if I could take another route? Suddenly, I had an idea.

I walked around for about an hour before heading back home. I walked into the apartment around 4 p.m., still well before Lauren was going to get home.

Leah was sitting on the couch, highlighter in hand as she read a giant book. She looked up and gave me a casual "Hey," but I was pretty sure I could sense some nervousness.

I went into the bathroom, took a leak, came back out and grabbed a beer from the fridge. I sat down next to Leah on the couch and turned the TV on.

We were both silent for a few minutes before Leah spoke up. "I saw your briefcase on the counter," she said, her face turning slightly red. "Did you stop in here while I was in my room?"

What a loaded question. I smiled.

"Yes, yes, I did," I said, laughing slightly.

"Oh, my gosh," Leah said, her face now bright red. "I'm guessing you heard ... things. That's so embarrassing. I didn't expect you home till later."

"Yeah," I said. "My boss let us leave a little early today. ... So who was he?"

"Oh, just some guy from law school," Leah said, thinking I was just trying to razz her a little bit.

I paused, thinking about whether I really wanted to do this. As I looked at Leah's long, perfectly tanned and smooth legs up on the coffee table, I decided I did.

"Oh. I didn't know John was in law school," I said. That was a dagger.

A frightened look came over Leah's beautiful face.

"How did you know?" she said.

"Well," I said, "I recognized his voice, but there was also his ID sitting out on the counter."

With that, I took out my phone and called up the video. Leah watched in horror.

"You can't show that to Stacy," she said. "Please, please, please. Stacy would never talk to me again. We've only done this a few times, and I promise I'll end it. Fuck, why did you even take that video? I thought we were friends."

"We are friends," I said. "And I didn't take this video to show to Stacy. I mean, I sort of did, but I hope I don't have to. I hope no one else ever has to see it."

I let my words sink in. After a few seconds, Leah realized what I was getting at.

"What do you want me to do?" she said, her shoulders slumping. "Your laundry? Dishes? Clean the bathroom every time it's your turn?"

I could tell she was hoping that was all I wanted, but that she knew it was going to be more than that.

I chose my words carefully.

"Leah, you're gorgeous. Any guy with a pulse would want to fuck you," I said. "But unlike John apparently, I love Lauren."

I saw relief flash across her face. It wouldn't last long, though.

"So what you're going to do is figure out a way to get Lauren to do a three-way," I said. "I don't care how you do it. But she can't know that this was my idea. You make it happen within a month, and I delete the video from both my phone and from the cloud server where I uploaded it."

Leah looked annoyed now.

"And if I can't?" she said. "Lauren is a fucking prude. She won't go for that."

"That's not my problem," I said, feeling a little bit like a dick, but not backing down. "If you can't make it happen, then one month from today I will show that video to Stacy."

There was no way I was going to do that. One of my biggest weaknesses is that I'm not a big enough asshole. If Leah failed at what I had told her to do, then I'd probably just delete the video and call it a day. But it was worth a shot.

"You're a dick," Leah said.

I smiled at her sadly. "Leah, like I said, I don't want to show Stacy the video," I said. "Try to have some fun with this."

"Whatever," she said. She looked back at her book, but I could tell she wasn't studying. We didn't say a word to each other the rest of the night.

*****

The next night, I went out for some drinks with friends after work. When I got home, Leah and Lauren were sitting on the couch, watching a movie. Leah had put on "Wild Things" on demand.

I laughed to myself and gave her a look that said, "Really?" It was toward the end, which was unfortunate. I had missed the part when Denise Richards and Neve Campbell fuck Matt Dillon. I would have loved to have heard whatever smooth line Leah came up with to try to lay groundwork with Lauren.

Sure enough, later that night, when we were in bed, Lauren said, "If you could have a three-some, who would it be with?"

"Hmm," I said. "Let's see ... Mila Kunis and Kristen Bell."

That earned a hard punch to my shoulder. I laughed.

"OK, if I have to include you —" another punch as I kept laughing — "I guess I'd say you and Kristen Bell," I said.

I did have a thing for blondes. And I knew better than to risk mentioning Leah or any of Lauren's friends, which surely would lead to, "Oh, so you have a thing for her?" In fact, Lauren sometimes was told that she looked like Kristen Bell, so I hoped she'd take it as a compliment.

When she didn't answer, I said, "Why do you ask?"

"Oh, we were watching that movie earlier, and there was a three-way scene," she said. I laughed inwardly at her ignorance to the fact that every male on the planet knows that scene.

"Leah asked who I would pick if I were to have a three-way," Lauren continued. "It was a little weird, but I kind of just laughed it off and said I'd pick Denise Richards because she seemed to know what she was doing."

"Did Leah say who she would pick?" I said, trying not to seem to anxious.

"She said Stacy and John," Lauren said with a giggle. "She said Stacy told her John has a big one. So I told her I bet yours is bigger."

I smiled. Well played, Leah.

With that, Lauren stuck her hand in my boxer-briefs and started stroking my thick, 8-inch cock. I leaned in to kiss her, and a few minutes later we were fucking. I thought about Leah the whole time.

*****

We didn't see much of Leah over the weekend, and things got pretty busy for me at work the next week. I had pretty much pushed the "challenge" to the back of my mind. Subconsciously, I think I figured there was no chance it would happen, and that I'd end up just deleting the video.

The following Friday night, there wasn't much going on so the three of us grabbed some drinks at the bar down the street.

It was a pretty normal night. As is usually the case when we grab "a few drinks," the girls were getting a bit tipsier than me, since they were drinking wine and I was drinking beer.

When we got back to the apartment, I had a pretty good buzz on, and the girls were slightly drunk — though not sloppy.

I grabbed a beer and opened a bottle of wine for the girls as Lauren headed for the bathroom. Leah looked at me nervously and bit her lip but didn't say anything. Was she going to try something tonight?

I got my answer a few minutes later. As the girls drank wine and laughed, Leah suddenly said to me, "So, Ryan, Lauren says you have a bigger dick than John."

"Leah!" Lauren said, slapping her on the shoulder playfully.

"I don't know," I said, playing it cool. "How do you know how big John's dick is?"

Leah froze. Luckily, though, Lauren didn't see it.

"Stacy told her, you big dummy," Lauren said.

Leah nodded, relief washing over her face.

"Yeah, Stacy said John's is 7 and a half inches long, and as thick as a D battery," she said.

"Ryan's is bigger," Lauren said, falling onto the couch laughing.

"I don't believe you," Leah said, baiting my girlfriend.

Lauren sat up and thought about it for a moment.

"Ry, just pull your pants down and let her see through your boxers," Lauren said.

I pretended to hesitate but then obeyed, unbuttoning my jeans and pulling them down to my knees.

"This isn't fair, though," I said. "I'm not at ... full strength."

Lauren knew immediately what I was talking about. My flaccid dick was unimpressive, to say the least, through my boxer-briefs. I'm one of those guys whose dicks grow to about twice their size when I get hard.

"Fuck. OK, we can deal with this," Lauren said, slurring her words slightly. She reached over and grabbed my dick through the boxer-briefs. I immediately felt myself start to harden. As Lauren started rubbing my dick, I looked at Leah. But her eyes were transfixed on my quickly hardening dick.

After only about 20 seconds, I was at full mast. Lauren moved my dick to the side, pressing it against my leg, and stretched the boxer-briefs tight, to the point that Leah could see every vein in my rock-hard cock.

"Still think John's is bigger?" Lauren said, challenging Leah.

Leah's eyes were still locked on my cock. "No. I'll admit, that's thick. And you weren't lying about it being 8 inches," she said.

Lauren smiled, satisfied, and reached out to grab my dick again.

"Still want to have a three-way with Stacy and John?" she said.

Leah smiled. "OK. No. I'd pick you two if I were going to have a three-way. But I'm not going to. You wish," she said and turned to go pour another glass of wine.

Maybe it was wishful thinking, but I could have sworn I saw a hint of disappointment in Lauren's expression. After a few seconds, she said, "Well, obviously, neither am I."

Lauren let go of my cock then and walked into the kitchen to refill her glass, too. I stood there, not moving, until Leah said, "Hey, Ryan, are you going to put that monster away?"

I guess so, I thought to myself. I guess we're slow-playing this. Dammit.

Nobody said another word that night about three-ways or my dick. We ended up getting nice and drunk, having a fun time. We went to bed, and I fucked Lauren until we both came. Again, I thought about Leah.

*****

The next morning, I decided to help Leah along a bit with a risky maneuver.

On weekends, Lauren and I usually fooled around in the morning before getting out of bed, and this Saturday morning was no different. After a short makeout session, I kissed her neck and her collarbone for a bit and then spent some time on her nipples. Then I kissed my way down to her pussy, which was already soaking wet.

After a minute or so of teasing her by breathing on her pussy but just kissing her inner thighs, I finally used my fingers to spread her little pink lips and licked slowly up the length of her pussy.

Lauren writhed in pleasure as I continued licking, going up and down and occasionally getting my tongue as deep into her as I could go, but not yet touching her clit.

Finally, I made my move and just barely touched her swollen bud with my tongue. Then I pulled back.

Looking up at my beautiful girlfriend — who shot me a look as if to say "Why the fuck did you stop?" — I whispered, "I think Leah wishes this was her tongue doing this."

It was a risk. Lauren had never shown any lesbian inclination. In fact, she always acted grossed out by the idea. My comment could totally kill the mood.

But it didn't.

Lauren laughed quietly and just said, "Shut up." Then she closed her eyes and squeezed my midsection with her legs, urging me to return my face to her honey pot.

Mission accomplished. Whether she would admit it or not, she was going to be thinking about Leah while I brought her to orgasm with my tongue.

I licked up and down her inner lips a bit more, flicking her clit a few times. Finally, I stuck a finger in her sopping wet hole and focused my tongue entirely on her clit. I wrapped my lips around it and flicked with my tongue while sucking on it, all the while fingering her furiously.

Within less than a minute, Lauren was pulling my hair and moaning in ecstasy as she came. I kept my mouth on her clit until she was done and then let go and looked up. She was laying there, eyes closed, with a satisfied smile on her face.

As I got up and walked to the shower, the smile on my face might have been even bigger.

*****

For the rest of that week, I decided the best thing I could do was just make sure to let Lauren know how much I loved her. Leah could take care of getting her sexually interested in a three-way; I wanted to make sure that once she was interested, she was emotionally OK with it. I didn't want her to be afraid of me having a romantic interest in Leah.

I told her I loved her a bit more than usual, and we fucked every night that week. I made sure to be extra attentive to her needs.

Still, Leah had a tall task ahead of her.

*****

The following Saturday morning — two and a half weeks into Leah's challenge — I went out to run some errands.

Later, Lauren and I grabbed a late lunch at a little outdoor café around the corner. As we waited for our food, I learned that Leah had upped the ante.

"So, funny story. This morning, when you went out," Lauren started, "I guess Leah thought I had gone out with you. I was still in bed when she got in the shower, but sound of the water woke me up, so I went to make a pot of coffee."

I liked where this was going.

"Anyway, I guess Leah had bought a new razor and left it in her room," she continued. "And since she thought no one was home, she didn't bother covering up with a towel when she got out of the shower and went to grab the razor. She came out of the bathroom buck naked, dripping water. She saw me, and I swear it was like that scene in 'Something's Gotta Give,' when Diane Keaton gets caught naked and freaks out. Leah screamed and tried to cover up, but let me tell you, she wasn't lying about those D-cups, and those puppies were not going to be covered up with just one arm!"

Lauren was laughing by now. If it had been me in her place, I probably would've been too mesmerized by Leah's naked body to see the humor in it, but Lauren got a kick out of it. And while I would have bet my left nut that Leah pulled the stunt on purpose, Lauren apparently had no idea.

"So what happened then," I said, trying to sound like I just wanted to hear the rest of the funny story — and trying not to drool.

Lauren, still laughing, continued: "She stood there for a few seconds trying to cover up and trying to explain that she thought no one was home, but then we both burst out laughing, and she just ran into her room, grabbed her razor and ran back into the bathroom. It was freakin' hilarious."

"That is funny," I said, deciding to leave it at that.

Our food came pretty soon after that, and we dug in. I had a bacon cheeseburger, and Lauren had a chicken Caesar wrap.

As we finished up, Lauren surprised me.

"You know, if I were to ever go lesbo, it would be with someone who has a body like Leah's," she said casually.

"Whoa," I said, smiling. "Do I have anything to be worried about? Maybe I should stop leaving the two of you home alone."

"Shut up," Lauren said, embarrassed. "You know what I mean. I'm not a lesbo. I was just saying, if I were to ever ... experiment ... well, I've never been turned on by a girl before, but Leah is fucking hot."

"Well, yeah," I said. "She's a good-looking chick."

"No, Ry," Lauren said. "I'm telling you, if you could've seen it ... her skin is just flawless, all over. She has no tan lines. And with the water dripping down her ... and her butt is perfect, her boobs are perfect ... I'm jealous of her. Any human being, gay or straight, would have to admit she's just a perfect ... I don't know."

"Specimen?" I said.

"That's the word I was looking for," Lauren said, clapping her hands.

"Gotcha," I said.

We sat for about a minute in awkward silence after that, but then Lauren brought up something else and the Leah incident was forgotten.

*****

The next week was uneventful. Well, when it came to Leah, at least.

I made sure to give Lauren amazing sex every night, hoping somehow it made her more susceptible if and when Leah finally made her move.

Lauren didn't mention the shower incident again. But every time we had sex, I wondered if she was thinking about Leah. I certainly was.

*****

The next Friday night — three weeks and two days into the challenge — Lauren, Leah and I went out for drinks at the bar down the street. We did that a lot on Friday nights, since most of our friends only partied on Saturday nights.

We drank a lot, and the girls danced a little. Then we headed back up to the apartment to postgame.

We sat on the couch, Lauren sitting between Leah and me, and watched the end of the movie "10 Things I Hate About You" on HBO while the girls drank wine and I had some more beers. We were all drunk, but not ready to pass out.

Leah had the remote, and when the movie ended, she flipped through the TV guide.

"Goddamn, there's nothing on," she said.

Then she stopped at one of the other premium channels that we had — Cinemax or something. There was a softcore porno on, and there were two girls making out with a guy. I wondered if Leah had planned this — after all, it had been her who suggested we leave the bar a bit earlier than usual, and she had grabbed the remote right away when we got home. Had she checked the listings earlier?