My Girlfriend's Roommate

"Good idea, Lucas," she said, still giggling as Jake got in a few more tickles on her legs and sides.

I pushed my glasses up my nose and focused back on the work while Jake and Stephanie settled down, cuddling and watching the basketball game together.

When I finished, I looked back up at them, but when I did, my mouth fell open in shock. I noticed that a big tent had formed in Jake's boxers! I could only stare in awe for a second. Not only did he have an obvious erection, but it was huge! And they were both just sitting there like nothing was going on!

I saw Jake notice my gaze and he discretely brought a finger to his mouth to silently shush me as Stephanie continued watching TV, seemingly oblivious.

Again, my natural passivity toward guys like Jake kicked in, and I just nodded. Finally, Stephanie noticed me looking back at them and said, "Oh, um, are you done, Lucas?" She pushed herself off of Jake's body, seeming not to notice his massive hard-on.

"Uh, yeah," I said, watching as Jake adjusted himself, although his erection was so big, he couldn't really hide it.

"Thank you so much," Stephanie said to me. "Um, so, like, about our date..."

My ears perked up as she mentioned our date, and I focused back on her. "Oh, yeah, maybe I could, like, take you out to dinner this weekend? If you're free?" I asked.

"Sure, that sounds great," she said. "How about Belle at 8:00 on Saturday night?"

Belle was the fanciest restaurant in town. It was super expensive, but that was okay, I could afford it. "Great," I said, grinning. Jake's tented boxers vanished from my mind.

While Stephanie began packing her materials up, Jake made eye contact with me and motioned for us to move toward the door. "Hey, can I talk to you for a second?" he said softly. As we walked to the door, my eyes couldn't help but dart down to his crotch. His boxers weren't completely tented up anymore, but there was still a pretty big bulge there. In a soft voice, so Stephanie couldn't hear, he said, "Hey, I'm really sorry about that, man."

I felt super awkward and just stammered, "Oh, uh, it's, uh, okay."

"Listen," he said. "There's something you should know about Stephanie. She, um, doesn't have a lot of experience with guys, ya know what I mean? Like, she's never actually...ya know..."

My mouth fell open. "Really?" I said. "She's a...virgin? But she's so...uh..."

Jake nodded. "I know, a lot of guys assume because of the way she looks, and how she dresses, that she must be a total slut," he said. "But she's actually never done anything more than kiss a guy. Is that, like, okay with you? I know some guys might be weirded out by it, so if you are, you should tell her now and let her down easy. I'd hate to see her get hurt."

"Oh, uh, no, it's okay," I said quickly. "I, um, I actually don't have any, uh, experience either."

"Oh, really?" Jake asked. "That's actually really cool, that could make you two a really good fit."

"Um, yeah, I guess it might," I said, smiling a little.

"Well, anyway, I just wanted to tell you, so that you know she's, like, really innocent. That's why she doesn't seem to notice when I...ya know..." He motioned down at his crotch, referring to his erection.

"Oh...really?" I said awkwardly. "But it's...I mean...it's so...big."

He smirked a little. "Yeah, I know," he said. "But I guess she doesn't really know much about stuff like that, so she doesn't really notice when it, ya know, pops up."

"Oh...wow, okay," I said.

"But don't get the wrong idea," he said quickly. "It really doesn't mean anything. I'm just a red-blooded straight guy, I can't really help it when a girl like her is rubbing up on me like that, ya know? Even if she is just a close friend."

"Right, okay," I said, nodding and letting out a sigh of relief. I know how naive it sounds now, but at the time, I felt completely reassured to hear this explanation from him. "Thanks, man."

"Yeah, no problem," he said, slapping me on the back. "So, like, if you ever see me, ya know, like that again, just remember, it's no big deal, right?"

"Right, yeah, no big deal," I quickly agreed.

"Cool," Jake said, smiling at me. "You're the best, Lucas."

Just then, Stephanie interjected from across the room. "Are you two talking about me?" she asked.

"No, no!" Jake said, covering for us. "Just getting to know your new boyfriend over here, that's all."

He and Stephanie laughed at Jake's teasing. "Oh my god, Jake, you're the worst!" she said.

"No, but seriously, he seems like a really nice guy," Jake said.

I smiled. It felt good to be complimented by a guy like him. Stephanie walked over, and Jake gave us some space. She walked me to the door. "Um...so...see you on Saturday?" she asked shyly.

"Uh...yeah," I said, wondering if I should kiss her. She stood there expectantly, and I decided to go for it. I leaned toward her, and she leaned in to me, giving me a kiss on the lips!

It was a really quick kiss, more like a peck really. I thought to myself that Jake was right, she was really innocent and obviously wanted to go slow. But that was fine with me, given my lack of experience as well. Any kiss at all was amazing. "Um...good night," she said, smiling at me.

"Good night," I said, smiling back.

As soon as I left, I could hear the two of them laughing together. I smiled, thinking that she must be really excited to have landed a date with me!

Of course, when I got home, I closed my eyes and thought of her while I stroked myself. But this time, to my surprise, images of her running her fingers along Jake's abs would flash through my mind, along with the big tent in his boxers. It was a little weird, but I quickly squirted picturing them cuddling together as he got a big hard-on.

***

That Saturday, Stephanie and I went on our date to the fancy French restaurant. She wore a beautiful, sparkly blue dress that she looked incredible in. I was really nervous, but she seemed to have a good time. She laughed a lot at every little joke I made and seemed to be flirting with me a lot. I couldn't believe it, but it was true. I didn't even mind that she ordered all the most expensive items on the menu!

We briefly talked about Jake, just because I was kind of curious about him. "So you and Jake have known each other for a while?" I asked between the fourth and fifth courses.

"Oh, yeah, we grew up next door to each other," she said. "We've always been best friends. It was so great when we ended up going to the same college together so we could be roommates. He's the best, right?"

"Yeah, he seems like a really good guy," I said sincerely. "It's nice that after all this time, nothing's ever gotten in the way of your friendship."

Stephanie giggled. "Yeah. I mean, I used to think maybe he had a little crush on me. Even now, he sometimes gives me these funny little looks, especially if I'm wearing something, ya know, kinda revealing..."

I swallowed uncomfortably. "Oh, really?" I asked.

"Yeah," she said nonchalantly. Then she smiled mischievously and leaned in closer to me. "I mean, I don't think he realizes that I know, but sometimes when I cuddle with him, I can see his...ya know...his thing. Like, getting big and hard!"

My mouth fell open. I felt bad for Jake, knowing that he had told me his erections didn't mean anything serious. "Oh, uh...wow, you can?" was all I could say.

"Yeah," she said, nodding. "But that's not a big deal, right? That's just how boys are, isn't it?"

"Oh, yeah, I definitely don't think it means anything," I said confidently, wanting to reinforce what Jake had told me so that Stephanie wouldn't get the wrong idea.

"Yeah," she said. "It's really cool that it doesn't make you jealous or anything. You get that we're just close, right?"

"Yeah, totally," I said, nodding in agreement. I tried not to think about how I had even jerked off picturing them cuddling together as he got hard. "Um, what about your friend, Rachel? She's dating him, right? Does she mind?"

"Oh, not at all," Stephanie said. "She's really cool about it too. She doesn't mind at all that he gets excited like that around me."

"Oh, uh, cool," I said.

"She thinks it's funny that he thinks I don't notice," she continued. "I mean, it gets sooo big, there's no way I could miss it!"

"Um...uh...oh..." I said awkwardly.

She giggled a little, then narrowed her eyes at me. "It's okay, Lucas," she said. "You can be honest. You saw him getting big and hard when I was cuddling with him the last time you were over, didn't you?"

I felt myself turning bright red. "I...uh..." I said, trying to lie, but the look on my face must have already given me away.

"I knew it!" Stephanie said. "That's so sweet of you that you didn't say anything, though. I'm sure a lot of guys would get all angry and jealous about that kind of thing. But not you, right?"

"Right," I said, nodding.

"That's one of the things I like about you," she said, then reached over and took my hand.

I felt my mouth going dry at her touch. "Um, thanks," I said.

She giggled at my nervousness. After that, we moved on to other topics and had a great time together. After I paid the bill, I drove her back to her place, nervous about what I should do when we said good night. When we pulled up to her building, she was quiet and looked kind of nervous. "Lucas," she said, looking down in her lap. "Can I tell you something?"

"Of course," I said.

She looked up at me. "I, um...I'm a virgin," she said.

I was silently thanking Jake for telling me this so that I didn't look really surprised and make Stephanie feel bad. I just nodded comfortingly and said, "That's okay, Stephanie." Then I swallowed nervously and added, "Actually...I am too."

"What? Really?" she asked. "Wow, that's so surprising. I would think a guy like you would have been with lots of girls."

I smiled, amused that she didn't seem to realize that guys like me usually didn't end up with girls like her.

"Well," she said. "I just wanted to tell you, because I might not be ready to, like, go as fast as you would like."

I reached over and took Stephanie's hand in mine, then looked her in the eyes. "Stephanie, it's totally okay. I don't want you to feel pressured to do anything. We can go as slow as you want."

She smiled. "You're so sweet," she said. "So it would be okay if we just, like, kissed and that's it?"

"Of course," I said, overjoyed that she even wanted to kiss me.

"Okay," she said, looking at me expectantly.

"Oh," I said, realizing I should be making my move. I leaned in awkwardly and pressed my lips to hers. This kiss lasted a little longer than the one she gave me the other night, maybe five seconds. I didn't dare try to use my tongue or anything like that. I just pulled away and she smiled at me.

"Good night, Lucas," she said.

"Good night," I said.

I practically floated home, a smile on my face the whole time. When I got into my bed, I was quickly jerking off, and it only took me about thirty seconds for me to get off thinking about her. Yes, some images of her cuddling with Jake flashed through my mind, her wearing some skimpy outfit and rubbing his chest while he got a huge tent in his shorts and her smiling down at it. But I tried not to think too much of it.

***

That week, I went over to Stephanie's place again to help her with another essay. Stephanie greeted me at the door wearing just a big t-shirt that went down to her upper thigh. Again, I could see her nipples poking through the shirt, and I was pretty sure she was only wearing panties underneath. My mouth fell open a little as I looked her up and down.

She giggled at my reaction. "Oh, yeah, sometimes I like to get comfy and just wear one of Jake's t-shirts, ya know?"

"Oh, um, yeah, well, you look great," I said.

"Thanks!" she said. "Come on in!"

When I walked in, Jake was there on the couch, shirtless and in just a pair of mesh gym shorts. A girl was sitting with him. She was a very attractive black-haired beauty wearing sweatpants and a tank top, with no bra. They were cuddling on the couch together.

Stephanie welcomed me inside and introduced me. "Lucas, this is my friend, Rachel," she said. "Like I told you before, she's Jake's girlfriend. Rachel, this is Lucas."

"Hi, Lucas," Rachel said with a smile. "I've heard a lot about you. All such sweet things, of course."

"Oh, okay," I said awkwardly. "Um, nice to meet you, Rachel."

"Hey, buddy," Jake said to me, squeezing Rachel tightly in his arm.

"Hi, Jake," I said. Jake clearly felt completely comfortable sitting around the house without a shirt on, even with his girlfriend and his female roommate around. But I knew guys with bodies like his probably didn't think anything of it.

I sat down at the coffee table and looked up at Stephanie. "Ready to get to work?" I asked.

She looked down at me and scrunched her face up, which made her look so cute. "I think we know I'm not gonna understand it," she said. "Do you think you could just go ahead and do it for me again?'

I smiled. Even her ditziness was attractive to me. "Sure, no problem!" I said quickly.

She smiled and plopped down on the couch, on Jake's other side, casually curling up against him. Sure enough, when the oversized t-shirt that she had on crept up a little, I saw that she was wearing only a pair of pink cotton panties. I could hardly believe it, but the three of them were obviously very used to dressing like this around each other.

I watched Stephanie's hand move to Jake's chest. Jake casually slid his arm around her, and now both girls were cuddling up with him. I couldn't help but stare for a second.

Rachel must have noticed, because she quickly said, "Oh, don't worry, Lucas. I'm like you, I don't get jealous about Stephanie and Jake cuddling together. I know they're just friendly like that."

"Oh, yeah, don't worry, Rachel, I already told him," Stephanie said. "And he's super cool about it just like you. Right, Lucas?"

"Uh, yeah...no big deal," I said, still staring.

"Thanks, man," Jake said with a grin. "You're the best."

"Oh, um, no problem," I said, watching both girls rubbing his torso up and down. "Um, let me get to work."

"Yeah, you do that," Jake said.

I started writing Stephanie's essay as the three of them watched TV. It was another silly reality show, and the three of them kept giggling together at it, even at parts that weren't particularly funny. It was a little hard to focus, but I kept at it.

After a while, Jake put his feet up on the coffee table, right next to my face. I glanced up, distracted. "Sorry, buddy, is this okay?" Jake asked.

"Uh, yeah, it's fine," I said softly. I looked back at them, the three of them smiling down at me as they all cuddled together. Then I glanced down and saw a huge tent in Jake's shorts. He looked down at me and shrugged nonchalantly. I remembered how he had told me that if I saw him with another hard-on, that I shouldn't make a big deal out of it. I glanced over at Stephanie, who glanced from Jake's erection to Rachel, who smiled back at her. Then she smiled at me as she rubbed Jake's stomach, like we were all in on the joke. I'll admit, it was all a little weird to me, but I tried not to react too much. None of them seemed to think it was a big deal, so I turned back to Stephanie's essay.

"You have such a sweet boyfriend, Stephanie," Rachel said as I got back to work. "He's so nice to be writing papers for you."

"I know, right?" Stephanie said. "He's the best."

I couldn't help but break out into a grin. I forgot about Jake's massive erection and just basked in the glow of Stephanie's compliments.

They continued giggling behind me as they watched TV. Sometimes they were laughing even when it was just a commercial playing, but I didn't think anything of it. Finally, I finished the essay. "Okay, well, I'm done," I said.

I thought I saw some quick movements as I turned around, but I couldn't be sure. By the time I was facing them, they were all just looking down at me. Jake's shorts were still fully tented, and it seemed like he was breathing kind of heavily, even sweating a little.

"Thank you sooo much," Stephanie said quickly, then leaned down to give me a peck on the cheek.

I grinned and blushed, forgetting about Jake. Stephanie and I walk to the door. She looked at me kind of shyly, clearly a little embarrassed to be saying good night to me in front of Jake and Rachel. But she still leaned over and gave me a kiss on the lips, a couple seconds longer than the previous one she'd given me. When our lips parted, I could only grin at her stupidly. "Good night, honey," I said.

"Good night, sweetie," she said with a little giggle, and I left. As soon as the door closed behind me, I heard loud laughter. I smiled, thinking that they must be teasing Stephanie about our kiss. I drove home, got into bed, and quickly squirted a load into my hand, picturing both Stephanie and Rachel cuddling with a shirtless Jake and looking down at his big hard-on.

***

That weekend, Stephanie and I had another date. I took her out to a movie and another dinner. She asked me to get her lots of candy and popcorn at the movie, then wanted to go to another nice restaurant, but I was happy to treat her to all of it.

On the drive back, I was fully expecting just another kiss on the lips. The most I could have hoped for was a little bit of tongue. But when I drove her back and stopped in front of her building, she really surprised me. She looked nervous, but as we sat there in my car, she suddenly reached her hand over and put it on my thigh. "Um...Lucas?" she said hesitantly.

"Yeah?" I asked. I wasn't sure where this was going, but she was rubbing my leg, and I felt butterflies in my stomach.

"I, um...I think I'm ready to go a little further than a kiss this time," she said.

My mouth went dry. "Um...oh...really?" I asked. "Like...what?"

"Well," she said, biting her lower lip nervously. "I've never done this before, but...would it be okay for me to, like, try to give you a...handjob?"

I couldn't speak for a few seconds. Her hand rubbed my thigh a little higher, closer to my crotch, and I flinched away from her touch. This was way further than I'd ever gone with a girl. Shakily, I said, "Uh...well...yeah, okay."

She smiled at me. "Okay," she said, then reached over to unbutton and unzip my pants.

I could hardly believe this was happening, but just a few seconds later, she was pulling down my briefs. My penis was very hard from how excited I was, all 3 inches standing at full attention. She smiled down at it, hesitantly taking it in her hand.

"Oh, wow," she said. "It, um, it looks so...different. Ya know, from what I've seen of Jake's."

"Oh, um, well, I guess so," I said awkwardly, embarrassed at the comparison.

She looked at me with a little smile. "Um, so, I have a confession," she said.

"Oh? What is it?" I asked, breathing unevenly as she continued to touch me.

"I talked to Rachel about handjobs before this date," she said with a giggle. "She gave me some advice. But I'm...sort of confused. She said I should wrap my hand around it and stroke it up and down, but...I dunno..." She attempted wrapping her hand around my erection, but my penis was so small, it just disappeared in her hand.

I felt so embarrassed, but it helped that she didn't seem to know any better. "Um...well, uh, with mine, it's kind of better to put it between your thumb and your finger, like this," I said, showing her how I held it when I masturbated.

"Oh, wow," she said, then burst out giggling. I was mortified, but then she said, "I'm sorry, um, I'm just nervous."

"Oh, okay," I said.

"So...like this?" she asked, stroking my penis between her thumb and forefinger like I had shown her.

"Ohhh, uhh, yes, that's great," I said, my eyelids fluttering at her touch.