My Girlfriend's Roommate

"Good," she said. She stroked me like that for a few seconds, then said, "Um...it's kinda funny, Rachel said her fingers barely reach all the way around Jake's...ya know..."

I swallowed nervously. It was a little distracting hearing her talk about Jake's penis while she stroked me, but I just figured she was so innocent that she really didn't know she was saying anything wrong. Besides, her hand on me felt so good, and my hard-on actually kind of twitched a little as I thought about Rachel stroking Jake's big erection.

"She said she loves feeling his nice, hard penis in her hand, stroking it all the way up and down," Stephanie added in a hushed voice, leaning in so she was practically whispering in my ear. "She said it feels soooo big and powerful." She paused for a second, looking down at my penis between her fingers. "But I guess not all guys are like that, huh?"

"Uuhhh," I sighed. I couldn't believe she was saying this stuff without realizing it would make me feel inadequate. Still, the way she was stroking me was giving me a feeling of pleasure like I'd never felt before, and the images she was putting in my head of Rachel's small hand wrapped around Jake's big erection were kind of turning me on.

"I'm sorry, is it weird to talk about how much bigger Jake's penis is than yours? Do guys not like that? I just really don't know anything about this stuff," Stephanie said innocently as she continued stroking me.

"Ohhhh, uhhh, it's okay," I moaned. I closed my eyes, really just trying not to cum too fast. It was so humiliating hearing her talk like this, but she was still making me feel so good.

"Are you sure?" she asked, pulling her hand away.

"Yes, yes, please keep going!" I said quickly, desperate for her to keep touching me.

She smiled at me. "Oh, okay, I'm sorry, I thought maybe I messed up," she said, then brought her finger and thumb back to my penis and began stroking again.

I smiled and leaned my head back against the carseat, assuming she was done talking about Jake. I could just close my eyes and focus on the fact that a hot girl was actually touching my penis.

But after a few seconds of stroking, she started talking into my ear again. "So, anyway, I know from Rachel that Jake's is considered to be, like, really big. So is one like yours considered to be, like, average?" she asked me.

I swallowed nervously. I didn't really want to talk about this as she gave me a handjob, but I also didn't want to discourage her and cause her to take her hand away again. "Um...I guess it's kind of, uh, smaller than most guys," I admitted, feeling myself blushing.

"Aww," she said. "Well, that's okay, sweetie." She started sliding her thumb around the tip of my penis, which was getting slippery from all the precum that was coming out. It felt so good! "I don't mind if your penis is really tiny. I mean, sure, Rachel can't stop talking about how much she loves how big Jake is."

"Uuuhhnnngghh," I groaned, feeling her thumb swirl around the head of my erection. Again, even though it felt so demeaning to be compared to Jake like this, hearing about him and Rachel kind of turned me on. "Uh...she does?" I asked, a weird part of me wanting to hear more.

"Mmhmmm," Stephanie said casually. "She tells me such naughty things. Like how it's so big that she can take it in both of her little hands and stroke it back and forth..."

"Yeah...?" I said, prompting her to continue.

"And he gets soooo excited that he blows his big, sticky load all over her!"

"Nnnghh," I whimpered. I was so close to cumming, but for some reason she chose this exact moment to pull her hand away.

"Oh, sorry," she said. "My fingers were just getting a little tired." She wiggled her fingers around and smiled at me. "Am I doing a good job though?"

I nodded. "So good," I said quickly, breathing heavily. "Could you, um...please...keep going?"

She giggled and nodded. "Of course," she said. She took my hard-on between her finger and thumb again and continued stroking, then went right back to talking innocently about how small I was. "Anyway, like I said, it totally doesn't matter to me that you're so small I can only hold it between two fingers," she said. "Obviously, I've never held a big one like Jake's in my hand, so I don't even know what that would be like. Hmmm..." She began stroking me faster as she paused thoughtfully. "I'm even smaller than Rachel. My little hands would probably look so small wrapped around his big...hard...penis. Don't you think?"

Naturally, I began imagining Stephanie giving Jake a handjob, stroking his big dick up and down with both hands. "Nnngghh, oh god, oh god, ohhhhh goddddd," I groaned. Before I knew it, I was squirting my load onto her hand.

"Oh, wow!" she said, then began giggling. "Um, that's good, right?"

"Um...yes, Stephanie...you did very good," I said. "I'm, uh, sorry I got your hand so messy. There's some tissue in the glove compartment."

"Oh, that's okay," she said with a smile, opening the glove compartment to pull out the tissue. "From how Rachel described it, I thought there would be a lot more. But I'm so excited I could make you feel good like that!"

"Uh...yeah...thank you so much," I said.

She giggled, cleaned her hand off, then leaned over and gave me a kiss on the lips. "I'm sorry, was it weird that I kept talking about Jake and Rachel? Like I said, I really don't know about this stuff."

"Oh, um, no, it was, uh, okay," I said.

She smiled at me. "Oh, okay, good. Well, good night, sweetie!" she said.

"Uh, yeah, good night," I said. She got out of the car and skipped up to her apartment. I rested my head back against the seat and grinned. Sure, my first handjob from a girl had gone a little weirder than I might have expected, but I was still so grateful that it had happened, and with such a beautiful girl!

***

The next week, Stephanie asked if I would write a paper for a class she was in that I wasn't even taking. I told her I didn't know the material, but she said she had all the texts she was supposed to write about, and she was sure I would do a better job than her because I was "sooo smart." I really couldn't resist when she complimented me like that, even though I knew it would be a lot more work since I would have to do all the reading on top of writing the actual paper.

So I again found myself at her place writing a paper for her while she cuddled with Jake on the couch behind me. Rachel wasn't there that night, and Jake was again wearing just a pair of boxers with no shirt. I had mostly gotten used to this, but it was still a little weird, especially after I had listened to her idly musing about what it would feel like for her to stroke his big penis. But they both acted like everything was perfectly normal, so I didn't think too much of it.

Of course, it wasn't long before Jake got a big tent in his boxers again. As I was in the middle of trying to concentrate on what were actually some pretty difficult texts, the two of them started giggling loudly behind me, and I glanced back at them. There was Jake's massive erection pointing straight out in the air. Stephanie was looking down at it, her hand on Jake's abs, just inches away from it. She smiled at me mischievously when she saw me looking. I wondered if she was thinking about what it would feel like to slide her hand down, slip it under Jake's boxers, and take his big hard dick in her little hand. It was a little weird, but I started picturing it and getting a throbbing erection myself.

"You okay, sweetie?" I heard Stephanie ask, and I realized I'd been staring slack-jawed at the two of them for a few seconds now. I shook myself out of my reverie and saw Stephanie smiling down at me, her fingers tracing lines on Jake's abs.

"Yeah, buddy, you look a little flushed," Jake said. "Everything all right?"

His tone was so casual, even as his erection literally bounced up and down in front of me. I swallowed nervously, feeling myself turning bright red and starting to sweat. "Oh, uh, yeah, I'm, uh, I'm okay," I stammered awkwardly. "Let me just, uh, let me get back to Stephanie's paper."

"Okay," Stephanie said. "Thanks, sweetie. Remember, it's due tomorrow, so I kind of need you to stay focused."

"Right, yeah, sorry," I said. I turned around and returned all my attention back to Stephanie's paper. I didn't want to disappoint her by doing a bad job with it, so I forced myself not to turn around for the rest of the evening, until I was finished. I knew that for whatever weird reason, seeing them cuddling like that was just getting me too turned on, and then I wasn't able to concentrate.

It took me a while, especially with the two of them giggling behind me. They even changed the channel to some basketball game, and Jake started cheering for his team, saying stuff like, "Yeah, yeah, keep going! That's it! Don't stop! Yes!" And then at one point Stephanie had to reach over in front of me to grab a box of tissues off the coffee table, saying she was feeling a little sniffly. But I was able to ignore it all, and finally I was happy with the paper!

"Finished!" I said, then turned around.

To my surprise, Jake's boxers were no longer tented. He was, however, glistening with a light sheen of sweat. Stephanie looked a little flushed too.

"Oh, um, are you guys okay?" I asked, a little worried they were coming down with something, especially since Stephanie had said she was feeling sniffly.

"Oh, yeah, dude, we're fine," Jake said. "It's just really hot in here, don't you think?"

I found it to be quite comfortable, but I just shrugged and said, "Um, yeah, I guess so."

Stephanie leaned down and gave me a peck on the lips. "Thanks for the paper, sweetie," she said. "See you on our date this weekend, right?"

I grinned. "Yep, see you then!" I said.

***

After our date that weekend, I was so nervous. I had taken her out to have drinks at a fancy cocktail bar and then dinner at a nice Italian restaurant. She looked amazing in a sexy red dress. When I drove her back to her place, I was hoping she might give me another handjob like last time, but I was really worried that she might not want to after she had found out how small my penis was. But I was thrilled when she told me she actually wanted to take things even further!

"Would you maybe want to, um, come upstairs with me?" she asked, a mischievous smile on her face.

My mouth fell open. "Really?" I asked.

She put a hand on my arm, as if to caution me. "I'm not ready to...ya know...go all the way," she said.

"Oh, um, that's okay," I said. I certainly didn't want to pressure her into anything, although I did feel a little disappointed.

"But, like, maybe we could do...a little more than last time?" she asked.

"Uh, yeah!" I said eagerly. "I mean, if you're comfortable.".

"Yeah, I am," she said. "Let's go."

I parked the car and we went upstairs. Jake wasn't in the living room, but we saw the light was on in his bedroom. "Quick, let's go back to my room," she said.

We scurried down the hall to her bedroom. She closed the door behind her and walked me to her bed. We lay down on it together, then she climbed on top of me. She gave me a deep kiss. There was still no tongue, but it lasted a long time, like ten seconds! Then she reached down and unbuttoned and unzipped my pants. I was surprised at how quickly she was moving things along, but I certainly wasn't going to complain.

"So...if it's okay, I want to...um...give you a...ya know...a blowjob," she said.

I felt my cheeks turning bright red, but I was so excited. "Oh, wow, uh, yeah, that's okay," I said. "Are you sure?"

She nodded excitedly. I could hardly believe it. She pulled my briefs down, my 3-inch erection popping out. She smiled down at it, then looked back at me. "Um...so I talked to Rachel for some advice. She, um, told me about, like...deepthroating," she said. "Do you know what that is?"

I smiled at her innocence. "Um...yeah," I said.

"Rachel said it's when the girl slides the guy's penis, like, all the way down her throat," Stephanie said.

I nodded. "Uh, yeah," I said.

"She said she loves doing it with Jake."

"Oh, um, ok," I said. I was already getting a little nervous, knowing that Rachel deepthroating Jake's big penis was going to be a very different experience from Stephanie putting my little penis in her mouth. It didn't seem like Stephanie had thought about this, though.

"Can we try it?" she asked.

"Um...yeah, sure," I said, not knowing what else to say.

She smiled and slid her body down so that her face was at my penis. She was still in her dress, and I kind of wanted her to strip down a little more so that I could finally see her naked, but I was too shy to ask about it. As I looked down in awe, she brought her mouth to my penis and put it between her lips, sliding up and down on it and swirling her tongue around. It was the greatest thing I had ever felt in my life. I threw my head back in pleasure and let out a moan.

After a few seconds, she pulled her mouth off and looked up at me, a little confused look on her face. "What is it?" I asked. "Is everything okay?"

"Yeah, it's okay," Stephanie said. "It's just...I guess I didn't think about how small yours is. Rachel said I'm supposed to feel it going down my throat and stuff, and that I might even gag on it, but, like...yours barely goes past my lips?"

I started blushing, feeling so embarrassed. "Um, yeah, well...I guess my penis isn't big enough to, like, really deepthroat," I said apologetically. "Not like Jake's."

"Aww, yeah," she said. She kind of absentmindedly took my penis between her thumb and forefinger and began stroking it. "I guess I should've realized that, huh? That's too bad, though. Rachel made it sound really fun." I was crestfallen hearing her express her disappointment. She must have seen the look on my face, because she quickly said, "I mean, um, it's okay, though! I still like doing it. Does it still feel good to you?"

She put my penis between her lips again and sucked it the little bit that she could. "Ohhh, uhh, yeah, it definitely feels good," I groaned.

"Oh good," she said, taking it out from between her lips and going back to stroking it between her fingers. "It's funny, I never knew guys' penises could be soooo different in size! I mean, Rachel says she can't even get Jake's all the way down her throat because she starts to choke on it!"

"Ohhh," I groaned. What she was saying was kind of making me feel inadequate, but in a weird way, I was also getting more turned on, probably because I was now picturing Rachel sucking on Jake's big erection until she gagged.

Stephanie kept blowing me, then giggled and looked up at me. "Yours kind of feels like sucking on a straw," she said. "But, ya know, shorter."

"Uunnghh," I whimpered. I supposed she didn't realize she was insulting me, but I didn't really mind, anyway. What she was doing just felt so good!

She started stroking my penis between her fingers and flicking it with her tongue. I was in heaven. I was so impressed she was this good at it even though it was her first time! Then she looked up at me and said, "Hey, you wanna hear something kinda funny?"

"Uhhh, sure," I said, my eyelids fluttering from the pleasure she was giving me. I kind of wished she would just focus on the blowjob and stop talking, but I didn't want to seem rude.

Stephanie giggled. "Rachel says she's something called a 'size queen,'" she said. "Have you ever heard of that? It means she only has sex with guys with really big penises, like Jake." Again, she flicked the head of my penis with her tongue while she stroked me. "So, like, she'd never do anything with you, since yours is so tiny."

"Nnnngghhh," I groaned. Whenever her tongue touched my penis, I would get so close to cumming. "Uhh, that's interesting," I said awkwardly.

She giggled. "Yeah, I thought so too," she said. "Obviously I wouldn't know, but she says it just feels soooo much better when a nice big dick like Jake's goes really deep inside her wet pussy!"

"Ohhhh, god," I groaned. I'd never heard Stephanie use words like this, but I supposed she was just repeating what Rachel had told her.

"Yeah, she's so funny," Stephanie continued. "I don't know why, but she said she'd never be able to get off with any penis smaller than 7 inches. What's yours, like, 2?"

"Nnngghh, uhhh, closer to 3," I corrected her.

"Hmm, if you say so," she said skeptically. "Well, either way, I guess you'd never be able to get a girl like her off in a million years, huh?"

"Oh god, oh my god, ohhhhhh god," I groaned, then suddenly began squirting up into the air as she stroked me.

"Oh, wow!" Stephanie said, watching me cum. "Well, that didn't take long, did it? Did I do a good job?"

"Uh...yeah," I said, catching my breath. "That was amazing." It was true, I'd never had such a strong orgasm in my life.

She giggled. "Oh, good, I'm really glad you enjoyed it," she said. "I'm sorry I talk so much, I guess I just get kind of nervous. I know some guys kind of like, ya know, 'dirty talk.' But I don't really know how to do it. Was I saying the wrong kinds of things? It's okay, you can be honest."

I thought about telling her to maybe not talk so much about how small my penis was. But something made me hesitate. "Um, no, you did great," I said.

She smiled. "Oh, good. I mean, that's what I thought, based on how you were reacting. But thanks, I'm glad you liked it." She leaned over and gave me a peck on the cheek. "Um, listen, I don't think I'm really ready to, ya know, sleep in the same bed with another guy. So, would you mind, like...?"

She didn't need to finish her sentence. I was a little surprised, but obviously I wanted to respect her wishes, so I said, "Oh, uh, yeah, of course, I'll head out. Um, good night." I began awkwardly wiping myself off and putting my clothes back on.

"Good night, honey," she said, smiling as I made my way out.

I closed her bedroom door behind me and walked down the hall to find Jake in the living room cuddling on the couch with Rachel. Rachel was just in a pair of panties and one of Jake's t-shirts. Jake, as usual, was just in his boxers, which were again fully tented. "Oh, uh, hey," I said, surprised. "I hope I'm not interrupting anything."

They looked at me and smiled. "Not at all, buddy," Jake said. "Looks like you had a pretty good night, though, huh? I mean, look at you, you're glowing!"

"Oh...um..." I said awkwardly.

Rachel slapped his chest. "Stop it, you're making him blush!" she said.

"Aw, come on, I'm just saying, it looks like he showed Stephanie a really good time!" Jake said.

I blushed and looked at the floor. Now that Jake mentioned it, I was realizing that not only had Stephanie not gotten off either time we had done stuff together, she hadn't even seemed particularly aroused...except maybe when she had been talking about Jake's big dick.

Rachel giggled and said, "Aw, Lucas, I'm sure you did fine."

"Thanks," I said to her, then noticed her hand sliding up Jake's upper thigh, close to his hard-on. I thought about what Stephanie had said about how much she liked to deepthroat him until she gagged, and how good it felt when he was deep inside her wet pussy. Even though I'd just gotten off, I felt myself getting hard again. "Um, well, I gotta go," I said, then quickly left. As soon as I got home, I was jerking off thinking about how Jake was probably fucking Rachel right at that very moment. As I pictured it, my mental image of Rachel, naked and spreading her legs for Jake's big dick, suddenly transformed into Stephanie, and I immediately began squirting my load into my hand.

***

I know, by this time I should have realized what a pathetic cuck I was. I could have just gone to Jake and begged him to fuck Stephanie for me like I had fantasized about. But it takes time to accept these things.