My Girlfriend's Roommate

In my mind, I was still enjoying a great relationship with a stunning girl. Sure, it was a little weird that both times Stephanie had made me cum, she had either been talking about how big Jake's dick was or how small mine was. And sure, most guys probably didn't jerk off imagining their girlfriends getting fucked by other guys. But I tried to brush all that aside.

So on our fourth date, when she finally told me she was ready to go all the way, I was over the moon. I still couldn't believe a girl as hot as her was even interested in me, let alone wanting to lose her virginity to me!

I had taken her out shopping at the mall as part of our date that day. I bought all sorts of different clothes for her, and I was happy to do it, although it was kind of a lot of money. At the end, she took me into a Victoria's Secret and said she wanted to pick something out for her to wear for our "special" night. She winked at me, and I could tell she meant that she finally wanted to have sex!

She looked at all sorts of different incredibly hot pieces of lingerie and finally decided on a bright pink bra and silk panties. I couldn't wait to see her in them. I carried all her shopping bags to my car and loaded them into the trunk, then took her out to a nice dinner. All I could think about was how eager I was to get back to her place.

On the drive there, we kept awkwardly giggling and smiling at each other. I was so nervous. When we got inside her place, she said, "Jake's out on a date with Rachel. I think they're going back to her apartment after, so we have the place to ourselves."

"Great," I said, carrying all her shopping bags.

"Let's go to the bedroom," she said, leading me down the hall.

She had me put all her shopping bags down in her closet, and I gave her the bag from Victoria's Secret.

"I'll be right back," she said with a smile, then slipped into the bathroom to change.

I could hardly contain my excitement. My penis was completely hard just thinking about what she would look like in the panties she'd picked out. I lay down on the bed nervously. Finally, the bathroom door opened and she stepped out. My jaw fell to the floor and I practically came in my pants then and there.

She looked incredible. Her round, perky breasts bounced lightly in her bra as she walked over. Her flat stomach looked so perfect, as did her tight, round little butt.

"Do you like it?" she asked.

"I...I love it," I said. "You look...absolutely stunning."

"Thanks," she said. "I'm...I'm kinda nervous."

"It's okay," I said. "I, uh, I am too. We can go as slow as you want, and we don't have to do anything you don't want to."

"Thanks," she said. "You're so sweet. Should you, um...?"

"Oh, yeah," I said, feeling stupid for still being fully clothed. I nervously pulled my shirt over my head, revealing my slim, pale body. I was obviously not built like Jake, and I felt really self-conscious showing a girl like Stephanie my body, but she just smiled and put her hand on my chest, rubbing it lightly. It felt so good. Then I unbuttoned and unzipped my pants, pulling them down and laying there in my briefs, my three-inch erection straining against the fabric, a little wet spot already forming.

"Oh, did you, um, bring a condom?" she asked.

My mouth fell open. I hadn't even thought about a condom. How could I have been so stupid? "Oh, no...I'm really sorry," I said.

"Hm," she said, clearly disappointed. But then she seemed to get an idea. "I know! Jake has plenty. I'll just run over and grab one from his bathroom."

Before I could say anything, she skipped out of the room and into Jake's bedroom next door. A few seconds later, she came back with a condom in her hand.

"Here ya go," she said.

I had a feeling this wasn't going to work out, but just to make sure, I tore open the condom and pulled it out. When I held it to my penis, it was obviously not going to fit.

Stephanie couldn't hold back a giggle. "I'm sorry, I should've realized the kind Jake uses are way, way too big for you."

"Um, yeah, sorry," I said, blushing. "What should we do?"

She looked momentarily conflicted, but then she said, "Well...I really want to do it, so maybe you could just, like, pull out before you...ya know...?"

I was relieved she wasn't putting a stop to things, so I quickly agreed. "Yeah, sure, no problem," I said.

"Great," she said. She smiled at me and lay down on the bed. "Okay," she said nervously. "Do you want to, um, get on top of me?"

"Uh, sure," I said, a little relieved that she was guiding things along, since I had absolutely no idea what I was doing. I climbed on top of her awkwardly and looked down at her. "I can't believe this is happening," I told her in a soft voice.

"Me neither," she said. "I'm so excited though."

I leaned down and kissed her. For the first time, we slipped our tongues awkwardly into each other's mouths, just for a couple seconds. It felt weird. Then she reached down and pulled my underwear down, so that my penis was rubbing up against her stomach and her panties. My eyelids fluttered from the pleasure I felt.

Cautiously, my hand slid up her body and tentatively groped at her breasts. She smiled up at me. "Do you, um...want me to take my bra off?" she asked shyly.

"Uh...well...only if you're okay with that," I said respectfully.

She smiled and nodded, then reached behind her and undid the bra, slowly sliding it off her. For a while, I could only stare in awe at her perfect breasts, so round and perky, with pointy little nipples. "Can...can I...?" I asked, my hands hovering over her breasts.

She giggled and nodded. "Go ahead," she said.

I reached down and squeezed her breasts, savoring the feeling. As I did, she wiggled out of her panties. I looked down in awe. I noticed she was shaved down there, which looked amazing, although I was a little surprised that such an innocent girl like her had thought to do that.

Then, finally, she spread her legs for me, and my penis was at her opening.

"Are...are you ready?" I asked, taking a long, deep breath.

She nodded, then closed her eyes, as if bracing herself.

This was it. Slowly, I slid my penis inside her. I closed my eyes too, taking in the intense pleasure of being inside this beautiful girl. Very gently and very slowly, mostly so that I didn't cum too fast, I pulled out and slid back in.

"Just tell me when you're inside me, okay?" she said, her eyes still closed.

My heart fell. "Oh, uh...I already am," I said.

She opened her eyes and looked down in surprise. "Oh!" she said, then looked up at me with a smile. "I"m sorry. I, um, I couldn't tell."

I was so embarrassed. My penis was so small, she couldn't even feel it inside her!

"I feel it now, though!" she said quickly, clearly just trying to comfort me. "It, um, it feels good!"

"Does it?" I asked skeptically.

She smiled and nodded. "Does it feel good for you?"

I slid out and in, out and in, slowly and carefully. "Y-y-yes," I stammered, almost overwhelmed by the pleasure.

"Mmmm," she moaned. "Good."

I slid in and out of her like that for a couple minutes, looking down at Stephanie's perfect body and feeling like I wouldn't last much longer. "Uh...do you feel like you might be close to, like...having an orgasm?" I asked her.

She had a funny look on her face, like she was about to laugh, but then she said, "Um, ya know, I think maybe my body isn't quite ready for that yet?"

"Oh...okay," I said, disappointed.

"But, um, it still feels good," she said sweetly. "And I want you to enjoy it. Are you, um, getting close?"

I nodded, my breathing getting more rapid. "It feels so good, Stephanie," I said.

"Good," she said. "I'm sorry if I'm not being, like, loud enough."

"What do you mean?" I asked, confused.

"Oh," Stephanie said. "It's just that, well, sometimes I can hear Jake and Rachel, ya know, through the wall. She always sounds really, really excited and loud. I'm sorry I don't sound like that."

"Oh, uh, it's okay," I said.

She giggled. "I hear Rachel saying such dirty things."

I swallowed heavily. "Um...like what?" I asked, too curious not to ask.

"Hmmm," she said, thinking about it. "Stuff like, 'Ohhhh, Jake, please give me your big hard cock! Fuck me nice and deep! Pound my tight little pussy!'"

"Ohhhhhh, wowww," I groaned. I had to stop thrusting into her to keep myself from cumming.

Stephanie giggled. "Ya know...I told her about our last two times together," she said.

"You did?" I asked, a little surprised. I slowly started thrusting in and out of her again.

"Mmhmmmm," she said. "She was so funny when I told her how small you are."

I swallowed heavily. "She was?"

"Yeah," Stephanie said. "She was actually kind of mean about it, but, ya know, that's just her sense of humor. She doesn't mean anything personally."

"Oh," I said.

"Do you...wanna hear what she said?" she asked.

I hesitated. "Um..."

"Oh, nevermind, I'm sorry, we're in the middle of having sex!" she said, as if she had forgotten I was in the middle of fucking her. "I shouldn't be telling you that stuff now, it might make you feel bad. That's so silly of me."

I let out a sigh and kept thrusting, but part of me had a burning desire to hear what Rachel had said. I couldn't believe I was pushing her on this, but I looked down at her and whispered, "Uh...it's okay...what did she say?"

"You really want to hear it now?" Stephanie asked, a little smile on her face.

I nodded eagerly.

"Are you sure?" she said. "Like I said, she has kind of a mean sense of humor. So she was kind of making fun of you a little."

"It's okay, please just tell me," I said, practically begging.

"Okayyy," Stephanie said with a giggle. "She said that little shrimp-dicked guys like you don't deserve to fuck hot girls like me."

"Ohhh," I moaned.

"Isn't that funny?" she said with a giggle.

"Mmhmm, yeah, it is," I agreed, thrusting faster now. "What else did she say?"

"Well...she said if I ever did let you put your little thing inside me, I probably wouldn't even be able to feel it," she said. "I guess she was right about that, huh?"

"Unngghhh," I groaned. "Yeah, I guess so."

"Yeah," she agreed. "I mean, look at you go, but I really can't feel a thing, you're just sooo small."

"Nnngghh," I moaned.

She giggled again. "I guess that's why Rachel said a hot girl like me should only spread my legs for real men...with nice big dicks...who can stretch out my tight little pussy and fuck me deep and hard."

"Ohhhhhhh, holy shit," I groaned. Uncontrollably, I felt myself start shooting my load into her. I pulled out as fast as I could, the rest of my cum squirting out onto the bed sheets.

Stephanie couldn't stop herself from laughing. "Oh, wow, baby," she said, giggling. "I'm sorry, I didn't know you were so close. That was, uh, really fast, huh?"

"Um...yeah," I said, breathing heavily. "Uh...I'm sorry, but I think I, um, squirted some of it inside you."

"Aww, that's okay, sweetie," she said comfortingly. "You just really couldn't help it, huh?"

"Uh...no, I guess not," I said, my head resting on her shoulder.

"I'm really glad you liked it, baby," she said, patting my head. "But...does it usually only last a few minutes like that?"

I picked my head up. "Um, no, I don't think so."

"Yeah, me neither," Stephanie said. "Rachel said Jake can keep going until he's made her cum over and over again."

"Oh...uh, I'm sorry about that," I said. "I'll make sure it's better for you next time, I promise!"

She smiled. "Okay, sweetie," she said.

***

The next day, I was full of conflicting feelings. I felt overjoyed that I had lost my virginity to such an amazing girl. It had felt so incredible. But it had also been so strange how I had gotten off so hard hearing what Rachel had said about me. And I worried that she was right, that I was never going to be able to please a girl like Stephanie.

So I decided I had to find a way to make the experience better for her. I didn't really like admitting it to myself, but it was pretty obvious my three inches were not going to be enough to please her. Like she had said, she hadn't even been able to feel it inside her. So I did some research online to see what guys with little dicks can do to keep their girlfriends satisfied. The main thing I found was to try to incorporate toys into the sex. So even though I felt really awkward about it, I went out and found a sex store where I could buy a dildo.

That weekend, I texted her, asking if she wanted to go out on a date and letting her know that if she wanted to have sex again, I had gotten something that I thought would make it a better experience for her.

"Oh, really?" she texted back, along with a blushing emoji.

"Yeah," I replied. "Only if you want to, obviously"

"Yeah, we can try it," she said. "I'm pretty curious what you got! But we're going to have to skip the date. I have some plans with a girlfriend this evening. Why don't you come over to my place after? Like around 10:00?"

I replied that this worked for me, secretly thankful I wasn't going to be doling out the money for some expensive meal.

That night, I arrived at her place, and she answered the door in a tank top and a pair of pajama shorts. Her hair was messy and she looked flushed and sweaty. "Oh, hi, Lucas!" she said. "Just in time! Come on in."

I stepped inside and saw Jake sitting on the couch in just his boxers. His chest and abs were lightly glistening with sweat. "Uh, hi, Jake," I said.

"How's it going, buddy?" Jake said, giving me a smile and a wave.

I turned to Stephanie. "Um, how was your evening with your girlfriend?" I asked, although it didn't really look like she had just been out.

"Oh," Stephanie said. "She actually canceled at the last minute, can you believe it?"

"Oh, that's too bad," I said.

"Yeah," she replied. "It wasn't a total loss, though. Jake and I decided to use this time to work out together since we both skipped the gym today."

"Oh, okay," I said. "I was wondering why you were both so, uh, sweaty."

Stephanie giggled. "Yeah, ya know, just some cardio," she said.

"Pretty intense cardio," Jake added, and Stephanie giggled again.

"But now that you're here," Stephanie said. "Why don't we head back to my bedroom?"

I smiled. "Have fun, buddy," Jake said as I followed Stephanie down the hall to her room.

After she closed the bedroom door behind us, she smiled and asked, "So, what's this special thing you got for us?"

I nervously pulled the dildo out of my bag. "Um...what do you think?" I asked nervously.

"Oh, wow," she said, staring at it. "Great idea, sweetie! It's sooo big. Actually, it looks about the same size as Jake's!"

"Uh, yeah...that's what I thought too," I said, nodding.

Stephanie lay down on the bed and looked up at me sexily. I briefly hesitated, wondering if I should suggest that she go take a shower since she had just worked out. But I didn't want to be rude, so I just got in the bed with her. Besides, it was kind of hot seeing her all sweaty like this.

"Come here," she said, and pulled me to her in a deep kiss.

We kissed for a few seconds, then began taking our clothes off. I was so nervous. Hopefully this time Stephanie would have a better time, and I'd get to see what she looked like when she got really excited!

After a few minutes, we were lying in bed naked together. I reached over to grab the dildo from the nightstand, but she took my arm to stop me. "Um...would it be okay if maybe you tried...?" she began asking hesitantly.

"What is it?" I asked. "What can I do?"

"Well...I've heard sometimes guys will, like...lick the girl...down there?" she asked.

I smiled. It was so cute how innocent she was. "Of course," I said, excited to try this out.

"Thanks," Stephanie said. "You're the best."

I kissed her, then slowly kissed my way down her body. It was so hot to kiss her perky breasts and then kiss down her flat stomach. When I got down to her vagina, I noticed it looked a little bit different than the last time I had sex with her. It was a little more red and was glistening with wetness.

"Wow," I said. "You're, um, pretty wet! Are you, like, getting excited?"

"Mmm, yesss, baby, I'm really turned on," she moaned.

I couldn't believe it. She was actually getting aroused by being with me! I was so excited. A little hesitantly, unsure of myself, I leaned in and licked her vagina, looking up at her to gauge her reaction.

"Mmmm, that feels good, keep going!" she moaned.

Encouraged, I kept licking. I didn't really know what I was doing, but I tried to respond to the sounds she was making. She seemed to particularly like it when I slipped my tongue inside her, so I started lapping hungrily between the lips of her vagina, sliding my tongue as far inside her as I could get it.

"Ohhhh god, that's it, Lucas, just like that!" Stephanie cried out.

I continued eagerly. Every now and then, I noticed a kind of weird, salty taste in my mouth, but I figured this must be normal when you were eating out a girl who was getting really into it. And was she ever! She was moaning loudly, her body writhing against the bed. It was amazing to see her getting so excited.

After a while, she looked down at me with a smile on her face. "Does it taste good, baby?" she asked.

By this time, I had adjusted to the salty taste and actually started to really enjoy it. I smiled up at her and nodded. "So good, baby," I said. "I really love it!"

She giggled and said, "That's so hot." Then she patted my head and said, "Um, I think I'm ready for the toy now. You did such a good job, though!"

I had almost forgotten about the dildo. I pulled my head away from her vagina and smiled. "Thanks," I said. I wiped my face and crawled up next to her.

She leaned in and gave me a big, deep kiss. "Mmm," she said sexily, a little smile on her face.

I grinned and reached over to grab the dildo. "Should I...um...?" I asked, motioning to her vagina.

She bit her lower lip and nodded.

Nervously, I slid the dildo down between her legs, putting the tip at her opening. For a second, I hesitated. "Are you sure it's not, like, too big?" I asked. "I don't want to hurt you."

It looked like she wanted to laugh for a second. "I think it'll be okay, sweetie," she said. "Go ahead."

"Okay," I said nervously, then slowly slid it inside her.

"Mmm," she moaned. She reached down and began stroking my penis between her finger and thumb. "Is it okay if I do this?"

"Ohhh god, yes," I groaned, pushing the dildo a couple inches deeper. "Does it feel good?"

"Ohhhh yesss," she moaned. "Put it all the way inside me, please!"

"Oh, wow, okay," I said, surprised that she wanted to take the whole thing. I slid it in further, until all eight inches were inside her. I looked down in awe at the way it stretched her open. It was so hot. I silently wished my penis could do that to her. "Is that okay?" I asked.

"Oh my god, wow, yes, it feels soooo good!" she moaned. "Please slide it in and out of me!"

I didn't need to be told twice. She kept stroking me as I thrust the dildo in and out of her. Her perky breasts began bouncing as the pace of her breathing increased. It was so hot.

Her moans increased, but after a few minutes, her hand slipped off my penis as she began to get lost in her own pleasure. She glanced over at me apologetically and said, "Oh, I'm sorry, sweetie, it's just hard to focus on stroking you when this feels so good."

I didn't want anything to get in the way of how much she was enjoying herself, so I quickly said, "It's okay, honey, don't worry about it, I'll just stroke myself!"

She smiled. "Are you sure? You don't mind?" she asked.

"Not at all," I insisted, taking my penis between my finger and thumb and stroking it with one hand, while I continued thrusting the dildo in and out of her with my other hand. "See?"