My Girlfriend Needs a Larger Man

"Dude, those must be the baggiest swim trunks I've ever seen. Are you planning on swimming in those or using them as a parachute?" Thomas teased. My girlfriend Madison and I were hanging out at our friend Thomas's pool. Well, it was actually his parents' pool, but they were usually traveling. So even though Thomas had his own place, he'd often entertain our circle of friends at their house.

I didn't want to call attention to it, but I wore shorts instead of swim trunks for a reason. I picked them, because they looked like trunks and the fabric was thick. The thing was, I was shy about the size of my penis. "Yeah, it's just more comfortable is all. I needed extra room, if you know what I mean." Might as well lie. They'd never know.

Unfortunately, my ruse was short-lived. As I walked by her, another friend, Becky, tugged my shorts down. My penis bobbed into view of everyone. I tried pulling the shorts back up, but Becky held them down. By the time I pulled my shorts back up, everyone had seen everything. They all roared with laughter.

"Don't be embarrassed Christian. So what if you have a small penis?" Olivia said as her laugh finally subsided. "We all know now, anyway."

"Yeah dude. No one cares." Benjamin tried reassuring me.

"I'll be honest, I would have guessed you had a big dick, or at least average." Brianna added.

"I'm just surprised it doesn't hang down. I've never seen a penis like that before. Does it always just point out like that?" Becky asked.

"Um, I guess.." I replied.

"Yeah, that is weird. It's like a kid or something. I don't mean to be rude. I'm genuinely curious. Did you.. have puberty?" Becky inquired further.

"Of course." I replied tersely, offended at the suggestion. I'm a full grown 28 year-old man dammit.

"Well, I didn't know." Becky shrugged her shoulders. "That would just be one explanation. And you don't have any pubic hair, so I figured you either shaved or didn't grow any."

"I thought it would make it look bigger." I replied sheepishly. Everyone chuckled. If I hadn't shaved, my penis would've barely been visible, so I suppose it would've looked pathetic either way.

"Maybe he's a grower?"

Madison, my girlfriend, shook her head. "No, I mean it gets a tiny bit bigger, but it's still really small."

I instantly felt even smaller. I had always known I was below average, but this is the first time I had heard Madison acknowledge it. Could they please just talk about something else I thought?

"It's not a problem for you?" Thomas asked Madison.

"I don't know." Madison shrugged. "Truthfully, I am curious what a normal sized or bigger would be like."

Brianna looked at me. "You haven't considered letting her experience something bigger?"

"What? No!" I replied defensively.

"Come on, it's the least you could do for her." Olivia said.

"Yeah man, don't be selfish." Benjamin added.

Brianna put her hand on mine, almost like she was trying to reassure me. She gave my hand a small squeeze. "It's not your fault you have a small penis, but you really should let Madison have a satisfying sex life."

"It's not like it's that much smaller than normal." I argued.

Brianna shook her head and smiled to herself. "You know what? Jeremy, show them yours."

"What? Really? You sure?" Jeremy asked.

"Yeah, I'm your girlfriend and it's ok with me if they see it come here."

Jeremy stood up next to Brianna, and she pulled his swim trunks to his ankles! This entire experience was so surreal. Having everyone seeing my small penis was embarrassing enough, now here was Jeremey's obviously much bigger dick just dangling there to further highlight how small I am.

"Now look. You can see this is what a normal penis looks like. See, it's hanging down, reaching the bottom of his balls." Madison locked her eyes on Jeremy's penis while Brianna took it in hand and stroked it to an erection. My girlfriend gasped when it reached its full size. "And this is fully erect. Madison, you want to touch it? Sorry I won't let you sleep with him, but you can at least feel the difference."

My utter shock prevented me from stepping in. I was powerless as I watched my girlfriend wrapping her small soft hand around another man's penis. Her delicate touch felt every facet of it. She had never shown this level of interest in my privates.

Finally, Madison turned to me. "Christian, do you mind pulling yours out again?"

I hesitated, there was no way I wanted to show everyone my penis again! Especially since, for some reason that I couldn't fathom, watching Madison grope Jeremy had given me an erection. The group encouraged me to comply until at last I just gave in.

"Oh my goodness Christian, look how much bigger Jeremy is than you!" She took hold of my erect penis while still holding Jeremy in her other hand. "You know what's funny is that your hard is about the same size as Jeremy's was soft."

I can't explain it, but Madison's last comment sent me over the edge. I had an orgasm and my cum shot out to the ground in front of me.

All my friends almost fell over laughing. "Whoa, what's going on here?" A familiar voice asked. It was Logan, Thomas's little brother. He still lived at their parents' house and he must have just walked outside. I pulled my shorts back up as quickly as I could. Even though Logan was 18 now, I still looked at him as this punk kid. Now he walked out just in time to see my girlfriend with another guy's cock in her hand, me cumming from it, and that I have a small penis. I was so embarrassed, I felt so emasculated.

"Well, I'd say today was informative. Don't you agree sweetie?" Madison said, looking up at me with her sweet eyes, still holding Jeremy's cock.

Madison and I left shortly after. I hoped to pretend nothing happened, but Madison wasn't going to let that happen. "I was thinking about it and I think our friends are right. You really should let me try sex with a larger man."

"You can't be fucking serious." I replied.

"I am serious. Just listen. You're the only man I've slept with and I'm sorry, but I feel like I've missed out on an experience. Who knows, maybe I'll find out I only like little penises like yours. Maybe big ones will hurt. I won't know until I try. And not to hurt your feelings. Sex is fun, but it feels like something is missing. It's like I feel like I'm still a virgin. You're just so small that it's almost like until I've had a real man in me, I'll still be a virgin." Madison paused momentarily. "I'm sorry that came out wrong. You are a man, but it's more like... for example, if a girl were fingered then she would still consider herself a virgin right? It's like that."

Putting aside for a moment that my girlfriend just argued that my penis was so small that sleeping with me doesn't count as sex, I started to accept that I might not be able to stop this. "Do I really have a choice?" I asked.

Shaking her head Madison answered, "no, not really. I never knew how to say it, but something has been missing with sex for a while. For our relationship to work, I need to experiment a little."

I sighed. "Where do you even plan on finding a guy anyway."

"Actually, I already have one in mind. There is someone I used to work with. Remember Zach? He flirts with me all the time, even sent me a dick pic once. So I know he's pretty average, like a couple inches longer than you and thicker. I am thinking I'll drop you off at our apartment, then head over to his place."

"Right now?" I asked in shock.

"I don't see what the big deal is. It's going to happen, anyway. Might as well start now. He was sending me flirty texts just this morning. I'm sure he'll be willing. I'll call him right now to put your mind to ease, ok baby?"

Madison pulled out her phone and immediately called and put it on speaker. She seemed to misunderstand that my lack of ease had way more to do with her having sex with another guy than the possibility he might say no.

"Hey girl." Zach answered.

"Hi Zach, can I ask you for a favor?" Madison asked.

"Yeah, sure. What do you need?"

"This is going to sound crazy, but I need your dick." Madison told Zach.

"For real? Did you and Christian break up?" Zach asked.

"No, we are still very much together. I have his blessing though." Madison assured Zach.

"Really? He's letting you have sex with me?"

"Yeah, it's kind of an important experiment. We agreed I need to try sleeping with a guy that has a bigger penis. Christian is on the smaller side." Madison said.

I heard Zach laugh hysterically through the phone. "Wow, um. Yeah, of course I'll help you out."

"Yay! I'll be there in half an hour!"

Madison hung up. I closed my eyes and sighed. "You at least need to use a condom, ok?"

Madison nodded. "I'm sure Zach has some." We pulled up to our apartment and Madison put her car into park. She gave me a kiss and said. "I'll be back later and tell you every detail, ok?"

Madison barely waited long enough for me to close the car door before she sped off. I ambled into our apartment, barely able reconcile the day's events. First my humiliation, my small penis being exposed to all our friends, and now my girlfriend was heading over to another guy's house to have sex. My mind raced with images of Madison's encounter with Zach, him pulling off her clothes, her small hands pulling his erect cock from his pants. Maybe she tells him it's so much bigger than mine. My stomach feels tight, I'm embarrassed and stressed, but also an unexpected reaction. Without realizing it, I had pulled out my penis and was masturbating. I envisioned Madison taking Zach into her mouth, then straddling him and lowering himself herself down. My fantasy had barely started when I came. I closed my eyes, wondering why I had just masturbated to thoughts of Madison cheating. I zoned out, the day's events kept playing in my head. I wasn't even aware of the passing of time.

I was pulled from my trance later by the sound of our apartment door opening. Madison bounced in and started speaking to me excitedly the moment she saw me. "I have so much to tell you. That was so much fun. Now Zach was only average, maybe 6 inches, but I definitely know now I prefer larger over smaller. I had an orgasm, during intercourse! I never had that with you babe!" The excitement in her voice was obvious. Madison sounded like a kid who just visited Disneyland. "It will still be necessary to try an actual big one, but at least we know now I need bigger than yours. Before going back out, I'm going to need new panties though. I'm still leaking into these."

"I don't understand. I thought you were going to use a condom?" I asked.

"No.. Sorry, I was too excited. And I didn't want to diminish the experience. It would kind of defeat the whole point of what I'm trying to do. I don't really like condoms anyway."

"If you don't like them, then why do I have to wear them?" I was angry. Madison and I had never, even once, had sex without a condom.

"That's different, babe. I have you wear those so that you'll last longer. You tend to cum too fast. Zach doesn't have that problem, so it really wasn't needed. In fact, he lasted longer than you do, even with your condoms."

I sighed. I was annoyed, but no amount of complaining would change what had already happened. "Do you at least have this out of your system now?" I asked.

"Um, no." Madison laughed. "Like I said, I discovered size does matter. I'll need to experiment more, but it's obvious now that we'll need to keep our relationship open. I already have another guy in mind anyway."

"How can you already have someone in mind?"

"Becky has an ex that she's still friends with. She texted me while I was at Zach's place, knowing that I might want to know after our talk earlier. Becky is still friends with him and she said he's got a big one and he thinks I'm cute so I figured, why not?"

"I can't believe you just cheated on me and you are already talking about doing it again the very same day." I complained.

"Um, baby, this isn't cheating. We've been over this. You aren't satisfying me. Thanks to our friends, we've been able to establish you have a small penis. That means trying sex with bigger men is really the only option. So, when you really think about it, it's not cheating as long as the other guy has a bigger dick than you." Madison took my hand into hers. "Honestly, I think this saved our relationship. I really want to be your girlfriend, but was starting to feel like there was no solution to your disappointing performance. I was considering the possibility we might need to end things. But now we found a way I can get satisfied. I think you'll feel better if I tell you about how amazing everything was, then you can be as excited as I was! Come on, I'll tell you while I get changed."

I followed Madison to our room as she began stripping down.

"So I get there and Zach asks me if I'm sure about what we are about to do. I answer by kissing him. He kisses me back and we are making out hard. Hands are roaming all over each other's bodies. From there, Zach led the way. He got my top off and began feeling my breasts. He was so confident and dominant that in an instant, I was completely turned on. I think Zach picked up on it, because he wasted no time yanking my bottoms off and getting a finger inside of me."

Madison now dropped her panties to her ankles and was completely naked.

"At this point, I reached in and grabbed his dick. It was so hot, feeling it in my hand. It was a lot like Jeremy's, so you know average sized. But way larger than you. I wanted him in me so badly, I was so horny. That was when I decided that I had to feel him and experience Zach without a barrier and that I wouldn't make him wear a condom. It was a strange feeling. I've never had that desire with your small penis."

There it was again, Madison reminding me how small my penis was.

Madison began to put on her change of clothes. "The moment he went inside of me, I knew it was better. Just the fullness and the pleasure. I'm sorry honey, but it was obvious from the moment his penis was inside of my vagina that I needed bigger than you."

"If you're so sure, then why do you need to go out and do it again?" I asked.

"Like I said, I need bigger than what you have, but now it's just a matter of figuring out how much bigger. So I'm going to need to continue experimenting with other men. So I will keep sleeping with bigger guys until we figure this out, so don't worry ok?" With that last comment, Madison gave me a kiss and headed back out.

After Madison left, I returned to our room. I saw her panties on the floor that she had just stripped off and picked them up. There was a dampness I could feel on my hand. Inspecting the panties more closely, I saw the crotch had a wet spot. Looking at it from the inside, it glistened, and I felt it with my finger. It was Zach's cum mixed with Madison's juices. I couldn't believe I was looking at cum that had been inside of my girlfriend's pussy. Cum that wasn't mine. In fact, my cum had never been inside of my girlfriend, because I've never fucked her without a condom.

Not knowing what to do with myself, I played video games to pass the time while I waited for Madison to come back. Eventually, I couldn't wait up any longer. I walked to our room, collapsed on our bed and fell asleep.

I woke later, hearing Madison return. She walked up to the side of our bed and squeezed my shoulder to get my attention. "Bigger is for sure better! Look how much he came in me!" Madison dropped her pants and pulled down the front of her panties. They were absolutely filled with cum. It was sticking to her pussy and crotch of her panties.

Madison looked down and grinned. "Is that a little tent I see? Christian, I didn't realize this would turn you on so much." In fact it did. I had gotten hard seeing the aftermath of Madison's night. She rested her hand on my crotch and gave me a squeeze.

"No it doesn't." I protested.

Madison freed my erection from my underwear and stroked it with her thumb and forefinger. "Oh you like it. You've never been this hard before. Let me tell you about all the details."

I would have objected, but I was far too focused on not cumming.

"You know, after he came in my pussy and pulled out I sucked his cock clean. His soft was bigger than you are now." She held a finger an inch past the end of my penis. "That much longer." Then wrapped her hand around me, leaving space around my penis. "And that much thicker. That was him soft honey!"

I closed my eyes, focusing harder to not cum and prove Madison right.

"Then he got hard again and well.. Let's just say, size-wise, you aren't even close. I was shocked at first at his second erection, because you never get hard again. That's one of the reasons there is so much cum. He finished inside of me twice."

I couldn't stop it anymore, despite fighting it as hard as I could, cum dribbling out of my cock and on Madison's fingers. She wiped her fingers off on my shirt. "Yeah babe, you totally don't like it." Madison laughed to herself and walked to the bathroom to cleanup.

The following morning, Madison left and did not return until the afternoon. When she came back home, she was not alone. Thomas's younger brother Lucas, the same one who had seen my humiliation the day before, walked in behind her.

"Hi honey, you remember Lucas? He texted me out of the blue this morning!"

"Yeah, Tommy told me about everything that went down. I knew I'd be able to help out." Lucas smiled. "Let's just say I'm blessed."

"So I decided to go pick him up! And well, I couldn't wait, so Lucas and I played a little in my car. Let me tell you, he wasn't lying. He's huge, more than twice your size! Anyway, we'll be in the bedroom. Just give us some privacy for this first round, ok?"

Madison lead Lucas by the hand into our bedroom and closed the door behind them. I sat on the couch and did the only thing I could do, wait. Turns out I did not need to wait very long, I heard Madison through the door.

"You are so fucking big." Then silence. The quiet continued for over a minute, until I heard Madison quietly moaning. It gradually got louder until Madison's moans had given way to literal screams of pleasure. She had never made sounds like this with me.

After what seemed like an eternity of hearing my girlfriend get fucked by another guy, Madison came out of our room. "Lucas was the biggest yet. I didn't even bother putting my panties back on. Here, give me your hand." She grabbed my wrist and forced my hand under her skirt and between her legs. Madison's pussy was a wet and sticky mess. "Isn't there so much cum?"

I pulled my hand back and looked at Lucas's cum sticking to my fingers, trying to wrap my head around this.

Madison continued. "Well, sweetie. Now that I've been able to try a variety of different sized penises, I can say with certainty that I'm a size queen. Comparing the smallest, yours, with the biggest the result is clear. It's not just that they feel better or that I have a preference, I literally have a kink for big dicks. Seeing a big one actually turns me on." As though there had been any doubt since this entire thing began. Ever since Madison admitted my penis was too small for her, she's made no attempt to hide that she liked the big ones more. "Now, I'm not going to start fucking a ton of guys left and right. I know I recently have been doing just that, but that was for the sake of experimentation. However, going forward you won't be my primary sexual partner and I will need to have a friend with benefits." Madison sat down and put an arm around me. "And I realize this is embarrassing for you, but I want that to be your best friend's little brother. I know Lucas is only 18, but he's mature for his age. And even though he's younger than you, his penis is a lot bigger than yours."