My New Girl Wants Bigger

I looked down as Kayla's head bobbed up and down on my cock. This was only our third date, so I was excited to be getting a blow job! Kayla had let her eat me out on our second date. She was going to give me a blowjob right after, but once she worked my cock out of my pants, she hesitated and suggested we don't take things too fast. It didn't bother me. Kayla was kind, funny, smart, and smoking hot. Way out of my league, so I'd do just about anything she wanted.

Kayla must have sensed I was getting close and broke the BJ and told me. "Hey Ben, just give me a signal when you are going to cum. I don't really like cum in my mouth, so I'll finish you with my hand into a towel."

I nodded and Kayla returned to the BJ. Her mouth felt amazing and less than a minute later I croaked out, "I'm close."

With that, Kayla pulled my cock from her mouth, pulled a towel over my cock and continued stroking it. "That's it. Be a good boy and cum for me." She said in an almost nurturing tone.

It was weird. No woman ever spoke to me like that during something sexual before. It felt almost a little demeaning, but for some reason it turned me on more and I came into the towel instantly.

"Good boy!" Kayla said, patting my softening cock through the towel.

For the month or two, our sexual encounters were largely limited to oral. I'd go down on her every time, but she'd only go down on me maybe every third time. Each time I'd have to finish in a towel. There was one thing I didn't understand though. We spoke a lot about previous sexual encounters. Kayla would speak a lot, often with a lot of excitement, about past sexual acts with other guys. Including swallowing their cum. If she loved it so much in the past, what changed now? Still, she was out of my league, so I didn't complain. It was kinda hot hearing about her past encounters as well.

Finally, after a few weeks and lots of conversation, we agreed to have sex. We were both naked. I had just gotten her off and Kayla had my cock in her hand. She gently stroked it to get it hard, then paused. "Do you mind wearing a condom?" She asked. "I'm on birth control, but it's easier cleanup and less messy."

I happily obliged, I had brought some with me, assuming we'd be using them anyway. Unfortunately, I only lasted a couple of minutes. Being the awesome girlfriend that she was, Kayla didn't complain and reassured me that it was good. I then went down on her and got her off with my mouth.

Over the next three weeks we continued having sex, and I'd eat Kayla out both before and after. The blowjobs completely stopped, but since we were having sex, I didn't care. I thought things were going great! Until one night we were snuggling after sex.

"Can I talk to you about something? Kayla asked. "You probably know that you're a little smaller than average, or rather a lot smaller than average, right?"

I was caught off guard, a bit embarrassed, but also fully aware Kayle was correct. "I guess. I mean I've measured it and looked up the statistics online."

"Ok great, so you already know then. Out of curiosity, what is the actual measurement? Like 5-ish?"

"Um, four and a half." Honestly, four and a half inches was even a bit of a stretch, but this admission was already humiliating enough.

"That makes a lot of sense! Before you, I don't think I had ever been with anyone below 6 inches. Even like when I first started dating in high school. So I figured you were in that smaller range." Kayla said. I instantly felt even smaller with this humiliating information.

"Anyway, I really like you. We have a great time. You're cute and treat me well. And you are actually really talented with your fingers and tongue, but I'm struggling with your size." Kayla said, continuing to explain.

"To me, sexual satisfaction is really important. To get my needs fulfilled, I really need to have penetrative sex where I feel full, you know? I was hoping I could just adjust to your smaller size, but I can't get off during intercourse with you. I need a larger size."

I just nodded along silently. I mean, how do you even respond to being told your penis is too small to get your girlfriend off?

"I want to find a way to make it work. Since we just started with dating, I was hoping we could make an arrangement. I'd like to have a partially open relationship. I don't want to date anyone else and sorry, but I don't want you having sex with other girls. I'd be too jealous. But I'm hoping to have sex with other guys to kind of fill in that missing piece in our sex life. What do you think?" Kayla asked.

"Um, I don't know how I feel about this." I replied.

"Come on babe, please? You're great, and I really want to find a way to make this work. Do you think you can do that? Work with me to try to find a solution? I promise I'll be transparent about everything and keep you involved. What do you say? Can we give it a try and give our relationship a chance?" Kayla asked.

I felt like I was being put on the spot, like I didn't have time to think things over. But I didn't want to break up, so I nodded and said, "ok."

- -

Only a few days had passed, and Kayla already had prospects. She had been texting several men that she met who knows where. One in particular had really caught her attention.

"Ok, so I've been sexting this guy. His name is Rick. My hope is to ease you into this, so I want you to look at these. These are a few videos I sent, mostly me masturbating. There is also a picture of Rick's cock. I'd really like to you look at it. I think it'll be easier to adjust if you can see the penis that will be inside of me."

It was weird looking at a picture of another man's cock on my girlfriend's phone. I've seen pictures of other dicks before, but it's weirder seeing an actual dick pic, especially since it was intended for my girlfriend. It was emasculating as well. This guy wasn't just ripped, but his dick was way larger than mine!

"So this first one is just showing his naked body. His penis isn't hard yet or anything, but you can see it's definitely bigger. And you might find this interesting. Look at how it's hanging down. Now, maybe you don't really know this, because I don't know how many other dicks you've seen. So, when you are soft, you know how your penis sticks straight out?" Kayla asked with her thumb and finger help about an inch apart. "Most guys aren't like that after they've hit puberty, actually I've never been with a guy that didn't hang down when soft. Well, other than you. Rick is a little bigger when soft than normal. You can see his penis hangs down past the bottom of his balls. Most guys probably hang down even with the bottom of their balls. I know yours doesn't hang down, but if I pushed it down, it would probably go only halfway to the bottom of your balls, maybe not even that far. Really interesting, right?"

"Um, yeah." I replied meekly.

"Ok, so in this next one, Rick is hard. Why don't we pull yours out to compare? I'll give you a handjob. It'll be fun!"

Kayla unzipped my pants and pulled them down with my underwear, then took my dick in her hand and giggled. "Hi there little fella!" She said.

It didn't take her long to get me hard. "Isn't it funny how I need to give you a handjob? Like with my thumb and fingers?" Kayla asked. "If I were to simply wrap my hand around it like I would with a normal guy, it disappears. See! Like a magic trick!" Kayla laughed at her joke. "Ok, so let's get to comparing, shall we?"

Kayla held up her phone and looked back and forth at both penises.

"So a lot bigger right?" Kayla asked with a little laugh. "He is a little bigger than average, but barely. I'd probably consider him on the larger side of average. Like six and a half inches, at least a couple inches longer than you. He's a lot thicker than you, but believe it or not that's actually average thickness."

Great, so I'm dwarfed and humiliated even by an average sized guy. But Kayla playing with my dick sure felt great.

"Anyway, I've noticed how you get hard when I tell you stories about my sexual adventures."

"No, um, I don't-" I started to say before Kayla cut me off.

"Shh, it's ok! You don't need to be embarrassed. And now, you don't need to rely on old stories." Kayla said, holding up another closeup of Rick's cock. "I'm having this inside of me tonight! Isn't that exciting?" Kayla squeezed my penis as she asked, and to my humiliation, I came immediately. "Well, look at that! Good boy! Although, you should warn me next time. You know I don't like getting your cum on me." Kayla then casually wiped my cum off her hand using my shirt.

--

We had spent the rest of the day getting ready for Kayla's visitor. I even helped her with shaving, getting her pussy totally smooth for Rick. We were waiting for him at my apartment. She chose my place because I had a larger bed.

"Ok babe, Rick is going to be here soon. I'll do introductions then will take him into your room while you wait out here. Eventually you'll be able to watch, but I know this will be a lot for you to get used to, so we'll ease you in step by step."

We heard a knock and the door and Kayla answered it, letting Rick in. "Hey babe, come meet Rick. Rick, this is Ben, my boyfriend."

"Hey, Ben, Kayla has uh, told me a lot about you." Rick said, shaking my hand.

Kayla giggled, "yeah don't be embarrassed babe! Rick understands why he's here and that you have a really small penis. So it's like you aren't even strangers. For example Rick, Ben here has been studying the pictures of your penis very closely. He could probably draw it from memory."

By now, my face must have been as red as a strawberry. Kayla was embarrassing me on levels I never thought imaginable.

Kayla took Rick's hand, "ok, let's go!"

I waited outside of my own bedroom listing as another guy fucked my girlfriend. I thought I knew what it sounded like when Kayla was getting off, but this was on another level. I'm sure the neighbors heard her screams of pleasure. On the bright side, maybe they'd assume I was the one getting her off.

After what seemed like an eternity, Rick came out of my bedroom. He looked at me and said, "Kayla asked me to send you in. Uh, anyway... Thanks bro, have a good one."

As he walked out, I heard Kayla yell from my room, "thanks Rick! I'll text you later!"

I entered my bedroom, and Kayla was naked on my bed, with her legs spread. Her pubic bone area was covered in a pool of cum. It looked like a lot to me, hard to believe it came from one guy.

"I had Rick pull out and cum on me this time, again, to ease you into this. It's ok, come closer." Kayla said, motioning for me to approach. "I'm sure you haven't seen another man's cum in person. It probably looks like a lot to you, but this amount is pretty typical."

"Go ahead and touch it. Feel it with your fingers." Kayla took hold of my wrist, and moved it to the cum. Texturally, it felt like mine, just more of it. It was such a weird experience, and touching it was almost more humiliating than listening to Rick fuck my girlfriend. "See? It's just cum. Nothing scary, nothing to worry about." She said.

"Now, use your fingers and push it into my vagina." Kayla instructed. I froze. "This will help you get used to the idea of another guy's cum being in me, and since you'll be using your fingers to put it inside of me, I'm hoping it makes it an easier step forward." She explained further.

I supposed on a certain level it made sense, and I was this deep into it, would seem like a waste to back out now. I scooped up some of Rick's cum from my girlfriend's pubic area, then pushed my fingers into more vagina.

"Mmmm, that feels good. More cum babe." I couldn't believe I was essentially shoveling another man's cum into my girlfriend's pussy. It reminded me that Rick had just fucked her without a condom, something I hadn't even had the privilege of doing. "Mmmm, babe, that feels great. Give me all of Rick's cum. I want it all inside of me."

I complied, and after another minute of fingering her, Kayla stopped me. "Ok, good boy! You took another step forward. I'm proud of you!" Then Kayla smirked. "Good, now put your fingers in your mouth." She must have sensed my hesitation again. She rested a reassuring hand on my arm. "Again, this is all for you. It's all to help ease you into this."

Kayla took me by the wrist, pulling me from her pussy and guiding my hand to my own face. Then gently pushed my fingers into my mouth. She softly told me, "ok, good boy, suck them clean."

I had never tasted cum before. It was mixed with the familiar taste of Kayla's pussy.

"See? His cum doesn't taste bad, right? Especially mixed with me. This is what it'll be like when you go down on me after I have sex with him."

Wait.. She was really going to make me eat her out after letting another guy cum inside of her?

"Good boy! You did really well. See? It won't be so bad! And I have a treat for you. We can have sex now!" Kayla said.

It was a relief knowing after everything I went through that I'd still get to fuck her.

"Don't worry, it might not do much for me, but that doesn't mean I won't have sex with you anymore." Kayla added. While not a huge boost for my ego, I was still happy to get what I could. And once she pulled me in, started kissing me and stripping my clothes off, I was quickly hard and ready for action.

I got up on the bed and positioned myself between Kayla's legs.

Before I could start, Kayla held up a hand. "Hold on! Don't forget to slip on a condom first, silly boy!"

I had really hoped that since she had just allowed Rick to fuck her bare that I'd get the same privilege, but I was too horny to argue and slipped on a condom.

"That's better go ahead." My girlfriend said and I pushed forward, god it felt amazing! Kayla hadn't let me have sex with her in days. I wanted to prove myself after she had sex with Rick, but knew I wasn't going to last long. Kayla's face didn't show any sort of reaction. In fact, it looked a bit confused.

"It's ok sweetie, I said you can put it in," Kayla said sweetly. The humiliation that I was apparently too small for her to feel it sent me over the edge, and I came. "Oh my god did you cum already?" She asked in shock. "I guess you really enjoy our new arrangement!"

"Um, sorry." I said.

"Don't be sorry babe! I've already been satisfied by Rick. I'm not expecting sexual pleasure from your penis. I understand it just isn't built for that! And that's ok!" Kayla said reassuringly. "Now come snuggle. I'll show you some more pics on my phone. Rick is not the only man I've been sexting, and you are in for a treat. The next guy I fuck is going to be huge!"