My Girlfriend & My Best Friend

Andrew and I had been best friends since grade school. We shared the same sense of humour and listened to the same bands, and we were both known pranksters at school. While not exactly popular, we were adept at making our schoolmates laugh and this gave us a certain credibility. At 18 years-old we were pretty inseparable.

While I was definitely the better looking out of the two of us (Andrew still had traces of teenage acne) there was one area where I was fairly sure he'd have me beat. While I couldn't be certain, having never seen him fully naked, I was often curious whether he had a bigger dick than me. We didn't talk much about that kind of stuff as it was considered pretty gay, but since I measured my own cock regularly, I knew I was pretty damn small down there. When we changed for gym class or stayed over at each other's houses, we were pretty discreet about it, but I sometimes noticed what appeared to me to be a pretty sizeable bulge in his tight jockey shorts, and I was at once jealous, excited and intimidated that he might out-man me where I knew it really counted.

My hardon measured a pathetic 4", small even for a kid several years younger than me. I'd even quit the swim team since soft my penis was barely 2", and the regulation team speedos were an embarrassment. I'd only recently grown pubic hair too, having waited until I was 16 before a light dusting appeared above my little cock. Having to wear tight speedos which clearly showed the outline of my tiny penis and small balls, then showering naked with other dudes who had manly cocks and thick bushes of public hair, whilst I still had the hairless penis and small, partially retracted balls of a child had convinced me to hang up my swimmers. After one of my teammates wandered up to me in the locker room, his cock swinging between his legs, a respectable bush of pubes above it, glanced at my hairless eighteen year-old boy dick, and handed me his little sister's bikini bottoms saying, "Try these on for size, your speedos are way too baggy dude," my decision was final.

Somehow I'd managed to start dating despite my concerns over my little dick. Jen was a nice girl, brunette, slim but with a great ass and fairly big, firm tits. We'd both been virgins when we'd met, and had waited a few weeks before finally having sex.

The night of our first time was awkward. First of all, the condom didn't fit.

"Did you get extra large or something?" I whined. "It won't stay on..."

"No, they're just regular ones," Jen replied, looking puzzled.

"Well I swear these are meant for a porn star or something." I said, complaining as Jen tried to bunch the thing down on my stiff little penis.

Finally I managed to fix the loose condom on more securely and got on top of Jen, ready to rock her world. No sooner had I entered her though, and started thrusting and humping for all my worth, than I suddenly blew my load, letting out a girly whimper and apologising wildly.

"Oh fuck yeah! Oh yeah! Urgh... Oh my god, I'm so sorry..."

"Did you really just finish?" she asked, disbelieving.

"Um, yeah. I'm so sorry. I just couldn't help it..."

"Oh... well. I mean, that's okay. Next time you'll last longer." She sounded so disappointed.

"Did you cum?" I asked.

She smiled and shook her head.

"It felt really nice, but no I didn't. I'm sure I will next time though!"

But the next time was a repeat performance.

In fact, every time I fucked Jen I would cum prematurely, sometimes in seconds, and I could tell she could barely even feel my dick in her. She would lie back and look bored, then make a soft little gasping noise as I loudly squirted my load, trying to convince me that she'd climaxed too. This became our sex life, and if Jen didn't mind it was probably because to her my desperate, horny teen boy humping sessions were more of a mild inconvenience than anything else - and they were always over so fast. Needless to say I stopped apologising for cumming fast.

In fact, after a while I began to think of this as 'good sex', and would initiate fucking whenever possible. I guess Jen thought this was how sex should be too, since she'd usually relent and let me fuck her whenever I asked. I even bragged to Andrew that our sex life was "Awesome" and that Jen "Loved it." I could tell he was pretty jealous since he was still a virgin, and this made me feel like a badass.

--

So we were at Andrew's parents' house, getting drunk, being loud teenagers and probably making fools of ourselves. It wasn't a big crowd, maybe eight or nine of us, all getting tipsy from his parents' liquor cabinet. They were away on vacation somewhere, so we had the place to ourselves.

Jen had been moody for a couple of weeks now. In my oblivious state I didn't really consider why, and while in hindsight it's easy to see that she was incredibly sexually frustrated with her selfish, quick-shooting underhung boyfriend, I think I assumed she was just being weird.

As we sat around in Andrew's living-room, chatting about music and films and other random stuff, I found myself staring at this hot girl Rachel's impressive cleavage and feeling increasingly horny, my stiff little dick was rock hard in my briefs, not that anyone would notice.

Eventually I couldn't take it any more and started bugging Jen, hassling her to go upstairs with me so we could do it in one of the spare bedrooms. I could tell she didn't really want to, but guess she figured it was better than me pestering her all night.

"Where are you guys off to?" asked Andrew.

"None of your business," I replied winking, giving Jen's ass a little slap. I didn't see her scowl.

Andrew grinned, "Have fun guys!"

We headed upstairs together and found a guest bedroom, or maybe it was Andrew's little sister's room as there seemed to be boyband posters covering the walls. I didn't care, I was super horny and rock hard, quickly taking off my shirt to reveal my thin, smooth, hairless torso. Jen carefully undressed as I threw my clothes on the carpet, my undersized, boyish little boner sticking up at its full four inches and already dripping precum.

As we lay on the bed I started my usual fumbling excuse for foreplay, squeezing Jen's tits while we made out, but secretly thinking about Rachel's more sizeable assets. I was desperate to fuck, as usual, and pushed Jen down onto the bed, climbing on top of her in my usual missionary position. She obligingly spread her legs to reveal her neatly trimmed, tight little pussy, and I slipped on the condom from a box I'd ordered online ('XSnugger Fit').

I slid my little dick into her, feeling no resistance but noting that she wasn't really that wet. It didn't matter to me since I already felt my orgasm building and began thrusting up and down, grunting and making little moans as she silently lay there. After maybe ten pathetic pumps I let out a loud moan, imagining that I was fucking Rachel and making her cum.

"Ahhh, yeeessss! Ahh, yeah you fucking like that! Urgh... fuck..." I rolled off of her, spent.

What happened next took me by surprise.

"Actually I didn't." Jen said, sitting up and resting her weight on one elbow.

"Huh? What do you mean?" I asked dumbly, trying to figure out what was going on.

"I didn't 'like' it," she said. "But you did, that was obvious enough."

"Um... what, didn't you cum? I mean I thought that was pretty damn good," I said, suddenly sounding whiny and defensive.

"Forget it, it doesn't matter," Jen said, getting up to put on her clothes.

"C'mon, it's not my fault if you don't cum every single time, you don't need to act like such a fucking bitch about it," I said harshly.

Lying there naked I looked down at my penis and testicles, the latter were high and tight, the former had already shrunk down to a post-orgasm 1.5" nub. Even I had to admit at that point, my dick looked absolutely tiny and pathetic, the light dusting of pubic hair was the only sign that my cock and balls weren't those of a boy.

Jen looked down at me now, and she was obviously pissed. Like, really pissed. I was actually humbled by the look she gave me as she slipped on her heels and walked out the door. I noticed a poster of Justin Bieber, topless and wearing a pair of jockey shorts, his bulge looking obscenely huge. It reminded me of Andrew's bulge in his jockeys. I quickly slipped on my briefs, barely making any bulge in them at all, got dressed in the quiet, empty bedroom of my best friend's little sister, and hurried downstairs.

--

"Well, that was quick!" Rachel said, laughing as Jen and I walked back into the living room.

Shit! I hadn't been thinking. We'd obviously gone upstairs to fuck but in total we'd been away for less than five minutes.

"Uh, w-what was quick?" I said, stammering. "We were just talking."

"Yeah, right," Rachel rolled her eyes. "You're totally flushed, Simon, it's obvious what you guys were up to. But holy shit, are you always that fast?"

I tried to laugh, but instead I felt paralysed. I couldn't even speak. Andrew was sitting on a sofa giving me a questioning smile, and Rachel was cracking up. Jen took a seat next to her.

"N-no... I mean. Well, it was a quickie, y'know." I gulped. I felt very alone standing there in front of my friends. It suddenly felt very hot in the living room right now.

Rachel turned to Jen, looked serious and pretend-whispered, "Jen, tell me he's not always that fast."

There was an agonizing pause.

"Actually, tonight was a record, he's usually so much quicker." Jen gave me a look of pure hostility. I mentally willed her to take it back, or at least to shut up.

"Shut the fuck up, Jen! I am not!" I said, sounding entirely unconvincing even to my own ears. Actually I just sounded petulant and childish, like I was about to start crying or some shit.

"Oh my GOD! That's hilarious!" Rachel shrieked. "So what was it, like a minute?" Rachel was cracking up as I continued blushing furiously. Even Andrew was grinning now and shaking his head.

"I sometimes count," Jen said calmly, crossing her legs. "Tonight was... ten seconds? Yeah, I think he lasted ten."

The room was silent for a moment.

"Jen, shut up..." I said. "Why would you even say that?"

"It doesn't really matter that he's so fast," she continued, turning to Rachel. "Since I can't even feel him in me." She nodded towards the flat, bulgeless front of my jeans.

"Don't say that." My voice was hoarse, all eyes on me now. I wanted to disappear.

"Sorry, am I acting like 'a total fucking bitch' just because my so-called boyfriend has such a small dick that I can't even feel him in me? Or that he can't even hold in his cum for more than ten seconds? Well, I guess I am then, but I'm not sorry, because it's the truth. I faked it every time, unless I was just too bored. You never made me cum, never even got me close. And that, up there," she gestured up towards the stairs. "That was the worst sex I've ever had, or ever hope to have, in my entire life."

More silence.

"Wow, fuck, Simon. Guess you guys are finished now, huh?" Rachel was still smiling, but had clearly been taken aback by Jen's outburst.

"You are a fucking bitch, Jen." I said, holding back tears.

"You are such a child," she said, giving me a dismissive look. Her eyes glancing down again to my crotch, she held up her pinky finger, and she carefully said, "In more ways than one."

--

That night I got pretty drunk and passed out on the couch. Andrew had kept Jen and I apart and fed me with alcohol while I loudly complained and tried to dismiss her remarks, embarrassing myself further by insisting to him that, "I do not have a small dick!" I felt shamed that he would ever know this about me.

He said he believed me, that she was clearly angry about something else, etc, etc, but I could tell that news about this would travel around school. I just figured it was a good thing I was off to college next year.

When I woke up it was totally dark out. My phone said it was 3.30am. I was alone in the living-room with a blanket draped over me. I must have undressed at some point since I was only wearing my skimpy white briefs. (Had Andrew undressed me?)

My hangover, already forming, made me wince in pain. I stumbled around in the dark, groaning as the memory of the night before hit me... "Such a little cock that I can't even feel him... can't hold his cum for more than ten seconds..."

And that's when I heard the noise.

Walking through the dark hallway I could see up towards the landing, and it appeared that a bedroom light was on upstairs. I could also hear voices. Curiosity got the better of me and I crept softly up the stairs.

It was Andrew's bedroom light, his door was open and he was talking to some girl in there. At first I smiled, thinking maybe he was finally going to lose his virginity, then I frowned when I realised it would probably be to Rachel whom I had wanted to fuck. Then I remembered that Rachel had heard Jen's outburst and so that ship had probably sailed - Rachel was a known slut and would never fuck me now that she knew I had a tiny, quick-shooting dick between my legs. I silently cursed Jen again; I had really wanted to fuck Rachel at some point.

I continued up the stairs and that's when I realised the voice of the girl wasn't Rachel. It was Jen. This was when I realised that I was trembling, actually shaking with a mixture of fear and excitement. What were they talking about up there?

The thick carpet muffled my footsteps and I was able to stop just outside Andrew's bedroom door. From my position, a wall mirror in the hallway reflected the scene in Andy's room, and I could see perfectly both Andrew and Jen sitting on his bed together, illuminated by the soft light from Andy's bedside lamp. In the darkness of the hallway, they couldn't see me.

"I'm sorry about tonight. I basically ruined your party," Jen was saying now. She had taken her shoes off and was sitting on the bed with her legs tucked under her. Andrew was sitting across from her, his legs stretched out, and, to my horror, the bulge in his tight jeans was on prominent display. I wondered if he had a hardon.

Andrew sighed, "God Jen, stop apologising. It's cool." He actually laughed and sat up, scooting a little closer to her. "But there's something I wanna ask."

Jen flicked her hair, something she always did when she was flirting. "Okay, shoot, I'm probably still drunk enough to answer whatever it is."

Andy grinned. "Well, me and Simon have been friends forever, but we've never, like... been naked around each other, and-"

"You're not missing much," Jen snorted.

"Ah, so you weren't lying about..."

"No, that was the truth," she said firmly.

And I am fucking shaking!

"That Simon's got a small dick, or that he's got no self-control?" Andrew was enjoying this; he was actually leering. Jen was smiling too, relishing this private confession.

"Both!" she said laughing. "Seriously, it's totally tiny!"

Andrew laughed too, "Oh my god, that's kind of hilarious. Is that wrong, to laugh?"

"Not as far as I'm concerned," Jen smirked. "The amount of times I had to reassure him he was 'a good size', I was getting so tired of pretending to enjoy it when he fucked me."

"And the, uh, quickness thing?" Andrew said, inching closer. "How fast are we talking about here?"

"Like I said, usually about ten seconds. Enough for him to hump up and down on top of me a few times before he'd make this totally cringy, girly little moan and finish."

"Damn, that's embarrassing," Andrew said, wincing.

"He'd always say something, 'You like that, huh bitch?', like he was some macho stud. I had to try not to laugh, but it was hysterical. Like he thought he was really 'giving' it to me. But I couldn't really feel anything at all. At first I felt sorry for him, then I realised what an asshole he could be." Jen lay down on the bed now, exhaling noisily as she stared at the ceiling.

"Is that why you blew up tonight?" asked Andrew.

"Kind of," she replied. "Actually I got talking to Rachel."

"Uh oh."

"Yeah, a few days ago, I asked her what it's like when she fucked a guy. I didn't say anything about Simon, but she told me how her orgasms felt, how guys would go down on her and make sure she came before fucking. I guess I realised just how selfish Simon was in bed, like he didn't care at all if I was enjoying it..."

I felt a sudden pang of shame and guilt. It was true, I'd never cared or even given much thought to Jen's pleasure during sex. I'd always try to skip foreplay and get straight to fucking, horny and desperate to cum.

"That's gotta be the guy's number one priority for sure," Andrew had started to lightly stroke Jen's hair. "I didn't realise Simon was so sexually immature. He always said you really liked sex."

"What? Really?"

"Yeah, he'd brag all the time about how his technique was great and he made you cum three or four times a night just from fucking. I actually bought into most of it, even felt a little jealous."

"I can't believe he'd lie like that," she said, sitting up. "Actually, what am I saying, of course I can..."

"Guys are like that," Andrew purred. "Well, some of them. Not all of them."

"Then!" Jen suddenly says. "And then she shows me her vibrator, and holy shit, I basically freaked." Jen turned and looked at Andrew, eyes wide in mock amazement.

"Oh yeah?" Andrew smiled. "Why? Is it... like, big?"

"She pulls it out a drawer and she's like, 'It's only seven inches', and I'm thinking, 'But it's huge compared to my boyfriend!' Seriously, compared to what Simon's working with seven inches is colossal!"

"Yeah, well seven inches is above average," Andrew says, playing it cool. I could swear the bulge was growing in his tight skinny jeans. "I mean six is basically average."

"That's what Rachel said. I guess I was pretty naive."

"So, what's Simon working with exactly? Five?" Andrew asked casually. I suddenly realised my cock was rock hard in my briefs, knowing Jen was about to tell Andrew my humiliating size stats.

"Five? Five I could have worked with. Five would have been a holiday. Simon is four inches, on a good day!" Jen grinned at this, no doubt pleased that she was finally able to talk about my little dick in the past tense now.

Andrew actually looked surprised.

"Really? Four inches?" he said.

"Yeah, Simon actually measures it like daily, hoping it'll grow. Did you know he only just got his pubes?"

"Oh my god, really? I got mine when I was like... eleven I think." Jen looked impressed, glancing down at Andrew's crotch. "But he's really only four inches? I mean, that's like, seriously small. I had no idea Simon had such a tiny dick. It does explain a lot though, I always thought he was overcompensating for something with his bragging about sex and stuff."

"How come you didn't know this about him?" asked Jen.

"I guess he doesn't really like to show it off, and now I get why," Andrew laughed. "I mean I knew from when he did swimming and I'd go to the meets that he didn't show much of a bulge in his speedos, or really any kind of bulge at all come to think of it. Even compared to the junior swimmers it was pretty obvious he wasn't packing much. I felt kinda embarrassed for him, but I just assumed, y'know, shrinkage or whatever."

Embarrassed for me? What the fuck? ... I remembered one swim meet, Andrew coming down to the poolside to commiserate me after I came last in a race, me in my tight blue speedo, feeling awkward being on display like that in front of my bud, him casting a quick glance at my crotch, then looking away... "Sorry dude," he'd said.