My Girlfriend & My Best Friend

By swimfan2.


Andrew and I had been best friends since grade school. We shared the same sense of humor 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 certain credibility. At 18 years-old we were 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 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 discreet about it, but I sometimes noticed what appeared to me to be a 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 hard-on 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 that 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 pubic hair, while 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.

He 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 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, 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 apologizing 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 OK. 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!”

However, 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. Eventually, I stopped apologizing 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 jealous since he was still a virgin, and this made me feel like a badass.


Therefore, we were at Andrew’s 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 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 anymore 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 I 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 boy band 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. Finally, 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. So 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, and the latter was high and tight. The former had already shrunk down to a post-orgasm 1.5” nub. Even I had to admit at that point, and 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. The look actually humbled me 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 paralyzed. 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, ya 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 in 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 pinkie 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 me 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 shame 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 the 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 3.30 am. 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 realized 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 realized the voice of the girl wasn’t Rachel. It was Jen. This was when I realized 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, and 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 apologizing. 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, Simon and I 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 number 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 Simon 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, and then I realized 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 was 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 realized 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, and 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 realize 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 realized 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, and 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, ya 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.

“Nope. Tiny dick.” Jen shrugged. “But haven’t you guys changed together? I mean, don’t you sneak a peek out of curiosity?”

“We’re both pretty discreet, I suppose.”

“Really? Why are you discreet, Andrew?” Jen bashed him on the shoulder. “Embarrassed about your own size?” They both giggled at this. Meanwhile, my stomach was in knots, but my stiff little penis was leaking precum into my briefs like crazy. It felt like I’d cum in my underpants right there.

“Well, no, not exactly.” Andrew bowed his head sheepishly.

“Well, since I’ve told you all about Simon and his premature four incher, let’s hear about you,” Jen said, sitting up now. “I’ve always thought it’s unfair that you men can see us women’s breasts upfront, but we can’t tell what you’re packing.” She paused, “Though, in those jeans, I guess you do get an impression…”

“Really?” Andrew looked down, feigning surprise.

“Unless you got a sock down there. You’re not hard, are you?”

“No, I’m not,” Andrew laughed.

“So tell me, what are you working with, Andy? Six inches?”

“Um… well, honestly, I’m bigger than that.”

“So you’ve measured.”

“All guys have.”

“God, that’s so hot.”

Jen didn’t react when Andrew put his hand on her knee, didn’t flinch or protest. She was starting to blush, though, turning red.

“You think it’s hot that guys measure their dicks?” Andrew asked.

“Sure… well, not when I think about Simon doing it. He always got so angry when it hadn’t grown any, then he’d be pissed for the rest of the night, and I’d have to pretend to enjoy the pity sex I let him have.”

Andrew laughed, “God, he sounds so pathetic, taking it out on you just cos he’s got a fucking baby dick.”

“I know, right?” Jen smirked at the memory. “But you’re stalling, mister. I asked what you’re working with down there. I really wanna know now. Is it… seven?”

Andrew grinned. “Um… bigger than that…”

And I’m thinking: Shit, I knew it! I knew he had a big dick!

“You’re kidding me, right? You’re bigger than Rachel’s huge vibrator?!” Jen’s eyes were wide, disbelieving.

“Well, seven is above average, but it’s not ‘huge’ exactly…” Andrew’s bulge was definitely getting bigger now, his hand had traveled up to Jen’s thigh, and she showed no sign of resisting its upward climb.

“So… what, you’re eight inches then? I mean, that’s twice Simon’s size.”


“I’m actually…” Andrew took a deep breath. “I’m actually ten inches, by around six inches.”


Jen was quiet for a moment, eyes on Andrew’s now huge swollen bulge. Andrew’s hand rested on her thigh just beneath her crotch. Then she looked up into his eyes.

“Can I…” she said.

“What?” Andrew’s voice had a slight laugh within it.

“Can I see it?”

“You want to see my dick?”

“Well, yeah. If it’s really ten inches, I want to see how it compares to Simon’s.”

“Uh… well, I mean, I guess so.”

Jen actually licked her lips. Andrew wasted no time now. He undid his belt and top button and began to unzip his fly. I was breathing heavily, as too, I noticed, were they.

“So, you want me just to take it out?” he asked now.

“Yeah… go on.”

Andrew slid his jeans down slightly, revealing a massive bulge in his tight red jockey shorts.

And then he slid those down too.

From out of Andy’s jockeys sprang a dick bigger than any I’d ever seen – bouncing slightly, growing even harder and stiffer now that it was free. His foreskin was drawn back slightly, revealing a huge head, his long shaft was thick and girthy. I could see large, egg-sized balls beneath his enormous cock, and above that, an impressive, thick bush of pubes. I actually gasped.

Jen’s mouth was hanging open. She looked up from this incredible piece of meat and met Andy’s eyes. He was smiling innocently as if it were no big deal, but I could see Jen was absolutely stunned.

“So, um, how does it compare to Simon’s dick?” Andrew asked, grinning now.

“It’s… I mean… It’s just so big!” Jen said, looking back down at Andy’s massive, swollen cock.

Andrew laughed, “Well, thanks! I guess I knew I was pretty big down there.”

“It’s… It’s so much bigger than Simon’s! I mean… I just can’t believe how much… bigger…” Jen was still having trouble forming words when Andrew leaned forward and kissed her on the lips. At first, she seemed surprised, but after a moment, she relaxed into it and began to return his kiss – a kiss which lasted around ten seconds as Andrew’s dick became fully hard, and I realized he hadn’t been exaggerating. He was at least ten inches long and incredibly thick.

When they finally broke contact, Andrew looked away. “I’m sorry, I shouldn’t have done that, Jen. It wasn’t really fair.”

Jen leaned forward and kissed him again, and this time there was more passion. The kiss seemed to last a long time, during which I noticed Andy’s monster cock twitching several times, and after it was over, she whispered something in his ear, stood up, and began to undress.

Andrew seemed to waste no time sliding off his jeans and jockeys, and soon they were both naked, breathing hard, looking into each other’s eyes as they stood facing one another, Andy’s fully erect cock jutting out between them. Andy looked to be in better shape than I’d remembered, and I wondered if he’d been working out. He’d never been a gym rat, but it was clear to me then that he had more muscle tone and definition than I had…

The front of my briefs was now soaked with pre-cum, my stiff little dick making a tiny tent in the material, and I was still shaking, trembling as I realized that my best friend was about to fuck my girl with his massive cock.

“Are you sure you want to do this?” Andrew asked Jen, his voice hoarse.

Without saying anything, Jen reached out and gently took hold of Andy’s thick shaft, and he exhaled softly at her touch. Her slim, delicate hand looked tiny wrapped around his engorged cock – it was so thick she couldn’t get her hand all the way around his shaft.

“Is it true you’re still a virgin, Andrew?” she asked him now.

“Uh… well, yeah,” he said, blushing slightly.

“Well, in a way, so am I,” she said, smiling. “I mean, I could never really feel Simon’s penis inside me, and he definitely never made me… you know… cum.”

“Think you’ll feel this?” Andy replied, grinning.

With that, Jen pushed Andy playfully onto the bed and climbed on top, straddling him, his huge hard dick sticking upwards as he lay on the bed, slapping against her flat stomach. Andy reached into the drawer of his nightstand and pulled out a condom. Squinting in the half-light, I could tell it was a Magnum XL.

“Wow,” Jen said, looking at the tightly wrapped square packet. “Extra-large makes sense!”

She leaned down and kissed him again, and Andy got busy unwrapping the condom. Jen took it out of his hands and slowly unrolled it over the full length of his hard cock, but it didn’t quite reach the base where his shaft met his large balls.

“Oh fuck, Andy, I want you inside me so much right now!” she gasped, staring down at his massive dick.

As I stood in the hallway, my stiff little prick still hard and desperate for release, I watched as Andy slowly pushed his cock into her eager tight pussy. I saw her expression crease in pain as he slid his cockhead inside her, and he paused and asked if she was okay. Even just the head of his cock was more than I’d ever been able to offer her, bigger than my entire package.

Jen nodded, and Andy continued to work his dick into her wet cunt, eventually pulling out slightly and then pushing back in, creating a rhythm as he managed to get another inch inside each time. The initial pain Jen had experienced seemed quickly to subside and give over to relief and then pleasure. After a few minutes of this, Andy was almost fully inside her. It was hard to believe that his cock could fit all the way into her pussy, and I knew that now she’d never be satisfied by a guy my size. I could see that Andy’s dick was stretching her out, how she responded by arching her back and thrusting into him, pumping her hips and loudly moaning in pleasure, hair falling over her face as she bucked up and down.

They were both sweating, their bodies glistening in the lamplight. Andy was grunting, running his hands across her thighs as he fucked her, and Jen’s moaning, interspersed with calling his name – “Oh Andy, oh fuck, yes, fuck me!” – Grew louder and soon she seemed lost to the ecstasy his huge tool was delivering her. I watched as Jen came loudly, her pussy juices drenching the base of his cock and running down his large hairy balls, but he didn’t seem even close to finishing. They kissed again, Andy reaching up and massaging Jen’s full tits, tracing his fingers around her stiff nipples, causing her to gasp and moan, his dick still pumping in and out of her pussy – she arched again, and I could tell she was on the verge of another powerful orgasm.

Without realizing it, my hand had reached down towards my own tiny dick, and I had started to fondle myself inside my little briefs. My penis responded immediately, and after a few light strokes, my eyes fixed on the image of my girlfriend and my best friend having what seemed like the best sex in the history of fucking, I blew a load right in my underwear, my legs buckling as I let out an involuntary moan. Simultaneously, Jen called out Andy’s name as she also came. I felt a sense of almost overwhelming humiliation, blowing my load in my tighty whities as my girl was pleasured so profoundly by my hung buddy, but somehow it excited me so much that I just couldn’t help myself. The pleasure flowed through me, my legs feeling weak as I experienced one of the most powerful orgasms I’d ever had.

Just then, the outside security light suddenly lit up through the hall windows. Maybe it was a cat walking across the garden lawn. I gasped all of a sudden, and the hallway was bathed in pale white light.

Jen had her eyes closed, and she was so into Andy’s cock at that moment that she might as well have been on the moon. But Andy’s eyes were open…

He turned then and caught sight of my reflection in the mirror through which I had been spying on their fuck session. My hand was still inside my briefs, covered now with my own cum as I groped myself. He looked almost disbelieving at first, staring at me as I stood in the hall almost naked in my cum-soaked underpants. But then his mouth formed into a cruel smile, and he slowed down his near-continuous thrusting. I looked back at him, uncertain how to respond, when he suddenly pushed his hips back into Jen, pumping his enormous hard cock back into her dripping cunt. She let out a gasp of pleasure, her eyes still closed. He continued to perform a series of short thrusts in and out of her pussy as he arched his eyebrows at me and grinned, Jen clearly enjoying this change of pace.

My legs refused to move. I stood rooted to the spot. Andrew slowly and deliberately continued fucking my girlfriend. Smiling, he stared at me, and I stared back at him…

Silently he mouthed the words: “She loves it.”

Finally, I forced myself to slowly back away, my body still trembling at what I’d just witnessed. I withdrew into the darkness of the stairs and almost tripped, stumbling as I began to navigate my way back downstairs.

Behind me, I heard Andy laughing.

Back in the living room, I lay on the couch and listened to them fucking for over an hour. I heard Jen cum again multiple times, Andy’s loud groans suggesting that he’d managed several repeat performances as well. My briefs were soaked with my own semen, and my tiny soft penis was totally spent.

The sun was coming up when they finally finished, and I found myself drifting off to sleep. I knew tomorrow was going to be extremely strange. Andy now knew my secret, that I was a liar, that my dick was pathetically small and inadequate, that I couldn’t last in bed and hadn’t even cared about pleasuring Jen. Moreover, he’d now done what I never could, given her the sexual release that she so obviously craved while she’d been with me.

Nothing was going to be the same.


The End.


Leave a Reply

Your email address will not be published. Required fields are marked *

Translate »

You cannot copy content of this page