Greg’s Housewarming Party
We started great. I went to work, Dan did his homework and went to class, then Friday nights, he would have a party. Dan wasn’t really any better looking than me. We were both about 6 feet tall, and he had blue eyes to my green. He had black hair to my blonde hair. He had a lean swimmer’s build while I was more broad of shoulder and stout of the chest. But neither of us was out of shape or terrible to look upon. But Dan had one thing I didn’t have. He was incredibly confident.
I don’t know if my lack of confidence was from having a stepdad at a young age, not being particularly great at sports or school, or… more likely because of my diminutive dick. I hadn’t seen Dan’s since we were kids, but mine hasn’t grown much since we were young. I have 4 inches when it’s hard, and it’s about the same in girth. When I’m soft, though, it looks like an acorn with two pea-sized balls. I shave completely bare, but that’s more because I like the feel of it than anything.
I mostly watched porn. My specific favorite had been cuckold porn. Something about a guy with inadequate sex organs marrying a hot girl who later made him accept his inadequacy just turned me on. It probably didn’t hurt either that I had been with 2 girls. One was a pity fuck and the other a steady girlfriend, her name was Emily. The pity fuck was pitiable as I came from going down on her. The girlfriend was pathetic too. I never lasted long enough to make her moan with my dick. But I did get good at following orders on where to lick.
Dan, as far as I knew, had tons of girls. He’d have new ones come over to our parent’s house all the time, or conversely, he’d stay out all night and come home smelling of perfume.
On our first Friday as roomies, Dan was having a party. He invited a lot of beautiful girls over. I tried to sneak off into my room, but two girls were making out on my bed when I opened the door. One was a girl I had been crushing on for a while. Her name was Michelle. She was about 5’4″ with curly red hair, blue eyes, perfect C cup boobs, and a great big-toned bubble butt. I had seen her at the beach once in a thong bikini and almost came in my shorts from her sunbathing. It was beautiful.
The girl she was kissing was pretty as well. I had just met her the other day. Her name was Sierra. She was shorter than Michelle, maybe by an inch or 2. But where Michelle had tits that fit her body type Sierra had enormous melons easily DD’s maybe bigger. Her butt wasn’t as big and juicy as Michelle’s, but it was still pretty nice if her booty shorts were anything to go by. Michelle has pale white flesh kissed with a few freckles, while Sierra has an olive skin complexion.
I didn’t know what to do at first, so I stood there and watched them kiss and grope each other. I felt a rise in my pants. It felt urgent. Not like a normal hard-on, but the kind that consumed your mind completely. I closed the door quietly behind me.
I don’t know if I thought I would get a threesome or if it was a voyeuristic compulsion. But I side-stepped away from the door as quietly as possible and got myself in a good position to watch. I wasn’t hiding, but I also wasn’t announcing my presence. Michelle slowly removed Sierra’s top and her bra.
“Oh my god, these things are beautiful, and your nipples are so cute and tiny,” she said as she started to suck on Sierra’s small dark walnut-sized areolas.
Sierra moaned and grabbed Michelle’s ass. She squeezed it and smacked it. Michelle’s jeans did nothing to hide the ripple effect, and I felt my dick twitch again. The tent in my pants was small, to be sure, but I definitely noticed the tightness of my pants right then. Precum started to collect in the front of my boxers, but they still hadn’t noticed me. Or at least they didn’t say anything.
Sierra took off Michelle’s top and showed her puffy pink nipples. They were almost as erect as Sierra’s. She started to circle her tongue around them and slowly unbuttoned her pants, and tried to maneuver them around her big perfect ass. Once they were all the way down and Michelle was in nothing but her lacey pink thong, my dick spasmed. I didn’t cum, but I was definitely getting close. Sierra got behind Michelle and kissed her perfect cheek, and slapped it. Both Michelle and I moaned at the same time.
They both stopped and looked at me. “Are you Dan’s brother?” They asked, not shocked more an honest inquiry than anything.
“Yeah, I’m Greg, the older brother,” I said like an idiot.
“You’re a lot different than you’re brother, aren’t you?” Sierra asked, still on her knees admiring Michelle’s work of art.
“Umm yeah… I guess so. Why do you say that?”
“Because he would have pulled down his pants and joined us by now, but you’re over there cumming in your pants,” Michelle said, laughing a little.
I stood there trying to think if this was an invitation or if they were simply amused at my timidity compared to my brother. Sierra slid Michelle’s thong down her legs and kissed both cheeks before throwing her back on the bed facing me. Her legs were open, and I saw it. She had a perfectly shaven mound leading down to a moist pink pussy that was begging for some big cock. Sierra instead met her with 3 fingers and a tongue and went to work. Michelle moaned louder than before and then looked me in the eyes.
She didn’t say anything, but I knew this was a test. I hoped that she was so horny that my size didn’t matter. I even reasoned that I was probably bigger now than I realized because of how turned on I was. I dropped my pants and boxers, releasing my dick from its denim prison and showing the girls (albeit just Michelle right at this moment) what I had to offer.
She choked on her laugh, which caused Sierra to stop what she was doing and look behind her to see my fully erect 4-inch snake leaking precum like a busted hose drips water.
Sierra looked back, confused at first, then she began to show a wicked grin. I looked down to see what they were seeing. My dick like it always looked when I was horny. It was its full 4 inches with my circumcised head dripping precum. My balls were fully retracted into my body, signaling how close I was already to cumming, but as she held out her pinky toward me, I bucked my hips forward. I was begging for this humiliation.
I wanted to partake in this sexy pairing of curves and shaved mounds, but even more than that, I wanted them to give me unfiltered opinions on my shrimpy boy dick.
“Oh my god, it’s so tiny and already about to cum. You’re nothing like your bigger brother,” she said with an emphasis on bigger. “Well, what do you want to do, baby dick? Do you want to watch us? Or do you want to help me get this beautiful big bootied babe off?”
“I want to help,” I blurted out, surprising myself.
“I don’t know how comfortable I feel with him touching me, Sierra. I mean, he’s so tiny, it would feel like I’m fucking a little kid. Even if he did buy all this beer for the party, his dick… it’s just so pathetic,” Michelle said in earnest.
And that was all it took.
My dick twitched and started to spurt. Two small ropes of cum shot out of me and landed on my foot. I was still at maximum arousal buy my dick started to deflate into its more normal state. When soft, the only thing noticeable was the tip of my head, and my pea-sized balls hung a little lower. However, they stayed retracted into my body, making it look like I just had an overgrown clit.
“Is that better? Now he looks more like a woman,” Sierra said.
Michelle laughed but nodded her head in assent. Sierra directed me toward her ass, and she dove into her pussy. Michelle was moaning and writing against Sierra’s face as I kissed Sierra’s bare ass.
Eventually, Michelle grabbed onto Sierra’s head and screamed her rolling orgasm to the world. It wasn’t as plump and perfect as Michelle’s, but she did have an arousing starfish staring me in the eye. Eventually, I relented and went from kissing the cheeks to just kissing and licking that. I heard Sierra’s muffled moans as she continued to rock Michelle’s world with her own tongue, and that made me feel good.
Michelle and Sierra switched spits as she started to kiss the inside of Sierra’s thighs leading up to her own clean-shaven moist lady mound. Michelle had her ass up now, looking directly at me. It was magnificent. I was drooling with anticipation, I wanted to make sure it was okay before I started worshipping this work of art, but I also didn’t want to interrupt.
Sierra saw my face and smiled again. “Do you want to kiss her ass, baby dick Greg?” she asked.
“Yes…yes,” I stuttered, still intimidated by it.
“Then beg her to do it. I’m sure she’ll let you.”
“Can I please worship your perfect ass?” I asked with every ounce of humility I could muster.
“You want to kiss, and tongue punch my ass?” Michelle asked, taking a break from Sierra’s inner thighs.
“Yes, please…” I said, bordering all the way into pathetic.
She turned her back to me and planted her face squarely into Sierra’s lower lips while raising her ass toward me. I didn’t skip a beat and went right into worshipping it. I kissed each cheek and thanked her profusely for the opportunity to do so. Meanwhile, Sierra moaned and writhed in pleasure as Michelle’s tongue brought her immense pleasure. Finally, I decided to start licking her perfect hole.
I grabbed onto Michelle’s waist to get in deeper when I heard her moan. I dug my face between her cheeks and licked and entered my tongue inside as deep as it would go for what seemed like both an eternity and seconds. That’s when I realized that my cock was raging once again. This was far and away the most sexually satisfying moment of my life, and my dick was all the proof I needed.
“Oh my god, Greg. You’re such a good ass-licker. Keep it up, and I might let you do this more often.”
I was getting praise from the girl I had crushed on. I was bringing her sexual satisfaction. This was the greatest moment of my life, I thought. That’s when everything went wrong also. The door opened though I didn’t hear it as I was working with complete focus. Sierra and Michelle were both very close to climaxing based on their moans and how Michelle’s pussy was dripping onto my chin and chest. I could feel her burying her own face into Sierra also. Then I felt a hand on my shoulder.
I looked up. My concentration was broken. Not realizing the severity of this situation or the fact that I had just been caught with my face in a goddesses ass or that I obviously was the 3rd wheel here, I made eye contact with Dan.
“Hey bro, thanks for getting her all lubed up for me, now. Can you get out of the way?” he said with a smile, but I could tell in his eyes that he was dictating the terms of me staying in the room.
I was to be an observer from her on. I was thinking about protesting, but I saw him stroking his cock. Still soft. But it was absolutely massive. He was definitely bigger than me, even at this moment where I was leaking precum and making a puddle on my carpet. His girth was frankly more than my length. He was stroking it, so it was hard to say for sure, but I estimated that he was 7 or 8 inches with about 5.5″ or 6″ in girth. I would bet.
I was amazed, as was Sierra. “Hey, Dan. We wondered if the BIG brother was going to make an appearance or if Michelle and I were just going to have get each other off with help from baby dick Greg here.”
Dan got his dick at the maximum hardness and started inserting fingers into Michelle’s ass. He started with 2. She moaned and had to take a break from Sierra’s cunt for a second. Sierra didn’t seem to mind. She just started rubbing her very hard clit. I moved slightly more out of the way and started to tough myself. But I saw Sierra look at me and shake her head no. I placed my hands behind my back and watched as Dan’s member started slapping Michelle’s cheeks. Where I had been kissing and worshipping, he was now cock slapping and biting.
“Are you ready for this?” he asked.
Michelle moaned yes as Dan was pumping his 3 fingers in and out of her hole. He applied some lube from my nightstand drawer (not sure how he knew to look there, but oh well) and rubbed it down the length of his cock. Now I saw it in all his glory. He had to be 9, maybe 9.5 inches long. At least 6 inches in girth, maybe more, definitely thicker than a coke can. I just thought of me putting mine inside a toilet paper roll and not being able to poke out. Michelle bent her ass higher in the air for Dan as he slowly inserted his cock head into her ass. Sierra continued to finger herself and rub her clit furiously.
“Yeah, that’s it, Dan, fuck this sluts big ass.”
Dan started working his cock in slowly. It took maybe about 5 minutes before he was a full 2 inches inside her, but Michelle was screaming. She sounded like she was in pain, but she was telling him to make her his slut.
“OH MY GOD, DAN MAKE ME YOUR SLUT, FUCK ME. FUCK MY ASS HOLE!”
She started to rub herself too, but Sierra noticed and grabbed her wrists. Michelle, not knowing what to do with her hands, started fingering Sierra.
My dick was jumping, and I was humping the air again. I was humiliated and aroused. I wanted to take part, but my timidity was too powerful for me to interject myself the way Dan had.
“Can you believe you wanted to fuck Greg tonight?” Sierra said to Michelle.
I was amazed. Michelle wanted me? And I blew it? ‘Oh my god,’ I thought. But my cock responded with another twitch and more precum coming out the tip. Dan laughed as he was about two-thirds of the way inside of her ass.
“You wanted to fuck, baby dick Greg?” he asked, still slowly pumping himself into her. “What changed your mind?”
“Mmmmm. OH MY GOD. I saw his tiny dick cum hands free, and I knew I’d rather just fuck a girl than his tiny dick,” Michelle said.
I was shattered. Well, I thought I was. My cock responded by shooting a load across the room and landing halfway between Dan and me fucking my crush’s ass.
“Aren’t you glad you held out for this?” Dan asked as he plunged the rest of his cock inside of Sierra’s asshole.
Sierra started moaning, but she hadn’t had the earth-shattering orgasm her friend had. She screamed her assertion that she was indeed happy while she also came like a waterfall onto my floor. Finally, after about 10 more minutes, Michelle tapped out. Dan still hadn’t cum yet, so he moved onto Sierra’s begging lower lips. I continued to stand there as my dick went back down to its sad, soft status. Sierra pushed Dan onto the bed and sat down on his cock facing him. She started to fuck him up and down his massive tool. Dan finally made eye contact with me and snickered once again.
“Get over, bro,” Dan said. “Make yourself useful since you’re the first one to cum twice now on the floor.”
I don’t know why I did it, but I listened to him. I walked over to them. He pointed to the floor, and I got on my knees. I was 6 years older than this kid, but I was following his command immediately right now. On my knees, I made mine over toward him and Sierra.
“Lick my asshole, you prejac baby dick,” Sierra demanded.
And I did without a second thought. Michelle sat beside me and laughed at my inferiority as I repeated my efforts with her on her Sierra. She came up and whispered in my ear, “Your brother used to fuck Emily after you would bust in 3 seconds. I didn’t believe him when he said how pathetic you were. But now I’m glad I listened.”
She started to move her hand over to my now rising dick. She was able to grab my tiny balls and pecker in her small hands. My dick kept getting harder. Michelle cupping my package, noticed I was getting hard. Sierra enjoyed my tongue as I didn’t let Michelle break my concentration, but she enjoyed Dan’s cock more. Every time she went up and down with more force, I was hit in the chest with her juices.
“Are you getting off to being pathetic?” Michelle said in my ear a little louder this time. Then she used her pointer finger and thumb to grab my mostly hard member. “You know I saw my little brother in the shower, and he was bigger than you. He’s not even in high school yet, dude. You’ve really got more of a clit than a dick, don’t you?”
Sierra came down on Dan’s cock one more time as she and he both had enormous orgasms simultaneously. Her fluids squirted everywhere. Both me and Dan got hit. His load, though, went all the way inside her, and as she came down one more time, some got pushed out of her pussy and into her ass. I didn’t react in time. Before I could realize my job was done, I accidentally ate some of Dan’s cum.
Michelle was still stroking me when it happened. “Oh my god, you just ate some of your own brother’s cum. You’re such a little bitch.” she said.
Sierra got off Dan’s softening cock and turned toward me as she sat on my bed with her cum soaked pussy. “Do you want to finish the job? Cement your status as the beta brother?” Sierra asked.
Then Michelle stopped jerking me. “I have an idea,” she said.
She pushed on my shoulder for me to get down on the ground on my back. I did as she wished, wondering and hoping I was going to get to cum again. I wasn’t throbbing yet, but I was definitely hard again. She grabbed my legs by the thighs and lifted them off the ground. My feet were bent back towards my head, and she started to lick my dick.
Not suck but lick, as she had done to Sierra. She licked me for a few seconds, and I started to moan and squirm.
“Yeah, you like having your clit licked, don’t you, Greg,” Sierra said.
Before I could say yes, Michelle had inserted 2 fingers into my virgin ass. She was pumping and licking while I started holding my legs back to give her more room. I don’t know why I did it. It was humiliating. But it felt so good. Within seconds I could feel my balls tightening again.
“Beg for it bitch. Ask her to fuck you like a slut, or I’ll make her stop,” Dan said while Sierra leaned her head against his chest laughing.
“Please, don’t stop, Michelle. Fuck me like a slut,” I begged as Michelle put in the 3rd finger and went deep into my ass.
She was Definitely on my prostate now as she started to press. She stopped licked, sensing I was about to blow. And I did. Rope after rope of cum hit my chest, face, and stomach.
Then she removed her hand, leaned toward my face, and whispered, “Good gurrl,” before getting on my bed with Sierra and Dan.
That night they slept on my bed, and I slept on the floor. This was the beginning of something for me, but I wouldn’t know what for several years.
*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Just remember, even with the limited editing we do, it doesn’t mean any possible major flaws in this story were fixed.