I Am Probably Too Late to the Party
by IHateDrFreud
Copyright© 2025 by IHateDrFreud
Coming of Age Sex Story: I go to college but I've never been a social person, so I can't imagine how a game of Truth or Dare with my sister, my brother, and his girlfriend would led to an unexpected revelation and ended up this wild. Oh crap! Everyone has already gone to the party, but me!
Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa Heterosexual Cuckold Sharing Light Bond Gang Bang Orgy Swinging AI Generated .
After months of noisy dorms, overcooked dining hall food that tasted vaguely of sadness, and party crazes, being home was a comfort. The holidays had rolled around. It was winter break, the first time we were all back together under the same roof since summer: my older brother Jason, our little sister Layla, Jason’s girlfriend Vanessa, and I. This was Vanessa’s first time really joining our family for the holidays, and Jason was particularly eager to show her off to us.
Tonight, our parents have gone on their night out, leaving us with the house to ourselves. Naturally, Jason took that as the perfect excuse to throw a private party. Which meant drinks, music, greasy pizza boxes on the counter, and some drinking games, which I had zero interest in.
Jason was half-sunk into the couch, beer in hand, with Vanessa practically draped over him. He was that type of hot guy who spent years on the football field. He made girls turn their heads without trying. Tall, broad-shouldered, with a messy mop of dark hair and a charming face. His confidence was magnetic and effortlessly cool.
Vanessa was laughing at something Jason had said. Despite my brother’s best efforts to include me in the party, the only reason I had agreed to join them was Vanessa. She was a stunning girl with a smile that melted the hearts of young men. Her slender frame was like she had stepped out of a magazine. She had been my masturbation fantasy for months, ever since she started dating Jason. I found myself having a hard time not staring at my brother’s girlfriend too much.
Layla was curled up on the floor with a blanket over her legs and a glass of Tequila in her hand. She was still in high school, but mature beyond her age. She was confident, smart, and had a mouth on her when she wanted to. She was not the kid who used to follow me around with a juice box anymore.
I sat on the other side of the room, leaning back against the wall with a drink I wasn’t really drinking. I was trying to enjoy the sight of Venessa, but I never felt quite as comfortable at any party.
“Alright, Layla, truth or dare?” Jason asked. We’d been playing this boring Truth or Dare game for a while now, and the questions were definitely getting less and less innocent.
Layla rolled her eyes but smirked. “Truth.”
Jason chuckled and leaned forward. “How many guys have you slept with?”
“Asking your little sister that question?” Layla was caught off guard for a second, but then settled back, calm and unapologetic. “Eleven.”
“Eleven?” I exclaimed, unable to hide my surprise.
Vanessa grinned, clearly amused. “No judgment, Ethan. Girls have to have some fun. We don’t want to waste our youth away!”
“Venessa’s right.” Jason leaned in, clearly interested. He then turned to Layla, “So, you’ve got a solid sex life. Come on, tell us more about it. Don’t be shy. I’m pretty sure that’s a lot less than mine or Vanessa’s number.”
“You get only one question, Jason.” Layla shot back with a smug grin. “Nice try, though. My turn. I’ll ask your girlfriend.”
She turned to Vanessa with a sharp little smile. “Vanessa, truth or dare?”
Vanessa’s lips curved up, eyes sparkling. “Truth.”
Layla leaned in, smirking. “Who was the most inappropriate guy you’ve slept with?”
Vanessa didn’t even flinch. “Let’s say ... one of my professors who is fifty-two and married.”
“Oh my god!” Layla gasped, eyes wide. “Did you at least get an A out of it?”
Vanessa smirked. “A-plus. Not for the grade, though. It was more of a situation. His daughter, who used to be my bestie fucked my ex. So, in revenge, I got back at her with her dad. And he is pretty hot, too.”
“Damn, Vanessa,” Layla said with a grin. “You became my favorite big brother’s girlfriend now!”
Jason laughed, tipping his drink toward her in a kind of salute. Layla shook her head with a laugh, clearly amused.
I was shocked knowing that my brother’s sweet girlfriend had slept with someone who was old enough to be her dad to get back at her friend. Jason didn’t look all that fazed. He just nodded, like he’d heard this one before. Maybe he had. Maybe they talked about this stuff all the time, like it was just part of their world.
“My turn,” she said, facing me. “Ethan, truth or dare?”
“Truth,” I managed.
She tilted her head, a playful curiosity in her eyes. “Weirdest place you’ve had sex?”
My cheeks flared. I inhaled slowly. “Uuh ... Well ... I’ve never ... you know...”
“Never done it outside the bedroom?” she prompted.
“Never done it ... period,” I confessed with sadness in my voice.
“Seriously, Ethan?” Layla exclaimed, her tequila glass sloshing dangerously as she gestured.
I felt the heat spread from my cheeks to my neck, but I forced a shrug. “It’s my turn now. Layla, truth or dare?”
“Truth,” she said without missing a beat.
“When did you lose your virginity?” I asked, hoping to throw the spotlight off me.
Her grin widened. “Almost a year ago, when I was babysitting Pam’s little brother.”
I blinked. “Pam? Our neighbor Pam?”
Lily nodded, sipping her tequila like it was no big deal.
Pam had been our neighbor since we were kids. She used to come over for barbecues and birthday parties, and we’d stayed close, especially now that she went to the same college as me.
“So, you lost your virginity ... at Pam’s house? While babysitting her brother?” I said, trying to wrap my head around it. “I hope her parents don’t know that.”
Layla shrugged. “Don’t worry. They’re still hiring me to babysit their son.”
She swirled what was left of her drink and glanced around the room with that same smug grin still plastered on her face.
“My turn,” she said, locking eyes with Jason. “Truth or dare?”
Jason leaned back with a lazy smile. “Let’s go with dare. Why not?”
Layla raised an eyebrow, clearly pleased with herself. “Alright, big brother. I dare you ... to help Ethan lose his virginity and figure out his sex life.”
Jason blinked. Vanessa let out a little laugh. I froze, unsure if I’d heard her right.
“Are you serious?” Jason asked, squinting at her like she might be joking.
Layla just kept smiling. “Dead serious. He’s clearly overdue. And you know a lot of girls. So, help him out.”
Jason looked at me. Then at Vanessa. Then back at Layla. “You want me to, what, find him a girl? Set him up?”
“That sounds like a plan,” Vanessa teased, sipping her drink.
“Come on, big bro,” Layla said, shrugging and flashing a knowing smile. “Remember when we were kids? Ethan was always the last one to learn how to swim or ride a bike. You were the one who taught him everything, helping him figure it out. This ... this is just another time you’ve gotta step up and do your big brother duty.”
I wanted to disappear. My face was burning.
Jason rubbed the back of his neck, clearly weighing it. “You know what? You’re right. Challenge accepted.”
“Guys, come on. This is stupid.” I protested, but none of them looked away.
The night had stretched long, and the house was quiet except for the low thump of music. Mom and Dad hadn’t come back yet, probably still at whatever charity event they’d been talking about. The clock on the wall glowed past midnight, but no one seemed to mind. Jason was sitting back, looking a little more serious now.
“Alright, Ethan,” he said, “I’m not just going to leave you hanging like this. I’ll introduce you to my circle. We have a club where we throw parties. There’ll be girls, drinks, and a whole lot of sex.”
I nodded, unsure if I was excited or terrified.
Layla stretched and gave Jason a knowing look. “You’ve that kind of club in your college? Okay, nice plan, but how exactly is Ethan gonna fit into one of those parties? He barely had any sexual experience. He can’t just walk in as a virgin.”
Jason shrugged. “Guess we’ll have to get you some practice before that.”
Vanessa chuckled, took a slow sip of her drink, and then looked directly at me with a sly smile. “What if I helped?”
The room seemed to shrink around me as Vanessa’s words hung in the air. I swallowed hard, trying to keep my voice steady.
“Helped? Like ... how?” Jason asked.
Vanessa leaned in just a little closer. “Maybe by taking your brother’s cherry. He will learn some tricks in a safe environment. What do you think?”
My heart skipped a beat. Did she really just say that?
“Whoa, Vanessa. You’re serious? You’re my brother’s girlfriend,” I stuttered, the room spinning slightly as the reality of her offer sank in.
“Yeah, why not? Venessa and I have an open relationship,” Jason said, with a mischievous glint in his eye. “And, if you actually join the club, you’re going to be running into Vanessa there anyway.”
Layla tilted her head, eyes narrowing with curiosity. “Wait, hold up. You and Vanessa have an open relationship? And what’s this club you keep talking about? It sounds fun.”
Jason grinned, clearly enjoying the attention. “It’s kinda like a secret society for the wild side of campus. We throw exclusive parties, and the only rule is that what happens there, stays there. And yeah, Vanessa and I met at these parties, so we’re not keeping ourselves exclusive.”
My head was spinning. An open relationship. A secret society. Parties with a whole lot of sex. Vanessa, my brother’s girlfriend, offered to be my first. It was too much, too fast, too ... everything. My brain struggled to process it all. Part of me, the naive, insecure part, was screaming in terror. This was wrong. This was insane. This was Jason, pushing me into something I clearly wasn’t ready for.
But another part, a darker, more desperate part, was stirring. Vanessa. My fantasy. The chance to finally shed this humiliating ‘virgin’ label and enter the real world. I wanted to be like him. I wanted to fuck a lot of girls.
I looked at Vanessa. Her smile was still there, a challenge, an invitation. She wasn’t judging me. She was offering. And then I looked at Jason, my older brother, who was watching me with an expectant and proud look. He wasn’t going to let me down. Not now.
“So, what do you say, little brother?” Jason prompted. “Ready for sex life?”
My mouth felt dry. The words caught in my throat. But the thought of going back to my lonely dorm, to the pitying glances, to the endless cycle of masturbation fantasies, was unbearable. This was my chance, a terrifying, exhilarating, and utterly insane chance.
Layla watched me, “You should totally go for it, bro. I’ve been sexually active for almost a year, and it is so good. I want you to experience it too.”
“Okay, okay, okay.” I managed to croak out, yelling. “Fuck Yeah. I’m in!”
Jason’s grin widened, a triumphant flash. “That’s my boy!” He clapped me on the back, a little too hard, making me wince. “Let’s three of us ride a bike together again, Ethan.”
I nodded, trying to keep my composure. I could not be so sure about Jason, Layla, and me riding bikes together, but I knew that soon, I would be riding Venessa.
To my surprise, the arrangement suddenly happened right away. As I followed Vanessa up the stairs to my room. Layla was asking Jason about his club. She sounded so excited, so eager to join it in college.
Vanessa opened the door to my room and stepped in, the light from the hallway casting a glow on her perfect skin. She turned to me, her eyes sparkling with mischief. “You know, Ethan, I’ve been watching you stare at me for months. It’s kind of cute.”
I swallowed, trying to ignore the way my heart was hammering in my chest. All I managed to say was “Oh?”
“Yeah,” she said, moving closer to me. “You’ve probably thought about fucking me while jerking off, haven’t you?”
I gulped, my throat dry. “Many times,” I admitted.
With a smile, Vanessa began to peel off her clothes. When she was down to her underwear, she looked at me expectantly. “Is this what you’ve been dreaming of?”
I couldn’t believe it was happening. Here she was, the girl I’d jerked off to countless times, standing almost naked before me, asking if she matched the fantasies that had kept me company on lonely nights. She unhooked her bra, and her breasts bounced slightly. They were perfectly full, beautifully natural in their low-hanging shape, and adorned with brown nipples.
Then she slid her panties down her legs, revealing her pussy. It was the first time I saw a real one up close. It was wet, and I could see the shine of her arousal in the dim light. She stepped closer, and I could smell the faint scent of her, something musky and intoxicating. Vanessa lay on my bed, her legs parted, presenting her pussy that my brother had probably fucked countless times to me.
“See my pussy, Ethan?” Vanessa urged, a seductive whisper. “Come. Use it. Fuck me like how you’ve imagined!”
I nodded, my hands trembling as I approached the bed. She reached up and began to unbuckle my pants. My cock was already rock hard, straining against the fabric of my boxers. She pulled them down, freeing my erection.
Vanessa reached down and took my cock in her hand, guiding it to her waiting entrance. She was wet and slick, and my dick slipped into her with ease. Her pussy was warm, and it felt so much better than my hand. I could feel the walls of her cunt gripping my shaft as I pushed into her. I couldn’t believe it. This was it. I was fucking my brother’s girlfriend.
That night, Vanessa let me fuck her three times before my balls were fully drained. I watched my cum running down her inner thighs, while she walked away from my bed, naked and unashamed. As she left my room, I heard her laugh lightly to Jason and Layla, and the door closed with a click.
The next couple of days were a blur. I felt more and more like a man and less like the inexperienced virgin I had been. Vanessa made her way to my room every night. Jason told me to use Vanessa whenever I wanted. So, whenever the house was empty, Vanessa would sneak into my room, teaching me how to fuck a girl properly and letting me fuck her.
When the holidays were over, it was time to go back to college. My sex life with Vanessa was replaced by the chaos of dorm life and the never-ending pile of textbooks. But the confidence I gained after losing my virginity was like a secret power source. I walked into the crowded classroom with my head held high, and I couldn’t help but feel like I’d leveled up in some weird video game.
My major was literature, which was a surprise to no one who knew me. I had always loved books, the way the words could sweep me away from the real world into something more exciting, more dangerous, more ... sexy. And apparently, a lot of girls loved books too, because my classes were full of them.
My core group of friends, all in similar classes, includes Mark, our chubby resident nerd, whose reading list spans erotica, hentai, sci-fi, and superhero comics. Pam, the neighbor, is a striking, boyish girl with an athletic build and good looks. There’s also Becca, an idealist whose captivating sharpness and intellect shine through. Rounding out the group is Anne, easily the most beautiful in our major, with her long brown hair, striking green eyes, and an innocent yet highly sexually enticing face and figure that many men on campus lusted after.
Anne has been my secret crush since my first day in college. It was a miracle that she had even noticed me, let alone become my friend. She was always just out of reach, dating some guy from her high school, leaving me with nothing but admiration and becoming my main jerking material.
But something shifted when she broke up with her boyfriend last year. When they split, Anne stopped coming to class for a week. When she returned, something in her felt different. She was the same gorgeous girl with the same captivating smile, but there was a new way she carried herself. She had become more attractive. Other men and I grew more sexually aware of her, and it was intoxicating.
In the last semester, our professor assigned a paired analysis project for Eastern literature. Randomized groups. Of course, and somehow, I ended up partnered with Anne.
I tried to play it cool when the list went up on the projector, though my heart had been trying to practically sprint out of my chest. Mark gave me a look across the room, his eyebrows raised with a knowing smile. Anne just nodded when we caught each other’s eye.
Later that week, she suggested we work on it at her place.
“It’s quieter than the student lounges,” she said casually. “And my roommate’s away this weekend.”
Her apartment was off-campus, in a quiet residential block with warm lighting and way too many plants. Her room smelled like something soft, lavender or tea or something else I couldn’t name. There were books stacked in corners, cozy throws on the bed, and her laptop sat open on the desk beside two mugs of tea already waiting.
We worked for hours. Talking through passages, writing notes, laughing more than I expected. At one point, we both reached for the mouse and our hands touched. She didn’t pull away immediately. Just looked at me, eyes curious, and then smiled and kept writing.
At some point, the sky outside had turned deep blue, and neither of us had noticed.
“You can stay over if it’s too late to walk back,” she said, not looking up from her screen. “I’ve got extra blankets.”
I must’ve hesitated because she glanced at me and added, “It’s no big deal. I trust you.”
I didn’t know what to say to that. Just nodded.
She tossed me one of the extra pillows and made space on her bed. I lay down fully clothed, staring up at the ceiling. The room was quiet except for the hum of the heater and the soft rustle of her sheets.
She fell asleep quickly, curled up on her side, her breathing steady.
I stayed awake a lot longer, heart pounding for reasons I couldn’t explain. It was my first time sleeping in the same room as a girl. Nothing happened that night, except for the occasional brush of our legs. But the proximity, the quiet intimacy of it, was like nothing I had ever experienced before.
But through it all, Anne remained just a friend. We never talked about that night. We never talked about the way our legs had tangled together. I never told her that my cock had thickened against my jeans all night. We never talked about it, but it was always there, and I felt connected to her more than any friend in our group.
Back to today, the rest of college went on. Boring, predictable, with the occasional thrill of a good book or a decent essay. The days and nights on campus went on the same. I’d sit in my dorm, writing my latest erotic story online. My roommate, a stoic engineering student, was rarely around. The room was my sanctuary, my fortress of solitude, where I used to contain.
And then, one day, I got a text from Jason.
Jason: Are you free this weekend?
Me: Yeah, why?
Jason: I’ve got something you might be interested in. The club’s throwing an intensive training camp this weekend. It’s a leadership development kind of deal.
Me: Why should I be interested in a leadership camp?
Jason: Don’t be stupid, bro. It’s not really a leadership camp; it’s a full-blown orgy weekend. The club’s got a cabin near a lake, totally private. Just a wild weekend of sex and partying.
Me: An orgy? Are you serious?
Jason: Yes, we’re basically running a sex club. We throw this kind of party every month. I know how much you’ve been wanting to find out about your sex life. Now it’s time!.
Me: Every month? Then why didn’t you invite me sooner?
Jason: Look, Ethan, this circle is exclusive; you can’t just walk in. I had to pull a lot of strings to get you cleared. Plus, there’s a strict cap on how many people can join each party. Luckily, I managed to lock in a spot for you this time. We’re in.
The next few days felt like an eternity. The anticipation of what was to come had taken hold of me, and I couldn’t focus on anything else. The classes, the homework, the mundane conversations with friends, they all seemed so trivial compared to the promise of the weekend. The thought of the cabin by the lake, the secret society, and the wild, uninhibited sex was all I could think about.
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