Prom Night Tryst (The Beginning)

My little sister is a good looking gal. Always has been. My older brother and I never had any problems attracting ladies, so it would make sense our sibling of the opposite gender would also be attractive. We all grew up playing sports, and being active and athletic was just natural in our family. Thomas is four years older than I am, and Alyssa is 18 months younger, but two years apart in school. She was always the baby of the family, and I've always been particularly protective of her, being the only brother close enough in age that we went to high school together.

My friends learned pretty early on that I didn't find humor in their comments about her being hot, pretending they were going to ask her to go to homecoming dances with them, or anything along those lines. The age difference was close enough that we mingled in the same social groups to some degree, and I even dated girls in her grade a time or two, but never any of her close friends. My friends knew better than to even try going out with her, too. She occasionally hung out with guys in my class, but they knew better than to be anything less than respectful to her. It went unsaid for the most part, but they knew I'd beat the shit out of them if they crossed the line with her.

I also made sure to be respectful when it came to dating girls she was friends with, and a couple times even chose not to pursue girls she was friends with to avoid making her uncomfortable. She had one friend in particular who was always flirting with me from the time we were in middle school that I secretly always had a crush on. Her best friend, Madi, played soccer with her, was in the same dance classes growing up, and spent a lot of time around our house. Alyssa became well aware of her friend's attraction towards me, and as time went by, mine towards her. I never wanted to get in between their friendship, but I'd be lying if I said I didn't want to get with Madi.

During the fall of my senior year of high school, my sister knocked on my door one day and I told her to come in. I was reading a book lying in bed, and Alyssa crawled up and sat against the headboard beside me.

"What's up, sis?" I asked her.

She was straight to the point. "You know Madi likes you, right?"

I pretended to be surprised. "Well I'd hope my sister's best friend likes me! What kind of brother would I be otherwise?"

"No, dummy, I mean she likes you likes you. She thinks you're the hottest guy in school. Yesterday she was joking around and said if she married you one day that she and I would be sisters forever. You know? Like sisters-in-law?"

"Don't worry, Alyssa. I wouldn't do that to you. She's your best friend. I wouldn't take that away from you. Madi's pretty and a sweetheart, but you come first in my life and always will. I promise."

"Well, honestly, all the guys in our grade are immature and dumb anyways. I can't believe I'm asking you this, but what do you think about her, like aside from just my friend?"

I was taken aback.

"Are you asking if I'm interested in her romantically?"

"Yeah. Like have you asked anyone to prom yet?"

"Uhm, not yet. I haven't really thought much about it."

"Well, I just want you to know that I wouldn't be mad if you did. I know you would treat her right and wouldn't do anything to get in between our friendship. So I guess what I'm saying is you have my blessing."

"Are you sure, sis? I don't think I'd feel the same if my friends asked you out. Now I feel like a hypocrite."

"I'm sure, Jack. I'm not pressuring you to do anything, but I'm honestly saying I'd have no problem if you and her got together. You've always had chemistry and it would be kind of cute, even if it was weird at first. Just think about it."

Alyssa got up and walked out of my room and left me to my thoughts. It didn't take much time for me to get on board with the idea. I already had Madi's number, and I called her and asked her to prom that night.

The awkwardness of the situation faded pretty quickly, and by the time prom came around three weeks later, Madi had become my girlfriend as well as my sister's best friend. We all hung out together a lot as Madi and continued dating after I graduated and enrolled at the local university the next fall.

Our friend groups basically became one, and Alyssa and her friends spent a lot of time at my dorm and then at the off-campus house i rented after freshman year. Another weird coincidence, or maybe one of the reasons Alyssa and Madi had always been so close is that they shared the same birthday, June 9th. Madi and I were going pretty steady by the time I finished my freshman year of college, and the two girls were still best friends.

Naturally, they wanted to have a big double birthday party when they turned 18, and Alyssa asked if we could have it at my house. It was the only way my mom and dad would allow her to stay out overnight, knowing I wouldn't let anything happen to my little sister. We were all looking forward to it. I was especially eager for the day to come. Madi and I had been together over a year by then. due to the fact she was my sister's best friend, and because she was 17 years old throughout our relationship to that point, we had yet to sleep together. I had hooked up with a couple girls before we started dating, but Madi was still a virgin. We had chose to wait until she was 18 to change that, even though the consent laws in our state didn't require us to. The waiting and anticipation made it even more exciting.

The party was a lot of fun. Everyone was playing drinking games and it didn't take long for Madi to start giving me doe eyes, and I could feel my prick harden inside my pants. She was being touchy-feely with me more so than usual and I was beyond horny. I texted her, "my room," and casually walked away from the main group and made my way to my room upstairs.

Minutes later, Madi entered and we began passionately making out immediately. My hands found her perky breasts underneath her shirt which I slid off of her. I unhooked her bra and began licking her nipples as my hand slid down the front of her pants and under her panties to her smooth wet slit. My finger easily poked inside her opening and she gasped as I slid past my knuckle into her pussy. I wasted no time and pulled her pants and thong off and buried my face in her virgin sex and licked up and down her slit then nibbled on her swollen clit as I fingered her.

Her hand found my cock and she wrapped her fingers around it and told me to lie back. She put her mouth on my cock and I was in heaven. Before I allowed myself to come I told her to stop and lay her flat on her back and led my cock to her opening and slowly entered her virgin pussy. Just then we heard a knock on the door, and the handle twisting. I pulled her into a spooning position and covered us up with the blanket.

"Thank god you guys are here!"

It was Alyssa's voice. She walked over and sat on the bed beside us.

"I'm druuunk!" she giggled. "Is it ok if I sleep in here? I don't feel comfortable passing out with all those people around."

"Of course you can, Alyssa," Madi replied.

My cock was still rock hard, pressed against Madi's ass from behind as Alyssa giggled and talked about the different boys hitting on her. She snuggled in closer to Madi and I draped my arm across both of them as I pulled the blanket tighter over all of us.

"Ugh, I'm too warm. I'm gonna take off my sweatshirt," my sister said as she crawled out from under the covers.

I could see her silhouette as she pulled the hoodie over her head. I fingered Madi's soaking pussy gently from behind as she breathed heavily.

"Take off your jeans, too, babe. It's hot I'm here," Madi said softly.

Alyssa giggled. "Are you sure that won't be weird?"

"It would be weird if you didn't," I replied.

She laughed and slid her jeans off before crawling back into the covers. As she was standing I had guided my cock to Madi's entrance and slid slightly inside as she pushed her ass back towards me. When Alyssa snuggled back in I draped my arm across both girls, my hand landing on Alyssa's belly, covered by her t-shirt.

Madi lifted her leg and lay it over Alyssa, providing me clear access to fuck her from behind. I pushed in slowly and she moaned quietly. My hand went under Alyssa's shirt and I reached up and felt her naked breast as I slowly pumped my cock into her best friend. She said nothing.

"Did you hook up with anyone?" I asked her. Her nipple was rock hard as I pinched it gently.

"Uhm. No."

Alyssa turned around and faced us, looking me in the eye as I fucked Madi from behind. I stared into her eyes as I thrust my cock inside her friend.

"Maybe Madi will give you a little kiss. I don't mind sharing."

Madi turned back and looked at me. I just nodded.

"Alyssa, sweetie, come closer."

Madi was practically whispering.

My sister looked uneasy, but she did as she was told. They kissed each other lightly at first. I reached over and grabbed Alyssa's panty covered ass. Her eyes opened and darted at me before she closed them and kissed my girlfriend more passionately.

"That's more like it."

I became more bold and slid my hand underneath her panties to grab her bare ass. My cock was as hard as it could be as I gently fucked Madi from behind. I grabbed ahold of my sisters ass somewhat aggressively and let my fingers wander a little bit. I felt the wetness of her pussy as my fingers made first contact. I pushed my index finger lightly into her gash, and she sharply inhaled as my finger disappeared two knuckles deep inside her.

I fingered my little sister as I continued fucking Madi. Alyssa draped her leg over her best friend, allowing me free access to slide my fingers in and out of her. At a certain point I was putting more effort and vigor into finger fucking Alyssa, while my cock barely moved inside her friend. My sister was panting as I let my hand wander her entire soaked crack.

Madi looked back at me, seemingly surprised at how far this has gone. She slid out, repositioning herself on her back, beckoning Alyssa to lick her pussy as she lie spread eagle. I coaxed my sister as well, and soon she was on her knees leaning down between my girlfriend's legs licking her slit. As Madi guided her to play with her clit and get into it, I positioned myself behind Alyssa, sliding her panties all the way off. I made brief eye contact with Madi as I guided my cock into my sister from behind and began fucking her gently at first.

"Oh my God that feels good," my sister whispered.

"You like taking your big brother's cock, don't you?"

I returned the pillow talk as I sped up my pace. The wet smacking noises of my thighs clapping against her ass as I buried my cock inside her became louder and faster.

I had practically forgotten about my girlfriend at this point. I was fully immersed in passionately penetrating the pussy of my dreams. Alyssa bucked her ass back at me as I let my thumb push against her clean shaven ass hole, slowly breaching the tight barrier and inching inside the tightness. She was no longer servicing Madi. She looked back at me as I lustfully locked eyes with her.

"Are you going to put it in my butt?"

"Anything you want, sis!"

"Do you have any lube?"

I looked at Madi for the first time in a couple minutes. "Babe, can you get the lube?"

She seemed in shock as she slid out from underneath us to retrieve what I asked for, handing it to me and watching me lather my sisters crack generously before lining up my completely engorged dick with Alyssa's bum. As I entered my sister's most private hole, it crossed my mind how Madi and I had never had anal sex. But now she watched as her best friend took her own brother's cock in the ass, mouth agape with a mixture of shock and jealousy.

Madi began to put her clothes back on as we fucked each other, lost in forbidden desire for one another.

"I think I should leave."

I barely heard my girlfriend's quiet remark. I was fighting every urge to explode inside my sister. Madi was an afterthought at the most at this point, and I barely registered the gravity of the situation. She was realizing in the most explicit way possible that I was in love with my little sister. This was no drunken threesome anymore. She was witnessing pure incestuous passion, learning her friendship with my sister and her relationship with me weren't nearly as meaningful as she thought. I heard the door open and close but didn't stop my aggressive pounding of Alyssa's ass. Moments later i felt her spasm in orgasm as she screamed my name into the pillow. I pulled out and flipped her onto her back and vigorously rubbed her swollen clit as we began making out.

She grabbed my cock and guided it to her gaping pussy and I was back inside her and pumping as hard as I could again. Just as I was about to pull out and come, I heard the door open. Looking over, a group of our friends from the party stood in the entrance staring at me fucking my sister. Alyssa pulled me back inside her. "Come inside me please."

She either didn't notice or didn't care about our new audience, and I was too horny to care. I buried myself inside her as I sent ropes of cum deep in her virgin pussy while our friends watched. Finally, I collapsed on top of her, looking over to the crowd.

"What. The. Fuck? You guys are disgusting!"

Her friend, Katelynn was disgusted. The reality of what was going on suddenly became ever so real. Our fiends just watched us fuck each other. Everyone would know about this. Alyssa's pussy spasmed on my cock as I looked at the crowd in the entry. I saw the flash of a camera as someone captured our forbidden position. I came again as I looked in terror. This was about to become the most scandalous situation any of us had ever been a part of. I pictured my dad hearing about the ordeal. I looked down at my naked sister with her eyes closed and her big brother's cock inside her. Lust, terror, and shock couldn't quite grasp the enormity of the emotions I was feeling. What the fuck just happened?

To be continued...