Double Date [Group]

A few years back my girlfriend at the time, Katie, sent me a fairly innocent text:

“hey is Brett still single?”

Brett was a guy who I met through a mutual friend. I rarely saw him in person, but we had been gaming together for years with a squad of dudes, so I knew him well. He’s shy at first, but funny when you get to know him. I like the guy a lot. And he was still single.

“yeah I think so, why?”

“Heather was wondering if I had anyone I could set her up with”

Heather was Katie’s close friend. They knew each other through school. Heather was NOT shy at first, but she’s also pretty funny. She’s extremely bubbly and extroverted. I liked hanging out with her in small-to-medium doses.

“uhh I guess I will ask him and see if he’s interested!”

This kicked off a wild series-of-fortunate-events that eventually culminated in the four of us sharing a bed after a night of partying.

———-

The next time we were gaming, I sent Brett a private message over Steam. I know he’s a shy guy so I didn’t want to ask him in the group chat and put him on the spot.

“hey man, no pressure if you’re not interested, but Katie has a friend who’s single and looking.. she’s pretty cute and fun. let me know if you want us to set something up!”

After a little pause I saw the message in the Steam chat window “<Brett’s gamer name> is typing a message…”. He stopped and started typing many times and after a couple minutes I got the reply.

“yeah sure I’d be interested.. would you guys want to do a double date?”

I didn’t, really. I liked all the people involved, but I felt a bit too old to be sitting through an awkward first date. Nonetheless, I agreed for his sake and relayed the message to Katie.

“OH WOW THAT SOUNDS SO FUN!” she replied, “Let’s all get dinner then go out dancing!”

“Greeeaaaaat…” I thought to myself.

———-

Saturday rolls around. It’s 4 p.m. and Katie is in the shower. I’m horny as it had been a couple days. I strip down and barge into the bathroom. She yelps in surprise as I catch her in the middle of shaving her legs. My dick hardens as I join her in the warm water.

“You can shower here but we don’t have time to do anything, I’m already behind on getting ready!” It’s 4 p.m. How could she possibly need more time?

“Come on baby, help me out with this?” I said, gesturing towards my hard dick.

“Later,” she replied, “wouldn’t you rather wait until tonight anyway? I’ll probably be drunk and then you’ll get pornstar-Katie instead of stressed-getting-ready Katie.” That was a good point. Pornstar-Katie was always an amazing time. I showered then left to get ready myself, leaving my cock and balls aching for attention.

A few hours later, Katie emerged from the bathroom. She’s a stunner. She had long brown hair in loose curls, and her makeup was perfectly done with winged eyeliner that made her hazel eyes look even prettier. She was in a skin-tight floral dress that wrapped her hourglass body perfectly.

“Damn girl, I would.” I told her, and she giggled. “You will.”

———-

We got to the restaurant. Brett and Heather were already there in the waiting room but were not talking. We all had an awkward laugh as they had guessed that each other was the blind date but were both too shy to ask if that was the case. Whoops, we probably should have tried to get there first. Poor Brett was stiff as a board when we finally introduced them.

Dinner was better. Teppanyaki. Delicious and entertaining, but expensive as fuck. The girls gushed as the chef did his little knife dance and chopped up the food.

Katie and I sat in the middle, all four of us facing the chef. The girls dominated the conversation, mostly talking about their school stuff. Heather was looking real cute. She had blonde hair, wore a green dress, and was done up to the nines as well. I admit I had to sneak a peek of her ass as she went to use the bathroom. I usually found Heather to be more cute than sexy, but after the afternoon’s tease I probably could have found anything to be sexy.

After a few beers, Brett loosened up and joined the conversation more, asking Heather about her life and her family, etc. Eventually we swapped the seating order so that the boys were in the middle and girls were on the sides, so that they could chat easier.

Katie leaned up and whispered into my ear “I think it’s going well! Are you having fun?”

I said I was and wrapped my arm around her.

She continued whispering to me, “I can’t wait to fuck you tonight” and she squeezed my dick through my trousers underneath the countertop.

I hurried up the team to finish their drinks and we paid and left.

———-

“So where should we go dancing?”

Brett froze up. I know that look well. I also hate dancing. It’s a social anxiety nightmare. Time for a bro-move.

“What if we went to the casino instead? You girls picked out the restaurant, let us pick the entertainment?” I offered. Katie pouted but agreed in the end. A couple glasses of wine usually made her quite agreeable.

Brett would later tell me that he was relieved by this change of plans.

At the casino we got more drinks and tried blackjack. We lost. Then we tried the slots, and lost more. We’re cheap and we only played a couple bucks at a time, so it wasn’t too bad. We all collectively laughed at our misfortune. Brett and Heather were talking more and more, getting closer to each other. He would jokingly pretend to steal her chips and she would slap his hand away, laughing hysterically.

We moved to roulette. The alcohol kept winning, and we kept losing. Heather asked me what I was going to bet on for this spin. I said I’m doing 5 bucks on black. She said that was boring and then in a seductive voice, she said “We need to spice it up a bit”. I was instantly intrigued.

“What did you have in mind?”

“If you lose, you have to grab Katie’s boobs right here at the table”.

“What the fuck?!” said Katie, but she was laughing playfully. It was super crowded so I doubt anyone would really notice, but it was still risky because I didn’t want to get kicked out. All three of them looked at me, as if I was the captain of this drunk shit-show. Obviously it was a no-brainer for me, either I win money or I get to grab some titties.

“All right, let’s do it!” The ball spun around the wheel and the four of us all watched. It spun around for hours, but finally landed on… Black! I collect my winnings, surprised to finally get chips back rather than give them away.

Heather was disappointed but I assured her the risk made it more fun. Now she stepped up to play, and turned to looked at us, daring us to throw a bet onto it. I waited for the other two to say something but nobody did, so I pushed the envelope: “If you lose, you and Katie have to go to the bathroom and text us a topless pic of you guys.”

“Why am I always the loser of these?” Katie asked, still laughing.

Heather played red and lost, Brett and I were thrilled. They giggled their way to the bathroom and sure enough we got a grainy picture of the two of them standing titty-to-titty beside each other in one of the stalls.

After they returned, the game was fully on. We went round after round taking turns playing roulette with extra bets on the side. Brett lost and had to tell us all a graphic story of the last time he got laid. He was VERY embarrassed about telling the story and the girls didn’t let him off the hook as they dug for the dirty details. Katie won next, so she didn’t have to do anything. I lost so I had to go refill everyone’s drinks. Katie lost so she had to go to the bathroom and come back with her panties in her purse. Brett lost again and had to sneakily reach up Heather’s dress to feel her ass.

This continued on for a while until Katie went up for a final spin. Heather was really starting to feel bold so she said “if you lose, then we get to watch you give <me> a blowjob.” Holy shit, now it was getting really wild. Katie replied, “Okay but if I win then you’re sucking off Brett”. The girls agreed to the terms while Brett and I exchanged “are you kidding me?” looks.

The ball spun around and around and the girls were holding onto each other, both scared shitless of the outcome. Finally it landed on red, so Katie won her bet. They both burst out laughing and Katie gloated. Brett was cheesin’ from ear to ear.

“Okay, so where are we doing this?”

———-

We cabbed back to our apartment.

While Katie and Heather poured more drinks, I checked in with Brett to see if he was still good. He said Heather is wild but in a good way, and that he was having a blast. Katie pulled us all into the bedroom and told Heather, “Alright, let’s see it!”

Heather didn’t even fake being shy. She launched into Brett and pushed his back into the wall, forcefully making out with him. Poor guy was almost knocked off his feet but he started kissing her back and feeling her up. Katie and I sat on the bed watching them make out for a while until Katie said “Let’s go, I want to watch my porn show!” Heather laughed and then got down on her knees. She unzipped Brett’s jeans and pulled out his dick, licking it up and down before popping it in her mouth. She moaned and he sucked in a sharp breath of air.

Katie and I were transfixed. I’d never been this close to another dude getting sucked off, so it was quite the thrill. Heather was looking like an experienced pro, taking him deep for a while, working his balls, then slowing down to lick his head.

“Grab her hair, she’s a big girl, she can take it” Katie encouraged. Brett tentatively reached both of his hands down and grabbed onto the back of Heather’s head and she moaned as he gently pumped into her. Katie continued her role of the blowjob facilitator. She got up and pulled Heather’s dress up over her head, revealing her black, lacy bra and panties.

Meanwhile I was rock hard in my pants still. It was so painful to be hard this afternoon, at dinner, at the casino, and now here on my own bed without any sort of release. Katie, bless her heart, must have sensed this and she turned around, got down on her knees, and pulled my dick out too. She took me into her mouth and all the pain finally slipped away. My world started spinning from the alcohol and the pleasure and I closed my eyes, enjoying the moment. Katie reached up with her hand and stroked my abs as her warm mouth slowly sucked on my hard cock. The girls kept up their hard work as time seemed to slip away… I opened my eyes and Katie was staring right into my soul. She stopped sucking and gripped my dick tightly. She gestured over to the others and winked. “What do you think, should I?” she mouthed to me. I nodded and gave her the green light. She stripped totally naked and then crawled over beside Heather. The two girls giggled and took turns sucking Brett’s dick and licking his balls. Brett looked over at me as if to say “Shit dude, is this cool?” and I just smiled. He kept gasping and saying “oh fuck, oh fuck, that’s so fucking good.” I watched until the girls stopped and Heather said assertively “alright boys, our turn!”

Heather got naked and laid her back down on the bed with her legs up in the air and her ass hanging off the side. Katie got beside her in the same position. Brett and I also stripped down. I knelt down and I buried my face into Katie’s warm and wet pussy, and started licking her clit the way I know she loves. She usually likes some butthole action too when she’s drunk, so I brushed a finger over it and she moaned loudly. I took the hint and started slowly licking lower and lower until I was licking all around her asshole, but not quite on it. I stopped rubbing her clit and kept slowly licking a big circle around her ass. She moaned louder and started whimpering, eventually using her foot to push down on my head. I figured that’s enough teasing and I dove right in with my tongue just as I continued massaging her clit with my fingers and she yelled out in pleasure. Heather was also moaning away and the two girls were rotating between gripping our heads, gripping the bed, gripping each other.

Katie stopped me and got up on her knees, with her ass still hanging over the side of the bed. “Give me your dick baby, I need it” she said. I was happy to oblige and I sank right in to her warm pussy. Heather was now watching us with glazed-over eyes as Brett kept eating her out. Eventually he got up and went to go fish out a condom from his pants. He came back and mounted Heather on the bed in missionary position.

Folks let me tell you.. if you can afford it, a king size bed is worth every penny. The 4 of us continued fucking with enough real estate to really swing our weight around.

Katie switched to being on top, riding me with her hands on the head of the bed. Heather and Brett came up beside us and followed suit for a while. Then they switched to doggy while facing us and I got to see Heather’s surprisingly huge tits swinging away as Brett pounded her from behind. All four of us were moaning with the occasional dirty talk. Katie asked me while she was riding on top, “Do you like watching my friend get fucked?” Hell yes I did, but I gave a diplomatic answer, “You both look amazing getting fucked”. As I said this I was rubbing her clit with my thumb and she yelled out “Oh shit I’m cumming!” and the other two stopped to watch as she shook violently on top of me for the duration of her orgasm. She sighed as she came down and then bent over to kiss my neck, something she knows I love. “Come on baby give me your cum, I need it” she whispered in my ear as the others resumed fucking. She always knew the best way to coax the cum out of my balls, so she kept sucking my neck and begging me for it. “Please cum baby I need it inside of me. I want to feel you fill me up.” Pornstar-Katie was here and she meant business. I hit the point of no return and roared out as I emptied my balls deep inside her pussy. She collapsed onto me while I was breathing heavily. We were a sweaty mess.

She turned her head and we both started watching Brett and Heather. Heather’s eyes were closed and she was moaning loudly as Brett kept pumping her from behind. “I want to finish all over your ass” he said suddenly and aggressively. I think all of us were a bit surprised to see a dominant touch from him. Heather smiled and replied “Wherever you want, I’m yours!” So he pulled out and practically ripped off the condom and stroked several ropes of cum all over her ass and up her back. We all laughed as we came down from the sex high and quickly discussed how crazy this was. Crazy but amazing. Brett and Heather went up to shower first and then Katie and I went second. It was deep into the morning so we lent them some pajamas and we all crashed into bed together. When we woke up, it felt a little bit tense at first, but we all powered through the awkward feelings and ate breakfast together and didn’t make things weird. They ended up dating and we all stayed close friends for a long time.

Source: reddit.com/r/gonewildstories/comments/ge2vb0/double_date_group